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Track Star Sissy

Track Star Sissy Author's Note - I actually ran track and cross country while I was in college. While I was never good enough to receive a scholarship like the protagonist in this story, the story is interspersed with tidbits from my time in college plus fantasies of mine. Some of the fantasies are somewhat dark and involve forced feminization or humiliation. I realize these aren't for everyone but I hope you enjoy reading as much as I did writing it. Chapter 1 -...

Miss Keven Jeanne Bardot Is SUCH A SISSY

I have this one regular who comes in every Sunday night. He never gives me money, because for one thing, he’s just not a trick; and for another, he knows I want him probably more than he wants me. He fucks a lot of strippers at the club next door – in fact he’s even fucked my ex wife. I didn’t tell him that she’s my wife, but I asked him once if he’d ever been with Cherish - that's Dani's stage name - and he said he had. I don’t even know his name, but we’ve been having sex together for over 4...

Sound Sissy

Sound Sissy By Karen Singer Written in 2003, this is the first story I ever wrote. In fact, I thought I hated writing until I decided to write this. Now I can't stop writing. I am submitting it here to serve as a marker to show how far I've come as a writer since then - now that I am actively trying to find an agent for my "legitimate" books. As such, I've done almost no editing so it is pretty much in its original state. I know I went horribly wrong with this story near the...

The Slave and the Sissy

She had always been very rough with him, the big woman, but this morning was exceptional, and different. She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or had him lick her till she grunted out yet another orgasm, before serving him with cane or whip. Now morning was here she face sat him;...

SISSY

SISSY Looking at me now, one will have an extremely difficult time believing this story. But let me assure you that every word is true. It started late one spring afternoon. The weather was typical spring weather, windy, wet and cold. I was walking home from high school, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was very small, looked 16 and feminine. If you’re thinking...

TIGHTY TIGHT SISSY

POLLY GLOSS HOOKS UP WITH TWO UNHAPPILY MARRIED MEN FOR TIGHTS/LYCRA FETISH FUNI met Pat and Len via a fetish forum for lovers of crossdressers and tights enthusiasts. We shared saucy messages and pics. It was fortunate that they lived nearby, as I had told them in no uncertain terms, that I wanted them both. My hungry eyes behind my shiny stocking mask longed for their hard mature cocks in their tights, in my mouth and, naturally, up my arsehole. The fact that they had wives only deepened the...

Many Firsts for Sissy

I have always had a desire for dressing femme and having submissive thoughts ever since I can remember. I started like many other gurls by trying on my mother's lingerie and loving it. Things gradually escalated to shaving (thankfully I am blonde and not very hairy naturally), experimenting with make-up, and inevitably sucking cock at the park toward the end of my college days. I was on my way to being a true sissy gurl now that I reflect on it. Everything I did was subconsciously geared toward...

Birth of a Sissy

I met Jeff one day at the nearby tennis courts. I could never have imaginedwhat the result of that meeting would be. I suppose I should tell you a bitabout me. I'm a happily married 34 year old. About average in mostrespects. A little spare tire trying to form around the middle but indecent shape. I wear my hair short with a mustache and goatee. I had beenmarried for about 6 years and had been physically faithful to my wife. Isay physically, as I did think about other partners on occasion,...

Being a good slutty Sissy

Being a good Sissy for my mistress“Hey Martina. do you like what you see?” Samantha, a very beautiful shemale with tits size D, asks standing in front of me. A smile curls her lips as she strokes her 8 inch cock.“Yeah, I'd love to play with a cock that big.” Martina says licking his lips at the sight of pre-cum dripping from the tip of her cock. I’m a 5 feet 11 tall sissy original called Mark. If I have to dress for my shemale mistress as a sissy gurl I call myself Martina. “Well then, come and...

A Cockold Sissy

A Cockold Sissy Part 1 By Tiffany Scott 2006 Denise, the woman I had been married to for the last 11 years knelt between my spread legs with one hand planted firmly on my lower back for added support, while she grasped the terrifyingly huge cock that stuck out where her thighs met with the other. She laughed as she listened to the muffled sounds that managed to make their way past the fat ball gag filling my mouth. "Oh don't worry my sweet little bitch," She coo'd as she rubbed the...

Truck Stop Sissy

I had passed the layby numerous times on my way to work, always with an eye to using it on one of my 'walks on the wild side'. Well tonight was the big night, dressed in my purple PVC slutty mini dress, black and purple lacy basque with integral suspenders holding up black fishnet stockings. Panty wise I had on a purple G string that barely contained my throbbing cock. I say barely, it was quite embarrassing that my cock was small enough to fit, even when hard! A thought that sent a...

Brian and Brianna Chapter One

“Nothing… not a thing on except soaps and court TV.” I continued flipping through the channels for a few more minutes before giving up and handing her the remote. She flipped through them as well, but couldn’t find anything interesting either. “Hey, can you keep a secret?” she asked with a little gleam in her beautiful blue eyes. “That depends… is it gonna get me in trouble?” I teased. “Well, maybe, and maybe not if you can keep quiet about it.” I thought for a second before...

