Shemales Porn Stories
Page 11

Letting my neighbor see me jacking off!

Yes, i am lucky to have a hot neighbor, a guy who likes to watch me when i am outside, in the yard or even geting into my car, it seems that when i go outside, there he is! So, why not give him what he wants, whether he knows that i am a shemale with a hot 7 inch cock, or as he might think, a girl with a wet, pink pussy. I know he jacks off to me, i did see him in his upstairs window last month, shades pulled up, jacking his big cock off as i wa outside in shorts up to my ass. He shot a load on the window and i know he knwos that i saw it all. so? My turn! Shortly thereafter, i went outside in... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 3655  |  
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A busy Friday night. [CD/Gloryhole/neighbor]



I had been looking forward to this weekend for a month. My wife was going to visit some friends in NYC, and I was staying home, by myself. Yup, just me and all of my favorite things, like stockings and panties, and sexy little outfits. The torture was finally over, and the Friday she was to leave, arrived. I was still at work when she called me to tell me she was on her way up rt. 95. I wished her safe travels, and told her I would talk to her tomorrow.

I immediately left work, and headed for my car. I was so excited that I practically ran out of the office. I was going to indulg... Continue»
Posted by pbg732 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3656  |  
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Bi male and anal sex

Thru out my adult sex life I have always enjoyed having my ass teased and played with. 
Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. 
Then one night things changed. After a hot night of wild sex, she slowed things down before excusing herself. But before she left, she rolls me over on my chest, which to me means she want to tease my ass. I hear her in the bathroom , toilet flushes and I hear her returning to the bed, straddling my legs, she racks her fingers up and down my back before she l... Continue»
Posted by rogue-1966 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3647  |  
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becoming Rachel

I was about 15 when i found a bounty of porn magazines and female lingerie in the park near my parents house. Without thinking at all i grabbed it and took it home. that night after getting horny reading some of the porn magazines I tried on some of the stockings and silky lingerie. it was the sexiest feeling i had ever felt. they seemed like a natural fit for me, as i had a slim and somewhat girlish figure.

Over the next few months i regularly played with myself while dressed up and reading the mags. but after a while, without the magazines, imagining I was a girl, with my legs spread wi... Continue»
Posted by rachel_cd 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3641  |  
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Impregnated by tentacles

I had just finished a session up at the gym and began walking back to my car. It was dark out and the large car park was empty, nobody could see me. I was wearing just a tight grey leotard. Like this…

My big bulging cock showing clearly up my stomach, small wet patch from a little pre cum, my tits free, no bra, nipples erect from the cold, wobbling as I walked, along with my ass and thighs.

As I got to my car I got in and got myself comfortable, suddenly I was locked in my own car, from under my seat crawled fle... Continue»
Posted by shemalecharlotte 6 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3638  |  
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Me and my part time job

I was always doing part time jobs to help the f****y with the bills, I was the youngest of 10 k**s ,but the only son. As I was walking home from school one day This guy asked if I was looking for a part time job that he had to clean out his basement and garage I was very very happy to say yes I'm always looking for extra money he asked me to come in. The Large house had a lot of antiques in it, The man "James" introduced me to his wife "Diane". We went into the kitchen for coffee and what they needed me to do then she kissed her husband and went to work.

James said that the junk was going t... Continue»
Posted by sissytimmy 10 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 3634  |  
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The Girl? Next Door

A knock at the door, it was her of course! She came in and look a little d***k too, we sat and talked for a short time. I was wearing shorts and she noticed that my dick was slowly get a semi just checking her out. Thats when i noticed her hands go down on to my shorts where my dick is, she looked at me licked her lips knowing that i wasn't very experianced told me tonight she would be boss, i eagarily agreed. She took my pants down and while kisses me was rubbing my cock up and down, wow this felt amazing the way she moved on my cock was almost as good as me, she wet her finger and while... Continue»
Posted by ts_lover69 3 years ago  |  Categories: Shemales  |  Views: 3631  |  
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The Bike Path

I've been wanting to submit a story for a long time. I have a ton of ideas for some fictional sex stories but very few real life stories to talk about since my sex life is fairly normal. this story was special because it happens out of the blue and with a dream girl.

My buddies and I had been planning to attend this festival downtown. To avoid the traffic and trying to find parking, which can always be a bitch and not to mention the parking tickets if the meter runs out, i decided to leave the car at home and public transport. This also left me the option to drink and not drive or even t... Continue»
Posted by mikmarkham 1 year ago  |  Categories: Anal, Shemales  |  Views: 3626  |  
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Chloe's Slutty Night at the Truckstop

If you have read any of my previous stories, you know that the freedom of college took my secret life as a slutty cross dresser to a whole new level of naughty. I became a great cocksucker and I started to constantly crave a hard cock in my boypussy. I started dressing more often, going from 1 or 2 times a month to at least once a week. I was building up my collection of clothes and toys and getting more and more daring every time I went to meet a guy. I started to just go to my destination in full slut attire instead of getting dressed when I got there. Anyway, this constant escalation of my ... Continue»
Posted by cumslutchloe 9 days ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3629  |  
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SHEMALE SURPRISE

while in our early teens my cousin nicolas and
i used to look at porno mags and videos up in my
tree-house which was quite a ways from any other
structure. during these sessions nic and i would
whip out our young hard-ons and whack off to the
images of naked women and men of all ages. we got
together to do this about once a week and discuss
the sexual escapades we may or may not have had
with girls we went out with during the week. a week
after nic had graduated (i was still a junior) he
came over to the tree-house and said
he was leaving for the city "to find himself."
when i... Continue»
Posted by qrystofer 12 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3621  |  
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Vicky's Pink Diary 01

There he is sat on my bed, my Uncle, Uncle Creep, well that's what I call him. I'm just staring in shock as he flicks through it.

