Working With Will

[Kyanimal]

Hmmmm ... very, Very, interesting update! In fact, I'm not exactly sure what my impressions are. I am sure that I need some more time to wrap my brain around that one. But ... I'm going to plunge on, anyway! ...

I don't have ANY doubt about Voyager's post! I was quite impressed by it, and am hoping to hear more from him around here! I'm quite glad to hear that You did get back to him!

As for Your own, sincere, intentions of contributing even more (I doubt that You fully appreciate what You have been giving to Your readers, already!), I'm sure it will be quite Valuable and Insightful! I thought I was already as Impressed with YOU as much as I could be! And, then, You go and prove me wrong!!

Now ... just where the Hell was Will coming from with his "escort question"?? What would prompt him to even bring that up? I doubt it ... but was he maybe thinking that the two of you could make some good, fast, bucks? Him being your "manager" perhaps?? No ... that just doesn't sound right! I mean ... knowing what we know about Him!

But ... he does seem to think, that if You would consider going that route, that You would be quite successful! Seems that He is Very Impressed with You, too!! So ... maybe He was just letting You know, in a "safe" way, what He really thinks about You?? We already know that He thinks You are Sexy, but THAT appealing/attractive??!! Hmmmm ...

And ... his follow up about Your doing it if someone like Him wanted to hire You? Fishing for a compliment from You, maybe? But, Man!, I loved Your answer! Set that poor Guy right back in his tracks!! I'd be willing to bet that what He might have been expecting (perhaps Hoping for?), was something more along the lines of, "Why would You want to "Hire" Me, when You know I'm more than willing to "do" You for Free?"

Now, Will has a bit of "unsurity"! (I know that's not a "real" word, but it should be!) And, I think THAT is a "good thing"! Keeps him just a tad off balance! And, gives Him a bit more to think about!

Is Will a little more curious about boys than He's willing to admit? I'm thinking ... "Oh, Yeah!"

Sorry to hear about the toe!! Which one, and what did You do?? Take Good Care! And, of course, no matter what ...

Keep smilin'!!
Chaz

 

[nautiboyjeff]

I think you should continue to ask him to come to your place, watch TV, go to movies, just do things together. He seems very comfortable spending the night. Ask him to sleep with you. You jumped to the sucking part, but maybe you can back up and see if he is interested in some intimacy. For example, if he spends the night, just watch tv and touch each other, ever so slightly and see how he reacts. Make him dinner, dote on him. Men love it.

I would suggest that if he sleeps with you see what happens and get what you want out of it. If he kissed you as a dare, see if he will kiss you intimately in the dark when you are laying together.

He might not know what he wants and so saying anything really isn't in his realm of thoughts, but he might know what feels good and right.

Think of it like a man does a woman, romance him some. You don't have to be sappy. Just show him you like him.

BTW - as a OU grad and Sooner fan - the Sooners are back in the hunt!

 

[yeahman21]

Just tell him he can stay in your bed instead of staying on the couch.

 

[Diodorus]

Oh so sorry to hear about your toe. That has to hurt. I have a similar situation with a male and the friendship so out weighs an orgasm. We have no trouble telling each other we love each other. These are incredibly rare souls on this earth and we're lucky to know them.

 

[comedycentral]

I have kind of the same problem. I have been buddies with this guy for about a year and a half, and he has gotten more and more "flirty" in the last few months. Last May, we had a chance to hang out like everyday because he was still in town for Maymester (a semester that is only like 3 weeks long) and I was still in town because of my job. We were kind of the only ones in town, so we hung out everyday and I guess kind of got close? I've had a huge crush on him ever since i met him, because he is hot as hell. Its not super overt, but it definitely seems a little more than just joking (even though that's the way its spun). He has that joking kind of personality, but it just doesn't seem like he acts quite the same way around me as he does other guys. Its a very subtle difference, which is why I'm really apprehensive about it. He is a huge player, and hooks up with a ton of girls because he's jacked and what girl wouldn't want to get fucked by him, but still, there is something about him. He kind of has a way about him that makes me think he doesn't think the same way about gay guys as a lot of guys do. I've never told anyone that I'm bi, so he has no idea i like guys, and he really doesn't have any reason to think that, because I'm not the "flamey" type at all. Maybe that I haven't hooked up with that many girls, but still.

