Shemales Porn Stories
Page 121

Smoking TV tart

My makeup was perfect. Well, I say perfect, others would disagree. My red lips glistened with 4 coats of shiny lipgloss. Outlined in black liner, overdrawn to make the lips look large, and inviting. Heavy red blusher outlined my high cheekbones. My eyes were coated in a mix of eyeshadow and vaseline, giving the pink and white segments a shiny wet look, below the two inch long, heavily mascara'd eyelashes. The back combed platinum blonde wig, piled high above large diameter, dangly hoop earrings. He hadn't specifically asked for the OTT drag makeup, but had demanded my black PVC leotard, and ma... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales  |  Views: 854  |  
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Teen Cross dressers First Man.

This is a true story that happened to me only a few monthe ago.

I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy.

One Friday after a grueling 4 hour study session at school one of my classmates, who I didn't know very well, invited me to have a few drinks... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 712  |  
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Always knock first!

As the title says, it is always best to knock on a closed door prior to going in to someone whom you know is in that room! My bad! Earlier this week, i went in to see my boss, a hot guy whom i have fantasied having sex with, to check on my hours scheduled to work , as a swim instrucor. i did not knock i just opened the door and walked in, and there he stood, holding on to his desk, looking at a pussy magazine, and just jacking his lovely huge cock, with a huge mushrrom head on it, and then he saw me, and he froze
He kept his hand still on his cock, and i just laughed so hard, which made him r... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 2541  |  
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My highschool girlfriend 2

It had been a week and me and my girlfriend had not done anything else, but ofcourse we talked about it. Her mostly, saying "I was so sure you were so strait, im so happy your okay with my cock" all I would say was "I was so sure I was strait too, but being with you, just changed that I guess but I love it, you make me hornier than a girl with a vagina ever could." She also brought up another point, that the anal can go both ways, and ask if she could be on top next time. I was kinda scared it would hurt, but thought it may be fun, and told her that and she said she would make it painless, by ... Continue»
Posted by suckmedry69 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1737  |  
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My highschool girlfriend

I am a good k**, senor in highschool, dark brown hair, long for a guy, and in shape but not super athletic. It was about mid-way throgh our year when I finally started talking to this girl I had been eyeing all year. She was perfect, pretty, funny, always interesting, easy to talk to, laughed at all my jokes, and we had a lot of fun. She had long dark brown hair, eyes I could stare into forever, beautiful body, nice ass and medium sized boobs. I finally asked her out, and she said yes, and for about a month we hung out a ton, making out on the third date about 2 weeks in. A little after our on... Continue»
Posted by suckmedry69 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2760  |  
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Tgirl fun

Because it was a little cold I went out dressed in a nice pair of tailored jeans, which show of my bum beautifully, black bra, lacy top and a really tarty shimmering jacket. I was wearing a lovely pair of ankle boots and was able to quickly slip out the front door of my house and into my car. It felt wonderful to be dressed up and driving through the rainy streets. People were able to look at me when I stopped at traffic lights but no one seemed to notice anything amiss. I wasn't able to park too close to Mandy's flat so had a longish walk before I got to her front door. I loved the sound of m... Continue»
Posted by TaniaHarvey 3 years ago  |  Categories: Anal, Shemales  |  Views: 1533  |  
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Anal with Annabelle

It started early on Saturday when I had a nice hot bath and shaved myself nice smooth. I followed that by dressing up and taking some very sexy photos of myself and then emailing them to the Tgirl i was going to have sex with later in the day. I left my holdups and leather and lace leotard on under my street clothes and got a train to London. It felt so nice to feel the tightness of the holdups around my thighs and the leotard chaffing my cock and balls. I arrived at my lover's house in north London and carefully applied my makeup and put on my latex mini dress over my leotard. Annabelle was w... Continue»
Posted by TaniaHarvey 3 years ago  |  Categories: Anal, Shemales  |  Views: 914  |  
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I am such a slut...........12

I am such a slut...........12



Please read my other blogs to catch up. They are true and part confession, part cathartic. I am a man in the process of becoming a woman and loving it. I welcome your comments....Dani


I was lost with desire, dressed as a slut, a sissy slut. on my knees in a hotel room sharing the cock of a man named David who I had just met minutes earlier, sharing it with a young blonde woman who’s name I still did not know. Sucking his cock and licking his balls. Our tongues touching and sharing sensual kisses, all the while Derek, who’s personal slut I was quic... Continue»
Posted by snuggle11 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 2097  |  
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The experiment

I'll admit that I was a little bit d***k when she sat down beside me at the hotel bar.

Another business trip, away from home, this was getting to be a drag, and sipping on some bourbon helped a little. The smell of her perfume as she sat down snapped me out of my haze, and I looked at her. She smiled, turned to the bartender and ordered a drink. Looking back at me, she said "Can I freshen your's up too, darling?" I must have looked like an idiot, staring dumbfounded at her. I looked down at my glass, then back to her and said "sure." Her voice was surprisingly deep, but she was pretty. I ... Continue»
Posted by abend 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2143  |  
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My first Crossdresser - Part Four

I'd have been happy to make love to her right there in the doorway, but she had other ideas. We kicked off our shoes. She led me into her huge room and sat me down on the couch. She stood over me motionless for a moment, and then slowly began to strip. First her blouse, unbuttoned very slowly to reveal a sheer lacy demi bra. Then her skirt, slipped down her beautiful legs revealing her garter and sheer lacy panties. She stopped there. Her skin was flawless, pale and smooth. Her stomach flat, a dangling jeweled ring accenting her perfect navel. And her panties, while trying their best, were fai... Continue»
Posted by abend 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 601  |  
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I am such a slut..........11

