Who's The Sissy Now? free porn video

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Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going through something of an identity crisis surrounding my body and my blossoming sexuality. The feelings that I had always had as a c***d that me being a boy wasn't quite right were now increasingly pronounced. Of course, under the circumstances, this just made me more embarrassed and insecure, I was so different from the other boys and the way that they teased me about my girlishness made me feel that it was somehow a terribly wrong way to feel.

As would be normal in a young girl my age, had I only been born a girl, I was also starting to look at boys and feel new urges and desires for them. One boy in particular drew my attention and that of many of the girls at school. Greg Ellis was the school's star athlete and had a toned, trim, muscular physique to match. He also had a cocky, arrogant streak that just made the girls want him more. He knew he was good looking and knew that all he had to do was turn his attention on a girl and she'd do anything for him. He was also the very worst bully of the lot of them. Like many good looking, tough guys, he felt a need to assert his masculinity and his dominance over the other guys at school and he mostly did this by putting down any of the easier to pick on k**s.

I don't know whether he chose me as the brunt of his worst behaviour because he sensed the way I looked at him, the way I lusted over him when he wasn't looking, my shy glances like those of so many of the girls. Whatever the reason, if he wanted someone to sling insults at to impress people or boost his own self esteem, it was usually me he called a dirty fag or a sissy. The whole class joining in to try and impress him, pushing me around and teasing me about my pathetic girlishness was bad enough, but for it to be the boy I so wanted to like me that was doing it was especially painful to me.

Still, I got through high school and after years of grappling with my identity and sexuality, I finally was able to truly express myself as the real me and was completely transformed. I was born again as a new person, a beautiful, sexy woman, the kind that drew the kind of attention from guys that I had always yearned for. More than that, I was finally confident and comfortable in my own skin. My feminine body, slender waist and long legs, my pretty features, long lashes and full lips, the very things that had encouraged the high school bullies were now what I loved so much about myself and took all the chances I could to show off in glittering make up, high heels and short skirts. I was also finally comfortable with my sexual desires and, having missed out for so long on the pleasures of being a girl and then a woman, I pursued men with a passion, desiring all the ecstatic sexual pleasures I could get, I became the mistress of my own desires.

Where as a young guy I had been so insecure, becoming a woman had unleashed a new side to me, one that liked to take control of any situation, especially being the boss when it came to men. In my experience, it had been the case that most men when faced with my beautiful body and aggressive approach became pretty easy to manipulate and willing to do anything to please me. They didn't even seem that bothered when they discovered the truth about me. In fact, they didn't seem to take much encouragement at all to get down on their knees and take my swollen dick in their mouths. Yes, I had kept one part of my old masculine self still very much alive. My cock was the source of so much of my sexual pleasure that I couldn't be without it. Besides, at a thick seven inch length, it was one part of me that had always been impressively masculine, even more so when compared to my mostly petite girlish body.

This was the point I was at in my life when chance through up the opportunity to get back at my teenage tormentor, Greg Ellis, now all grown up. He was about to find me a changed person, sexy, sassy and confident, I was about to reverse the situation that once existed between us completely. He had made my high school years hell, but I had emerged a stronger person and he was about to find out just how I could control a situation now.

As usual on a Friday night, I was out in a bar looking for hot straight guys whose lives were about to be turned. I was dolled up in the kind of clothing that made me feel sexy and drew no shortage of admiring glances from around the bar, a short black, pleated satin skirt and a sparkly silver top. My long legs were shown off in nylon hold-up stockings and a pair of five inch heeled black patent pumps. My long lashes were enhanced with glittering mascara and sparkling blue eye shadow. My lips were painted a wet pink that also shimmered in the light.

