First Times and Good Times: An Open Letter to Those Curious About Sex

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The first time I bought condoms, I tossed them in a grocery basket with pita chips, Goldfish, and two Blue Books. My best friend, who had already been sexually active for a while, helped me pick them out. All I had told him previously was that we were going to Walgreens for “supplies,” and I led him on a winding trek around the store picking out the essentials. Then I escorted him up the escalator to the family planning section and, facing the racks of latex, non-latex, slim, normal fit, ribbed, studded, and lubricated condoms, I asked him, “So…which one should I get?”

Without missing a beat, he sifted through the shelves, eliminating swaths of products with a flippant wave of the hand. “For a new user? You don’t want the ribbed ones, at least not until you’re more experienced. Does he have a latex allergy? Better to get pol-poly—stick with the non-latex ones to be safe. And don’t get the magnum ones. That’s what I get for my boyfriend, and he’s thick.” He held his hand up in a circle shape for emphasis.

We settled on a box of slim, non-latex ones, checked out, and I, upon exiting the store, registered that I was going to have a penis in my vagina for the first time ever.

Well, of course that wasn’t the first time I’d had that thought. I had a plan of action walking into that Walgreens, even if it took a bit of backtracking and positive self-talk first. Actually, immediately before going to buy the condoms, I had met up with my boyfriend to discuss what I was going to do. He took my hands, clammy as they were with nerves, and told me he had planned to do the same at Meijer that night. That’s when I knew I was making the right decision to protect my health, although it’s always a good idea to come prepared.

Our inside joke, even when the idea of us having sex was ambiguous and distant, was that we were waiting for marriage; it just wasn’t our marriage. His sister’s wedding was taking place that weekend a few towns over, and as such, she and her fiancé had booked us a hotel room together, separate from the rest of the wedding party. Three days, two people, one bed… Literally, I know, it was the setup to a soap opera. We could be together, all night, undisturbed by roommates and the other hassles of dorm life. 

The night before the wedding arrived, and I, condoms stashed in my duffel bag, checked into the hotel with my boyfriend, who hadn’t looked quite so ravishing in weeks. And, I suppose, being in an elegant yet flirtatious floral-print dress, neither had I. At any rate, we ascended the elevator to the fifth floor, entered our room, and breathed a sigh of relief to be alone at last.

I remember the room being particularly charming, spacious yet cozy, clean but not sterile. When we entered, the lights were low and calming, and the bed lay freshly made around the corner, which definitely was not doing anything to subdue our horniness. We set our bags down, took off our coats, and stretched, each waiting for the other to fall onto the pristine bedspread first. Then when we got tired of stagnating, we pulled each other down onto the bed and became enveloped in each other’s body.

I’ll spare you all the details, but a little while later, I lay flat on my back, fully undressed, pillow under my open hips for comfort. He hovered over top of me, supporting himself on my knees. “Are you ready?” he asked, mere inches separating us now. I replied with a breathy, but active and enthusiastic, yes. He smiled in excitement and lowered himself onto me, the gap between us growing smaller, smaller, until we were almost there and we were almost one and I almost knew what it was like, and—


He missed the mark and slipped out, so he tried again.


Third time’s the charm.


…maybe not.

Pretty soon, we did manage to get it in, but we couldn’t get farther than perhaps an inch, plus he kept slipping out as soon as he started thrusting. After a few minutes of attempting, the stress made him start to go soft (we later found out that he was wearing the wrong condom size, too, even after all that work), so we stopped for more foreplay before trying again. Still, he couldn’t stay put or hard, and after cycling between arousal and attempts for about two hours, we decided to call it quits, neither of us that satisfied.

I remember lying in bed that night curled up with him, doubts and wonders racing through my mind following a total of approximately six seconds of insertion. Was that sex? Was I still a virgin, or did our genitals just butterfly-kiss? Could I get a redo?

Don’t get me wrong, I fully enjoyed my partner and the time we spent in that room, and I wouldn’t have wanted it to go any differently (more or less). But now that I’m on the other side of being sexually experienced, I wanted to share my thoughts with my fellow proud vagina-owners who haven’t had their first experience yet. As teenagers learning to feel strange attractions toward members of a certain sex, we are lectured on the dangers of intercourse, among them the biological, like pregnancy and STIs, but also the puritanical, that the first time should be special and that sex can’t be taken back. We’re regaled with anecdotes of people who defiled themselves too young and later regretted it. Parents, teachers, and relatives warn us of the lewd, singularly focused intentions of young men (ignoring, of course, the fact that guys aren’t everyone’s type) and pry us away from situations that might lead to illicit activities. Over the course of an adolescence, these messages accumulate and mutate into a fearsome, confusing, shameful mess. When puberty ends and we earn the freedoms of adulthood, we’re not even sure if the pleasures of sex would outweigh the hurdle of overcoming those messages and actually doing it.

In the hours leading up to that night, I wondered if I would feel any different, and if I did, would it be for the better or the worse? Would I regret it? Would I like it? Would I categorize my life, from then on, as Before and After? When I returned to school on Monday, would I be able to focus, or would I be buzzing with an internal glow, tender parts still tingling from the sensation?

As I stared myself down in the mirror later that evening, I looked for signs that I had matured or changed or crossed a threshold in some way yet found nothing. I didn’t feel anything different, either, except for a stronger bond with my partner. It was like being nine years and 364 days old again, being psyched out of your mind to finally be in the double digits, to experience the thrill of being 10 years old. Then when you wake up in the morning, you find that you feel precisely the same as the day before, just that a fact about you has changed. That’s what sex was for me, and what I’m sure it what it would be for many others if societal taboos didn’t keep us from discussing it, just a new fact. Something about me changed, yes, in that I had done something I had never done previously; however, I did not change. Even now, after doing the nasty a full four times, I’m still the same old me—I just make worse innuendos.

This isn’t to say that sex isn’t intimate or special, especially the first time. It is. It’s just not the sacred, life-altering milestone we’re made to believe it is, and nothing gets “lost” when you lose your virginity. I’d rather spin it into the positive and state what I know: I had sex. With a penis. That was inside my vagina. And I am still the same person I was before because nothing can be done for the first time twice; it just so happens that we have a specific word for this particular act.

For those of you still waiting on your first times, I leave you with this summation of consummation. I wish for it to be on your terms. I wish you the clarity of mind in the moment to make the right decision for yourself. I wish you the power to say no and the power to say yes. I wish you the strength to overcome others’ expectations and evaluate your own. And above all, I wish that your first time, if and when you choose to have it, be every bit as enjoyable and memorable as mine, and bonus points if it’s more successful and pleasurable, too. Your body belongs to you for your own use; joining with another’s body is just another choice for you to make.

Cielle Waters-Umfleet

Staff Writer, What The F Magazine

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