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33 Tutoring 18...and it's getting interesting.

S

samuncut

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I'm 33. I'm bi-sexual but honestly prefer the company of men. I haven't been with a woman in about one year. I am currently single and dating (not exclusively) and live alone. I don't believe most people would suspect my sexuality but whenever anyone asks me the question, I do tell them the truth.

I tutor my best friend's brother. My best friend is 28 and straight. The younger brother, the focus here, is 18. I don't get paid for this tutoring, this is not my business or profession. I don't do it for anyone else. I guess it is just a courtesy/friendship thing. I do have a reputation for being smart so I think it does make sense that I was asked by his family if I could help him with his schoolwork. I agreed to do it and really didn't even think twice when I was asked.

The guy has a girlfriend that he has been with for three months or so. He is fit and attractive. He seems to have a good group of friends and is social and hangs out. He also plays sports for his school and seems to be a good athlete.

He has never asked me about my sexuality. If he knows, it is because his brother, my best friend, or his mom, told him. It seems more likely that the guy has no idea I'm bi-sexual, recalls me being on double dates with girls with his brother when he was younger and I would be around his house, but I really don't know. I'm just guessing at this point.

I've always been nice to him when he was younger but we really have nothing other than a passing knowledge of each other in his house when I would see his brother when he was growing up. I've never even eaten at a restaurant or anything with him. There is not even any of that hanging around and annoying older/younger brother type of history here...I really just didn't get to know him as a person at all until very recently.

Our three total tutor sessions have each taken place at my house. These are not scheduled for a certain time. He texts me to ask if I'm free on a day/time and if I am I will agree and we make the appointment. In general the dates seem to fall one or two days before a due date for the homework. The three sessions have been early December, last week when school went back and this past Sunday.

The schoolwork that I am helping with is on a laptop that he brings with him.

He honestly is not (that's right, not) particularly capable of the work we're doing, and I am somewhat carrying him so that his work gets done. I believe he is trying, but he can't grasp it. again though, I'm not in the education field so I don't know if he is or is not capable, neither do I know if I'm a good teacher. This seems to be a tough subject for him. I think he's trying but I could be getting hustled.

On the very first of these three sessions I observed some jpegs in his Recycle Bin with names like "cock1" etc. I guess I laughed or made some joke. I've tried to figure out if this was a staged event and I can't be sure. He always controls the laptop, I just look at it and point. My instincts make me think it was an accident and not intentional. When I asked about the pictures, he got visibly anxious, I just changed the subject back to the proofs we were working on, and we got back to work for another hour or so. When we were finished he said something to the effect of "those are pictures of me that I sent to my girlfriend." Then he asked me if I wanted to see them. I said yes. He showed me and they were in fact his dick. I can't deny that I liked what I saw. He cycled through them somewhat quickly and then returned them to the recycling bin and then actually emptied or deleted them for good. I said they were great, complimented him on what I saw and told him something along the lines of to be careful sharing them and to expect if he emailed them that they would get around eventually.

The second time he came over he was almost immediately upon arrival going on with "I'm horny, I really want to have sex with my girlfriend..." and such things. We're working again and he's interjecting these same comments often, like every 5 minutes or so. I don't really find the level of familiarity out of place because I've known his brother and family so long. I wasn't shocked, but kind of annoyed that the work was a struggle. While he is saying these things he also was rubbing his crotch. It was getting more than distracting. I tried to ignore and re-direct him but honestly it was getting me excited. After about two hours we were basically done or at least wrapping up the work and he suddenly said "you liked my pics, do you want to see the real thing?" I said yes. He closed the laptop, stood up, unbuttoned and unzipped and then pulled his dick out over the top of his boxer waistband. I looked of course. Maybe it was 10-15 seconds, I saw he was getting hard and he quickly tucked it back in, and then turned and walked out to the kitchen. About a minute later he came back with a drink and was smiling. He then says "your turn." I asked to be sure that he wanted to see mine, he said yes, so I unzipped my fly, while still seated, and took my dick out. He looked and smiled, and said, "wow cool." That was it.

The third time was this past Sunday, and this time we were sitting on the couch working on the laptop on the table in front of us. I got up and left the room. I came back and he had the laptop actually sitting on his lap. I sat down again and he turned to me and smiled/laughed. I asked him what he was laughing about, and he lifted the laptop up to reveal that his hardon is sticking out of his zipper and it basically bounces up. He just left it there and put the laptop on the side of the couch. He then said "let's jerk off." I absolutely one hundred percent wanted to do so immediately but I just laughed and said, "come on, let's get focused and finish this work and then we can have some fun." He bitched a little but did get back to work. He joked around a bit, but we worked for another hour. His mom called and told him he had to do a chore right away, and so he kind of had to rush away. As he is leaving he says, "next time for sure we are jerking off." I went with "let's see."

