I’m a ‘try-sexual’— my biggest fantasy just became a reality

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 single Kelley Nele, a 28-year-old trans woman andsex educator from South Africa.

The last time we spoke with Kelley, she told us about her love of ‘outercourse’, and how she prefers to focus on the pleasure that comes from foreplay and dry humping.

But since then, Kelley has started to enjoy penetrative sex, and this week, she’s chatting to us about her fantasies – and what it’s like when one finally became a reality.

While Kelley enjoys an active sex life now, masturbating every day and having partnered sex twice a week, it hasn’t always been this way. Prior to transitioning, aged 19, she says she felt ‘out of place’.

But now, she says: ‘I find it easier to be myself and 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.

‘My family and friends accept me, most men hardly flinch when I tell them I’m trans,’ she says. ‘Since I’ve come out I experience joy more often.’

Kelley adds that she has an ‘open mind’ when it comes to sex and is ‘eager to explore most avenues available’.

‘Like Samantha Jones, I’m a try-sexual: I’ll try anything once,’ Kelley says. ‘I plan on being single for the next few years so I can experiment freely. I’m currently only open to short term flings.’

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

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

Sunday

My phone buzzes, it’s Antonio. We met at a mutual friend’s house party earlier this week and have been texting for the last few days. 

He sent me yet another snap of his capacious penis, his fourth this week. I blush and ask him if he’s on demon time (aka horny). ‘Always,’ he replies. 

Antonio asks me if I care to hop on Facetime and watch him play with himself. I eagerly say yes.

Despite only knowing each other for a few days, I’m perfectly comfortable doing this with him – I’ve always gotten an overwhelming thrill out of phone sex.

I tell him he’s not allowed to finish without my permission and it’s precisely what he wants to hear. The pleasure on his face is the reason why I have phone sex often (at least a couple of times a month). I love taking turns playing the dominant and submissive role, each role makes me feel empowered and sexy in different ways.

As long as I’ve established a rapport (usually via phone calls) with the people I’m having phone sex with, it’s never awkward. If anything it’s exhilarating.

Antonio smiles and tells me it’s my turn. I give him the best performance I can, not just for him, but because I enjoy the idea of him watching me. There’s something about being watched that makes you feel like the sexiest person in the world.

Monday

He’s asked me out on a date tonight and I arrive at the restaurant to find Antonio seated. He’s even more handsome in person than I remember. 

Before long, we place our order and start exchanging naked truths.

We’ve got a lot in common – we’re both social butterflies who love a busy social calendar.

I get good vibes from him all night, so we head back to my apartment to do the deed. It’s our first time having sex but I know it will be just as good as on the phone.

We take turns going down on each other before we start humping, missionary style. After we’ve finished, he stays for a while before he leaves. 

Tuesday

I’m waiting for my food order at the mall when I’m approached by a man who looks a lot like Antonio. I know it’s not him because he’s at least three inches shorter, bald, and has less facial hair. 

He tells me his name is Pedro and that he felt compelled to introduce himself. I ask him for his last name and it’s the same as Antonio’s. They have to be related – but I don’t say anything yet.

He asks me out. Surely I couldn’t go out with someone who’s possibly related to someone I’m seeing, could I?

But he’s so attractive, and he has just as much sex appeal as Antonio does. I surrender and say yes even though I know it’s probably wrong. I can’t help it: he’s just so damn hot.

I do feel guilty though, not because Antonio and I are serious (we never will be) but because I’ve never intentionally gone out with siblings before.

We exchange contacts and he tells me he’ll text me later.

Wednesday

I’m torn between going on my date with Pedro and cancelling. I’ve never dated two brothers at the same time before. This feels deceptive, wrong. Everything inside me is telling me to cancel, but it’s too late now.

I arrive and Pedro immediately rises from his seat to greet me. He pulls my chair out and I flashback to when Antonio did the same for me. 

He compliments me and I skirt right past it, telling him I need to ask him something important and he says he’s all ears. 

‘Do you by any chance have a brother named Antonio?’

He tells me he does and asks me what’s going on. I tell him all about how I’ve been seeing his brother and he basically shrugs his shoulders. He says it’s happened before and that he’s learnt not to be bothered by it. In fact, he and Antonio have competed over women before. 

He tells me he doesn’t mind and I try my best to tuck all of this in the back of my head so our date can finally commence.

