Shemales Porn Stories
Page 66

A Girl To Remember

Senior year is supposed to be the best year of high school. For me it was absolutely remarkable. Junior year, second semester, I went to the office for my teacher. A girl I liked helped in the office for her free period. She was Japanese with long black hair that fell down her back. She had icy blue eyes that were accented by her black eyeliner. She had on black lipstick, black converse, and a black and purple skirt with black pants on and a black t-shirt with purple letters that read, “If you think you’re normal. You are weirder than me and I’m a Goth.” She looked like a little Gothic fairy. ... Continue»
Posted by nightheart13 1 year ago  |  Categories: Shemales  |  
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First Time By Transsexual

When I was 21, I spent a summer in a southern city doing a service project. I was engaged to a girl and excited about marriage, but I was also extremely curious about the male body. I was one of those k**s that masturbated constantly, and almost always about sex with a man or a transsexual. The summer before my senior year, I was down in this southern city living completely on my own for the first time. Since I was doing a service project, I only got one night a week off. I wasn't sure what to do with that night since I didn't know anyone, so I decided to get d***k. Several times, I just went ... Continue»
Posted by kbking64 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Ebony TS of my dreams


This story is about one of the most memorable piece of cocks I've ever experienced in my 30 plus years of getting fucking. I just thought I'd write it down and share it simply because I'll never forget it and because I'm a married man and it most likely will never happen again.

It happened about three days ago with TS Dominique I met through the internet(EROS). She was 23, but she easily looked 20. She kept her body pretty fit. She was about 5'11 and 135 lbs. I love tall women because I'm physically a big myself--6', 245lbs. It's hard to be fucked by a woman bigger than yourself. Plus, I... Continue»
Posted by yesamwilling2 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Old Black Carl (part 3)

Old Black Carl (Part 3)
After the long night, we slept in late, the next day. Carl made me suck his cock again, and of course, I enjoyed it. He said he had some things to do and that he would drive me home, so that I could rest, and that he would be picking me up again that evening. He drove me home with his arm around me, and of course, he had me play with his big cock while he drove. He dropped me off in front of my parent’s house, and told me to be ready about 6. I nodded, and walked into the house. I knew I probably smelled like cum and sweat, so I went directly to my room. I thought abou... Continue»
Posted by cocksucker4bbc 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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More Dirty Sex with Tania. Part One Hotel Sex

More Sex with Tania


Part One. Hotel Sex

It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch and myself at about 3ish. We agreed it that way so it gave Tania time to dress and get ready, however it did mean that I would have to arrive dressed as Joanna. I have a lot of confidence when dressed, as Joanna but most of my forays have been either a... Continue»
Posted by joannacd1 4 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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my first time

this will be the last story i write unless someone asks me personally for more... as Andy i felt no one loved me and if i was a girl i could be that slut and try to feel some kind of love from someone. when i was Andy i dated 6 girls in the course of 2 or 3 years and 4 of the 6 cheated on me and the other two clearly hated me and made my life nothing but misery... Ana was my only way to feel any kind of love or happiness.. when i first dressed as Ana no one was interested in me i was shy and i was still trying to find the right look for me... one night i decided to go to a party and find the d... Continue»
Posted by drewcd 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Dawns Early Light

Almost closing time and I was enjoying a wicked high but not quite d***k. Looking around the Bar I saw almost nothing that would make my night any better and thought I'd simply head out for home. The other Bars were letting out and people were sorting out their options and pouring into their vehicles or making last ditch efforts to not go home alone. The Cops were out in f***e in the area watching for belligerent d***ks and last minute d**g deals. I knew I shouldn't be driving so I thought I'd stop at a local eatery for breakfast. It was a popular place and a lot of folks coming and ... Continue»
Posted by Keith_Walters 1 year ago  |  Categories: Shemales  |  
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An unusual surprise

This storey is a bit different to anything I have written before. It was written for a friend as this was a scenario she wished to explore.

Sally contacted me and asked if I fancied some fun, never being one to turn down a good time I immediately agreed, she said she had a little surprise waiting and I was intrigued. I arrived on time and was stunned to see Sally sat with another beautiful lady at the bar, after greeting both ladies Sally suggested we head straight to the room as she could not wait to show me what the surprise was!

As the room door clicked shut behind us I watched as yo... Continue»
Posted by zibbles 4 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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cross dressed cocks

I was looking forward to the fun I could have in my own place. I spent some time on the male chat line looking for someone to play with. he to liked to dress but like me was not at all passable . when he showed up at my place he hade on black thigh highs open toe heels and a corset ,he was taller then me and of average build . it was the bulge in his panties i was interested in. I was dressed in pink thigh highs red strappy heels pink panties and a light purple chemise with a pink bra under it.

we sat on the couch watching some porn he took out his semi erect cock and told me he wanted to s... Continue»
Posted by amitokinki 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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The real me part one

Well let me began Iam not in the closet, I grew up in small town my mom raised me cuz my dad was not around. This town was dead and in my school days there was only myself and friend of mine that were the only k**s in town. It was summer and my friend had left to go spend the summer with his grandmother in other state.
My mom was a 5'9" 130 lbs d breast woman that raised me and worked her but off doing it as only hair stlies around for a 100 miles. She always wore dress and skirts and heels dolled up everyday. So oneday I was bored around the house when she was home taken a break. We were... Continue»
Posted by cdpaula 3 years ago  |  Categories: Gay Male, Shemales  |  
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late night hotel halls

I am 46 years old and travel quite extensively for
businss. I dress in my hotel room at night when i travel.
I sometimes entertain in my room. Sometimes I get very bold and wander out to the soda machine dressed sexily. Its about as bold as I ever get. I am quite tall and do not pass in public. But i am very smoooth and try very hard to look fem.

