I love sex — but this simple act with my partner beats it every time

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 Tilly*, a 29-year-old trans single writer, who tends to have sex around once a week.

Tilly, who is bisexual, has gone through long dry spells before, and says she has a fraught relationship with sex because its ‘hugely intertwined with [her] self esteem and sense of identity’.

Tilly realised she was trans in her early twenties after years of wrestling with her gender identity as a teen.

‘I came out to my family and friends right at the end of 2018 and I’ve been living full-time as a woman since July 2019 — it’s the best decision I’ve ever made,’ she explains.

‘I now know exactly what I want and don’t want in the bedroom and I’m confident enough to communicate that with my partners.’

While Tilly originally relied on sex to feel good about herself after her transition, her perspective has now shifted and she cares much more about the connection with a partner, than physical sex.

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

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

Monday

I have two notifications on my phone when I wake up. One is a text from the girl I’ve been sleeping with for the last two months – we fell asleep texting each other last night and she’s responded this morning with an inside joke.

The second is a dating app notification – I’ve got a like from a straight man whose profile is packed with blurry stag-do photos and winky faces. As a bisexual trans woman, I take interest from straight men on the apps with a pinch of salt.

It’s not that a straight man couldn’t be interested in me – I’m a woman after all! But I’ve grown a sixth sense for when they might be fetishists in search of something they’ve seen in porn, rather than a real person. This guy looks like he fits into that category, so I dismiss his profile.

I roll over in bed. Before my transition I’d usually wake up horny on a Monday morning. Now, thanks to the effects of oestrogen, I just wake up with a yearning for a hand to hold. I prefer it this way, but it doesn’t make the loneliness any easier.

Tuesday

During my lunch break today, I have an appointment to get a blood test. Since I work in an office in central London, I only have to travel a couple of stops on the tube to get to 56 Dean Street, the Soho clinic which specialises in LGBT sexual health and has a gender identity service on the top floor.

I was here last week to see a gender consultant, and today I’m back to get my hormone levels tested, along with tests for all major sexually transmitted infections.

I’m embarrassed to admit that I’ve had not-entirely-protected sex with a few different people since I was last tested 18 months ago, so I’ve been keen to address that.

The nurse asks me about the kind of sex I’m having, and it throws me for a moment when he uses the words ‘top’ and ‘bottom’. I’ve never heard a healthcare professional use these terms before, but I suppose this is Soho!

After the initial surprise wears off, it makes me feel safe to hear the nurse speaking my language. Gingerly, I tell him that recently I’ve been bottoming.

It isn’t how I’ve always done things, but as someone who’s so often the biggest character in a room, it can be nice to be the little spoon in the bedroom.

“Any fisting or chem sex?” he asks me.

I shake my head.

Wednesday

I have a dinner party tonight with the girls. Among them is Ciara*, who I met at the age of 19 and was in a relationship with until I was 25. We lived together for four of those six years, and she saw me through my transition.

The process wasn’t always a smooth one, but she’s someone I’ve always felt able to confide in, and coming out to her was no exception.

Then in 2021, we decided our relationship had gradually changed and we’d be better off as friends. There were some naysayers who said there was no way we could stay close, but we’ve proven them wrong, and I would still call Ciara my closest confidant.

We share a bottle of red over dinner and talk about our love lives. When we first split, Ciara and I would be selective about what we shared, but now we’re both happy to get into the gory details of who we’re dating and what we’ve been up to.

Maybe it’s the wine, but I feel very sentimental and proud of how far we’ve come as mates.

I get a reassuring text to say that I don’t have HIV, nor Hepatitis of any kind.

Thursday

After a gruelling day at the office, I decide to have an early night. Before going on hormones, I’d have masturbated every day, and looked at porn several times a week, but these days I rarely feel the urge.

Today though, I decide to treat myself to some me-time.

I haven’t yet pursued bottom surgery – in part because I’ve spent the last five years on an NHS waiting list, and in part because I’m still not sure it’s the right choice for me. So, for now, I still have my original equipment.

Sex, both alone and with a partner, can make me feel dysphoric, so it’s about making sure I’m in the right mindset to allow myself to be swept away.

