Shemales Porn Stories
Page 56

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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my date with jennycumslut part two

The second part of my story about my date with Jennycumslut. This memory will be burned in my mind forever and thinking about it drives me wild to know I did what I always fantasized about! Hopefully this will make you cum hard...

I left off that I had just made plans with Jenny to see her later that evening. I was out for a nice paced walk in the park close to my apartment at the time we had made plans so I hurried back home. After drenching of sweat from hurrying home since I was to meet her in less than a hour I quickly showered and didnt have time to shave my pubes down.

Me and her t... Continue»
Posted by redhotnailpolish 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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Gary's Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov... Continue»
Posted by palmorr 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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The last time I was a slut for cock

This is an account from my diary about the last time that I was a total slut for cock, before I realised that there was power in being dominant.

Went over to see Peter yesterday, it was about 8pm when I left his house but I didn’t have to worry about rushing home.
It was nice being with Peter again, he’s taught me so much the past year and he loves me in feminine clothes but he wouldn’t let me take the dress that I’d worn for him home. He let me go home wearing the bra, pants, stockings and suspenders though, it felt lovely wearing them when riding my bike. I felt so happy having spent th... Continue»
Posted by angelatvdom 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Old man fantasy

I have always been aroused by horny old men,I always wanted to be exploited by a group of old horny men until one day when i got this job that required me to take care of a 66 y.o gentleman.
He seemed so nice and since it has been my passion to serve other men i accepted the job without thinking twice.Things went well and we got along just fine..he was really funny and we became close friends very fast.
One day he called me and told me that he must speak with me face to face so that he can share a problem that he had for years with me,I rushed over to his place worried that something may hav... Continue»
Posted by cutecdkiss 1 year ago  |  Categories: First Time, Mature, Shemales  |  
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Vicky's Pink Diary 04

My head is spinning now, and as my uncle slowly pulls my panties down, I close my eyes dreading my fate!

I watch as he pulls my case out from under the bed. He takes a key out of his trouser pocket and unlocks the padlock.

"My god, how long have you had a key?!"

"Vicky, surely you remember losing a key a little while ago. It fell out of your jeans when your stepmother pulled them out of the washing machine. She didn't notice, but I did. Now I don't want to bring the other you up, but I did wonder why you would have a key in your jeans."

I knew I'd lost one of the keys, but I ne... Continue»
Posted by sparkyking 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Vicky's Pink Diary 03

So here I am waiting for my Uncle to come home for his tea, wearing Donna's knickers! Vicky's wardrobe is quite sparse, due to having just one locked suitcase hidden under my bed. I'm lucky that my stepmother is roughly the same size as me, and a total slut! Probably the only thing I like about Jenny is her clothes, she dresses like a girl half her age, and I know for a fact she shags around. I know my friend Sean has had a few narrow escapes from my stepmother. Then one day when I ask him about the way they smile at each other, he owned up. So I now know that they have fucked, I finally got i... Continue»
Posted by sparkyking 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Male to female transgender. Had no idea!

This is a true story. This was a time in my life where I was sort of a bitter person. This story is geared more about the things that led up to my encounter. This was a result of a series of events led up to this point in my life. Let's begin with the basics. I was in the military. I enlisted because I had one full time job and two part time jobs and still had trouble making ends meet. I was seriously overworked and my wife refused to get a job. So logically, I weighed out my options and decided to enlist into the military. It would be one full time job with a slew of benefits. Once I graduate... Continue»
Posted by fortworthfitness 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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Wife and Sissy invited to a party

My wife and I were invited to some friends’ house on a beautiful estate in TX for a weekend party. While we were both well aware of the debauchery that could occur at the event, we had no idea how much participation we would both play. We were just getting off the plane to meet our driver when my wife handed me a slutty little maid outfit, and told me to go into the bathroom in the airport and change before we got out of the terminal. I did as she asked and then tried to walk out without anyone noticing but too many people in the airport to hide from as I only attracted more attention.

When... Continue»
Posted by moeclitty 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Jake and sexy Tgirl Amanda were next on our "

So after we went out with Pete and Becky all day
Jet Ski's, Diving, and sneaking off for some impromptu blowjobs or a quicky, Alex and I decided that we'd ask Pete and Becky if they'd mind if we brought Jake and Amanda into our group. We described them to them, and they were hooked.

That evening at dinner Alex took it upon herself to make the first move. She sent over some drinks, and they came over to our table and that's where this story begins.


