Best Friend Obsession

My best friend from 18 until now has been Issac. I’d known and been his friend to some extent since we started school at 5. But for many years he wasn’t as well liked by anyone including me because he had this god awful temper. He’d fly off the handle, sometimes get violent and start fights. But when that kind of passed and some of my other friends just became more distant, I found I like Issac more and we spent more time together and, as I have explained elsewhere, a huge reason was I thought he was cute. I was really attracted to him. We became friends because I pursued him but also because he somewhat idolised me as I was a smart kid and he just really liked talking to me for some reason – impressed by the fact I was a “science nerd” and liked being asked about it and, rarely for a nerd I was also popular among the some of the more popular kids in the more popular groups – which Isaac wasn’t so much. Also, we lived in walking distance from each other. So as the friendship deepend, the visits became more frequent which deepend the friendship – which was awesome for especially the first 3 or 4 years or so, then for 2 or 3 years super close but more dramatic with turmoil thrown in,  and then it kind of became the friendship of actual adults who had their own lives and eventually families: one that involves only infrequent visits but a very swift slide into old rhythms and a friendship that seems it’s one of those that will last right up until the first one goes.

But this story is about my first sexual experiences with him. For the first 3 years of our “best friendship” which really is very much like a marriage of kinds we were always explicit and suggestive with each other. We loved porn, talked openly about sex and I would always get secretly turned on hearing him talk sex in any capacity. He became almost the sole focus of my masturbation fantasies. But he wasn’t gay or, so it seemed, interested in guys in any capacity. He had a girlfriend and cutting to us both at 21 he’d been with her – Haley – for over 4 years and she was now in her final year of school. Issac and I hung out together when Issac, Haley and I weren’t hanging out. Well it felt like that. And we really loved each other’s company. Enough intro:

One day in my room Issac and Haley are on my bed watching tv and I am at my desk looking up something on my computer and they’re giggling more than normal behind me and I turn around and Issac is reaching into her pants and bra and giving me the beginnings of a show. I think Issac said something like, “Have we been like this infront of you before?” and I’m laughing it off with like “Yeah. You’re in love we get it!” and he keeps going and I go back to the computer and then say something like, “Damn printer…hold on I have to go find paper,” over my shoulder as I leave the room. Which I did because I knew exactly what was going on and being suggested and offered. But I was a virgin AND I was in love with that guy in there – I had fantasised seeing him naked, seeing him cum over and again…and here it was coming true. Ok, his girlfriend was going to be a part of this (though she was, objectively speaking cute with a very hot body - I felt exclusively attracted to him…for the moment anyway!). So I had this stupid stumbling reason to leave the room. My parents were home anyways so I wasn’t being offered there and then. We were due to go out to a party together which is why they were there – to pick me up. All I could think to do, imagining them waiting for me to return, was call two of my other close male friends and tell them straight up what was happening to get advice quickly. One friend basically said: no advice. Be careful – it’s friendship after all. The other said to get back in there and do something! As I’m gone for about 5 mins and by the time I’m back inside they’re ready to leave for the party.

In the car on the way they’re saying, “This isn’t about changing a friendship – it’s about just having fun.” And I can’t think what to do and for some reason just want to string out this part of the whole “dance” a bit longer so I’m playing dumb with questions like “why would you want to change a friendship?”

“We don’t. We’re saying we don’t won’t to change it.”

And I said, “Well look. I don’t want to change this friendship either, bad as it is. I don’t have the energy to do anything different.” And just joking to make out like I’m utterly missing the point and I’m getting excited by a song on the radio and changing the topic by singing then asking if they know who else is going tonight and they’ve just given up for the moment. So we go to the party and Haley and I just ignore it in our conversations but Issac keeps saying things like, “You won’t make this easy, will you?”

I’ll say, “What?”

He’ll say, “Exploring – doing something different.”

And I’ll say, "Doing something different?" Like saying something that doesn’t go in a circle.

And so this cat and mouse goes until even he’s bored. And we go home from the party and the following week it’s a little more awkward than normal and Issac makes it clear he’s a bit shitty with me because HE KNOWS that I KNOW. And he knows there must be a reason I’m not just leaping into discussing it. But I’m not exactly sure why he doesn’t just saying explicitly he wants a 3 some. My guess is that at this point he was too scared of rejection and/or changing the friendship for the worst, permanently. Truth is, I was not ready to decide. I had no clue and was sort of worried but way more curious to take the opportunity to be nude and hard with Issac.

So one day that week I finally relinquished and said, “So you want to have a threesome”?

