Rosie Helps Wendy - Sex Stories

Rosie Helps Wendy

... your mind. If you say no, that means you can’t bring it up again, period. If you say yes, my guess is that Wendy will take your permission and run with it. Well, not run with it, but rather fuck with it.”

“Yeah, she’s made it clear what she wants. I want you to say yes because I want to see her from the outside having climaxes or orgasms. I want to really see it happening with me watching. But it’s scary too.”

He stopped talking, trying to think. He shrugged his shoulders and continued,” You’ve seen it? You've seen it when a guy is cuckolded for the first time? The very first time, when they saw it happen?”

If he only knew that I had when I’d cuckolded Jason. I’d seen it up close and personal. That first time with Ted, I can still feel his cock as it took me that first time. The wonderful feeling that I was on top of the world as I felt him on top of me with his cock releasing the essence of sex inside me. Yes, I’ve seen it happen for the first time.

“Yes, I have; once at least, the husband loved it and I’ve heard that they are still doing it. But it depends on both the wife and husband if they can come to a balance between the two of them.”

“You’ve seen the first time a guy was cucked, cuckolded?” Jay said, “How the hell did that happen where a guy let someone else watch?”

"Well, the opportunity doesn’t come often, but it does happen. Um, Wendy kind of promised that I’ll be able to watch you the first time.”

I looked him in the eye and said, "So, are ...

... you ready to leap? Are you ready to let Wendy take trips off the reservation? She wants to know. She told me to tell you that if you say yes, it’s not a one-time thing. If you say no, she doesn’t want to hear about it again. ”

I can see the agony he’s going through. Ha, I know what he’s going to decide, but I love seeing his indecision. I’ve seen cuckolds going through the same pain as they’re trying to decide to let their wives have fun. I want to prolong it, but that’s not fair to Wendy.

“Do you want to see Greg undress Wendy? Can you picture Wendy undressing Greg so he can fuck her? Look and watch as he’s playing with her tits and cunt, getting her ready. You’re going to have your hand on your cock when his cock slowly penetrates her cunt; you're going to cum when you see him cum in her, aren’t you? You want it, don’t you? Just tell her. Tell her that you want to watch. Well, if she agrees, at least. Maybe she won’t let you watch.”

I glared at him before saying, “I’m tired of your indecision, and so is Wendy. I want to see you watching Wendy’s first time cuckolding you. So just tell her. Tell her you’re releasing her from her vows of faithfulness. From now on, she can fuck anyone she wants without worrying about you.”

He couldn’t look at me. I could see him trembling as he tried to respond. Instead, he got in his car and left. About an hour later, I got a text from Wendy.

God, Rosie, what did you say to him? He’s already called Greg, and Greg is going to be ...