Shemales Porn Stories
Page 11

My First Girly Cock

It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. I don't consider myself being gay, but I always had that ardent lust to be with a transsexual woman. I just couldn't get them out of my mind.

This passion started a couple of years ago, while I was surfing on the Internet looking for hot stuff. Immediately I felt something. That first time, when ... Continue»
Posted by jimpgr 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 4207  |  
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Sissification continues

As I sat in front of the mirror my long locks looked great and as I applied my final bit of red lipstick to my lips I looked the sissy slut I had craved to be ever since I had been introduced to cock by my now ex girlfriend.

Tonight however was going to be a new experience for even me with my introduction to Black Cock and just hoped I looked sissy enough for them. I had been chatting online with two guys both in their 50’s and after very little persuasion I was inviting them to my house.

Then the knock at the door came, it was time for action. Opening the door the two guys smiled their ... Continue»
Posted by sissyman71 21 days ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 4196  |  
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My brief stab at prostitution

This happened when I was 22, I was broke and hanging out in my hometown, a large eastern New England city of about 500,000. I was hanging out on what was the main drag looking to see if i could get picked up by a guy for sex. I got a lot of interest but no one was stopping. after about 90 minutes I said "fuck this" and decided to go to a diner about a block away. I cut down a covered alley that cut through a huge department store and started walking up toward the diner. it was chilly and the wind was gusting as i crossed the street. I sort of noticed a van following me on the left. I figured t... Continue»
Posted by aurora_dream 1 month ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 4178  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 4181  |  
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Paying rent

I’ve always enjoyed getting dolled up like a sexy girl ever since I hit puberty. Doing my hair, wearing frilly panties, skirts, painting my nails and doing my makeup. But being a boy that isn’t viewed as proper behavior. Which is why I’ve always had to dress in private. But luckily with the power of the Internet I’m able to express my inner girl. I run a blog where I post dirty pics of myself dressed up, erotic stories of young crossdressers being used by older men, captioning dirty pictures and I do webcam shows just about every night. I even get tipped for my webcam shows and can use the mo... Continue»
Posted by ScarlettMaeBottom 2 months ago  |  Categories: First Time, Shemales  |  Views: 4162  |  
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I was bored one afternoon...

It was my day off. I was bored, and very horny. I can't help myself some days. Well, I thought to myself, I can either jerk off quickly or take a drive to one of the two adult stores with peep shows. It didn't take too long to decide.

I live in a very cold climate, and it was fairly cold out today, so as tempting as it was, I wasn't going to dress up in a cute skirt. I slipped into some tight jeans and looked at my profile in the mirror. I sure wish I had a better ass. Just a bit more of a 'bubble' would be nice. I put on a cute shirt and put a generic dark blue hoodie on. Dressed l... Continue»
Posted by zaria_ts 19 days ago  |  Categories: Shemales  |  Views: 4161  |  
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Down the Path

Down The Path


I hear the knocking on the door. Have my panties on under my shorts and tshirt. Nervously open the door and the man comes by me and I follow him into the living room.

He stops and turns. 'On your knees now'. He moves in front of me showing me his ID so he knows I know who he is in case he gets out of line. 'Tell me why you invited me here.' Looking down embarrassed to have to say it. 'I invited you here to treat me like a faggot Sir. I need a real man to come over occasionally and show me just how much of a fag I am.'

He lifts my chin with his finger then suddenly he s... Continue»
Posted by lookin02 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 4149  |  
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Finding a Great Roomate

I had just moved to the Great NorthWest and was lucky enough to land a job as a convenience store clerk working a shift from 8pm to 4am. Money was tight so I went to the classified to look for an apartment to share. I found one that was fairly cheap and close to my job. It was a two bedroom apt. and I would share the kitchen and common area with my roommate. I gave the guy a call and set up an appointment to see the apartment and be interviewed by him. I went to the address and rang the bell. The door was opened and there stood huge guy, well over 6' tall and I would say around 260lbs. H... Continue»
Posted by rikki50 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4145  |  
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Fist visit to my sexy new female doctor

Yesterday I went to the doctor because i felt like i was peeing too much, i'm sitting in the waiting room and the doctor calls me, and she is the hottest woman i have ever seen. Late 20s/early 30s, gorgeous middle-eastern face, nice curvy lips, big dark eyes. She's very friendly with a thick Persian accent which i find very sexy. i explained to her my situation, and then she asked if i was sexually active, and i said no a bit too quickly, and she looked surprised for a second. She got me to pee in a jar, dipped the testing strip, and came over to show me the results. She got me to hold one end... Continue»
Posted by wet20 11 months ago  |  Categories: Sex Humor, Shemales  |  Views: 4143  |  
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My First Cock

I always knew I really was meant to be a girl. For a while I thought I was simply gay, but I loved wearing thongs and bras. I loved masturbating while pretending my asshole was a vagina. I never made it a secret. I'm very flamboyant and girly. I still managed to have lots of friends in high school. Several of them knew I wished I was a girl.

