My Sissy Fantasy free porn video

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Same characters as my previous (very long) story. Includes both sissy and cuckhold fantasy



Ring, ring, ring

The doorbell kept ringing and ringing as I try to ignore it. There's an election coming up so presumably it would just be some bloody politician telling me why I should vote for them. I tried to concentrate but frankly the persistent ringing of the doorbell had wrecked my concentration. Ring ring, ring ring, they were very persistent, why wouldn't they just go away.

Let me set the scene.

I was sitting on an armchair with my knees hitched up on its arms, totally naked, and an erection poking up. I had slid my arse forward in a chair so that I could insert a vibrator into my ass, a vibrator which was gently buzzing, sending waves of pleasure through my body. On my 52 inch TV was a video of a stunning shemale with a nine or 10 inch cock getting a blow to from an inadequate man at her feet. My laptop was scrolling through a goon/humiliation slideshow reminding me that I was "married to porn" or "an inadequate little wanker" on the side table beside me was my bottle of beloved baby oil.

The doorbell kept ringing, and I kept trying to ignore it.

I had planned tonight for the past week. My wife told me she was going to go straight from work out for drinks and dinner with the girls and maybe a nightclub afterwards, so not to expect her home. That just meant one thing to me, an opportunity to wank myself looking at X hamster indulging my perverted sexual mind in all manners of depravity. I had even left work early, knowing my wife wouldn't be home so that I could maximise my time doing what I love best. Giving my heart and soul to pornography.

Let me explain, I have a tiny penis, maybe 3 inches when erect. So how did I get married you ask, the answer is I really don't know. I guess I had a good job and a comfortable life and I met my wife when she was on the rebound and maybe getting a little bit desperate. I popped the question quickly and we were marching down the aisle before the reality of my inadequacy had dawned on us both. She wanted c***dren, and made me get my sperm tested, on the basis that someone with a tiny cock was probably infertile as well.

Anyway, I wasn't and I guess that's what she settled for. But it didn't take long after we were married for her to realise what a mistake she had made. When we had sex I could never make her cum, so I would always end up eating her out, then six months into the marriage she started using a vibrator after we had sex. I would sit there beside her while she teased an orgasm out of herself, lost in her own world, completely oblivious to me sitting beside her on the bed tugging at my little cock, indifferent to whether I had any pleasure or not.

Increasingly she became dismissive of me, never missing an opportunity to tell me how pathetic and inadequate man I was, remarking on other men when we went out "did you see the size of his package" or "his wife looks like she gets a really good fucking, unlike me". Within months of this I had withdrawn from any sexual contact. I even moved in to our spare bedroom, on her suggestion. She preferred to use her vibrator and not to have 2 to put up with " her pathetic husband".

Inevitably, I turn to pornography. Increasingly in the evenings I would come home from work and after a brief meal I would go into my room and cruise the Internet looking for something to turn me on. It started with plain vanilla sex, then anal and a range of other hard-core, fisting, pissing et cetera. But what really got me off was realising that there were creatures call shemales. Stunningly beautiful women with great bodies, and cocks. I became obsessed, initially I wasn't sure why, it's not that I dislike pussy but the whole shemale package really got me off big time (when I say big time, I mean I had an orgasm but maybe a teaspoonful).

Increasingly rather than starting with plain vanilla videos I would go straight to my favourite shemale videos, in particular, I love to see men sucking beautiful female cock. Inevitably I could get my own little penis to cum looking at this. I loved humiliation videos and slideshows. They told me what I already knew, I was sexually inadequate, I was lucky to have these stunning women to wank to and yes they did become my life and it was easier to completely ignore my wife and concentrate on my pornography.

Over time I developed a routine which varied according to the amount of time I could devote. I took particular pleasure in imagining myself as the inadequate man, the cuck only deserving of humiliation and rejection, only worthy of wanking by himself to a video or a slideshow. I had finally understood my role in the sexual hierarchy, a bottom feeder. I had reconciled myself to a life of marriage to pornography. And I was happy with that.

While I looked at each shemale getting a blowjob and imagined myself as the guy with the cock in his mouth I never thought it would happen. When I saw a beautiful shemale reaming some guys or girls asshole, I closed my eyes and imagined what it would feel like. But I never thought it would happen me in real life, that felt too complicated and too messy. That was the level of how pathetic I was, I couldn't even in real life be the pathetic little sissy, it could only be a fantasy for me. That really was the bottom of the sexual pile.

That's why I was so excited tonight, I had hours and hours, I did not need to rush my orgasm, I could just sit there feeling my oiled up body the vibrator gently humming in my arse hole and my little cock begging to be touched and explode. I had perfected
the art of edging, holding my orgasm back until the very last minute, and frequently not even being able to achieve orgasm

Ring ring ring ring.

