Shemales Porn Stories
Page 5

Gurl Story – Be Careful What You Wish For

“This one right here” Max said. “This little sissy is perfect!” Max and his two friends had spent the last few weeks scouring Craigslist personal ads for a small crossdressing sissy that they could take advantage of in the back room at Max’s dive bar. “I’ll email the cunt with a few pics of my nine-inch cock – see if she bites!” he bragged to his friends. Sure enough, two hours later, the CD named Holly liked and commented on Max’s pictures. Throughout the day Max and Holly swopped information and emailed each other, then Holly decided to send Max pictures that he wanted (face, her little siss... Continue»
Posted by MatureBrownMan 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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First time used

James didn't know at the time that the hairdresser wanted him. He could feel the press of his bulge on his forearm but in his innocence thought nothing of it and sat still answering the questions he was asked.

'16. So what are your plans now?'

'Not really sure, I am thinking of going to college.'

The hairdresser positioned a mirror behind James head, placed a hand on his shoulder and said, 'Doesn't that look good?'

It did look good, thought James.

'So, Jimmy, do you smoke?'

'Cigarettes?'

The hairdresser laughed, 'No, weed.'

James did, although he had only smoked h... Continue»
Posted by waraxe13 1 month ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Karen My School Teacher 4

My excuse for a cock got hard again. My horniness got the better off me. I went to lock the front door. Took my shoes, pants and sweater off. I stood in the hallway only in pantyhose and t shirt. Don't do this. Walk away from this now. But you go to boarding school soon. You will never have a chance like this again. Was way too horny to let this pass. I sat next to her again. “Karen. Hey sweety. Are you there” But nothing… Mmmmm my cock was hard. My pantyhose legs touched her pantyhose leg. Oh my, it felt so good. I took my cock out and started playing with myself with one hand and the other t... Continue»
Posted by HosieryQueen 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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Meister - T - Sissi Hooking

Meister – T – http://xhamster.com/users/meister-t
Erziehungsplattform Mann – Frau – Sissi – Paare Frau und Mann
Aus dem Leben eines Meisters.

Sissi "Schwanz und Eier "Hooking"

Ein Meister – der sehr strenge –
packt die Eier enge –
drückt sie – bis auf Boden –
haut dann noch – die Hoden,
an diesem schönen – Leiden –
tun sich gerne – weiden –
Sissis – und der edle Mann –
der so immer – gerne sann –
zu dienen – einem Meister –
der auch kennt – die Geister

Heute ist ¬ die große Feier ¬
denn erzogen ¬ werden Eier ¬
von de... Continue»
Posted by Meister-T 1 month ago  |  Categories: Anal, BDSM, Shemales  |  
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Gurl Story – Be Careful What You Wish For

“This one right here” Max said. “This little sissy is perfect!” Max and his two friends had spent the last few weeks scouring Craigslist personal ads for a small crossdressing sissy that they could take advantage of in the back room at Max’s dive bar. “I’ll email the cunt with a few pics of my nine-inch cock – see if she bites!” he bragged to his friends. Sure enough, two hours later, the CD named Holly liked and commented on Max’s pictures. Throughout the day Max and Holly swopped information and emailed each other, then Holly decided to send Max pictures that he wanted (face, her little siss... Continue»
Posted by Browncherrygurl 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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My Two Traps! Part 1

It all started one night by me being d***k and a little high. I was cruising the personals online looking for a couple. I had a real need for licking some pussy and sucking some dick. I generally prefer females but have been known to mess with couples and single males. For some reason a regular couple didn't seem kinky enough for my mood. I decided to place an ad for two trannies or crossdressers. Most of the replies to the ad were junk mail.

