Trapped in Panties or How My Wife Trained Me To Be A Sissy (2022)

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Category: Missy Satinpanties
Written by Missy Satinpanties

Well, I've been forcibly feminized, cuckholded, and, now my status was going from bad to worse. well... wait a moment and let me start at the beginning. That way you can understand what I'm talking about...

It all started about 3 years ago, about six months after Connie and I got married. I was working as a mid-level mechanical engineer for a large engineering company, and Connie was working as a customer service rep for a national insurance company. Neither one of us made piles of money, but together, we made enough to afford everything we needed, and to slowly acquire the things we wanted. We rented a small apartment, and were devoted to each other. Our devotion and financial situation, though, changed drastically, although I'm still not sure which changed first.

Connie and I are about the same height. I'm 5'7", and she is an inch shorter. Now I was about to say that I didn't mind it when she wore heels, and was taller than me, because I'm secure in my manhood. That too seems to have drastically changed. Now Connie is a slender, small breasted lady who is perfectly put together, from her long, lustrous black hair, to her small, perfect, and perfectly pedicured feet. Me, I'm slender, with a mop of blonde hair, with hazel eyes to her gray- green set. So, that's us. Now on to what happened.

We were married about 8 months or so, when the whole thing really got going. She had stepped into the bedroom in a pair of white silk panties with black lace that I had bought her at Victoria's Secret. You see, I'm a sucker for lingerie. I always figured that it was a present that she could unwrap first, and then I get to unwrap it later! With a matching bed jacket and a pair of white high-heeled sandals, she was so beautiful and sexy, it took my breath away. She casually began to rub her shaved pussy through the thin silk, smiling at me in a most enticing manner. Just as casually, she slid the delicate undergarment down her long, beautiful legs, and with a flip of her foot, launched them at me on the bed. I caught them, and held them to me nose without even thinking, my hard on bobbing in front of me, informing Connie just how much I was enjoying the delicious scent.

"Hey Stud," she purred, "why don't you put them on, and we'll match! Then I get to take them off you!"

If it meant sex with my beautiful wife, I would have done darn near anything! I quickly pulled the soft panties up my legs, and settled them in place, my hard on making a white silk tent. Our sex that evening was some of the wildest ever. I ate her to several orgasms, and after we made love, ate her to another, oblivious to the fact that I as swallowing my own cum. After that night, nothing of the sort happened for a week, and sex went back to good, but sort of plain vanilla. That next Friday, though, she repeated the episode, with a pair of peach satin panties, and the sex jumped from plain vanilla, to a banana split with whipped cream and two cherries!

Now I was hooked. If she tossed me a pair of panties, they went on like a shot. After several months of this, she looked at me sitting on the bed, once again wearing the white silk panties with that sexy black lace trim.

"You know," she said quietly, "you would look a whole lot sexier if you didn't have all that yucky pubic hair."

When I protested, weakly, she replied, "Well, you like me shaved down there, why can't you repay the favor? Why do you think I don't like to give you a blow job?"

A minute or two later found me naked in the bathroom, with depilatory cream spread on both legs, my crotch, ass, and underarms. As my wife snapped off the disposable rubber gloves that she had used to spread the cream, she told me to stand there for twelve minutes, and then get a shower, using her loofah to get all that nasty hair gone. Then I was supposed to pull those cute little cock-hardening panties back on, and get my ass back into bed! Needless to say, I planned to follow directions! When I stepped out of the shower, I saw that she had laid out one of her pink bath sheets, and that not only were the panties on the little table, but the bed jacket as well. Drying myself off, I was amazed at how different it felt with no hair, and almost came on the spot when I pulled that silk up over my smooth legs, and how it flowed around my shoulders and back. When I got into bed, she was all over me like a lioness on a wounded zebra!

Fast forward now, about 4 months. I was keeping my body hairless, and now, when I wanted to initiate sex, I would go into her drawer, or into the hamper, and put on a pair of panties, and sometimes (at her urging, at first) one of her sexy little chemises, or baby doll nightie. Sex with my wife had never been better, and I was learning to equate the feeling of lingerie hugging my body with the best orgasms of my life. Yeah, you bet, I had fallen into the trap, and wasn't even looking for a way out!

One Monday morning, as I was getting ready for work, I opened my dresser drawer, and instead of my underwear, it was full of pastel colored, nylon panties. Nothing radical, just sort of everyday panties, well, everyday for a woman! When I asked Connie what was going on, she just smiled, and sort of purred, "Well. You like wearing panties for me, and I love seeing you in them, so, please baby, wear them for me!" How could I refuse! Now for the next two weeks, all I wore under my clothes were panties, and I had to admit, the feeling of my hairless balls and ass in the nylon was pretty great! Along came another Monday, I opened up the drawer, and once again, was confused. All the plain panties were gone, and in their place was an array of frilly, fancy, and sort of sissy-styled panties. I pulled out a pair of full cut, baby blue, satin panties with lace around the leg openings, and four rows of lace across the ass, a pair of pale lilac nylon bikini panties decorated with lace, seed pearls, and white satin bows, a white satin thong that had a sort of sheer skirt or veil hanging from the rear, and a pair of ivory satin panties with what looked like laces up the back in pink!

I just stared at these, and dozens more of the girliest, sexiest, panties I had ever seen! In the back of mind, though, I did notice one thing. There was not one pair of black or red panties in the bunch. A pair of pink panties with black trim was the closest. Again I demurred, Connie purred, and an hour later I was on my way to work in baby blue, satin sissy panties! Again this went on for a few weeks, until it felt sorta normal. Again it was another Monday. I didn't know if I was looking forward to these days, or dreading them, but I knew that the sex was hot, and if wearing different underwear that no one ever saw but Connie and me, well then, the hell with it! I was a'wearin' panties, pardner! This day, I saw a pile of nylon, satin and lace next to the panties, and picked the top one up to reveal a pale pink camisole with white lace trim. Under my tee-shirt and heavy oxford dress shirt, there was not a hint as to what I was wearing, and you guessed it, from then on, it was panties and a matching cami every day.

This continued for about 3 or 4 months, with me in panties and a cami every day, keeping my body smooth, and occasionally wearing a nightie to bed. That, though, changed to every night after a while. Thanks to my dear wife, I had a nice collection of satin nighties, a pair of pink silk pajamas with lashings of lace all over, and several peignoirs, including one suitable for a bride's wedding night! So, when I tell you that I was secure in my manhood, I'm not too sure if I really had any manhood! Still, I was enjoying the whole thing, and my regular underwear was just in another drawer, if I should change my mind. You see, I still thought that I had some control over the situation. What a fool I was!

The next change wasn't a Monday, but a Thursday night. I came home to find Connie already there, with a letter and a rueful smile. It seems my aunt (whom I hadn't seen in at least 12 years as she was living abroad in Paris) had died, and Connie just found out that through the tragedy of her death, we were now, after taxes, $12,575,000.00 richer! After we both calmed down, we talked about what to do, and Connie once again took charge, and reminded me about the house out in the country that we had seen and fallen in love with the week before while "aimlessly" driving around on a Saturday afternoon. It was a beautiful craftsman style home, with 3 bedrooms downstairs, a large living room/dining room, a master suite upstairs, and 3 acres of land that promised peace and quiet. Needless to say, 3 weeks later we moved from a small in-town apartment, into our own dream home.

Of course Connie quit her job, as we didn't need the small income that she brought in. While I was tied up at work on a major project for the government, we decided, or maybe I should say, Connie decided that she would handle the move and the new furniture and decorations for the house. I planned on "retiring" in about 4 months, following the completion of this project, so that was really okay by me. Once again, I thought that I was on top of things, and had no idea that I was nothing but a pawn in a chess game being played by a very sexy master of the game. Now I have to admit that this project was near and dear to my heart, as it stemmed from one of my proposals. I gave my final task for the company my undivided attention, which meant 12 to 16 hours at work every day, and often on Saturday. Well, I was getting out after this, so I wanted to go out on top of a success. Sex was cut way back as I was exhausted in the evenings, and we sort of dropped back into vanilla sex on Sundays. After a couple months, though, Connie was back at it with the lingerie, and even though I was tired, she managed to get me into satin and frillies at least two nights a week, and I was still wearing panties to work every day, although since it was now summer, and I was wearing open collared shirts, the camis were out for a while.

Fast forward again to October. The project was over, and I had to travel to Seattle, and then to Washington DC to wrap things up. This was a 3 week trip, and when I got home, I knew I would be home for good. Or, not-so-good as things turned out! I called Connie every night, and she gave me the news that she had been doing a bit of remodeling and decorating. I asked what she had done, and she told me that I would just have to wait and see what she had done, but she was sure my libido would like it. Boy did this peak my curiosity!!!

I got home on a Monday night, and there was my beautiful, sexy, and devious wife waiting at the door in a silvery-blue silk teddy that clung to her curves like it was painted on. There were ruffles around the leg openings, and this led my eyes down her magnificent legs, which were now covered in sheer white stockings, to her feet which were encased in a pair of silver sandals complete with little ankle straps, and at least 5 inch heels. She was a knockout, and now towered over me with those heels. She wrapped me in an intense embrace, and kissed me so hard I almost lost my breath! She pulled me inside, and slammed the door, ignoring my protests that my luggage was still in the car. She then practically pulled my clothes off, and drug me onto the couch, pulled down my panties (I painted my toenails pastel pink, and bought the frilly panties in an upscale DC lingerie store, and then wore them home because she mentioned on the phone how much she looked forward to getting me into panties, and then into bed. lucky for me, no strip searches at the airports!), and damn near raped me! About an hour later as we lay there sweating, she told me to come upstairs with her, so I could shower, and she could show me some new things she bought, and some work that she had done. Again the docile little man followed the big strong woman, straight to my doom.

Now the second floor of the house is basically an open loft, with a two huge walk-in closets to the left, and a little corridor between them that goes into the bathroom. To the right, is a small room or alcove that is separated by a partial wall and arched opening, which the real estate lady was proud to point out could be a sitting room, a little office, or even a nursery when the time came to have a baby. I allowed Connie to lead me into the bathroom, where she told me to soak in the tub for a few minutes, and then take a shower and wash my hair. After I was done, she said, we could have some more fun. Twenty minutes later I stepped out of the shower, and saw that there was another of her fluffy pink bath sheets waiting for me, and a note pinned to the sheet.

"Darling, after you dry yourself off, please use some of the dusting powder that I laid out for you on the sink. After that, open the big box on the floor, and get dressed. I know some of it may be a little new, and sort of silly, but indulge me. I want this to a night of sex and satin, and a night that you will NEVER forget!" As a final little tweak, it was signed, "Sexy Connie" in pink ink.

Now dry, and hard, I used the perfumed body talc, wondering why she wanted me to wear such a girly scent, but following orders just the same. Sure, they were couched as a suggestion, but looking back, they were orders just the same. Now dry and smelling sweet, I slowly opened the box. On top of a layer of tissue paper was a pair of pink satin panties. Now these were a lot like the blue ones I already owned, but these were not from Sears or some other store! First of all, no manufacturer's tag, the satin was double layered, there was no cotton crotch, and the workmanship was superb.

Shrugging my shoulders, I pulled these soft, heavenly panties up my legs, and settled them around my already hardening cock. Next up was a pair of white nylon ankle socks with a cloud of pink lace around the tops. These went on too. I looked under the next layer of tissue, and found what can only be described as a training bra that exactly matched the panties, with a cute little white satin bow in the middle, and ruffles on the shoulder straps. Yep, that went on, too! I had come to love the feel of nylon, satin and lace, and associated them with great sex, and lots of it.

That association would change a bit in the coming days, although I had yet to realize that. I stripped another layer of tissue, and saw a mass of white frothy lace, with a little note.

