Shemales Porn Stories
Page 9

I Knew I Was A Sissy (Part VI and half)

I started dressing full time at home. The minute I would return I would immediately take off my clothes and transform in a girl. Men clothes became my outfit for my day life. Each time I was dressed my sexual desire was increasing immediately; I wanted to get fucked hard, I wanted to suck cocks. Unlike when dressed in man’s clothes. None of my classmates ever thought I was a sissy, very few considered me as gay. It was strange to them that I didn’t had a girlfriend but as I was staring all the time at them they were not suspicious. They just thought I was shy on approaching them. What they did... Continue»
Posted by georgette32hk 3 months ago  |  Categories: Anal, Gay Male, 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 2 years ago  |  Categories: Gay Male, Shemales  |  
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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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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 3 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 2 years ago  |  Categories: Fetish, First Time, 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 5 years ago  |  Categories: First Time, Shemales, Taboo  |  
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How My Life Changed

How My Life Changed


Chapter 1
My wife Mary and I had been married for over eight years and I thought our
life was very good. She was an attorney for an important law firm and rapidly
rising towards a partnership. She made a lot more money than I did in my job as
a fast food worker. That didn't bother me as much as it might have many men.
We had a nice house and lived well. Mary is 28, 5'6", 120 pounds and had 38D
breasts. She is a beautiful brunette with brown eyes. I am 5'8", 140 pounds
and used to taking orders from the people I work for. As my wife gained more
... Continue»
Posted by klammer 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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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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Dominant Sex Therapy

I had to go see a sex ther****t because I was addicted to jerking off. Little did I know she had a surprise waiting for me when i got there. I sat down and she got right to the questions. "So how long have you been jacking off" She asked. I said "about 20 years now" She nodded her head and asked " Do you watch porn when you jerk off?" I said "Yeah every time" She said "Good. How many times a day do you jack off" I said "all depends sometimes once, If i get a really good scene I try to break my mind from cumming too fast so it can be, 4-5 times a day." She said "Wow that's a lot of masturbat... Continue»
Posted by michneo 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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How Nick became Nicki. A sissy story

This is the story of Nick. Nick was straight.
It was Friday night and she was getting ready to go out, she had something special planned tonight. She had her favourite pair of red and black lace lingerie on, the panties cupping her round smooth cheeks, her light blue pencil dress that hugged her figure and gave her a passable cleavage, white heels that make her look sexy even though they squeezed her toes and rubbed her heels and she had barely got the hang of walking in them. She had done her make up too, as well as she could, a little eye shadow and a cherry red lipstick. Her stomach was af... Continue»
Posted by ilgreturns 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Fucked by daddy's friend

This story was a fantasy of mine from when I was about 11yrs and still think of it happening now even tho the guy in question, is in his mid 60's

I'd be at home from school alone as my parents were at work. This is when I would go through my mums sexy underwear draw. I picked out a black suspender belt, matching bra and see through panties and some black seamed stockings. Luckily I was young enough to have a hair free body and was the same dress and shoe size as my mum. So I picked out a dress theat finished half way up my thighs but covering my stocking tops and a gorgeous pair of black 4"... Continue»
Posted by danny241976 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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Mrs. Thompson

Mrs. Thompson


It was a friday morning and beautifully sunny too without a cloud in the sky. I pulled into Mrs. Thompson's drive-way ready for what should of been half a days work flooring out a loft space. I parked up and rang the doorbell thinking about getting this job done quick so I could have the rest of the day off.
A beautiful lady who I assumed was Mrs. Thompson because I had only spoke to her over the phone, answered the door. Now Mrs. Thompson was at a guess, early thirties and around 5'8" tall with long legs, a nice lean body and shiny dark hair that fell just below her sho... Continue»
Posted by Davey76 4 months ago  |  Categories: Anal, First Time, Shemales  |  
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supermarket tranny

It was a typical Saturday morning. I was at the grocery
store doing my weekly food shopping. As I was perusing
through the vegetable section my eyes caught sight of a
a very attractive woman. She had long dark brown hair,
pretty face and a nice body.

