This took place in September 1997. Even though she was 3 months older than me, she was a sophomore and I was a freshman. We had been dating just over a year at this point.

We will call her Jane. She was 5'7, shoulder length curly blonde hair, full 36C boobs. I was 6', 210 lbs, short brown hair, and was a college lacrosse player. Earlier that night we had a fun round 1. We were spooning on my bed and I was grinding into her from behind. She was wearing mesh shorts that she usually wore to bed and had no panties on. She grinded her ass into me and the head of my cock was rubbing against her butthole, she moaned and remarked how good that felt. My hand went down her shorts and she was already soaking wet.

The next words out of her mouth shocked me. "I think I want you to fuck my ass. But promise, if it hurts, we'll stop."

"Of course I will if it hurts."

She pulled her shorts down and took my cock. This was unplanned, so there was no lube, so she went down on me for a couple minutes. She gave the sloppiest blowjob she knew how to give so I was covered in her saliva, she rolled back so we were spooning, gripped my cock and guided it to her asshole, then said "Push gently."

I pushed and felt the head of my cock enter her virgin ass, she was very tight and it was warm. She pushed back into me, letting me go deeper. She moaned in pleasure, then said "Go slow."

I slowly pushed in, then slowly back out, each stroke getting an increasingly intense moan each time. B Between moans she blurted out "I bet a cock in my pussy would feel amazing!"

She then started rubbing her clit, then asked me to rub it instead. She was soaking wet and I rubbed her clit as she liked. She then asked me to go harder and j picked up the pace. Her moans grew deeper and more from her gut and she is grinding back. She then starts reminding me to use my hand to, and then starts grinding back and I go deeper and deeper, she then starts loudly moaning and saying "Hands! Hands! Hands!"

She then screamed "I'm cumming, ohmigod I'm gonna cum!"

At this point I can no longer hold it in and tell her I need to cum and she shocked me and said "I need to feel you cum inside me. Cum in my ass!

She was grinding harder back and I exploded into her ass. She pressed back so I was as deep as I could be as I squirted a couple more times. We laid there for a bit, in aww of the moment. When she got up she felt the cum run out of her ass down her legs.

She said "I don't know why girls say that hurts, that was amazing. Don't think we will do it every time though."

Within 2 months, she actually looked forward to her period for "anal week".