My first time happened as a unification of two lonely and horny people living hundreds of miles away. A typical May-December relationship of the seductive woman and me the naive kid. She wasn’t much older, but enough to teach me a thing or two.
We met on the internet and agreed to come out to visit me in college. Most exciting time in my life I must say. Pussy is coming to me! Me? Yep me.
It was kind of a birthday present for her and she wanted to try out a few things. So while home for a weekend from college I went to the local adult store. This was not one of your nice and new adult megastores, no this was your typical one on the east coast you’d find only one day while lost and never forget about it: dirty, grimy, and ironically on the other side of the tracks. I went in and bought her a ‘purple jelly dong’ and some Astroglide™ as per her asking. Twenty five dollars later I had my non-descript brown paper bag and was heading home.
The night before I left back to for school (and a nice 4 day introduction into sex) my father was helping me load up my car. He came up stairs and looked me in the eye scared and just said “Please tell me that’s not for your roommate Joe”. Right there that should have warned me that this week would be bad, but no pussy was on my mind.
She arrived that Friday at the airport. I picked her up and was just so excited. I’m gonna get laid, I’m gonna get laid, I’m gonna get laid. That mantra still goes through my mind today before I have sex, but I think it has quieted down. We went and had a fabulous dinner at the Ponderosa and then went back to the hotel. We were on the bed, watching Independence Day the movie, a very romantic movie about aliens attacking the USA, when we started to kiss. She actually said, “Hold up there cowboy” as I started to frantically undress her.
I still think she was beautiful. It’s tough to convince her of that, but I loved her. Her creamy white 38D’s just pouring out of her chocolate brown bra. It was phenomenal. I remember her scent, Freesia, Bath & Body Works. The super 32 pack of condoms I got would come in
handy I thought as I unrolled the first of many and entered her. It didn’t last long, but we both did come, and at the same time. On the TV, I could see the aliens destroying the White House the same time as I climaxed.
We tried out her birthday present after that. Turned out the damn thing was broken. Who would have guessed a 20 dollar dildo would break. Well it became a dildo instead of a vibrator as it was supposed to be. C’est la vie.
We both tried anal sex for the first time ever that weekend. It was started during oral sex. I was eating her out, running my tongue along her clit and fingering her, when I took my hand out and ran it down to her asshole, rubbing the pink bud and slipping my index finger inside. Probing her. She loved it. It helped bring her to climax. After that we tried the astroglide. My cock was sheathed in a condom and ready to go in. I positioned next to her waiving ass, fingering it furiously before pushing my head to her asshole.
The next part will forever be burned into my memories:
She – Ok I’m ready
Me – Ok, I’m going……
She – Mmmmm, oww, oww, oww, OWWWWWWWWWWWWWWWWW
That was the last time I ever had anal sex, btw.
I lost time how many times we had sex over that extended weekend. That was also the last time we ever had sex. I brought her back to the plane, she called home and had about 5 messages from my mom looking for me. We kissed goodbye and that was it. She entered the airplane to be gone forever. The End.
Except my mom.
She called the cops to report a missing person and came to college looking for me with my dad. My roommate knew where I was basically, but is he going to say “Yeah he’s off fucking for the weekend, want me to call when he’s done?” We sat there in Ruby Tuesdays after my parents showed up at my dorm around 8pm with the campus police. They took me out to dinner and scolded me, well my mom did. My dad knew basically what I was doing.
I still think about her. Not that I think we’d have a great relationship, I just want to know what effect I had on her. Maybe none, maybe a lot. I guess I’ll never know.
