Shemales Porn Stories
Page 78

First Encounter With A Ladyboy

A couple weeks ago I met this fine girl walking down the beach. Looked a little asian, but maybe she was one of those latina aztec chicks that just look asian. I go up and talk to her, shes got a really sweet voice, tells me her name is Jazz. I start talking with her about where she lives. Tells me she lives a couple blocks away and she tans all day long next to her pool. I look at her.. and damn shes right, cuz she has a really nice golden tan. I ask her "well why are you at the beach? "Cuz Im tired of tanning and not showing off my body to anyone!" I say, "oh well that definitely makes sense... Continue»
Posted by bnrslyr 1 year ago  |  Categories: Anal, Shemales  |  Views: 2898  |  
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Mile High (caught in panties and pegged at thirty

Mile High (caught in panties and pegged at thirty thousand feet)

By Mikaho

Edited by g1dnshwrgr1 (many thanks!)

NOTE: This is my story and is originally posted under my profile on literotica.com. You can see it there under my same user name. Enjoy!

I boarded the plan and was taking my seat when I noticed the most mature of the three stewardesses. She was beautiful with a classic flair; her pencil skirt perfectly presented an hourglass waist, defined hips, and a round butt.

The image of her shapely form flitted around the edge of my thoughts as I started answering email on my... Continue»
Posted by Mikaho 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 2517  |  
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my first cock experience (true story crossdressing

I will never forget my first experience with another cock , it was the only time I have ever been with another man, now saying that I do date ts women, I love them as much if not more then I do genetic women. I was 12 years old and like any young boy , very horny . At that time my best friend liam and I would have sl**p overs and do normal k** stuff , sports , video games , camping , never did I think that one day I would have his warm milky cum in my mouth or his warm hard throbbing Dick inside my ass pussy .

It all started when we were looking at a magazine and saw a picture and article ... Continue»
Posted by dickissogood 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4906  |  
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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: 6414  |  
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7/11



his name was jason. he was just a workin class guy, not much in the way of looks, slightly longer hair than normal, somewhat athletic, and gifted with a 11 inch penis and good sized testicles.he would go out after work and survey the bars and theaters, goin to concerts or events and haveing fun. the guy was a social maveric and great with girls. well, he knew how to get girls. he wasnt so good at choosing them.
jason decided to go to the local bar after work one day and found it half deserted. it was around 7:15 on a saturday night. it didnt make since for the place to be mostly empty. th... Continue»
Posted by mj2397 2 years ago  |  Categories: Anal, Shemales  |  Views: 1118  |  
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Domestic Bliss, caught dressing and my life was ch

As I mentioned in another story, I started dressing when I was around 11, at first in my older s****r’s clothes, she was just getting into her teens and had her first bras and stockings and I had my first thrill wearing them. There were just the three of us at home, Mother, s****r and I, father had long disappeared. Mother worked in the fashion industry so back in the 1950s/60s/70s when there were still the classical fashions being worn daily, she was always immaculate.

As I got older, I started to wear her clothes and then one day, my s****r, who was supposed to be out, walked in and cau... Continue»
Posted by antoniaf 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 819  |  
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Our First Time

I take my hand a gently begin caressing the ever increasing bulge in your pants while tenderly kissing your neck. I push you onto the bed and crawl up to you and begin to unzip your pants. I take my hand and grasp your rock hard shaft and begin to stroke you. I can feel you get harder in my hand. I stroke you faster and faster until you almost can't handle it, I stop. I pull your pants off and your shorts and begin storking again. I open my mouth and wrap my juicy red lips around you and begin to play with your head with my tongue. My other hand begins playing with your sack, massaging and twi... Continue»
Posted by uatu40 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1328  |  
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bookstore sissy slut

My name is dollie I love to be a girl and being very petite and pretty long black haired its easy for me too feminize. And until now I wouldn't go out, dressed up, sometimes a quick walk around or a short drive but nothing real. And one time in college I walked around the campus. Anyway I ignored all the signs being overly sensitive for a boy It should of clicked when I was diagnosed with disphoria. I knew I liked being girly but I really thought all teen age boys were like me. Always being a pretty-boy girls always came my way but they all end the same I get hurt because just like a girl ... Continue»
Posted by dcdollie 1 year ago  |  Categories: Fetish, Shemales  |  Views: 1844  |  
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A Day at the Beach

A Day at the Beach
By Lorenqt

I lay face down on my towel, basking in the sun, almost falling asl**p. My boyfriend Jake, he would be my husband if it were legal where we live, walked up and sat next to me. He gently stroked my left arm, "The water is great, Loren. You should try it."

Without opening my eyes, I turned my head towards him, "I think I'd rather just lay here in the sun."

He started rubbing my shoulder a little harder, "Come on, sl**py head. Get up."

"Stop it Jake!"

He gave me a quick kiss on the cheek then he whispered in to my ear, "Or, would you like me to ma... Continue»
Posted by lorenqt 11 months ago  |  Categories: Anal, Shemales  |  Views: 3284  |  
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How I want fucked

I show up to my apartment after too many to find my new neighbor had a few, as well. She is doing better than me, but clearly hornier.

I bring her inside, light the candle, play some music and try and be sensual. Grab some drinks, and get ready for as little talking as possible.