Brian

Brian was a good find. A good phuk. A one in a thousand.He was in his late 40s when I met him - me in my late teens. For quite a while he was a sugar daddy - best years of my life.He had a big cock (over 8”) which was quite intimidating at first but the money was good and his expert-level experience in the bedroom was a huge advantage. I was not too sure when he requested (at our 2nd meeting no less) anal. I refused and all was good but by the time we met 5 times he was practically insisting...

Brian and Aunt Em

Brian and Aunt Em This is a fantasy about Brian and his Aunt Em – which evolved into a full blown relationship. My Aunt Emmy was the younger sister in my mother's family. Back in 1962, when I was just eighteen, she was thirty-eight years old. At five foot five inches tall, she weighed about 140 pounds. Her blonde hair, which was dyed, fell at shoulder length. Although her figure was average, she had some prominent features. Her 38D size breasts, a rounded belly from child bearing matched her...

Brian Guess What Chapter 1

"Oh, Brian, you'll never believe what Becca told me. She watched Tyler masturbate!" "Woah, sis, what?" "She watched her brother jack-off, you know..." "And how did this happen?" "Well, she came home from school yesterday and went upstairs to change. Ty's door was open and she saw him naked on his bed and doing it to a Playboy magazine." "Did she just stand there and watch?" "No, he didn't know she was there until she said, 'Havin' fun, big brother?' and he pulled the...

Cuckold Sissy

Cuckold Sissy It began at my wife's Christmas party. Consuming too much wine, my lovely wife wanted to dance with everyone. She was having the time of her life but everything changed in a matter of minutes. As I watched her change dance partners, Marcus, a large muscular jock finally got his turn with her. Fortunately, or unfortunately, the music changed to a slow dance. Ann seemed to just melt into his arms and body. She was tired and drunk. Marcus moved slowly with her, holding her...

Used Sissy

I was now a fully fledged Crossdressing Sissy Slut even though still only in my teens I needed and craved cock……….any cock as long as it was loaded with spunk for me to swallow. I had been sucking cock at various toilets around my town and had met some really kinky bastards in my time but John was way ahead in his kinky ideas. He was a mature respectable male in his late 50’s a white collar worker with a nice property in the country…..he was married and had 3 k**s so to any one taking a casual...

My Life As A Feminine Sissy

Here are a few of the things men have said to me in the adult video preview booths:"Nice legs, fag.""MMMM! Fuckin' smooth! You shave your legs?" (Said while feeling up my bare legs just prior to fucking me.) "Those tits real?""Man that pussy is tight!""Get on you knees and tell me what you want, bitch.""You are the most feminine man I have ever seen,""You eat ass?"I have to admit that when I hear comments like this I am thrilled.I got a comment on my prison turnout post from someone who went...

SISSY

SISSY Looking at me now, one will have an extremely difficult timebelieving this story. But let me assure you that every word istrue. It started late one spring afternoon. The weather was typicalspring weather, windy, wet and cold. I was walking home from highschool, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was...

Mommy and sissy

I really had been expecting to be shopping most of the morning, but I got to the mall and miracle of miracles, not only did I find a place to park close in, the mall wasn't at all as crowded as I had expected. I got in and picked up the few things I needed, and headed home. One of the things I had to get was a couple of new bras. It just seemed that the elastic in the ones I had were wearing out. I sort of calked it up to their being more cheaply made, every thing was any more it seemed, being...

Collette s Sissy

I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade off in one way or another and being Collette's kept man is tricky. I have to recognize her complete authority as she owns everything, but she's not harsh with me and truthfully I feel like I'm on an...

Lane Bryant Sissy

Lane Bryant Sissy By nysilksissyboi Wow, Who ever would have though a chance visit to a mall to handle a panty fetish, would have my life end up the way it has! Ever since I can remember as a kid, I have had a silk/satin fetish, even would steal my sister's panties as a kid and wear them, a few times a dress or slip but nothing more than that. AS a teenager and in college, I bought myself men's silk underwear and nylon briefs and a few robes and shorts to deal with my...

Sissy Mission 6 Poodle Skirt Sissy

Sissy Mission 6: Poodle Skirt Sissy By Cheryl Alison I sat on the bench assessing my surroundings. It was a well-kept small town, with a cobblestone main street and nicely maintained historic buildings. Banners and awnings in the front of shops fluttered in the breeze, advertising everything from antiques to hardware. Since it was a town located on a large lake with lots of recreation opportunities, it was busy on this early June day. People strolled up...

Pink Plastic Sissy

Pink Plastic Sissy Caroline Richards 29 Nov 2006 I have my head buried in her lap facing her as usual. She lifts her skirt and exposes her nakedness and guides my head in closer to her. I begin to lick and suck just as she has taught me for the past three years. I feel her move and the moistness of her on my lips as my tongue probes gently inside of her. She reaches inside my plastic panties and my nappy. I now wear them at all times I am with her like this, and I feel her touch...

