Blowjob Contest Ch. 05

"You make me cum like I've never cum before. I'm starting to feel guilty that I leave you like that," she motioned to his throbbing cock that looked like it might explode from the inside out it was so engorged.

"Six more days," he said.

"Yeah, six more and you're free. You're amazing to put up with this. You're the best boyfriend I've ever had," she said, sitting up and kissing the purple head of his engorged cock.

He wanted to grab her head and fuck her mouth until he came. It would be a perfect ending to fucking her today but he knew he couldn't. Not yet anyway.

When Rachel kissed his cock, she had a huge urge to suck him. It was all she could do not to grab hold of his hot, throbbing shaft and suck him off until he exploded in her mouth. She wanted to so bad it hurt, making her exhale loudly with frustration.

"What's wrong?" he asked.

"I would tell you but it wouldn't help your situation," she said.

"Tell me anyway."

"Okay, but you better step back," she began. He stepped back as she continued. "I just got the huge urge to suck you off until you cum in my mouth. Standing like you are it would have been perfect way to finish you off."

"Fuck! That was exactly what was thinking!" he gushed.

"Well, at least we are on the same page," she said, despondently.

"Cheer up, six days will go by fast," he said, lying to her.

"You're a bad liar," she smiled and stood up.

His cock wasn't going soft and she stared at it hungrily. "You better get dressed or something because I can't take seeing your cock like that and not do something to it."

"Okay," he said, turning around to gather his clothing.

His clothes hid the erection from view, but did nothing to calm his urges or hardness. "Well, I was hoping this would go down a little before my next class but I guess not. I'll have to walk across campus with a hardon again."

"Sorry, sweetie. I'll see you tonight, after classes... Oh wait... I can't tonight, I've got plans with the girls," she said, remembering her anal practice.

"That's fine, probably better we keep our distance as much as possible for this last week."

"I don't want to," she said, embracing him at the door.

"I don't either but it's better not to chance ruining the contest. It's almost over," he said, hugging her back.

She felt his hard cock press against her body, her loins twinge and a letdown of arousal in her sex.

They broke the hug and he kissed her quick before darting out the door, leaving her naked and alone in his room.

**

Sam was on her hands and knees on her bed, her large breast rolling forward and back as Jordan fucked her from behind over and over. They had been going at it for over an hour, making up for the time off last week. They were changing positions like porn stars, keeping Jordan from cumming too soon. He had her by the hips, slamming his cock deep each time and admiring her sexy ass and back, with an occasional glimpse of her side breast as it rolled into view. His cock making sloppy moist noises as he penetrated her, finishing off with a slap as his hips met her plump round ass.

He liked finishing on her tits and this position didn't make that very easy, unless she rolled over on her back when he pulled out. He doubted she would think of doing it, especially the way she was acting. She had cum twice already and was apparently on the verge of another one. Grinding away at her clit was helping. He could feel her fingers graze his shaft as she played. He could hear her breathing increase and her legs began to shake as the orgasm took over her body. She started panting and ended up collapsing on the bed in a fit of pleasure. Jordan was getting close but he still had some work to do, but with Sam falling on the bed, his cock had popped out of her quivering pussy, leaving him wanting.

He gave her a few seconds to calm down and to see what she would do. She was usually really good about making sure he came so he waited patiently. Slowly she rolled over opened her eyes with the look of contentment on her face.

"Three times, Jordan... you made me cum three times, I'm exhausted," she said, looking up at him.

"I told you we had to make up for last week."

"You sure did. Now you need to cum, but my pussy is done and you probably don't want a blowjob," she inquired.

"It's fine if you want to do that," he said.

"Why don't you slide between my boobs and finish on them," she said.

"Oh... okay... great," he said, crawling toward her.

He threw his left leg over her body, positioning himself below her large breasts. She had the best breasts for tit-fucking ever. All she had to do, once he placed his cock between them, was push them together. Her cleavage was so deep and firm his cock stayed put even without her hands over the top. His cock was lubed pretty well from her wet sex but as he started to slide back and forth between her breasts, both of them could feel it begin to dry out. Leaning forward, she released her breasts and let him put his cock in her mouth, where she added a lot of saliva she had been saving up in anticipation of this very thing. Back between her tits, Jordan fucked them faster and faster, letting the bliss rise unfettered.

