Shemales Porn Stories
Page 58

First Time being fucked by two Men. (True stoy)

I was at a Jewelery convention in Flordia and my friend and I decided to go out and see what Orlando had to offer before our late company arrived ;). (Now we are two young women in our twenties and both athletic toned me hazel eyes and brown hair tan skin and her brown eyes with brown hair and fair skin!) We ended up going to the House of Blues. We started dancing with a few guys but none of them turned me on and I was ready to get fucked that night! Finally after going to the bar I spotted two sexy men dancing with these older ladies. I thought they can't be with them could they? Well one loo... Continue»
Posted by seksapilen8 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3033  |  
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The Cheaters

“God yes,” Lisette moaned as her husband flicked his tongue in and out of her hole. The five-foot-ten-inch brown-skinned beauty grabbed his head with both of her hands and pushed his face deeper into her ass crack. As he made love to her tranny pussy, her body, all one hundred and forty-five pounds of it, squirmed. She wiggled in every direction effectively working the fitted satin sheets off of their California king size bed. Her barely functional clit stiffened. “Fuck me,” she squealed.

Sensing his oral work was finished; Deitrick emerged from her anal cavity and stood on his knees. He ad... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1637  |  
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A Soul touching story from my Beautiful Master, De

I come home, I'm wearing the suit you like me in, you always get so aroused seeing me in this suit, it's power, the lines, the way it d****s my masculine physique, it just speaks to the man I am and the man you love.

I'm tired, but you've been home all day, waiting for me, dressing up sexy, trying on different lingerie, you can't wait to see me. I perk up, my lovely sissy needs some attention. So I relax on the sofa, instructing you to crawl to me, your soft smooth ass cheeks rising and falling as you approach me like a lioness. I unzip, unfold my cock, and let you go to work on me, you nee... Continue»
Posted by Hotassboi 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 447  |  
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Sissy's stroke story for Deebsflo. Part one

Cast: Dee (The Master), Jennifer James (The Movie starlet)
The Sissies: Mika, 5’11”, light brown long hair. Sammie, 5’9”, peroxide blonde, with a fringe. Bobbi, 5’7”, brown curly shoulder length hair.. Glenda, 5’4” brunette, bob-cut style, Toni, 6’, leggy peroxide blonde, long hair. Terri, 5’8” Brunette with a fringe and Alexi, 5’9” natural blonde with long platted hair.

Part one

In all his years, Dee could not recall seeing such a look of desperation and desire as he did now with Mika. ‘She’ had evidently been preening herself for hours, trying on different colored hotpants and t... Continue»
Posted by Hotassboi 1 year ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 393  |  
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Caught by Neighbor

Caught by Neighbor


- 1 -

It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled my tracksuit pants down, admiring the bright pink, silky panties that I'd been walking around in all day.

I'd been cross-dressing for many years before I met Sam, but it really wasn't her thing. So I tended to ... Continue»
Posted by Femluver 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 8449  |  
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Paying for my own birthday present!

My wife told me that she'd arranged for us to spend a weekend in London, see a show and do a bit of shopping for my Birthday.

Great I thought.

We got to London, from Wales, early evening on the Friday. Checked into a quite nice hotel in the west end and headed up to our room. When we got up there, my wife headed for the bathroom and told me to come with her. Knowing what to expect, I stripped off and laid in the bath. She climbed in, pulled up her skirt, moved her g-string to one side and pissed straight into my mouth. We'd been in the car for about 5 hours, so what I got was stale and b... Continue»
Posted by garyw 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2031  |  
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My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.

One day I was home alone, my parents were away for the week and my s****r was staying with her boyfriend. I turned up the music and got dressed from head to toe. I was pretty much smoo... Continue»
Posted by VirginAsAGirl 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 1850  |  
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Transformation

This is a cross between real life and fantasy. A deep, dark desire which may never be fulfilled but I can't help a part of me wanting it anyway. I hope you enjoy.

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I was a usual guy. Or I had thought so anyway. I mean, I had worn some of the female members of my house' panties and swimsuits on occasion as a young boy but I always thought that was normal. I mean, apart from the silky smoothness of lace and satin massaging and teasing the penis, y-fronts are exactly the same really... just with less frills. It didn't last long though, I mean, how can a boy in a strict and straigh... Continue»
Posted by shyadam89 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1601  |  
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Fulfilling my babys fantacy

Fulfilling my babys fantacy

You and I have been having trouble letting each other know what our fantasy's are.
You finally told me about your transsexual interests thinking that I would think your weird.
But was happily surprised that I fully supported you.
We had been chatting with fairdesire for a few months and I wanted soo badly for you to fulfill your fantasy.
I seen several raffles for to win trips over seas and bought several.
I WON THREE !!!!!
Oh my goodness, I had a hard time keeping my mouth shut about winning 3.
I only told you about 1.
And sent on... Continue»
Posted by tnt88jean 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 1032  |  
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Come as you are!