I got one response with some pics and a phone number. It stated that there were two femboy traps looking for fun. They wanted to party and play. I cal... Continue»
Posted by captainchaos01 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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Transition to Vikki, part 3

Next part of how Steven Jennings became Vikki. Mk 2 version. Original script had too many typos and grammar errors for my liking,



One moment I was sipping wine, the next I'm pinned to the bed under Gina's body. She'd pounced on me like a cat, knocking my glass and wine all over myself and the duvet cover, and then started to move herself around in a way which would certainly get a response given time. I could feel the bars of her protruding nipples digging into my chest as she moved about, could feel her hips as Gina gyrated and ground herself on me. I could feel her begin to grow and harde... Continue»
Posted by fluffy1 1 month ago  |  Categories: Anal, Shemales, First Time  |  
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My Life As A Sissy

My Life As A Sissy

From the earliest awakening of my sexuality I felt a strong desire to be girly. I was the smallest boy in my grade at school and my slender body was milky white and nearly hairless. I felt that my penis was unusually small as well, and I didn’t have any pubic hair until at least a year later than the other boys. My first reaction was to shave it off, which I did on summer vacations so it wouldn’t be noticed in the shower at gym. I was back to being deliciously smooth, and by now I was starting to get erections and masturbate, though I hadn’t had an orgasm yet. My fav... Continue»
Posted by pinkydik 1 month ago  |  Categories: Fetish, First Time, Shemales  |  
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His first time.

He sat in front of the mirror, as he slowly put on the makeup and applied lipstick to his mouth, making it seemed more luscious and full. He then got out of his chair, and went to his cupboard to look for his attire for the night. He was debating in his mind if he should put on the OL attire, or if he should go for the Japanese schoolgirl look. It was then he remembered the client specifying that he likes girls in their schoolgirl uniform as they look pure and wholesome. He also remembered the client mentioning about having hard-on when he sees schoolgirls in their colored, lacy bras through t... Continue»
Posted by jillc94 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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growing up

i had a super crush on my friends mom growing up, i stole her panties and bras and hot clothes , whatever i could get my hands on you know, they lived right behind me in a small village almost rural, doors never locked. when they were home i just walked right in. i was over all the time. even tried some peeping tom type stuff but not super into it. shit started to get real though around 14-15 yrs old about 2005. the mom(stephanie) caught the husband cheating on her with this super young chick who was married to a guy that worked for his construction business, well they're super catholic and th... Continue»
Posted by nickymyself 1 month ago  |  Categories: Shemales, Fetish, Masturbation  |  
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Anal fantasy

I'm just an anal slut. That's all I like. The feeling of a huge cock breaking down my defences, a giant and throbbing hard member forcing itself inside me, and stretching my anus until it breaks open just drives me mad. Then I want to feel the entire length burning its way up my rectum and starting to pound me like the cock whore that I am. But it's a fantasy. I'd be too scared to carry it through.

Anyway, I went shopping after work the other night. I stopped by my appartement first to get changed. By the time I went shopping I was wearing high heels, white fishnet stockings, a very shirt a... Continue»
Posted by Chazzbuzz 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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Used like a BBC Whore

This is a story I wrote about one night being used at the sleazy hotel I lived at. If you've seen it before it was posted



About a year ago while living in a hotel and living there as a Transexual I was used by a young black man as his whore for the night.

He moved in about two weeks ago with a couple friends. They where maybe 5 rooms away from me on 1st floor. As the week wore on I would be coimg and going and would notice them watching me. When I would walk by they never said anything but one of the guys always smiled at me.

While one night I got a phone call and he said his name was R... Continue»
Posted by faggotsissy 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Playtime Stories 18 - Minivan Ménage-a-Trios

This was crazy and hot...the third in a mini-series about adventures in the IE. Enjoy and comment!

18 Interracial Minivan Ménage-a-Trios

Still on my glorious business trip, I had enjoyed a LOT of cock at arcades and some nearby hook ups. After being fucked so well by Dommie’s huge hard BBC I went on a night-long binge. I sucked and fucked every cock offered, but never hit my itch exactly right.
I took a day off from being a whore.
The following day the cock-binge hunger returned. Dommie was working the rest of the week and wasn’t available. So I went with the backup plan... Continue»
Posted by 6988slutty_rbckyy 1 month ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Playtime Stories 17 - BBC Afternoon Delight

The second in a short series of stories set in the IE. This one was INTENSE. Enjoy and please comment!