Prissy Sissy

Prissy Sissy By Cheryl Lynn This is a short work of fiction rushed to a conclusion. It may be downloaded for personal use only, any other use forbidden unless approved by the author. All the usual disclaimers apply. Not for the faint of heart or sweet/sentimental reader. I was going to submit this to tgstories.com but decided to leave it short and unsweetened. Constructive criticism and comments welcome at [email protected]. Prissy Sissy Ned Baxter was a fairly normal...

Stroking Sissy

STROKING SISSY by Throne My wife June told me to get out of my apron, put on what she'd laid out for me, and then come to the bedroom. As she sauntered away I couldn't help admiring her trim but sexy figure and pixie-cut blond hair. I sighed and went to my room, where I slept on nights when she banned me from her bed. It still upsets me to see my space, small and decorated the way a girl in her early teens might like, all pink and white, with rainbows and unicorns. Right in the...

So you want to be my sissy

So you want to be a little slut, do you?Sometimes I have to wonder if you know who you are dealing with. If you know how cruel I can be. Sometimes I wonder if you will try to back out once you see the tools I lay out that I plan to use on you.You don't understand how much pleasure I will take in turning you into a pathetic little sissy. How I will strip each piece of clothing from you with a razor blade as you stand, wrists chained above your head, blindfolded, with my penis gag locked deep...

Learning to be a submissive sissy

For a month before meeting you have not let me cum.But each night you make me lie on my bed and finger my ass.You text me just before I go to bed: 'You have to open yourself up for me. Play with your nipples as you do it. This is how you must masturbate now, bitch.'During the day you make me send you images every hour of people in bondage being used or sissy captions.I think to myself, why do these pictures turn me on? You make me describe the pictures to you. You keep me in a state of constant...

Sissy

Well. That was interesting, wasn’t it? We’ll play with your little titties again tomorrow. For now, just close your eyes and rest. Did you have a good nappy? Do you need to go potty? Ok. But remember to catch the little dribbles with a tissue. You wouldn’t want to stain those cute little pink panties. Now that you’re back, I think it’s time we did something about that little tiny – it’s too small to call it a cock, don’t you agree? It’s not even a dick. Dicklet. A dicklet. That’s all it is. Not...

its over sissy

It has only been 3 days and i can only blame myselfI love to have a cock in my mouth and there nothing to change this now as I became a owned sissy white boy with a tight pussy my friend Mike is using at his convenienceI was stupid to start thinking he just wanted my mouth oncein his car one night smoking weed i succumbed to his teasing and he convince me to tryi started and he help me love ithis 8 inch so big i felt weak under his control mouth full of cock and loosing myself as he...

My Life As A Sissy

My Life As A SissyFrom the earliest awakening of my sexuality I felt a strong desire to be girly. I was the smallest boy in my grade at school and my slender body was milky white and nearly hairless. I felt that my penis was unusually small as well, and I didn’t have any pubic hair until at least a year later than the other boys. My first reaction was to shave it off, which I did on summer vacations so it wouldn’t be noticed in the shower at gym. I was back to being deliciously smooth, and...

Best friend makes me a sissy

I waited nervously at arrivals. His flight had landed 20 minutes ago so I guessed he would be through quite soon. He wasn't expecting me, but I wanted to catch him by surprise, and also thought if I relied on a normal venue I would back out………. let me explain.My life had fallen apart over the past two weeks. I had always hidden my perversions from my wife (her description, not mine). However once too often I had decided not to go on a night out with her which had raised her suspicion. I left...

SISSY

Looking at me now, one will have an extremely difficult timebelieving this story. But let me assure you that every word istrue. It started late one spring afternoon. The weather was typicalspring weather, windy, wet and cold. I was walking home from highschool, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was very small, looked 16 and feminine. If you're thinking that's normal...

Becoming Sissy

Looking at me now, one will have an extremely difficult timebelieving this story. But let me assure you that every word istrue. It started late one spring afternoon. The weather was typicalspring weather, windy, wet and cold. I was walking home from highschool, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was very small, looked 16 and feminine. If you're thinking that's normal...

Gary s Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games. One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from...

Bathing my Sissy

Before i left the house,i told you that i want to take a bath with you today,till im back you should make yourself ready for me.As I come home,you are standing infront of me, the whole body shaved,a sexy long hair wig, slutty makeup with thick red lipstickand big carol shadow.You are wearing a bra, stockings, a garter belt, and a tiny string that can nothide your cute sissydick.You are looking almost like a girl with your smooth skin,that view gets not least supportedtrough the feminine round...