So far, the talent in the bar had been nothing special, until a group of lads about my age walked in. They were a bunch of toned, athletic guys, just my type, and they quickly drew my interest. Maybe this night would turn out better than I had anticipated. I sauntered passed the group towards the bar, swaying my hips in the short skirt that brushed against my stocking tops, feeling their eyes watch my movement, lustfully taking in my long legs and pert little arse. Suddenly, I was stopped in my tracks by a voice I thought I recognised but couldn't quite place.

"Woah, check out that nice piece of ass," he said, obviously the ringleader of the little group, speaking loud enough that he clearly intended me to hear, "I wouldn't mind hitting a bit of that!"

"Nah," said one of the other guys, as I was still trying to place his friend's voice, "She's out of your league, Greg."

Greg! That was it, the name recalled to my mind instantly the owner of the voice. As I turned to give him a quick once over, checking him out as he had me, I could now see that it was unmistakably my high school bully, looking better than ever. The ten years since we had graduated school had allowed his tall, athletic frame to fill out with muscles in all the right places. As he turned from me, I could see the kind of tight, toned arse that was just what I looked for in a man. Confusingly, as all those feelings of anger at the way he had humiliated me in school came rushing back, so did feelings of lust arise in me.

"Hi guys, I'm Candy" I said, turning slowly to give them the full benefit of my hot, womanly body, my curves and long legs in stockings and a very short skirt, I could see from their expressions that they liked what they saw, "Are you guys checking me out?" I asked flirtatiously. "You're kind of cute," I said, addressing Greg, "Maybe I'll let you buy me a drink."

I didn't quite know what I was doing but a plan was forming in my mind, something was telling me that maybe I could find a way to get back at this bullying, homophobic arsehole and get some great sex with a hot guy at the same time. I could tell that he certainly didn't remember me at all, I guess I'd changed a bit since then.I could also tell that he was pretty into me. As I beckoned him over from the group and had him buy me a drink, he was totally compliant, no more of his brash posturing. I was already in control of the situation and this made me feel pretty good about it.

His friends looked pretty astounded that I had made a move on their boy and seemed to be enjoying his company. As ever with groups of lads, they were both egging him on and laughing and mocking him at the same time. After a couple of drinks we began to dance together. By now he was no longer so completely under my spell, and his brash, showing off side came back as he began to grind his body against mine, running his hands over my pert arse.

"Look at those fags," he said, indicating his friends, "So fucking jealous, they could never get a hot girl like you to even speak to them. None of them are real men, just a bunch of queer sissies."

The way he spoke about the other guys brought me back to how he treated at me at school, even while the closeness of his fit, athletic body began to make me a little hot and flustered. Unlike at school, when he used to drive me to tears, now I smiled inwardly at the thought that even while his talk was all gay bashing, he had completely failed to notice the cock hanging beneath the skirt of the gorgeous girl he was pressing his body close against on the dancefloor. Well, I was now pretty convinced that before the night was out, he was going to know about it. I was going to turn him into the cock loving queer he liked to bully.

At one point, when Greg went to use the bathroom, one of his friends came over to talk to me.

"Hi," he said, being kind of shy and cute and polite, "I just kind of wanted to ask what you're doing with Greg? I mean, a stunning girl like you is way better than a guy like him. I know I'm sort of his friend but he's an arrogant, bullying prick. Just thought you needed to know really."

"Oh, don't worry honey, I already know that pretty well," I grinned.

"So, what are you doing with him?"

I glanced around the room to see that nobody was watching and then decided to take a chance. After all, part of what I wanted here was to humiliate Greg with his friends. So, I took the guy's hand in mine and brought it under my short pleated skirt, placing it on the bulge in my panties. His eyes widened and his mouth fell open with shock as he simply stared at me for a few seconds, his hand still feeling my cock, struggling to comprehend what this meant. Then, at last, a nasty smile grew on his lips as he understood that his bullying queer bashing friend was about to go home with a pretty girl with a dick.