For instance, yesterday me, him, and another one of our friends went snowboarding. We got back pretty late, and I was exhausted and beat up, so I went to bed early. I get a call at 3 a.m. and its him, kind of drunk, wanting to smoke a bowl. I'm always down to smoke, so I say sure, and he comes over and we smoke. But when he got to my room (I was just in my boxer briefs because that's what I sleep in), and he comes in and says something and touches my bare shoulder in a way that I thought was kind of borderline homo. I'm regretting that I didn't do something else, like get out of bed in my boxers and walk around/sit on my bed with my buldge sticking out, but I didn't. I am really trying not to sort of place a false meaning to the things that he does out of sheer desire for him, but I am a pretty smart, unbiased guy so that seems unlikely. Next time it happens I'm going to do something to test how in to me he is, but its obviously a very thin line to walk, because the worst thing that could happen is he actually WAS just joking and realizes that I like guys. I guess the only good thing is that he would PROBABLY be a lot cooler about it than all of our other friends but still, its not really an option in my opinion.

But it sounds to me like you have a pretty good chance with your guy. good luck.

 

[voyager]

Thanks for the PM James! I was not expecting such a personal response. It was my first PM, and everyone says your first time should be with someone special! HA!

I am surprised by Will's questions about being an escort also. I am glad that you told him that you had to move on because things seemed one sided. At least he knows that you too have emotional needs that need to be fulfilled. From his obvious concern about your possible "change in feelings towards him"(that is ... just being friends), could it be that he is afraid that you might "move on", and then he would have missed an opportunity with someone that he really cares about? While he is coming to grips with his new feelings, I am sure he is scared a bit, and maybe, he felt that if you were involved in just casual relationships such as escorting, this would give him time to sort out his feelings and you would still be available when he is ready.

From things you have said in different forums, if you are the same in real life, he has to know that you are more complex than that, and that a casual type relatinship over and over is not your thing. You are much too emotional to enjoy the one night stand, and I believe you would prefer romance and passion, the hallmarks of a deeper, more satisfying partnership. I really think he is afraid that if you become involved in a deeper relationship with someone else, he will regret letting you go.

So, I agree with others who have said that you should continue with the nights out with him. Offer him the couch, but as you go to bed, tell him that your door is open should he want to hold, be held or just cuddle. This is a simple non-threatening way for him to ease into his feelings. He may not jump off the couch right away, but I bet as the night goes on, he will be awake weighing the pros and cons, and will eventually slip into your bed. And if you are dressed only in boxers, I would bet that cuddling will lead to other things. Remember, he has never touched another guy before, but if the opportunity exists, and he feels comfortable as I think he does with you, I am sure he will be more daring and take some initiative. While it may be tempting for you to offer another BJ, this would be a step back to that one sided relationship that you already told him would not work. I think Will now understands that there has to be some reciprocal emotional gratification.

I think Will is ready to make a move, but until meeting you a short while ago, these feelings were all foreign to him. While he seems very put together in the way he did not let your first encounter become and obstacle in your friendship, I am sure he still fears what his own reactions will be if he take things to the next level. He needs some time to sort this out, to accept the fact that as a "straight" guy, he has developed feelings for another man. Knowing that you are there, willing to help him at his pace will be a great comfort. If you were to make the moves, he might feel threatened, and if uncomfortabe, back away because of this apprehension. Being there and letting him progress at his his pace will be less threatening to him.

As always, I anxiously await any update from you!

 

[voyager]

That plan sounds good! Hoping for the a positive outcome . . you deserve it!

And thanks again for your kind words!

 

[cityboi]

Hope you find yourself in his loving arms!

I just got together today with a bi buddy I hadn't seen in four months. I missed him so much. He may be moving in with me for a while to get away from his usual environment....

