Confession Phone Sex: He Told Me His Cuckold Secret and I Made Him Stroke to It

It was almost one in the morning when he called, and I could tell from his breathing he had been working up to this for days. His name was Tom. He said, I have never told anyone this, and I said, good, that is exactly what I am here for. Tell me. The real stuff, not the cleaned-up version.

It came out in pieces at first. He is married, ten years, loves his wife, but for the last two years he has not been able to stop fantasizing about her with someone else. Specifically, he said, her boss. A big guy, confident, the kind of man Tom feels small next to. He told me he pictures them at the office late, her bent over the desk, and he pictures himself watching from the doorway. His voice was shaking. He said, I think there is something wrong with me.

There is nothing wrong with you, I told him, and I meant it. I asked him what part got him the hardest, and after a long pause he whispered, when I imagine him finishing inside her. I asked him what he did while he fantasized, and he admitted, even more quietly, that he wore her panties sometimes. Black lace ones. I smiled in the dark and said, are you wearing them right now. Silence. Then, yes.

I told him to take his cock out, slow, and just hold it while we talked. I could hear the rustle, the shaky breath. Good, I said. Now tell me the rest. What does the boss say to her. And Tom started talking, halting at first, then faster, describing how the bigger man would tell his wife she needed a real cock, how she would moan, how Tom would stand there hard and aching and useless. I asked him how small he felt in the fantasy, and he whispered, so small, and I said, that is the hottest part for you, is it not, feeling small while she gets stretched. He whimpered. Yes.

I started guiding him then, gentle but firm. Stroke slow, I said. Just the head, light touches, while you tell me what she sounds like when she comes for him. He described it, groaning, and I could hear his hand moving. I teased him a little, told him his tiny cock probably could not even fill her up halfway, and he loved it, he actually thanked me. Not everyone wants it cruel, I kept it sweet, like a secret between us. I told him to stop, to edge, to hold it right there on the brink while he confessed the deepest part.

And then it came out, the real confession under the confession. Last month, he said, his wife came home late from a work dinner, flushed and happy and smelling like cologne that was not his, and instead of confronting her he went to the bedroom alone and touched himself to the thought of it. He had never told a soul. I was quiet for a moment, and then I said, Tom, that is the most honest thing you have ever said out loud, and I am so glad you told me.

I let him stroke again, faster now, and I talked him through it, describing his wife taking that bigger man while he watched in her panties, helpless and throbbing. When he was right on the edge I whispered, come for me, let it all go, your secret is safe with me. He came with this broken, relieved sob that I will remember for a long time.

We stayed on the line a while after, just breathing. He said he felt lighter. That is my favorite part of what I do.

Whatever you have been carrying around, the fantasy you have never said out loud, bring it to me. I have heard worse, I promise, and I will love hearing it from you. I am listening.