Shemales Porn Stories
Page 118

My First threesome Part 2

After Ray's step-mother put make-up on me and fixed my already long hair she had me looking like a young sissy boy, that's saying a lot because I was 23 at the time. She then had me slip out of the outfit Ray had given and put me in a red throng and matching garter belt and bra. She had me wear black seamed stocking to make me look like a real slut. She then told me that she had to get ready for Ray's father Bob to get home and that I was to go down to Ray's room and sit with him until then.
When I got to Ray's room he was already dresses similar to me except his lingerie was white, and bo... Continue»
Posted by billieearls 3 years ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 1593  |  
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A Dogging tale

Last month I went dogging. I don’t often go out to dogging sites as there is always a chance of police being around and you sometimes meet the oddest of characters. But I was feeling very horny and there was nobody around to play with so I got dressed and drove off.
I wore some black sexy lace panties and a matching bra, a black half slip and a blue mini skirt and blue top. Also I had on black holdups with a nice lacy top, shiny black court shoes. I was fully made up with lots of pink lipstick and my hair was brushed into a short but femme style. I lube dup my arsehole in anticipation of find... Continue»
Posted by aln1174 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 2755  |  
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Venegeance is sweet

Sequel to „A dominate Goth“

All my stories are absolutely true

2010 August, 11
About 11:15 am

What a warm day. Really hot, perhaps even the camels fainted in the zoo because of the heat. The thermometer reached 35°C that day. At these temperatures people usually aren’t up to do anything. So did I, because I sat together with Claude in his front yard. We were both sitting on our beach chairs below a large sunshade. While I was browsing in a magazine Claude uninhibited showed no manners.
He had his boots, together with his socks, pulled off and wore light blue jeans. On his upper bod... Continue»
Posted by Bea69 3 years ago  |  Categories: Anal, Lesbian Sex, Shemales  |  Views: 1244  |  
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Sweet Charity

You may have heard of the phrase sweet charity, well in my case it was certainly sweet to me. I have built up a large part of my CD wardrobe through judicious visits to charity shops wherever I may be in the country. In one of my local charity shops there's an assistant called Wendy who I would judge is in her mid fifties but looking well on it. She's always well turned out in neat blouses, always a just above the knee skirt, never bare legs and 3 to 4 inch heels of various kinds. I must admit that my fairly frequent visits to this particular shop engender a feeling of hornyness on two counts.... Continue»
Posted by MichaelaCD 3 years ago  |  Categories: Shemales  |  Views: 1060  |  
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My first threesome.

My lover and I just finished sucking each off and were laying next to each just talking and he ask if I had any fantasy's and I said I like dressing in lingerie. He went to his closet and came out with a black bra and panty set along with a full black slip. He asked if I would put these on and I was up so fast I tripped and fell to the floor. I didn't think I made any noise and started to get dressed. He went into his bath while I was dressing and then his bedroom door open and in step his step mother. I didn't know what to do but stand there in the lingerie. She just smiled at me and wa... Continue»
Posted by billieearls 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 2541  |  
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Weekend visitor

Well...my recalling of an experience dressed in a swimsuit didnt seem too popular so perhaps you may prefare the story of a weekend visitor I once had. It was 1981 and I had just got my own place, a nice modern 1 bed flat.Apart from bedsits as a teen this was my first real place of my own.
In these pre internet days we had such mediums as contact mags, specialty mags and such and it was though one of these that I got in touch with Colin.....that wasnt his name but the rest of the story is true verbatim. He described himself as being athletic and in his 40s, I was 27 and he was hoping to meet ... Continue»
Posted by holaryhilary 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 439  |  
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first time with a Tranny

My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits. We dated for about a month when talk her into just taking her shirt off, after a while without her shirt off she finally took her bra off. I would make out with her and suck on her tits, lick her nipples. One day we were together I decide to change it up so I took my pants off in the bedroom and ... Continue»
Posted by theho_1 3 years ago  |  Categories: Anal, Shemales  |  Views: 4443  |  
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Swimsuit summer 2010

This really happened and even now I got both excited and scared thinkig about it.
Near me there is a bay that's very quiet, even in the height of summer its rarely visited, and I took to driving there in my car and sunabathing in just my swimsuit and hairpiece...seeing as many females of my age ar'nt stunning beauties and rarely wear make up whilst sunbathing I knew I'd pass at a distance .
On the first occasion, a man came quite close and said 'hi' as he passed and I just raised my head and nodded as I lay on my tummy. A couple passing by also gave me a wave and I waved back , apart from th... Continue»
Posted by holaryhilary 3 years ago  |  Categories: Shemales  |  Views: 1420  |  
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SISSIES TRAINING PART 1

SissyIndy©

I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often moving the same piece of furniture to what seemed like the same place it was originally. Finally he decided he liked the new arrangement, which wasn't that drastically different than how it looked when we started. Obviously exhausted, I sat down on the couch. He asked me if I'd like a Ga... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3299  |  
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A Fulfilling Life

A Fulfilling Life

by Abrum Liquor (the first "r" is silent)
(aka Roblon)
07 / 99

Sophia Sappho, a beautiful society woman of 37 years, is having a few girlfriends over for cocktails one evening. Unbeknownst to her friends the hostess has a male washroom attendant available in the powder room.

The first guest retires to the powder room a little urgently. Frantically she lifts her skirt, pulls down her panties and with eyes shut, emptied her bladder. Her eyes open wide as she suddenly hears a man’s voice offering, “Do you require any assistance ma’am?”

Startled, the woman jumps ... Continue»
Posted by roblon 3 years ago  |  Categories: Fetish, Shemales  |  Views: 405  |  
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Summer Fun

*Crossdress Story*


Living with your parents is exceptionally annoying, especially when you're 26 and have a fetish for crossdressing. It kind of hampers your "need" for putting on slutty outfits and parade yourself in front of a webcam with a pink-glass buttplug up your ass and a giant rubber cock vibrating away as it burns down your last pair of batteries.
But alas, it's the position i'm in and somehow i've made it this far without too many suspicions.
There was the incident a few months back when my mum and dad were at work and I took the opportunity to clean all my sex toys; taking t... Continue»
Posted by KitsuneTV 3 years ago  |  Categories: Shemales  |  Views: 1403  |  
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Abused as a tranny at a sex party with my mum

This story is a follow up to "Caught wearing my mother's stockings"

I decided to go to the party and be the tranny slut they were looking for. After all, it's nice to be wanted and I really would do anything to keep those photos of me dressed in my mum's stockings, private from my friends.

I've never had anything up my ass before, in fact I've never even had sex at all. This was going to be my first sexual experience. Unless you include being wanked off by my mum or kissing and groping fat girl, Stacey Williams at the school Christmas party. So the idea of being the centre piece at a sex... Continue»
Posted by petearch 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 3813  |  
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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: 1392  |  
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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: 699  |  
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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: 522  |  
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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: 1507  |  
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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: 596  |  
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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: 1314  |  
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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: 1189  |  
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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: 1049  |  
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