Shemales Porn Stories
Page 4

One man's shemale and lesbian adventures

It was my girlfriend Kami’s birthday. She had always been more into girls than guys and so I had arranged a surprise for her - and a treat for both of us. A girl I met earlier that week was to come over to hers that night, and I couldn’t stop the thought of the awesome threesome we were going to have from going round in my head.
Kami was, like me, in her early 30s, but looked younger and had no problem attracting all the girls she wanted. And wow, she did get through a lot. Only a couple of times a week was I allowed to see her, but I made the most of her gorgeous, tall body with its long leg... Continue»
Posted by skorga2 29 days ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  
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A Early morning Visit to Boston...from Providence,

........the road to Boston...interstate 295
several years back, when I was about 25, I would take a ride up to Boston from Providence?..Id usually call a girl friend the night before and arrange a weekend on the town ...My plan was to leave before the sun came up to try to miss the morning rush,,,, this morning, I got up early and had a nice bubble bath and shaved my legs and any place that needed a touch up..wash and dry my long reddish blond streaked hair and curl it,,,, and do my nails or that was my plan,,

,I spent the night before getting my style together so it should have been easy!... Continue»
Posted by Sissy_jamie_RI 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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TEEN CD SLUT AND LUVING IT PART 3

I was between Mr J's slowly sucking his cock as he lay on my bed,here I was acting out my fantasy, all I was thinking about was how great it felt , he seemed to be in his own world also and was finely getting what he wanted,sex with a CD,and being able to leave the closet.
I took my time, licking him up and down,slipping his hard cock as deep into my warm mouth as I could, I love it's feel,stiff and firm,my saliva had him so slippery I had to rub him over my face,again and again as I kept sucking ,my own cock was full and heavy... Continue»
Posted by geoff19 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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My first and only time with a transvestite

This is a true story that I would like to share, and happened during a holiday trip to the beautiful country of Philippines, 4 years ago.

A group of four friends and myself, decided to spent a week at a resort near Cebu city. The guys were talking about the crazy nightlife,
and how they wanted to meet local girls and get hammered. I mostly wanted a peaceful few days next to a pool bar. I had the luck to had
had extensive holidays in my time, as I was mostly working at resorts around the med for many summers. Sex was plenty, as was short term
relationships, of which I had had enough in ... Continue»
Posted by hrnytaken 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Saturday Night at the truck stop

Last evening I took a ride to one of my favorite truck stops. It was hot and muggy out so I decided to wear a yellow flowered sundress(so cute) Also a yellow lace push-up bra (32A falsies), Yellow sheer lace panties with shit lace trim, white fishnet stockings and a jet back 6 strap satin garter-belt with red lace trim, white heels. Had on my long blond wig and of course no Gurl would go out without makeup.
As I entered the truck parking lot I heard a loud whistle followed by MICHELLE MICHELLE I stopped and a trucker I had serviced many time before ran to the car.
"Was hopping you would... Continue»
Posted by MichelleSissy14 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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I'M A TEEN SLUT CD,I LUV IT PT2

IT was a few months since I first sucked a cock and I was hooked, I kept going to the park and the ABS,I's stay in the both as long as I could,sucking s many cocks as that came through the gloryhole,I loved the feel of a hard one in my mouth and the cum tasted so good. Then one night as I wa getting ready to leave I saw him, my neighbor, he was entering a both, I had know idea about this secret he was keeping from his wife, he would always talk to me when I was around the house and now I knew why, he was in the closet.
For the next few weeks I spent more time in... Continue»
Posted by geoff19 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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Becoming my friends sissy

I was standing in the pub toilet having a piss. I had been in the pub for a couple of hours and had had a few pints with my mate Roger. I had tried to slip off for a piss by myself while Roger was up getting another pint. As I stood really close to the trough my little cock was dribbling, when Roger came bounding in. There you are Tom, I thought you had done a runner, he laughed. He stood beside me and fished out his enormous cock from his trousers. Unlike me he stood about a foot from the urinal. I glanced down, knowing that I would see a magnificent big cock, I guessed 6 inches flaccid and a... Continue»
Posted by tinycockhetro 1 month ago  |  Categories: Shemales, Anal, First Time  |  
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CREAMPIE TRIO IN THE PARK

