Shemales Porn Stories
Page 7

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 5 months ago  |  Categories: Shemales  |  Views: 4561  |  
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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 10 months ago  |  Categories: Anal, Mature, Shemales  |  Views: 4558  |  
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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, single, mid 30’s, worked for a software company, and drove a nice car. Had bought me... Continue»
Posted by MacDaddy714 1 year ago  |  Categories: Anal, Shemales  |  Views: 4533  |  
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Moms Trannie

It was Saturday night and my friends had told me about a new club. It was about an hour out of here and had an older crowd. This sparked my interest some what having a fondness for older women.

I walked into the place and looked around, not much going on so I wandered over to the bar and ordered up a beer. A little while later the crowd picked up and things started to get moving.

The women were defineatly older here, I asked a few to dance and had a few takers but couldn't seem to lock in with them.

While I was dancing I must have missed the two that came in, a blonde and brunette wit... Continue»
Posted by frswriter 1 year ago  |  Categories: Shemales  |  Views: 4531  |  
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Best I ever had

I was at work one night closing up shop when my buddy Nick shows up and asks if I want to come over and party. I say sure. When we get there he tells me his girlfriend Nora might be interested in a little playtime. Now this might not happen again if it does happen he tells me. Well I'm certainly interested. You see we both met her about the same time and she was a hot little number. About 5'1" or so she claims. tight petite little dancer's body. Perky A nearly B cup breasts. Medium length honey blonde hair ang... Continue»
Posted by aladinane56 5 months ago  |  Categories: Voyeur, Shemales  |  Views: 4512  |  
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MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few stools away from me at the bar, and I couldn't take my eyes off of her. She was a raving beauty, with... Continue»
Posted by fukkerguy 10 months ago  |  Categories: First Time, Shemales  |  Views: 4467  |  
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Old trannie gets a boys virginity

Oh dear I’ve been a bad, bad old trannie. I let a teenage boy seduce me.

I normally only go with guys over 30 at least. But this teenager contacted me on a dating site. I gave him the normal “Thanks but I’m in my 40’s you’re a bit on the young side for me” reply. However he kept contacting me on the site. He was very curious and quite sweet. I chatted with him online and he said that he would really love to meet me.

I told him if he wanted to meet me that he could find me at my local sex club. He said he couldn’t go there. After a deep thought I said it would be O.K to come round on the... Continue»
Posted by toniparr 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4456  |  
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Business Trip

My boss had sent me to Brighton at short notice as she decided at the last minute that she didn’t want to go. Apparently she had something better to do. The fact that it was my birthday didn’t seem to bother her too much. I usually liked the chance to get away for a couple of days as I’d sneak in some of the wife’s sexier things in my bags and spend my evenings in my room all dressed up and nowhere to go. But this time I would be missing out on spending quality time with Suzy. We’d only been married three years so we still made the effort when it came to birthdays. I had thought of bringing Su... Continue»
Posted by annav 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 4446  |  
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The office girl

Tamsin was the new girl in the office and she was clearly shy. Unlike the other girls who splattered make up all over their faces and spent hours on deciding which dress to wear, Tamsin was rather plain. Her typical outfit was a smart suit. It became very clear very quickly that she felt very awkward in the new environment, so I thought I'd try and help her settle in.

Over the next few weeks we quickly became close friends, often laughing at each others jokes while our co workers were still trying to work out the punchline.

Out of the blue a office night out was arranged. I asked Tamsin ... Continue»
Posted by kinkymister 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4446  |  
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Ladyboys: Moving to Thailand and my first Ladyboy


After living in the Netherlands for 33 years I was ready for a big change. I had been toying with
the idea of moving to another country to get away from the stress of it all for a while.
I had girlfriends in the Netherlands. Wives.
I had one nighters and 2 nighters. I wasn't doing bad for myself.
But, there was something missing on the girl side. I love variety. I think I've been with
every kind of girl I COULD be with in the Netherlands. I started thinking about other countries.
Other girls. Other types of girls...
I had seen shemales in Amsterdam. Emphasis on the boy part. And they ... Continue»
Posted by casinocock 2 months ago  |  Categories: First Time, Shemales  |  Views: 4435  |  
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first time with a Tranny

My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits. We dated for about a month when talk her into just taking her shirt off, after a while without her shirt off she finally took her bra off. I would make out with her and suck on her tits, lick her nipples. One day we were together I decide to change it up so I took my pants off in the bedroom and ... Continue»
Posted by theho_1 2 years ago  |  Categories: Anal, Shemales  |  Views: 4431  |  
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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 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4376  |  
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My First Gangbang

For as long as I can remember, I have always enjoyed wearing women's clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing with peckers too ;-)

As you may imagine, I became VERY popular! Pretty soon, there wasn't a sl**pover in the neighborhood that I wasn't invited to ;-)

I quickly developed what would be a lifelong obsession: semen. And no matter how much I got, I still wanted more! The feel of it squirting into my... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 4369  |  
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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 11 months ago  |  Categories: Anal, Shemales, Taboo  |  Views: 4351  |  
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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 6 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4341  |  
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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 3 years ago  |  Categories: Shemales  |  Views: 4330  |  
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Male to Female Transformation

Male to Female Transformation

Genre : TG SOS or Surgery/Transformation Male to Female
Story : Cristine Carter
CH - 1

The last thing I could remember was walking out of the Bank
and crossing the road to my car. I had just been to see my
bank manager to discuss transferring some money from one of
my accounts into a high interest savings account.

I had won quite a bit of money on the Lottery, enough to
change my life. I was unaware just how much my life was
going to change.

I had just reached my car door when I felt someone bump
into me. Then everything went blank...
... Continue»
Posted by cristinestone7575 6 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4315  |  
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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: 4277  |  
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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 9 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 4271  |  
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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 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4260  |  
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