Shemales Porn Stories
Page 7

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
- 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 ... Continue»
Posted by Asmarani 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 6499  |  
95%
  |  4

During the divorce 15 years ago

I am older maybe wiser but still a k** at heart and love to pretend. I get home Saturday around dinner time, after horrible (He’s Cheating, Has other women) things are said by my supposed loving wife of 15 years about how I mentally abuse her or the he doesn’t love me anymore innuendos. A Saturday meeting with attorneys because she cannot meet during the week due her job, this won’t be cheap. The divorce is painfully slow, meetings about this and that are beginning to feel like a hot sweaty day covered in glue rolling through broken glass! I get home and pretend that my c***dren are st... Continue»
Posted by Chartless 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 4202  |  
93%
  |  9

Crossdressers First Time

I was in my mid 40's and divorced and living a great life. I ran my own successful business from home and lived in a large house in its own grounds at least 5 miles from my nearest neighbour.
Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they wished.
Debi was 50 a successful lawyer and very dirty. Helen was 60 a retired busin... Continue»
Posted by maninnylons 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5754  |  
100%
  |  3

First big cock.

So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective.

I tried an online dating site and eventually met a white guy in his 40s well built professional that likes to top. I told him that I was a beginner at being a bottom and that I thought he was really handsome but his cock was just way too big for me to have sex. We became friends and chatted all the time. Until one weekend he got a hotel room and sa... Continue»
Posted by Cutiecdny22 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6268  |  
100%
  |  5

Polly and Guy

I met Guy at work. He was a client of ours and used to come and see me at the office so I could help him find work. He'd come over from France 15 years before and although he was good with English I arranged for him to go on different courses to help him get a new career. Over the weeks as I gave him one to one support in the office we got to know each other well.

We always had a laugh and he used to try and teach me French. He was very handsome and if I'm honest he made me go slightly weak at the knees whenever he came in. I wouldn't have known if he felt the same way at first as my work ... Continue»
Posted by leotardlust 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 2211  |  
100%
  |  3

Cindy's makeover

I do not claim to be a grammar expert and as such you will find some grammatical errors in this story. The errors can be the switching of tense, spelling errors, or typos. I ask if you find an error please send me an email so I can correct and make the story enjoyable for others.

WARNING!
This text file contains sexually explicit
material. If you do not wish to read this
type of literature, or you are u******e
Eighteen, PLEASE DELETE THIS FILE NOW!!!!

Cindy's Makeover
CindyUSA
cindyusa58@yahoo.com
I would like to share my latest cross-dressing experience. Like many cro... Continue»
Posted by cindyusa58 1 month ago  |  Categories: First Time, Shemales  |  Views: 2358  |  
100%

Baby Sitters Secret


The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated on my wife, I had never lied to a friend, and I had certainly never slept with a girl that young before. All of that changed within a matter of hours. But you know what? I wouldn't change what happened for the world.

Years ago, I moved to the small town of Emberton, Rhode Island to take a job ... Continue»
Posted by drew1207 1 month ago  |  Categories: Anal, Fetish, Shemales  |  Views: 9576  |  
98%
  |  14

My First BBC

It was not long before I told my wife about who I really am, that I was having serious desires to be taken by a real man. I have / had no true preference, but something about getting pounded by a cocky and arrogant black guy really turned me on. But I wasn't looking for some thug or prick to just have me. I wanted a man!!! A black man.....a BBC man!!! One who had a hot bod, aggressive demeanor, and of course a huge cock. So I had my expectations, and I was anxious for this experience.

I had been dressing in full for a while at this point, but my wife wasn't actually aware. Porn was... Continue»
Posted by Ivygurl86 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 3766  |  
100%
  |  9

Playtime Stories Ch. 8 Caught by the Motel Manage

8.

I love sleazy places. I feel at home and strangely comfortable. The motel I used in my home city was comfortable. I guess it was too comfortable.
One day about two weeks after the Levonne whore-fest I went to the same motel with a wonderful afternoon of phone sex, porn, masturbation, and perhaps random strange cocks planned. There was a possibility that a guy I met in an arcade would stop in and fuck me.
I dressed in my usual- all black slutty clothes, the strappy heels, the thigh-high stockings, the waist cincher with six double-attaching points, my spandex panties, the sa... Continue»
Posted by 6988slutty_rbckyy 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1175  |  
100%
  |  1

Baby's Surprise

Baby's Surprise

After a long hard Stressfull month at work I came home Friday and Lisa was not home and had left a note
(Hey Baby unwind and take a shower I left somethings on the bed for you wink wink, See you in an hour xoxo Lisa)

I sit down turn on the stereo and get loaded, I get up and go to start the shower and take a shower and shave
all over and clean out. Lisa's wink wink is a hint to shave and clean out back there she wants to play.

Back Story 10 years ago Lisa and I ventured into Strapon's and then one night as she was using the Strapon
in Me she said Hey Baby I want yo... Continue»
Posted by Bi_Norfolk_cd 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 4181  |  
83%
  |  1

HEAVAN PART 4

PART 4 THE PLANTING OF HEAVAN'S SEED

Heavan has her huge tall daughter carry me up to the next floor where there was a special bed constructed with a small pocket that her daughter lay me down into it so my body was sunk down even with the bed ,strapping me in so I could not move or resist what ever Miss Heavan had in store for me , some thing about I being the one for the use ,for what use.
Miss Heavan entered the room and sat next to me on the bed and told me what I had been chosen for <as Miss Heavan spoke off in the other side of the room her tall hulking daughter was undressing and I ... Continue»
Posted by huge_cock_rules 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 967  |  
100%

How my chastity started

There was this woman where I worked at. She had a thing for retro and would wear business skirts, high heels and actual real stockings every now and then. She had a body to die for and legs that just simply made me melt. When she walked by I would simply melt. Could not explain it this power she had over me, it was more than just sex or lust, it was like the magnetic pull that keeps the Earth in orbit. I started small talk with her and over time we began chatting now and then. I WANTED TO HAVE SEX WITH HER SOOOOO BAD!!! But would not even flirt with her in that direction because I knew from of... Continue»
Posted by debbielynn 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1541  |  
90%
  |  1

My adventure with a shemale

My friend’s son was getting married and he wanted us all to go on his stag do in Amsterdam. Having flown from London we were soon settled in our hotel and the beers kept coming, it didn’t take us long to get steadily pissed. Soon everyone was pissed out of their skulls except myself and were soon falling asl**p, I decided to have a walk around the city.

