Today being the second day of Sally and my adventure, I sat up exhausted by the evening - tired from cleaning her home, washing, ironing and setting her clothes, doing the dishes. The maid uniform now a tad heavy to carry.
Mistress Sally had just sent a text, "go fetch and use the things in the kitchen right cabinet. Make sure you've used them all by the time I return. Coming back by 8. Keep dinner ready. We're going out tonight." Excitedly, I race to the cabinet, only to find KY jelly, condoms and a regular sized gherkin. It had a post-it note reading, "for your practice today". Weirdly I did get excited at the thought of being instructed to violate myself. I took the three things, and headed to the guest bedroom. Heading back to Sally's bedroom for her laptop, I started the little film she had prepared of pleasuring herself, which she made me watch as she penetrated me with her strap on the previous night. Today was a substitute to her instructed daily fuck.
Setting the laptop on the bed, I undressed completely, and knelt on my knees on the floor along the bedside. Putting the condom on the gherkin, I got a serious erection. Lubed up my backdoor. Got ready for what was to come. As I started watching the video, I slowly gathered the courage to push the already placed thing into my butt. Slowly it went in. Excessively painful. Continued for a while, until I felt exhilarated.
After this was done, already 730pm, i quickly cleaned up and got ready to get some food. Set up the table as she was about to reach home. Suddenly realized I'm in regular guy clothes. Quickly changed into a long frilled skirt and T-back. Added a golden bracelet as a final touch. Then rang the bell. Sally's home. Delighted to see the house clean, she gave an affectionate peck, and whispered in my ear "good girl". We quickly had dinner, changed into normal clothes and then we headed out to town for a drink. Her friend Pooja was meeting us. As we drove there, Sally gave a brief introduction about her and the yearly appraisal that was to come up. Turns out Pooja was Sally's manager and had been given a hint of Sally and my arrangement, and that Sally could lend her 'bitch' to pooja for a while, in turn off a good job rating.
Sally urged if I would be good enough to give Pooja a good time. Would be helpful in her annual review. I said will think about it.
Meeting Pooja over drinks was not fun. She seemed an up nosed aggressive and socially awkward single woman. And was she tall. Dressed in her business suit, I figured she'd just returned from work.