Becoming A Sissy free porn video

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Previously published, but in separate parts, this one is the whole story start to finish.


This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation (that being said humiliation can be a turn on!)


I'd been married for about six years but our sex life had gradually fizzled out as I proved incapable of satisfying my wife. I have a small dick and while I was able to make the most of it for a few years, increasingly the only way I was able to get my wife off was through eating her pussy (which suited me, my inadequacy was becoming more and more obvious which made me less and less capable of using my limited dick to please her). It got to the point where sexual contact became further and further apart. I rarely initiated, and only occasionally would my wife push my head down between her legs to get some relief.


We sort of lived separate lives but were able to keep it together for family occasions and friends et cetera. Increasingly though my wife developed a social life of her own. I guess I could have done the same, but the realisation that I couldn't satisfy my woman really impacted my confidence. I discovered porn which seemed to be made for someone like me. I could spend hours and hours trawling the Internet watching videos, and gradually became a pathetic gooner. I could rub my dick for hours looking at these stunning women knowing I could never get them. My porn taste evolved from vanilla to anal, pissing and then to my surprise, shemales. It really surprised me when I developed a really strong interest in shemales. It's probably obvious, but I didn't really know why. Up until then I had been a pure tits and pussy type of guy.
Now I understand exactly what my journey was about. Knowing how inadequate I was I could fully appreciate a beautiful shemale with a magnificent cock. I wanked thinking of kneeling between their legs and worshipping their cock, balls and licking their arse. It just seemed to make complete sense.

X-hamster became where I spend every minute I wasn't working. I built up a huge library of video, photo and gif porn. Increasingly the only things I downloaded were shemale cock worship, sissy caption photos as well as masturbation and humiliation photos and gifs. I guess I was gradually becoming reconciled to my future, (perhaps the role I was born for), as someone who was to be humiliated and used and frankly I loved it.

My wife had never really demonstrated any interest in how I spent my time, although she was capable of the odd biting remark "off to play with your tiny dick" or "I bet you can't even satisfy yourself, never mind a woman" the latter remark was closer to reality than she could have known. I was now gooning so much I regularly lost the ability to get an erection irrespective of how many hours thinking about cocks, balls and ass licking I did.

While I was very careful about password protection, closing down my computer et cetera I suppose it was inevitable that while we were living under the same roof my wife would find out about my porn habits, although the way she did was to deliberately catch me out.

She had gone out to see some friends for the afternoon and I quickly established my wanking den. I set myself up in the living room turned on the TV with one shemale video playing on it, whilst flicking through sissy caption photographs on my laptop and started wanking gently to my shemale beauties.

By this stage I was pretty regularly mixing up pissing and humiliation with my shemale adoration. I would drink lots of water and then Goon and Goon until I had to relieve myself. I would then go down to the bathroom lie in the bath on my back raising my hips up in the air and proceed to piss down my chest and onto my face and hair. I loved it, it reiterated to me what I pathetic sexual individual I was. I would then lie in my piss and attempt to wank myself to completion.

The afternoon in question about an hour and 1/2 into this session, I was lying in the bath covered in my own piss and jerking my cock when my wife walked into the bathroom. She burst out laughing saying "I always knew you were a pathetic little wanker but this really is even worse than I thought" she took out her smart phone and clicked me lying there trying to cover myself up. All I could say was "babe babe please don’t……………."

Then she marched out of the bathroom and went into the living room. I quickly had a shower, covered myself in a towel and ran out to see what she was doing. I found her with my laptop going through all my porn files. When I came out she was clicking through my master file of sissy captioned photos and masturbation and humiliation photos. I tried to take the laptop from her but in the struggle she just reached down, grabbed my cock and balls and squeezed them as hard as she could. "Sit over there you pathetic little man, I'm going to find out what you've been spending so much time on" she spent the next hour going through everything, looking at the shemale videos (making sure to admire the size of their cocks) and even looking at a video clip I've taken of myself while pissing in the bath.

After that everything changed from my wife's point of view. While I'm not sure if she had been unfaithful to me in the past she was making pretty obvious that she was completely within her rights to go out and get fucked by a real man (her words obviously). I guess one of us should have called it quits and divorced but frankly her being out more and more just enabled me to spend more and more time on my porn addiction.

The incident with my wife really brought it home to me that I was a sissy. Again what is now obvious seemed to be a revelation back then. The fact that there was no pretence between my wife and myself, and the fact that she obviously did not care any more really gave me even more freedom to explore my sexuality.

I started wearing women's underwear. I had initially thought of buying these over the Internet or taking a couple of pairs of my wifes, but that appeared to me to be too high risk of her finding out and frankly the prospect of going to a lingerie shop to buy my underwear both scared me and excited me in equal measures. It was bound to be humiliating, but by that stage I was embracing humiliation (all those hours of x hamster slideshows telling me what a pathetic man I was had done the trick).

So one day I took the afternoon off work assuming the shops would be quiet and ventured into a department store. I had rehearsed the "I'm looking for something nice for my wife" and "she's about my size" lines so that I thought I could deliver them without blushing. My heart was beating my chest as I slowly made my way through the womenswear department to the lingerie section. As I had hoped it was pretty quiet, but unfortunately that meant the sales staff had plenty of time to help their one male customer who was presumably out of his depth. I had just started to rifle through some beautiful silk camisole bottoms when the sales lady approached me.

Can I help you sir? I will spare you my humiliation but no sooner had I got the "I'm looking for something nice for my wife" words out of my mouth, I blushed profusely. The lady put her hand on my arm and said "it's okay dear, I'm sure we can find something, what did you have in mind?" by now my heart felt like it was in my throat I was beetroot red and starting to sweat. As a result my voice became slightly high-pitched "these look nice". She smiled gently and agreed "yes these will suit you perfectly". I hung my head in shame and was about to bolt when she said "please don't worry sir I will be very discreet and find you something that you will love" I paused and looked into her kind face and decided to stay. 20 minutes later I was walking out with about 20 pairs of women's underwear (I know, overkill, but I didn't want to go back and do that again). I got immense joy out of wearing these over the next number of months.

The natural extension of my feminisation was that I completely shaved my body on a regular basis. Not only did I love the smoothness of my skin afterwards but I loved the process of turning myself into a sissy. I would look forward to the time when I knew I would have a couple of hours free to have a bath and slowly shave my body from armpits to my legs. To me it felt like a very feminising process, I even lit candles sometimes (I know, what a sissy).

