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I had been slowly stroking my cock for the last hour, putting on a show for no one, but building up a light sweat. At ten inches long I had to use both hands on my shaft or else my cock would jiggle and spray jizz everywhere. With both hands keeping my cock steady I was heavily leaking a good stream onto my chest while I goonedCough“Get a room.”Da fuck! I jumped at the sudden noise. My jump caused my cock to spray. Looking up I had to catch my breath. Standing in the entry way, was Jake, my sister’s longtime boyfriend. He was only a few years older than me, but damn he was hot. Seeing him looking at me caused my cock to lurch and squirt a little bit of pre-cum.“Here for another date with my sis? This is what, the big goodbye?” I couldn’t resist teasing him.“She’s only gonna be at the program for three weeks, why is everyone acting like she’s leaving forever!”I couldn’t resist getting up and walking over to give him our customary brotherly hug. I moved toward him but Jake knew better,. He pulled and tugged the blue dress over his head and finally fastened the buttons up the back, the hoops on the underskirt made the dress stand out at least 3 feet either side and as he glance at his reflection in Jack began to feel a stir of excitement in his panties. The heavy satin dress and underskirt made any chance of Jack playing with his penis almost impossible so he headed towards the make-up table.The make-up was theatrical make-up but would be sufficient for Jack's purposes so he proceeded to apply the 'grease paint' to his face. Fifteen minutes later Jack had a heavily made-up, pale face with dark eye make-up and bold red lips. There were no wigs for Jack to try on, but a black bonnet that he found was enough to hide his final trace of masculinity. The bonnet appeared to be made from cardboard or something, covered in black satin, with frills along the front edge framing his face with a 2 inch circle of satin. Long ribbons were used to secure the bonnet under the chin,.
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