Humourous, Rather Desperate Cross-Dressing Story

Cadere

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Oct 23, 2011
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It's a thought that has been drifting around my head for a bit...

It's pretty much a playful poke to the idea of cross-dressing, but this is just an idea that I will--hopefully--act upon and form into an actual story.

~

So it's a group of friends--Greg, Michael, Muhammad, Veora, and June (3 male, 2 female)--who hang out all the time. Nice, blended group with a mix of interesting personalities, around their early twenties. The only people of the group who have had sexual relations are the two key characters, Greg and June. Greg likes June very much and hopes to have a deeper relationship with her; June prefers to keep it casual.

The two have been dating for quite some time and Greg is getting attached to his lady friend, but on advice of Veora, June decides it's time for her to move on and experience more. Greg reluctantly lets her, attempts to branch out himself, but finds that he wants June to be his one and only.

Some months go by after the breakup. Though the gang usually meets up for fun times, June shows up less and less. Turns out she's dating Tom, an obnoxious, pompous stud that the men of the group know (terrible one-sided rivalry that dates back?). Though the men actively try to convince June he's a horny, womanizing jackass, Veora blindly supports June's decision to date him, as long as she is happy. June doesn't seem to have any problems with Tom and finds him to be a nice guy. Both girls are poorly informed of his dating history.

Greg, determined to get June back, decides to expose Tom for the flirtatious bastard he really is by having June catch him in the act (in some way).

Mike and Muhammad run through some ideas with Greg, and decide (somehow) that the only way is to seduce Tom into a trap. They plan on double-dating with Tom and June in order to reveal Tom's true nature in plain sight of June. Failing to find any women to help them form a plausible couple, they decide to change their own identities through disguise. Mike and Muhammad force a reluctant Greg to dress as a woman, and Muhammad is agreed to be his date. Greg actually looks pretty.

Greg and Muhammad find out June's plans from Veora, and find her and Tom at a restaurant, where the men just force themselves into their evening meal as "long-time friends of June," triggering a series of subsequent double dates. June is openly incredulous and embarrassed that easily-noticeable Greg and obvious Muhammad are doing this just to prove something she so vehemently disagrees with, and Tom is oblivious to the whole situation. Greg unwillingly makes subtly suggestive comments and motions to provoke Tom, Muhammad is straightforwardly neglecting Greg in order to give off the impression that his lonesome date sorely needs a loving partner, June is playing along with sarcastic undertones, and Tom is almost playing into the whole thing as planned.

All characters are heterosexual.

~

So...
1) What do you think? Would you be interested in reading this if published here on Lit?
2) I don't know how to end it the fiasco. I know I want swinger Tom caught, but I don't know how. I'd like it... in an unexpected way.
3) I already know whether or not June decides to get back with Greg after all that, so I don't need suggestions on it.
4) I can't think of a good background story for how the guys know about Tom.
5) Any other suggestions and feedback would be extremely helpful.
 
C'mon, guys

It doesn't take long to read and contribute, right? D:
 
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