Where it happened: Her room
Langauge: English
Sex: Male
Rating: 5
Category: Straight
We had been dating for two years, but had put off having sex because we were both going to college far apart and didn’t want to open that can of worms…until the summer.
Her parents were out of town and we were making out on the bed. I knew that she had condoms in the room, so I said that I thought we should have sex. She nodded, so I slipped a condom on and slipped my cock…
Except it wouldn’t go in. It was like trying to fuck a cinder block. At first, I thought I was trying to put it in the wrong spot. I felt around with my fingers, acting like I was doing some slick sex move, but I think she could tell something was wrong.
“Just put it in.”
“I know.”
“What’s wrong?”
“Nothing, I’m on it.”
Poke…poke…poke?
“What’s wrong?”
She grabbed my cock and guided me in…and this time, I got the head it. She winced; she was a virgin, too. I knew from fingering her that she was tight, and my penis is pretty thick…but I didn’t realize that it was going to be this much of a problem. I basically forced myself in, up to the hilt. I could tell it was excruciating for her, so I pulled out and started thrusting really shallowly. Then I made a fatal mistake.
“Why don’t you be on top, so you can control how deep I go?”
She liked this idea, so on she climbed and then slide down my…
Except her muscles still weren’t relaxed enough, so instead of sliding down my cock gently, nestling me deep inside her, she slammed down and, you guessed it, pretty much sprained my cock.
Everything was throbbing, but I was too embarassed to say anything.
“Baby, I think I’ll go back on top.”
Now I’m throbbing, she’s wincing every time I move, but I’m determined to finish this thing right, so I start going at it, pumping like a porn star, holding back tears. It hurts so bad that I can’t even think about cumming, and I can tell that she’s in a lot of pain, too…
So I faked it. I pretend to cum, pull out, run to the bathroom, and bury the condom as deep as I can. She never found out.
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