Shemales Porn Stories
Page 6

My Uncle Wally's Sissy Boy Wife

Penned by: Miss Deborah (Debi) Leigh Johnson



One



I did not know what I could expect, as the Greyhound pulled into the
bus station. I did not know a whole lot in fact, as I was a rebellious
know it all, fifteen year old brat.

My parents were pretty good as far as parents went. I had not locked a
roof over my head, or enough food on the table, but I had always
resented the fact that my parents were not rich enough to give me
everything that I wanted. I knew in the back of my mind that this was
a pretty immature attitude, but what the hell, it was the way I
felt. I also di... Continue»
Posted by jayymie 4 months ago  |  Categories: First Time, Shemales  |  Views: 5204  |  
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My first time with a shemale



Let me tell you a little bit about myself I'm five feet 10 inches tall around
220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer.
Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort
Lauderdale, when one night I heard a commotion in the parking lot. There were
several men beating up a beautiful woman, when I tried to break it up I ended up
getting very banged up myself.
Her name was misty, she thanked me for helping her and a... Continue»
Posted by palitro1 10 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 5183  |  
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How I became gay pt 1

When I was in my teens I was only interested in girls and thought that being involved in a gay experience was completely disgusting. I never would have even thought of it if it wasn't for what happened when I turned 17.

On my birthday me and a few friends got fake I.D.'s and went to a bar in town. We all started drinking and getting as shitfaced as we possibly could. There was 4 of us and my three friends had all spoted the girls they wanted to fuck that night so I was left alone at the bar.

Within a few minutes this girl sits next to me and I immediately started checking her out. Sh... Continue»
Posted by Gayluva67 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5176  |  
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Fantasy cums true

I was on a business trip staying in a nice Hotel. After a business meeting in my room I called down for room service. The maid came up a few minutes later and I let her in. She was stunning, 5' tall with black hair and the bluest eyes I have ever seen. Under her uniform you could tell she was very well endowed at least a 34 DD. She came in and took care of the room. Thru small talk I found out her name was Terri, she was 28 and single. I thanked her and gave her a tip when she was done. As she left I had to watch her walk down the hallway, her little heart shaped ass swaying back and forth.

... Continue»
Posted by tittie-baby 1 year ago  |  Categories: Shemales  |  Views: 5172  |  
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The Room Mate

The Room Mate
My wife and I have been happily married for about nine years now. We had never slept with anyone else during our relationship. I have greatly enjoyed my time with her. However a few weeks ago a coworker of my wife’s moved in with us. Her name was Denise and she had just lost her job, car, and about everything she owned in about three days. We were glad to help her out in any way we could. We set up a second bedroom in our modest apartment.
At first things were normal, at least for having another person living with us. Then something happened, something I did not expect. I need... Continue»
Posted by raastible 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 5167  |  
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Mommies little sissy slut


I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever seen complete with calf length stockings and a garter belt. I wasted no time stripping off and sliding on the sexy underwear, next I found her makeup bag and applied some red lipstick and black mascara. that was when I heard the front door open, my mum was home early!! I tried to hide but before I could she strode int... Continue»
Posted by momandboys 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 5144  |  
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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 9 months ago  |  Categories: Interracial Sex, Shemales, Taboo  |  Views: 5117  |  
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SUBMISSIVE HUSBAND CD



SUBMISSIVE HUSBAND

Chapter 1

Aas is usually the case, three years of marriage our love making had grown
a little stale. I decided that we needed something to spice it up and I
broached the subject of adult videos to my wife to see if she would like to
try something different. She was initially hesitant about anything
"pornographic" but I told her it was just "soft porn" and thought we ought
to try it just once. My wife is very strong minded and was raised very
strict so I knew it would be a big job to sell her on it but I kept after
her. She finally agreed and I stopped ... Continue»
Posted by aimen72 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 5116  |  
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my girlfriend Allison has got a cock

MY GIRLFRIEND ALLISON HAS A COCK
I met Allison 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 ... Continue»
Posted by pesty 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 5041  |  
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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 8 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 5034  |  
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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: 5013  |  
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my Tranny Bud

I am straight. ok, so a couple years back after the divorce, had to go live with my b*****r. he gave me a little front room and I can never repay him for that. I had a female friend who's b*****r was a tranny. I wanted some hydro he sold. so called my friend to send her b*****r tranny over. he came after 1am. my b*****r was crashed. we smoked a little and talked about past experiences. obviously his were way more exciting. I mentioned that I loved to jack off in front of my wife while she was watching PORN, drove her crazy. ok got late, so he split.

3 months laters I was able to afford my... Continue»
Posted by flashmetal 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 5015  |  
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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 3 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 4989  |  
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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 7 months ago  |  Categories: Voyeur, Hardcore, Shemales  |  Views: 4978  |  
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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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4903  |  
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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 11 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4895  |  
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My job inLingerie shop Part 2

The owner got dressed and I put on my satin seethrough shorts and matching vest
Your a good girl Ann your cock has made me very happy he said smirking
Now sell some gear darling he slapped me on my arse as I headed for the front of the shop
Rachel and Mia were nowhere to be seen and the boss was behind the counter
One old guy was going through a rack of lacy coloured pantys
He was longily feeling them and he looked up and saw me and beckoned me over
I strolled over letting my still erect cock swing back and forth in my satin shorts
His eyes were glued on my cockwhich gave me a horny fee... Continue»
Posted by juicypantys 23 days ago  |  Categories: Anal, Mature, Shemales  |  Views: 4874  |  
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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 2 months ago  |  Categories: Shemales, Taboo  |  Views: 4848  |  
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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 3 months ago  |  Categories: First Time, Shemales  |  Views: 4847  |  
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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: 4845  |  
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