I’m writing a series describing all the women I’ve had sex with.
**1 – Losing my Virginity**
**Meeting**
I was a big nerd in high school, so the story of me having sex doesn’t start until I’m already 18 years old, in my senior year. I had dated like 2 girls during high school, kissing but nothing much beyond that.
I was a huge music nerd, in orchestra, band, and choir, as well as playing jazz outside of school. My main instrument was jazz upright bass. I met my eventual girlfriend through music. I would play with a guitarist in my area who had a few restaurant gigs and loved to throw parties at his own house. He was fairly well off, living on a lake and partying with his other lake friends. One of these friends lived across the street from him and had a daughter my age – we’ll call her T. She attended our rival high school, so we knew none of the same people.
At the first party gig I played, I noticed her but thought she was way too young for me. But, her mother dropped a bunch of not-so-subtle hints during the party and basically told me she was my age and we should date. I was still super shy and awkward, having almost no experience at all with anything like this, so I did nothing.
But, T. would not be so easily deterred. She had her eye on me, and we would meet frequently since I was always across the street from her house rehearsing. What was she like? Well, she was really cute and thin, standard cute blonde girl. But – and I say this not to be mean but just because it is true – she was the stupidest person I have ever met. In addition to being a music nerd, I was a “smart kid” who never studied and got As. So this was completely new to me. She listened to the top 40 radio station that I detested. She was transparently manipulative. She watched MTV instead of reading books. She smoked (!) Marlboro Reds. We had no shared interests. I mean, she was just a complete moron. Again, not to be mean, but that’s just the truth. But, she was also really cute, and as I was later to learn, she was a horny sex maniac.
**Hooking Up**
Eventually, after weeks of her aggressive overtures, I invited her to my house. I was giving her a massage on the couch and she said, “You can do something if you want.” Yes, I was so clueless that she had to instruct me to make a move. So I kissed her. She grabbed my hand and stuck it down her pants. Needless to say, this surprised me. But holy shit, I was touching her pussy! Okay, whatever, I fingered her while we made out, trying my best to do a good job. According to her, she had several orgasms, but she was always talking about all the orgasms she had, so now I think maybe she just didn’t know what an orgasm was.
After we finished making out, I drove her home, kissing her at every stop sign. I was convinced that I was in love. After she got out, I left her shitty top 40 radio station on all the way home. Looking back, I can see that I was completely unprepared.
But, I knew what to do when I was facing an unfamiliar situation. I went straight to Barnes and Noble and spent a few afternoons in the Sexuality section reading as many books on the subject as I could. I was very intent on doing a good job – this would become a pattern in my sex life. And the books actually helped a lot! I knew where the clit was, what the g spot was, and most importantly, we could talk about what we wanted and what was happening.
Not long after our first kiss, we were sitting on her parents couch, and she put her head on my lap. Her parents were upstairs, or on the patio or something. All of a sudden, she starts biting at my cock through my shorts. Now, I thought oral sex was serious business, but here she was with her mouth on my cock while her parents were home. I squirmed away, shocked and anxious that her parents would catch us. She smiled and giggled, then attacked my cock once again, putting her mouth around the bulge in my shorts. I was still terrified that her dad (who looked like Mr. Clean and had a safe full of guns) would catch us, so I kept trying to get her to stop. But she was intent on embarrassing me, and just kept at it, chasing me around the room trying to put her mouth on my dick. Needless to say, oral sex started soon after.
I will spare you the details because I don’t remember them. But suffice it to say that I spent a whole lot of time 69ing for the next few months. I remember that I started by trying to fuck her with my tongue, like sticking it as far as I could up her vagina. But eventually I paid attention to what made her cum and got better at it. She didn’t like me to cum in her mouth, so I would always tell her when I was going to cum, and she would hold up a tissue. Adorably, we would always brush our teeth afterwards.
So eventually, she told me “I want your dick inside me,” and we made plans to have sex. Yes, she was the one who brought it up. Even after all this, I was still too timid to make an advance. So, with the help of my older brother and his credit card, I booked a hotel room for us and we made plans for a special night together. I told my parents I was sleeping over a friend’s house, and T was supposed to do the same. But, she didn’t – in fact, she didn’t tell her parents anything. She just disappeared and didn’t come home.
So here I am in a hotel room with a pack of condoms and my sexy girlfriend who wants to fuck me. And … I couldn’t get it up. Maybe I was nervous because it was my first time. Maybe I was afraid that her father would find us, kick in the door, and shoot me to death. Whatever the explanation, I couldn’t perform. And indeed, I eventually got a call on my Nokia from her father. I still remember his voicemail: “I wanna know where my daughter is. I’m pissed off. Call me back.” Ah, the game was up.
So what did we do? Call back and explain? Drive home? Stay in the hotel and have a great night? No! None if those things. I have said that T was stupid, but looking back on it I was not the brightest crayon in the box either. After getting that voicemail from Mr. Clean with guns, we decided to flee the hotel and go to my friend’s house to sleep there for the rest of the night. Why? I can’t remember why we thought that was a good idea, but we did it.
The next day we went home to a torrent of admonitions from all of our parents. But here’s the funny thing – her parents didn’t object to us continuing to see each other. Maybe they realized that I was not a complete fuckup like the rest of her friends (who I never met by the way). To top it off, she had accidentally tossed a cigarette into the back seat of my dad’s car and burned a hold in the upholstery. Still, no red flags or alarm bells were going off for me.
**Cheating**
So, before we actually fucked, she went on vacation to Florida and had sex with the son of one of her parents’ friends, who was also on the trip. She told me about it because she was incapable of keeping a secret. I was upset, of course, but in my youthful naivete, I thought to myself that I still loved her, and love was the most important thing, so we should be together. Well, looking back on it I’m actually glad I did that. Because we had a shit-ton of sex. I would go over he house every day, go right up to her bedroom, and we would fuck straight through until I had to leave. I remember once we could see her parents’ car coming down the street, and I was about to stop, but she pulled down her pants, bent over, and said “Please? One more time?” Ah, young love.
By this time, you have already guessed what ended our relationship. She cheated on me again at a graduation party. At that point, I said “I still love you, but that’s not enough for a relationship, and we can’t be together anymore.” A few months later I heard that she was pregnant.
Looking back on this, I was dodging bullets like I was in The Matrix. But I’m glad that I had my relationship with T. We always played safe, which is the main thing. The heartbreak fades, but the pussy-licking skills I learned have lasted a lifetime. So for any young people reading this post (if you are too young to be reading this post go back to playing Minecraft), go ahead and fuck that sexy person you have nothing in common with. As long as you avoid diseases and pregnancy, you can have a bunch of good sex and get out whenever you feel like it. Enjoy your life.
**Future Installments**
Here’s the full list of hookups, which I’m posting here just so I don’t forget it. Sexually aggressive women are a theme.
Losing my virginity
Jazz singer from Colombia
Two in Peru
12 years older
8 years older, living together
5 years younger
College girl
Chubby
Lavalife
My wife
Dancer/fan
Craigslist 1
Bartender/stripper
Friend of a friend
Craigslist 2
Craigslist 3
Adult friend finder
20 years old
Tinder 1
Tinder 2
Tinder 3
Tinder 4
Tinder 5
Source: reddit.com/r/gonewildstories/comments/jew9sr/all_my_hookups_1_losing_my_virginity
So where is the description of you losing your v-card?