When I was younger, I always wanted to save my virginity for the right guy. I had a couple high school hook ups who tried to push me into having vaginal sex with them. I was always open to giving hand jobs and blow jobs, but wasn’t ready to fully go all the way.
The first time I offered my ass was after a party where I had been drinking. The guy I was with was someone who was older and definitely not a virgin. We were making out on my couch and he asked me if we could fuck. After telling him I was virgin he sort of laughed it off and told me he wouldn’t push any further.
We ended up naked and things started to get really heated. He had a pretty thick cock and kept on rubbing it up against me.
“Just let me put in the tip. I promise that’s it. You’re getting me so hard and your body feels so good.”
Part of me knew he was just gassing me up to try and take my virginity, and it was working. I wrapped my lips around his cock and started sucking on him in the hopes it would appease him.
“Bend over. I want to try something.”
I bent over, my pussy and ass fully exposed to this man. He started rubbing his naked cock against my holes and it was driving me mad. I could feel the dampness seeping out of my pussy as he rubbed his cock on it.
After a few moments of rubbing and driving me mad I said “you can try my asshole if you want. But please don’t fuck my pussy.”
I heard him gasp in surprise behind me. He spit on to my asshole and he started with a finger in my ass. It hurt and was uncomfortable, but I would be lying if I said it didn’t feel good.
He got his tip inside of my ass and I remember almost cumming from that. The sensations from the pain felt really good.
“Fuck your little asshole is tight you slut.”
He eventually got his entire cock into my stretched hole and came within a minute, deep inside of my poor little asshole.