True story about a ladyboy first timer fucking her customer’s ass

Ladyboy first timer from Obsessions bar in Nana Plaza violates the ass of her very first customer in the rawest way! Hotttt story!

Those of You that dream about having a beautiful Asian ladyboy fuck your ass will certainly love this naughty story posted by our reader Tommy where he got his asshole violated by a cute ladyboy. Did I mention that she was a first timer and Tommy was her first customer? 😉

Hi, me again with another shemale episode to share with you. This time I was hanging out with friends at Obsessions in Nana Plaza – not a place to go if you don’t want hot transexual action! A gorgeous tall ladyboy was dancing on the stage and I couldn’t take my eyes off any inch of her. After the dance was over she came over and we had a drink and kissed and fondled each other. She didn’t have great tits – OK but not knockout, but a lovely face and great skin and nice figure.

But let’s cut to the chase – I could tell there was a very nice solid cock coming to life down under in her panties. In no time we realized things were heading for bed so I paid the bar fine. She was really very happy that I’d picked her and only later she confided that she’d just started work there a few days ago and I was her first real customer. I can’t vouch for that but as I found out later she certainly wasn’t that experienced. We jumped in a tuktuk and went round to my apartment. I poured us drinks while she went into the bathroom to do whatever ladyboys do to get ready (I must find out some time!).

She came out topless – very nice body – but still wearing her short jeans skirt which I absolutely love to see on a Tgirl. She went up to the mirror above the desk and leaned over invitingly – in no time I was there rubbing my bulging cock against her ass and caressing her tits. Next stop – the bed and she got on all fours. After gazing in her lovely pantie bulge for a while (and you know how much I love that if you read my other adventures) I peeled her panties down and went to town with my tongue on her sweet asshole. In no time she was starting to breathe hard and she flipped over demanding me to suck her cock. In no time at all she was fully hard and my god it was a good 7 incher at least and it was flawless. It was too good to waste so I dropped my pants and bent over to get a good fucking.

She put on a condom. Well, here’s where her inexperience came into play. Instead of loosening up my ass with her fingers or tongue, or lubing my anus or just gently nudging my bud with the tip of her cock – she just slammed the whole nine yards deep into my poor little asshole! I couldn’t help but cry out and it felt like I was split in two and had to beg her to pull out for a while. When my nerve endings had settled down a bit and some lube had gone on we got back into business. Much better. Her long cock seemed to fill every inch of my ass and I could feel the head of her cock every inch of the way as she fucked me.

Awesome! But I do like to be on top sometimes. I got her to sit with her back to the wall, legs spread and cock standing to attention at 45 degrees. I sat over her legs and moved myself forward with my hands behind me on the bed to support myself – and guess what – her cock slipped perfectly into my eager loosened ass.

We fucked like that for ages – a position I’d never done or seen before but I recommend it. After a while she came in big waves and I could feel her cock pulsing against the wall of my anus as she did – a first for me! After a few minutes her cock got soft and slipped out of my ass – but she was shocked that she couldn’t see the condom anywhere. Then we realised it was still hanging out of my ass! It was dripping cum which was a very erotic sight and in no time I was hard and ready to return the favour. After fucking her for just a few minutes I was ready to deliver so pulled off the condom and sprayed my load over her mouth and face. Now, that’s something I like a ladyboy to do to me – let me tell you about that in my next letter.

7 thoughts on “True story about a ladyboy first timer fucking her customer’s ass”

  1. Hello my name is Merle Dean Shamblin and I would like to be your new friend. I sure could use somebody to chat with. I am a 47 year old long haul truck driver who currently lives in Duncan Oklahoma. Dec 8th 1960 I was born in Fairview Oklahoma. Moved to Caddo and Washita counties where I attended school at Colony Hydro and Weatherford. My parents Malvin and Wanda Shamblin were cotton and peanut farmers. Dad died in 99 from lung cancer. Graduated from SWOSU with a business degree. My two sisters are LaDonna Hubert and Malva Burrahm. Dennis is my brother. I have been a truck driver for 14 years and have driven 2 million paid miles. I have received many safe driving awards over the years. I am single and have never been married. I have a wide range of interests and am pretty much an open book. Currently I drive a 2006 Freightliner for a major carrier. I dont go to Canada very often. I dont have a dedicated route so I run the entire lower 48. I enjoy reading cinema music sports travel etc. I am gay and versatile.

    1. Howdy Merle. I am Allen from Texas, but live in Thailand now. I am bi. I have lived in OK, NM, & Col. I have traveled all over the world. I am here, becasue of the sex attitude of Land of Smiles. You should come over for a vacation, you will go wild over the ladyboys here. They are much better looking in person. I am lonely tho, and would love to talk to you at lenght about anything.

  2. thnkzz for sharin dis me radin it makes me feel happy i cnt belvie am not da only one who likes shemales..p.s. lucky man i wish dat happenz 2 me sumtime

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