Contest Ch. 05

Story Info
Danielle loses her ass cherry.
2.8k words
4.52
236.5k
25

Part 6 of the 13 part series

Updated 10/30/2022
Created 02/18/2005
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Goldeniangel
Goldeniangel
12,549 Followers

Danielle was rather perturbed when she couldn't get in touch with Violet, after the party or the next morning… she wondered just what her friend was up to and worried that maybe her day off from a task had set her back further than she had thought it would. Last night's task had not been very arduous at all, although it had been rather embarrassing for some many people to watch her cumming all over Jared's face as he ate her out… if Violet was out working it she'd better get herself together too.

Deciding that since last time Jared's friend Chris had given her such an intense orgasm, she might as well go ahead and see if he had someone else who'd be willing to take her anal virginity… god that made her wince. It wasn't really as though she thought that anal was morally wrong - like she told everyone - or that even lesbianism was wrong… it was just that the thought of either totally grossed her out. Seriously, why would anyone want to stick something up her butt? It made her shudder just think about it. But, having someone up her butt was definitely preferable than having to be in someone else's pussy… she didn't even really like the feeling of her own. She never masturbated with her fingers, and she didn't particularly like the taste of her juices. Much better to give up her anal virginity… it might hurt, and it might be gross, but at least the grossness wasn't on her.

Jared sounded very pleased when she called him, he said that guy he'd originally thought would be perfect for her was actually resting up today after a while night with Violet - although he wouldn't tell her what they were doing. Instead, though, he said he had another guy who would probably do just as well, he just had to call him. In the meantime, she should dress in something sexy… and she might want to stretch out her ass a little to make things easier.

Danielle made a face as she got off the phone, no thank you. She'd rather suffer a little bit more pain than stick something up her butt on her own. Putting her blonde hair up in a long pony-tail she looked at her reflection in the mirror… yes. Perfect. Most of the attention was on her hips with the short skirt hugging her curves, and the shirt covered most of her boobs, making them look a little smaller. Pouting her lips she giggled as she watched her reflection… it was kinda fun to get dressed up and go meet a random guy. Well, hopefully it wouldn't be too rough on her… Violet was definitely already ahead of her if she'd had a wild night last night.

The phone rang.

"Hey sexy girl, my friend Karl says he'll be happy to assist." he gave her directions to Karl's apartment, "Enjoy yourself!"

"Right," she muttered under her breath as she got into her car.

***************************

Meeting Karl was a pleasure, he was a big black guy like Jared, very sexy and very powerful. Immediately, when she met him, she could feel herself starting to feel a little submissive… there was just something about tall confident men that did that to her. And he was very attractive which was nice.

When she came in, he led her into the living room where the center of the room was completely clear with a camera pointing at it from the side. Obviously, that was where she'd be losing her ass cherry. Standing a little nervously, she tilted her head up to him as he stepped in front of her. Smiling, he stroked one strand of blonde hair out of her eyes.

"You are very pretty," he told her, "I'm a little partial to blondes."

She smiled back nervously, "Does that mean you're going to go a little easier on me?"

A wide grin made her heart sink a little, "Not at all… but you'll enjoy it at the end."

Danielle nodded and he lowered his mouth to hers, sinking is tongue into her mouth as his hands began sliding her clothing from her body. When he got to her breasts, he pulled away, his eyes lifting as flesh spilled out through his fingers when he squeezed them, "These are a lot bigger than they appeared." she blushed and squirmed a little as he handled them… she hated how everyone had to pay so much attention to her huge boobs, but she did not want to insult the guy who was about to stick his dick up her ass. Seeing the look on her face though, Karl interpreted it correctly and decided to push her a little.

Smiling genially, he lifted her breast up, it was so big that her nipple was right outside her mouth when fully extended upwards, "Lick it." Tentatively, hesitantly, looking at him to see if maybe he was joking, her little pink tongue flicked out of her mouth and against the erect nipple.

"MMmmmm" he murmured as he began handling her big boobs, lowering his mouth to nibble on her nipples. It started to feel very pleasant as he handled her breasts skillfully, and he apparently got a lot of pleasure out of squeezing them and seeing her flesh spill out from between his fingers. After a few moments of playing with her boobs, he finally starting pulling her skirt off and slid two of his thick fingers into her pussy, she was very wet.

Standing before her, he ordered, "Take off my clothes."

Willingly, Danielle began stripping him, he had an impressive body. Lean black skin wrapped around long muscles, although he was rather slim, he was packed with muscles. A hard washboard stomach led down to his pants, and she ran her hands over his shoulders and chest, down the planes of his stomach as he watched her with a slight smile on his face. Unbuttoning his pants, she rolled them down his legs and gasped as his dick came into view.

