Rosie Helps Wendy - Sex Stories

Rosie Helps Wendy

... for sure: it’s not going to be like you described it. For Wendy, it can also be exhilarating, intoxicating, and addicting. Notice the word addicting. For a lot of first-time cuckoldresses, it is addicting. They don’t want to stop. Often, they can’t stop.

“You’ve helped her break the taboo—the main taboo that keeps wives faithful. Hell, it may already be too late. She’s already pictured the first time in her mind being fucked with a different cock, a different man fucking her, demanding new things from her. Jay, can you picture Wendy like that? Could you enjoy seeing her being fucked like that? If you can’t, then you don’t really want her to cuck you.”

I looked at Jay and Wendy, waiting for Jay to answer.

Wendy responded, looking at Jay, “That sounds interesting, doesn’t it, Jay? Exciting. I’d love for Gary to fuck me like that. I can see what Rosie is saying might happen. I can see why I might need to continue. Damn it, Jay, who do you want to be my first? You said, Eric and Gary. Eric is married so unless he has an agreement with Lois, he’s a no. But Gary? Is that who you want? My first, Our first? Gary? His beard is going to make it different when he's kissing me; I can't imagine what it's going to feel like when he's going down on me. Is that what you want?

"What do you want, Jay? Who do you want to see taking my pussy away from you?"

At this point, both Wendy and I waited for Jay to answer.

I can tell I shocked Jay. He was imagining sterile sex, a ...

... penis, a vagina, and a little cum. He has no idea what it’s going to be like. I still want him to decide, yes. I want to be able to watch Wendy fuck Gary for the first time. Don’t make it seem too hard; just enough to make it a challenge, Rosie.

“Ah, I’m … “ was all he could say at first.

“It’s up to you, Jay.” I said, “How much do you want it? A lot of men get off on it, can you? It’s not just addicting for the cuckoldresses, it’s addicting for most of the cuckolds, too. My dad needs it; that's the best description I can make. He needs it.”

I decided to end it here, with Jay still thinking about it. Thinking about it is good. I think he’ll convince himself, so I won’t have to do it.

“You need to think about it. Wendy is not saying no, not ever, but she is saying, be sure what you want, Jay.” I looked at Wendy and said, “Isn't that right, Wendy?"

She slowly nodded and then said, “Yes, Jay, be sure. It may be a decision you can’t change.”

I left them in the park, talking to each other.

We didn’t talk about the meeting until Monday, when she brought it up. “Um, Rosie, the other day, when we talked to Jay, um, he’s still not sure. He talks about it, and I know he still wants it but … Hell, just but. He can’t make up his mind, but now that he’s made me think about it, I can’t stop.”

She grimaced and then added, “I sometimes think about doing it, fucking Greg, just to get it over.”

“Maybe if I talk to him again, Wendy. Just me and Jay talking, what do you ...