A Girl And Her Sissy

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A girl recounting the feminization of her boyfriend.
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TollWard
TollWard
18 Followers

Life is good. Life is really, really good. As I write this I'm sipping on a very expensive wine and wearing a very expensive dress while sitting in my very expensive apartment. I no longer work, having not needed to earn my own income for little more than a year now. That probably leads you to wonder how I pay for all my nice things. Well while I enjoy my luxuries my boyfriend is in the room next door making the money. I can hear him now, working hard to pay for my lifestyle. A soft sucking sound interrupted by the occasional gag is all I need to know he is doing his job.

You see, a year ago I became tired of how little he did to contribute to our relationship, and not knowing what to do I stumbled upon something very interesting on his computer. Of course it was full of porn, and at first I was angry. I work all day and he is pumping away without a care in the world? He barely even had sex with me back then, occasionally rising to the occasion and leaving me completely unsatisfied. I was considering leaving him at that moment, but then I really looked at what he was wanking too. Pictures of the usual slutty women, sucking cock and being fucked by big burly men. However, these were covered in text. They had strange slogans written write across them like, "you yearn to suck daddy's cock" and "bend over, it is what you were made for". Also many of the images referred to who ever the reader is as "sissy".

I was so confused, was my boyfriend gay? Bi? Does he want to be a woman? I decided to research what sissy meant to try and figure out what the hell was going on in my boyfriends head. I spent hours going through forums and blogs, finding out about the wonderful world of feminization. Apparently some men fantasize about becoming more feminine, dressing and acting like a girl during sex. Many of them wish that this was was done to them by a woman, forced to act like a slutty girl by a powerful Mistress for their amusement. They become a feminized slave, bending over backwards to satisfy their dominant woman's desires. I remember thinking to myself, "but James is so lazy?" I couldn't believe that he fantasized about becoming a sissy, being ordered to act like an obedient sex slave when he wouldn't even do the dishes! This made no sense.

Then and there I decided to forget about it, turn off the computer and never think of it again. I would just go back to thinking of James the way I used too, but I couldn't. I started to return to those blogs. Whenever I saw James I began to see him all in frills, with long hair and painted lips. I started to notice I was becoming aroused at the thought of James dressed up like a girl and being fucked by big, strong men. What the hell was wrong with me? It felt like an addiction, an infection of the mind growing and growing.

Finally, I knew I had to do something.

******

Jamie has finished with her latest client now. She came out of the bedroom with her face covered in the man's cum, her make-up running down her cheeks. I scolded her, calling her a filthy slut and told her to go wash. All she did was mumble, yes Mistress. Now she is in the corner doing my ironing. She changed out of the very short, tight red dress she wears for clients into her adorable pink maids uniform. Even after all this time, all the horrible things I have made her do she still has that smile when she is dressed all femme and doing house work. I am looking her up and down. She looks so different now from the lanky boy she was a year ago. The exercise has toned up her body, and the corset training has given her some very feminine curves. Her hair is long enough that the wigs are no longer necessary and the electrolysis has done its thing to the rest of her hair on her body. Her make-up technique has really improved and really brings out the feminine features of her face. Her walk and movements in general have all grown more feminine, having become more gracefully and elegant.

She is sitting next to me now, head on my shoulder watching TV. We still like to act like a couple at times, but it feels more like I have a girlfriend now than a boyfriend. She has defiantly become more affectionate too since her transformation. At times I wondered if James ever cared about me, but Jamie can't go five minutes without telling me I love you.

Just now I asked her how her client was. It was so adorable, I want to tell you what she said just to show how much she has changed.

"Oh mistress he was so sweet. He was so shy, and didn't know where to look so I decided to make him feel more comfortable by starting slow. I kissed him and rubbed up against him, and it seemed to completely change him. He began grabbing and squeezing me, his hands roughly exploring my body. I guess he found his confidence because soon he was forcing me to my knees and shoving his cock in my face. I was so big mistress! Not just long but wide too. I didn't think it would fit in my mouth, but the man didn't seem to care.

Soon he was fucking my face so hard I couldn't breath. After a while he got tired of my mouth and threw me onto the bed. He ripped off my thong, and seeing my boi pussy and caged clitty he seemed to get even harder somehow! He was relentless with his fucking, ploughing me with every inch of his cock. I orgasmed twice, you know those sissy orgasms. My whole body was shaking with pain and ecstasy.

He decided to finish on my face, telling my to keep my mouth open. I knelt there with his cum dripping down my chin as he cleaned himself off. He also gave me a kiss before he left." She blushed at the last part. She gets so enthusiastic then realises what she has just said and gets all embarrassed. It's soooo cute!

