My Lucky Sissy

Dear Altairboy:

Well, after two months of no cummies for my sissy rachel, she got very lucky in the month of December.

Let me explain. I am sissy rachel's key holder. My rules for her are very simple. At home she is to wear any one of her sissy outfits or lingerie with high heels and make up in the daytime, and sexy nighties at night. She wears panties 24/7, and I love to add a bra and a garter belt and thigh high stockings just before she leaves for work. It makes my day to see her in tears of embarrassment as she drives off to work. Of course she has to sit to pee at work, because I have her little dickie locked up in her cb2000.

We both love reading the stories on your web site, my rules are designed around the stories posted there. When ever you put a story on line, sissy get's to cummie. Real stories only, evaluations do not count. Some times I giveher a short time limit, some times I make her come to the very edge for hours before her little squirt. Sex is with her own hand only. Sex with me is with her mouth and her fingers. I never touch her little dickie. Her useless penis is one inch soft and four inches long on her best day. She doesn't get hard enough for penetration, and that little thing wouldn't do me any good if she could. Thank god for her great oral skills and our sex toys.

Up untill December, things were going great for me. The stories would come, one or two at a time, then nothing for a couple of months. I missed reading the stories during this period, but watching her frustration as she checked your site twice a day was priceless.

She would do anything I desired, knowing that small infractions would get her a panties down spanking, and a large infraction would void the next story. In December there were so many lovely stories, and so many chances for my sissy to cummie. I ran out of little humiliating ways to let her cum. After every cummie, she has to drink her cum from her condom, or lick up the mess from her hand. When she came the last time, I made her empty her condom on her face and leave it there for her to smell and feel all night.

Now it's 2012, and I am changing the rules. I am going to humiliate her in a major way for every release I let her have. Our little games were very privite untill January 2nd. She was thrilled to find two stoies that day, but before we had a chance to read them, Libby, an old friend stopped by for the first time in a year. Sissy was in her lingerie so she ran upstairs and washed her face, and put her sweats on over her lingerie.

Our friend knew nothing of our chastity life style, but I saw her looking at sissy's attire, and you could see her stockings. Sissy had always been intiminated by Libby, so I decided to start the year off in the most humiliating way I knew.

I called her over to where Libby and I were sitting and asked her who gave her permisssionto wear boys clothes today? She almost fainted when I said take them off. Sissy begged and pleaded for me to let her go to her room. I told her she had just earned a spanking in front of Libby. She took off her top to reveal her lacy bra with bows. Then she dropped her pants and showed Libby her vanity fair panties withthe lace inserts, and a sexy garter and thigh highs. Libby is usually quite shy, but she finally broke down and started pointing and laughing.

After a few minutes of sissy jokes and a lot of laughing, I made her lay across my lap, with her head in Libby's lap, and for the first time ever, I spanked her till she cried. When sissy stood up, I made her show her cb2000 to us. I thought I had humiliated sissy rachel as much as possible untill Libby asked if she could look closer and maybe touch it. She commented on how tiny sissy was and started to touch it. That's all it took, my little sissy humiliated herself even more by cumming all over herself. Then out of habit sissy reached down and licked up the mess. Libby fell out of her seat from laughing so hard.

I sent sissy rachel to put on her pretty pink sissy dress andmake up, while I shared the most intimate details of our sex life with our friend.

I have no idea how I will humiliate her next time. I'm thinking her ex girl friend might like to play along, or maybe the man next door. Whaever, I would really like to have them help me give my sissy the cummie of a life time!!!!

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Page last updated 2012-Jan-14 by: Altairboy@aol.com