I went from one bar to the next and when I went in the fifth bar this girl came up to talk to me, she was 21 years old, long black hair, slim and had a lovely pair of tits on her, she said her name was Domeak. As I bought her a drink we sat ... Continue»
Posted by smallcock 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 3021  |  
100%
  |  2

Foursome, the best way to start.

It started as Tiffany and I. She's a taller than me, we are both very fit, I'm a bit more petite. She and I like pegging, she's very dominate. I had my chastity cage on since early in the morning, it had made me pretty horny so I thought I would play to Tiffany's dom-side and get one of Anna's cheerleading outfits. She and I are about the same size and Tiffany likes a flirty girl type.

Tiffany got her strapon and Anna got curious so she wanted to come watch (watching is not uncommon in our house, you might do it while your texting or something). Tiffany put me on my knees and made me start ... Continue»
Posted by JamieCD90 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1238  |  
79%

how i got my start as a sissy .

Growing up was tough . I spent a lot of my younger years trying to figure out if I was normal or not . Had many girl friends but still I had an attraction to cock . This all started at a very early age and abuse continued till upper ages from both sexes . I really started exploring my sexuality after I joined the army and got away from home . There I was used by other army high ranking men who knew what they were looking for . I had a command sgt. major for my first dom who took me out one night , Made me dress for him and then proceeded to **** me . I found that this turned me on deeply and h... Continue»
Posted by mendytgirl 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 2248  |  
100%
  |  1

Crossdressers first time

So let me begin and say this is my actual first time of being dressed in front of someone and my first time with a guy.
It all started when i was 21. I was in college but on christmas break and my friend pat was having a party. Living only 5 minutes away i said i would go. Party was small 5 guys and 3 girls there. The girls were getting bored after a while and were going to leave but they started whispering to each other and said lets play truth or dare. With all the guys desperate to not let this party turn into another guys night we all agreed to play. It started out typical all the gir... Continue»
Posted by Missterious999 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 2269  |  
95%
  |  3

Hello guys bbc story happen

Sorry guys my stories r truth so some time takes time big event happen
Sorry in advance my English and grammar not good

As u guys know I'm shemale skinny and cute pic in my profile

Lately I start my new business remodeling small business retail stores I meet this client 7ft tall very muscular and very rich and yes his black from Africa some island and he open new shop here in my city for female clothing and undies and after my team finish Remodel his store they left I'm at his waiting for him to come over pay me rest of money we agree on its was late around 9:27 pm he knock on glass d... Continue»
Posted by shawn777 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 951  |  
100%

Bondaged and fucked at a hospital: Pt 3

It's my third day at the hospital and I learned something new today. The pills they had been giving me to "ease the pain", were mixed with other ones and I hadn't known about it until this morning. These other pills had secret side effects which were only used for "different" medical needs and they seemed to slur my speech making it hard to understand what I was saying. At first I thought that it was for a short period of time but I after an hour of attempting to speak it only seemed to get worse. 

Another nurse walked in who wasn't Lisa and I wanted to ask her about my condition, but as I ... Continue»
Posted by adblman 2 months ago  |  Categories: BDSM, Hardcore, Shemales  |  Views: 4072  |  
100%

BECOMING THE SECRET FISHING CAMP PRINCESS


BECOMING THE SISSIFIED FISHING CAMP PRINCESS!!!!!!!!
Between being raised by a strict single parent mother, and living far out the boondocks of a small remote New Hampshire country town, my life was different than that of the other town boys.. Yes homework and then houseword were all I ever seemed to be doing.
By fully LEGAL age 18,
I was a good three to four years younger in mental developement as my mom was super protective of me, I was also still the physical size of most jr.high school boys but I could cook just about anything and even sew and do every single bit of household chore... Continue»
Posted by cddixie 2 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 4518  |  
100%
  |  3

BECOMING MY BOSS MARGO'S SISSY BITCH BOY TOY.

WHEN I GOT CAUGHT GIVING A SUPPOSEIDLY QUICKIE BJ IN THE MENS ROOM STALL TO A CO-WORKER OF MINE, I WAS SURE MY FIVE YEAR JOB AS AN UNDERWRITER AT MY INSURANCE COMPANY WAS A THING OF THE PAST. LUCKY FOR ME, THE GUY I WAS PLAYING WITH WAS ONE OF THE OWNERS NEPHEWS, SO I WAS CAREFULLY TRANSFERRED INTO AN NEW POSITION ON THE SIXTH FLOOR AS THE ONLY MALE IN A SEVEN PERSON RESEARCH TEAM. MY NEW BOSS WAS AN OLDER (LATE 40'S)VERY CONSERVITIVE WOMAN NAMED JOAN. FOR THOSE FIRST TWO WEEKS, I WORKED LONG AND HARD IN ATTEMPTS TO NOT ONLY REDEEM MYSELF, BUT TO FALL INTO HER GOOD GRACES AS WELL. JOAN ... Continue»
Posted by cddixie 2 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2859  |  
88%
  |  1