Shemales Porn Stories
Page 59

Unexpected visitor.............

So Tony had left and I was a fully satisfied girl, although naked under my white silk robe with the exception of my black kitten heels I felt at one. Alexander, my wife's lover was coming for supper, I had all day to prepare. I poured myself a stiff gin and pondered where I had come in the last month. My transformation from software engineer to beautiful woman was slowly coming on. My breasts were small but pert, my weight loss accentuated their size and my hips although male were sufficiently rounded to be passable. The treatments at the spa had removed all unwanted hair, with eyelash extensi... Continue»
Posted by LaceTops4U 1 year ago  |  Categories: Fetish, Mature, Shemales  |  
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There Are No Limits, part one.

*This story is a work of short(ish) fiction, and despite the tribute that I would like to pay to the real people these are based off of, their names have been changed. Chicagoland area residents will recognize some of the places despite the name changes.*


Part 1:

Sheridan and I have been partners at the Wesley Avenue Police District for something like six years. We're part of a larger group of six: Me, Bonds, Martinez, Sheridan, Maurice (the only one who uses his first name) and Woodard. Officially, we're known as the patrolmen on the night shift in Lakeview, but the brass calls us the... Continue»
Posted by asphalt3 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be there
i did think it would be nice to have it up here as well though :)

Entry #1:

I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :P


I decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there)

She told me she’s looking for a slave to entertain “them”
Thought it was a spelling... Continue»
Posted by CutiePie89 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Fucking A Cute Asian CD

I've always wanted to fuck a cute young tranny. I love their femininity - those gorgeous gurl bodies and the way they are into the lifestyle. Such a turn-on.
I pulled my cock out of my boy Kevin the other night and the two of us collapsed in a heap, satisfied with what we'd just done.
As we lay in post-fuck bliss, kissing each other and stroking our dicks, he blew my mind with what he said.
"Yasmina wants you. You can have this place on Wednesday night while I'm at the football."
Asif is an 18-year-old lad, new on the local scene and a cute flirt. Attractive boy, very girlish in the way he... Continue»
Posted by sexlover19 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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jobsite surprise

The other afternoon I went to deliver an estimate for a large gardening job I had been working on. When I arrived at the house I rang the bell and waited. There were two cars in the driveway but no answer at the door, so I walked around the back to the pool. As I came around the corner to the large hedgerow separating the back yard from the pool I heard two female voices talking and giggling. Passing the hedge, I froze dead in my tracks. My eyes flew open wide and my jaw dropped at what I saw.
Beside the pool, the lady of the house was making out with one of the most beautiful women I had eve... Continue»
Posted by leadpencil21 4 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Fucking a hot Sissy in the woods

Well, this is what got me into CD myself I guess. Despite getting off being the subbie from some men and women, I always liked girls, gurls and sissies. These I liked more from an angle of domination. So this beautiful early summer day I am out on the streets with my car, doing my "travelling salesman"-job. Taking a short break, I start browsing profiles in "gayromeo". I stumble over "Melinda23". The picture was only her chin and lipstick mouth and a sweet snub nose. She wrote that she's looking for a sensible, dominant man to explore the world and have a nice fuck :) She was obviously around ... Continue»
Posted by Cellboy1 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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From Femboi to faggot Madison

From Boy to faggot sissy Madison

I meet Maddi Ng one night as I was heading back to my hotel form a sales meeting. I noticed this young lady walking down a dark street while being followed and heckled by 4 thug looking guys. I pulled over and asked her if she needed a ride or to use my cell phone, she jumped in so fast I thought she was going to rip the door off my suv. As I drove away I looked over and noticed that she was actually a very feminine boy. I asked “what was going on” and she whispered “I promised to meet those guys for some fun but chickened out”, I asked “why would you want ... Continue»
Posted by BigDaddyJSubStable 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
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A Slut is Born

A Slut is Born
I am a bottom for sure. It has been a long time, 20 plus years, but do miss it alot. Back then, I was in my 30's and this guy I met while I was tending bar talked me into coming to his camp for some fishing. Needless to say I was the fish and did not know it. He picked me up and we went to his camp which was 1 big room with a kitchenette and a big bed, sofa and a TV. The bathroom was small with a shower only. I noticed right away he had a wall filled with VCR tapes and I am a movie buff so went over and started checking them out. HMmm, I did not recognize the titles but felt t... Continue»
Posted by iwannabeacumslut 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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the first tranny I looked for

So i've had some tranny experience unwittingly. I respond to this ad on craigslist from this 19 year old tranny who lives fairly far away, but her picture was so sexy I decided to take the hour drive. So I drive to her parents house, nervous the whole way, when I get there I get out of the car. Stone sober, knock on the door and this little hottie answers. Black and white floral blouse, visible cleavage, tight little leather shorts and a bubble but that would make real girls jealous and about 5'3". She invites me in, she shows me around the house offers me a drink, we go around to the back whe... Continue»
Posted by hothothot103 3 years ago  |  Categories: Anal, Shemales, Taboo  |  
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Travelers

It had been a long day for Nick Jackson. He had two more nights left on his five-day training stint in the small college town. He worked for a software company and had been flown down to instruct a new client’s employees on how to use the program for maximum benefit. After picking up a small salad and taking it to his room, he decided to hit the hotel bar for a glass of chardonnay. The place had a smattering of other business travelers peppered out amongst the tables – and actually there was at least one inhabitant at each. He got his wine and left his personal credit card to open a tab. Nick ... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Sissy Mailee's first black cock - part1

As long as I could remember I have always had a craving for black cocks. My first time was a few years ago after partying with a friend of a friend.

