I actually kind of enjoyed the experience especially when he came inside my bum hole, which didn’t take him very long. I had mentioned to Ted a couple of times it was something I was keen to try again and he made it clear it wouldn't be with him.So when we were next on a Caribbean holiday after I had experienced my first anal I thought it would provide a good opportunity for me to find someone willing to “scratch my itch” so to speak. We had experienced some rather fun moments on previous Caribbean holidays and there seemed to be no difficulty in finding nice young local guys who were more than willing to satisfy the urges of a 50 plus slightly overweight tourist.I had told Ted what I was up to and he was all for it. I also told him I wanted to see if I could arrange it myself as he had always arranged, or rather engineered, meetings on previous occasions. A few days into the holiday and feeling nicely relaxed I had identified a couple of possible candidates amongst the pool bar. She supposed that whilst they lived with her, she always would. She knew Suzy had been sexually active for a while, and trusted that she played safe. Tom had been going out with a girl for a while, but Elaine wasn’t exactly her number one fan. She supposed it would be difficult to accept anyone was good enough for her boy. Tuesdays and Thursdays were Elaine’s days off work, and those were the days when she’d sort out the washing, and more often than not, sit in front of the computer for a couple of hours. She’d soon strip to her panties behind closed blinds, and rub her clit through the fabric of her underwear. She’d then find a webcam she liked the look of, and arrange a private session. She’d tell the girl what she wanted to see her doing to herself, and would mimic the action on screen. She particularly liked watching them push their fingers slowly into their anus. Elaine loved anal, probably because that was what Paul liked.
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