**********

I remember the night she first lost her anal virginity. She was about four months into her training and I thought it was about time she earned her first pay check. I posted an ad online, showing off my little sissy. I could tell she was scared and embarrassed but she never asked me not to do it. No matter how humiliated she got she knew this was what she needed.

We went out that day to buy her a new outfit. We had found a lingerie shop that was understanding of our relationship, so she spent the day modelling outfits for my approval. We settled on a black mini dress with matching black heels. I also brought her a new bra and thong and garter belt, all black and lacy. One of the attendants gave her opinion too. She knew all about Jamie's sissyfication and had become a good friend.

I had Jamie return home in her new outfit. She had started to pass for a girl for a few weeks now so I wanted her to finally go out femme. She was terrified and wouldn't let go of my arm the entire walk back to the car. I don't know how many people knew she was really a boy but she definitely got some strange looks.

I got her home and started to get her ready, doing her hair and make up. When I was done I was no longer looking at that lazy guy I used to date. Now, I had a sissy girlfriend who was about to get fucked by a guy for the first time. I kissed her then, never having loved her as much as I did at that point. I could have torn off her clothes then and there,... but no. This was her night.

I ordered her to prepare her boi pussy while I got our bedroom ready. I changed the bed clothes to black silk, lit some candles and set up the camera. I planned to fully document the loss of Jamie's sissy virginity (an excellent idea from Mistress Alex). I was feeling so horny my panties were slick with my juices. I called in Jamie to satisfy be before her date came.

The John arrived right on time. I answered the door, Jamie behind me with her head bowed. I greeted and invited him in and offered him a drink. I introduced Jamie and the man immediately kissed her hand. Jamie blushed so hard I thought I might laugh. We went into the living room and talked for a while. I told the John all about Jamie's feminization, the things I have made her do. I could see a bulge begin to form in is trousers, and knew Jamie could see it too.

I didn't want to wait any longer. I suggested we moved to the bedroom and the John quickly agreed. We moved into the bedroom, the John's arm around Jamie's waist. I sat back in a chair I had put in the corner and left the boys too it. Jamie was clearly nervous and let the real man lead. He pulled her into him and kissed her, moving his hands down to the bare flesh between the end of her dress and the beginning of her stockings. Slowly he pulled up the silk fabric of the dress up over Jamie's head, revealing the black lingerie.

The John looked her body up and down, and so did I. Her soft skin was truly remarkable, and had made me envious many times before. Jamie's head was bowed, but with a thumb and forefinger the John raised her chin up to meet her eyes. They began to kiss again, the John's hands no longer restricted by the clothing.

I smiled as I saw Jamie fumble at the John's fly, letting his trousers fall to the ground. A large, hard cock bulged against a pair of boxers. I saw Jamie quiver when the John whispered, ''You ready to find out what cock tastes like slut?'' She said nothing, only nodded and dropped to her knees. With trembling hands she grabbed the elastic of the man's underwear and gently pulled it down. The cock sprang free, almost hitting Jamie in her face. She stared silently for a while, the cock swaying a mere inch away from her face. I could tell she was scared and needed my help.

''Don't worry sweety, I'm here.'' I knelt down next to her and took the cock in one hand, and placed the other on the small of her back. '' Just breath and open your mouth.'' She took a deep breath in and, closing her eyes let her mouth fall open. Her tongue hung out slightly, pink and lovely. I guided the John's cock slowly forward and gently pressed it onto her tongue. The most submissive moan I have ever heard from her vibrated the cock, making the John grunt.

She did nothing for a while and I had to tell her to start licking. She did, slow and clumsy movements at first, she started to lick the swollen head. I gently rubbed her back as she slowly gained her confidence and moved her tongue further down, worshipping the whole shaft. Soon she was taking the cock in her mouth, bobbing her head up and down. The John was now grunting in harmony with Jamie's little moans.

I moved back to the the chair, removing my panties as I did so. Touching myself I watched as slowly more and more of the cock disappeared into Jamie's mouth. The moans became gags as the John began to fuck her face, plunging his cock deep into her throat. I saw the John tense and knew what was coming. Quickly he pulled Jamie's mouth down to the base of his cock, the whole shaft filling her throat. He held her head there as he began to rock and spasm. Jamie choked as cum was pumped directly into her stomach.

When the John finally pulled out Jamie gasped for air. The John didn't leave her any time to recover though as he picked her up and tossed her onto the bed. She lied there on her back and looked up at him as he removed the rest of his clothes. He towered over her, his cock stiffening again. He grabbed her thong and tore it off her, making her yelp. I went to the bed and once again knelt beside her. I wanted.... no, needed to see her eyes. The look on her face when that cock finally went in, the moment where she will never be able to be a real man again.