After Greg got back, I grabbed his arm and whispered in his ear about wanting to go back to his place and we left pretty quickly, he was obviously as eager to see what was inside my panties as I was to show him, of course he was in for something of a shock. As we left the bar, I noticed out of the corner of my eye, Greg's friend pointing something out to the rest of the group. They were trying to stifle laughter. I smiled to myself again. Whatever happened tonight, I had done some damage to his reputation as a stud even while he was seen leaving the bar with a gorgeous girl.

Greg's place was a large flat in a nice part of town. It was clearly the bachelor pad for his single existence as the furniture and decor clearly had little of a woman's touch. The furniture was bland and functional and the place was a bit of a mess. Never mind, I wasn't really interested in interior decoration. My mind was going wild with lustful thoughts for the hot guy who owned the place and the fact that I was so much desiring revenge on my high school bully was just even more of a turn on.

Pretty soon we were making out, our bodies pressed tight together, our lips locked in passionate kisses. I decided to take control, invading his mouth with my tongue, running my hands down his back to clasp that nice, firm arse of his. He didn't seem to mind, he obviously had no problem with a girl who likes to be in charge. As for me, I could feel a telltale stirring in my groin as we kissed, as my breasts pressed against his hard chest, my cock was becoming hard and still he didn't seem to notice quite the sort of girl I was.

"Take your clothes of honey," I said, pushing him away from me, "I wanna see that nice arse completely naked."

I've never seen a guy strip quicker. In a couple of minutes, his firm, toned body was completely naked. I drank it in with my eyes, licking my lips. He might be a bit of a dick, but he was certainly hot. He had nice, rippling abs, strong thighs and a middling size cock (not as big as mine though), already growing quite hard just from kissing me. He grinned at me as I pulled my sparkly silver top over my head and unclasped my bra to let my nice, round breasts fall free.

"OK, now it's your turn," he grinned dirtily, "I wanna see your hot body before I fuck your brains out. Don't worry, Candy, it's gonna be a night to remember."

"Oh, yeah, I'm sure it is," I said, smiling to myself, "But first, turn around, let me see that cute arse of yours."

He did as I said, turned his back to me and bent slightly over, showing me that naked, firm arse. Just the way I like it, I was going to enjoy fucking that. I landed a playful slap on his arse.

"Nice," I giggled, "We are going to have some fun."

"Oh yeah, baby, we're going to have plenty of fun," he said, turning back around, "How about you get down on your knees and wrap that pretty mouth around this," he began to wave his semi-erect cock in my direction.

"I think I've got a better idea," I said, as I unzipped my short, pleated skirt and let it fall to the floor.

Underneath, my black satin panties were already becoming stretched a little by the strains of holding in my growing erection. I could see Greg do a double take as he looked down my beautiful, curvy body and saw something he didn't expect in my panties. As I let them drop as well, leaving me dressed in nothing but stockings and heels, showing off my long, sexy legs, my cock sprung free and left him in absolutely no doubt as to the kind of girl that he had brought home with him. I grinned naughtily at him and began to stroke my dick, making it even bigger. I looked down at his hard-on and then at my own.

"Looks like I'm the one that's more of a man where it counts," I smiled, "Maybe it's you that should be on your knees sucking me off!"

"Oh no. No no no," he said, shaking his head as if he couldn't quite believe it, "No..that's not...I didn't want that...I'm not some kind of fag. I don't like dick."

"But you like me, don't you Greg?" I smiled, nice and seductively, "You like beautiful girls, well look at me. Tell me I'm not one of the most gorgeous girls you've ever seen. It's ok to want me, it doesn't make you gay. Look at my long, sexy legs in stockings and heels, my nice round breasts, my pretty girlish face. Don't you want to show what a studly man like you can do to please a hot girl like me?"