And he was like, “yes”. Cut to the weekend and I’m over his place and so is Haley and his parents are out and we’re in his room after having had dinner and it was all so “expected” and heavy and I am fiddling with a soundsystem looking for music and suddenly Issac is going down on Haley and Haley reaches into my boxers to be the first girl to ever touch my cock (and first other person at all since my first encounter with a guy in high school). Soon we’re all completely naked and I am sucking on Haley’s cute little perk tits – which I just did not know how to enjoy entirely back then because I was utterly distracted by Issac. But if it isn’t obvious to the reader, this is intended, it seems, to be a straight 3 some. Two guys fucking a girl. The two guys don’t get involved with each other. So I’m pretending to be fully into the breast sucking but I’m looking at Issac to catch a glimpse of his cock.

Eventually he decides to fuck her and I see it for the first time. He says he, “Isn’t as hard as he expected,” and that sticks with me for years – he was kinda saying he wasn’t as turned on as he expected which I took personally – even though he later admitted that this 3some was actually the second time he and Haley were having sex that day. So of course he wasn’t in tip-top-testosterone. So his cock was big to me. The biggest I had ever seen in real life. Maybe 17 cm. Mine was 15cm and a little thinner but with a better shape. His head was a bit lopsided. Of course it looked delicious to me but our next position was me getting head from Haley and Issac fucking her. Eventually he announced he was cumming and I was so excited to see that. He came in her and then went and had a shower while I had sex with Haley but I think I was too nervous to cum. So that was the first time.

We must have had 3somes dozens of times after that. Then I began to get a little possessive of them both and became jealous of when I wasn’t invited into their bed and so there were times when the sex would stop and it would become a big issue for me which became a big issue for the friendship. But we weathered it pretty well. One things to come out of the 3some gradually declining in frequency was that I felt way more comfortable being affectionate with Issac – initially during the 3somes maybe a touch here and there and maybe once it was all over the 3 of us just lay naked together for a while or showered or slept together – which led to cuddles in bed. And it was still common for Issac to come to my house or me to his and we’d “stay over” in each other’s bedrooms and until recently that was all. But it began mainly with the fact Issac liked a massage – foot massage and eventually leg massage.

One day, and we both of us each year now acknowledge the date with a text to each other, early in the morning – like 6am – an hour before we were due to get out of bed, we are laying together and I am hard as a rock as I usually am when laying next to him because of his cute eyes and gorgeous face and especially in these situations his hot body and smooth olive skin the only part hidden was by a pair of loose boxers. He’s atheletic – super fit from competitive soccer – but not super muscular. Toned but hard muscled. He was laying on his stomach as he often did and so driven by horniness I just took a risk and went to the other end of the bed and began massaging his feet. I knew what he liked and spend a good 10 minutes there until I could tell he was both awake and liking it. I moved up his calves and upper thigh and then butt and this meants eventually I pulled on his boxers and he raised his hips so that they would slide down over his perfect smooth bubble butt, down over his runners thighs and hamstrings and eventually off him altogether so he want completely nude but facing down. And I returned to massaging his butt and making it sensual and pushing his legs apart so I could play between them and begin a massage of the spot between the anus and cock where you can feel that someone has a hard on if you press. I could feel he was hard now and I was massaging his inner thigh and butt and he had a hardon. Eventually he couldn’t resist longer and simply rolled over naked and fully hard. So I just went straight for it. First I used a hand just to explore it as this finally was the fantasy come true. Issac’s eyes were closed as he faced the ceiling not seeming to want to watch – wanting I guess to try to pretend he was still entirely straight by imagining it wasn’t me but a girl.

So I gave him head and it took a good bit of work. Maybe 10 minutes all up even. But eventually he grunted, “Keep going,” and “Don’t stop,” and he came in my mouth and I was so turned on and I tasted it (it tasted just like mine) and I swallowed it all.

I said I needed the bathroom – which I did. I came back and he was fully dressed on bed with his head hanging down as if something super dramatic had happened. Which I thought had – but he wasn’t quite so buzzed as I was. But he was fine – little was said except he had to get home to change and get to work.

But guilt got to him, or catholic shame, and Issac said after a few weeks that it was a first and a last for that kind of thing. Which was hard. And I didn’t take it well. But the threesome happened a few more times at quite lengthy intervals given how we were still spending significant time each week with each other. I was reasonably happy with the arrangement but just as emotionally it did fuck me over in ways I never contemplated or imagined when the offer was first made to have a 3 some with my best friend and his girlfriend, I think the reality of introducing sex into a relationship among 3 young people who don’t understand much about relationships and sex affected Issac and Haley too – and not for the better. I learned only recently that I wasn’t the only one to be involved with Issac and Haley but that actually they’d invited Haley’s best friend and her boyfriend to partner swap with them. So that did something to the dynamic as well. So whatever the case, Issac became more distant and moody from both of us who kept trying to cheer him up and interest him. Eventually this culminated in Issac deciding he needed a holiday – alone and overseas for a good 6 weeks without us. So it was Haley and I for that time. And we found comfort in each other. I think by now she’d noticed I had a thing for her boyfriend and that in the bedroom I had clearly been ogling him and touching him more. But I think she liked it. But while he was away we began spending nights together watching tv until late in my bedroom where often I’d end up massaging her which would always end up in me eating her out and fingering her to intense orgasms that way (apparently a skill I have developed) before she made me fuck her until I came inside her (she was on the pill). So without Issac I was absolutely able to become more and more focussed on Haley and find her a turn on. Clearly I was bi.

