I really want to (finally) hookup with my closest friend

[CockMySuck]

Hi everyone! So, I got back from our trip together, and wanted to update you on our time together from Thursday to Monday.

Basically, Anderson and I were getting together after 5 months without seeing each other in person. We live in different cities and this was really special because, the only longer time we'd spent apart (usually pretty good at having trips together every couple of months or so) was at the start of the pandemic.

What was so amazing about the trip was that, while we went to a big city, we spent most of that time together at our place. I won't try to go through the details day by day, but listing out some of what happened. Keep in mind that I really was going into this wanting to hook up with or be more sexually open with him in some way.

Listing out some of the things that guys here will like to hear about before I get to the meat of it:

• We traded long, sensual naked fully body massages... face down only this time. I always make sure to give thorough massages to him and especially focused on his hips and ass. This time, I also worked on massaging his groin muscles – like where the leg and hip meet the groin – so I spent time near his dick doing that. While I massaged him, over the course of about 30 minutes, he let out a few really hot moans. When he started to massage me, he started with my legs and ass, and I felt him spreading my ass a little bit as he slowly, softly rubbed me from head to toe. I fell asleep during this massage and I'm still kind of kicking myself for that.
• In general, beyond massages, we were and are very touchy feely. For example, when we said goodbye on Monday, it was about 5 minutes of deep hugs. He has a way of really leaning into my neck and shoulder and nuzzling himself into me. We spend a lot of time touching and showing each other friendly affection, though he really holds on.
• There were a lot of conversations, and a lot of innuendo between us, too much to remember. For example, at one point, we were talking about our deep conversations and I mentioned teasingly liking it deep. He responded, "Oh, we'll get there eventually." There were a few similar comments from him all weekend.
• We had a few long conversations about our relationships, and friends having sex with friends. I was telling him about a trip I went on with gay guy friends recently where we ended up hooking up in a bathhouse. He had so many questions (as someone who is more innocent than many queer men) and was talking about how he wished he were in that situation.

The spicier stuff:

• We slept in the same bed one night. The first night, we spent a lot of the night cuddling. The thing is, I was naked from the waist down and, at one point, woke up to him as the big spoon. No boner or anything, just him holding my ass. That position didn't last long, but it was hot to feel him against me like that in bed. I was super horny that night (the drinking helps with that) and, the following nights, we found an air mattress which one of us would use each night. Otherwise, we wouldn't have gotten to sleep at all. We still had some naked time together after this in the bathrobes where we were staying.
• Sunday night, the night before we left, I spoke with him about jerking off and even mentioned to him that I would be open to doing it together. It all started when, one night, we watched some movie on Netflix where jerking off came up, a few times. Our conversation after the movie veered in that direction, and I mentioned that I might need to jerk off and that, if he wanted, he could join. Hours later, I did jerk off in bed that night (in the middle of the night) and was so quiet because I didn't want to wake him up. The next morning, I told Anderson and mentioned that I felt weird choking back my moans and being quiet jerking off around him – like I didn't want to feel shame around him because we're so close. He agreed that we should be more open about that stuff, and mentioned that he often overthinks things. I explicitly told him I'd love to jerk off with him sometime and he told me to bring some toys next time, and it would happen. He came up to me and gave me a hug, at which point I felt his semi-hard dick against my leg. Without thinking I moaned "fuck" into his ear, and he moaned meaning into the hug and nuzzling my neck. I even kind of let go at one point and he kept his body pressed into mine. There was so much tension and, rather than push things further right then and there, I kind of just let him lead in that moment. That may have been his overthinking, which he again brought up after this... I'm okay with him to take time to think and prepare.

I'll see him again definitely in early June if not in late May for a trip. We didn't make any huge leaps forward in terms of our physicality together but it was really hot, and we're already planning to jerk off together. Part of me wishes I would've brought it up earlier in the trip but I'm glad I didn't leave town without actually asking about it.