Thinking about being a sissy I started to increasingly experiment with my anus. Obviously I had occasionally lubed my finger and stock at up my ass whilst masturbating, but knowing I was a sissy meant I had to explore this more which proved another very rich perversion to explore. On a trip into London I decided to buy some sex toys which would help me in this exploration. I had been very turned on by watching my porn idols with butt plugs in their ass. I bought a set of three and had endless enjoyment opening my anus with those, even keeping them in for a day and sometimes through the night. That then led me to buying a dildo. Over a period of time I used a bigger and bigger butt plug and got an incredible charge from wearing panties and occasionally a butt plug in everyday life. At this point I never really thought that it was ever going to go beyond me just enjoying myself and my addiction to porn. If you had asked me then I would have said I had the perfect life. The appearance of being in a relationship without any of the restrictions enabling me to pursue feminisation through my porn addiction, but I guess something had to give….

Part 2

The beginning of the end was when my wife started to see a guy who was in our social circle, actually he was a friend of my best friend Tom. Everybody knew what was going on. Nobody said anything to me (I knew as well) and things just sort of went along. However one night I got a call from Tom, usually I didn't pick them up as I would either be in the middle of or about to indulge in my new sexuality. Anyway, this night I was just sitting watching the football match having a beer, so I answered the phone.

"Hey mate I'm in the area, what about you and I have a beer and watch the game together?" All the excuses were running through my mind when he said "why don't I come around to yours, as you're already watching it by the sounds of it" before I could say anything he said "I'll be there in five minutes" and hung up the phone.

This didn't feel right. While we had been good friends for a long time we had drifted apart, mainly my fault but also I guess he felt awkward that my wife was pretty openly in relationship with one of his friends. I sensed an intervention, and I was right.

As promised Tom, arrived within five minutes carrying a sixpack of beer. Despite my sense that there was an ulterior motive it was definitely good to see him. We had been friends for a long time and shared a lot about the ups and downs of our respective lives. As usual Tom threw out his arms and gave me a big hug. He is about 6 foot three, 4 inches taller than I and a big solid bloke. His arms went around my shoulders and mine under his arms and around his back, briefly my head rested on his shoulder. "Great to see you mate, it's a long time since we had beers and talked shit together" we disentangled and I have to say I felt a little emotional that I still had a really good friend. Anyway, we sat down and watched the football and knocked back the beer pretty quickly. We talked a lot about the old days (we always do that) of hanging out together before we were both married. I felt more and more relaxed in his company and my nervousness was going away.

When the match ended I thought Tom would be on his way as I was sort of looking forward to a quick wank session.

I turned the television off and was making the usual moves to say goodbye to him when he turned and looked straight into my eyes and said "what's going on what you and the missus" I was a little bit surprised, I guess the beer had lowered my guard and I started to mumble "oh you know, going through a rough patch, everything will work out fine, relationship ups and downs you know…" Tom could sense my rising panic and just kept looking straight into my eyes, and a soft voice he said "mate, you can talk to me”………………….. He just left that hanging in the air and kept his eyes locked on mine. I felt a huge buildup of emotion in my chest, flushed red in my face and actually started to cry (what a fucking sissy). Tom just opened his arms and pulled me towards him and hugged me, this made everything even worse I started to bawl crying on his shoulder. "Tell me what's on your mind, maybe I can help, you know a problem shared is a problem halved" with that he started to chuckle a little and I joined in. "Christ Tom what you think of me? Blubbering on your shoulder like a little girl".

With that Tom pulled away from me held my face in his hands and said "you've got to tell me what's going on"

I knew that if I wanted to keep Tom as a friend, and I really did, (tonight had reminded me how safe, secure I felt in his company), I would have to at least give him the outlines of what had happened. Interestingly, perhaps the one thing I should have felt most nervous about, the size of my cock and its inadequacy, didn't bother me that much. Like I said we had been friends for a long time and we' had definitely seeing each other's equipment at different stages. His was a good 6 inches flaccid and I guess a reasonable handful around. In fact it looked pretty much like those Goddess shemales I adored. He knew mine was pretty tiny but had never teased or belittled me about it.

So all of these emotions were going through my head, and I decided to spill my guts a little bit. "Well, what have you heard?) I asked "what are people saying about me". "Well you know people are talking, what with your missus messing around with that prick Kevin…… to be honest I prefer to hear everything from you, and please know that this will make no difference to our relationship" I started to relax a little, "after all" he continued "I've known you for longer than I've known my own wife and all of my mates, I'm on your side".

So I sat down, looking at the floor still pretty ashamed that my life had come to this, I had to explain to my best mate why my wife had to get sexual satisfaction somewhere else. But was this going to be worse than buying underwear for myself in a department store? I hoped not.

For the next 30 minutes I went through the whole story from beginning to somewhere before the end! Went through my inadequacy, how myself and my wife had grown apart and how she had sought release elsewhere and that although I had not been unfaithful to her, that i had devoted myself to porn. At different stages Tom just nodded and occasionally made a comment but was pretty noncommittal. At the end I was finally able to lift my eyes from the floor and look at him directly in the face, hoping I wouldn't see disgust and rejection. To my great relief I just saw the kind understanding face of my friend. I started crying again.

"Mate, mate please don't cry, you really don't have to worry about this, shit like this happens all the time with people, I'm just glad you felt able to share it with me" with he stood up threw his arms out again and gave me a big hug "don't worry, everything is going to be okay" he said in a very soothing voice.

In the days after that evening I felt like a huge weight had been lifted from my shoulders, he was right a problem shared was a problem halved. But there was something else. Before this I had never thought of Tom in a sexual way. He was my best friend. Okay I knew he had an impressive cock and big balls that look like the shemales I admired so much, but he was my best mate nothing more. After that evening though I couldn't get it out of my head that my shemale fantasy was really a deep-seated fantasy for Tom. Now whenever I was gooning it was Tom's knees I was between, his massive cock I had in my mouth,his beautiful balls that I played with and his anus I tried to penetrate with my tongue. My perversion really was reaching new depths, or should I say heights. I had no problem reaching climax for the next week I can tell you.

