Shemales Porn Stories
Page 8

Male to Female Transformation

Male to Female Transformation

Genre : TG SOS or Surgery/Transformation Male to Female
Story : Cristine Carter
CH - 1

The last thing I could remember was walking out of the Bank
and crossing the road to my car. I had just been to see my
bank manager to discuss transferring some money from one of
my accounts into a high interest savings account.

I had won quite a bit of money on the Lottery, enough to
change my life. I was unaware just how much my life was
going to change.

I had just reached my car door when I felt someone bump
into me. Then everything went blank...
... Continue»
Posted by cristinestone7575 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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First big cock.

So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective.

I tried an online dating site and eventually met a white guy in his 40s well built professional that likes to top. I told him that I was a beginner at being a bottom and that I thought he was really handsome but his cock was just way too big for me to have sex. We became friends and chatted all the time. Until one weekend he got a hotel room and sa... Continue»
Posted by Cutiecdny22 11 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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True story of an old man in the woods

I was just a young lad the first time i did any thing with another guy, i was still living with mom in the house she inherited from her father after he died in a small village that mainly had elderly people living in it.
There certainly wasn't any one my age about so contact with other youth's was limited to school.
Most of my time was spent playing alone or helping mom about the house, then some thing happened that was to change me for ever.
It was a Sunday morning and mom was home doing some house work, i was watching cartoons on the TV when she called to me to help her get the washing in... Continue»
Posted by fun_boy_fan 10 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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A Bra And Panties?

It had been a long day, my friends and I had been on long ride in our local forestry area. We always parked our cars away from the usual cyclist parking areas so it was pretty well deserted. As we approached where we had parked we saw what looked like a lady by a tree in her undies. As we got closer we could see it was a guy in women’s underwear, stockings, suspenders, bra and silk panties. We had a small giggle and rode past but as I, looked it appeared that he was tied to the tree.

At the cars, my friends loaded their bikes and left so I got on my bike and cycled back to where the guy was... Continue»
Posted by ClassicCockx 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Gracie and her best friends son...

Gracie was attending a birthday party at her friend Rachel's house, who's son was turning 18...

Gracie:
"I've known Rachel for more ten years now and she is one of the few type of friends who actually stick around. It felt as if not too long ago I was turning 18, but I was now in my early thirties and Rachel probably felt old too now that she was was nearing forty!... But anyways let's continue with the story...

There was plenty of alcohol available, for those in the appropriate age range of course, and Rachel loved her drinks whenever the occasion called for it. I was the only other f... Continue»
Posted by adblman 2 months ago  |  Categories: First Time, Shemales, Taboo  |  
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sissy blackmailed by teamviewer and exposed


my fantasy about being blackmailed and totally ruined

watch out this could happen to you

im a sissy faggot I live in st Louis mo im in the closet no one knows i dress in femine clothes I was married when I was 20 and straight after a year I caught her cheating on me , we only had sexy 3 times I couldn't get hard with her , I was allways thinking of men, masters, tops, at home I stole her panties bras high heels lip stick, and would dress around the house, after the divorse I got the house and I started to wear panties to work everyday and shave my legs smooth , somedays i wear stocking... Continue»
Posted by sissypattie 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 4 years ago  |  Categories: First Time, Shemales, Taboo  |  
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My First Time

It must have been 4 years ago.
I was alone and curious, and had been for a while now. I had plenty of girlfriends and knew I was not gay. I just never had feelings for guys, only women. But sex..... sex is sex I thought.
Looking at pictures, watching videos, toying with myself while dressing up in panties and other girly things, had kept me amused up until now. But my desires had grown too strong.

I had frequented a few chat sites, getting into kinky conversations with guys, loving the way they all hit on me and tried to seduce me. It drove me wild and gave me more confidence all the whil... Continue»
Posted by MissieUK 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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My First Time

when i was 18 i first started to dress up when my mom was out and i loved it. well this is a story of my first time and i would like to share it with everyone. me and my mom live alone and she used to always bring guys back to the house and i used to always hear them having sex and it really turned me on so i tried to peek into the doorway each time and one time a guy left is underwear in the hallway so i picked them up and smelt them and it made me really horny. however this guy turned out to be my moms boyfriend so he came to our house on a daily basis but one time when my mom was out and i ... Continue»
Posted by MegCD 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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A Friend's Treat

had recently split with my wife and was feeling very down.

I was invited to spend a few days with my old friend Dave and his wife Tracey.

The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse.

I hadn’t known that Dave was in a club and was surprised to find he was a member of one. He had refused to reveal what type of club we were going to.