I could see he was wavering. He didn't come over to me but neither did he back off. He stood there staring, still completely naked. I noticed how obviously his gaze ran over my feminine curves but lingered most of all on my thick, hard meat. He was obviously thinking quite deeply about it and, if his own arousal was anything to go by, some part of him obviously liked what he saw. I could see from experience that it wouldn't take much to push him over the edge. He had already been so easy to control and do what I wanted this evening and now he seemed fascinated by my sexy feminine body and hard masculine cock together, he couldn't draw his eyes away. I could tell that in his struggle between the desire not to appear like the sissy queers he had always hated and the intense lust for my beautiful body, the latter was beginning to win out.

"Come on Greg," I said, putting on my most pleading,seductive tones, licking my lips and playing with my breast with one hand while I continued to slowly stroke my cock with the other, "I'm sooo hot and horny, I really need a man to get me off. Won't you be the one to do it for me, pleeease? Come on over here, lover, and help me out..."

That seemed to do it. He walked over to me and, when he was standing right in front of me, I pushed him onto his knees.

"Oh, Candy, you're such a sexy girl," he sighed, with his face just inches from my hard cock, "I'd love to be the one to please you."

"Mmm, what would you like to do to me?" I grinned, standing over him in my heels, looking down on him kneeling in a position of supplication, "You'd like to suck this nice, thick cock, wouldn't you, honey?"

"Oh yes, Candy, let me suck your lovely, tasty meat. I'm not gay but I'll be a cocksucker for your beautiful member, Candy."

He leant forward and wrapped his lips around the head of my cock, flicking his tongue across it. He opened his mouth and tried to swallow as much of it as he could, but, obviously not being much experienced at this, he only managed a couple of my seven inches. Still, his oral attentions were turning me on and my cock was growing harder and more excited. Although I think this was more from the position of standing over my former high school bully while he sucked me off than any of his cocksucking skills. Trying a different approach, he let my cock slip from his lips and began to lick it, running his tongue up from my balls along the base of my cock right back up to the tip, which he kissed. While at first he had been tentative, now he began to eagerly lick all around my cock, which was by now rock hard and extended to its full length.

"Mmm, oh, Candy, your cock is so big," he moaned, "I've never seen one like it before, especially not on a beautiful woman. And it's so good to eat it. I love to lick your big hard cock."

As he began to once more suck on the swollen purple head of my large member, he reached out and began to stroke the shaft with one hand while the other went to wank his own, slightly smaller, dick. I grabbed the back of his head and pushed him down further on my cock.

"That's it, swallow my big cock," I moaned, "I can see how much this is turning you on, my submissive little cocksucker. You might say you're no fag but you sure seem to love the taste of cock."

He gasped as I let up my hold on his head and let my cock out of his mouth for a second.

"I admit it, Candy, I never thought there could be something better than a hot girl's pussy until I got a taste of your cock!" he said, "I'd love to suck your pretty meat whenever you want."

With that he opened his mouth and managed to swallow about half of my full length. He was so eager that he was really quickly becoming a much better cocksucker. I'd never have thought it of the macho posturing he usually put on but he was so quickly manipulated into being completely submissive to me and this thrilled me every bit as much as having a hunky guy going down on my cock. But I kept thinking about his nice firm arse and what I really wanted to do to him, even as I continued to push his mouth down onto my dick, fucking his face.

"Mmm, oh yes, oh fuck, that's it, suck my cock, bitch," I moaned, "You're getting pretty good at this, honey. I can't believe you've never thought about how great it could feel to suck a nice juicy cock before now. You just love playing the submissive bitch don't you, honey? Submitting to the power of a girl with a nice hard dick."

"Mmmm, urgh," was all he could grunt and gag as I shoved my cock right down his throat.

As I let his head slip from my cock and allowed him to gasp for air again, this time I stepped back away from him, so when he leant back in with his mouth to try and envelop my cock once more, he got nothing but air. I laughed at him.

"God, you're so eager for it aren't you," I smiled, stepping back again as he reached up to try and touch it.

"Yes Candy," he gasped, "I want it, I want your beautiful cock, please give it to me!"

