The small of his back rests on my thigh, just above my knee. His head compresses the pillows. When I twist my fingers inside him—index and middle, plunged into his hole as deep as they can go—his shoulders dig into the mattress. He lets out a wail that’s half animal, half supernatural.
But he’s not in pain. There’s a world of difference between agony and what this man is feeling. I stare him in the face as he writhes and moans and bucks his hips. He can’t see me. His face is screwed up too tight, his eyes clamped shut as he loses himself in the sensations my greased and twisted digits arouse. Once more I twist in the other direction. Like he’s pedaling some invisible bicycle, his hairy legs bend and paw toward the ceiling. “Am I hurting you?” I ask.
He takes a moment to answer. “What? No.” He sighs the words so that they arrive with the scent of his breath, still faintly smelling of the cinnamon gum he’d chewed after dinner. “Please don’t stop.”
“I have no intention of stopping,” I tell him. Truer words have never been spoken. I made a promise to this man, and I intend to keep it.
I see tears in his eyes as he looks at me. He has to wipe them away with a free hand. Simultaneously, he starts to laugh at himself, as he pictures how he must look to me. “It doesn’t hurt,” he assures me. “I just didn’t know it could feel so good.”
I receive the compliment with a curt nod. No words. But I take my ring finger and, when I withdraw the other two, add it to his hole. The extra girth causes him to squeeze shut his eyes again. His head presses back against the headboard, and his whole body shudders.
“I know it feels good,” I tell him. “I know it’s all new and scary to you. But you wrote me for a reason. Remember?”
“Yes,” he breathes.
“What reason is that?”
I can only see the bottom of his chin, his neck is extended so far back. “Because I want you.”
“And why do you want me?”
He’s struggling to make his higher functions work, when his body is wracked with thrill. “Because you’re hot.”
“No.” Not it at all. “Because you trust—“
Now he remembers. “Because I trust you—“
“—to do it right. That’s what you said.”
“Yes.” He nods his head. “Because I trust you to do it right. I want you because I know you’ll do it right.” He’s panting like he’s run a two hundred-meter race.
“That’s right,” I say with approval. Gently I remove my knee from beneath him, and let him settle into the mattress. I shift myself so that I’m between his legs. My cock is rigid. If he looked down, he’d see how red and angry it is as I continue to deny it what it so badly wants.
This isn’t about me, though. It’s about him. When a handsome man has read my blog for two years and gotten up the nerve not only to contact me, but to fly from the west coast to east specifically to visit me, I take my time with him. When he’s booked that long flight and a hotel room in the city for the night and has escorted me to dinner to prove himself a gentleman, he gets everything he wants.
When he’s offering me his anal virginity, I don’t poke at him and go. I set the pace. I maximize his pleasure and erase his doubts and fears. I do it right. I aim to make him remember me. Like I tell guys, I want to fuck him so well that afterward he regrets any cock that’s not mine.
What is he? I can’t remember from his profile. Thirty or thirty-one. Something like that. A professional man. Cool and confident on the exterior, but I know he’s been worried all night about this moment. “Now, I am going to hold your legs up,” I tell him, while still I manipulate the soft, wet flesh with my hand. I’ve spent the last hour and a half making love to this hole…touching it, kissing it, licking and eating and fucking it with my fingers. He’s ready for cock. He might not know it, and he might not believe it, but he’s ready. I know. “And you are going to look into my eyes . . . and you are going to relax . . . and you are going. . . .”
“I’m going to get fucked.” His square-cut jaw trembles slightly.
“You’re going to get fucked,” I agree, in a low and breathy voice. I’ve withdrawn my fingers. I’m pleased to see his hole retaining the gape. I position my cock head at the space I’ve left behind.
“Oh god,” he whispers. His legs start to jerk when I push in. I hold them immobile.
He’s whimpering the entire time my head stretches his hole. “You want this,” I remind him.
“I do,” he says, suddenly worried I might change my mind. “Oh, I do. I do want this.”
“You’ve got to be taught,” I say, “what your hole is for.”
He repeats the words like a hypnotist’s subject. “I’ve got to be taught,” he says. He winces and breathes in a hiss, as I slide a little further in.
“Tell me you want it,” I instruct him.
“I want it so much. Please.”
“You flew a long way for this,” I say. “You picked me out for this moment.”
“I want it,” he says, still in a trance. “I want it to be you.”
I keep him focused on the need. “Look at me,” I instruct. “Look at me.” He opens his eyes and stares into mine. Our faces aren’t too distant. I could lean forward and kiss him, if I wanted. “You feel good. Do you know how good you feel?” He shakes his head. “I am having to do everything in my power to keep from raping your tight little hole right now, because that’s how good it feels. I bet you didn’t know you were a hot little fuck.”
When I crack a smile, he can’t help but return one in kind. “Really?” he asks, struck shy.
“Really,” I tell him. “You are a hot . . . little . . . fuck.” I’ve been sliding in the entire time. My head nudges against something familiar. I’m in. “Now, did that hurt?” I ask him.
“No,” he whispers. He’s in awe, like prophet receiving a revelation. “How . . . how much more is there?”
I don’t answer him directly. Instead, I take his hand and pull it around his hips so that he can feel for himself.
“Oh my god.” His eyes widen as he realizes. “You’re all the way in.” I nod, very slowly. I’m breathing through my mouth, heavy and slow. My heart is pounding like a timpani. “You’re all the way in,” he says, as his hole clamps down on me.
“Sssssh,” I tell him, with a gentle kiss on his lips. “Relax.”
“Am I doing okay? Do I feel all right? I want to be okay for—“
I shake my head. Kiss away the question. “You are wonderful,” I tell him. I burst into a little bit of laughter. “You really don’t know how wonderful you are at this, do you?” My words make him unclench again, enough that I can rock back and forth. I’m not thrusting—not yet. But I’m letting him feel the ebb and flow of my hips, getting him used to the rhythm that will build and grow and sweep us away as I take him to the place he wants to go.
His eyes are very serious as first. Then, as he realizes he can trust me, he exhales a breathy little chuckle. His lips curl into a smile. I nod. Now that I’ve given him permission, he settles into the pillows. He relaxes—really relaxes. My cock can feel the difference. “I want this,” he tells me, meaning it.
I nod with approval once more. “You want this.”
“I’m being fucked,” he whispers. I can see the joy in his expression, when he realizes that the long-held fantasy has finally been made real. “I’m being fucked.”
“Oh, you are definitely being fucked,” I say, rocking my hips in a longer arc.
“It’s. . . .” As my rocking turns into small thrusts, and as the small thrusts broaden into my inches sliding in and out of his slick, hot chute, he struggles to find words. At last he sighs and regards me with the infatuation of the deeply happy. “Amazing.”
I accept the compliment with a slight smile. “You’re a very, very good learner,” I tell him, as I lean in for a deep kiss. I slide my wet rod so deeply in his hole that his hips lift off the bed. He grunts and rises to meet me, as our tongues entwine.
He doesn’t know it yet, but the man is in for a long night. I promised to teach him what his hole is for. And I’ve a lot of lessons to get through.