Eventually Issac returned and Haley and I didn’t mention anything about the sex we had with each other while he was away. It felt like a betrayal and yet at the same time – we’d all been in a 3some together so in my mind was never a big deal.

Months went by and all was coming back to normal except that Issac was becoming quite moody all over again and impatient and seemingly bored at times with us. Sometimes, as with the holidays but on a smaller scale, he’d just cut us both off and make it clear he’d rather spend a Saturday night doing something else than spend it with us like we used to always do and never tire of. Haley and I hadn’t tired of each other or of him. It was solely him seemingly tired of us. I think because he felt under far too much pressure being the central focus of attraction and desire. As it was one Sunday night he told Haley he didn’t want to spend the night with her watching tv so went to his father leaving her alone but with his blessing to come and see me and do whatever.

So she came over and yet again the tv watching on the bed turned to touching, then a massage, then nakedness, then sex. And midway through this session between Haley and I, yes: Issac snuck in, barged in the door to the bedroom seemingly knowing full well what he would find, and promptly left by slamming multiple doors and speeding off. Haley was beside herself as was I. Longstory short they broke up for a week or something before reconciling and Issac refused to speak to me for some 2 months or more – during which time I was just devastated and guilt ridden and desperate. But then eventually we too reconciled. And this time what happened eventually, to help us “get over” the whole trauma Issac got us some pills. So he and I in my bedroom, took ecstasy for the first time. So I was finally able to just say to him, “I’m in love with you,” and he said, “I’ve seen it.” And we hugged naked all night and I massaged him and gave him head and it was beautiful.

We did that many more times over the next 2 years when, finally, Haley and Issac broke up for good when she admitted to finding someone else. He was devastated for a time after dhe left him for good. But he was motivated to make a big change so he and I moved overseas together working in New York. There we lived in the same sharehouse for 8 months or so but grew further and further apart sometimes going weeks at a time barely speaking for 2 people who lived across the hall from one another. We weren’t hostile or fighting or even “not friends” – we were just, I think, searching to fix something which wasn’t us exactly. I know he had a few flings there but he seemed to have a plan or something I wasn’t at this point aware of. As for me, it was in New York that I finally gave into the whole, “I’m gay” thing even though, technically I was bi but for that time in New York I seemed to be obsessed with guys, going to gay bars, picking up guys, taking drugs, having sex. I was changing entirely.

Coming back to my hometown, followed by Issac I was completely into the gay “scene”. I soon had a boyfriend who is my first and only real boyfriend and who is still with me. Issac is married with 2 kids to a woman – Linda - he had met overseas all the way back when he and I finished school. When he, Haley and I had started to experience a rough patch, I would later learn by piecing together stories Issac told – that he was in touch at the time with Linda. That holiday he took for 6 weeks: with Linda. His hitting the roof when he found Haley and I in bed together: he seemed to be considering the possibility of using that to break up and go to Linda. Linda was the reason he was sometimes distinterested in us and Linda was someone he cheated on while with Haley – both from a distance and for 6 weeks on a holiday – before judging Haley and I for having sex. Linda was there in the background for our entire friendship and Issac was pining for her, thinking of her, frustrated he was unable to be with her and regarding Haley at times as the “love the one you're with”. I personally felt betrayed and it still plays on me. I am not as close to Linda.

But with Issac now, with all that history behind us, he recently came to visit my boyfriend and I, and after some intoxication, he was naked and getting head from us both. He is seemingly always keen for something more exotic than his wife just to keep things interesting. It's rare now but when I am alone with him, it's still got some of the excitement, from my end anyways, of what it was like when we were 20. And for him, I know he loves me deeply. But just as what begins for me as being sexually drawn to him still bleeds into a deep Platonic love for him, so what for him has always almost entirely been a deep Platonic friendship - I think he just "goes with it" when he feels that so keenly it feels like he just wants a headjob from his best friend. So we're still finding each other so much fun because we care for each other and can flirt and tease each other as a bit of flavour outside our own otherwise monogamous relationships.