Okay, at this point I knew they were not going to go away, I quickly pulled on my trousers and T-shirt turned off the vibrator, but left it in my ass of course, and went to the door to tell them to piss off. "I'm busy working in here, why don't you piss off" I said as I opened the door. Except it wasn't a politician, it was my mate Tom. "Geez Peter what are you up to, I was sure I could hear you there, so I wasn't going away." With that Tom brushed past me carrying a sixpack of beer and marched into my house.

Thomas was my best friend since we were 11 years old. We make good friends, he's everything I am not. He's definitely a man's man, 6 foot one, handsome and yes of course a fucking huge cock. He recently divorced his wife and was known to be fucking around every woman that moved. And apparently he didn't care if they were married or not. I haven't seen much of him, I preferred to stay home with my perverted friends than be reminded how pathetic I was compared to Tom.

I assumed he would stop in the hall or going to the kitchen, but he took an immediate left into the lounge room, shit, I was busted. I had only paused the TV and my laptop was still playing the humiliation slideshow. The baby oil was even sitting on the table beside my armchair. "What's going on here appear, looks like I have interrupted the worlds greatest wank session" he slapped me on the arm and started laughing. " Why not, obviously your missus is out, show me what you've got."

Six months ago I would have rushed Tom out the door totally embarrassed at the depth to which I had sunk, but today I didn't care. I knew what I was and I was comfortable with. And frankly if Tom became aware that I preferred to sit here with the curtains closed jerking off, well then maybe he wouldn't bother me any longer and I wouldn't have to make excuses for not showing up for nights out.

He picked up the laptop and watched the images flashing by with their degrading humiliating messages "porn is your life"" I think it's totally hot that you jacked off for me, edge from me baby" Tom looked at the stunning women and grading messages scroll through their slideshow "for me that's a bit heavy, but in fairness the women are all fit., What's the video?" He asked

I turned on the video to see shemale fuck a guy in the face. It was one of my favourites. He licked her balls, making love to her superiority. "Okay mate, I thought we might watch the football, but why not let's have a wank together, we never did that when we were k? Wit"

With that he pulled over an armchair and sits down. Hesitantly I sat in my chair and we watch video after video for about 30 minutes. I then noticed Tom starting to rub his hand down the front of his trousers. "Let's make up for our c***dhood, it’s never too late to be wank buddies" said Tom, as usual taking charge of the situation. With that he stood up and took off his T-shirt to reveal his gorgeous muscular broad shoulders and sixpack. There was not a hair to be seen on his body, and his skin had a golden colour is the result of a recent holiday. I felt like I had been punched in the stomach.

He really was a superior alpha male. Then to my surprise he kicked off shoes and standing up dropped his trousers. He turns toward me so that I can see the magnificence of his manhood. His cock hangs a flaccid six or 7 inches thick as my forearm. His gorgeous massive balls hang behind, the centre of his spunk making universe. My tummy flipped over and my breath caught in my throat, he was gorgeous.

"Okay mate you joining me?" Aware that I still had my vibrator embedded in my arse hole I turned away from him, pulled my trousers down as I sat on the sofa and pulled my T-shirt off. Emboldened I took some of the baby oil in my hand and rubbed it over my body and handing it to him said "want some?" "Fuck yeah" with that he squirts all over his torso legs and cock rubbing and tugging and is beautiful manhood. Jesus I envied him. I sat back in my chair trying not to reveal either my pathetic cock or the vibrator.

We watched video after video and gradually Tom's penis became bigger and bigger as he nonchalantly pulled and tugged on his cock. At one point he pulled it tight to his stomach and reached down cradling his balls and gently massaging and squeezing them. I could see this out of the side of my eye, and it was magnificent. My own breath was becoming shallower and shallower, I reflected on how this was a perfect fantasy for me and yet I felt unable to act. I looked from the video to him. I was deep deep in a sexual fog.

Reality had disappeared and for those brief minutes I was the pathetic little man on X hamster. I had lost all sense of who I was with the exception of the realisation that I was in the presence of sexual greatness. Unable to contain myself I lay back in my chair to turn on the vibrator in my arse. Tom saw me, and laughted loud "fuck me Peter you're not messing around"

I was delighted the ice was broken. Everything was on the table now, he could see how pathetic I was, he could see me with a vibrator in my ass and for this reason this I took more risks. I openly looked over at him masturbating his foot long cock. I was in cock heaven, I was awestruck. It was simply the most beautiful awe-inspiring thing I had ever seen. Something within me changed, something was telling me I had an opportunity.