"These are petticoats, sweetie, you step into them, pull them up around your waist, and tie them tight. I can't wait to see you, and show you the rest of my surprise!"

Again signed the same way, and again, I followed the directions. I sort of had an idea of what lie beneath the next layer, and I wasn't wrong. I had never liked Connie in slutty clothes, so always wanted to see her in cutesy lingerie, sort of little girly, or demure like a virgin bride, so I guessed she was reciprocating. If it ended in more great sex, I didn't care!

I gently removed the pink satin creation, and looked it over. It had a full, but short skirt, a high neckline, with a little collar, and short cap sleeves with little white satin ribbon trim on each shoulder. It took me a while to get it on right, and get it zipped up, and when I looked in the mirror, I saw that any bending would show off my sissy panties to the world.

"What world," I thought laughing, "It will just be Connie and me!"

Next up was a full apron in a sheer, sparkly, white material. Again a note informed me that this was a pinafore, and it went over the shoulders, and tied in the back. Just do the best I could, and she would tie the bow pretty for me. I got it on, and looked in the mirror again. The pinafore made me look, for all the world, like an illustration out of some book, like Alice in Wonderland, or something. Very demure, very girly, and on Connie, it would be very sexy. I had already seen that there were shoes in the box, so pulled them out, and got a real surprise! They were satin Mary Jane shoes, which had been dyed pink to match the dress. Okay, no real surprise there!

What got my attention was the darn near sky-high heels! I later found out that they were "only" about 4-and-a-half inches high, but I had never walked in heels before. Good thing these were kind of thick, and not some sort of stiletto heel, I could have killed myself trying to walk! After fastening the little strap across the instep of each foot, I carefully stood up, and tottered over to the box to see if I had missed anything. I had indeed! There was a blonde wig with two pigtails in the box, which went right on, and a pair of what looked like pink satin mittens, with no thumb!

I had no idea what to do with these, but again, a note told me that they were, indeed, mittens, and I was to pull them on to "complete" the outfit. It also informed me that I was to call Connie as soon as I was dressed. I did so, and she entered full of oohs and ahhs, and hugs and kisses, and lots and lots of fussing! My bow was straightened, and she did something to the back of the dress, up by the collar. I figured she was fastening the little button that all ladies' dresses had. She was fastening it, all right! There was a small padlock holding my dress closed! She also pulled the laces tight on the wrists of my mittens, and I realized that there was a very thick layer of cloth, sort of like an oven mitt, between the inner and outer layers of satin, and with them tied off at the wrist, my hands were useless, and I had no way of removing the mittens. She told me not to worry, that this was all part of the game, and led me out into the bedroom.

About a year earlier, she had gone to a sex toy party that one of her friends from work had thrown, and came home with a couple of vibrators, and a set of 3 butt plugs, small, medium, and scary. She also had a thin anal vibrator. She never used the butt plugs, but I used the thin vibrator on her sexy ass a few times when we made love. I now saw it was lying on the bed.

"Oh boy, this is going to be great!"

It was, but not for me. She led me to the bed, and told me to stand at the foot of the bed. She then bent down behind me, kissed me on the ass, and while I was distracted, she looped a Velcro strap around each of my ankles, and bound my legs to the bed. Standing up, she took another strap, looped it around my useless wrists, and took the attached rope, and tied it off at the headboard, pulling me forward, and causing my satin and lace encased ass to stick out. This was going way too far for me, and I told her so. She didn't say a word, just climbed onto the bed, and started kissing me, caressing me, and pushed one of her breasts up and out of the teddy for me to suck on.

This might not be so bad after all, so I loosened up. She told me that she wanted me to feel what she felt when we made love, so please, please, just for a few minutes, go along with the program! I said I would, and she clapped her hands and giggled like a schoolgirl. She then reached into the drawer in her nightstand and brought out a large pink ball, with straps running through it. She told me it was a ball gag, and that she wanted me to wear it, just for a moment, it would be fun. I wanted no part of that, but she grabbed my nose, and when I had to open my mouth to breathe, she forced it into my mouth, and buckled it tightly around my head. Now I was scared. I had no idea of where this was going, and in my wildest imagination, I could not have foreseen what the next few minutes had in store for little ol' me.

Getting off the bed, and tucking her tits back into the teddy, she pulled on a matching sheer robe and walked behind me. I heard her lifting something, and when she came back into view, she had the little 19" LCD TV with the built-in DVD player. She set it on my nightstand, plugged it in, and told me enjoy the show. When she hit play, I was shocked, and nauseated. She told me that she had placed video cameras all over the apartment, with three of them in the bedroom, and then she had edited all the video down to this 90 minute movie of me.

There, on the screen in front of me, was me, begging to be allowed to wear her panties, pleading with her to wear panties to work (Of course with her teasing that led to these events edited out). Me dressing in a nightgown to go to bed, me putting on panties, and then my slacks to go to work, me painting my toenails, and then begging to paint hers, and on, and on. "By the way," She said, "This is just one of about 25 copies of this DVD. I have some hidden in the house, one at a friend's house, and one in a safety deposit box, so don't get any ideas of destroying this copy, it won't help! Oh, and Honey, I want you to know that there were two cameras in the bathroom, to record you getting all dressed up." While the movie was still playing, she again walked behind me. I thought that things could not get any worse, and again, I was dead wrong!

I felt her hand under my (MY?) skirt and petticoats, and then I felt my panties being pulled down. She now inserted her lubed finger into my ass, worked it around, and pulled it out. I remembered seeing that skinny vibrator on the bed, and relaxed, as it wasn't any bigger than a finger, and shouldn't hurt too much. Too late, I saw that one still on the bed, as she began to force the medium size plug up MY bottom!

"Relax, and push like you are taking a dump, and it will hurt much less," she said, "you might as well help, because this plug is getting rammed up your ass with or without your help! The more you relax, the less it will hurt, although I promise you, it WILL hurt!"

As I tried to relax, breathing hard through my nose, she got the nose of that monster against my sphincter, and began pushing. I thought I was being ripped in half, and screamed for all I was worth into the rubber ball gagging me. With tears streaming down my face, she forced that plug into me, ignoring my muffled pleas and tears, until I felt like the Goodyear blimp was filling my ass. I couldn't believe the pain! I'll leave you alone with your movie to get used to your new friend, she said nastily; as she pulled my panties back up, and re-arranged my skirt and petticoats. And then, she left. She left me tied to the bed, my poor ass in terrible pain, watching me make a simpering, sissified ass out of myself on video.

After a few minutes, I heard her come back up the stairs. She turned off the TV, then reached out to my wrists, and using an attached hook, clipped my wrists together. Then she got down behind me, and quickly released my left leg, and pushed it over, and clipped a 12 inch chain from ankle to ankle. Following this, she unhooked my right ankle from the bed, and let loose the rope to my wrists.

With her help I minced over to a chair in the doorway to the little alcove off the bedroom. I noticed right away that the legs to the chair had been cut down, and it was only a foot off the floor. It was also painted pink, and seemed to be bolted to a 4' X 4' piece of plywood. She pushed me down into this chair, and quickly hooked my wrists to a short chain that came up between my legs. She then grabbed my ankle chain, and pulled my feet forward. There were two eyebolts that came up through the plywood, and once my ankles were hooked to these bolts, and my hobble chain removed, I was sitting in a little chair with my legs spread wide. I had no balance to even try to get up, and anyway, my hands were chained to the chair.

Connie now went behind me again, and placed a collar around my neck, and I could hear it being fastened to the high back of the chair. Now legs spread, forced to sit bolt upright, dressed a baby sissy, gagged, and in great pain as the huge (at least to me) butt plug was pushed even harder into my bottom by the hard wooden chair, I sat and waited to see what would happen next. I was so confused! My beautiful, loving, sexy wife was treating me like, like, like I don't know what! What had I done to deserve such treatment? And, maybe more to the point, why was I hard as a rock under my panties????

"Well, little Emily," Connie began after she sat on the bed facing me. "Yes, Emily. I can hardly call a panty wearing sissy, who begs on tape to be allowed to dress up for his 'mommy' Mike, now can I? From now on, you name is Emily. Now let's see, I'm betting you have a lot of questions for me, don't you Emily?"

I tried to nod my head, but had no movement because of the collar. She continued, "You see, I met a man, a REAL man about 3 or 4 months after we got married. Yes, you were a sweet husband, and your very talented tongue made up a lot for your lack of cock, but when I found a man with a thick, juicy cock that really fills me up, I had to have it, and have more and more of it. So, you see, I came up with a little plan. I have been steadily sissifying you over the last couple of years. Those vitamins I got you to start a few months ago because I thought you looked run down? I bought a bottle of vitamins, threw them out, and replaced them with female hormones. When you asked me if you were putting on a bit of weight, that was your little titties starting to form, and your body beginning to soften a bit. You have noticed that you don't get hard as often as you used to, or even as hard when you do? That's the hormones! I won't increase the dose, because I want you as a semi-functioning man. Now let's see, oh yes! Your aunt! I knew at least 6 months before she died that she was in a coma, and that you had left orders for her to be kept on life support for six months, to she if she had any sort of chance to regain her conciousness. What, you never did that? Hmmm, maybe I did sign your name for you, and maybe when the French hospital called to confirm, maybe my boyfriend did the talking for you. Gee, I forgot! When we went for that little drive, and just happened to see this place, and it just happened to be for sale, and I just happened to want to go in and see because it just happened to be the open house... You guessed it girly! I had already talked to the real estate agent, and had made a tentative offer at full asking price. All I had to do was make it look like it was your idea. Just like the panties, and the nighties, and shaving yourself smooth for me, it was all so damn easy! Now with the power of attorney that you made out before your trip, all the money, and the house, are mine! You really should read what you sign, you silly little sissy! I have decided to keep you here for a year, and use you to have a bit of fun. Then I'll let you go, and give you enough money to get going. It's the least I can do for you."

She got off the bed, and started to walk toward me, swinging her hips, and even though I was scared to death of her now, she was so damn sexy!

She stopped right in front of me, and I saw now that my face was at the level of her crotch. I could see the damn stain on the teddy, and could smell her sex. This only made me more confused, and harder than ever.

"Now my little sissy husband, there is one eensy, teensy thing I forgot to tell you," she started in a syrupy sweet voice, "and before I tell you, I'm going to take out that nasty gag, so you can talk."

(Video) My mum caught me wearing her underwear Audio/Crossdressing/M2F/Genderswap/TGTF/Boy2Girl/Feminization

With that she unhooked the straps, and gently pulled the ball out of my aching and drooling mouth. Taking a hanky she wiped the drool off my lips and chin, and asked me if I wanted a drink. I told her that I did, and she held a child's sippy cup to my lips, and then fed me some apple juice. I didn't care, I was thirsty, and explanations could come later!

After I had enough liquid in me to allow me to actually talk, I began to yell at Connie, demand that these restraints come off, demand...well, you know what I demanded. I yelled at her that I was not a cross dresser, that I only did what I did because she wanted me to, and it seemed to make sex better. finally, though, I was all yelled out, and through all of my tirade, no matter what I said, or how loud I said it, all the did was sit on the bed, look at me, and smile this little cat- that-ate-the-canary grin. Finally my throat was sore, and I was exhausted, physically and mentally, and just wound down. She sauntered over with that damn sippy cup, and offered me another drink, which I took, which turned out to be another of my many, many mistakes. Did you know that you can conceal a very powerful sedative in apple juice?

When I came to, I was still very groggy, and my first thoughts were that this was all some kind of horrible dream, and all I had to do was to open my eyes and everything would be just fine. So, I slowly opened my eyes, and reached up to rub the sleep out of them. Or, at least I tried to reach up. My hands were still restrained, although not between my legs.

