By the time I was naked he was standing in front of me with a bundle of clothes in his arms. 'Dress up' he commanded while handing me the clothes. As I was picking up the bundle I realised it was all girl clothes. I've stared at it for a few seconds, confused. And then it dawned on me, he wanted me to dress up as a girl!'Seriously?!' I exclaimed incredulous. 'Yea! Fen's stuff should fit you alright, plus she has a really good taste.' he replied excited and winked at me, 'It's gonna be real fun, trust me! You will love it!'I stared at him still clutching the bundle, disbelief evident throughout my face.'Oh, go on!' he urged me, 'At least try it. And if you don't like it, we'll stop. I promise.'.Still unconvinced I started dressing up. First came a skimpy pink, laced thong. I was quite surprised that it actually managed to hold my now semi-limp cock and balls. I next put on a pair of white & pink, striped, holdup stockings and a blue, tartan, plated mini skirt. After fumbling with the. I started rubbing her pussy. Then I traced my finger down on her pussy lips.With my other hand I pulled her legs apart. Now I could c and feel her whole pussy. I took a handful of spit and rubbed it on her pussy. Slowly I put my smallest finger in. It went in an inch and would go no further. When I applied force she moved. I withdrew and got oil bottle from the dressing table. After oiling my finger I re-inserted it in her pussy. It now entered smoothly but could not go further than an inch. Suddenly,I realized that she was a virgin. I realized that she did not, perhaps, fear my touch so much as losing her virginity. I oiled her pussy well. I un-pocked a condom and put it on my pulsating dick. Then I positioned myself between her legs and tried to enter her. My aim was wrong. I rose re-aimed my dick and tried to enter her tight pussy. I was able to enter a little as my weight pushed it in.She felt the pain and pushed me away. She did not say a thing and just upped her panty and.
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