A good laugh turns into a new experience

I have a friend that works in theater and makeup, one night he got tickets to a "trans" ball and invited me to go with some friends as a joke. So I figure, throw on a skirt, toss some apples in a bra throw on a wig and go party. I show up at my buddy's house around 8. I figure we're gonna pre-game. He answers the door in full drag. He pretty much could've passed for a woman.

He took one look at me and said "dude you have to shave the beard". He proceeded to tell me how I was going to fuck up their good time of looking like a gang of sluts. So I head into the house and I see some acquaintances also dressed up, I say my hellos and head into the bathroom to shave. As i'm shaving he makes his way into the bathroom with what I can only describe as the ugliest crotchless bathing suit i've ever seen. "I'm gonna wear that?", "under your clothes" he replies "it's a padded bodysuit to give you hips and titties. Great. So I finish shaving and sloppily re-apply some makeup. He comes over and tells me to sit on the toilet and he'll do it.

In 15 minutes I had layers of a cake plastered on my face to the point where my skin was invisible. "I'm gonna sweat this off man" I told him. "Hey as long as you start out looking awesome. So I pull on the bathing suit thing and grab my little skirt and he points at my legs "dude you've gotta do something about the hair." I'm not shaving my fucking legs, I tell him. Here wear this. He tosses this stretchy denim one piece jumpsuit at me. "What am I a mechanic?" Jennifer Lopez wears those things. So I just roll my eyes shake my head and pull this thing on. I barely pull this thing on, practically popping out of it at the seams and he comes in with boots for me - i'm thinking to myself this guy is way to prepared for this shit.

So I squeeze my feet into these little boots (killing my toes). He's like "dude you look like a chick". I take a long look at myself in the mirror and sure as shit i looked like a chick - a 6 foot tall chick but a chick. So we all go out to the kitchen whored up. Take some tequila shots, take a group photo and we're off. I'm taking my own car because if this is lame i'm going home. So we all head to the bar, I pay $15 to valet so I'm already in a bad mood. We get to the door it's a $10 cover. We all head into the bar there's some loud techno trance like music playing the lights are low, we all scoot up to the bar, I grab a shot of whiskey.

They all hit the dance floor and start dancing with each other. I'm not much into dancing so I stay at the bar and suck down a few drinks. A couple of guys grabbed my ass, one wrapped his arms around my waist and traced his hand down my zipper. I pulled away. "i'm outa here". I'm bombed, so I walk down the street a ways to the next bar. Pop in and get myself a glass of whiskey. An older guy at the bar, obviously drunk, compliments me on what a strong drink for a lady and compliments my outfit. I finish my drink and head over to the restrooms...now i'm in a kenundrum i'm sure some people are sober enough to tell i'm a dude but do I want to get beat up for cross dressing if its confirmed? So to the ladies room. I grab a stall unzip the jumpsuit and pull it down maneuvering roughly to get it off. I pull it back on and I feel the seam along my crack tear...now my ass is exposed - great.

So I reach into my buddys purse and grab a black bar napkin that was in there that I used to temporarily cover the seam. I head out to the bar to close my tab and the older guy offers to buy me a drink - hell i'm sitting here - i'm out - it's early, I just blew through nearly $60 - i'll take a free drink. He orders me a cocktail, than another, he keeps going on and on about his ex wife, how he loves my jumpsuit, how he wishes she dressed like that for him. In the meantime i'm getting really drunk and really horny. I start looking around the bar for a girl to take home and then I realize that i'm in drag. The guy asks me to go over to a booth with him - so we do.

He moves to kiss me and I move away. I notice now his shiny crotch. "Are those leather pants?" Yes they are he responds. Now I love it when women wear leather pants, I love rubbing my cock up against their asses and now he was - oddly enough - beginning to turn me on. In a drunken extremely horny mood i'm getting irrationally turned on. I want him to rub is ass on my dick but doing that might end with me getting beaten to a bloody pulp. Knowing he wanted me - which felt empowering - I get up and sit on his lap. grabbing the side of his leather pants. He begins to grope me from my fake his running his hands up my denim to my fake breasts.

Next thing I know we're leaving the bar, attached at the lips in a very sloppy fit of drunken passion. He lived on the next block so we made our way over there. We fumble into his apartment, he pushes me on the bed and goes to unzip my jumpsuit. I catch his hand "i'm really not comfortable with my body" He jumps on top of me and locks lips he grabs my crotch doesn't even notice my cock, I don't think I even noticed, I was literally in a drunken haze of bliss. Within a period of 5 minutes he found the rip in the seam and stuck his finger right in my ass "I can feel your pussy" he said.

Alarms are going off in my head to stop but as I feel him worshiping my body wrapped in all this denim, I have my hands clawed into his leather ass. He in one clumsy motion unzipped his pants, pulled his cock out and shoved it straight into my ass - even wasted it hurt. As he pounded me into oblivion I came in the jumpsuit I felt his cock pump cum into my ass. Then he rolled over and passed out. I let myself out and went home. I didn't sleep at all that night I had a lot of shit to figure out...needless to say that wasn't my last night in the jumpsuit.