Shemales Porn Stories
Page 11

My Shemale Mom and Aunt chapter 2

When we three got home Mom told to me go to my room and wait for her, about 5 minutes later I was sitting on my bed. She walked in with one of the bags of goodies we bought, Mom said I think you should call me "Jenna don't you Timmy".

Jenna started to strip so I went to her and got down on my knees, she said later Timmy hop in the shower NOW!. Mom/Jenna undressed and joined me in the shower she grabbed the the shaving lotion and her pink razor, she shaved every thing except my testicles, she dried me off and said lay on the bed while I finish, I laid on my back and pushed my knees to my ch... Continue»
Posted by sissytimmy 1 year ago  |  Categories: Anal, Shemales, Taboo  |  Views: 4435  |  
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A Different Kind of Prom

When we were both five years old I told Brenda Anders that I
loved her. She told me that she loved me too. I told her that
she was pretty. She replied that I was pretty as well. I told
her that I wanted to marry her. "I'm sorry," she replied, with
seriousness that now seems silly in a kindergartner. "I don't
want to marry a man."

"Then I'll grow up to be a woman."

"You can't do that, goofy."

"You watch. I'll grow up to be a woman. Then we can get
married."

That, of course, was almost thirteen years ago, and my desire to
marry Brenda hadn't decreased at all with time. She cer... Continue»
Posted by lana100 11 months ago  |  Categories: Lesbian Sex, Shemales  |  Views: 4416  |  
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How I got started dressing my true story.

As far back as I can rememeber I have always gravitated towards fem things. As a young boy I played with whatever girls clothes I could get my hands on. Which wasn't much. At 12 y/o I had a few pairs a panties and bras stolen from my cousins. One thanksgiving after dinner the girls changed and one of them left behind a black knee length dress and white pantyhose in the guest bedroom. I was so excited when I found them...needless to say she never saw that dress again. With the bra and panties I alrady had from her and the new black dress and white pantyhose...I had my first total outfit. My tr... Continue»
Posted by Sarahaspencd 1 month ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 4383  |  
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Daddy's whore

I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shaved... Continue»
Posted by vince01 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 4376  |  
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My Girlfriend's Mother Has a Secret

A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-).

Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pride and joys. Normally, this would help her relax and unwind, but tonight, and on several other nights, she found that remained tense. She couldn't get over the feeling that somebody was watching her, for several days, perhaps a week; when she was alone around the house; she'd have an odd sensation ... Continue»
Posted by Asmarani 8 days ago  |  Categories: Anal, Mature, Shemales  |  Views: 4420  |  
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My Life as a Shemale Part1

In this story, many will find what happened to me socially unacceptable. But since this has happened to me, I get to tell it and if you like, listen.

I was very young when I found myself on the streets and it seems long ago that some things I do not remember but its the important stuff that I do. And yes, like so many other stories start, here is how I looked. 4 foot nothing, skinny, long blond hair and even then had more angelic features then not. I do believe that now, that I was a woman even then but as nature would have it she would have a sense of humor and endowed me with a large peni... Continue»
Posted by gigi750 1 month ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 4362  |  
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Cheating Bastard

I began to suspect that my husband was cheating on me about 6 months ago. He'd call me and tell me he was working late or he'd show up to different events claiming that his boss needed him to finish a project before he could leave. Then his phone started to have more activity than normal. He'd often move to another room to take calls or messages. He started hiding his phone whenever he was asl**p so I couldn't go through it. The final clue came when he started to smell different. I had been married to him for many years so I knew his scent well but whenever we made love I could detect ano... Continue»
Posted by RyleighM72 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4351  |  
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Josie's Awakening

My name is Joseph, and this is a wonderful trip down memory lane for me. Join me as I relive the first few experiences of what would soon become a life changing event......

######



Jason and I were always best friends. We grew up together, we played sports together, we got laid at practically the same time by another pair of best friends, everything. This is our story......

I was out of town for a few weeks on business so we hadn’t had a chance to hang out for a while, so once I got back into town I called him up to see what he was up to
"Hey man what’s up"
"Nothin, my s****r is... Continue»
Posted by qqqqq2qq 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4342  |  
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Job Interview

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Keliana Kotey, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company’s receptionist, Paula, put her head around the office door to tell me that Miss Kotey was waiting and asked if she should show her in. I agreed and sat back to watch the view of Paula’s nice arse as she walked away from me. A twenty two year old gorgeous blonde, Paula was the kind of person who brighten... Continue»
Posted by keliana 4 years ago  |  Categories: Shemales  |  Views: 4330  |  
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My Aunt Gave Me A New Life




My Aunt Gave Me A New Life

As i already wrote, my Mistress has threated to turn me into a gay
shemale slut -- and i'm terrified. Last night i began thinking about how
this whole thing began.