His balls tightened on her lower chest and he admired the huge breasts around his cock as his orgasm approached. He was one lucky son of a bitch to have a girlfriend this hot and this endowed. He loved watching his cock head poke out the top of her cleavage and the added stimulation actually made her nipples harden and pull her areolas tight and darker. He was on the verge and lost it when she leaned forward again and licked his head as it reached its furthest point. A huge burst of cum shot forth into Sam's mouth, catching her off guard. She spit the semen out and released her breasts as another shot hit under her chin and pooled on her neck between her collar bones. Jordan grabbed his cock, sat up a little more and stroked the rest of his load onto her breasts, making sure to give each its fair share. The hour long sex session produced a significant load and by the time he was done, each of Sam's large, perfect breasts were painted well.

"Wow, look at all that cum... you like climaxing on my boobs," Sam stated.

Jordan smiled down at her and pressed his cock head against one of her rigid nipples, swirling it around in his semen. He played for a few more seconds before she shook her head and told him to find something to clean her up. If she let him, he would have twirled his cock in the mess until he was completely soft. He liked playing in his load, especially on her breasts.

"You're going to be late if you don't stop," she said.

"I'm already late," he said, moving his cock over her nipple and breast one more time before getting up.

He found a towel and returned to the bed to clean her up. He admired her semen covered breasts one more time and she swore he almost looked sad he had to wipe it all up.

**

Rachel spent the rest of the day alone, thinking about the evening practice session upcoming with her friends. She attended classes, studied a little but her mind was preoccupied with the medium plug. She remembered the wonderful orgasms from the smaller one and wondered if a bigger toy would produce a bigger orgasm. She got a few texts from Brandon but they didn't see each other the rest of the day. Her last class ended and she headed back to her dorm room only to find all three of her friends already there. She was slightly surprised to see Becca but didn't mention anything about it.

"You guys are early," Rachel said, dropping her book bag on the floor next to her bed.

"Nothing else going tonight," Julie said.

"You didn't cancel plans on my account did you?" Rachel asked.

"Maybe, but what are friends for," Julie said, laughing.

"I don't know if I should feel honored or embarrassed," Rachel added.

"You're just being smart, planning ahead for the inevitable," Sam said, turning around in her chair.

She had been studying when Rachel came in. "We all know how big Brandon is, might as well make it as enjoyable as possible for both of you," Sam continued.

"She's right. Brando's a nice guy and if he sees he's hurting you he won't have as much fun as he could. I'm not saying he'd stop, not after what he's been through, but if you take him relatively easy it will be better for both of you," Becca joined in the conversation.

"That's a good point, Becca," Rachel said, smiling at her. "You probably want to see the plugs," Rachel continued, walking over to her dresser and retrieving the collection of plugs.

She carried them over to her bed with some lube and Becca joined her, sitting on the bed to examine the plugs.

"Wow, the large one is wider than Brandon... if you manage to take this okay, you shouldn't have a problem with him."

"That's the plan. But today we're going to try this one," Rachel said, picking up the medium plug. "It's just a little smaller than Brandon's width, so it will be good practice before the big one."

"So when do we get started?" Julie asked, excited.

The rest of them laughed and Rachel said, "I've got to use the bathroom first and then we can start."

**

Rachel was glad the animosity between she and Becca had seemed to vanish. Rachel wasn't really mad at her anyway, not now that she had Brandon and it was Becca that pushed her over the line to finally dump Ryan. Becca can be a bitch at times but she usually was the most honest and blunt of her friends.

Rachel used the dorm's bathroom and returned to her friends, who were eagerly awaiting her to come back. Maybe too eager.

"You ready now," Julie asked, rolling the medium plug in both hands back and forth.

"You guys are making me a little nervous," Rachel explained.

"Why? We're just here to help," Julie said.

"Then help, don't pressure me," Rachel said.

Julie dropped the plug on the bed and shrugged her shoulders. Rachel locked the door and kicked off her shoes. "For some reason you guys have made me hesitant, which is weird since I've been thinking about this for most of the day."

"Just come sit on the bed and relax," Sam said. "We're in no rush."

