Shemales Porn Stories
Page 63

A Different Kind of Woman

As I was leaving work, a car stopped at the corner in the drivers seat was the most sexiest woman that I have ever seen. She had a pair of breast that was to die for, and legs that seemed to stretch for ever, and a smile that would bend steel. She saw me looking at her, probably with my mouth hanging open, she smiled and sorta of waved than drove off. I could not get her out of my mind, when I got home I jerked off thinking about her.
Two nights later I was at the corner waiting for the light to change, the same car pulled up, as I stepped into the streets, she moved forward just a little... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 915  |  
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A Slut Is Born

There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?

It had all started a few months ago. I was locked out of my house in the pouring rain, and I went over to our neighbor’s to see if I could hang out with him until my parents got home. He was a cool guy, single, mid 30’s, worked for a software company, and drove a nice car. Had bought me... Continue»
Posted by MacDaddy714 1 year ago  |  Categories: Anal, Shemales  |  Views: 4538  |  
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Crossdressed bondage

She was proud of her position. Headmistress of the Finishing School for TGirls.

So many beautiful shemale girls had left her careful administration and gone on to happy lives, or sometimes porn careers. Sometimes they had been bought outright to be used as sex slaves, but always they had gone in the best possible way.

She smiled as she looked down at the latest batch. The youngest were 18 and they were often brought in by rich families that didn't know what to do with their very effeminate boys who had painted nails and lips.

The school was there to bring the best out in transgender... Continue»
Posted by davinna_lush 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 874  |  
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My First Bukkake

It was shortly after my 14th birthday and I had already discovered (at the tender age of 12) how much fun it was to have sex! Me and my BFF, Ashley, were always finding people to get naked and have fun with and we were ALWAYS together ;-) We quickly learned that we enjoyed wearing stockings and heels, wigs, makeup and sexy outfits, dressing up like whores for men. We quickly learned that we loved sucking cocks and licking balls. We learned that we liked having our blossoming, young bodies provide pleasure for men. But most of all...we learned that we enjoyed making men cum...older men...well-h... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 3343  |  
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Gloryhole

I have had a fantasy since college. I was in the adult viewing booth when I heard a tap. I loooked down at the hole and heard a womans voice asking if I wanted my dick sucked. Obviously I did, so I pulled it out and stuck it through the hole. At first it was just licked with some tugging on my balls. Once I was fully erect she took into her mouth. She sucked it with just her mouth at first. She then started working it with one hand while gently rubbing my balls with the other. I counldn't hold back any longer. I came with such intensity I thought I would pass out. It was the best blowjob I eve... Continue»
Posted by swordlvr69 2 years ago  |  Categories: First Time, Shemales  |  Views: 1720  |  
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Shemales- The Martini affair - Part 3 - finale

I could not stop thrusting back with my ass on her face as her tongue went crazy over my anal clit and tight bud. But I could not take it for long as I fell to the floor turning around to face her on my back. As if knowing what I had in my mind, she looked into my eyes and slowly took my cock throat deep in her mouth. Just as she did that I pulled her ankles and she knew what I wanted.

So very gently she moved her hips towards me and came over me with her glistening throbbing precum weeping cock right above my eyes. I took a moment to take in and enjoy that beautiful view. Then grabbing bot... Continue»
Posted by socuri 3 years ago  |  Categories: Shemales  |  Views: 447  |  
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Sissy Emma is Turned Chapter 5

After that they let me go home.

Everything had been removed other than the cage which they said should remain on throughout the week to ensure my mind was attuned to being a sissy. Once home I showered myself completely and fell into a deep exhausted sl**p.

The following day I went to work and tried to act as normal as I could despite the fact that I was wearing stockings and panties underneath as instructed, not to mention having a butt plug stuffed up me and my 'sissy clitty' in a cage. All day the sensations reminded me they were there, the silkiness of the stockings against my hairle... Continue»
Posted by emmahighheels 1 year ago  |  Categories: Shemales  |  Views: 1356  |  
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Sissy Emma is turned

I had been a crossdresser all my life but completely in the closet and hidden from all my friends and f****y. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.
I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean I talked of having implants, of being tattooed, hair permanently removed etc but did I really want that? I also talked ... Continue»
Posted by emmahighheels 1 year ago  |  Categories: Shemales  |  Views: 4238  |  
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Guess I'll let you suck my dick!

I pulled into a rest area with a full bladder, and drove into the picnic area. I did not want to go into the rest rooms dressed as slutty as I was, and not really passable, at close range anyway.
I'd been driving dressed for hours and loving the attention of onlooking truckers checking out my legs. I'd been listening to their comments on a portable cb radio, and having a blast. So, i figured a quick pee in private in the picnic area and then I'd be back on the road for more fun. As I finished doing my business and was getting back into the car, I was startled by a man approaching and calling ... Continue»
Posted by dana213 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 2223  |  
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A Different Kind of Woman pt2

My hands were at one and eleven o'clock tied to the bed, the beautiful creature that I was so infatuated with turned out to be a shemale and I was at her/his mercy. Tiffany was working her/his penis up my butt with precision all the while stroking my penis keeping me rigid hard. Each time I thought I was about to shoot Tiffany would stop long enough for me to calm down.
Tiffany had called some body named 'Joliet' and told her(?) to bring 'Bambi' with her(?). Tiffany was having her/his self a fantasy come true pumping her/his penis deep into my butt, all I could do was grunt and groan with... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1161  |  
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I Told You

“No, please…” I barely audibly whispered.

“Shut up you little cum whore!”

“So... ohh god, no... Fuuuuuuuck,” the words leaked through my painted lips.

