I (F37) played with my boss (M66) in exchange for a cruise, and hubby (M38) watched…

NSFWAge Gap

Ex boss that I had never actually met before (online job) kept trying to get me to go on a cruise with him. To politely decline his advances, I’d always say, “only if my husband can go to.” However, one day he said ok.

I kinda jokingly brought it up to hubby and he was shockingly interested. He just said, “as long as you don’t have sex with him.” I was shocked and at this time had to decide if I really wanted to go through with it. After a couple weeks of negotiating we settled on an arrangement and after a couple months of planning and anticipation it was time to go.

Basically we agreed to a girlfriend type arrangement starting at dinner time through the next morning with oral once per day and sleeping in just my panties.

Knew it would be awkward anyway but didn’t plan on hubby sleeping on a pull down bed basically over our bed

We met for the first time in the cruise terminal in Miami. Everything went pretty much as anticipated only he was pretty handsy at dinner and made a point to tell anyone who would listen about the arrangement

It’s still something we don’t regret and are considering doing it again. (Already have)

Posted Sep 12, 2026, 9:31 PM UTC

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