It wasn't for another week that I heard from Tom, and I must say when I saw his name flash up on my phone I was relieved. This time I was wanking to a gorgeous shemale with a magnificent cock, but I didn't want to miss Tom's call, I wanted to talk to him and know that we were still good friends. "Hey mate hows it going" he asked "what are you up to" briefly I thought about lying to him, but then thought, he knows everything anyway why continue with life. "Tom, you know what I do with my evenings I'm on the Internet watching filth and trying to get an erection" I laughed. For a secondthere was silence at the other end, and I thought I had blown it, then I was relieved to hear Tom laugh out loud and say "hey, you've got to get your kicks". Then he asked "what website are you on?" Which surprised me a little. By this stage my desire to lie was completely gone "X hamster" I answered they've got some of the best stuff online and you can even create your own page with favourites and sufff" I just realised that I given Tom a big opening and he didn't mess it "oh yeah what your username on the site? Maybe I can check it out, see if we've got shared interests" fuck me I had really blown it. Oh well in for a penny in for a pound "snoozer 2000, but remember this is all fantasy stuff, you know stuff to get me off, not the real me". Tom started laughing out loud "you think I don't wank to porn online? Relax, this is just something we can share, let me check out your site and I'll let you know what I think, chat to you in a few days" with that he hung up.

I was immediately seized with terror. Okay I understood that Tom was no saint and that he was a good friend, but the truth is what he would find out about me when I looked at my page, was exactly who I was in all its filth and perversion" he would find out that I liked pissing on myself and got off watching others doing it, that I had a massive fascination with big cocked shemales which seemed to be boundless. He would see the sissy galleries which openly belittled and humiliated me identifying me as the sissy I am. For a few seconds I thought about deleting some of the more extreme videos on favourites but to be honest it would have taken me too long and I'm sure that before I had hung up the phone Tom was already registering.

I went back to my x-hamster page and logged on, and lo and behold within 10 minutes got a friend request from somebody you identified themselves as "bigtom" the message read "hey snoozer2000 you seem like a pretty kinky guy, love your page". I accepted the friend request, what difference would it make he knew my username.


Part 3.

Tom's story.

Myself and Peter had been friends since we were in school together were we had an interest in supporting common which really kept us as friends for years and years. We finished school, went to college got our first jobs and settled down all the time being in touch with each other, helping each other and basically being good mates. I had been divorced about three years earlier and Peter had been a real help to me during that time. My wife had just lost interest in me and frankly I had in her. We probably should never have married, but still it was a shock to the system which Peter helped me through. After the divorce I decided to fuck around as much as I could, why not, pussy was served up to me on a platter. I guess word got around about how big my cock was, it was like bees to honey. I had a no intention of settling down, once was enough, so maybe this whole development in Peter's life came at the right time.

I hadn't really been specific with Peter about what I had heard about his missus (Sarah) and Kevin. One bimbo that I had fucked claimed she knew what was going on. The word was that Peter couldn't satisfy his wife because he was so inadequate in the cock apartment (no surprise to me, but what did I care?), and Kevin really could apparently. I laughed when the bimbo, reassured me that Kevin was nowhere near as big as I was (she'd been there, done that). But I have to admit, I, like all the men I knew thought Sarah was definitely someone we would like a crack at, but hadn't because of Peter. Even more worrying about the rumours, was that there was supposedly a photograph of Peter lying in the bath, jerking off in a pool of his own piss. What sort of a bloke does that?

Being his best mate obviously it was no surprise to me that Peter had a tiny cock. When we had been out for beers et cetera I had seen it, or rather not seen it when we'd stand for a piss, he would always lean in more while I would stand back and admire myself. Occasionally I caught him glancing at me, but I guess that's natural.

Anyway all of this stuff was going through my mind when I decided to call around and see him.

The stuff I learned that night really explained an awful lot. His inability to hold onto Sarah the fact that she was seeing Kevin etc

When Peter told me about his porn habit, I guess it made sense to me, a bloke does need a sexual outlet after all. I was glad we had the conversation and frankly when he told me about the website he used I really wanted to find out more about what he was into.

Fuck me it was astounding. He clearly was submissive, a sissy in porn language, looking at all the photographs and videos which really could only have turned an already slightly submissive person into a complete sissy. Then there was all the shemale stuff, cripes this was new to me. Stunning birds with huge cocks!

I felt my own big unit start to stir. Why not I thought, I could really do with relieving the pressure in my balls. I pulled out my cock which was a big handful around and when I get erect, 9 inches of male perfection (my ex-wife's description). I started jerking off going through these videos, trying to find more and more out about Peter's new sex life. Then I came across a story he had apparently written. It was all about submission and the sexual pleasure of being pissed on. I didn't think about it too much, it was perverted, but I have to say my cock was loving it. What drove me over the edge was finding a gallery which was all about Daddy's. I wasn't exactly sure what that was until I had flicked through a few of the photographs. It became obvious that Peter was turned on by the idea of being submissive for his Daddy. Whether it was kneeling between a guys legs, sucking his balls, deep throating his cock or assuming the doggy position opening his smooth ass for daddy, it was a huge turn on. That's when I busted my nut. I came and came and came.


Later as I reflected on all of this stuff it did cross my mind, did Peter see me as his Daddy?


Peter

I really didn't know what I was thinking, there was a night out planned for all of our friends months ago and I never got around to telling people I wouldn't show up. Ordinarily this would have been exactly the type of evening I would have made my excuses and stayed at home with my beloved porn, but for some reason Tom called me and convinced me that it would be a good thing to go along, besides he wanted to catch up with his friend. I was a little puzzled by this, he hadn't said much about the X-hamster, perhaps he hadn't spent much time on it and had accepted my "it's all a fantasy excuse".

The minute I arrived at the venue I knew this wasn't a good idea. Sarah made it more or less obvious that she was with Kevin. Because of that I guess Tom seem to go overboard in his friendliness to me, bringing me to the bar having a drink and all in all making it obvious that we are friends. I guess if he had't done that I would have just sat in the corner, crushed by my wife's very public infidelity
I sorta took it for a while like the sissy that I am. But then at one stage she was sitting beside him with her hand on his leg rubbing up and down with the desired results. Finally I had, had enough. I didn't know what to do, I couldn't go up and confront her with Kevin beside her, could I? So in the end I just sent her a text "time to go, are you coming". I looked over when she received the message and a grin broke across her face. She fiddled with the phone for a while and then obviously pressed send and looked over at me. I almost cried when I saw the message which read "do you seriously think I'm going home with this" which was followed by the photograph she had taken of me in the bath, covered in my own piss with my tiny erection on show, the rest of the message read "when I can go home with this" underneath was the photograph of what I have to say was a magnificent cock, presumably Kevin's. She showed the messages to Kevin and both laughed out loud and looked over at me.

