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We met via mutual friends, hung out at parties and at home. Angela is in every way your typical young women next door. A bit on the chubby side, blonde hair at shoulder length, always properly and modestly dressed. Everybody would agree she had the cutest smile on her pretty face. And for me it was certainly that pretty face that drew me to her. She just always had that little look in her eyes that seemed to tell me she could be into me. But I could never fix that gaze, as she would quickly look away or do something goofy when I tried to fix it. So I let it go.One night I was talking about her with my wife when she said, "Angela is into you, I can tell. I've seen her look at you. You should try and ask her over one night." Now this may seem strange to you, but as I said before, we live a very open sex life. Now I have several girlfriends that I see, but making a move on Angela was very hard, because she was so casual. Other girls send out very clear messages, but Angela only had that. A rather large butt-plug was clearly visible sticking from my ass and a ball-gag completed the ensemble.“Um, am I interrupting something?” Emma asked. Jess seemed legitimately confused before following her gaze to me on the floor.“Huh? Oh! Nope, not at all. 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.
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