What’s on his mind when he first sleeps with you?

After years of being with the same woman, men reveal the anxieties caused by someone different on the scene.

Portrait of Tammy Strobel

After years of being with the same woman, men reveal the anxieties caused by someone different on the scene.

Coordination Sasha Gonzales Photos Jalag/Rusch, Thomas/Seasons Agency & 123rf
Coordination Sasha Gonzales Photos Jalag/Rusch, Thomas/Seasons Agency & 123rf

“I’m usually too focused on pleasing her and not embarrassing myself to think about anything else!” – Ed Ho, 30, engineer

“If she does something incredible in bed that I’ve never encountered before, I’m all ‘Hmm, where’d she learn THAT?!’” – Charles*, 39, financial consultant

“If she’s doing everything right and enjoying it, I’m just working out how I can convince her to keep doing this over again with me!” – Garry Ang, 33, writer

“The first time with a different partner is always hot because I never know how far she’ll let me go. Being a man, I’m secretly hoping it’ll be all the way, and it won’t ruin the relationship we’re already in.” – David*, 33, IT manager

“If I hold my stomach in any more, I might just faint!” – Allen*, 39, accountant

“I think about what moves I should go for that have worked with partners in the past.” – Patrick Lim, 40, travel writer

“Keep it slow! I’m used to long-term relationships, and I don’t play the field in between. When I sleep with a new partner, it’s because I really like her, so not being too quick is my main priority.” – Vincent*, 33, consultant

“Whoa! My ex didn’t let us try this!” – Joshua, 41, art director

“I’m not looking for a serious relationship, so if I’m with someone new, I worry she might get emotionally attached to me. During sex, I’m into the act, but mentally and emotionally, my thoughts are usually elsewhere. Like at a foodcourt…” – Mike*, 29, account manager

“The view of my abs is making me regret living on mee goreng and beer since my ex left me!” – Jono, 30, civil servant

“If I’m sleeping with her and she’s someone I’m starting to fall for, all I can think is: ‘Please don’t screw this up!’” – Gary Chia, 42, self-employed

“How much dirty talk is appropriate? Not all women like it, so during our first time, I’m figuring out how much I can get away with.” – Amarjit*, 38, lawyer

“I pay attention to the way she moves, and the things she does and says while we’re at it. All this gives me clues as to the kind of lover she is, and if it’s a relationship that I’d like to continue.” – Benjamin*, 34, photographer

“Maaan, I am so out of practice! GOT to get back into the gym…” – Jason*, 38, marketing strategist

“I split up with my ex a few months back and don’t think I’m over it. I feel really bad for admitting this, but when I recently slept with someone I’d been seeing for a while, I couldn’t stop thinking about my ex-girlfriend. (Yes, I did break up with the new partner afterwards.)” – Jonathan*, 41, insurance agent

“Is the sex we’re having really good enough to make me want to see her again?” – Trevor*, 37, business manager

“It’s difficult for me to orgasm with someone new – it takes ages. So I’m usually giving little consideration to the woman; rather, I’m focused on making it to the finish line myself.” – Steve*, 39, teacher

“If she’s being unresponsive, I get paranoid that she’s bored. If she’s super-enthusiastic, I worry that she’s bored. New sex takes time to figure out, which is why I’m always hoping I can provide a more satisfying ‘Round Two’!” – Kevin*, 32, stylist

“I think about how my body feels to her, if she likes my buff arms and taut stomach, if the sensation of my hands and mouth on her skin is turning her on…” – Rick*, 40, personal trainer

"Am I as big as her ex? Please let me be bigger than her ex!" – Ray*, 31, artist
*Names have been changed

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