Shemales Porn Stories
Page 15

First time

Continuing with my life stories, this recounts my very first man.

I was still a teenager and still at school. Those were mere technicalities and certainly had no bearing on my libido and overwhelming desire to experience a man for the first time.

I had heard through various sources and local papers that there was an increasing issue with gay men cruising in a certain park in my town. I had to find out more. One day I told my parents that I was staying late at school to catch up on some homework. This gave me the opportunity to check this park out, plan my strategy and eye the talent t... Continue»
Posted by TerriSlut 1 year ago  |  Categories: Anal, Shemales  |  
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She was a he

Few years back I was in a bar in London getting a round in for the lads before we hit Fabric.
I will be the first to say I'm not the fittest of guys and rely a lot on my charm. I took the drinks back to the table and returned to the bar to grab mine when a stunning Asian girl caught my eye and smiled at me. She glided when she walked, a smile that made your heart melt and a body to die for, why was she heading over to me....?

We chatted for a while and I agreed to meet my friends in the club a little later so I could get to know this amazing angel. We chatted, flirted and laughed until th... Continue»
Posted by dirtydisco99 2 years ago  |  Categories: First Time, Shemales  |  
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My future wife

The last couple years of my life I have not really had a steady girlfriend. I’ve seen some girls off and on but nothing lasting longer than a month or so. I haven’t had the sexual desire to find a girlfriend with all the sexual encounters I have been having with my gardener or neighbors. However I was missing the companionship that having a girlfriend brings.

There is this girl at my office that I have been pretty good friends with at work for the past few years. Her name is Samantha but we all call her Sam. We go to lunch on occasion and I have hung out with her in a group setting outside... Continue»
Posted by handiman1980 2 years ago  |  Categories: Anal, Shemales  |  
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Exploring My Husbands Sweet Tight Little Ass

Several months back my husband & I were having some intimacy issues & we just weren't connecting sexually like we used to......but that all changed over night a couple weeks ago. We had decided that this rut we were in was going to end one way or another & so we made plans for the upcoming weekend & booked an expensive 5star suite at a hotel for the entire weekend. Well we still had to make it through the week before our little get away. So we went about our normal routine getting up in the morning & going to work & then coming home & eating dinner together......you know all that normal every... Continue»
Posted by AryanGoddess_1488 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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A dream comes true

This is a story that I made. The high school part is the real part in my life that happen, the rest of the story is part of my fantasy.

I was down on my luck, my girl left me after I left high school. We both almost liked the same things, we both liked the same video games, anime hated the Twilight series(ugh even typing it make me feel sick even if it is over) I tried moving on but it was hard but couldn't get her out of my head. When I was not thinking about her my head brings me back to her sometimes for the good time but usually saying "what did I do wrong?" even in my dreams she appear... Continue»
Posted by southwestwarrior 15 days ago  |  Categories: First Time, Shemales  |  
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Restaurant Futa Fuck (Part 1)

"Did you want to grab something to eat this afternoon? My treat?" I said, eagerly awaiting Sar's response.
"Sure thing, Bianca! I have a lunch break at one. Wanna meet up?"
"There's a great Italian place not far from your office. Paradise Restaurant I think it's called. I've been thinking of trying it for a while." I lied. I had been there before, but I wanted her to feel like we were experiencing something new together.
"I think I know the place. I'll see you there soon."
"Sounds good!" I hung up the phone and let out a deep breath. Sara was gorgeous, with long ... Continue»
Posted by BiancaBigTits 2 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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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 2 years ago  |  Categories: Lesbian Sex, Shemales  |  
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Little Panties for a Little Cock


Little Panties for a Little Cock
bySarahCD


It was Saturday morning and I decided to get my laundry done before going out for lunch. I took my stuff down stairs to the basement laundry room, loaded a washer and started the cycle. I was about to go back up to my place when I noticed a basket of laundry on the table. I went over and found a mix of girls and guys stuff, I guessed they belonged to the young couple in the apartment opposite mine.

I glanced around and since I was alone I could not resist reaching out and touching a skimpy pair of pink bikini panties, I love pink and thes... Continue»
Posted by keripinkpanty 5 months ago  |  Categories: Group Sex, Masturbation, Shemales  |  
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Used by a gorgeous ladyboy.

(Yeah it's been a while but i'v been busy … doing the thing in real life with a new guy i met and there is not much need for xhamster at the moment :) . The story below is based on a true experience and i just changed a few details to spice it up a bit)

This story is based on a true experience and happened a few years ago, on a great night out in Amsterdam. It was before i had sex with guys on a regular base and i entered a complete new and exciting world...

During that period of my life i was single and i only recently started watching ladyboy porn and started to like seeing dicks in my... Continue»
Posted by abitqueer 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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Closet Sissy step Son Made Into step Daughter 2


My steps****r had just come out of the closet with a handful of clothes and told me to take off the swimsuit. She laid out a pair of white cotton panties with cherries on them and a matching bra. A short pleated plaid skirt and a white button down shirt. She also laid out some white thigh high stockings and some black Mary Jane platform shoes. She said this one was mine.

She laid out a nearly identical one except that her plaid skirt was green whereas mine was red. She told me to get dressed... Continue»
Posted by Batman_112 2 months ago  |  Categories: Anal, Taboo, Shemales  |  
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Getting back at the bully

Hi, my name's Rose Marie, and though you may have already guessed, I'm a hermaphrodite. Don't let that fool you though; I'm not some wimpy little girl. I'll admit I can get a little rough, but I can be laid back too. I just turned 17, and just like a lot of other people, the good 'ol hormones are ragin, but I do a lot better job of hiding them from most people, when I want to that is....

