Another 'help Me Get A Str8 Guy' Post

How could I go about asking someone I don't know to send me naked pics or j/o videos? Haha...there's a guy I know only on the Internet who has done some art projects for me that I paid him for. (He does a lot of bizarre/psychedelic art.) He lives several states away from me. Super hot. But he's straight and has a gf.
Think there'd be a good way to go about asking this?

 

Just come right out and ask him.. I have always shared photos of myself to whoever as asked. At first I send images of my naked lower self and once I get to know and trust them then I sometimes will send photos of myself in full.

 

Straight forward about it...hm....I'm not sure if he'd do it without some incentive. Should I offer to pay him?

 

EDIT: ugh double post

 

I mean, he has a girlfriend, so that kinds of puts a damper on things lol.

Maybe you could text him and be like, "Hey, so I have a pretty outlandish request." see what he says. If he says, "Okay, what?" then be like, "Look, I find you extremely attractive and I've been thinking about you.....this is an odd question, but do you think I could get some pics?" and then go from there, aha.

 

So the guy I want pics/video from.....

He's been texting me about how he is hurting for money, and having trouble paying his bills and stuff. Which I'm sympathetic about.

But could I use this as an opportunity to get him to send me something? Something like, "I know you're really hurting for money right now. And as you know I think you're really good looking. What about an exchange...I'll send you some money and you send me some pics. Or videos."

But I don't wanna come across as a creeper and totally weird him out or make it so that he doesn't wanna chat anymore. What you guys think?

 

Also forgot to mention his gf broke up with him so that's not a factor anymore.

 

Personally, I think paying him for the pics (even if he has financial problems) might make you come off a bit creepy and he might even think you're just taking advantage of his situation.
Try telling him about your feelings first, see how he reacts.

Best advice I can give you: if he says no, accept the no. Don't keep asking. Fifty no's and one yes don't make a yes.

 

True......yea I don't wanna come across creepy, even though it kinda is to even be asking for that kinda stuff in the first place I guess.

And I do actually like him as a friend, albeit an internet friend. But we talk on the phone, text, etc pretty often.

 

Just ask him nicely, slowly lead the topic into the conversation and ask him. If he says no and you accept the no, he won't think anything of it as long as you drop the subject afterwards. At least, that's how I would react.

Give it a try, the answer might surprise you.

 

But even when going about it slowly.....I've never asked anyone for something like that before...how do I get from point A ("I think you're really hot") to point B ("show me dat dick")?

 

It depends on the conversation. When I do it, it usually starts off with just small talk about relationships and sex.
From sex it gets dirtier and dirtier (the convo), until the question is dropped.

 

Sounds pretty solid. I do feel like a bit of a creep...but I also want what I want lol.

I'll try it. Might be hard talking to a straight dude about sex since I have no real experience with women. And it might not be the best time since he's dealing with money shit and his gf breaking things off......

 

If you feel this isn't the best time, then be patient. But at least talk to him about it. Like I said, you don't know what the answer is until you ask him.

 

Yea....probably will be better way to go about it than offering to pay him I guess

 

So I didn't follow your advice and instead just went right for it. Well, sort of.

I texted him.....
"So I was thinking about your money situation...and I had an idea, but it's gonna sound weird...and it could even make you mad, idk, but I hope not......bc even if you don't like the idea, I hope things will stay cool between us...so just let me know when you're ready for me to drop this bomb on you..."

To which he simply responded,

"I got my money figured out already brotha... Well kinda"

So, I guess I blew it lol. And maybe he saw what I was going for too....?

 

Most Likely He Thought You Were Going To Offer Him Money For Sex, So

Hopefully You Will Get The Opportunity To Explain That All You Would Have

Liked Was A Pic Or Two.

Stay Calm You May Yet Get Your Pic....



Cheers Glen.

 

Maybe I should just tell him what I was gonna ask. YOLO amiright?

 

So yea since I've already started this, I'm just gonna send him a text saying what I want and see how he responds....shit shit shit...kinda scared but we'll see.

 

I told him. He didn't say no, just said that he and I were cool and things weren't gonna be awkward (bc I mentioned how I was worried they would be). He said it was all good and no big deal.

So I guess that's probably his way of saying no. Oh well!!!