The following content contains mentions of menstruation; dysphoria; vaginal, oral, anal, penetrative, and group sex; and kink.

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

Tomorrow I’m going to a leather play party for women and trans people. A friend I had met on Grindr is a regular there, and took me for the first time a few months ago. I hadn’t realized how much of an actual party it would be, with people catching up or hanging out with their partners. I had always pictured cruising as the silent, cis gay male kind, and was a bit overwhelmed when I had to put my socializing hat on. I also considered myself something of an exhibitionist when it came to sex in public places, but when ten people were standing around a bed watching me get eaten out, I found it hard to let go of performance and focus on myself.

Now that I know more about the vibe and my general preferences, I’m excited to try again. My friend and I do a quick check-in to prepare. She wants to top me, make out a lot, get topped by someone, and maybe suck a cock together. Kissing is off the table for me (I have to really know someone before going mouth to mouth), and I’m on the last days of my menstrual cycle so I’m not obsessed with the idea of anything penetrative. I don’t have traditional dysphoria symptoms around many things except bleeding, so I try to do as much as I can to forget about it when it happens. Period underwear helps a lot, because it takes away the bulky feel of pads and liners. I assume this is going to be a mostly giving and spectating party for me.

Day 2

My friend and I meet at a bar a block away from the party, then walk over together. We’re encouraged not to linger outside the door, so the location remains a secret. We present our IDs and negative COVID tests to the volunteers, check our bags, and change into our gear. People are wearing puppy masks, lace sets, harnesses, horns, tails, chains, mesh, and normal street clothes. My friend gives me a quick tour, and then we settle down to watch the lesbian porn made in 2002 that’s playing on a TV. It’s still early in the night and everyone watching is very polite. I find myself focusing on the technique and cinematography rather than getting horny.

My friend and I start doing laps of the space as more people trickle in. There are bandanas available for flagging and a helpful chart to indicate which color and side coordinates with what. I grab a light blue one and tie it around my left arm to flag as an oral top. My friend cruises someone they know and tells them to find us in the maze if they want to get up to something later. I keep an eye out for a T⬆️4⬇️T cutie who I saw volunteering at the last party and who I’ve been talking to on Grindr, but it doesn’t look like they’re around.

We head to a room where a woman is sitting in a swing with an electric charge tied around her leg. A domme takes her time sliding different metal instruments over the woman’s body, electrocuting her—first a fork, then a knife, pastry wheel, a deshedding tool for animal grooming, a flogger with metallic or foil streamers, and different wands and prods.

In the center of the room someone is splayed out on a bench, getting their ass flogged, beat, and kneaded with someone’s fist, elbow, and boot. A leather daddy who is getting their boots shined in the corner complements the S/M top’s rhythm. I look behind me and notice someone is having their thighs clamped with clothespins, and someone next to them has been sitting quietly this whole time with their wrists bound together.

Phones are not allowed and I don’t own a watch, so I have no sense of time, but it feels like everyone in the room must have been going for at least 25 minutes. Someone dances by waving a yellow bandana. “Piss tops, calling all piss tops, there’s someone in the bathtub for you.” All the dommes are doing their aftercare now, hugging and cooing in their bottoms’ ears, which is very sweet to watch.

I had a great time spectating and then go to check out the piss bottom. There is someone positioned very expertly over them, standing on the sides of the tub. They seem to be manifesting a stream that isn’t coming yet, and the area does smell like piss, so I move on pretty quickly. All the beds in the back room are filled up now, and I join a crowd of people peeping through a large window. There are seven or eight groups fucking on the beds, swings, and couch, which are covered with pleather for easy clean up. Some pairs are standing up and fucking against metal bars.

I’m getting jealous and horny so my friend and I try to find a vacant swing, or any available surface area really. I want to fuck in the maze but all the corners are taken, and when I peep through the holes in the wall it’s all hair and moaning and cumming.

