I went on five minute date with a stranger then we had hot sex against a wall

Welcome to How I Do It, the series in which we give you a seven-day sneak peek into the sex life of a stranger.

This week we hear from Nina*, a 26-year-old publicist. She’s currently single, but has a friend with benefits, and usually has sex once or twice a week.

This year, Nina has been trying to ditch the apps, and have more ‘organic’ sex – although she often gets lured back in.

‘I’ll delete all dating apps, as I know what a wasteland they are – but then I end up redownloading them,’ she says.

‘I’m using at the moment because my self esteem is a bit low and I want the validation, which is sad but true for a lot of people.’

As an alternative to apps though, Nina has been curious about ‘dating events’, such as dinner parties, speed dating and singles nights.

‘I find that there’s usually far more chemistry and a much better story in it – and the sex is often much better too!’ she adds.

‘In person flirting creates a sexual tension that I just don’t think is there with online dating, which for me equals far more fireworks.’

Although, Nina does add that her relationship with sex is ‘a conflicted one’.

‘I love having sex, but I’ve had a few long term boyfriends, and with each of them I faked orgasms pretty much constantly,’ she explains.

‘It’s not that they were all awful in bed, but I think I’m definitely a people-pleaser – I worry that I’m taking too long and so fake it just to seem willing.’

Now, Nina is trying to change her old habits: ‘I’m looking to explore things with people that make me feel totally comfortable and I’ve become more outspoken about what I like and want.’

So, without further ado, here’s how Nina got on this week…

The following sex diary is, as you might imagine, not safe for work.

Monday

Today I’m working from home, a real relief because I recently got back from holiday and I’m still knackered. I spend the day ‘lightly’ working (having my laptop open while I lie on the sofa and watch TikToks).

It hits 5pm and I begin to get ready, because I have a date tonight. It’s a Hinge date (sigh).

I have some supper and then go off to meet Marcus*. He’s deeply pleased with himself, and asks a lot of sexual questions early on into the date. I want the vibe to be flirty, but when someone’s this aggressively sexual straight away, it’s a real turn off.

I tell him about my holiday and his first question is whether I’d ‘put out’ while I was away. Then, I mention I’d been to a wedding a couple of months ago, and he asks if I’d hooked up with one of the groomsmen.

He seems very keen to go home together but it’s a no from me. After two drinks, I make an excuse and head off for an early night.

It’s disappointing we didn’t click more, but I don’t want to force something with someone I actively dislike – I know it wouldn’t do the sex, and my levels of comfort, any favours.

Tuesday

This morning I wake up, feeling refreshed and pleased with myself that last night I called it and left my date early. There was a stage a couple of years ago where I would have just got drunk and slept with him.

When I used to do this, I’d wake up feeling full of shame. I’m a real people-pleaser, but I’m realising the most important person to please is myself.

Today I actually have another date, this time with someone I know for real.

James* works in the same industry as me – and we went on one date two years ago that didn’t go anywhere – but he recently slid into my DMs asking for a do-over.

That first date was fun but after he invited me back to his he got incredibly nervous once we were in his bedroom, and nothing happened. We just sat there speaking about our favourite films for 40 minutes.

I know he’s been in a relationship since, and I’m hoping this means he’s a bit more confident. I go to meet him, and it’s actually lovely. As we chat, I notice that feeling of ‘I Fancy This Man’ – obviously a good sign.

He walks me home and I do slightly have to goad him into kissing me, by teasing that he’s still nervous after two years, but once he bites the bullet it’s a good kiss.

I pull away first – I read a magazine article when I was about 15 that said ‘you should always leave your man wanting more’ by being the one to end the kiss. Is it effective? No clue at all, but it’s my signature move now. 

I don’t invite him in but it’s been a really good date.

Wednesday

I wake up and have a text from James, asking if he can see me again sometime – I’m on holiday again next week and slammed until then, but we set up something for when I get back.

I have work again today, but afterwards I’m going to meet some friends for drinks and dinner.

We go, and after the usual catchup, the conversation, as ever, turns to dating. There’s a lot of debate about dating apps vs meeting people in person.

One of my friends agrees with me, and is strongly in favour of eschewing apps, but a couple of others say it’s easier to weed people out on them. A fair point.

After my date with Marcus, I’ve deleted Hinge again.

Thursday

Today I have the day off from work, because I’m going to the Eras Tour. I’ve been looking forward to it so long, it feels quite surreal that it’s finally come around.