Nicole had this thing for public sex,and so did I. The chance of getting caught and a pair of extra eyes was an enormous turn-on.
We would meet in a bar and after a few drinks I would feel her hand in my crotch, rubbing my dick. She was always dressed for the occasion in a way I would have easy acces: short flimsy skirt and a wide shirt. This time it was a summer night and we standing at the bar of this grand café and she was really in the mood rubbing her crotch against my leg
"I'm already wet," she whispered.
I slipped my hand under her skirt and felt her slip which indeed felt moist and ... Continue»
Posted by FetishFreddie 1 month ago  |  Categories: Group Sex, Shemales  |  
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A copy of a text i sent to my female fuck buddy ab

I have had a BBW fuck buddy for over 10 years and together we have had MFM threesomes, dogging fun and lots of dress up fun too, we swap lingerie and share stories, sadly she hasn’t been able to play for a while but loves to know what I have been up to. Below is a copy of a text I sent her today following on from a lovely morning of sexy CD fun

So, Andrea. I turned up and he was dressed in a skin-tight dress, black stockings, heels and full make up and wig, he was very skinny and looked amazing and I was so horny. We had a chat about what we both liked and I popped off and got changed, I c... Continue»
Posted by PortsmouthCD 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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Training my daughter to be a bimbo, part 7

Part seven of my story.


I came home to be greeted by Cindy standing at the door. She looked stunning, obviously she had been to the beauticians that morning as everything about her look perfect, her gorgeous platinum blonde hair, her nails, make up a slight pouting lips hinting at some Botox and of course she was dressed like a complete slut.

She took me by the hand and led me into the living room where she sat down and looked up at me "is daddy hungry?"

This was now part of our routine, any time Cindy spent the morning at the beauticians it also meant that she was completely bald around h... Continue»
Posted by snoozer2000 1 month ago  |  Categories: Anal, Shemales, Hardcore  |  
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I'M A TEEN CD SLUT, AND I LOVE IT

In high school I realized I was gay,during gym class ,the sight of the other guys showering really excited me,watching them them soap up,there smooth bodies with almost hairless cocks,tight butts,as they stood washing,bending,turning,the water running over them. It was all I could do from kepp from getting an erection, after class I went to the nearest bathroom and jerked off as I thought about there cocks and what I wanted to do with them,I just wanted to suck them and taste their warm cum,it was all I began thinking about.
One day as I... Continue»
Posted by geoff19 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Year 2489 (Part I)

There was not a single sunbeam in sight, yet the city was practically littered by various sources of light. Whether it was the screens embedded into the windows of the shops alongside the shopping promenade, or all the advertising neon signs which made the hole scenery of the city as brightened and overcharging as Robert was experiencing it at this very moment.
Yet, it was all due a natural evolution of this planet, wasn't it? He asked himself for a moment. Then he noticed that he reached his destination. The corner of sections 22a and 22b, building number 239. Oddly this part of the city was... Continue»
Posted by MimiCD2016 1 month ago  |  Categories: Shemales  |  
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The Saturday night Gangbang---afterwards

I spent all day Sunday trying to wrap my head around what happened to me the night before. I was shaking from fear just knowing that had things gone differently I might not be around anymore. I finally got really pissed off and sent a text to Mr. 9er letting him know that he had used me for the last time. Nobody has the right to put anyone's life in jeopardy like that. My ass was on fire all day from the hours of being pounded by incredibly huge hard cock. T!#a makes guys go all night long. I kinda wondered how the 2 girls were feeling, but they did have the advantage of having more holes, so ... Continue»
Posted by LRock4fun 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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My journey part 111.

My journey part 111.

