Secret Sex Diaries: the T4T couple in a long-distance relationship

A week in the sex life of... a 25-year-old having the best sex of his life after one year on T

Hero image in post
photo: Team Woo
Hero image in post
photo: Team Woo

A week in the sex life of... a 25-year-old having the best sex of his life after one year on T

By Anonymous17 Jul 2023
10 mins read time
10 mins read time

One-night stands may be on the decline, but a new generation is giving us insight into the who, what, where and why of hooking up in our anonymous, monthly Secret Sex Diaries.

Letting us into the details of a week in their sex life is a 25-year-old trans guy in a loving, long-distance relationship with his polyamorous girlfriend. Read on as he navigates sex parties, meeting the parents and aftercare.

Vital statistics:

Age: 25 Gender: trans man Relationship style: solo polyamory – currently in a long distance relationship with one person Sexual orientation: bisexual queer

The week in numbers:

Partnered sex and kink: 4 Solo sex: 2

I’ve been having the best sex of my life. Despite being polyamorous, over the last seven months it’s all been with my girlfriend of four years. The kink and sex we explore requires an extremely high level of trust. That kind of sex is incredibly hot to both of us, but requires a lot of communication. Luckily we’re both autistic sex nerds who like talking about sex!

I’ve also never been more comfortable with myself or my body than I am right now. I’ve been on testosterone for more than a year now, and no longer feel the need to keep my boxers on during sex because I’m so scared of my own junk. I know that my partner sees me as who I am and we have sex that is incredibly gender-affirming, using the words ‘dick’ and ‘cock’ to describe, equally, my clit with a year’s worth of bottom growth, my packer and my strap-on.

Even though both the partnered and solo sex I’m having are incredible, my severe depression impacts everything. While sometimes sex can help with that, I’m getting to know myself and my own boundaries better. I’m learning to respect my own boundaries and needs too; while my girlfriend has always respected my boundaries, I’ve sometimes ignored them for fear of being “too needy” and hate how vulnerable having needs – something perfectly normal and human! – makes me feel.

"I know that my partner sees me as who I am and we have sex that is incredibly gender-affirming"


I’m having a hard day so I only think about sex when I get home from work at a coffee shop and sit down to pee. The smell of my junk hits me. I WhatsApp my girlfriend, asking them if I can share a pervy thought. When they consent, I explain I’m turned on by the smell of my own dick and am thinking about them stuffing my boxers in my mouth.


I want to jerk off; testosterone has made my desire so much more spontaneous. I grab my vibrator and open my laptop. Despite Tumblr’s 2018 ban on adult content it still has NSFW content. I scroll through my most recent ‘liked’ posts, many of them about stress positions. I’m into the aching cramps that come from being ‘forced’ to hold a painful position

It takes me over an hour to orgasm. I love how much my dick has grown, but I need to work out how to readjust so I can come with a vibrator pushed against my dick.

It’s been a few weeks since I’ve seen my partner, but we sext or talk about sex most days. so we compile a list of highlights of kinky things to do. One of our compatibilities is how important sex is to both of us and the overlaps of what we’re into. It’s a way of saying ‘I love you’ outside of words

"Gentle, comforting touch turns to groping and soon I’m on top of them"


When my girlfriend arrives I cling on to them for a while. I feel like I should kiss them, but instead I just hold them and let them hold me, being comforted by their presence.

After a while we kiss, strip down to our underwear and climb into my bed to watch a show. They remind me there’s no pressure to have sex. But lying next to them makes me want more. Gentle, comforting touch turns to groping and soon I’m on top of them.

I grab my strap-on and hunt for a condom. They lie on their back and I cuff their hands to the headboard before positioning myself between their legs. While the idea of me fucking them with very little warm up is hot us both, I end up having to pull out. After some kisses, we try again, this time I work them open with a lubed-up finger. Even though there aren’t actual nerves in the dick inside them, it still feels like I can feel the moment when the resistance goes and my full length slides inside them.

I fuck them as hard and fast as I can, slamming into them and getting increasingly turned on by the sounds they make. I wish I had more stamina to go for longer, but their noises make it clear how much they’re enjoying this, and I know I’m stronger and better at topping them than I was a year ago, before starting testosterone.

We reposition so I can fist them for the first time, but the prospect adds too much pressure. Suddenly I’m stressed, and they suggest we take a break.

Later, our spooning turns into me touching their dick. We’re both very hard and want to get off. We buy a porn scene of a very hot T4T couple and watch it together while jerking off. They lie on their back, stroking themselves, while I lie on my front, a wand vibrator between my legs and pressed against my junk.

