My teachers and parents told me that I would date, fall in love, and lose my virginity to a wonderful Jewish boy, wearing a condom of course. That was my fantasy as a teenager, but that didn’t exactly work out.

When I was 17 I realized my attraction to women, while still being attracted to men. What follows is a sexual comparison of sorts, exploring intimate moments with both men and women. Most of these experiences were not with Jews, or in relationships.

I lost my virginity in a Columbia University dorm room, to Johnnie. We spent a few months fooling around on the weekends when I came home from college. He wasn’t the best kisser, ignorant about the female anatomy, over eager, but attractive. He also was the only guy at that point who wanted to see me naked, so it was boost to my low self-esteem. I still didn’t have the guts to say what I liked, but he did make me moan.
He asked me, “Can I please put it in”?
“No”.
“Please”?
“Ok, just a little”.
Well, a little went most of the way; it lasted two minutes, it hurt, I freaked out, and he stopped. I cried, and said, “Oh my god, that wasn’t sex, right? Oh my god, s**t, oh my god…”

I kissed a girl for the first time in college. It didn’t take me long to love breasts, the scent of perfume, and the improved kissing abilities.

I was much more eager about having sex with women than with men, I just didn’t have the opportunity to act on it. It didn’t scare me as much, it gentler, more pleasurable, and, for obvious reasons, less risky.

I didn’t date much in college, so when I graduated I ventured into online dating, seeking both men and women.

The boys I dated (from JDate) were a mixed bag. Some were terrible kissers, hairy, and just too eager to turn me into a one-night conquest. My favorite line was, “Oh my god, I want you so bad, pleeeeeeeeese”?

“No”. Haha.

Others were amazing kissers with soft lips, kind eyes, and made my knees wobbly.

I remember how some boys just lacked etiquette when they were finished. They would aim up, or at me, getting the sticky substance all over my stomach, or hand, or yes, even my face. Usually there were no tissues around. Why? Because they are men, and they have no manners when they are in moments of ecstasy. Maybe there was a t-shirt on the floor, or they would say “sorry”, and I would walk to the bathroom to wipe off.

Men also don’t seem to realize that breasts have nerves and muscles. Why do they squeeze and grab so hard? I never understood that. That was always my biggest pet-peeve, after bad kissing. It ruins the moment. One guy even left a bruise from squeezing my breast so hard. I would get them to slow down, be gentler, but it seems like so many men make the same mistake.

After a night of passion, I think two boys had the decency to get dressed, walk me out, and help me get a taxi; most just stayed in bed as I picked up my crumpled jeans from the floor. I never spent the night unless it was really late. They would roll over, and fall asleep.

Then there are the women: those lovely, non-hairy creatures.

I made love to a woman, my first girlfriend, when I was 23. It was romantic, and nothing like the awkward experience with Johnnie. Danielle was an amazing kisser, and amazing at everything else. We laughed, and smiled. She made me feel sexy, and cared for me at the same time. We would hold and kiss each other afterwards, until we fell asleep.

There have been other women since then. They would check in and ask, “Is this okay”? They would give feedback. In return, I felt comfortable saying what my needs were because they actually cared about what I wanted, what felt good to me. Even during one-night stands. There were always tissues on hand, or something else to clean up with. There were sex toys sometimes, and massage oil. There was sensuality, there was foreplay! After sex, we would cuddle, or lie comfortably next to each other.

Thinking back to the list of people I’ve kissed or been nude with, (yes, I actually have a list), the better kissers, the better lovers are usually women. Like I said, I have made out with some hot guys who had the most delicious lips, but I never got far enough to see what else they would be good at. The good female kissers always seem to outnumber the bad ones.

I wish I knew what it was that makes women better lovers, but I don’t know if I will ever find the answer. I also wish I had been with a guy long enough to teach him, or at least speak up while he was clumsily taking off my bra.

In the end, sex education and the silly books didn’t teach me much other than “use a condom”! What they failed to address was same-sex intimacy, and that losing your virginity isn’t a romantic, life-changing moment that films, television, and books make it out to be. I however was lucky that I got a second chance to do in the way I had always wanted, with care and affection. Chicks rule.