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drakestories:

So here he was in the back office again. Jack lost the fantasy football league and he was never one to squelch on a bet. A week, 7 full days, of bending over for his coworker. The first time it hurt like bajeezus going in. Mike was not a small boy, and Jack was near virgin… completely if you don’t count that drunken night after a college fraternity party. Even though the victor took his time pushing in, it was one hell of a tight squeeze and Jack had to shut his eyes and take deep breaths to get through the ordeal.

Day two was easier. His anus was still stretched and relaxed from the day before and it took his coworker only a few minutes to prep and penetrate. If Jack was loosened up, Mike couldn’t tell. His buddy’s ass felt unbelievably snug against his thrusting lubed boner. His trigger cocked and loaded within three minutes flat.

Day three was different. Jack started to like it. He covered his face and leaned down again. Only this time it wasn’t to brace from the pain, but from the positive sensations vibrating in his butt nut and radiating outward. He prayed Mike wouldn’t make him cum hands free but feared he was having a losing battle with his own body.