Embarrassed I rushed out of the club, hoping I would never see any of them again. However, Tom rushed after me, and tried to calm me down. "Don't mind him Peter, she'll soon get tired of that idiot and want to come back with you, just bide your time" I looked up at him and said "you've looked at my X-hamster profile, you really think I actually want her back? I think that ship has sailed and frankly I have changed too". He looked at me for what felt like a minute and said "yes I have to say I was a bit shocked, but I know you have to get your rocks off so no big deal, and by the way your profile is helped me get my rocks off a couple of times" he grinned and looked directly at me. "Anyway I've had enough of this night you fancy going somewhere else for a beer?"

I really wasn't sure, but even though I really wanted to go home and humiliate myself with lots of sexy porn, I was intrigued by the fact that Tom had followed me out and wanted to go for a drink. So we went down the road a bit, found a bar and started to have a few drinks, like the old days. Inevitably my small bladder got the better of me I had to go to relieve myself. Tom followed me in and we ended up side-by-side, which we hadn't been for a long time. As usual I was leaning in trying not to piss all over my shoes, while Tom was standing almost 1 foot back and pissing with power. I looked down at what I had remembered to be a magnificent cock. I got absorbed in it and for a few moments imagined I was lying in my bath at home and Tom was pissing all over me.

Needless to say I ended up pissing on my shoes! I looked up into Tom's face and he was looking into mine, "I hope this is turning you on, I saw some of your videos and I guess a big cock like mine pissing might get you off?" I zipped up quickly washed my hands and went out. I waited for him for a few minutes until he finally came out.

"Interesting, I thought you would have gone home humiliated, but then again I guess that's your thing" I looked up at him hoping I would still see my good friend, and indeed I did. He was making fun of me, not trying to humiliate me. He continued, “I gather this stuff turns you on, like I said I've been getting off to it too, but I'm interested how much of it is a fantasy? Have you made any of this reality, yet?"


I looked at him intrigued, I really hadn't expected him to completely cut me out of his life, but nor did I expect him to be as interested and questioning as he was being. A tiny part of me was thinking about what I'd seen in the toilet, and what I would like to happen in the future. He slightly cut me off balance when his next question was "tell me about this sissy stuff".

I went beetroot red, I wasn't sure I was prepared to have this conversation with Tom, but again I did slightly wonder if he was asking me to seduce him. We moved over to a table in the bar with no one else around so we could have the conversation in private. I explained how having experienced all the rejection from Sarah I had totally lost my confidence and explored the internet for stuff that got me off. Sissy and humiliation really did it for me. I guess it spoke precisely to my lack of manhood. Occasionally Tom would ask me to clarify, for instance "do you dress up?". I explained about how I loved the bodies of the sexy shemales, especially how smooth they were, so that yes I shaved my body from head to toe and had taken to wearing women's underwear. He was full of questions about where I got them et cetera and when I explained he just shook his head saying "how humiliating was that". He asked me had I ever had another man fuck me.

I quickly reassured that, no, all of this was just a fantasy for me to play out at home. "Sex toys?" He asked me. Jesus this was like being interrogated by Special Branch. Again I explained that as part of the fantasy I did use butt plugs and occasionally a dildo in my arse. I even told him that the night he had called over with the beer to watch the football I was wearing a sexy little Thong and a butt plug in my arse. He burst out loud laughing saying "if I'd known that, I would have wanted to have a look".

I looked at him sideways and said "I am tonight as well" I left it hanging there, enjoying his embarrassment and obvious discomfort for once. We said nothing and I went up to the bar to get us another drink, we knocked that back quickly and I could see that he was deep in thought. It was important that the next move was his, and I wasn't surprised, given how manly he is that he didn't back down "okay mate let's go home and see what you have to offer".

I couldn't quite believe this was going to happen. We made our way back to my flat, and I was reassured that Tom was taking charge of this situation (like he always did) and I was happy to follow. When we got home he really took charge, but still in a nice way.

"Tell you what, I'm going down to have another piss, why don't you set up your TV so we can go through some of your porn, and you can explain some of this stuff to me" I quickly scurried to get my laptop and connected it up to the TV in the lounge room. I pull two chairs together and waited for him to come back. As soon as he did I fired up the computer and started showing some of my personal favourite videos. I deliberately kept it pretty vanilla (or as vanilla as I had on my laptop) so as not to put him off. It was things like Gina Gerson blowing a big bloke with all of the enthusiasm she always has. Then I thought I would be a little more adventurous and show a Bailey Jay video where she is getting a blowjob. I was finding this quite a turn on, not so much the videos which were at the tame end of what triggered me but the fact that Tom was sitting beside me absorbed by it. "I think your stuffs a bit harder than this, are you going easy on me?" He asked.

I debated it for a minute and then just put on a slideshow of my favourite sissy and humiliation photographs which had a pretty liberal mix of Daddy stuff in it as well. "Oh yeah, this is the stuff I saw". This whole situation was getting too much for me and I started, I thought surreptitiously to rub my little clit. I guess Tom was looking out for it because he looked over at me and said "one thing we've never done is jerk off together, why don't we do that" with that he stood up and came over to me, pulling me into the standing position.

"Let's see this smooth body you've been hiding" with that he completely took charge pulling my T-shirt over my head, checking out under my armpits, and then undoing the belt in my trousers. I put my hand on his "do you really want to go through with this?" His answer was to brush my hand away and continue with undoing my belt, my button and fly and taking my trousers down to my ankles. He stood back and whistled quietly, "not bad, not bad" at this stage I was well past embarrassment, there I was standing with a completely shaved body and in a little red thong. I kicked my trousers and shoes off when Tom held my hand high in the air said "give us a twirl that" I giggled and complied. Just as I was about to turn around to face him again he stopped me by putting his hands on my shoulders saying "I think you've got something else to show me" then he gently pushed my shoulders down so that I was bending forward


His fingers reached under the top of my thong and pulled it down to my ankles where I stepped out of them in my best impression of a sissy. He bent my head further forward so that my arse was in the air. Then I felt his hands pulling my arse cheeks apart, revealing my little butt plug. "So you weren’y just teasing me" he laughed. I didn't say anything but maintained my position whereby he started gently tugging at the butt plug just a little at first and then a couple more centimetres and a couple more centimetres in the end he was gently fucking me with the butt plug, this went on for a few minutes and not to my surprise my clit started responded. I was partly humiliated mostly embarrassed but very turned on. He stopped and then raising my shoulders turned me around and looked down at my clit. "Yeah that's how small I thought it was" he said in a very matter-of-fact way. "Why don't you sit down and make yourself comfortable


