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1st time with a shemale

I have always enjoyed playing with my ass hole, about two years ago I was in Chicago and went online to Eros and chose a shemale named with held. I called her up and she came to my hotel room. I was very nervous when I opened the door. She was about 6' tall and was a very good looking Latino. She bent down and gave me a kiss right on the lips and man where her lips where soft. She went into the bathroom and asked me to relax and she will be right out. I was lying on the bed and she came...

How I Ended Up a Submissive Shemale Slut Part 1

I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly f***ed blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own stories and beginnings, and this one is mine. I am a very...

Shemale Subway Sex

I was out at a dance club with some friends on Saturday night. Clubbing isn’t really my scene though, and I soon found myself very bored. Looking at my watch, I saw that it was almost 1 o’clock in the morning. I was having an awful time, and if I didn’t leave then, I would miss the last subway train and have to take a $50 cab ride home. So I said goodbye to my friends, and caught the very last train home. The subway ride from the club was going to be around 40 minutes. At first, the car was...

first time with a shemale

Anyone who has read my other stories will know that they are based on real events, this one is also based on an actual event. It happened on a recent trip to Thailand.We arrived in Thailand on a Friday morning, looking forward to a well-earned break. Jaq and I worked long hours, and we lived for our holidays. We had decided to visit Thailand as we were both curious about the availability of good looking shemales.It had long been a fantasy of ours to try a threesome with a shemale and hoped this...

Shemale Fantasy

Recently you've started to wonder what it would be like to be with a shemale. You've always been attracted to women and have no homosexual interest at all, however the fascination of a women with a penis has made you curious of what a sexual encounter with a shemale would be like. Curiosity finally getting the better of you, you decide that you're going make it happen just once.

First Time with a Shemale

This is a true story about my first time being with a shemale. I happened just over a year ago on the tail end of a business trip to Amsterdam. I had a couple of free days at the end of my trip to enjoy and explore the city. So naturally, I decided to check out the night life and that meant a visit to the Red Light District.I spent a lot of time just walking around and taking in the sights and sounds of the area. There were so many people walking around and it was alive with all their energy. I...

Shemale at the airport

The first shemale story I ever read and still one of my favourites...Layovers are a pain at the best of times but the prospect of five hours at theairport was not a good one. My inbound flight had been delayed and I had missedmy connection, so there was nothing for it but to wait out the afternoon andcatch the next 'plane home to the wife and k**s.The only saving grace was my business class ticket, meaning that at least Icould loaf around in the executive lounge and not in the main...

Shemale at the airport

This is the first shemale story I ever read and is still one of my favourites...Layovers are a pain at the best of times but the prospect of five hours at theairport was not a good one. My inbound flight had been delayed and I had missedmy connection, so there was nothing for it but to wait out the afternoon andcatch the next 'plane home to the wife and k**s.The only saving grace was my business class ticket, meaning that at least Icould loaf around in the executive lounge and not in the main...

A shemale couples vacation in Thailand Part 1

I'm neither a professional writer nor a native english speaker. So let me apologize beforehand for my bad grammer and writing skills. This story includes mainly: Shemale on shemale , Interracial , Domination , Submission , White , Asian , Ladyboy , Some light cuckolding.I'm a Trans-girl also known as a Ladyboy, living around the area of Pattaya at that time. I was just 22 years old then but dispite my age, i had already multiple sexual encounters with other ladyboys. And yes i said ladyboys...

One of my shemale escapades from back in the day

A number of years later, after my first shemale expereince, I still had a penchant for a hot shemale or a slender sissyboy who was passable. That's when I met Gina, who fit the mold of a slender sissyboy who was much more than passable, she was gorgeous.The first time we got together was on a rainy Sunday afternoon. My wife was out of town and I was cruising aroind on AOL in the SoCal Shemales chatroom. I came across her screenname and we started to chat. We traded writen descriptions of one...

The Studio and the Shemale Pt 3

4 years have now passed since I went to work for George as his apprentice. George has semi retired and left me to run the Studio with Amanda as my receptionist. Amanda and I are still as in love as ever. We leave our flat and walkk to the Studio at about 12 and stay open till quite late in the evening. Most of our work is with shemales now but we do have a few crossdressers on our books and we will do photographs for crossdressers if they want it. Amanda or Jessica will do their make up.We have...

My second shemale A true love story

Having just left Amanda’s, my very first shemale, I found myself still lusting for more. I had just cum twice, (the joys of being young) but wanted, needed more. I quickly flipped through pages of my adult personal newspaper and found “Jennifer.” She looked beautiful in her ads picture. There is nothing more attractive, nothing sexier than a shemale and my lust for them seemed to have only increased. Jennifer lived in a busy apartment complex and I nervously searched for her door. “Paul” I...

My first Shemale a true love story

Even from a pretty young age, I loved Shemales. I loved everything about them. They seemed to me to be the perfect object of sexual desire. Beautiful, feminine, tits and a cock. My first introduction happen by accident, in a way. On the other side of town was a row of newspaper stands that sold adult newspapers. Late one night, I rode my bike to them and with a pocket full of quarters, bought every one. When I got home, i couldnt wait to look at them and in the darkness of my bedroom, saw my...

A teenie niece s first shemale experience

I heard my phone buzz one afternoon, just as my hard cock was sliding effortlessly into Lela’s smooth arse tunnel. “I’d better just check that” I said to my panting shemale lover, given that I was supposed to be working from home.It was a text from Jess. It simply read, “I’m bored and fingering my hairy cunt. How about you come over and fill it with something bigger?” Jess knew I was at home, and she knew I wouldn’t be doing any work! However, she was about to be surprised with a threesome. “We...

My first time with a shemale

OK, I was wasting my time on shamble videos and pictures on the web for about 8 years! When I first entered a porn site I almost got sick, but soon I got really curious about it but didn't dare to click that button; couldn't explain why I wanted it so much though. Eventually I pressed it. I started with shambles alone, then shambles fucking girls, then shambles fucking shemales and end up with shemales fucking guys... I started loving it, watching it on a daily basis. My fetish for thong...

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