Straight Friend Playing Around Too Much?

Or at least stop wasting time with the hand jobs and just put it in your mouth. He won't expect that and I doubt he'll stop you.
If it wasn't related to my boss I would, but I'd rather not attempt to do something like that if there's a chance he won't be into it. I said he has a lot of issuses regarding his homophobic upbringing, so i don't wanna go all out unless he gives me actual signs
 
If it wasn't related to my boss I would, but I'd rather not attempt to do something like that if there's a chance he won't be into it. I said he has a lot of issuses regarding his homophobic upbringing, so i don't wanna go all out unless he gives me actual signs
Ok fair point. At the very least you should ask the next time he let's you at him. From what you've told us the urge is surely there, the issue is getting him over the hump.
 
My friend, you both need to shit or get off the pot. I understand at 23 you don’t have a wealth of experience to fall back on. I know I didn’t. You both have unsorted emotions. Make a decision. Stick with it. Be happy. Y’all like each other’s dicks clearly. Why the unnecessary complications? A lot of us had religious upbringings and we ultimately make our own decisions about what we want. We get one life. We need to live it for us and be happy.
 
My friend, you both need to shit or get off the pot. I understand at 23 you don’t have a wealth of experience to fall back on. I know I didn’t. You both have unsorted emotions. Make a decision. Stick with it. Be happy. Y’all like each other’s dicks clearly. Why the unnecessary complications? A lot of us had religious upbringings and we ultimately make our own decisions about what we want. We get one life. We need to live it for us and be happy.
I have to agree. If your emotions really start to get to get entangled in this, it's going to be a real shit show. If, and this is only if you actually want him, and he's not ready to go there you may have to remove your self from the situation until he figures out his feelings.
 
I wasn't going to put this because I know some of you are ready to hear "oh yeah I blew him" or something, BUT that hasn't happened. It's been 2 months so I'll post something. We hung out the other day and as usual I started playing with his dick. Someone facetimed him, but I kept going and put my hand down his pants. He didn't react to it so I took it a half step further and unbuckled his pants and pulled his cock out and jerked him off. He kept talking to the girl he was Facetiming and talking to me like nothing was happening BUT he kept getting quiet and breathing heavy. Honestly I thought he was going to cum lol. But he stated he always has trouble finishing so I didn't really expect it to happen. He was leaking a lot though hahaha. I had to go eventually though, but he said he wanted to hang out again today...so maybe another update?
 
I wasn't going to put this because I know some of you are ready to hear "oh yeah I blew him" or something, BUT that hasn't happened. It's been 2 months so I'll post something. We hung out the other day and as usual I started playing with his dick. Someone facetimed him, but I kept going and put my hand down his pants. He didn't react to it so I took it a half step further and unbuckled his pants and pulled his cock out and jerked him off. He kept talking to the girl he was Facetiming and talking to me like nothing was happening BUT he kept getting quiet and breathing heavy. Honestly I thought he was going to cum lol. But he stated he always has trouble finishing so I didn't really expect it to happen. He was leaking a lot though hahaha. I had to go eventually though, but he said he wanted to hang out again today...so maybe another update?
Well at least it's an update. He's not having trouble finishing, he's holding back.
 
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Next time he drips pre on your fingers..lick it off your finger...see how he reacts? He might ask if you want it directly from the source...or he might ask how it taste...if he does..put you finger towards his mouth... see if he licks it or sucks you finger., Im in a very similar relationship... it can be frustrating...but I value our friendship.
 
Next time he drips pre on your fingers..lick it off your finger...see how he reacts? He might ask if you want it directly from the source...or he might ask how it taste...if he does..put you finger towards his mouth... see if he licks it or sucks you finger., Im in a very similar relationship... it can be frustrating...but I value our friendship.
So what exactly are you getting out of this friendship? I'm genuinely curious because it seems like the sex can screw with that bond.
 
I remember meeting one partner once at the local pool.

I used to go swimming several times a week at the same time and naturally you tend to bump into the same people who have a routine.

There is this one older mature gentleman that would often say hello and chat a little bit to me both before and after my swim. Over the course of several weeks we develop a friendship and discussed swimming. Occasionally he would comment on a few women that he noticed swimming and I just totally assumed based off that he was straight, looking back I guess he was testing my sexuality. Up to this point there was no indication to me that he was gay or bi with anything he said or the way he looked at me. Mind you I was younger and very inexperienced. If there was signs, I wouldnt have known.

