Shemales Porn Stories
Page 7

Mom Transforms Son into a Transsexual.


I'm a very sensitive white teenage boy who's always been close to my Mother,but my Dad looked upon me with disgust calling me fairy,sissy,faggot, and other choice words, Father was a Marine he is six feet seven inches tall, black hair, Blue eyes, and a Alcoholic. My Mommy is six feet three inches tall, 42DD 28 44 inch frame, long red tresses that flowed over her Boobies and she like to show them off. My parents divorced two years ago he drifted off into alcoholism some place, I was watching porn on Moms computer checking out Shemale and Cross dressing web sites when all of a sudden I heard... Continue»
Posted by sissytimmy 1 year ago  |  Categories: Interracial Sex, Shemales, Taboo  |  Views: 5118  |  
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My b*****r's Lover

I was eighteen and in high school when it happened, my b*****r was twenty and still living at home. I had to borrow my b*****r's computer one day to do some work for school and I guess maybe I let my curiosity get the better of me a little as I found myself instead of writing the essay I was supposed to be working on, looking through what files he had saved on his computer. I was pretty interested in particular by a very full folder hidden away in a place that you would not expect to find it. Now, I'd been a teenage boy for long enough to know that I had probably just stumbled across my b*****... Continue»
Posted by sparkyking 10 days ago  |  Categories: Shemales, Taboo  |  Views: 5138  |  
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Happy Birthday to Me

So last month, I was lucky enough to experience one of my favoritest annual events ever: my birthday party!!! Now, for those that don't know, I take my birthday VERY seriously. You see, I was only 12 years old the first time I played with a pecker...and I've been lickin' 'em and suckin' 'em and bouncin' up and down on 'em ever since :-) I suppose my love of being gangbanged and making guys cum on my birthday all began on the eve of my 14th...

It was a hot night in June and I had invited about 20 friends to a backyard birthday party sl**pover. 14 of my best buddies showed up. I had blown... Continue»
Posted by cdsexslut 3 months ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 5056  |  
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Me, Mom and the Hair Dresser

Growing up as a only c***d I was smothered by my Mother, I don't know if it was normal ,but at 14 she was still breast feeding me,bathing me, and sharing one bed . I was a very shy boy, we moved every year so I was always getting beat up at the new school. I had no thoughts until my 14th birthday. It's funny how these things change so fast,I had received my first computer, I was looking up and typed in the words "Mother and Son" I was directed to a porn site one of the pictures was of a mature woman pegging a teenage boy wearing lingerie I got my first erection. So when Mom called me for break... Continue»
Posted by sissytimmy 11 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 5052  |  
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My Shemale Stepmother

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly following the divorce and had already found someone new and I had to say, he had done pretty well for himse... Continue»
Posted by bi_hengst 8 months ago  |  Categories: Shemales  |  Views: 5020  |  
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Sucking my straight friends dick

It was a typical Friday evening; I had just got done hanging out with a group of friends, and one of my friends decided to come over to my house and hangout for a while. My friends name is Dave, I met him in highschool when I was on the football team my sophomore year, he was a big time jock and became a co-captain on varsity as a middle linebacker. I quit all sports basically, but we remained to be kind of good friends over the years, and through our main group of friends we developed a nice relationship. Dave is about 6’2 and like 220 pounds, so he’s way bigger than myself, he’s basically yo... Continue»
Posted by pantycum666 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 5004  |  
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couples sexual exploration

So here we are at our hotel room, on vacation for a week in Hawaii. This is our second night and we decided to bar hop. We had fun at the first bar, we stayed for three or four drinks (wife drink faster than i do), we were supposed to stay for one. We decided to hop to the next, this one bar was jumping! And not a line outside so we went in and head to the bar. This one girl started conversation with my wife as we wait for our drinks. She was petite a couple inches shorter then my wife with nice c cups tits, long silky brown hair looked mixed or Latina, pretty but didn’t think much of it. ... Continue»
Posted by welove2sex 6 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 4994  |  
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Paybacks Are Hell - The Gangbang

Paybacks a Are Hell
So I get a call from Denise, a friend that I haven't spoken too in about four years. She tells me that she was in town and would like to get together. I tell her that I am meeting my husband for lunch and she was more than welcome to join us.
As I see Denise walk in she looks just as she did when I had last seen her. Denise is 38 years old, she is a petite woman 4'8" about 118lbs, nice sized breast, light milky skin with deep natural red hair, married with one daughter in collage. She was a wealthy stay at home mom, dressed quite modestly and was always very involv... Continue»
Posted by jm6060 10 months ago  |  Categories: Voyeur, Hardcore, Shemales  |  Views: 4978  |  
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Picked up in the Park

It was a beautiful sunny day and I decided to take a nice walk in a local park. I wore a loose t-shirt and a pair of gym shorts so that perhaps I could get some sun tan on my freshly shaven bare legs. I walked my dog in this park from time to time and I was aware that it was kind of a cruisy place sometimes although on this particular day the park seemed fairly empty. I walked through some of the trails and it felt like I had the whole park to myself. I was feeling so horny that I almost ducked off into the woods to jack off when I spotted a guy coming towards me on the trail. He was abo... Continue»
Posted by rikki50 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4932  |  
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Panty Boys

