Shemales Porn Stories
Page 77

HOW I BECAME A TRANNY WHORE (PART 2)

HOW I BECAME A TRANNY WHORE (PART TWO)
After my first night working for Mama T, I was hooked. At least once a week I was a worthless whore at her trailer. I would be at her trailer, ready to serve her cliental. Of course most the Johns picked one of the real girls over me, but there were the occasional guys that wanted some thing different or couldn’t wait. I didn’t mind. I just craved being in this sleazy environment knowing I was nothing more than a piece of useless meat on sale. After all I was tainted merchandise; I had a cock between my legs instead of a juicy cunt. The other gir... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  
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Sissgirl's sweet Adventure part Two

Sissygirl was a only a little nervous as the cab dropped them back off at her apartment; she had made sure everything was ‘just so’ at her place; a sweet perfumed incense hit their nostrils as she as eagerly gripped his hand and pulled him through the front door for the first time. Her heart was pounding as she closed the door behind them; there was no going back now, both cocks rigid in anticipation of the sweet lust to come, both yearning to shoot their hot gifts in honour of their love for each-other. He held her firmly and she giggled softly as their stiff excited members were squeezed to... Continue»
Posted by midsummerman 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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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  |  
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saturday at the Park

Saturday afternoon at about 3PM I left a bar after lunch and a few drinks. On my way home I passed a park that typically is crowded but today there weren't many cars so I went back. In the park I saw a few people at the entrance but no cars parked in the back half.

I parked on the side of the road and I looked around once again and no one was in sight. I pulled my jeans and underwear off and slipped on panties and hose. I took my T-shirt off and slipped a bra around my chest. Snapped in on then spun it around in place. Stuffed my socks in the cups. Lastly I put on a silky slip and a dress. ... Continue»
Posted by Sigrid-DWT 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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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  |  
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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  |  
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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  |  
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made to be his gurl

After waiting tables for a good 6 months, I had finally got myself clear and could maybe get myself back to California. But I wanted to get there with some money in hand, so to save the air fair I thought it would be fun to share an the ride with someone or ones. I put an ad on Craig’s list for a ride share.

I got about 4 responses and thought I had better meet with um to see if I could deal with a 4 day trip. The second guy that rumbled up was a long haul trucker, with a sl**per cab. He told me that he’s just got back from a slow go thru Texas and was about to go back same way and c... Continue»
Posted by bucketface 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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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  |  
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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  |  
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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 3 years ago  |  Categories: Anal, Mature, Shemales  |  
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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  |  
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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  |  
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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  |  
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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  |  
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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  |  
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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  |  
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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  |  
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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  |  
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lesbian adventure

I had worked a day shift - I got off at about 5 and wanted to go do something. My two buddies, Niles and Will, were there and they asked me if I had ever been to this little bar in the same strip mall as the club I worked in. I hadn't. It looked dingy and dark from the outside, and since I didn't drink, there hadn't been much to tempt me in I thought. They told me I should check it out.

So we go into this place - it didn't even have a doorman! - and my eyes have to readjust to the dark. There's a stage, but no one is dancing. They order drinks - and a club soda for me - and tell me to relax... Continue»
Posted by leadpencil21 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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