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That was my first memory of crossdressing. I must have been 13 at the time. I don’t remember what I wore but I remember the feeling. I had the harde...t erection ever and I started playing with myself. I was staring at the mirror for like 50 minutes just jerking off non-stop. When I orgasmed, it was like 4 years worth of cum. It was my first orgasm. I think because my first orgasm was connected with crossdressing, my brain probably associates the pleasure of orgasm with dressing up like a girl.. I told Kat, "You can start at four thousand dollars a month, room and board included."She stared at me in shock. I saw the tears start rolling down her cheeks and I took that to mean that she was not only interested in the job but happy for the offer.I leaned over the armrest and put my arm around her. She covered her face and cried quietly for a few moments while I held her. Finally she started digging through her purse for a tissue. She wiped her eyes and blew her nose. Then she quietly said,. “Do me -deeper -” Ryan obliged her, forcing his cock all the way into her, sliding back out like a piston. She pushed back against him until her arms were resting on the windowsill, her breasts swinging like heavy hanging pendulums beneath her. Ryan moved faster, rewarded as he felt her pussy squeeze him tighter.He reached his hands around, gripping her breasts, her nipples trapped between his long fingers. “Ah - “ Me. O’Negai groaned. “Sq- squeeze them!” she groaned as Ryan started pulling at. When I told her I was cumming she sucked my cock deep in her mouth and took my whole load. She waited until I finished then opened her mouth to show me my cum then swallowed. She seemed pretty proud of herself and smiled “ I don’t know why I never tried that before” she said .”Maybe you should have made me do it like Randy did, I will do this any time you want now”she said sitting back on the floor. “Something else he did was lick my pussy”she said then spread her legs . Wheel if she wants it I.
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