Tranny for a Night

by Diego

Due to peer pressure (i.e. my Hag begging me to do drag), I finally got around to dressing like a tranny and hitting New York City's She-Male nightlife.

My Fag Hag and I hit up Broadway for the essentials: Victoria's Secret $25 push-up bra (I'm a 36-B), frilly pink dress at Express ($35), cheap Sephora make-up (their own line, $6 per item), black cardigan to cover up the biceps at H&M ($19.99) and a silver clutch at one of those shady Chinatown kiosks ($12).

I didn't know about any Tranny bars so I posted a "Anybody knows of Tranny bars for tonight?" ad on Craigslist. Most of the responses were versions of "Why go to a bar when you can just come over and suck my cock?". But a couple other trannies were nice enough to suggest a couple places, so we ended up cabbing to Maya Lounge (on 14 E. 33rd St., between Madison and 5th Ave.).

My Hag did a good job covering my beard and making me look like a chic She-Male, not some cheap-ass crack whore. So I was feeling confident. Interestingly enough, I feel more "in drag" when wearing a suit and tie than when wearing a brunette wig, high heel fuck-me boots and a push-up bra.

The place wasn't packed, but the atmosphere was surprisingly friendly. The bar changes colors and the light is dim, which shows they know their clientèle (God only knows how fast my beard grows). There were plenty of post-op-looking trannies in skanky-ass outfits and acting like total whores. So I was the demure, sophisticated bitch by default.

This black guy approached me and started chatting me and my Hag up. Drinks were $13 a piece so I was hoping the motherfucker would buy me one. But he didn't want to waste any time: "Let's go to your place; you can suck my dick while I eat your friend's pussy". Which is a black man's version of white men's "Can I take you out for dinner?".

Anyway, I wasn't about to stick around all night waiting for Prince charming. I could always post "Tranny Whore Needs Some Pounding" on Craigslist, have a couple of Brazilians over and call it a night -- in case the black guy disappointed.

Which he did even before he took his clothes off. "Are you gonna rape me? Are you gonna dress me up in a thong and rape me?", he asked. Excuse me. Way to not have no idea of what this is really about, fool. I'm the bitch, you're the rapist. Anyway, he was married and had 6 kids, so whatever, that was hot enough.

He drove us home and my Hag immediately opened her Mac -- bitch can't stay an hour without her Craigslist. So I brought black dude to my room and he flipped me over and touched my body like only a straight married man does: with actual lust. None of that theater gay guys have to go through: pretend you're butch and I'll pretend I believe you.

This man's cock was so fat it seemed sick. Like bee-stung or something. His sexuality was so bottled-up (therefore fucked up), he kept uttering things like: "Am I gay? Am I a faggot too?". And I said "No", to which he said "Come on, tell me the truth". And the truth is, if you're 38 and you still don't know, then I don't think you have enough time left to figure it out, so go ahead and eat my coochie, fool.

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