Planning for Success: A Virgin Story

Editor’s note: This post is part of a series about losing your virginity. This series was inspired by this Rookie Mag post. We hope it offers a glimpse at the experience of losing your virginity and all the complexities that come along with that. These pieces have hints of the explicit and are not for the easily offended.

This post, in particular, is not safe for work.

If there is one thing that Myers-Briggs got right about me it’s that I am a judger. I organize; I structure; I plan. At any point in my life I can tell you what my schedule is for the next five minutes or the next five years. I value knowing what’s coming and being in control of my circumstances. Having a solid plan under your belt—not to mention several contingencies— is my recipe for success.

Planning takes brainpower. You gotta consider the costs and benefits of any particular action. When I was younger, the risks of sex far outweighed any potential benefits. Growing up, I watched more than one of my friends get pregnant and drop out of school, perform a “home made” abortion, or contract an STI. Who knows what my parents would have done if I’d gotten pregnant? To top it all off, everything I heard about having sex, from my mother and my friends, made it sound pretty awful, particularly if you had to sneak around.No. At 15, sex wasn’t even on my agenda. No marriage. No sex. Ever.

But even the best made plans need to be flexible. By the time I hit 18, my priorities changed. Risks went down and benefits went up. Not only was I ready for sex, I was impatient for it. I even tossed around the idea of having my high school ex-boyfriend fly across the country to help me out. Oh, yeah. I wanted it bad.

Ultimately, though, there were still risk factors to mitigate. I needed someone who I could trust, was able to stick around, and invested enough to help me through whatever psychological issues I was expecting to have. Planning requires patience. I quelled my impulses, slid sex into the schedule, and waited.

Har. See what I did there?

So I walked my virgin self to a fraternity at Georgia Tech. There, a shy nerdy man with shoulder-length dreadlocks, a lean build, and the most beautiful brown skin I had ever laid eyes on expressed his interest in me. He was quiet, observant, and jaded—my opposite, on the surface. He spent the night on our second date, but before any “funny business” happened, I laid down the facts: Not only was I a virgin, but I had never had my breasts fondled, never given a blowjob, never received oral, or, pretty much, ever been naked in a room with another man. I wasn’t just a virgin; I was Supervirgin, and I had no intention of significantly changing my state that evening. He and I crossed the first experience off of my list before cuddling up to watch a movie and falling asleep.

After agreeing that we wanted to pursue a relationship, we made a plan: No intercourse for three months. He needed to build trust as much as I did.

For three months, he and I explored corners of our sexualities with the full understanding that we didn’t have to have intercourse to be intimate. I cried the first time I gave him a blowjob because I got frustrated and my mouth was sore.  Cunnilingus was a lot messier than I had expected. In the meantime, we made all the preparations: He went and got tested for STIs; I schluffed over to an OBGYN and got a diaphragm. Together, we crossed off all the items on my “to-do” list, and even found a few more things that I hadn’t even considered doing before, all without inserting a penis into a vagina.

I am, however, also a stickler for deadlines.

Don’t get me wrong. I was having fun, but by the time our three-month marker came up, “impatient” would have been a mild word to describe me. I was ready to get ‘er done, even if I was so nervous that he felt the need to give me a full body massage before the foreplay even started. My impatience might have been the cause of our less-than-adequate plan. We didn’t really think out what position beforehand, and that’s where the trouble began.

Missionary hurt. It burned. Like someone was stretching my skin past where it was supposed to go. I tensed, he backed off. Rinse and repeat until I was so aroused and frustrated and confused that I started to cry. He lay down next to me and pulled me into his arms, telling me that we could stop for now and try later.

Um, fuck no. I hadn’t put up with three months of perpetual foreplay with the hottest guy I had ever dated to give up because I had forgotten to work out a few steps. Sometimes, a little improvisation goes a long way. I flipped myself on top of him and positioned my partner’s half-slackened penis where it felt right, determined. This time, I had control. This time, it felt better. Before I knew it, the burning sensation was just one more feeling flooding my body, giving an edge to the satisfaction as we inched closer and closer to full insertion. Eventually our hips touched, and we smiled.

My mother once advised me that my first time would be awful. She said it would be awkward, painful, and traumatizing. I shouldn’t  expect to enjoy it. Out of all the things I have proven my mother wrong about in my life, I think this is my favorite. My partner panted in time with me as I moved, tentatively at first, then boldly. I moaned. Loudly. His housemates teased me for it afterwards, but it was worth it. To this day, the sound of my partner murmuring “Oh, I think she likes it” in my ear that night is the most erotic thing I have ever heard.

I announced my lack of virginity to the world the next day by leaving a group on Facebook called “The Sexy Virgins,” and I updated my status to say “Gina Luttrell is a little sore.” I wasn’t ashamed to announce it. Having sex was never a shameful thing to me. I planned; I followed through; I got an amazing return. Who wouldn’t be proud of that? I didn’t lose my virginity. I put it aside, proudly, unabashedly, and without regret, because the next section of the agenda was beginning.

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5 thoughts on “Planning for Success: A Virgin Story

    • Yeah, when I wrote this I definitely paused over the best way to describe it. I certainly didn’t *lose* my virginity, like it was an accident, and I didn’t really “throw it away” either, because I never thought of it as something bad that I wanted to get rid of. I felt like “putting it aside” was a good way to phrase it because it was just moving from one state of being to another, but it was a move that I actively chose for myself.

      Thanks so much for your comment and compliment! I’m glad you liked the piece! :D

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