Shemales Porn Stories
Page 4

The Postman Always Rings Twice

After I moved away from home, I felt pretty good. No one could tell me what to do. I missed only one thing: The closet of my big s****r. Since I was 13, I regularly wore her clothes, especially the underwear. As soon as I was home alone, I went to her room, and started to try on her thongs, bras and stockings. At the same time I played with my little clit and sometimes I slid some vegetables into my boypussy.
I really missed these little dress-ups, so one evening I decided to buy some own lingerie. For the beginning I ordered a cute bra with a matching thong and a pair of thigh highs. I could... Continue»
Posted by notgeile_fickstute 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 6582  |  
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Car Bonnet Cockriding Whore

Hi Guys,




This true story dates back about 4 1/2 months now, and takes place outdoors, well over a car bonnet to be exact.


I had been chatting to this lovely guy called Dave, we had been chatting on a different site and arranged for him to come over from where he lived to where I live in Droitwich. Well I had been getting my self ready most of the evening showering, shaving my self totally smooth including my pussy, made a real effort to look hot with my makup and clothes. The usual things, stockings suspenders, 1/4 cup bra with matching thong, and high heels, a loose fitting top ... Continue»
Posted by donnamarie09 1 month ago  |  Categories: Anal, Shemales  |  Views: 6563  |  
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peeping

Peeping

I was sitting on the bed in my room. I was reading Penthouse Forum and
read a letter about a peeping tom who became a sex slave after being
caught when I began to hear voices coming from next door. My house is
only 5 steps away from our next door neighbour's so in my room I could
hear anything from loud music to sex. To investigate the noises I ran up
to the window and moved the curtain slightly to see what was going on
through the next door neighbour's window. To my shock I saw a man and a
woman having sex. The man happened to be my neighbour, Dan. He is tall
man about 6'... Continue»
Posted by aimen72 1 year ago  |  Categories: Shemales  |  Views: 6460  |  
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It started w/the neighbors wife then her husband.

About 5 yrs. ago on new years I was invited over by the neighbors to party, they had some friends over; we were getting plastered and eating food celebrating the New Year. When out of the blue in front of her husband and friends the wife starts kissing me, I gently pushed her away not knowing how the hubby would react, much to my surprise, his reaction was almost as if he didn't mind to the point where it looked like he was turned on by it.
That night after everyone had gone, the husband had been long passed out, we went to my house next door, & I ended up fucking her. I remember her saying h... Continue»
Posted by MyaTranny 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 6463  |  
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My mother, my lover

Wow
I have no idea where to begin with this story. My mom came by yesterday while the k**s were off fishing on the lake.
I knew when she got here that there was one thing on her mind, and she was not shy about letting me know either. I was painting our daughters room when she came in calling for me, I knew just by seeing how she was dressed that my implant was in for a workout.

She walked into my bedroom and starts calling out " Baby mommy wants to play".
I walked into the room and saw that she was only wearing a smile on her face, both nipple rings, her tongue piercing, and on her toes... Continue»
Posted by Taboo69 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 6393  |  
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My Wife's Affair With The Shemale

My wife Tracy were not married for that long when she had her first affair. I met Tracy in high school and we dated for years before we got married when we were twenty two. I hit the jackpot with Tracy because she is absolutely gorgous and just an all around sweetheart. She has long blonde hair with brown streaks, hazel eyes, long legs, large tits and a tight ass. Tracy has always loved taunting her body wearing cloths like short jean shorts to show off her legs and tank top shirts to show off her stomach and belly button ring. I have always thought of it as a double edged sword because I lov... Continue»
Posted by anonymouspervert69 12 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 6373  |  
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Cum hungry paper boy sissy

Cum hungry paper boy sissy



When I was thirteen our next door neighbor Pat offered me a summer job
helping him deliver papers and magazines. I quickly said yes and my
foster parents agreed. I liked Pat a lot as he always patted my ass when
Vance and Liz were doing something when he came over for dinner as he
smiled and winked. I loved the way it felt and smiled back as my cock got
hard.

I was light build and kept my long blonde hair in a pony tail and always
wore cut off jean shorts. I had also been jerking off and eating my
creamy delicious cum loads for over a year as I loved... Continue»
Posted by jayymie 4 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6331  |  
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Start of a new life

One day I got a text massage on my mobile while I was at work, it was from an unknown number, it said come home now. So as I only work down the road from where I lived and also I was just going on lunch so I made the 5 min drive home. When I got there, there was a man standing in my door with a box in his hand. When I got to him he said do you live here and is your name Lucie, I said yes but a bit puzzled as I only use Lucie when I am dressed as a girl. He said good now open the door and let me in. After we got in he gave me the box and a letter. I read the letter it was from my master, it sai... Continue»
Posted by dallasrose 9 months ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 6324  |  
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mom teaches son to be a slut

I loved women. A lot. My obsession with women later became a desire to wear women clothing. One day, three months after my 18th birthday, I could not hold back any longer, and I put on the the most accessible lingerie I could find - that of my mother.

Since then, I frequently visited my mom's wardrobe whenever she was out. I would wear her clothes, and it would make me feel sexy. I would pretend I am a woman, and take sexy pictures of myself. I realized how much I liked this, and this led to me realizing my bisexuality. I wanted a man to make me his woman.

