Shemale Stories

If you like the idea of a girl going at it with a ladyboy and follow the ladyboy stories section of our blog for some time, you should remember the story about Thai ladyboy Nan that our reader Julia wrote. Well, this is her second report and I hope you enjoy it as much as the first one.

This time I actually had a reason to be in Bangkok as my company needed me to go there and meet a client. However that remained my secondary objective as I had to catch up with ladyboy Nan. Once I had checked in at my hotel I called several times and finally tracked her down at her apartment, I guess it was early afternoon. She agreed to meet me at my hotel in an hour or so.

I was like a virgin about to experience my first time as paced, thought about things and smoked too many ciggies until I got her call that she was down in the lobby. There was a problem and she couldn’t access the room floors. I tarted myself up and raced to the elevators and down to the lobby. I found Nan sitting at the bar waiting for me and what a site she was. Her makeup impeccable and sitting there in a short red skirt, thigh length red PVC boots and a skimpy little halter top. She was nursing a beer and smoking at her bar stool. Actually she was smoking more more ways than one. I nearly lost my breath just looking at her there.

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Not only the readers of our ladyboy blog love jerking off to our shemale sex stories, some of them are also willing to share. A guy named Steve was always curious about how a shemale cock would taste in his mouth and he just had to let it all out. TFS, Steve.

I have always wanted to know what it is like to suck a beautiful shemale cock and would have a fantasy of deep french kissing a sexy women and would slowly kiss my way down her breasts down to her tummy using my tongue over every inch of her body. Then i would slowly pull down her panties to see that beautiful pussy just to be surprised to find a very succulent looking cock that i could put in my mouth! I would be like oh you have a cock and she would say you don’t mind and i would then tell her i always wanted to suck a shemale cock and asked her to show me how.

Rosalinda was her name and she slowly put her shemale cock down my throat and worked it in and out of my very wet mouth until i wrapped my lips around that nice piece of meat and took over her thrusting and started sucking it on my own. She started to moan and i could tell she was getting ready to shoot her load in my mouth which made me even hornier than i already was. I wanted her shemale cum to shoot down my throat when she asked if i wanted to do anything else and i stopped sucking her cock just to jump up and take my clothes off so we could 69 each other.

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I know, I know, many of you have been wondering why there were no updates at Trans Ladyboy for more than a month. The reason is simple, it’s all that frigging global financial crisis to blame and Your most humble servant had some really important things to take care of (unfortunately, to the detriment of shemale porn).

Anyway, life goes on and while I was away many interesting things happened at our forum. I’m going to present you a new work of our forum member Randolph whose hot tranny stories have been already published here several times. Today’s story is about a married guy whose wife found his collection of shemale porn and they had to split up. This was only for the better, otherwise Charlie wouldn’t have met a tgirl of his dreams, Khloe Hart (no less) and his magical transformation wouldn’t have taken place. This is a purely fictional fantasy with a very promising beginning and a surprise ending. Enjoy reading.

Charlie was an investment broker living the good life in a Hollywood hills mansion. He wisely sold most of his investments’ just before the crash. His assets now consisted of the mansion, a Murano, a Tesla, lots of cash and some good stocks. They (he and his wife, Darla) had a gardener and a maid, Kim. It was a bright sunny Saturday morning when Charlie went down stairs for breakfast. His trophy wife, Darla, was sitting there waiting for him. He kissed her good morning and she looked at him with a solid cold stare. Is something wrong, he said? She looked at him with contempt for a few moments and then said. “I checked your computer for some news and found your collection of shemale porn. You son of a bitch are you some kind of pervert? Charlie was at first speechless, he thought he had secured his shemale porn collection. Well now you know, he said. I also know some things about you, my dear. I have noticed how friendly you are to Kim, how you are often touching her. Late the other night, I noticed you were not in bed so I went down stairs to see what you were doing. As I passed Kim’s room I heard soft moans. I carefully opened the door slightly and peeked in; you and Kim were both naked. Kim was on her back and you were eagerly licking her pussey. So if I am a perverted son of a bitch, what are you? If you prefer being a lesbian so be it. Shall we split up? That’s fine with me she said. I want the house, the Murano, plenty of cash and of course Kim. Ok you can have it; I will take the Tesla, the stock and half of the cash. There are other good things in the world besides pussey, he said, with a slight grin. They agreed, signed divorce papers and Charlie prepared to leave.