Sissy

Well. That was interesting, wasn’t it? We’ll play with your little titties again tomorrow. For now, just close your eyes and rest. Did you have a good nappy? Do you need to go potty? Ok. But remember to catch the little dribbles with a tissue. You wouldn’t want to stain those cute little pink panties. Now that you’re back, I think it’s time we did something about that little tiny – it’s too small to call it a cock, don’t you agree? It’s not even a dick. Dicklet. A dicklet. That’s all it is. Not...

Granddad s Sissy

Granddad's Sissy by Steve Andrews Part 1 The following is a true account of what happened to me when I was 21 years old and began one of the most exciting and yet frightening periods of my life. I had moved out on my own shortly after finding a management job out of college. As a child I had been diapered for bed wetting up until I was 12 years old and it had set the tone for my interest in wearing diapers. I was an only child to well-to-do parents who spent more time...

Sissy Mission 1 Balloon Sissy

The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 1: Balloon Sissy By Cheryl Alison As I entered the suite of offices, I looked for the directory. It was there on the wall, just like every other corporate accounting office. I scanned the names. There... Bruce Jones, Managing Director. He would do. I approached the...

Sissy Mission 2 Tutu Sissy

The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 2: Tutu Sissy By Cheryl Alison I entered the dancewear shop, nervous, and a little hesitant. There were several women browsing the racks of leotards and dance dresses, presumably shopping for their little girls. I walked up to the counter. The saleswoman, whose name tag...

Sissy Mission 3 Rummage Sale Sissy

The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 3: Rummage Sale Sissy By Cheryl Alison I stepped out of the car and walked up the driveway of a beautiful suburban home, the green grass manicured carefully. The driveway was full of middle-aged women picking through the cast-off items of a rather well-to-do family. I...

Hi Tech Sissy

Hi-Tech Sissy By Jane tv ([email protected]) They say it takes all kinds to make a world, but Ted and Carol had begun to take a jaundiced view of this old chestnut. They had arrived at a corollary of startling directness and simplicity: Certain types of people can make life a real bitch for the rest of us. Engineering manager Carol and engineer-physicist Ted worked at Optical Design Inc, a small high tech company located in a Chicago suburb, which produced lens system...

How I became a Sissy

This is a true story some of the actual words may have been altered slightly but the events are the same Please feel free to email me with any comments you may have Kelly is interested in hearing them. Thanks. How I became a Sissy By Britney Hi my name is Dave and this is the story of my relationship with my girlfriend Kelly, and some unexpected changes that occurred between us. I guess I shall start around the time period just after my 23rd birthday. Kelly and I had...

Sissy Mission 8 Up do Sissy

I sat in the car, taking a few deep breaths and trying to calm my nerves. My Spanx body-shaping briefer tightly held my lower mid- section over my sheer pantyhose, which provided some comfort as they hugged my legs. As I slid from the seat to get out and enter the mall, I felt the cool silk of my nylon panties on my bottom underneath all those layers. I walked into the mall past the throngs of people typically roaming the polished floors on a Saturday. My heart was beating fast, and...

The cycling Sissy

Cycling Sissy My wife does ride a road bike that part of the story is true the rest is just a dark fantasy.... this is just a short story I thought of when I was putting some of her cycling clothes away... Sarah my wife doesn't drive, never bothered to learn... But her vehicle cost almost the same as my car. Its a top end 3 grand carbon Road bike... I called it a racer when I first saw it just after we started going out... Oops I don't think I've ever seen her as pissed...

Cucked and Fucked Sissy

My wife and I were out getting groceries and she wanted to stop at the liquor store to get some beer. I had plenty at home so she just went in while I stayed in the truck. A little later she comes walking out with a nice-looking black guy. They are both coming to the truck as they are talking and my wife is laughing. He opens the door and she gets in. I’m a little confused as she looks at me with a smile. She says, “this is Brad, and he’s coming over tonight to fuck us both, but especially...

I m A Cuckold Sissy

I'm A Cuckold Sissy by Throne My wife Tracy is observant and clever. During the first months of our marriage she noticed my natural submissiveness and how I loved her clothes. I didn't want to wear her panties and stockings. Their appeal was more like a fetish. Except that a fetish is usually exclusive to one thing, like shoes or furs. I liked everything she wore, from a full length leather coat to ankle socks with lace around the tops. The clothes were exciting enough in...

Jacob made me a sissy

All this was going on for a few weeks. I particularly liked gay older men specially those who are hairy. I mostly sexted with men, i never met anyone. I was still a virgin. Now i never revealed my identity or shared any pics. One day i received a message from a hunky bear. He was hairy in his 50s. I really felt attracted to his body. He even had a monster cock. He had a veiny 9 inch cock. Now we talked and we sexted, like sexted alot. I was really into him. He would often send me pics of his...

Vickie dickie the Pissy panty sissy

All throughout grade school, Victor had been teased and picked on, called a sissy and laughed at for his high-pitched voice, shy manners and disinterest in the manly art of rough-housing. But the other kids would have had a field day of torment with him had they known what lay beneath his mild mannered exterior, the real Victor who lay hidden beneath his clothes. Victor hoped to keep it that way ... hidden. From kindergarten through eighth grade kids played some sports in the schoolyard, but...

