Shemales Porn Stories
Page 61

My afternoon getting some(true story) BB creampie

It was a Sunday afternoon and I was emailing with a guy I just met on craigs list. I was having a few drinks while starting to get in the mood. We exchanged phone numbers had a little chit chat on the phone, he told me he was straight but always wanted to experience a TS. Well this is the type that I love to entertain. So we set up a time to meet and gave him directions. I quickly jumped in the tub to wash up, shave my legs, gave myself a enamma. I had a couple hours before my man would arrive so I took my time doing a really good job my makeup (especially we where meeting during the day time)... Continue»
Posted by sarahcd_legs 3 years ago  |  Categories: Shemales  |  Views: 1890  |  
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Spontaenously meeting a straight and fucking bareb

I went out as a guy one night in my local town and I was extremely d***k hehe.. This guy was buying me drinks all night long and was very flirtatious towards me, he said he has seen me as a TV on a site and I was slightly dazed and shocked that he knew this about me.. So privately I confirmed I am a TV. When I told him that I could see he loved it that I was. So we partied until very early hours but the only thing that was slightly awkward that all my friends were there as well. But we kept it quiet that we knew what both us were. As the night grew, we went to the bar together and he was buyin... Continue»
Posted by kellyslut26 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1453  |  
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Once a Slut Always a Slut

I held my breath – and then I knew I had crossed a line – I had become by my submission, in that instant of time, another individual.

I had known Paul Phillips since I had arrived at the local school in the village some 6 years before. We had moved on together to the grammar school in a nearby town a couple of years later. We had been sort of friends from the start but as we grew older he became one of the ‘in-crowd’ and it seemed everyone sought his company and approval – for why I am not entirely sure but perhaps it was that he was a keen sportsman; good-looking bloke with an acerbic wit... Continue»
Posted by charlottekerscot 3 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 1060  |  
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A Special Girl - Prologue

A Special Girl - Prologue

By Alhana Escher


James was nervous. Alice would be arriving soon and he had a feeling that their relationship could be moving onto the next stage that night. He and Alice had been friends for years, and he had fancied her for most of them. He could still barely believe that they had been seeing each other for the last few months. He could still remember staring at her in school. She looked so sexy in her uniform. That blue pleated knee length skirt, white blouse and blue blazer. The way her socks came to just above her knees, leaving just a littl... Continue»
Posted by AlhanaCD 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1328  |  
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My first meeting with Henry - Story 2

Background: Me - Closet bi-crossdresser (Katie) - 48 yo 5'11" 185 fit; smooth all over; office manager. Quite passable except voice, sexy, attractive, submissive and horny. Only wear dresses, no jeans or skirts. Try to be a girly girl. Black lace thigh highs, red and black lace teddy, black lace panties, long auburn wig, black open toe heels, bright pink nails. Him (Henry) - 43yo construction worker 6'1" 195 toned 8 1/2" uncut muscular fat veiny cock groomed naked.

As Henry opened the door to his house, we said hi and I proceeded to walk away across the room, my short black dress, ... Continue»
Posted by hotcdsub 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 909  |  
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My First Girly Cock

It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. I don't consider myself being gay, but I always had that ardent lust to be with a transsexual woman. I just couldn't get them out of my mind.

This passion started a couple of years ago, while I was surfing on the Internet looking for hot stuff. Immediately I felt something. That first time, when ... Continue»
Posted by jimpgr 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3772  |  
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Thai Ladyboy Interview

An Afternoon With Some Thai Ladyboys

I spent this afternoon with 6 Thai ladyboys. No, don't go thinking that I tried them out. I didn't. I spent a few hours chatting with them, finding about them, trying to understand what makes them tick and learning about their experiences and the guys who utilise their services.

