Ignoring the parlour visits as a teen that resulted in barely any sex, lots of pointless chatter about kids/horses/prison and questionable hygiene, one of my worst but also memorable meets was with a thirty something milf I'd visited in the valleys. She looked far better than expected (curvy yet tight size 12, 5'5, blue eyes, nice smile) and she said she thought I was attractive too so things started off well. Her house was in a decent area, detached with discrete driveway and although it was full of kids stuff, still clean and her bedroom was nice and welcoming.
The ordeal started when she got hold of my cock. Her oral technique was unbelievably bad. I felt like she was trying to suck my cock straight off, it was bloody painful. After about 10 mins of me biting my lip, I offered to give her oral and that provided a moment of sweet relief. But soon after I'd started she pushed me onto my back, popped on a condom and started riding me. I've never experienced such eye watering grinding in my life. She almost broke my pelvis and can only assume her ex was an absolute unit with a cock cast out of iron. I couldn't see how nobody had told her to slow down and be gentle before. She left me questioning my masculinity.
As I was quite a way away from popping, she asked if I wanted to take off the rubber! I said no, but we could do some oral. I finally came in her mouth and she swallowed (first time for me). I don't know how/where I found her advert but it soon disappeared after that. About 4 months later I received a text from her asking if I wanted a repeat for £40. I declined but I was left feeling that she wasn't a 'proper' jobbing escort and was probably just a single mum needing a little cash. Ignoring the horrific levels of physical pain, I've never had a more natural interaction with a woman I'd paid to have sex with.
