Shemales Porn Stories
Page 15

Losing my Cherry

Although l have been secretly cross dressing for years I have never took it beyond the confines of my bedroom or hotel room. Well I have been really wanting to take this to the next level. So as I was traveling on business this past week I answered an ad on Craigslist for a massage in my hotel room from a male masseur I made the appointment and waited with anticipation for my masseur to arrive. At promptly 8:00 there was a knock on the door and when I answered there was Chris a very handsome young man, I invited him in and he promptly set up his table..
As he was setting up his table and ... Continue»
Posted by mikkas72 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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becoming a slut

It all started when I was 13 and discovered the joys of wearing women's clothing. It started with my older s****rs panties then my highschool girlfriends things by the time I was 18 I had a pretty good collection of womens clothing even with never having the nerve to purchase any of them myself. Then came the urge for more when dressing up and masturbating wasnt enough I wanted more. I always considered myself straight despite my crossdressing but when dress would get the urge to please a man. So one day I got my s****rs 7 inc dildo. I got dressed up in some sexy thong panties some nylons and ... Continue»
Posted by RenoBoi 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Double Anal With a shemale

....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36 D and she was 5'9 with heels on. She went over to him and kissed him with lots of tongue. She then grabbed his dick through his sweats and said "Hard already we haven't even started. Where's your girlfriend?" He said "In the bedroom prepping her asshole" She said "mmm maybe we can get a quickie, He... Continue»
Posted by michneo 4 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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The Truckers Reststop

I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem myself up it was already 8pm, so I thought what the heck I'll drive up the Interstate just north of Seattle to a truckers rest stop I have gone too before. The weather had cleared up a bit, so I was hoping for some fun. I dressed in my short wrap around skirt, red thong panties, red Bra, and a shea... Continue»
Posted by cd_lorretta 4 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Shemale Summer

Once again, this is not a story written by me! It was stored in my computer for ages and decided to share it with you. Hope you like it!


One hot summer day, my friend Sam and I were scoping out the babes at our local beach, as usual. I saw this really hot, busty blonde a few towels down giving me the eye.
"Hey, check her out!" I said to Sam. He peeked up from beneath his Ray Bans and shook his head.
"Forget that one," he said. "She's not your type."
"What do you mean?" I said. This girl would be anybody's type—even blind men!
"Just take my word... Continue»
Posted by freegre 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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Sex with teacher(sissy)

I was the 2 year of high school back then. My grades werent going realy well moastly becuse i spent most of my freetime blowing guys,and sticking thing in my ass,then studying.My parents one day decided that i need some extra classes,so they hired a tutor. I wasn't realy up for that idea,but they somehow talked me into it. After a while it was the time for me to have my first class. My parents left for work,and i was home alone waiting my teacher.Then the dorbell rang , i felt so nervous as i opened the door. In walked a handsome 25-6 year old man,fresh out from college,in a very nice suit. We... Continue»
Posted by sissygirl1988 1 year ago  |  Categories: Anal, Shemales  |  
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My first time being taken dressed as a woman

I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman.
Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a few months ago.
As it turned out my wife would be away for 3 weeks and opportunity presented itself. I quickly got down to planning and slowly but surely a plan came together, well sort of anyway.

I went online and ordered some womens lingerie, wigs, panties, make up and a few slutty costumes, ... Continue»
Posted by jimbo70xyz 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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Tranny gang bang

It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place.

What was I doing in here? In truth I did not know but I was 16, horny and wanted to find out about the rumours about sexual activity.

I was still a virgin and although had messed around wanking at home, I was very naïve.

I walked into the last cubicle, shut and bolted the door, took my trousers down and sat down to relieve myself. As my eyes became accustomed to the gloom, I ... Continue»
Posted by allisontranny 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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Frank's Friend

Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a little d***k. Frank pulls up to this leggy blonde in a short skirt and fishnet hose and asks how much. She told us she would do us for free for a ride home. We said fuck yes. Frank had me drive to her house while he had her in his lap, kissing and groping her. We got to her house and went i... Continue»
Posted by biguy52x 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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she trained me

I was sent to Aunt Fergie when my parents were killed. She is about 5'7"
and 200 lbs she was your stereotypical aunt with some fat and wide hips and
big breast. She picked me up at the bus station in her car.

She said," My household is different and special I have girls who you
will find are very unique. I too am unique and I will show you what I mean
when we go home."

We rode for a half-hour and we arrived to her big old which I would find
was an old Victorian with a widow's roost on top of the roof.

She e****ted me to the bedroom that would be mine and told me," Put your
... Continue»
Posted by pcarter 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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SOMETHING ABOUT DANNY

What was it about my daughter's boyfriend that turned me on so much? No one characteristic comes to mind. I suppose it was a combination of things. And perhaps a certain time in my life also. I was 52, divorced, alone and quite bored.

I had been divorced from my husband Jerry for 12 years and didn't really have a steady boyfriend. Jerry and I remained friends but he seemed to be turning into an old man. I was still young at heart, or so I felt. But the more men I met the more disappointed I became. It had been getting to the point where I would rather stay in my apartment and read than go o... Continue»
Posted by couple_kinky 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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The Tgirl Hooker

All my stories are based on real life experiences.

