Shemales Porn Stories
Page 112

A true story: me and a transvestite man - part 2

OK this is the second part of my true story. I was going to leave it at two parts, but I think there's enough to make it three parts, now!

I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.

However, this early experience was enough to leave me curious as to what it would be like to have fun with a cock. As you may have read in part one of this story, I was rapi... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1053  |  
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A true story: me and a transvestite man - part 3

This is the last part of my true story. I had expected it only to need two parts, but it seems that I'm quite a wordy writer, so it now spans 3 parts.

Where did I leave off last time? Oh yes; Toni, the gorgeous Brazilian TV was leaning forwards, dressed in her black lingerie, her firm arse towards me, ready for me to enter her. Read on...

I wasn't expecting this to go well, as I'd only had a little anal sex before, with a woman, and this had been on a bed, where I could jockey around for best position. However, thanks to my extra height (6'3" against Toni's 5'10" or so) we seemed a p... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 670  |  
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Out of Town Meeting



Dinner was seamless, the food, the music, the wine, the company. Tony’s out of town business meetings were usually painful, in that he hated living out of a suitcase and eating alone in overpriced restaurants. This trip, he was enjoying every second of it. He’d met up with Chantal, a woman he’d met online a few months back. They’d hit it off and started talking on the phone. It was a casual thing; neither of them stopped seeing the people in their lives and neither of them had a desire to take the relationship to a different level. They both enjoyed the same kinks, they had some late... Continue»
Posted by AfroerotiK 3 years ago  |  Categories: BDSM, Hardcore, Shemales  |  Views: 513  |  
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Ally...


I was at a customers' house doing some yard work as they had paid me
in advance for just minor clean up, pulling weeds, mowing, trimming the
hedges. I was finishing trimming the hedges in between the neighbors and
their house and as I finished up the neighbors' wife came out or so
I thought.

She politely smiled and waved to me and I nodded trying hard to act as
if I was not noticing her in a skintight bikini with a lacey French cut
bottoms. She could tell and began to tease me by dropping her towel and
turning her back to me showing her pear shaped bottom with the long legs
leadin... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1506  |  
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Sally the seducer...


I had been chatting online with her for about a month and she finally
asks me to stop by. My butterflies are churning in my stomach, as I have
no real idea what to expect I have only seen tease pictures. You know
the kind, no face barely a body part in the picture.

I pulled up to the address she gave me and knocked on the door. I did
not think she was going to answer and this man answered the door.
"Hi, come on in. "I will be ready in a minute." I was
shocked the woman on the phone sounded female so sultry making me long
to touch her. He disappeared into the bedroom chatting with m... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 595  |  
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Friday night...

So its another Friday night and I was just driving around looking
for something to do. I had already stopped by the local bookstore
and didn't see anything I was really interested in so I kept
driving. I saw a small bar down the street from the bookstore it
looked quiet and not too busy for a Friday night so I stopped in for
a Coke. I don't drink so I just sit at the bar and soak up the
atmosphere.

I was sitting at the bar for about an hour nursing the Coke, thinking
about leaving and then she sat down. A beautiful, tall woman with
shoulder length auburn hair and the sexiest eyes I ... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1324  |  
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Brianna...

Rob asked me to house sit and I didn't hesitate since he lives in a
beautiful big house on the end of a Cul de Sac. There is only one
house next to his and no one can see his backyard except the house
next to his.

His neighbor Bryan is a local college professor at the community
college and doesn't seem to mind when we skinny dip in the middle of
a Saturday afternoon. He seems cool so I thought this was going to
be a great two weeks. I had no idea what was going to happen during
these two weeks.

It was the first Saturday of my two week stay and I was sitting in
the back yard enjoy... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1191  |  
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Glory...

I walked into the bookstore paid my way and went into the peeps; I
usually avoid the theatres since there is not any privacy for
playing. I guided my way in the dark letting my eyes adjust in the
dark. I walked to the back where the stalls with the gloryholes are
and found an open booth.

I sat down and pushed to find one of three channels I liked and there
it was the shemale channel, with a sexy shoulder length blonde and
redhead with deep dark red lying on her shoulders. They were kissing
and touching and boy was I getting aroused, so much, so that I did
not notice the booth next t... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1050  |  
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Desiree...

I was walking around the local mall just doing some casual wandering shopping, not really looking for anything including what I found. I rounded the corner and there stood this amazing creature with long brown hair, deep blue eyes and the fullest lips I have seen in some time.

She was a fuller figured beauty and I was very intrigued with what I saw since she was very sultry and definitely sexy. I followed her into a couple of normal stores when she led me into a store I was apparently not paying attention to when I entered. It is hard to act casual when you realize that you are in a lingeri... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 494  |  
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Tonia...

One night I went to a different club to check things out. By now, I
knew what I was looking for and where to find it. I was cruising the
area with several bars for people with my kind of preferences you
know women with more to offer a man.

I parked out in the lot and began to walk in as I did I noticed this
beautiful brunette with long legs. I was very interested in
following her into the bar. I rushed to open the door for her as she
just politely blushed and smiled at me. I tipped my head to her in
respect trying hard not to blush too. She smelled very beautiful,
the sweet smell of... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 470  |  
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A true story: me and a transvestite man - part 1

This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.

