Shemales Porn Stories

A surprise at a wedding

Me and my friend attended the wedding of one of his old mates and I was pretty much invited along just to keep him company, and it was beautiful, a big fancy wedding, delicious food, and lots, I repeat, lots of great looking women.

It seemed pointless me being there because it wasn't long before my friend hooked up with one of the bridesmaids and just left me alone at the bar, sipping on my drink, until low and behold, I caught a cute, petite woman staring at me with a smile on her face, I decided to make a move.

We got to chatting and I quickly realised that this girl had an amazing per... Continue»
Posted by wherethewhitewomenat 8 months ago  |  Categories: First Time, Shemales  |  
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How Kenny got his promotion.

For the last 15 years I have been working in the same boring office and as a result I have actually worked my way up to quite a high up position, my own parking space, my own office, all of those benefits you get, and as part of my job I am responsible for and have to support the work experience fellows we have that do general admin duties and sorting out mail, there's very rarely any complications.

One day I'm just finishing up some paperwork and can't wait to get home as I have a nice a lovely bit of pulled pork steaming away in the house, when all of a sudden a work experience boy comes ... Continue»
Posted by wherethewhitewomenat 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My step mom turned me into a sissy slut for dad

When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere.
During the week they would work all day and I would have the place to myself. I would always go into their room and see what I could get into. I found some picture of the 2 of them nude. Well after that I was always in their room jacking off to the pictures of my step mother naked. Little by little I would find other thing to help with my fantasies. I got into her dressed and wou... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales, Taboo  |  
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Our New Life

Our New Life
By C. G. Drought

I was halfway between sl**p and fully awake effort to breathe. It is
being done for me. I can hear a mechanical sound that coincides with
every breath I take in. A click starts it and then the whirring sound
of an electric motor running.

The first few times I awoke to this sound I went through a period of
confusion and it still affects me that way but to a lesser degree. I
know the sound is the motor operating the bellows of the Iron Lung I
am locked inside. The feel of the leather straps holding my arms and
legs tightly to the... Continue»
Posted by klammer 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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A little favour

Day 1 – Friday

My neighbor Kathleen called me up one Friday evening and asked me if I could come over to her apartment and help her with something. She lives in the apartment next to mine, so I went over there. She was sitting at the kitchen table talking to a girlfriend. They were finishing up a bottle of wine and opening up another one. Kathleen invited me to grab a glass and sit down with them. We sat around the table talking and drinking wine. We drank that bottle and then another one. I was definitely feeling no pain.

Kathleen spun one of the bottles on the table. It stopped and poi... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Auntie's Panties


Auntie's Panties

I've always had this serious thing for women's' underwear. Even as far
back as grammar school I loved to sit on the ground in the school yard
to watch the girls jump rope and show off their frilly little panties,
just for me.

I was always so jealous of my s****rs! They got such pretty, pink
ruffled undies to wear while I was stuck with boring white BVD's. It
was so unfair, I thought!

I loved the exciting feel of their lace and silky nylon dainties, so
cool and silky and smooth to the touch. By... Continue»
Posted by aimen72 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Adventures in Babysitting

When I was 14, me and my BFF, Ashley, started our very own babysitting service. She made an announcement during church and we immediately started getting phone calls.

One day, Ashley said, "Come here...U gotta check this out." And she pulled out a handful of 20's. "Damn, where'd you get that?" I asked. "Babysitting," she said with a smile. I counted it...just a little over $200. "How'd you get $200 babysitting," I asked. Now, Ashley was the neighborhood nymphette and I was the neighborhood crossdresser and I soon found that babysitting services weren't the only thing that men in th... Continue»
Posted by cdsexslut 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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My first time with a shemale(True Story)

This is a true story about my first experience with a shemale.

I was sitting around the house the other day horny as fuck. My usual girl that i call on when i get that way had f****y in town for christmas so she couldn't meet me. So i decided that i would look on craigslist and see if i couldn't find someone that wanted to fuck as much as i did. As i was looking through the ads and as usual not finding any women that were real on there i clicked on the T4M section. I had always been a bit curious about being with a shemale and decided that i would respond to a couple of the ads. The fir... Continue»
Posted by wild_wolf_03 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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Surprise surprise for the babysitter

It was September of 2009 and I was coming home from my high school when my mother called me with the details.

“Hi mom, what’s up?”

“Lex, you remember the Jones’ right?”

“Sure, they have the twins right? How old are they now?”

“Well, I think they just turned twelve last month…but anyways, Mrs. Jones just called me not ten minutes ago to see if you could head over to spend the night. They received an emergency from the hospital where her mother lives and they need to leave now and they cannot take the k**s with them.”

