How I taught a bottom to top

Anything is possible with patience and Viagra

This article by Kevin Moroso was originally published in Xtra Magazine as part of the Filling Station column.

I know bottoms. Since I mostly top, most of my lovers are bottoms. And as I’ve had more than my fair share in my bedroom — well not just the bedroom — I’ve come to figure out what makes them tick. There are roughly two types of bottoms, in my opinion: those who prefer to bottom after trying it both ways, and those who haven’t been able to top successfully and think they’re not made for it.

I became vers (versatile) because I felt I was missing out on sexual connections with far too many top guys. But there was another reason. If I’m going to have a genuine long-term sexual connection with someone, sticking to one role just isn’t adequate. And, I’m not going to lie, if I am going to feel fulfilled with someone, we need to exchange semen…

This dilemma arose last year. I’d been conversing with this guy, Jake, online for a long time — upwards of two years. We were finally going to meet; he was going to come visit Vancouver for a couple of weeks. Our conversations had been sexual, of course, and he was a 100 percent bottom. 

When Jake arrived, he was as gorgeous as I expected him to be: lean, smooth and tattooed with flowing dark hair and olive skin. I picked him up from the airport, took him back to my place, and we were naked in three, two, one — penetration. 

For the next few days, we stuck to our respective roles; I topped and Jake bottomed. I even took him to the bathhouse one night, got us a room, blindfolded him, wrote “cum dump” in Jiffy marker on his ass, and brought guys in to fuck him. His ass could take anything you threw in it. My ideal man. 

As we got closer over those few days, however, we talked more about him topping. It wasn’t that Jake didn’t want to top; it was that he’s never been able to. So we talked through the issues. He told me when he tried, he didn’t stay hard enough to remain inside a guy. We both deduced this was likely related to anxiety about his ability to perform — the pressure to stay hard made him soft. 

The great thing about being with someone you actually know, instead of a hookup, is having the patience and time to work through something like this. There were two things we needed — to enjoy pleasuring each other’s bodies without the need to focus just on sex, and the pharmaceutical miracle Viagra.

We had all the time in the world. We were in a cabin on a lake together, just the two of us, with nothing else to do but focus on each other. We could relax and enjoy the journey. Box one: ticked. 

As for the second box, I had just what we needed. A few years ago, I’d had a couple of incidents in which I went soft during sex. It was frustrating, particularly as a top. So a friend told me I should get Viagra. At first I was aghast — that’s what old men use when they have medical problems! But he assured me it wouldn’t be a problem to get from a doctor. He was right, and I began taking it regularly. The bonus: I often stayed hard long after I came, to the delight of many bottoms. 

I gave Jake half a pill of Viagra and we began making out. We both became rock hard. Jake realized it was now or never, so I laid on my back and he lifted my legs over his shoulders. He put some lube on his cock and on my hole and started to push in. Unfortunately for Jake, I don’t bottom much so I was tight. He pushed and pushed and went soft.I grabbed his dejected face, pulled it towards mine, kissed him and told him to stop worrying and to get back to making out.

As he stopped worrying about what had just happened, he began to get hard again. He took a deep breath, returned me to the same position, added a bit more lube and tried again. This time he managed to push in a bit but, as he slid in deeper, I could feel him softening. Again, I told him not to sweat it. We stayed in the same position, kissed some more, and then tried again.

He pushed in and this time penetrated down to the base of his cock. A wave of confidence overtook his face. He began to thrust. I’d seen him as a submissive bottom the last few days, but he looked different now. I was glad I was on my back so I could see him. He looked tough, sure of himself and full of enjoyment. He was the most gorgeous man I’d ever seen. He told me he was about to cum and I looked into his eyes and told him I wanted it inside me. I could feel his dick pulse as he shot his load into me. 

He stayed inside me as he leaned down to kiss me. Jake had never ejaculated inside someone. I was happy to be his first; he was elated.

Over the rest of his trip I still mostly topped, but Jake topped me a couple more times. Jake has also topped since he went back home, so I’d say he’s at least vers-bottom now. As is often true with sex, it took some trial and error, patience and an understanding partner. Oh, and Viagra. We mustn’t forget the Viagra.