The following content contains mentions of genitalia, vaginal, anal, and oral sex as well as body / gender dysphoria.
Welcome back to our Anonymous Sex Diaries series where queer and trans people from around the world let us into a seven day snippet of their sex, love and dating lives.
Day 1
As John Green described it in The Fault In Our Stars, “I fell in love the same way you fall asleep, slowly and then all at once”. That’s exactly how I would sum up my relationship with my boss. When we first met in November 2022, I was attracted to her at first sight. Not love or anything but yes, I was attracted to her. I’d pitched her a few ideas for her editorial via email and she responded that we should meet for coffee and discuss them further.
Now, what started off as an innocent crush has become a full blown desire to tell her every little detail about my day. I realised then that I’m actually falling desperately, genuinely in love with her. Almost a year later, I still feel very much the same. There are two problems with this relationship we have however, she’s nine years older than me and she has never had a sexual relationship with a trans man.
Today, Monday the 2nd of October — we had heated sex. Perhaps you’re asking yourself how did we get here. It happened quickly. I was submitting the team’s content calendars for the remaining months of the year in her office. She briefly spoke about how her morning therapy session went and I skated on thoughts that perhaps she does like me enough to talk about these things to me. I’ve always held her in the highest regard, but now all I want is to make love to her against the wall, respectfully.
Not knowing what to say, I offered to buy her lunch and said, “or we could just have an early lunch and eat each other right on this desk.” She paused for a good minute. I thought I might actually get fired, and quickly apologised for crossing the line. Standing up and taking calculated strides towards the window, I followed her and hugged her from behind. Before we knew it, my mouth was on her neck and her moans filled every corner of the office like an orchestra of unfinished sentences.
My groggy fingers tip-toed over her nipples, cascading down her ribs and back to firmly grab her behind. She dug her nails intensely into my back. My tongue ravaged every part of her and I made my way to her vagina. No, I didn’t take her pants off. She pulled up her skirt, and lifted her leg up onto her desk, inviting me to please her the best way I knew how. I shifted her underwear to the side and I was inside her, harder and faster. She bit my shoulders, her moans fighting to make their way out of her mouth and I was fighting every urge to say “I love you.”
We’ve been having sex since mid-September. She turns my stomach upside down, calls me Clyde and lets me hold her pinkie finger with my clumsy fingers on the elevator. I don’t know where we stand exactly because we never ever talk about it. I don’t know how to shake her off my bones and frankly, I know I might be the one who’ll end up getting hurt but if someone were to ask me what is it about her, I’d tell them it’s everything!
Day 2
I couldn’t see her today. My day was too busy, I could barely get some time to breathe, let alone think. I had media events to attend and although I knew she might be busy too, a part of me wanted to call her just so I hear her voice. You see that right there, that was troubling. But how do you know when you’re crossing the line?
On this evening, after an eventful day, I took a shower and warmed up some leftover pizza. While watching Scandal for the 17th time, I realised then that I’d much rather be watching it with her. Suddenly, it became easier to imagine spending years deep inside her body — and simply next to her. I started trying to jigsaw her into my future. I fit the piece of her onto a big porch in the country house and us making dinner on rainy days.
Before I knew it, I was watching porn and touching myself on that very same couch. My train of thought dove into the explosive sex we had yesterday. I moaned and groaned out her name twice, filling all my empty spaces in my house, squeezing my cushion tight as if it was her thighs I was squeezing. Perhaps, one would call me a pervert, lonely and stupid for thinking I could roll a god between my fingers and let everything wrong take my breath away.
But God, there is something to be said about days like this, that can put hope back on your map until you learn that you are here. And it’s exactly where you want to be.
Day 3
I had no reason to be at the office today, but I went there. I had to see her. For two hours, I was on my desk computer Googling ‘how can you tell if a woman likes you’ and watching videos of old men telling me about the philosophy of love. The internet didn’t give me much of anything, really. I stood up to make coffee, and there she was with our account manager heading to his office. My knees forgot to fight gravity in that moment and I thought I might actually fall. It wasn’t jealousy, but needing to be closer to her.
I didn’t want to intrude, to go to her office like I’m a fifteen year old who happens to have fallen in love with his English teacher. I went for a smoke, thinking my pulse pounding thoughts would quiet. I jerked my head up towards the sky as if it had all the answers. There was nothing. She came to the smoking area and said she didn’t expect to see me in the office today. She didn’t look in my direction. I was surprised that she followed me, but I chuckled and say something like, ‘well I still work here after all, right?’ She laughed and nodded. We went silent for a moment.
“I’m thinking of calling it a day. I’m beat,” she sighed as if she had the weight of the world on her shoulders. Trying to read between the lines, I offered to drive her to her apartment and surprisingly, she said “yes” with a warm child-like, smile.
