My First Jack And Jill

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My First Jack N Jill

One of the masturbation experiences I had never had was a Jack N Jill or mutual with another guy. My wife and I masturbate together on occasion, and have shared fantasies with each other for years. She is very open-minded and adventurous, but one of the things she did not get into was the idea of a Jack and Jill party. And as far as group sex, she was happy with the one threesome we did early in our marriage.

Sue does not mind that I browse erotic Internet sites, she has even gotten on with me a few times and enjoyed the chats. One night I got in a private chat with a 36-year-old fellow (I'm 45) who was very interested in my descriptions of Sue and I jacking off together. When I told him about cuming on her face and sharing my semen in playful cum kisses he got really hot. He told me he was jacking his cock (which I was also) and wished he could cum on my cock while I was playing with myself. The erotic picture of doing that got me off. It was an altogether decent chat session. And it got me thinking about possibilities.

I found the same fellow on the chat site a week later and suggested a meeting. I was in his area on business and invited him to my hotel. We met in the bar, had a few drinks, and then went up to my room. I put an erotic movie on the TV, got us another drink and kept the conversation going.

'John' was very nervous and at one point was about to back out. Fortunately, there was a cum scene on the movie that appealed to both of us and that broke his tension. We got undressed and jacked off watching the show. I enjoyed watching John as much as the movie, and he admitted the same. He wanted to hear all about Sue and I masturbating together and cum kissing. I was happy to oblige. When it seemed the moment was right, I asked him if he still wanted to cum on my cock. He was shy about it, but said yes.

We stood facing each other with our cock tips just touching. John concentrated on my cock and shot wad after wad of cum onto my hand, cock and stomach. When he was done, I let my load go and wet down his crotch with my cum. We did it a couple of more times that night before John had to go.

Before he left, I asked him if he would be interested in a Jack and Jill party. He was, and left assuming he was going to party with Sue and I. I knew that was not going to happen, but I had a plan.

I made several dates with escort services before I found the right woman. Allison is in her mid-20s, a petite and very pretty girl. She is a brunette with a 34-22-34 type build, medium breasts and a beautiful shaved pussy. She's very opened minded and agreed to a Jack and Jill three-way and cum kissing right away. Half the fun of the session was planning it with her and then cuming on her face for a big cum kiss. I booked her for a full evening the day John was going to visit.

John and I met in the hotel bar again. He was disappointed it was not my wife, but was all for meeting my 'girlfriend.' When we got to the room, Allison had a sexy movie on and was wearing a see-thru baby doll negligee. She served drinks and seductively undressed us. We sat on the bed, watched the movie and masturbated. We filled the first hour with sexy talk about 'first times.' First masturbation, blowjob, fuck; that sort of thing. Allison was into it just as much as we were. The only time her fingers left her pussy was when one of us licked it or she gave some head.

I started the main event. I knelt in front of her and shot a load of cum into her mouth and onto her cheek and chin. I licked up a rope of my cum off her chin and feed it into her mouth. She responded by using her tongue to flood my mouth with my jizz. We spent five minutes swapping my milk back and forth for John to watch. Then it was John's turn.

He rose to the occasion and let out a much larger load than mine. He was very tentative at first, but got his tongue into Allison's mouth and had his first, but not last, cum kiss that night.

We went on to some mutual masturbation that night, but the highlight was watching John jack off and share his jizz with a pretty young girl.

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