Rachel joined the other three on the bed. Sam started rubbing her shoulders, helping her relax.

"You are a bit tense, I can feel it in your shoulders," Sam said.

Sam's hands felt good and Rachel rocked her neck back and forth as Sam kneaded her shoulders, helping Rachel feel calmer. After about a minute, Rachel reached down and pulled off her shirt, leaving her bra on. Sam continued, working down her back and up to her shoulders again.

"There you go, getting looser now," Sam said, unclasping Rachel's bra.

Rachel didn't mind, letting it fall off her small, round breasts. She felt her nipples tighten and a stirring in her sex for what was to come. Sam slowed her movements and Rachel lay down on her back. Julie helped her out of her socks and shorts until all she had on was her panties. Those soon were gone and Rachel was naked lying on the bed with her three friends surrounding her. Rachel closed her eyes and let her hand glide down her flat stomach to her shaved folds, barely brushing her fingers over the sensitive skin. A rush of arousal seized her and she took in a sharp breath, adding more force to her folds.

With the tips of her fingers she grazed the skin folds over her clitoris, sensing it begin to plump with blood. Her heart rate increased, her nipples hardened further and the skin began to pull back off her nub until her fingers came in contact with her sex organ. She arched her back and pressed harder; moaning softly and pretty much forgetting her friends were even in the room until the cap popped open on the lube.

Rachel peaked through her eye lids and saw Julie squirting lube on the medium plug, wiping it around with her finger. Rachel closed her eyes fully again and ground down on her plump clitoris before letting her fingers spread her sex open to find her wet vagina beneath. She felt Sam's and Becca's hands on her legs, spreading and lifting them for access to her anus. Once she was exposed her friends wasted no time. Rachel felt the cold end of the plug touch her puckered hole. Thinking Julie was going to go slow, she wasn't worried but then the unthinkable happened.

Julie was too excited, too eager to put the medium plug inside Rachel's ass and pushed too hard too soon. A sharp, excruciating pain gripped Rachel's ass to the point she screamed and pulled away from Julie's hand. The plug wasn't fully inserted but it didn't matter. Julie had gone way too fast and Rachel's ass had tightened up even with the lube. The pain was horrible; causing Rachel to cry out and roll on the bed even after the plug was pulled out.

"Fuck, fuck... Shit, what the hell did you do?!" Rachel screamed.

It was the worst pain she'd ever felt down there before and it wasn't going away. Her ass was cramped and the pain was intense. Sam and Becca looked accusingly at Julie who seemed about to cry as Rachel continued to squirm on the bed for over a minute until the pain began to subside.

"Oh, shit... maybe this wasn't a good idea," Becca said.

"This didn't happen yesterday," Sam said.

"Yesterday, Julie didn't try and impel me before I was ready!" Rachel hollered.

"I'm sorry; I guess I went too fast."

"You think! Fuck! I've never felt anything that bad before... it just kept hurting and I couldn't stop it," Rachel explained.

"Well, I guess we learned something then. You're going to have to be very ready for Brandon or this might happen again with him," Becca stated.

"I can't stand that again... I can't, maybe he won't ask for anal... maybe I'll just turn him down if he does, but I can't do that again," Rachel blubbered.

The three other girls looked at each other worried. They knew Brandon would and they knew he would be very pissed off if she didn't let him, especially after what he's gone through and what she had promised.

"Now, let's just take a minute and think about this," Sam began. "It's going to be okay. You'll get past this, but you know you can't say no to him, Rachel."

Rachel took a second or two to consider what Sam had said. Then she spoke, "I know... but man that fucking hurt. I know I've got to try."

"This might be a good thing," Becca began. "I mean at least we know what caused it and we can learn how to avoid it with Brandon."

"Yeah, I guess," Rachel said.

"Do you want to try again tonight or wait until later?" Sam asked.

Julie wasn't saying anything. She felt horrible for what she had done and didn't want to speak, fearing she might make it worse.

"We need to try again, I don't have much time before Julie's turn with Brandon, but maybe I should be the one putting the plug in my own ass," Rachel said, staring at Julie.

"Here, sorry," Julie said, handing the slippery toy to Rachel.

