Shemales Porn Stories
Page 85

Panties For ME

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. I'd just broken up with a girlfriend and I'd decided I'd finally give in to my urges and try the sissy thing for a few months.

After many advances, I ended up going with someone a little older and little less hot than the others because he had the ingenuity to ask what my fantasy was and actually asked m... Continue»
Posted by rikkk72 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 763  |  
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Abigail's First Time

This is the story of the first time I dressed for a man. I had been with men before, but had never been with one as a girl. I would say 95% of it is true. I tried to keep it as close to the truth as possible. I will say that the acts described actually happened, and we really did go four times. I leave you to decide which parts you think are the false ones.

I checked my hair and makeup in the mirror for what seemed like the millionth time. Nerves I guess. Tonight was the first time I was going to meet a man while dressed and acting as a girl.

I adjusted my dress, a dark blue bodyc... Continue»
Posted by cdboy22 2 years ago  |  Categories: Shemales  |  Views: 496  |  
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good fucking

thank god 3 months at sea not had rest or sex havin men around 24/7 can do things to a man,singapore been here few times wid times and some fucked up shit wow,
left for land 3 days leave was gonna make the most of it.
went in couple bars checking things out see what was happening,
found out there was a lady boy competition on thought what the hell always good for a laugh, never thought anything about it, as in men being women,
got in the club it was packed with sailors all with the same idea spose,
any way the guy in charge started to speak to the crowd asking if there was anyone
who w... Continue»
Posted by peternorth111 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1106  |  
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My sexual fantasies



Well, I've always had sexual fantasies, since I was very young, I discovered the joys of masturbation around the age of 8, I remember playing in my bedroom with my pillow, I imagined it as a woman, or something like that, and so I took the pillow and I put it between my legs, rubbing my little cock against the pillow in a sensual movement, thinking about dirty things, until I reached the orgasm and jizzed over the pillow, it was so exciting for me and I enjoyed very much those situations. I remember several afternoons playing with one friend of mine in the staircases of my condominium, we ... Continue»
Posted by Porcellone 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 1254  |  
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Turning my neighbour on in pantyhose

One of my neighbours whos in his early 50's and clearly a man of taste;) asked me recently had we got a cleaner in?! I said yes a couple of times a week. He seemed happy!
I know why..... My name is Lucy and I love strutting around in front of the window with sexy outfits on. I'm meant to be our new cleaner but I have to be honest, I don't do much, just a lot of bending over and stretching up high!
Yesterday I was dressed as 'Lucy the maid', shall we call her? I had 4 inch black leather heels on, which make my calves look fab!My favourite stocking patterned tights which are as equally shin... Continue»
Posted by lucyslegs 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1710  |  
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Why did I settle for that?

Just made it back from Miami, was a great visit, but it could have ended after the first night, and that would have been alright. Hated the dirnking and the smoke, but did meet another lovely tranny who did give me the tour and the break from this horrid northern weather.

Although the sex with her was good... Ok, average, I didn't think it was worth the money that spent getting there and back. Why did I let her shit on my chest while skull fucking me anyhow? Some things shall always be a mystery I suppose.

I did love what she wore, how she looked, and her long slender candy, it fe... Continue»
Posted by Stickpiggy 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 819  |  
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monsters that crave sex part 1

there wans was a mad docter named hojo who studded how monsters get there mana back when it is used up or even if they even run out like humons do wan day he was working on some experaments to make humens be able to have ever lasting mana with out rest or food so they would never run out and need to rest but some thing whent wrong the monsters broke free i was is lab assistent at the time and was the first to expernce how the monsters truely got there mana they stoll it from us i was in my lab when i saw her she walk in the door naked i was soo shocked i didnt realize the alarm was going she w... Continue»
Posted by gothicrockersexslave 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 292  |  
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T V times

I had an amazing experience a year ago when I was on here previously , I became friends with a sexy cross dresser called Dark Angel; we messaged each other and arranged too meet when my husband was away .. well to cut a long story short we ended up in bed together both in stockings and heels . I am on my back with my leggs wrapped around angel whilst she is fucking me on top. Because we were alone I had left the door open, suddenly I noticed my husband standing there watching . I thought he was going to explode but he put his finger to his lip as to be quiet . To my amazement he pulled out his... Continue»
Posted by tiger061 2 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 1522  |  
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Last night I drank my own cum

Once upon a time...

There was a regular boy, who was always fascinated by women, but one day (casually) discovered the dirty and horny world of the "third way" of sex, the fantastic shemale-ladyboy-tranny universe, and it was like a shock for him, a very sweet shock, he never believed or thought in exciting himself by watching a girl with a cock, but instead that new world electrified him, and made himself very curious about these she-males, widening his love above women and becoming a real sex pig and an orgasm addict.


