I know, the title seems hard to believe. Until I reached my early to mid twenties, I could easily miss hints and cues directed my way. That’s probably part of the reason I was still a virgin when I graduated from high school in the late 80s. I had gotten as far as French kissing a girl, but that was it.
I enlisted in the Air Force, and after Basic went to the base where I would learn my career essentials. While there, I did manage to get to 3rd base, both in the base movie theater (very stupidly risky in hindsight) and the dorm TV room. The dorm, itself, was co-ed, but the bays were not. During my stay there, there was a female I had hoped to hook up with, who was known for being generally inclined to have fun. For easy reference, I will call her “B”. Unfortunately, I never did get a chance with B while at the training base.
As luck would have it, though, she and I did end up at the same base for our first duty assignment. I hoped to trade in on the “only friendly face” connection, and headed over to her dorm room. Thankfully, her dorm was right next door to mine. Knocked on her door, and B’s roommate answered the door. Her roommate was fairly average looking, some might say plain or homely, depending on your standards. I would eventually find out, though, that her body was just fine.
I don’t know if I could remember her roommate’s actual name at this point, but I do recall as part of our introduction (during which I explained that I knew B from tech school), she gave her nickname as “Risky”.
Risky and I started hanging out, talking, and for the life of me, don’t remember if we watched movies. I do remember that at one point, we started giving each other neck and shoulder rubs.
Yes. I know. Remember where I admitted I was pretty clueless? I also wasn’t reading anything into it because she was engaged.
As time went on, she would receive her back rub shirtless (but still wearing a bra). Then, the bra would stay on, but she would unhook it. Eventually, she would remove the bra from underneath herself.
I guess she finally got tired of waiting for me to get the hint, and one evening told me to stop for a second. I did, and she rolled over. These were the first tits I had seen outside of the various Playboy and Penthouse magazines my dad had stashed in the attic.
But, I digress.
Thankfully, the cluebat hit me upside the head about then, and we started kissing. It wasn’t porn story/movie level, but it was sweet, tender, and I was very nervous. I couldn’t tell you how long we kissed, or how long I licked and sucked her nipples. She signaled at some point that she was definitely ready to be fucked, so I rolled a condom on, and slid in to her. The warmth was like nothing I had ever experienced before.
Unfortunately, due to nervousness and the condom, Junior wasn’t entirely cooperative. With Risky’s permission, I removed the condom and went bareback.
Words can’t do justice to experiencing that warm, wet, soft grip as your cock slides in. I didn’t last long after that.
We remained “friends with benefits” for several months after that, highlighted by the time my roommate walked in on me fucking her doggy style. He smiled, apologized, and left.
(He and I would later joke it was payback for when I walked in on him getting head from his girlfriend).
So, not exactly a super descriptive sexual encounter. Apologies if it disappoints.
Source: reddit.com/r/gonewildstories/comments/a5zacs/lost_my_virginity_when_i_wasnt_expecting_to_mf