Last night I was taken private by a guy.
He took me private for 4 hours.
Now. This was amazing and not just because 4 hours at 1.99 a minute adds up to a pretty good pay cheque.
It was amazing because I really got to know him. Most guys who take me private take me into quick 5 minute privates. 20 minutes is long for me, usually.
We spent the first 30 minutes or so just talking. He told me he had a cuckold fetish. He explained that he wanted to do a roleplay with me where I was his girlfriend, and we loved each other very much but I didn't find him sexually satisfying anymore, and wanted to have sex with a bigger, stronger man, with a larger penis than him.
He wanted us to role-play that we were lying in bed and I was telling him about how I had cheated on him, one night at a party, unable to stop myself because I was getting so sexually dissatisfied with him. I craved more.
But it was complex. Because he didn't want me to just talk dirty and tell him about all the big strong men I wanted to fuck. He wanted me to tell him lovingly. Convincingly. He wanted to believe that I really loved him, and that it pained me to tell him these things, but I just had to tell him because I valued our relationship.
He wanted to see my face close up (I was fully clothed the whole time… he didn't want me naked) and he wanted to pretend we were staring into each others eyes and really holding each others gaze.
He wanted me to reassure him that I still loved him, hold him close, and then break him. Talk about how I desperately needed another man to give me what he couldn't. Describe in detail all of my sexual fantasies and affairs. All the mutual friends we knew, who I wanted to fuck. How exactly they could please me in ways he never would be able to. All the while holding him close, talking lovingly and reassuring him of my care and affection.
In between role-plays (we probably role-played about 3 different scenarios that night, all involving the same bedtime pillow chats), we would break character and just talk normally.
We talked about gender roles. Why he felt such a thrill from imagining himself as lesser than a big strong masculine man. He had been fairly gender confused as a teenager, and had never really had a relationship with a woman. He said what he really desired in a woman was someone who viewed him as a non sexual creature. Someone who viewed him as like one of the girls and they would have a really intimate, relationship, with lots of cuddling and kissing but no sex and then she would go out and have sex with other guys, come home and tell him all about it.
We both stayed up till about 4am, then we realised it was late and we had to go to bed. We lovingly said good night to each other and he told me my performance deserved an Oscar. I told him I hoped he found a girlfriend who could provide him what he was looking for, he thanked me and then I never spoke to him again.
It's a strange thing sharing that much with someone, and then never knowing what became of them. I still think about him sometimes, and hope he managed to find his ideal relationship and become one of the girls.
