Shemales Porn Stories
Page 66

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.

There is no cross dressing in the story but this is how I began my transformation from
regular boy into cock suckking teenage crossdresser.

We were having a really hot heat wave. i meat with my older b*****r (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going to the movies by myself but I really did want to see that inception movie. I looked up whe... Continue»
Posted by srlvictoria 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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mommy's new girl

It's true that I had become accustomed to drama in my f****y. My father was loud and mean, especially when he was d***k, which was most evenings and every weekend. He would back my poor mother into a corner of the kitchen and berate her, towering over her in that threatening way that I knew so well, telling her she was fat and ugly and stupid and spending too much money on me. He would get louder and louder until she finally began to tremble and sob – then he would storm out of the house in disgust, as if her crying gave him the right to leave his "silly emotional wife" and visit his drinking ... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Mature, Shemales  |  
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White sissy tp black man

On the bed in the guest room, Jamie lay back against the flowered pillows, feeling pretty in his pink satin nightie, his stockinged legs spread wide, and the long black vibrator pressed to the mound in his panties that betrayed his tied-back cock. He slid the straps of the nightie off his shoulders and pulled one pale little tittie out a frilly lace-lined cup. He squeezed the small sensitive nipple and took the vibrator off his already wet panties and placed it instead against his tight asshole.

"Oohhh…" he moaned, licking the raspberry lipstick off his lips.

He opened his made-up eyes a... Continue»
Posted by jeffreybarnes 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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the making of white sissy girl for moms black love

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I’d said something to offend him and responded by saying, “Well, no one’s ever told me that I was unattractive.” When I suggested that was because no one had had the occasion to be brutally honest with him, he got visibly pissed off and blurted out, “Well, my mom thinks . . .” and caught h... Continue»
Posted by momandboys 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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sold into sissyhood

They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car.

It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. Im very easily intimidated. And there I was in a tiny plaid mini and white pump sandals about to mince my way passed a group of young black street-toughs. Even in broad daylight, even in guy-clothes, I'd have been terrified…

Lise sat behind the whe... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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One for the team

Bored, she began to flick through the radio stations. Where was he, the game had finished ages ago but there had been no sign of anyone. Most of the crowd had already gone home, just a few stragglers and the cars of the players remained. He knew she got horny watching him play, it wasn't fair to leave her frustrated like this. Eventually she could stand it no more, getting out of the car she began to walk over to the dressing sheds. As she got half way to the sheds she paused as she saw two guys emerge, but neither where her man so she began walking again. At that moment one of the two guys lo... Continue»
Posted by ghtaree 1 year ago  |  Categories: Group Sex, Shemales  |  
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My night as a woman

My name is Samuel Adams. Not the famous one, just a regular one. When I woke up today, it was like any day. It was Saturday so I didn't have work, and I slept till god knows when. I felt funny though. My head was fuzzy and my stomach kind of felt weird. I felt hungover but I honestly didn't drink the night before. My chest was really tight too. Like something was hanging off my shoulders.

I was walking around my home for evidence of my roommates. They were no where to be seen. The house just felt empty like things were missing. Like they moved out the night before. There was furniture in th... Continue»
Posted by slamadams 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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SHEMALE SURPRISE #2


as niki and i sat on the sofa fondling each other niki whispered,
"you know jay that last time in the treehouse when we gave each
other hand jobs i wanted so much to have your hard-on in my mouth
and have you cum in my mouth, and i still do. am i sexy enough for
you that you'll let me suck on your cock?" i gasped in reply, "oh
yeah niki you are very sexy and i want you to do whatever you want
with me. but first i'd like to fulfill a fantasy of mine first."
"you have a fantasy concerning me jay?" niki asked. i answered,
"well now that you look like you do now i sure do." "What's your
... Continue»
Posted by qrystofer 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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SHEMALE SURPRISE #2


as niki and i sat on the sofa fondling each other niki whispered,
"you know jay that last time in the treehouse when we gave each
other hand jobs i wanted so much to have your hard-on in my mouth
and have you cum in my mouth, and i still do. am i sexy enough for
you that you'll let me suck on your cock?" i gasped in reply, "oh
yeah niki you are very sexy and i want you to do whatever you want
with me. but first i'd like to fulfill a fantasy of mine first."
"you have a fantasy concerning me jay?" niki asked. i answered,
"well now that you look like you do now i sure do." "What's your
... Continue»
Posted by qrystofer 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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hotel steam room

Once I got to high school my thoughts of wearing panties and sucking cock subsided as I became a normal teen with a girlfriend,It wasn't till I was 22 that I would realise my true passion.I traveled to Toronto with my b*****r and his girlfriend so she could right an exam.We were on a budget so we all shared a room downtown.The first evening I was tired so they went for dinner while I stayed in.While getting a beer from the fridge I noticed her suitcase open and a bra laying on top.I immediately got hard as I looked at it and had memories of my younger days wearing Lingerie.I locked the door so... Continue»
Posted by sluttysherri 1 year ago  |  Categories: Gay Male, Shemales  |  
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but was it REALLY all about the big black dick?

so...

i'm certainly not complaining, 'cause i'm actually pretty happy about it, but you've kinda fuk'd things up for me.

