Hello, I am a 20-year-old male and am going to relate an event that happened six years ago that totally changed my life and lifestyle. I am sitting here in a chair with my step-aunt sitting behind me urging me on (in more ways than one)...but I digress.
My father has a job that takes him out of the country on business quite often and he normally takes my step-mother with him, which used to have them leave me with my step-aunt. When I was fourteen (and she twenty) is when my story begins. Lana was quite the looker (and still is) but it was thought that she related to other women only and had nothing to do with men. Even so, I found her very sexy and she was nice enough to me when I was in her charge. She seemed to think nothing of going around the house in her skimpy babydoll pyjamas which drove me wild as she has a fantastic ass, long lovely legs and quite large breasts.
One day when she was out of the house, I got the strange urge to try on her babydoll pyjamas to see how they looked and felt on me. Wow, total turn-on and I was prancing about the house in a state of extreme arousal when all of a sudden she appeared, much to my shock. I tried to run out of the room but she had me blocked and asked me what I was up to. I tried to tell her that I was only seeing how they felt but she; now with a grin on her face; told me that she could see that I enjoyed wearing them. She asked if I liked being a sissy to which I could only stammer that I was sorry and it wouldn't happen again. Nonsense, was her reply and said that I looked darling but needed further help to complete the image.
She then had me sit down and applied makeup to my face and then put one of her wigs on me and a pair of pink fuzzy scuff slippers. This only made my apparent erection more obvious to me and whereupon she indicated that my big 'clitty' needed some attention. She then stripped down to her panties only, exposing those lovely big-nippled breasts to my gaze and told me to lie down on her bed and she would take good care of her Jeanette (the name she gave me).
She bent over me on the bed allowing me access to her breasts which I reached for and managed to get one of them in my mouth. Her hands immediately found the bulge in her pyjama panties and started slowly rubbing it in an up and down motion causing pre-cum to flow freely from the tip. All the while she was softly urging her sissy girl to cum for her. Once her other hand found my balls I could stand no more and completely soaked her panties with my juice. She then lay on top of me and ground her panty covered mound against my thigh until she screamed in delight with an orgasm. We then cleaned up and put on fresh lingerie for the rest of the evening and later that night slept in the same bed with our legs intertwined.
From that day on, whenever I stayed with her, I was her Jeanette and was clothed in nothing but feminine clothes. We had many more episodes over the next six years which brings me to the current moment.
She is now behind me; nibbling on my neck; with one of her hands rubbing my panty-covered erection and the other lightly pinching my bra-covered nipples; telling Jeanette to hurry and finish so that she can see me cum for her once again. I must go now as I am close to another shattering orgasm. I will tell of more adventures in other postings.....Ohhhhhh!