Rainbow Jockstrap

It had been a while. Four years in fact; a painful breakup and the time I needed to focus on my medical transition had gobbled up the months at speed. My top surgery and the recovery period; resting, then slowly regaining my range of movement. Gentle exercise at home and then making it back into the gym, lots of little milestones, like finally being able to do pull ups again, or stretch out my arms fully without feeling tightness and tugging. Allowing myself time to integrate the change and appreciate my healed body, sitting with the comfort and joy I felt now; the most loving thing I had ever done for myself. Then the long process of accessing testosterone and the profound impact that had on my mental health and clarity, feeling present, a cloudy veil lifted from in front of my eyes. Finding a new job and new home, both in myself and in reality. Finally leaving my ‘old chapter’ flat and my ex behind.

Despite all the things I had to focus on, and all the change I was navigating, I still found in the quiet moments I was craving human contact. The more I felt myself, the more I wanted someone else to feel me, too. My sex drive was growing, tension building, increasing horniness that often felt uncontrollable. The hunger was powerful, strong enough for me to download endless hook up apps—but my nerves and fear always blocked me from going through with anything. A quick coffee and then a ghosting, a fleeting kiss and then excuses until they lost interest and left me alone. I was trapped in a cycle of digital edging. Sometimes it was a lack of chemistry, but usually it was me holding me back.

The anxiety about putting myself out there wouldn’t quit. Lingering damage from past comments haunted me—the relentless concern that I would be rejected for my transness. After years of performing for others in my sex life, it was terrifying to show up as myself, to take off the mask. The fearful side of me wanting to never let another soul near me no matter how much I craved contact. Not wanting to be vulnerable, to give anyone that power. If this went badly, it would only reinforce the negative voice telling me I was undesirable as myself, shattering the confidence I had worked so hard to build.

Those insecurities still gnaw at me now as I hover on his doorstep. The sounds of Soho on a sunny morning bustle around me, coffee shops are full of lingering couples and dogs. The neon signs in the sex shops still dimly pulse in the daylight, a street cleaner passes me with his brush. Just another weekend morning to everyone else, but a big moment for me. I raise a hand to the doorbell, rest a forefinger on the slightly dusty surface. Am I about to do this? He’s very cute, I know that much. Our conversation has been sweet, mostly wholesome. He seems very thoughtful and open. He’s shared a lot with me, despite not knowing me well. I know how badly he was hurt by his last boyfriend and knowing this makes me feel safer. He gets it, he understands.  Both of us have deep wounds around rejection and a fear of getting close to anyone. He’s the first person I’ve connected with on a hook-up app who seems real, like he isn’t putting on a two dimensional show. We’re both being cautious—at the same time, we both know why I’m here. 

I withdraw my finger, remove my sunglasses and step back to check my hair in the shop window next door. My brown curls have a tendency to go a bit wild, but they’re behaving today. I straighten my shorts, tucking in the edge of my tank top. Fiddle with my rucksack a little and then accept that I’m just engaging in nervous procrastination now. I look as presentable as I’m ever going to, so I draw in a deep breath and push the doorbell. I hear his footsteps and stand back; the door opens and there he is. A tight t-shirt and jeans, tousled hair. His tattoos are on show and I want to trace them all with a finger. The t-shirt clings to his toned torso. He looks fresh, like he stepped out of the shower five minutes ago. The perfect blend of groomed but not overdone.

“Um…hi! Come in.”

I hear the uneven tone in his voice when he speaks, his breath is unsteady—it could be the stairs, or it could be nerves. 

I follow him up to his flat and it’s like a set from a film. Twisting stairs that pass other flats, personal items hanging outside. A building with history, the Victorian era whispering at me from the walls as I pass. He lives in the attic flat, a loft room with an incredible view of London. His walls are covered in art, an easel in the corner. Erotic polaroids of past lovers adorning the wall. 

My rucksack goes on the floor and I settle on the couch, my can of sparkling tropical energy drink clutched in my hand. Sipping it helps me center myself as he settles near me. We make small talk, the energy between us crackling. The air feels solid, charged. The sense of anticipation growing, I wonder who will make the first move. I want it to be me, but I need the confirmation that he wants me. He touches on his dating history, all cis men so far. This is validating and reassuring, I know I’m not dealing with a chaser, but the insecurities raise their head with renewed vigor. Will he really want me? Am I enough? He starts to flirt; he likes my sports socks. He runs a hand over my calf muscle when he says it. We’re inching closer to one another on the couch, our legs almost entangled.