As I sat down he stayed in the position facing me, but just out of my reach. He too pulled his shirt over his head revealing his hard muscular chest and arms. Wow I thought, Tom's been working out! Then very deliberately keeping eye contact with me he kicked off his shoes and trousers. I was surprised to see he wasn't wearing any underwear, (Tom going commando, what a stud). He just stood in front of me for 10 or 15 seconds with his magnificent cock just hanging there, backed up by his huge balls. I was afraid to even touch my little clit for fear that I would shoot my load. Then he just went and sat back in his chair and said "let's make this a good one"

The next 30 minutes are a daze, I went through video after video, lots of shemales giving and taking large cocks to a range of shemales, men and women. I was afraid to touch myself, because this was already driving me nuts. Rather I just looked over at Tom who had his cock in his hand and was wanking it to his hearts content. He looked at me and if winked saying "why didn't we ever do this before" he laughed.


The next video I called up was entitled "Sissy husband sucks BBC" the video started with some role-play you know, hot wife with a pathetic white husband and her black boyfriend with huge cock. Within two or three minutes the dominant wife and the BBC have the white guy on his knees sucking a huge black cock, and they switch to her straddling the BBC and ordering him to lick her ass, and the next scene was ordering him to kneel between the BBC's knees and lick his balls while she fucked him.
At this point Tom just looked over at me and said "so is this just a fantasy of yours or would you really like to do it? Because if you want to do what that Sissy is doing now is your chance" he opened his legs wide shifted his bottom forward in the chair and gently rocked his hips up and down with the effect that his cock was bouncing around, to my mind begging for attention. I stood up from my chair, determined to find out if this was just the fantasy of a porn addictg or my role in life. As I stood up, Daddy said "I don't think so sissy, shouldn't you be on your knees?" I smiled, Tom had really done his work, and yes this was going to happen.

I got down on my hands and knees and slowly crept over to him, keeping my eyes on the prize, that huge deck and those big balls. They were going to be mine. When I got to him he slid his bottom further forward in the chair and lifted his knees up to his chest "ass first".

I looked up into his eyes and said "Yes Daddy” for the first time. I leaned forward taking in the impressive view. I sniffed the aroma and pure a****l lust shot through me. I started licking this beautiful anus. For the next five minutes I lapped and lapped at his gorgeous butthole alternating between long wet licks and shorter stabbing ones, trying to penetrate his sphincter.

After that there followed a series of commands with my obedient reply "Yes daddy" "suck my left ball" followed by "right ball" followed by more of a question "both? I was in sissy heaven, Obviously, I was really lucky to have such a fine specimen to worship, I loved taking his balls in my mouth and toying with them loving the smooth skin, but knowing that they were full of sperm which drove me crazy. It was somewhere between having both balls in my mouth and responding to his order to take the gorgeous mushroom head of his cock in my mouth that I spilled my girly cum on the floor.

Whatever, I knew why I was here and it wasn't anything to do with my pleasure, rather everything to do with Daddy's. I played and played with the head of his cock alternating between gentle licks and then taking it all in my mouth. Then I heard his command "take more" and I knew that we had reached an important point, he wanted me to take his monster as far down as I could. I have to say that I was somewhat nervous but knew I had to serve Daddy as best I could I rose up on my knees and angled his cock towards my mouth so that I could maximise how much I could take. I opening my mouth as wide as I could and gently lowered my head over it. It was an incredible incredible feeling which I don't think I will ever be able to replicate. A sissies first blow job is a momentous occasion.


On the one hand, I know this sounds bizarre, I felt incredibly powerful. I had the ability to give pleasure to the most important person in my life with my tongue and throat and it felt exciting.

At the same time I was very aware that I was kneeling in my own lounge room with my sissy underwear on the floor, my pathetic shaven body which was neither male nor female with its tiny pathetic little clit. I had dribbled my cum on the floor and was kneeling between the legs of this powerful man with his cock down my throat. There was some humiliation there but I have to say I was very aware that I was pleasuring Daddy and that made me happy and fulfilled.

I continued to attempt to deep throat his cock but could only really take half it. He gently pulled his big hands on the side of my head and rocketed it forward onto his manhood. I was aware that he was getting closer and closer to climax. He started rocking my head faster and faster and then gave his final command "swallow it" within five seconds he was cumming in my mouth and down my throat. He stopped fucking my face and left his cock deep in my mouth grunting as he shot each load of beautiful cum down my throat. I struggled manfully (okay like a sissy) to take it all and was mostly successful. A little bit dribbled down the side of my mouth and on to my chin, but for a first effort I thought I had done a good job.

Then Daddy collapsed back in the chair which took his cock out of my mouth. Aware of my duties I kept his cum in my mouth and played with it, tasting it, getting used to its consistency. I then open my mouth to show him before very deliberately closing it and swallowing my first load of cum. Using my finger I pushed the cum on my chin into my mouth and swallowed again (you see my hours of porn addiction had not gone to waste).

Just then we became aware of the sissy video that had been playing. In a stern voice the hot wife instructed the sissy, “now clean him up”.Myself and daddy both burst out laughing. But then he stopped, raised his eyebrows looking at me and didn't need to say any more. I shuffled in closer so that I would be able to honour my daddy's request while allowing him to lie back and relax in the afterglow.

I started with his cock, sucking and cleaning all of the spit. I paid special attention to the head which was still dribbling cum. I went down the shaft kissing nibbling and licking up the mess I had left. Then down to his balls nuzzling them and licking them making sure they were clean for my Daddy. Finally with his encouragement I licked his ass clean. This whole process was turning me all over again, not that anyone cared.
When I thought I had done a satisfactory job I sat back on my heels and looked up at him. He looked down inspecting himself and nodded with appreciation "good job Sissy".

With that he stood up and reached down for his trousers and started to get dressed, when I started to do the same he stopped me saying "stay how you are, you don't need to get dressed until after I've left". I was a little surprised and started to say "but Tom" when he looked at me and it was then I realised that Tom and Peter had gone replaced by Daddy and Sissy. I felt part humiliation and part ecstasy. In my mind Daddy had just made a commitment to me, I guess you could say I was in Sissy heaven. Peter got dressed and without giving me another glance just said "I'll give you a call when I'm horny" and went out the door.


