*Well, that is if all the boys and men who’ve come in and out of my life since I was 13 were actually my lovers.
About 9 years ago, I read the book How To Date Like a Man by Myreah Moore. I don’t remember much from the book. However, I do remember that she suggests that women should date 100 men before settling down. It was then that I decided to take on this challenge. Now, my list is sort of all-inclusive, meaning I include the boys since I was 13. They also play a major role in shaping how I relate to men. I started studying Judaism at 13 because of one of them. Oy vay. I also include men I haven’t technically dated, but they’ve made some impact on my love life. So I’ve loosely based my list on Ms. Moore’s model.
I classify the men into 8 categories, including the list of The Sex That Got Away men.
Here’s the list in numbers:
96: the number of boys and men
15: the number of lovers I’ve had
34: the number of lovers I’d have had if I slept with the sex that got away men
75: the number of lovers I’d have had if I had been looser (I’m sort of uptight); were sexually active at 16 (like everyone else I knew); had lower standards; and/or had been with men I just found sexually appealing (includes men who I do not consider the sex that got away).
1. Lovers and Live-ins – 15
These are the men who had me, and I had them. I lived with 3 of the 15, but one was after the break-up. Big mistake. I don’t remember #8’s name. There’s a reason why. When I met #8, he introduced himself as “John Doe.” A few months later, when he came into town to vote, we had a short fling, and I learned his real name. The sex was terrible. He couldn’t stay hard. So, while his struggling penis was still inside me, I started masturbating with my best friend, hand. That was when I learned that when there’s a penis (or something) inside me, simultaneously as I’m stimulating my outer vagina, I orgasm out of this fucking world. And that is when I discovered how to guarantee an orgasm while having sex. Of course, I must be on top to manipulate this, and I’ve learned how to do it without my hand by pressing my vaginal bone against his pelvis. I just need him to lie there and let me do it. It’s quite the experience for him too as he gets to feel the inside of my cumming, spasmodic pussy. So, while I may not remember John Doe’s name, I did learn something. The first time I did it with my succeeding lover, Steven, was amazing. The look on his face was one of wonder as he was learning what I was doing. His cock was ginormous, so there are no words to describe what happened. Every high-pitched noise that came out of me as I came was genuine. Unfortunately, I have not done this enough, with men anyway.
2. The Sex That Got Away – 19
I dated some of them. I made out like a horny teenager for weeks with some of them. I spent one great night talking with some of them. I went through emotional sagas with some of them. But, we never made love, had sex, or fucked. I think about them all the time. What would it be like to have an affair with them? Some of them I can actually envision a relationship with. Some I just see a healthy, fun fling. This category has subcategories which I will get into later when I share more about the men.
3. Dating Only – 10
These are the men who I dated. We either went on one date or several, but they don’t classify as The Sex That Got Away because I have absolutely no desire to know what sex would have been like with them. If I wanted to, I could have slept with them. One of these guys was a wealthy, redheaded twin with a very odd look and probably a closet full of fetishes. He was just fucking weird. Somehow, he got me in his bedroom. When I wouldn’t get into him, he whipped out his tiny dick and started jerking off. Out of sheer shock, and because he sort of asked me to, I stayed there while he talked dirty (to me, I guess) and finished. His twin and two of my friends were in the living room. I have done many, many, many things just for the experience.
4. Crushes and attractions, requited and unrequited – 18
These are men who I either crushed on or they crushed on me. In some cases it was requited; in others, it was not. Of these men, if I’d wanted, I could have had 17 of them as lovers. One was my boss, and I just don’t think he would have been willing. He knew of my crush, and I’m sure he was intrigued or flattered. The rest of the list is colorful including a political organizer who I met while campaigning in Vegas. Despite my attraction to him and vice versa, I thought he’d be a better fit for my lawyer friend. A few months later, they met by chance in Vegas and hit it off. Small world.
5. Could have been one night stands – 5
I could have slept with all of these men, and, without a doubt, they would have all been one night stands. One was my aisle mate on a flight from New York to Los Angeles. I met the other four at bars, and we made out. I just didn’t go home with them. And the attempt to connect a second time never worked out. I did not date these men.
6. Guys Whose Names I’ve Forgotten – 11
Because I feel so bad about forgetting their names, I think they deserve their own category.Nonetheless, of the 11, there are 8 I would have slept with if I’d wanted to. Some of the highlights from this group include a medical student I was having a wonderful time with on my last night on a cruise until I got food poisoning. He sat outside my room and listened to me vomit. He was very kind and wanted to take care of me. I sent him away.
7. Virgin Territory – 14
These are all the men I loved, dated, crushed on and made out with before I was giving up the goods. It includes the young man who took me on my first date on my 16th birthday; my senior ball date who I made out with for hours in the backseat of his father’s Volvo. He touched mine. I touched his. Of the 14, I’d do 10 of them if given the chance today. But they aren’t really the sex that got away. Due to the wonderful world of social media, I’m still in contact with six of them.
8. Long Distance/Online Flirting – 4
These are men I’d love to meet. We’ve been introduced and conversed through social media and done some flirting. I talk about how horny I am with one of them. We’re always talking about sex. If we were in the same town, we’d fuck. Then, after awhile, we’d go our separate ways.