Three times, but not in years. Pre-covid. I think the lockdowns, job-losses and increase in the cost of living sparked a lot of people to start offering more with their at-home massage businesses, and also generally raise prices. I jumped into this stuff around 2017, looking for legit massage at an affordable price and without having to wait a week or more for an appointment. So I tried craigslist and Kijiji. Back then, people did actually advertise legit massage a lot, not SW. Nowadays, I'd say over 90% of legit-looking ads (that aren't on LL or other such sites) are SW. Back then it was the other way around. It was a side-hustle or a stay-at-home-mom job.
Two of the experiences I had were older women, both single. Both did nails, facials etc as well as massage. A home spa.
I saw one of them about 5 times before she started dating somebody, so that was the end of that, but we had a ton of fun during that time (everything but FS). The second I saw twice, she just wasn't my type or very attractive to me but she was fun. That lady, she told me she was happily single but she used this as her way of getting her sexual excitement if she found the guy attractive. She was pretty open and honest, lol. She got off on rubbing men's bodies, and if she got a reaction she'd go further. If not, she'd get herself off after the session when he was gone.
The one I saw 5 times, she was pretty awesome. Maybe late 40's, early 50's, curvy mom-bod, looked like anybody's next door neighbour. First session was like a scripted home-made "reality" porn lol. Normal massage on the back, lots of talking, when I flipped and she started doing my front, she stopped all chit chat. When she moved the towel off my thigh to do my legs, I popped out and I expected her to re-cover me, but she didn't. So she spent a lot of time on my thigh... I opened my eyes a few times, and each time she was staring directly at it. Like I said, it was like a bad home-made porn lol. So after a while of this, I just went for it - something I'd never normally do - and moved my hand down slowly. Figured if she stopped what she was doing or said something, I could play it off as adjusting or re-covering myself, but she kept massaging my thigh, so... I just started stroking myself. And she didn't stop rubbing my thigh, wohoo! Eventually she took over, starting on my balls while I was still handling myself then I took my hand away and she took over completely. So I started fondling her ass and back of her thigh. She switched hands and stuck the other down her pants and we both finished and it was awesome lol.
Texted her later that day to say thanks and all that, and she started chatting with me. Told me the second I left, she went and got her dildo and had a good old time lol. I was like holy shit, bingo! Made a second appointment right there, for a week or so later.
Showed up for that one and she answered the door wearing a tshirt with no bra. Normal massage on the back, no teasing or brushing, and when I flipped it became more sensual. She took her top off AND her pants, angled herself towards my face with one leg on the table, and the next 20 minutes were a blur.
Had 3 more appointments with her, 2 similar, the last was just a basic massage and HE, nothing else. Next appointment I tried to make with her, she told me she had started seeing someone and it was serious, so no more "fun"
Never saw her advertise again after that