I'll be a junior in high school this year, I’ve had a mostly quiet summer. I have dark red hair, I put some white streaks in it with one of those hair styling kits, I’m not trying to be the center of attent... Continue»
Posted by wheels1825 3 years ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  
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Marinate with cum.. I mean love ;)

You see, I am a cum slut. I love to take cum all over my face. The more cum I can get the better. The place I usually go is a local adult movie theater with stalls in the bathroom. What are nice about these stalls are the glory holes. I love to suck cock through glory holes. There is something about sucking a cock from a total stranger that you can't even see. I have sucked a bunch that way, but I am beginning to want something more. I want a cum bath, a bukkake session. I want to be in a room with 10, 20 or even 50 guys with the sole purpose of having them all jack off onto my face. What foll... Continue»
Posted by CumLovingKitty 11 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Morning Surprise

Not my story

I walked into the hotel bar after the closing reception of my week- long conference ended and she was sitting there. Absolutely gorgeous. Blonde, about 30, maybe 5' 4", probably 110# and a 34C. I was stunned, but with nothing to lose I wandered up and took the chair next to her. She acknowledged me as I ordered a drink. We chatted and I noticed she turned towards me opening her legs slightly. Her body language told me I had made a good decision to sit by her.

We enjoyed several drinks as our inhibitions dropped. We chatted and laughed. I realized it was time to make my move,... Continue»
Posted by drew1207 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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glory hole dressing

I had the night off and decided to go down the block (WeHo) to a local book/video store. I got dressed into my sexiest short skirt and slinkey top (with my latex boobs) wig,makeup and "cleaned up" below.

I walked the the store and a few jaws dropped as I slowley looked around. I picked out a small butt plug ,some lube and went to the counter and paid for my items...and asked for 5 dollars in quarters,winked at the cashier then strutted off to a booth in the back.

At first I just wanted to watch some movies,but I got so hot I placed a drop of lube on the plug and eased it in slow...POP...... Continue»
Posted by sodeep2 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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CaughtWith MyPants Down


When they walked in the unlocked door, I froze like a deer caught in headlights. Although Carol was my girlfriend and we had great sex, I still enjoyed my closet dressing. Well one afternoon when no one was around, I took a bubble bath and pampered myself. Then I dressed entirely in Carol’s lingerie and sexiest short skirt. I was feeling sexy when in through the unlocked front door, Carol and her s****r walked in, I couldn’t say or move a muscle. Carol and her s****r just casually walked around me and looked me up and down. I was totally surprised when her s****r took my... Continue»
Posted by dlishmis 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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What Happens In Vegas! (copy, I wish i was able to

Hi there! I'm Ann. I would like to share a true lifestyle story with you that has been permanently embedded in my memory and makes me cum every time I think of it!
Let me begin by giving you a bit of background about my husband, (Tony), and my swinging history. Tony and I are a happily married couple living in Las Vegas and have been in the lifestyle for over 15 years now. We have certainly enjoyed our adventures over the years and have brought every fantasy we have had to reality. Living in Las Vegas, we enjoy the fact that we have a constant source of play mates in the large number of tour... Continue»
Posted by pervert76 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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FIRST TIME WHORIN'

FIRST TIME WHORIN'

I was just 18 when I went out whorin' for the first time. It was something I had an overwhelming urge to do after fantasising it countless times. I had been painting up and dressing since I was 13 and my 18 month older b*****r had been fucking me regularly since I was seven until he went away in the Army when I was 16, plus I had been shoving all types of objects in my pussy almost daily. My desire to have my pussy ravaged was insatiable. I used cucumbers and even a slender long Japanese eggplant about two inches in diameter, fantasizing it was a BBC. I reveled as I watc... Continue»
Posted by tvsllutmichelle 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Moms friend Vanessa


My mom had a best friend named Vanessa. She was more like an aunt

and always was around. She had big tits, a thin waist, a fat ass,

and nice big legs. She would always wear short skirts or short

summer dresses that showed her wonderful legs. One time my mother

was at work and Vanessa was watching me until she got home. I was about

8 at the time watching tv in my spiderman underwear laying on the floor.

Vanessa was sitting on the sofa reading a magazine. She crossed her legs

just as I had looked up. What I saw made me very curious to say the least.

I saw what look... Continue»
Posted by moms_sissy 3 years ago  |  Categories: Mature, Shemales, Taboo  |  
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The Fam...CH 1

Key Players;

Father - Dave

Mother - Brenda

Male sibling- Stevie

Female sibling - Alicia

Neighbor mother - Lakeysha "candy"

Neighbor twins - Keke & Tricia






"Fuck daddy...that was fucking hot" Stevie said while scooping up his f@+=€r's cum from the side of his face with his finger. Stevie was kneeling by the side of the bed with Dave's quickly deflating 9 inch black cock only inches from his face. Stevie is a young tw€|>e year old b•y that has recently been diagnosed with gender identity disorder. He is the youngest product of an interracial marriage between Da... Continue»
Posted by TS_LoverBoy 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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My Crossdressing Teen Neighbor

There is a duplex across the street, the kind with an ill arranged addition that sprouts out of the top and basically looks like shit. It's a slum lord house, geared toward your average broke ass people. You'd think I was complaining, but I am actually quite glad such a place is right in plain view.
There is a young couple that lives there, hipster punk types. The dude is nice enough but a little awkward, but the blonde chick is a little flat chested blonde hottie with piercings and pastel highlights and a plus size ass. Needless to say I'd like to breed her good. Someone looks to ha... Continue»
Posted by cumquarts 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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