I worked my way over to her and checked her left hand
for a wedding ring. She had none. I made some remarks
about the slim pickings the supermarket had. She and I
quickly engaged in conversation about cooking etc.

We walked around the store side by side picking our own
groceries an just having a good time. It was time to
c... Continue»
Posted by rickk1 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Deer Hunting with Daddy

Every year, a group of my f****y members, mostly uncles and male cousins, all pack up our gear and head into the mountains every fall for the yearly deer hunt. I had been going since I was 5. All the younger cousins slept inside an uncle's trailer, while the adult's and older cousins slept outside in a tent. This tent was huge and was intended to hold up to 10 people.

One year, when I was 8, I was having trouble sl**ping. I left the trailer and went to the "grownup" tent. As I got closer, I could hear strange noises...grunting and moaning noises ;-) I quietly unzipped the tent, but only en... Continue»
Posted by cdsexslut 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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The heavy girl in the bar.

This is one of those stories from my past that I wouldn't consider rather astounding except for how it ends. It was a monday about 2 years ago. I was recently single and pretty horny so I figured my best bet aside from dating websites would be to go out to a bar and find a girl to hookup with. I hopped from bar to bar in town and everything was pretty empty with mostly men. I got to the last bar I would visit for the night, it was a bit more upscale than usual but there were a few women there. I flirted with them but they turned around at the bar and started ignoring me as if I didn't exist wh... Continue»
Posted by experiencedjojo 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Halloween Night.

My wife has been at her mothers the other side of the country and will be for a few months, so I thought this would be the perfect time to go all out and see how convincing of a woman I could make myself. I bought hair removal cream, razors, new sexy lingerie, a sexy Halloween outfit, a wig and make-up. Naturally i received a few looks from cashiers, but I managed to smile and make a comment about how my wife's at work and leaves everything to the last minute.

As soon as I rushed home and got inside I began preparing even though it was still early, I knew id need extra time since iv never d... Continue»
Posted by RocknLoad 7 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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The special overnight bag

I did not want to have another boaring sales trip,so I packed up my special overnight bag for this trip. All the items a gurl would need to have a special trip. Inside were a few skirts some stockings and two wigs ( I can never decide)a few items so I could get clean and my laptop and camera.
After my sales meeting I went back to the hotel,took a long bath,cleaned myself and shaved everything smooth. Put on my make up ( this time I got my eyes perfect !) put on my stockings slinkey red skirt and this time I opted for the long black wig.

I felt so slutty walking down to the bar in the hotel... Continue»
Posted by sodeep2 2 years ago  |  Categories: Anal, Shemales  |  
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Sissy for BBC use and a b u s e

My Dear little sissy s****r, lezzie lover and slutty confidant...


Thanksgiving saw me full of BIG BLACK COCK...my mouth, my sissy pussy and my belly were full of so much BBC and SPERM from Big Black Daddy Dick (s) annnnd I was good little bitch in the Doggy position for the Black Daddys' and their DAWG POUND(ING). I finally hooked up with my own BBC GANGBANG SQUAD from the adult bookstore. They used me for well over 24 hours of serious sissy-slut abuse, degradation, domination, humiliation and more, much, much more! I can't wait to tell you about it. I wish you were with me so w... Continue»
Posted by santtxx 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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My Parents Had Gone Away on Vacation

My parents had gone away on vacation for a week. I was thrilled!

On my own for a whole week, free to do whatever I liked. And truth be told, what I liked was being nude, as well as dressing in women’s clothes. The first day they were away, I began enjoying my newfound freedom.

I am very slight of build, feminine really. My body is hairless save for in my crotch.

After dinner, I decided I wanted to enjoy myself nude. I turned off all the bright lights in the house, and left on a few lights that were dim. All the blinds in the house were open. I stripped off all my clothes and walke... Continue»
Posted by ssup28 1 year ago  |  Categories: Shemales, Voyeur  |  
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