"Put that down, it's private," I manage to blurt out.

"Don't worry, you poor little thing. I've read it right through a few times. I won't tell anyone, Vicky, isn't it?"

I'm shaking in horror, my diary, my pink diary with all my secret thoughts and wishes, my fantasies, and things I've done, embarrassing things. Well how many 18 year old boys get a kick out of wearing their and their stepmother's underwear and dresses? How many boys write things like tha... Continue»
Posted by sparkyking 7 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 3607  |  
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My New Girlfriend Turns Out to Be a Shemale.

Where do I start?
How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I dress nicely and have a good job.
My friends Don and Lisa were feeling sorry for me they knew how ugly my divorce was and how lonely I was so they invited me to their pool party last weekend. They said there would be some single women there and I might find someone I like.
Okay, I thought at... Continue»
Posted by triphammer73 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3602  |  
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An amazing true story

okay never done this before but here goes =) So i had just broken up with a girlfriend a couple months ago, and had been feeling pretty down and unhappy. I had a friend of my f****y invite me over to hang out and play some video games and eat some dinner. When i got to their house Jan and Ted, they have been married as long as i can remember about my parents age, were glad to see me and felt some relaxing fun would take my mind off things and everyone could have a good time. So we started playing some video games and drinking some wine when ted had to get up to do a little work and left Jan an... Continue»
Posted by xnotclspamx 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 3594  |  
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throat fucked by two black photographers

Well for a very long time i would go to a hotel room to dress up in my sexy outfits and set my camera on auto and take my own pics .After a while i got bored with that and wanted to do a photoshoot with a photographer so i rang around and found a guy who would take my pics .I went out and brought this sexy nurse outfit the day of the shoot this was the first outfit i wanted to wear .The night finally was here i am all dressed up make up on feeling very nervous but excited i reakon you could see my heart pounding out of my chest.There is the knock on the door when i opened it there was two very... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 3589  |  
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My first time

I sat in the car outside the address and to say I was nervous is a understatement. This was the first time I had ever done anything like this and I was half thinking of just driving away.

I had got messaging to Sara a month ago after liking the pictures they had posted. I was really in to clothed sex and the pictures showing Sara in a selection of boots whether they be leather or pvc, knee high or thigh high I didn't care as long as they have a stiletto heel l love them.

As for clothes I get hard for the slutty secretary look, a nice tight pencil skirt with some stockings and high heel... Continue»
Posted by big_rob49 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3582  |  
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Little MIss Sissywhore




Little Miss Sissy Whore


Chapter 1 -- The Pick-up

Every year I waited eagerly for the three days when PC-Expo was back in town. In the past, I was always able to find some willing and naive out-of-town female to pick up, "do the nasty," and say my hasty good-byes. Most of them were from some small hick town and were entranced with the Big Apple. In fact, that was both the nickname for the city, and for me. Most women just couldn't wait to sink their teeth into me. So there I was, looking for some love, on the last day of the three-day convention. I walked up and down the ... Continue»
Posted by klammer 3 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 3581  |  
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Caught by my wife

I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and came in the side door of the garage, I use the garage to film my escapades. And all this time I've never been caught, now I'm caught and can not go back... I am passable. I'm always dieting, I work out but I work out to slim and femme myself.. My wife has the most beautiful body ever, and thats why... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3571  |  
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Sissy Serving Poker Night

I was terrified when I was actually invited to serve at the usual Friday night poker game with 5 guys I had been talking with online. Three of them are black and 2 are white. I arrived at the house to find a nice setup in a basement rec room with a card table and a pool table.

I was nervous as I approached the front door and knocked having never done this before. The party host answered and immediately I was told to get dressed in something sexy and start serving drinks. Well since the only thing I brought with me was my thong and high heels, I put those on and came out, trembling with nerv... Continue»
Posted by johndavies4321817 8 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3565  |  
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Flying High



The plane landed as scheduled. Luckily it had been a very smooth flight. I made my way through the busy airport. While I was waiting for my luggage my eyes went everywhere looking for beautiful girls. I saw my luggage come around and went for it. At the same time a voluptuous brunette reached for the same bag.

“Excuse me,” I said. “I’m pretty sure this one is mine.”

“Oh I’m so sorry, the look like mines.” Her voice was soft and sounds a little hoarsed. I looked her up and down. She had a very latin style, which my cock i... Continue»
Posted by Pedeco 2 years ago  |  Categories: Shemales  |  Views: 3556  |  
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Black Mamba - pt 2

As I entered the bedroom, Jennifer indicated that I should stand and
approach her. I rose to my feet and stood before her feeling intimidated by
her size and demeanor. Jen reached out and yanked my precum soaked panties
down to mid thigh, roughly f***ed my now withered member between my legs
toward my ass, then pushed my aching balls up into my body cavity. She then
drew up my panties tightly so that my cock was effectively trapped.
"When you are in my presence, your worthless clit is to remain tucked away
as it is now, unless I order you to do otherwise. Do I make myself perfectly
... Continue»
Posted by germanboi4bbc 9 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3556  |  
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