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Finally we were able to pick a good night to meet. It was a Friday night, so if things worked out I wouldn't have to worry about work the next day. We had each other's descriptions and to help spot each other we added some detail about what we would be wearing. Claire picked a pub near her place and a little more than a month after we first spoke I headed out to meet her. Claire lived near the Annex south of Bloor St, so it was a simple subway ride from my place over to her neighborhood. The Annex is right near the University of Toronto and it's a pretty active part of town with a great variety of bars and restaurants. Interesting stores too, especially if you count tastefully appointed Honest Ed’s – look it up. I walked into the pub where we were to meet and since it wasn't crowded yet, I presumed Claire would be easy enough to spot. As I walked past the car I noticed a nice looking girl with brown hair a bit past her shoulders. She was sitting at a small table on her own and. Time for afternoon training my sissy, get on hands and knees. Remove the butt plug and it better not be soiled, or there will be punishment. Butt plug is removed and clean, Mistress tells sissy to push back onto the electric dildo. Dildo is now in Mistress tries it and shocks sissies’ prostrate to test reaction. Has sissy put belt on to keep dildo in. Mistress leaves and returns in a few minutes in all black with boots with very high spike heels and breasts bulging out, with the small strap-on, looking absolutely beautiful. Mistress sits and tells sissy to suck her cock all while the dildo is pulsing in sissies’ butt. Mistress changes her cock to a bigger one, sissy is learning to force cock down throat, when gag reflex stops, Mistress gets bigger one. After a couple of hours of practice sissy is able to take a 7” cock into throat without gagging. Mistress then stops the electric dildo, removes the condom from sissies cage, which has a lot of prostrate milk in it. Empties the fluid.
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