dilemma

[NLbear]

Somewhere else on this site I have been telling about the boy I have "on loan" from a friend (acqaintance rather) because he was told not have anal sex for a while. This 24yo guy is more than hot. VGL muscle boy with huge smooth pecs and sensitive nips. Flat stomach, ass to die for and an 8-inch fat cock. He's been fucking me senseless 2-3 times a week and I love it. Fucking hot sweaty sex And he usually goes for a round two. Later I learned that my friend was paying him for his services. Which he uses for his education. 

After another round of athletic fucking I was catching my breath and he made himself comfortable waiting for his balls to fill up again. He purred he loved fucking me. He loved my sexual appetite. Unusual for older guys he said. I was sucking his nipple and stroking his big fat cock when he said his "relationship" with my friend had ended. Oh? He said my friend was told not have anal sex anymore. And with that his "services" were no longer needed. I looked up at him. What did that mean? Well, he needed to find another source of income. Ah..... I asked if he was looking at me for that? He hesitated a bit. Well, it would be nice but not necessary for now. He knew other Daddies who were more than willing to pay him. He grinned probably less sexual than me. Would even be better he said. We didn't talk about anymore. He was raging hard and ready to go again.

Now I don't know. I knew he was a Kept Boy but it really didn't bother me that much. I wasn't paying him. Now, unless he finds another sugar Daddy, he may be looking at me. And I'm not sure what I'll do then. He's fucking me so good and so often I don't want him to go. But I'm also against paying him. What to do?

[NordicBtm]

Well that seems like a difficult choice. Maybe you can be honest with him about not wanting to cross over into pure sugar daddy terrain, while you could find ways to support him if you can? I don’t think you want to enter the territory of him living off you, but I guess in the future I could see myself having someone like that live in a rental that I had for free, or something like that. I understand how difficult it is for the young people now, but at the same time I would only go as far as you feel comfortable with and for me providing assistance that is not directly paying money would be preferable to paying him money. Just how I feel about it but haven’t thought so deeply about it to be honest. Good luck!

[hntnhole]

8 hours ago, NLbear said:

What to do?

Be really careful.  At one time, I "kept" a cumdump for a few years.  The 'cumdump" part was glorious - but he had a little secret (drugs) that he managed to keep from me for quite a while.  While it's not my business who takes what, it does become my business when they live in my house.  Things went missing when I wasn't around (apparently tricks with sticky fingers), and the drug addiction made him more and more unreliable.  A ton of fun while it lasted, it didn't end badly - but it did end.  

Just be sure you know who the guy really is.  

[onlyraw]

That is one of the problems of being on older guy who enjoys the company of younger… (and clearly it doesn’t matter if you are the cum dump or they are) …. A lot of the younger guys are looking for sugar daddies 

so for you the question is, is this in your budget or not …. 
 

if not … than you just have to be honest and see if your ass is such a good fuck that he is willing to get a real job … or take out loans to get his education..so that he can say with you and keep breeding your eager ass

let us know how it all turns out …. Worst case is that you have had some great sex ….

[blackrobe]

11 hours ago, NLbear said:

[...] I knew he was a Kept Boy but it really didn't bother me that much. I wasn't paying him. Now, unless he finds another sugar Daddy, he may be looking at me. And I'm not sure what I'll do then. He's fucking me so good and so often I don't want him to go. But I'm also against paying him. What to do?

Be up front with him.

If he ends up asking you for money, and based on what you've said that doesn't seem as likely, tell him you love the sex you're having but that you're not in a position to pay him. Tell him that you understand if he needs to focus on what will fund his education and that you'll miss him and the fun you've both been having. I'd also let him know that you'd love to see him again when he has the income he needs sorted out.

[bbzh]

Find out from your acquaintance how much he was paying the guy. Hate to be blunt here, but if you're not willing to pay, then you are probably not going to be a priority for him. He's already "interviewing" his next sponsors. It's obvious you still want to play with him, but he's telling you straight up that he expects to be paid. It's probably best to just fade into the background and cherish the memories. And make sure you're not falling for him. His strategy may very well be "let me get the guy hooked on the sex before I terminate the free services." This is something all older gay men will have to deal with at some stage. I'm very suspicious of any guy under 35 showing an interest in me because what do you want? It can't be just sex you're after, although I'm aware there are guys out there who prefer the more mature guys. I've got several in my orbit now.