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I spit on his asshole a few times to lube him up so that it wouldn’t be too painful. His hole was very tiny and I knew it was going to hurt him a bit. I lined up with the hole and slowly pushed. The initial pressure made him cry out in pain, but I pushed anyway. Once I got the head in I stopped and told him to relax. He whimpered a bit, but I felt his hole loosen slightly so I pushed a little further. Once again he cried out in pain. Once I got half way in I stopped again and reassured him that I was almost in and that it would stop hurting soon. I decided to put the last few inches in a lot faster to minimize the length of his pain, like ripping off a band-aid. I pushed in the whole way and he screamed and I mean screamed in pain. I stopped and leaned forward hugging him and kissing his neck and whispering that it would feel better in a little bit. He turned his head to the side to look at me and there were tears in them. I felt so bad that I had hurt him so much, but. Soon six red lurid marks showed on Mum's bum.Mr Miller ordered her to bend over again and spread her bottom for him. She flexed her asshole in and out as he took our tub of butter and smeared a small piece around his dick to lubricate it. I caught a glimpse of him putting his bulbous prick tip to her naughtiest hole, then she went "OOOOOOOOUUURRGH! You dirty man!" as it plumped into her creased starfish and shoved right up her bum!Mz. B stood nearby, arms folded and chiding Mum again. "Whoooo, ha haaa, Teresa! You Dirty Mom! Bum Bitch! Remember your video? The willy bum exercise? Do the willy bum!"They made Mum do squat thrusts on the floor, her bare feet going back and forth and her bum bobbing up and down, as Mr Miller took her anally. Her ankle chain shook around as her sexy body moved in rhythm. He slapped her ass and bossed her about as he took her asshole. "This is the Extra, Teresa, but it's not the Extra Extra, you know that don't you?"Mum nodded and agreed, as she did the.
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