They were now strapped to the arms of the pink chair. My hands were still in their mittens, my legs were stretched out and spread and still hooked to the bolts, my neck collar was still hooked to the chair, and from the pain in my backside, I knew that the horrible butt plug was still in my poor bottom. Also, my jaw was sore, and my mouth was very, very dry.

As I got a bit more awake, I noticed that instead of being dark outside, like it was when I was strapped into this chair, it was light, and from the angle of the sun, it must be about noon, or just early afternoon. That was when I realized I had been drugged. I also saw a new addition, which was her full length mirror, set up in front of me. There I was. Pink satin dress, stiff petticoats, panties on display, no, wait a bit, those aren't the same panties... They appeared to be pink plastic panties, and as I wiggled around, I felt something thick and soft, and then it hit me, DIAPERS! The bitch had put me in diapers and plastic panties!

I tried to yell, but only got out a weird sound. I felt something in my mouth, and looked again in the mirror. I had on some kind of gag, but not a gag. Whatever it was was held in place with straps of clear plastic that seemed to be hooked behind my head, but under the wig. I began feeling with my tongue, and found that I had a ring of some sort in my mouth that sat on my teeth, and had a ridge on both sides, so that it held my teeth apart, and thus my jaw, and would not slip off, either in or out. With some effort I was able to close my mouth enough to lick my lips and make them feel a bit better, but I could not completely close my mouth. I had no idea of what kind of Hellish torture device this was, or what its use was, but I knew I wasn't going to like the answer!

A moment later I heard her high heels on the wooden stairs, and she walked in with a big smile on her face.

"Aw, is my widdle baby Emily awake?" she cooed in a sickening sweet voice. "I'll bet someone needs a widdle dwink after their sleepies!"

I started to yell at her, and she just smiled, pulled something off the bed, and walked over. Now I was to find out a little about this appliance in my mouth. Without a word she shoved a thick rubber gag in through the ring in my mouth, and with a little twist, locked it into the ring.

"Now little baby, I won't have to listen to your pathetic whining!"

She just stood in front of me, wearing a long, black silk peignoir set, and a pair of black peep-toe pumps. I didn't recognize the peignoir, and realized that either she had bought it for herself, or her lover gave it to her.

As if reading my mind, she spoke up, "Do you like Mommy's new nightie? Mark bought this for me last night. Yes, that's right, last night, while you were sleeping like a widdle baby. By the way, Mark thinks widdle Emily is so-o-o cute! He can't wait to, well, you'll learn soon enough."

While Connie was talking, my tongue had been exploring the gag in my mouth. It had a flange or something near the rounded end, and there seemed to be a hole through it. I tried sucking air, and sure enough, the hole, though tiny, went right through.

Again this beautiful, sexy, but evil bitch read my mind. "Do you like your new gag? Let me explain it to you. You woke up with just the ring in your mouth. You see, this keeps your mouth open, and lets things go in your mouth, and you can't stop them, or more importantly, bite them."

This statement scared the hell out of me! She went on, "And, as you have found out, I can slip a few different gags in place, to boot. Now you have a small penis shaped gag in, which has a hole in it to allow me to force feed you liquids. There is also a small penis gag with no hole, and a really, really big cock that will fill that sissy mouth of your from front to back, and bottom to top. Now I know you'll like that!"

No I wouldn't, and tied to shake my head, but only got a little movement. "You'll notice, I'm sure, that I have put my widdle baby in a big soft diaper so she can go pee-pee when she needs to, because Mommy's widdle baby won't be allowed to use the big potty for a while!"

With that she just smiled. She walked up to me, and lifted the hem of her nightgown up, and over my head. Now my face was inches away from the pussy that I had worshipped these last three years. All that separated me was a thin, and very wet, piece of almost transparent black silk, and this damn gag. She reached under her gown, and pulled the little bows on either side of the panties, and they fell off and fluttered to the floor. I could smell the ripe aroma of her arousal, and knew that this was getting her off. I was horny, sad, scared, hell, I don't know what I was, all I really knew was, that like the trained animal I had become, all I wanted to do was stick my face in that pussy, and make her cum. Sick, ain't it? All that she had done to me, and I still wanted to lick her, taste her, and... Oh well.

Laughing at the predicament she knew I was in, she backed away, pulling the soft silk tent off of me. Then she reached down, and picked up the tiny little wisp of black silk that had covered her pussy, and almost carelessly, draped it across my face so the fragrant wet stain was in front of my nose. So, there I was, gagged, diapered, dressed as a baby girl, and my wife thought it was an added kick to arouse and further humiliate me. At least I thought I was as humiliated as I could get. I was wrong, very wrong. The worst was to come right now...

I heard another set of footsteps coming up the stairs, but this tread was heavier, and softer. My questions were answered when a tall, dark haired man stepped into the bedroom. He was wearing a pair of soft leather slippers, and was wearing what looked like a dark red silk kimono. He walked right up to Connie, wrapped his arm possessively around her waist, and kissed her deeply. So, this was her lover, Mark. He began to fondle her delicious nipples, and then pulled up the hem of her gown, and began to finger fuck her in front of me. They both watched my reaction, and laughed at my ineffectual squirming as I tried to get free, or at least turn my head, neither of which was possible.

They both came closer, and Mark began to walk around me, examining me. He reached down, and pressed his hand against the diaper and laughed, "You're right, Sweetheart! The fucking little sissy IS hard!"

He stepped back, and Connie just looked at me, and then looked at him and said, "Well, go ahead, Lover, take the pathetic little sissy to her destiny."

With that he untied his robe, and let it fall to the floor of, what was so recently my bedroom, leaving him wearing only a matching pair of boxers, well tented from his hard on. My wife knelt down, and slowly pulled these down his muscular legs to his ankles, and helped him step out of them. Planting a kiss on his huge cock, she stood up and walked over to a padded dressing table chair that was sitting off to one side. She sat down, and with her chin in her hands, and her elbows on her legs, she prepared to watch the show. I was ready to skip the show, but as you know, I had no choice, not now, and it seems, not ever.

With a sharp twist and pull, the gag was yanked out of my mouth. He also pulled the panties away from my face telling me that I didn't even deserve to sniff her dirty panties. He then stepped in so that his cock was at my mouth, and I could smell the musty aroma, and could also smell my wife. He had fucked her, never even cleaned himself, and now that cock was going to be in my mouth! I started to yell, but didn't have the energy, and what came out was a whimper, and then I started to cry.

That seemed to be the signal, and he jammed his hard cock into my strained and aching mouth. My lips were wrapped around his cock, and the ring with the clear plastic straps held my teeth off of him. I saw several flashes and knew the event was now recorded on digital film for whatever she wanted to do with it. I was giving my first blowjob, albeit a forced one, and I was giving to my wife's lover, the man who was taking my place in my marriage bed! I tried to hold my lips away from his warm cock, but to no avail. He was ramming his meat into my mouth, choking me, making me gag, and, I'm sorry to report, actually sort or turning me on. Finally the assault on my poor mouth was near the end. He jerked spasmodically, and shot a load of cum into my captive mouth. Since he did not pull out, and then grabbed my nose and held it shut, I had no choice but to swallow it, so I could continue to breathe around his softening member.

With that he pulled out, looked at my wife, and announced that he was taking a shower, and when he got out, they could put the sissy in her new home. I started to yell again, asking what the hell was going on, but Connie never said a word, just shoved that damn gag back into my mouth, twisting it into place, and silencing me once again. Then she put on that sweet mommy voice and asked, "Is Mommy's widdle baby thirsty after her nice blow job? Ahh, I'll bet she is, so Mommy will give baby Emily a very special drinky-poo, that will help widdle baby understand just what her place will be in this family."

With that cryptic comment, she pushed a clear tube into the penis gag's hole, and yelled out to Mark that she was ready, and out of the bathroom he came, with a large plastic syringe about the size of a soda can. It was filled with yellow liquid, and it did NOT take a rocket scientist to know what it was, or where it had come from! Connie pushed the tip of the syringe into the tube, and began to push the hot, acrid, and salty piss into my mouth.

"Now Emily, you only have two choices. You can swallow the nice pee that Mark brought you, or you can be stubborn and drown or suffocate on it. I really don't care. I'm sure, however, that when the paper's learn that you died choking on piss, that your family will be real proud of their fucking sissy!"

With that warning, and no desire to die in any fashion, I swallowed the hot piss in big gulps as she forced it into me. Now the average bladder only holds about a half of a liter of liquid at best, but this felt like gallons of piss being forced down my throat. I sat there, swallowing, crying, and hating my wife, hating Mark, and hating myself. I hated myself for ever getting into this situation, and really hated myself because my cock was still hard under the damn diaper!

"Does my widdle sissy husband want to know an itty bitty truth?" she asked while pumping the last of her lover's piss into my mouth. "I don't love Mark, or the other two men that have been my lovers over the last few years. You are the only man that I have ever loved. But I have found two things that I love even more. The first is sex. I love sex, crave sex, live for sex, the wilder the better. But, there is something out there, that for me, trumps loving you by a mile, and even trumps great sex. Do you know what that might be? Care to guess? No, silly, it's not boys in panties and diapers, although that is cute!! What I love, more than anything in the entire world is POWER! And now, I have complete and total power and control over you, and my pussy is dripping just thinking about that! No man has ever got me this hot, and kept me as hot as this total domination over you!"

So that's what my wife has turned into. A power mad, I don't know what, who is willing to destroy what she claims to love for the kick. When I met her, she was shy, demure, loving, and had only known one other man (so she claimed), and now she was the she-devil of all times, willing to do anything for a power-high. Even though I now understood, that really didn't help me out. I was still trapped.

I sat there with the taste of Mark's piss in my mouth for a few minutes, until he stepped out of the bathroom naked. He grabbed what used to be my wife, and threw her onto the bed Whew! At least it doesn't look as though he plans on using me any more for a while, at least. They began kissing, and his hands were all over the woman I thought I loved. I couldn't watch, but couldn't close my eyes, either. She slid down, and looking at me sideways, took his cock into her mouth as if to say, this is how you make love to a penis, learn from me!

She sucked that monster into her mouth, and began to bob her head up and down. Mark reached down and grabbed her head, and held her against him, his cock fully into her throat. After a moment, she pulled back and began to kiss and lick his balls, and even lift them up and lick down towards his ass. Kneeling on the bed, she pulled off the sheer robe, and then the gown, and lowered herself onto his pole. Mark was moaning as she engulfed his penis with her beautiful pussy, and he began to play with her tits.

They were fucking like two people who knew what each other liked, like long time lovers. I was sad, but turned on. My little cock was trying to rip the cotton diapers! Finally Mark rolled over, and pulled her to her knees and elbows, and took her from behind, pounding into her pussy until he came. I was mortified to have watched and enjoyed this. Naked, Mark came over, unhooked my feet and arms, and removed the collar. I could smell the sex, and could see the juice from my wife's cunt on his cock. Connie just languidly stood up, stretched, and pulled her sheer black negligee back on, and slipped her feet back into her high heeled bedroom mules.

I was free, but I had been in the same position for so long that I could barely move my muscles. Taking advantage of this, he quickly hooked my wrists together, and did the same thing for my ankles. He then picked me up, quite effortlessly I must say, and threw me on the bed. When I hit, the butt plug jammed into me again, re-awakening a fiery pain that spread throughout my body. Finally Connie came out, wearing jeans, sandals and a cotton blouse. She grabbed a towel and draped it over my head, blocking my vision, and Mark threw me over his shoulder, and together, we all went down the stairs.