Well, that regular boy was me. I consider myself as ... Continue»
Posted by Porcellone 2 years ago  |  Categories: Masturbation, Shemales  |  Views: 1637  |  
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CD meeting

It was mid-morning and a CD friend was passing through, I got a text asking if I wanted my cock sucking, well I don't need asking twice lol. I told Jo that I wouldn't be able to dress up, she said that was no problem. We were to meet in a layby on the A30 just up from Chiverton Cross, at the time there were roadworks taking place so the traffic was not moving very fast. As I drove to meet Jo my heart was racing and I was trembling with excitement and fear, this was to be the first time I had met with a crossdressser. I pulled up in front of her crewcab pickup she was using to do a delivery.... Continue»
Posted by KirstyNylonlover 2 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 957  |  
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The ConVentioN part

2. Arrival
Pulling against the chains that secured her arms over her head, Sasha whimpered in frustraition
yet again. Her bonds hardly rattled at all as she shook and twisted her body to try and get free.
All she succeeded in doing though was making her heavy tits jiggle and bounce painfully. Alone
and naked save for the few cow patterned garments her mistress had allowed her, Sasha cried
softly in the darkened room. Her breasts were swollen with milk, now each one was larger than
her head! Pink bands had been tied to the base of her nipples, preventing any of her milk from
leaking out.... Continue»
Posted by peterbtrs 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 871  |  
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fgjghjfgjfg

My mouth was super dry
can i feel your, luscious, lips locking with mine
sweetylittle smooth pussy was saturated with her moisture
u separate my pussy lips and drove ur tongue in
plese held my breasts against ur mouth and starting sucking on them
shall i softly, caressing ur breasts.
laying on the bed, hands in her pants,
i also rarely wore a bra
stuffed her fingers into her pussy
She never wore underwear
pulling her pants off or by sticking my cock in her hand/mouth
three fingers stuffed into her pussy with one hand and was rubbing her clit with the other
walked over to me,... Continue»
Posted by kelly_hot 2 years ago  |  Categories: Sex Humor, Shemales  |  Views: 295  |  
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A busy Friday night. [CD/Gloryhole/neighbor]



I had been looking forward to this weekend for a month. My wife was going to visit some friends in NYC, and I was staying home, by myself. Yup, just me and all of my favorite things, like stockings and panties, and sexy little outfits. The torture was finally over, and the Friday she was to leave, arrived. I was still at work when she called me to tell me she was on her way up rt. 95. I wished her safe travels, and told her I would talk to her tomorrow.

I immediately left work, and headed for my car. I was so excited that I practically ran out of the office. I was going to indulg... Continue»
Posted by pbg732 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3655  |  
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A night with Rebecca

My heart was beating fast as Rebecca answered the door and invited me in. After months of swapping photos and chatting the moment had arrived. I was floored by how much more sexier she was than the photos we had been exchanging. My cock instantly became enraged as I stared at her. Rebecca had the cutest cheeks and eyes and she new how to do her makeup to accentuate her beauty. She wore a nice shoulder length brown wig. She had on a nice layer of foundation, her eyebrows painted dark. Eye lashes thick and full with eyeliner and sexy eye shadow under and around her eyes. Her full lips painted ... Continue»
Posted by Zeffer1 2 years ago  |  Categories: Shemales  |  Views: 1493  |  
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Bar trap

Bar trap
By slut michelle

Steven was a dead-normal guy. At the age of 28, he felt very happy.
Everything had developed in the last few years like he always wanted it
to be. His job in a big insurance company was secure with an outlook of
a promotion in the next year. His partner, Nancy, was a very ambitious
lawyer. That meant some days with long working hours for her. But as
Steven was quite proud of her, being so successful in her job, and
because they still had enough time for each other left, he didn't
complain. Steven met Nancy shortly after both of them had left Uni. It
wasn't... Continue»
Posted by trans_michelle 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1265  |  
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Bar trap 2

Bar Trap 2 (Part time whore)

I was supposed to put on heavy makeup. Starting with the foundation, I
applied a generous layer of a brand especially designed for the use on
stage, that did a very good job covering up any dark shadows. After I
was satisfied with the effect, I used a brush to put on powder and make
it all smooth and feminine.

Next I did my eyes, first with a black eyeliner on the lower lid, then
a white, thicker one on the upper lid. Black shadow followed, and white
towards the eyebrows. Three coats of mascara on both lashes to make me
subtly wink with them at anyone ... Continue»
Posted by trans_michelle 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 484  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 865  |  
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Getting caught on purpose ( true )

I had gotting tired of my mother showing up at my house everyday with out notice.She always came in and whated to move stuff around and say something about a dish in sink or what I had cooked for dinner last nite.I love her but since her boyfriend past away she was driven me crazy.
So I woke this morning early and asked her if she wanted to go shopping with me.She said yes I bought some heels bras painties and we went got our nails done.She asked do you own any male clothes I told here no.Well I dropped her off at her house and left and 20 minutes later she showed up I tried to tell her cal... Continue»
Posted by cdpaula 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 4126  |  
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Jeffrey and Jayne

Jeffrey and Jayne

Jayne lay there awake again. She had Just looked at the clock and it was 2am, she had to be up for work in 4 hours! However much she tried to nod off she just couldn’t, she was far too frustrated.
It started when Jeffrey got home from work, as it always did.
She called “Hello sexy, I’ve run you a bath!” As he walked through the door, then “Tea will be 20 Minutes!”
All she got in reply was “I’m hungry and tired!”
He had a bath and then ate his tea in silence. After he had eaten she tried to snuggle up with him on the couch, then he put the football on and told ... Continue»
Posted by slave_ariana 2 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 754  |  
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Learning how to deep throat pt2

Looking up at me from her kneeling position she said 'you aren't to let me choke my self on your cock, but you get the idea.' She stood up, I knelt down, she reminded 'make a fist with your thumb inside and squeeze tight, you will be able to take my cock in you mouth and possible your throat.

I followed her example and was able to get the entire length of her cock into my mouth and she was right, her penis glans was at the entrance of my throat and I was not gagging on it at all.

Chandra lovingly cupped my head in her hands and gently fucked her stiff cock into my oral orifice. Her... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 664  |  
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