The lights in my room are off, and she says to keep them off. She wants a back rub.

I don't even know her name yet, but I leap on without asking. Her shirt is off, her skirt is still on, as are her panties and bra. I rub the shoulders, I rub the neck, I kiss the neck, I kiss the ears. I lick down the b... Continue»
Posted by getdown 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 2457  |  
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How I became gay pt 1

When I was in my teens I was only interested in girls and thought that being involved in a gay experience was completely disgusting. I never would have even thought of it if it wasn't for what happened when I turned 17.

On my birthday me and a few friends got fake I.D.'s and went to a bar in town. We all started drinking and getting as shitfaced as we possibly could. There was 4 of us and my three friends had all spoted the girls they wanted to fuck that night so I was left alone at the bar.

Within a few minutes this girl sits next to me and I immediately started checking her out. Sh... Continue»
Posted by Gayluva67 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5174  |  
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Sissy For My Flatmate, Chapter 2 – The Contr

If you've only just tuned in, here's what's going on in my life. Until recently I was a closet crossdresser trying to keep my hobby from my flatmate. When he caught me in the act, I found out that not only had he known about me for a long time but it was a turn on for him. I agreed to become his sissy slave and started the most incredible journey of my life.

Arriving home after from work, I threw my jacket down on the sofa and breathed a sigh of relief. It was Friday and I now had the weekend to look forward to. I slowly unbuttoned my short to reveal a short corset. It's been a few we... Continue»
Posted by Yosho 2 years ago  |  Categories: BDSM, Shemales  |  Views: 618  |  
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Airconditioner repairman laid some pipe

I was literally bored to death when my mom went on a vacation, i was hoping that i was gonna enjoy freedom when mom's away but things got worse as i found out the air-conditioner wasn't cooling the house, it was the dog days of summer and i really hate this muggy, hot weather. So i gave a call to the place where we bought it and asked them if they could send someone to fix it. Like i said, the weather was terribly hot, therefore i was wearing a micro-mini short which was showing of my curves in a very revealing way. It was almost 4.00 pm when the doorbell rang. I was expecting the same guy... Continue»
Posted by Slave4str8twinks 9 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3239  |  
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The continued adventures of Allison the cumsissy

The Continued adventures of Allison the cumsissy
This is a continuation of the same sissy slut’s story from my two previous works about Allison the sissy schoolgirl and her black daddy.

After the week long fuckfest, Allison the sixteen year old sissy schoolgirl boybitch had with her black daddy neighbor, she realized she was meant to a be a sissy cumwhore and decided to shop for as many sissy items as she could afford as soon as she could discreetly do so. As luck would have it, the following weekend her parents informed her that they would be going out of town yet again to visit his mothe... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1900  |  
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First time in Bangkok

If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floor of a 5 star hotel in Bangkok, which was pretty nice. I had just turned 39 and was looking forward to my first visit to Thailand and seeing my friend I had not seen in 4 years.

Now, I have travelled very much in Asia: PI, Hong Kong, Tokyo, Singapore, pacific islands, and Hawaii, but not Thai... Continue»
Posted by mahuluvr 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 2527  |  
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Teen Cross dressers First Man.

This is a true story that happened to me only a few monthe ago.

I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy.

One Friday after a grueling 4 hour study session at school one of my classmates, who I didn't know very well, invited me to have a few drinks... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2266  |  
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My firs time as a crossdrese

Hi,i am 19 and i have always liked wearing womens clothes.While wearin them i always imagined there was a nice older guy fucking me and cumming on my face. After a while i decided to try my fantasy for real. I got in contact with an older men and we decided to met. He said that he would come for me in a car and that we will go to his house and have a lot of fun. I was so nervous and could hardly wait to meet him. The next day i was waiting for him at a spot where we arranged to meet. He came in his big black suv and opened the door and said to get in. I got in and sat next to him. He had dark... Continue»
Posted by nikoletakurva 3 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 1740  |  
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Tania

Tania was different! She looked and smelt so feminine. I'd been with other tgirls in the past but she was just different.

We'd been emailing and swapping sexy pics for some months now but now the day had finally arrived when we were at last going to meet. We'd arranged to meet in a lay-by just of the A46 just past a little village called Upton Crosby. I'd spent the last couple of days in a state of constant turmoil! What to wear? What would we talk about? What would we do? Would she like me? There were so many questions going through my mind. I so much wanted it all to be just right.

The... Continue»
Posted by joannacd1 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 1356  |  
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Turning my neighbour on in pantyhose

One of my neighbours whos in his early 50's and clearly a man of taste;) asked me recently had we got a cleaner in?! I said yes a couple of times a week. He seemed happy!
I know why..... My name is Lucy and I love strutting around in front of the window with sexy outfits on. I'm meant to be our new cleaner but I have to be honest, I don't do much, just a lot of bending over and stretching up high!
Yesterday I was dressed as 'Lucy the maid', shall we call her? I had 4 inch black leather heels on, which make my calves look fab!My favourite stocking patterned tights which are as equally shin... Continue»
Posted by lucyslegs 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1710  |  
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Would love a shemale like this !!

****d (sort of) by a Shemale!

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon.

I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.

Her hair was dirty blond and loosely curled, and her face was quite beautiful. She w... Continue»
Posted by loverboydjinn 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2081  |  
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