"Wait, are you serious?" He said it like I'd just told him I was secretly famous or something.
I nodded. We were sitting on his bed. My legs crossed under me, his hand still on my knee from where we'd been making out thirty seconds ago. I'd just said the thing. The thing I always have to say. The thing that goes one of two ways.
He looked at me. Down, then back up. "I literally never would have guessed."
"That's kind of the point," I said. Smiling but my stomach was doing flips.
He didn't leave. Didn't go quiet. Didn't do the weird thing where they suddenly need to check their phone. He leaned forward and kissed me again, harder this time, and grabbed my waist and pulled me closer and that's when I knew this was going to go very well.
His name was Derek. I met him at a bar the weekend before. He was with a group of friends. I was with mine. He kept glancing over at me until I got tired of waiting and walked up to him and said, "Are you going to talk to me or just stare all night?"
He laughed. Bought me a drink. We talked for two hours while both our friend groups slowly disappeared around us. He was twenty six. Worked in something with computers that I nodded along to without understanding a word. Tall. Dark hair that kept falling in his face. Big hands that he talked with. I liked him immediately.
We texted every day after. He was sweet in a casual way that didn't feel like he was trying too hard. He'd send me dumb memes at midnight and then text good morning at seven like he'd been thinking about me the entire time he was asleep. I melted over it every single time. I also knew I had to tell him before anything went further.
So I went to his place. We made out on his couch for a while. It was getting heavy. His hand was going up my shirt and I was pulling at his belt and I stopped. Pulled back. Said it. Just straight, no buildup. "I need to tell you something before this goes further. I'm trans."
And he said that. "Wait, are you serious?" Not disgusted. Not confused. Just surprised.
He kissed me again and pulled me into his bedroom and I was so relieved I almost tripped over his shoes in the hallway.
On his bed he unhooked my bra and slid my shirt off. Looked at my chest. Small tits, barely A cups, still new enough that I'm self-conscious about them sometimes. He cupped one in his hand and ran his thumb over my nipple and I shivered so hard he smiled.
"Sensitive?" he said.
"You have absolutely no idea."
He put his mouth on one and I grabbed a fistful of his hair and pulled. His other hand was on my waist, holding me tight against him, and I was grinding on his thigh without even deciding to.
"Tell me what you like," he said against my skin.
I told him. I told him I liked being touched. Being stroked. That I'd get hard and I wanted him to not be weird about it. That I wanted his hands on me.
He pulled my skirt up. Found me already hard, pressing against my underwear. He traced the outline with his palm, slow, watching my face the entire time. I whimpered. Actually whimpered. He looked up at me with dark eyes.
"I'm very okay with this," he said. And I believed him.
He laid me on my back. Pulled my underwear down slowly, never breaking eye contact. When my cock came free he wrapped his hand around it and stroked, slow, base to tip, and I arched off the bed and grabbed the sheets.
"You're so pretty," he said. Nobody had ever said that about that part of me before. But the way he was looking at me, with this focused, hungry expression, I didn't question it for a second.
He put his mouth on me and my hand slammed against the headboard. He was good. Embarrassingly good. I suspected this wasn't his first time. He knew exactly how much pressure to use, exactly how fast, swirled his tongue around the tip until my thighs were shaking and I was gripping his hair with both hands.
"I'm going to cum if you keep doing that," I said.
He pulled off. Wiped his mouth. Smiled. "Not yet."
Bastard.
He stripped. He was hard and big and I wanted him so badly I could feel it in my chest. He grabbed a condom and lube from his nightstand drawer and I rolled onto my stomach because I knew where this was going and I was done waiting for it.
"Eager," he said behind me.
"Just shut up and fuck me. Please."
He prepped me slow. One finger first, gentle, giving me time. Then two. He kissed the small of my back while he worked me open and it was so tender and so filthy at the same time that I pressed my face into his pillow and breathed through it.
When he pushed in I exhaled so hard it sounded like a sob. He went slow, inch by inch, checking in. Asking if I was okay. I kept saying yes. He went deeper. I grabbed the sheets and bit down on the pillow and let him.
He started moving and I stopped being able to think about anything else. His hand reached under me and found me still hard and started stroking me in time with his thrusts. His pillow was muffling the sounds I was making, which was probably a good thing because his walls were thin and I was being very, very loud.
"You feel so good," he said. Low and rough against the back of my neck. "You have no idea."
I came with him inside me. Shaking, face down, his hand tight around me. He followed maybe thirty seconds later, pushing deep and going still and breathing hard against my back.
After. He pulled me against his chest. Big spoon. His chin resting on top of my head. His hand flat on my stomach.
"Stay the night," he said.
"You sure?"
"I'll make pancakes."
I stayed. He made pancakes in the morning. They were genuinely terrible. Burned on the outside, raw in the middle. I ate two and told him they were great.
I still see him sometimes. He always makes breakfast after and it's always bad and I always eat it. Thats how you know I actually kinda like him.