Approaching str8 student

[+ FreshFluff]

He thinks I am str8 but may be reflecting on why I chose him, as there were a couple dozen guys working there.

 

Most str8 guys don't think about these things that way. He probably thought, "Awesome, extra money."

 

Also, if you're going to try this, I recommend starting with more general conversation about his classes, how he likes college life, whether he decided to pledge a fraternity/how he chose his dorm. Nothing threatening.

 

Forget ethics and the image of gay men for a moment. Your profile says that you live in a southern city. Many frat types in those areas are packing heat. For your own safety, you need to make sure his body language and words show real interest before you hit on him.

[rvwnsd]

I think you are going about this all wrong. Consider hiring someone for sex and then ask if he would consider doing yard work. That way, if you get turned down, you still got laid. The way you are doing it, all you get is a clean yard.

 

A few years ago I hired this one guy on a regular basis. He started out working a retail job and then was going to school. I mentioned once that I was looking for a cleaning lady to help me do a deep-clean of my condo. He offered to help me clean for a reduced rate in conjunction with a post-cleaning escort appointment. He started out fully dressed and ended up completely naked and hard. Best damned cleaning job!

[maninsoma]

5'10" and 145 pounds and that's the guy you chose to help lifting heavy objects? I understand he might look awfully cute with those stats, but he surely doesn't sound like he has much muscle if he's that thin.

 

Situations similar to the one you're proposing happened to me when I was younger. I didn't take any of those guys up on their offers and, frankly, even though I knew I was gay the offers felt creepy to me because they were so aggressive. If you're intent on trying to make this fantasy a reality, I echo the suggestions above to approach it in a much more subtle way by offering a drink, making small talk, and seeing how he responds when you make little comments that indicate you find him attractive. Unless he already is an escort (or has thought about it), making a blunt offer of money for sex probably wouldn't go over very well.

[wayout]

All I can think of if this works out for you is that it would make a great porn flick

 

I consider myself a low to moderate risk taker so I don't think I could do what you want to do. So it is difficult to think like someone who is a higher risk taker than I normally feel comfortable with. However, I think there are some good suggestions from others and perhaps I would (after verifying his age as another poster recommended) offer a cold beer,hoping it would lead to some casual conversations about life and love in general which would open the door for sharing some of your own interests, allowing you to gauge from his reaction how to proceed.

[+ sync]

If things should go south, he may opt to share your propositioning him with his boss, his friends, his school, and/or his family. In that event things could go further south.

[+ newatthis]

... I do not think that many of you are waiting on pins and needles, but I will let you know how this works out.

At least one of your readers is waiting on pins and needles .

[+ Gar1eth]

Jake (I hope you don't mind me shortening your name here),

 

I'm going to assume you are mostly gay. I'm just wondering how you would have felt if a mid '40's to 50's year old woman-let's say in average condition after a few children-a widow- had needed a 'poolboy' back when you were say 20? And then after a few visits started coming on to you. I'm just wondering.

 

Gman

[+ Chris Eisenhower]

I think you are going about this all wrong. Consider hiring someone for sex and then ask if he would consider doing yard work. That way, if you get turned down, you still got laid. The way you are doing it, all you get is a clean yard.

 

Really, this is the best suggestion yet.

[Kenny]

When the young man is working in the yard and bends over, move up behind him, put your hands around his waist, and grind your crotch into his butt. If he responds well to this, you'll have some idea of what he might do for cash.

 

I saw this once in a porn movie and it worked like a charm. So...

[Rudynate]

I have some heavy property work I need help with and approached a cute college student working at a local nursery and he is coming over Sunday to give me a hand. Naturally I would like to hire him for bigger and better things. Sure I know the correct answer is that approaching str8 guys is risky and I should stick with well reviewed personnel on this site. Given that I seem to gravitate toward risk, do you have any suggestions on how to bring the subject up of a willingness to hire for more than yard duties?

 

I have known guys who specialize in this sort of thing. They seem to really enjoy the chase and the risk involved. But guys who are good at it, are REALLY good at it. They regularly score with incredible-looking straight(ish) men. And it often turns into something regular. I was always drawn to it, but could never push myself to take the initial plunge. At 62, for me, that train may have left the station.

 

One closely-related thing that I love is to hook up with other gay men in unexpected places. A very long time ago, I did a lot of union catering/hospitality work. I was working at an APA (American Psychiatric Association) convention, and I was walking across the exhibit floor. One of the attending psychiatrists and I exchanged one of those looks, where it's all said and done in a half second without a word being spoken, and I joined him that evening in his hotel room for dinner and fun.

 

I have an old friend who had a regular thing going with a married guy that he met on CL. The guy would come over, they would get high, and my friend would blow him and rim him. The rimming was what the guy was really after because he couldn't get his wife to do it for him.

