Shemales Porn Stories
Page 5

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 4 months ago  |  Categories: Interracial Sex, Shemales, Taboo  |  Views: 5116  |  
100%
  |  4

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 3 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 5051  |  
82%

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 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 5042  |  
100%
  |  8

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 4 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4996  |  
96%
  |  4

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 2 months ago  |  Categories: Voyeur, Hardcore, Shemales  |  Views: 4978  |  
100%
  |  2

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 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 4971  |  
100%
  |  7

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: 4904  |  
93%
  |  17

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 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4891  |  
100%

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: 4870  |  
99%
  |  15

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 4 months ago  |  Categories: First Time, Mature, Shemales  |  Views: 4830  |  
100%
  |  6

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 9 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4822  |  
100%
  |  12

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 10 months ago  |  Categories: Gay Male, Shemales  |  Views: 4815  |  
100%
  |  6

Used by a gorgeous ladyboy.

(Yeah it's been a while but i'v been busy … doing the thing in real life with a new guy i met and there is not much need for xhamster at the moment :) . The story below is based on a true experience and i just changed a few details to spice it up a bit)

This story is based on a true experience and happened a few years ago, on a great night out in Amsterdam. It was before i had sex with guys on a regular base and i entered a complete new and exciting world...

During that period of my life i was single and i only recently started watching ladyboy porn and started to like seeing dicks in my... Continue»
Posted by abitqueer 5 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4787  |  
100%
  |  6

Mom Transforms Son into a Transsexual. Part 2


Mae and me were laying in bed cuddling when our Mothers walk in and informed us we had a doctor appointment Mae and I exchanged looks and went into the shower Willa came in the Bathroom and told us to shave each other's body.

We finished as told and dressed each other in our best prissy outfit and walked down stairs we quickly left, jumped into Moms Caddilac we drove for about a half hour then pulled up to a Medical Building. Me and Mae waited in a room while our Moms Talked to a doctor, 90 minutes later a Nurse marched us into The doctors office. The sign read Dr. Goldstien Our mothers w... Continue»
Posted by sissytimmy 4 months ago  |  Categories: Interracial Sex, Shemales, Taboo  |  Views: 4780  |  
100%
  |  3

Moms friend Vanessa


My mom had a best friend named Vanessa. She was more like an aunt

and always was around. She had big tits, a thin waist, a fat ass,

and nice big legs. She would always wear short skirts or short

summer dresses that showed her wonderful legs. One time my mother

was at work and Vanessa was watching me until she got home. I was about

8 at the time watching tv in my spiderman underwear laying on the floor.

Vanessa was sitting on the sofa reading a magazine. She crossed her legs

just as I had looked up. What I saw made me very curious to say the least.

I saw what look... Continue»
Posted by moms_sissy 10 months ago  |  Categories: Mature, Shemales, Taboo  |  Views: 4701  |  
68%
  |  5

The Fam...CH 1

Key Players;

Father - Dave

Mother - Brenda

Male sibling- Stevie

Female sibling - Alicia

Neighbor mother - Lakeysha "candy"

Neighbor twins - Keke & Tricia






"Fuck daddy...that was fucking hot" Stevie said while scooping up his f@+=€r's cum from the side of his face with his finger. Stevie was kneeling by the side of the bed with Dave's quickly deflating 9 inch black cock only inches from his face. Stevie is a young tw€|>e year old b•y that has recently been diagnosed with gender identity disorder. He is the youngest product of an interracial marriage between Da... Continue»
Posted by TS_LoverBoy 7 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4695  |  
100%
  |  3

The Triple X cocktail - Wife Shares Shemale With H

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up.

The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known Tara since 6 months now since she busted me from one of the restrooms of her restaurants. Well wh... Continue»
Posted by Copious 2 years ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  Views: 4598  |  
96%
  |  12

Getting back at the bully

Hi, my name's Rose Marie, and though you may have already guessed, I'm a hermaphrodite. Don't let that fool you though; I'm not some wimpy little girl. I'll admit I can get a little rough, but I can be laid back too. I just turned 17, and just like a lot of other people, the good 'ol hormones are ragin, but I do a lot better job of hiding them from most people, when I want to that is....

I'll be a junior in high school this year, I’ve had a mostly quiet summer. I have dark red hair, I put some white streaks in it with one of those hair styling kits, I’m not trying to be the center of attent... Continue»
Posted by wheels1825 1 year ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  Views: 4577  |  
100%
  |  6

scoring an old black woman

A couple of years ago, I moved into an apartment complex in a pretty bad part of town. The neighbors next to me were a woman and her mom (both black). The daughter was about 35 or something. The mother must've been in her mid 50's or so.

They were pretty plain in the face and had pretty large noses, and the mother had her hair buzzed down like some older black ladies get their hair done, so they don't have to fuss with hair straighteners and such. The daughter had an awesome bubble butt and hips and was feminine (painted toenails, long painted fingernails, makeup) and dressed pretty slu... Continue»
Posted by bbwlover1138 2 months ago  |  Categories: Shemales  |  Views: 4566  |  
92%
  |  5

Four (4) in 3 days, no wonder my jaws ache

Yesterday was Sunday and I hoped it would be a day of rest. I went into the local market in drab, did a little shopping, decided I had the start of a cold and took my time doing very little.

My nipples were still sore from Saturday evening's little escapade and my jaws were aching a little, I seemed to have sucked a lot of cock in a very short time.

I spent a very quiet afternoon, rinsed out my collection of stockings, put off washing my lingerie until today and settled down for an online session without much hope of getting a date. By 6.00 pm I decided I did have a cold and was going ... Continue»
Posted by antoniaf 6 months ago  |  Categories: Anal, Mature, Shemales  |  Views: 4559  |  
100%
  |  1