” I knew I was asking for the impossible, but it was worth a try.“Right, the first stroke coming right up.”I placed the cane in the middle of her bottom. At this point, you could cut the atmosphere with a knife. I lifted the cane and delivered a firm stroke right in the centre of Pippa’s bottom. Her head jerked up and she stamped her foot.“One, sir,” I heard Fiona announce.“Now you know what to expect. You have five more to come in this session. Prepare yourself and push your bottom up again.”“Yes, sir, thank you, sir.”I chose to ignore that I had asked her not to speak.Strokes two to five proceeded, Fiona kept count and Pippa managed to take her punishment well. Each stroke produced foot stamping and wriggling with various “oohs” and “arrrs” but she did remain in position and kept her bottom pushed out.For the final stroke, I decided to deliver this at the sensitive point where thighs meet the bottom.“After this stroke, remain in position until I ask you to stand.”I tapped the cane. “So tell me about your gay fantasy when you masturbate?” He asked.With that, I explained my two gay fantasies and as I did I could feel my cock getting firmer.As I finished, he leaned forward and kissed me on the lips. I froze for a moment and then leaned in again for a second longer kiss. As we kissed, Jack rubbed my thigh and let his hand brush against my groin where he found my hard cock.“Jack, I want to see you naked,” I said boldly.“OK, let’s get out of here,” He said at the same time as he stood, taking hold of my hand and helping me out of my seat.As we headed outside I asked Jack, “would you like to come back to my hotel?”He said that would be great as he still lived at home with his parents.I let us into the room and turned on the bed side lamps. I turned around and we kissed again. I stroked Jack’s bum through his chinos. As I did this my cock began to regain its full stiffness and I pushed it against Jack so he knew I was hard. I could not wait to get Jack naked, so I.
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