Anyway, very recently i wandered into the hotel halls about 3 am at a business hotel I was staying in outside of
Indianapolis. The soda machine was at the end of the
hallway. I looked up and down and when i thought the coast was clear I... Continue»
Posted by cherylfabrizio 3 years ago  |  Categories: Shemales  |  
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Alice 2

Alice part two

I checked out and drove home in deep thought, I knew I was in love with Carol, I could only hope that she felt the same about me. How am I going to explain to my dad about dressing up and most importantly about my job. I decided that I would be dressed when he got home from work, then tell him what has happened, he obviously would have found me out anyway. I arrived home about lunchtime, I stripped off, had a shower and douche, I picked out a nice black above the knee cocktail dress, nice silky black underwear, near black ... Continue»
Posted by ratty9uk 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
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THE BUSINEES TRIP - PART I

HI

This is another one of my real life experiences. All my cross dressing and sex experiences are on my work trips as that is the only time I am alone and I can indulge in my pleasures ( as I live in a joint f****y n India so cross dressing at home or in my home town is not possible).

So here I was getting ready to go on another work trip to Lucknow ( a big town in the state of UP in India). I reached there by train around noon and since the office was about 60 kilometers out of town I hired a cab as I would be staying there overnight. I contacted the travel agent at the rail station and... Continue»
Posted by hornyboyind 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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xdresser foxxiroxxi fucked by daddies poker buddie

So I have finally got my men doing what ive wanted for a long time now and I have never been so horny . John is licking and fingering my ass while im getting marcuses tounge shoved in my mouth all the while my daddy and his buddies are outside . Fuck me im so fucking horny these guys could do anything they wanted to and I wouldn't stop them. Johns fingers start at one then two big black fingers slowly stretching my virgin ass then he slipped a third in and out licking and sticking his tounge in my ass then fingering me ,he kept the same pace making sure he didn't rip me so it would be a pleasu... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Summer affair with a latina ts mmmm

So, we all are busy and have our jobs n all and not much time for fun...So i'd thought ill try craig's list for the hell of it-which was something I would never have tried in a millions years lol. Jokingly I was repulsed by what i saw under the casual encounters but decided, "what the hell." I put up an ad with a toss away email saying something along the lines of 'big black juicy cock for horny latinas and white.' Mind you in the small town of Chico California i doubt any one would even check it, even left my cell number on there as well lol. So far, tons of spam, a few responses but they wer... Continue»
Posted by iluvtgurl 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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my fantasy part I

I've always been interested in being a prostitute but never had the guts! This is what I would do if given the opportunity!!

It was another morning alone in my dump of a one bedroom apartment. Sexy shemale porn playing on my laptop and me performing my usual morning edging session!! I was strolling the web and came across some pictures of sexy crossdressers hooking on the streets! This made me want to cum so bad but I couldn't because I was edging and it felt to good when I stopped myself from cuming. I usually edge for an hour or two until I get so much precum my hand is sliding up and do... Continue»
Posted by nebraskasissypussy 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Whore For Two Mexicans

One night I came home from work and saw a old beat up truck from Texas parked in in spot next to my room. As I walk to my room I looked in truck and the back was full of tools and junk, then looking in the cab I could sdee it was a mess with trash everywhere. I thought who ever it belonged to must be slobs. As I got to my room I saw my guess was right as two mexican guys came out of room next to mine and they were a dirty mess. I looked at them and said hi and sort of smiled, they both had sort of nasty grins on there face as they looked at me.

That night I was standing outside having a bee... Continue»
Posted by sissy_gurl 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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One night I

The last time I got fucked was in may or june 2011,. in spokane, wa. I was horny and d***k in my mums apartment with no privacy,. so I got on craigslist,. and sent out a few emails to people who have posted looking for a bottom boi, or something to that extent. I got a few replies back but chose the one closest to me (just north of the fred mayer on freya) cause I didn't have a car,. and would have to hike over to meet him. luckily it was only a few blocks away.

I got to his place and waited around the back for him to come to door,. I didn't knock ,. but texted him and let him come outside ... Continue»
Posted by villelohne 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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caught masturbating & crossdressed living at a

This is the first story of a few that I was so lucky to be a part of and I would love to share them with you!

I had hired this woman as a delivery driver because the store I had just taken over had ruined the reputation of the business with terrible service. Her bubbly demeanor, bordering on ditzy was cute and she was herself a beautiful 40 year old woman and a milf for sure! She would be my best tool in the road to rebuilding the business. The customers will love her. She was tall with long slender legs and a real nice round ass, small titties with huge pinky size nipples. Her hair wa... Continue»
Posted by happytayls 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.

We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.

Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or would prefer to wait in the room while she finished dressing. I told her I would like to wai... Continue»
Posted by johnny_antares 1 year ago  |  Categories: Shemales  |  
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