I sensed that we were heading into one of the spare bedrooms. We have three downstairs. One has a small en-suite bathroom, and the other two have a small bathroom that separates the two rooms. It was into one of those that I was carried. When I was sat down, and my wrists strapped to the arms of the chair, and my legs strapped the chair, I realized that I was sitting in a tall chair, as my feet did not touch the ground. Then the towel was taken off my head, and I almost passed out with what I saw. I was in a little girl's nursery, complete with an adult sized crib that had a locking, barred top, a play pen, a changing table, rocking chair, and what I was sitting in, a high chair!

The walls were a pale pink, and there was a border of Barbie around the room. All the furniture was glossy white with flower appliqués, while the linens were pink, as were the curtains. With a flourish, Connie went around the room, showing me everything, and opening the drawers and closets to shoe me the baby dresses and rompers, the diapers and plastic panties, the cute widdle toys, the baby bottles, all for me. I could say nothing, do nothing, so I did the only thing I could do, cry. Great, silent heaving sobs left me, the hot tears running down my face as I realized that this was no one-time game, no show of force before I was tossed out like yesterday's newspaper. This thing that used to be my wife was going to make me live like a baby girl!!!!

Again things just couldn't get any worse, and yet again, I was dead wrong. I was released from the high chair, and as soon as I could, I tried (tired, in a short dress, thick diaper, a thick penis gag locked into my mouth, and wearing silly high-heeled Mary Jane shoes) to run. Mark easily grabbed me, and after spinning me around, landed a punch in my balls that had me on the floor in the fetal position, fighting to breathe only through my nose.

After about 10 minutes or so, the pain had subsided enough for me to try to stand, and Mark just stood there, watching me. I knew, beyond a shadow of a doubt who was in charge, and it wasn't me. Finally Connie, who had been silent through all of this, looked at me, and in a kind voice asked, "Are you okay? I really don't want to hurt you, but you have to understand who is in charge, and what is going on around here. You are now my toy, and I plan on using you for my own entertainment. If you don't do things my way, you will be hurt again, but next time, you may not be wearing a thick diaper to cushion the blow. Do you understand?"

I nodded that indeed I did understand, and with a big smile, she took my still mittened hand, and told me that she had another surprise for me. She led me through the connecting bath, which was done up with lots of pink and lilac accessories, and into the next room. I walked right into a little girl's fantasy bedroom, complete with white French-Provincial canopy bed, dresser, make-up table, and nightstands. The walls were the same pale pink as the nursery, but this time there were a few boy-band posters on the wall, a Barbie Play House in the corner, and what appeared to be a mess of lipsticks and nail polish bottles on the vanity.

Never letting go of my hand, Connie led me to the bed to show me some of the "neat features." The spread was pink satin with lace, and the canopy itself was pastel pink with a pink sheer netting and lots of lace. There was a big satin bow at each corner of the canopy, making it look like a bed for a deranged princess. Looking closely, I also saw an eyebolt in each of the four canopy posts, about 6 inches off the bed, and on the two posts at the foot of the bed, there were eye bolts about 2 and 4 feet about the bed.

She then led me to the nightstands, both of which were locked! Pulling a key out of her pocket, she showed me an impressive array of restraints, gags, and the like, which had me so scared that I finally just lost it.

I stood there, crying into my gag, and my bladder just let loose, filling my diaper with warm wet pee. I felt as low as I had ever felt in my life. She then led me to the closet, which was filled with dresses and nightgowns. She showed me at least three little girl party dresses, a beautiful wedding gown, two complete French Maid outfits, one in pink satin, the other in black satin, both with white lace trim, a cocktail dress in royal blue, and several blouses and skirts, most of which were suitable for a girl up to about the age of 10, with a few older girl/womanly things, such as the wedding gown, and maid's outfits.

The final things in the closet were the shoes. High heeled sandals, Mary Janes, pumps, ballet slippers, and one pair of pumps with heels that were 6 inches (at least!) high! Leading me to the dresser, I was shown corsets, panties, stockings, ankle socks, training bras, camisoles, and the like. Finally she took me to the middle of the room, and showed me her final indignantly. On each wall, on two of the canopy posts, and (she said) in a few other locations, were cameras. "What are the cameras for, sweetums? Well, when the big strong men pay to have sex with our little sissy, I want it all on tape, so that when we make the feature film about the making of a sissy, we'll have the material we need!"

Dazed, confused, and overwhelmed, I allowed myself to be led back to the "nursery," where Mark hoisted me up on the changing table, and strapped my arms down with the attached nylon straps. Connie pulled off my plastic panties and diaper and then with a sharp pull, ripped the plug out of my abused bottom, making me scream into the gag with the sudden, and intense pain.

Quickly she reached under the table to one of the shelves that were built in, and pulled out two stainless steel poles, and fitted them into sockets at the end of the table. I looked at these poles, and suddenly it dawned on me that they were leg stirrups like an OB/Gyn would use, but these had straps to secure the feet to the appliance! My shoes were then taken off, and sure enough, I was strapped into the stirrups, my feet high in the air, legs spread, and poor bottom on display.

Now Connie reached back under the table, and I heard a bolt being drawn, and the end of the table folded down, so my naked bottom was right at the edge of the table, holding my open hole at the right height, and in the right place to be taken by anyone she chose. So, this was my fate. Trapped into a nightmarish hell of gay sex perversions. So, why was I hard again?

Again Connie filled me in. "Ah, the widdle sissy is hard again! That's so cute! You see, Mark, I told you that those custom hypnosis tapes he has been listening to would work! The company recorded them over the sound of waves on the beach, and for a year, he has been using them to relax and get to sleep! He is ours to use as we please, and he will even respond for the boys!"

Laughing Connie raised the table again, and unstrapped my feet. I was re-diapered, had clean plastic panties pulled up my legs, and was stood on the floor. My dress was unlocked and removed, as well as my petticoats and training bra. I stood there in diapers, a wig, mittens, and gag as Connie selected a nightgown from the closet, and pulled it over my head. I was now wearing a peach colored satin nightie that seemed to be too long for me.

Again Mark picked me up, and lay me in the crib, and Connie pulled the material down below my feet, and tied it off, forming a bag. My gag and wig were removed, and Connie pulled a baby bottle off the shelf and stuck the nipple in my mouth.

"Now" she said sternly, "you have a choice. You can either drink this apple juice all down like a good girl, or you can have another serving of piss. Your choice, I don't care which you want."

(Video) Caught in a dress, Babysitting. M2F, Crossdressing,Genderswap,TGTF,Boy2Girl,LGBTQ,Feminization.

With that I began sucking at the bottle, holding between my useless hands. She swung the barred cover into place and locked it, leaving me in baby hell. As soon as the bottle was gone, she took it, pushed a teddy bear through the bars, and holding each other and kissing, they left the room. It wasgoing to be a very, very long night. As they were leaving, Connie looked back, and with a laugh told me to get some sleep, because the day-after-tomorrow their first client was coming, and he had paid good money to fuck a little sissy girl, and, "oh yeah, he paid to play with you for the whole weekend, too! You'll love him, Sweetie, he is so-o-o big! And he has some really kinky scenarios planned for you! Nightie-night!"

Chapter 2 The Sissy Horror Continues

I woke up slowly out of my drug induced sleep, and started to assess the situation. I was still locked into my crib (Why did I call it my crib?), I was still in my satin sleeper, tied off at the bottom, but something else was different. I reached up to rub my eyes, and figured out what was different right away. My arms were secured to the side bars of the crib, and there was a strap across my thighs, both contriving to hold me firmly in place.

I also found that the gag was back in my mouth, although when I turned my head to the left to see what was over there, I saw that I could see myself in the mirror, and that instead of a gag, I had a large pacifier in my mouth, and it was tied there with pink ribbon around my head., and my head was covered with a pink satin bonnet. As my mind became clearer, I thought back, and could remember a tape playing beside the crib.

I could remember a woman's soothing voice telling me that I loved to wear panties, and things about service, love, and, well, I really don't remember any more. I assume that this was a hypnosis tape, and that I was being brainwashed while I slept. I tried to raise my head, but I was still a bit woozy, and quickly gave that up. But, as I was laying my head back down, I heard a voice over the house intercom.

"Oh goody, widdle baby is awake!" a bright, cheerful, and totally unknown voice said. "Just lay quietly widdle Emily (like I could do anything else!) and Nanny will be in to take care of you in just a few minutes. Now remember, Sweetums, you're wearing a nice thick diaper, so if you have to go potty, you go right ahead. And anyway, that's the only potty you are going to use for a while."

With that cheerful pronouncement of doom, I realized that there must be active cameras in the room, and that I DID need to go potty. I held on as long as I could, and then threw the last little shred of dignity to the wind, and let loose a stream of warm pee into my (again with the my!) diapers. Right away I felt better, and extremely embarrassed. I didn't have a choice, but I still felt bad that here I was, over 21 years old, and I was peeing in a diaper. I couldn't help myself, and just started to cry. I guess the hormones I was ingesting might have something to do with that, or just the total breakdown of who I thought I was, and a complete, total, and seemingly permanent loss of my dignity, freedom, wife, and my whole life. I lay there crying, and not even trying to stop.

After a few minutes a tall, very pretty lady opened the door and came in. She had blonde hair, worn up in a sort of bun, and was wearing a teal dress that would have looked right at home on Leave It To Beaver, of My Three Sons. She was wearing a frilly apron that also looked straight out of a 1950's magazine describing the perfect housewife. She was also rather large breasted, but had a skinny waist.

She came over the crib, and pulling a key out of a pocket on her apron, she unlocked the top, lowered one side, and then unhooked my wrists, and then took the strap off my legs. Then she lifted me easily up and carried me to the changing table. Here a strap went quickly across my chest, pinning me to the vinyl pad, and then she clipped the D-rings in each mitten to snaps on the sides of the table.

I was, once again, a prisoner in diapers. She then untied the bottom of my nightie, and lifting my bottom, she slid it up to expose my wet diaper.

(I can't help it; I'm starting to think of these sissy things as mine. The hypnosis must be working better than I thought it was.) She slid the plastic panties off, and then removed my diaper, and wiped me with a baby wipe, sprinkled a bit of powder, and re-wrapped me in a clean, very thick, diaper. It was so thick, I could not bring my legs together. A semi-transparent pair of pink plastic pants were pulled up, and then she reached back into the pocket of her frilly apron and pulled out a little padlock. She pulled a string or cable, or something around the waist of the panties, and padlocked them onto me! A strap went quickly across my legs, and I was told that if I moved, I would be spanked so hard that sitting would be impossible, even with a diaper on, and as further punishment, all I would get to drink today was a bottle of pee. I resolved to be a still as a statue!

My hands and chest were freed; Nanny sat me up, and removed all of my clothes, except my pacifier and my diaper. Then she fetched a basin of warm water, and a soft rag, and gave me a gentle sponge bath. She raised up each arm, and clucking a bit, brought out a razor, and cleaned up my underarms. After drying me off, she praised me for being such a good baby, and picked up a peach colored satin baby-doll nightgown, and slid it over my head.

Finally she removed those horrible mittens from my cramped and sweaty hands. Warning me to sit still, she picked up the rag, and cleaned my hands and dried them. Then she picked me up, and carried me over to the rocking chair. She sat down and arranged me on her lap.

Then she did something that really surprised me. She began to unbutton her dress, exposing a white, lacy bra. I could also see that she was wearing some kind of a girdle or corset under her dress, and yes, I was right, she was wearing a pair of black stiletto heeled pumps.

She then unhooked part of the bra (it was a nursing bra!) and exposed a large nipple. Removing my pacifier, she pushed me face towards her tit, and told me to enjoy my breakfast. OH MY GOD! I was about to be wet nursed!

"Now babykins, it's time for your breakfast, and remember what your alternative is. Now enjoy your nice milk, and no biting!"

