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Femboy

straight guy paid me for his first time w a femboy and had to ask out loud for everything

Straight guy books a femboy escort for his first time with a guy. Kit makes him ask out loud for every step, sucks him at minute fifty one, then lets him fuck.

First timePatient soft-domNo shame arc

18+ Adult fiction. Everyone in it is an adult.

adult sexual contentoral sexmutual masturbationpaid sexual services
first-time-with-a-guyoralmutual-handjobpraise
straight

I had been staring at the booking confirmation on my phone for eleven minutes when the studio door opened and the person I’d hired walked in.

He was — okay. The first thing I noticed was that he was short. Shorter than me. The second thing I noticed was that he was wearing a pink cable-knit sweater, soft-washed jeans, and a pair of platform sneakers that did not pretend to be anything but platforms. His eyeliner was sharp enough to cut paper. He smiled at me like he had all the time in the world, which — given that I was paying him by the hour — he technically did.

“Hi,” he said, and stuck out his hand. “I’m Kit. Pronouns today are he/him, but I switch it up. You can ask any time and I’ll tell you.”

He was twenty-six. He’d told me that in the messages, in the same breezy tone he’d used to say he liked pineapple on pizza. He’d also told me he was a femboy, that he’d been doing this work for three years, that his rates started at a hundred and eighty for a ninety-minute session, and that he had a soft spot for first-timers. I’d asked what “this work” meant and he’d sent me a single sentence back: anything you want to try, exactly the way you want to try it, at exactly the pace you can handle.

I shook his hand. It was smaller than mine and very warm.

“You’re Henry, right?” he said. “Twenty-nine, no experience with guys, no experience with femboys, no experience with paid sessions, and you’d like to start slow.”

“That about covers it.”

“Cool. Sit anywhere. I’m going to make us both some tea, and you’re going to ask me the first three questions that come into your head. Don’t filter them. The unfiltered ones are always the most useful.”

I sat on the low velvet couch. The studio smelled faintly of cedar and orange peel. There was a thick rug under my feet, a wall of bookshelves, and a single softbox light in the corner that had been deliberately left off. I could hear, very faintly, the sound of someone else’s conversation two rooms down.

The questions that came into my head, in order, were these:

“Are you — is this — are you a woman?”

He laughed, the kind of laugh that doesn’t want anything from you. “No. I’m a guy. I just like the way I look better when I look like this. Want to see what I look like in a T-shirt and shorts? I can show you.”

“Maybe later.”

“Later works. What’s question two?”

I picked up the courage from somewhere. “Have you done this — like, with a guy who has never done anything with a guy — a lot?”

“About a hundred times,” he said. “It is, genuinely, the most fun job. You guys are so nervous that you are also extremely polite, and I get to teach you things that nobody ever bothered to teach you.” He poured hot water into two mugs. “Green tea is fine, right? I asked in the messages.”

“Green is fine.”

“Good.” He brought both mugs over and sat in the armchair across from me. He sat cross-legged and the sweater rode up at the hem. I saw, just for a second, the flat plane of his stomach and the waistband of jeans cut low enough to suggest, without confirming, anything at all. He didn’t pull it. He also didn’t yank it down. He just kept sitting.

“Third question?”

I sipped the tea. It was very good. “If I freak out halfway through, what happens?”

“Then we stop,” he said. “No questions. No charge for the second half. I walk you to the elevator if you want, or you stay and finish your tea, whichever. I have a panic button under the register that pings my friend downstairs, but I’ve never had to use it. The worst thing that’s ever happened on a first session is a guy who cried and then felt silly about it, and I always tell those guys the same thing, which is that crying counts as feeling something, and feeling something is the whole point.”

He was watching me. Not the way you watch a thing you want. The way you watch a thing you’re holding carefully.

“You’re going to be fine,” he said. “You picked me because I am very patient, and you picked a ninety-minute session because that’s the right amount of time. You’re going to do exactly as much or as little as you want, and I’m going to be there the whole time, and the only thing I’m going to be doing besides being there is enjoying myself. I genuinely enjoy this. That’s the trick.”

We sat for a few minutes. I drank half the tea. He drank half of his. Outside, a train went past, and the building hummed the way buildings hum.

Then he stood up, very slowly, and took off his sweater.

Underneath, he was wearing a white tank top and a thin gold chain. His shoulders were narrow but he had the kind of arms that came from climbing, not lifting. His chest was almost completely flat. He had a small tattoo on his inner bicep — a pair of scissors crossed with a needle, like a tailor’s mark.