Part 4.

Toms voice

"Fuck me daddy, fuck me daddy, use me like the Sissy that I am, FUCK MY BOY CUNT, Give me your cock Daddy" I had my hands around the sissies hips as I fucked her doggy style pulling her pussy onto my hard cock, pounding and pounding. "Please daddy cum on me, paint my Sissy face, I want your cum on me, fuck me harder, I've been a bad boy"

I loved the power Sissy submission gave me. I was a fucking sex god getting the respect I deserved. As I looked down at her back I could see the butt plug winking at me from her anus. Fuck, this sissy had really come prepared for action, the thought that I would later be invading her anus drove me wild.

I fucked and fucked harder as the sound of my heavy, spunk filled balls could be heard smacking against sissies clit, I came closer and closer to exploding if if. If "Assume the position CUNT" She quickly dismounted my cock and assumed the perfect obedient wanton sissy position, kneeling, mouth open panting for my cum. My cock exploded with rope after rope of cum landing on her face, lips, in her eyes and hair, but like a good sissy her mouth stayed wide open to collect as much cum as she could. Just in case there was any doubt I took Sissys head and drove my cock into her throat, holding it there as she tried to lick my balls.

I then used my cock across Sissy's face to push my cum into her mouth. She took it like her life depended on it. Showing me my cum before swallowing it. “Thank you Daddy” Hours of work for sissy to have the perfect hair, lips, eyelashes and make up destroyed by 15 seconds of cum exploding all over her face, and all for my pleasure. I could really get used to my role as daddy.

Let me explain. As I got deeper and deeper into understanding Peters sexual perversion, spending every waking (wanking?) hour on X hamster, delving into control and submission it began to make more and more sense to me. Before talking to Peter about his porn habits and exploring X hamster my sex life had just been about finding some slut and fucking her. I'm not saying that was a bad thing, but it was obvious there was a whole world of sex I had not explored. This was a world which was uniquely open to me. MY POWER came from my cock and balls. You can dress it up any way you want but my cock and balls meant I was an Alpha male, and that meant there were pussies, cunts, mouths and arseholes out there, attached to submissive sluts (men and women) that would worship me. Peter made me aware of that and I intended to take what’s mine.

First I decided to test drive this new power with a dumb bimbo called Mandy. It's her face I came all over. I had fucked her once before but frankly the massive fake tits didn't do it for me. But when I thought about it, it occurred to me that her whole life, her whole being, was about pleasuring men, how submissive is that? I called up and asked her did she want to come over and get fucked. I said “I’m the daddy and you’re my sissy”

It felt good, after all I was probably making her year. The only problem is a took her five hours to get me. The dumb bitch went to the beautician, the hairdresser to get perfectly prepared for my cock. But then again I can't blame her, she knew that she was lucky to get another crack at me and her bimbo instincts kicked into overdrive.

I almost broke out laughing when I answered the door. There she stood with her long blonde hair, cock suckers lips, fake eyelashes, too much make-up, fake tan and those 44 double tits that didn't move. She was barely dressed but what she was wearing was pink. Built to use, and boy was I going to. I said nothing and turned and walked into my flat as I could hear her clip clopping behind me in six-inch heels. What a fucking joke.

Still, one thing I can say for her is that she knew all about daddies and sissies. Immediately she got on her knees and started crawling over to me. "please daddy can I see your cock" and "please daddy put your cock in my mouth" et cetera et cetera I loved the begging and subservience and control. Finally my massive cock and huge spunk filled balls were getting the respect they deserved.

After I came I lay on the bed and said "clean up your shit" she crawled up to me until she got to my balls and started licking her slime off a them. I lifted my knees to my chest presenting my anus, and she didn't even blink, her face was between my ass crack licking and sucking it clean. Interesting. Then she got my cock, I finally understood the real meaning of cock sucking lips. She used them to clean all the spit and slime leaving it in perfect condition. With that she slid off the bed and went to go to the toilet.

Interesting, I guess she thought she was finished. I followed her into the bathroom and there she was sitting on the toilet pissing. I said "I need a piss" and she started to get off the toilet I said "no, in your mouth" she looked at me with her dumb face as both her brain cells tried to compute what I just said, and then it clicked. For a second there was hesitation and then " please daddy give me your piss" she threw her head back, opened her mouth wide and stuck out her tongue. I walk forward, my legs straddling her sitting on the toilet and put my cock in her mouth and started to piss. I never thought having a piss would be such a turn on. I Gushed into her mouth and down her throat as she bravely tried to swallow again and again, only succeeding in the piss going down her face and over her tits and body.

I had thought that this might even be a step too far for me, but it wasn't about the piss. It was about the fact that this dumb bimbo would allow me to do it, and it was a huge turn on.

When I finished Sissy swallowed for the last time and looked up at me for reassurance. "you've been a great little sissy, now I'm going to fuck your ass"

We went back to the bedroom after Sissy had cleaned herself up a bit. "Daddy's cock is so big and powerful I need to get my little sissy anus ready for daddy, is that okay?" Fair enough, I thought, I might enjoy the show.

With that sissy, still in six-inch heels, went to her handbag and took out some lube and what looked like a bigger butt plug than the one already embedded in her ass. She got on the bed on all fours, and reached around and took out the butt plug. There was no way it had prepared her for my cock ploughing her ass. She got the bigger butt plug put some lube on it and slowly inserted that past her sphincter. She played around with it, obviously getting her sphincter ready for anal invasion.

Despite myself I found I was getting a grudging respect for Mandy the bimbo. She took this shit seriously. She continued to play with the bigger butt plug, stretching her ass by rotating it. As she did it was clear it was turning her on as her breath became shallower and shallower. She then dropped the second butt plug and lubed up her fingers. Three fingers went into her ass easily and then she pushed and pushed until her hand, up to her knuckles had entered. She started masturbating herself, pushing her hand in and out, stretching her ass. By this stage I had a raging hard on. While I was enjoying the show I couldn't wait to invade her anus and leave my load in there.

Finally Mandy got her whole hand into her ass, and fucked herself with it. What a show! But she didn't forget why she was here. She turned her head to me and said "sissies ass is ready for daddy, can I have your cock in my ass now please" there was a whimper in her voice, I understood again the joy I was going to be giving her when I reamed her ass.