Thankfully X hamster providing me the perfect opportunity. The next video was one of my relatively few all gay videos. It was of a cute little twink blowing on his partners huge cock. "Geez Peter this is horny, even if it is Gay" overcome with a powerful urge to copy what I was seeing on the screen I decided to risk everything and asked "do you want some help with that?" I looked at him knowing I had taken a huge risk but frankly not caring, what is the worst that could happen he would leave, we would never speak again and I would have more hours to pull my little cock and worship at the Altar of Porn.

He looked at me smiling "I won't tell if you don't" and winked at me. I looked to the TV I decided I would take my cues from that I turned up the vibrator a little and jolted with the intensity of the pleasure washing up from my anus. I was completely in the grip of my sexual drive. Never breaking eye contact I looked into Tom's eyes and crawled over in front of him.

I took about 10 seconds to look directly at his cock and balls, I was breathless, it was love at first sight. Having had plenty of practice fantasising about exactly this situation I decided not to rush it. I gently pushed his cock back so that I was lying along his belly, deciding to worship his spunk filled balls. I pushed my face into them licking and sucking taking them in my mouth caressing them with my tongue then rubbing my own slime over my face, lost in my own lust of cock worship.

Above me Tom's magnificent cock started to leak pre-which dribbled gently down its length. As I sucked on his balls gently he rubbed his cock over my forehead from side to side as if anointing me. "I hereby appoint you Lord Cock Boy" he joked, and we both laughed. I gradually moved away from his testicles, sucking licking and biting at the base of his enormous weapon. The pre-cum dribbled down and I licked it up, savouring it's taste and appreciating the nourishment it would give me. Every fibre of my being was worshipping Tom and his manhood.

He threw his head back and closed his eyes this, perhaps imagining that somebody else was between his knees? I decided to bring him back to reality.

I gradually licked up the length of his cock while caressing his balls in my hand. I slid my hand underneath him gently toying with his rosebud. He raised his eyebrows, but was clearly enjoying so didn't stop me. Emboldened I inserted my finger into his arse, while at the same time taking the gorgeous mushroom head of his cock in my mouth. It was huge like a ripe plum and I gave it all of the attention it deserved. I nibbled on his head, gently sucking the increasing flow of pre-cum into my mouth.

"You going to swallow?" He asked. In answer I kept my mouth exactly where it was, and squeezed a little bit harder on his testicles which had tightened, signifying his impending orgasm. My finger invaded his arse, causing him to groan in pure lust, and I fucked his cock with my mouth taking three or 4 inches at most. His hands came down either side of my head, gently encouraging this head fuck. I could sense his building orgasm, his scrotum tightened in my hands so I pushed my finger further up his ass searching for his prostate.

"Fuck …………………………, here I cum, take it all you little cock sucker" Tom exploded in my mouth and for the first time in my life I tasted another man's cum and right there and then I knew but from a sexual point of view, this was where I belonged, my lover's balls in my hand, my finger in his ass, and his cock in my mouth spewing cum. Without touching it, my own little cock came and I dribbled on the floor.

For 30 seconds he shot rope after rope of cum in my mouth. I savoured it's heat, and the richness of its texture, concentrating on keeping it all there. Understanding the satisfaction that he would get from seeing it in my mouth then sliding down my throat. He stopped coming with a final grunt and let go of my head allowing me to lift my head up and look at him directly. I opened my mouth and stuck out my tongue so you could see his spunk in there. Then looking at him directly I closed my mouth and swallowed.

He fell back in the chair I took the time to take in the of his beautiful sight masculine body. I reached up and with my thumbs gently stimulated his nipples as I went down on his cock I'm cleaned up my own slime. He slid forward, lifted his legs and invited me to lick his arse hole. I buried my face in his groin, feeling his hot balls on my forehead as my tongue invaded his sphincter. Despite having just come myself I was again overtaken by a primal a****l lust. Something deep within me knew that I had found my calling.

As I continued to on Tom's cock it regained its rigidity. I felt honoured that I could have this effect on the ultimate alpha male. But clearly Tom wasn't your typical "Wham Bam thank you ma'am" type of lover. He had stamina.

I paused and sat back a little to take in the view of his enormous cock. The only sound that could be heard was the vibrator buzzing in my house.

"You don't think?.................... oh nevermind" Tom mumbled. I immediately understood.

"Tom for the past six months the only thing which is been able to get me off is the view of an inadequate little man sucking a magnificent cock, swallowing a huge load, and taking it up the arse like the little bitch that I am" I looked directly into his eyes and asked "Will you do that for me?"

Tom hesitated, but only for about two seconds. "Peter I would be honoured to take your anal virginity, stand up and turnaround"

I did this he asked, bending over so that he could see the vibrator in my ass. He started to gently rotate it, understanding that to take his girth I would need some loosening up first. "Do you have anything bigger than this?" He asked.

