Contest Ch. 06

Violet was on her way to getting a head start on Danielle… she knew that her friend had taken a brutal beating on her massive tits - and quite frankly that thought turned her on quite a lot - and the pretty half-Asian was going to take good advantage of the fact that her friend needed a day of rest!! She was going to get what she thought might be the most physically demanding of her tasks: taking on an anal train.

Anal was not something that she thought was morally wrong, like Danielle, or that she thought was particularly perverted; it was just that as a more dominant personality it wasn't something she allowed her lovers to do to her. Still, it was something she had always been curious about, especially because a few of her male lovers had particularly liked having her use a strap-on in their asses and two of her three female lovers had as well. There was just something very submissive about it though, and she'd never been able to bring herself to ask for it from someone else… now here was the perfect opportunity presenting itself and she was definitely going to take advantage. The thought of it being an anal train did worry her a little, but she's come to terms with her fear of that. If nothing else, she wouldn't be behind Danielle since she was taking a day of rest today… if Violet needed a day to rest up after this, it wouldn't be a problem at all.

Dressing sexily in a mid-length tight black skirt that had a slit up that back nearly to her ass, and a short, tight dark red button up shirt that heightened the color of her slightly tanned skin and the highlights in her hair, she decided to do without underwear for this. It wasn't like she was going to be wearing it for long anyway… and there was something decadent about dressing a little sluttishly. She decided to put her long dark brown hair up in a ponytail to get it out of the way of everything, it flowed down to about her midback, two short locks framing her round face. Brown eyes glinting impishly, she blew a kiss to her reflection before heading out the door.

Jared had given her directions to his friend Jake's house, telling her that Jake and three of his other friends would meet her there. One of the nice things about using Jared's friends was that the video camera was always set up, she didn't have to lug around her own stuff or try to find a good place to put it. Also, she trusted Jared to keep make sure his friends were clean - after all, the loser of the contest would be with Jared for a night and he wouldn't want to put his own body at risk.

Arriving at Jake's house she wasn't surprised to find it as big and beautiful as Jared's own. What she was surprised at was the fact that Jake was Asian and only an inch taller than her scant 5'5"… she just wasn't all that used to men being on her eye level. Still, he wasn't very intimidating because of that and it made her feel more at ease. Slipping off her shoes in the hallway, he led her into the living room where she was immediately the center of attention for four new guys. Jake introduced her to all of them; Ned was the tall blonde with green eyes, Hank was the skinny and very tall black guy, and Brett was of middling height with brown hair and brown eyes. They were all already naked although they weren't hard, and they were all looking over her body with anticipation and lust. It made her shiver a little to have all their attention so close on her.

"Why don't you strip for us," Hank suggested, which the other guys immediately backed up. Jake took off his own pants as Violet posed a little and began slowly unbuttoning her shirt, revealing just the curves of her perky 34C breasts until she reached the last button. Turning to the side a little and pouting at them, she wriggled her shoulders so that the shirt slid off, baring both slightly tanned shoulders, as her shirt slipped off her arms were still hiding most of her breasts so that all they got were glimpses. It was still enough for them all to start getting a little hard, and she turned her back to them without letting them get a full view of her body and then started to pull down her skirt, bending from the waist as she slipped it off. She heard one of the men groan as they got a great view of her upturned ass and pink pussy, turning quickly she posed so that they could get the full effect of her body being displayed for them, grinning mischievously. Violet was one of those girls that had teasing men down to a fine art.

Looking them over as they watched her, she was a little surprised at the differences in their dicks. Hank's was the longest, but it was also the skinniest - but the length was such that if it hadn't been skinny it would have been rather frightening, he looked to be 10 or 11 inches long, the head bobbing way out away from his body. Jake's didn't look very long at all, but that might have been because he was as thick around as a coke can… she hoped that he wouldn't be the first in her ass, she'd much rather have length than thickness when it came to stretching her hole. Both Brett and Ned were somewhere in the middle, with Ned's being more long and slender (although not as long as Hank's) and Brett's being less long and more thick (although not as thick as Jake's.).

Jake quickly pulled an ottoman into the center of the room while Brett turned on the camera, and as Violet arranged herself on the ottoman so that her ass was at the very end and her chin or cheek could rest on the leather fabric, Brett grabbed the camera and circled from her face to her ass.

Behind her, Ned got into position and slid a lubricated finger into her ass, wriggling it to stretch her out. She grimaced a little, it felt uncomfortable but not necessarily painful… mostly it felt like something that didn't quite belong there that she wanted to push out. A second finger slid in beside the first… that did hurt a little bit, but again it was mostly the discomfort and the feeling that she needed to poop that bothered her more than anything. After a few moments of his fingers sliding in and out of her ass, until she stopped clenching down on him every time he slid in, Ned pulled his fingers from her ass. Out of the corner of her eye she could see Brett getting close in with the video camera as Ned placed the tip of his dick at her ass.

Turning her head slightly, she asked, "Please… go slow, I'm a virgin in that hole, I don't know if Jared told you."

