Review: Cherish O'Riley

General Details

I really appreciate spending time with mature women who have the confidence to dress very sexy when they go out for a date to a nice restaurant, show etc. It's great to be with a woman who tastefully pushes her wardrobe to the limit by wearing a short, tight dress, stilettos, and thigh high stockings or something just as sexy. I like being with a date that turns heads when she walks in a room, knowing full well that we'll be exploring our own erotic adventures later that evening. I've been with Cherish a few times in the past and she's fully aware how I like her to dress for our dates. She's never disappointed. This time though, I decided to take the initiative and shared with her a couple of looks I wanted to see her wear during our upcoming date. I like the faux leather, wet look skin tight leggings look on a woman and asked Cherish to order a pair from a catalogue I shared with her. We intended to head to a club after dinner where erotic club wear is encouraged so I asked her to pick up a short, skin tight wet look dress from the same catalogue for her to model along with her black thigh highs and stilettos. Cherish ordered both items and let me know how hot they looked on her. I knew she was looking forward to wearing these looks. I think a lot of woman really like it when men take a real interest in dressing them. And I also think some women don't realize how hot they look and how sexy they'll feel when they wear hot looking things that tastefully push their wardrobe boundaries.

I scheduled an all night date with Cherish. We planned to meet in the hotel bar early in the evening, have a drink to catch up on things, head to the room for an hour and a half to get better acquainted before dinner, have dinner, head to a club for a drink before we headed back to the room for a night of erotic activities.

When I walked into the hotel bar, I was blown away as to how hot Cherish looked in those skintight faux leather leggings with her stilettos and hot purple top (no bra of course). She looked very classy, with a healthy dose of "really hot", just enough to to attract everyone's interest. I realized I needed to spend some "quality time" with Cherish before our dinner plans at a great steakhouse so we headed to the room.