I hook up with people twice a week — but I’ve never had penetrative sex

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 Kelley Nele, a 27-year-old relationship and sex educator, living in South Africa.

She’s a single, transgender woman, and despite not being in a couple, she still has partnered sex twice a week on average.

‘I’m both comfortable in my skin and comfortable sharing my body with whomever I please,’ Kelley says.

Kelley says she’s all about ‘outercourse’. She prefers to focus on the pleasure that comes from foreplay and dry humping, referring to herself as a ‘side’ rather than a top or bottom.

But while Kelley loves her body now, this wasn’t always the case. ‘My earliest memory of feeling out of place was when I was five years old. I didn’t realise I was trans until I discovered the term when I was 15,’ she says.

Kelley began transitioning at 19. ‘I started off braiding my hair and getting extensions, and introducing the world to the new me little by little,’ she says.

‘After a while I started going to university in feminine clothing, then friend’s parties, and then events with over 50 people.

‘At first, I felt deeply self-conscious. Suddenly, I was turning heads no matter where I went.’

But Kelley says her coming out journey has been ‘mostly positive’.

‘My family and friends accept me, most men hardly flinch when I tell them I’m trans.

‘Since I’ve come out I experience joy more often. I find it easier to be myself, be forthcoming about my gender identity and in turn have more intimacy in all of my relationships.

‘Where I was once more guarded and ashamed, I am now more expressive and liberated—both emotionally and sexually.’

Without further ado, here’s how Kelley got on this week…

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

Monday

I shut my computer and sigh in relief. My chores and work for the day are done; I can do whatever I please. I could catch up on the latest episodes of Highbreak High, play video games, or workout. But, right now, I’m in the mood for something a little more… sensual. 

I follow my standard routine; shut the blinds, close the door, collapse onto my bed, and scroll through my spank-bank. 

For some reason the content on my phone just isn’t doing it for me. I’m excited but not as excited as I could be. I try harder to immerse myself in the content, but to no avail. 

I exit my hidden photos, throw my phone beside me, and sigh in frustration. I want to masturbate, desperately. I’m just not finding the content very titillating. 

Then I remember an old friend: Dipsea. Bingo!

Dipsea is my favourite audio erotica platform – it’s written by women for women, so the characters feel so real, are the stories so relatable. It’s easy to find a scene that fits my current mood.

I settle on a threesome scene with two men with devilish voices; every girl’s dream.

I move my hand down south and play.

Tuesday

I’m off for the day. I’m all caught up on my favourite series. My friends aren’t available, there’s nothing exciting in the world of social media. I’m bored and have nothing to do. 

I haven’t been on a date in ages. A few guys have asked but none of them piqued my interest. It would be nice to get dolled up, to flirt and be flirted with.

I click on the app store and re-download Tinder. I promised I would never use this God-forsaken app again but desperate times call for desperate measures. I deleted my old account so I have to start from scratch. I create a new profile, swipe away and wait patiently for the herd of potentials to come flocking in. 

It’s been a few hours and there’s now a pool of viable matches. I sift through them and a few of them catch my eye. I message them back and the verbal ping pong begins. 

I don’t plan on going out with any of these men tonight; there’s still a lot of vetting to do (us trans girls can never be too safe). But at least I have something to do now. 

I only tell the guys I’m interested in taking things further with that I’m trans, the rest get lost in the sea of matches. In the past I’ve been too nervous to tell men I’m trans but now I simply rip the bandage off. By the way, I say mid conversation early on. You should know, I’m trans. Most of them don’t care, some do.

Wednesday

There’s one guy who’s stood out from the rest; Dylan*. He’s my usual type; tall, dark, and thick. Like most guys I encounter, Dylan knows I’m trans and doesn’t care. We’ve exchanged numbers and have been chatting on Whatsapp.

Dylan has sent me a couple of voice notes and his voice is just as gorgeous as his face. I’ve thought of touching myself every time I’ve received one.

He asks me when he can see me and I tell him we still have a lot to get to know about each other. He tells me to ask away and so we can do precisely that.

