Shemale Stories

This sweet ladyboy sex story was shared with us by Julie and it’s about a girl who wanter to try lesbian sex but ended up being with a ladyboy. As you will see this only upset her for a moment, and now she regularly visits Thailand to meed her new ladyboy friend Nan.

Coming off a very nasty divorce in Singapore I took a weeks hols and went to Thailand. So many elephants and cultural shows were enough. The last night I wandered through the bars in an area of Bangkok. After a Barcadi and coke I am digging through my handbag looking for my cigerette lighter when this stunning blonde thai girl offers me a light. Her English was I suppose halting to say the least but she offers to show me around the nightlife spots. So we walk off in search of fun, after a few bars and too many Bacardis I am starting to like this girl and even thinking of just what Lesbian sex would be like.

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Another little lovely reader submitted story. Thanks for sharing, Frank Carson 😉

A few years back I was in Pattaya on hols from Aussie. I met this chick, well I thought she was a chick anyway. Too many beers maybe at the time! When we got back to my hotel we sat on the balcony having a brandy before what I thought was going to be a night of fantastic sex. This chick takes out a packet of Menthols and asks for a light, no worries she smokes there and we natter over shit various. After a period of time her hand moves over to my groin and old fella starts to get excited. In no time she has him out of the jeans and he is getting a very slow but pleasurable hand job.

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In this little story by our reader Jim, he met a beautiful nurse in a dentist’s office and asked her out for a drink. Little did he know that this special lady had a surprise for him 😉

I am employed in maintenance of medical/dental equipment in the greater LA area. Last year I checked in at this Culver city Dentists office to do some work. I knocked at the door and heard this voice telling me to come on in. I opened the door and saw this blond honey out on a balcony having a smoke. After introductions I went about my work as she chatted to me from the balcony over her coffee and cigarette. I asked if she was the dentist as she was setting a poor example regarding the health issues and smoking etc. I have to say she was cute, damn cute. She explained to me she was the hygiene nurse and did the cleaning/scaling on patients teeth, she was also the assistant to the main man.

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Here’s another one of those “first time with a shemale” stories posted by our reader. Thanks for sharing, Randolph, and if all of this is true you must be a very lucky guy 😉

Randolph sat at his computer working on his journal. He found it difficult to put into words the experience with Misha. Her appearance in the femdom outfit surprised him and also made him feel uneasy. He had never experienced femdom before but after reading the Playboy article he realized that Misha’s performance was a very mild version of femdom. Pain and suffering and extreme humiliation were not things he wanted to participate in and he was glad it didn’t happen. However, the sex fantasy role playing was fantastic. He had not realized how much effect imagination combined with a sexy provocative image can have on desire for sexual experience. He realized that the femdom role made him focus on oral sex, during the time Misha was on top of him, the thought of intercourse with her did not occur to him, all he wanted to do was lick her sex. The combination of her aggressiveness and the intense desirability of her swollen wet sex overwhelmed his senses and his cock exploded with cum without being directly involved, his mind took care of it.

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It’s not always that the first experience that guys have with shemales is a bliss and a dream come true, there can be unlucky exceptions too. Our reader, who calls himself John Doe, was hooked on shemale porn for a long time and finally decided to turn his fantasies into reality. What a big disappointment it was for him.

I was stationed in the middle east, and everything was ok, until a few months later when we got the internet in our rooms. That was the best thing that ever happened. Being so horny all the time, and being in such a shithole place, I started to experiment with all sorts of different porn genres. Finally I was exposed to shemale porn, and I got hooked like a fish on a fishing hook.

I consider myself straight, and have always been sexually attracted to genetic females, and have always had sex with genetic females only…UNTIL

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Our reader, Pete, posted this comment at our blog and i was deeply touched by it. It goes to show that even if you consider yourself to be an old man whose sex life is in the past, you can still date a transsexual lover and be happy again.

I am a 65 year old black man. I have just recently been involved in an affair with a 34 year old Transsexual woman. We have been for sometime conversing over the internet, we got to meet for the first time face to face on my visiting the U.S. as I live in a Foreign Country.

At first I was not too sure about her being a TS, but reading through her letters it became very clear that she was.

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Our forum member, Dutchboi, had this fantasy of being dominated, sissified and humiliated by nine Asian ladyboys, with Mint and Nancy being two of them. For some of You this story may sound too cruel, others will find it really hot.

My fantasy is to be at a ladyboy’s apartment and fall alseep after I fucked her. Then I wake up because I am turned around and I find the ladyboy sitting on my back and attempting to lock my second hand in the handcuffs. I struggle but she is pretty strong so she succeeds. She then lets me know I won’t be going anywhere for a long time. She then puts a leather collar around my neck and locks a chain to it, the other end of the chain she locks around an old>

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• Your wildest ladyboy or shemale fanatsy

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.

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Another lovely short shemale story from our forum member, this time from a guy who calls himself “I Fucked A Shemale”

I was at my best friends house a couple of years ago. I was maybe 18 i believe. His step mom was there. Well his new step mom that his dad just married like a few days before. Well I had to go to the bathroom, so i went to the bathroom. I had walked on in and then i heard the shower on. It was his step-mom. She told me dont worry to come on in. So i came on in sorta not wanting to. Only because i was a virgin either way and i was still insecure about my self. So i just decided to sit down and pee. I was there and my eyes started to wander. I then started to look behind the curtain. Then I saw her standing there. She was wet and i could see her nice ass. So I got hard and started beating off. Then all the sudden she turned around and saw me there beating off.

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Our new forum member who calls himsels BigBell609 has recently visited Moscow and obviously had some fun time with Russian shemale escorts. Now he wants to share the juicy details of his fun time in Moscow. I know, you’re going to like that 😉

The first day, I was with my Russian friend, who introduced to me the Russian shemale escort. Since I know he is a big fan of shemales, so I wasn’t shy of asking him about shemale escorts in Russia. He called in a shemale escort for me rightaway. I was staying in a hotel in downtown Moscow. Since my company paid for the expenses, I was staying at a quite nice 5-star hotel.

Soon (about forty minutes later), someone was knocking on the door. Then came in this astonishingly good looking lady. My friend talked to her briefly in Russian. Then he turned to me asked me to give her $$$ (apparently she did not ask for Russian money), which I happily complied. My friend waved to me goodbye and he went out of the door. To tell you the truth, I was extremely nervous. I have been to other shemale escorts before in the States, and not being this nervous. In fact, if some of you have read my other post, you know I had a shemale girlfriend a few years ago. Well, maybe because I was in a foreign country.

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