Should I Make an Offer?

[Guest zipperzone]

Another good question, zipperzone. Hmm.

He just works the front desk; sadly, I've only seen him changing twice. He didn't seem modest like so many 20-somethings do these days (none of that changing underwear under a towel stuff). But no posing for me, either.

I think I'm beginning to realize that if the guy really wanted something he would have made it more obvious by now.

If he just works the front desk it sounds like he is in a service position, not unlike a doorman or concierge in a hotel and could therefore be just hinting that he thinks he should get the occasional tip.

[msclelovr]

I accept that I'm shameless, but I'm amazed that everyone is coming up with such coy responses. If he's cute, what do you have to lose by being direct?

Next time, he mentions his lack of money I suggest you say one of two things...depending on how confident you feel:

1. Well,you know I'm single and I dont know whether its appropriate but I would be happy to take you out for dinner one night. Would that help?

2. I know some guys, who are as good-looking as you, that earn good money escorting or doing massage

As long as you're polite, smile and seem relaxed about it, I can't see how he can take offence. And if he asks you any further questions, you simply suggest coffee or a drink and take him somewhere neutral.

I used the first approach last month with a handsome young straight man, who works in a restaurant I go to frequently. I took him out for lunch and we had a little fun afterwards. I've also employed the second tactic successfully; I've had one-off sex with several broke young guys, newly out of university; the best was a hot guy who for a modest amount of cash did all that I like, and he even volunteered to get tied up and spanked!

[Guest Hoover42]

I'd just smile at him and say, "You're a handsome young man. I'm sure you'll figure something out." and see how he responds.

Another great suggestion, thanks caeron!

[Guest Hoover42]

That's the best response posted to date. You could also wink when you say it.

I'm going out to eHow now to check out the "How to wink" instructional videos

[Guest Hoover42]

Hi Msclelovr,

[...] I'm amazed that everyone is coming up with such coy responses. [...]

My original message indicated that I was trying to avoid get myself into trouble; I think some of the responders are just trying to fit within that restriction.

Thanks for both of your suggestions. The first one actually looks like something I might able to try without breaking out in a cold sweat.

I've got at least four days to prepare, so I should be ready by Thursday (I think he'll be working on Christmas Eve).

[Guest Conway]

I accept that I'm shameless, but I'm amazed that everyone is coming up with such coy responses. If he's cute, what do you have to lose by being direct?

Next time, he mentions his lack of money I suggest you say one of two things...depending on how confident you feel:

1. Well,you know I'm single and I dont know whether its appropriate but I would be happy to take you out for dinner one night. Would that help?

2. I know some guys, who are as good-looking as you, that earn good money escorting or doing massage

As long as you're polite, smile and seem relaxed about it, I can't see how he can take offence. And if he asks you any further questions, you simply suggest coffee or a drink and take him somewhere neutral.

I used the first approach last month with a handsome young straight man, who works in a restaurant I go to frequently. I took him out for lunch and we had a little fun afterwards. I've also employed the second tactic successfully; I've had one-off sex with several broke young guys, newly out of university; the best was a hot guy who for a modest amount of cash did all that I like, and he even volunteered to get tied up and spanked!

As a guy who actually does this thing with some kind of regularity, I think this is a good approach. Rather than dinner, I would invite him out for beers under the guise of telling him what I do professionally and how we might have something for him at the office. You want to focus on being friendly and accessible versus appearing creepy and desperate.

As the two of you get lubed up and loosened up, get a bit physical with him. Rub his thigh briefly, let your hands brush his across the table. His body language will tell you everything that you need to know. While me may say no to your initial advance, it will be on his mind. And, as he gets more comfortable with the idea, he'll probably bring it back up to you as he starts to think about it. Don't be surprised that, if he rejects you, he brings it back up again fairly soon.

Last summer, I was hitting on this 22 year old cutie at a bar one Saturday afternoon in Chicago. We were getting pretty drunk, so I dared him to take his shirt off. He did.

After a while, I made my move and he flat rejected me. "would never sleep with another guy individually" he said. But was open to a two guy, one girl threesome. he was letting me know that he wouldn't totally rule it out.

The real problem was that his buddy from back home in Wisconsin was in the bar, too. And, he was concerned about being outed to his friend. I told him that I understood and offered to help he and his friend get tickets for the Cubs game the next day. I gave him my number so he could call me.

The next morning, he called and asked if he could stop by and get the tickets. He showed up and made it very clear that he intended to thank me for helping he and his buddy get tickets 9and for picking up a big bar tab the previous day). 45 minutes later, he was on his way to the game and I had a smile on my face..

[Guest zipperzone]

The next morning, he called and asked if he could stop by and get the tickets. He showed up and made it very clear that he intended to thank me for helping he and his buddy get tickets 9and for picking up a big bar tab the previous day). 45 minutes later, he was on his way to the game and I had a smile on my face..

Two tickets and a big bar tab...... do you think he ever figured out that he was a hooker?

[Guest Conway]

Two tickets and a big bar tab...... do you think he ever figured out that he was a hooker?

Chuckle. Most likely not. Cute? Yes. Rocket Scientist? No.

[Lucky]

Hoover, if nothing else you have created a great thread. And Conway's "Chuckel" made me think about Chuck50...wonder how he is doing.