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Losing My Cherry 2

by Matt25


After my football-player roommate nailed me over the dresser I didn't know what would come next. The only other time we had sex, when I sucked him off, he pretended nothing happened and kept talking about pussy. I didn't know if he'd do the same now or if he'd want to play again.

He was a party boy and was out late more often than not. I was pretty quiet and usually in bed by the time he got home.

A couple nights went by and I heard him come in. I was awake in bed, but pretended to be asleep. I heard him close the door and start getting out of his clothes. His took his shirt off and I heard his jeans and belt hit the floor. He got out of them and his socks and then took off his undershirt. He was in just his white Jockey briefs now, with a big hard on stretching out the front.

He opened his drawer and got a rubber out. He dropped his briefs and rolled the rubber over his big prick. He walked over to my bed and slipped in with me, slipping on top of my back, massaging my back, and kneading my butt through the Sears boy’s briefs--I still wore then. After a minute he pulled down my briefs, rubbed his dick over my crack and then pushed it in. He groaned and started to fuck me harder, with the bed frame creaking loudly. After just a couple minutes he groaned, "fuck yeah" and came hard. He went back to his bed and went to sleep.

At this point, I figured he was convincing himself that I was his "pussy". I didn't care, since I was enjoying the "attention!"

My suspicions turned out to be true. One night he was out as usual, and I was getting ready to go to bed. I turned down the bed and found what was apparently supposed to be my outfit: a pair of nylon panties, a bra, and one of his (for me) huge undershirts. I figured "what the hell?" and put the outfit on, getting an immediate hard on.

He came home and went through his usual routine, putting on a rubber and sliding in my bed. He was really worked up when he saw me in the outfit. When he reached up and fondled my panty-covered ass he groaned and came immediately. He said "Fuck!", got up, took off his cum filled rubber and rolled on another one, never losing his hard on.

He came back and his hands were all over me, grabbing, fondling, and unhooking the bra. He pushed my panties to the side and fucked me hard while i was still wearing them. He came pretty fast and I shot in the panties. He pulled out, saw me in the cum-filled panties and smiled and said, "You better rinse out your panties."

The next day he came in with a huge box of Trojans, and I knew our "relationship" would be continuing.

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3 Gay Erotic Stories from Matt25

Losing My Cherry

I was a pretty small dude in college: only about 5'6 and about 135 pounds. My freshman roommate was a big, strapping football jock: probably 220 and about 6'2". We didn't have that much in common but got along okay anyway. When school started it was pretty hot in our dorm since we didn't have a/c. He spent a lot of his time hanging out wearing not too much…usually just briefs and t-shirt

Losing My Cherry 2

After my football-player roommate nailed me over the dresser I didn't know what would come next. The only other time we had sex, when I sucked him off, he pretended nothing happened and kept talking about pussy. I didn't know if he'd do the same now or if he'd want to play again. He was a party boy and was out late more often than not. I was pretty quiet and usually in bed by the time he

Nailing the Pizza Man

I was planning to go out partying, but decided I should eat something before I drank too much. I called my favorite pizza place and ordered a large pepperoni pie. The pizza's good and the delivery is fast, but the pizza men have never been anything too look at. This time was different. The bell rang and I opened the door. In front of me was an incredibly hunky dude, about 24, handsome

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