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Old 06-06-2009, 11:37 PM   #1
Cornoggin
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Crossdresser tricking a straight guy

Are there any stories like this?
Like where a crossdresser goes to a club dressed as a girl and starts dancing with a straight guy, or some other situation where a straight guy will go pretty far with a crossdresser before realizing they're a guy?
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Old 06-06-2009, 11:43 PM   #2
Cornoggin
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If somebody wants to try writing this, my request would be college-age, that's about it.
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Old 06-07-2009, 07:51 AM   #3
sirhugs
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not something I'd likely write, and I've got lots ahead of it, but I did a simple story search for you. Some of these should do the "trick"

http://search.literotica.com/search....ry&q=trick&cid[]=48&db=text&date_from=&date_to=newer&sort=relevancy&sort_order=desc&author=
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Old 06-10-2009, 10:15 AM   #4
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I am not into gay stories, but when I think about it ...

Imagine, the crossdresser offers this guy a blowjob. He accepts and then, the crossdresser also wants oral sex. The guy likes pussy licking, so it's no problem - until he sees, that there is no pussy, but a dick ... now the question would be: would he run away screaming ? Or maybe, after some hesitating, he would return the favour. Maybe he is bi-curious.

By the way, I once saw two similar stories in a porn magazine, but with different endings: A guy is in a disco, flirting with a girl. She is really hot, with big boobs, blond hair, long legs. They both become horny, so they want to fuck. There is a park near , so they leave the disco. In the park, it is very dark, so they have sex on a secluded bench. However the girl tells him, that she prefers anal sex, so the guy fucks her up the butt. The sex is really great, but when the guy wants to finger her pussy, he is surprised - she has a dick. She was a guy who always wanted to be a girl, so she got silicone boobs. And soon, the penis will also be removed, so she will be a perfect girl.
As I said, one story ended with the guy running away, but the other one ended with the guy starting a relationship with the girl.
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Old 06-10-2009, 01:39 PM   #5
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I think this would be interesting in a historical setting.

Two I've read:
- Gay man at a masquerade ball is baffled to feel attracted to a woman, until he figure's out it's a crossdresser. Then he's amused at the chance to make out in front of everybody for once instead of having to hide his sexuality. The crossdresser escapes after some making out because he doesn't realize the man knew he wasn't a woman. So now the man has to figure out who the crossdresser is when not in costume if he wants to get laid. Meanwhile others are gossiping and also trying to figure out who was the woman the man was making out with...

- Gay 18 year old is an orphan and half-starving - he puts on a dress and goes to where a band of mercenaries has just camped near his hometown and offers to sell blowjobs so he can get some money. A mercenary soldier is going to hire the 'woman's services, but goes to grope 'her' chest and discovers the truth. The soldier is loudly furious about the deception/humiliation, and going to beat the crap out of the crossdresser, but the captain intervenes, repeating a previous rule that the troop members are not allowed to harm any civilians because the troop needs to maintain good relations with this town to buy supplies and get non-fighting jobs here like being hired to help build a big wall. The soldier demands his money back, and names an amount twice what he actually just paid the crossdresser. The crossdresser turns over the actual fee and has no more - the soldier says he's hiding it and wants to rip his dress off as part of a strip search. The captain says he'll do it and takes the crossdresser into his tent. The captain knows there isn't any more money so, once in his tent, he tells the crossdresser to stay put or else and gets the remainder out of his own coin purse. The captain goes out pays the soldier, but warns him to shut the hell up and not bother any civillians including the crossdresser. Then captain goes back in the tent to talk to the upset and scared crossdresser, who the captain thinks is quite attractive. The captain asks why the young man is pretending to be a woman and trying to sell his services. After ascertaining that the young man does actually like giving blowjobs the captain hires him to do so, for a much more generous amount of money. Later they fuck too, which the young man hasn't done before.
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Old 06-10-2009, 01:56 PM   #6
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Actually, as the two previous posters say, these stories are fairly common.

The best one I’ve read in this genre was about a macho guy who was out one night tossing back a few beers with his buddies. In walks this gorgeous woman who has curves in all the right places. She sits down at a table nearby and the guy and his buddies are ogling her. One of the buddies then bets the guy $20 that he can’t pick her up. The guy takes the bet, downs his beer in one gulp and heads over to the “woman.”

He lays his macho charm on her and he feeds her all his best lines while rubbing his hand on her thigh and trying to get a peek down her blouse. The woman has a deep voice but this turns the guy on because he’s always had a thing for Kathleen Turner. He invites her to step outside with him for a smoke and she quickly accepts.

Once outside, the dude lights up and then starts being more direct. He tells her how much he likes her ass and her tits and how he hasn’t been laid this week and he’s getting worried about the massive sperm build up in his balls. The woman says, “I can help you with that” and drops to her knees and unzips his fly. She pulls out his massive dong and begins sucking for all she’s worth. When the guy finishes his smoke, he pulls her up and says, “That’s some good head. Now turn around and bend over so I can have a crack at your pussy.” The woman obliges, but she tells the guy that she is on her period so he’ll have to give it to her up the ass. The guy says, “Even better. I haven’t butt fucked anyone in a month.”

