One Giant Step for Jim

I had a date with someone named Jim. He’d emailed me via the personals. He had an awful photo, making him look like Mr. Spock had an affair with one of his fans. But his email was articulate and correctly spelled, so why not, I figured. Plus, Jim was 25, so there was no way of me being intimidated.

We met at The Dove, which Citysearch promised was quiet and romantic. It was heaving. I snagged a table near the window. A bit after 8:00 p.m. I noticed a man pacing on the sidewalk outside. I knew it was him, and when I went outside, our eyes met and we introduced ourselves.

Dear me. Jim was skinny and awkward, with acne and acne scars, and he was wearing chinos or something equally unattractive. And he ordered a Coke.

But since he looked so unprepossessing, I felt sorry for him, and worked hard at conversation. As it turns out, Jim is quite well read and, after he warmed up a bit, a decent conversationalist. So the effort was well rewarded, even though he still seemed uncomfortable. But I ordered another drink and so my increasing confidence made up for his lack.

We stayed about two hours. I found myself thinking along these lines: “He’s a nice lad,” and “Maybe with a better haircut…” and “I wouldn’t mind seeing him again…” hardly indicators of flaming chemistry, but still.

Jim decided to take the same train as me partway home. While we were waiting on the platform he took off his glasses. Suddenly I noticed that he was standing close to me, and looking at me, and despite the fact that he was a young whippersnapper of incredible dorkiness, I felt a bit of a frisson, as they say. And then he pointed out that he had two different colored eyes: one blue, one brown. I looked into his eyes. “Wow,” I said.

He was so much better looking without his glasses! It’s strange, because often I think men look better with glasses than without. But without his specs, Jim looked both stronger and more boyish; his smile seemed brighter; I don’t know.

The train came. We sat on a bench next to one another, our shoulders touching.

“You have really small hands!” He exclaimed, putting his palm to mine to compare. The hand comparison is almost always a prelude to lacing fingers and clutching palms, itself a prelude to the goodnight kiss. We laced fingers, and somewhere around 23rd Street, Jim moved his face towards mine and kissed me.

I had thought he’d need a bit more encouragement. But I wasn’t complaining, and I liked that after all my work at drawing him out, he was taking the lead. He was a nice kisser – firm lips and not too sloppy and, thank God, he smelled right. I breathed him in with relief.

We kissed without stopping. I mean, there was none of the breaks to press foreheads and smile, or to exchange the smaller, more delicate kisses. This was just high school making out. “Get a room!” a teenager shouted.

If we kept going he was going to miss his stop. And I thought, Why shouldn’t he come home with me? Why not? And when I calculated we had passed his stop we broke apart and I breathed, “You missed your stop.”

Then we started kissing again.

The train was running express, and soon enough it would be my stop. As it came up, I tugged his arm. “This is my stop,” I stood up. “I guess you’re coming home with me,” I smirked.

Jim didn’t object, but instead gazed at me moonily as we waited for the local. When we got off at my stop, he took my hand and clutched it as we walked to my place. He’s so young, I thought, and felt a little embarrassed, as if afraid someone I know might see us.

At my place I offered him something to drink, like an ordinary hostess, then led him to my bedroom. We lay on my bed, kissing, and I could see he had a nice, straining erection. We got naked pretty quickly – he had trouble with my bra -- and he lay on top of me, kissing me everywhere. It was obvious he had very little experience. He wasn’t slobbering all over me, as inexperienced men are supposed to do, but he seemed so thrilled, so eager, so amazed, that I ended up feeling a bit detached. He bent over my stomach: “You have… the most… perfect belly button,” he murmured, kissing my belly. Aw. Juvenile excitement has its compensations.

Jim had a nice sized dick; one of the bigger I’ve seen. I stroked it approvingly. I was on my back with my legs spread, and he was on top of me. He started to push his cock into me.

Was he kidding? “Hey,” I tried to make my voice sound gentle rather than panicked or outraged, “I don’t do anything without a condom.”

“Oh, right. Right,” said Jim.

We paused, and I lay back against the pillows. “Look,” I said. “Are you sure you…?” I started again: “I just think … You seem … vulnerable, and I don’t want to hurt you or anything.” Oh, well, might as well: “Can I ask you a few questions?”

Jim nodded.

By now I can recite them all from memory. “Have you ever injected any drugs?”

“No.”

“Have you had sex with a man?”

“No.”

So far so good. “How many women have you slept with in the past year?”

He circled his thumb and index finger: “Zero,” Jim said, scrunching up his face in embarrassment.

Not a surprise. “And how many women have you had sex with ever?” I was betting one, two tops.