As Anderson and I talk about the trip and anything that happened, I'll let you know if anything interesting develops.

There's a slow build for this one and so I appreciate you all rooting for me and sticking with me here. I'm honestly not exactly sure where things are going but I have a feeling the flood gates will start to open when he each have our hard dicks in our hands... just a hunch!

 

[Aphradight]

He wants you bad. Go further when he hugs you, when you’re in bed, and especially when you’re naked together.

 

[ambrose speIlman]

I am so invested in this journey it's crazy. Looking forward to wherever things end up the rest of this year

 

[CockMySuck]

He wants you bad. Go further when he hugs you, when you’re in bed, and especially when you’re naked together.

I can believe it. I think if I went further, he'd go with it. Right now, I almost want him to come to me, because I want to be sure he doesn't regret it – there's still a chance of that, even though it wouldn't ruin our friendship. Maybe I won't be able to help myself when we're jerking off together, but I guess we'll see.

My biggest thought now is just how we'll keep up the sexual energy (and flirty vibes) while we're apart the next couple of months. Going to try to make sure we keep things warm.

 

[Anonn0027]

Hi everyone! So, I got back from our trip together, and wanted to update you on our time together from Thursday to Monday.

Basically, Anderson and I were getting together after 5 months without seeing each other in person. We live in different cities and this was really special because, the only longer time we'd spent apart (usually pretty good at having trips together every couple of months or so) was at the start of the pandemic.

What was so amazing about the trip was that, while we went to a big city, we spent most of that time together at our place. I won't try to go through the details day by day, but listing out some of what happened. Keep in mind that I really was going into this wanting to hook up with or be more sexually open with him in some way.

Listing out some of the things that guys here will like to hear about before I get to the meat of it:

• We traded long, sensual naked fully body massages... face down only this time. I always make sure to give thorough massages to him and especially focused on his hips and ass. This time, I also worked on massaging his groin muscles – like where the leg and hip meet the groin – so I spent time near his dick doing that. While I massaged him, over the course of about 30 minutes, he let out a few really hot moans. When he started to massage me, he started with my legs and ass, and I felt him spreading my ass a little bit as he slowly, softly rubbed me from head to toe. I fell asleep during this massage and I'm still kind of kicking myself for that.
• In general, beyond massages, we were and are very touchy feely. For example, when we said goodbye on Monday, it was about 5 minutes of deep hugs. He has a way of really leaning into my neck and shoulder and nuzzling himself into me. We spend a lot of time touching and showing each other friendly affection, though he really holds on.
• There were a lot of conversations, and a lot of innuendo between us, too much to remember. For example, at one point, we were talking about our deep conversations and I mentioned teasingly liking it deep. He responded, "Oh, we'll get there eventually." There were a few similar comments from him all weekend.
• We had a few long conversations about our relationships, and friends having sex with friends. I was telling him about a trip I went on with gay guy friends recently where we ended up hooking up in a bathhouse. He had so many questions (as someone who is more innocent than many queer men) and was talking about how he wished he were in that situation.

The spicier stuff:

• We slept in the same bed one night. The first night, we spent a lot of the night cuddling. The thing is, I was naked from the waist down and, at one point, woke up to him as the big spoon. No boner or anything, just him holding my ass. That position didn't last long, but it was hot to feel him against me like that in bed. I was super horny that night (the drinking helps with that) and, the following nights, we found an air mattress which one of us would use each night. Otherwise, we wouldn't have gotten to sleep at all. We still had some naked time together after this in the bathrobes where we were staying.
• Sunday night, the night before we left, I spoke with him about jerking off and even mentioned to him that I would be open to doing it together. It all started when, one night, we watched some movie on Netflix where jerking off came up, a few times. Our conversation after the movie veered in that direction, and I mentioned that I might need to jerk off and that, if he wanted, he could join. Hours later, I did jerk off in bed that night (in the middle of the night) and was so quiet because I didn't want to wake him up. The next morning, I told Anderson and mentioned that I felt weird choking back my moans and being quiet jerking off around him – like I didn't want to feel shame around him because we're so close. He agreed that we should be more open about that stuff, and mentioned that he often overthinks things. I explicitly told him I'd love to jerk off with him sometime and he told me to bring some toys next time, and it would happen. He came up to me and gave me a hug, at which point I felt his semi-hard dick against my leg. Without thinking I moaned "fuck" into his ear, and he moaned meaning into the hug and nuzzling my neck. I even kind of let go at one point and he kept his body pressed into mine. There was so much tension and, rather than push things further right then and there, I kind of just let him lead in that moment. That may have been his overthinking, which he again brought up after this... I'm okay with him to take time to think and prepare.