He leans in and pauses, there is a moment when we both look at one another, both asking the question and getting an answer at the same time—then we’re kissing, furiously and intensely. My hand is in his hair, pulling him towards me, dragging down to rest on the back of his neck. My other hand finds the belt loops on his jeans, hooking my fingers in and pulling him towards me. Now that I have permission, the floodgates have opened and I am absolutely desperate to finally release the torrent of sexual energy that’s been building for so long. 

His hand is on the side of my face, the other travelling down to my waist. He pulls back from the kiss for a moment, panting. 

“Do you like sucking dick?”

 I nod, “Yeah, I mean I haven’t been with many men, but I want to learn.”

He smiles at me, “I can give you pointers if you need them, don’t worry.”

His hand on my waist pulls at my t-shirt and I raise my arms, helping him pull it off me. He takes a moment to run his hands over my torso, complimenting my tattoos and my muscles.

“Fuck, you’re so fit, so strong. It’s really hot.”

I melt at the gender euphoria I get from his words, at finally being appreciated for what I love about my body. These things make it really mine, make it feel like home, at last.

I can’t hold back a grin when he tells me he loves sportswear—my everyday staple is sports shorts and a t-shirt, or some variation of gym wear. 

He fiddles with the edge of my shorts, “Have you ever worn a jockstrap?”

I shake my head, I haven’t. I have always felt a little intimidated by cis gay culture, always lingered adjacent to it but never had the confidence to take up space.

“Would you like to? I think it’d look so sexy.”

 The little lurch in my stomach tells me I would and when I nod, he pulls out a rainbow jockstrap from a nearby cupboard and tosses it into my lap.  

I tug my shorts and boxers off quickly, but the vulnerability of being totally naked hits me and I’m glad to have the jockstrap to pull on. He’s lowering the blinds and doesn’t watch me change, but when he looks back up, his eyes widen.

“That is so fucking hot!”

With renewed confidence I approach him and he guides me to my knees on his mattress, unzipping his jeans, dropping his boxers and weaving a hand into my hair. I open my mouth and he pulls me forward, onto all fours so he can lean over me. His dick is long, smooth and slides easily past my lips. I breathe in through my nose and try my best to open my throat, to take it as deep as I can. He moans and starts to thrust gently, reaching over me to rub across the jockstrap between my legs. A rhythmic stroke that brushes over my hard T dick up to my ass crack and back again. I spread my legs wider, dropping into a deeper crouch, pushing my face further into him. 

“You’re taking it so deep, good boy,” he murmurs gently.

The praise sets off a small explosion in my head and my groin simultaneously. No one has ever spoken to me like this before and I love it. Both hands move to my head, his thrusts get faster and quicker. “I want to face-fuck you, is that okay?” 

I can’t use my words and I don’t want to stop sucking, so I moan instead and he tightens his grip in my hair.

“You are made to suck dick,” he says, and then his thrusts become all I can think about. Everything but carefully timing my breathing and relaxing my throat are forgotten. The physical sensations are overwhelming. The drool is pouring from my mouth, running down my chin and puddling on the sheets beneath us. The pure mindfulness and presence, the reality altering state of pure surrender. Time has no meaning, until he slows down—

“I want to cum inside you,” he reaches over, stroking me between my legs again, making his meaning clear. 

I murmur my assent and as he withdraws from my mouth I sit back on my heels for a moment and catch my breath, he passes me a small towel for my face. The moment I have wiped it, his hands are on me again and I’m guided onto my front, light headed and dick-drunk. 

“Arch your back,” he tells me, “Present yourself for me like a slut.” And I do, feeling him pull the jockstrap aside, aching for what’s coming next. I feel the tip, the moment of resistance and then, my involuntary gasp of need as he pushes in, opening me up. 

Daylight filters in past the blinds as they blow in the breeze and I watch the shadows dancing on the sheets beneath us as he builds speed. The air is cooling the mingled sweat on our skin as he moans in my ear, grunting, “You’re a good boy, so tight for me.” I push back, grinding against him as one of my hands finds my own hardness and rubs. When I cum, it’s explosive, my lower body shuddering, the intensity between my legs almost more than I can handle. The release is exquisite, four years of holding back and I’m finally letting go. 

Today, for the first time, I get to fuck and be fucked as myself, in a way that makes me feel truly seen.

I clench hard around the dick inside me. He groans and leans down to my ear, “can I cum inside you now?” I nod, enjoying the sounds of pleasure he makes as he too, is letting go.