A Cuckold's Pleasure - Her Love - Sex Stories

A Cuckold's Pleasure - Her Love

Helen and I are both in our seventies now, and we’ve been married for well over forty years. I’ve been Helen's cuckold for most of them. I’ve been following KeylimePi’s stories since he started posting the Cuckolder Stories.

I thought a lot of them were hot, but they missed why I’m a cuckold and still married. I want to share my experiences as her cuckold and my reasons for staying married to her.

It was my thirtieth birthday, the first time she made me a cuckold. I’d talked to her about it for a couple of years, and as usually happens, she’d turned me down flat. We’d talked about it again, and we even role-played it a few times, but nothing beyond that.

First lover

That lasted until one time we were in Santa Barbara for my birthday. We were at a resort on the ocean where we could hear the waves as they crashed on the rocks near the outdoor bar. We were sitting there, enjoying the waves, and I’d just made a comment about strange lovers, testing to see if some hot roll-play might be interesting, when I had to use the men’s room. On the way back, I saw a guy standing by Helen, talking to her. I stepped back out of sight, looking at them. She finally asked him to sit down at our table and continued to talk to him. This was a script we’d used before in our roll-playing, where I was away from her table and a guy came by, hitting on her. She’d pretend to get a text message from her mom, telling her to have a good time at the resort.

I decided I wanted to get Helen ...

... started on the script. So I texted her.

Hi darling, This is your mother telling you to let loose, and if you can, take him to our room. I want you to enjoy him there. Yes, that way! When he leaves, text me.

I saw her look at her phone, and she tried not to look for me. She read the text again, then texted me back.

You’re sure. You want me to go all the way with him? All, all the way? The way we pretended I did last month?

I sent back some heart emojis, along with an explosion one.

Is this the time Helen goes for it? I can’t believe it’s going to happen. My heart was in my throat, and my hands were trembling. I could feel sweat on my forehead, and my cock was tenting my trousers. This is what cuckolds talk about. The excitement and the dread at the same time.

I moved to the bar, where I could watch. She ordered a glass of white wine, and he ordered something like a whisky. Luckily, I’d left before we’d ordered drinks, so there was no sign of me there.

I could tell he was hitting on her, but it didn't turn her off. I could make out a few words, like kiss you, just before he leaned over and kissed her. Then he moved his chair, so he was sitting closer to her. He was making progress because I could see the slight flush she gets.

He took her hand and said something to her that made her shake her head no. I could lip-read, “Not yet.” Okay, he’s still making progress. He was holding her hand and giving her some kisses. After a half hour, I could tell he said ...