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I’m very proud to publish this mysterious and very erotic and romantic story by our forum member, SMC. This story is indeed very unusual, it combines romance and sex and I’m absolutely sure you’re going to like it as much as I did.

It is one of those days of drudgery, tied to the computer, working for hours, trying to write. It is not going well. I am too distracted. Perhaps things will go better if I work somewhere else? Sometimes, moving from my office and the desktop computer to the living room and the laptop helps. I decide to give it a try.

Nothing doing. I am just as distracted. Only now, away from my office upstairs, with all the reminders of work, I find it even easier to drift away from my work tasks, and I look for anything to do but work. After drifting around on the web from news site to social networking to whatever, I check my email. There is a message from an address I have never seen before: her@want-me.net. The subject line reads: “I am not spam.”

That catches my attention. Of course it is spam, I surmise, but I must admit to being impressed by the cleverness of the subject line, so instead of instantly relegating the message to the trash, I decide to look. The message content is simple: “It’s me. Click here.”

I put the cursor over the clickable line to see what will show up at the bottom of my screen, fully expecting some long string of unintelligible letters and numbers comprising a URL somewhere in one of the spam or phishing capitols of Africa or Eastern Europe. But again, I am surprised. It reads: “This is real.”

How did the spammer do that? I wonder. Now I am more than curious, and against my better judgment I click, fully expecting it to be the last time I will get any use out of my laptop computer.

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For those of You who ejoyed reading the 1-st part of the story about Leona, i’m finally publishing the final part. Thanks again Cham for writing these awesome tranny stories.

I would have cried out with ecstasy but Hilda’s cock rammed down my throat and she told me to suck her. I sucked and she was tasty. But she soon pulled out and I saw Jamie’s cock above my face. Hilda’s cock was pretty much like Leona’s, both had smooth cocks that stood to the right and had large ball sacks. Jamie’s was different. Of course, it was black, smaller than Leona’s or Hilda’s, and had an extreme curve, almost a kink, to the left. Coupled with her angelic smile and voice, I think I was in love and eagerly took her into my mouth.

They took their turns with me, “A whore for shemales,” as Hilda put it. Veronika’s cock was a fat and uncut black beauty and I looked forward to taking it in my ass. Mandy was tall, slim and fair, and her cock resembled her except that it looked small until roused and then curved straight up and back leaving the head touching her body. I enjoyed her cock as well. While one would stuff her cock into my mouth the others would toy with my cock and balls. Soon they raised my legs and began to play with my ass as well. I had died and gone to heaven.

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Our dear forum member Cham wrote a sequel for his erotic story about Leona, his shemale lover and i’m extremely proud to be the first one to publish it here at Trans Ladyboy for all our horny readers. Mad props to Cham for his outstanding work!

Lust and Love with Leona
By Cham
This is a work of fiction.

The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn’t pull in a bar. But I found that I could not stop thinking of Leona and that I stayed at home fretting and looking at shemales and ladyboys on the internet. I had Leona’s number but was terrified of calling her in case she was working and I disturbed her.

I just wanted her to be back and worried that she may not want to see me again. My cock was perpetually hard and leaking pre-cum. Luckily I run my own business and have an honest manager. I put him in charge of things and took the week off. After much introspection, I had the brilliant idea of visiting the bar where I had first met Leona. So one evening I got dressed and ready to go out, but as I was about to leave, a niggling thought that had been at the back of my head came up right in front of me. If it wasn’t Leona, it would not be the same. It had to be Leona, I wanted to re-create my first time with her.

