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The Story of My History With Women – Part 2: Losing My Virginity

September 8, 2016

My story continues! Hereâs part two of my history with women. If you havenât read part one yet, you probably should or you may not understand everything; itâs right here. When we last left teenage me, I was in high school with hardcore oneitis for a girl. Now I roll into my senior year, much more confident. Shortly after that, a very big event occurs…


By the time I hit senior year in high school, while I was still pining for Christy, I had built up enough confidence to ask girls out on dates. Even very pretty ones. I could walk up to a super hot girl, even one I barely knew, and ask her out on a date right there. I couldnât do this with all the hot girls, but I could with many, particularly if they were younger than me.

Even when they said no, I felt bad, but I was impressed with myself. It was a 180-degree difference from the terror I felt regarding women just four or five years earlier.

Many said no when I asked them out…but some said yes. This taught me something very valuable that would come in handy later:

Lesson Two

Whenever a pretty girl says no to you, never forget that thereâs always another pretty girl right behind her who will probably say yes.

Years later, after my divorce and getting into the dating game, even with limited experience, I still only dated very attractive women. I never fell into the trap so many men do, of only having sex with mediocre women and then having some kind of reluctance or complex about sleeping with pretty women. I think this experience in high school was the reason.

When I was in high school asking these girls out, I didnât see the point in asking out the average looking girls. It didnât seem logical to me. If I only asked out the hot girls, if any said yes, Iâd be really happy. Whereas if I only asked out ugly or average girls, if any said yes, Iâd be mildly satisfied. If I was going to get shot down, I might as well be shot down by really hot women.

When youâre out on a date with a really pretty girl, youâre not thinking about the three or four other girls who said no to you. Instead, youâve got a big smile on your face. This was my experience in high school.

I went out on lots of first, second and third dates with a few several pretty girls that year, impressing my friends and my sisters (who went to the same high school as me), which, as a teenager, was important to me. Regardless, I never got past making out and squeezing a few boobies. The negative Catholic programming from my mother was still strong in my mind, even stronger than my burning sexual desire.

In 1990 I finished high school and entered the work world at age 18. I could see that college was simply a way of going into debt and doing useless homework instead of making money, so I skipped it. For several years I worked very hard and purposely avoided women and sex regardless of how much it hurt to do so, which it did. I was focused on my overall life goal back then: making $100,000 a year.

At around age 22 I started working with a woman who Iâll call Penny. She was cute, funny, vivacious, just a little crazy, and we became close friends. She was about 40 years old at the time, and married. Though she wasnât blonde, she had the âChristyâ body I had been wired to like (shorter, long hair, big boobs, big butt, but not fat).

Our conversations were natural and effortless. She made me feel relaxed, happy, and excited all at the same time. She was very feminine, which always gets me excited. We often talked about sex and dating too. It wasnât something I did on purpose; it just happened. Like I said, talking to Penny was effortless.

In an attempt to protect my young and fragile ego, I even lied to Penny and told her I had already had sex with âabout four or five girls,â when in fact I was still a virgin. I was hoping she wouldnât ask a lot of questions about it, since I wouldnât know what to say. Fortunately for me, she didnât, so my secret was safe.

One night after the office closed, Penny and I were talking alone in the parking lot, there was an energy between us that started to make my heart pound and my face get a little red. She felt it too, and started bouncing up and down and touching my face a little as we talked. I had no idea what to do, so eventually we said our goodnights and I went home alone.

The next time I visited her office, we both decided to âgo for a drive.â Even as a young virgin I had a feeling I knew what that meant, but I tried to hide my excitement.

She drove her minivan and I sat in the passenger seat. We stopped off at a convenience store, got some juice, and continued onto a ridge overlooking the airport where we parked.

We sat and talked, and within about 30 minutes we were making out. My hands were all over her and I was getting super excited. I wanted to go further but she was too scared to do so in her car. Being a pussy, I didnât push it. (We could have had sex right then and there in her car if I had been more confident. She was all warmed up and ready to go.)

A week or two later we met up at a hotel, and it finally happened. We had sex, although I couldnât get it up. My virgin 22 year-old cock had no idea what to do with this excited naked woman laying before me. It was confusing to me, because I didnât feel scared or nervous. It just…didnât work. I wasnât scared, but my subconscious was terrified.