Landscaper Ass Pumped Sissy

“Let’s rotate that shoulder now,” said the occupational therapy assistant.Bradley Hunt had been rear-ended a couple of months ago causing this injury, He was now going to the Naval Health Clinic Charleston weekly to rehabilitate his shoulder. Fortunately, he had missed very little pay because he owned a landscape design firm and a Little Caesars pizza franchise.“How does that feel,” the slender, brown-eyed, blond-haired healthcare worker asked.“Not too bad,” squinted the rather in-shape...

Life For An Adult Arcade Sissy

The back was dark, lit only by a few dim red bulbs. He walked up the corridor, which was lined with booths. A light above the door of each booth indicated whether or not the booth was occupied; if the light was on, it meant it was occupied. There were signs saying, "NO LOITERING, NO SMOKING," and "ONLY ONE PERSON PER BOOTH." However the presence of several men lurking in the hallways, some of whom were smoking, led the man to believe the rules were not rules at all. As he rounded the...

Shemale on Male A boy can t outrun his fate of becoming a sissy

It had been about a week now since Nim had arrived at the Lunarfall Garrison in Shadowmoon Valley. It was the biggest choice he had made so far in his life to travel to the alternate Draenor, but it had been a relatively easy choice considering the life he was leaving behind. Nim had been gifted with quite the feminine body, so much so it had begun to get extremely tiring of constantly being mistaken for or picked on for being so lady-like. It was mostly from behind that his gender was...

3 LOVE DOVE 4 HISSY SISSY

Roxanne knew Sean would be getting home soon and came over to be there when he arrived. “Shaw-nee-poo! How did it go?” Straight-faced, “What did you get me into! Those kids are a bunch of belching, spitting terrorists!” Empathetically, “Oh, I’m so sorry, Sean.” “Count me out. Call Burt to find another coach. I got a bad migraine.” Sadly, with a comforting embrace, “Oh, oooh.” “Gotcha!” “What????” With a big grin, cheek to cheek, “Roxanne, I had the time of my life. Thanks...

BECOMING KATHY A SLUT SISSY

Any one that knew me saw an average 18 year old teenage boy , friendly , a good student who worked a part time and lived with his divorced mom an older sister . That's what I wanted them to see , only a few special friends knew the real me and my secrets . In junior high I realized my growing sexual attraction to the other males and living with my mom and sister it wasn't long before my feminine side began to show . It was a Saturday morning mom and Sue my sister were just leaving for the for...

Story Time with Daddy and Virgin Sissy

Me:fuck my cock is throbbing in my jeansYou:imagining me lay there waiting for you to tear my panties aside and take care of that large problem in your jeans?Me: You're a frisky little girl. You:SometimesMe:You ever been fucked? You:No, daddy. I'm a virgin. Me:No way. You:Never even been kissed. Me:That's a shame. You've got beautiful lips.. You:wouldnt mind a kiss from you stud, anytime, and you know im just lay here in a bra and panties right nowMe:mmm here's what i'd do if i had you...

The college secret sissy

Iam one of those shy white boy with a little cockI tried to not think about getting a toy to fuck my bubble smooth ass after inserting the handle of a screw driver in me, the toy shape handle pumping in me , making me shiver of pleasureI thought a lot about having a nice cock toy, something i could suck on and have fun in secrettoo shy and living with mom and dad Until i got to college and being alone in my dorm room, away from my family , it just happened one weekend i order it on a toy vendor...

Going full Sissy

After my last adventures (see my previous story, Two BBCs in Three days) I needed to catch my breath. What was happening to me? Here I am, a middle-aged guy, married with a couple of k**s, willingly getting down on my knees and sucking cock. However, instead of feeling repulsed and guilty, I felt content and satisfied. It was like a finally found myself. Once again, I found myself constantly thinking about the dicks I had sucked and thinking about sucking more. I had truly become a submissive...

My life as a SISSY

From the earliest awakening of my sexuality I felt a strong desire to be girly. I was the smallest boy in my grade at school and my slender body was milky white and nearly hairless. I felt that my penis was unusually small as well, and I didn’t have any pubic hair until at least a year later than the other boys. My first reaction was to shave it off, which I did on summer vacations so it wouldn’t be noticed in the shower at gym. I was back to being deliciously smooth, and by now I was starting...

I am Sissy

The year was 1888. My name was Sebastian but I was now called Sissy since I was taken a slave. My father’s merchant ship was captured and sunk by the pirate crew of the Black Bess. I alone was saved for Captain Booth's pleasure. He was an escaped convict from the prison island of Australia. He was a huge beast of a black man, dark ebony skin stretched tight over enormous muscles that bulged everywhere. He towered over every other man I have ever seen and he was not a kind man at any time. He...