I am such a slut..........11


Please read my other blogs to catch up. My stories are true. Part confession, part cathartic. I welcome your comments....Dani



I had turned a corner from which there was no going back. Walking down a path to becoming the woman that I desired to be, driven by my lust for men, for their smell, their taste. The feel of their cocks in my mouth.....and in my ass. The desire to be used by them as their slut, their whore, their toy. It was now Saturday evening and Derek had asked me (told me rather) to come to a party that he was having. He gave me the roo... Continue»
Posted by snuggle11 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1284  |  
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My first Crossdresser - Part Three

Harrah's was crowded, loud, and bright. She walked in front of me, holding my hand and leading us through the maze of people. I didn't mind being led because I could watch her walk, her ass and legs were as sexy as any I've ever seen. We made it through Harrah's, lurched onto the street and into the cool night air. The sidewalk was crowded still, but now we could walk side by side, hand in hand. I could hear giggles and whispered comments as we passed other pedestrians, but I didn't care. We crossed the strip in front of Caesars Palace and made our way to the Bellagio fountains, where she want... Continue»
Posted by abend 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 353  |  
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My first Crossdresser - Part Two

We finished our drinks and got up from the table. As we walked out of the restaurant I could feel everyone's eye's on me. On us. Uncomfortable to say the least, and I wondered for a moment just how it must feel to her, or to anyone who lives outside the norms that our society dictates. We walked through an open lobby and entered the Sahara casino side by side, but a group of oriental tourists rushed past us and she stepped ahead of me to get around them. As she walked in front of me I once again saw just how sexy she was, and for the time being my discomfort took a back seat to lust. Beautiful... Continue»
Posted by abend 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 420  |  
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Shopping with my s****r - Part 2

Continued...

We drove along chatting freely, laughing when we saw guys checking out the two hot babes in the car next to them. Jane told me what purchases she planned for me, practically a whole new wardrobe I thought to myself, but hey who am I to complain. Jane pulled up in a quiet corner of the carpark and leant over and kissed me gently on the lips, her tongue probing mine. "Come on Dannii, lets go shop!" she giggles.

I climbed out of the car as ladylike as I possibly could, feeling the fresh air up my skirt and flow over my balls felt amazing, a nervous excitement building in... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 6112  |  
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Fucking my boss´s shemale secretary

I had found her house when I followed her home. When I knocked at the door she didn´t seem suprised at all. As she turned her back on me and bent over her desk to pick up some papers I zipped up my pants and started rubbing her wonderful ass with my dick.
She said-What are you trying to do? Do oyu want to fuck me hmm?
Under her arousing moaning I took of her clothes and saw that her huge dick was really hard.
I said-Now I will fuck you.
Then I got out the bondage equipment that I had borowed from my boss at her house.It included a:
a ball gag
a one sleeve
a leather blindfold
a huge vib... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  Views: 923  |  
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Shemale boss fucking

God, I felt like it wasn´t my day.

I had been sent to the boss office one day and I tought that I was gonna gett fired or something like that.
When I came into her office I saw that she was dressed kinda sexy. She was wearing a suit that had a lot of cleavedge. When I got there she said:
-Do you know why I have called you here?
-No. I answered
-I wanted to ask you if you can come to my house tonight and have a litle chat. She said.
-Okay

When I got there I was a bit nervous. I knocked at the door and strangely her sexy secratery opened the door for me and asked me to come in. After ... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  Views: 2551  |  
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Only a Dream?

First i want to say, that this ist my first try to post a story in english, also my english is not very good, i can use it at everything in IT but i`m insecure writing about emotions.

Only a Dream

i looked up and saw i was somewhere in a cafe but i didn`t know how i get here.

The next look around me show me that i didn`t sit allone, next to me was this beautyful Man i know from the videos i saw the last days again and again.

But only his smile and the remembering of this videos told me that he must be this beatiful Lady in front of me.
He wears a white blouse which was transpare... Continue»
Posted by Cailly 3 years ago  |  Categories: Shemales  |  Views: 220  |  
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Crossdress fuck

One day while at university I went to the toilet. There was some one in the next cubicle. I could see a shadow under the partition. It was moving back and fort very fast. Was he wanking? I started to feel horny thinking about it. As a cross-dresser i was wearing a satin night-dress under my clothes. I decided to get brave. I stood on the toilet and looked over the thin wall. Oh god ya, he was masturbating hard. I pleasured my self as I witness something new & exiting. Then I let out an unexpected moan. He quickly turned to his left to find me staring at his dick. I jumped off the toilet, tuck... Continue»
Posted by monkeynuts0 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 2115  |  
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My first Crossdresser - Part One

When she walked in to the restaurant I knew I was in trouble.

It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.

Convincing she was not, a crossdresser without question. But pretty, really pretty. And the way she walked, shit, I was getting hard just watching her. She wore a tight bla... Continue»
Posted by abend 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1526  |  
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Weekend with my s****r - part 1

Continued from sunbathing with my s****r.

The week went so slowly, my mind always wandering back to our day together....stroking my cock endlessly replaying each and every kiss, touch and stroke. We stuck to our agreement of not talking about it when anyone else was in the house, not touching or staring was the hardest part, the sexual tension between us was incredible, I can't believe our parents didn't sense anything. We did leave bedroom and bathroom doors open just enough it was safe. Each morning when Jane left for work she'd leave some underwear on her bed for me.....twice it was e... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 5955  |  
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