Amanda asked if we were swingers, when I spoke up and told her that even better than that, we're all bi swingers. Her jaw dropped and he... Continue»
Posted by SpicySide69 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Deflowered at 17...Part 1 (ENGLISH VERSION)

Many friends, some of them curious and excited by my (recently discovered) Polaroid pictures made at the seaside (with stockings) when I was 17 years old, asked me to tell the story associated to them. Someone also pointed out, "but if in one of your stories you talk about your first man -see story “my first man”- after having been “initiated” by a trans, then who was actually your first man? "
First of all, let me say that I can assure you that my stories are not fancy, they are absolutely true. I can change some details, names, situations, ... but I do not not invent anything. Anyone who... Continue»
Posted by AngelicaTrav 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Deep throat Made Easy

Deep throat Made Easy -reposted fro menext


Here for the first time ever are simple and explicit instructions on how to deep throat a penis. Position is important; you'll want to in position where you can extend and straighten your neck by slightly tilting your head back. This helps line up your throat with your mouth allowing the penis to slide in deep. The best position for beginners is with the receiver lying on his back with the giver lying on the stomach along side. You can prop yourself up on your elbows.

The penis must be THOROUGHLY LUBRICATED! I can't stress this enough. An... Continue»
Posted by bigdaddycoolzz 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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''What's a man to do'' Pt


We reached the fun chamber and I unlocked the door and told the lady's to go in and get to know each other while I went and fetched some glasses and a two bottles of red and a bottle of bubbly.
I returned to find the girls siting on the edge of the bed chatting and giggling like two school girls. It surprised me that Elke hadn't this hot little thing between her legs licking her pussy out. Usually my wife doesn't waste time chatting when she has an itch that needs scratching.
I locked the door, not really because I didn't anyone walking in on us, after all it was a sex party, but because a... Continue»
Posted by guru6969 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Pai-chan’s long walk home

School-gurl Pai-chan took the short-cut home from school, through the Sakura sweet smelling woods one Friday after class. The trail went past an old hut and as she approached it, a masked man jumped out from behind her, grabbed her by the arms and slipping a ball-gag into her mouth, d**g the sexy gurl into the hut.

There was a dirty, stained mat in the hut and her a*****or threw Pai-chan onto it. He lit a cigarette, his eyes glinting through the mask as he watched her struggle uselessly against the bonds.

“No... Continue»
Posted by tuckpussypeachpie 1 year ago  |  Categories: Fetish, First Time, 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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My Fucking f****y 2

My s****r had just come out of the closet with a handful of clothes and told me to take off the swimsuit. She laid out a pair of white cotton panties with cherries on them and a matching bra. A short pleated plaid skirt and a white button down shirt. She also laid out some white thigh high stockings and some black Mary Jane platform shoes. She said this one was mine.

She laid out a nearly identical one except that her plaid skirt was green whereas mine was red. She told me to get dressed but that she would help me with the stockings. "You know I have always wanted another s****r. "Someone t... Continue»
Posted by 6270daniel 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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''What's a man to do''...

After a long week in work I didn't really feel like going to the party we'd been invited to.
My wife said ''We have to go and you never know who might be there''.
I agreed reluctantly and showered and changed and we headed off to the party.

Now at this stage I must tell you these are no ordinary parties we attend. We're part of a group of people that like to play. Yes it involves swapping and doing kinky things with other naked people.

We arrived a bit late and so some of the guests had already shed their some of their clothing.
A few topless women sipping wine with men with bulges ... Continue»
Posted by guru6969 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Helping a gurl out

Just to explain a few things, we live on an island in the irish sea between Britain and Ireland. T-gurls are rarely heard from, nevermind seen for fear of negative comments.

Vikki was a t-gurl that my wife (K)and i met via a swinging site and had played with on a number of occasions. She would visit the island with work and when done for the day would indulge in meeting anyone who wanted to fuck her.

Vikki arrived on the island on the Wed and we met her on the Saturday. As this was our 3rd meet with her we had all got quite familiar with each other and enjoyed a very sexy evening togethe... Continue»
Posted by ManxTightslovers 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Cd Fuckdoll

I’m a part time cross dresser, and when I’m in fem, my name’s Koni, at least that’s my name when I’m a blonde bimbo. Last Saturday night… I had arranged to meet this guy at his house. He wanted me to park in the alley behind his house and come in through the back gate. So I arrived early, so I’d have time to put on my makeup and long blonde wig. I was already wearing my black-lace panties under skin tight black leggings and a pink halter-top over a strapless bra, giving the impression I had some perky breast. When I was as confident, despite my fear, I texted him, "I'm here," He replied to le... Continue»
Posted by Konicum 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Prostate Milking, Endless Orgasms!

if she wanted breasts."

"Oh no. That's the amazing part. The more I dressed him the more feminine
he became. By now I'd moved him her and her clothes into the other
bedroom. She wasn't happy with that but we came to an agreement; I'd milk
her once a week and she would sl**p in the other room with all her
female clothes. I'd even started teaching her to flirt with a guy although
I didn't tell her what I was teaching her or why. She really was becoming a
real woman. She'd grown her hair and I taught her makeup, had her ears
pierced, got her some jewellery, even got her some bra inser... Continue»
Posted by moekoes8 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  
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