I'll see him again definitely in early June if not in late May for a trip. We didn't make any huge leaps forward in terms of our physicality together but it was really hot, and we're already planning to jerk off together. Part of me wishes I would've brought it up earlier in the trip but I'm glad I didn't leave town without actually asking about it.

As Anderson and I talk about the trip and anything that happened, I'll let you know if anything interesting develops.

There's a slow build for this one and so I appreciate you all rooting for me and sticking with me here. I'm honestly not exactly sure where things are going but I have a feeling the flood gates will start to open when he each have our hard dicks in our hands... just a hunch!

Whooo whieee!!! He's definitely thinking to go further but as you said "overthinks" maybe if he finally overcome those emotions you'll be in for a ride.

 

[Aphradight]

I can believe it. I think if I went further, he'd go with it. Right now, I almost want him to come to me, because I want to be sure he doesn't regret it – there's still a chance of that, even though it wouldn't ruin our friendship. Maybe I won't be able to help myself when we're jerking off together, but I guess we'll see.

My biggest thought now is just how we'll keep up the sexual energy (and flirty vibes) while we're apart the next couple of months. Going to try to make sure we keep things warm.

I’ve made the mistake of not going for it, and very much regretted it. I’m telling you, he want you. Just go for it. I do think he can tell more clearly other than saying it out loud.

 

[Shag471]

It’ll get there eventually I’m sure. My straight best friend and I are pretty close to him letting me suck him off. He loves me massaging his feet and we jack together all the time. He even lost a bet once and let me give him a hand job. So keep your fingers crossed and I’m sure it’ll happen soon.

 

[deleted15862221]

I dunno, at university i fucked my best mate and it ruined everything. He kinda went distant and got reasons I won’t go into went back to women.

 

[CockMySuck]

I dunno, at university i fucked my best mate and it ruined everything. He kinda went distant and got reasons I won’t go into went back to women.

How long had you known each other and how close were you? I’ve found on here that guys have varying definitions of best friends and closeness. I believe the depth of the friendship and closeness make all the difference, and I know we’re already insanely close. We’ve known each other most of our lives at this point and have been the best of friends over the last 5+ years.

 

[deleted15862221]

How long had you known each other and how close were you? I’ve found on here that guys have varying definitions of best friends and closeness. I believe the depth of the friendship and closeness make all the difference, and I know we’re already insanely close. We’ve known each other most of our lives at this point and have been the best of friends over the last 5+ years.

Probably about 2yrs, his past played a role, but I wouldn’t do it again. Well getting married in August so. Was shame, lost a good mate.

 

[AJbrown]

I'm definitely not in love with or interested in Anderson in a romantic or relationship way, but I do love him as a friend like I've loved most of my friends. Maybe that wasn't clear in the post but just clarifying that now. We're best friends and I am not interested in anything other than that. But I also don't think friends can't be sexual or get off together.

No, I'm not trying to "seduce" him or entice him or trap him. Some of the responses sort of lean to that. I just want to tell him how I'd love to be able to get off with him, and then go from there. Like I said a few posts ago, I'm going to have that honest, open, clear conversation with him when we're together in a few weeks. I'm opening the door to something I'm open to with him, and he knows me well enough to know I'd never cross a line or do anything he's not okay with. Again, we're that close – especially for a male friendship.