Playtime Stories 17 - BBC Afternoon Delight

I put a prostate stimulator up my ass and moaned. My dick jumped and I smiled at myself in the mirror and called myself a fucking slut. I jacked myself a few times and nearly came. I wanted to save my orgasm. I had so many possibilities and so many ideas of what to do for the rest of the day and the night. I liked my lips and preened in a slutty way.
I was in town for part one of the closure of a project and arrived early so I coul... Continue»
Posted by 6988slutty_rbckyy 1 month ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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Playtime Stories 16- Toppin' a Cuckhold

This is the beginning of a short series of mostly true Inland Empire adventures. What a deceptively freaky place.
Enjoy and comment!!

16 Topin’ a Cuckhold

Finally! I thought. A big business deal was nearing completion with two other partners. I would tie up the loose ends in one city and then fly to the other partner to conclude the deal. My boss was pleased and even told me to add in a day between stops to insure all went smoothly. This was going to be great!

I packed up my bag and tucked away a couple of outfits and both shoes and boots for wear as Rebeca. I got the ear... Continue»
Posted by 6988slutty_rbckyy 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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That certain girl

I met her in the old yahoo chat rooms. We talked for about a month, then she started to cam with me. She was very pretty. No nudity or anything on cam. Just talking. We talked about all kinds of things. This went on for about 2 years. We only lived an hour apart, so the hesitation was due to both of us being attached and the fact that she was not a normal girl, but a transexual. I guess it was fear on my part.

One day I was at work (which was just a few miles from her home) and at lunch we both were on messenger. I told her where I was, and she said to come over. She said we did not need to d... Continue»
Posted by dualcoil 1 month ago  |  Categories: Shemales, Taboo  |  
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My first ladyboy experience -unintentional

My aim whilst in Thailand was to try a d**g that translates to crazy medicine. A small smoke able red pill.

Due to my inebriation I pulled up next to a ladyboy. Her lips so appealing, she was short but thick set in a power type way. Her thighs were thick and her boobs busty. I found her sexy as she was majorly feminine in all featured.

She offered me sex for 500 baht and I struck a deal with her to share her crazy medicine at hers now and I will give 500, no sex involved.

She seemed to like this idea a lot and said ok but she also said I will definitely fuck her.

We arrived at her ... Continue»
Posted by upforanything121 1 month ago  |  Categories: First Time, Shemales, Taboo  |  
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Halloween sissy slut

Halloween. It's just an excuse to go out drinking with friends like any
other night, only this time in a ridiculous costume. And since my friends
and I definitely like to party, it makes sense that I dress up for the
occasion.

This year, I decided to surprise the guys by dressing up as a girl. At
costume shops they have a thousand different "sexy" costumes. Sexy cat,
sexy cop, sexy pirate...I always loved it when I saw girls wearing these
costumes, so I thought it would be fun to put one on myself. I grabbed one
off the rack at a pop-up Halloween store near my house. Luckily, I'm sma... Continue»
Posted by bfer13 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Nicoletta's Sissy Abenteuer

Es war ein etwas launiger Herbsttag. Die Dämmerung brach langsam ein und ich setzte mich gerade an eine Hotelbar in der Münchener Innenstadt. Im Hintergrund bemerkte ich wie eine kleine Männergruppe, in etwa in ihren Vierzigern, sich zu mir umdrehte, als ich mich auf den Barhocker saß. Der kurze pinke Bleistiftrock hatte sein Wirkung wohl nicht verfehlt. Darunter trug ich eine mit Spitze gemusterte schwarze Strumpfhose und einen roten String. Meine blonden Haare wellten sich entlang der weißen Bluse bis zur Taille. Ich wollte gerade einen Drink bestellen, als der Barkeeper sagte, der nächste D... Continue»
Posted by xXNicolettaXx 1 month ago  |  Categories: Shemales, First Time  |  
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Caras first time with a man

This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in my showgirl s****r's outfits and feel the soft touch of her dresses on my skin. It's just felt right to me all my life and I guess that's the way I'm programmed.

After many years of just dressing in the clothes I eventually began using make-up and wigs to complete the look and to compliment the wonderful feeling of wearing women's clothes. Th... Continue»
Posted by cara_elaine 1 month ago  |  Categories: First Time, Shemales, Anal  |  
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