I tried, and tried, and tried. She also tried. Nothing worked. I was furious. I tried not to get upset. She felt sad. âIs it me?â she asked, âItâs me, isnât it?!?â It honestly wasnât. It was me. Dammit.

It took four separate âvisitsâ for us to attempt sex before my dick started to work correctly. When it did, oh man, it worked great. I started seeing Penny regularly, most weeks, for over about a year. Her husband was gone for long stretches for his work, so this was easy to do. With me being a virgin and her being married, we were both STD free (though she made me get a HIV test before we started having sex, which was expensive as hell back then) and she had her tubes tied so she couldnât get pregnant. I had so much fun with her, my memories of that time still make me smile to this day. It was my first ongoing relationship with a woman.

She was able to teach me some basics about sex but nothing earth shattering. Towards the end, to my surprise, she started getting real feelings towards me. This stunned me. She was married to another guy and still loved him. Her and I were just fuck buddies, at least as I understood the term back then (what little I understood anyway). We were close, and I cared for her deeply, but she was married and I was damn near 20 years younger than her. I had feelings for her, but eventually she wanted romance. I was confused. It made no sense to me at the time. This was another new lesson I learned about women.

Lesson Three

Most women (though not all) are hard-wired to start getting feelings for any man they are having regular sex with, regardless of the nature of the relationship they have with him, or his lack of desirability or compatibility for her long-term future.

You can logically say to a woman, âweâre just friends with benefitsâ all you want, and that might work for a while. But if youâre having regular sex, eventually, and it might take a while, most women (not all, but most) will start to get some feelings for you, even if she loves another man. Itâs how women work.

This doesnât mean you canât have very long-term FBs. I do all the time. You just need to realize that eventually an FB will LSNFTE you for a beta boyfriend if she doesnât feel her feelings are being returned. (And if you do everything right, sheâll eventually come back.)

During this time, when I went right from high school right into the work world of adults, I noticed several things.

First, I noticed that most women over the age of about 30 were always bitter about something; bitter about their divorce, bitter about men, bitter about their financial situation, upset with their âstupidâ husbands, stressed out about their kids, etc. This was a shockingly stark difference from the girls I had known in high school, most of whom were happy, carefree, and loved boys.

Second, I noticed that men who were unmarried tended to have happier demeanors than men who were married. This was very strange to me, since I had been told my whole life that marriage was the one great goal all men should have, and that you werenât happy until you were married to That One Special Girlâ¢.

The married guys always seemed to be whining about something they wanted to do but âwerenât allowedâ to do. This kept happening so often that I started making fun of my married work buddies. âHaha! You have to go home now because youâre ânot allowedâ to have fun! Iâm getting pizza! Haha!â

Third, I noticed that unmarried guys who had girlfriends had their own set of problems. They were certainly happier than the married guys, that was obvious. But they also seemed to have more drama. It seemed to me that guys with girlfriends were always on the phone with them, constantly saying things like âOkay, okay! Sorry!â or âGod! Whatâs your problem? Why are you yelling at me?â

To my shock, and I really was surprised and confused about this, the consistently happiest men in the adult workplace I saw were guys who didnât have a wife or a traditional girlfriend.


It quickly became apparent to me that my relationship with Penny was far superior to that of the married guys and the girlfriend guys I knew or worked with, at least in terms of how happy it made me (and her).

Though I wasnât exactly right, I had no idea that I was really on to something back then, and what big things had been started from those thoughts and observations.

Eventually, with my new sexual powers awakened within me, I started having sex with other women, which was a lot easier now that I had lost my virginity. It was as if losing my virginity had removed a huge sea anchor I was dragging around.

Soon I had to reluctantly say goodbye to Penny. It was amicable, and weâre still friends to this day.

One of the women I met during this time I would end up marrying, and oh boy, did that change things…

To be continued…

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Post Information
Title The Story of My History With Women – Part 2: Losing My Virginity
Author BlackDragon
Date September 8, 2016 12:00 PM UTC (6 years ago)
Blog Caleb Jones
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