I'm really not sure what my questions are now that I re-read this. I'm kind of confused about what is going on here. I really am not interested in any kind of long term relationship with this guy, but I undeniably would be interested in screwing/playing around with him. In the back of my mind I am wondering if maybe he is using his body to get me to do his homework? That is a stretch I think, but I can't just blindly ignore the possibility. The other thing is that maybe being 18 has changed since I was 18...I just can't imagine me doing this kind of stuff at that age...or maybe I was just a wimp...

I also am kind of feeling a little "old" because of all of this. Before I tutored him these three times I honestly really felt I was pretty young at heart, i'm still playing video games and drooling over cars and listening to rap music. However, now I'm thinking that there is a guy I'm closing in on twice the age of who actually thinks I'm interesting....maybe time to grow up?

I guess I should also explain that I don't really worry that this would become an issue to my best friend or his family. I know them, I'm not embaressed or feeling guilty. I don't think there is any risk of some kind of blackmail from this younger brother or anything. I'm of course prepared to be advised otherwise, but I honestly am not stressed or worried if they were to find out that there would be some negative repercussion that could hurt me. I do think their mom knows I am bi, and certainly she doesn't seem to mind him being at my house...

So, I don't know, maybe just let me know what you think?
 
For me, the age gap isn't a problem. The best friend's brother might be, but I'm sure he can get over it. What is the problem is he has a girlfriend. You are older so you should probably set a good example (since you are analyzing it). He's going to be doing this for a long long time throughout his life. Might as well teach him how not to go about it.
 
If you think your best friend would be fine and his family would be fine with it then that's not the problem. But I think this has all been staged. People just don't do that. He's clearly knows you are bi then and is either wanting to experiment with someone he feels safe with or he is wanting to use you to do his work for him. I don't know him so i can't say but those are the two things that I think are likely based on what you've said. If you think his brother would be totally ok with it then you should ask him what he thinks.
 
As somone who spends 8 hours a day around teenagers, I can assure you that they are, as a whole, far mor sexually knowledgable and adventurous. It doesn't mean that they are any more mature, but they certainly don't have any problem saying what is on their mind. If the situation really is as you describe it then he wants to hook up. So long as he is 18, you need to think about how this will affect the relationship between you and your friend, because very few people can keep secrets, teenagers especially. If you dont think your friend will care than go for it!
 
Hmmm. Whatever happens, I think this has bad idea written all over it in big thick black permanent marker.

Maybe your friend and his family are cool with the idea - great, sort-of. Perhaps you have a fling, or just a few hook-ups or whatever - is that not going to get weird with your friend eventually? Especially if it doesn't pan out, or one of you wants to make it more permanent or something and the other doesn't - surely that's just going to make things tricky for your friend because his loyalty is going to be stretched one way or the other. And this is still the best-case scenario.

Alternatively, perhaps your friend or his family isn't cool with the idea - if yes, surely this is shaping up to be a massive train-wreck.

I'll admit I've been in a similar-ish position - same sort of age gap (12 years) with a guy I worked with. The attention was cool; I also felt much younger (and your idea of fun matches mine, if you substitute rap with modern rock) and more bullet-proof than usual. But it didn't happen, and although I wonder how much fun it would have been (a lot, I'm sure!) I think that was probably for the best.

Good luck!
-d-
 
man... if you want to keep you 'best friend' as your best friend... well then quit tutoring his little brother..
who knows if this kid is messing with you or not... is it worth it to lose your best friend over it?
Up to you to decide.

I'd let this 18 year old move on...
 
i think that you should first try to figure out what is in his mind. try to talk with him.

and don't forget, he is your best friend's brother. He and his family are trusting you. So one more time, first try to figure out what is in his mind.

(this is a 19 year old talking)
 
Wow, I feel for ya man! I was in the same situation for a longer period of time with my best friends brother, but my hell started when he was 16. I won't go into details, but I finally had to tell him the "come ons" had to stop or I was going to tell his brother, which of course ended it... Three years later at his brother's wedding, guess who came knocking on my hotel room door @ 2am?

I'd think really hard about your decision, your friend probably wouldnt find out, but is it worth what guilt you might be feeling if you go thru with it? From the sounds of your note you would feel guilty, so if I were in your shoes I would be the grown up and pass :)
 
Its a double edged sword for the OP now, because if he does say No then he could tell his brother about what they have done which is enough to end a friendship anyway.... but if he says yes he could do that anyway.
 
I got hard reading about your problem. LOL

I tend to like men my own age or older, but sometimes the idea of a young stud is exciting.

Keep posting updates!
 