By Fred Gingerman

Chapter One - Nerds United
My name is Mickey Donaldson. For most of my 16 years, the k**s have called me Mickey Mouse, because of my size and because of my shyness. I was only 5'3" and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5'4" and 120, but we weren't being recruited for our high school football team. Chess team was more like it.
We were pretty much classic nerds. Shy. Picked on. Ostracized. Intelligent.
But we were still 16-year-old boys and our hormones were stirring. Boiling actually. ... Continue»
Posted by BeeJay69 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4910  |  
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my first cock experience (true story crossdressing

I will never forget my first experience with another cock , it was the only time I have ever been with another man, now saying that I do date ts women, I love them as much if not more then I do genetic women. I was 12 years old and like any young boy , very horny . At that time my best friend liam and I would have sl**p overs and do normal k** stuff , sports , video games , camping , never did I think that one day I would have his warm milky cum in my mouth or his warm hard throbbing Dick inside my ass pussy .

It all started when we were looking at a magazine and saw a picture and article ... Continue»
Posted by dickissogood 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4904  |  
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My first time with another crossdresser.

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my b*****r and s****r. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer to waist with reinf***ed toe suntan wolford pantyhose. They were incredibly silky and soft. i rubbed t... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 4908  |  
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A Halloween Party

I've always loved Halloween. It's the one day out of the year where I am confident to go out fully dressed as a CD. If anyone objects, I just say I'm going to a costume party dressed as a woman. I've seen lots of straight guys do it. . .or, maybe they're not so straight after all. Anyway, I was getting dressed up to go to a party at Doug and Jeannie's house on the waterfront in Mercer Island. The perfect venue for a Halloween party - both Doug and Jeannie were bisexual and very open about it and their parties were always filled with diverse folks from all lifestyles. The vibe at their ho... Continue»
Posted by rikki50 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4894  |  
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Daddys little helper 2

I was in shock. I had just watched a video of on my father's computer of my dad and my best friend Sam on the very bed I was sitting on. My friend was dressed in sexy pink lingerie and had sucked my father's dick until he had exploded all over Sammi's (as daddy called her) face. The pair of them had very obviously enjoyed the experience.

That wasn't what had really shocked me though, the shock came from a couple of things. The first was that as my father had unloaded his come all over my best friends face, I had been thinking that it should be my face that was receiving his tribute. The oth... Continue»
Posted by sparkyking 5 months ago  |  Categories: Shemales, Taboo  |  Views: 4860  |  
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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 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4854  |  
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Spit roasted in an Adult Theater

One day I was feeling particularly horny from not having any satisfactory hookups in quite some time. So I showered and shaved my legs smooth and slipped on a pair of bright pink bikini thong panties. I put on a pair of sweat pants that I could easily slip off and just put on an old sweat shirt as a top. I then headed off to a popular adult theater a few towns north of where I live, about a 45 min. drive away. I paid the $10 admission, got my ticket and walked inside the theater. I immediately headed for the back row and sat down in the last seat next to the wall. Next to me on my left w... Continue»
Posted by rikki50 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4844  |  
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She was a he

Few years back I was in a bar in London getting a round in for the lads before we hit Fabric.
I will be the first to say I'm not the fittest of guys and rely a lot on my charm. I took the drinks back to the table and returned to the bar to grab mine when a stunning Asian girl caught my eye and smiled at me. She glided when she walked, a smile that made your heart melt and a body to die for, why was she heading over to me....?

We chatted for a while and I agreed to meet my friends in the club a little later so I could get to know this amazing angel. We chatted, flirted and laughed until th... Continue»
Posted by dirtydisco99 6 months ago  |  Categories: First Time, Shemales  |  Views: 4835  |  
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Becoming Lisa

From when I was as young as 9, smooth and long blonde hair, I was always dressing in my older s****r's panties and bra, panty hose. My breasts were kinda girlish and i had long nipples that would get hard when I played with them. I was older now, but still only had a small 4 inch cock when it was hard. At least I could cum when I played with myself like this. We lived on a lake in the country in Texas and one day, I was playing with myself in the bathroom, in her pantyhose and bra one day when I thought no one was home and Linda, my mother's college roomate, who was visiting, walked in on me. ... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: First Time, Mature, Shemales  |  Views: 4832  |  
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Crossdressing - Teen fantasy with Panties to Cock

Confessions of a Crossdresser

I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to understand how I have evolved.

If I was a woman, I would be a cum dumpster: intelligent, attracti... Continue»
Posted by ericalace 3 months ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 4830  |  
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my mom turned me into her sissy




"Mom! I called out as I got home from baseball practice, "I'm home!"

"Hello Danny, we have to talk," she responded, while exiting my room.

When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store.

"Please explain where these items came from."

I should have told her I was sorry, and that it was just the one time,

But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I was a sissy."

The next thing I knew, I was in big, big trouble with Mom. I... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Fetish, Shemales  |  Views: 4810  |  
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