“There,” he said. “Now you can see the part I don’t usually show people on a first session. No makeup. No platforms. Just the guy.” He sat back down. “Look as long as you want. There’s nothing wrong with looking.”

I looked.

He was a guy. He was also — separately and at the same time — extremely pretty. The two things did not cancel each other out. They sat next to each other, in the same body, the way a song’s verse sits next to its chorus.

“Can I ask —” I said.

“You can ask anything.”

“The thing I’m not sure about. The — the part I keep going back and forth on.”

“The downstairs part,” he said gently. “I have a penis. Yes. I’m a femboy, not anything else. I take hormones for my skin and my hair, not for anything you’d notice, and I keep the rest of me the way it came. I am, anatomically, what you’re worried I might be. And I am also the person sitting across from you in a tank top offering you tea. Both of those are true at the same time.”

“Right,” I said.

“I can answer that question a hundred more times,” he said. “Or you can take a minute and let it be settled.”

I let it be settled.

“Okay,” he said. “So here is what I think we should do for the next hour. I think we should sit on this couch. I think you should sit on one end and I should sit on the other. And then I think we should touch — slowly, gently, you on me first, then me on you, with the lights on, with all our clothes on, and we should stop and check in with each other every ninety seconds. If you want to keep your shirt on, your shirt stays on. If you want to take your shirt off at minute forty-five, your shirt comes off at minute forty-five. If you want to take your pants off at minute eighty, we talk about it first. If you want to stop at minute eleven, we stop at minute eleven.”


“That sounds like a lot of check-ins.”

“It is exactly the right amount of check-ins for a first session,” he said. “The second session is fewer. The tenth session is basically none. But the first one is the one where you build the muscle of saying what you want out loud, and the only way to build that muscle is to use it.”

“Alright.”

“Alright. Couch. One end each. Shirts on. Lights on. Clock starts now.”

We sat.

The couch was soft. Kit tucked one leg under himself and left the other foot on the floor. The tank top was thin enough that I could see the small movement of his breathing. I kept my hands on my own knees for the first few minutes, and he didn’t tell me to do anything else. He just sat there. He smelled like green tea and something faintly herbal — shampoo, maybe. His eyes were the kind of brown that looks gold near a lamp.

I reached out, finally, and put my hand on his wrist.

He didn’t move. He just said, very softly: “That’s good. Take your time.”

I ran my thumb along the inside of his wrist, where the skin was thin. I could feel his pulse. He was calmer than I was, which I appreciated more than I can say.

“Can I —” I said, and stopped.

“You can.”

“Can I put my hand on your chest.”

“You can. Above the shirt or under it?”

“Above the shirt is fine for now.”

I put my hand flat against his sternum, over the white cotton. He was warm. His heart was steady.

“How’s that feel,” he said.

“Okay,” I said. “Really okay.”

“Good.” He put his hand over mine for a second, then took his away. “My turn. Can I put my hand on your arm?”

“Yeah.”

He put his hand on my forearm, very lightly, the way you’d touch a book you hadn’t read yet.

For the next twenty minutes we did that. His shoulder. My shoulder. The back of his neck, which made him laugh and then stop laughing. The muscle along the side of my thigh, which made me stop breathing for a second. The small of his back, which I asked permission for and which he gave immediately.


Every ninety seconds he would say, in a different tone, the same question. How’s that. Still okay? Want to keep going? Anything you want to change?

Each time I answered yes, or stay, or keep going, or — once — slower, please.

At minute thirty-eight he said, “I want to try something. I’m going to put my hand on the side of your face. Is that okay.”

“Okay.”

His palm was smaller than I expected and warmer. He turned my face, very slightly, toward the lamp.

“You’re going to cry in about thirty seconds,” he said.

“I am not going to cry.”

“You’re going to cry in about thirty seconds, and that’s allowed, and I’m going to stay exactly where I am.”

I didn’t cry. I came close. I felt, instead, a wave of — I don’t have a good word for it. Relief, maybe. The relief of being seen by someone who had decided in advance to be kind.

He kissed me, very softly, on the corner of my mouth.

“How was that?” he said.

“Good,” I said, my voice a little ragged. “Really good. Can you do it again.”

He did. He did it again, and again, and again, each one a little less corner and a little more mouth, and after the fourth one I tasted green tea on him and I knew exactly what I wanted.

