I recently entered into a relationship with a coworker/friend. The personal connection on both ends was intense. Intense in a super good way. We were quick to be comfortable enough to share many deeply personal things with one another—a strong emotional connection that I rarely feel in relationships. Additionally there was an equally strong physical attraction on both ends. Things were going quite well.

The road block: we are both bottoms. I personally recognized the challenge of that, but was willing to take that risk and see what happens. He on the other hand is deeply conflicted about taking the risk. He has concerns that if the physical relationship becomes a deal breaker down the line (which can always be a possibility), it would be too late to sacrifice any kind of friendship. Now he is debating if that risk is worth it. For him, fear is winning. Yet he acknowledges he has anxiety knowing he is possibly missing out on what could continue to be an incredibly valuable relationship.

What advice do you have for two bottoms who work everywhere besides the bedroom? Ideas to make the bedroom work?

Conflicted Bottoms

My response... after the jump.

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Here you go.

I'm not being glib, CB—well, not entirely. Double-headed dildos are a workable and fun option for a gay male couple composed of two bottoms. There's also pushing yourselves outside your comfort zones/usual roles, i.e. you both learn to enjoy topping and take turns. And there's also the monogamish option. If having each other means never getting fucked again, I could understand the other guy's hesitation. But it doesn't have to mean that. Even if neither of you can learn to enjoy topping, CB, you can still enjoy oral and mutual masturbation with each other—incorporating your collection of double-headed dildos into your mutual JO sessions—while occasionally inviting a total top over as a Very Special Guest Star.

Lay out these options for your coworker/friend, CB, and see what he says. If he isn't willing to give you guys a shot—along with double-headed dildos and taking turns and monogamishamy—then he's either completely invested in the idea of being with a total top or he's not interested in you for some other reason(s) and "But we're both bottoms!" is a white lie designed to spare your feelings.