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She liked having her ass played with, and wanted more. The tip of a feather playing on her asshole tickled, but her loud moans indicated that it also brought her great pleasure. For several minutes I spread the cheeks of her ass with one hand while I continued to tickle her asshole with the tip of the feather. She grabbed at the bed covers with her hands, moved her ass up and moaned loudly. “Fuck, yes. That feels so good.” “Are you going to fuck me in the ass again?” “I can’t stand it anymore. Fuck me in the ass! I want your cock in my ass!” Ignoring her, I used the feather on Gail’s hole until the tip of the feather was all wet. Tossing the “ass feather” aside, I slid a wet finger into her ass, and then two fingers, and slowly fingered her hole. She pulled on the bed covers, and told me over and over how good it felt. After several minutes of fingering her hole, Gail was breathing heavy, moaning, telling me how “fucking good” it felt, to go faster and harder, and to stop. Or I could drop Joanne off and then turn around… I mean…’ And he was all like, ‘it doesn’t matter.’ So I put my plan into action and said, ‘well, we’re closer to Joanne’s now so I’ll just drop her off first.’ (smooth right??? just wait, it gets better!). Well ALL day I’d been going ‘This is the day, I’m going to do it I’m going to do it’ and at first I was going to do it during lunch… but then I didn’t and then during play practice… but I didn’t. While I’m driving I’m thinking: ‘as soon as I park the car I’m just gonna go ahead and ask him. I’m going to, as soon as we get there, I’m just gonna DO it!’ As we’re turning into his court he asks, ‘So uh… who are you going to prom with.’ And me – being the smooth operator that I am – went, ‘Um..oh, I don’t know… do you wanna go with me?’ Oh man, my stomach DROPPED. I was like, ‘fuck, I am just the biggest freaking loser in the ENTIRE world.’ (That was obviously in my head.) and he was all like, ‘I don’t have any money…’ I just.
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