‘Afternoon delights’ with strangers stop me from falling in love

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 Cheri*, a 27-year-old bisexual writer.

She’s currently single, but is keen to explore new people and sexual interactions.

‘One thing I’m particularly happy with about my sex life is my ability to separate sex from emotions, which makes casual sex enjoyable,’ she says.

‘But I’d like my sex life to be more frequent and to try some more kinky things.’

Cheri’s four year relationship ended two years ago, and since then she’s opted for no-strings sex because she ‘tends to fall too hard, too soon’ when dating.

‘This approach avoids me feeling lonely while single, but also ensures I remain focused on myself and my work,’ she adds.

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

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

Saturday

I’m spending a week in Oxford for a change of scenery, and once I arrive, I get off to a wholesome start. I unpack my bags, touch up my mascara, and head into town to explore. It’s my first time here and I’ve got plenty of recommendations from friends.

The sun is shining, and the city is filled with tourists and students. I spot a nice cafe and decide to sit down for a while. Out of the corner of my eye, I spot a couple at the next table. He has his arm around her and is kissing the top of her head as she nestles into him.

For a moment, I feel slightly envious. I’ve been single for a few years now, and for the most part, I’m very content with it. I’ve grown to enjoy all the perks of singledom, like having full control over Netflix and getting an entire double bed to myself.

The only thing I miss is that physical touch. I want to have sex again.

Sunday

I look at the options of dating apps on my phone. Will I go for Tinder, Bumble, Hinge or Feeld?

I decide that I’ll put my efforts in Bumble this time. I’ve tried all the apps while travelling around the UK and Europe, but Bumble is definitely my favourite.

I update my account with some recent photos and check my prompts. Then, it’s time to swipe. I always start very picky and then slowly deteriorate and lower my standards. But I pause when I reach Josh’s* profile.

His first photo features him on the beach, a cheap way to show off his extremely toned physique. I hope he’s still this tanned, as he looks absolutely delicious. I feel a familiar stirring in my body; I’m definitely attracted to this man.

His profile doesn’t reveal much about him, just that he’s 26 and a tennis coach. I swipe right for Josh, and every time I get a Bumble notification about a new ‘bee in the hive’ (aka a match), I hope it will be him.

But it’s all the other men I swiped right for who suddenly seem less attractive in comparison.

Monday

Waking up on a Monday morning is never enjoyable, but I spend a few minutes with my trusty vibrator to ease myself into the week. I imagine a man touching my body as I press my trusty toy against my clit. I really want to have sex soon.

Once I finally get out of bed, I check my phone and discover Josh matched with me at 2 am last night. I wonder why he was on a dating app at that time. Was he looking for a quickie? Was he looking at the photos as he touched himself?

I message Josh and decide to make a joke about whether he’ll give me a tennis lesson. He replies within minutes. We chat, flirt a bit, and the conversation is easy.

I decide to be completely transparent and tell him exactly what I’m looking for out of this. I’m only in Oxford for a few more days, and I just want a fun one-night stand with no strings attached.

As soon as I send the message, a wave of embarrassment washes over me and I briefly debate deleting the app. But then he replies, saying he’s definitely interested, topped off with a cheeky emoji.

Tuesday

The hard part turns out to be planning our one-night stand. I’m leaving on Friday, and Josh is working in the evenings this week, teaching tennis to kids after school, or professionals who work their jobs during the day.

His one-night stand could only start at about 11pm when I’m usually tucked up in bed. I also don’t love the idea of meeting someone for the first time that late at night.

Josh suggests we meet in the afternoon instead; my instinct is to decline. I can’t have sex with someone in the middle of the afternoon…right? A one-night stand must happen at night, an inherently sexier time of day.

But then I think about it for a moment. I love getting my sleep at night, and this way, that wouldn’t be disrupted at all. Also, meeting up with a stranger for sex in broad daylight is probably way safer. Why not have a one-night stand in the afternoon?

I agree, and we plan for Josh to come over tomorrow at 2pm. I’m looking forward to it but I’m also terrified. Either way, I’m having sex tomorrow.

Wednesday

The hardest part turns out to be creating a sexy daytime outfit. I settle on a fitted long skirt, a black t-shirt, and some natural looking makeup with a bronzed glow.

Josh arrives right on time, and I open the front door to see him strolling over. Oh, he is just as cute as his photos. We naturally both move into a hug, which shouldn’t feel this awkward since we’re [hopefully] going to be naked together soon.

We head to the living room and I make us both a cup of coffee. We talk a bit, and there is soon a lull in the conversation. I offer a ‘house tour’, and Josh eagerly agrees. I show him around, and then we reach my bedroom. Josh looks around and then sits on the bed, watching me intently. Alright, this is happening.

I walk over so I’m standing between his legs, and I lean over and kiss him. Josh responds eagerly, wrapping his hands around my waist to pull me closer. We fumble onto the bed, making out as if we’ve known each other for a lot longer than twenty minutes.

Our clothes are quickly shed, and Josh nuzzles his face into my neck, telling me I look ‘so gorgeous’. I giggle and thank him.

I go down on Josh, and he returns the favour. I tell him I want him and he immediately moves up. I remind him to grab a condom, and he obliges with a mischievous grin. We have sex, first in missionary and then moving into doggie-style, at which point I orgasm. Josh gives my behind a playful smack, and I urge him on.

Once he finishes and disposes of the condom, we lie down, both panting and laughing together about the fact that we first met in person about an hour ago.

‘Have you ever done this before?’ I ask Josh. He says he’s had casual sex, but never this quickly, and definitely never in the middle of the afternoon. I like the thought that I’m his first; it makes me feel special. We have sex again and end up in doggie-style again to finish it off.

Thursday

I message Josh to tell him that I had a great time. He tells me that he keeps thinking about taking me from behind and the view he had from there. After a few saucy messages back and forth, we plan for Josh to come over again this afternoon.

I kiss Josh as soon as he walks through the door, pushing him against the wall. He seems to enjoy my forwardness, and we quickly move upstairs. He asks me to go down on him again, and I gladly comply.

We start with me on top, and Josh seems to really enjoy it. I’m surprised that I don’t feel more self-conscious about my body in this position, considering I don’t know him, and he is so toned.

But something about the casual nature of our meetups allows me to shed my insecurities and just enjoy the sex. I know I’ll never see him again, so it feels like a business arrangement almost. If I’m not trying to impress him I can just embrace my larger body.

In the break between sessions, we talk openly about our lives and sexual interests. There’s a sense of intimacy in both knowing exactly why we’re here and not hoping for anything more.

Friday

I wake up to a message from Josh saying he had a great time and safe travels. He tells me to ‘hit him up’ if I’m ever back in Oxford. I reply saying I definitely will and good luck with everything. He doesn’t reply again.

As I’m packing my bags, I discover a discarded pair of underwear on the floor, likely tossed to the side in the throws of sex. I have a ‘sex flashback’ to looking up at Josh while on my knees.

I cringe slightly at the memory, my cheeks flushing, but I also feel strangely comfortable with everything that happened.

I get on my train, leaving Oxford, Josh and my first one-afternoon stand behind me. It definitely won’t be the last time I enjoy an ‘afternoon delight.’

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