Grabbing her ankles the John moved himself to her waiting pussy. With his cock in hand he began to rub her hole, sending whimpers moving through her. I held her hand tight and looked her straight in the eye. ''In a few seconds my love, all that is left of your masculinity will go and all that will be left is my pretty little girl.'' My words made her smile and I gave her a light kiss before waiting for the moment to come.

Her eyes swelled and mouth opened, but no sound came out. It was partly the pain, but I could tell it was mostly the sudden realisation that all those fantasy's, those nights rubbing to sissy porn were now, in this moment real. She was a real sissy with a real cock in her pussy. A tear rolled down her cheek and I knew she was broken, that from this point she would be nothing but a cock whore.

I kept a hold of her hand as the John humped away at her pussy. Jamie moaned and cried at times. I knew it was just hormones, she was in a very emotional state and just needed to cry. I kissed her lightly, cooing in her ear. ''Good girl. I'm so proud of you. I love you''. With mascara running down her cheeks she turned to me and smiled, a trail of cum still trailing down her chin.

'Thank you. Thank you so much,' she whispered before closing her eyes and rocking in time with the thrusts. She had accepted who she was, and was now truly happy. I kissed her cheek and left the room. This was her night, not mine. As I closed the door I saw the John pick her up and lay on the bed. I lingered as she knelt over him, cock still firmly in her pussy and started to bounce. She was lost. Lost in her slutty, sissy ecstasy.

It must have been an hour before the two emerged, the John pulling up his jeans and Jamie covered in my dressing gown. I said goodbye to the John before leading Jamie to the sofa. I wanted to ask her how it felt, but I knew it wasn't the right time. I pulled her close, letting her head rest on my breast. Soon she was asleep in my arms, the cutest of smiles on her face. As I sat there with my cum filled sissy boyfriend sleeping blissfully I thought how strange it was that the closest I had ever felt to him was while he was being fucked by another man.

Jamie stirred from her slumber and looked up at me with her sleepy eyes. 'Hello Mistress.' Her voice was low and rough but hadn't lost any of the feminine quality we had been working months on to perfect. I drew a hair out of her face and smiled.

''Hello my little sissy. How are you feeling?'' I could tell by her expression that so many emotions were running thorough her head, fear and doubt, excitement and arousal. She had just been fucked like a woman, the thing she has wanted for longer than I could possibly know. This was possibly the most intense night of her life, but in spite of that she simply said...

''Happy.''

********

Wow, retelling that story has made me all hot. Jamie is currently looking over my shoulder, giving out little moans as she reads this. Yes I can hear you dear. I have been thinking why I am writing this. It has been officially a year since Jamie has become my sissy slave. Maybe this is to commemorate that day, but I don't think so. Recently we have been talking about taking things further, and Jamie has been feeling like she still doesn't feel, ''right.'' She says she is not there yet, but doesn't know what there is.

I think we both know there is only one way to progress. I may call Jamie a girl, treat her and fuck her like a girl, but she isn't. This, I think is the problem for her. I don't plan to force anything, this is her choice, but I would be lying if I said it didn't excite me.

TollWard
TollWard
18 Followers
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13 Comments
jennifurzoejennifurzoeabout 2 years ago

Such a beautiful story and such a very caring Mistress to help her sissy become as she was meant to be.

AnonymousAnonymousover 5 years ago
you forgot

the part where the john left her 2 quarters on the night stand and you asked if he really thought jamie was so good he should pay her double what you had agreed she should earn for her cherry!

Riki1942Riki1942over 5 years ago
Sissy

I have had girlfriends, and was married for a while, but nothing like this happened to me. I don't usually have sex with strangers because my Boyfriend does me bareback and we like to stay safe. I'm a cross-dressing Sissy and I can relate to the feeling of the first time. I had wanted it badly for a couple of years but I wanted my first time to be the real thing; bareback. It took a while, sucking a few guys off wearing condoms, before getting to know one special guy that I trusted. It was everything, and more, that I longed for! The feeling, physically and emotionally, was such a feeling of pleasure, release from my wanna be status, joy and pride that I was actually for real and had been fucked and filled with cum! The pleasure just keeps getting better, but the first time was one that I will never forget!

AnonymousAnonymousover 6 years ago
Lovely story

I wish my girlfriend would discover my sissy side...

AnonymousAnonymousalmost 7 years ago
great

love your story. would like to read more of it!

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