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This is a story about a first-time crossdresser and some sex that starts out as slightly violent and non-consensual. If you're into that kind of thing, enjoy! If you're not, or if you're under 18, or if this is illegal where you are, go turn on the Disney channel.
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Halloween. It's just an excuse to go out drinking with friends like any other night, only this time in a ridiculous costume. And since my friends and I definitely like to party, it makes sense that I dress up for the occasion.
This year, I decided to surprise the guys by dressing up as a girl. At costume shops they have a thousand different "sexy" costumes. Sexy cat, sexy cop, sexy pirate... I always loved it when I saw girls wearing these costumes, so I thought it would be fun to put one on myself. I grabbed one off the rack at a pop-up Halloween store near my house. Luckily, I'm small enough to fit into the one-size-fits-everyone-but-the-fat-girl costume--at 5'7", 135, I've never been accused of having a buff physique.
My name is Jeremy, by the way, and I'm 25. I work in a law firm as a paralegal, but I don't really love it. The money I make pays for my real life outside of work. My friends and I go to concerts, take vacations together, and party. I'm at that stage of life where I feel invincible and just want to have a good time. Which might explain why I left the house looking like a total slut that night.
The costume came with patent leather Mary Janes with a little bit of a heel, knee-highs, a short (OK, a VERY short) plaid skirt, and a white oxford crop top shirt with a sexy little necktie. I really wanted to sell this look, so I bought a pair of very girlie panties--thin cotton with little red hearts--and a blond wig. I did a little makeup on my face thanks to some how-to videos on YouTube. I shaved my legs above the knee-highs. I don't have a ton of body hair, but if I'm going out as a sexy girl, I want to look like a sexy girl, not a militant feminist.
When I put the whole look together, I was surprised by how good I looked. At first glance, I looked like a girl dressed up as a schoolgirl rather than a guy having a laugh.
A word here: up until tonight, I would have told you I was a completely straight guy. Now, I don't have a girlfriend and spend all of my time with my guy friends, but in my mind, I was just a regular guy. That night, my perception would change abruptly.
I got to the bar where a few of my friends had already gathered. Pete, dressed as Obi Wan Kenobi, gave me a full-on sexy smile before he realized that it was me. "Oh shit!" he blurted, "I thought you were a beautiful girl coming to hit on me!"
"Has that EVER happened to you before?" quipped Joe, dressed as a sailor.
"There's a first for everything, even Pete getting laid," responded Bryan. Bryan claimed he was dressed as Mitt Romney, though he had pretty much half-assed it with a blue suit and an overly styled hairdo.
The evening continued like this, my core friends and a few other people having drinks and making fun of each other. It was a fun, unspectacular night. Like I said, the usual weekend night, plus costumes.
Well into the night, I leaned back into the bar to get another drink. To my surprise, the bartender already had set one in front of me, a shot of good tequila. "From the gentleman," the bartender explained, nodding at a guy at the other end of the bar. He was a bigger guy, maybe 6'1", kinda buff, a little tougher looking than the crowd I was with. He was dressed as a pilot, and looked the part with a short haircut. I smiled at him, gave him a playful wink, and downed the tequila shot. Then I ordered another drink. What can I say? I was 25, and my liver was in fighting shape.
I didn't think anything of this guy...if you looked at me for more than 30 seconds, you could figure out that I was just a guy dressed for Halloween. He must have been having a laugh with me, right? But as the night went on, and we all got drunker, I found out that he was not just having fun.
The bartender tapped me on the shoulder. "Another one from your admirer." A shot of Patron Silver sat there on the bar. I looked down the bar to see this guy's eyes fixed on me. I swear, no man has ever looked at me that way before. It was like something out of a nature movie. This guy looked like he wanted to own me. For the first time, I felt a little uneasy.
I picked up the shot, and looked down the bar. I guess that was this guy's cue, because he began walking through the crowd towards me. I slammed the shot to steel my nerves as this guy approached. He stood right in front of me, closer than you would in a normal social situation, close enough that I could feel the warmth of his breath on my face.
"You wanna dance?" he asked, somewhat expectingly.
"Oh...no man...thanks for the drinks, but...I'm really a guy," I stammered.
"Well you look like a bitch to me," he said. Somehow it didn't sound like an insult, more like a statement of fact. And really, he was right. Here I am, dressed like a slut and taking free drinks from this guy. I didn't know what to say, so I smiled and looked into his eyes nervously.
He spoke again: "Why don't you come back to my place? I've got a thick problem that I think you can help me with."
He took my hand and put it on his inner thigh, where I felt the outline of a big, throbbing dick. I felt so vulnerable that I let him hold my hand there, and for a second I was enthralled with his massive member, as well as the fact that he appeared to be aroused by me.