[Guest Starbuck]

When I was a year out of school, working on a college campus in a non-academic capacity, I was invited out for a drink by the chairman of one of the departments. We had cause to interact professionally and he casually proposed the idea after the third or fourth time we’d spoken to one another. I thought he was just being friendly until instinct belatedly kicked in and told me what he was really after. I was too young and inexperienced to fully trust that instinct. I didn’t want to seem unfriendly by declining the invitation and I sure as hell wasn’t going to tell the guy what I suspected. It was awkward on so many levels—the unequal power dynamic of our jobs, the age differential (late 40s/22), the common workplace and the fact that we were going to keep bumping in to one another, that we were going to have to interact professionally. Anyway, we went out for a drink. He did his best to get me drunk, but I was still sufficiently in control of myself that when he finally kissed me—when I had the confirmation of my instinct that I needed to finally speak up—I told him that I was involved with someone. I handled it as well as I knew how at the time, trying to minimize embarrassment in the interest of being able to work together without a hideous degree of awkwardness.

 

There are differences between my experience and the scenario described in the original post, but there are enough similarities that one called the other to my mind. Draw your own conclusions about how a young man put in any similar situation by a much older one will feel 99% of the time. Decide for youself whether you’d feel good being that older man.

[+ WilliamM]

When I was a year out of school, working on a college campus in a non-academic capacity, I was invited out for a drink by the chairman of one of the departments. We had cause to interact professionally and he casually proposed the idea after the third or fourth time we’d spoken to one another. I thought he was just being friendly until instinct belatedly kicked in and told me what he was really after. I was too young and inexperienced to fully trust that instinct. I didn’t want to seem unfriendly by declining the invitation and I sure as hell wasn’t going to tell the guy what I suspected. It was awkward on so many levels—the unequal power dynamic of our jobs, the age differential (late 40s/22), the common workplace and the fact that we were going to keep bumping in to one another, that we were going to have to interact professionally. Anyway, we went out for a drink. He did his best to get me drunk, but I was still sufficiently in control of myself that when he finally kissed me—when I had the confirmation of my instinct that I needed to finally speak up—I told him that I was involved with someone. I handled it as well as I knew how at the time, trying to minimize embarrassment in the interest of being able to work together without a hideous degree of awkwardness.

 

There are differences between my experience and the scenario described in the original post, but there are enough similarities that one called the other to my mind. Draw your own conclusions about how a young man put in any similar situation by a much older one will feel 99% of the time. Decide for youself whether you’d feel good being that older man.

 

When I was a freshman in college in 1962, I remember a cute classmate and friend reading "Another County" by James Baldwin. He then told me about several experiences like the one explained by Starbuck. By then, he was already very concerned about any older man who approched him in too friendly a manner. Reading "Another Country" was a way to obtain some more knowledge. As soon as I read Starbuck's comments, I immediately remember that day over fifty years ago.

[+ purplekow]

When I was a freshman in college in 1962, I remember a cute classmate and friend reading "Another County" by James Baldwin. He then told me about several experiences like the one explained by Starbuck. By then, he was already very concerned about any older man who approched him in too friendly a manner. Reading "Another Country" was a way to obtain some more knowledge. As soon as I read Starbuck's comments, I immediately remember that day over fifty years ago.

I have told this story in the past on this forum. I was hitchhiking home from college classes and was picked up by a man in his 40's who easily directed the conversation to oral sex. Asked if I had a girlfriend. Asked if she was cooperative sexually (getting awkward) and then saying he could do a better job and would pay me to prove it. Needing money and a bit curious, I exchanged seats with him and drove the car as he gave me a blow job. When he wanted to stop because his back was hurting, I forced his head down and made him finish. He did not pay me in full the agreed upon price. So it can turn out the way you envision, but this is not my type of game.

[Rudynate]

When I was 18-19, I was a magnet for older men, and I enjoyed talking with them, but I wasn't ever attracted to them. Often, after a short conversation, a guy would give me his card and invite to his place for a weekend, or some such. I was too dumb to realize that sex was implicit in the invitation and it took accepting a few of these invitations and having it all go wrong before I figured out the rules. Once I did, I began to limit my interaction with older men because I preferred not to deal with those awkward situations. Eventually, I learned how to deal with them in a way that allowed everybody to save face and move on. Took a long time, I was a slow learner.

 

One of the privileges of what I do professionally is that I get to interact all the time with bright, educated young men. I call them "smart boys." It is really a pleasure, but I don't allow sex to ever enter the equation.

[corndog]

I'm going to offer a dissenting opinion...

 

I wouldn't write this situation off completely. Instead, I'd approach it with subtlety and finesse, view it as a long-shot, and enjoy the journey.

 

First of all, DO NOT offer him money for sex. As you're working with him, keep the conversation light and friendly, and take an interest in him and his life. Offer him some beer after the work is done, and try to develop a friendship, or at least a friendly rapport. Try to find additional work that you'd like him to do in the future, so you have a good excuse for ongoing contact. Keep in mind that as you get to know him, his attractiveness might evaporate, or it might become clear in conversation that it's just never going to happen.