The pain had pretty much disappeared with only a slight murmur of remembrance on the tight right of Rachel's sphincter. She took the plug and lay back down with it in her left hand. She began touching herself with her right, and immediately enjoyed her fingers on her sex once again.

She played for a few minutes before speaking gain. "Maybe you guys could use your fingers and start adding some lube and maybe the tips of your finger at first."

"I'll do it," Becca said, popping the cap on the lube again.

Rachel closed her eyes once again and began grinding on her clit and sex. A few seconds later she felt the cold slippery lube on Becca's finger find her tightly puckered asshole. Becca only rubbed it around and it felt really good to Rachel, who sped up on her clitoris. A little time later, Rachel felt Becca pressing firmer on her tight opening with the pad of her index finger. Rachel relaxed and her tight hole opened slightly for Becca's finger. Soon, Becca inserted the tip, and Rachel let out a pleasure moan, sucking Becca's finger deeper.

"Oh yeah, now that's much better," Rachel said. "Just hold it there for a bit."

Rachel felt the familiar pleasure she had looked forward to, glad the pain hadn't returned or hadn't left any permanent damage. She played and played, letting her arousal climb to where she was humming with pleasure.

"Use the small plug now, I'm ready for it," Rachel said.

Sam found it and added more lube. When Becca took out her finger, Sam eased the small plug in without any resistance. It was wider than Becca's finger and felt amazing to Rachel who started to cum as the end cap pressed against her butt.

"Fuck! I'm cumming!" she screamed.

"Damn, she is," Becca said watching her friend shake on the bed as she ran her whole hand up and down her sex.

"I told you she has amazing orgasms with the plug," Julie added, watching the whole time.

Sam was holding the small plug in because Rachel's contractions almost pushed it out before Sam caught it and eased it back in. Rachel came for over a minute before falling limp on the bed and breathing heavily. Her friends waited for her to return to the present, which took a couple more minutes.

"Oh wow, I hope I can cum like that with Brandon. It's amazing with the plug," Rachel said, returning her hand to her very damp sex.

She played while her friends watched and waited to see what she would do next. "I think I'm ready to try the bigger one. Sam, pull out the small plug for me."

Sam grabbed the slippery end cap and twisted the plug around and around as she pulled it out. It fell out easily and just as it did, Rachel pushed the medium's tip into her ass before it closed. She spun it around slightly and all eyes were on her.

"Okay, here it goes, nice and slow," Rachel said, pressing firmer on the end of the plug.

The three watched in awe as the rubber plug began to disappear into Rachel's ass very slowly. It widened and stretched her tight ring with each millimeter.

"Oh wow, it's definitely bigger," Rachel breathed, feeling the strain.

She paused, breathing heavily and wanting to play with her clit better, but it was difficult to do both. She didn't know if she trusted he friends to go slow enough but she did want the help. She looked around at them and decided to ask Becca to help this time.

"Becca, I want you to do it for me so I can play. Just go really slow and listen to me, okay?"

"Okay, I got this," Becca said, taking the exposed half of the plug in her hand.

Rachel immediately began playing with her sex with both hands, and the very act loosened her enough for more of the plug to ease in without Becca really doing anything.

"Oh, much better. Gawd it's so much better when I play," Rachel gushed.

The plug was about an inch away from the widest part. Becca took her time, just turning the plug gently back and forth before trying to press anymore in. She watched Rachel, she could tell when she was ready for more because the toy spun more easily and Rachel's nipples hardened as another orgasm neared. Becca pressed gently on the end cap and a half of an inch entered Rachel before she stopped.

"I'm okay... keep going," Rachel said, feeling the plug widen her more.

And suddenly with one more push, the plug popped past the widest part and into Rachel's body. They watched her tight ring hug the rounded plug until it slid down to the narrow neck before the end cap.

"It's it!" Julie screamed.

"Yep, sure is," Becca said, pressing the end up against Rachel's ass and letting go.

"How's it feel?" Sam asked.

"Not bad at all, it's bigger, fills me up more and now that it's in there is no strain at all."

"Yeah, that could be a problem," Julie suddenly said.

"What? Why?" Rachel asked.

"Well, Brandon's cock isn't shaped like a plug. He's going to be stretching you wide all the time he's fucking you. You're going to have to get used to a wide object sliding in and out for a while, probably."