The door opened as we approached and a dinner suited do... Continue»
Posted by maninnylons 1 year ago  |  Categories: Gay Male, Shemales  |  
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Lodgers Surprise

I had started my first job after leaving university. Having moved to a small town where I knew no one I had taken lodgings with a couple who had a large house a short walk from my office.
The couple were called Jenny and Mike. They were both in their fifties and had retired early and took in the occasional lodger. Jenny was about 5 foot 2 and was plump and sexy. She had good tits and fine legs which I often admired when I thought she wasn’t looking. To my joy she always wore nylons either stockings (I could see the garter bumps) or tights when she was wearing tighter clothes.
Mike was 5’11” ... Continue»
Posted by maninnylons 10 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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THAILAND SEX TEENS MILFS LADYBOYS PART 1

My wife Phil and I decided to have a horny sex holiday in Thailand
We are both bi sexual with a real delight in fucking young girls and boys
Phil is a tall skinny brunette with small but pert tits and gives the impression she is very conservative
but she loves all types of sex play and is game for anything
We decided to holiday in Thailand because you could cheaply buy any sex fun you desired
We both wanted to try everything
We flew to Bangcock what a great name for the worlds sex capital and were met by our individual
tour guide a beautiful 21 yr old Thai girl .She was tall like Phil ... Continue»
Posted by xxxdonal 1 month ago  |  Categories: Anal, Shemales, Taboo  |  
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The Neighbor...

My next door neighbor had never shown any interest in me before. He was married and straight, as far as I could tell.
One night, however, there was a knock at my door. I looked through the peephole and saw my neighbor standing there. He was tall and stocky, with a beer gut that I found sexy.
I answered, not knowing what to expect.
"Hi. I'm sorry to bother you so late." He said.
"Its ok. Is there something wrong?"
"Look, I don't really know how to do this... so I'm just going to be blunt. I know that your gay. My wife and I have seen several different men coming and going at all... Continue»
Posted by bttmblw 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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Tranny teacher

Hi Al, how is your house sitting summer going ? Pretty good Tim a little boring but the beach is nice. By the way, I didn't mean to but I saw you last night through my window... you were wearing woman's underwear. OH I hope I didn't disturb you Al. Actually I was totally turned on, especially when you pulled out your hard cock.

Really, if you like I can arrange for a private show ... interested ? I don't know I have never seen a man up close before. Ah.. well if you pretend I'm a lady I can walk you through some fun. So you will put on your stockings and the silky things. OH yes and a wig ... Continue»
Posted by TenderLoins 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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]Aunt Karen and Her Niece Andy




Aunt Karen and Her Niece Andy

My name was Andy now it's Amy. This is my story.

When I was twelve, I became fascinated by women and their clothes. I
still don't know what caused my fascination. I do know that my
interest increased with each passing day. Maybe it was puberty, or an
imbalance of hormones or as I've recently come to believe, I was a
person born genetically different. All I'm really sure of is ... I'm
glad it happened.

The initial stages of my quest for feminine knowledge took the form of
comparing women when they weren't conscious of my appr... Continue»
Posted by klammer 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Tutor and Jenny

The Tutor and Jenny (Part 1)
by Claude van Feinbode


Every once in awhile I find myself working as a tutor while earning my PhD. The university offers tutoring to high school students that demonstrate exceptional academic skills. So during the cold winter months I find myself tutoring students that probably never get past first base because they are more worried about their rock polisher or telescope than trying to get in the pants of some beautiful young coed.

Imagine my surprise when a goddess like in a French art film arrived unexpectedly. The door opened and squealed sl... Continue»
Posted by NiceGuyz4u 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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Becoming a Sissy Cocksucker (true story)

I always loved feminine things. I'd wear my s****rs panties as often as I could. I loved the way they felt, the soft fabric, the high cut legs, and especially the frilly lace edging! I graduated to bras and padding them and wondered what it'd be like to be a girl.

I always loved watching porn where a guy is sucked off by a
woman. I started to realize, what turned me on the most about it was watching his cock when it orgasmed! I LOVED watching the cum shoot out and on to her face and in her mouth! I used to watch it (and still do) dressed in panties. Well, fantasy eventually took over, I wo... Continue»
Posted by vickiebicd 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 4 years ago  |  Categories: First Time, Shemales, Taboo  |  
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Car Bonnet Cockriding Whore

Hi Guys,




This true story dates back about 4 1/2 months now, and takes place outdoors, well over a car bonnet to be exact.


I had been chatting to this lovely guy called Dave, we had been chatting on a different site and arranged for him to come over from where he lived to where I live in Droitwich. Well I had been getting my self ready most of the evening showering, shaving my self totally smooth including my pussy, made a real effort to look hot with my makup and clothes. The usual things, stockings suspenders, 1/4 cup bra with matching thong, and high heels, a loose fitting top ... Continue»
Posted by donnamarie09 1 year ago  |  Categories: Anal, Shemales  |  
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take at the mall

I was out shopping with my mom and this guy kept following us; overtime my mom was not looking he would grab his cock which was getting hard and bigger. I had no idea how he was not getting noticed by the other shoppers. I told my mom we need to split up so I can shop for my own clothes and would meet up at the food court in a hour. I found a baby changing room and did not lock the door and waited; he came in a locked the door; I was so hot and horny I thought my little cock was gonna explode in my panties. He grabbed my neck and ripped my yellow t shirt; “oh fuck” I thought what am I gonna do... Continue»
Posted by kellyblue66abc 24 days ago  |  Categories: First Time, Group Sex, Shemales  |  
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