We Started From The Bottom

Henry was my dormmate in secondary school. He was one of the hottest guys in school, if not the hottest. Everybody who had a sex organ wanted him. He was in SS2 and was dating an SS3 girl – a girl who belonged to that league of girls that were regarded as hard to get. The fact that Henry had “gotten” her sort of solidified his status as a really hot piece of ass.

Henry was good-looking. Tall, with smooth chocolate skin, a slim, toned body, and a smile that could make you fall to your knees and beg him to love you. He was smart and charming, but he was also well aware of how special he was, which made him very entitled and oftentimes rude.

I was in JSS3 when we became dormmates. I was the only junior in the room, with two other seniors. Our relationship was cool as long as I was respectful of them. Henry came from a well-to-do background and we bonded over conversations about trips abroad. Although I was a junior, he treated me well, letting me sit in on his gisting sessions with his classmates and not turning me into a perpetual errand boy like most seniors liked to make juniors be.

He also took liberties with my body, often randomly smacking my ass regardless of where we were. It could be at the assembly, in class, on the way to the dining hall for lunch. Anyone who went to a boarding school would know this wasn’t uncommon, and isn’t entirely indicative of the person’s sexual preferences. I didn’t think Henry was into boys for simply smacking my ass.

But I found what he was doing both embarrassing and annoying. And one day, when he smacked my ass really hard, I lost my temper and right there, in front of some of his mates, I lashed out at him, telling him to stop doing that. He was taken aback by my reaction, and immediately the words left my mouth, I suddenly realised my station as a junior student and wished more than anything that I hadn’t said what I said. I thought for sure that he would react aggressively, maybe beat me or punish me or something.

But the words he said startled me into amusement. He looked at me and then told me to get on my knees and blow him right then and there in front of his classmates.

Thinking he wasn’t serious, I laughed and turned to leave.

But he grabbed my arm and said with a very stern expression: “Are you mad? I told you to do something and you’re laughing. If I slap you eh! I said, get on your knees and blow me!”

I was caught with both terror at his fountaining anger and mortification at the thought of him making me perform such an intimate act on him with an audience of his classmates. I began trembling, not sure whether to stay defiant or submit. Fortunately, his friends intervened and told him to leave me alone. Soon, they were all laughing and walking away.

And I was left standing there, thinking about how crazy this guy must be. Was he really serious about what he’d ordered me to do? Would he have actually made me blow him? Was he even gay?

That incident marked a turning point in our relationship. A few days after that, I used his perfume without his permission, and when he found out, he told me to give him head as my atonement. I could either give him head or buy him a new bottle of that perfume.

At this point, I figured: this guy was either gay or really, really into wanting me to give him a blow job. This time, there was no audience and it was a no-brainer. Not like I had any money to buy him a new perfume. And he was hot. Giving him a blow job would bring me so much pleasure.

His dick is something I still remember. Long, fat, easily about 7 inches lengthwise and 4 inches thick. I often wonder how I was able to fit that piece of meat into my mouth. But I did.

And that blow job led to other blow jobs. Before long, Henry and I were hooking up on the regular. We didn’t do anything heavy. Just making out, blow jobs, and dry humping. We never got to actual penetrative sex. I would suck him off on the regular, and he would suck me off too occasionally. I didn’t mind that I wasn’t getting as much head from him. The mere fact that I was often running off to some empty room or bathroom to do the nasty with a hot piece of ass like Henry was gratification enough.

Then one night, I was mad horny. I waited until our other roommate had gone to sleep, then I crept into Henry’s bed and whispered into his ear, “I’m horny.”

I thought he would turn around for us to start sucking each other off. Instead, he did what surprised me. he pulled down his boxers to reveal his perfectly-shaped ass and simply said I should go ahead.

This was new terrain for me. I’d never fucked anyone before. And I certainly had never envisaged that I would start by fucking Henry’s ass. But he was offering, so I took it. I slowly stuck my dick into his warm, tight hole and began to slowly rock back and forth, thrusting in and out. I didn’t even know whether I had my dick properly anchored inside his asshole. I didn’t know what I was doing, except that something like this was what I saw heterosexual people do in the movies. And he felt very amazing and tight and loose in the right places, warm and comforting in some weird way. I just carried on rocking back and forth until I came. Then I slid out of him and pulled on my boxers. He did the same and we both went to sleep.

But life doesn’t give free stuff. Two days after that night, when Henry and I came together for our usual heavy petting, he said to me, “I want to fuck you.”

My “No” was swift and strong. At that age, I couldn’t even fathom anyone sticking anything inside my ass. Of course, he made the argument that he let me fuck him and so it was only fair that I let him do the same to me. But I maintained my “No”. He gave up and asked if he could just fuck my thighs and I said OK.

So, I turned around, curious to know what it felt like to be fucked between my thighs. He smeared the backs of my legs with cream, and then slowly began to thrust his dick in between my thighs. He went in and out for like a minute, before he began begging for me to just let him go all the way into my ass.

I was already in position and he was being so persistent. So, I caved, telling him to “just get it over with.”

But I very quickly changed my mind the moment he began to insert that monstrosity that was his dick inside my virgin ass. It was painful as fuck. Our other roommate was sleeping at the other end of the room, so screaming out loud was not an option. I began to struggle, but Henry had already had a taste of what he wanted and was not ready to give it up. As he fought to subdue me, he was persistently maneuvering his dick inside the terrain of my asshole. He was both gentle and a skillful lover, and I soon gave up the struggle and began getting into the groove of the fuck. Even though it was still painful, I welcomed him as he thrust in deeper and deeper, while jerking me off simultaneously. It was an onslaught of pleasure and pain rocking through my body.

