A "straight" guy didn't find out I was trans until we were naked in bed

That is the first thing he said after he found out. His hands were still on my waist, our lips were still wet from kissing each other, and he was looking up at me from between my legs where he had just been kissing his way down my stomach. His fingers had just gotten to my underwear for the first time and that is when he felt it. Usually I am a little more proactive, but this time I guess I just got carried away a bit.

"Yeah," I said. "Seriously."

His name was Adrian. Met him at a rooftop party I went to with my friends. It was honestly kinda off the chains so far as parties go. There was a lot of degenerate behavior going on. We hit it off pretty quickly at the party and he is the one who approached me in the first place. I wasn't sure if he could tell that I was trans or not, but I guess I need to accept at this point that people can not in fact tell.

I mean I know what I look like. Long hair, short dress, slim waist and legs, small boobs. I look like I was born as a girl.

He came up to me and said "I was trying to think of something smooth to say, but I couldn't so I am just going to tell you you're beautiful and hope that works."

"It works," I said. I actually appreciate that kind of approach. It feels honest.

We talked for an hour or two. He was funny. A little nervous, but authentic. Which I liked.

When he kissed me at the end of the night as we were leaving, his hands went to my waist and he pulled me in and I felt everything. He felt fit. I could tell he had more muscle than it looked like. He wasn't bulky, just lean.

"Come back to mine?" he asked.

So I did. That easy. I'm not the hardest girl to get into bed with I won't lie.

This tends to be the part where things always get… Potentially messy. I have been kicked out of people's apartments before. It sucks, but I deal with it. I'm not gonna play victim.

We were on his bed. He took my dress off, slowly and sensually. He was kissing my neck, my cheeks, the tops of my small boobs. His mouth finally found my nipple and they are super sensitive so it made me press into him and I was already getting hard at this point. He was working his way down slowly. Kissing my stomach. Getting ready to take everything off.

I put my hand on his. I needed to tell him. I could feel in my chest that he didn't already know, and it would be wrong of me to not disclose.

"I need to tell you something first." I told him.

He stopped. Looked up at me. "What is it?"

"I'm trans," I said. "I have a cock."

That's when he said it. "What the fuck are you serious!"

He seemed shocked enough that I kind of felt bad for him.

I nodded. I always get this weird feeling in this moment. Shame mixed with nervousness mixed with anticipation. It is hard to explain if you haven't experienced it. I never know which way it is gonna go. Sometimes it blows up.

He sat back stunned. He looked at me. All of me, lying on his bed in just my underwear now. I could see the shape of my cock through the fabric. It is honestly crazy we went this long without him knowing.

"You're so pretty though" he said. He seemed sorta disappointed.

And then he pulled my underwear down.

I was fully hard now. Pressed up against my stomach. He stared at me for a second, and then he wrapped his hand around me and I stopped breathing.

"Is this okay?" he asked.

"Very okay."

I'm happy this one worked out. I think a lot of you guys would be surprised how often guys don't care. Ask them in public and you get a different answer, but in private? Whole new world.

He stroked my cock, slow, looking at my face while he did it. I could feel his hand shaking a little. Nervous. Maybe even confused. I think he was surprised by how much he wanted this.

"Can I suck on you?" he asked. Straight guys always ask. I'm not sure why.

I nodded yes and he lowered his mouth on to my cock and started to bob up and down. It was clearly his first time with a cock. I felt his teeth and then he overcorrected and went too wide. I didn't mind. I love being a guy's first. He just wanted me to feel good and he was doing his best and figuring it out as we went.

I put my hand in his hair. "Use your tongue more. Yeah. Like that." I said to him.

He moaned around me and the vibration felt good.

I was close to cumming embarrassingly fast. I think the situation kinda turned me on extra. I pulled him off and he looked up at me.

"I want you to fuck me now" I told him.

He stood up and took his clothes off and he was hard. Really hard. He put on a condom and I told him where the lube was in my purse and got on my stomach.

He was really slow at first. Almost too careful. I had to push back against him before he got the signal that I could take it.

"God, you're tight," he said as he slid the tip of his cock into my ass.

"And you're going slow" I giggled.

That is when he stopped going slow.

He fucked me face down on his bed. With one hand flat on my back holding me down. I reached around under myself while he fucked me and stroked my cock in time with his thrusting.

When I came, it was all over his sheets. I moaned loudly. He felt me tense up and squeeze his cock tightly with my ass and I think that is what set him over the edge. He started cumming and he thrust all the way into my ass and unloaded while inside of me.

We lay there for a while. Sticky. Breathing hard.

"I've never done that before," he said.

"Done what?"

"Any of it. All of it." He paused. "You're really hot. I just want you to know that." he told me.

I rolled over and kissed him. That was sweet of him to say. I slept over that night.

The next morning, his roommate saw me coming out of the bathroom in his shirt and he just nodded at me, completely unsurprised, and went back to eating cereal. Adrian turned bright red. He may have done something new last night, doesn't mean he is fully comfortable with it yet. I'm not judging. It takes time.

I still have his shirt. He hasn't asked for it back. I honestly don't think he will.