Blowjob Contest

The medium plug was a success, well... after it was done right, anyway. Rachel woke up wondering if her ass would be sore from the evenings 'practice'. She was pleased to find it wasn't. No ill effects hampered her even after the horrible pain she felt when Julie went too fast. Rachel was on track to be ready for Brandon. All she needed was to handle the large plug and then practice with her new Anal Twist to make sure she could handle a wide object repeatedly thrusting in and out. She had a few more days to make it all happen. She doubted Julie would beat Sam's time, and really it didn't matter, Rachel was out of the running anyway. She just wanted the contest to be over so she could have Brandon fully with no restraints on him.

Rachel had slept well again. All the orgasms before bed made her sleep so soundly she couldn't even remember dreaming. She had woken up before her alarm even, feeling wide awake. In the dim light she watched Sam sleep in the bed across the room. She was on her back, her large breasts rising and falling slowly with each breath. Rachel thought to herself, "Those tits gave her a big time advantage and she knew how to use them." Rachel really didn't care; she ended up with a great guy from the contest so she considered herself the winner even though no one else did.

Figuring since she was already up, Rachel turned off her alarm and headed for the showers. The only other person she saw up was Becca, heading to soccer practice.

"Hey, going to soccer?" Rachel asked as Becca stepped out of her room.

"Yeah, wow, you're up early. What's the deal?" Becca asked.

"I slept great and woke up on my own. Figured I'd just go and shower and maybe study before class."

"Huh. Well okay... must have slept so well because of last night," Becca said.

"Yeah, I think so too? I was exhausted."

"You looked like it was worth it though."

"It was. Anal is surprisingly good, well... if done right," Rachel said.

"Yeah, if done right... we learned that, didn't we?"

"Yes we did."

Becca smiled and headed to soccer. Rachel showered all alone and took extra time since she had it. Back in her room, Sam was just getting up when she returned.

"You already shower?" Sam asked, when Rachel came in the room.

"Yeah, I woke up early."

"Wow, that's new."

"I know, right?"

**

Brandon woke up with a hardon like normal. Placing his hand around it, he stared up at the ceiling of his dorm room and thought about Rachel and the deal she had made with him. The words echoed in his mind over and over. "Just remember I'll make it worth it to you. You can fuck me in any hole you want and cum anywhere you want as much as you want."

He squeezed his cock thinking, "She does realize what she said? She does realize where she has basically given me permission to fuck? She's got to know I'm going to put my cock in her ass, right? She has to. She wouldn't have said "any hole" if she wasn't planning on me fucking her ass."

He stroked his cock just one time. Shit he was horny as fuck and if it wasn't for this damn contest he would have grabbed a sock and rubbed one out. His mind was preoccupied with anal sex now and it was all Rachel's fault. He wondered if she hadn't said anything if he would have ever thought about doing anal with her. It's not like their budding relationship needed some adventure already. Hell he was very content with her mouth and pussy. But now he had a chance to have a girl's ass for the first time. He couldn't let that slip away. He had to go for her ass once this contest was over.

He grabbed his phone off the nightstand next to him and typed into Google, "How to have anal sex for the first time." When he started reading, he noticed most of the results were written for the woman and how she could prepare for anal sex. He figured the guy had the easy part. He read a few, most said the same thing. Relax, go slow, and use tons of lube, the standard stuff. He also read about women using plugs before anal to loosen themselves up and to prepare ahead of time. He wondered if Rachel was doing anything to prepare. The horror stories he read worried him. About women saying how horrible it was, how bad it hurt and it ruined sex for them. Brandon wondered if it would be worth it to even try. He didn't want to hurt Rachel or worse, ruin their new relationship. He considered not asking for anal, but every time he did, he couldn't kick the thought that this might be the only time he'd get the chance. You don't throw once-in-a-lifetime chances away, you just don't.

**

The entire gang didn't meet up until biology, and that included Brandon. Before class started, Sam asked Rachel when she wanted to try the large plug and the dildo thingy.

"I can't tonight, but tomorrow we will, that gives me another couple of days to try if I'm not successful."

"Okay, so not tonight but tomorrow. Why not tonight?" Sam asked as they walked to class.

"Brandon has invited me to hang out with his buddies. Probably will be late."

"Okay, well then I guess I'll expect you late tonight."

Rachel smiled and the two walked into class. Later on in biology Julie asked Sam about more 'practice' for Rachel.

"Nothing tonight. She wants to do it tomorrow."

"Okay, cool... I'll go to Rob's tonight then," Julie said.

