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This seemed reasonable to me, and after a few more chats we agreed to meet, we arranged for him to come to my place and fuck me there. It was during one of our chats that brian asked me something that no one else had ever asked before, he requested that I crossdress for him if would be comfortable with it. Now personally I had never contemplated crossdressing before, yes I had fucked cd's on occasions and have very much enjoyed the experience but to do it myself felt daunting. After some consideration I decided that I would indulge brians fantasy, but not go the whole distance, I settled on wearing some sexy knickers a bra and some hold up stockings and heels, but not getting fully dressed up with wig and all that.I had three weeks to prepare myself for the arranged meeting, so during that time I went out and purchased a black lace padded bra, matching hipster style lace knickers and some black hold ups. Heels on the other hand were a different issue, I finally tracked down a pair of. ”She convinced me. “OK, as you wish. But first, I will prepare myself.” I reached over to the bedside drawer, opened it and pulled out the packet of condoms and tube of lubricant that I had bought in advance of our first time. As I came to grips with putting a condom on my cock for the first time, Emma once again got on all fours. I applied lube to the tip of my sheathed member, smoothing it down for coverage; I then applied a dollop of lube onto her puckered hole, prompting a reactive jerk as the cold gel hit her skin.“Ooh, that’s cold!” she exclaimed.With everything in place, I moved into position. “OK, Emma. Take a deep breath and relax," I softly spoke. I placed the tip of my cock on her arsehole. “I love you, Emma, and I don’t want to hurt you.”“I love you, Francis, and I won’t let you hurt me," she replied.“Take a deep breath.” As she breathed in I slowly pushed myself into her. At first, my cock flexed as her hole resisted entry but soon the combination of force and lubrication.
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