The road was mostly empty, more so than anticipated, but then again, it was still within work hours. Everything goes by much faster in the car. I could feel her glances on me and oddly enough, I had nothing to say. Out of the blue, she said, “you’re strangely beautiful” the way people say it in movies – breathless, every syllable begging me to believe it. You ever feel your bones melting? I pulled over. I just couldn’t drive anymore.
With my hands on the steering wheel, palms sweating, she pulled my face towards her. I told her that she was strange, but I liked it. She kissed me like she hadn’t been kissed in years – greedy, her lips determined to turn my mouth into a feast. My whole skin was burning. I touched her as though I couldn’t believe she was real, like at any moment she might vanish into thin air. She said my name like it actually had purpose bigger than life, and it felt like the sun rose inside my chest.
She sat on top of me and I touched every part of her body like I was gathering missing pieces. She choked me, and I gasped for air. There was not enough room to move inside the car and she’d occasionally bump her head on the roof and we would briefly laughed and get back into devouring each other. The windows went moist, my fingers went inside her. We were like teenagers having sex for the first time, sipping in the adrenaline of it. It wasn’t the potential of getting caught that thrilled us, it was simply that nothing could contain us. Nothing.
Today, nothing existed except that moment, those passing cars, strands of hair hanging onto our skin, the sweat, each teasing breath of wind, every boomerang heartbeat. She squirted all over me, all over the car, and her screams shot up through the car’s sunroof. “I want you so bad” rolled off my tongue. She chuckled and called me “delirious.” I don’t know what that means, but when I was driving her home, we talked about anything but us or what we were doing. We got to her home and she didn’t invite me in. I convinced myself that maybe we still needed more time before playing house.
Nothing screws up a mind like not knowing where you stand.
Day 4
I don’t know. Maybe I’m in denial or plain out ‘delirious’ as she puts it. Am I wrong for wanting more? Okay, if we’re being honest the signs are always there but we often choose to ignore them. I might be shooting myself in the foot here, but there’s always hope. That’s what I titled my new playlist, ‘there’s always hope.’ I was listening to music on Spotify and now, I’m making a playlist for her. “I’d like to think that you’d stick around” Lana Del Rey says on “Love Song” and I’ve been playing that on repeat with her perched on the back of my mind.
I told our mutual friend today about how I feel about our boss. I know I shouldn’t have because workplace relationships hardly ever work out, but I needed to talk to someone and I trust him. Of course I didn’t tell him about the fact that we’ve been having sex for weeks on end now, or whether it’s reciprocated. We were in the offices drafting digital cover shoot ideas for next month. K says it’s just a crush, will pass soon, but I can’t tell him in detail.
I saw her today in the hallway and she avoided eye contact. Fair, I guess. The intensity of even passing by her consumes me. We have a real connection, no denying that. An hour later, she texted that we need to talk. Nothing throws a guy like a ‘we need to talk’ text. I swear.
We met later at a pub for a drink after knocking off at work. Our conversations often drift from the Rugby World Cup that’s currently taking place or media events that we often attend. Every once in a while we say something like ‘oh damn, that’s what I was thinking too’ and burst out laughing. I enjoy talking to her. Sometimes, I feel like that’s the only intimacy that matters, talking. I mistakenly touched her thigh and she didn’t move my hand. My hand went in between her thighs. Intentionally. She bit her lips, closing her eyes shut.
“Let’s get out of here,” she said.
It was around 9 p.m and the parking lot was eerily empty. Outside, around the back of her car, we kissed and spanked each other. I pulled her hair until she screamed. I awkwardly stopped but she said, “fuck me like a slut” and of course I obliged. It’s scary hearing those words from your boss but she doesn’t look at me like I’m a kid who doesn’t know what he’s doing. She lets me lead, be dominant. With my belt, I paddled her and turned her around like I hated seeing her face – laying her upper body on the car. I went down on my knees, tongue on her clit, licking her and her asshole pretty fast, with my two fingers inside her as if God had granted me permission to be nasty, all until she squirmed, not fully reaching her orgasm.
I didn’t want her to cum so fast. I admired her body. She’s a gym fanatic, spends six mornings at the gym in a row. I opened the back doors of her car and we got in, still hot in each others arms. She laid on her back and put her legs on my shoulders. We went on and on until we got our satisfaction, until our wells went dry. If I could give her babies, best believe I would have done it today.
I can’t tell who is more of a sex addict, but I can tell that it’s not going to end well. Hell though, I’m hoping it doesn’t end at all.
Day 5
I was waiting for her at the restaurant. She’s the one who said we should meet and talk. We’ve had lunch in public places before, but we were always with our colleagues. Even then, I’d make sure I got to talk to her about literally anything, just to keep the conversation going. Besides her looks, she’s highly intelligent and can hold a conversation. It’s one of the main reasons I’m so attracted to her.
