This past fall, I (38) took my family on a Caribbean cruise. That family included my wife, our kids, and my MIL Anne (61). We spent a week hopping from island to island.
It might be strange to take the MIL, but we had our reasons. We are very close with Anne. She has been divorced since my wife was a teenager. She is so much fun and we love having her around. She’s also a built-in kid watcher.
When I say we are close, this includes the ability to joke about ANY topic. It’s double the fun since she looks like my wife’s older twin and she is super active and very fit. 5’6”, shoulder length brown hair, handful of tits.
We sprung for a fancier suite on this cruise. It was two bedrooms with a small shared living room and a shared larger bathroom. Larger bathroom on a cruise ship means two people can be in it at the same time, though it is still just one large shower stall with a toilet and a vanity.
My wife and I stayed up late catching shows one night. Anne and the kids had gone back to the room. It was late late when we called it a night.
The next morning I was out. The kids were up early so my wife took them to breakfast and then went exploring around the ship. By the time I woke up I assumed I was alone.
I stripped, grabbed my towel, and headed to the common area towards the bathroom. I didn’t know Anne was in the other bedroom preparing to do the same thing.
I brushed my teeth standing naked at the sink before getting in for a long hot shower. I washed and then began to stroke my cock. Something about having a quiet moment to myself made me take advantage of the situation.
I was jerking for a minute when I was startled back to reality by Anne’s little voice. “Leave the water running when you’re done having your fun, I’m getting in after you.”
I could barely see over the top of the curtain. Anne was standing at the vanity wrapped in a towel. That alone was a hot enough picture to keep me going.
But aside from being startled I was also embarrassed that I was caught. She knew I was masturbating.
“Jeez, I didn’t know you were here,” I said. “I can be done.”
I stuck my face back in the water and rinsed my hair again. There was nothing to rinse, I was just buying time for my full erection to go down. I knew I would have to pass Anne with nothing but a towel. I didn’t want to make it weird.
With my head in the water, I heard the shower curtain slide open and Anne step in behind me.
“Don’t move,” she said. I couldn’t if I wanted to. Space was tight and I was frozen not knowing what was about to happen.
Anne’s naked body pressed against me as she reached around and took hold of my cock. I tensed up, but she told me to relax as she began to jerk me off.
I leaned back into her a bit; I could feel her nipples against by back. It was so hot. The hot water ran down the little space between us as she tugged with one hand and massaged my balls with the other.
It was not long before I blew my load on the shower wall.
She released me and I splashed some water to wash my cum down to the drain. I turned and hugged her, sneaking a peak at her tight little body. “You’re welcome,” she said. “No go so I can shower and we will go get breakfast.”
I did as she told me. I got dressed and waited until she finished getting ready. Then we went about the day as normal. We had breakfast together before meeting with the rest of the fam.
We never spoke about it. It didn’t change the nature of our relationship. It just happened, and it was amazing!