How to Do It is an advice column focused on sexuality.Do you have a question?Submit it here anonymously.
Dear How to Do It,
I’m a 45-year-old gay man dealing with complex sexual trauma, and I’ve recently embraced sobriety. For the first time in a long while, I feel mentally prepared to connect with others. I’m looking for a casual friends-with-benefits arrangement—something that’s low-pressure yet still meaningful.
Here’s my concern: I find receiving oral sex to be physically challenging. I’m well-endowed, and new partners seem eager to engage, but I often find myself going soft during the act, no matter the circumstances (even with Viagra). This isn’t about shame or lack of attraction. It’s a response tied to trauma. Yet, I can’t just dive into that explanation with a hookup, and many partners tend to take my reaction personally.
Giving oral can evoke similar triggers for me. As a bottom, I want to please my partners, but the act can sometimes be overwhelming. I want to be honest but without oversharing or killing the mood. How can I convey this early on without derailing the whole experience?
—Head Games
Dear Head Games,
It’s perfectly reasonable to clarify what you’re comfortable with before a hookup. If you’re meeting through apps, consider adding details to your profile (like “No oral, only anal”) or sharing in your preliminary conversation. In-person meetings can be handled with a simple chat about your boundaries.
That said, this upfront communication might unsettle some potential partners, and you need to be okay with that. If someone can’t accept your limits, they’re not the right fit for you. Many people might be looking specifically for oral, but plenty of bottoms are out there who understand your boundaries. It won’t shatter a seasoned top’s understanding of their desires. Often, the real dealbreaker is if you express a disinterest in giving oral, but I think you’ll still be fine even with that limit presented upfront. You’re not alone in this—I’ve seen numerous profiles where tops specify they’re only interested in anal. Finding the right people often requires a little patience and rejection along the way. Remember, if someone opts out because of your limits, it’s not personal; they don’t know you well enough yet for it to be about you.
Dear How to Do It,
I’m a gay man in my mid-30s in a committed, monogamous relationship with a wonderful partner. Before him, I was quite active in the hookup scene. Though I don’t judge others for their choices, I’ve realized my past promiscuity stemmed from a desire for intimacy and acceptance. It’s been a journey to address the shame and guilt from that time, but I’m slowly accepting my past as part of my growth and learning to view myself with compassion.
That being said, my partner and I have an active sex life, and each encounter is better than the last—he consistently thinks of new ways to pleasure me. However, while I’ve had numerous hookups in the past, they didn’t require much creativity from me. My partner solely tops, which means I’m the bottom. Aside from riding, what other positions might suit a bottom who wants to ensure his partner’s pleasure? Additionally, I enjoy performing oral, but his penis has a curve that sometimes triggers my gag reflex. I want to bring him as much pleasure as he gives me, so any tips would be greatly appreciated!
—I Want to Blow His Mind
Dear I Want to Blow His Mind,
Congratulations on navigating your past challenges. You mentioned that previous tops didn’t require you to be creative—does this relationship feel different to you? If not, then you might be okay. Many tops simply want to be able to use a receptive partner without much effort. Traditionally, topping is considered the “active” role; that’s just how it tends to be. Still, you might find that you can aim for mutual satisfaction without straying too far from that. You seem eager to surprise your partner, but in terms of sensation and vibe, he might prefer a simpler approach. It would be wise to talk with him about whether there’s anything he’d like you to try. The key is that various positions can work for a bottom wanting to please, depending on both partners’ preferences and willingness.
That said, if you’re feeling adventurous, try adjusting your thrusting positions. For instance, if he’s penetrating you from behind, you could initiate movement instead of him. As for oral, consider changing your approach. If you generally come up from below while he’s standing, you might try having him lie on his back instead and approaching from the top, like in a 69. That could help manage the angle better and accommodate his curve. If you dare, you could position your head over the edge of the bed while he thrusts towards you. Just take it slow at first; an overly enthusiastic partner can complicate things.
Send Us Your Questions About the Workplace!
The columnists behind our advice column want to assist you with workplace dynamics. Are you being bugged post-hours by a colleague? Has a workplace romance soured? Ask a question here!
Dear How to Do It,
My partner and I used to have amazing sex, but recently, she’s experienced chronic pain flare-ups after orgasms. We’ve adjusted positions to ease her discomfort while giving and receiving, but now, I’m finding less pleasure in these new arrangements. Plus, I had an incident where I squirted during sex, and she reacted negatively.
Shame has entered my sex life, which I’ve never encountered before. Coupled with childcare and exhaustion, we now find ourselves having infrequent and unsatisfying encounters. I’ve typically had a strong desire for sex, yet lately, I’m just not feeling it, which has hurt my partner’s feelings and left her feeling rejected. I want to regain my libido and enjoy great sex again. Help!
—Ashamed But Horny
Dear Ashamed But Horny,
You may be overcompensating. While you’ve been considerate of your partner’s limits, it appears to be at your own expense. You might want to explore further adjustments. The goal is to manage her discomfort while still ensuring your pleasure. This requires close collaboration, which might be the biggest challenge you face.
Working together in a personal space becomes more challenging when negative feelings inflate the situation. It seems your issues might extend beyond positioning; the shame in your bedroom is a hefty barrier as well. Your partner’s reactions haven’t been ideal. While she’s being honest about her feelings, the sensitivity you require seems lacking. She should recognize your physiological responses as just that—responses—rather than personal rebuffs. If neither of your approaches perfectly aligns, that’s part of navigating intimacy, and it’s worth discussing further. After all, the connection doesn’t have to be personal until you both know each other well enough for it to be.
—Rich
Dear How to Do It,
I’m a bisexual woman in a marriage. Recently, I realized I may have romantic feelings for my best friend, who has permission from her boyfriend to be with me. Although I felt flattered, I turned it down because I haven’t discussed it with my husband and fear he’d see it as infidelity, which seems fair. Still, I’m somewhat intrigued. I’d be willing to pursue something with her, but only if my husband is onboard. I don’t want to hurt him and am uncertain about the outcome. What should I do?