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Sifting through the comments that readers leave at Trans Ladyboy, i have found two really hot shemale fantasies that I would like to devote separate space to. They are both written by two horny guys, wyocock and Eddie, who dream about being with shemales all days long (the only difference is that Eddie have already found her lady to spend naked time together).

Our reader wyocock writes…
I would just love to have a sexy shemale laying on my bed. with her head it the end of the bed. and she has her hand wrapped around her hard cock. she’s slowly stroking her lubed cock. and with her other hand, she has it around my ass as she’s pushing my hard cock in her waiting mouth. I’m holding her sexy tits with my hands. and she starts to stroke her hard cock faster and faster with her hand while I’m fucking her throat. I’m driving my throbbing hard cock deeper and deeper down her hungery throat untill my tight hard balls are ready to explode.

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Yargh! Today, my horny readers, i want to tell you a sex story about a rough sailor that accidentally got turned into a shecock lover by two sexy Filipina ladyboys. All this time he thought he was screwing two beautiful GGs when he suddenly felt something stretching his virgin anus. Enjoy this lovely story by our reader who just calls himself Sailor.

I was 21 and was walking to my girlfriends place around 100am when I walk past 2 sexy filipinas walking the same way. They started talking to me and when we got to their palce they ask me to come in for a beer and in I went, thinking they were girls the whole time. After a beer they both started sucking my cock and one got down and the other lifted her dress and aim my cock in her ass, wow it was heaven, I blew my load in her ass and the other lick my cum out.

We drank a beer again and when I was hard the other got down on all fours and the first one aim my cock in her ass, they both said it was their time of the month. The first one I fuck stared licking my asshole out and it was heaven and then I felt something go up my ass while I was fucking the other girl. That when It hit me that they both were ladyboys and wow it was great.

I fuck them both and they both fuck me, it was 5:00am before I got to my girlfriends place and my asshole was filled and licked so much that nite, I was so scared being in the navy that I never told any one till now. I married my girlfriend and never been with a ladyboy since, well I did suck one off in Singapaore.

Any ladyboys want a good blow job here in eastbay of San Francisco? I love sexy women with cocks to suck and to pound my ass. Forget pussy, ladyboys are the best.

Our reader, Matt J, have recently visited Pattaya and, as you can see from his story, it was a very fruitful visit! He had a petite ladyboy Lo spend a night with him during which he came countless times, and now he says he’ll be coming back for more. Who wouldn’t? 😉

I recently indulged a few of my fantasies in Pattaya with a very sexy Katoey who like me enjoys latex and smoking. Lo is a petite 5ft 5in ladyboy who came onto me in a bar looking for company and to make a buck or two. In the end it worked out very well for me and as a first timer I enjoyed myself.

As she emerged from the hotel bathroom wearing black PVC thigh boots and matching basque and wearing these elbow length gloves smoking this long white ciggie I was a gonna. She dropped my bathrobe from my shoulders and kissed me with passion for several minutes before placing my erection between her PVC thighs and boot wanked me for all of 1 minute before I lost the lot.

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• Smoking ladyboy in latex indulges my fantasies

Today I’m very pleased to publish a story by our reader Tommy. He’s seen lots of talk here about having sex with t-girls and shemales and not much action. Now he’s happy to say he’s taken the plunge (!) with a tranny and it was a very pleasurable experience which he would like to share in the hope that it pushes some of you guys to go for it!

I used a site in the uk especially for trannys and admirers and found a girl in my area who agreed to meet me at her apartment for a bit of fun. When i arrived she opened the door wearing stockings, corset, a lace night gown and large heels. She was really tall and quite intimidating and i must say it really turned me on!

She invited me in and as i entered i saw the bedroom lit with a red light and a huge dildo stuck on the door and thought i’m going to be in my own porno! We talked for a little getting to know each other and watching a shemale dvd on tv and after a while she got impaitent and simply said ‘so do you want a blow job or not?’ to which i replied ‘of course!’

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