In terms of "not liking what comes after", here's how I feel: if me being myself and letting him know what I want or how I feel is enough to ruin our friendship, it's clearly not as close as it seemed. I'd rather be open, honest and my full self than repress that desire.

To that point, I have another close friend who, after years of friendship, we actually opened up to each other about wanting to hook up and explore together about a year ago. We're still only friends and it will stay that way, but I love that we can also be sexual and not repress that aspect of ourselves.

All to say, many of these situations work out, especially when you have the self-awareness, strong bonds and mutual respect needed to maintain these situations. At this point, I'm pretty confident Anderson and I do.

You seem very self aware and in control of your emotions. A lot of people on here are speaking from their own experiences and frankly seem like they have unresolved issues as a result. Just because others can’t imagine having an open/intimate relationship with some they love, doesn’t mean it’s not possible. After travelling in Europe I realized North American society is very uptight sexually and often dramatize most situations, even if it’s unintentionally and inadvertently.

 

[4_men]

He is definitely into you. Alcohol always work

 

[EnglandLad]

It’ll get there eventually I’m sure. My straight best friend and I are pretty close to him letting me suck him off. He loves me massaging his feet and we jack together all the time. He even lost a bet once and let me give him a hand job. So keep your fingers crossed and I’m sure it’ll happen soon.

If he enjoys you sucking him off then he’s not really straight, is he? Anyway, good for you! I wish I have a bestfriend like that!

 

[Shag471]

If he enjoys you sucking him off then he’s not really straight, is he? Anyway, good for you! I wish I have a bestfriend like that!

I said he hasn’t let me do that…yet.

 

[brandon38]

Hi everyone! So, I got back from our trip together, and wanted to update you on our time together from Thursday to Monday.

Basically, Anderson and I were getting together after 5 months without seeing each other in person. We live in different cities and this was really special because, the only longer time we'd spent apart (usually pretty good at having trips together every couple of months or so) was at the start of the pandemic.

What was so amazing about the trip was that, while we went to a big city, we spent most of that time together at our place. I won't try to go through the details day by day, but listing out some of what happened. Keep in mind that I really was going into this wanting to hook up with or be more sexually open with him in some way.

Listing out some of the things that guys here will like to hear about before I get to the meat of it:

• We traded long, sensual naked fully body massages... face down only this time. I always make sure to give thorough massages to him and especially focused on his hips and ass. This time, I also worked on massaging his groin muscles – like where the leg and hip meet the groin – so I spent time near his dick doing that. While I massaged him, over the course of about 30 minutes, he let out a few really hot moans. When he started to massage me, he started with my legs and ass, and I felt him spreading my ass a little bit as he slowly, softly rubbed me from head to toe. I fell asleep during this massage and I'm still kind of kicking myself for that.
• In general, beyond massages, we were and are very touchy feely. For example, when we said goodbye on Monday, it was about 5 minutes of deep hugs. He has a way of really leaning into my neck and shoulder and nuzzling himself into me. We spend a lot of time touching and showing each other friendly affection, though he really holds on.
• There were a lot of conversations, and a lot of innuendo between us, too much to remember. For example, at one point, we were talking about our deep conversations and I mentioned teasingly liking it deep. He responded, "Oh, we'll get there eventually." There were a few similar comments from him all weekend.
• We had a few long conversations about our relationships, and friends having sex with friends. I was telling him about a trip I went on with gay guy friends recently where we ended up hooking up in a bathhouse. He had so many questions (as someone who is more innocent than many queer men) and was talking about how he wished he were in that situation.

