Can I call you sir?

A Sexual Fantasy

— By August B

All my relationships thus far have been with women, but since starting my gender transition, I find myself fantasizing about men, coming back to one fantasy in particular.

I have never had anal sex with a partner, but I cannot stop thinking about getting taken from behind. It's sometimes all I can think about while I masturbate, imagining myself sucking on someone until they're ready to fuck me. Would I want to get fucked hard and fast, or deep and slow? Would I even like it? Would I be able to get off? Would any guy even want to fuck me?

I imagine myself finally biting the bullet and downloading a gay hookup app. I agonize over my profile, writing out and deleting words and wondering if I'm inviting the shitty messages that I'm sure will come. I finally settle on something direct, hoping to stave off more awkward messages: "27, Chubby, trans guy looking for a guy to show me the ropes and teach me a thing or two." Then I wait.

Then, I get a message from him. He is an early 40s bear, with salt and pepper hair all over his face and body. Broad chest and arms covered in tattoos. His first message is simple and we continue back and forth, both knowing where this is going, talking about pronouns, how we like our partners to refer to our bodies, and sharing our status.

I tell him honestly that I've never done anything like this, and he responds, we can always take it slow and stop at any time. It's all I need to hear before we are setting a time to meet.

I imagine him coming over and asking if I like to hug. We embrace and I feel myself already getting turned on. I pour wine and we settle on the couch, his arm laying across the back, body turned toward me. He can tell I'm nervous and says some funny things to lighten the mood.

Finally, I look up at him and ask: "Can I call you sir?" He smiles and nods before leaning in to kiss me. My hands are on his chest, feeling his muscles and running up to his head, pulling his face to mine.

I feel him getting hard and reach down to touch him over his pants, moaning into his mouth. He takes off his shirt and then asks if he can take off mine. I'm completely smitten with his check ins and say yes. Our chests press together as I get on top of him, straddling his lap and kissing him deeply.

Before we know it, we're in the bedroom and he is laying down while I undo his pants. "Can you tell me what you like, sir?" I go down on him, feeling him get harder in my mouth and listening to his moans and small exclamations. I come up to kiss him, not ready for him to cum quite yet. He asks if I want him to touch me or go down on me. I think for a minute and say yes. I tell him to finger my cunt slowly and suck on my cock. He feels beyond amazing and I'm getting so wet and hard.

He reaches to the bedside table for some lube, he looks up at me and I say "yes please, sir." He puts a little on his finger and starts to massage my ass hole while still sucking on my cock. I moan and I feel myself eagerly grinding against his hand. He smiles and comes up to kiss me while he continues to finger my hole, getting me ready.

Finally I reach over and fumble with a condom. He takes it from me and hands me the lube to get ready. I'm starting to get nervous as I lay down, all thoughts of getting on all fours behind me because I don't think I can hold myself up. He gets on top and I feel his hard cock brush against my stomach. "are you ready?"

"Yes, sir."