Not even fully hard, it was one of the biggest dicks she'd ever seen… about 2" long and already 8" long, which was obviously not its fully length. She was shocked at its size as it continued to grow another two inches in front of her eyes, finally standing out proudly big and black away from his body. Almost reverently, she reached up to touch it… and as her fingers wrapped around its thickness, she remembered where it was going to go and looked up at Karl with fear in her blue eyes. He grinned at her malevolently, knowing exactly what anxious thoughts were running through her head.

"You're lucky Jake was busy with Violet last night," he told her, "He's not as long as I am, but he's thicker." Danielle shivered at the thought… although she wasn't sure if longer was all that much better than thicker. He was going to be awfully deep in her shithole.

Karl turned her around and put her on her hands and knees as he set the camera up so that it would get the best possible angle as he took her ass cherry. Flicking it on, he went over behind her, grabbing a bottle of lube from a nearby table. Settling behind her, between her legs, rubbing his hands over the fleshy globes of her ass… Danielle looked over at her shoulder at him, watching fearfully. She wanted to know exactly when he was going to start sinking that long black monster into her poor hole.

First though, Karl covered his fingers with some lube, and sticking the tip of the bottle into her ass, he squirted some directly into her tight hole and she winced as the cool liquid slid into her body. Pressing one big black finger against her hole, it slid in easily with all the lube, although Danielle moaned as her asshole stretched out a little around him. To her surprise, it didn't hurt that much… in fact it felt almost pleasant. Then he pushed a second finger in alongside the first, his thick digits spreading her open and she winced as it sent a little jab of pain through her ass. Pumping his fingers in and out of her slick hole, he made sure that she was at least a little stretched open, in fact she was starting to push back against his probing digits a little.

Pulling the fingers from her ass, Danielle looked back at him again, eyes big with anxiety as he spread some lube over his long thick cock. Looking her in the eyes, he smiled as he placed head of his black dick between her creamy cheeks and began to push the head into her ass. Danielle groaned as her ass started to stretch wide open, her head swung back around as she tried desperately to relax her burning ass hole.

Karl didn't give her a chance, he just pushed and slid partway into her ass, pausing with his hands on her hips as her back arched and she cried out as her ass was opened up about 4 inches, wider than it had ever been. With her head high and chin tilted up, Danielle's eyes were wide open as her ass clenched and released around the pole invading her ass, trying to adjust. Running his hands over her back, he massaged her lower back muscles as her head slowly lowered down and she looked at the floor, still gasping and panting a little as his hands massaged her creamy butt cheeks. For a moment, she wondered what it looked like, his black dick between her white cheeks, sliding into her hole. She didn't know how far he was in but since he wasn't pressed up against her she knew that it wasn't all the way… god… it felt like there was an awful lot of it in her ass. Little did she know that she still had about six inches left to go.

"Please," she begged, "Just do the rest, get it over with."

"I never turned down a lady," Karl smiled at the irony of calling her lady while his dick was splitting open her ass, he also had the feeling that she didn't know how much of his dick that she had to take. But, she'd asked for it. Leaning his body back a little so that the camera would catch the rest of his long black dick sliding into her ass, he thrust his hips forward until his balls slapped against her open pussy.

"OHHHHHHHHHHH…. FUUUUUUUUUUCK…." Danielle screamed as her ass split wide open, it felt like a baseball bat had been shoved up her tight hole. Karl just closed his eyes and enjoyed it as her clenching ass massaged the thick shaft of his dick, watching as the gasping girl's forearms gave out on her. Tucking his hands under her hips, he made sure that her bottom stayed high in the air as her upper body fell forward, her face buried in her arms as a few tear drops fell from her eyes. Her boobs were so big that they were flattened slightly against the carpet, rubbing against the nubby fabric as she heaved a little, trying to pull away from the cause of her pain.

Slipping his fingers a little lower on her hips, he began rubbing them in her pussy, and as he deftly elicited pleasure from her little clit some of the pain in her backdoor started to ease a little. Slowly, Karl drew about half of his dick out of her tight hole, enjoying the slick grip of her ass as it moved around his dick. Slamming back in, he jolted her forward a little on the carpet; so he got a better grip on her hips to keep her in the same place. Danielle moaned and whimpered as her nipples and breasts rubbed against the carpet, her ass burning as he began pushing in and out of her, while her clit and pussy tingled with pleasure as his fingers played in her wet folds.