With that she pushed her nipple into my mouth, and I began to suck. The milk was thin, and had a sweetish, but very odd flavor. I can't say I liked it, but having no alternative, and being very thirsty and, since I hadn't eaten for two days, I was starved!

I suckled at her tit for a few minutes, and then she gently pushed me away, and after a bit of re-arranging, moved me over to her other breast, where I once again gave in and sucked away. Of course this was all being recorded for "posterity" on at least one camera. What could I do. I was trapped into doing exactly what Connie wanted, or, well, I'm not sure how bad the "or else" would be, but I was afraid to find out. Of course every minute I stayed with her horrible program, I got deeper and deeper into a situation where I knew there was no way out, now, or ever.

After my "breakfast" was done, I was sat on the changing table, and Nanny did up her bra and dress, and then stood up and walked over to me. I then made my first mistake of the day. I asked "Nanny" if I was going to get any solid food to eat for breakfast. In a move that was quicker than I would have given her credit for, she had me flipped over, and brought her palm down on the backs on my thighs in several loud, stinging slaps.

"Now little baby, I don't want to have to gag you for the rest of the day, and I'm sure you don't want your 'special' drinky-poo, so no more big person talk out of you! I have been given strict orders, and one of them is that you are to lose 25 pounds, so you had better learn to live with this."

25 pounds!! Good Grief, I was already pretty slender! I would be weak as a kitten if I lost that much... and again, too late, the truth suddenly dawned on me. A little girl is skinny and weak, therefore, I was to be skinny and weak. It all made perfect sense, if I looked at it through Connie's warped lens.

Nanny sat me back up and told me that for the rest of today, I would be in girly school. I would learn how to walk in very high heels, how to put on some very basic makeup, like lipstick and a bit of eye shadow, how to sit and stand like a lady, and how to properly suck a cock. With that statement, I jumped up and started to waddle towards the door.

"And where you might you be going, Emily!" Nanny asked with a laugh. "Are you going to run away in your nightie and diapers? All of your man clothes are gone, and if you remember, you are locked into your plastic panties, so go ahead. I'll even go ahead of you and open the door, but I'll also close and lock the door behind you. Oh, I know! You're thinking about your suitcase that you left in the car, the one that Connie had Mark take out back and burn. You see, you have nowhere to go, and if you try to go anywhere, you do it as a dressed up sissy. So, be a reasonable baby, and come back in the nursery."

Hanging my head, I turned around, and went back to the table. Now Nanny told me that for trying to leave, she had to make the lessons harder for me. She grabbed me, and put me up on the changing table. Once again, a strap went across my chest, and my hands were forced back into mittens, this time peach colored to match my outfit. My wrists were then hooked the table, my plastic panties unlocked and pulled off, and my feet were buckled to the stirrups. This time I found out that the stirrups were adjustable. My legs were spread wide, and pushed up in the air, leaving my ass off the table, and me in pain. She then dropped the end of table, leaving my ass floating in mid-air.

Seconds later a ball gag was forced into my mouth and buckled behind my head, and my diaper was unpinned and removed. And then she produced "it."

"It" was the largest of the three butt plugs that Connie had purchased, and I knew that it was going up my still tender backside, and that I would hurt me terribly. Nanny lubed her finger, and forced it up my ass, then spread more lube on the plug.

With only a "here we go" for a warning, she jammed that thing inside of me, causing me to scream, and scream, and scream into the gag. Tears fell down my face like hot rain, and I felt that there must be blood pouring out me by the gallon, because I had been split in half. She kept me there for about an hour, so I could get used to my "visitor." Finally my diaper and locking panties were put back on, and I was released from my bonds.

For the next five hours I learned to walk in high heels ranging from about 2 inches, to a pair that were a bit over 6 inches high. In those, you didn't so much walk, as mince a bit, and very little of that. My legs were in agony before I put them on, and after about ten minutes of mincing back and forth across the room, I thought the pain in my legs, combined with the pain in my bottom would make me lose my mind! I also practiced putting a finger into my mouth, and sort of twisting my right foot around while looking at the ground like an embarrassed little girl, and then I worked on my curtseys until I could perform them to Nanny's satisfaction.

Finally I was allowed to take off the heels, and go back to a pair of black patent Mary Jane shoes that really felt comfortable after all of that. It's amazing what you can get used to.

Now Nanny announced, it was time for my lunch. Another session of breast feeding (I have to admit that I loved suckling on her beautiful breasts!), was followed by being seated in my high chair, and being spoon-fed several little jars of baby food. They were bland, and not all that nice, but I was so hungry I would have eaten darn near anything to try to fill up my growling belly. Dessert was a jar of strained plums, which were actually quite nice, and a baby bottle of apple juice.

I was re-assured that this bottle did not have any drugs in it, as we still had some school left for the day. Nanny wiped my face, and left me sitting in the high chair, while she turned on a TV to the Teletubbies, and left the room. Now this show is insipid to the nth degree, but I had received no stimulation outside of pain and humiliation for the last few days, so I actually sort of enjoyed watching the show. Soon I felt the familiar symptoms of a full bladder, and once again, held it as long as I could. I finally gave up and peed my diapers, knowing that this was what was required of me, and that I didn't have any other choice anyhow!

Nanny came back in, and again, placed me on the table and changed my wet diaper. This time, though, she played with my cock, which she called my clitty, for a bit, getting me hard and excited, but not letting me cum.

"Now widdle baby Emily," she said, "if you are a good widdle girl, and do your afternoon lessons properly, Nanny will give you some relief. If not, Nanny has some nasty punishment waiting for a naughty baby girl, and she will be forced to take her lessons."

I was set on the floor, and told to get on my knees on a thick pink rug.

"Alright, Emily, you can either do this willingly, and get rewarded, or I use the ring gag, you still get the lesson, and you get punished. I don't much care either way, as your beautiful wife is paying me very well for my services."

At this she chuckled, "Of course some services I give to your wife for free!"

With that cryptic comment she walked over to the closet, unbuttoned her dress, and slipped it off. She stood there in an old fashioned, open- bottom girdle, with garters holding up her stockings, white lacy panties and the nursing bra I had come to know so well. She took a hangar off the rod, hung her dress up, and reached up on a shelf.

Stepping sort of into the closet, I couldn't see what she was doing, but when she turned around, there was a strap-on penis bobbing in front of her. It was about 6 inches long, and sort of thick, and I groaned at the thought of this plastic cock going in my mouth, and began to tear up at the thought that this was training me for the real thing, just like this horrible butt plug was training my bottom for a real cock.

We "practiced" with this cock for about an hour, 'til my jaw was aching, and my knees hurt. She told me not to move, and went back to the closet. Again she was blocked from view, but when she turned around, the cock had been replaced with one that was at least 10 inches long, and as thick as my wrist!

Furthermore there were realistic balls hanging below that monster! Nanny the proceeded to jam this down my sore throat for the next 20 to 30 minutes, teaching me to lick the balls, and to suck them, how to use my fingers (or in this case my mittened hand) on the base of the shaft while I sucked and tongued the head, and how to deep throat the whole thing without gagging and throwing up. Finally when I thought that I could take no more, she thrust one more time down my throat, and pulled that horrible, horrible thing out of my battered mouth. She went back to the closet, removed the harness, and put her dress back on.

Returning to where I was still kneeling on tired knees, she reached down, took me by the upper arms, and helped me stand up. She led me to the changing table, and instead of picking me up, she merely assisted me in sitting up on the table, and then lowered my head so I was once again on the pad.

To my surprise she removed my mittens, and then, without any restraints, placed my oversized pacifier in my mouth, and began to remove my panties and diaper. With a warning that this would hurt, and that I was to hold my pacifier in my mouth and not make a sound, she removed that huge butt plug from my now aching tushy. Dropping it into a basin for washing, she gently cleansed my bottom with a soothing wipe, and then applied an ointment that she said had a very strong topical anesthetic, and would help me feel better really soon.

The pain subsided to a dull ache, and I felt better than I had in the last few days. Days? It felt like weeks since I had come home to what I thought was a loving and sexually adventurous wife, to find that I was reduced to a cock-sucking, cuckholded, panty wearing, breast-fed, sissy of a man, who was under the care of a Nanny.

Speaking of Nanny, she now removed my nightie, and telling me to stay put, went into the bathroom where I could hear water being run into the tub. After a few minutes, I was told that it was okay for me to get down, and to come into the bathroom. Once there I saw a hot tub of water, with fragrant lilac steam rolling off the surface. Nanny helped me to get in, and I don't think a bath ever felt better, or more soothing to anyone, at any time.

I soaked for about 15 minutes, or until the water started getting cool, and then Nanny helped me out, and stood me on the rug so she could dry me off with a fluffy pink (of course) towel. Once dry Nanny handed me a pair of beautiful pale blue satin panties with ruffles around the leg opening, and a seam of elastic down the center of the backside, so that when I put them on, they hugged my bottom, and the seam sort of pressed into my crack. This was followed by a matching camisole and a pair of ivory colored ballet slippers.

Once I was "dressed," Nanny pulled a stool over to the sink, and told me to sit down, facing away from the sink. She had me lean back onto a plastic device that fit into the sink, and proceeded to wash my hair with a lilac scented shampoo and conditioner.

She dried my hair with another pink towel, and then placed a plastic cape around my shoulders, and proceeded to go to the intercom, and tell someone that it was okay to come in. Another young lady dressed in a white smock, and carrying a yellow plastic tool box came in. She told me her name was Mandy, and that she was going to "do" my hair.

An hour later my unruly mop of longish blonde hair was cut in a very feminine, but little girly style, with a part down the middle, and the hair just touching my collar, and curling about my ears. She put a light blue satin covered plastic hair band over my head, and stood back to admire her work.

Seemingly satisfied that I looked like a second grade girl on school picture day, she reached back into her box and brought out a bottle, some cotton swabs, and a gun-like thing.

"Now Sweetie, I'm going to pierce your ears, and it will sting a bit, so try to be a brave little girl!"

(Video) The Women's Job - Guy Working In Woman's Office

She swabbed both ears, and then with a loud snap, and a sharp pain, I had a little heart-shaped gold stud in my left ear. Another snap and burst of pain, and I had a matching stud in my left ear. Now with the exception of a penis, I looked for all the world like a cute little 7 or 8 year old girl ready to get dressed for a party, but felt like I was at the bottom of a deep well, which was only getting deeper by the minute.

Nanny (I really wish I knew her name, but I suppose this is one of the pieces of the humiliation puzzle) now took me by the hand and led me not back into the nursery, but into the pink, white, and satin parody of an innocent little girl's room.

Nanny sat me on the edge of the bed and told me that I now had a choice of reward. I could either have sex with her, which wasn't such a bad prospect, as she was a very attractive young lady, or I could oral sex with my wife. She told me that it might be the last time I had straight sex with a woman for the next year, but almost certainly the last time I would even see my wife's naked pussy up close, ever. I wanted my wife, even after everything that had happened, I loved her, and the thought of her sweet pussy was almost overpowering.

Then the thought of Mark fucking her, and the knowledge that the warped bitch would almost certainly be feeding me a "cream pie" of his cum, rose up in my brain, and I meekly looked at Nanny, and asked her please let me make love to her like a man, instead of as a little girl. Nanny took me in her arms, and held me, and I just started to cry. She held me for the longest time, and when I had cried myself out, she took out a tissue, helped me blow my nose, and I knew that my days as a man had ended. Nanny told me to wait here for a few minutes, and she would be right back.

A very short few minutes later she swept into the room wearing a breathtaking white satin negligee, a pair of silver high heeled sandals, her blonde hair down and brushed until it shone and wearing pink lipstick that seemed to glitter. She was a beautiful young lady, and when she came to me, I stood up and we held each other close. Now she was at least 6 inches taller than me, and with the heels, that put me almost at nipple level, but since I was wearing blue satin panties and a training bra anyway, the whole macho thing was sort of a moot point.

