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Should I offer to send new nudes to a guy I’ve been talking to for over a year, or wait until things feel flirty again?

A guy and I have been talking for about a year and a half now. We’re long-distance but hoping to meet up soon. We’ve planned to a few times, but life and busy schedules have always gotten in the way.

Over a year ago, he asked to see ‘more of me with less on.’ At the time, I sent him some older nude photos and a newer swimsuit picture since I didn’t have time to take new actual nudes. He responded with, ‘holy shit, you’re hot.’ Shortly after that, we hit a rough patch because he came across a Reddit profile that had posted an inappropriate picture of me and private information about us. He thought it was me at first, but it turned out a now-ex friend had shared it there. We worked through it, and we’ve been talking ever since.

We’re not officially together, we agreed to wait until we meet in person before taking that step, but we still talk and flirt like a couple when we have time and neither of us has been seeing anyone else. He’s asked for butt pics a few times (we’re both into BDSM/spanking, so that fits our dynamic), and he’s complimented me and even referenced the old nudes I sent or mentioned taking pictures and videos when we are together, but he hasn’t asked for new ones, he’s also seen the back of me nude due to corner time and our dynamic but I don’t really consider that the same thing.

Lately, I took new nudes and boudoir type shots and have wanted to send them for over a month, but we’ve both been so busy between our jobs and college that our conversations have stayed short and not very flirty or longer but on the more serious side of things. I’ve been thinking of saying something like: ‘You mentioned before that you wanted to see more of me with less on and all I had then was old pics…well, I finally took some new ones. If you’d like them, just say the word, no pressure though.’

That said I just don’t want it to make things weird. It’s hard because sometimes it feels like we’re in a relationship in every way but name, and other times I can’t tell exactly where we stand and it seems like we are just more platonic/fwb like kink partners but most of the time when I feel that way it’s when we’ve been forced to be distant due to our lives being so hectic. What do y’all think? Should I bring it up, or leave it alone for now? I feel like most guys would never turn down nudes, and I am hopeful it will create more flirty conversation again when we have time, but like I said I just don’t wanna make things weird if he’s not on the same wavelength.
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GinPanda · 26-30, F
Do what feels right but do not feel pressured. Maybe just something flirty and see what the reaction is
DDK98 · 26-30, F
@GinPanda see that’s the thing is I want to send them. Like he hasn’t pressured me in the least even when he has asked for them in the past. That said I don’t want it to just come out of nowhere and blindside him or make things awkward if he’s not in that headspace right now because without a true label on things and with things being a bit more distant and less flirty recently (which I believe is due to our lives being insanely busy lately but still I gotta overthink everything) I could see it making things weird if he’s not on the same wavelength as I am. That said if I ware for the perfect time it could never show.