I was overnighting on a business trip and as was my kinky little habit, I crossdressed at night. My room, which was on the second floor, had a full sized sliding glass door and balcony. Another motel across the parking lot from mine had windows facing mine. I dolled up in my skimpiest black lingerie with high heels, wig, and full makeup and kept my lights off so that I could walk around on the balcony safely. All the curtains were drawn on the motel across the way, so after a while I got a bit careless about the lights and left them on after going in to fix another drink. As I stood out on the... Continue»
Posted by dana213 1 year ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1782  |  
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new roommate

I enjoy sucking real man cock....it was figured out at a younger age then some. I was 18 just moved to college and ended up in a dorm room with someone right around my size. I never played sports never got fat just stayed in regular skinny shape, he on the other hand had a really muscular ass and waist it was just shaped like an apple however he stood and it reminded me of a womens booty. Also his thighs were extremely smooth and skinny and he stayed tan. I didn't talk to him much the first week. But that cbanged the day I left for work on a saturday and forgot my bag when I got back to the ro... Continue»
Posted by 612Goo612 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 2929  |  
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Fulfilling My Babys Fantasy

Fulfilling my babys fantasy


You and I have been having trouble letting each other know what our fantasy are. You finally told me about your transsexual interests thinking that I would think your weird. But was happily surprised that I fully supported you. We had been chatting with fairdesire for a few months and I wanted so badly for you to fulfill your fantasy. I seen several raffles for to win trips over seas and bought several. I WON THREE !!!!!

Oh my goodness, I had a hard time keeping my mouth shut about winning 3.
I only told you about 1. And sent ... Continue»
Posted by tnt48 1 year ago  |  Categories: Group Sex, Shemales  |  Views: 590  |  
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The woods

I met my sissy boy slut at the pathway to a secluded woods. Our eyes met as I walked past her and continued down the path, she followed without being asked and caught up And held my hand as we made our way to a hidden spot. My arousal was growing as she rubbed my arse through my trousers, I stopped by a large tree with a branch we could use to fuck on and over. I kissed her and ran my hands over her body the tight jeans allowing her bulge to been seen I un zipped her and put my hand in to feel silky panties and a hard cock! Then slowly pulling her jeans and panties down that rock hard little c... Continue»
Posted by kawa696969 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1876  |  
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my dream neighbour

if only this was my neighbor

I had a neighbor who was a beautiful lady at my apartment I
lived at in town. Her name was Sally Williams. She was 25 and she was
5'9" weighed 128 lbs had 30 c cup breasts i would guess she had dark
brunette hair down to her back and amber eyes.
She called me over and asked," John how would you like to
spend Saturday night with me here?"
I said," That sounds fun what time would you like me to come
over?"
She said," How about 6?"
I said," 6 sounds good to me."
She said," I have a special movie I would love for you to
watch it is very erotic."
I said,... Continue»
Posted by leadpencil21 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2956  |  
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my dream girlfriend

I have had many girlfriends over the years but the one I have now is very different. Her name is Kim and she has a cock that is as big around as a beer can and about 8 ½ inches long. Kim is a beautiful woman with a cock.

When we first started dating I had know idea that Kim was packing a big cock along with two juice balls. The night I met Kim we ended up outside sitting in my car with my cock down her throat. She sucked my cock like I had never felt before. I shot so much cum my balls ached.

I sucked on her tits but every time I would reach for her pussy she would pull my hand away. The... Continue»
Posted by leadpencil21 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1659  |  
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caught spying

i would love to re act this with someone ;) any offers?


A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-).

Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pride and joys. Normally, this would help her relax and unwind, but tonight, and on several other nights, she found that remained tense. She couldn't get over the feeling that somebody was watching her, for several days, perhaps a week; when... Continue»
Posted by leadpencil21 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 2483  |  
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new girl in town

would love this to happen to me ;) anyone want to help me :P


come home and have dinner, but sometimes I go to the bar down the street and have a few drinks for a couple of hours. About a week ago I noticed a new girl at the gym working out by herself and I couldn’t take my eyes from her. She was gorgeous, big boobs and sun tanned skin, 42 inches round ass, nice flat belly… She had long blond hair, green eyes. I had been watching her work out everyday for a week. Then, on Friday, after work, I went to the bar and I was sitting there having some drink. I was enjoying my beer when all of sud... Continue»
Posted by leadpencil21 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 797  |  
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CD at truck stop with three men

Went to a truck stop last night after a party around midnight in my sexy short dress, got out and bent over looking at my tires for assistance. Gave a nice view to whoever was watching of my smooth white ass and sexy black panties with pink trim with half of both cheeks exposed. A nice older (63 yo) black guy (Ted) asked me from his truck if I needed help. We talked and then thanked him and asked if I could help him for helping me.

We walked over to his truck and got in his sl**ping quarters. Gave him some more intimate show of my nice ass, turned around, unzipped his pants and began ... Continue»
Posted by hotcdsub 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3631  |  
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A date with a straight college student

I had been chatting with this boy for a while when he finally told me his parents were out of town and he had his father's car. So we set up a date in the evening. I told him to pick me up by his car from somewhere. I was pretty excited, this jock was a very good looking guy with a slender athletic body type, brown hair/blue eyes. I always had a thing for blue-eyed boys. I was thinking about those whilst putting on make-up in front of the mirror and combing my hair.
I was a lil bit nervous when he picked me. He looked even much more handsome than his photos. Because he was lacking a web cam, ... Continue»
Posted by Slave4str8twinks 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1810  |  
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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 1 year ago  |  Categories: Fetish, Shemales  |  Views: 1840  |  
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