Then I came to my senses. My friends were at the bar, I had probably had too much to drink (about two tequila shots' worth), and... I was straight! I pulled my hand away and slurred, "I'm sorry, I gotta get home." I made a hasty retreat towards the door. My friends made some jokes about me being a lightweight, and I stumbled into the cool night air.
I lived close enough to the bar that I could walk, maybe 6-7 blocks. The air was cool and moist, and gave me goosebumps on my shaven and exposed legs. It was late by now, maybe 3am, and most of the Halloween revelers were passed out or in bed by now. My heels clicked on the pavement as I walked the deserted blocks back to my place.
As I made my way, dressed way too scantily for this weather, I began to sense someone was following me. I tried to quicken my pace but I heard footsteps getting closer. I looked back to see the guy from the bar. He grabbed my arm, spun me around, and pinned me up against a brick wall.
"You can't take drinks all night from a guy and not expect to put out," he said as he pressed his body closer in to mine.
"You don't understand," I whimpered.
"I understand perfectly. You're a cocktease, and you're going to get what you deserve."
Jesus. This was no longer funny. I had to get away from this guy. I ducked from between his two arms and took off running. He followed me, but I'm pretty quick. If I could get to a main street I would be safe. I was gaining ground on him. I looked back, and just as I did, I twisted my ankle from these stupid heels. I wound up on my hands and knees, my shaven knee scraped on the pavement.
I thought, briefly, at that moment of a decision I had made. A series of decisions, really, but one in particular, and I would think about it for years to come, wondering... had I brought this on myself? Is it possible I wanted this to happen?
Before I went out that night, I had fully lubed my "pussy"--that thing I normally thought of as my ass. The thoughts I have about why I did that run wild and deep... but not on Halloween night. I did not have time to ponder it.
He was on me in a second. "OK, bitch, time for you to get it." I could hear him roughly unzipping his pants as he held me down against the sidewalk. With his left hand, he reached under my skirt and pulled my panties down just enough to expose my asshole, and with his right hand he put his huge, hard cock in place. With no preamble, he shoved his thick dick two inches inside me.
Was this really happening? Was I really dressed as a slut, on my hands and knees, getting raped? His dick was impossibly thick; it felt like he was driving a baseball bat up my ass. The pain was such that I couldn't breathe. I laid there, the wind knocked out of me.
"Fuck, that's tight." He insistently pushed more of himself inside me. To minimize the pain I had to adjust my back, sticking my ass up in the air. "Yeah, bitch, take it." After some consistent pressure, I could feel his pelvis meet my soft ass. His big balls rested against my shaven thighs.
"Please..." I whimpered quietly. I couldn't cry out. Maybe I didn't want to. This guy was filling me completely with his dick, and all I could say was "please."
He took to fucking me. He dicked me aggressively, like you do when you are deep into a passionate fuck. He pistoned in and out of me. I began to arch my back to meet his thrusts. I could feel my ass opening up, and my prostrate squeezing off the head of his dick. I thought to myself that this was a hot fuck...it's just that I was the one who was taking it.
As he got into his rhythm, my pain and embarrassment was replaced by a new feeling: an extreme need and pleasure. I found myself involuntarily grunting like a bitch with each thrust deep into my pussy. Worse still, I was getting aroused myself. My dick was hard in my thin cotton panties. Jesus, he had me so worked up.
My grunts and moans built, and his pace and pressure picked up. My ass was gripping his fat dick like a glove. I felt a surprising but familiar feeling... I was about to blow my load. Against just the friction of my panties, my little hard dick was about to blow. I was so embarrassed but I couldn't control myself. I tried to hold back, but exploded into the most powerful orgasm of my life. I must have woken up the neighbors with my shrieking. I'm sure they just thought it was some drunk slut behaving badly on Halloween. And come to think of it, they were right.
As my orgasm subsided, this fucker was still thrusting hard into me. I came back to my senses. I took stock of where I was: on my hands and knees, dressed as a slut, with a thick dick buried in my tight, formerly straight ass. And worse still, I had gotten off by getting this guy off. I came from getting assfucked.
These thoughts were replaced by having to brace myself as this guy reached his peak and exploded his load inside me. He must have cum for 20 seconds, each time injecting his dick deeper inside of me. I had a load of cum in my panties and one deep inside my ass. I felt somewhat humiliated but strangely satisfied. As this guy pulled out of me, I felt naked, empty. I reached behind and pulled up my panties and scrambled to my feet.
As he stood up, breathless and with a look of utter satisfaction on his face, he said, "meet me at the same place next week."
And the crazy thing was, I thought to myself that I probably would.
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