I was never a sissy but my third session was close when I was a 20 yr old college kid with little cash and my first Mistress, a true 48 or 50 year old MILF, took pity on me. So the third time I saw her I was a house slave. Well, a "Roman bath slave." The Mistress suggested I go to her apartment and wear the loin cloth made of rags I had for my first two sessions. I got there 7:30 am or so, showed me where the bathroom was. I was told to put on my loin cloth, run a bubble bath and wait their for her to return. I did as told and she returned in a white robe, slipped it off and she was nude. I helped her into the tub, took my time bathing her, and dryed her off. It was glorious and my arousal was evident. She told me to clean up the tub, dry off and get to her bedroom to help dress her.
What I found out was that dressing a Mistress is as big a turn on as watching a Mistress undress. When I completed my task, and seeing my situation, I was ordered to pleasure myself with her foot nearby for me to worship. Then there was a quick, "CLEAN UP, GET DRESSED AND MEET ME INSIDE." I did, she showed me to the kitchen to make her coffee and and serve muffin or something. When I was serving her coffee - she never asked me to have any - she said, "When do you have to go to class?" She grinned and added, "I want you to meet my maid." I had a job interview before class, I said I had to leave soon. Disappointed, but understanding, she wished me luck and I left. As I walked to down the hall and saw someone got off the elevator from a distance. Looked like a tall thin middle-aged woman. As the person got closer and closer it was evident the person was a guy dressed, in a sophisticated manner, in drag. I did a double take, we passed each other and I got to the elevator and took a look back. The lady must've been the Mistress' maid because she knocked on her door.
Relatively innocent about BDSM at that point, crossdressing for sure, I was completely spooked, thinking if the Mistress had something in mind for me to do when the maid arrived. Immediate fear gripped me. I dropped out of the scene for several years after that, my precious 20 year old male ego couldn't process what I was thinking what might have happened if I had stayed. LOL!
