Love & Sex

My First Time: Male, 26, Massachusetts

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Male • 26 • Massachusetts

I was on a second date with a girl who I found rather attractive, and she had a proposal. "Let's play the sexual partners game." Despite not knowing what that game consisted of, as a twenty-six-year-old virgin (long story), I assumed it wasn't going to produce a favorable outcome.

"What is that?" I asked, not masking the fact that I didn't really want to hear the answer.

"You have to guess how many people the other person has slept with. The closer guess wins." She made it sound so simple. "You go first."

My competitive nature precludes from me turning down any challenge I think I can win, even if it means embarrassing myself in the process. I took a good look at this petite twenty-four-year-old blonde sitting across from me, and tried to imagine how many guys had been inside her. I had few clues about her past, but I did know she was a fairly devout Catholic. I couldn't decide if that would make her more or less promiscuous, but I decided to err well on the side of caution: "Hmmm, I'll go with five. Your turn."

I didn't realize it at the time, but she was working me over. This was not a game, but an elaborate setup.

She began to look at me like I was a jigsaw puzzle or an Escher lithograph. I would later discover that she had an uncanny ability to read men — accurately estimating their net worth and endowment in mere seconds. I didn't realize it at the time, but she was working me over. This was not a game, but an elaborate setup.

"I'm going to say seven," she held out the last syllable, coyly reading my reaction.

My acute sense of comedic timing acted up. "Close. Only off by seven."

She feigned shock. "You've been with fourteen girls! I'm impressed." (She wasn't.)

"Actually," I said, "I've been with zero." Lying about being a virgin was something I had vaguely considered in the past, but she'd caught me off-guard. In this case, it seemed the truth had worked in my favor. I had passed the elaborate test.

"Wow, I'm really impressed you would admit to that." The words seemed genuine. "I think it's great that you're a virgin," she said. She was laughing slightly, but it didn't seem directed at me. "I've only ever been with one guy, and I really don't have much respect for people who sleep around."

If she was simply trying to make me feel better, it was unnecessary. Victory was at hand. "So, I win? I was only off by four!" I raised my arms in mock triumph.

"You're so innocent and naive. It's really cute." She was glowing. "I'm going to enjoy corrupting you."

Over the next few weeks she did her best to tease and test me, enjoying every second of my reactions to her games. She told me that she was going to take my virginity, but she gave mixed signals on when and how that would actually happen. The culmination of the teasing came when we were naked in a whirlpool tub. She told me we weren't going to have sex for another month, and then spent about two hours grinding on me in the steamy, bubbly water. I enjoyed it too much to be pissed off.

The next day, I decided that I needed to take control of the situation. I suspected that she had really wanted me to take control the previous night in the tub, despite her verbal misdirection. So as we sat on her couch watching the History Channel (sexy, I know). I started slowly inching my hand into her pants. I was particularly proud of the pace and subtlety of my execution. She put up no resistance, and was soon cooing and breathing softly against my face. Meanwhile, George Washington was crossing the Delaware.

She took some initiative and started returning the favor. She unbuckled my belt, and, in a matter of a few minutes, was going down on me. The sensation was indescribable, but I was afraid that I wasn't going to be able to get off from it. This made me try harder to focus on getting off, which, of course, is counterproductive. Fort Ticonderoga was slowly falling to the British.

I was dead-set on ending my twenty-six-year drought.

After a few minutes, I said she could stop because it wasn't going to do anything for me. She said that's not why she was doing it, and, in what seemed like one fluid motion, yanked her jeans off and got on her back. I slid off her panties and she wrapped her legs around me, stared submissively into my eyes, and didn't say another word. Benedict Arnold's treacherous plans were brought to light.

At this point, I was giddy with adrenaline and testosterone, but I managed to keep a look of steely resolve on my face. I was dead-set on ending my twenty-six-year drought. I tossed my shirt across the room, and without stopping to think, took the plunge. I really had no idea what to expect, but needless to say, it felt incredible. All of my life I'd assumed I would last about seventeen seconds my first time, but to my surprise, I made it a solid four or five minutes. After waging war for years, the British were surrounded, and forced to accept defeat to this new, emerging nation. We came, nearly in unison. It was glorious.

We collapsed in a heap of sweat, ecstasy, and joyous laughter. She had exacted her revenge against the nameless guy who took her virginity and broke her heart, by taking my virginity (and a few months later, breaking my heart), and I had achieved my longstanding goal of having sex (with a hot chick, nonetheless).

Forty-five minutes later, we were at the local pharmacy buying the morning-after pill. I can only imagine what was on the TV at that point.