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It was a bit of an obsession of mine, an obsession that got me into some very interesting circumstances.It started when I was in college. Nothing but time on my hands, and even though I shared a room with another girl friend, I found time to adventure. It started with my fingers, rubbing and circling around my puckered hole while I fingered myself, the tingling pleasure had me hooked. I'd then adventure to fingering my ass and pussy at the same time; the first time I filled both my holes I orgasmed so hard I squirted a bit. A bunch of firsts for me that night. Curiosity got the best of me and I moved to using multiple fingers, then eventually my dildo to fill my ass. Feeling my hole envelop around the head of the fake cock, before sliding it deep inside me was almost enough to get me off right there. When I'd slide it all the way out then jam it back in, it drove me wild, and the orgasms kept coming.Of course having a roommate had its challenges. One time I was home alone in the. Stalling for time, you answer, “I don’t know,” and she smiles sympathetically. “It’s okay to be scared, I’d be scared too, if I was you. Just know, I’m not going to hurt you or anything like that, not unless I ask you first and you say it’s okay . . . okay?”Five minutes later you’re in her back seat, naked, wiggling your way into a pair of panties that are nowhere big enough to contain your excitement. She’s watching you in the rear-view mirror, and smiling back at you. Then she hands you the cuffs and tells you to cuff yourself to one of the two “whoa shit!” handles mounted to the ceiling. Once you’ve done that, you’ve relinquished all control over your fate to her, and the feeling is terrifying. Your heart is pounding as she climbs out of the driver’s seat and re-enters the car via the cramped backseat and closes the door behind her, sitting herself between your legs so they are pinned open. You can barely see her in the dark but you feel her hands sliding up and down your thighs,.
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