If he is really over 18 you are both consenting adults. What you do in the privacy of your own home is your business. He obviously knows that you are Bi and is exploring his sexuality with someone he trusts. It's up to you how much you are willing to teach him. ;)
 
If he wants to experiment it it'll either be with you or some random guy he finds off Craigslist, or in a bathroom, etc. Frankly, I wish that I had a trusted family friend to experiment with when I was 18.

If your story is accurate, you're not pressuring him in any way. I don't see anything wrong with it.

I suppose it would be awkward to ask your friend's permission, but your friend may be glad it's you and not some crazy dude that's into drugs or has an STD.

A horny teenager has no problem getting laid. But they sometimes get laid by the wrong people.
 
theplayerking said:
If he wants to experiment it it'll either be with you or some random guy he finds off Craigslist, or in a bathroom, etc. Frankly, I wish that I had a trusted family friend to experiment with when I was 18.

If your story is accurate, you're not pressuring him in any way. I don't see anything wrong with it.

I suppose it would be awkward to ask your friend's permission, but your friend may be glad it's you and not some crazy dude that's into drugs or has an STD.

A horny teenager has no problem getting laid. But they sometimes get laid by the wrong people.
Click to expand...

great point of view
 
Hes probably just normally horny and since on the first session you already went through awkward sexual phase he just feels more comfortable around you to just be more open. i don't think hes looking for anything other than a quick jerk.
 
If anything happens, just let it happen naturally;

Chances are, someone so young wouldn't want to be in a long-term relationship; it sounds like he knows about you, you're someone he can trust and have fun with.

If he's over 18, he's an adult, and he sounds smart enough not to tell everyone.

However, since you know his brother and family so well, tread lightly, and cautiously. You seem to have a good intuition, and I'm sure that you'd probably put a stop to it if the train is about to wreck.
 
You sound like a very thoughtful and smart guy based on your details. I'm the same age as you are and I'm currently a little angsty about my own attractions to someone who is 19. I'm inclined to say you shouldn't worry too much about this and you should enjoy it for what it is, but you know your good friend more than we can. I don't know why it would ever have to be an issue between you and your friend even if he did find out (and I kinda doubt he will, at least for some time). If you guys are friends, he should be okay with you "dating" his family members. Otherwise what kind of friend is he? I would assume he is a friend of yours because he thinks you are a good person. Me, I would want my family members being with good people. Go for it, but be careful. As others said, I'm interested to hear how this works out, so please follow up.
 
Not to make this thread about me, but I want to tell a story and maybe we can find some common ground to help eachother.

About 5 years ago, I was employed in the public school system as a teachers' aide. During that time, I had interactions with many students, but only as handful in a professional sense. Tyler, one of the students I knew but did not work with, was in 6th grade when I met him. He was polite, nice and a funny kid.

Fast forward 6 years. Tyler is now 18. I ran into him in town and we started talking. He was interested in photography, and I do a lot of my own developing, phtography etc. He said he wasn't interested anymore, but would like to model. I told him he'd be a great model and would he like to model for me. He said "YES!" and weas really excited. He texted me that night with ideas for shoots etc. I shot him a week later in a hotel room with a 70's junkie theme. Washed out color, high contrast, etc.
Pics came out great. He asked if I shot porn, I told him I had before. He asked if I'd like to shoot him, I said maybe but not that night, as we were done. As I'm packing he pullsd his dick out and starts stroking. I start shooting pics and bows his load opn his chest. I ask if I can lick it up, and he sayd yes. So I do. Now... I still have many ties to the school, although I'm no longer employed there.

Tyler has become a good friend and I've shot hoim a few times, all with the same ending. He's "straight" but thinks its "cool" that I'm gay.

At first I felt creepy because I had known him when he was young and awkward, but I certainly don't anymore.

What I have realized recently is that your sex life is private, you don't owe anyone anything. This is between you and the kid, and me and Tyler. I say have your fun, but maybe keep that part seperate from the tutoring. Maybe? I'm not sure it matters.

Best of luck Sam!
 
It's easier to find a fling than a best friend, so I wouldn't risk damaging that friendship. Your best friend and his family sound cool, but who would be cool with their 33-year-old friend having sex with their 18-year-old brother when you're supposed to be helping him with school? None of us know them, only you do, but it still seems like a stretch that it wouldn't have a negative impact. Sometimes friends surprise us with their reactions, especially when it comes to family and, on top of that, sex.

Even if they wouldn't find out, is this being a good friend? Wasn't that the whole point of tutoring him in the first place?

I think some of these comments are romanticizing the situation because it sounds like a fantasy. But are we really to believe the only options for him are you or some dangerous boogey man you'd be saving him from? Doubtful. You're prob just a blip on the radar until he finds someone his own age to mess around with.
 
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