To date, Jack's favourite crossdressing moment had to be Hillary's junior prom night. Hillary decided to get dressed to the nines, which fortunately f...r Jack included her choice of hose. Hillary and her mom went out together to pick out her dress, a black strapless mini-dress. Hillary tried the dress on and admitted that her regular hose looked horrible with her elegant dress.When Hillary came downstairs to go to her prom, Jack immediately noticed sheerness of her black hose. It was his sister,. Sure enough, early the next evening she gave me a call. I asked her if she was willing to do a little household cleaning because I had a chore I needed done and had been putting off doing it myself. She said “Yes, when can I do it?” I told her “now if you are available.” Her response was a quick and eager “Yes!” I gave her my address and less than 30 minutes later she pulled into my driveway.I met her at the door, led her into the kitchen and told her she could put her purse on the island. She. PLEASE!"He removed his hand and placed it back on her hip."You may cum, my little slut, after ten more thrusts. Will you count them for me, my little slut?"Panting between every word, she said she would. He made them count, shoving himself into her ass as far and fast as he could, making her cry out before she could say the number each time."... Unh. Eight. Unnnhhh. Nine. Ooooh! TEN!"He reached down and stroked her swollen and slippery clit and kept thrusting. She exploded into her orgasm, her. "But before wego, I need you to put on these nylons. With a nice dress like that, alady should always wear stockings." Are you sure?" she asked. I could tell she was uneasy with the idea ofwearing such an intimate article of women's clothing."Of course, sweetie! Would I steer you wrong?" I asked in an innocentvoice. The sooner Jim became accustomed to wearing women's clothing, thebetter. "Now off with the dress!"I stepped behind Jim and unzipped the back of the form fitting blackdress she was.
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