Shemales Porn Stories
Page 72

First experience

I want to tell you about my first experience in cross-dressing and what happened afterwards.
First some explanations. When I was 12 or 13 years old I was a slim and tender boy with long hair (early 70’s it was normal for boys to have long hair). I lived in a neighborhood with a lot of c***dren my age (some a few years younger or older). So I had a lot of friends to play with. One of our favorite games was “cowboy and Indians”. We played this in the woods not far from our street. It had most of the time the same scenario. The older boys (2 or 3) would be the Indians and I and the younger boys ... Continue»
Posted by Catharina 3 years ago  |  Categories: First Time, Shemales  |  Views: 2079  |  
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“Some first date, huh”

So I had just gotten this new job at a fast food/dine in kind of place for the summer trying to make some extra money before the fall semester started. And there was this boy named Danny that would come into the restaurant every so often. He was really cute and had nice lean looking body. He was pretty shy but I could tell he was in to me because quite frankly the food wasn’t that good and he would always stop by during my shift checking me out. So a few weeks past and he had yet to make a move. I was a little hesitant as well because I didn’t know how accepting he would be of my “situation”. ... Continue»
Posted by pleasurenfun 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 2287  |  
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He NEEDED me!

I had gotten dolled up nice and slutty looking in my motel room, and had been internet chatting for a couple of hours, so I was feeling very sexy. All dressed up and nowhere to go in a small southern town. I peeked out my window and could see that the place looked pretty dead. No lights were on in the guest rooms; no cars on the street, nothing going on at all. Here I was, in platform shoes and a mini dress, face made up, and a very wet g-string from being horny and tucked for hours. I locked the room and strolled around the parking lot, then across a grassy area to where the highway bordered ... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1712  |  
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My new ladyboy- LittleLi - Part 1

It was nice to meet my new freind littleLi. I met her at the library at college one day and was immedietly attracted to her. Her long dark hair and big brown eyes, with a lovely sweet smile. She was wairing a little cropped T shirt with a hello kitty picture on it, showing off her smooth honey coloured tummy, cut off denim shorts, white frilly ankle socks and black patent pumps. I thought to myself, only an asian girl could wair little frilly laced ankle socks and mary janes and get away with it! I had known for ages i was bi, so i was not suprised that this fanatastic girl standing in fron of... Continue»
Posted by igglepiggle 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1885  |  
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Bookstore Babe Chrissie

My room mate and oldest friend Kelly found ourselves with a four day summer weekend and so Kelly decided to rent us a cabin on the lake. We invited a couple of Kellys’s lesbian sorority s****rs to join us but they wouldn’t be arriving until the next day.
We packed the car, loaded the cooler, rolled a few joints and set out around 11AM on a gorgeous Friday morning. Whenever we travel by car Kelly has to drive. I believe that it’s all a part of her dominant lesbian personality. When we’re together she assumes the male role and becomes my protector and decision maker. It’s not as bad as it migh... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 932  |  
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My first time

I sat in the car outside the address and to say I was nervous is a understatement. This was the first time I had ever done anything like this and I was half thinking of just driving away.

I had got messaging to Sara a month ago after liking the pictures they had posted. I was really in to clothed sex and the pictures showing Sara in a selection of boots whether they be leather or pvc, knee high or thigh high I didn't care as long as they have a stiletto heel l love them.

As for clothes I get hard for the slutty secretary look, a nice tight pencil skirt with some stockings and high heel... Continue»
Posted by big_rob49 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3581  |  
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First time fun

Been dressing for about ten years, started with few items now got full wardrober. Gone the extra mile by shaving all over and shedding some serious pounds to look good. Found a great site in US who sell made to measue mens CD TV Clothing so know I look good. Anyway, on a few websites and cam wanked a few times, but a while ahgo something caught my eys, or should I say someone!!!
Get loads of messages on AFF from loads of guys but its the CD ones that attracts me until had one from a guy who said was shaved ALL over. I adore shaved, I hate hairs, I wont 'play' with anyone in hair at all.
We e... Continue»
Posted by aroannecd4u 1 year ago  |  Categories: Anal, Shemales  |  Views: 563  |  
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Taken Care of My Lovers Cousin pt2

It was about ten Saturday morning when I woke from my slumber, Joliet was still lodged in my anus her/his penis soften but gripped by my anal sphincter muscle. I looked around and could not see James, I began to feel my aching butt hole. Even with Joliet's cock stuck in my butt, I could still feel the ghostly memory of James' massive fuck tool ravaging my butt.

Joliet began to stir as I moved and pulled me closer to her/him, 'David,' Joliet whispered into my ear, 'did you enjoy your little romp with my cousin James.' I thought to myself [how could you let him tke advantage of me knowing... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 486  |  
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It doesn't get any better than this!

