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She stopped me briefly to let me know that she had never had anal sex before so if that was my plan, I needed to take my time and be very gentle with her. It was an unexpected invitation and it drove me crazy but I slowed down and lubed her ass with my tongue while rubbing my wet fingers on her clit. Her body was heaving with pleasure and I finally moved upright and gently pressed my stiff cock against her extremely tight little hole. I spit in my hand and rubbed the wetness over the head of my cock and then pressed a little firmer. She kept moaning ‘Gentle’ and I took my time working the head of my cock into her. It seemed to take forever and I could tell it was a pain and pleasure experience for her. But I went slow not wanting to hurt her for her first anal experience. I leaned down to kiss her and my 8” cock popped in almost half-way. She was wiggling and moaning loudly and I wasn’t sure if it was hurting or pleasing her but I continued to work it in further so slowly. The grip. I certainly was not going to wear the mules or the babydoll! I didn't know what else to do though. Ok, no laughing, but eventually I found a pair of denim shorts with a large pink star on the butt. To this I added my barely serviceable wing tips. In addition I carried the change purse Stephanie had given me. My nails were clear, but long. My hair was platinum blond. I probably should have just bitten the bullet and worn a dress, but I had to draw the line somewhere. That evening Stephanie made me hop, skip, jump, pivot, dance, stand on one leg, and anything else she could think of. I passed, barely. "I'll give you a passing grade, but you need a lot of work. From now on, you will wear heels all the time. The higher the better." Then, for spite, she made me dust her (formerly my) office while she watched. I lost the office when I lost my job. Now she had the key and I was only allowed in under supervision. "You have very sexy legs. Those slippers are very sexy on.