Prom going wrong

by BillyBoy

11 Jan 2022 6501 readers Score 8.9 (63 votes) PDF Mobi ePub Txt


A few of us didn't have proper girl dates. it's our last dance. Senior prom and we all graduate next month. Jeff and two other guys suggested we go as each other's dates. Two of us were picked out to be girls. I wasn't really ready for that. But everyone thought it would be fun, and a bit of a joke for everyone. So I agreed. 

"This is the stupidest thing I've ever done. But I'll take one for the team."

My sister helped me dress. She took this very seriously. When I saw the other boy in an old, sloppy-fitting dress, costume wig, and tennis shoes, I was really embarrassed. I looked pretty cute. Perfect make-up, a slinky dress, mom's best blonde wig, and 4 inch high heels. Jeff grabbed me right away. He whispered to me in the car all the way to the dance. 

"If you don't tell anyone, I'll give you a real nice goodnight kiss after the dance."

We didn't stay long. The other boy took a lot of shit for his costume. But no one really said anything about me. I don't think anyone could tell I wasn't a girl! After we got our pictures, Jeff took me by the hand and whisked me out to the car. We left the other boys at the dance without a ride. In his driveway, Jeff leaned in and went for the kiss. We had both been drinking a bit. And when you're 18, it hits you pretty hard. The dress and tight girly underwear had done a number on me. I was feeling the vodka and the feminine side of me, too. I slowly opened my mouth and let him do it. His tongue was warm and wet. I rolled it around in my gently sucking mouth. His hand slipped up under the hem of my dress, past my waist, and up over the pretty lace training bra I was wearing. 

He stopped kissing me for a short, very important moment. 

"Unzip my pants for me."

I looked at him with big, round open eyes. He was staring back at me. Waiting. No one spoke. The moment lasted forever. I took a gulp. My head nodded a tiny bit. I heard my lips whisper a nearly silent" "Ok."

The kissing started again. deeper and wetter. I was drooling as I fumbled with his leather belt, button, and zipper. His hand was groping my chest and his fingers were pinching my sensitive nipples in the soft training bra. He slowly rolled back. His legs were spread out as I opened the slacks letting his young, rock-hard cock pop out. There was a little pressure on the back of my neck. I knew what he wanted. I immediately gave in and dropped my head into his lap. I quickly had replaced his tongue with the tip of his throbbing cock. I had a handful of it, squeezing it hard. I sucked the tip, then slowly slid down the shaft to the top of my hand. It tasted so fucking good!

Jeff's hand gripped a handful of my hair. Pushing my head down further. "Oh my God!" He gasped. My mouth filled up. He blew a huge load right inside. I blew snot and cum out my nose. It was a real mess. I didn't know what to do. I supposed I should swallow as much as possible. I did my best. He came again just a moment later. I had to start over. More cum. More swallowing. 

The car door opened and we fell out. He was going to help me clean up before I walked home. My dress was half off. We were pulling and tugging our clothes back to where they belonged as we walked into the house. Jeff's dad was watching TV. He barely acknowledged our entrance. After some giggling and a few minutes in the bathroom, I quietly made my way back through the house for the front door. I didn't see his dad in the chair. I was trying to figure out the front door's deadlock when I felt a hand on my shoulder. 

"We need to have a little chat. You and I."

The man quickly pulled me back through the kitchen and down the back basement stairs. I wasn't sure if I should be worried or pissed off. When I tried to complain he took a dishrag he had brought along and stuffed it in my mouth. He held my arms tighter and pushed me faster through the basement into a back room. 

"Jeff brings a few of his little gay friends by here now and then. But you are the best one so far. I want a little too. Do you understand?"

I felt like I'd just had much the same sort of offer a half-hour ago with Jeff. I reached up to remove the rag from my mouth. I slowly nodded and said "Ok."

His rough stubble face was all over mine. Kissing and licking me. His hands were all over me. Before I knew what happened his finger was in my ass pushing hard to get in further. I let out a little squeal. Like a girl would! The rag was back in my mouth. This time he pushed it deep and held it there. His tongue licked the side of my face as he spoke.

"Let's keep this in here. I don't want to disturb Jeffrey while we are doing this."

I can't explain how everything else happened. All I know is I was face down on this old bed with his cock sliding in and out of my tight, 18-year-old virgin ass. One hand was holding the dishrag in my mouth while the other one was pulling my butt cheek to the side, making his entry a little easier. He was grunting and kissing my face as he pumped harder and faster. 

"Oh fuck yes, you little tramp!"

"Mummph! Mummph! Mummph!!!"

Fuck! Finally! He finally came and stopped hammering my sore little butt hole. gees! He slowly moved off me. I rolled over on my side, taking the rag out of my drooling mouth, trying to catch my breath. I was really wet down there. I'd cum all over myself. What the fuck?

by BillyBoy

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