Welcome to The Last Time… our bi-weekly anonymous diary that looks into the last time our audience did something totally Sextras. This week, our deputy sex editor Amelia Reynolds speaks to a twenty-something gay man about his experience having a threesome on holiday.

Thanks for talking to me today! Let’s get straight into it. When was the last time you had sex?

When I was on holiday about a month ago. I have entered a *hopefully short* dry spell since then.

Oh wow! How did you meet the person/ persons? 

It was a classic Grindr hookup. I was actually talking to these two guys separately. It turned out that they were boyfriends, so we all got together.

Oh a threesome, how fun! How did that come about, what was the conversation like? 

So, after a while of talking, one of them (the slightly less chatty one) was like “Hey, I think you’re talking to my boyfriend”. It said open relationship on his profile and he sent over a few pictures of them together. He said they were heading to a spa and asked if I’d want to meet them for a drink and hang out.  I wasn’t going to get back in time from where I’d been that day, so I just went over to their hotel.

How did you feel when you found out they were together – were you immediately open to a threesome?

I would say I was down straight away! It wasn’t explicitly said that it was going to be a threesome – I mean it’s a hookup app so “hang out” was in inverted commas. 

It’s not my first time in a threesome, or with two partners that are in a relationship, so I felt comfortable with what that would look like, and they seemed sweet.

Entering a threesome with a couple might be a little daunting for some people. How do you avoid any awkwardness as a new person in a couple dynamic?

I think just be yourself. There’s not a whole lot you can do to be honest. If they’re not entirely clear on the set up or have doubts amongst themselves, it’s always going to be awkward.

I would say though, make sure you’re giving everyone equal attention (if they want it), even if you’re slightly more attracted to one person.

How do you overcome those pre-hookup nerves? 

There are two outcomes: a) you don’t. If you’re not feeling comfortable or excited, absolutely back out. Trust your gut. b) If you're feeling excited and just a little nervous, get ready, put your shoes on, and start walking. Most of the time I find I just need to get myself through the door and then I’m chatting and having a good time. 

How was that initial interaction when you got to the hotel? 

When I got there I was a little nervous – I usually am a little bit before a hookup – and hotel rooms are quite a small space for three people just meeting for the first time. But it was cute, in a sort of strange way. They sat on the bed against the headboard and I sat cross-legged at the end of the bed like some sort of interviewee.

What did you talk about before the hookup? Did you go over boundaries/ things you would like to do?

We talked for probably 25-30 minutes about all sorts: our jobs; our holidays so far; British politics. They offered me some grapes, it was chill. 

Our conversation came to a natural lull after a slightly unhinged monologue from me on how much I hated living in Britain sometimes. We looked at each other and then one of them said “on that note, let’s have sex”.

In terms of boundaries, we’d talked about what our general likes were and what we were down for beforehand. A standard Grindr “what are you into” exchange.

I've never had a threesome before so I feel like my view of them comes from things I've seen in the media. I think I expected the whole interaction to be a bit more clinical than that.

Oh no definitely not clinical, very human and casual. I feel like gay men can be pretty up front about what they want when organising things like this, but if any of it had felt too clinical I don’t think I’d have been into it from the outset.

What kind of things did you agree on? Were there any boundaries they put in place as a couple or were they pretty much open to anything?

We met under the proviso of “let’s see how we get on”. Consent and boundaries are never set in stone and basically everyone I’ve slept with has understood that. There was no particular mention of anal beforehand, for example, so we just left that up to what the vibe was and how we were feeling with each other.

I think if any of us had felt uncomfortable with anything, we would have felt totally able to say. When we began having sex it wasn’t silent or anything. We kept talking about what we liked and wanted, etc. 

What makes you feel comfortable during a threesome?

As much as I don’t want to say it’s a vibe – it is just a vibe. If people are smiley, if there’s humour in our conversation it can help to put you at ease not – super serious. It's nice to have that hangout before sex and in this case, these guys were really kind, friendly and we had a lot in common. 

Did you start off with any foreplay?

Yeah, we all kissed for ages. I’m not sure we actually did that three ways haha. More like we would switch partners periodically. Then one would kiss other parts of the body when the others were kissing, or focus on oral sex. So a bit of everything really. No rushing, we just spent the first part getting to know each other’s bodies and rhythms. We didn’t end up having any anally penetrative sex in the end, all agreeing we hadn’t really prepared for it and were totally fine with just oral.

How was the sex overall? Did you enjoy it – did you come? 

Yeah I would say so! It was really nice. We all finished (on me).I wouldn’t say it blew my mind or anything, but it was good sex, and I enjoyed it. Actually all the more because we’d chatted and got to know each other a bit. I think if we ever ended up in the same place again by chance, we’d meet up again. Also crucially, there was no weird partner dynamic or general vibe, which I know some people are anxious about with threesomes.

Have you ever experienced this before with a threesome – that awkward feeling? 

I’ve only ever had three threesomes, but I have had group sex scenarios. Sometimes during those I’ve felt pretty anxious. I think generally in unplanned  encounters – cruising-type encounters feel more anxiety inducing. People don’t talk, it’s pretty silent. That doesn’t suit me, I like to talk to people I’m having sex with – that’s how I feel comfortable. 

What did you do afterwards? Did you restart your conversations about British politics?

We chatted a little more about our plans for the rest of our trips and the best things we’d seen so far. Things like that. Ultimately though it was getting late and I left them in peace and went back to my place. I had a second dinner on the way home as a treat.

A threesome and a tasty treat all in one night! What did you eat?

Anything is possible when you put your mind to it. I had a steamed bun and a microwavable cheeseburger from 7-Eleven, which is nowhere near as gross as it sounds. I’m always ravenous after sex. I have this theory that all the kissing tricks your brain into thinking you’ve been eating when you haven’t.

How did you feel afterwards?

I’d say I felt good and sleepy, it was nice to meet some new people. When I’m travelling solo it’s always good to make connections with as many people as I can, it stops me getting lonely.

Did you all exchange contact info or is it more of a  if the universe wants us to meet again we will kinda thing?

We follow each other on Instagram and will probably continue to like each other’s stories once in a while for as long as we live. The usual.

You gained a new sexual experience and two loyal Instagram story viewers

What more could a girl want?

Was this the first time you had sex on holiday? What do you like about it?

Certainly not the first and I hope it won’t be the last. Sex on holiday has a special vibe in that the fact you’re unlikely to meet again (at least outside of the immediate future while you’re on holiday) is common knowledge from the outset. 

I find the way sexual partners abroad can be entirely separate from your friends, family, and everything you know back home quite freeing I think.

Any advice you have for people wanting to try a bit of holiday sex?

Put yourself out there and maybe try to be a little more adventurous or confident or flirty or whatever than when you are back home. No one knows you! That’s exciting. Some of my favourite memories and even close friends are people I hooked up with on holiday.

Thank you for telling me about your last time!

The pleasure is all mine.