Shemales Porn Stories
Page 74

Old trannie gets a boys virginity

Oh dear I’ve been a bad, bad old trannie. I let a teenage boy seduce me.

I normally only go with guys over 30 at least. But this teenager contacted me on a dating site. I gave him the normal “Thanks but I’m in my 40’s you’re a bit on the young side for me” reply. However he kept contacting me on the site. He was very curious and quite sweet. I chatted with him online and he said that he would really love to meet me.

I told him if he wanted to meet me that he could find me at my local sex club. He said he couldn’t go there. After a deep thought I said it would be O.K to come round on the... Continue»
Posted by toniparr 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4461  |  
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A Quickie For Jemima

I checked my make-up and adjusted my brunette, bob cut, wig in the bathroom mirror. Pleased with the results I then ensured that my clothing was right. I was a vision of darkness: black G-string under black thin denier tights, 3 inch heels, black satin vest top and black mini skirt. I was sure Simon would approve.

I walked slowly yet purposefully to the bedroom. Simon was sitting on the edge of my bed naked stroking his cock looking at me “mmmmmmmm,” he said seeming to approve “ Why don’t you cum and join me the doors open?”

Out of habit I shut the door as I enter in case we made a lot ... Continue»
Posted by JemC 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 835  |  
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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 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 7051  |  
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Ladyboy Secrets

LADYBOY DIARY
by utubeslut

forgive the misspellings but inocent words get sensored
by the auto censeless

Diaries can be dangerous and have unexpected
consequences if they fall into the wrong hands.
Or the right hands ….


Early Spring and that meant a visit from my
Aunt Becky and my cousin Susie.
I loved Susie but she was kinda weird.
She had mood swings like she had permanent
PMS, very unpredictable.
Otherwise she was very sweet.
Crazy bitch.

The neighborhood girls were drawn to Susie
like a magnet. Crazy peop
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Lesbian Sex, Shemales, Voyeur  |  Views: 1218  |  
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The Arrangement





My wife and I have been married for 10 years and are very much in love but we do have our own little fantasies as we have learned over the years. She is 5'8" tall, blonde hair blue eyes, in my mind, quite a sexy body, with great legs, a nice ass, and ample breasts. She really looks pretty hot.......when she wants to. As for, me I am 5'10" about 165-170 lbs, and as her I have blonde hair and blue eyes. I have a fairly nice build, having been a collegiate athlete and still in ok shape.

That being said let me set the scene for what has taken place in our lives. Early in our marriage w... Continue»
Posted by lonicd 2 years ago  |  Categories: Fetish, Shemales  |  Views: 1853  |  
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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  |  Views: 1565  |  
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Adult Bookstore Dancer

Adult Bookstore Fun
At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make about me in the front as much as I did sucking off cum filled cocks in the mini booths in the back.
One of stores had girls working in the front that would give you a privet dance, for a fee, in one of the many privet room available. I meant Ida there. I was in drab and looking at the BDSM magazine... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  Views: 886  |  
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tranny hooker ( UK GUY SEEKING CONVINCING TV &

I was out late looking for a cheap hooker with £15 in my wallet I should at least get a blowjob. After 20 minutes of searching I see a young girl stood on the corner. I pull up along side her she tall long legs short skirt stockings m holdups long dark hair as she bends down I tell her how much for a bj. For u darling £10 for everything I m more than happy with that. Once in the car she tells me to drive down the road and take 2nd left. We end up down a dark alley at the end a quite car park. Once there I turn off the car she opens her legs grabs my hand and slides it down the inside of her th... Continue»
Posted by crbigboy 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 874  |  
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me and connor say goodbye..

Connor and i were f***ed to separate some time ago due to his f****y moving for work. he never specified where but when he told me this we only had a few days together before he had to leave.. we spent the next day trying to figure out if there was a way for us to have a long distance relationship, and we did our favorite thing to do which was to walk through sex shops together, and we saw some kit to clone a dick.. i got excited because i thought maybe i could give it to Connor as a piece of me so we would stay somewhat close... Connor didn't know i was making it but i had it ready the day be... Continue»
Posted by drewcd 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 248  |  
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Riding the Lakefront-Chapter 2

August 13, 2008...8pm....Rec lot...Irving Park Rd...Chicago lakefront bike path

The event that actually changed my life began when I needed to piss about 6:30pm while on my bikeride. Tightfitting bike shorts were worn because of the padding in the ass area. But had I worn a pair of shorts with a zipper, none of this would have happened. Had I not worn a zippered tight biker shirt with my 48D tits showing, this might not have happened. But, it also was extremely hot and to be zipped up would have been ridiculous. 95 degrees, humid...typical August summer late afternoon/evening. Even a... Continue»
Posted by titsR4abuse 2 years ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 884  |  
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Sissy slut training ends in 3 BBCs final chapter

Well after getting fucked in the car park on the front of the limo by the driver my arse is ready to be fucked by my three black bulls.I have been waiting a long time for this and now I am ready for to be fucked like a slut my arse is Gunna get stretched to it's limits by these black studs cocks .The limo pulls up outside the apartment and my heart starts pounding so hard with excitement I can't wait .We go upstairs and as soon as we get in the door I'm sorounded by all the guys they are kissing me on the neck and in the mouth they take turns stiking there tounges in my mouth .But misstress x... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 323  |  
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First Sissy Fuck Part 3

With cum leaking out and slowly dribbling down the inside of her thighs, she kneels and starts to take long and slow licks up the length of my wet cock. Then she teases the tip with her lips and slides a finger into my ass.
The feeling is delicious.

