Shemales Porn Stories
Page 59

The Blind Date Night Part 1

The date was arranged by a good friend of mine, she said she'd shown my picture to Warren and he kept pestering her to arrange a meeting. I finally agreed to meet him with no strings attached or promises. I had no idea what to expect or how far things might go but I always like to be prepared. I showered, shaved my legs and any other area that needed attention, shampooed my hair and perfumed and powdered my body. I decided to wear black thigh hi stockings, a black push-up bra and the cutest tiniest string bikini panty. The panty was black with a touch of lime green lacy trim. The lime green st... Continue»
Posted by chrissieCD 1 year ago  |  Categories: Anal, Shemales  |  Views: 661  |  
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BLIND DATE NIGHT part 2

He grasped my hand and we walked briskly from his car to the door of his condo with my 5 inch black heels clicking madly against the concrete. We moved in such haste that I was afraid I'd come tumbling down from the height of my heels. Once inside the condo he roughly grabbed me and pulled me tightly against his taut gorgeous hunk body. He leaned down and locked his lips to mine. He used his tongue to easily part my lips and f***ed his tongue down my throat. Our tongues quickly met and began a dance of passion. I was in heaven and ready to give myself to him totally, wantonly, eagerly and sure... Continue»
Posted by chrissieCD 1 year ago  |  Categories: Anal, Shemales  |  Views: 661  |  
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Afternoon's Delight

She stood at the folding table in the apartment's laundry room. She saw him across the room, reading a paper, but not really. She could tell from the glances around the paper every now and then that he was checking her out. She smiled to herself. She enjoyed being checked out, especially by an older guy. She stood five feet six inches, and had rich thick brown hair, with some sun bleaching, lightening it. Right now it was up in a pony tail but unpinned would fall to her lovely tan shoulders. She was wearing a halter top, one of her faves. It accented her full 36C breasts besides exposi... Continue»
Posted by sliplover 10 months ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 661  |  
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The Bondage Whore, Chapter 4

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 4 - First Day on the Job

Rachel barely slept that night, wondering and worrying about what exactly was going to happen on Thurday. It was terrible when she crawled into bed, realizing that she wouldn't be able to finger herself to orgasm, a nightly ritual for her. As she laid in bed, she chanted "$2,000 a week, $2,000 a week" to herself to try to keep herself upbeat, that she had made the right decision.

She finally rose at around 2pm, and showered. Her bladder felt full and she could feel pressure in her intestin... Continue»
Posted by thongcutoffs 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 660  |  
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Fantasy Cum True

I have always had a "thing" for she-males, but growing up where I have and hanging with the crowd I hung with, it was taboo to express this thought. I used to go home d***k and pull up shemale sex videos on my computer after hanging with the fellas and I would be so horny watching these creatures that looked like women, with curves and all, but nice juicy cocks to go along with it. I would often fantasize about an abrupt meeting with a shemale and for whatever reason, we would talk and become cool. In my fantasies i knew what I was meeting and wanted it. We would talk and everyone around u... Continue»
Posted by heater31 1 year ago  |  Categories: First Time, Shemales  |  Views: 659  |  
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Aimee and Me

My name is Shaye and I’m a 27 year old pre-op transsexual. This is the story of my only sexual encounter with another shemale, which turned out to be one of the most intense sexual experiences of my life.

I first started speaking to Aimee about two years ago on an adult chat site. We had some cyber fun for a few months, jerking off on cam and generally having a good time. Eventually, Aimee asked me if I wanted to go around to her place for some real fun. I didn’t need to think about it and I arranged to go to her house a week later.

