My daughter has a professor who is being extra hard on her, and not in a good way. My daughter does not do D’s, unless we are talking cup size. So, I arranged a meeting with him. Now, I know my baby girl is all grown up and can fight her own battles, but I am a cougar in every sense. I am very protective of my cubs. When I was meeting with Professor Allen, I noticed he couldn’t take his eyes off me. I wondered if he liked his women mature. I crossed and uncrossed my legs several times, dangled my heel; and his gaze never left my lower half. He was not looking at my face or even my breasts. I accidently on purpose dropped something, and he rushed over to pick it up for me, and he started salivating at my pantyhose. I knew what kinda guy I had here.
I invited him back to my place to discuss my daughter’s progress more intimately. He jumped at the chance. Once there, I showed him my closet. I knew to a man like this, my big walk in closest filled with shoes, pantyhose, sexy lingerie and clothes, would be a sissy’s paradise. I encouraged him to dress up, even said I would help make him a pretty girl just like me. His pecker sprung to life when I said that. We talked about my daughter as we played dress up. I had him put on a pretty pink panty and bra set, a garter belt and stockings and one of my black suits. I even gave him a pair of sexy heels and a wig. I made him model for me. He was in sissy heaven. I snapped a few pics of him and told him he could be my sister. He loved that. We did look alike.
I poured some wine and kept pouring it as we talked about being pretty girls. Told him I could always use a new sissy to play with. The drunker he got, the more fun I had teasing him, well now, her. I gave her a little basket and had her skip through my house. I had her give me a pedicure. I then had her rub her little clitty for me. I explained she had a clit stick and it belonged always in panties. I gave her a big stack of pretty panties and explained that she was only allowed to wear panties while teaching. Of course I snapped more and more pics. She got so drunk, I had to drive her home.
The next day, when Professor Allen came back to my place to get his car, I showed him all the pics of him dressed like me. I asked him if he was wearing my panties and he pulled down his dress slacks and revealed a pretty pink pair with little flowers on them. I told him that he was a good sissy boy. I was actually quite surprised that in his drunken stupor, he remembered to wear the panties. I then informed him, he could continue to be my pet sissy boy and all these photos would stay with me as long as she passed my daughter with As in her class. I explained that my daughter would have a set of all these pics so she could upload them on the campus server for all the students and faculty to see if she got anything less than a B on any paper, quiz or test. I even said we could all play together too when I visit my daughter. The funny thing is, she didn’t care that I was blackmailing her. All she cared about was that she could be my sissy forever and ever and ever. And that I would fuck her pretty ass with the strap-on she spied in my closet. Turns out this was gonna be a win win situation. I get a great new sissy boy to play and shop with; and my daughter gets to not stress about abnormal psychology. And, my daughter has her own private sissy boy as her bitch at school, because what is mine is hers, even a sissy bitch.
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