On top of this, I had a bad bout of depression in 2022 and eventually had to see the doctor when I wasn’t able to coax myself out of bed. Since then, I’ve been on anti-depressants, a side-effect of which is that it can be hard for me to reach orgasm these days, especially when combined with my hormone replacement therapy.

Whenever I masturbate, I have to focus more on the journey than the destination.

I weigh up a set of vibrating anal beads buried in my make-up basket, before deciding I’m not feeling so adventurous tonight. Then I get into bed and scroll through some erotic stories online.

The one I land on is about a young lesbian bookseller being dominated by an older customer.

By the time I finish the story, I’m feeling like maybe I could orgasm after all, so I head to OnlyFans, since I recently subscribed to a new creator on the platform.

At one time I’d have felt embarrassed about being an OnlyFans user, but these days I feel like if I’m viewing porn, the least I can do is pay the people who’ve made it.

I flick through a bunch of ‘T4T’ (‘trans for trans’) sex scenes between her and a series of mullet-bearing, tattooed trans men. It’s a diminished orgasm, thanks to my medication, but it’s an orgasm, nevertheless.

Friday

I’ve been seeing Lucy* for the last couple of months. We met on Hinge, but the same day we started talking we realised we’d been at the same gig that night. Since then, we’ve been seeing each other about once a week.

I have a date with her tonight. Well, I say a date. She’s going to come over and we’re going to watch a Wallace & Gromit film and order a takeaway.

Lucy is trans like me. She’s not the first trans girl I’ve had sex with, but she’s the first I’ve had an ongoing sexual relationship with, and I’ve found it really rewarding.

Lusting after her and her body makes me feel better about me and mine, and there’s a special intimacy that comes with sharing your whole self with somebody who feels your perspective and struggle.

We kiss for a long time before moving on to anything else. I’ve been involved in my fair share of adventurous sexual experiences, but ever since my first kiss as a teenager, nothing has ever come close to the magic of snogging.

I even have a tattoo on my thigh that says ‘LIVE, LAUGH, SNOG’, in playful tribute to this feeling.

Eventually, the kissing develops into going down on one another, then she puts her fingers inside me, then finally, after applying a healthy dollop of lube, slides her penis inside me.

Maybe at some point I’ll top her, but right now I’m quite happy to be railed to my heart’s content.

For trans women, penetrative sex either way can be a very vulnerable thing, but with plenty of communication and respect, Lucy and I have found a way to make it work.

I was worried I was spent after last night’s orgasm, but Lucy works her magic and gets me there.

Saturday

Lucy and I have a long cuddle in the morning (this is almost always the best bit) and I plate her up some mushrooms on toast and make us coffee.

We have a lazy day on the sofa, then in the evening I’m heading out to a comedy show with some friends. I’m keen to keep seeing Lucy, but I’m not sure I’m ready to be in another relationship right now.

In the past I’ve been guilty of moving too quickly, so I’m trying to act with caution.

When I get to the comedy show, I instantly catch sight of a girl across the bar who I went on a date with a few months ago. There was no real spark, and after exchanging a couple of polite text messages, we agreed there’d be no second date.

She’d suggested we could be friends, and I played along, but privately I knew that this wouldn’t happen. I have enough friends!

Being bisexual, I date people of all genders, but I’m afraid to say however that I’ve often found that men will generally decide whether they’re attracted to you quite quickly, then completely check out of the conversation if they’re not.

The woman and I make a bit of small talk at the bar, and I tell her to enjoy the show.

Sunday

I wake up with a hangover. The comedy show had become drinks in the bar afterwards, which had become another glass of wine or two on the sofa.

My eyes are all puffy, and I have makeup residue on my face. When I look in the mirror though, I like how I look, so I take a couple of selfies in my pyjamas, followed by one with my boobs out.

I text Lucy asking if she wants to see a picture of me. Of course she does.

I ask her if she wants to come over tonight. We never finished watching Wallace & Gromit. I don’t know if I have another orgasm in me this week, but God loves a trier.

About 90 minutes later, Lucy is at my door. We don’t have penetrative sex because we’re both tired, in fact, we barely touch each other at all.

Tonight, it’s enough to just look one another in the eyes, do some good old-fashioned snogging, and each masturbate to completion. We turn the lights out, satisfied.

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