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 1 year 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 1 year 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 4 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 3 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 5 years ago  |  Categories: BDSM, Fetish, 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 4 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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Cutting Ms Betty's Lawn

My mother had suggested I might consider cutting Ms Betty's lawn as none of the other boys in the neighborhood would. All the other mothers hated Ms Betty and wouldn't allow their sons to associate with her. She was one of my mom's friends and I thought nothing of it, so I agreed to do it every week. It seemed Saturday mornings would be best, so I put her in my schedule and planned on the following Saturday to the first.

I was doing a great job with my lawn cutting service, picking up new clients from word of mouth after I did a lawn or two, but my schedule was becoming full. I needed to sa... Continue»
Posted by goodsonformom 7 months ago  |  Categories: First Time, Mature, Shemales  |  
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Bobbi






Bobbi - New Girl in Town
(TV, Transsexual, Prostitution, Gay & lesbian sex, Anal, Oral)


[Note: the original author of these stories prefers to remain
anonymous]

Margo sat next to me in the coffee shop late that Saturday afternoon.
His real name was Mark, but he was one of the loveliest Drag Queens in
New York City. I had been dressing secretly at home in my mother's and
s****r's clothes for just over three years, but at 18 years old, I had
never been in public as a woman. Margo lived now as a female, and could
pass anywhere. I complimented "her" on it, and "she" said,... Continue»
Posted by klammer 1 year ago  |  Categories: Gay Male, 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 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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my first time exploring a Tgirl

long time ago as a straight men i was at a big Mall looking for a new pair of pants. There was this lovely young woman named Sherry working there, who was very solicitous, helping me find my size and select a pair of pants that weren't too out of style. I hate to shop, you see, so I usually wear a pair of jeans or shorts. These sort of clothes don't require trying on and are really never out of style. But this time, I wanted to take my time and get a nice pair of pants that fit well.

She was a redhead, about five and a half feet tall, with a very attractive, thin build. I prefer natural rou... Continue»
Posted by mandy_66_night 3 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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Cutting Ms Betty's Lawn ~ Chapter 2

Chapter 2

I nodded, of course I did. I wanted my pants off and I wanted to be touched and sucked. I loved sex and would if asked, say I was addicted to it. Betty undid the button on my shorts and they fell to my ankles as I stepped out of them. "Oh my......you have such a lovely cock G......so smooth and hairless.....do you shave it? she asked. "Well.....a little.....I hardly have any.....but the few I have look stupid.....so I take them off." Betty cupped her palm over my cock. It felt warm and I shivered thinking how much she seemed to like it. "Oooooooooh.......did you just tremble?........ Continue»
Posted by goodsonformom 7 months ago  |  Categories: First Time, Mature, Shemales  |  
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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 1 year 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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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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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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HUSBAND AND WIFE USED BY MR. BIG BLACK COCK


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 4 years ago  |  Categories: Gay Male, Interracial Sex, 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 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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The Transformation --- Prologue

I come from a very poor f****y of eight. My father is a mine worker who became very ill only a few months before the beginning of this story and got into early pension for a very small income. My mother is from very orthodox origins without any school and she can barely read and write so she was a housewife for her whole life. As the oldest male c***d from 5 s****rs and 3 b*****rs I had to quit school and find work to earn something so our f****y was kept fed. Our only property was our house in a very bad state so we had nothing to sell to get some money. If we sold the house we would have now... Continue»
Posted by harloch 7 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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My Transgender BFF

One of my best friends Sarah is a transgender. When we first met I had no idea, no one did. She has always looked very feminine, I sometimes think that she looks better than me. She had some classes with me so we started to talk and we became friends quickly and started hanging almost every afternoon. Eventually she stayed the night at my place.
Things were normal until it got late and we were both in my room laying down. She was going to sl**p on the ground but instead she was laying in bed with me because we were chatting. We were both facing each other and my bed was small so we were v... Continue»
Posted by sweetiepi99 3 months ago  |  Categories: First Time, Shemales, Taboo  |  
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