We lay down on the bed, and we kissed for the longest time, and then she moved down and began to suckle on my nipples, making me hard, horny, and very, very excited. She continued down my smooth stomach, and then started kissing my thighs, while rubbing her hands across my panty-clad ass and "clitty."

The foreplay went on for quite a while, when she suddenly sat up, moved up to my head, lifted the hem of her negligee, and lowered her pussy onto my mouth. I knew that this was the first and only time that I would make love to this woman, and that after this, it was back to a Nanny-child relationship, and that this might be the only sex with a woman I would have for a while, so I wanted to make it last, and make it the best sex possible. With that in mind, I threw my tongue into high gear, and ate that delicious pussy to at least three orgasms. When she slid off my wet and sticky face, she slid down beside me, and we began to kiss, and she licked the remains of her pussy juice from my face.

"Now Sweetheart, do you want me to give you a blow job, or fuck you?" she asked softly.

Moments later I was on my back, as she lowered her hot slit onto my now iron-stiff clitty. Even now, I noted, I was not in charge, but I didn't care. When I finally blew my load, I felt like a man, for at least a few seconds, and a very satisfied man, at that. Again though, she slipped up, and placed her sopping pussy above my face, and again, my tongue went to work, this time, eating my own cum along with her juices. Finally she lay down beside me, and I noticed that the front of her gown was damp, so I slid the lacy shoulder straps down, and began to suckle at her nipples, first one and then the other, drinking her milk, and reveling in my last good sex for a while. Tomorrow, my life would go from bad, to much, much worse.

After another quick bath it was back into a clean diaper and plastic panties, and then into my sleeper, with the hem tied off below my feet, and those "lovely" mittens on my hands. Nanny, now wearing the robe of her negligee, gave me a bottle of apple juice, telling me that it had only half of last night's sedative in it, just to help me sleep, because tomorrow was going be a very stressful day for me, and she wanted me to get through it like a brave little girl.

After my bottle, my pacifier was placed in my mouth and it was tied off behind my head with pretty ribbon, and I was locked into my crib for the night. My thoughts were not pretty, but I could see no way out of the situation. Nanny turned on the tape player, making no secret of the hypnosis tapes, making my last coherent thoughts a combination of the woman on the tape saying, "Frilly, girly panties are what I live for," and my own thought that it was very early, the sun was still up. Then I slept.

I was awakened early by Nanny, who got me up, and removed my wet diaper and panties. In only a few days I had not only gotten used to wearing them, I was peeing in them automatically, and without waking up. Could I ever go without them after I left here? Would I ever leave here?

My feet were placed back in those damn stirrups, and Nanny asked me if I had to be restrained, or would I try to be a good girl. I nodded and mumbled around my gag-like pacifier that I would try to be good. She repeated the ceremony with the lube, and with fear and nausea, I waited for the horrible pain.

She placed the head of the butt plug against my anus, and slowly pushed. I was relieved that she had chosen the smallest of the plugs, as it went in fairly easily, and there was not too much pain. After a fresh diaper and a pair of see-through white plastic panties with zoo animal cartoons were in place, she slid a yellow T-shirt over my head, and then pulled it down between my legs and snapped it closed.

I looked down and the words "Sissy Slut in Training," were emblazoned on the front in glittery letters. I must have started crying, because I heard Nanny say, almost sadly, "I'm sorry, Emily, this is what I was told to do, and how to dress you this morning. We have to get you ready for your appointment, and I've been given strict orders as to what to do."

She then asked me to hop off the table, and join her on the rocking chair. My Nanny was wearing a beautiful deep blue nightgown that had two spaghetti straps at each shoulder, and exquisite lace at the bodice. The gown went down to her ankles, and I could see a pair of black slides with clear acrylic high heels. She was beautiful! She sat down in the chair, and I sat on her lap. She removed my pacifier, and lowered the shoulder straps over on one side, exposing her nipple for my lips. Either I had come to like this in only a day, the hypnosis tapes were working, or I did not want to disappoint my Nanny, whom I had come to think of as my only friend, and the only one in this world who loved me.

Of course it was a bit of all three, and the latter was as well planned out as any experiment Pavlov ever performed on his dogs! After I had emptied both breasts of their morning's milk, she led me over to the high chair, and after locking the tray in place, she fed me a bowl of oatmeal, two jars of strained plums, and my bottle of apple juice. She also gave me two pills, one the hormone and the other a real multi- vitamin, because I would need my strength.

After my breakfast, I was taken to the bathroom, where I was allowed to use the toilet to poop, although I had to sit backwards on the potty, even though I don't know why. Once again I slathered in depilatory cream, showered, and had any remaining hair whisked away with a new razor. I was then led, naked, back into the nursery, where I was led back to the changing table, feet back in the stirrups, and the butt plug removed.

Again apologizing, Nanny pushed a thick penis gag into my mouth, buckling it behind my head, and then strapped me to the table. Cooing at me, just like I was a real baby, she took what looked like a hot water bottle with a plastic tube and nozzle attached to it, and hung the bag on the left hand stirrup support. She pushed the odd looking nozzle into my bottom, and then opened a valve, letting what I had already figured to be an enema flow into my bowels. I began to squirm as the warm liquid filled me to bursting, and I began to cramp up. Still, the liquid flowed into me.

Finally Nanny removed the tube, but not the nozzle from my bottom, and attaching what looked like a squeeze bulb, she began to pump, and I could feel the nozzle expand and fill my bottom like a plug, but without the pain of insertion.

I was told to lie still, and relax. The inflated plug would help me to hold the liquid in for five minutes so I could be clean and sweet for my appointment in just a little while. After the longest five minutes ever recorded, I was released, and allowed once again to hobble to the "big girl potty,' where the plug was deflated, and I quickly sat down and expelled the mess into the toilet.

Nanny told me to sit there for a few moments to make sure I was empty, and then led me back to the nursery. Again on the table, where my bottom was cleaned with several wipes, and then Nanny pushed a tampon into my bottom, to, as she said, catch all the drips. While I was lying there, Nanny left the room to get dressed.

She returned in a classic black satin French Maid's outfit, complete with lacy choker, cap, lacey half gloves, and high heeled black pumps. She was wearing a satin pinafore, and looked ever so sexy!

As she went about the room, gathering my "wardrobe" for the day, I could see her black satin panties, with rows of lace on the bottom, poking out from under her crinolines. As she pulled open drawers and closet doors, she explained a bit of the program.

"Your appointment today wants a baby girl in diapers. I have to warn you that he is into bondage, humiliation, and pain. I expect you will be paddled at least once, if not more, and I'm reasonably sure you will spend much of the day in some form of restraint. Please, little Emily, do whatever he wants you to do without hesitation. I do want you to act scared, which he loves, and will probably not be an act, anyway. Mistress Connie has promised me that if you refuse anything he asks, you will be punished, and I will also be punished. I don't know what your punishment will be, but I have been promised that you will in no way enjoy any of it."

With this dire warning ringing in my ears, she came back over to the table, removed the tampon, and cleaned my bottom one more time. Once again, the hated butt plug was forced into back door, and I was placed in another extra thick diaper, with what she called a thick soaker pad between my legs.

I would be lucky to be able to waddle, let alone walk, and I think this was just what was looked for. A pair of plastic panties with a peach colored satin cover, complete with rows of sissy lace across the bottom and around the leg openings were pulled up my smooth, hairless legs, and a pair of matching booties were placed on my feet, over a pair of baby sissy socks.

I was sat up, and she pulled a peach training bra over my head, commenting that Mistress Connie had ordered several of these sets from a very talented lady in England, so I had better appreciate the effort. Now a lovely peach satin sissy dress with built in petticoats was pulled over my head. My hair was brushed and fussed over, and then I was stood up on the floor so the dress could be buttoned up the back. A pinafore of lace encrusted white satin was tied around my waist and over my shoulders.

Again the dress was so short that it barely covered the top of my diaper cover, let alone hide the fact that I was diapered. Finally my hands were put back into restraint mittens, and clipped together behind my back, a fluffy peach satin bonnet with lashings of lace was tied on my head, and my pacifier was tied back in my mouth. Nanny sprayed me with a bit of perfume, stood back and surveyed her work, and must have thought it looked good. She then looked at me for a moment, and walked to the phone in the corner. She dialed one number, asked a quiet question, nodded, said yes, and then walked to the door.

A few moments later my wife walked in, wearing only a black sheer robe which showed off her tight, B-cup breasts and their stiff little nipples, a pair of black nylon bikini panties, and a pair of tall black high heeled sandals with sexy little ankle straps.

As she came in Nanny dropped to her knees, and kissed Connie's shoes, and when Connie told her to stand, she stood up and curtseyed. Connie walked over to me, and examined me closely. Telling Nanny to put some blush on my cheeks, she laughed and after warning me to say a damn word, she pulled out the gag. She stood back and told Nanny to stand behind her, and to reach around and make her cum through her panties. Nanny began to kiss the back of Connie's neck, and caress those lovely breasts, then her right hand snaked down and began rubbing that wonderful pussy through the smooth nylon of the panties.

After just a few minutes Connie arched her back and moaned. Telling Nanny that was enough, she then ordered Nanny to remove the panties, and, "She knew what to do with them. Nanny knelt in front of my wife, and slowly slid the soaked panties down her shapely legs. Looking up at Connie, Nanny placed a kiss on her smooth, hairless pussy, and then as Connie raised one high heeled foot after the other, the panties were removed. Nanny then went to the changing table and came back the large Nuk pacifier. She told me to open my mouth, and then shoved the fragrant panties in, and followed them with the pacifier. My bonnet was removed, and the ribbon tied very tightly behind my head, and the bonnet was then replaced. Connie just stood there and began to laugh. She told Nanny to sit me on the high chair, strap me in tight, and to stand beside the chair. She then picked up a digital camera from the dresser, and took several photos of us together, a trussed up baby girl, and sexy French Maid-Nanny. I knew that this day was going to be a black one indeed.

Chapter 3

Connie looked at me like I was a piece of art to be appreciated, chuckled to herself, and walked out of the room, her beautiful ass swinging naked under the sheer robe. "As she was leaving, she looked over her shoulder and told Nanny that she had only a few minutes, and it was time for her to finish getting ready. I looked at Nanny, but she was walking out of the room behind Connie. I was now officially scared! I wanted to ask Nanny what was going to happen, a question that I had been too scared to ask, but now she was gone, and I was gagged anyway. All I could do was wait. I sat there for only a few minutes before Nanny returned. She was walking slowly, and I could see a short silver chain between her ankles that limited the size of her step. She was also carrying a few things in her hands. As I watched, she placed a large, black silicone penis gag in her mouth, and buckled it behind her head. Then she placed a large leather cuff on each wrist, and sat down in a chair beside the high chair.

Only a few moments later Connie walked back in, this time wearing an absolutely stunning black silk dress with an illusion neckline, ¾ sleeves, which looked like a beautiful black bridal gown. I could also tell that she was wearing a tight corset that pulled in her already trim waist, and pushed her breasts up, making them seem larger. As she walked in, I could just see the black lace stockings, and the very tall high heeled sandals. The sheer stockings allowed me to see that her toes were painted the same deep pink as her fingernails.

This all contrived to make her look both sexy and virginal, and in spite of myself, I was as hard as a rock, and yes, I wanted this woman! I wanted this woman who had violated a sacred bond between us, violated me, cuckholded me, forced me into being a sissy. This, sexy, seductive, and yes, evil woman was my only desire! As she stood there, she looked us both over, and told Nanny to stand up. Connie strolled over to her, and after kissing her on the cheek, and I saw for the first time, that the lacy choker around Nanny's neck was made of lace trimmed leather.

