His Secret Pegging Fantasy: A Confession in the Dark

It was past midnight when Derek called, and his voice had that tight, tired sound men get when they have been holding something in for way too long. He said he was stressed, could not sleep, just wanted to talk to someone. I said, of course, baby, talk to me. I am a good listener. That is what I do.

We talked about nothing for a while. Work, the weather, his dog. Normal stuff. But I could feel it underneath, the real reason he called, pressing up like something trying to surface. So I said, gently, Derek, what is the thing you actually want to tell me. The thing you have never said out loud to anyone. There was the longest silence. Then he said, very quietly, you will think I am weird.

I will not, I told him, and I meant it completely. Whatever it is, I have heard worse, and I promise I will understand. Another silence, longer this time. Then it came out in a rush, like he had to say it before he lost his nerve. Sometimes, he said, I fantasize about a woman taking charge of me. Completely. Like, tying me up a little, and, and using something on me. You know. Back there. He stopped breathing. I could hear his heart hammering through the phone.

Oh baby, I said softly, thank you for trusting me with that. There is nothing weird about it. Nothing at all. Do you want to tell me more about it. And slowly, haltingly, he did. He told me he had felt this way for years, that he had bought something online once and thrown it away unopened out of shame. He told me he dreamed about a confident woman who would not laugh at him, who would tell him exactly what to do. His voice was shaking so hard by the end.

I asked him if he was hard right now. He whispered yes. I told him to take himself out, slow, just hold it, do not stroke yet. I could hear him moving, breathing shakier. Good boy, I said. Now I want you to close your eyes and imagine it is me there with you. I am going to tell you a story, and you are going to do exactly what I say. He whimpered, okay.

I painted it for him, gentle and vivid. I described tying his wrists loosely to the headboard with one of my silk scarves, straddling his hips, teasing him until he begged. I described slicking up my strap-on, pressing it against him so slowly, telling him to breathe and let me in. I told him how good he would feel, how beautiful he would look giving himself to me completely. He started stroking without being told, and I did not scold him, I just said, that is it, baby, just like that.

I guided him through it, my voice low and warm. I told him when to go slow and when to speed up. I described pushing deeper, his moans getting louder, the moment he would let go completely and realize there was never anything to be ashamed of. I kept it tender, never cruel, because that is what he needed. Not everyone wants it harsh. He needed soft hands and a kind voice telling him he was safe.

When I finally whispered, come for me, Derek, let it all go, I have got you, he came with this deep shuddering sob that sounded like years of tension leaving his body all at once. We stayed on the line afterward, just breathing together. He said, I have never told anyone. I have never even admitted it to myself, really. I said, I am honored I got to be the first. How do you feel. He laughed, watery and real, and said, free.

That is why I do what I do. For that moment when someone finally stops carrying it alone.

Whatever secret you are holding, the one that keeps you up at night, bring it to me. I will hold it gently, I promise. I am listening, baby. Always.