Ned grinned reassuringly at her, "Don't worry he did, and I've done this plenty of times. We've got an order set up too, me first since I'm more slender than anyone except Hank - and he's kinda long - and then Brett, Hank and finally Jake."

Jake laughed a little, "We're not going to hurt you too bad Violet, it'll be fun in the end… pun intended."

The men all chuckled as she made a face at the low humor, turning back around to place her cheek on the soft tan leather of the ottoman as Ned's dick began to slide into her ass.

He went slowly, pushing just a little in before pulling out again and then pushing a little more in, but it still burned a little as his dick pushed into this previously unexplored territory. Slowly her ass stretched open for the intruder, inch by inch as he humped her, the camera catching all of it as Ned slowly disappeared into her ass. Finally, he hit bottom, and held it there a moment for her to adjust. Although she was grimacing a little in discomfort, Violet wasn't in any pain, Ned's slow movements had allowed her body to adjust to his width and his length easily. In fact, it felt kind of good to be filled up in her ass… the pleasure in the fullness of her hole was something she had not expected at all.

Pulling about halfway out, Ned thrust in again, eliciting a moan from the bent over girl as he plunged back in to her tight hole. Violet shivered as he began to fuck her ass, thrusting in and out slickly as the lube eased his passage, it felt very full and very good… the little nerves all around the outside of her hole were tingling as his dick slid past her opening. With every thrust home his balls slapped against her open pussy with a wet smacking noise, a few times it would even hit her clit and she was starting to get a little turned on, both by the feeling in her ass and the occasional impact on her clit.

Reaching around her body, sliding his hands under her chest, Ned began to squeeze her round breasts as he pushed in and out of her deflowered ass and Violet lifted her body up a little to allow him better access as she moaned in pleasure. Having him thrusting in and out of her ass while his hands played with her breasts and his balls slapped against her pussy was feeling a lot like foreplay. Not enough to get her off, but definitely arousing. She began to push back a little against his body, and to purposefully clench down on his dick feeling it twitch inside her in response.

With all his attention focused on the tight warmth of her ass and the pleasure he was feeling, it didn't take Ned long to start groaning how tight she was as his cum spilled into her. The first load of cum that she'd ever taken in her ass… it amazed her how different it was from when a guy came in her pussy. Sometimes, in her pussy, she could feel a guy's dick pulsing, right now she could feel every ripple, every twitch, every spurt of cum as it traveled through his dick and into her ass. It made her shiver around him a little, which only intensified his orgasm.

As he pulled his hands from her breasts and his dick from her ass, Violet let her body relax onto the ottoman as she eagerly awaited Brett. Her arousal from Ned was high, having him cum in her ass had been a rather intense experience and her pussy was already wet. She didn't have to wait long, almost as soon as Ned had moved away from her Brett had apparently passed the camera off to one of the other guys already and was in position behind her, his slightly thicker dick stretching her hole as he pressed inward. Even though she was already well-lubricated from Ned's cum and the lube that he'd put there, Brett had put some lube on his cock anyway, knowing that she'd be stretched a little wider when he fucked her hole. Pressing into the slick tight space, Brett moaned as her ass spread for his cock, she felt spectacular. Sloppy wet and still very tight around his very hard dick. Violet felt good too, to her pleasure the stretching of her hole burned a little, but it was a pleasant burn, adding to her arousal and the wetness in her pussy. Rather than working his dick in and out of her as he slid in he just slowly pressed inward without stopping until he was buried in her ass. It was a rather nice sensation really and she gasped a little as the pleasure ran through her body.

Like Ned, Brett reached around and grabbed hold of her breasts, although unlike Ned he ran his fingertips across her hard nipples as well as squeezing her breasts while his dick began pumping in and out of her ass. Violet was starting to feel very horny as her hole burned pleasantly after being stretched, her pussy getting even wetter as a new pair of balls slapped against it. Her nipples liked the attention too. Wriggling her ass a little, she moaned as that caused the dick inside her hole to move side to side in her, creating new pleasant sensations that went straight to her leaking pussy. She began slamming her hips back each time he thrust forward, deliberately clenching her ass tightly as he slid in so that it burned pleasantly for her and he groaned in pleasure at her gripping tightness. Arching her back lustily, Violet found more new angles for him to thrust into her at, filling her with pleasure as the new sensations made her body quiver.

Brett was losing his control very quickly, the combination of the tightness of her ass, her own excited wiggling and the buildup from watching Ned take her first all compounded to make his dick very excited. As Violet began really heaving back against his dick he lost it as she clenched down hard, his dick felt like it was encased with pleasure, the ring of her tight hole squeezing the very base of his cock. Every spurt of cum felt like it was forcing its way out of his dick she was squeezing him so tight, her asshole like a cock ring, enhancing his pleasure as he howled and threw his head back. She was amazing, her rippling ass massaging his dick as it flung jet after jet into her dark hole, mixing with the cum that had already been deposited there.

When his cock had been completely milked dry he pulled out of her with a soft plop, and Violet panted a little. She was now very aroused, her pussy actually leaking down her thighs a little, her ass feeling slightly swollen but very stimulated as well… her swollen clit burned with need. To her pleasure, Hank turned her over on the ottoman so that she was on her back, breasts jutting into the air with her erect nipples looking pink and proud on her chest. Jake and Brett held her legs in a wide "V" shape as Hank pulled her hips to the edge of the ottoman. Behind him, Ned hovered with the camera, getting a shot of her entire body as cum started to drip from her ass.