It took me two hours or so to drive to her house. More ... Continue»
Posted by gellid12 5 months ago  |  Categories: Shemales  |  Views: 659  |  
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defeated...

alone in her ugly room, staring at her flabby figure in the mirror, aroused, taking pictures of her reflection with a cell phone, hiding her boyish face behind it, not caring about the pile of dirty laundry in the frame, the tip of her little cock, sticking out of her tiny immature panties, squeezed between her thick pale thighs and her round belly fold, her soft moist skin glistening after a shower, pink flesh, her tender budding tits in a black lacy bra, her adorable chubby feet out of frame.
on her back, lying on a wet towel she spread on the floor, legs pulled back in the air, her little ... Continue»
Posted by enkaiein 2 years ago  |  Categories: Shemales, Voyeur  |  Views: 658  |  
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Talyns Adventures: Part 1

(This was a story written on request by a good friend of mine. Hope you enjoy!)

(FANTASY story: F/S ahead. Fetish is Fantasy setting with awesome elf.)

Her name was Talyn, and this is the beginning of her true adventure. Talyn was an elf, a beautiful young woman that stood slightly taller than most of the other women of her city. She was considered beautiful among the elves, and a rare flower with her striking red locks. They swayed slightly with each step they took, back and forth just above her large, firm ass. She dressed differently than most adventures, and her weapon was certainly ... Continue»
Posted by JasmineCS 12 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 656  |  
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my best friend

when i began dressing as Ana i had three sexual experiences one with girls and two with boys.. this is the experience i had with my second boyfriend his name was Connor and he was this cute shorter boy with longish brown hair and he was so cute. anyways when we first met i could tell he knew somehow i was a boy but he still loved me and kept trying to be my boyfriend. one night we were in a movie and he began feeling me up.. i let him do what he wanted while we made out because he never grabbed for my crotch that was until now.. he grabbed my cock but he didn't pause or was surprised , but i w... Continue»
Posted by drewcd 1 year ago  |  Categories: First Time, Shemales  |  Views: 654  |  
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Oh,,,,,,,, so helpless

The ankle straps of her five inch heels connected by a short chain and secured in place with tiny padlocks. A virtually unnoticeable black cable secured around her waist held the shiny steel handcuffs that pulled her silken gloved hands behind her, leaving white glossy fingers resting on the very large white satin bow that in turn hung across and down the short black silky smooth skirts and numerous frilly petticoat layers of her French maid uniform. Zipped to the neck and edged in brilliant white lace frills, the locked bodice of her dress was clinging tightly over the uplifted bosom and cor... Continue»
Posted by maidtracie 1 year ago  |  Categories: Shemales  |  Views: 654  |  
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TRANSLESBIANS [this is a true story ]

When I first got married in 1992,my exwife,and I were getting along well,everything inbetween,ecept for sex,either I was stressed out from work,or somthing else.well one night we were talking in bed,and were dicussing what we wanted to try out in the bedroom.I'd say well blindfolds,and being tied up sounds nice,or even whipcream,and some type of cream dessert,where we would smear over are bodys and lick it off.but then it happen,I told her that I use to dress in drag,she replied what?she new what I was talking about,and went to raing hell.after a few hours of arguing,she finaly calm down,wasn'... Continue»
Posted by blonde68 10 months ago  |  Categories: Shemales  |  Views: 650  |  
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My New Whore

Disclaimer: All characters portrayed are over the age of 18. Any similarities between persons living or dead is entirely coincidental and unintentional. These characters are entirely of my own creation, and thus don't belong to you. Don't use them or this story for your own purposes. There's a reason they belong to me.

Justin's body trembled, as he sat in his chair, his eyes glued to the floor. It was obvious from his reaction that he hadn't expected me, or anybody for that matter, to walk into his apartment that night. We had been friends for several years now, and though it ... Continue»
Posted by BigStevieAwesome 2 years ago  |  Categories: Anal, Shemales  |  Views: 649  |  
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the real me part 4

I took our ice tea back into the den.Mike an I were on the love seat kissing and fooling around.When our mothers came in an sat down too.We all talked and watched some tv show.When my mom and becky said they needed me to come upstairs for a few minutes.
The 3 of wentup to my moms room were they had me get undressed.They had me put on a white and pink full corset with white seamed stockings they hook the gartor straps to the stockings. I put on pair of pink stillettos and sheer white short camsole and sheer pink long robe.Mom and Becky figured know painties was best route.I looked at myself ... Continue»
Posted by cdpaula 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 649  |  
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came to play pt.2