Because I wanted a man so badl... Continue»
Posted by momandboys 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6329  |  
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Becoming a Black studs ultimate fuck toy

It all started the day I laid my eyes on my first BIG BLACK COCK ,I had been dressing up as a girl since the age of about 12 wearing my mums panties and pantyhose around the house getting turned on by the feel of the pantyhose and panties . At the age of 15 I realized that I loved pretending to be a girl as much as being a boy ,one day I approached my mum to tell her of my sexual orientation. My mum so supportive and helpful I was really surprised with how she reacted . Son you will always b... Continue»
Posted by foxxiroxxi 4 months ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 6314  |  
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Holloween with a surprise

I read this story on literotica and just had to share it with my Xhamster friends.
Here goes.

Halloween my favorite holiday of the season. If you think a twenty five year old does not like going to costume parties, you've' got no idea what goes on in my life. Everyone I hang out with likes to enjoy themselves to the best of their advantage, and Halloween is one of the best ways we can accomplish that. This year, like the last four years in a row, I was hosting a Halloween party at my apartment with a number of friends coming over and naturally, it was a costume party. There was Jessie who... Continue»
Posted by miguym4m 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6289  |  
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My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.

In August 2007 I was 24 years old and was constantly masturbating to shemale porn. My best friend was getting married and ... Continue»
Posted by feinor11 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6281  |  
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After School Dick-tention

I was late for class. Again. I slowly opened the door to my classroom, hoping Ms. Peterson was absent. Just as I managed to open the door enough to peer inside the class, I saw her. She had her back to me, as she was writing down notes for the students to copy, on the blackboard. I couldn't help but admire her form. This was her first year teaching high school history, and she had no shortage of teenage boy admirers. She was tall, I don't know how tall she was bare foot, but in heels (which she always wore) she was taller than most in the school; faculty or student. If I had to guess, I would... Continue»
Posted by SlaveX 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 6272  |  
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He transformed me to his bitch

This happened during summertime. Just after the end of school period, last summer before college. All of my friends had left the city for a beach house they rented. I was to go several days later. So I was alone in an empty city, since everybody was away for the summer holidays.
I was waiting at the bus station when a stranger came and asked me if I knew some decent place to have a beer. I suggested him a few pubs that were close when he asked me to join him. I was surprised and a bit scared, so I kindly declined saying that my friends were waiting for me. He insisted suggesting to meet for ... Continue»
Posted by georgette32hk 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6269  |  
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T-Girl University

Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for her from all those west-coast surfer dudes. He hoped she wouldn’t forget him and made a vow to himself to stay faithful no matter what. But there would plenty of temptation for him as well: Jason was going to a small northeastern college that, until recently, had been an all girls school. Jason’s in... Continue»
Posted by slatemhor 4 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 6188  |  
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Made my hubby crossdress and get fucked by bbc!

Finally convinced me husband to stop watching me take big cocks and to put on a pair of heels and to get fucked while its my turn to watch him!

ive always loved being a cuckold wife, meeting new people, having fun wherever it happens to be at, it really improved our marriage, finally i took it to the next step.

i spend alot of time at nights checking out mostly pics on xhamster and few videos. ive always been turned on by crossdressers, cumshots, and a few others fetishes im into. this time i finally got to see a live crossdresser fucked, my cuckold husband!

so we arranged to meet a f... Continue»
Posted by discreet4rmlanc 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6178  |  
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Shopping with my s****r - Part 2

Continued...

We drove along chatting freely, laughing when we saw guys checking out the two hot babes in the car next to them. Jane told me what purchases she planned for me, practically a whole new wardrobe I thought to myself, but hey who am I to complain. Jane pulled up in a quiet corner of the carpark and leant over and kissed me gently on the lips, her tongue probing mine. "Come on Dannii, lets go shop!" she giggles.

I climbed out of the car as ladylike as I possibly could, feeling the fresh air up my skirt and flow over my balls felt amazing, a nervous excitement building in... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 6112  |  
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Caught By My Black Stepdaddy

I was 19 and had just finished my first year of college and I couldn't wait to get home. It's not that I didn't have fun, I did. But I wasn't able to do my favorite thing. You see, I have a little secret... I like to wear...BLACK PANTYHOSE AND RED SPIKED HIGH HEELS WITH ANKLESTRAPS and dress up as a girl. And after nearly a year without doing so, I was just a few hours away from being able to feel like the sexy girl I knew I was born to be. What made things even better was that my stepfather Marcus, a big and sexy black man who I've found very attractive ever since my mother started dating him... Continue»
Posted by whawha1976 10 months ago  |  Categories: Sex Humor, Shemales  |  Views: 6096  |  
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My First Time

when i was 18 i first started to dress up when my mom was out and i loved it. well this is a story of my first time and i would like to share it with everyone. me and my mom live alone and she used to always bring guys back to the house and i used to always hear them having sex and it really turned me on so i tried to peek into the doorway each time and one time a guy left is underwear in the hallway so i picked them up and smelt them and it made me really horny. however this guy turned out to be my moms boyfriend so he came to our house on a daily basis but one time when my mom was out and i ... Continue»
Posted by MegCD 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6082  |  
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Paying rent

I’ve always enjoyed getting dolled up like a sexy girl ever since I hit puberty. Doing my hair, wearing frilly panties, skirts, painting my nails and doing my makeup. But being a boy that isn’t viewed as proper behavior. Which is why I’ve always had to dress in private. But luckily with the power of the Internet I’m able to express my inner girl. I run a blog where I post dirty pics of myself dressed up, erotic stories of young crossdressers being used by older men, captioning dirty pictures and I do webcam shows just about every night. I even get tipped for my webcam shows and can use the mo... Continue»
Posted by ScarlettMaeBottom 1 month ago  |  Categories: First Time, Shemales  |  Views: 6076  |  
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