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About an inch in he hit resistance and I could feel him hit the barrier. Jason pushed gently forward trying to break through. I felt as...if he was tearing my insides out and I cried out in pain. Tony held me firm. Jason pulled back a little and thrust forward again. Again I screamed out in pain as tears formed in the corner of my eyes and flowed down my cheeks. Tony urged his older brother to do it hard and fast don’t worry about my pain as It was obvious that wanted to get. I started pounding faster. Denise moaned. I shot my load in her ass. “That was great,” Denise said as I withdrew from her ass. “I can wait five years for your dick. I’ll keep relaying this night in my mind until you return.” We said our goodbyes while I changed back to male mode. My last date was with Darcy. Darcy is a she male who decided not to go full transition. She still wanted to fuck men and women. My dates with Darcy were the same as my dates with Dennis but Darcy and I fucked each. In mild frustration, she took his hand and moved it to stimulate her part, explaining that this felt extremely good and to watch as she orgasmed.He was fascinated and looked for a discharge as it happened. His trousers were tented and she remarked that this was the big difference between a man and a woman. He acted puzzled so she told him to open his pants and let that stiff organ be free. Inwardly he was absolutely delighted.Grabbing a nearby cloth to catch the eruption, she rubbed his. You're too lost now to care whether this is right or wrong, you just want more. You want that finger deep in your asshole, fucking it, and for a change you get your wish as you feel my finger slowly slide inside you, your asshole sucking it in place. You feel me moving it around inside you, rubbing the inside of your asshole, before gently pulling it back until only the tip of my finger remains squeezed in by your tight ass. It yields again as my finger pushes back, finally beginning to fuck.
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