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Ian whined when he felt Grant’s fingers separate his ass cheeks. He shivered as a big finger rubbed at his tight anal skinny flower. Lubing it. Circling the virgin hole. His whole world seemed to spin with the motion. Ian hissed as the finger pressed inside him to the first knuckle. Painful and intrusive. Then it was gone. Grant leaned into the sissy. Grabbing his hair and yanking his head painfully up. His big, lubed dick rubbed against Ian’s round ass. “Time to truly make you my little bitch.” Grant hissed into his ear. Then with no more fanfare he took the last of Ian's manhood. Spreading apart the wimp’s asscheeks and pressing the tip of his cock to the sissy’s clenched pucker. Ian squealed as the cruel dick pierced him. Like it was drilling into his soul. His ass spread open in a burst of pain. Sissy tears pit-patted onto the wooden desk. Grant grunted in pleasure as his big dick painfully jackhammered amateur into the tight pansy ass. Through clenched teeth Ian begged tits "N...god no! Please! Uuunh!" As the man’s big cock hammered him, Ian's own penis got hard as well. It slapped up and girlfriend down into his sissy tummy, as Grant fucked him from behind. Ian was reduced to painful grunting. His body tingling all over. He couldn’t help pressing back into the man violating him. Helping the Alpha painfully ram home. He could feel Grant’s balls slapping against his thighs he was so deep. With a smile Grant triumphantly fucked the sissy secretary. Now seemingly a willing participant in his own anal violation. Soon Ian was coming all over the front of Hardcore his boss's desk. His sissy cum drizzling down the front. I opened the drawer quietly – sure enough my panties were sitting on top of the pile of items inside. Once my Hardcore energy reached the desired levels I began stripping my clothing from my body. "Your learning. I glance back inside and notice that the home is clean, tidy, and girlfriend organized. So tits did the young man on the balcony on the other side of us. A few minutes later, Steve was on his back on the white sheepskin rug in front of the fireplace. At one point he approached her to show her the last shot he had taken. As soon as I was close enough to him my dad roughly grabbed my arm and tried to throw me out the door. “Thank you, I will,” she said over her shoulder as she headed off toward the stairs. The tiny aperture of my sinful hole dilated, and I shrieked in terror as it slowly expanded. She had a sexy daughter. “I'm not sure why I changed my mind. Just like how I skinny shaved today. She just nodded amateur unable to verbalize any words for the moment.