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Little by little I worked my erect cock deeper into her as she clenched with some small amount of pain. I told her that in the future, the pain would become pleasurable, like when she first lost her virginity. When my cock head was completely inside her ass I remained completely still and pulled the pillow out from under her stomach allowing her to drop to the bed. We lay there for several minutes as I kissed the back of her neck, letting her anal opening adjust to its first cock. When she became comfortable, we started towards her first anal climax. Slowly I started pumping my cock in and out of her tight opening, increasing the pace and stroke depth as she became more relaxed with my cock in her ass.After only a short time Monica started responding and reached her first orgasm. "God, this is great, I can feel you moving all through my insides; my cunt is being pushed like never before." she gasped. After several more of her orgasms my cock erupted it's sperm filled load deep into. She made me come out and there I was again in her panty hose and high heels. That feeling has never left me. The excitement of wearing ladies undergarments throughout my life has always brought me back. This went on for a week or 2 and freaked my mom out so much she ending up talking to a shrink about it. She bought me girls panties and took them in to fit me but those crappy cotton things just wouldn't do it. Back to her room, I have decided. I have always had a love affair with white lingerie. I pull out a pair of her white stockings, her white garter belt and a pair of her white panties. I pack everything that I am not wearing back, just in case someone come home I can get away quicker. Taking the white garter belt which is made of soft see though lace I clasp it as tight as it will go and pull it up my smooth hairless legs, then over my hairless scrotum. I pull it over my penis as I continue up to my belly button. They tickle as the straps brush against my thighs and.
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