"That's hot." he said, watching another glob of white cum slide out of her hole and onto the ottoman.

Her eyes slightly glazed with lust, all she said was, "Fuck me please."

Grinning widely, Hank positioned his long black cock at the entrance to her ass. Violet propped herself up on her elbows, watching as best she could as he began pushing in… it slid in easily as it was more slender than both Brett's and Ned's, but it had a much longer way to go. When it only had about 3 inches left to go, Violet's head was already hanging back and she was panting a little, it felt like a very long hard and skinny baseball bat had been pushed up her ass. It burned too, a little uncomfortably as she felt like she was cramping a little, but her pussy was so aroused and wet that it didn't matter as he pressed in until his groin was against her wet pink folds. She moaned as his body rubbed against her aroused pussy and clit, his dick bouncing a little in her ass… laying back down since her arms didn't feel like they would continue to support her much longer, she just relaxed and enjoyed the ride.

Hank began by pulling halfway out and then pressing back in quick and hard, making her body jolt and her breasts bounce on her chest. The guys watched, enjoying the view as he began pounding her hard, her breasts flopping in every direction on her chest as she moaned and clutched at the ottoman. Violet was building to a climax with his body pressing against her pussy and clit every time he was deep in her ass, he was slender enough that he could push easily in and out of her and very quickly too right from the beginning. The impacts against her pussy were driving her crazy. When both Jake and Brett reached down a free hand and began playing with her breasts, she thrashed a little as the pleasure coursed straight to her pussy.

Now juices were freely leaking from her pussy down to her ass where Hank was already making soft squishing noises as he thrust in and out of her sloppy hole. Her ass was so slick with two loads of cum and lubrication, and now her own pussy juices, that even when she clenched down on his dick it didn't slow his thrusts at all. Hank put his hand on her mound, thumb rubbing firmly on her swollen clit as he pounded her slick asshole.

Violet let out a long, high wordless wail as her orgasm crashed over her, her ass clenched tight around the long thrusting dick, and still he moved quickly in and out of her. Her nerve endings burned with pleasure as the friction actually increased as her ass tried to grip his moving dick, and her pussy was quivering with pleasure, her nipples and breasts tingling as her back arched and she convulsed in ecstasy. Hank continued to make circular motions with his thumb on her clit, drawing out her orgasm until he finally thrust one final time and added his own load, much deeper in her ass than the first two had gone. Violet shuddered one last time in orgasmic heat as he added his cum to the mix in her asshole.

The poor girl was completely exhausted as Jake took his place between her legs, and he put her in a new position as well. Turning her slightly on her side, he had Brett continue to hold one of her legs up. When he pressed his thick cock into her ass, it was at a sideways angle, making her shiver as it stretched her ass to its widest point yet and at an odd angle. Her head was resting on the ottoman, completely contented and exhausted, although grimacing a little as her ass was stretched wide. It burned with discomfort, and yet didn't bother her in the least. Jake groaned with heat, her ass was so slick and wet and tight that it could have been a virgin's pussy that he was sliding his dick into. He, like Hank, moved quickly and roughly, really pounding her ass hard. To her surprise, Violet felt her orgasm building again, her body was sensitive to the fucking she was getting after such an intense first orgasm. Moaning a little, she couldn't really push back against the dick in her ass because of her position, so instead she started squeezing her own breasts and pinching her nipples. Ned moved to a position where he could get the entire picture of Violet playing with her breasts while Jake's thick cock ravaged her ass.

Grinning widely, Hank decided to add a little to the tableau, leaning back so that camera could still see everything, he slid two of his thick fingers into Violet's pussy, rubbing his clit with her thumb again as his fingers crooked to find her g-spot. Jake was the most aroused since he was the last to go and had had to watch all the other men partake of her sweet ass first, so he wasn't going to last long. The men all knew this, and Hank deftly worked Violet's pussy as she played with her breasts, quickly bringing her to another, higher, orgasm and she screamed loudly with heat as pleasure rolled over her in waves. With her body heaving and her ass clenching tightly around his dick, Jake didn't stand a chance and he began shouting loudly as he continued to thrust in and out of her slick hole as his cum was added to the mix.

His thrusts got slower and slower as his dick finished unloading and began to soften, and finally he stopped altogether and pulled from her ass. Holding her leg high, Brett also reached his other hand down to lift up her cheek, giving Ned and the camera a great view of her gaping hole, filled with four men's sticky white loads of cum. Violet just lay on the ottoman, completely exhausted.

She went to the bathroom after resting for a bit, and then came out and talked and joked with the men who fixed her a drink and gave her some food as well. It was almost 3 in the morning when she finally left. They saw her to the door and she gave all of them an extremely affectionate kiss, and although she was walking rather funny as she went to her car she was very satisfied and happy.

However, when she got up that afternoon she decided she would definitely need that evening off to recover. Her ass hurt.