One day after a few weeks, he sat next to me in the spa. I noticed and felt his leg rest/touch my leg. I was very flattered that he felt that comfortable and at the same time didnt make anything of it as I just thought he was manspreading and it as more accidental contact than deliberate. Not to mention there was other people in the spa with us, so we were not alone.

The next time we sat in the spa together it was just the two of us on this occasion and everytime he wanted to ask me a question he placed his hand on my thigh to get my attention, until he finally just rested it there. Of course I loved it and got extremely turned on, as this was the most public I have ever been with another guy, but being naive I just continued to talk to him. I still thought that was just the manner in which he communicated and he was just being friends with me.

He then slowly moved his hand over and rested it on my erect throbbing dick. At this point I was only more nervous about being caught then anything else. I guess it was only now that I realised that we were not "just" friends.

I was careful to not make him feel that his advances was not welcomed as I didnt want to scare him away. So I told him what he was doing felt really good, but was feeling hungry for lunch and suggested we could go back to his place. We both showered at seperate sides of the male shower rooms and I just met up with him at his car. On the short drive back to his place, we chatted normally and when we got to his home, he actually served me lunch to my surprise as I thought we would immediately be into it when we got there. I think he was just making sure I was totally comfortable and not scare me off.

After lunch we sat on his couch watching TV for a while, before he made his first move. He layed me down on his couch and started passionately kissing me, while undressing me and the rest is history. It remains as the longest foreplay I have ever had with a guy where it took several weeks for us to go from "just friends" to sex.
 
So what exactly are you getting out of this friendship? I'm genuinely curious because it seems like the sex can screw with that bond.
I'm not trying to sleep with him haha (at least not go all the way). I just want to figure him out and hopefully help him accept himself. Sure he needa to do that for himself, but considering his upbringing and the people he feels like he has to be friends with he can't. At least I want him to be able to be himself around some people because rn he hates being alone and as he puts it "loses interest after he sleeps with a chick"
 
As far as updates go we haven't hung out too much, but we have the past 3 days. Monday and Tuesday we just chilled in his car. However I've been trying to be more bold. I would rub his back and cuddle against him to see what he would do and he never reacts. Well, he doesn't pull away or flinch. If I cuddle against him he uses his other arm to use his phone or whatever.

Those 2 days we chilled at my house and I would unzip his pants and pull his cock out and he never says anything about it. We just go about our conversation or he'll keep talking to whoever on the phone/facetime. (People are at home so can't do too much). I haven't made him cum yet, but he has mentioned how difficult it is for him to get there. Maybe I'll stay the night with him and see what happens. At this point I def wouldn't say he's straight which was kinda the point of the thread? Should I keep updating?
 
As far as updates go we haven't hung out too much, but we have the past 3 days. Monday and Tuesday we just chilled in his car. However I've been trying to be more bold. I would rub his back and cuddle against him to see what he would do and he never reacts. Well, he doesn't pull away or flinch. If I cuddle against him he uses his other arm to use his phone or whatever.

Those 2 days we chilled at my house and I would unzip his pants and pull his cock out and he never says anything about it. We just go about our conversation or he'll keep talking to whoever on the phone/facetime. (People are at home so can't do too much). I haven't made him cum yet, but he has mentioned how difficult it is for him to get there. Maybe I'll stay the night with him and see what happens. At this point I def wouldn't say he's straight which was kinda the point of the thread? Should I keep updating?
If you're trying to get to another level with him or whatever, you're going to have to do more than just handle his dick. He's in FaceTime anyway, you may as well get down there. And yes keep updating, we invested at this point.

Lastly, I see your location is Alabama. If that's true, BE CAREFUL!
 
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Small, kind of cute, update. A few days we hung out and I did the usual pull down his shorts and play with his cock. Not much different there. Honestly I think he would let me suck him off, but I want to make sure he's okay with it and I have a good place I can do it without worrying someone will see us. But it was getting late and he told me to text him when I get home and I said I would. Well a minute into my drive he calls me and we just talk. He asked my opiniom on a few things, but a light-hearted convo. Since then he's called me at least once a day and texted me wanting to hang out. I've been too busy this week though. I think I'm going to try and stay the night soon