Truth #23

When did you lose your virginity?

I suppose by what I write and how I act at this point in my life the average reader would likely make the erroneous assumption that I was an early bloomer. Wooing women and wrestling pimples simultaneously. This, as much as I wish it were true, just isn’t the case.

I didn’t have my first girlfriend until I was I college and even though I believed the relationship was fantastic in reality it was merely stupid puppy love. I had no clue how to conduct myself at the time and it’s hard to not look back at my actions with embarrassment. Suffice to say the relationship didn’t last long and certainly did not last long enough to become intimate with her.

A year or two went by and I didn’t fare any better with girls. I was very good at making friends with them but couldn’t seem to take the next step. Now last Monday truth I discussing cheating and how I had been involved in a cheating situation during my first time. I had said it was under the surprisingly exhilarating cloud of cheating but I have to clarify. While the situation was exhilarating, the sex definitely was not.

It was horrid. Despite her being in a long term relationship, and despite her proclamations of her vast skill, she had none. Without a doubt she was the worst kisser I have had the displeasure of experiencing. Though she claimed to be an excellent kisser and how all the men she had been with had told her this, she was utterly awful. Her “technique” if you could even call it that, was to jam her tongue as far as she could into my mouth and then simply swirl it around clockwise over and over and over again. It was horrible. She wasn’t so much kissing me as she was showing me what it would be like to be infested with an alien parasite.

Her skill in bed was equally pathetic. I had anticipated foreplay. I was ready for it. I was jazzed up for it. All the reading, studying, thinking pondering, all that time wishing for some chance to take theory into practice was finally here. Or so I thought. Apparently for her, the kissing was enough. But I was young, stupid and inexperienced, so regardless of me not being in the moment at all, my penis was very much ready to rock.

Now in every movie or TV show I had seen up till that point, they always had made fun of a boy’s first time because it seemed to be over so shockingly quick. I agonized over this. I was so worried that when it came to my chance that I would be one of the infamous ‘minute men’. Once more, however, my fears were assuaged by her. I didn’t have the opportunity to be a ‘minute man’ because she took that role instead. Because of my lack of experience, something she was acutely aware of, she decided that she would take charge. I was on my back, lying down as if a bear was attacking and I was feigning death. About three minutes later, or maybe even less….she was done…and that was that. She collapsed next to me, muttered something about my “cock is amazing…and…that was amazing….” and then cuddled with me in my tiny twin bed for a while before deciding to slip out and go home before her boyfriend got home from work.

“We need to do this again sometime.” was the last thing she said to me that night, before I closed the door behind her. I just fake smiled and nodded then locked the door. When I turned around I saw my roommate who was getting milk in the kitchen. He looked at me and gave me an approving, “duuuuuude” nod and I slinked back to my room.

I had sex with her twice more in the following weeks. One may ask, “Why? Why would you do that if it was so horrible?” It’s because, I didn’t know it was horrible. I had no frame of reference. No understanding of what good sex was like. Sure I had seen porn, sex scenes in movies, I’d read and written erotica by then as well, but I had never experienced it firsthand. After the first time I was actually quite worried. I thought maybe there was something wrong with me. She, after all, was so incredibly excited and I was nowhere close to that. Maybe I was broken? Maybe I’ve got a problem? Maybe……I don’t know? I worried. I fretted and became so obsessed with figuring it out, that when she came onto me again I once more let it happen. It was marginally better the second time, but only marginally. She lasted a full five minutes I believe, but once more she came, and I didn’t. She didn’t appear to notice. She didn’t appear to care. I was beginning to wonder what the hell all the fuss was about. Why were my classmates so obsessed with sex? It wasn’t interesting in the least! It was barely exciting, and hardly felt good at all. After the third time with her I decided to stop being so worried about getting laid, because clearly it wasn’t worth it. The next time I had sex was several years later and was so much better it was only then that I realized that it was her, my first, that was the problem and not me.

She romanticized the moment too, which in retrospect was quite funny. She swooned over the idea that she would be my first. “You never forget your first.” she said on multiple occasions. I’m sure that she thought that all my memories would be of fondness and obsession for the excitement of my first time. In reality, however, she goes down as the worst lay I’ve ever had in my entire life. She is the benchmark for bad sex. She is the mark of the lowest tide. In her mind, I’m sure she still considers herself to be a sultry minx, which is hilarious because for that amount of self delusion you’d be surprised of her current profession. She is……a psychologist.

Anyways, the question was when I lost my virginity not how. So I was 21 at the time. That’s the when. But answering a question with a simple one sentence answer seemed very curt and boring, hence the story. I hope you found my tragic first, second, and third experiences amusing. I think it would be a delightfully cathartic experience if you, my readers, share your own.

Good, bad, or horrible. Share your first time in the comments. Let’s all enjoy our naivety together. 😉



Next question?



2 thoughts on “Truth #23

  1. My first time was with my best friend of four years. We were both 16 almost 17 at the time. We fumbled around as you can imagine since we were both virgins. It wasn’t a bad experience by any means physically, but it was nothing spectacular. (We did it once at our high school under the auditorium stage on his trench coat on one of the sofas used for a prop in plays 🙂 ) I didn’t have high expectations and for me sex has always been a lot about intimacy. It was the emotional aftermath of that relationship that really sucked since two months later he told me he wanted to “see what else was out there” and broke off all ties with me. He then dated the first girl he went out with and his relationship with her lasted for three years. All things considered I have to say that the hardest part was loosing my best friend. After that I am very happy to say that men, all always several years older than me, have treated me quite well.


  2. I was 16 almost 17 and he was 19. He had been my crush all of my freshman and sophomore year in high school. I was his gf for less thank a week when he decided he wasn’t ready for a relationship. The dumb hopeless romantic girl that I was decided that he was the one I was going to marry. So the night before my junior year started I snuck out of my room, walked to the park that was close by, where he was waiting for me in his expedition, and he took me to his apartment. We started watching Rent but once we started kissing it was hard to stop… There was so much sexual tension between us it was so intense… I told him I didnt want to several times but my body wanted it so bad that I gave up. I remember him ripping my pants off and telling me he’d buy me a new pair lol. He was a bit gentle at first but as time went on he became rougher and rougher. He told me he loved me but I knew it was a lie… I think we went at it for almost 3hrs he was so good. Sorry I got too excited haha. Even though he hurt me a lot emotionally he knew how to please me physically. He was like my drug, every time I felt depressed he was there to help me through sex. But yea that was my first time (:


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