My sister and I had never had a calm relationship. She was my parents' favorite. Always pretty from an early age, she blossomed into a true beauty. By the time we reached high school (she's a year older than I), she was the most popular among the 'in' crowd. A champion cheerleader, with her classically beautiful face, long flowing brown hair, and perfect body, Sarah was destined to be voted 'Best Looking'. All of this attention and ego stroking, however, made her a real bitch. I was painfully shy and extremely introverted. Sarah constantly teased me, saying that I was a wimp, that I would never get a date, and that I was probably a 'fag'.
In the pain and confusion of my adolescence, I turned to cross-dressing as a release. By the time I was eighteen, I was proficient enough at dressing up that I could probably pass for a real woman. During my teens, I spent hours in my bedroom, dressed in silky panties and thigh high hose, masturbating. My fantasies ran the gamut from being seduced and dominated by a powerful man to being humiliated by a true dominatrix. These were the dreams that got me off, and these fantasies were a lot better than the two real life sexual experiences I had. They both involved a chubby, near sighted neighbor's daughter. The first incident ended in premature ejaculation, the second with my vomiting in her lap after too much to drink.
One spring afternoon when I was eighteen, I knew I was going to be alone in the house, and couldn't wait to get dressed up. My parents were away on vacation, and Sarah wasn't due back from college for another two days. I got my makeup perfect, just like those fashion models in the magazines. For my lingerie, I chose satin panties with lace trim, a satin lace bra, nylon hose and a matching garter belt. Over all of this I wore a shimmery lycra mini-dress. The final touch was a pair of three-inch toeless pumps. When I was done getting dressed up, I admired myself in the mirror. I was quite a vision. So much so, that my cock began to swell and I had to masturbate. I lay down on my bed and stroked my cock and massaged my asshole. Soon I was writhing in ecstasy, my lap soaked in pre-cum. I was so caught up in my reverie, that I didn't hear the front door open and close. Suddenly, though, I heard footsteps coming up the stairs and two voices. It was Sarah and her boyfriend Brad, back from college early.
I overhead Brad say something about "your weirdo brother, Michael". Then, Sarah said something about how I must be napping, and that they should barge in and surprise me. Flustered, I quickly pulled my dress down. Sarah didn't know about my hobby, and it was going to be doubly embarrassing being seen by another man like this.
As my mind raced, I saw my doorknob turn, and in barged Sarah, with Brad right behind her. First, she did a double take, probably amazed that there was a woman in my room. Then she realized it was me, and gasped.
"Michael! Oh my god!" she started, "Or, maybe I should call you Michelle! You little sissy!"
Brad just stared at me in amazement, at least partially at the fact that I resembled a fairly attractive woman, albeit with a hard cock under my panties and dress.
"Oh boy!", Sarah said, "What if mom and dad knew about this? You little sissy!"
I was totally flustered. I didn't know what to do. My eyes darted back and forth between Sarah and Brad. My mother was a very religious woman, and my father was extremely conservative. If either one of them knew about my cross-dressing, there would be hell to pay.
"Please, Sarah!" I stammered, "This is embarrassing enough being caught by you two! Please don't tell mom and dad! I'll owe you big time, I promise!"