A small nook with a bench opens up, and I get on top of my friend and grind against her, unzipping her jacket and pulling her bra down so her tits fall out. I grope her boobs and squeeze her nipples, which makes her yelp. At this point I don’t care about my bleeding anymore, and I suck her girlcock until she gets hard. While I’m doing this a couple asks if they can fuck on the swing next to us, and I have to answer yes because my friend looks like she’s elsewhere.

My friend asks if I want to ride her, so I do that for a while until she tells me to turn around—and thank god, because even when I’m on top I’m still a bottom. She fucks me from behind and slaps my ass, which feels good, but I can’t find time to muster up the words and tell her to do it more. A demo starts while we’re fucking and I’m kind of sad to miss it. You can’t have it all! The couple on the swing keeps fucking too. I feel someone watching us and turn my head away so I don’t get self-conscious. I think it’s hard for my friend to cum nowadays because of her estrogen, but when she is generally finished she gets up and we put our clothes on and do a quick clean-up.

We catch the very last of the demo, which looks like it involved candle wax and rope bondage. The person we were cruising seems to have partnered up with someone and my friend is hungry again, so we head out and end the night with pizza. I get home around 2:30 a.m. and go to sleep immediately.

Day 3

I had signed up to volunteer at a 10 a.m. neighborhood event, so I have to pull myself out of bed for that. It’s very cute and fall-esque. My favorite top is coming over in the afternoon, so I head home to do some work and chores and wait around for that.

We met on Grindr over a year ago. He’s the only person I still talk to who’s fucked me both pre- and post-top surgery, which feels significant for reasons I can’t articulate. I like him so much I like to lick his sweat and sleep in his cum. He and his partner are going monogamous at the end of the year, so all our fucking feels melancholic now.

He arrives earlier than expected. After giving him a tour of my new home improvements that ends at my bed, he takes my pants off and eats me out, bending my legs over my head. I stroke his arms and his hair until he gets up. Before he can move on to something else, I pull him on top of me so I can choke on his cock. He really likes throat fucking, so in my free time I practice with dildos and poppers and toothbrushes.

He turns me onto my stomach and lays flat on top of me, wrapping his bicep around my neck and shoving three fingers into my mouth while he fucks me from behind. I suck his fingers then spit them out to bite his arms. He puts me in different positions until we’re both standing up over the bed. I lose track of how many times I cum.

He wets his thumb and slips it in my ass. I vaguely remember texting him that I wanted him there a few weeks ago. I wonder if he remembers this request or if he is just making it up on the spot. He fucks me in the ass for longer than I can remember ever being fucked in the ass, and the whole thing feels wet and easy, as in I don’t have to remember to relax. After he finally cums inside me, I turn my head to kiss him and we lay on top of each other until we both calm down. He does that magic boy thing where he falls asleep instantly; I close my eyes, enjoying the weight of him. I forget until then that I am still bleeding a little. I reach behind me and realize there is a stain of dried blood on the insides of my thighs.

I wake him up to shower and we rinse off. He turns me around to fuck me under the hot water — I have to lean forward and balance on my toes—then he pushes me down in front of his cock. I suck on him and he cups my throat from underneath. With his other hand he maneuvers his skin around, and I tilt my head up so he can cum on my face. I make sure to take some in my mouth, sticking my tongue out so he can see it before I swallow, smiling so he knows I am happy. I imagine myself as one of the suckermouth catfish I used to keep in my aquarium, latched onto his cock. He is very good at staying hard long after he cums. I continue licking him until my neck and legs are fatigued. I’ve resolved to keep going until he tells me to stop.

When he finally pulls me up, I turn the shower off and we hug for a while. I put my head in his neck, on his shoulder. We take turns drying each other off with the same towel. I rub, he pats. He tears up when he smiles at me, but I don’t address it in case he doesn’t want me to notice, the way I usually don’t want people to notice. Now I regret not asking and knowing what it was about.