"Oh, don't worry boy, you're going to get it," I smiled, "But you're going to take it how I say. You got that? If you want my cock then you'll have to submit yourself to whatever I ask."

"Yes Candy, I'll do whatever you want, you're so gorgeous, what a hot girl and what a lovely cock, I'd do anything for it."

"Well then," I smiled, "Turn around, bend over and let's see that nice, toned arse of yours."

He looked nervous and hesitant, as if he had suddenly realised quite what I meant to do to him.

"No, I can't...I won't do anything like that," he said, trying to sound tough and masculine, but when he was there pleading on his knees, with that same mouth that had just begged to suck my cock, his own dick still rock hard at the thought of it, he didn't really convince.
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"Don't forget, my cock loving submissive boy, that you promised to do whatever I want," I said, "Don't be so nervous, I can tell you really want it, want to feel my hard cock sliding inside you. You've already told me how much you love cock, how much more will you love being completely dominated by it."

"I'm not sure," he said, trying to regain some control and dignity, "I'm not gay, I'm not having a cock stuck in my arse, even by a hot woman."

I saw now that the time had passed for me to be the beautiful seductress, I now had to be the dominant, in control woman, making him do just what I wanted.

"I wasn't asking you. I'm telling you," I said, changing my rich, soft tones to a commanding, angry voice, "Turn around and show me that arse. NOW. You say you're no queer but here you were a few minutes ago begging for cock. Don't k** yourself, honey, I know guys like you. So desperate to prove yourself a manly stud, but all you need is a big hard cock up the arse."

I could see from the shock on his face that he didn't quite know what was going on but still he did just as I said, getting down on his hands and knees and presenting that firm, toned arse to me. I licked my lips. I was going to enjoy this. It was a while since I'd seen an arse that fine and to be the first one to stick my dick in it was going to be quite a thrill.

"Urgh," he grunted as I shoved two wet fingers up inside him, exploring his anus. God, it was tight, I didn't know quite how it was going to fit my massive, thick member inside.

After a while trying to loosen him up a bit with my fingers, I leant over him so my breasts were pressed up against his back and the head of my cock nestling in his arse crack. My face was next to his, and I was able to whisper in his ear.

"Don't worry, it'll hurt at first, but soon you'll be loving it and I guarantee you, once you've had a cock up your arse you'll never go back."

There was a real expression of fear and panic on his face as he turned his head to look back at me standing over him, standing tall in my heels, long legs in stockings, my breasts and cock naked and exposed and a very naughty grin spreading across my lips. I spat on my hand and used the saliva to lubricate my cock a little before kneeling down behind him and pushing up inside his arse. With just a couple of inches inside, the tight grip of his virgin anus on my thick hard-on was already incredible.

"Aarrrrh," he cried out, "God, it hurts, please don't. Stop, I don't want this."

He seemed about to get up but I grabbed him violently by the waist and levering myself like this, pushed much deeper inside him.

"OH MY GOD! AAAARGH!!!" he cried out even louder.

"You wanted my cock, well now you're getting it," I said nastily, pushing deeper and deeper until he was completely impaled on the full length of my shaft.

Completely inside him, I had to pause for a minute, my head was swimming, I was stimulated in ways that I hadn't been in a long time. The tight clench of his arse on my cock, the feeling of totally dominating this arrogant stud who had made my teenage years a misery but now was bent over with my cock stuck up his arse. He was almost in tears now, not really sure how the situation had got to be this way so fast. One minute he was picking up a hot girl in a bar, the next she had a cock bigger than his and was forcing him to take it up his virgin arse, understandably it was all a bit much for him.

Slowly, I slid my cock back out of his arse and then rammed it back in causing him to cry out again. But I wasn't about to show him any mercy, as I began to get into a rhythm, withdrawing from his tight anus and ramming my dick back in, harder and harder, deeper and deeper, tearing into him, violently taking his cherry.

