Shemales Porn Stories
Page 75

A young cross dresser's first gay experience

I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my s****rs red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my s****rs bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I was besides myself I could not believe ... Continue»
Posted by alex_boycd 4 years ago  |  Categories: Gay Male, Shemales  |  Views: 9921  |  
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Ladyboy DP for Thai Wife

I opened my eyes and lay still in bed, awake unusually early. I could feel the warm presence of Noi snuggled up in bed bedside me. She was sl**ping face down with her little bottom next to my right hand. I reached out and touched the warm butt cheeks of Noi's tight and shaped ass. I gave them a fond little squeeze and felt my cock stirring with desire.

Noi was your typical lovely pleasure loving Thai woman, very petite with a slender shaped body and girlish hips. She had lovely soft silky brown hair and a wonderful pair of red lips that were delicious to kiss, as feel heavenly wrapped arou... Continue»
Posted by sanpeesua 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 2096  |  
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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 3 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 2284  |  
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Fantasy cums true

I was on a business trip staying in a nice Hotel. After a business meeting in my room I called down for room service. The maid came up a few minutes later and I let her in. She was stunning, 5' tall with black hair and the bluest eyes I have ever seen. Under her uniform you could tell she was very well endowed at least a 34 DD. She came in and took care of the room. Thru small talk I found out her name was Terri, she was 28 and single. I thanked her and gave her a tip when she was done. As she left I had to watch her walk down the hallway, her little heart shaped ass swaying back and forth.

... Continue»
Posted by tittie-baby 1 year ago  |  Categories: Shemales  |  Views: 5173  |  
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Crissie Fucks the Neighbor

It was a Saturday afternoon and I was all alone in the apartment as my roommate Kelly had gone home to visit her
mother for the weekend. I hadn't had a date or been more importantly been laid in several weeks. Needless to say I was very horny.
I quickly flipped through the TV channels and as usual there was nothing worthwhile to watch so I clicked the off button.
I'd already read the days newspaper and even completed the crossword puzzle.
The weather was fairly warm so I was dressed in tight cut off jean shorts and a snug fitting ladies t shirt. Underneath i was wearing
a skimpy leopard ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Mature, Shemales  |  Views: 2670  |  
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dressing up

have been ‘dressing’ from a young age, the usual situation occurring, finding an aunties pink satin brassiere, a long line one which just hung on me, but that didn’t matter and also the matching corset also too large, but it felt so natural to wear these items, it gradually developed into wanting to dress more and more frequently, then it was dressing from there on.

My final transformation started about 7 years ago my wife had arranged to go away for a weekend with friends, a sort of girls weekend. I was ecstatic, my chance to dress for a weekend properly with no interruption. After she ha... Continue»
Posted by manfed 3 years ago  |  Categories: BDSM, Mature, Shemales  |  Views: 824  |  
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Riding the Lakefront--Chapter 4

Friday, August 15,2008....9pm....A Change is beginning....

Friday night, you are to go to a private party and you are going to be the guest of honor. You will come ready! Shaved. Hole greased. Clean. Arrive at 9pm. Side entrance.

These were my instructions....I would get a call and for the address. These bastards really had me over a barrel. No idea what they looked like. No names. Voices...was all. But distinct. They had done their research on me. But why me??? Like they said, a thing. That is what I was viewed as. A freak. What was the attraction? How had I 'wronged' them? Nothi... Continue»
Posted by titsR4abuse 3 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 560  |  
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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 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 848  |  
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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 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1458  |  
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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 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 927  |  
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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: 1785  |  
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Crossdresser drinks cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she wanted me to pop, she'd plunge her head all the way down my pole.

Less than three minutes into the BJ, my cock disappeared into her face. I shot my load. Nikki froze while I unloaded. She couldn't say a word, but the bemused look in her eyes told me she was loving every second of it. I must've d... Continue»
Posted by MasterDavidsslut 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2016  |  
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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 2 years ago  |  Categories: Shemales, Voyeur  |  Views: 780  |  
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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 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1334  |  
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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: 1898  |  
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The First Step With Hope- part two

I felt immediately at ease with Hope’s friends; the ‘blokes’ were much as I was, and the ‘girls’ were all very sweet and feminine, preoccupied with their nails and how their bra-straps looked etc. None of them asked too many prying questions, they seemed immediately at ease with me too and smirked at Hope as she sat close to me, eyeing me constantly and holding my hand tightly, lest I should suddenly disappear in a puff of smoke. When she did eventually accompany one of the girls to the lady’s room, the other girls jumped onto the seat next to me and the men leaned forward; all told me how ... Continue»
Posted by midsummerman 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 823  |  
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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 1 year ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 13112  |  
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Showing off

So for those of you that know me and what I like to get up to, know that I like to dress in sexy lingerie, heels and skimpy outfits.

I was doing just that earlier today, just driving around some of the quiet spots that I frequent with my camera. I deceided to go somewhere new, a small industrial estate right on the edge of a country village.

I was parked up, right out of the way when a van came past and unnerved me a little so I decided to move. On my way down to this little spot I had passed an oldish man just getting out of his car to take his dog a walk, well as I slowly drove past hi... Continue»
Posted by andismithtv 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1262  |  
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PantyBoy Gets A Reaming

I love to get really in touch with my feminine side. I get so turned on when I watch a man look my body up and down while I'm wearing some really sexy lingerie. I feel so naughty and slutty, knowing that I am going to let him do anything and everything he wants to me!! I was chatting in a room on one of the big websites when an IM from a guy in my area came across my screen. He wasted no time telling me how he liked my pictures that I had posted and how horny they had made him. I told him that flattery would get him everything, and he immediately invited me to his place. I don't usually meet i... Continue»
Posted by LRock4fun 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1182  |  
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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 4 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3783  |  
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