Rosie Helps Wendy - Sex Stories

Rosie Helps Wendy

... wants to watch! Did you understand? Rosie?”

"Um, did you say that Jay wants to watch you … fuck someone else? He wants to watch it? Oh wow, Wendy. Now I see why you’re having trouble telling me. Is he serious? He really wants you to … um, cuckold him? He wants to watch it happen?”

Wendy seemed less nervous now and slowly said, “If cuckolding means what I think it means, then I guess yes. This started last year, when he mentioned it a couple of times. I just dismissed it then, but he’s talking about it more now. I thought it was just a ploy to let him screw around, but I just don’t know.

I wasn’t expecting this, no way. But since I learned about Mom and Dad’s cuckold marriage, I’ve been running into people I can introduce to it. Olivia was the last one, and she’d consummated her cuckold relationship with Alan and then, a month later, with Jamie. Oh, and I guess I should add the fact that I’m cucking Jason now. I don’t need to share that last. Hmm, this is the first time the husband has asked his wife to cuckold him—at least that I’ve been involved with. This could be fun, but I need to start seriously.

I started by saying, “Wendy, um, what he’s talking about is cuckolding—modern cuckolding, that is. In the old days, a cuckold was a husband whose wife screwed around behind his back um, often putting other men’s babies in his nest.

"Nowadays, the husband knows about it and usually gets off on it. That’s what it sounds like Jay’s talking about. I’ve known several ...

... cuckold couples—ah, cuckold marriages. It can work if both halves are okay and want it.

“What is your reaction when you think about it? Hell, I can tell you, my parents have a cuckold marriage. I learned about it when I was nineteen. They’d been doing it since before I was born. I’ve introduced a few married wives to the lifestyle. So far, they have all enjoyed it.

“What’s your reaction to Jay saying he wants you to cuckold him? My first guess is that he probably does want it, not as a means to, as you delicately put it, screw other women. I can help you decide what Jay’s really trying to have happen. That’s if you’re interested.“

Wendy looked at me and then said, “You know women—uh, wives—that..." Her voice trailed off. Then she said, “You know women that screw around with other men? For real?"

“Yes, I do. I don’t know why, but after I learned that Mom cuckolds Dad I’ve run into,” I hesitated to be careful with what I said. I don’t want to out anyone.

“Wendy, it's not common, but there is a lot more of it going on than you’d believe. A lot of friends—people I know—have talked to me. Kind of like you have today.

“When I was living at home, my folks introduced me to a lot of people in the lifestyle. A lot of, well, some of the marriages imploded because of it. Anyway, that taught me you need to be careful if you want to protect your marriage.”

I waited for Wendy to say something.

Wendy looked at me, then hesitantly said, “Your friends, … the people that ...