I quickly got on the bed and availing of her gaping ass hole slid the head of my cock in, quite easily. Sissy gasped as she realised that for all her preparation, this was the real thing. I pushed about half way, encountered some resistance and then gently started to increasingly invade her anal passage. Sissy whimpered "yes daddy, yes daddy, my ass is all yours" it took me about 10 minutes to get my whole cock in their, but when I did I felt magnificent. I felt like I was finally getting the respect and worship that I deserved, that thought drove me wild and I started to plough into Sissy's ass.

I fucked her hard for 10 minutes as Sissy encouraged me and begged me for more, my balls smacked against her clit probably driving her wild as my orgasm built and built and built. I felt like a bull, a total fucking stud claiming what was his. Sissies ass started to pulsate and throb, massaging my cock, and that drove me over the edge I buried myself deeper into her bowels and exploded inside her, I closed my eyes imagining it was Peter below me, and with that I almost fainted.

When I'd finished I rolled over onto the bed, seeing stars. Sissy again crawled up between my legs, taking my cock which had just been in her arse and started to clean it. She licked and lapped and sucked the spit from my cock and balls. At some point, I fell asleep, but not for long. I opened my eyes to see Sissy standing beside my bed looking down at me. When she saw me wake she asked "Will that be all daddy" I nodded, closed my eyes and as I fell asleep could hear her totter on her high heels to the door." Thank you Daddy, thank you for everything" and with that she left.


Well, if that was the appetiser and the test drive, I definitely wanted to move on to the main course. I knew now that being a daddy was what would fulfil me, and I decided that I would seduce Peter into being my first real sissy. I didn't think it would be that hard, so when I heard about the night out I decided to make my move.

Mandys Story.

Only joking, nobody cares.



If you like my story, or even if you don't please leave comments below, or failing that, thumbs up or thumbs down if you didn't like it. Two more parts to come over the weekend I hope


Part5.

Sarahs story.

I finally realised that I'd made a mistake getting married to Peter. I guess if you were to describe me would say I was a loyal and sympathetic person and it's probably those qualities which led me to marry such a wimp. So why did it take so long for me to realise? Because I never really had a proper sex life. I met Peter, fell in love with him and figured that's what marriage is about, so that's what I did. It was only when I opened up to the girls that I realised I was really missing out on something. Peter's little penis couldn't give me an orgasm and I finally got tired of that. Obviously my turning off sex with him did nothing for his confidence, but that's the loyal sympathetic Sarah speaking, what I wanted was to get well and truly fucked.

My girlfriends were astounded that I had put up with "pathetic Peter" as they called him for as long as they did. It's interesting, in the past I would have walked out if somebody had said that about my husband. But they weren't being mean, it was just a fact. He was a pathetic weak man with a tiny penis. What else could you call him?

They really got enthusiastic about making sure I would have a fulfilled sex life. Obviously, they were worried that my cunt wouldn't be able to take a real cock. So one night when I turned up for a drink I found that they had clubbed together and bought me a range of sex toys butt plugs, dildo's and vibrators. They ranged in size from about twice as big as Peter to something as big as my arm. Seriously, would I be able to get that inside me?

We all got a bit pissed, and the jokes were flying about me going home to fuck King Kong. Anyway I was on my way home with Julia, who lives nearby. "Well, you going to use them tonight?" She asked. I told her I wouldn't be able to as "pathetic Peter" would be at home, as he always was. I could see a mysterious smile on her face and she said "come around to my place, I'll be able to supervise you, just so you don't injure yourself" she laughed. I jumped at the opportunity, I know I was a bit tipsy but Julia was a good friend and I thought she would be able to help as she seemed an expert.

When we got in her door she took me by the hand and brought me to her bedroom. "Tonight, you're going to lose your virginity" while it wasn't technically true it did feel a bit like that. I had butterflies in my tummy and I could feel my cunt begin to tingle. I felt like a virgin on her wedding night as Julia led me by the hand up to her bedroom. When we got there she threw me on the bed and said "I'm going to the loo, make yourself comfortable". All of a sudden it dawned on me that I was going to be naked and presumably playing with those sex toys in front of another woman. I panicked a little and instead of making myself comfortable just sat on the edge of the bed waiting for Julia to return.

She came out of the bathroom totally naked. I was shocked, I hadn't expected that. She looked at me and teased "is my virgin a little bit nervous". "Don't worry, this is just an extension of trying on clothes in front of each other, or getting our Brazilians done at the same time" I looked up at her, puzzled " don't tell me you don't trim your garden?"

I was starting to get really embarrassed "well I do trim it a little, but by myself". Julia crawled up behind me on the bed and removed my jacket, as she did her hands brushed over my breasts and seemed to linger on my nipples, she got an instant reaction. "That's interesting, I'd say you were so horny you are about to explode" it was true, while in my head I thought I should resist, my body was betraying me.

I leaned back into her which enabled her to kiss me gently on the side of my face and neck. "I've always wondered what your tits look like, they look magnificent encased in this blouse, but I think they will look better with me sucking on them, don't you?" By now I was starting to moan a little, her hands were gently toying with my nipples and it felt amazing. She took this as permission to start unbuttoning my blouse, then gently pulled it back over my shoulders. She started to giggle" Jesus Sarah where do you buy your undies, in Marks & Spencer? I think I'm going to have to take you shopping" she undid my admittedly very plain bra from the back releasing my 36D tits. She reached around cupping my breasts in her hands, we both moaned.

With that she came around in front of me and I got to see her body properly for the first time. She was much more petite than I, very slim with small tits and I realised a completely shaven pussy. It was a real turn on. She pushed me back on the bed and climbed over me, and started to suck my breasts, paying special attention to my nipples. I was lost, I had never done anything like this before, but it felt amazing. I felt like I was the centre of attention and that my lust was finally being acknowledged and served. Julia kept licking and sucking and occasionally very gently biting around my nipples, I felt intense pleasure and then with great shock felt my body getting lost in a shuddering orgasm. I close my eyes, and stuck my hand down the front of my skirt and started to rub my clitoris. I had never felt like this before. All too quickly my orgasm came crashing over me , leaving me breathless and panting on the bed. As I recovered I opened my eyes to see Julia smiling down at me, "I'll take that as a compliment"

Julia gave me a couple of minutes to recover and then encouraged me to move up the bed. As I did, she stayed where she was saying "let's see the rest of your hot body" 30 minutes earlier I would have been shocked, now I just raised my hips so she could pull my skirt down and I could reveal myself to her. No sooner had my skirt hit the floor than she push my legs up to my chest saying "let's give your cunt some attention"

With that she went down on me licking my pussy paying special attention to my clit. Having just cum I wasn't sure there was any point, but as Julia continued to pleasure me I felt the joy of another orgasm building. As she was licking me she started to gently explore my cunt with her long fingers. For a moment I felt angry, why had I wasted all those years with Peter? Julia continued giving me pleasure and I started to wallow in it.

