Shemales Porn Stories
Page 9

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 6 months ago  |  Categories: First Time, Group Sex, 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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A COMING OUT PARTY

We had met on XHamster.com. Our profiles confirmed we lived in the same city. We exchanged private messages at first then we started exploring mutual fantasies. How we like to dress in women’s clothing, especially the lingerie. We shared masturbatory stories with one another. Finally, we agreed to skype while we were dressed. We wore masks for our mutual protection. This went on for a few weeks until one day he took his mask off. What could I do? I had to reciprocate, even though I was terrified of being outed. No one, not even my wife knew of my little hobby. I had managed to keep it hidden f... Continue»
Posted by justluvtrans 4 months ago  |  Categories: First Time, 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 7 months ago  |  Categories: First Time, Shemales, Taboo  |  
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My Ex-Girlfriend's Mom #2

I still couldn't believe all this was happening! I had just met up with my ex girlfriends mom randomly in a bar, found out she had a dick, (a big one at that), came home with her, given my first blowjob, received my first load of cum in my mouth, got caught doing so by my ex girlfriend, and found out she had a dick too! This had been one crazy night, to say the least! And it looked like it was about to get even crazier!

Jill looked amazing. Even better than I remembered. She must have had a boob job, because I remember her only having about a B cup. Now she had to be at least a D cup, proba... Continue»
Posted by naughty_bi_interest 7 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Like Mother

It was no wonder Lori grew up to be a whore. She grew up listening to her mom fuck men at night. There would be a knock on the door and her mom would answer it and let him in and take him back to her bedroom and Lori would lay and listen to them fuck. Sometimes their was lots of dirty talk. She would hear a man tell her mom "Get down here and suck my dick" or "Spread your legs and show me that nasty cunt." "I am gonna shove this big dick in your cunt and fuck you so hard." "Stick your ass up here you dirty whore." Even "How do you like a big black cock?" Lori liked when they left the door ope... Continue»
Posted by homewithdaddy 27 days ago  |  Categories: Anal, Fetish, 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 5 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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]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 1 year 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 5 years ago  |  Categories: Anal, First Time, Shemales  |  
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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 4 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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Closet Sissy step Son Made Into step Daughter


Why was I on all fours with my dad's cock in my ass and my s****r's pussy in my face? Well little did I know that my mom knew about my secret. She knew that I had been wearing her and my s****r's lingerie.

It started when one day I was home alone and wandered down to the garage to play around on the air hockey table. I got bored and looked around as we had a lot of stuff down there. Boxes were piled up on one side and I looked in a few of them and found something that made eyes pop open.

I saw a naked g... Continue»
Posted by Batman_112 20 days ago  |  Categories: Taboo, 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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My Steps****r has a Bigger Dick than Me


We'll just start with the basics, first thing is my name is Carter. I'm a 18 year old boy and currently a freshman in college and living with my parents and s****r. Some things about me: I'm an athletic person and I play a couple different sports (football and swimming), and I also generally get pretty good grades. I think I'm relatively smart, but if you're smart you also tend to question whether or not you're actually smart and who really even knows anyways? I wouldn't say I'm very popular, I'm a much m... Continue»
Posted by Batman_112 13 days ago  |  Categories: Anal, Taboo, 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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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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