I’ve learned from my previous 2 week ban and won’t be attaching a pic to this post but have included one on my profile.

This encounter was from a post that I reached out to. A little older than my usual range at 38, but I’d never been with a self described ‘cougar’ and found the idea intriguing.

Travelling from out of town for a week and staying in a hotel in Yorkville the stage was set for an evening of fun. I believe she had so many offers she created a google doc survey to narrow down to a select few guys which I found amusing. So some of you reading this may have partaken in that as well.

We sent a few pics back and forth early on to confirm attraction - she had a petite frame which I liked. A sophisticated, glamorous looking woman, the type you might see attending a symphony orchestra, and also a mum of 2. I asked her to wear a gown/dress (she mentioned she’d packed for a separate event) to the hotel, which she obliged… and surprised me by also wearing a butt plug.

We had decided in relative terms how the evening was going to go. We’d do the usual ‘Are you an axe murderer? No, I prefer cyanide poisoning’ conversation over drinks, and then upstairs to her room for the evening.

We’d expressed a few kinks we each liked over text beforehand and were both comfortable enough to vocalize them throughout the events as well which added to the experience, although I won’t bother going into all the details. The room looked out over Bloor, at one point we were getting into things in doggy with the curtains fully drawn open and a view of about 40 units looking directly into our room from across the street.

This woman ended up being very submissive, took direction well and, in her words, really enjoyed herself. Not sure if she’ll share everything she did with her husband but maybe that’s their thing. Once we were both finished we said our goodbyes and I left - Good, clean-ish, safe fun.