One night I was very upset about God knows what. I was crying with a good friend of mine at his house. He was straight and had a girlfriend (another good friend of mine). I began venting to him about wanting to dress like a girl and be treate... Continue»
Posted by hotchickinchitown 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4140  |  
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Getting caught on purpose ( true )

I had gotting tired of my mother showing up at my house everyday with out notice.She always came in and whated to move stuff around and say something about a dish in sink or what I had cooked for dinner last nite.I love her but since her boyfriend past away she was driven me crazy.
So I woke this morning early and asked her if she wanted to go shopping with me.She said yes I bought some heels bras painties and we went got our nails done.She asked do you own any male clothes I told here no.Well I dropped her off at her house and left and 20 minutes later she showed up I tried to tell her cal... Continue»
Posted by cdpaula 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 4130  |  
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MY GIRLFRIEND HAS A PENIS???

I met Gina at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to find such a babe here and she likes ... Continue»
Posted by laceysgirl 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4120  |  
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Wife turns white hubby into black cock cuckold s*s

"Oh my god!"

My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?"

"Kelli what the fuck's going on here?!"

At that, the black guy turned and shot me a nasty glance. "What's it look like we doing, genius? I'm dicking your old lady. Now get out of here fuckshit I ain't finished."

"Better go downstairs dear," Kelli said, smiling. "I'll be down later to explain."

Of course I was shocked, but what else could I do? I went downstairs poured myself a drink ... Continue»
Posted by whitewhores 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 4102  |  
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Slutty Sissy Used in a Cheap Motel Part 2

After being fucked and bred by the first 2 strangers and watching my sissy hypnosis videos I was definitely ready for at least one more deep fucking. It was around 10 p.m. when the next guy knocked on my door. I opened the door to find a very large black man about 6'8" and a smaller black man who was about 6 feet even. I invited them both in and was very excited that I was going to be tag teamed by 2 black cocks. These two guys were very demanding and knew exactly what they wanted. I knew that I would do whatever they told me to do, because every ounce of my male thought process was gone and m... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4069  |  
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The Truckers Reststop

I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem myself up it was already 8pm, so I thought what the heck I'll drive up the Interstate just north of Seattle to a truckers rest stop I have gone too before. The weather had cleared up a bit, so I was hoping for some fun. I dressed in my short wrap around skirt, red thong panties, red Bra, and a shea... Continue»
Posted by cd_lorretta 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 4067  |  
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Losing my Cherry

Although l have been secretly cross dressing for years I have never took it beyond the confines of my bedroom or hotel room. Well I have been really wanting to take this to the next level. So as I was traveling on business this past week I answered an ad on Craigslist for a massage in my hotel room from a male masseur I made the appointment and waited with anticipation for my masseur to arrive. At promptly 8:00 there was a knock on the door and when I answered there was Chris a very handsome young man, I invited him in and he promptly set up his table..
As he was setting up his table and ... Continue»
Posted by mikkas72 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4044  |  
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Sex with teacher(sissy)

I was the 2 year of high school back then. My grades werent going realy well moastly becuse i spent most of my freetime blowing guys,and sticking thing in my ass,then studying.My parents one day decided that i need some extra classes,so they hired a tutor. I wasn't realy up for that idea,but they somehow talked me into it. After a while it was the time for me to have my first class. My parents left for work,and i was home alone waiting my teacher.Then the dorbell rang , i felt so nervous as i opened the door. In walked a handsome 25-6 year old man,fresh out from college,in a very nice suit. We... Continue»
Posted by sissygirl1988 1 year ago  |  Categories: Anal, Shemales  |  Views: 4043  |  
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becoming a slut

It all started when I was 13 and discovered the joys of wearing women's clothing. It started with my older s****rs panties then my highschool girlfriends things by the time I was 18 I had a pretty good collection of womens clothing even with never having the nerve to purchase any of them myself. Then came the urge for more when dressing up and masturbating wasnt enough I wanted more. I always considered myself straight despite my crossdressing but when dress would get the urge to please a man. So one day I got my s****rs 7 inc dildo. I got dressed up in some sexy thong panties some nylons and ... Continue»
Posted by RenoBoi 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4040  |  
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Transexual Brothel

While I was on vacation, I went to a famous brothel. It was a large place with several different bars, a room with stripers, a video bar. etc. I wondered around for a while taking it all in. I settled down in a little quiet bar with a classic old black-and-white porno movie playing on the TV. I was propositioned by several women, but they didn't really turn me on so I turned them down.

I nice-looking woman set down at the bar across from me. She was a little older than me, probably in her mid-thirties. She didn't look like a hooker. She looked nice. I smiled at her and she smiled back. I w... Continue»
Posted by slatemhor 13 days ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4066  |  
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Sissyfied

Not so long ago I was a your standard guy into women etc so how did I become so sissified, well i blame my ex partner lol.

We always had a great sex life and were occasional swingers which she started. Now we always liked to swap our love juices but this one time she went a stage further when she sucked off our swinging friend, until he blew in her mouth, she then walked over to me and while our friends wife rode my cock my ex proceeded to kiss me hard letting his cum into my mouth. Now I always liked the taste of my own cum but was not sure how i would react to another blokes cum in my mou... Continue»
Posted by sissyman71 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 4029  |  
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