It Happened On Manhunt: The Closeted Crossdresser

Things got ugly the last time cross-dressing was brought up on Manhunt Daily. However, while some of you may be violently opposed to the topic, the fact of the matter is that some men get off on dressing up in women’s clothing. And some men like sleeping with those men.

In fact, there are certain occasions when the latter group falls in love with their panty-wearing brethren. Today’s edition of It Happened On Manhunt is an electrifying read from start to finish, in which one member shares his experience with Nico— a fellow who preferred to go by Nicolette in the bedroom. You don’t necessarily have to be turned on by the scenario, but we encourage you to treat it with respect.

Oh, and if you wind up reading this and thinking to yourself, “Hey, I’ve had something crazier or hotter happen to me on Manhunt! Why isn’t my story featured on here?”… Well, you’re in luck! We’re still on the search for the best of the bunch.

Simply write us an e-mail at with the words “Best Manhunt Story” in the subject heading. Remember, the folks behind the top entries will receive a FREE month of unlimited membership to Manhunt. So what do you have to lose?

NOTE: The man behind last week’s story, “I Met The Man Of My Dreams”, sent over a few additional details to satisfy those of you who longed for more. This may or may not include references to fisting. Head over here to revisit his experience!

– Dewitt

To read this member’s story, follow the JUMP:

I suppose my story starts off not unlike countless others. Boy has friend, friend has secret. Boy discovers secret, relationship is forever changed. However, the details of this little story make things all the more juicy…

I met Nico when I was a freshman in high school and he a sophomore. We were both runners, so we spent three years running Cross Country, Indoor Track and Outdoor Track. We bonded while running.  When we ran together, it was as if we were always running toward some elusive finish line neither of us knew the location of.

Nico came from a very Christian family; every Sunday church going, conservative, God-fearing people. Nico always seemed to take things a step further when it came to voicing his beliefs, something that both intrigued and enraged me.  For I was sure I was gay by this point, but coming out was made difficult when one of your best friends preached hell, fire and brimstone to those deemed “sinners”.

Nico graduated a year before me and went off to college two states away.  We kept in touch through the internet, and I saw him when he was home for breaks.  However, he seemed very different. He would go through periods of extreme rage and joy. When I asked him if something was the problem, he said it was no big deal and to drop it.

I ended up selecting a college not too far from Nico’s. Nico had begun to build a life for himself in the area. He was a volunteer firefighter and doing really well in school.

Meanwhile, I wanted to finally begin enjoying my life—both sexually and emotionally.  A hook-up of mine told me about Manhunt, so I signed up and began to explore. One day, one of my searches came up with a profile of a cross dresser named Nicolette. Curious, I messaged him. At this point in my “Manhunting” experience, I only had a cock picture up. Nicolette responded complimenting me on a nice piece of meat and asked for more. I told him I would trade dick for dick, face for face.  So he sends me his screen name, and shock and surprise… It’s Nico!

I hastily sent Nico a message saying I had an emergency and would hit him up later. Unsure of whether or not to continue talking to “Nicolette”, I created a new screen name and messaged him. After talking about how he loves getting his man-pussy pounded and being treated like a hooker, I asked him if he wanted to trade pictures. After sending him my face picture, he signed off and didn’t speak to me for a whole week.

Later, he called and said he wanted to meet up to talk about what happened. He told me he had always felt like he belonged in women’s clothing but never knew how to express it. He said he always exaggerated his anti-gay sentiment to prevent anyone from catching on. Then he said he wished he knew I was gay earlier, so he could have acted on his crush much sooner.

Emotions (or hormones) took over at this point. I leaned in and kissed him, not sure of what would happen when it was over. The kiss lasted over two hours, in addition to the removal of clothing and some of the best sex I’ve ever had. We spent the next two years together, and I found myself making love to Nico but fucking Nicolette like the whore she wanted to be treated as.

It seemed to me that happily ever after might have been found for both of us. However, his God-fearing roots ran deep, and when the topic of the future came up—and he wasn’t able to dodge it—he said it wouldn’t be something he could give me. I ended it with him because he was never going to change for me.

He went back to his old anti-gay ways, of course, and ended up marrying the first girl he knocked up.  He went back to our hometown and moved in with his parents while he tried to find a way to support the wife and baby. Every once in a while, I’ll see him when I return home; and I’ll notice the residue of blush and eye-liner he tried to wipe off. He calls as well, wanting to get together so “Nicolette” can be used. I haven’t since those days in college.

Part of me would love to have him back in my life, as either Nico or Nicolette. It’s a cruel twist of fate that my first love, my first true love, was the friend I ran to that elusive finish line with. Part of me feels we’re still both running to that goal, but I doubt we’re going to cross it together.

While this may not be the “Best” Manhunt story, not all stories have happy endings.  Sometimes, we let our feelings fall by the wayside so our love can get on that plane or finally be at peace.  However, I do feel one day my story will have a conclusion… Or at least one hell of a sequel!

9 thoughts on “It Happened On Manhunt: The Closeted Crossdresser

  1. Ohh my!!!! you can call me old fashion but i still getting off by another man image L0L

  2. Nicolette sounds like she is dumber than a box of rocks and Nico is not that far off either, sounds like the other guy is way better off without the she male that doesn’t know her own mind & is as flighty as a feather.

  3. D: You coulda warned us it was a sad story! Not the first thing I wanna read in the morning. It was beautiful in all aspects, but I just like happy things in the morning.

  4. It’s their demeaning attitude towards women which wind me up. I see so many profiles from trannies with phrases like ‘oooh I’m such a dirty slut’ and ‘treat me like the nasty girl I am’. It’s like the only way they can feel comfortable with their desire to suck some cock or take it up the ass is to play dress up.

  5. that was a great read!

    i appreciate the detail given (because it doesn’t make me believe this is a faker story), like a couple of other entries in this series.

    a “slice of real life,” i might opine — and yet another tale of how Homophobia ruins a potentially beautiful relationship.

  6. I would like these posts if they were actually a bit more believable, but they make for nice stories.

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