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Male Fraud: The True Story of a Guy Who Had Sex With a Tranny and Didn’t Know It.

ladyboy 300x199 Male Fraud:  The True Story of a Guy Who Had Sex With a Tranny and Didnt Know It.

Guest Blogger Kelly Kreth on the perils of getting too drunk for your own good.

At dinner with a friend this week, I heard the most darkly funny sex-related story. My friend–we’ll call her Ellen–took a work colleague out for drinks to thank him for doing a good job on a project she hired him to do. He was a consultant, strapping, amazingly gorgeous and young. She said what made him even hotter was that he had two beautiful kids and a pretty wife who he seemed so into.

At lunch, the first thing he ordered was a vodka straight. Ellen thought it was odd to kick back that much at noon, but went with it. After pounding a few more back she realized that he was excited to have a day to be a guy where he could throw caution to the wind in the City and drink and relax. No problems with that. It was a Friday after all and he wasn’t expected back in NJ until at least 10pm.

After a liquid lunch, Ellen and the consultant, along with a few other co-workers, met up with a bunch of other friends for happy hour. At happy hour Ellen’s closest and very gay friend, Ed, came by the bar. He and Rory had known each other also for some time because they had also done some projects together. Ed brought Simone (otherwise known as the pre-op tranny, formerly known as Simon.)

Simone was from Thailand and working as a woman in fashion. Ellen said she had met “her” several times before and that she looked enough like a girl because she was small and dainty, but that at the end of the day there was a bit of shadow on her face and because she was pre-op she still had no real tits (padded bra), a bit of an Adam’s Apple and a cock.

By this time Rory was rip-roaring drunk and it was well past 10pm. It was clear that this was his day to blow off steam and act out. There was no way he could get on a bus to NJ, so Ed, Ellen and Simone headed back with him to Ed’s place so Rory could sober up and make the last bus out of the City.

While Ellen and Ed sat on the couch, Simone and Rory went on the terrace to smoke  make out! Ellen went to ask Rory something and happened upon them in a full liplock and embrace. She ran back to tell Ed. Both rather tipsy themselves, that at this point, they didn’t know whether to laugh or die of horror. Rory was married, with kids and was cheating on his lovely wife in front of them….with a chick with a dick.

Surely he didn’t know, reasoned Ellen, not that that makes up for his bad behavior, but something had to be done. Ellen asked Ed to delicately extract Rory from the terrace and once done, Ellen told Rory he was way too drunk to go to NJ and that she’d take him in a cab to her house so he could call his wife and sleep on Ellen’s couch. Rory had in the course of his wild night lost not only his keys and jacket but cell phone.

Good going Rory!

Rory wasn’t having it. He could barely stand but said, “Nope, I’m staying here, at Ed’s, with SIMONE!” Ellen, begged him to go, but couldn’t get him alone to explain that it wasn’t merely that she was frowning upon his extramarital activities, but that he was also having an intragender encounter he apparently wasn’t aware of.

Rory is a big tough guy and Ellen was scared when the embraces got too raunchy, Rory would figure out Simone was excited, but not in a way that he was hoping for.

Before Ellen could say anything else, Simone and Rory locked themselves in Ed’s bathroom. Ed, being a gay man that thinks every man is actually gay, found it all rather hysterical and had another drink. Ellen was beside herself but took a cab home telling Ed when the shit inevitably hit the fan, to call her and she’d send a car for Rory.

About 30 minutes later she got a slurred call from Rory saying he was heading to hers to sleep it off. She was beside herself wondering if, and how, he found out that Simone had a cock.

While Rory was in a cab headed to her place she called Ed who said that apparently Simome told him that she and Rory had been in the bathroom kissing and Rory said, “Get a condom” and of course, Simone had one, but it broke so they couldn’t fuck–how were they going to without him finding out she was a dude, I have no idea–so instead Simone blew Rory.

Rory was none the wiser that he had just kissed his first man and happily got to Ellen’s and fell into a fast sleep on her couch. She left him $100 bucks to take a cab to NJ in the morning saying that she didn’t want to be awakened.

When she finally tiptoed out of her room that afternoon, Rory was gone. She has no idea how he explained his not coming home all night to his wife or how he lost his cell, keys and coat, but more so she is in a dilemma whether she should tell him about Simone’s secret.

I like this story for a variety of reasons. I love that in NYC you could go out and try to cheat on your wife and unbeknownst to you end up having much more than a simple affair. I like how karma is a bitch with a dick and this should be a lesson to all taken men that cheating on their wives could be more traumatic than they ever imagined. Most of all, I love how Simone said she claims she laid on the futon with Rory and disrobed except for panties and he didn’t realize she was a dude. The best part is that Simone didn’t think to ever mention it.

I am DYING for Ellen to get the courage up to fill Rory in on the bits about Simone’s bits.

I can only hope she does soon.

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5 Responses to “Male Fraud: The True Story of a Guy Who Had Sex With a Tranny and Didn’t Know It.”


  1. Rory knew what he was doing.

  2. Reid

    Kelly, love your stories! I wonder how often this happens – where a guy hooks up with a tranny, and doesn’t realize it until it’s too late! Fun times in the big city..

  3. Lee

    You do know that referring to a trans person a “tranny” is akin to calling a gay man a faggot? Isn’t this the kind of othering – she’s really a dude story that was old in the early 90′s?

    Oh – there’s “tranny’s” out there! And – they might have sex!

    Be careful girls!

  4. ra

    many guys get fooled in the red light districts in Thailand by these ladyboys. Too drunk to see anything as often these ladyboys are better looking than females. Other guys know who they are dealing with but want to experience something that they would never dare trying in their country.


  5. Wow! What a site you have here. You have a real knack for making a tranny blog pleasing to the eyes and feeds fantasies very well. Some sites look like train wrecks, but not yours – it

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