Cindy's First Anal
Copyright 2000

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......, and,  " Uh, I've never......", she says, then "Oh!, OH!", again as I pressed the smooth, oiled tip of my cock hard against her puckered brownie-pink 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, even though for reasons we needn't examine I was pretty mad at sweet Cindy, mad enough to start assfucking her as a kind of relationship punishment, I still 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 (well, hoping anyway) that if I waited for my pleasures she would soon be my total anal conquest.

I wrapped my arms around her, and was kissing her and saying, "oh, you're so good, you're so good...", and then my hand finds one of her pert little tits, and I started massaging it and rolling her nip with my fingertips. I'm holding real still but she starts to wriggle underneath me, and that makes my cock move around deep in her ass, and as it moves, she's making little mewing sounds, "mmmhh, mmm, mmmmohhhh, mmmuhhh...". Now, these are definitely not sounds of protest, so I start to move myself, just a little bit, and right away Cindy's mewing starts getting more and more exotic, and I can hear the surprise in her sounds, and there is no question she's beginning to discover the secret of anal; that when you do it right, no other type of sex produces as much raw pleasure.

Now, this turns me on, and I can't help but stroke harder, which is a mistake, because she's not really relaxed yet, and that longer deeper stroke hurts her, and her mews turn into a loud squawk, and then a deep grunty "OWWW", and she convulses in my arms, and tries to wriggle up, looking back at me with that "you bastard" female glare. But I don't let her up, and now I'm trying to be sweet, saying "I'm sorry, I'm sorry, you seemed to be liking it, I didn't mean to make it hurt.", and kissing her eyelids and her ears and her lips and her neck, and saying "I couldn't help it, it felt so good...", and other those other sweet lies men know how to tell women when they're fucking them. And all the while I'm doing this my cock is still nice and deep in her asshole, and we're moving a little, and I can see (and hear in her breathing, in all the little getting-fucked sounds she was making) that those slow deep small movements are something she definitely doesn't want me to stop.

We're sort've laying on our sides now, spooning, although I have her twisted around so her face is toward me and and tits are pressing down into one cupping hand, which is roaming back and forth between nipples, working first one to hardness, then the other. We're kissing, and I reach down and grab her hip in one hand, and start a slow pull of my cock out of her ass, taking at least 5-6 seconds. As I do this, her hands grab ahold of me fiercely, and she closes her eyes tightly, and grimaces. I push in, much quicker, and watch as her mouth pouts out into a quivering "ohhhh", followed by a little squeak as my cock thudded home at the rim. I wondered if I was hurting her, but once again, at that moment, I didn't care.

I hold still for a second, but then start another slow withdrawal of my cock from it's home deep in her slick rectum. Once again she grabs me fierce and grimaces even more fiercely, and then my concerns about hurting her vanished, because she lets out with the most extraordinary sound of female pleasure I have ever heard. It was this deep growling grunty kind of moan, followed by gasps that rocked her body, followed by a breathy yipe! as I pushed back into her.

I do this 3, 4, 5 more times, and each time she is louder, and each time the look on her face is more and more amazed, dazed, and desperate. Then I start to pull out the sixth time, and I go even slower then before, and when my cock has come about 2/3rds of the way out of her now wet and softening   asshole her eyes bug out, she starts screaming in what sounds like disbelief, and Cindy starts coming on my cock in her ass like she has never come before. (In retrospect, I often wondered what her roommates thought, because Cindy is yelling like she's about to die, it's about 4 o'clock in the afternoon, no doubt poor Cindy got herself a little bit of reputation out of that one...)

Now, there's no way in the world I can resist this. Cindy is squirming on my cock, her rectum is spasming around my cock, and she's she's shaking and yelling and gasping and making other "God I'M CUMMING!", sounds, so I grab her and roll her down a bit and roll myself over her and start pumping her more seriously.

Now, it's like this makes her explode, and it's clearly almost more than she can handle, cause she 's gasping like she can barely breathe, and she pretty franticly starts to cum again, convulsing, but still gamely pushing her ass back into me.

Watching this hits my buttons and I know I'm also cumming. I slammed my cock into her bottom hard, then held it there, and let the feeling of her ass around my cock pull the cum out of my balls. I wrapped my arms around her, my whole body stiffened and started it's own waves of convulsion, and everything went blue electricity and I pumped semen again and again into her body.

We lay there, locked together in a sweaty pile of male and female flesh, both of us completely blown away. I looked at her red face, and knew that she was realizing that she had just had the most amazing sex of her life. I kissed the sweat off her face, and mumbled into her ears "you're so good, you're so good...".

"Oh god,", she said,"I think I have to go to the bathroom...". My cock was still a little hard, and I tried to pull it out gently, but Cindy was by now a little sensitive, and she moaned a complaint as I pulled out and then popped out. A little stream of foamy oil and shit ploooped out of her anus. "I'll bet you do...', I said to her, and I grabbed my T-shirt and pressed it against her butt, and then helped her get up and put on a robe. In a second she was rushing to the bathroom. I lay on her bed, feeling the cool air dry my cock.

She kept the t-shirt- washed it of course- and used to wear it all the time. We only were together for about a month after that, but during that month, it became a standard secret ribald joke between us, that "tonite she might need that t-shirt", which meant that tonite she might be getting sodomized.

And so, If you buy me a beer, I just might tell you another Cindy Anal story, and let me tell ya, I've got some doozies...