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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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GeorgeTBH · 31-35, M
He seems like he is interested in them if he was asking about them but only send them if you want to if you are comfortable with him seeing them next time he asks send if not then don't. Don't do anything you would regret

And ya no guy would turn down nudes if offered
DDK98 · 26-30, F
@GeorgeTBH I mean yeah but that was a year ago and I sent him some then they were just older. Since then he’s asked for some but only of my ass which I’ve also sent. That said these ones are of more than just my ass and I’m just not sure if he still wants nudes like that, but I took them and I feel confident in most of them a few I’m a little iffy on but I figure it’s fine because he either loves me for who I am and how I look or he doesn’t. Anyways I want to send them but are conversations haven’t gotten super flirty lately because we are both so busy and I don’t want to make it awkward by bringing it up if he doesn’t want them
DDK98 · 26-30, F
@GeorgeTBH and yeah would never feel pressured. He is super sweet and always even when he’s asked for them in the past has put no pressure on me at all. As far as regrets so far he hasn’t shared any of the pics I’ve sent him so hopefully he won’t but it is what it is. I try to live my life to have more oh wells than what ifs. That said maybe I should take that advice and just send it!
GeorgeTBH · 31-35, M
@DDK98 I'm sure he would love them and that's good there is no pressure on it I'm sure it wouldn't be awkward if he has asked for them before

Or you can wait to see if he asks again or just suprise him if you want to send them to him


Honestly suprise nudes from a woman are hot
DDK98 · 26-30, F
@GeorgeTBH lol I would surprise him but he’s typically at work, in school, or around his family at which point in any of those situations if someone happens to be over his shoulder it would be a disaster.
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DDK98 · 26-30, F
@GeorgeTBH lol yeah I definitely wouldn’t want it especially if it was his family who ends up seeing it and he would very much so not be happy about it. Lol would get the opposite reaction than hoped for
GeorgeTBH · 31-35, M
@DDK98 yeah you wouldn't want that a good reaction from him but not his family lol but ya you wouldn't want anyone over his shoulder well family wise at least
GeorgeTBH · 31-35, M
@DDK98 at least when people have seen mine it was just random people looking over my shoulder 😂 i don't know if they enjoyed the show lol
DDK98 · 26-30, F
@GeorgeTBH lol yeah random people I don’t care so much about I’ll never have to see them again. His platoon sergeant or sergeant major would be terrible if never live that one down and his family would just be straight up embarrassing.
GeorgeTBH · 31-35, M
@DDK98 lol ya you wouldn't want them to see maybe they would enjoy it but it would be embarrassing if you ever met them they would have seen you
DDK98 · 26-30, F
@GeorgeTBH yeah I don’t need his dad or his sergeant knowing what I look like naked. No thanks!
GeorgeTBH · 31-35, M
@DDK98 true you wouldn't want that hopefully he has some free time with no one over his shoulder soon and hopefully he returns the favor for you
DDK98 · 26-30, F
@GeorgeTBH haha that would be nice!
GeorgeTBH · 31-35, M
@DDK98 well hopefully he would you don't want it to just be one way
DDK98 · 26-30, F
@GeorgeTBH haha he’s sent a few before. It definitely goes both ways :)
GeorgeTBH · 31-35, M
@DDK98 thats good he did and im glad it does it's not fair to you if he gets all the fun 😃

It sucks when it can just be one way