He hangs back in the bathroom before joining me on the bed; we burrow into each other until he has to leave. I spend the rest of the night crying because I will miss him, spot cleaning blood off my comforter, drinking freeze dried miso soup and eating marshmallows filled with chocolate.

Day 4

Today is my recovery day before the work week. It’s rainy outside and cozy inside. I go to a fitness class that is so difficult my arms still shake afterwards, standing on the street. I have been thinking a lot about being principled and disciplined, both in my actions and in my body, and how I can derive pleasure from it. I ran a half-marathon for the first time recently and almost cried during the last mile, because I was so delirious. It wasn’t an official race; I just ran the distance to know I could do it.

I stop at a bookstore nearby and pick up A Self-Defense Study Guide for Trans Women and Gender Non-Conforming / Nonbinary AMAB folks, which I’m now realizing is free online. The part I fixate on is “The BEST way to avoid danger is to appear dangerous.” I read somewhere, probably a TikTok comment, about a woman who openly held a hammer while riding the Chicago subway, so people would think she was the scary one. I think I present as very soft, but inside I feel violent all the time. Someone I know articulated his feelings better. He said, “I hate so much.”

Day 5

Back to work in the capitalist hellscape. I was worried I wouldn’t have enough things to write about in this diary, so I used it as an excuse to finally purchase a packer. I’ve been thinking about packing for a long time, not because I have lack-of-penis dysphoria (that I know of), but because I enjoy the idea of hugging someone and rubbing a bulge against them, or poking them with a boner.

I was planning on putting it on for the first time and wearing it around the house, but I still feel emotionally wrecked from the weekend and the world, so I will lay off of it for a while. It’s still in the opaque plastic bag it came in.I feel like even looking at it could be emotionally tumultuous.

Day 6

Feeling recharged and horny. I wanted to jerk off last night but was too sleepy and went to bed at 12:30 a.m. Now I’m trying to figure out if I have time to jerk off between my meetings, since I work from home. I think I can only fit it in if one of my meetings ends early. Pray for me!

2:37 p.m. Hurrah! 20 minutes of my time back and I head straight to bed, where I spend way too much time looking for adequate porn while swiping away Slack notifications. I find a bondage one I like and jerk off for what feels like a long time, but is probably only five minutes.

Puttering around the neighborhood in the evening, I fantasize about telling people I’m writing an anonymous sex diary. “You should give me something to write about.” It’s only a fantasy, though. I haven’t been seriously looking for anyone new since early this year.

Day 7

I had a bad sleep and my mood’s tanked again. Unfortunately, I have obligations outside today and have to pretend to be a normal person in the world. During my commute, I reflect on the leather party and am a little miffed I didn’t cum. Of course it’s not the whole point, but I think my needs could have been more attuned to. I was surprised when my friend told me she usually tops.

A while ago, my gender friend and I realized we had both searched “power bottom” on Autostraddle, within the same week. When I was a cis woman, I was obsessed with being a top because it made me feel more masc. Now that I’m baseline transmasc, I feel liberated to be the subbiest, femmiest, faggiest bottom in the history of bottoms. I think of my bottoming in terms of “reviews.” How many people got off, how many asked to see me again, how many never text back. I don’t take it personally, yet for me it is always in relation to the other, to who I am with and how they feel. My pleasure is tied with your pleasure.

All day I feel fragile. I text my favorite top that I am sad, because I don’t want to bother my friends with problems concerning men, and why not go to the root? He says he is sorry and asks if there is anything he can do to make me feel better. We negotiate whether or not we will stay in contact once he is monogamous. I had planned to cut him off completely, but at the slightest suggestion that he is surprised by this, I turn back, waffling.

I don’t let myself cry until I get home. I think about the “it will pass” line from Fleabag, even though I’ve never seen the show. Historically, I find someone I am romantically and sexually interested in every two years. I calculate. Next time should be 2024, which is not too far off. And I always feel better in the summer; it will probably happen then. And then it will pass.

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