This happened about 6 years ago around Thanksgiving. I was 23, she was probably 19 or 20. For some context; I was a virgin and had been on the online dating scene for a few years, courtesy of an old college friend. I’d been out on a few dates, but nothing like this. I was raised very traditionally, and while I wanted more than anything to have sex, I struggled for a long time with balancing my desires with my upbringing. This story was the first time I had a chance to actually hook up with a girl. Sexy stuff after the *******
It was a slow Saturday night. I was browsing around and came across a beautiful brunette, I’ll call her Michelle. She had a few cute photos, and I was instantly turned on. I hadn’t had any since early college, so I was a bit nervous. We matched, and had some idle chit chat. We talked about college (she was still in), past relationships, and whether or not we’d had sex before. Told her I was a virgin, she told me she wasn’t. Eventually she asked me, “What are you thinking about?” I replied, “You as my first.” Super. Response.
Fortunately she was more horny than critical of my lame replies, and she invited me over. It was around 1am, so I snuck out and bought my first ever box of condoms. I had no clue what might happen, but best be prepared, right?
When I arrived at her address, I saw it was a sorority house of sorts. Imaging something a la American Pie, I really had no clue what to expect. I nervously rang the doorbell, and the door opened to a wonderful sight. Michelle was stunning. Her waist-length brown hair, gorgeous blue eyes, and she was perfectly dressed in short shorts and a white tank top, with a clear outline of her black bra underneath. She invited me in and led me upstairs. I remember being at eye level with an amazingly plump ass, and I was instantly hard.
She led me up to her bed, and it was legit the most awkward opening moment I’d ever experienced. We eventually started talking, which led to kissing, which finally kicked things off.
*********
I was laying on top of her, and we broke our kiss long enough for her to pull her white tank top off and toss it to the floor. I immediately went back to kissing her…after too many years not having kissed anyone, I was lost in the feeling. She pushed me up, then led me to remove my shirt. She then nudged me down, and I kissed over her bra and down to her shorts. She lifted her butt slightly up off the bed, which I took as a cue to slide her bottoms off. She had the most amazingly smooth, white skin. She wasn’t completely shaved, but it was the loveliest thing I’d ever seen at the time.
I immediately went in and started kissing her mound, then slowly down over her lips. I slid my tongue in, and immediately her back arched. She started to moan softly as my tongue circled her clit. Then, all of a sudden, her moans got louder and I felt a warm pulse on my tongue. She grabbed my hair, pulled me up, and kissed me.
I then pulled her up & unclasped her bra. Her plump, 32B tits bounced down. (My last girlfriend had pretty large boobs, and I was insanely turned on at smaller ones to play with.) I wanted to kiss them, but she pushed me down and removed my pants. I was hard as hell, freshly shaven for the occasion. She smiled a bit, then straddled me.
More context: my last girlfriend and I were always nervous about getting pregnant, so we never had our genitals anywhere close to each other. Fast forward to then, Michelle slowly lowered her warm pussy onto my throbbing cock. I was in heaven. She slid up and down my shaft, and I could feel her wetness pushing down on me. It was an incredible, unforgettable feeling. She then motioned for me to “get something”, to which I eagerly did.
I’d never put a condom on before, but I quickly figured it out as she sat next to me rubbing my shoulder. After it was on, she got back on top of me and kept sliding.
We made out a lot more, she kept straddling, but never pushed me in. After a while, we were just laying there, and I asked her if she wanted to actually have sex. She told me that she had this gut feeling that I wasn’t ready, to which I (thankfully) agreed. It was the strangest feeling ever – I was incredibly turned on, but it just felt wrong. She climbed off me, and I spooned her as we talked about life and our upbringing. After a while, we agreed I should head home. So, we got dressed, I picked up my opened box of condoms, and headed out the door, greeted by a peaceful sunrise.
When I got home, I jerked off & came in about .5 seconds. We never talked after that, and it began a long journey of trying to figure out if everything I was led to believe growing up was what I really wanted.
(This is my first time writing, hope you enjoyed it! If there’s interest, I’ll share more in the future.)
Source: reddit.com/r/gonewildstories/comments/k3phsw/my_first_hookup