I must have dozed off, when I came to I was being felt on by the janitor who I knew well, he seemed to really enjoy what had taken place, infact I dare say he has quite the soft spot for girls like me... Well anyway we chatted to ease the tension from me and we both finally got interested in fun time, he removed his cock which was roughly 4-5 inches and I asked him if I made him cum would he help me get home.. he chuckled and said if you make me cum ill give you a ride home and dinner honey... I slurped him down quickly, but he took forever to cum, I tried everything even as far as putting him... Continue»
Posted by reefermcrevolver 1 year ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 648  |  
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Wealthy Sissy Surrender Station

Fire immediately engulfed the house just next door after an earth shaking explosion rocked the neighborhood. Fear was setting in. The rebels were getting closer and closer, Inch by inch. Relentlessly. Terror crept in as silhouettes and shadows extended deeper into the darkness with sudden flashes of light exposing their footsteps. I held my breath and cowered in the corner of the room. Shock waves riddled the streets. Please, let this end. Another bombardment shook the ground pushing me around and tossing loose paper in the air. I started to cry and that's when the pamphlet slowly fell into my... Continue»
Posted by amberfemxd 2 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 648  |  
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Help or give tips please.

OKay so Ive been having sex frequently,with different trannys (bareback) of course.And everyone of them seem to complain alot about prostate massaging.About 5-6 minutes of intercourse they have to cum, but yet their not touching themselves at all.I thought it was because I thrust way to fast, but even when I go slow they have to cum.Some of them tell me to stop when their about to cum but when I do so they tell me it hurts while they try to hold it in.

My doctor told me my girth may be a little too big, he said try not to use any lube so I didn't & the T-girl Ive had sex with was telling me... Continue»
Posted by guess1tw3ll 2 years ago  |  Categories: Shemales  |  Views: 647  |  
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A true story: me and a transvestite man - part 3

This is the last part of my true story. I had expected it only to need two parts, but it seems that I'm quite a wordy writer, so it now spans 3 parts.

Where did I leave off last time? Oh yes; Toni, the gorgeous Brazilian TV was leaning forwards, dressed in her black lingerie, her firm arse towards me, ready for me to enter her. Read on...

I wasn't expecting this to go well, as I'd only had a little anal sex before, with a woman, and this had been on a bed, where I could jockey around for best position. However, thanks to my extra height (6'3" against Toni's 5'10" or so) we seemed a p... Continue»
Posted by LookingForSomething 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 647  |  
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black man's sissy boy

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 was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by jeffreybarnes 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 647  |  
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The Football Jock and Chrissie

The Football Jock and Chrissie

Back in college, sharing an apartment with my BFF/roommate Kelly, a lot of my dates and hook-ups were arranged by Kelly. For some reason she always seemed to know just who was into what when it came to sex. She learned a lot about other people’s likes and dislikes from hanging with her lesbian crowd. She was also super inquisitive and fancied herself as somewhat of an amateur detective. I just thought she was nosy.
It was 1998, the middle of our junior year, and I had already been transforming from Christopher to “Chrissie” for 4 ½ years by this time. Needl... Continue»
Posted by chrissieCD 10 months ago  |  Categories: Anal, Shemales  |  Views: 646  |  
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Cumming of Age

When I was younger I can remember summer vacations with the guys. We were a small group of six or seven close friends. I can't remember who made the suggestion but we would set or stand in circle facing each other and masturbate. I'm sure that is when I first sensed a curiosity of having sex with another guy. I know I've always enjoyed watching another guy get off ever since those early days. Glory holes would cum later.

When I got older my sexual thoughts pointed me in the direction peep shows. It was pretty much an age of sexual freedom when the only worry was how fast could I get a... Continue»
Posted by milkmanj 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 645  |  
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