My Smoking Mistress

I am a recently divorced closet sissy with a very successful career that allows me a great deal of freedom to do as I please. About a year ago I discoverd that my now ex-wife had been cheating on me for most of our marriage. Apparently she loved the perks and accoutrements of being in a high income household but hated me and my feminine mannerisms, my smoking and my inability to sexually satisfy her so she ventured out for a man who could give her the hard, deep fuck that my 3 inch erect cock could never provide. She obviously knew all about my pathetic cock from the beginning but I guess she was willing to tolerate my femininity, cigarettes and sexual inadequacy as long as she drove a brand new BMW and could go wild with my credit cards on designer clothes, shoes and handbags. Quite the gold digging bitch as it turns out. Of course I didn’t mind all the designer crap since I had my own secret collection of expensive designer glamwear. In fact I used to masturbate and cum in her hottest high heels all the time and she knew it. I would have divorced me too. Pathetic. She’ll be better and happier without me. Now that she’s gone I can dress as I like around the house and be the smoking sissy faggot I was meant to be. My newfound life as a single sissy faggot has allowed me to visit a trans escort several times a week which has been wonderful. Love worshipping and getting fucked by the magnificent cock on my trans friend! But recently I put out a classified ad offering my services as a sissy maid and I was surprised at the response. Several mainly idle rich divorced women responded and wanted to set up interviews. One of the interviews lasted for three hours as we both tried to gauge our compatibility. She checked all the boxes for me and I for her. She loves feminine sissy males. She smokes, loves fashion and she needed someone to clean her house and be her chauffeur. Moreover she is a kinky rich lady who had been looking for the right opportunity. I was hired at minimum wage, shaved, locked in chastity and made to sign a one year contract of sissy servitude and obedience. After a few months of low intensity getting to know each other, I am now her sissy bitch with the possibility of moving in with her as her full-time live-in bitch. I clean her home on Wednesdays and maintain her huge yard on Saturdays. She summons me for chauffeur duty when she needs me and I am to keep her fully supplied with cigarettes and the condoms she needs for the wild romps she enjoys with her various young studs. Of course Mistress saves the cum-filled condoms for me to consume in her presence which is a huge turn on for me as I used to retrieve used condoms from both my sisters’ wastebaskets after they got their brains fucked out by their hot boyfriends. I do love the taste and texture of a young stud’s creamy release especially with a luscious Virginia Slim 120…god I’m such a faggot. Meanwhile Mistress encourages me to continue my tryst with the aforementioned trans prostitute and eventually wants her to visit the house for a steamy display of filthy gay sissy sex for her erotic entertainment. I look forward to that day. It goes without saying that Mistress has taken hundreds of pictures of me in my sissy state and has them safely stored for future use if necessary including images of me licking her gorgeous vagina and tight pink butthole. Mistress loves having her pussy licked therefore I spend a lot of time on my knees with my head buried between her thighs. When I make her cum she rewards me with a nice strap on session until I sissygasm through my chastity cage. My time with Mistress has not always been perfect as she has taken issue with some of my behaviors for which I was severely punished but overall we are both very happy with our arrangement. To be continued….

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