The spicier stuff:

• We slept in the same bed one night. The first night, we spent a lot of the night cuddling. The thing is, I was naked from the waist down and, at one point, woke up to him as the big spoon. No boner or anything, just him holding my ass. That position didn't last long, but it was hot to feel him against me like that in bed. I was super horny that night (the drinking helps with that) and, the following nights, we found an air mattress which one of us would use each night. Otherwise, we wouldn't have gotten to sleep at all. We still had some naked time together after this in the bathrobes where we were staying.
• Sunday night, the night before we left, I spoke with him about jerking off and even mentioned to him that I would be open to doing it together. It all started when, one night, we watched some movie on Netflix where jerking off came up, a few times. Our conversation after the movie veered in that direction, and I mentioned that I might need to jerk off and that, if he wanted, he could join. Hours later, I did jerk off in bed that night (in the middle of the night) and was so quiet because I didn't want to wake him up. The next morning, I told Anderson and mentioned that I felt weird choking back my moans and being quiet jerking off around him – like I didn't want to feel shame around him because we're so close. He agreed that we should be more open about that stuff, and mentioned that he often overthinks things. I explicitly told him I'd love to jerk off with him sometime and he told me to bring some toys next time, and it would happen. He came up to me and gave me a hug, at which point I felt his semi-hard dick against my leg. Without thinking I moaned "fuck" into his ear, and he moaned meaning into the hug and nuzzling my neck. I even kind of let go at one point and he kept his body pressed into mine. There was so much tension and, rather than push things further right then and there, I kind of just let him lead in that moment. That may have been his overthinking, which he again brought up after this... I'm okay with him to take time to think and prepare.

I'll see him again definitely in early June if not in late May for a trip. We didn't make any huge leaps forward in terms of our physicality together but it was really hot, and we're already planning to jerk off together. Part of me wishes I would've brought it up earlier in the trip but I'm glad I didn't leave town without actually asking about it.

As Anderson and I talk about the trip and anything that happened, I'll let you know if anything interesting develops.

There's a slow build for this one and so I appreciate you all rooting for me and sticking with me here. I'm honestly not exactly sure where things are going but I have a feeling the flood gates will start to open when he each have our hard dicks in our hands... just a hunch!

Wow I want this work for you guys he care about you reminds me my friend I love him but he so straight but you guys think are just scared and it ok to be just enjoy each other .

 

[CockMySuck]

Hi everyone! I wanted to write with an update after a couple of weeks staying with my friend, Anderson, 1-on-1. We had a very physically and emotionally close time together, and I wanted to share some of the highlights with you all. I'm hard writing his and love to please, so I hope many of you are too.