Connie took each of Nanny's wrists, and hooked them to the collar, so that we were now both restrained, and had no choice but to play along in the little drama that the mystery man had paid for. We would not have to wait too long to find out what that drama was, as the doorbell rang, and laughing, Connie tweaked one of Nanny's nipples, kissed us both on the cheeks, and told us that our playmate was here, and that she hoped we had "fun."

A short minute or so later Connie led a tall, well tanned man into the room. He had the build of an athlete, with the polish of a corporate CEO. A very nice suit of navy wool was tailored to his body, offset by a crisp white shirt and pale blue tie. He was at least 6 foot tall, and had dark brown hair and eyes to match. While he was a good looking man, I was scared to death.

Connie introduced us, telling them man that I was his very own sissy, Emily, that Nanny was his maid for the weekend, and telling us that this man's name was either "Sir," or "Master." Connie stepped out and said something to someone, and the fun began. With a warning whispered in my ear that if I made a sound, I would have my mouth filled with shit, Connie removed the pacifier and panties, and replaced them with the ring gag, minus the rubber phallus.

She then released Nanny's wrists from her collar, and told her to go to the next room and ready the chair. I had no idea of what "the chair" might be, but I really didn't think I would like it!

I was released from my chair, and led out of the nursery, and into the little girl's bedroom. There, on the floor, was the short pink chair that had been my seat for Mark's humiliation of me. Nanny curtsied to Connie, and then to the man, and took me by the arm. Once again I was seated in the chair, and once again, my wrists were restrained, a collar was around my neck and hooked to the chair, and my legs were spread, and with the soles of my feet flat on the floor, straps were looped around each ankle and secured to the floor.

I was right at Master's waist level, and had no illusions of what was to come. Master looked at Nanny and told her to come closer. He ran his manicured hands over her body, lingering on her ruffled ass.

"You may undress me, Maid," he said, and as Connie laughed, Nanny began to help Master remove and hang up his suit. Now he stood there in just a pair of gray silk boxes, and his cock made a tent in them big enough to live in! I thought that the plugs and gags were huge, but this man looked twice as big, and I hadn't even seen his cock yet!

At a nod from Connie, Nanny went to the dresser, picked something up, and returned. I now saw that she had a large, yellow, plastic bib in her hands, which she proceeded to tie around my neck. She then retrieved a large bowl from under the bed, and standing behind me, held it under my chin.

"Master" then removed his own boxes, and I could see a huge hard cock, pointing right at me! I found out later that it was almost 9 inches long, and it looked as thick as it did long! He moved in towards me, and with a warning to drink every drop, he shoved the head of his huge cock between my lips and began to piss!

I swallowed as much of the evil tasting piss as I could, and what I didn't swallow ended up in the bowl. When he was done, the force- feeding gag was shoved back into its mount, the leftover piss was again loaded into the large syringe-like feeder, and it was forced into my mouth, and down my throat. Now I was crying for all I was worth. What had I done in my life to earn me this kind of punishment and humiliation? Why was this being done to me, and by my own wife? Why the hell was I as hard as a rock!!??

The rubber cock was once again pulled out, and was now replaced by the real thing. As wide open as my mouth was being forced, his cock felt like it stretched me even further. He pulled out after on a moment, and told Nanny to remove my ring gag.

Then he leaned over and whispered in my ear, "Now little Emily, I am going to fuck your mouth. If you bite me, or if I even feel your teeth, I have your mistress's permission to fill your sissy mouth with my shit. Now that might turn me on, but I don't think you would like it very much, now would you?"

I frantically tried to shake my head no, and even though I was tightly restrained, he understood my reluctance to be punished in this way. Now that we had an "understanding," he shoved his thick cock back into my mouth. He pushed it all the way to the back of my throat, and I did my best not to throw up, but gagged mightily. He pulled out a bit, and then rammed it back in.

Connie told me to try and swallow the head of the cock, just like the dildo that I had practiced on, and finally I was able to hold the cock in the back of my throat. I lost track of time as he brutally fucked my mouth. I had been ready to have to give him a blow job, but this was just oral rape, sanctioned by, and probably filmed by, my wife, and there was nothing I could do about it. When he was finally done, he pulled his softening cock from my aching jaws, he laughed at the cum trickling from the corners of my mouth, and just told Nanny to, "Get the little sissy dressed and ready. I'll be back in an hour."


With that he pulled his boxers back on, and took a thick terry cloth robe that Nanny held out to him, and he left.

I had no idea of what was coming as Nanny unhooked me from what I now thought of as my "potty chair," but was too darn afraid to ask. As Nanny put the chair in the closet, she told me to sit on the edge of the bed, and she would help me get ready for the next "scene".

She came out of the huge closet with a white garment bag, and some other items, and laid them on the bed. Then she came around to me, and began to remove my baby outfit. After I was naked, except for the diapers and plastic panties, she told me to stand up. Taking my hand, she led me into the bathroom, where the bathtub was already full of hot water. Stripping off my wet diaper (again, I never even noticed that I peed myself!) and panties, she helped me into the tub, and quickly picked up a soft cloth and washed my sweaty body.

I was lifted up, and set on a large pink rug, where I was patted dry, and dusted with perfumed body talc. I was told to stand on the stool at the sink, and brush my teeth. A stool? I was tall enough to reach a sink! Then I noticed for the first time, that the sink was much taller than an ordinary sink, and that while my Nanny, who was at least six foot tall, could use it easily, I had to stand on a stool that read, "Sissy Emily's Booster Stool."

I picked up the pink toothbrush, and finally brushed the taste of his piss from my mouth. I was physically and mentally exhausted, and just decided to let things go. What the hell could I do? I was nothing but a pawn in a game. In fact, I was in a game; and no one would let me read the rules of play. My role was whatever Connie decided it was. I would just have to wait, and maybe things would change in my favor, if only for a little while.

Taking my hand again, just like a little girl, I was led back into the Little Girl Emily's bedroom. Nanny told me to sit on the bed again, and she began to lay out my new outfit. I didn't want to, but I had to look. What I saw was the most beautiful white satin wedding dress! It was awash with white satin bows, had kind of capped shoulders, and the sleeves were sheer lace that ended in white satin triangles, which had a loop that slid over my two middle fingers.

I did notice that the dress was shorter than a normal wedding gown, and I figured, rightly, that it was half wedding gown, and half sissy dress. Within moments, Nanny had me standing up at the foot of the bed, and had tied my hands to one of the eye bolts. She told me that I had to be quiet or I would be gagged early. I nodded, and she picked up a white satin corset that was itself a beautifully made garment. I would learn how ugly it was in moments. Tighter and tighter she laced it around my poor middle. Telling to take a deep breath and hold it, she cruelly pulled it one last time, and with a quick knot, I was held tight in a white satin prison.

Nanny then folded a flap of material over the laces, and hooked three buttons, and one small brass padlock. I was now locked into my first corset, and really didn't like it one bit. Now I was sat back on the bed while a pair of sheer white stockings were pulled up my legs and attached to the garter straps from the corset. The stockings had a beautiful white bow at the back of each ankle, and lacy tops, and were gorgeous!

I was told to stand, and the dress was slipped over my head. I realized that this dress must have been custom ordered, and the size very carefully chosen, as it barely fit around my now corseted middle. I glanced in the mirror and saw a sissy parody of a beautiful bride looking back at me. Asking me to lift one foot at a time, she slid a pair of white satin panties that were just dripping with lace, up over the beautiful stockings, and settled them in place over the garter straps of the corset.

A final box was opened and I watched as a pair of slim, white satin pumps were removed. Nanny explained that these were custom made, just for me. The heels were 6 inch stilettos, and there was an ankle strap with the obligatory small hasp for a padlock. After my shoes were locked onto my feet Nanny showed me a special modification that had been made to both the dress and the corset.

Pulling the loops of elastic off my fingers, she pushed the sleeves of the dress up a bit. Then she produced two cuffs of white leather, which she proceeded place around my wrists, and buckle. The sleeves were once again pulled down and the loops placed over my fingers, effectively hiding the cuffs. A sewn hole on the inside of each satin sleeve end allowed the D ring from the cuff to protrude, and I was shown where there was a matching D ring that was attached to each side of the corset, which again protruded through two holes in the sides of the dress.

It was not only a humiliating sissy version of a beautiful wedding gown; it was its very own bondage suit of virginal white satin! The ring gag with the penis was shoved back into my mouth and buckled behind my head. She then placed a flowered ring on my head, with a veil that sort of covered the straps to the gag. A quick click with a snap ring, and my wrists were hooked together, and a bouquet of daisies was placed in my hands.

I was led, tottering on my too tall heels, out into what had been my living room, and found my "master" and my "wife" waiting for me. He was wearing a pair of black silk boxers, and a black silk T-shirt that clung to his muscular body.

As soon as Nanny led me from the room, Connie pushed the start button on a cassette player, and "Here Comes the Bride" blared out from the small speakers. Connie just stared at me and laughed, as red faced with embarrassment, I was led to the "altar."

After a short joke of a wedding service, I was led by Nanny back to the bedroom, and told to lie on the bed on my back. My wrists were clipped to straps that were hooked to the posts at the head of the bed, and a strap was hooked into each of the side D rings on my corset that were apparently hooked to the side rails of the bed. These straps were all tightened down, and I was held, arms akimbo, and tight to the bed. Now each ankle had a cuff attached, and my legs were now spread, high over my head as the ankle straps were hooked near the top of the head posts.

I didn't need a guide book to tell me that my ass was exposed, even though it was covered by a pair of sissy panties, and I was helpless. My "marriage" was about to be consummated.

"Master" walked into the bedroom and I could see his huge hard on tenting his black silk boxers. In spite of myself, I was starting to breathe harder, and was actually salivating around my gag at the thought of that huge cock filling my backside. Now I knew. The hypnosis really did work.

I was scared too, at the thought of that huge cock ripping into me. He walked up to the bed, and began to caress my helpless body, running his hands along my stockinged legs, fondling my satin and lace clad ass. Nanny approached the bed and asked if he was ready.

When he nodded, she removed his boxers and T-shirt for him, and then reached down, and with a short rip of Velcro, pulled down a flap at the back of my panties, exposing my virgin hole for his attention. Nanny then applied lube to my ass, and I could feel the cool lube on her soft fingers as she rubbed it in my hole. That would be the last "soft" thing I would feel.

The next moment I could feel his cock head at my boy pussy. He began to force it against me, and Nanny whispered in my ear that I needed to push to help him in, and it wouldn't hurt as much. I relaxed as much as I could, and pushed. Suddenly, the head of his cock pushed past the ring of muscles in my bottom, and the pain made me scream into my gag, and my whole body writhed as I tried to get out of my bonds and away from this monster in my bottom.

Tears were flowing down my face, and I continued to scream and try to squirm away from him as he relentlessly pushed his cock into me. He never gave me a moment's rest as he buried it up to the hilt inside of me, and then began to rhythmically pound my ass, his balls slapping against the satin and lace panties that still covered my quivering and burning ass. Again and again he slammed that huge cock into me until I thought I would pass out from the pain and humiliation. Finally after what seemed like hours, he grunted, then moaned, then filled my ass with his cum.

I could feel his monster shrink inside of me, and he finally pulled out, whereupon Nanny quickly shoved a tampon up my butt to keep from soiling the bed or my clothes, and closed the flap on my panties. "Master" then went to the bathroom, and I was "treated" to a video replay of the consummation ceremony, complete with full color and audio, on the 60 inch plasma screen on the wall at the foot of the bed.