“I want to take my shirt off,” I said.

“Okay,” he said. “I want to take mine off too. Together or one at a time?”

“Together.”

“On three. One, two, three.”

We took our shirts off at the same time. He was flatter than me and his skin was paler and he had a small constellation of moles over his left shoulder that I wanted, suddenly and very much, to count.

“How do I look,” he said, smiling.

“Like a person I want to keep looking at,” I said.

“Good answer.”

He leaned in and kissed my chest, right over my heart, then lower, then looked up.

“Minute fifty-one,” he said. “You have thirty-nine minutes left and you have a face on.”

“What face.”

“The face of a man who wants to talk about pants at minute fifty-one instead of minute eighty.”

I laughed, and it came out shaky. “Can we?”

“We can do anything you can ask for out loud.”

So I asked. Out loud. It took two tries. “I want to see you. All of you. And I want you to—” I stopped.

“Say it.”

“I want you to touch me. Under. With your hand.”

“Okay,” Kit said, very gently. “Me first, so you see there’s nothing scary.”

He stood up in front of the couch and unbuttoned the soft-washed jeans and pushed them down with his underwear, and stepped out of them, and stood there with the lamp behind him.

He was half hard. Smaller than me, cut, flushed pink at the tip, and I looked at it for a long time while he just stood there and let me. The thing I’d been going back and forth about for three months. It was just part of him. Pretty, the way the rest of him was pretty.

“Still okay?” he said.

“Yeah.” My voice was gone. “Yeah. More than.”

“Your turn. Or I can do it for you.”

“You do it.”

He knelt on the rug between my knees and undid my belt like he was opening a present he already knew he liked. Jeans, boxers, down to my ankles. I was so hard it was embarrassing. He wrapped his hand around me, slow, warm, and looked up at me.

“How’s that.”

“Good. God. Good.”

He stroked me with his whole fist, unhurried, twisting a little at the top, and every few strokes he asked, a different word each time. Okay? Like that? Faster? I said yes, yes, please, and then he said, “I’d like to use my mouth. Do you want that?” and I couldn’t answer with words, I just nodded about twelve times, and he laughed and took me into his mouth.

I had been sucked before. Not like that. Not by someone who’d decided in advance to enjoy it. He went slow and wet and deep, his eyeliner perfect, his eyes on my face the whole time, and when I put my hand on the back of his head he hummed and let me, and when I pulled my hand away, embarrassed, he took it and put it back.

“Kit. Kit, I’m—”

He pulled off. “Not yet. One more thing to ask for. You’ve been looking at me this whole time.”

I had. He was fully hard now, kneeling on the rug, and I’d been looking at it like it was a question.

“Can I touch you,” I said.

“Yes.”

He climbed up onto the couch beside me, and I reached over and wrapped my hand around another man’s cock for the first time in my life. It was hot and smooth and it jumped in my hand, and Kit made a small happy sound and leaned his forehead against my shoulder.

“Like you’d do yourself,” he murmured. “You already know how.”

I did know how. That was the strangest part. I stroked him the way I’d stroke myself, and he stroked me, and we sat there on the velvet couch side by side with the lights on, jerking each other off, his breath going faster against my neck. He talked me through it the whole time. Not instructions. Praise. That’s so good. You’re doing so good. Look at you. I didn’t know I wanted that until I was drowning in it.

He came first, on purpose I think, so I’d see. He tensed against me and gasped and spilled hot over my knuckles, and I watched it happen in my own hand, and it was the most intimate thing I had ever seen. Then he tightened his fist on me and said, “Your turn, Henry,” right in my ear, and I came so hard I made a noise I didn’t recognize as mine.

We lay back on the couch afterward, my head on his shoulder, his arm across my chest, both of us sticky, the lights on, the rest of the time stretching out in front of us like the rest of a book you want to read slowly.


“Minute seventy-four,” he said. “You were very ahead of schedule.”

“Sorry.”

“Don’t you dare apologize.” He handed me a tissue box off the side table with the confidence of a man who keeps one there professionally. “Now I’m going to ask you the question you’re going to have to keep answering for the rest of your life. Are you ready?”

“Yes.”

“Do you want to do this again?”

“Yes.”

“Same person or someone else?”

“Same person.”

“How soon?”

“Tomorrow. If you’re free tomorrow.”

“I’m free tomorrow,” he said, and kissed me, on the mouth, with the lights on. “Bring questions. The asking is the game.”

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