Thru high school I had several girlfriends for varying amounts of time and a number of single dates. I wasnt the class stud but did manage to get laid...occasionally. I also had my first sex with an older woman. Near the beginning of my sophomore year, Mrs. Brown, my homeroom and English teacher caught me and a girl making out in an out of the way spot behind the building at lunch. The girl had my cock out, in her hand as she jacked me off while we kissed. Mrs. Brown ordered us to come to her. She looked stunning in a short denim skirt with a tight top, showing plenty of leg and cleavage, and knee-length black boots. She looked so hot I could have happily bent her over the table there and then!When Tom arrived I could tell he liked what he saw. We all had a few drinks and then left for our place. When we got home Rachel went upstairs to freshen up whilst I poured us all some drinks and put on some music.When Rachel came down Tom and I were happily chatting when she turned the music. Danna stepped into the hallway. Bill sent a sub-vocal message to Dewey to have a salad waiting at the cafeteria for him."Bill Jenkins," Hobson rarely called him sub-vocally at school. "I have two messages for you." Go ahead Hobson." Peter Elway, the boss at the sheep ranch wants to speak with you." Hobson paused waiting for a response."Is he free now?" Elway's brood had seven dependents at the school. "Second message please, Hobson." Danna has asked for after hour tutoring times." I'll see her. Then Timal and I placed a wildly struggling Chloe into the pillory and curved her round bottom as taut as possible. Timal picked up the strap so I fetched the Number 2 rod.We took up positions on either side.„Start at the top,“ I advised, „work down...then back up again. Take it slowly.“ Those second ten strokes were going to be the purest agony for young Chloe. Timal swung up.THWWWAACCCCKKKK! The heavy leather tawse cracked loudly across the naked bottom.A second later, my cane came down and.
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