One voice note he sends me details his turn-ons and turn-offs and I do the same. He asks if I’m a giver or receiver and I tell him that, while I don’t engage in penetrative sex and prefer outercourse to intercourse, I like being in a dominant position. 

In fact, I’ve never tried penetrative sex, but I feel that it’s profoundly overrated. I prefer hand jobs, oral and jean-jamming, otherwise known as dry-humping.

For me, not being into penetrative sex is simply a preference – nothing deeper. I don’t think it’s linked to my journey as a trans woman, I’m just not into it.

But, it’s often seen as an ‘immature’ version of sex. I find this so frustrating. Is sex not the consensual meeting of two (or more) minds and two (or more) bodies? Why does it have to be penetrative to qualify as real sex?

I always tell partners that I’m neither a top nor a bottom. which is actually pretty common in the queer community. Sometimes this puts them off, but that just shows me they’re not the type of person I should be sleeping with.

Dylan tells me he’s not very familiar with jean-jamming, but that he’s willing to learn. I tell him that’s perfect. We love an open-minded king!

Thursday

My phone vibrates and it’s him. I unlock my phone and up pops an intimate photo of Dylan in front of the mirror. Yum…

I ask him to what I owe this beautiful surprise to and he tells me he was simply thinking of me. I tell him he’s making it difficult for me to focus on my work but that was his plan. 

Dylan suggests we hop on FaceTime when I’m free later and we can explore one of the various forms of outercourse.

He answers after the second ring because he’s been awaiting my call eagerly and I tell him I’ve been looking forward to this all day.

After some friendly chit chat, Dylan flips the camera to expose himself, in all his glory. He tells me to strip down, lie on my bed, and to do as I’m told. He talks dirty to me as he tells me exactly where to touch myself.

While I prefer to take the lead, I’m not opposed to being put in my place once in a while. I get comfortable and follow his every command.

Friday

I arrive at the restaurant and Dylan is already here, seated. He rises from his seat and pecks me on the cheek. He smells just as good as he looks. 

The waiter appears and takes our order, while we continue our dance of getting to know each other; taking turns leading the conversation.

We’re both a few drinks in and sore from all the laughing. I knew I liked Dylan but I didn’t expect us to get along so well. I feel a lot more comfortable around him—and it’s not because of the booze.

We’re not having sex tonight; not only because we hardly know each other, or because we’re a little tipsy, or because we’re pretending to be civilised, but because the anticipation makes it so much sweeter.

Saturday

We’re playing pool tonight; my favourite game.

Dylan asks me if I’m down to lay a wager and I agree depending on what he has in mind. Winner gets a kiss, tongue and all. The game commences.

I beat Dylan, 2-1. Did he let me win? I suppose it doesn’t matter; wager in mind, we’re both winners tonight. He asks me if I’m ready to leave and I nod.

We arrive at his apartment and he offers me a drink. He’s new to the whole outercourse thing so I give him a play-by-play of what’s about to go down. He smiles and tells me I have his consent.

He moves closer to me and we make out. We take our clothes off and I take the lead. I want explore every single one of his erogenous zones, before we start humping. For me, climax is the goal in hook ups like this – in a relationship, sex might be more about expressing intimacy – but that’s not what I desire today.

After a mind-blowing orgasm, Dylan and I cuddle and all I can think about is how the sex was better than I expected.

Sunday

I wake up to an empty bed. There’s music coming from the living room. 

Dylan is singing and dancing as he cleans. He gets timid when he realises I’m watching. Cute.

He was just about to make breakfast as soon as he’s done cleaning apparently, but I tell him I can’t stay.

He says I don’t have to do the cool girl thing and that he doesn’t mind sharing a meal with someone he just slept with—you know, like a normal person. I assure him that’s not what’s happening here.

He proposes one last tumble in the sheets before I go but tempted as I am, I have plans. He books a ride for me and I gather myself.

After walking me to the car he kisses me goodbye. I don’t know if I’ll ever see him again, but what I do know is that this was a night I’ll always remember.

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