Me being sissy

Let me start at the beginning .. I have always known I was bi having been married bit enjoying the taste and feel of solid cock. I first started wearing panties stockings a few years ago and soon began to love the feel and look of being dressed sexy. It was about 3 months ago I was on grndr and started chatting with a guy called David he was 57 I am 46 slim tonned he much bigger than me... after a while of chatting and flirting swapping pics I asked if he likes guys in panties stockings his...

BLOWJOB SISSY

Gobblers, the Squat and Gobble These tranny "blow job" bars are exactly that. They are where you go to have a shemale who sucks dick. The way it works is you choose the sissy you like and then you go in the back of the bar where they have small, cubicles. There she will suck you off. The cost is about $20. Squatting in just a pair of high heels on the dirty floor the naked Caucasian prostitute performed a nasty spit dripping blow job on a big black dude who was sitting on a bar stool, sipping a...

Neighborhood Sissy

If you read my earlier stories, you might have caught on how I began to be the sissy of my older neighbor. And I must confess that this silver fox of a daddy has a high sex drive which does catch me of guard. Cause after the last story iv spend countless minutes on my knees sucking him of in front of the tv. Its almost gotten a habit where he will text me to come over, and there he will sit with a white tanktop, a old porno-movie on his widescreen, no pants, but his dick is all ready to go. So...

Used Sissy

I was now a fully fledged Crossdressing Sissy Slut even though still only in my teens I needed and craved cock..........any cock as long as it was loaded with spunk for me to swallow. I had been sucking cock at various toilets around my town and had met some really kinky bastards in my time but John was way ahead in his kinky ideas. He was a mature respectable male in his late 50's a white collar worker with a nice property in the country.....he was married and had 3 k**s so to any one taking a...

my mom turned me into her sissy

"Mom! I called out as I got home from baseball practice, "I'm home!""Hello Danny, we have to talk," she responded, while exiting my room.When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store."Please explain where these items came from."I should have told her I was sorry, and that it was just the one time,But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I...

mom made me her sissy

"Mom! I called out as I got home from baseball practice, "I'm home!""Hello Danny, we have to talk," she responded, while exiting my room.When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store."Please explain where these items came from."I should have told her I was sorry, and that it was just the one time,But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I...

Confessions of A Lovestruck Sissy

Confessions of A Lovestruck Sissy rrrrrinnnggg RRRRRRRRINNNNNG I started...slowly rousing myself from the floor of my cage... "Mistress!!!" RRRRINNNNNNNGGG "Mistress!!!" nnnnnnnhhhh... "Whaaaaaaat???" RRRRINNNNNNNGGG "Oh...the phone!" RRRII "He-llo?" (Mistress did have a wonderful way of speaking on the phone.) "Oh hell-oh, darling...oh, I've been sleeping it off, dar-ling." (Mistress giggled coquettishly.) "...Brutus was around last night, and he WORE ME...

Gym Sissy

Gym Sissy By Sssydiane I was a few years out of college, with a good job at a corporate accounting firm. I worked long hours, but the pay was very good. My boss liked me, and my prospects were good. I didn't yet have customer contact, but I was primarily responsible for several important clients. I was never athletic. In fact, I was a bit of a weakling growing up. I've always been slender, or I should say I used to be slender. Since I now lived a pretty sedentary life, sitting...

Bubba to Sissy

Bubba to Sissy It was a sad day for me when I received word that my Aunt Beatrice had passed on. Not that I hadn't been sort of half expecting it, at least in the back of my mind. She'd been getting on in years and was in poor health. I regretted not visiting her more towards the end, but we had written to one another on and off. She was very special to me, the first person I ever came out to. I really only confirmed what she had always guessed, she always saw the real me, even...

America s Next Top Sissy

America's Next Top Sissy Blinking slowly, Jim's blurred vision started to clear. The strong lights pointed in his face made Jim squint, but his hearing was as clear as a bell but his head was swimming. A camp male voice spoke clearly to somebody but Jim still couldn't quite see who was talking or who was being spoken too. 'Welcome ladies, too the new series of America's Next Top Sissy' echoed in Jim's ears as the camp voice continued ... 'All of this years contestants have been...

The feeding of sissy

I hold a prominent position in a world wide business firm and make a six figure salary and had been divorced for several years. I met Wendy through a newspaper add in the singles columns, she was a knockout looking gal. We dated for some time and she moved in with me. One night when we were out having drinks she ask what my deepest secrets were. She would share hers with me in return if I told her mine. This took a lot of convincing and a lot of drinks. She went first telling me she prostituted...

My work friend makes me his sissy

I'd always been a little insecure about my sexuality but was embarrassed by my fantasies and had never tried to explore much.I had recently moved to a new town and didn't have too many friends but wished I could meet some more. I had a coworker that I was kinda friendly with so invited him over to puff a blunt and watch some TV one day. I wasn't intending on anything sexual and still kinda thought i was straight but he was pretty attractive. He was tall, black and muscular, about 2 years older...