“Wow…uh, sure, I can head over. They’re in the new part of the ... Continue»
Posted by 6270daniel 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and before I knew it, he had lost the money we had to get back home.I was so mad that i had to just walk away. About 15min. later I went back to where I last saw him but he was not there.Just as I was going back to the room I saw him at the bar with a high roller guy that had taken most of our money at ... Continue»
Posted by goodwifebad4black 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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My Shemale Stepmother

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly following the divorce and had already found someone new and I had to say, he had done pretty well for himse... Continue»
Posted by germanboi4bbc 2 years ago  |  Categories: Fetish, Shemales  |  
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Horse Cock Girl Part 1

Amy awoke, startled by the shrill chiming of her alarm. She settled back into her pillow and looked sideways at her clock. Reading the digital display she sat bolt-upright.

"8:30? Shit, I'm going to be so late!"

Amy jumped out of bed and dressed as quickly as she could in her jeans and a long-sleeved shirt. As soon as she was decent she rushed downstairs to the kitchen and grabbed a banana and an apple for breakfast. She'd have to skip the normal coffee and cereal if she was going to get to college on time.

She rushed over the road to her bus stop just as the bus arrived. She sat at... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Sex Humor, Shemales  |  
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Photographer's Assistant

By Teresa Wood

Photographer's Assistant

It had been my mom's idea that I get a part time job, but I certainly
didn't argue with her. I was going to be sixteen in a few months and there
wasn't any other way I would ever get a car. Not that I really needed one. It's
not like there was anywhere I needed to go.
My name is Louis, just plain `Lou' to my friends or at least the casual
acquaintances I've made at school. The truth is that I'm a loner, I just prefer
my own company, and so my list of true friends is pretty short. Not that I'm
disliked or anything. I'm quiet and most of the... Continue»
Posted by jayymie 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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The morning I needed a hand job, part one

I had just woken from a deep restful sl**p to the sound of my s****r Lori giggling in the open door way of my room . My eyes slowly opened and focused on her standing there in her pink nightie. She never wore panties or a bra to bed and I could see right though.
As I realized what was happening I felt a soft tug on my hard cock I saw a feminine hand softly stroking my morning hard on. It was
my mom's best friend Sandy. She lived with us and often came up stairs to wake me on school days when I overslept . That's when I realized what happening. The night before I had spent the evening dres... Continue»
Posted by michellesilk 20 days ago  |  Categories: Gay Male, Shemales, Taboo  |  
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The pretty girl with her thumb out

It had been a couple of years since my wife left and I was finally starting to enjoy trips by myself. So that fall I through some stuff in the car and headed out to see things and clear out my mind some.

As I turned at the freeway ramp there was a young woman standing at the side with her thumb out. So I quickly pulled over and, with a smile, she hopped in. As we chatted I learned Chris had recently turned 18 and was using her new status as an adult to head north to see a friend. That worked out great since it was the direction I was already going for my trip.

Chris had long blonde hair ... Continue»
Posted by need2try 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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school teen gay crossdresser first time sex

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 new 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 new 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 w... Continue»
Posted by allisontranny 11 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Neighbour fucked my s****r - but it was me

When I was 16 I stayed home alone for a week when my parents were on holiday. My s****r Jenny had just left home - she was 18. I'd been crossdressing for several years already, and I loved nothing better than to turn myself into a pretty teen girl in private. Fortunately for me, Jenny had left some of her clothes behind.

One night that week, I decided to play some dress up. I went into Jenny's bedroom and opened her drawers and closet door. I knew her clothes so well. What would I put on?

First I chose one of her bras. It was pink and heavily padded as Jenny had small tits. I put it on m... Continue»
Posted by pollyperverse 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Gloryholes and hot cum

I was young when I first started to think about what it would feel like to have another mans hot cock in my mouth. I used to fuck around with this guy all the time at his parents house. They would be sl**ping upstairs meanwhile we were 69ing on the queen cot down stairs. I would sl**p on the floor and I laid in wait for a quick tug of my shirt, just to raise up and stuff this thick monster in my throat......soon it turned into me fucking him up his ass. Which felt amazing sinking my hot thick cock deep into his waiting ass was pure bliss for me and even though i never not had luck with th... Continue»
Posted by chuckdawg802 11 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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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  |  
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Thailand Part 2

I woke up after the wank session hearing somebody in the apartment making coffee, I got up in my underpants and found my friends wife in her Brazilian type bikini behind the counter making coffee. This bikini did not cover up much and her heavy tits were just covered while her arse and cunt was split by a string. I could see her pussy lips spread by the string and I had the starting of a boner.

After coffee we went down to the pool and managed to get a couple of sun beds by the pool, she asked if I would rub lotion on her back and I worked my way from her shoulders, down her back to her bum... Continue»
Posted by daveaverage 2 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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