As she lubed up her plastic cock she looked directly into Tim's eyes. She could see the fear in his eyes building and she loved it! "Spread your legs ...ice and wide for me baby."She took a glob of lube and smeared it on Tim's asshole. "Ready baby?" Its okay baby, just relax your ass and it won't hurt. If you clench up it is going to hurt a lot."Nancy positioned the head of the strap-on at the opening of Tim's asshole and started to firmly apply pressure. Slowly the head of the strap-on started. I sat in front of his desk trying not to piss myself in terror."Is Jeff Stevens your boyfriend Alyssa?"I looked at him and nodded slowly. There was no rule about having a boyfriend. Only about immoral conduct. The only time Jeff and I had had sex was off school campus."I intercepted this note Alyssa. Why don't you read the highlighted part for me." I took the note, and read the lines silently."Out loud please Alyssa." Alyssa, I love you so much and I think about you all the time. I count the. Then he said there were 2 very serious failings I had which must be addressed , but first asmidnight had come and gone he could now and wanted ; to whip me again , he leapt out ofbed and the room ,returning with a medium weight cat , saying that as I still looked sore onthe shoulders I would only suffer 25 strokes at half power. Even though each lash seemed tojust caress my back ; the pain was reawakened making me twist and squirm ; thankfully itdid not last long , after stroking me over my. Icarefully removed my clothing down to the corset, hose and shoes andwaited for my escort to unlace the corset so that it could be alsoremoved. "you have had the corset on for some time, so I will onlyloosen it so that you can adjust to the change in support. If I releaseit suddenly, it will cause you great distress. When I finish, thenrelease the latches on your shoes. When you are ready, remove your shoesand hose and I will then release the clasps on the corset." As she didso, I could.