 

[ziyingoliver]

I feel not lonely anymore after I joined the Jub,as a 29yearold gay man,I have no luck at all ,I wish someday someone would fall into me like Will do to you

 

[Coffee]

Then he asked if it was someone like him that wanted to hire me. I asked him what the relevance of that was and he said that there may be guys that I'm interested in that would hire me. What then? And I just laughed at him and said "what makes you think I'm interested in you? I thought we were just friends? I've moved on, Will." And he actually seemed upset! It gave me the chills--the good kind--when I saw how he reacted. I wish I could explain the face he made. It was like he was stunned. He asked why I'm not interested in him anymore(!!) and I just told him that it was a one-way crush with no mutual attraction, so I had to move on. It was unhealthy. He said he didn't know I liked him that much. So I told him maybe I still have a little crush. haha. I still can't believe we had that conversation. It was like something out of a dream. I've wanted to see him upset over me for a long time.

wow I missed your story recently. Due to this quote, I think that he may wanna ask you out for a party or something... and you said no, that ruined his plan and drived him upset, cuz he was pretty sure you would say yes...

 

[Noodles]

So, I agree with others who have said that you should continue with the nights out with him. Offer him the couch, but as you go to bed, tell him that your door is open should he want to hold, be held or just cuddle. This is a simple non-threatening way for him to ease into his feelings. He may not jump off the couch right away, but I bet as the night goes on, he will be awake weighing the pros and cons, and will eventually slip into your bed.

I think I've been following this thread too closely lately.... after reading this late last night I had a dream involving a guy that I like. In the dream he stays the night on my couch after a night of drinking and I go off to my room. At some point in the night I awake to find him sitting on the edge of my bed in his boxers, back turned to me. I pretend to still be asleep and after a few minutes of silence and no movement on his part, he quietly lays down beside me and rests his head on my chest. We fall asleep that way... I haven't been able to get the dream out of my head all day, it was hot!

Maybe this is how things will turn out for you... best of luck man!

 

[nautiboyjeff]

I am dreadfully addicted.

 

[josher]

James, you are a warmhearted, caring. smart, funny and very attractive guy.

You deserve a partner as great as you are.

Why do you keep putting yourself into these unrequited relationships?

If you can play around with this guy sexually and truly keep yourself from falling for him, OK. Enjoy it while you can.

But seeing who you are from all your posts, I believe you're going to get your heart broken again.

Maybe Will is a closet case, and your friendship with hin will let him admit who he is and come out. Anything's possible.

But I've observed dozens and dozens of these kinds of relationships (and almost got into one or two of them myself), and they've all ended badly for the gay guy.

I admire you and hope you find a great guy who will be able to love you in every way for who you are.

 

[blogthissucker]

so i am another one of the people who has lurked by this thread for a long time. i was trying to think of something to post that hadn't already been said and i think i've finally come up with something....

i really like the "i'm wearing your boxers; you're going to have to take them back" idea. I know you missed the chance but I think you should go out of your way to come up with other things like that... forget yours at his place and see what he does, or do something with lockers/his clothes if you guys change at work. If your friendship with will is anything like i picture it, he would find the "take back your boxers" idea hilarious and fun. The thing with that is that it's such a blatantly sexual game, but it still seems natural in the context of two guys just joking around. Going on the idea that will is at least bi-curious (which seems to be a given by now) I think that's probably the way he'd be most comfortable progressing. If you think back to stuff like the bj, it was the same way: blatantly sexual, but it's a drunken dare so he could convince himself it doesn't mean as much. I think the "come to bed if you want" thing is a little more toward being just sexual and might not be as likely to get results (although it still could).

I think it's safe to say that will is pretty comfortable with the idea of you coming on to him, if you want to, although you saying you're no longer into him kind of makes that awkward. So I've taken the liberty of writing the next chapter in the Will/James saga as I think it should take place... I think it's your duty to act it out.

