His asshole looked tight, but glistened with the lube we’d been playing with. I took some more from the jar and gave it a good fingering, getting th... slippery lube deep inside him. He groanedIt was time.I positioned myself behind him and allowed the strap on to slide up and down his crack. Each time it slid over his asshole I pushed a little, until it just slid in. I heard him gasp, then felt him pull away slightly. ‘No’, I said, you stay right there’I pushed forward a little, he was still.. " So you're okay?" Yeah," I wheezed."Are you having another asthma attack?" No," I replied weakly. "He just stepped on my ... um ... well, never mind. I'll be all right. Honest." You're sure?" she said.I tried to sound less like a wuss and again told her I'd be fine."So what's up?" I finally remembered to ask."Oh!" she yipped. "I completely forgot about something and it means we can't go out to eat tonight."Great. This was going to be one of those days.She told me about the chaperone gig and. More

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