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Today is our” - and by ‘our’ she meant ‘my’ - “anal training day. I’m gradually working Aaron up to accepting larger and larger plugs. He has to hold that plug for thirty minutes before we move on to a slightly wider one.”“It looks like he doesn’t mind too much,” Emma commented, gesturing to my erection sticking up between my bound legs.“No, but he’s not allowed to orgasm during this time. Sometimes the pressure on his prostate will cause him to ejaculate spontaneously, and he’s not punished for that, but he isn’t allowed to otherwise touch or play with himself during the training sessions,” Jess explained. She returned her gaze to Emma. “Now, tell me how things went!”Emma stared at me for another few seconds before returning her attention to Jess. She gave jess a full play-by-play, leaving out no details.“Jess, it was wonderful!” she finished. “I think that...” she said, trailing off.“Yes? You think what?” Jess prompted.“I think I might be falling in love with Brent,” Emma said. She didn’t particularly emphasise still feeling queasy but knowing her well enough, it was probably the case as she normally hides stuff like that quite well.Her traipsing around in sleep shorts didn’t do my case any good either. Look, she is weeks away from fifty and she’s still got it. Slightly greying, she still looks thirty-five, a bit of extra around the hips but still a looker in many ways. She’s not very sexual, not like me, (hell, I am halfway through my fifties and not slowing down yet) but she gets drenched in seconds the moment I enter her. Looking at her, moving around I groaned inward and thought, ‘Toots, I’d love to take advantage of your little body’, you know, said with that smirking expression.Eventually, we announced it was shower time for us; we do it together most of the time except maybe during the week. It’s our time and the opportunity I particularly look forward to as I get to get close to her, skin on skin… and try my luck.I was already semi-hard and rubbed.
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