SUGGESTED SCENE: HAS NOT ACTUALLY OCCURED
[J has made sure that W has nothing to do on Friday night and suggested some vague plan... W is walking toward his car to leave after work... J cuts him off with his car]
J: Get in
W: What?
J: Got anything going on tonight?
W: lol, no
J: Now you do. Get in.
W: Wha?
J: It's important.
[W gets in. J speeds off, cue intense driving music]
W: Why the hurry?
J: I'm horny
W: What?
J: I was thinking about what you said.
W: Said about what?
J: About how you want me.
[J switches gears, close-up of shifter then cut to car speeding down the the street and cue intense rev sound]
W: WHAT!?
J: Oh, sorry, not you, your face. You were sad I didn't like you any more. So you like me. Ready to return the bj?
W: Uhh.........
J: [grabs W's crotch, feels movement]. Sweet! Let's go get drunk first so we can blame the alcohol.

Then, on TV, you'd arrive at some store to do an errand RIGHT AFTER DELIVERING THAT LINE and just disappear for like 5 minutes (iunno, picking up dry cleaning), giving him enough time alone that you could start a new conversation and pretend like the original one didn't really happen.... in lieu of dry cleaning you could try cranking the radio really loud for a few minutes...

J: So what kind of beer do you want?
W: [still kind of shocked, but secretly interested] You really think I'm going to suck you off?
J: [mock confusion] What? You want to suck me off? What the hell are you talking about [wink]. ....What kind of beer do you want?

And then off to drinking, with the clever understanding that you'll both be trapped at your place when you can't drive any more. He knows what's coming and he knows it's your idea. Then after you've both had a sexually charged evening of anticipation find some excuse to wrestle him to remind him that you're expecting physical contact...

And try to forget to get clothes from his house. Then have him borrow a bunch from you and see how he returns them... or give him a pair of boxers from when you were like 6 and then "wait, those don't fit, take them off" and spend like 5 miuntes trying to find a pair that really do fit. "Find" a pair that's dirty first and see if he takes them... lol, i'm getting ridiculous. time to post. basically just ignore my ideas, lol.

 

[Coffee]

lol... I think that's called good boy gone bad. Anyway, I think that he's been playing the two ways card. You know, like "if someone like me ask you out" or so. He seems wanna move closer to you but still having the safe exit. But like you said, don't make you one day, in the future, keep saying "what if...". Just try charming him

 

[GL]

Josher, thank you for voicing your concern and still being willing to support me if it's something I really can handle. I think about this all the time--that I keep falling for guys who are more or less unavailable. I've debated it in my head so many times. The only conclusion I've come to every time is that I'm having fun. I have something that makes me enjoy going in to work everyday. I have someone that I think about when I wake up and when I go to bed. For the last week or so, there have been very few times that I have instigated any flirtation with Will. It's been my decision that if he wants anything to happen, I won't stop it. I'll go at his pace and allow him to explore his curiosity. I admit, I can't say I don't have any expectations, hopes or desires. Of course I do. But I won't let that get the best of me. I realize this may never turn out to be anything more than it already has been, but I don't want to look back one day in 10 years and wonder what could have happened if I had just been willing to go along for the ride.

i have to say that i agree 100% with what josher has already said. i think you're a great guy james and deserve to have someone to love. but i would wish it were someone who can be upfront with his affections.

and then i read that last sentence.

i know i look back now on my life and can see several instances where i wonder "what if?"

it is better to live your life without regrets.

 

[evanrick]

i think any time a guy does something "flirty" or "borderline homo" they are obviously testing boundaries like others said.

some guys just may want to have a gay relationship or encounter but dont want all the labels that comes with it.

 

[Coffee]

^ that advice is genius

 

[walsh0829]

u sound like a pretty cool guy, someone i wished i work with, better yet went home with..hah
very nice pics in your gallery as well any man would be lucky to curl up in bed beside you...wouldn't mind seeing u painting naked either

 

[GL]

^ well the first thing you could do would be to fold up whatever money you plan to give him, walk up close to him preferably face to face and slip the cash into his back pocket. make sure he can feel your hand against his ass!

just make sure to tell him 'thanks for helping out' so he doesn't think you're propositioning him.