He pushes her drawers to the side and starts to work his rock hard prick into her tight backside. Once he’s all the way in, he starts pounding her ass like there’s no tomorrow. Right before he’s ready to cum, she asks if he would give her a “reacharound.” The guy assumes at first that his girl wants for him to finger her clit so she can get off too. But when he realizes that she has a schlong, he pulls out and immediately goes limp as a noddle.

“That’s some fucked up shit,” he says to her as he zips back up. “I should have known you were a dude when I noticed your moustache.” Anyway, the story ends with him going home with a serious case of blue balls since he didn’t get a nut.
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Old 03-18-2010, 09:22 PM   #7
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Quote:
Originally Posted by Cornoggin View Post
Are there any stories like this?
Like where a crossdresser goes to a club dressed as a girl and starts dancing with a straight guy, or some other situation where a straight guy will go pretty far with a crossdresser before realizing they're a guy?
Did you ever get your request?
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Old 03-19-2010, 10:07 PM   #8
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Just scroll through the Transsexuals and Crossdressers section. You will find enough there to keep you busy for a long time. Some are extremely good -- if you enjoy this genre.
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Old 03-20-2010, 01:25 AM   #9
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In real life, I've heard of people in denial who would purposefully let themselves be tricked. Maybe you can try something like this and write about the emotion struggle within.

This would make a good story thats also about emotions and personal demons.
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Old 03-20-2010, 02:40 AM   #10
Carnevil9
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I have a story much like that, it's called "His Better Half." See my sig. It was actually suggested by a poster on this forum, and I wrote it up based on his ideas. I think it kind of works......Carney
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Old 03-21-2010, 07:43 AM   #11
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A bus driver is on his last run of the night. It's dead quiet and the bus is empty. He stops at a bus stop and a young nun gets on.
"Hello, Sister," says the bus driver. "How are you tonight?"
"Not so bad, except that I'm dying of cancer."
"Oh, that's terrible. Sorry to hear that."
"It's fine," says the nun. "If God wants me early, He must have His reasons."
"I guess that's one way of looking at it."
"I see that you have a crucifix around your neck. Are you a good Catholic?"
"Yes, I am, Sister."
"I do, however, have one regret," says the nun. "I was raised in a convent since I was a very young girl, and I've never known what it's like to be with a man."
The bus driver, like all bus drivers, is a horny old dog, so he offers to help out in any way he can. Without much hesitation, the nun thanks him, and takes him up on his offer.
"I do, however, have two conditions," says the nun. "First, you must be a single man. Marriage is very important in the Catholic church and I would not wish to play any part in a man breaking the sacred vows he made in the house of God."
"I am not married, Sister."
"That's good. Secondly, I must still technically be a virgin when I finally meet St Peter. That means you may only do it in my bottom and not in my other place."
The bus driver's up for some anal, so he agrees. Ten minutes later.the bus is parked up in a deserted side street and the nun is on the back set on her hands and knees, while the bus driver fucks her ass. When it's finally over, the bus driver suddenly feels guilty (he is Catholic, after all).
"I'm sorry, Sister, but I have a confession to make. I lied when I said I wasn't married. I have a wife and three fine sons at home."
"That's okay," says the nun. "I lied too. My name is Kevin and I'm just headed for a fancy dress party."


Given the name of this thread, the outcome was obvious, but I thought I'd share it with you anyway. Of course, when telling the joke, it's always best to camp up the last line a bit.
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Old 03-21-2010, 05:21 PM   #12
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Lola of the Kinks song "Lola" was a woman, not a cross dressing man.
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Old 03-22-2010, 04:10 PM   #13
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Tricked by crossdreser

Quote:
Originally Posted by Cornoggin View Post
Are there any stories like this?
Like where a crossdresser goes to a club dressed as a girl and starts dancing with a straight guy, or some other situation where a straight guy will go pretty far with a crossdresser before realizing they're a guy?
This is an old, old, old story. I have heard it told many times by straight guys. It usually ends with, "...and when I put my hand between her legs, I felt a cock bigger than mine." They never go on to tell what happened next.

I think there is a point of no return in a situation like this. If a cross dresser tricked me, I would go all the way with it.

I just posted a story similar to this theme. The difference is that the guy is bi-sexual and the cross dresser at a certain point confesses she's a man.
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Old 03-25-2010, 03:11 PM   #14
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Isn't that Lola?

Quote:
Originally Posted by squarejohn View Post
This is an old, old, old story. I have heard it told many times by straight guys. It usually ends with, "...and when I put my hand between her legs, I felt a cock bigger than mine." They never go on to tell what happened next.

I think there is a point of no return in a situation like this. If a cross dresser tricked me, I would go all the way with it.

I just posted a story similar to this theme. The difference is that the guy is bi-sexual and the cross dresser at a certain point confesses she's a man.
At the risk of sounding obvious. This scenario is ultimately similar to the glory hole stories, too, where a non-gay guy stumbles upon a men's room so equipped and doesn't think twice about sticking his unit thru one, but then faces a "hard" decision when faced with a reciprocal boner, close by his face.
The gent typically overcomes his initial reluctance, kisses, licks and then mouths the proferred member, and then enjoys the hell out of giving his first hummer.
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