The 6 ladyboys are all with Ladyboy-For-You.com, a ladyboy e****t service. We met up in a central Bangkok bar and over a pleasant lunch we chatted about life in general, and specifically, life as a Thai ladyboy. There are many rumours and much misinformation about ... Continue»
Posted by CrashBoom 2 years ago  |  Categories: Shemales  |  Views: 1038  |  
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Alanya's Alternative Experiences

When i decided to write my blog i thought i would recall the early times of my crossdressing and how i started and how i felt emotionally. I suppose my first feelings of wanting to experience and develop the feminine side of my personality was when i became aware of the beauty of the a womens body and the softness of the female persona, from that moment just thinking about changing my male public image to my feminine image gives me a wonderful comforting and exciting feeling which is unsurpassed by anything i had ever imagined.That is just thinking that i might make the change, actually making... Continue»
Posted by alanyagirl 1 year ago  |  Categories: Shemales, Voyeur  |  Views: 777  |  
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Caught cumming

When we moved into our new house I got first pic of bedrooms, instantly I chose the bedroom in the loft with a nice big skylight, I love having the sun in my room and when it's raining I like watching it drop all on the window.

One day I decided to have the blind open while I went to bed, waking up the next morning I had discovered my favorite place ever. I stripped naked and lay on my bed again, my huge tits flat on my chest as I lay there I began to wank. Where we had moved to was across the road from an all girls school, what I noticed was at the right angle I could see up under the bri... Continue»
Posted by shemalecharlotte 7 months ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 13088  |  
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Fun with Stephanie-Gurl at the Park!!!

Fantasy Story: Fun with Stephanie-Gurl at the park.

After weeks of chatting online I was able to convince Stephanie to meet me but she had one condition it has to be in public place. Now I am not one to hook up in public but I was dying to meet Stephanie and have a little fun. I knew of a park that was nearby that we could meet at late at night and she agreed to the location. That night I arrived at the parking lot of the park around 11 o’clock and waited in my car. Of course being the sexy gurl she is, she made me wait. We had agreed to meet around 11 but I was waiting for almost 45 min... Continue»
Posted by Ryu1313 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1553  |  
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The Developing of Emma Part One

From an early age it had always been the same; an attraction to girly things, never quite fitting in with the boys. When adolescence brought out its spots and downy genital hair, it also brought the urge to dress in s****r’s clothes when no-one else was at home. The feeling of a tight bra and panties contrasting with the airy freedom of a thin cotton dress, whilst perched precariously on high heels, always guaranteed a healthy erection followed by most gratifying hand relief. Oh to be a girl! On one of these occasions, as an eager cock erupted whilst viewing dress and heels in the mirror, ‘... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1765  |  
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Chrissie Learns A Harsh Lesson PT 2

Chrissie Learns A Harsh Lesson Part 2

I returned to the small adjoining room as he had instructed me and once again I amazed at the accumulation
of S and M devices. The difference this time was now i was expected to select three different spanking implements
that he intended to subject me to. I suppose I could have just refused and ended this ordeal but a part of me wanted
it to continue.
"You don't have all night to make your selections you know" he bellowed "I am going down to shut the lights out
in the store and I expect you to have made your choices by the time ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 441  |  
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Training of stacy

Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions.

To make the action flow more freely and the stories light-hearted, I have taken a socially naïve approach and have not included the usual protections that intelligent people would choose such as condoms, birth control and out safeguards against sexually transmitted diseases. Such risky behavior as those exhibited by the characters of this story... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1365  |  
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She became He

The day started as normal, wake up get dressed, have breakfast,but today was going to be anything but any normal day.

I decided that i would take the day off work and visit a local sex cinema,i had never been to one before and was a bit aprehensive but i thought sod it let's just do it.

Upon reaching the cinema i stopped as my heart started to race,after a minute or so i carried on in and paid my money and went inside.

