Shemales Porn Stories
Page 85

The Ebony TS of my dreams


This story is about one of the most memorable piece of cocks I've ever experienced in my 30 plus years of getting fucking. I just thought I'd write it down and share it simply because I'll never forget it and because I'm a married man and it most likely will never happen again.

It happened about three days ago with TS Dominique I met through the internet(EROS). She was 23, but she easily looked 20. She kept her body pretty fit. She was about 5'11 and 135 lbs. I love tall women because I'm physically a big myself--6', 245lbs. It's hard to be fucked by a woman bigger than yourself. Plus, I... Continue»
Posted by yesamwilling2 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1564  |  
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A Quickie For Jemima

I checked my make-up and adjusted my brunette, bob cut, wig in the bathroom mirror. Pleased with the results I then ensured that my clothing was right. I was a vision of darkness: black G-string under black thin denier tights, 3 inch heels, black satin vest top and black mini skirt. I was sure Simon would approve.

I walked slowly yet purposefully to the bedroom. Simon was sitting on the edge of my bed naked stroking his cock looking at me “mmmmmmmm,” he said seeming to approve “ Why don’t you cum and join me the doors open?”

Out of habit I shut the door as I enter in case we made a lot ... Continue»
Posted by JemC 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 831  |  
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How it all Started....

Back in 1997 I was living in my dads place a condo on the beach.In the summers I had a friend come down from new york with her f****y. She was 3 yrs older then i was.I loved going to the jacuzzi the building had by the pool. one day I was seating in there and her grandfather and she came in. we where all in the hot water and i feel as where talking my foot being played with. after a while the foot got higher un till it was almost at my thigh inside my trunks. I got hard. I must of been twelve or so....As my friend get up to go to her towel. I figure out that It wasnt her, that was doing it.. ... Continue»
Posted by lucifer696 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2050  |  
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A Pleasant Surprise 


I really do enjoy my swing life style. Here is an example of one of those times. 
My lady has this friend, "G" and I wasn't to keen on her. But thank god she lives 4 hours away. I usually bail out on my lady's visits and she is cool with it. But then once my lady begged me to go with her on the next visit. I declined. 
A few days later she asked me again but said she would make it worth my while. Besides it was a huge cook out that we were going too. 
-fast forward to the weekend-
My lady and I took Friday off so we drove out to her friends Thursday after work. After that 3 hour drive, w... Continue»
Posted by rogue-1966 2 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 2342  |  
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Delilah and the Deep Blue Sea. (Part Two)



When I awoke the next morning I was alone. I rose up from my bed amidst the ruins of the villa and peered around cautiously. There was no sign of her. Carefully I tip-toed out from the ruins and conducted a quick scan of the surroundings. The little olive grove was quite deserted other than the small creatures with which I shared the island. These seemed busy at this early hour. There was a little dark grey bird singing from the scrub at the edge of the olive grove. It had a musical voice I found quite soothing. I was to become familiar with that little bird and the mate he found to build ... Continue»
Posted by Mikebasil 2 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 994  |  
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my first tranny pt. 2

it hurt so bad but felt so damn good. I told her just to stay still so I can get use to it. get use to having a cock in my ass. that was a totally new feeling. it was something I always wanted to try. now I was.

she slowly started to move back & forth. not really pulling out, just enough to make me feel better about it. she was stroking my cock, which was rock hard. I could feel her balls on my ass. deep down i was freaking out. this is really happening. I knew that coming here I was going to fuck some ass. not get my ass fucked.

eventually, I got use to her cock in my ass & she was pu... Continue»
Posted by radec_24 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1442  |  
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I've always wanted to meet a gurl!

First of all I would like to apologize for my English.
Hello there! I live in a small country's biggest city and here people are strange. If they are crossdressers, shemales, trannies, tgirls, gurls (actually we have only 2 words for a shemale, so I don't know which one is NOT offending please excuse me I do not want to offend you or what so ever) usually do everything for money, or they lack good health, hygiene or I haven't met the right one. This is was a bit new for me. I've always wanted to date a gurl. Not just the sex part, but actually get to know the person, to fall in love and thin... Continue»
Posted by AngelPetrov 2 years ago  |  Categories: Shemales  |  Views: 467  |  
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helping friend in need

It was a quite normal saturday I just got home from getting my nails filled and eyebrows waxed,till a female friend of mine came by very upset and crying.I asked her what was wrong and she showed me a letter that she got in mail saying she had to pay $2800.00 dollars by Monday 4:00 pm or go to jail for 6 months. Her exboyfriend got some tickets in her car and never told her or payed them. Since they were all on her car she was the who had to pay them.
I told her if I had money I would lend it to her but I just payed off my house to get out of the interst rate I had.I said to her if she coul... Continue»
Posted by cdpaula 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3067  |  
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Shemale secretary fucking

Ms Boss had said that I was to see her secretary concerning "letting of some steam". She and I had been at each others throats lately and Ms Boss didn´t like her two slaves to argue.
So we were left alone in the break room after most people had gone home. And we were not to leave until we could get along!
We started aruing about everything, from work stuff to personal tastes to sex. Culminating with both of us claiming to be Ms Boss´s favorite.
The competition was clear. Fuck each other so good the other one yealed.
We nearly tore our clothes of and started kissing and touching each oth... Continue»
Posted by Ankakalle 2 years ago  |  Categories: Shemales  |  Views: 1029  |  
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From Andy to Amy


Story codes: CD TV mf voy mast nosex

If you are looking for serious one handed reading, then you are in the wrong place. I hpe you like this. It's the stopry of a young man's first venture into cross dressing. Any similarity to me is entirely coincidental!

Title: Andy to Amy

"Why are you staring at my knickers?"

