Halloween always brings back this memory. When I was a teenager, I always dressed up as a girl for Halloween because I could easily pass. I was slim, pretty much had a hairless body other than my public hair until I was in my mid-twenties and soft features. With a wig and nice make-up it was hard to tell I was actually a guy. When I was seventeen, I pushed my costume to the limit for a party I was going to wearing full panties, stuffed bra, school girl outfit, socks and heels. I wore a long brunette wig and looked good with my brown eyes. A couple of girls I was friendly with did my make-up. I looked really good that night. We went to a party put on by one of my friend's co-workers. We were probably the youngest people there, most of the guests were in their late 20s and 30s, some even older.

Men in costume were hitting on both the two girls I was with but also me too. They were all drunk and thought I was a girl. After awhile I had a few drinks and was buzzed. My friends were talking with guys and I was on my own. This big guy in his 40's started talking to me, telling me how hot I was, I said many times it was the costume but he wasn't listening. He was right up on me, touching me and at one point put my hand on his cock which was really hard and really big.

I was nervous and scared looking for my friends to rescue me but he stepped back and said he was sorry and went off. Then he was back with drinks for us. Mine was really strong and my head was spinning. He managed to walk me outside. He showed me around, his hand around my waist, touching me here and there while ignoring my excuses to go back inside.

Next thing I knew we were in a garage. He showed me where he and the person whose house it was worked on motorcycles then I was in a little alcove off the garage. He was in the doorway, a huge muscular guy, a young skinny me in the tiny room which was taken up almost entirely by a dirty looking bed. He said he slept there once in awhile and that he sometimes fucked girls there. I was so nervous I was afraid to speak.

He asked me for a kiss. I said no it's just a costume, but he insisted, pulled me to him and then his tongue was in my mouth, his hand was under my skirt squeezing my ass, his other hand around my waist keeping me from pulling away. He held me like that tongue kissing me for awhile then He put my hand on his exposed cock he had taken out. It was hard, thick, hot to the touch but his skin was really soft. I was shaking as he used his hand on mine to make me stroke him.

His cock was much much bigger than mine and I was starting to worry what he was going to do when he realized I was a guy. He pushed me down on the bed and there was his cock, in my face. He held me by the back of my head and moved his cock to my mouth, I wanted to pull away, to scream for help anything but I also wanted to see what it would be like. My curiosity won out because I licked my lips and in he went. I sucked and licked. He asked if it was my first time. I nodded yes. He said to follow his instructions. I listened and did what he asked, swirling my tongue, using my lips on the head just so, taking him deep and letting him pump my throat as deep as I could take it. When he was close to cumming he said something like, "no way, I'm cumming in your pussy" and before I knew what happened, I was on all fours on the bed, my panties were yanked off, and I was yelling "no wait, wait" but he didn't. He spit on his hand a few times and I felt his fingers on my asshole lubbing me up. I tried to squirm away but he was really strong, then I felt pressure which turned to pain as he slowly forced his dick into me, up my ass one inch as a time until he had bottomed out. He slow fucked me for what seemed forever it was so uncomfortable but after awhile It started to feel good. Now I realize he probably knew I was a guy the whole time but I'm not entirely sure.


I transitioned from whining in pain to grunting in pleasure. He moved me a few times to get just the right angle then he started to fuck me hard. Really hard. So hard it hurt so bad I tried to get away. He pulled me to the corner of the bed with one leg on either side, pushed me flat on the bed, pinned my arms behind my back holding them together with both hands and used my arms like handles to fuck me. He was standing, squatting down, jamming his cock into me, pulling and pushing on my arms to make me ride his dick. He fucked me super hard, his sweat dripping on my ass, the sounds of my grunts and his balls slapping me all I could hear. After ten hard minutes I realized not only was I hard as a rock but my cock was throbbing. It was rubbing against the sheet with each thrust which was going to make me cum. I felt that tingle when you're about to cum and tried to move to avoid it but he just fucked me harder thrusting his cock as deep as he could. I cried out when I came, feeling my cum shoot out then smear all over under me. He just kept thrusting.

After a few more minutes he lifted my hips just a little then changed so that just his cock head was sliding in and out right at my asshole then he said "oh yeah" and drove his cock deep when he ground out a load deep inside me. He pulled out hard when he was done and left me lying there, sweaty, sore, ass full of cum. I eventually got dressed and went back to the party. My friends wanted to know where I was, thought I had been with a girl. I could feel his cum oozing out of me, I had to go to the bathroom to clean up a few times.

When I got home I showered and spent the next six months terrified people would find out. No one ever did and now it's a stimulating memory. Thinking of dressing up like a sexy woman and finding a powerful masculine man to take me is a huge turn on. When I think about it I get crazy hard and usually fuck the hell out of my wife or jerk off. I think I'd be too nervous to ever actually do it at this point but I don't think I would resist if a man tried to force himself on me which sounds crazy I know.