"Oh no, Oh God, fuck, don't! Please, I don't want this, I don't deserve this. Please, Candy..." he cried.

"Don't deserve this, sissy?" I said nastily, as I shoved my dick inside him, my balls slapping his arse, his own cock swinging beneath us, "You asked for it. Besides, I know you, how you bully people, calling them fags and sissys. You made my life hell."

"What?" he said, still in tears, not understanding.

"I wasn't always beautiful Candy," I said, angrily, almost in tears myself, "I was once Andy Read, we were at school together. You made my confusing teenage life a misery. Well, now it's you whose going to be so troubled by your desire for a nice thick cock."

"Oh, I remember you," he said, trying hard to regain his nasty bullying ways and macho strength, but it was quite hard when on his knees with his arse being ploughed by my cock, "You really did turn out pretty fucked up, you dirty fag."

"That's pretty rich, honey, coming from you," I said, fucking him as hard and violently as I could, my cock almost ready to explode, "I grew up to be a beautiful, confident, in control woman. And here's you, begging for cock from somebody you just met in a bar, having your sissy arse fucked. Who's the dirty fag now?"

"Urh, ahhh, mmm," he grunted and groaned as I fucked him, "No, aaah, this isn't what I want. Oh, God, Candy, no."

"Mmmm, don't play that game with me, fag, I can tell you're loving this as much as me," I sighed, seeing his dick was still so hard, "Oh yes, you're arse is so tight, it feels great to be the one taking your cherry and my cock must feel sooo good up inside you."

"Aaah, oh, fuck, yes, yes Candy it does," he gasped, "You're right, it's urgh, ahhh, sooo amazing, feels soo good. I can't help it, I love your cock and it feels so good inside my arse."

"That's right, my cock loving sissy queer, it's you who loves cock in your arse but don't worry, I'm gonna give you just what you want. Your tight arse is gonna make me cum."

"Oh sweet Candy, yes, I want to make you cum, let me feel it. Let me taste it. I'm sorry for whatever I did to you before but I'm now your bitch and you can do what you want with me."

"Mmm, fuck, that's good," I smiled, this had gone so much better than I'd dared hope, my former bully now my submissive bitch, "I think you deserve a reward for admitting what a closet cock loving fag you are, for getting that hot arse fucked well for the first time, I'm going to feed you my cum."

I took my dick, almost ready to explode, from his arse, and pushed him to the floor, turning him so he lay on his back. His cock jutted up in the air, harder than it had been all evening, he began to feverishly masturbate as I crouched astride his chest and jerked my own cock off within inches of his face.

"Ahhh, God, here it comes," I gasped as my cock exploded, shooting streams of my warm cum across his face.

It made me smile to see that face formerly so smug, arrogant and macho, now covered in sticky white cum, his mouth desperate to catch what I spurted out of my hard cock, licking whatever he could from his lips.

"That's it, my sissy bitch," I smiled, "Drink it down, taste my hot cum. You're hooked on cocks for life now, fag. There's no going back."

"Oh fuck, urgh," he grunted, as, stroking his own meat, he too came all over his naked, muscular chest, "Oh Candy, I love to taste the cum from your beautiful cock almost as much as I love feeling it up my arse. You've shown me pleasures I never imagined, I totally love cock and want nothing but to worship it now!"

Finally, I finished cumming, soaking his body in my sticky juices. I put my clothes back on and left him there, sticky and cum drenched, my school bully turned fag cum bucket. It certainly had been an evening to remember and it was always nice to think that right here was a hot, hunky guy who would worship my thick cock. A week or so later, I ran into his friend from the bar again who told me that Greg had continued his usual macho posturing and homophobic bullshit when out the following night but that after the violent arse fucking I had given him, he seemed to have a bit of trouble walking. I told Greg's friend everything that had happened between us that evening. Even though he'd been a great submissive fuck, it still thrilled me to know how this in denial closet cock loving fag was going to be exposed and humiliated in front of his friends, just as he had once done to me. Hell, the thought of it was getting me quite hard and aroused right there. Fortunately for me, I had a grateful and eager to please guy right there. Oh well, I guess my teenage years had been bad but as an adult I was getting all the luck.