They come with me squeezing their tits while they moan my name. I lick up their come and kiss them. I take longer to get off, and worry they’re getting bored. They reassure me and, with a hand on my lower back, force my dick into direct contact with the vibrator. As the pressure builds, I beg them to push my head down into the pillow. My orgasm is drawn out and intense, and when I raise my head to look at them, they call me a good boy.

"My girlfriend's respect for my 'no' is why I can say 'yes' to things that feel incredibly vulnerable"


We have brunch with my parents – I’m incredibly anxious as it’s the first time my mum is meeting my girlfriend. I’m extra worried my parents will say something rude about transness or polyamory or will misgender my girlfriend. It goes well but I was more stressed than I was willing to admit, my girlfriend gently points out, so I feel wrung out.

We don’t have sex, and I’m surprised that I don’t feel guilty about it. One of the reasons I love them is that they never make me feel bad if we don’t have sex, even when we’ve planned a hundred filthy things we’d like to do together. Their respect for my no is why I can say yes to things that feel incredibly vulnerable.


I love kissing them first thing; they taste completely of themselves. After breakfast, we agree to go to a kink club later. I’m a little anxious - it’s the first time we’ll have played in public. I’m also worried that if I’m going to be at least semi-naked, some people may read me as a woman.

We arrive early and a staff member gives us a tour, introducing us to the dungeon monitor who we have to run any scene past before starting. We stash our clothes and the toys into lockers, and wander slowly around the play spaces again on our own, discussing what we could do. They bend me over the spanking bench and spank me, just to try it out.

We end up on the red leather sofas in a room with a St. Andrew’s Cross. I straddle them and we let our hands wander over each other. I’m more on edge than I want to be, because this feels hot but also vulnerable. We grab the toys we need for the scene and they cuff me to the cross.

They ask me to pick a number, and then they deliver that number: six hits with their leather strap. Three kisses. Twenty seconds of tickling until I thrash and shriek. Nine pressure points they push down on to make me moan. Seven seconds of them pinching my arse, the pain getting more and more intense. I’m completely at their mercy, and by making me choose a number, they make me complicit in my own torment. It’s playful and fun but it’s also very hot, especially when they pretend to lose count and start over.

Part of me wants it to go on forever, but the cuffs aren’t quite the right size, so my hands start tingling, and my legs ache from holding me up. We finish the scene with them asking me to pick a number between 99 and 100, and then subjecting me to a torturous 99 seconds of tickling while I giggled manically and tried to squirm away from them. When they uncuff me, I collapse on to the red leather sofas while they gather our items together. We head to one of the aftercare rooms and climb up on to the bed. When I roll over on to my side, they spoon me without me asking them to.

We stop by McDonald’s on the way home. I’d planned to cook, but I didn’t have anywhere near enough spoons. As we watch a TV show I fall apart again. While rationally I know it’s sub drop - a low felt by submissives after an intense scene - I feel weak and useless. I’m sure they must hate me. I hate me.

Their patience and love and care is so persistent, even when I feel like a giant mess. And I’ve been working on letting go of self hatred recently, so I take a deep breath and let myself believe it when they tell me they love me.

"We wrap ourselves around each other, whispering I love you and teasing each other with gentle touches"


My girlfriend didn’t take off their makeup last night, so their eyeliner is softer and smeared. We wrap ourselves around each other, whispering I love you and teasing each other with gentle touches.

They admit they’re in the mood for some pain play, so I grab one of their paddles. I give them a long warm up. I wasn’t a very experienced impact top before meeting them, and it feels good to now have the skills and confidence to deliver the beating that they crave.

We progress to a flogger and as I find a rhythm their noises of pleasure and pain get louder. It’s hot and fun to ask them what they want, making them use their words. As well as admitting they want more, they tell me how to throw the flogger. I adjust my position and it makes a massive difference.

Though there’s so much else we want to do together, we wind down sex a few hours before their train is due. Aftercare is important, and we can’t go straight from an intense scene to being outside. We need time alone to be present and intimate.

After leaving them at the station, I meet a friend for a walk. I know sub-drop is going to hit me again later – or a combination of sub-drop and girlfriend-drop anyway. The endorphins of the exercise help, and talking to my friend distracts me from missing my girlfriend.


Waking up without them is hard. Having sex this good leaves me wanting more. I feel hungry for touch in a way I’m not usually aware of, and it makes it harder that they’re not here. Rather than feeling guilty that I’m too tired and ill to work, I try to just let myself rest and recover.

Part of the aftercare I need is to talk about the sex we have, and today our debriefing evolves into flirting and sexting. Sometimes their words are so hot and filthy that I feel heat twist in my stomach.