• Pretty standard for us: We had a hot tub for the time together and visited it frequently, always naked and always together. One thing I thought was interesting is that I noticed him looking at my dick in the tub more, and him also looking at his own dick. At one point, as he looked at his uncut dick and as it was out over the water, I brought up his dick and we started talking about his foreskin and his balls. That might've been the thing that first prompted him to talk about wanting his girlfriend to play with his balls. This was the first time but it happened after the fact, a few times a day at least, that we'd talk about his uncut dick, and especially about him wanting his balls sucked and licked. He has big balls, and these conversations were an excuse to just stare at them and marvel over them. She doesn't play with his balls and he doesn't know how to teach her. And clearly he's very horny for someone to really take care of his balls.
• On a related note, just generally, all week he was full of sexual innuendo and conversation between the two of us. We got very sexual in terms of the stories we told each other – a woman he dated who craved sex, a guy who'd invite him over to smoke and who tried to suck him off, a guy he used to jerk off with when he was younger, his girlfriend and what she's into, the things he would want a guy to do to him. At one point, he went on a rant about how guys are so much better at sucking dick and he wishes things were just more open socially so everyone could just experiment and explore with whoever, without getting so tied up on sexuality. My ears perked up and, among other things, we talked about the hypothetical and about my experiences with men and women, and the differences. He made a lot of other random references to me ass and my body, and me flirting, and even grabbed/patted my ass a little bit.
• Also, a general note, we were often naked, in underwear, or in robes.
• I took him out to his first gay bar. It was a very lively place and, actually, we went back for happy hour a couple of days later. He was the designated driver and allowed me to drink, and it was something about the vibe there that led me to hold his hand, fingers interlaced, and have a deep conversation with him. I flat out asked him about his sexuality today, and he described it as 70% women, 30% men. We also talked about how he's happy he told his girlfriend he was bi, so they could have conversations about it. There was a lot we talked about while there are the bar, for a few hours, but one of the most notable is that I took a chance and told him that I was more than willing to suck his dick and his balls. He said "I know" reassured me he would let me know when he wants it – though we continued to talk about it for the rest of our time together, the next few days.
• We also came around to talking about topping, bottoming, being vers. One thing I asked him about is if he'd be down to get fucked or have his ass played with if his girlfriend wanted it, and he said of course. We spoke a lot about how to get her into some of these things.
• We continued to be very physically close, giving each other naked full body massages. There was one night I gave him a massage where he was face down, and I was really into it, working on his whole body including his ass. I decided to get bolder, and really found myself spreading his ass, massaging closer and closer to his hole, and even massaging his taint. He was moaning during this and kept telling me how good the massage felt. I wasn't daring enough to touch his hole or play with his balls, but I'm so close to doing it next time we're together.
• We didn't jerk off together this time, but I had a long conversation with him about how jerking off helps me relieve stress, and he shared his own experience with that – specifically how when he's horny sometimes, his girlfriend will just tell him to go jerk off, which isn't usually enough. We talked extensively about a bunch of the porn we like, and I was super hard under the robe I was wearing... maybe he saw that. Knowing that we had to get ready for plans we had that evening, he said to me, "You should go jerk off and shower". I pushed back saying something and he reiterated, "Go jerk off". I did and came hard, and loud... not loud enough for him to hear me but I was less hesitant since he encouraged me to do it. After, he asked me about how it was and how I felt. He made a couple of references to me "letting a big load off".

We had this great conversation at the end of the trip, because I admitted I was worried about loving him as a friend... I let some of you get in my head about not bothering getting sexual with him to not try to lose a friend. I told him how I felt and what I was afraid of, in the middle of a very emotional conversation about life for the two of us. He assured me that we'll never stop being friends, that we'll stick together forever, and that I had nothing to worry about. He went out of his way the next day to reassure me I'm his best friend for life. I'm glad I let him know I was a little worried about that – and about going too far – and I'm glad he could put me at ease.

I'll see him again in the next couple of months, for more time like this. Every time we are together, things go that much further, so I'm curious to see what the next time will be like. I wouldn't mind playing with each other a little bit more hands-on (especially playing with his hole and balls), and it's interesting to navigate his boundaries with all of it. Going to message him about the porn we discussed and mention jerking off to it. Would be nice to be in a mode of recommending videos to each other. Anything to talk sex and be openly horny together.

 

[Aphradight]

Definitely gotta play with his hole and balls next time.

 

[yos]

So I don't get why during nude massages you don't do more, not because there's a line drawn but because you talk about more and also because he talks to you (several times now) about the kid he used to jo with. He also commented bring toys but every few months you do the same thing. You went from massaging his thigh to, spreading his cheeks to his taint but it's been dozens of massages. Why not massage him and forearm his dick and see what it does?

 

[lordassriel]

The guy is clearly sending messages to you, dude. Just go for it already.

 

[jjdiamond]

Hi everyone! I wanted to write with an update after a couple of weeks staying with my friend, Anderson, 1-on-1. We had a very physically and emotionally close time together, and I wanted to share some of the highlights with you all. I'm hard writing his and love to please, so I hope many of you are too.

