Shemales Porn Stories
Page 6

Shemale massage

It has been one of those long and stressful weeks. I’m in desperate need of relaxation and relief so I head over to an Asian massage parlor for a typical happy ending massage.
The girl who usually massages me isn’t available so another girl is suggested which I accept. I think to myself that she can’t be much different than my usual so I don’t care much. I just need a massage badly.
She comes out of the back from another massage and introduces herself as Jessica. I smirk a bit knowing there is no way her name is Jessica but I go with the bit and am happy as she is quite attractive and alread... Continue»
Posted by malesub01 3 years ago  |  Categories: Shemales  |  
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My First Time Dressed as a Girl (PT 3) (Consequenc

Well. I had written a follow up to ‘My First Time as a Crossdresser, PT 2” but Microsoft decided that the moment I attempted to upload was the perfect moment to update and erased the whole story, which means I had to rewrite the whole thing. So...

After I dressed in the schoolgirl outfit that Gunther had put out for me, I pulled my hair into a high ponytail and put on makeup emphasizing my eyes and lips without going overboard. I walked out into the living room to discover that Tracey had left and Gunther was dressed in a pair of slacks and a very expensive looking Cashmere cardigan. He s... Continue»
Posted by sbobbi66 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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my friend's new roommate and her surprise

So my friend Rebecca and I were planning on going to this bar for the evening but she called me and said she was running a bit late and that I should wait at her place and that her new roommate Shawna should be there to open the door for me. Rather, than wait in my car I went upstairs to her apartment like she suggested. The door was slightly open so I walked in saying hello; to see if anyone was home. I heard some noise in the kitchen so I walked over to check it out. It was Shawna cooking. She was actually a pretty cute girl. She was wearing a white tee shirt that just about covered her ass ... Continue»
Posted by pleasurenfun 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Summer transformation Part 1

My jaw hit the floor as I read the first email I ever received from John. My mind twisted, heart raised, and my pussy pulsed repeatedly.

A week earlier I had posted an ad on craigslist... One of those late night d***ken fantasy ads where you spill your darkest desires, wake up the next morning and think "wow... I really am a pervert!" My ad was placed M4M, M4MM, M4MW, and T4M. I wrote:

" 18 year old looking to experiment. 5'5", 170, naturally smooth. School is out so I have lots of free time, super horny all the time, looking to learn. Discretion is a must, can`t host, love mature ... Continue»
Posted by archerfan88 9 months ago  |  Categories: First Time, Shemales, Taboo  |  
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First Blowjob

I pulled into the reststop needing to pee badly. As I walked into the restroom, I spoke briefly to a trucker, and went about my business. While I stood there peeing, he took a peek at my dick. At the time, I hardly even noticed it.

As we went to leave, he said he was going the same way as I was and would be monitoring his CB radio for reports on where cops might be. He then invited me to follow him. I agreed since I wanted to make good time. We drove for about an hour when he pulled over. I thought maybe something was wrong so I pulled over too.

He got out and walked back to my truc... Continue»
Posted by KaylaCD15 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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My Ex-Girlfriend's Mom

My name is Bobby. Before I tell this story, let me set it up by telling a short story first.

At the end of my senior year in high school and into the beginning of the summer, I dated a girl for a few weeks but never got past making out with her. Her name was Jill. One weekend Jill and her mom, Lana needed to leave town and asked if I would check in on things at their house. I did as they asked and once, while I was there, I got on the computer and watched some porn, shemale porn.

A few days after they got back, Jill and I got into an arguement and I broke it off with her. She tried calli... Continue»
Posted by naughty_bi_interest 10 months ago  |  Categories: First Time, Shemales  |  
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Going to the Gym

“I’m headed to the gym, baby,” the six-foot-three-inch two-hundred-sixty-pound Black man said to his wife of seven years.
“Ok,” she replied barely looking up at her beefy, brown-skinned husband. “I’ll be at the hairdresser by the time you get back.”
“Alright. See you later,” Darius Woodham smiled.

The former Division One linebacker started his black metallic 2012 Ford Expedition and backed out of the driveway. At the end of the street, he stopped at the intersection and pulled out his phone. He sent a message to the person he was heading to see.

Three months prior, Darius was watching ... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?

This is a real life story of a crossdresser caught in the act!

This happened around when I was 15 yrs. old.

As my s****rs were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my s****r’s jean skirts and a blue and white sweater with some black 3 1/2 heels.

I put my ma... Continue»
Posted by sparkyking 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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Brittany The Cheerleader

It was my second year as an assistant counselor at River High School. I was young, in my mid twenties. Everything was typical in the small town school. I would help students with scheduling issues, direct them towards colleges, and help them with different scholarships and programs that would benefit them. It was entirely unremarkable and nothing out of the ordinary happened until I met Brittany.

One day a woman walked into my office. She was tall for a woman of her age, yet very slender and petite, with an almost non-existent chest, gorgeous round bottom, tanned skin, and long deep brown... Continue»
Posted by wedgietime 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Becoming the neighbourhood slut

The following is a fictional story but mixed up with some real experiences and a few of my actual desires :)

The first real days of spring were finally upon us. This was extra cool since I would be alone for a week or so. I took a few days off of work too, so I can spend the time dressing up at home and possibly try to find some real fun too.