15 years ago, I went into my older b*****r's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out my cock, and have at it. When I opened the mag, my jaw dropped and my dick got so hard, so fast it practically popped out of my pants! I could not believe what I was seeing! It was a gorgeous babe alright, but she had a BIG hard-on where her snatch was supposed to be! My cock was pulsing in my pants,... Continue»
Posted by bugaboobed 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3703  |  
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My absolute ultimate fantasy

When I was growing up my pops had a auto repair shop out in the country right off the crossroad of two main highways we were never going to be rich but we were very comfortable When I graduated high school he gave me half of the business,so I could take over when he retiredThat first summer is one that has shaped my life all due to a Texas gal named amie Belle. When you are young and full of energy and wanting more out of life sometimes you can go a little overboard.Many mornings we would get to rhe shop and there would be a traveller broke down sl**ping in their car waiting for us .I bought a... Continue»
Posted by diamondave65 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3309  |  
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THE TRAIN JOURNEY IN INDIA PART II


This is continuation of ' THE TRAIN JOURNEY IN INDIA PART I '

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well as you all read the ticket checker was in my cabin in the train

He was in his mid forties i guess and 5ft9 with a beer belly and chubby all over.

he was stared at me for a cpl of minutes and then removed his coat, shirt, pants and boxers. He had his back to me i couldnt get a view of his cock. he wore his pyjamas. I had meanwhile turned to face away from him and said "Bhanu did you lock the door?" and he replied "it is not Bhanu it is me Ramesh Sharma and I have locked the door !!". He had a gru... Continue»
Posted by hornyboyind 1 year ago  |  Categories: Anal, Shemales  |  Views: 773  |  
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careful what you wish for

a saturday afternoon hanging out up in the balcony of the old mid town theater in mobile alabama, under my street clothes, i have on a pair of sexy tight bikini panties, training bra, and a slip. as i stand up to the wall behind the seats i'm approched by two men, one on either side, they have apparently noticed that my shirt is open and have seen the top of my slip, bra, and the collar around my neck, before i can do anything, they are all over me feeling me up, and strip my street clotes off, so i'm standing there in my panties bra, and slip one of the men grabs my hands, pull's them behind ... Continue»
Posted by robinlikesitrough 2 years ago  |  Categories: Shemales  |  Views: 1240  |  
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Hotel Surprise

Working in the big city has it's perks and drawbacks. The other night some of my coworkers and I went out for a small celebration at a local restaurant. Everyone ordered drinks and we enjoyed our latest professional success. Finally the crowd thinned out and I was leaving with some others. One of the guys suggested a place near the art center for the city to listen to some soft jazz and blues. A few of us met there and were nursing drinks not really wanting to get d***k just feel good. I noticed an attractive woman sitting by herself at a small table. Our eyes met several times and fina... Continue»
Posted by biguy52x 2 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 1971  |  
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Gloryhole slut last night.

Well I was a horny slut last night and went to this little arcade in the city last night. Fully slutted out and in a new pair of silky nude hose I was hoping not to be disappointed....I was not!

I payed my fee and went into the back to the booths where there were a massive amounts of guys in the booths and just standing around. I was a little nervous waiting on a gloryhole booth to open but was catching the eyes of all the horny cocks also waiting for a turn in the boths. Finally after a few minutes 2 booths opened up and I went in hoping to get my hungry lips working right away. No soon... Continue»
Posted by luvpantyhose67 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 2881  |  
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Paying the rent in a special way!

When the rent is due, it must be paid, one way or another, usually the conventional way,which is cah or a personal check. Yet when neither is available at the time, well, other ways can be found! my landlord came over the other day, as he always does once a moth, to collect the rent, which i always pay on time and with a check, yet this time, short of cash and could not find my checkbook, i tried to explain to him that i would pay itthe following day, but he was adamant that i pay it right there and then! Well, i asked if he was thirsty, he said sure, he came in, we both had a cold one, and i ... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 2014  |  
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first time with both

I was young and I had a girlfriend who I confided a dark secret with, which I had never felt comfortable to tell anyone. She asked what I wanted to tell her and the suspense in the air as I told her was quite thick.
"I've always felt like a woman trapped in my body." I casually said.
"Why did you never tell me?"
"you are the first person I have trusted to tell."
She looked at me for a while, but then told me it was cool, and that I really had the body to pull it off. I was so relieved. She brought me sexy lingerie to try on and it fit, except for in the bust. I didn't care though I even s... Continue»
Posted by Lauren_lee 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 2703  |  
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Passionate Sex with a Beautiful Shemale

a man and his shemale lover get down to business
Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.

“Mmm,” she moaned, feeling Will’s lips kiss the nape of her neck, causing her to break out in goosebumps.

She turned to face him, wrapping her arms around his neck, drawing him close. They kissed, tongues ... Continue»
Posted by adel5000 3 years ago  |  Categories: Anal, Shemales  |  Views: 913  |  
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My very first experience with my classmate (episod

He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i felt the tears running down my cheeks as a result of this emotional discharge and hugged him,saying ''I was scared to death..of losing you...I thought you would never talk to me again''...Maybe i was being hysterical but i really wasn't thinking healthy at that moment..a typical girl:) I started to ... Continue»
Posted by Slave4str8twinks 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 1404  |  
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My first BBC fuck!

I went clubbing last week with my girlfriends that I work with and they recommended a hip hop club in a seedy part of town. I was alittle scared but we went anyway and well, and we were really having some fun there!!! I decided to dress like a real lil slut this night, a black minidress, lacey thigh highs and garters and black fuck-me pumps.

My girlfriends hooked up with some cute black guys and took off leaving me there kinda by myself. I was being hit on constantly by these hot black guys but I wanted a white guy, or at leas... Continue»
Posted by sataori_fukame 1 year ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 3111  |  
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A cum slut is born

There's little doubt about what turns me on most -- just check out my favorite videos and photos. Cum, Cum, and more cum. I'm a late bloomer as far as discovering my kinky side. After a long, dull marriage consisting of vanilla sex, I got divorced a few years back and decided to explore some fantasies. I love porn, and I've always been somewhat envious of the chicks in the xxx vids, they always seemed like they were having tons of fun getting their cunts, mouths and asses filled with hot cum. Multiple cum shots really turned me on. But I'd always identified as heterosexual -- so how could it b... Continue»
Posted by jizzlover123 2 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3528  |  
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