I Had Sex With Two Best Friends

As long as you’re forthcoming with your intentions, there is nothing wrong with hooking up within the same friendship circle

Ah, the eternal question of life. Who came first, Joe or Ryan? Ryan or Joe? My memory is a little foggy, but I am 99.9% sure Joe came first (pun intended). He and I went to the same school though we had never spoken. He was in university and I, being a year behind, was on an extended break studying for my A-Level exams in an abandoned classroom. Why was I at school? The luxuries of being a boarder.

I was bored, so I decided to scroll on Tinder, and I saw I had a match. He recognised me instantly. Though I only vaguely remembered him — this was around the time where Tinder started showing the number of mutuals you shared with an individual and ours was in the hundreds so I knew he was telling the truth — but me, being myself, grilled him for never making a move prior (in his defense he had a long-time girlfriend).

The next week we spoke on and off continuously. He had decided not to leave the city for university, so he was living at home, henceforth why we still matched on Tinder. He and his girlfriend had broken up as soon as school had ended and he was enjoying the single life. Much like me, he was also bisexual (though this is years before I came out). There was no romance, but the infatuation was intoxicating, so soon we both decided to meet up.

Things move fast in the realm of Tinder — in my opinion, meeting up quickly shows that you have little to hide. But having been to school together meant that there was minimal risk of me meeting him at his place (though admittedly this has never stopped me before).

We met up on a Saturday morning. I know because every Saturday we hosted rugby matches at the school. Most of the boarding teachers went down to watch, leaving one teacher on duty supervised us. Being in the last year of school also had its perks, we were free to go wherever we wanted as long as we signed out and returned in time for mealtime.

On this day, he had invited me over to relieve some “exam stress”. So away I went. His house was a two-minute taxi ride away, and I arrived just in time for the end of his band practice, though his friends were still there. I said a quick hello to both of the gentlemen putting away their guitars before following Joe to his bedroom.

I won’t lie. There was very little talking. Clothes were off, and his penis was in my mouth before the bedroom doors were shut. This was during the time I still gave blowjobs, but to date, Joe is one of the only men I don’t mind giving one too. His dick was perfectly proportionally in regards to thickness and length, so it fitted perfectly in my mouth. Sucking him off was always enjoyable, and he didn’t taste bad too. The sex was passionate, rough and electric.

After as the room began to still, we got to talking properly in person for the first time. It was oddly familiar. I remember mentioning how peculiar it was that he’d wanted to have sex with me all this time, and it had finally happened. Now this phenomenon is… not as shocking as it once was.

From that first meet up a distant friendship blossomed. We were on the same page regarding expectations and would meet every once in a while to have sex. This lasted for a few years.

The first time I spoke to Ryan was when I went to sell a few things in CeX. I have one of those faces where everyone thinks they know me from somewhere. So when Ryan said this to me, I assumed it was another case of mistaken identity. It wasn’t. He remembered me from when I’d gone to Joe’s house. In fact, he’d been the one who had invited me to stay and smoke with them (I declined as I had exams to study for). So he mentioned that I owed him one whenever my exams had surrendered. I told him to add me on Facebook so it could be arranged.

He added me on Facebook, and we got to talking. It turns out he was a man of his word, and he invited me over to smoke with him one evening. The innuendo wasn’t subtle, but at the time I’d never had sex high, so I thought why not.

A part of me felt a little weird fucking Joe’s childhood best friend, but we had defined the relationship as strictly casual early on. Not to mention, he wasn’t my best friend, so the issue of loyalty wasn’t my burden.

I had had it in my mind that the sex would be similar between the two (I don’t know why it’s not like they were brothers) however it couldn’t have been any more different. Whereas the sex with Joe was coloured red and temperate, with Ryan, it was calm and mellow. He moved in me in perfect sync with the music. It was a world-changing experience. But unlike Joe, Ryan was a relationship man. So though we only met up a few times over the years.

There is this unwritten rule that you can’t hook up with someone your friend has been with. That once your friend has been there once (even for a fling) the person is out of bounds. But I disagree and think it is ok as long as boundaries are clearly defined.

When we first met I asked Ryan whether he had found it weird that he’d had sex with a girl that had just been with his best friend and to my surprise, he had already casually mentioned it to Joe, who didn’t care (the conversation entailed some smirks and a high-five).

It has been many years since meeting both of them for the first time, and there was no fallout. Though, perhaps this is because we were all looking for something casual? But I think it is because they were both secure enough in their friendship to know that the sex was just sex and that the situation didn’t need to be complicated.

I did find it a little weird how I’d alternate who I slept with, but they were okay with it, so I was fine with me too. So from this experience alone, I believe as long as you’re honest and forthcoming with your intentions, there should be no issues. It is also a fascinating experience I would recommend to anyone to try. I guess because they were so close I had assumed that there would be overlap in technique, but there wasn’t. Though they had different bedding styles, both experiences were great in their own right.

So my advice if you want to sleep with someone your friend has been with is, ask them. Communicate your desire to remove any chance of envy, toxicity or overlap. The worst thing that can say is no and best-case scenario; you’ll have an exciting story!

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