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Cindy was an anal sex virgin and here is the story of her first anal.

Cindy fancied herself a hippie-chik, and kept her dishwater blonde hair long and flowing, with one of those perms that gave it a bit of a zigzag wave. Pretty. I had her long hair bunched up and wrapped around my left hand, and had near perfect control of her with this hair grip. She had some sort of coconut oil scented massage shit in a jelly jar by her bed (she'd actually massaged me with it, not bad really), and I scooped up the oily semi-solid and anointed my cock with it. Another scoop went directly into her asshole-- I tried to get it to squirt in a little, and stuffed my fingertips pretty roughly into her anus. "Oh!", she gasped, then "Oh, no...", she says...... " Uh, I've never......", she says, then "Oh!, OH!", again as I pressed the smooth, oiled tip of my cock hard against her puckering anus. I started to pull, good and hard, on her hair, down and towards me. This curved her back, forced her to hold up her butt, and angled that virginal asshole of hers exactly in line with my cock. All I had to do was make sure to position the tip of my cock correctly and my greased hard-on slipped into her asshole half it's length, in three successive little pops. " Oh my God! ", Cindy yelled, then another softer "oh my god, you really got it in there, nobody else could ever...".

I looked down on her butt, two pearly globes, held up on trembling smooth thighs, with the angry red ridged shaft of my cock firmly held by her sphincter muscles. For various reasons, none of which I'm gonna go into at this moment, I was not inclined to be a "nice guy" with Cindy. I scooped another glob of coconut oil onto the exposed shaft of my cock, then I grabbed her hip with my right hand, firmed up my hold on her hair with my left, and pulled her right up onto my cock.

She gave out this amazing kind of grunt, this pleasure-pain sound that sent a thrill through me and I swear stiffened my cock up another 50%. In fact, my cock throbbed in her asshole and with each throb Cindy gave out with another "ugh-oh-ooh". Then I made a little stroke into her, which definitely hurt poor Cindy, cause she gave out with a "Owwwhhhhlllll, Noooo, ooooowwwwhhhhhllllhh.". Now, I wanted to give Cindy the kind of assfucking that girls dream about for years afterwards, so I held still, just held myself and her still, knowing that if I waited for my pleasures she would soon be my total anal conquest.  

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