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

This encounter was from a post 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 set up a google doc survey to narrow it down to a select few guys which I found amusing. So some of you reading may have partaken in that as well.

We send 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 at a symphony orchestra, and also a mum of 2. I asked her to wear a gown/dress, which she mentioned she’d packed for a separate event, to the hotel bar for our drinks 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, do the usual ‘are you an axe murderer? No I prefer cyanide poisoning’ thing over drinks at the hotel and then upstairs to her room for the evening.

We had expressed a few things we each liked over text beforehand but we were both comfortable enough to vocalize throughout the events as well but I won’t go into all the details. The room looked out over Bloor and 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.