He Came To My House A Top And Left A Side

We met on Facebook; we began chatting and getting acquainted after he sent me a friend request which I accepted. His name (for the purpose of this story) is Andy. I’d checked out his page first and found him to be very attractive in his photos before accepting the request. And soon after, we were chatting. It was quickly established that we went to the same university, even though I was a few years ahead of him.

We also established that we were both gay, and as it usually is with any two attractive gay men in each other’s DMs, our chats soon veered towards topics about sexuality and sex.

However, the moment our sex chats took a steamier turn, he sent me a message that stopped me in my tracks.

“I don’t really know much about sex,” he said.

“What do you mean?” I asked.

“I mean, I haven’t had sex before.”

I stared for a long time at that message, not knowing how to react. I mean, I don’t know about y’all, but sex with a virgin isn’t exactly my favorite thing in the world. When I get down with a guy, I like him to know as much of what he is doing as I do.

Wanting to be sure I wasn’t jumping into conclusions, I typed a question to him: “So, you’re saying you’re a virgin?”

“More or less,” he replied.

This response weirded me out because it made me begin to think he was much younger than I’d imagined him to be. Based on our conversations about school, without asking him, I’d pegged his age to be somewhere between 26 and 30. But I could not imagine any 26-year-old gay guy still being a virgin, so much so that I began to think he was perhaps 21 or 22. And that age felt too close to teenagehood for my peace of mind.

I was prepared to shut down our chatversation at this point, or at least steer it back to the formal grounds of career choices and living gay in Nigeria. But then, I skipped over to his profile and began scrolling through his pictures in an effort to convince myself that it wouldn’t be my loss if I didn’t have sex with this guy.

But he was just too attractive. A stocky build with grooves in the chest area of the T-shirts he was wearing that hinted at defined pecs. Small, almond-shaped eyes that crinkled prettily when he smiled. And sensuously thin lips that were my best feature on his face.

I sighed. Who was I kidding? I wanted to shag this guy! I just had to be sure what his answer to my next question would be.

“So, whenever you imagine yourself having sex, what role do you think you’d prefer playing?”

“Top,” he replied promptly.

I didn’t know what I’d been expecting him to say, but seeing that answer caused my heart to sink further. I play bottom; and no Bottom – at least, not the many I’ve interacted with – want to be topped by a guy who doesn’t at least know how to point his dick in the correct direction of their asshole.

A virgin Top! I was perplexed. Even if he was 21 years old, how had he managed to not fuck anyone in all his years on earth? While I could imagine a Bottom staying virgin till 21, I couldn’t imagine it for a Top, primarily because topping isn’t as stressful as bottoming. Clearly, from our chats, Andy seemed willing to hook up. So, abstinence or an internally homophobic abhorrence of gay sex wasn’t the problem here. So, how come not one of the many Bottoms crawling about the surface of the Nigerian earth had been able to get this guy and disvirgin him?

You’re trying to talk yourself out of this hookup again, a voice in my head admonished. Don’t. He wants to fuck you.

Yes, but can he? I snapped back.

Well, maybe not, the voice replied. But think about the privilege you’ll have from teaching him. Think about how you could use your desires as a Bottom to mould him into a Top that other Bottoms would love to shag. His sexuality is a blank canvas simply waiting for you to paint on it whatever you want your ideal Top to be.

I was very tempted by this train of thought. I was very tempted and I was relenting.

“I really need help in the art of sexology,” he messaged me in what was clearly intended to be a joke.

I chuckled and replied, “And you want me to teach you? Why?”

“You seem nice. I trust you,” he said simply.

That was very touching, and in that moment, I recalled a story I’d read here on Kito Diaries about a KDian who took on the responsibility of topping a virgin Bottom. I remembered how he had determined to go through with it just so the guy would have a first-time experience he would be very pleased with. I decided to set aside my own desires (and maybe satisfaction) and focus on giving Andy a good first-time experience.

So we scheduled a day for our hookup. The plan was for him to come to my place. The first time, he cancelled because he got choked up with his business for that day. The second time, I cancelled because an appointment suddenly came up on the morning he was supposed to come over.

But the third time was a charm; I was home and he was on his way. He soon got to my place and I finally set my eyes on him. He looked as good as he did in his pictures. He was a bit shy; at first, I thought this was because of us meeting for the first time, but I would later come to realize that he has quite a charming reticence about him.

He also looked older than 21. So I asked him how old he was, and he said, “Twenty-nine.”

My jaw dropped, figuratively of course. I had questions. Like, how was it that a 29-year-old gay man hadn’t ever had sex?

But I didn’t want to introduce any undue awkwardness to our situation, so I kept my questions locked away. We chitchatted for awhile, and then I leaned forward and kissed him. I wasn’t sure what I expected; perhaps that he would have so little experience, he’d kiss me back by either opening his mouth for me to dive in and encounter nothing but air and a hesitant tongue, or to find his teeth jammed shut, denying me entrance.

But he was a surprisingly good kisser. A really good kisser, in fact. A very non-virgin-like kisser!

Hmm.

We made out for awhile. Our clothes came off, and I was pleased to see that I was right; he had the body of someone who occasionally works out. We fell back into each other’s arms, kissing endlessly. I was so caught up in the passion of the kissing that I forgot momentarily that I was supposed to be guiding him.

Then I remembered and I took charge. I pushed him to his back and began tracing my lips and tongue all over and down his body, from his ears to his neck, down to his nipples. While he moaned as I licked and sucked at his ears and neck, he began to recoil as I took his nipple in my mouth. After a bit of sucking, I stopped and looked a question at him.