We've lived next door to one another for years, and i've always admired
Her from a distance. She is beautiful! She has a small frame, 5'2",
dark hair, beautiful eyes, a dynamite little body with good size breasts,
beautiful legs. i guess You can say that She was my fantasy. A number
of years ago, when they first moved in next door, She came over with her
daughter to introduce... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 4333  |  
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New Neighbors

My first attempt at writing one of these. Let me know what you think.

My roommate Mike burst into the room grinning, “Dude, have you seen the two girls that just moved in down the hall?” That caught my attention, “Wait, that blonde and brunette are moving onto our floor?” I had indeed seen them earlier outside the building. They had stood, laughing and chatting with one another, while movers unloaded boxes under their supervision. I couldn’t help but notice them; the blonde in a slightly too short summer dress that showed off her strong legs, and a low neck-line that promised never-ending ... Continue»
Posted by slatemhor 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4313  |  
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Daddys little helper

Maybe if I'd minded my own business and stayed off my dad's computer, my life would have been a whole lot different. As it is I wouldn't change it for the world.

My name is George Mason Jr. I was twenty years old when I moved back in with my father (George Snr, obviously) after my mum left him and took up with some arse-wipe she met at her gym. He had been devastated by the betrayal and I had moved back in to keep him company and make sure he didn't do something stupid. I was quite a good cook and a bit of a neat freak, so it worked out okay for both of us. I got out of my shitty one bedroo... Continue»
Posted by sparkyking 8 months ago  |  Categories: Shemales, Taboo  |  Views: 4287  |  
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Am I A Bad Aunt - Part 4

Am I a Bad Aunt - Part Four

By billy69boy

(Part Three ended with Aunt Eve and her niece Ariel getting ready to pleasure each other with Ariel's favorite black strap-on.)


Ariel pleaded with me to fuck her first, such was her heightened state of arousal, as she regaled me with the details of her first sexual episode with Malcolm. After she helped me adjust the straps, she handed me the baby oil, and bent over the end of her bed, reaching back to spread her ass as best as she could with one hand. She was silent as I first lubed the thick black dildo, and then I dripped some down her... Continue»
Posted by billy69boy 1 year ago  |  Categories: Lesbian Sex, Shemales  |  Views: 4285  |  
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How I got started dressing

I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just used sites like google or yahoo to find videos by typing in whatever I was into that day. It started out with just words like "blonde getting fucked" or "girlfriend giving blowjob." Once I started to get bored my words started to get more descriptive "Slut takes huge cock in ass."I was skimming throu... Continue»
Posted by pantyyboy 3 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 4280  |  
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Uncles Lessons

I posted this story on another site years ago. I had some nice feedback, but not many views.

In '91' during my senior year of high school my folks split up. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas.

Since I am older by about 7 years, and was in high school I did not want to leave town in my last year. No way did I want to be sent off to someplace I did not know, and be the 'new k**' loser.

Wit... Continue»
Posted by Cuckarama 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 4280  |  
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Night With A HOT Sissy!

June 28th, 2009. End of senior year of high school. I, Angus Corleon, actualy graduated. I wasn't a model student. I've been a leather jacket wearing, rebel rousin, beer drinkin, hell raisin son of a bitch since middle school. My parents didnt care about me, after all my b*****r is a cop and my s****r is a lawyer, and im the law breaker. Anyways, enough about who i am. My buddies johnny, brandon, timmy, and danny have a hell of a party planned for tonight. Big bon fire out in the back woods of where we live. Must be 200 people were expecting. We set everything up, fire pit, band equipment, cha... Continue»
Posted by CDboy9097 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4260  |  
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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 1 month ago  |  Categories: Shemales  |  Views: 4259  |  
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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 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4263  |  
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A Slut is born


There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends.
I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town,
dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?
It had all started a few months ago. I was locked out of my house in the pouring rain,
and I went over to our neighbor’s to see if I could hang out with him until my parents got home.
He was a cool guy... Continue»
Posted by vosmou_vrot 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4252  |  
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Black Mamba -

Most of the following is true. I'll leave it to the reader to judge what is
fact and what is fantasy. Until six months ago I was known as John Evers.
Blonde, five foot seven, slightly built and heterosexual, I had just gone
through divorce after a stormy six year marriage. Not into the bar scene and
at loose ends for things to do in my spare time, I decided to redecorate the
house the way I wanted it. The first order of business was to completely
repaint the interior which I proceeded to do. After prepping and painting
every night for two weeks, I was ready for a break from the tedium ... Continue»
Posted by germanboi4bbc 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 4240  |  
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