I had called up one of my CD friends, Suzy, to attend a Halloween party at a local warehouse. We had agreed that we’re both going to the party as slutty school girls. We met up at her place to get dress together. When I arrived at her place she told me she can’t go because she was coming down with the flu. There was no way I was going out in public for the first time by myself. I was super disappointed but she told me that her friend Brad woul... Continue»
Posted by aznfemboi 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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MY FIRST BLOWJOB

I met a shemale online called melisa and we had been talking over msn for afew days, mainly having saucy chats about sex and getting off. She asked me to meet her on the coming weekend which excited me as i was a virgin to cock.

We arranged to meet in a bar that was a stone's throw away from my flat, As i entered the bar it was pretty dark and i waited for my eyes to ajust to the dim lighting, then i noticed her sat at the bar wearing a skin tight, dark red dress that was knee high, she looked amazing. I walked over to her and straight away i was struck by a beautiful smile as she turned t... Continue»
Posted by handyman1991 4 years ago  |  Categories: First Time, Shemales  |  
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Thougt i could fool the staff

Realized this day would go on so decided to go buy lightbeers an two packs of ciggarettes..

Uppon arival i smoothly asked two female store attendants where i could find makeup.. yeah sure over here, they where holding back giggles i swear and as suave as james bond i just flat out lied someone is gonna look really pretty for his birthday! (u know im just getting supplies) then i asked them about what i thoght was foundation and they wher like yeah u use it to blabla and i said yeah just wanna make sure i got this note with me im not al so sure of what everything is...
So far so good..
... Continue»
Posted by tinyswede 1 year ago  |  Categories: Sex Humor, Shemales, Taboo  |  
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Sissy seeded by a black man

Hi there this is an honest, very explicit account of how i first got hooked into loving and adoring black men. If anyone is interested i will follow this post with my later varied experiences of how this has further developed.

Firstly i am a 40 year old plus transgendered person living in a female role and have done most of my adult life. At the time of this experience i was a very slim size 10 and always spent hours preparing to go out socialising or dating.
Over my adult life I had tried various types of relationship with varied genders and age groups but never felt fully comfortable in ... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Interracial Sex, Shemales  |  
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Cow Girl`s got something hard in her jeans

Last Friday night me and the guys from work stopped to have a couple of beers. which of course turned out to be a whole lot more. boy was i going to be in trouble when i got home. but when i got home it was all quite, too quite. then i saw the note. "You son of a bitch you knew we had that dinner at my mother`s!" i knew i was in big trouble now. being a little d***k i thought hell with it i am going to have a good time any ways. so i put on my boots and grabbed my cowboy hat and headed to the bar to do a little country dancing. as i looked around i noticed a nasty looking blond on the other ... Continue»
Posted by manard 4 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Allison and the Anatomy Teacher

Having recently turned 18 and exploring her sexuality with numerous hung black men, Allison the sissy boy slut was a senior in high school and going to her favorite class, Anatomy. Now, Allison is not a fan of the class as much as the hot older woman teaching it. Her name was Mrs. Ann. The anatomy teacher, Lisa Ann (not the famous porn star but did have an almost identical body) was an older woman but very fit, toned, and curvy in the right places. She was about 5’7, 130lbs, shoulder length dirty blonde hair, 34DD titties, and a bubble ass complimented by her toned legs and her preference of w... Continue»
Posted by AllisonCumms 3 years ago  |  Categories: Anal, Mature, Shemales  |  
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AdDicked to porn

Hi is Peter home. Sorry just me come on in. I wonder where Peter is but who the fuck is this babe? I'm Peters cousin in case you were wondering. My name is Julie and you? Ah Tim, I was blown away at how pretty she was. But its so warm why are you wearing a robe, I mumbled. Silly boy I only have on my new undies, I was trying them on. Oh sorry to intrude, I backed up but she stopped me and said how would you like to see them and let me know if they look good on me.

Sitting down in front of Julie she strips off the robe. My cock likes the undies. She had on soft silk stockings with a nice pri... Continue»
Posted by TenderLoins 2 years ago  |  Categories: First Time, Shemales  |  
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Adult Video Store #2

I got up and walked into the next room as she closed the door behind me.

I took a second to look around the room. First I noticed the desk she had been leaning against when she first appeared on the tv screen. Looking to my right, I saw a nice camera on a tripod. Behind it was another desk with more camera equipment and a computer with a large monitor. On the monitor, I could see the room I had just been in. The chair I had been sitting in was clearly visible in the center of the screen. I had a feeling, while I was in the other room, that she was able to see me somehow. Now I knew she had ... Continue»
Posted by naughty_bi_interest 9 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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My Evil Landlord..

This is my 2nd true story of my transexual life and the things that have happend to me in it. I moved into my own flat when i was 17, i needed the space away from my mum who was always drinking and getting fucked by strangers who she would bring back after a night out, many a time id hear the bed banging in her room and her screaming out a different mans name at night. Id find wet cum stains on her bed during the day or a pair of her panties lying somewhere that she had thrown and forgot about in her d***ken state. Always id find that the gusset of my mums panties were wet with mens cum and i ... Continue»
Posted by cinderella88 5 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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First experience

I want to tell you about my first experience in cross-dressing and what happened afterwards.
First some explanations. When I was 12 or 13 years old I was a slim and tender boy with long hair (early 70’s it was normal for boys to have long hair). I lived in a neighborhood with a lot of c***dren my age (some a few years younger or older). So I had a lot of friends to play with. One of our favorite games was “cowboy and Indians”. We played this in the woods not far from our street. It had most of the time the same scenario. The older boys (2 or 3) would be the Indians and I and the younger boys ... Continue»
Posted by Catharina 5 years ago  |  Categories: First Time, Shemales  |  
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