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Jack had been a cross dresser, in secret, ever since he got his own apartment. He had a few dresses he bought through the mail along with undergarments, wigs, jewelry and makeup, but it was unsatisfactory to him. He had much too masculine a body to dare go out in public so he dressed up in the house and had his fantasies. Jack dated women several times a month for appearances and he had even had sex with a couple of them. It wasn't good sex and he didn't really have an interest in it, not with women. He was skillful at creating the image of a young, athletic, stud but he really wanted to be a woman. He had never had anything even close to sex with a man, the chance he could get caught and what his father may do to him was too frightening. Jack also felt having sex with a man when he was still as a man wasn't right for him. Jack could dream about sex with men but only if he was a woman in his dreams, a real woman. Jack considered a sex change but the fear of his father kept him. I heard a muffled scream and then Lisa’s voice saying “ooowww… please take it out… not my ass… that fucking hurts… please stop.”As Lisa tried to struggle away from me I held her firmly by the waist saying “stay still you bitch. I let you fuck my ass so it’s fair that I fuck yours.”With that I continued pushing my cock into her tight ass until I was in as deep as I could go. I then pulled back a few inches before pushing in again and getting the last couple of inches of my cock into her tight ass.As I started fucking her ass, Lisa began sobbing and telling me “stop… please stop… it hurts so much… it’s too big.”On hearing Lisa’s sobs Karen yelled at me “stop dad; you are hurting her.”I shouted at Karen “shut up; and hold her still, I’m getting close to Cumming.”It took another few minutes of fucking Lisa’s tight ass before I was close to Cumming, and as soon as I could feel that I was ready.I leaned over and said to the now constantly sobbing Lisa “now you know what it feels like to.
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