Her ass was stretched wide, she could feel the head of his dick pushing deep into her body, making her stomach cramp a little as he slammed home in her tight hole. Starting up a steady rhythm in and out of her burning asshole, Karl rubbed her clit in time with his thrusts, pumping her ass and spreading shivers of pleasure through her at the same time. It benefited him too, because as her pussy rippled in pleasure so did her ass muscles, clenching and massaging his dick as he rode her. Using his hands on her hips, he started slamming her body back towards him every time he thrust forward, really burning and stretching out her ass hole as he plunged in to the very base of his dick. Rubbing his groin against her ass, Danielle moaned as her tight hole spasmed, his dick twitching and making circular motions, finding new unexplored territories of her ass to poke into.

Juices from her pussy were starting to run over his fingers as he slid them through her wet slit, pushing two of his fingers into her pussy he could feel his long hard dick through the thin lining. Pumping her pussy with his fingers, he used the palm of his hand to rub her clit as he rode her ass. Danielle wailed a little as he really slammed hard into her ass, the slick movements in and out of her back hole starting to get to her as his fingers rubbed against the g-spot in her pussy. She felt completely full of meat, her ass stuffed like a turkey at Thanksgiving, and her breasts were starting to get sore from rubbing on the carpet, her nipples stiff and raw.

Moaning as her pussy started to tingle with the familiar sensation of her build to orgasm, she started pushing her own ass back against him, the stretching and filling of her back hole beginning to feel incredibly good. Closing her eyes, Danielle managed to push herself up just a bit on her forearms so that it was just her nipples that were rubbing against the carpet. Shivers of pleasure went through her as her ass rippled around the thrusting cock, moving her hips against his hands as her nipples rubbed and tingled. Karl's hand that wasn't occupied in her pussy reached forward and gripped a large portion of her swaying long blonde hair, wrapping it in his hand and using it to pull her head back. As her body moved back with her upturned head, her back arched and pushed her chest more firmly against the floor, her ass high in the air as his dick drove even deeper.

"oh…. Oh…. OH MY GOD!!!!!!" she squealed like a stuck pig as his dick prodded her insides, "OH FUCK… OH MY GOD I'M CUMMING….. I'M FUCKING CUMMING WHILE YOU'RE FUCKING MY ASS!!!!!!! OH MY GOD!!!!!!!!"

Her body bucked and heaved, her ass rubbing against his body as his dick stirred in her clenching ass, groaning, he pulled back even harder on her hair as his dick pushed in its deepest yet and began spurting hot globs of cum deep into her body. Danielle could feel every pulse of his dick pressing on the tightness of her ass, every spurt of cum that flowed into her body, and she clenched hard around him as she rode out the last of her orgasm, her convulsing ass milking every last drop of sticky cum from his cock.

Karl pulled out, his dick making a soft plopping noise as it fell out of her stretched hole. Grabbing the video camera, he pulled it from the tripod as she stayed in her position, panting with her ass high in the air. Putting the camera right at the level of her ass, he did a close up of her gaping asshole, putting his finger into the center of the hole where it didn't even touch the sides because her asshole was so stretched out. He continued taping until the first white globs of cum began to run out of the slowly closing hole, Danielle just remained completely still, breathing heavily with her eyes slightly glazed over. She was in a bit of shock at her body's reaction so something that she'd always considered extremely gross and dirty… even the pain of it had felt good in some ways…

With cum dripping from her asshole and sliding down her thighs, Karl kissed her goodbye and sent her out the door. In a daze, she walked to her car and drove home… well, if nothing else this was definitely giving her an education in sexuality that she probably would have never tried on her own.

Goldeniangel
Goldeniangel
12,549 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousabout 10 years ago
good chapter....

but she didn't give or receive a rim job, so she technically didn't complete the task.....

msboy8msboy8over 18 years ago
Hot Chapter

I don't vote due to trolls and goblins. You accidently typed long instead of wide. so he had a 1 dimentional dick. Otherwise it was very sexy.

AnonymousAnonymousabout 19 years ago
Very Hot!

Kudos to you and your amazing erotic writing skills! Very sexy story.....I loved it!

Share this Story

READ MORE OF THIS SERIES

Contest Ch. 04 Previous Part
Contest Series Info

Similar Stories

Six Month Anal rape. Or was it?in Anal
Emmie Does Anal Sorority girl wants to keep her virginity & gives up her ass.in Anal
He Fucks My Virgin Ass He takes her anal virginity.in Anal
Julie's Asshole Is Used By Group Her secret anal cravings become a reality.in Anal
Heather's Virgin Ass Young innocent blonde resists her first anal.in Anal
More Stories