I go with my sister and friend, and I get deeply, deeply emotional, particularly during the Fearless era – I cry a lot and my makeup runs.

Taylor Swift has been heavily criticised for her relationships in the past. It’s a constant battle women face: too many partners and you’re a sl*t, not enough and you’re a prude.

She doesn’t play it on the night, but I always love her song The Bolter, and the lyrics in it: Ended with the slam of a door/ Then he’ll call her a whore/ Wish he wouldn’t be sore/ But as she was leaving/ It felt like breathing.

I feel it’s so relevant. I’ve been called emotional by men, yet in my experience, they’re the ones that can’t handle being rejected.

I find Taylor inspiring, and seeing her up on stage and thinking about what she’s achieved is mind blowing.

Friday

I wake up this morning feeling like I’ve been hit by a bus. The four hour concert last night and the scrum getting out of Wembley has ruined me.

I’m working from home, and I go to the supermarket at lunch to get a pizza to recover. Then, in the evening, my friend with benefits, Sam, comes over.

I’ve known him for years, after meeting at uni, where there was always a spark, but we were with other people. Then after we graduated, we got back in touch, and we’ve had an on-off casual relationship since.

We often go through phases where the other one decides they’re in love with the other, but we make it work.

When we were younger, he definitely had the upper hand, and I was fully wrapped around his little finger, but it’s switched now.

Although it sounds mean, I feel smug about that, because I know that at least a lot of the time, I could have him if I wanted. I told him about my Hinge date, but I’m always fuming if he gets into a relationship – that’s usually when I decide that I want more. But I think we like the idea of each other more than we’d actually like being together.

He comes over and we have a great time. Because we’ve been sleeping together for a while, I’m totally comfortable with him, and it means that the sex is always out of this world.

He’s very into going down on me, and he’s also very good at it – even while we’re actually having sex, he’ll pull out to go down again, which I’m definitely not complaining about.

Afterwards we lie in bed and chat and cuddle – but we draw the line at sleeping over together. That would make things even more complicated than they already are. 

Saturday

Today is a relatively calm day, I go on a run in the morning and then to a park to read my book.

After, I get ready and go to meet my friends – we’re going to a speed dating event tonight. I think that these kind of events are fun, and I’d so much rather do this with my friends than go on a Hinge date.

We go out for dinner first, then head over to the bar. It’s an event that we found on Instagram and our hopes aren’t high.

We get there, and instantly realise that some of the men there are taking speed dating very, very seriously. But out of fifteen, there is one man there who seems normal and nice, and luckily I click with him, even if we only have a five minute date. We leave the event early to go for a drink, and before I know it, we’re back at his.

It’s surprisingly good for a drunken first time, which is great – I love it when this happens.

He used to be in the army, and is clearly super strong. He picks me up and we have sex against his bedroom wall, which is a first for me, and really fun.

We’re definitely sexually compatible and I come twice, bliss.

He’s recently out of a relationship so although I think I’ll see him again, I doubt it will turn into anything serious, but I’m not sure that’s what I’d want either way, so it’s a bit of a win-win.

Sunday

I leave my fellow speed dater after he a) makes me come and b) makes me breakfast (poached eggs on toast, delicious).

We have sex again in the morning – it’s a bit more awkward than last night, presumably because we’re both sober, but it’s still good.

I’m on top for a lot of it, which I love, because it’s one of the main ways I can come during penetrative sex. I also enjoy having the control and being able to tease a bit more. 

We exchange numbers and agree we’ll hang out sometime soon. I get the bus back to mine, and go back to bed for a bit – I didn’t get much sleep last night.

Once I’m up again, I decide to have a self care day. I gather the energy to go out for a run, then come back and clean my room from top to bottom. After I’ve showered, I do a face mask and paint my nails.

I always like to keep Sundays quite clear, especially after a busy week, to really take some time for myself and make sure I’m feeling rested.

Sam asks if he can come over to ‘watch a movie,’ and although I consider it, I’m absolutely knackered. He’s been a lot clingier since I told him about my date, so I think it’s a good thing to say no.

I definitely do enjoy making him jealous but I also like having him in my life without being in a committed relationship, so I need to tread carefully. I don’t want to promise too much, or lead him on – but I don’t want to push him away either.

I think we’ll always have a soft spot for each other, but he’s not who I’m meant to end up with.

Instead, I batch cook a chilli and watch some Gossip Girl, the ultimate comfort show, before absolutely crashing at 10pm and heading to bed.

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