He held up the thumb and index finger again: “Zero,” he blushed.

Oh, my God.

“Oh, my God,” I said genuinely shocked. A 25-year-old virgin. Here! “Really?”

He nodded.

Oh, Christ! “Are you sure you want to do this?” Which was a dumb question. He was a 25-year-old virgin. With an erection. In my bed. “It’s just that I’ve never had sex with a virgin before,” I explained worriedly. “I feel a certain responsibility. I want it to be good for you.” This would undoubtedly be something he would remember. Could I bear the onus of being responsible for an indelible memory? What if it sucked?

Well, at least Jim’s erection showed no sign of buckling under the strain. I leaned over and reached into by bedside table for the Trojans. I put it on him carefully, and lay on my back.

He pushed his way inside me. We looked at each other. “How’s that?” I asked.

“Good…”

I figured he would come right away, and wasn’t expecting much. To my surprise, there was no gasp and collapse, just the rigid certainty of his dick inside me. I had nothing to console him about yet; that was good.

What the hell. “Can I get on top?” I asked, my most common question to the men I fuck, I expect. I started to ride him, and though I didn’t come I was glad to note that Jim had stamina, and seemed determined to please.

We fucked for quite a while, and he didn’t come at all, which I diagnosed as the result of about 15 years’ worth of masturbation techniques polished to a high degree of specificity. So he pulled off the condom, and started yanking on his cock with some violence. I watched him, and tried my hand at it (literally).

“Harder,” he said. Then, “Ouch!”

“Sorry!” I grimaced. I tried, but could not find the particular rhythm or pressure he seemed to require, so eventually I gave up and watched him manipulate himself.

“Before I come I have to switch hands,” he explained, as he switched from his right hand to his left. “And, oh God, this is so embarrassing – I have to make out with my arm, too, when I’m getting ready to come.”

“What?” I tried not to laugh, but just could not refrain. This made me picture Jim as a scrawny, gawky thirteen year old, jerking off to soft core magazines in a furnished basement with his parents upstairs. Aw. I leaned over and kissed him as he tugged on his dick, looking away politely as he exchanged passionate kisses with his upper arm.

**

Afterwards I noticed something awful: “Jim,” I asked, “Have you been wearing socks this whole time?”

He nodded. “Take them off,” I insisted, and waved a finger at him: “Never, ever wear socks during sex. It is the most unsexy thing you can do.” I was getting into this woman of the world thing, thinking how I could use my influence for good, and make his future lovers grateful for my gentle training, etc. “And always use a condom,” I added conscientiously.

In the morning we had sex again. He fucked me vigorously. Neither of us came. At last I lay on my stomach and had him enter me from behind. “Do you like that?” I breathed.

The proper answer to that is “Oh, yeah, baby.” (Like I said, I like the soft-core porn murmurings.)

“I like it if you like it,” was the lukewarm response.

I shook my head and smiled despite myself. “That means you don’t like it,” I said into the pillow. “That’s not much of an endorsement.” I slipped off of his dick, and turned around.

“Oh, sorry, you’re right.”

Jim was annoyed that he hadn’t come, but seriously, I thought he had acquitted himself pretty well for a first timer: no premature ejaculation, no nerves-inspired loss of erection, much attention to me and my wants. I wasn’t really inclined to console him at this point. After all, I hadn’t come, either.

We lolled around for a bit. “You know," I said, "You have a big dick.”

“Really?” Jim said. “I do? I always thought it was just average.”

“No, it’s a good size,” I said. I had suspected he’d be surprised at this bit of news.

“Awesome,” he grinned. “You just made my day.”

“Jim,” I said, “I just went down on you. I deflowered you, and that made your day?”

“But the compliment will last a lifetime,” he said happily.

**

Eventually we repaired to a diner near the train station. I sat there, feeling progressively more uncomfortable, while Jim stared into space.

“Is something wrong?” Generally I do not ask men this question – it is really only one step away from “What are you thinking?” and really – well, my guess is, if the guy wants to tell me something, he will. But maybe I had a special obligation (a geas!) to Jim, since I’d deflowered him after a scant three hours’ acquaintance? I dunno.

“What? No…” Jim flashed what might have passed for a smile.

“You’re just looking a bit grim.”

“No,” he said. “I was just staring at you.”

**

Finally I walked him to the train station. We kissed and kissed. Then we stared at one another awkwardly and I made some comment about how I hoped it had been a good experience for him, and he made some comment about how it had been a wonderful experience. Then we kissed again, and he ran down the steps. I walked home, feeling like I’d just lit a roman candle, and now I had to wait for it to explode.