YAY!!!

i mean, i used to go out at every opportunity i had & A: whore; B: hit the book store; or C: just roam the streets in general.

but being with you was just so fukin' wonderful that i've pretty much lost interest in doing all that. it just seems so dirty & cheap & doesn't mean the same things it did to me before. it had been about meeting people and having a chance to interact with them as gyrl. now... i've met you... our brief encounter filled me up with so... Continue»
Posted by roxxanna 1 year ago  |  Categories: Shemales  |  
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Me & the futa

my boyfriend & I are home when a friend of his comes in to hang out. I notice that she has eyes for me but dont say anything. Later my boyfriend leaves to go to the store for snacks but his truck breaks down in the parking lot. His friend & I watch the movie waiting on him when I notice that her skirt was lifting up.

"whats that?" i said. "it's nothing." she says as she puts her hand over her lap.

"huh? Are u sure?" i said as i get closer to her. she gets nervous & stands up fast, but she slips & falls over with her skirt up over her dick. i stared at it, shocked to see that she has a... Continue»
Posted by coconeko 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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caught wearing my aunts lingerie

Getting Caught Wearing My Aunt's Lingerie!

Since posting the story about how my aunt introduced me to makeup and crossdressing, I've decided to tell the story about my uncle. He was a man's man with the most beautiful cock I've still ever seen in person. Anyway, me and my cousin used to play with his mother's makeup and wore her lingerie while we jacked off and sucked each other's cock. We did this almost every day in the summer months from the time we were around 11 until we both were almost 16. It was great fun and we had many orgasms together.

One day my uncle came home from work ear... Continue»
Posted by momandboys 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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my aunt made me a transvestite

My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in her 3 inch heels. She had long auburn hair with beautiful waves in it. She wore a 9 1/2 shoe. Her hands and feet were large, but so sexy looking with nail polish on. Her blue eyes would melt you. She had a great mirrored vanity she would sit at for hours and try different combinations of makeup. Sh... Continue»
Posted by momandboys 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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Back lot slut

The following story is true ...

He works the night shift at a truck repair center on the edge of town, near a big truck stop. In our online chats his instructions had been specific -- I was to be there waiting for him at 12 midnight, and I was to wear my tallest high heels, my shortest skirt, stockings and garter belt, my cock rings and butt plug, and no panties. He would take it from there. But when I arrived he was nowhere in sight, and after waiting about 10 minutes I finally had to drive around to the side of the building and catch the attention of some coworkers. It was really e... Continue»
Posted by sherricd 2 years ago  |  Categories: Anal, Shemales, Voyeur  |  
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SHEMALE SURPRISE

while in our early teens my cousin nicolas and
i used to look at porno mags and videos up in my
tree-house which was quite a ways from any other
structure. during these sessions nic and i would
whip out our young hard-ons and whack off to the
images of naked women and men of all ages. we got
together to do this about once a week and discuss
the sexual escapades we may or may not have had
with girls we went out with during the week. a week
after nic had graduated (i was still a junior) he
came over to the tree-house and said
he was leaving for the city "to find himself."
when i... Continue»
Posted by qrystofer 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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For Hentai/ futanari lovers only

First it starts off with Jay and Hex spending time together for the first time since Jay came home from the military. After a day of hanging out at the lake the two decide to head back to Hex's place for jay to see where he lived since he moved out from home. Upon arriving at his new home they decide to order some pizza and watch a new movie that hex ordered on cable after they eat they continue to watch the movie. An hour into the movie everything goes black the two think the power went out but little did they know that no power was the least of their problems as the room slowly began to ligh... Continue»
Posted by HERCK 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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my week away with my Dom. BF

So, I am a cross dresser, a submissive cross dresser, and my BF knows how to really use me! We had talked about how I got turned on when he was rough with me, when he took me anyway he wanted to during the weekends we spent together. How I fantasized about being a slut for one or two more of his friends at the same time. How just talking about being the group slut, being at their mercy was such a HUGH turn on for me!

I knew he was going on vacation in a couple weeks, and would be gone for about 10 days or so. What I did not know was that he had set me up to be able to come along with him... Continue»
Posted by subrhia 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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The first night

We finally meet in a bar after exchanging messages. Admittedly I’ve been turned on by the thought of where the night could lead but you can tell I’m slightly nervous. As we enjoy our first drinks together we chat about nothing in particular but I notice a cute smile you have as we talk.

You can see that I’m becoming more comfortable and open with you so you decide to ask

‘hunni, what do think will happen tonight?’

I lean in close and whisper

‘I want you to be my first’ before kissing you softly on your lips.

We start to kiss passionately and then decide to leave the bar.

As ... Continue»
Posted by kinkymister 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Fucking my friend's little sibling

After a night out I stayed over at my friends sl**ping in the spare room. In the morning my friend had work and left without waking me but she told me the night before she had work and I could stay until she got home again.

Waking up in the morning I felt groggy and tired but one thing I did notice was I woke up with morning glory, I was rock solid and made a huge tent of the quilt. I needed to sort this out. I slid my hand down into my panties where it was stretching them and slid them off allowing my cock to grow to it's full size, I was so horny and instantly began wanking to hard and f... Continue»
Posted by shemalecharlotte 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
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