The night I stayed in Nashville as a sissy

I was traveling to Florida from Missouri to see my k**s. I new always stay the night in Nashville, and sense I would be alone in the hotel I thought I would pack a few of my sissy things. The thought had me hot the whole trip so I had to pull over early and slip into a rest room in a truck stop to put on some things for the drive. I put on some pink panties and stay up stockings, also a little camisole under my shirt. Wearing these under my cloths had me excited the whole trip. By the time I...

Black Man s White Sissy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin’ HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women. One day when my mom was at work,...

How i became a sissy

Hey guys im a 24 year old boy-girl and i felt like i needed to post about it in some place, since i was young back at highschool after gym class some guys would mock about my size wich is really really small and thin, and they would call me horny names like size queen, sissy bitch, but most of them did that just to humiliate me the funny thing was i got so excited that sometimes i had to lock myself in the shower so they wouldn't see me going hard (i was a little ashamed back them) but after...

Black Man s White Sissy

bynancyvasquez©I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.One day when my mom...

My first time as a sissy

As you seemed interested in my first full on gay experience, I thought I would describe it for you in more detail. After my split up with my girlfriend of 3 years I was quite upset and found myself going to the pub more frequently than before. One Friday lunchtime I got chatting to Andy who used to pop in occasionally either with his girlfriend Fiona or on his own & today he was single. I would have been just 21 & he was in his late 20’2.We chatted about this & that & eventually...

My first bbc as a sissy

When I was 18 I saw a porn film that changed my life. My mates and I had drinks then watched a straight porn film and for the first time I witnessed interracial porn. The scene was a black man about 55 years of age with a young blonde girl about 20 having sex in what looked like the woods. She was on all fours and they were both naked and he was fucking her doggy style and when the camera zoomed in the sight of his black cock sliding between her very pale pretty smooth arse cheeks was the...

Pretty Blonde Sissy

Naked and young - in bed with a big black MAN! Both of our naked bodies entangled together. I learned to give blowjobs early. I started masturbating when I was very young. Once I started doing it, it was all I thought about, 27/7 it seemed like. At that time I was living with my mom and her boyfriend Micheal. I never knew my real dad, Mom never talked about him; once, when she was drunk, she told me she wasn’t even sure who he was.Mom always had boyfriends as far back as I can remember. Three...

Folsom Street Sissy

As you enter the arcade you will notice that it is quite dark, with just dim lighting. What lighting there is only serves to illuminate just how filthy the place is. The stink of piss and semen is pervasive. You have to walk carefully because the floor is slick with semen. Once you get past this assault on your senses, and your eyes begin to adjust to the dim lighting, you notice the men. They are everywhere, lurking in the dark corridors, some on their knees right in the hallway, sucking other...

Coming out as a sissy

Such a cliche. My mother wanted a daughter. She already had a son. I was a 'miraculous' birth - couldn't wait to get out. Rushing to embrace the world. Then finding that the world wasn't quite so crazy about meeting me. When I told her I am gay she said, 'you were always different from the moment you were born'. I was a sissy from the beginning. I wanted dolls. Tiny china tea services. As I grew older, I played only with girls, loved only girly games, spent all my time with girls. The bullying...

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Dwight dropped his twins off at their elementary school. He drove the royal blue 2011 Chevy Avalanche as he made a quick call to his wife. He got her voicemail as he figured since she was at work. He was tired after pulling an all-nighter at the plant. But he had one more stop to make. He turned into the neighborhood and pulled to a halt in front of the white ranch-style house where his wife’s mother and stepfather lived. He knocked on the door was greeted by stepbrother-in-law. Dwight studied...

Black Man s White Sissy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.One day when my mom was at work, I...

my sissy

This is a total fictional story, and any names, and places are from my imagination. My name is Roger Jarnic, or RJ for short. I am 32, 6', 220lbs. I was on my way home from my mundane 9-5 job, when I came acrossed a car with it's hood up on the side of the road. It's hood was up, and a skinny, jean covered ass was sticking out from under it. I thought to myself that I should stop, and see if I could offer some assistance. So, I pulled my chevy over in front, parked, and as I was getting...

Chrissie Rhymes with Sissy

Chrissie Rhymes with SissyI first met my wife whilst I was on a break in Durban, South Africa fiveyears ago. I was based in Lusaka in the final year of a four yearassignment in Zambia and I needed a week or two in a somewhat normalcountry and found a small but elegant beachside guest house on theinternet and booked in for a week. The owner promised to send herdaughter to meet me at the airport in Durban and drive me to the guesthouse. There was no direct flight from Lusaka to Durban so I had to...

Becoming a Sissy

Becoming a Construction Site Sissy for AllI was just a few months past 21 when I left Mom and our small country trailer to try out life on my own. By this point in time, not only Mom but just about everyone in the rural country knew how queer I loved to be and act. Yes I can’t begin to count the cocks I had orally serviced and pleasured since my early days. While I had loved it more than anything, I had paid a strict price for my dick addictions. Verbal assaults every waking day, sometimes even...