I jerked upright. God, I really had been staring at her knickers - not the ones she was wearing, sadly, but a pair on the floor, presumably yesterday's pair. They were perfectly normal white knickers with little pink flowers on them and a tiny satin bow on the front - ... Continue»
Posted by justpeekinout 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1177  |  
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I want you ALL..I am curiously insatiable!

I mean it..I dream of it..one night, a sexy, hot shemale with a wonderful throbbing cock is fucking me like there's no tomorrow..my next dream entails my sucking the nipples of a horny, bi-curious gal like me..she's moaning and so am I because I am massaging her nipples with my tongue and I can imagine how hot it must feel and how wet her pussy must be getting..the next night, I dream of a sensual and beautiful couple..we are equally pleasing each other and the experience is so mind blowing that I wake up with an aching pussy ready to be satisfied..that's my story - but I no longer want it to ... Continue»
Posted by Kymylaya 2 years ago  |  Categories: Interracial Sex, Masturbation, Shemales  |  Views: 369  |  
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Delilah and the Deep Blue Sea. (Part One.)



This story has taken me forty years to tell and I only finally relate it now in the firm conviction that nobody will believe a single word of it. In many respects that doesn’t concern me. I have other motives than those of persuading the reader of the veracity of my tale. I write it more to exorcise a ghost that has haunted me for most of my adult life and will doubtless continue to do so for the rest of my days. It is a story, the memory of which, has been my constant companion these past forty years and has dominated my life in the sense that everything I am today has been shaped by tho... Continue»
Posted by Mikebasil 2 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 1540  |  
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Tranny's First BBC

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big muscular type African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him a little smile. When I could see him coming down the hall the next time, I got up and slowly walked around the corner into the next hallway so he... Continue»
Posted by kbking64 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1527  |  
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My Sissy Fantsy pt 002

I lie still not daring to move, holding onto the arm he has round me, slowly trying you control my breathing and my excitement. Crazy thoughts run through my head and I think I’m not gonna sl**p tonight, but then before I can realise how tired I am, I drift off to sl**p.
I wake the next morning with a sticky bum and groin, but lying by myself. Outside, I can hear the storm still continue to rage, but inside, the tent is nice and warm. I roll over to find a note on the pillow next to me.
‘Billi, I’m down in the showers, get your sexy little bum down here pronto! Jake.’
Remembering last nig... Continue»
Posted by monalottanow 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 578  |  
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My sissy Fantasy pt 003

We come to another set of double doors, though these are glass paned in Victorian iron work painted white, as is the wall which it I set in. But due to the humidity all the glass is misted, including the dome and I can’t see where they lead outside. Jake opens one of the doors and we step into the rain that has subsided only a little to find myself standing in front of a large infinity pool that seems to drop off the rear edge of the building into that amazing view of the valley. Either side of the pool is a large patio that must run the entire wide of the house before simply dropping away to ... Continue»
Posted by monalottanow 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 273  |  
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My Sissy Fantsy pt 001

Chapter 1

I reach the campsite just as the sun is going down and the clear sky is bright orange as if in memory to the beautifully warm day it has been. The campsite is popular yet set on secluded farmland and as the season is just over it is practically deserted. The whole camp is surrounded by woodland and a stream lined with more trees cuts through the campsite, dividing it into unequal sections. Walking through the larger first section I can see only ten other pitches occupied by either tents or caravans and I hurry past them. Crossing the rickety bridge I enter the second smaller secti... Continue»
Posted by monalottanow 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 452  |  
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My Sissy Fantsy pt 001

Chapter 1

I reach the campsite just as the sun is going down and the clear sky is bright orange as if in memory to the beautifully warm day it has been. The campsite is popular yet set on secluded farmland and as the season is just over it is practically deserted. The whole camp is surrounded by woodland and a stream lined with more trees cuts through the campsite, dividing it into unequal sections. Walking through the larger first section I can see only ten other pitches occupied by either tents or caravans and I hurry past them. Crossing the rickety bridge I enter the second smaller secti... Continue»
Posted by monalottanow 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 702  |  
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My first TS (Part 1)

I know most of these stories are often full of cliches and often I debate how true they actually are. So now that I have experienced one for myself, I thought I would give this a shot.

So, after spending the last few months planning and searching for ways to put my ultimate fantasy to the test: to meet and f*** a TS/ crossdresser, last week the dream finally became a reality. The person in question was a tall, pale TS called Chantelle and whilst she lived down in London, it was a trip I had to make. HAving shared pics and steamy chats, the time had finally come to meet up and act out what w... Continue»
Posted by geoff_lovemachine 2 years ago  |  Categories: Shemales  |  Views: 1176  |  
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my first tranny pt. 2

it felt so good to cum in her mouth. that wasn't planned. her mouth just felt so good. nice & wet. told her what really got me off so fast was having her cock in my mouth.

"in that case, come here & suck it some more."

she laid down with her legs open & her dick in the air. without hesitation, I got between those nice long legs & put her dick in my mouth. she was moanig as I sucked her cock. she was about a good 6 inches. I just sucked & sucked. she put her hands on my head & was making me go up & down. I got her cock nice & wet.

I never told anyone this but, I loved sucking her coc... Continue»
Posted by radec_24 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1125  |  
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Chaz

Chaz

I met Chaz online. It was to be the first time I met and dressed for a guy without my wife’s knowledge. She had stopped being into dressing me or letting me dress around her. She felt we needed to get back to “normal” play.

Chaz told me he wanted me to come over in the afternoon around 3 pm after he got home from his teaching job. From our online conversation I knew that he was single, had an apartment, was a top and was looking to get sucked. He seemed a bit indifferent towards my dressing but that was ok.

I arrived at his place which was on the second floor of a big three st... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 377  |  
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