Sex and the Big D

I was 21 before I learned to masturbate.

Up till then I hid my naked body from myself most of the time. I didn’t really even look at it when showering. 

Weird? Yes. But I was raised Southern Baptist and sexual sin was considered the greatest. Honestly, I think I was afraid of my body and what was ‘down there’. In addition, I’d taken the true love waits pledge and seriously believed I would wait to even KISS a guy until my wedding day.

My body scared me, boys scared me, all the sexual TERMS scared me. Blow job. Doggy style. Eating … I mean, what?? I had to often pretend like I knew what my friends were discussing, then run home and ask my mom which was even more embarrassing and terrifying. 

When I started to explore myself sexually, I had no clue what I was doing. I wasn’t even sure I wanted to figure ‘it’ out but from all the conversations I’d had with friends about it, it seemed like it was something I was gonna have to do eventually and I was pretty sick of being alone. I kind of felt like my V-card was becoming a burden. I thought if I figured out how to, you know, pleasure myself I’d have a higher chance of actually losing my virginity.

I’ll spare the graphic details but I will say was trying to learn to masturbate when you have no clue what’s going on down there is hilarious. Well … in hindsight it is. At the time it was frustrating. I tried a plethora of random things (like really random things), but no success. Because ummm, I apparently wasn’t paying any attention in biology and had no clue what (or WHERE) my own clitoris was. So … one day I borrowed my roommates computer and searched ‘how to masturbate’. I found a forum that explained how my body was supposed to work and eventually I figured it out. Wowza. 

I tell this story because, well, it’s funny (to me) and also it offers some insight into the type of person who jumped into a long term relationship at 23 with very little to no sexual experience. The intense level of guilt and shame I felt for even having sex in the first place took a long, long time to work through. Even inside of a committed relationship I would feel dirty having sex. But I also so deeply craved physical affection. Quite frankly, the guilt was another reason why I was convinced I needed to make my problematic relationship work despite all the signs pointing to us being completely incompatible. 

So when I separated from my ex, I was 31 and had had two sexual partners. What followed was a time of transformation and discovery and here’s the fun part. I decided to be a sexual explorer. I didn’t do this in my 20s and maybe that was a good thing. Because now I was divorced and in my 30s and after having been burnt and starved for affection in my last relationship, I was ready to try all the things that I’d always been curious about.

Enter ‘the Fuck-it list’. I didn’t actually have a WRITTEN list. But there were certainly things on my list that I’d subconsciously always been curious about, even during my 8 year relationship. For one, I’d always wanted to be with a girl. There was a time in my early 20s I thought I WAS a lesbian. Being 21 and having never kissed a boy or never having had a boyfriend, there was certainly a part of me that wondered, well maybe I’m gay? Maybe that’s why I apparently REPEL boys? In addition, women are beautiful, kind creatures that I had no trouble with interacting with.

So when my time of sexual exploration began, a threesome was at the top of my to-do list.

Let’s just double-check I even like penis and I’m not gay.

Which I had the luxury of one of the most perfect scenarios for such an encounter – a younger man and woman, college age, were also sexual explorers. They liked to occasionally have threesomes with girls they met. So they were basically strangers to me. Which I have to say is the ONLY way (in my opinion) one can have a threesome. I didn’t know them, but they were nice and funny and attractive and we all seemed to want the same thing. I will say this was one of the more beautiful experiences of my time of exploration. No jealousy, no body consciousness. It was kinda perfect as far as threesome encounters go. (And yes I fully committed and tried a girl. It was wonderful, she was GORGEOUS … but in the end, I still found myself wanting the man more.)

I’ve also briefly been a dom (I’ll write about that later), was involved in a sexual relationship with a bi-sexual man, had sex in various public places (thank god I never got caught), hooked up with men of all races, ages and body types, including a very promising and quite beautiful quarterback of a college team (literally the worst sex of my life). My number sky rocketed from a modest 2 to well above 40 in less than two years time. 

Why do I tell you this? Well for starters it’s part of my story. And that’s what this project is about for me. A tell-all, not that I’m all that important or that anyone should care. This is for me. An honest assessment of my life. You see, that time of sexual exploration was incredibly freeing. It was very important to me and yet I’ve often felt dread and shame at how high my number went. I believed in true love waits remember? So for a bit after I’d ‘calmed down’ I started to feel guilt and shame for my high number of sexual partners. For having one night stands and sex only relationships. For the sheer AMOUNT of sex I had. Ironically, men don’t really ever feel this level of shame or guilt. They don’t feel dirty for having slept with an obscene number of women. But guys don’t really want a woman with a past, eh? It is only now that I realize that my time as a sexual explorer is actually something I am proud of and grateful for.

So I have a past … and at the end of all that wild, crazy sex what have I learned? That yes, a threesome is a very ‘hot’ idea and yes sex with gorgeous, muscled men can be fun and sexy, but the best sex in the whole world is that deeply connected, passionate sex that comes from knowing someone intimately. Vulnerably. That is the shit. And nothing else, no matter how pretty or wild, compares.

But I’m the type of person that learns through experience. And I’m so glad I got to learn from that experience, from that time of exploration. This is the beauty of being single, truly single. And by truly single I mean, when you’re not looking for a relationship but you’re interested in learning more about you and what you need and want. I got to try things and figure it out for myself. I learned about what dick size I genuinely prefer (these are good things to know!). I learned my sexual boundaries, the things I like, the things I don’t like and that at the end of the day, a healthy sexual relationship is monogamous (for me at least), deeply connected emotionally and open to exploring. PLUS I’ve pretty much done everything on my fuck-it list, which is great. I’ve lived my life fully and there will be no moments of ‘oh I wish I’d done that. I wish I’d had that experience’.

I was definitely a bit wild. I’m not saying it was all roses and perfect and that there aren’t specific instances I regret. I’m very lucky that in my exploration I wasn’t harmed. And I would advise someone to be careful and safe as an explorer. But I would say, hell yes, to that time in my life. I’m so so grateful for it.

And I’m super proud of that girl who had to google how her body works and bought her first toy from a site called tootimid.com. What a brave, fearless woman she turned into.