MY GAY PRISON SISSY

I'm sure many of you have seen a number of movies or television programs based on prison life behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I'll now share with you first hand, some of the wildest and most unbelievable sexual experiences one could ever imagine. While still on parole now, I will change my name here and not mention the state facility involved. Other than to substitute a few names for some of the real ones involved, all of what I'm...

Black Man s White Sissy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.One day when my mom was at work, I...

The day I encountered a sissy

It’s a warm day when I arrive, you have followed instructions and have freshly shaved cock and balls, your pubic hair has been trimmed and you are wearing a nice lacy pair of panties. I am carrying a small bag with my equipment!!Under instruction you undress me carefully, avoiding any contact with my swelling cock or balls. I put a leather collar around your neck and order you on to all fours. You are instructed not to touch your own cock whilst you watch me put my ball stretcher weights onto...

My life as Daddy s sissy

Hello Daddy,I would so love this life…I wake up thinking of you, dreaming of kissing you, of sucking your cock, of feeling it fill my boicunt.I spend all day preparing for you, so impatient to be with you. You are at work and I’m home, enjoying my role as your slut and maid.I clean the house wearing pink sissy sweat shorts and a tank top, pink sneakers and pink socks. I want our home to be perfect for you, and I take pride in taking care of the house you work so hard to provide.I then go to the...

Prissies Sissy

Prissy's Sissy Chapter I Portland, Oregon, January 5, 2005... "I'll take this one," Alexandria del Torez said, looking at the profile of Randy Grey. "I think, this one will do fine." Miss Fredericks, a kind tanned lady, scrunched her eyes, doubtful. Tired of Mz Torez, she still asked, "Are you sure, Ms. Torez? We have no references on him, and he comes from the south, so, no offense, he's probably stupid." She winced at herself for saying that, but wasn't it true? Alex, as she...

Businessman is Forcibily Transformed Into a Sissy

Businessman Is Forcibly Transformed Into A Sissy By Sissycuckold It was a warm summer's day when it all began; I was a successful 34 year old, businessman man, with a large house, flash car, and a beautiful wife. As it was a Sunday I was out for any early morning walk, having just finished making love to my 27 year old wife Lorna, when suddenly a large black car screeched to a halt just before me. In a flash 4 burly men jumped out and I was unceremoniously...

Sheer Energy Sissy

I was tormenting my cousins as I always do and they would expect nothing less when I come over for the weekend. This time I put iching powder in their panties. The girls were running all over the place scratching thier asses. I was laughing the whole time as Jenny and Sarah tried to figure out what happened. Whats the matter girls? are your panties all in a bind? You little bastard, what did you do to our panties? I shrugged my shoulders as my Aunt came in to say goodbye. Now you kids...

Sorority Sissy

sorority sissy by sissy 4 u i had been dating karen ever since I started going to college about six months ago in a northeastern university karen was an extremely beautiful girl which was part of the reason why it was so easy for her to join the sorority delta kappa all the girls at that sorority about 50 in all plus a house"mother"who took care of the bills the dormitory and any trouble the girls might get into the resident girls of delta kappa as i said were were real "lookers...

Chrissie Rhymes with Sissy

Chapter 1 Chrissie Rhymes with Sissy I first met my wife whilst I was on a break in Durban, South Africa five years ago. I was based in Lusaka in the final year of a four year assignment in Zambia and I needed a week or two in a somewhat normal country and found a small but elegant beachside guest house on the internet and booked in for a week. The owner promised to send her daughter to meet me at the airport in Durban and drive me to the guest house. There was no direct flight from...

I Felt Like a Sissy

I felt like a Sissy Janet L. Stickney [email protected] I felt like a big sissy; from the ruffled panties to the cincher, pantyhose and dress, I looked like a little girl! I sat at mom's vanity doing my own makeup under her watchful eye, starting with foundation, then eyeshadow, eyeliner and mascara, followed by blusher and lipstick. She fastened the hairpiece on my head, brushing it out, then trimming my bangs. I clipped on the earrings, stepped into the short heels,...

From Husband to Castrated Sissy

From Husband to Castrated SissyKimmie Holland ?Oh my god!?My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. ?Hi honey. What are you doing home early???Kelli what the fuck’s going on here?!?At that, the black guy turned and shot me a nasty glance. ?What’s it look like we doing, genius? I’m dicking your old lady. Now get out of here fuckshit I ain’t finished.??Better go downstairs dear,? Kelli said,...

Breakout of the rut Sissy

I suspect many of us have a lot in common. I am married to a prude who wasn’t always a prude and knew I was going to wear lacy panties and thigh highs and encourage her to as well then talk to alpha males online before we married. I didn’t know I was a sissy, I didn’t know I wasn’t unique. She aroused me and still does only not as often. When we first explored and experimented I was able to mix my desires in with fucking her up theass or she’d strap on a dildo and fuck me as I spread my legs on...

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