Unexpected [MFM] from a Craigslist hookup many years ago

This origins of this encounter go back a while and I don’t really want to bore you with the details (at least not this early on). Put simply, I had been broken up with and I had a lot of demands that I wanted met for my own personal gratification before I could commit to another relationship. This is the story of one such instance.

I had swapped emails with what I assumed (correctly) was a woman on the now defunct Craig’s List personals. She was looking for a guy. I could tell by the word choices that she was a real person. She used the word groovy once… that pretty much sealed the deal for me. We met, had quality sex and when I was cleaning up, I noticed she had some other condoms in the bathroom trashcan. When I came out of the shower, I asked how many others had accepted her invitation. She said it had been “worth her efforts.”

“Why not call one of them, see if they’re not too busy,” I said. I had wanted a threesome, but instead of with two women, I wanted it a woman and another man. There were certain things that two men can do that two women simply cannot.

Pegging and anal fun with [M]y wi[F]e last weekend

When she told me she had something new in the plans for this weekend, I already knew what she had in mind. I saw the box on the stoop, I noticed that she closed the bathroom door for longer periods of time in the mornings. I just couldn’t let my anticipation show, otherwise she might not be as excited.

Friday night rolled around and after dinner we were sitting on the couch having a drink when she brought it up.

“I have something to show you,” she said.

I nodded. I didn’t want to tell her that I could see the outline on her dress.

She stood up in front of me and pulled her dress up, revealing a purple strap-on. It looked remarkably like my penis, except that mine isn’t purple. “What do you think,” she asked me.

“Looks good,” I said. “How do you feel wearing it?”

“I can understand why you like having yours so much,” she said.

She continued standing in front of me for a few moments.

“What are you waiting for,” she asked.

I sat back.