At the end of the evening Pedro asks me if he can see me again. Despite having a great time, I tell him I need some time to think about it.

Thursday

I call Pedro to let him know that I would like to see him again if he’s still open to it. I figured there was no harm in it, after all he did say he didn’t mind the fact that I was seeing his brother.

And I have no intention of being in a committed relationship with either of them — or anyone for that matter — anytime soon. Pedro invites me to have dinner at his apartment later and I accept.

Ever since shows like Supernatural and The Vampire Diaries came out, I’ve (secretly) always fantasised about being with two brothers at the same time. Maybe my fantasy is about to come true?

I decide not to tell Antonio anything yet, I want to wait until I’m sure there’s something between Pedro and I worth exploring.

Pedro’s apartment is more stylish than I would have imagined. Something in the kitchen smells divine, he’s made chicken alfredo.

Pedro dishes up, pours some wine for us and brings it all over to the coffee table. We eat on the sofa and I press play on the film Mortal Kombat.

Somewhere towards the end of the movie Pedro asks if it’s alright to kiss me. I’ve always thought it was hot when guys ask for consent before they kiss you. I nod and he kisses me with the passion of multiple fireworks. Before I know it, he takes my jeans off and goes down on me.

A part of me is profoundly aroused by this, another feels ashamed to be sleeping with Antonio’s brother. But, not ashamed enough to stop it from happening.

Then he humps me in missionary before flipping me on my belly and having sex with me from behind.

Friday

It’s noon when my phone buzzes, it’s Antonio. This is it. This is my chance to come clean. 

Antonio is shirtless and once again on demon time. I tell him to put his abs away, I have something I need to tell him first. I come clean about everything. 

I expect him to be upset, angry even, but he chuckles and basically tells me it’s no biggie. He also says this has happened before.

‘This is so outside my comfort zone,’ I tell him. I ask Antonio if he has any qualms about me seeing his brother and he says no. Despite this, I consciously decide there and then that I won’t date either of them – we’ll be friends instead.

This situation has easily been the messiest dynamic I’ve ever been in and I’m afraid things will only get messier. I pride myself on not getting involved in drama.

Antonio puts his abs back into the screen and asks if we can at least end things properly. I blush and oblige him once more.

We flip our cameras so they face our genitals and masturbate together. We finish almost simultaneously and exchange one last smile before hanging up.

Saturday

It’s mid-afternoon when Pedro invites me in to his flat. We both meant it when we said we’d only be friends, so the plan for the afternoon is simply to play some video games.

Keys rattle against the door and Antonio walks in. I had no idea they lived together, this is so awkward. Antonio greets myself and Pedro as if nothing ever happened.

I go along with it in hopes that Antonio will retire to his room soon, but he doesn’t. In fact, he plops down beside me and says he’ll play the winner.

I can’t help but feel as though I’m being punked. This isn’t normal. This can’t be real.

The awkwardness eventually subsides. Antonio seems to be handling the situation well, so I don’t feel the need to be nervous anymore.

We’re ordering takeout when Antonio decides to ask me who I thought was better in bed. I refuse to answer and redirect the conversation by asking Pedro and Antonio if they’d ever sleep with the same person at the same time. They chuckle simultaneously. 

‘Is that something you’d be interested in?’ Pedro asks. I tell them I’m simply curious and neither one of them believes me. Antonio says he’d be down and I chuckle. Pedro says the same.

‘Prove it,’ I say. Pedro leans in and kisses me. He then pauses and looks at Antonio as if to say it’s his turn to kiss me. My body surges with electricity. This feels too good to be wrong, so I surrender to the moment.

They’re consenting, I’m consenting, how could this hurt?

They help me undress. Our bodies are bare, forming all kinds of shapes: one of which is a slightly cooked Eiffel Tower.

The only way to describe the sensation is overwhelming, but in a good way. They both take turns giving me oral until I eventually finish. Then they proceed to stroke themselves until they finish.

I always knew that being pleasured by two men would be amazing, but I never expected it to be this great. I know for a fact that I will be doing this again.

When the deed is done, Pedro retires to the bathroom to take a shower and asks if I’d like to join him. While we scrub the last few minutes off I ask Pedro how he felt about what had just happened. If it was as hot for him as it was for me. ‘I wouldn’t be opposed to doing it again,’ he smiles. Neither would I, I think to myself.

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