I am very pleased at how jemima is developing into a perfect sissymaid. As I reported in my last blog, I am currently training her in her bedroom duties as my playgirl.
I recently purchased a double dildo strap-on, which I tried out with her a week or two ago. I was a little disappointed because of her constant moving about. I therefore decided to try it this time with her in restraints.
Before the session began, she had a nice cleansing enema and I applied some exotic smelling body lotion to her skin. I left her to put on her make-up and wig and had her dress in her pretty black corset and stockings. She looked delightful.
I led her into my bedroom and she dutifully dropped to her knees before me and gazed up whilst slowly licking the large strap-on dildo. As she took it into her mouth, her pretty painted lips stretched wide and left lipstick on the black rubber shaft. I could see her gagging a little as she did her best to deep throat the dildo.
I guided her to my bed and told her to kneel on all fours. Binding her wrists together, I brought her arms through her thighs and secured her bound wrists to her ankles. In this position, her bottom poked up provocatively. To add a finishing touch, I secured a penis gag to her mouth.
It was a little tight trying to enter her, but the pressure on my inner dildo brought me great pleasure. After a little while she seemed to relax more and was able to accommodate the entire shaft. Pumping away, the inner dildo inside my pussy was really turning me on and the action became more and more frenzied. I noticed that jemima was leaking from her little cage, encouraging more to pound her tight sissyhole.
I am not sure how long the session lasted, but by the end of it, I was covered in a sheen of perspiration. I removed jemima's gag and left my strap-on under her face telling her to lick my juices off the inner dildo. Leaving her restrained I took a long soak in my bath.
I returned to my bedroom and released jemima, telling her to clean herself in my bath water.
She can certainly now say that she is no longer a sissy virgin.