... (long and detailed, I'm pretty high right now and ideas are flowing!)I'm a 35 year old single male. I don't want to go into too many details and possibly expose myself, but here's some basics to give background. I'm recently divorced, live in a decent sized family home that I own, and have a over 6 figure income. I'm decent looking I'd say, but am bald (shaved clean and up-kept though) and should probably lose 15-30 pounds. I'd say I'm a solid 6 for most people by looks alone, and I think most people would agree that that is often raised to a 7 when they get to know me. I have strong social skills, a great friend group and professional network, and am generally well liked it seems. For a lot of reasons, I think my dating options should be decent.

Since I'm recently divorced and not ready to hop into something serious right away, I'd like to date casually. By that I mean we do "date" type things occasionally when schedules and interests align. Ideally, there would be a sexual element eventually, but I'm honestly not looking for a one night stand. A FWB situation would be ideal, but I'm open to more if there is chemistry and compatibility. I'd like to also point out that I'm more than happy to pay for dinner/drinks or whatever we do within reason. I work hard and make good money, and the good company of a good woman is well worth those costs.

However, the women that I'm finding are attracted to me are looking for serious long term relationships / their future husbands. This includes a lot of single mother's of all ages and women in their mid to late 30s that I'd assume would be considered in "my league". All this to say, I'm having trouble finding women who are interested in me AND the relationship / boundaries I'm seeking at the moment.

On another hand, I have never been into the idea of prostitution / escorts / s3x work of any kind. Personally, I think it should be legal and regulated. I respect sex work, it's just not my thing. I get off to my partner(s) pleasure and mutual interest in sexual activity, so paying for it has always been a turn off for me.

That said, given my situation that I've described, I acknowledge that my willingness to pay for dinner/drinks/activities/etc in order to hopefully getting laid by a woman that I'm not seeking a long term relationship with.... feels like a laundered form of prostitution. There are noticeable differences that we can point out, but is it really that different?

So all this got me thinking... A lot of these women could honestly use the... let's say $100 - $300, maybe more that I'm willing to pay for our date, than a night out. I'm kind of an introvert a lot of the time, so a night in would be preferable to me anyway. Stay with me here... We're adults. Most of us are desiring sex and intimacy at some point, and if we're going out on a date we can often infer (not assume or imply obligation of course) that there is at least some hint of physical attraction and therefore some possibility of eventual sexual desire for each other. Basically, I'm assuming most of the women I'm matching with on Tinder and DMing back and forth with on IG are at least not repulsed by the idea of sleeping with me at some point.

This got me thinking... as a man who really loves open and blunt conversation, especially about this kind of stuff... would it be possible for me to enjoy sex with someone if I'm paying them, but they're not a prostitute / sex worker / etc (with this obvious exception). Instead of going out and paying for the evening, we could hang out at my place. I could give her an agreed upon amount that we're both comfortable with, and we'd openly discuss what'd be on the table or not, boundaries, etc.

This also re-opens the door for me to single mothers. There are a few women that I've known for a long time that are divorced like me and have kids. They've expressed interest in me, but it seems like they're looking for something more serious. I also think that an arrangement where one of them could make a few hundred dollars extra to be treated respectfully and have a fun time would be pretty helpful to her financial situation.

For me, I'd like to add some safeguards for both of us. For instance, I'd like us both to sign a basic NDA so our arrangement would be a legally binding secret. Perhaps we could film it and cover the recordings in the NDA to ensure mutual consent... I dunno I'm high, maybe that's dumb.

I'd also like to agree on STD testing. Details could be ironed out, but I'd be uncomfortable if this woman was doing this professionally or having lots of casual and risky sex. Part of why this would be a nice mutual arrangement is the element of safety and trust.

I'll address this with myself tomorrow when I'm sober, but right now I think I could do it. I'd worry about how difficult this subject would be to broach, but there are a few women that I think may understand that I'm coming from a place of respect.

Sorry for the book, but there's a lot to explain about this. Honestly I'd love to hear what people think