Jocelyn has a problem. If only she can give Steve the fucking he wants, while keeping her virgin hymen intact. And, from the talk among the other girls, she has developed a plan. She's heard whispers of the pleasures (and the pains) of anal sex, and has decided that if she can only manage to learn how to let Steve fuck her teenage bottom, that illicit sodomy will tie him to her forever, while saving her precious hymen for the honeymoon night.

Jocelyn has always been the bookish type, so she studies up on anal sodomy. The secret of anal sex, she discovers, is learning how to relax and loosen her asshole, so that Steve's cock can go right in and rut and thrust deeply in her rectum. She practices with her finger and lotions, but nearly gets caught by her father, who stops by on one of his surprise inspection visits to her bedroom. As usual, he tests her hymen with a finger, but luckily for her he doesn't detect the lotion seeping from her puckering anus. After that close shave, she decides to continue her work in the locker room at the high school, where, as head cheerleader, she has nearly free rule over the girl's locker room and girl's showers.

She has handled Steve's cock, in her daily afterschool sessions of making out, heavy petting, followed by her skillful hand jobs that quickly lead to his cum explosion into the tissue which she holds neatly around the purple head of his cock. She knows to the millimeter it's girth and length, and from this hands-on knowledge she realizes that her finger will never open her asshole enough for her to let him in without screaming. So, from her best friend she borrows a "girl's best friend", a vibrating dildo, and also some new, clear, high quality lotion so that she will be able to do this right first time, every time.

Monday night, after practice, when all the other girls have gone home, Jocelyn brings out her borrowed dildo and lotion, and, thinking of Steve, she carefully inserts the dildo into her pussy, being very careful to insert it only part way, stretching her hymen but never, oh never, risking it's breakage. She strokes her clitoris with her finger, and then lets the vibrations of the buzzing dildo stroked over her pink clitty soothe away the anal fears that still trickle thru her thoughts. She thinks of how handsome Steve is, of what a good father and husband he will be, of the car dealership he will inherit from his father and the luxurious future it promises, and as she gets hotter and hotter from these dreams, she repeats her earlier fingering of her tight little asshole. The resistance of her anus surprises her-- it seems to be thinking of Steve's thick shaft, of how he might roughly stretch and tear her asshole open in his lust. Well, no tight little opening is going to defy her will and screw up her future!
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She gets on her hands and knees and presses the dildo against her anus. She tries to imagine how Steve will fuck her there, how he will shove himself into her, and she presses to shove the dildo into herself the same way. But, OH!, IT HURTS! The dildo's plastic is hard and unforgiving, and seems to be even sharp in some way as it presses home. She hears herself give a little squeal as the pointed tip of the dildo penetrates. But it's in only a little bit! "Relax, relax...", she thinks to herself, and she tries to move into a better position, arching her back so that her belly nearly touches the floor, and her ass, pointing up in the air, is naturally open and receptive. She starts to wiggle the dildo's tip in her tight resisting asshole, and discovers that her anus has indeed been relaxing, and that the plastic cock is sliding in a bit deeper. She's surprised to discover that after the initial pain, which was worse than she thought it would be, the wiggling and motions of the dildo in her 18-year-old ass are starting to feel more and more interesting. Without thinking, she pushes harder, and another inch slips into her butt, and this time, instead of a gasp of pain, a YIP! of a definitely nasty pleasure escapes from her lips. "Hey", she thinks, "This isn't so bad-- this just might work.".

However, try as she might, she can't seem to get more than a few inches of the plastic dick into her bottom before an uncomfortable pressure and feeling of tight resistance stops her. She tries several different positions, and in each of them she discovers that she is not yet ready to take anywhere near the full length of the rigid dildo into herself. Still, what she can take, she likes. "All I need is a few weeks of practice, and I'll be able to take Steve right to the root!", she decides. Her anus is a little tender, and she decides that she's worked enough for the day, hides her "girl's best friend" in her locker, and walks home, hoping that no-one will notice her slight waddle. (Moral of this story? Use lots of lotion and a soft dildo for anal experimentation.)
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But, what Jocelyn didn't realize was that Heather, who was indeed trying to steal Steve away, had spied on her experiments with anal dildo opening. Jocelyn had been so preoccupied that she hadn't heard Heather coming into the locker room after her own hidden bag of cigarettes, rubbers, and sex toys; toys which she kept locked safely away with her gym clothes. Heather watched Jocelyn from the shadows of the equipment room, feeling strangely stirred by the sight of the pure teenager probing first her pussy, then her asshole with a white dildo. Heather kept silent and waited as Jocelyn finished, dressed and left.