• Pretty standard for us: We had a hot tub for the time together and visited it frequently, always naked and always together. One thing I thought was interesting is that I noticed him looking at my dick in the tub more, and him also looking at his own dick. At one point, as he looked at his uncut dick and as it was out over the water, I brought up his dick and we started talking about his foreskin and his balls. That might've been the thing that first prompted him to talk about wanting his girlfriend to play with his balls. This was the first time but it happened after the fact, a few times a day at least, that we'd talk about his uncut dick, and especially about him wanting his balls sucked and licked. He has big balls, and these conversations were an excuse to just stare at them and marvel over them. She doesn't play with his balls and he doesn't know how to teach her. And clearly he's very horny for someone to really take care of his balls.
• On a related note, just generally, all week he was full of sexual innuendo and conversation between the two of us. We got very sexual in terms of the stories we told each other – a woman he dated who craved sex, a guy who'd invite him over to smoke and who tried to suck him off, a guy he used to jerk off with when he was younger, his girlfriend and what she's into, the things he would want a guy to do to him. At one point, he went on a rant about how guys are so much better at sucking dick and he wishes things were just more open socially so everyone could just experiment and explore with whoever, without getting so tied up on sexuality. My ears perked up and, among other things, we talked about the hypothetical and about my experiences with men and women, and the differences. He made a lot of other random references to me ass and my body, and me flirting, and even grabbed/patted my ass a little bit.
• Also, a general note, we were often naked, in underwear, or in robes.
• I took him out to his first gay bar. It was a very lively place and, actually, we went back for happy hour a couple of days later. He was the designated driver and allowed me to drink, and it was something about the vibe there that led me to hold his hand, fingers interlaced, and have a deep conversation with him. I flat out asked him about his sexuality today, and he described it as 70% women, 30% men. We also talked about how he's happy he told his girlfriend he was bi, so they could have conversations about it. There was a lot we talked about while there are the bar, for a few hours, but one of the most notable is that I took a chance and told him that I was more than willing to suck his dick and his balls. He said "I know" reassured me he would let me know when he wants it – though we continued to talk about it for the rest of our time together, the next few days.
• We also came around to talking about topping, bottoming, being vers. One thing I asked him about is if he'd be down to get fucked or have his ass played with if his girlfriend wanted it, and he said of course. We spoke a lot about how to get her into some of these things.
• We continued to be very physically close, giving each other naked full body massages. There was one night I gave him a massage where he was face down, and I was really into it, working on his whole body including his ass. I decided to get bolder, and really found myself spreading his ass, massaging closer and closer to his hole, and even massaging his taint. He was moaning during this and kept telling me how good the massage felt. I wasn't daring enough to touch his hole or play with his balls, but I'm so close to doing it next time we're together.
• We didn't jerk off together this time, but I had a long conversation with him about how jerking off helps me relieve stress, and he shared his own experience with that – specifically how when he's horny sometimes, his girlfriend will just tell him to go jerk off, which isn't usually enough. We talked extensively about a bunch of the porn we like, and I was super hard under the robe I was wearing... maybe he saw that. Knowing that we had to get ready for plans we had that evening, he said to me, "You should go jerk off and shower". I pushed back saying something and he reiterated, "Go jerk off". I did and came hard, and loud... not loud enough for him to hear me but I was less hesitant since he encouraged me to do it. After, he asked me about how it was and how I felt. He made a couple of references to me "letting a big load off".

We had this great conversation at the end of the trip, because I admitted I was worried about loving him as a friend... I let some of you get in my head about not bothering getting sexual with him to not try to lose a friend. I told him how I felt and what I was afraid of, in the middle of a very emotional conversation about life for the two of us. He assured me that we'll never stop being friends, that we'll stick together forever, and that I had nothing to worry about. He went out of his way the next day to reassure me I'm his best friend for life. I'm glad I let him know I was a little worried about that – and about going too far – and I'm glad he could put me at ease.

I'll see him again in the next couple of months, for more time like this. Every time we are together, things go that much further, so I'm curious to see what the next time will be like. I wouldn't mind playing with each other a little bit more hands-on (especially playing with his hole and balls), and it's interesting to navigate his boundaries with all of it. Going to message him about the porn we discussed and mention jerking off to it. Would be nice to be in a mode of recommending videos to each other. Anything to talk sex and be openly horny together.

When are you meeting again? Any updates?