“I don’t like my nipples being sucked,” he said.

I paused when he said this, his words registering in my head.

I don’t like my nipples being sucked.

Which means his nipples had been sucked enough times for him to know he didn’t like it.

Suddenly I wasn’t sure anymore what to think about this guy’s virginity. When he told me he didn’t really know much about sex, what exactly did he mean? I wondered. Did that mean he knew literally nothing about anything to do with sex? Or was he talking about certain aspects of sex? Because all that kissing had the experience of someone who’d been doing a lot of kissing. He clearly knew enough about that!

But this was no time for conversation. I left his nipples and slithered down to his dick. I took it in my mouth, and from the sigh of pleasure he gave, it was apparent that this he liked.

The foreplay went on for awhile, with him also taking over my nipples and dick with the same skill that had me rethinking everything I believed about him.

But he said he needed help in the art of sexology, for heavenssakes! How could anybody be this good in foreplay and claim to need help?

I got my answer soon enough.

After such a heated foreplay, I’d abandoned any pretense at being a teacher and simply settled for an equal participant of the sex. Our moves were fluid and organic, like two lovers who knew what they were doing.

Then I was spreading out my lubed ass in a doggy position while he was slipping on a condom. His dick was average-sized and firm as he slid it into my asshole. And then, we began to move, with me rearing backward to meet his thrusts.

Wham, wham, wham, we were going.

It was glorious. Sex was happening. Houston, this is a go! Houston, we are taking off!

And then –

Wait, what’s going on?

The shaft that was ramming inside me had started feeling less rod-like and more rubbery. The pleasurable pain that was coming from the erection hitting into my canal seemed to be reducing. Something was softening.

Houston, we’ve got a problem!

Even as I was realizing this change, Andy appeared to pick up speed as he began thrusting into me with the forcefulness of someone who was panicked. But that dick continued to slacken, until soon, it was a limp piece of flesh that couldn’t sustain any hardness to stay buried in my ass.

He took it out and began wanking, clearly desperate to get his hard-on back. I waited patiently. Every couple of minutes, he’d get some semblance of an erection and try to force it inside me. But either the dick would make it inside and then after two or three thrusts, it’d lose what little turgidity it had to begin with, or it wouldn’t even be able to get inside my asshole. It didn’t help that he still had on his condom, and the plastic sheath kept making the dick’s reentry into my ass more un comfortable than it normally should be.

After a few futile tries at getting our freak back on, I finally said, “Maybe we should rest and try again after a few minutes.”

The sigh he let out made me realize that he’d been waiting for me to say that exact thing, to give him permission to stop trying to get his dick back inside me. This piqued my curiosity and began shaping an explanation in my mind. But I didn’t say anything.

We rested for a few minutes, lying next to each other and gisting about random stuff. Then, to signal to him that we should get back to the business of the day, I kissed him. He kissed me back. Then he seemed a little too keen on just kissing me, but I wasn’t about to allow that. I broke the kiss and moved myself into position, tummy down, ass up.

He went back behind me with a renewed erection. He slid in and began thrusting. This time, when it happened, I was expecting it. The dick became flaccid and he began trying to get it back up.

I then turned to him and asked, “Tell me the truth, Andy. You don’t like anal sex, do you?”

His sigh this time was heavy and very telling. Even before he opened his mouth to answer, everything had suddenly made sense to me.

“No, I don’t,” he said in a tone of voice that seemed like he was apologizing to me. “I really don’t.”

“That’s okay,” I said with a chuckle. “You’ve never had anal sex with anyone, have you?”

“No.” Then he hurried to add, “It’s not that I haven’t hooked up with anyone before o. I have. But we just make out and wank or do lap sex. I’ve never tried anal because I’m not into it.”

“Why didn’t you tell me all this before?” I asked.

“I didn’t know how to. When we started talking about sex, you sounded so experienced. And I knew you wanted us to hook up, so I couldn’t tell you that I don’t like this one thing that most gay men like.”

“I wouldn’t have judged you if you’d told me the truth,” I said gently. “In fact, I happen to know that not all gay men like anal sex. Instead, they prefer every other thing but anal. And they even have a name for that preference.”

“What is it?”

“A side. Gay men who don’t like penetrative sex are called sides. It’s not just top, bottom and versatile.”

“Side…” he said quietly, slowly, as though tasting the word to know if it fits. “That’s an actual thing?”

“Yes, it is. You should Google it. Your sexual preference is very valid.”

“Wow.” He had this look in his eyes, like he’d finally found meaning for something that hadn’t made sense to him in a long while.

“And you’re not a virgin for not liking anal sex,” I went on. “In fact, anal sex isn’t sex. It’s just an aspect of sex. If you do other stuff but anal, you’re having sex your own way.”

He smiled and nodded at me.

“Can I fuck you my own way?” he said, his smile turning lascivious.

I laughed. “And what way is that?”

“Lap sex.”

“Sure.”

I turned around again onto my belly. But this time, instead of spreading out my legs and ass, I kept my legs tightly together, and the dick he slipped in and began thrusting in between the backs of my thighs stayed strong and hard till he came.

Then he wanked me to cum. And we laid on the bed, talking for a bit before getting dressed and he had to be on his way.

In the beginning, I’d been expecting him with the intention of being his teacher during sex, and I ended up teaching him something entirely different.

Written by Dubem