 

As your rapport develops, look for opportunities to gauge his comfort level. After a day of sweaty work, offer him a shower and see if he comes out fully dressed, or wrapped in a towel. Keep your actions on the borderline of sexy and innocent, and whenever you make a move, be sure that it is something that could be construed as a misunderstanding, or benign action. If he's receptive to your advances, he'll send signals. If he's not, make sure your actions are ambiguous enough that he can never be totally certain that you're a creep.

 

When the time is right, hire him for an afternoon of yard work, but start with the beer and conversation, and "oops, we never got around to the yard work."

[Rudynate]

I'm going to offer a dissenting opinion...

 

I wouldn't write this situation off completely. Instead, I'd approach it with subtlety and finesse, view it as a long-shot, and enjoy the journey.

 

First of all, DO NOT offer him money for sex. As you're working with him, keep the conversation light and friendly, and take an interest in him and his life. Offer him some beer after the work is done, and try to develop a friendship, or at least a friendly rapport. Try to find additional work that you'd like him to do in the future, so you have a good excuse for ongoing contact. Keep in mind that as you get to know him, his attractiveness might evaporate, or it might become clear in conversation that it's just never going to happen.

 

As your rapport develops, look for opportunities to gauge his comfort level. After a day of sweaty work, offer him a shower and see if he comes out fully dressed, or wrapped in a towel. Keep your actions on the borderline of sexy and innocent, and whenever you make a move, be sure that it is something that could be construed as a misunderstanding, or benign action. If he's receptive to your advances, he'll send signals. If he's not, make sure your actions are ambiguous enough that he can never be totally certain that you're a creep.

 

When the time is right, hire him for an afternoon of yard work, but start with the beer and conversation, and "oops, we never got around to the yard work."

 

 

You sly dog, you.

[Becket]

As one who enjoys the chase as much as the event, I say go for it, and have a great time. Nothing may come of it. But what fun you will have with all the build up! cheers

[TruHart1]

You sly dog, you.

 

I believe that's sly "corn"dog, Rudy!!!

 

TruHart1

[+ Gar1eth]

I make no bones about being prudish in many ways. I just don't understand why you think this would work unless the guy was actually gay or bisexual. I mean sure I can fantasize about my hunky straight neighbor. But I'm not going to make a move on him.

 

Why do I keep thinking of the old Penthouse Forum letters? " To The Editor-I am a student at a small Midwestern University. I never believed the letters in the Forum until I had to stay overtime stocking with the Head Waitress...."

 

This scene from Glee keeps coming to mind-but in my opinion it's not very funny.

 

 

Gman

[nate_sf]

I will be closely (very closely) working with this cute guy all afternoon in a sweaty operation. I need the help, but I crave the eye candy and proximity.

 

So leave it at that. Get the work done, enjoy some eye candy but I'll join the others in cautioning against anything more. It could go badly in so many ways, and him thinking you're straight could further complicate things. I'm not even sure I'd offer the beer. Just offer him a cold drink - if there are going to be any beers, let it be his idea.

 

Having said that, as others have mentioned sometimes these things do click under the right circumstances and when both guys are of the same mind. But if anyone's going to make a move, let him be the one to make the move. Does he take his shirt off and strut his stuff? Does he compliment you on your physique? Well then you might have something. But if he doesn't put himself out there, I wouldn't push it, and even then would take things pretty delicately.

 

Just on the most practical side of things, if it went badly would you be able to go back to that nursery anymore? Would he have told the other guys he works with, and now when you go there you'll be that guy? Best to just get the work done, enjoy the view and know you are welcome to go back to the nursery when you want some eye candy.

[JulianLondon]

I'd play the long game with him. No harm having him in for a beer afterwards. And hey why not just chat and be nice. What about trying that and getting to know him. Make it obvious you're a happy, sane guy, maybe leave an Advoctae or two around the place. Just ask him about college and life. Get him over again and if he turns up then you have a better chance. IMHO

[jakeleyman]

Hey guys - Just wanted to thank you again for the great advice. I have read every one of the messages and considered all the thoughtful advice regarding my crazy plot. Just received a message from Malcolm. He's coming tomorrow noon unless it rains as predicted on Easter Sunday...."Malcolm?"...well, I probably have a better chance with a Malcolm than with a "Buddy" in my part of the country. I think it will be entertaining at least. If you are going to do hard labor, which I had planned to anyway, when you are looking for butt cracks and jeans buldges, it could lighten the load. However the other develops - we'll see.

[Bryanforservice]

Just keep us posted! Regardless of the advice given, I think we are all interested to see how it turns out!

[+ dutchmuch]

I say Go For It, just don't want you disappointed - as I suspect you will be.

[banawe]

I think the idea of seducing a young college guy is hot! I'm sure it worked in real life, where would those porn plots got the idea from **cheeky grin**.

 

I had a similar experience when a neighbour hired 3 Dutch backpackers to do minor renovations in his apartment. I approached the cutest one but rejected my indecent proposal. He wasn't offended and was actually seemed flattered by my advances.

 

I think the youth nowadays are less uptight about this often seeing it as a compliment. I think you should pursue him but with extra caution.