When I got a few free days I always did the needed grocery shopping in the morning so I have the rest of the day completely free to dress up and stay dressed up. I usually went to a shop nearby, grab the needed stuff quickly and go home.

I di... Continue»
Posted by analhottie 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Scary!!!! my friend's mom has a dick!!!!

It happened last Sunday when I visited my new neighborhood Jack's house... They have arrived in the city a week ago from that day... Jack and his Mom(Aunt May). As we came to know aunty may was a single mother. She was a woman of 40-45 years with heavy tits and pale white skin. She looks like a perfect milf. Me and Jack has just completed our school so we were planning for some camping, hiking and mountain climbing. When I visited his house last Sunday then I came to know that Jack slipped from the stairs last night which cost him a fracture in his right leg. That was really surprising for us... Continue»
Posted by hunter043 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Fun with the Mechanic

Last weekend, I had a date to go out to a bar with some other CDs in another state and a 2 hour drive. I would get dressed when I got to the motel. On the way I had car trouble, but kept driving to the motel. Told the girls who were already dressed that I couldn’t go to the bar or play because I could not relax knowing my car was having problems. I was so horny because we had set this date up a few weeks ago and I had spent the day trying on my new sexy short black dress and getting ready.

I left the girls at the motel and headed home with the car having transmission problems. On the ... Continue»
Posted by hotcdsub 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
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I'm sure many of you have seen a number of movies or television programs based on prison life behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I'll now share with you first hand, some of the wildest and most unbelievable sexual experiences one could ever imagine.

While still on parole now, I will change my name here and not mention the state facility involved. Other than to substitute a few names for some of the real ones involved, all of what I'm disclosing here actually happened between late July of 2007 and Dec. of 2009. My work... Continue»
Posted by cddixie 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Bikini Boy

boy in panties – bisexual threesomes - bisexual lust – s****rs' panties – boy on boy sexfest – crossdressing pleasure – luscious girl on girl sex – secret lingerie stash

I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage. Then came the divorce. The fights, the yelling & screaming about the "other woman" resounded through the house & the k**s tr... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Kitty got caught - in college!

I love risky sex. I like to humiliation. I like to be treated as a useless piece of fucktoy for real men’s pleasure! I love the thrill in sex when there are chances of getting caught or something else that pushes me. So how did I figure that out?

Dressed in lingerie and wearing pink lipstick in my college, kneeling on the floor beside the toilet, waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it.

I remembered sitting on the toilet earlier today looking at my bright pink nylon and whit... Continue»
Posted by CumLovingKitty 7 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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mommy's new girl

It's true that I had become accustomed to drama in my f****y. My father was loud and mean, especially when he was d***k, which was most evenings and every weekend. He would back my poor mother into a corner of the kitchen and berate her, towering over her in that threatening way that I knew so well, telling her she was fat and ugly and stupid and spending too much money on me. He would get louder and louder until she finally began to tremble and sob – then he would storm out of the house in disgust, as if her crying gave him the right to leave his "silly emotional wife" and visit his drinking ... Continue»
Posted by momandboys 3 years ago  |  Categories: Fetish, Mature, Shemales  |  
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mom teaches son to be a slut

I loved women. A lot. My obsession with women later became a desire to wear women clothing. One day, three months after my 18th birthday, I could not hold back any longer, and I put on the the most accessible lingerie I could find - that of my mother.

Since then, I frequently visited my mom's wardrobe whenever she was out. I would wear her clothes, and it would make me feel sexy. I would pretend I am a woman, and take sexy pictures of myself. I realized how much I liked this, and this led to me realizing my bisexuality. I wanted a man to make me his woman.

Because I wanted a man so badl... Continue»
Posted by momandboys 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Fitting Room Fun

It’s about 8:45 at night and I am at this department store looking for some new clothes for the weekend partying. There weren’t too many people in the store, just an older married couple, a few employees, some teenagers, and a mother with her k**s. As I am headed towards the jeans/bottoms rack I notice a girl in some skinny jeans bending over. She had a cute little ass and a thin, slender body. She was pretty short about 5’4” with hair just down to her neck. I was about to walk up to her when suddenly she starts heading in my direction. That was when I noticed that she wasn’t a girl at all, bu... Continue»
Posted by pleasurenfun 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Boy gets Fucked by Shemale

This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when I was sixteen, I decided to see what it felt like to be a girl. I had never tried anal before (I could never bring it up to my girlfriend) but I knew I had to try something. So I gathered all the necessary tools and went into my room. I locked my door so my mom wouldn't accidentally walk in on me a... Continue»
Posted by ClassicCockx 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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A Nurses Fantasy

This is a fantasy. Very, very Loosely based off of my experience at a hospital over my 18th birthday. Enjoy!

When I was s*******n I found myself in the hospital for a few weeks. It just so happened that I was going to spend my 18th birthday in the hospital and was really bummed out at first, but I soon realized that being in the hospital wasn’t all that bad. Though the doctors set strict rules, I found out that the nurses pretty much ran the show because doctors never stuck around, and were pretty much never even in the hospital after noon. I am a pretty charismatic guy and my person... Continue»
Posted by wedgietime 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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