'Good girl' I say 'Let me take off the cage'

I sit on the edge of the bed and she stands in front of me with her sissy cock level with my face, I can smell a mixture of sweat, cum and perfume, I can see veins pulsing as she is obviously very aroused, and there is a bead of pre cum on the tip. When I unclip the cage her cock springs out and ... Continue»
Posted by honestjohn1962 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 946  |  
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Aint a woman that comes close to you

Angie slipped in the room for our occasional discreet encounter. This time she was dressed as a hot MILF wearing shoulder length blonde hair, dark red but lightly painted lips, trimmed dark eyebrows, lightly dusted eye shadow and rosy painted cheeks. She wore a pearl necklace with a white dress that covered her arms and stopped at her knees with nude colored hose and white heels. She wore two diamond rings that highlighted her freshly manicured fingers. “You look so sexy today” I whispered in her ear as I brushed her hair back and tasted her shoulder with my lips. She turned pressing her lips... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Shemales  |  Views: 379  |  
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She dresses him like a slut

My cock was as hard as it could get when Jaime came in the room. I could feel the moist pre cum rub on my thigh. Carol had made Jaime up to look like a total slut. Jaime had dark brown shoulder length hair, thick shades of blue that ran from the drawn on black eyebrows to her to long black eyelashes and around the bottom of her eyes, her lips painted pink with a thick coat of lipstick. She wore a tight black strapless cocktail dress that just covered her sweet spot with black nylons that had a thin dark stripe down the back stopping at her sexy black high heels. “Suck his cock now” Carol barke... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Shemales  |  Views: 1213  |  
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How I became a GURL part II

So I'm in college now, I've learned to love and use porn in all its forms, I've learned to be a great cock sucker and to have my ass fucked. I've learned to tie myself up -- as best as possible -- to pee all over myself to get that humiliating feeling. I'd spread the porn mags all over the floor and spend the entire night playing, trying to shoot my cum onto a photo of a cock so that I could lick it up.

The feeling of release whenever I gave in to all of those instincts was fantastic!

I loved cock! But I was a horny 20 something and still chasing pussy. Eventually the girlfriends star... Continue»
Posted by jenn1 3 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  Views: 902  |  
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3 Teen Cross Dressers Misadventure - Part 3 Final

I was with two of them on the bed. One of them spread my legs and began to rub his cock up and down my stockings, I could feel him growing hard. The other sat over my chest and told me to open my pretty mouth. I did but no way could I take it all, he must have been around 8". He shoved his cock into my mouth and down my throat thrusting as I gagged. Although I couldn't see, I heard pleasurable moaning from the man on the bed with Sean. Craig, on the couch with Brett said "I’m gonna screw that pretty little hole of yours and make you scream like the bitch you are." No words came from his mouth,... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 751  |  
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Tranny Gas Station Attendant

This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intimate, but I consider it just sex. When I say I'm not intimate with other guys, I mean I don't kiss or cuddle or anything like that. It's always just sex, with no strings attached.......usually! There are exceptions to any rule, and this experience is one of them!

... Continue»
Posted by panteeluvr 4 years ago  |  Categories: Shemales  |  Views: 1928  |  
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I posted a craigslist ad.

8 years ago I began crossdressing again and playing with toys. After playing one day while watching videos online I decided I wanted to take the next step and be with a man again. My holes craved it but the butterflies in my stomach had stopped me before. Afraid they would do it again this time I got dressed as slutty as possible and put up an ad on craigslist with a photo of me dressed and spitroasting myself with toys. Pic required I put in the posting. I was amazed at the responses and how many people couldn't read or just saw the photo and replied without reading. I didn't think it w... Continue»
Posted by bibottomboi 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1110  |  
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My first threesome.

My lover and I just finished sucking each off and were laying next to each just talking and he ask if I had any fantasy's and I said I like dressing in lingerie. He went to his closet and came out with a black bra and panty set along with a full black slip. He asked if I would put these on and I was up so fast I tripped and fell to the floor. I didn't think I made any noise and started to get dressed. He went into his bath while I was dressing and then his bedroom door open and in step his step mother. I didn't know what to do but stand there in the lingerie. She just smiled at me and wa... Continue»
Posted by billieearls 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 2542  |  
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My sister, my first, the tranny

A little something different to spice up your lives

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It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to... Continue»
Posted by 6270daniel 10 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 11238  |  
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