“You want that hole filled too, you little cocksucking bitch?”

“No, please! God, just stop please…”

“You’re so ready… I told you you’d be my bitch,” she taunted.

Of course, there wasn’t much I could do to argue with her. Regardless of the obvious physical advantage I would normally have over her, there was the small problem of being helplessly slung over the side of the couch with my hands bound tightly behind my back, while he... Continue»
Posted by Femluver 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1841  |  
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My first time with a shemale



Let me tell you a little bit about myself I'm five feet 10 inches tall around
220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer.
Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort
Lauderdale, when one night I heard a commotion in the parking lot. There were
several men beating up a beautiful woman, when I tried to break it up I ended up
getting very banged up myself.
Her name was misty, she thanked me for helping her and a... Continue»
Posted by palitro1 9 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 5184  |  
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Their First Adult Book Store. Part 4

Albert actually falls asl**p for a few seconds, before Gary opens the door to his booth. "Hey stud, thought ya might like some company over here."
Gary's cock is big and hard and right in Albert's face.
Albert's first thought is, 'I'm bigger than that'. He looks at Gary's face with its countenance of anxious, lustful anticipation. "Hey stud, to you too." Albert takes hold of Gary's dick. He starts to stoke it a little. "Wow, that is a nice dick you got there, Gary." Albert rubs up and down on Gary's cock awhile.
Gary asks “So Albert, do you and Joe…. you know… fool around with each other?”... Continue»
Posted by Michelle_Satin 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 824  |  
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Dress up fun for TV bride

I had Ben on a contact site and we live surprisingly close together in Manchester. Ben is a 6’2” black man who has a large sex drive and likes women and girly trannys.

I am a slim white guy who likes to dress like a smart woman, not a slut. I haven’t worn a wig for over 6 years and my hair is cut in a very female bob. But I like domain top men, especially those with large a cock who know what to do with it.

We had some fun chats on line and eventually met which developed into me sucking him off in a pub toilet, that when I discovered his thick 9” cock and how much spunk his manly balls h... Continue»
Posted by nikki_cd2 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 964  |  
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Sissy For My Flatmate, Chapter 1 – Caught In

My heart was racing as I gazed up at my flatmate, there was an something of an evil gleam in his eyes as he looked down at me and my mind kept jumping back to the events that lead to this moment.

I'm a closet crossdresser, yet now my flatmate (whom I managed to hide my “hobby” from for the past six months) had me on my knees, wearing what I can only describe as the sluttiest clothes I own, hands cuffed behind my back, waiting for the “surprise” he had planned.

The previous night:

Work can get pretty stressful, I'm not complaining – I enjoy my job and I have my own ways of dealing with... Continue»
Posted by Yosho 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1827  |  
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My Ultimate Fantasy...

Let me start with the details...

I'm straight, 21 years old, and am probably no more than 7 inches long. But if I may say so myself...it's a perfect cock, thick and veiny and almost always pulsing. I have always loved my cock, and rather recently I began to realize that I could no longer stop at just mine.
The more I watched facial vids, the more I focused on how hung the guy was and how thick his lines were. Now, I'm a fit guy. Work out daily, I think I have a pretty sexy body as far as gentlemen go. But, I simply don't think guys are attractive.
But I have this compulsion for cocks! I... Continue»
Posted by reddyforyou 3 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 1825  |  
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Brad, Chrissie and the Laundry

Brad and Chrissie and the Laundry

It’s amazing how much fun you can get into when you use the laundry room
In our apartment building. Let me tell you about one Saturday morning when I was busily doing a couple of weeks worth of laundry.
I was all alone in the laundry room and waiting for the dryers to stop so I could retrieve my garments. There was one other dryer being used but no one was presently there watching it.
It’s always so damned hot in the laundry so I was wearing just a t shirt and cut off jean shorts. I was braless but I was wearing a pair of baby blue thong panties. It wa... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Fetish, Shemales  |  Views: 1276  |  
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Carl's Day Off

Carl hung up the phone with his eleven year-old daughter that currently live half-way across the country. He opened the refrigerator in the kitchenette of his 350-square feet efficiency apartment and quickly realized that he had absolutely nothing to eat save for a box of Arm & Hammer and three bottles Bud Light Platinum. He headed over to closet and pulled out his worn leather jacket. Thankfully, he had shaved earlier that Friday morning. He put on his black Converse Rapid Response CT SZ work boots that he generally wore during his long days.

The 39 year old, caramel-skinned man rushed to ... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3064  |  
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hell of a night

I was about 18 at the time, and I did my usual Friday routine. Shower prettying up, then bored. I decided to go to my neighbors house, he was hanging out in his garage. In the recent months I would go over and hang out, he didn't care I was u******e and would let me drink. So I got ready after doing my makeup. I wore a black collar that was really frilly, with my playboy bra which helped with my not so awesome chest. My thong was black which matched my bra and the shirt. My jeans were blue and I thought I was smoking. I was sure to bring my purse and phone. I called him as I stepped out, just ... Continue»
Posted by Lauren_lee 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 2154  |  
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The Transformation

I woke up in a daze. It had been a night of drinking and all I could remember was everything eventually getting fuzzy. My head was spinning but that was the norm after a friday night "study night" with my friends. Most everyone was out of town but I had still gotten a ride over to my friends apartment. Anna and Heather's place, Anna is a tall redhead. She has lovely pale skin and a bigger build. Not fat just broad shoulders, massive tits, and a fitting frame. She never looked fat just healthy, always in good physical condition. Although she made me look ridiculous. I'm scrawny and 5'1... Continue»
Posted by fictiong 4 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1886  |  
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