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She wound the window down a touch and repeated her question. The small talk through her window lasted a while and didn't seem to mean a great deal until she said it was cold, and asked me if I wanted to hop into the passenger seat. I walked around the car and sat down.It was only then that I got a good look at her. She was attractive and I assumed she was in her mid to late 40's, but what was striking was that she was wearing a two-piece pyjama trousers and top set, and what appeared to be a pair of slippers.Through the small talk, she suddenly asked: "so looking for blokes tonight?".I was somewhat taken aback by the bold question, but answered honestly. "bi, so looking for whatever takes my fancy"."Let's see it then" she replied confidently. "Don't wait to be asked again?" I thought, and I slipped my semi-erect cock out of my tracksuit bottoms. She cracked a subtle smile and took a drag on her vape. "Go on", she instructed.I started to stroke my now hard cock slowly, hoping for some. I start to beg the chat to donate more so I can reach my target, I really wanted to know what it would feel like inside if it felt this good on the outside. After only a few minutes a loud ring sounded out, someone had dropped a large number of tokens and it wasn’t Biggie. It took me over the target and now I had to live up to my promise.I re-lubed the plug with my precum, circled my waiting hole a few times before finding the centre and applying some pressure, I could feel my ring give and the smooth metal tip start to enter. I was somewhat surprised that there was no discomfort, and I pushed a little harder. With maybe the first centimetre in, I started to feel more resistance and realised I was holding my breath and tensing up. Forcing myself to relax I released the air in my lungs, and it came out of my mouth as an elongated moan, without easing up on the plug every movement sent it a little deeper and further inside me.I glanced at the computer, there on screen lay a sexily.
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