Heather's pussy was soaking from her voyeurism. She pulled off her clothes as fast as she could, and pulled a 10" transparent soft jelly dildo from her bag of tricks. She started licking the tip and then shoved it into her mouth, imagining it tasted of Steve's thick quarterback prick. She knew  Steve would push it till she choked, so she closed her eyes and rammed the dildo into her throat. "Oooch, Gluuch,uuuulp,oooooCCChHlllpPP," came the involuntary noises as she  practiced deep throating. When she pulled the big jelly cock out she gasped and coughed., but inwardly she felt very pleased with herself, for she had taken the cock deeper into her spasming throat than ever before.

The dildo was wet with spit so she imagined Steve roughly made her bend over and take the cock from behind. She reached behind her and guided the head of the dildo to her vagina. Then she firmly grabbed the end of the dick and rammed it into her pussy. Heather's hymen was long gone, but there was still a tearing feeling as the dildo forced aside her pussy lips and burst thru her vaginal opening, and still more pain as the dildo plunged four, five, six, seven inches into her teenaged cunt, until all that was left outside her was the handle end held firmly in her fist. She screamed a little as she plunged herself, "AHHHHaaahh- AHHHahhhhhh ahhhhhhhhhAHHHHHHHH!". The fingers of her other hand made furious circles over her now-engorged clitty. God, it was almost as good as the real thing. Her knees were weak and she nearly fell to the floor. She rolled onto her back and, holding the dildo with both hands, fucked herself the way she wanted to be fucked, roughly, viciously, inconsiderately!

She thought about what Steve would want from her now, and remembering Jocelyn's anal sacrifice, she spat a wad of saliva into her painted fingertips, and pressed the lubricant against her anus. It was only the work of a second to pull the jelly cock out of her pussy and press it's bulbous tip against her now slickened asshole. How would Steve want it, she wondered. In her mind, a little voice whispered "just how you want it---- fast and rough.". She pushed on the dildo. Her asshole, which really wasn't any larger than Jocelyn's, resisted, fought the intruding artificial cock. She shook her head, gritted her teeth, and shoved. "OHHHHHH!", she squealed, but her shove did it's work, and the cock split open her asshole and pressed inside. "OH MY GOD IT'S HUGE!", she thought, then, determined, pushed again. Innnn the cock went, one inch, two long fat inches..... Then three inches.... Heather grunted, UH, UH, UH, and rested for a minute.

When heather moved the cock again, she discovered that the initial tearing pain of entry was going away, and that the remaining intense feeling of fullness and insistent throbbing pressure was starting to fill her groin and hips and bottom with a feeling of pleasure, a rich, fulfilling pleasure sort of similar to the pleasure of releasing a good healthy shit, but mixed with a grunty sexual sweetness. Oh, this was really very good, when it wasn't hurting. The dildo still seemed very large, and her rectum and anal muscles were clamped onto the thick shaft with a type of desperate burning stickiness. Oh, yes, this was very, very nice, she could see now why some of the football players liked to have their assholes fucked as much as they liked fucking girls.

Heather lay on her back and, holding the end of the dildo, proceeded to fuck herself over and over again in her anus. The cock made wet farting sounds as again and again she forced it in, as deeply as she could stand it. faster and faster she sodomized herself, and as she did, she found herself forced to make sounds, grunts, gasps, moans, and finally something more and more like a real scream as faster and faster the cock pounded her ass.

"Holy fuck, oh shit, oh fuck shit oh my god holy Jesus oh fuck me fuck me Fuck Me FUCK ME, OHHH STEVE POUND MY ASS, MY ASS IS YOURS ALL YOURS FUCK IT FILL IT FUCK ASS FUCK DEEP ASS FUCK IT FUCK IT FUCK IT!!!".

Heather didn't expect the anal orgasm, and when it hit her it was stronger than any orgasm she had ever had. She tried to shove every inch of the cock into her tight bottom, and every inch of it felt WONDERFUL. She rolled from side to side of the floor, gasping for breath, holding the jelly cock deep in her bum, until finally she began to relax.
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Suddenly she was feeling very full, as if she had to take a mighty shit. She forced herself up, still holding the dick inside of her, suddenly very aware that if she pulled it out she might have a shitty mess. She waddled over to the shower room, and, holding the wall for support because the pleasure of it threatened to make her knees collapse, she slowly pulled out the dildo. She dropped it on the shower floor, noticing that it was covered with shit, and waddled again to the toilet where her wish to relieve herself was answered by a foamy gush from her bowels. Her asshole throbbed, and she was weak with pleasure from that incredible, incredible orgasm. She was going to have to make sure she emptied her bowels before she let Steve, or hank, or Joe do that to her, she thought-- but she was definitely going to do that again. Soon!

She cleaned up the place, dressed, and still woozy from orgasm, headed homeward.

Unbeknownst to both Jocelyn and Heather, one of the school's janitors had a hideout and a digital camera, and he took these pictures and hundreds more, and sold them to me, so you can see them today.

This is an original fictional story, copyright