I scurried into my bedroom and got the dildo which I had bought but not yet used, nervous of the damage I could do. I brought it back and gave it to Tom. "I've never used this, but will you help me?" He gave it back to me saying "lubricate it". With that I started sucking and slobbering on the giant rubber dildo even managing to get 6 inches down my throat. I then presented to Tom and again turned around and bent over.

He took the vibrator out of my arse and gently pushed the head of the dildo into my anus. He pushed three or four times until it breached my sphincter. I felt like I was being ripped apart. But Tom was a gentle lover and started rotating the dildo aware that his massive cock had more girth. Then he started fucking me with it inch by inch.

Initially I thought I would pass out, I was seeing stars, and pain was washing over me. But then gradually the pain faded and the waves of pleasure increased. After about 10 minutes I responded to Tom's rhythm by pushing back against the dildo. Again I felt the return of sexual ecstasy, how could I not have known that my path to sexual pleasure was through my ass?.

Tom then withdrew the dildo and immediately placed his cock where the dildo had been. He rubbed the head of his cock around my gaping ass hole spreading his pre-cum as lube so as to ease his entry. He then inserted his cock into my ass. Because of the preparation I had received, I immediately felt an explosion of sexual desire. His cock was his flesh and blood, it felt both more intimate and more primal than its poor rubber substitute. I wanted it.

Taking him by surprise I pushed hard against him and took three or 4 inches into me. "Oh Christ, this is hot" Tom exclaimed "you really are hot for my cock, I'm going to start fucking you like the sissy bitch you are" clearly I was not the only one feeling the base sexual drive. With that Tom started to fuck me, giving me more and more of himself with each thrust.

I felt both pain as he invaded me more and more, but also satisfaction and yes I'm not afraid to admit it love. Tom was making love to me, and I to him. I reach between my own legs, ignoring my own pathetic little cock and grabbed his balls. "Give me everything you have" I panted "fuck me like a bitch, breed me, shoot your spunk inside me" the tightness of my arse was driving Tom to distraction. He was pounding and pounding, operating on a purely a****listic basis. I squeezed his balls harder and felt them tighten.

With that Tom grunted loudly and I felt his cum fill my guts. It was quite simply the greatest feeling I have ever had. If you asked me at that moment if it were possible to have Tom's baby I would have absolutely agreed. His power and strength had invaded me and made me complete.

When he stopped cuming we were just standing there both panting and processing what had happened. From my point of view, I knew there was no going back. I knew that taking Tom's cock and balls in my mouth and my arse were what I wanted. I hope he felt the same way.

As we recovered Tom's cock gradually deflated in my anus. As I stood there Tom pulled out of me and inserted the dildo. "I don't want you feeling empty" with that he collapsed back in the chair.

Clap clap clap clap.

We both jolted and looked over to the source of the noise. There was my wife Sarah standing in the doorway giving her appreciation for what she had seen. "That was an incredibly hot show, much better than those videos you look at" I was gobsmacked, but Sarah continued " So Peter, myself and Tom have something to tell you" Shocked I looked around at him unable to form a question (I did have his cum inside me after all).

"Peter myself and Sarah have been fucking for the past six months. Sarah saw your porn profile on your laptop one night and we understand what your preferences are. Tonight was all about finding out whether you wanted to take them from fantasy to reality, and I think we have the answer to that" he said shaking his cock and looking directly at me.

"its obvious that you are a sissy, and that you will get sexual pleasure from me using you like I did tonight, but the thing is, myself and Sarah fuck as well. It one of life's great mysteries how a pathetic little man like you ended up with an unbelievable specimen of womanhood like Sarah" he stopped allowing me to absorb what he was saying.

Sarah filled the gap "so here's the deal, Peter comes over and fucks me whenever he wants. But if I'm not here, or so sore from him fucking me that I need a rest, your arse will be his second pussy, what you think about that?"

I was stunned, two minutes ago I would have had Tom's baby, but now I understood it had all been set up. Not only was I a sissy but I was a cuckhold as well. As I thought about it, my body betrayed me. I started getting an erection which wasn't lost on Sarah.

"I knew it, he gets his kicks from being humiliated. He knows that he will the very lucky to have you pounding his arse" she said looking at Tom. With that she walked towards me reaching into her handbag. "As my cuckhold you now have to wear this all of the time, I may allow you to jerk herself off once in a blue moon" with that she took out a chastity lock and secured it around my cock and balls, clicked it shut and dropped the key into a handbag.

"Stand in the corner, and watch a real man make me happy"………… To be continued

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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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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

2 years ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

3 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

3 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

2 years ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

2 years ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

4 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

4 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
2 years ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. 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 portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

2 years ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

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