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One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...

4 years ago
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Sissy Stepson Part 1 Stepmothers Trap

Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...

3 years ago
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Sissy Therapy Case Study 2

Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...

2 years ago
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Crowd Sourced Sissy Spin OffMothers Milk

NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...

3 years ago
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My Young Sissy brother for Mens Cum today

sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...

2 years ago
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My Stepmothers Sissy Daughter part 3

My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...

4 years ago
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A Sissy and Four Brothers

A sissy and four brothers -What is it like? Mother is very strict about separating me from 'the boys' but they've never experienced a 'sister' in the house before so there seems to be a lot of snooping around. A few of my readers have asked me for some additional information about farm life and living as a sissy with four brothers, and I'll respond to the question about seeing Jack again. Jack's mother called me and told me that I'd done wonders about boosting his self-esteem and she...

2 years ago
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Sissy Julian Chapter III Further Development

Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...

4 years ago
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Mothers Sissy Teachers Pet

Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...

4 years ago
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CDg Sissy Slut Cocksucker goes to local Adult Theater

I love dressing up whenever possible, which is not often enough. But, what I love even more is dressing up as a hot and wanton sissy slut cocksucker and then going to the local adult theater for some great XXX fun. I am not totally passable, but have been told my legs are fantastic and my ass is nice and tight with a hot tramp stamp just above my ass. Most guys say it's sexy as hell while they are fucking me. Fortunately, my wife had to go out of town for a few days and thereby giving...

3 years ago
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My Stepmothers Sissy Daughter part 2

My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...

3 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

2 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

Crossdressing
4 years ago
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My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

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...

3 years ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

4 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Six Another Sissy for Ms Rebeccas Household

Teaching the Sissy Maid Workshop at the MVP, Chapter Six: Another Sissy for Ms. Rebecca's Household? After the workshop ends on day one, Ms. Rebecca stays to speak with some of the women attending the class and gets an unexpected offer that offers her some incredible rewards if she can take ownership of another young male submissive who is displaying sissy tendencies. After the workshop ended for the day, I stayed for a while to give me a chance to speak with some of the women...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

4 years ago
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Have sissy thoughts Pt1 What you need to know

If you are wondering whether being a sissy is for you, the following information will point out the many good things, and dispel any doubts or negative feelings you may have about becoming a sissy gurl. The rules are important, and obeying the rules will make you a happier sissy.Repeated reading of this and the subsequent entries will deepen and clarify your sissy state of mind: once you have freed yourself from thoughts of masculinity, you will be left with only the desire to please real men,...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. 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 Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

2 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

2 years ago
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Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

3 years ago
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The Young Sissy Chapter 3

I was running through an empty parking lot...looking for someone, or something, but I wasn't sure who I was looking for...or what. All I knew that was no matter how hard I looked, how far off into the distance I stared, all I saw was miles and miles of concrete. It was an oppressive emptiness, the vastness of the open space crushing me. I fell to my knees in despair. I don't know why I was looking anymore...everything I had seen up to this point was testament to the futility of hope. At...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

1 year ago
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The 150 Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

3 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Five Day One of the Sissy Maid Workshop Comes to an End

Teaching the Sissy Maid Workshop at the MVP, Chapter Five: Day One of the Sissy Maid Workshop Comes to an End After lunch the ladies and their sissy candidates assemble in break-out groups where the candidates are stripped, shaved and locked in chastity as each of the pathetic males experiences new levels of shame and humiliation as they are displayed publicly and most for the first time. As the sissy graduates helped herd the male candidates into the appropriate classroom I...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature

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