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He guided my hand to his shaft and I held it. I could fit my whole hand around the bit that was left. He groaned as I softly stroked him. I looked up into his face to see a wicked smile ghosting over his lips. He pulled out slightly and let me feel my wetness coating his shaft. Then he started to move again. I couldn’t believe the pleasure. It rolled in waves through me. Every time he slid himself further and further inside. It wasn’t painful, it was oh so good. The way he stretched me with every stroke was unlike anything I’d ever felt before. He worked himself inside me in a steady, slow rhythm until he was balls deep. Then he held. My body didn’t know what to do with this much pleasure. He was completely still inside me but inside I was contracting in waves and waves of ecstasy. He looked at me, and I saw how close he was. He was holding still out of necessity. He looked wild. My body continued to stroke him from the inside. I was building up to an amazing orgasm and he wasn’t. Kneeling behind him, Ann spread Will's cheeks and generously lubed his ass using two fingers. Then she lubed up the six-inch strap-on dildo.“As you told me the first time, relax and enjoy,” Ann told Will as she positioned the head of the strap-on at the entrance to his ass. Feeling him automatically tense, Ann moved back and twice smacked his ass with the flogger, both times enough to sting. He forced himself to relax as the head of the strap-on made its way into his entrance.Little by little, she inserted it into his ass until she gave one final push to go past his sphincter muscle. After giving him time to adjust to having something in his ass, she pulled part way out and added more lube. Slowly fucking him, Ann reached around and grabbed his cock, milking him as a farmer would his dairy cows – squeezing and pulling down on his cock. Ann slowly increased her speed until she was pounding his ass while she continued to milk him.Will was moaning, telling Ann, “Fuck me deep... Fuck me.
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