I took my seat about 3 rows from the back there were a few people inside but not too busy,anyway after about 15 minutes of the film and with my cock starting to throb i... Continue»
Posted by carlosos 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1434  |  
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Kelly gooes to college Part 2

I was a little shocked to here him say this, and i was a little buzzed, so i challenged kenny right then and there. "If you think I'm so hot big boy, why don't you fucking kiss me?" I said sassily as i stood with my hands on my hips as if to challenge him physically. To my suprise he took two steps towards me, wrapped his arms around me and kissed me deeply, our lips touching softly as they melded into one for a moment, then parted, our hungry tounges darting and probing each others mouths as we stood wrapped up in the heat of one anothers passion, never wanting the feeling of ecstasy between... Continue»
Posted by dirtygurl4u 3 years ago  |  Categories: Shemales  |  Views: 696  |  
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Summers of Love (Part 2)


The weekend following that memorable Ann Summers party saw part two of my sissy humiliation although to be honest, unbeknown to my wife, it was yet another dream coming true.

I was in my workshop grinding a cylinder block down when I became conscious of the distant sound of the front door bell ringing. It seemed to ring for ages and I was just about to wipe the excess oil off my hands and go and answer it myself when the constant droning stopped to be replaced by the excited chatter of female voices. I decided another coffee morning was in the offing so headed back to my workshop.

15 m... Continue»
Posted by MichaelaCD 3 years ago  |  Categories: Shemales  |  Views: 930  |  
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My proposal

As you know from my previous stories, I hooked up with one of my best friends, Sarah, and since then we were lover. After almost 3 years of loving each other, i decided to take my girl in a mini`trip to HongKong for our anniversary.

When we arrived there, we visited the town, and after some sex we went to bed. I couldnt sl**p so i`ve started to think about a way to propose to Sarah, and I had an awesome ideea, getting some help from a Shemale. I wasnt into shemale / male thing for a 3-way..but some of the asian shemales look too fucking awesome.

Next thing in the morning, while she was s... Continue»
Posted by mercander 2 years ago  |  Categories: Anal, Shemales, Voyeur  |  Views: 1036  |  
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My first meeting with Henry - Story 1

Background: Me - Closet bi-crossdresser (Katie) - 48 yo 5'11" 185 fit; smooth all over; office manager. Quite passable except voice, sexy, attractive, submissive and horny. Only wear dresses, no jeans or skirts. Try to be a girly girl. Black lace thigh highs, red and black lace teddy, black lace panties, long auburn wig, black open toe heels, bright pink nails. Him (Henry) - 43yo construction worker 6'1" 195 toned 8 1/2" uncut muscular fat veiny cock groomed naked.

I met Henry while drinking in a local bar after work in late August. (I was dressed in normal work clothes since I on... Continue»
Posted by hotcdsub 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 846  |  
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I wanted to be a woman



It had been about six months since my stepdad caught me dressing up like a girl and gave me my first taste of cum. I had sucked him off about once a week since then. I sucked him in many different positions since then. Sometimes I was on my knees. Sometimes he laid down and I took control of his dick. Sometimes I would lay down and he would fuck my face. Sometimes I could tell it had not been that long since he fucked my mom because I could taste her pussy on his dick. Most of the time he came in my mouth. I tried a couple of facials, but I preferred to taste the cum and swallow it down. ... Continue»
Posted by vince01 1 year ago  |  Categories: Shemales  |  Views: 501  |  
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Amy The Tranny Chapter 1

I met Amy at an adult theatre in town.
She was dressed to nines in a mini skirt, tight
halter top, and pumps leading up a pair of fishnet
clad legs. I invited her into a private booth
and once inside, went over her price for some
adult fun. She told me I couldn't fuck her as she
was on her period but I knew something was up and asked
her flat out if she was a tranny. She looked at me wearily and slowly nodded her head. I assured her I was into tranny sex and she relaxed and asked if I was into just a quicky or a longer more relaxing session back at her place. Of course I opted for th... Continue»
Posted by panteeluvr 2 years ago  |  Categories: Hardcore, Shemales  |  Views: 1388  |  
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