Today, today was different though. I was uneasy. She walked in ten minutes later, wearing a long skirt with a slit on the side, exposing almost all of her right thigh, and a black tight shirt. I stood up to open a chair for her and she smiled politely at that gesture. We ordered food, and I told her how much she just reminds me of Olivia Pope when she walks. She burst into laughter and immediately I wondered if I could ever just bask in all that beauty. We had half an hour of a great conversation. She said there’s a possibility that someone might have seen us yesterday. ‘Risky,’ is how she put it.
I plain-out asked her, “What are we doing, exactly?”
It was tearing me apart not knowing. It was like I flicked a button. She tossed her head backwards and sighed heavily. The awkward silence hovered over our heads; we didn’t know whose turn it was to speak.
“I don’t have the answers you’re looking for right now,” she said.
That wasn’t satisfactory to me. I asked her if there was any hope at all for us being together and she proceeded to hold my hand at the table. Because I’m a fool of course, I took holding hands in public as a sign of hope.
We continued to have normal conversations that didn’t include tearing each others’ clothes off. I liked that. We didn’t have sex today, and maybe that’s okay. I’ve figured I don’t want to have sex with her if there’s no hope. Here I go again, being ‘delirious’ haha.
Day 6
I wasn’t working today. Woke up feeling high, invigorated with adrenaline. I went to a media launch. With my media friends, we had a couple of drinks and by my third drink, I was feeling weak in the knees. I’ve never been much of a drinker; in fact I didn’t drink at all before I started my career in the journalism space. On my fifth drink, K tells me to slow down and says something like ‘you not gonna forget about your crush by blacking out.’ He finds it hilarious, the biggest joke of the year.
I go to the restroom. I usually take a piss in the men’s restroom, but today I didn’t care about even looking at the gender signs. I broke down inside the restroom. Being inside there always reminded me that I hated my body. There were layers. I realised that I hadn’t been allowing my boss to touch my breasts and other parts of my body since we started out. Maybe she’s holding back because I, too, have been not giving all of me to her.
I have a habit of making a nest out of my body where I feed it sadness. I thought hating my body was okay as long as I did it quietly and softly, but it was in fact affecting my sexual life. My boss never raised it, though. She never questioned me on days when I don’t want to take off my vest and expose my bare body. For some reason, I thought if she could see the toy inside, she’d take her luggage and leave. Well, she was standing in the door anyway – one leg in and one leg out. In that moment, I broke down and just called her. My boss.
I don’t quite remember what I said exactly on the phonecall, but I sent her my live location. Things seemed to accelerate faster in my memory. Life moves faster when your world is falling apart. I don’t know how long it took her to arrive at the event venue, but she came to the restroom where I was sitting down.
“You can’t do this, you can’t do this to yourself.” That’s the first thing she said.
I held onto her for dear life. She smelled so great, I could swallow her whole. I asked her to not talk at all. My attempt at kissing her and lifting her leg up failed and she said I should stop. Of course she was going to say ‘no.’ This is getting out of hand.
“I should’ve never let things get this far, “she said.
I believe it was there and then that I sobered up.
The heart works in mysterious ways. I stared at her for what seemed to be hours. And then it came, the nauseous feeling. I don’t know if it was my heart breaking out of my rib cage or if it was just alcohol playing tricks on me, but I puked. She held my shirt back as I kneeled down and puked my guts out. All the while I was thinking ‘I’m about to get fired.’ With good reason too!
There were distant voices and muffled sounds. I couldn’t care. With infinite tenderness, she took my hand and said she’d take me home. Her home.
Day 7
Half the time, I don’t know what I’m doing, but rarely do I wake up in strange houses. I checked the time and it was almost quarter past 1 a.m. I was sleeping on the couch and the lights were turned on. With a NASA shirt that was kind of big to be mine on, I quickly recalled in bits and pieces what actually led me there. Guilt got my mouth dry. I went to the bathroom to wash my face and take a piss.
I didn’t know if she was up, but the lights in her bedroom were on. Without knowing whether to just request a ride and go home, or stay on the couch until morning, guilt was eating at me. I didn’t want to complicate things, they are complicated as it is. The house was great, homely. Upon deciding to just stick to the couch, I stared at the ceiling trying to think. My mind was mostly vacant so I walked around the living room looking at her framed pictures and artwork. She has always looked fierce.
My boss came through her bedroom door. I said I was sorry for waking her up, bothering her earlier on with my mental breakdown and everything in between. She just said ‘it’s okay.’ I soon realised that a lot of our problems could be solved with just talking but we don’t talk here, in her living room, where it’s hot and heavy, yet welcoming, like being clasped in an embrace by something much larger than life. We don’t talk here but even if we did, the language wouldn’t be able to reflect the intense, beautiful mess we’ve become.
I love her.
I love her. I don’t think I can ever echo that loud enough. I find life is more beautiful at the curve of her neck and between her palms. I don’t just want to have sex with her if it means nothing at all, but at the same time, I don’t want to lose the sexual relationship we already have for something that might not work.
