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Next, she had me shave my legs and under-arms on a regular basis and had me start wearing pantyhose as well. I loved the way they felt on my legs and I didn't need much encouragement to wear them. Soon after that she bought me my first heels and started teaching me to walk like a woman. She had me wearing heels almost all the time at home. I loved the new additions to my wardrobe and worked hard at doing the things she suggested. It wasn't long after that, that she introduced me to wearing dresses and skirts. To say I was hooked would be an understatement and it drew Mary and I much closer together. She began to teach me makeup and also insisted I begin growing out my own hair. She assured me that once it was long enough to be styled in a feminine way she was sure I would be able to pass easily as a woman. I thought she was crazy but I knew that there were a few things I had going for me. I'm only 5'6" and slender. My beard is very light and I have very little body hair to speak of.. Before long, she said "lets try". I slowly stuck the head of my cock in her tight, but willing ass hole, she screamed a little when the whole head plopped in, but I kept going. Before long, I had it all in and started to pump. She was so tight, I had to go slow or I was going to loose it. I knew my buddy had only fucked her in the ass a couple of times, so she was mostly a virgin there. Before long her painful screams turned into those of pure pleasure, the harder I fucked her, the tighter she grabbed onto me, digging her nails up and down my back, harder and harder with each thrust. I was almost sure she was breaking the skin, but I didn't give a fuck, my cock was in heaven. About ten minutes in, she pulled me close and whispered "let me up, I want on top". No problem! I was exhausted from the heat anyway, although I hated to pull my cock out of her ass. So we switched positions and she climbed on top of me, welcoming me with a hot passionate kiss. By now, if we weren't before, we.
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