But soon, the pain took over again, as he began to concentrate more on digging his Mandingo deeper inside my ass. And as my ass was getting set on fire, because I’d essentially not prepared for an anal invasion, his determined penetration began to dig out fecal matter.

The moment the smell of shit hit our nostrils, he paused. Clearly, he hadn’t seen this coming. And I grabbed that opportunity to break away from him. I jumped from his bed and fled to the bathroom to take a long shower. My asshole was the kind of tender that hurt too much for me to touch. I went to bed both angry and depressed. I promise you, I couldn’t sit right for a few days after that night. And I realised then that that – which I would later learn is called bottoming – was just not for me.

Henry and I continued to hook up – without the penetration – until he graduated. And we lost touch and never spoke to each other again until this year, when I got his number from a family friend who I was delighted to find out knows him. I called him and he reacted with pleasure when he realised who was on the line. We chatted and caught up for a bit, before moving our conversations to WhatsApp.

Then he asked if he could come see me. And I very excitedly said yes. I hadn’t seen this guy in years. It would be nice to reconnect. To know if we’d still have a spark. To behold his dick again – supposing of course, he was still into boys. A lot of boys graduate from secondary school and like to chalk up their same-sexual experiences as experimentation.

On the day we were supposed to see, he called me to let me know he was at my place. I was home alone and opened the door to a marginally different Henry. He was still handsome, but he looked tired and dry. He still had that smile though. He came in and we exchanged pleasantries. We reminisced about secondary school and then about our hookups. He said he hoped everything we did then was consensual and that he hadn’t used his seniority to intimidate me into doing it. I said yes, it’d all been consensual.

He lit up a blunt. After a few hits, he gave me a look. The look. Then he said I should come to him. And he pulled down his pants to reveal that familiar big dick. And once again, I was reminded of how majestic his penis was. I didn’t need much prompting; I slid down to the dick and took it in my hand. I put my lips to the tip, tasting it, wrapping my tongue round the cap, before sliding down and attempting to fit it all into my mouth. I began sucking him, using my tongue and mouth on his dick while using my fingers to play with his balls. I gradually picked up speed, stretching my other hand up to his chest and playing with his nipples.

And then, the oddest thing happened. All of a sudden, I wasn’t feeling it. I don’t know what it was, but the konji died and I began to feel the blowjob less and less. I stopped.

“Why did you stop?” he asked in a voice made raspy with desire.

I told him I wasn’t feeling it anymore.

He told me to try, that I should just give it another try. I did, but I was starting to become aware of how much my jaw was hurting and uncomfortably big his dick was in my mouth: things you are not supposed to notice when you’re giving a blowjob.

I really was done.

I let go of his dick and told him as much.

“Why?” he asked again.

But I didn’t respond. I was trying to get up when he grabbed my arm and yanked me back down. My heart skipped a beat when I turned to look into his scowl.

“You cannot leave me like this,” he hissed.

For a moment, I felt fear. I looked into his eyes and I became afraid. He looked like he was ready to get what he wanted at all cost, and I was now acutely aware of the fact that I was home alone. Was this how it was going to be? Was this how I was going to become a victim of assault?

“Henry, I can’t…” I said softly, hoping that the gentleness of my tone would thaw whatever madness that was rising inside him.

It did. The stony look on his face broke and he said almost pleadingly that he’d been thinking about me since secondary school. Something I highly doubted. He said he wanted to have me like old times. I disengaged myself from him and went to sit a safe distance away from him. He told me to at least let him fuck me. I told him I was good.

“Besides, I don’t bottom,” I added.

He reminded me of how he’d fucked me back in school. I told him he was the first and the last, that it had only happened that one time. He asked if I wanted to fuck him. I told him I really wasn’t in the mood. He told me to help him out then. That he had to come. When I asked how he wanted me to help him come, he said I should finger him while he wanks. I said OK.

So, he spread his legs apart and started wanking. I slid down between his legs and reached for his asshole. I started with one finger. Sliding in back and forth. His breathing was getting heavier as he stroked his dick harder. I made it two fingers, then three. He moved his hips to meet the thrust of my fingers. I was looking him in the eye, and he was looking back at me.

And something about that situation began to turn me on again.

And he must have caught on to my reignited konji, because he rasped, “Do you want to fuck me?”

“Yes,” I said.

“OK,” he said.

Feeling suddenly eager, I withdrew my fingers and went to pull down my shorts.

“But you’re going to have to pay me 100K.”

I froze. I stared at him. “Excuse me, what?”

He had a small smile on his face as he shrugged. “To fuck me, you’re going to have to pay me 100K.”

I shook my head, as though I was having difficulty processing what he was saying. “What?” I said again.

He said he likes to get paid for sex. I was instantly furious.

“But you were willing to take my blowjob for free, right?” I snapped.

“Oh, come on –” he began.

“No! don’t ‘Oh come on’ me! if I wanted to pay for sex, I’d go for someone who looks like Jesse Williams, not your crusty ass. If you wanted money, why didn’t you simply say so, instead of trying to leverage sex.”

He flared at that. Snapped something at me. And I snapped back. He said something about how he didn’t need my money, that he was making good money. I said something about how being an escort must really pay well. Many things were said, and ultimately, he left and the visit ended on a sour note.

As I sat to watch a movie minutes after he left, I kept going through what had happened during that visit and what had happened all those years ago. How uncomplicated things had been back when we were in secondary school, and how now, everything was fucked up because of adulting and the influence of society. Henry didn’t respond when I later texted to apologize to him, and I figured, maybe it was for the best. Maybe some things are better left in the past where they belong.

Written by Rai