The rest of the weekend was much the same, as I got my ass reamed at least 4 more times, in various outfits. I sucked him until my aching jaw was ready to fall off my face, and endured a spanking that left my ass cheeks red for a month. Finally though, it was over. I was given a warm bath, put into a nightie and left in my crib, untied but locked in, for a night's sleep.

For the next 2 months I "entertained" about 15 men and two women who wanted to play with a sissy baby, or little sissy girl. I noticed that during this time, the hormones I was on kept me from getting hard most of the time, and that I was developing little A cup titties. They were very sensitive, and felt strange, but good.

The only "good" weekend of this period was one in which a married man wanted to play sissy baby. He was brought in by his wife, and while Nanny (dressed in her sexy 1950s teal dress and pinafore apron) transformed the man into a baby girl, she just watched from a chair in the corner. Nanny wore a black silk mask, like you might to a fancy dress ball, and Connie took photo after photo with a very expensive digital camera.

He was bathed, shaved, had his hair done, was given an enema while strapped to my changing table, and dressed in the most girlish lilac colored panties and dress, both of which were absolutely dripping with lace. Of course his hands were restrained in mittens, and he was gagged with a pacifier. All I had to do was sit in the playpen with him and play with dolls, and finally let him suck my little cock. That I loved, as I hadn't been allowed to touch myself for a while. Of course it was all to be used against the poor guy in a divorce proceeding.

Yes, I had learned to do things that I never thought I would have to ever learn! I also realized that Nanny was not my friend, or lover, but a well paid employee, and sometime lover of my wife. I also learned that Connie and her lover, Mark, no longer lived in the house. The upstairs had been converted into a video studio and office, and the rest of the downstairs was more like a reception lounge than a living room. That little fact, a forgotten degree, and Connie pushing things a bit too far were all to conspire in my escape from hell.

"Nanny" was in thrall to my wife. As her lover and well paid employee, she not only enjoyed Connie's body almost as often as Mark, but she was well compensated for humiliating me, something she seemed to enjoy as well. Wet nurse to a big sissy baby seemed to be fun for her, until one weekend, about 9 or 10 weeks after the whole thing got started. It was another session of "Baby Emily plays potty for master," as another customer got off on pissing in and on me.

This one had me kneel on the patio, dressed in my little girl frillies while he first pissed in my mouth, and then all over me. After Nanny got me cleaned up, and he drank some more beer, who should show up in my chamber of horror, but Connie and Mark. The next thing I knew was that both Nanny and I were tied up, rings gags in, and standing in for a urinal.

Mark then tied us both over the end of the bed, so that the current master, and another playmate, could fuck us both in the ass. I was dressed as a little school girl, in a short plaid skirt, white satin blouse, navy blue nylon panties with white lace around the leg openings, knee high white nylon socks, and black Mary Jane shoes, and to my great surprise, Nanny was in an identical costume, both of us gagged and bound tight. That afternoon was the straw that broke the camel's back, so to speak.

After tucking me into my locking crib, Nanny produced a bottle of wine and sat in the dark in the rocking chair, drinking and thinking. She must have been half in the bag, because she began to rail against Connie and the way she had been used that day. "That was never part of our agreement!" she fumed, and the more of the wine she drank, the more angry and morose she became.

I told her to hush (although my voice was muffled by the nightly NUK size 5 pacifier that was tied tightly into my mouth) because the video would pick up what she was saying. Drunkenly, she admitted that the video was turned off at night, as Connie already had footage of me tied into my sleeper, and lashed into a locking crib like a bad baby girl. This then, was the start of my plan.

Over the course of the next week or so, I talked to Nanny each evening, and emphasized the point that Connie only cared about herself, and that there was probably good video footage of Nanny performing sex acts that were either out on the web for sale, or soon would be. Nanny, who finally told me her name was Heather, informed me that Connie was doing the editing on four videos of me that were going to go on sale next month. She was not too happy to hear that she might be starring in some of them, as again, that was not part of the agreement.

"Come on," I asked her, "do you really think she would pass up selling video of you nursing me, or you bathing me, or the time you fucked me? How about last weekend when you were my water sports partner? That crap would be too good to pass up for her and her greedy lover."

"What could I do about it," she whispered. "I don't know anything about computers, and that's where it all is."

It was then that I informed her that I also held a Bs degree in computer programming, and that even though I hadn't worked in the computer field since gaining my Master's in mechanical engineering, I still knew my way around a PC.

For the next four nights, anyone watching us would have seen a strange sight. A man in a pink nightgown, girly long hair, and shod in high heeled pink mules, accompanied by a very sexy French maid, would make their way out of the nursery, and up the stairs to the office area. I found that Connie hadn't even encrypted the data I sought, thinking that I would never learn it was there, nor ever be able to get up the stairs to access it.

I started small, and placed a worm in the system to corrupt all video files if they were accessed. That took almost 6 hours of the first night, and was about all I could accomplish. The next night, I stumbled on Connie's financial information. The thought hit me that she only had a power of attorney, and I could still access my money! I began by moving a very small amount to an old "secret" saving's account that I still had open in another bank. Ironically, I had opened this account when we got married so that I could hide some money to buy Connie presents! When I saw that the transaction went through, I knew I had a new plan of attack.

I had a dedicated co-conspirator by the end of the next week. Another day, and another "Master" to please. Again against her will, Nanny Heather was a part of this scenario, also. Again it was a little girl Emily, not Baby Emily that I playing. This time, I was wearing a little sundress over my pink ribbon and lace trimmed white satin training bra and panties.

My hair was in ponytails, and I had the inevitable ankle socks and Mary Jane's on my feet. I was led out into the back yard, clutching a dolly, and told that I had a very special play mate coming. I heard a noise, and saw a man leading a pair of huge rottweiler dogs on a leash. I had a very bad feeling about this. The dogs were let off the lead, and I was told to stand still, and let the dogs sniff me. I didn't move, and soon learned that these dogs were pretty friendly. Just how friendly, I would learn in a few minutes.

I spent a few minutes playing with the dogs, all the while being video taped, and finally, we all went inside. Nanny was there, in the living room, dressed in her maid outfit. Before I knew it, I was on my knees, and tied down over an ottoman. A spreader bar was between my ankles, and my thighs and wrists were tied to the heavy leather ottoman's legs. With my pantied bottom in the air, I had a pretty good idea of what would happen next.

What did happen was that Nanny found herself tied up right beside me on the other matching ottoman. Both of had a ball gag shoved into our mouths, and these were buckled very tightly behind our heads. Both of our panties were pulled down, and two huge dogs, their front paws in some sort of socks to keep from scratching us, mounted us both and began to fuck our bottoms! I was crying with the pain and humiliation of it all. As the big dog cock formed a knot in my poor abused bottom, and the dog tried to pull away, I screamed with the horrible pain, and happened to look over at Nanny. Her face was red, and she seemed on the verge of tears, too, but she was holding them back with a great effort. I found out a bit later that she more consumed by anger than any other emotion

I learned that night that Nanny's real name was Heather, and that she was officially tired of "this shit." She had finally realized, as had I, that Connie was nothing but a manipulative witch, who only wanted the best for Connie, the hell with anyone else. The next day was Heather's day off, and she went down to see an attorney, and with a few pen strokes that night, and Heather putting a heavy envelope in the mail by the light of the moon, she was now the owner of the house where I was held captive.

While she was off mailing the deed, I downloaded all the video files, bypassing my worm, to newly opened home page, where I could recover them later. I wanted to keep them for legal reasons, and, I have to admit, being in sissy girly clothing turned me on like you would not believe! I guess this was partly as a result of the hypnosis, but maybe I had always had this desire. Anyway, I wanted to keep some videos to watch myself. The next step was to transfer all but about ten thousand dollars to my own account. I left that much there so that when either Mark or Connie tried to use an atm or check card, there would be enough money in there to work, and keep them in the dark for at least a few more days. Just a bit more time and our plan would pay off.

The rest of the week was a drag, or at least I was in drag! (I know, bad pun!) I had three "clients" that week that all wanted either a schoolgirl or a girl in her party dress, or other virginal visions. I hate to admit this, but I really enjoyed dressing in silk, satin, and lace, and the thought of a fat cock in my mouth made me salivate. Was I turning gay? Was I bi? Shit, what the hell was I becoming? I had started out as a very straight man, then started wearing lingerie just for sex with my wife, and now I was being pimped out to anyone who wanted what I had to offer, and could pay the freight! Thursday of that week, I had two male clients, and found myself handcuffed in my "best" pink party dress, and draped over an ottoman, with one cock up my bottom, and another in my mouth. I think that I enjoyed the session as much as, or more than they did! I was as hard as a rock and my little nipples were just as rigid!

Finally it was Heather's day off again, and the time to finish it all was at hand. A call to a local locksmith was made from a pay phone in town, and he showed up just a few minutes after Heather got home and unlocked my crib and let me out of the locking nightie-bag. She had just finished putting a new diaper on me, and was sliding on my plastic panties when the doorbell rang. Taking me by the hand, she went to answer it.

The locksmith was a bit surprised to see Heather in a Maid's outfit and to see her with man in a pink satin baby doll nightie, along with diapers, plastic pants, pink satin mittens on his hands, and a pacifier tied in his mouth. We had to do this, just in case Connie showed up. Of course by now, dressing like this was getting to be not only normal, but I was actually enjoying being babied! While he got to work changing all the locks, Heather calmly sat in what was once my living room, and gave me what would be my last session of nursing at her beautiful breasts.

It only took him 2 hours to change all the locks, and with that we were ready for the end of all of this. Of course it ended up with a lot of yelling, threats, and such, but legally, we held all the cards. I retained a lawyer and ended up by giving Connie possession of not only the condo that she had bought, but the boutique that she had just purchased. She also kept the ten thousand dollars, but I had the last laugh when she found out that Mark up and ran away with all but fifty bucks! He also took a bunch of her jewelry, her TV, and a few nice little pieces of bric-a-brac. Serves the witch right! Heather got to keep the house and all the furniture, plus I gave her ten thousand dollars for her help. So, what happened to me?

Well, I had Heather go into town for me and buy me some men's clothing. I still wore lingerie under them, but went out and bought a home in another state, and also a condo in the next city. Here, I stashed my huge girly wardrobe in the oversized walk-in closet, and decorated the whole place in a very girly style. My modest little house was as normal as normal could be, and I only kept a few pairs of panties, a couple nighties, and such there.

I could now lead two lives, and have enough money to enjoy myself. I went on cruises as Emily, and had so much fun! I went to all sorts of bars and clubs, some of which I watched, and others...well... I finally decided to open a store that catered to men who wanted to express their more feminine side, and hired Emily to work there for me! Quite a few men have been very shy and nervous when they came in, and really loosened up when they found a man dressed as a little girl, who was ready and willing to help them realize their fantasies. Sometimes, ALL of their fantasies! But, that might be another story...

(Video) My sisters sleepover, I had to be a girl. Crossdressed,M2F,TGTF,Boy2Girl,LGBTQ,Feminized,Genderswap

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1. My Mom's Caught Me While Crossdressing | Crossdressing Story
(About TG Life)
2. The girl next door forced me to be a girl. Crossdressing/M2F/Genderswap/TGTF/Boy2Girl/Feminization
(Crossdressed - Feminized)
3. My Mom Said I Should Wear Panties (Audio Story w/ pics) Ep1 How I Became A Sissy
(Sissy Gateway)
4. Caught in my little black dress. Crossdressed,M2F, Boy2Girl,Genderswap,TGTF,Feminization,LGBTQ.
(Crossdressed - Feminized)
5. When My Friends Forced Me to Crossdress, I Discovered my True Identity!
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6. Tessa punishes in sissy panties
(Ildimenyuszik Tangensrefujasutan)

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