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Another bit of weirdness.The machine immediately picked out a blank and the kid fetched it from a rack and stuck it into the slot. As the machine cut it, I made a joke about the sound reminding me of a cavity being filled. That struck a chord with the kid, who went on about how he hates having cavities filled, and the sound of the drill on his teeth, the vibration traveling from the bone into his skull, and if it weren’t for the Novocain, how bad would that hurt?The machine finished cutting. He now had to insert it into a different slot where it would be smoothed and any filings removed by a revolving wire brush. While he was doing that, I asked him which of the three local high schools he was attending. He told me, and as we chitchatted he mentioned he was 18, and a senior, and already applying to colleges for admissions.He removed the key from the slot and searched for one of those small, white paper bags to put it in. As he did that, I told him to have fun at college. And, looking. "You're still learning, slut, so we won't go too rough on you tonight. Do a good job and we can teach you more. If you use your safeword for a break, we might not invite you back." Daddy was stern, and it made me want to please him more. I heard a condom wrapper being ripped open behind me, and I moaned as Daddy held his grip tightly. "Yes Daddy, thank you Daddy..." I whimpered. I was nervous, but so excited, more turned on than I'd been in a long time. At that moment, I hoped I would be allowed to come back for more. I felt Sir's hands on my hips, his cock pressing against my loosened sissy hole as he knelt behind my bound form. Without anywhere to go, I took inch by inch as he took my sissy virginity. Already stretched and practiced, there wasn't much discomfort, just pressure and fullness as he went deeper. I held my breath as I was impaled, realizing that I had a real cock in me, panting again like a bitch. Soon it was all the way in, Sir using my hips to hold my ass close to him.
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