There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.

OK, about 10 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born with a male body, male genitals, but for whatever reason, don't want to live as men. Today,... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1080  |  
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He makes me feel so GIRLY

My friend that you all see fucking me and me sucking his big cock in my pics and videos. We will just call him Mister. Well he came over this morning for some Sunday fun. He is so good to me he really knows how to make me feel like his girlfriend. Today was so yummy I am still sexually excited just thinking about it.
I was dressed and ready for him when he arrived. I was wearing my sexy white lace halter top and black thigh high stockings, with the cutest little white G String with a sexy little flower in the back. Topped off with my silver jewelry and 6 inch black heels. I was so excited to... Continue»
Posted by Naughtynina 3 years ago  |  Categories: Shemales  |  Views: 1055  |  
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Caught wearing my mother's stockings

For as long as I can remember I've been obsessed with my mother's legs. My very first wank was brought on by the sight of her curvaceous stockinged legs in high heels. She also liked to wear knee high black leather boots which would send me into a frenzy. I once saw walked past her room while she was getting ready for bed and saw through the gap in the door that she was wearing those boots and nothing else! Needless to say my dad fucked her senseless that night and I listened with my ear to the wall, wishing it was my cock for fucking her beautiful curvaceous body.

I longed to kiss her stoc... Continue»
Posted by petearch 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 2975  |  
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Sex with Jan- part 1

Jan reached for her packet of Rothmans Royals 120s, and extracting two cigarettes, offered me one. I took it in my long black PVC gloved hand. The fingertipless gauntlets revealed 4" long black false nails, that guided the sexy cigarette to my bright 'diva' red, heavily glossed, shiny, cock hungry lips. 'Take things easy H, we've got all night. My wife's at her s****rs for the weekend, and my 3 video cameras are fully charged.' She stood up, switching the cameras all on, then looking at me dangling my Royal seductively, gently lifted her skirt, adding, 'Forgive me, but I've got to stroke it!',... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales  |  Views: 255  |  
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Office Fun - Part 2

Marcia was sitting in the car park of the office, about to leave having just finished work, when she saw Lee walk out of the building and head towards his car. It had been four days since they had fucked in the office, and she was eager for a second round. She checked herself in the rear view mirror before beeping the horn. Lee looked towards her and she beckoned him over, winding down the window as she did.

“Hey,” she said with a smile.

“Hi,” he replied, ducking his head in through the window. She caught him taking a quick glance at her cleavage.

“You wanna come to my place for some ... Continue»
Posted by gellid 3 years ago  |  Categories: Shemales  |  Views: 1100  |  
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Meet with Jan part 2

We sat down, chatting amiably, drinking in the view of each other. Jan had on her black PVC body, with matching corset, elbow gloves and midi skirt. The skirt was already tented, as her lovely big boner bulged below. She always wore black seamed stockings, each held by 8 suspenders, but they were mostly hidden by here shiny white patent, over the knee boots, with 6" metal tipped heels. She had her almost white 'big' wig, on top of her heavily black lined, bright blue eyeshadow, along with her de rigueur red lips, beauty spots, and extra long, drag eyelashes, topped off with half a ton of blus... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales  |  Views: 389  |  
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Meet with Jan part 3

'You look much better in the flesh, H. Love that mac! I'll go and get mine now, cos I was too hot before.' She returned shortly, dressed in a really shiny, very soft, black PVC mac, rustling down to her ankles. She swished around, giving me a twirl. 'I want one like your PVC catsuit. Leopard print PVC is soooo tarty, I love it!' She came over and rubbed my big balloon tits, asking mischievously 'Are they false?' 'I'm 100% false, Jan, except for my cock, ha ha!' 'I can see that!' she said, dropping her gloved hand to my groin. 'Cigarette?' she asked.... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales  |  Views: 430  |  
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Meet with Jan part 1

I'd asked Janice if I could arrive at hers dressed, because it takes me at least two hours to put my slap on! So I had to get dressed at a motel and drive over, under cover of darkness. She'd left her drive open, so I could park at the side of her house, and slip round the back of the large semi (hopefully!) unnoticed. As I tottered quietly to the rear of the property, I wandered into the open conservatory, knocking gently. 'Fucking hell!', I heard, as I peered into the kitchen. 'Fucking hell!' I replied back. We stared at each other, incredulous, like meeting a massive film star. Someone we'd... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales  |  Views: 493  |  
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Introducing......Janice, the smoking TV tart!

Janice and I had corresponded for many years, sending each other videos, then dvds of our antics, plus any other similar material we could find, of other OTT TVs in sexual situations, like Lady Tina, Barbi Satin and Alexis Divine. Usually with a smoking fetish theme, along with heavy makeup, and PVC and rubberwear. Jan lives in Oxon, but I got a chance to go and meet her, eventually, to do some filming together. She's 6'2", without heels, and such a horny tart. Her films always got me horny. The older ones (20 years ago, now!) nearly always had her getting a spunky facial from guys, or wanking... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales  |  Views: 244  |  
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Tranny and Me Meet The MILF

This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
Posted by adw276 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1785  |  
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