It’s time to play the numbers game for processing sake.
1. Lost my virginity in the winter. Sixteen going on seventeen. Chased him down, in a sense. Held a candle for him and even started smoking weed for the fella. He was sweet. After he pushed in, I must have been grimacing because he kissed me on the forehead and told me “it gets better.” It certainly does. I looked forward to it after that. We broke up in the summer. Had him as a booty call on occasion a couple of years later. The first time after we broke up, he kept moaning about how it felt different but so good. I still, to this day, don’t know why.
2. I can’t remember his name. I was nineteen and had an almost two-year dry spell. Some guy at a local college started chatting me up in Myspace. I remember going to his dorm room and he popped in Mystery Science Theater 2000. I don’t recall the contents. Just how much his rather large and half-mast penis hurt. If it started feeling better, I don’t remember. I didn’t sleep there. We tried to make plans a couple of times but we each blew the other off. Some time later, he would hit me up again. I think he forgot we slept together.
3 and 4. I was probably twenty. My first threesome was with one of my best friends (from when we were in middle school) and her boyfriend. She said it was a present to him because it would cross off two of his fantasies: having a threesome and doing it with an Asian. I’m half Asian so I guess that counted. Afterword, I slept on the floor while they slept on the bed. I pretended to sleep in the morning while they whispered to each other, arguing about him putting it in me. I remember it as not being spectacular. I think I would have considered this a good experience if I did not overhear the conversation.
5 and 6. Another Threesome. I was really into this guy who was flirting with me. Then his ex girlfriend wanted him back and she took a liking to me when we met. Next thing I know, they were propositioning a threesome. I was twenty-one and feeling adventurous after not getting any during my time away at college. They had one rule, I could not kiss either of them. It was too…intimate. Penetration was fine, however. I almost had my first orgasm but held back. I was still naive.
7. A crush I had in college would play games. One day he would be interested, one day he wouldn’t. I turned twenty-one and I wanted so bad to be with him but he was chasing another girl and it was only when I left the school, that he realized he felt the same. A couple of years later, I was in his dorm room and he came in two minutes. I never pursued him again. However…
8. One of his best friends pursued me and I would constantly ignore him until one day, I decided to give in and chat with him. From that, grew a flirtation. From that, grew a sexual relationship that lasted approximately a month. It was the first time I pretended to have an orgasm since high school.
9. I was twenty-two and out with my best friend of whom I met in college. She was, very much, into a guy and we met his friend. He was a marine who was back home to visit. He had recently had a divorce and was looking to have fun. We all went back to hotel. The marine and I were in one bed, my friend and her guy in the other. There was no shame. It felt good. I moved to North Carolina with him within four months of having a long-distance relationship with him. The sex was fantastic at first, but it died off. He broke up with me and made up with me a couple of times for no reason. Later, I found out he was carrying on inappropriate conversations with another girl so when he deployed…
10. I found myself in bed with a native North Carolinian. He was big but he knew how to use it. Probably the top out of the few I’ve encountered. I only indulged him twice before succumbing to the guilt. Two wrongs did not make a right. Not to me. When my boyfriend and I finally broke it off, I saw the North Carolinian for one last hurrah before driving back to my home state. I did not regret that night.
11. New Years Eve later that year, I was with a group of friends at First Night Boston. My friend had a half-brother who found me attractive. The group of us slept in the same hotel. He and I shared a bed and silently explored each other. I slept with him two more times before he had to deploy. He was in the navy.
12. A friend of my best friend’s boyfriend flirted heavily with me. I was 24 and found him heavily attractive. He invited me over to watch a movie. We had sex but then my period came. I felt bad. I whipped off the condom and finished him off with my mouth. I was a delightful one night stand. I do wish I could have experience sex with him to the fullest.
13. On the verge of turning 25 I met my sexual soul mate. I bettered my skills because of him. He was another friend of my friend’s boyfriend and we flirted heavily through texting and Facebook messages. We had sex nine times when we first met up. We would continue an on-again/off-again four-year relationship. We had many wild nights full of passion and pleasure. He gave me my first orgasm. Our final year together was sexless and it was then, I was able to walk away.
14. The first time my boyfriend and I took a break, I hooked up with a man with a rather large penis. I was not much into it and I can remember the smell of beer on his breath. I didn’t like it and did not see him again for a second time.
15. The second time my boyfriend and I took a break, I went on adult friend finder and met a man with a 9 inch penis. The sex was good but his size was a bit much for me. My ex was a seven that was more than enough for me as it was. I bought a 12 inch dildo to prepare myself for him. I saw him a few times before returning to my boyfriend.
16. When I finally broke it off with my boyfriend, I ran to a guy who was flirting heavily with me near the end of my relationship. We began a friends with benefit thing but he had multiple partners. I couldn’t resist the good sex, so I tolerated it. By the time I started having sex with him, I had finally learned how to orgasm without the other person having to put in any effort. I could now come regardless of how good my partner was. All I needed was penile to vaginal stimulation and I could do the rest.
17. I had another threesome with my friend with benefits and a tiny Scorpio girl. It was a good threesome and lots of fun but I would have preferred a woman who was more into women. She was young (mid-twenties) and had a tight body but she wasn’t my type. I was thirty at the time and would have preferred him all to myself. Not for a relationship. Just for the sex.
18. An old community college buddy from when I was 19 began messaging me. After some steamy messages, we agreed to buy a hotel room and have a tumble on Valentines day. He had a hard time keeping it hard. I made do with his unreliable penis for a month before giving up. I couldn’t take it anymore.
19. I succumbed to boredom and met up with someone from tinder. I instantly pegged him for a fuck boy and gave it to him for one night, while half-heartedly flirting with the idea of meeting up with him again. I did not meet up with him again.
20. My first pathological liar. Another tinder man. After a week of chatting, he absolutely couldn’t wait another day without seeing me. My brain took a vacation for the two weeks I was involved with this particular man. While his profile said he was 36, he told me he was 42 after we had a tumble in my bedroom. When I checked tinder the next day, his age was set to 42. The fucker changed it while I slept. He became upset with me when I refused to commit to only him. He was infatuated with me and I could not tolerate it. No sex, however good it was, was worth the red flags.
21. I decided not to have sex with him the first time I hung out with him alone. We met a couple of years before but I thought nothing of it. When we met again, we started a friendship. He finally hinted that he was trying to flirt and alluded to wanting something a little more than just the company of my friendship. I finally decided to give him a chance when I realized I might feel the same way. When we had sex, it had been a few months since I last done it. I came and dropped like a bag of bones. He did not want to disturb me, so he proceeded to finish himself off. I would have preferred to do the deed but was a bit too flustered at that point. I have never seen a man do this while staring so intently at my vagina. I tried another day to get things going. I had been fantasizing about going down on him all week and he seemed to be enjoying it. I didn’t finish him off because I wanted him to come as he did me. It was four in the morning and he ended up falling asleep with me left unsatisfied.
This was over a week ago and I find myself stuck in a place where I can’t get out. The flood gates have opened again and I need something to fill me once more. I pray I encounter something fun as soon as possible.