Shemales Porn Stories
Page 11

Meeting with the Boss

I arrived to work to find out that my boss wanted a meeting to discuss my future with the company. I wasn't sure if this was good or bad. My boss, Erica, is a very beautiful woman. She is hispanic with bronze skin. She resembles Eva Mendes and is about 5'7" tall, 130 lbs with great curves. She always wears tight skirts and blouses. I entered her office and she told me to sit. After talking for about 20 minutes I was thinking this is good because I would have been fired immediately.

She then asked me how dedicated was I to her and the company. I said very dedicated and that I love working he... Continue»
Posted by swordlvr69 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 3736  |  
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Caught by a neighbour in my s****rs clothes.

It was 10 o'clock on a Friday in late June of 1997. My parents were away visiting relatives for a few weeks. My s****r Kate had gone out partying with her friends for the night and wouldn’t be back till Saturday morning. Which left me all alone in the house.

For as long as I could remember I always loved dressing up in my s****r's clothes. When I was lucky enough to have a whole night with them out of the house, I usually went all out in my s****r's room. ??
I had been shaving what little body hair I had for years. I used to lie and tell anyone who noticed that a lot of swimmers and athlet... Continue»
Posted by kara_zor_el 3 years ago  |  Categories: Shemales  |  Views: 3732  |  
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It doesn't get any better than this!

15 years ago, I went into my older b*****r's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out my cock, and have at it. When I opened the mag, my jaw dropped and my dick got so hard, so fast it practically popped out of my pants! I could not believe what I was seeing! It was a gorgeous babe alright, but she had a BIG hard-on where her snatch was supposed to be! My cock was pulsing in my pants,... Continue»
Posted by bugaboobed 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3711  |  
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foxxiroxxi gets fucked by a black bull at a costum

I was invited to a costume party by a good friend of mine named lexi , she has been my friend since we were k**s and knows i love to dress up as a women from time to time so she invited me and i accepted . The theme of the party was tight and short so unless you had the dress code on you dont get in . Lexi and i had to go shopping for new outfits to wear , we head straight to this dress shop that only has sexy club wear and dresses that only just cover your privates which was exactly what we wanted . Now both us were going to this party looking like two girls that wanted nothing more than cock... Continue»
Posted by foxxiroxxi 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 3706  |  
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TRAP

I was dating this 27 year old fox. And I was luvn it. You See Im 44 years old a lil overweight and I have a 5 inch cock! So you can imagine my surprise when I picked this little honey up at the bar d***k and the next morning she didnt want to leave!
The first night I got her home and we dove into bed Im 6ft 230 lbs with strong arms and long flowing hair We sucked each others tongues at first. I felt that tight body up and my lil boner was diamond hard. I got up to get her a liquor drink and I let my eyes feast upon this 5ft 8in beauty 115lbs of pure sin. She wore a size six shoe and had a bi... Continue»
Posted by playingroles 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3685  |  
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My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the room. Like I said there were lots of beautiful ladys there but one caught my eye. She was not too ta... Continue»
Posted by wildbill975 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3677  |  
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CD at truck stop with three men

Went to a truck stop last night after a party around midnight in my sexy short dress, got out and bent over looking at my tires for assistance. Gave a nice view to whoever was watching of my smooth white ass and sexy black panties with pink trim with half of both cheeks exposed. A nice older (63 yo) black guy (Ted) asked me from his truck if I needed help. We talked and then thanked him and asked if I could help him for helping me.

We walked over to his truck and got in his sl**ping quarters. Gave him some more intimate show of my nice ass, turned around, unzipped his pants and began ... Continue»
Posted by hotcdsub 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3677  |  
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this year Dr. visit

My Annual Dr'S Visit 2014

i guess I'll describe this years visit and if you like reading them I'll continue to describe my annual Dr. Visits. I've been seeing the same Dr. and his Nurse for about 4 years now. The first one was mostly normal however the last two previous ones have been kind of embarrassing for me and I wondered how this year's would be. I made my appointment and and as usual the nurse came to the waiting room and got me and took me back to the exam room. She had me go into the changing room to put on the gown . I took off my shorts and top exposing my bra and panties like ... Continue»
Posted by sissygirl 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 3667  |  
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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: 3656  |  
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Unexpected friends CD fantasy

There really wasn't any planning to what had happened. Earlier that weekend, I had just felt this strange urge, so I decided to check online for something different to do that was new. Of course, I had done parts of this before, but most of them were separate in their operation. I had never done anything sexual with anyone, though I had posed, and the only time I had gone out as this was to see if I would be recognized. Maybe that was what convinced me to except his offer, as I somehow felt that I wouldn't be recognized by anyone locally.

So I had agreed to meet with a man at 8pm in a rathe... Continue»
Posted by RosalynLee3 2 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3651  |  
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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: 3651  |  
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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: 3647  |  
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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 7 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3646  |  
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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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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 4 years ago  |  Categories: Shemales  |  Views: 3633  |  
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three gets crowded

I was over at a 'friends' house the other day. Just relaxing on the couch snuggling up to him watching TV. His couch is halfway between a full couch and a loveseat. He is also a fairly large older man (in his 50's, around 6'2" and weighing between 240-250). Just how I like my daddies :)

I was wearing a simple outfit. A nice colorful skirt that went to my knees and a simple blue tank top. Plain, but comfortable. He had one hand around me, and was running his hand across the skin on my arms when the doorbell rang. I quickly got up and answered the door. It was his friend 'Jim'.

... Continue»
Posted by zaria_ts 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3633  |  
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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 11 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 3628  |  
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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3621  |  
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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: 3620  |  
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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: 3606  |  
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