I spent a few weeks looking at e****t sites, reading reviews, services, likes & dislikes, pictures... until Emma caught my eye.

Emma was Eastern European, had a tight slim body, blond hair, very fem and a nice cock. I wasted no time and contacted her to set up a visit and within a few hours she replied and we discussed what I wanted.

The day soon arrived and I was quite nervous through excitement. I had visited e****ts before but never a Tgirl. I pulled up to this house in a normal road and knocked on the door, and there stood Emma i... Continue»
Posted by dirtydisco99 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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My First BBC

It was not long before I told my wife about who I really am, that I was having serious desires to be taken by a real man. I have / had no true preference, but something about getting pounded by a cocky and arrogant black guy really turned me on. But I wasn't looking for some thug or prick to just have me. I wanted a man!!! A black man.....a BBC man!!! One who had a hot bod, aggressive demeanor, and of course a huge cock. So I had my expectations, and I was anxious for this experience.

I had been dressing in full for a while at this point, but my wife wasn't actually aware. Porn was... Continue»
Posted by Ivygurl86 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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S****r has a Secret

Sarah was rummaging through her bedside drawers, turning them out and messing up the room she shared with her younger s****r, Hope. She was looking for her ipod. She had no idea where she'd put it when she'd gotten home the night before.

It was when she reached her bottom drawer than she found something interesting. Pulling out the stack of photographs that she hadn't known was there, she became furious. They were nude photographs of her, in the shower and masturbating.

Sarah was a transsexual. She'd had a sex-change when she was 18 because she'd always felt wrong in her male body, thoug... Continue»
Posted by drew1207 11 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Dad uses me for his wife

After a long and unstable marrage of 20 years, the divorce papers finally came. My wife and I only had one c***d, William, and he is very gay. My wife was too much of a homophobic bitch to support him. Even when he was younger we knew he would turn out gay. Always wanting to wear girl's clothing, dress differently, speak differently, even walk differently. I always supported him as a dad and as his friend. I never understood and I still don't understand my wife and how she could just leave her only c***d and I. I remember it was his 18th birthday, about five months ago. She came home from work... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Shemales  |  
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the surprise I loved

I never had never heard the term shemale or transexual. Didn't know anything about it. I joined the military right out of high school. Ended up in the far east and started out on the town. I saw a great looking girl in a bar and started to chat her up. I bought a few drinks and we were both starting to loosen up. Then out of the blue she asked if I wanted to get out of there and sme place more private. Now I had a few girlfriends in high school and had sex with a few of them but i had never had anyone address me like this. I wasn't she what her intentions were but I knew I wanted to fuck her. ... Continue»
Posted by gayswitch 3 years ago  |  Categories: Anal, Shemales  |  
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Couple Uses Katie

So let me start off by giving you a bit of background here. This is a couple who I have played with a few times. They are really nice and understanding. They even allow me to come over and get all dressed there before we play. And yes they are an interracial couple. With that said.......

I don't know where I was or what I was doing, but I was bored and horny and looking for some fun to occupy my mind. Come to think of it, I'm pretty sure I was just in my house on a typical Saturday afternoon. I put out an online post for BBCs. I'm sure if you know me, then you would understand I... Continue»
Posted by Ivygurl86 12 days ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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On the road

Dannielle had decided to finish work at dinner time and go for a drive the long way home seeing as the day was so nice. As she got into her car she thought "i will put the soft top down and get a tan". As she got in the car she looked at herself in the mirror and checked her make up, hair and her top. She had noticed how the boys in the office had been looking her up and down during the day, well she had dressed for the attention. Her tight white top that showed her black bra off really well and her short black skirt that was so tight that you could notice the outline the suspender belt she wa... Continue»
Posted by danni1 4 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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My one and only experience with a tranny/shemale

One Friday night I decided to take a ride to Hollywood to check out adult theaters as i had always gotten my cock sucked at different adult movie theaters. As I parked my car on a side street i walked to this one particular movie theater I found myself at entrance and paid the 5 bucks to enter. as you all know, when you go into any movie house, its always dark and you wait for a few minutes for your eyes to adjust to the surroundings. i was standing near the entrance and looked around to find an empty seat. i always look to find one in the back near the isle, but they were taken, so i went... Continue»
Posted by 1superhornyguy 2 years ago  |  Categories: First Time, Mature, Shemales  |  
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My Transformed Wife Part 2

"Absolutely," I said, rising to my feet and offering her my hand. She took hold and I pulled her to her feet. Her knees wobbled and I caught her by the waist before she could collapse again. "Woah, easy there."

"I'm not used to using those muscles like that," she said, grinning.

"Yeah, I'll probably be walking funny for a while myself." I helped her into the shower and she sat down on the built in bench next to the shampoo and soap bottles. I pointed the shower head at the wall, turned on the hot water, and waited as steam began to fill our little alcove and condense on the glass door. M... Continue»
Posted by drew1207 10 months ago  |  Categories: Anal, Fetish, Shemales  |  
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