After a few minutes of this he asked if I felt ready and when I said yes he asked me to kneel in front of him facing away as it was not quite so uncomfortable in that position for the first time as I could move around more easily if I needed to do so, I did as he asked and he put more Vaseline in and around my arse hole and loads on his cock and came up behind me and steadied himself with one hand my hip using the other hand to guide his cock up and down my crack before finding my hole and gently pushing forward until I could feel his whole cock head in my arse, it was... Continue»
Posted by silknsatinxxxx 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Visit to the Doctor, part 3

It's worth reading the first two parts, but if you don't want to, a young man with a tiny cock visitors his Dr who recognises him as sissy material, he grooms him on X hamster, and the young man to his delight realises his role in life

Part 3

After the doctor had had his way with me (although in truth the dedicated sissy I felt that I had my way with him) we sat and talked for a while.

He was asking me how I felt about my transition from inadequate heterosexual to a promiscuous sissy who took great pleasure in giving her ass to cock. I smiled at his characterisation because it was e... Continue»
Posted by tinycockhetro 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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[Story 1] Pools are fun ♥

okay so this is one of the more sexy stories for me, so i`m putting this one up first, also as a heads up, even though i`m actually am a normal girl in actual life, i do (day)dream about what it`d be like to have a cock, while staying a girl. and remember, these are just dreams, and sadly not real stories, so here goes:


A short while ago i had a lovely conversation here that stayed in my mind so much i had a pretty vivid dream about it. It all started like this; i was just waking up next to Jenn Form2000 as usual, on an amazing Summer day, and we slowly woke up ... Continue»
Posted by LovelyNattie 1 month ago  |  Categories: Lesbian Sex, Mature, Shemales  |  
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Went to new job dressed a woman when boss was away

Hi, just started a new job working all week and occasional saturday. On friday, he told me, that i would work saturday and would have to work alone. So i figured, hell, I hadnt dressed in awhile, normally don't go out dressed in public. So I said F This, going to do it.

So i made my self passable, make up, hair, everything, but oh what to wear? I put on my new black bra, thru on a white panty, along with a cute top and jeans to start out with. Had a few cust's come in, didn't say anything on my look or anything, only one asked who i was and said i'm the new guys g/f, and he had to make a... Continue»
Posted by Shariwells11 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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Young Tranny Ch3 Restroom Fuck

This is the third story following "How I Started," and shares my experiences between the ages of 19-29. These are prelude stories to the series of "Playtime Stories" I wrote. I hope you enjoy them as much as I had "researching" them. They are mostly true so enjoy! I LOVE COMMENTS!!!!

3. Drive-Through Guy & Motel Gurl

I quickly became obsessed with sucking and fucking black cock in arcades. Actually, I was up for practically any cock in an arcade. The cocks turned away were few and far between. At the time I was in the deep south, most of the time I was either the only white pers... Continue»
Posted by 6988slutty_rbckyy 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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My First Time.

The evening had been wonderful. The first one in the several months since my wife had left. A few drinks after work, a movie, and then a late dinner. And Jamike.

Meche works with me in the law firm. We both share research duties as we prepare for the BAR. He, and his wife Chy, had been friendly with my wife and me. After she left they had seen me through some very difficult times. Now, as I was preparing to re-enter the social arena, they were making every effort to see that I enjoyed myself.

Jamikewas a former room-mate of Chy's; they had been best friends in college. When I expressed a... Continue»
Posted by agunna 1 month ago  |  Categories: First Time, Hardcore, Shemales  |  
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Visit to the Doctor, part 2

The doctors help X Hamster i discover my calling to be sissy.


As soon as I got home from the doctor's I fired up my laptop in my bedroom and logged onto X hamster. I immediately found the account for my doctor and spend the next days exploring it.

My perception of sexuality had dramatically changed. Going into the doctor I was convinced that I could only get and give sexual pleasure through intercourse with a woman. Having experienced what I considered to be mind blowing sex with the doctor my opinion had already changed.

X hamster showed me the path of exploration and I followed it with e... Continue»
Posted by tinycockhetro 1 month ago  |  Categories: Anal, Shemales, Hardcore  |  
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