"What about we see what your beautiful cunt can take?" With that she reached down to my goodie bag and took out the dildo's. She gave one of the larger ones to me "here, practice sucking on a big dick, it'll come in useful" with that she gave me the dildo and I immediately put it in my mouth sucking and licking on it like my life depended on it. At the same time she was doing the same to a smaller one and then brought the head of the dildo to my current lips. She gently pushed it in and surprisingly it didn't encounter too much resistance. "How does that feel?" My mouth was full of cock so I could just moan in acknowledgement, I took it out of my mouth and said "bigger". With that she took out King Kong and gave it to me. It was an enormous, like the size of my arm. "Get used to that in your mouth and give me the other one" with that she took the smaller dildo out of my cunt which briefly left me feeling empty. "Let me know what this feels like" with that she rocked my hips further backwards and started licking my anus. Jesus it felt like I had been given an electric shock. The waves of joy and excitement that washed over me were almost too much for me to handle. With my ass high in the air she took the small dildo and toyed with my sphincter. She raised her eyebrows looking at me and I nodded my permission.

I was about to be fucked in the ass for the first time. She gently pushed the dildo in and my ass greedily gobbled it up. I don't know which of us was more surprised. Julia had a puzzled look on her face and then looked at me and said "how did you survive with pathetic Peter for all these years" it looks to me like your ass was built for fucking, let's see about your cunt" with that she took King come from me and again looking at me for permission gently toyed with the opening of my vagina.

She spat on my cunt lips and licked King Kong and then very gently tested my opening. At first there was resistance until King Kong's knob went into my cunt. It felt stretched, a little sore, but if I was to describe the feeling I would say I felt alive for the first time. Julia gently rocked King Kong forward and back each time putting a little bit more inside me. I was greedy for more. My ass was already full of cock and I wanted my cunt to be full for the first time. I pushed back against King Kong taking another two or 3 inches. What did I feel like? I felt like a dirty whore, and I wanted more.

Julia was stunned. " Are you sure you haven't been playing away from home with a horse"? I giggled, "no but if you have one I might give that a go"

With that I pushed back against the dildo taking all 10 inches of it into me. The feelings in my body were intense and I started to rub my own clit aggressively, I wanted to cum again and knew it wasn't far away. Julia helped me by gently fucking me with both dildo's while I rubbed my clit. My orgasm came crashing through my body and I may even have fainted in the intensity. But I continued rubbing my clit and then the most amazing thing happened. My cunt started gushing, as if I was pissing, but I could not have cared less, I was in ecstasy. It gushed and gushed, all over Julia who got over her initial shock in time to put her lips over my current and drink down my cum.

It lasted 10 seconds, and I have to say if I had died then with a woman lapping my pussy, King Kong embedded in my pussy and another cock in my ass I would have been a very very happy woman.

We both collapsed on the bed panting and trying to make sense of what had happened. I looked at Julia and we both burst out laughing. "Jesus girl, you were built to fork huge cock, and while I'd love to give you this pleasure every night, I think we have to find you a living breathing penis"

We cuddled and I fell into the deepest most satisfying sleep I had ever had.


The next morning I woke up and immediately started to panic. What had I started? How could I have done what I did last night, was I just a dirty whore? Julia woke up and realised the cause of my panic. She reached up and started cuddling me bringing me back down beside her.

We talked for a long time and she made me realise what I guess I already knew, that I had to explore my sexuality, which I had ignored while being with Peter. The intensity of my orgasm and the pleasure the dildo's (and Julia) had given me meant there was no going back. But where could I find a cock which would satisfy me. I was surprised when Julia said "well of the men we know there is either Kevin or of course Tom" I looked at her puzzled and she started laughing "don't tell me you didn't know Tom was hung like a donkey" I hadn't, I guess all those years of suppressing my desire had meant I hadn't even been checking out was in front of me.

"Well obviously I can't go out with Tom, his Peter's friend, and while I don't owe Peter anything I don't want to rub his nose in it either"

A week later I manufactured a meeting with Kevin with the aim of seducing him. Almost immediately I regretted it. While he was well endowed, apparently he wasn't a patch on Tom, and my continued masturbation with King Kong led me to understand that only the biggest longest fattest cock would satisfy me. So when I went along to that party at the club and was all over Kevin it was just so I could make Tom jealous and want to fuck me. But to my surprise he was all over Peter, Jesus was on about? I guess they were friends.


if you enjoyed the story, please give it a thumbs up. Happy to hear your comments. The continuation of Peter's story will be next.


Part 6.

The story returns to find Peter in the aftermath of his mind blowing night with Tom, how would he react?


When Tom walked out the door and left me on my knees with my own cum stain on the floor, the taste of his arse, cock, balls and cum in my mouth I was stunned. The whole night was like a dream. Earlier in the day I considered myself to be a porn addict who would goon and wank for hours. Now? Well I had answered one question, this was more than a fantasy, the satisfaction I felt for giving such pleasure to such a magnificent Alpha Male told me my role in life was to be a sissy. I sat down in my chair, found my favourite Sissy Hypno video and jerked my little clit to completion. Then I did something I had never done before but which felt completely natural. I collected my cum in my hand, brought it up to my mouth and licked and slurped it into my mouth. If I was going to be a Sissy I had to get used to the taste of cum. While I enjoyed the taste and texture of my own, my memory of daddy's was that it was much richer and thicker which was to be expected, he was Alpha, I was Beta.


For the next four hours I sat watching sissy video after sissy video, observing how a good sissy worshiped an alpha male. I made mental notes of how I should crawl, swinging my ass and boy pussy from side to side, advertising my femininity.

I saw that to be a good sissy I had to know when to make eye

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It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
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Saturday Morning Sissy

Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
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Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

2 years ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

3 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

2 years ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

3 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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  • 38
  • 0

What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

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