After class everyone went their separate ways except Brandon and Rachel. They went together to the library to study. Even if they couldn't have much sex, they still liked to hang out with each other.

"So what are we doing tonight with your friends?" Rachel asked as the two of them sat across from each other at a library table.

"Nothings really planned. Probably just hang out at my dorm and talk. The guys wanted to meet you."

"They've met me, right?"

"Sort of. We usually just disappear into my room when you come over."

"Yeah, I guess."

"You don't sound excited. Would you rather do something else tonight?" he asked.

Rachel's mind immediately went to the large plug. There was something she rather do, but she also liked to be with Brandon and had told him she would hang out tonight. She shook her head no after the slight pause.

"Are you sure, you just looked like your mind went elsewhere. What were you thinking about?" he asked.

She couldn't exactly tell him the truth and blurt out wanting to try and fit a huge buttplug up her ass so she could be ready for his big cock. The thought did cross her mind as did the words. She grinned without knowing it and he shook his head at her.

"You have the most mischievous look on your face I've ever seen. What is up with you?" he asked.

She didn't want to lie to him and apparently her thoughts and expressions had given her away.

"Fine, I'll tell you. It's about that promise I made you... you know the one for after the contest," she said.

"Yeah, what about it? You're not thinking of going back on it are you?" he asked.

"Oh no, nothing like that... but it has been on my mind and I'm sure it has been on yours."

"I'd be lying if I said no," he said.

"Exactly and I'm not stupid and you're not stupid so we both know where you'll want to put it, right?" she asked.

"Yes, I suppose... so you're nervous?" he asked.

"Not nervous as much as being proactive," she said, smiling.

"What's that mean?"

"Alright, I'll just tell you... the girls have been helping me prepare... kind of practicing."

"Practicing?" he asked.

"Yeah, getting me ready," she said, looking around at the others in the library. "You don't want me to say it out loud do you?" she asked.

Brandon was speechless. A myriad of thoughts and images flashed in his mind, many of them very accurate to what had actually happened. He just stared at her, thinking about the three girls around a bed helping stretch Rachel's ass out. It was something he could scarcely imagine seeing.

"Brandon? You okay, Brandon... you left me for a second," Rachel said, getting his attention back.

"I'm fine, just trying to grasp what you just told me. So how long have you guys been practicing?" he asked.

"Not long, just since Sam and you and I realized I only have a week before the contest is over."

"I see, so you'd rather be preparing then hanging out with my friends tonight."

"It's not that, it's just on my mind. I already told the girls that we can't tonight so I'm all yours I promise."

"I could help you practice?" Brandon let the idea in his head out.

"What? You serious? But wouldn't that make you crazy and it even harder to keep from cumming," she said a little too loud.

A couple of girls on another table looked at them with big eyes and open mouths.

Rachel shook her head, stood up and started packing her books in her pack, "We can't talk about this here."

The two of them hurried out of the library and without thinking headed in the general direction of Rachel's doom room.

"I think if I just keep my clothes on I'll be okay," Brandon said as they walked.

"You really don't have to do this... Sam, Becca and Julie have really helped a lot and I'm progressing well."

"I want to... trust me I could learn as I go too."

"That's a good point... I was wondering how I could explain things when the time came. I know you're going to be excited and..." she trailed off.

"And I might hurt you in my excitement?" he asked, looking down at her.

She nodded. "I've done a little research myself. Practicing will be a good thing," he said.

"Okay... I guess but what about your friends?"

"Who?" he joked. "Trust me if they knew what I was going to do instead they'd understand."

Rachel giggled and they quickly walked to her dorm.

**

It had been a while since Becca had had sex with Jim. Last night's anal practice with Rachel had gotten her so horny but it had been too late to run over to Jim's dorm with soccer practice the next morning. All during practice she thought about anal and had worked herself up with the exercise. She took a cold shower to try and calm down. It hadn't worked. After biology she went right toward Jim's place intent on attacking him like she had the other day. Problem was, he wasn't in his room when she showed up. She remembered what day it was. He had classes for most of the day, making her problem even worse.

She felt like texting him and asking him to leave his class and attend to her, but she knew how hard his classes were and if he missed just one he would get behind and not know the material. She decided against it, trying to remember when he had a break or when his last class was. She pulled out her phone, still standing in the doorway to his room. One of his roommates had answered the door and was looking at her working through something. He knew exactly why she had come over and why she looked so flushed. Jim's roommates weren't dumb; they knew what the two of them did when she came over like this. He had told her Jim wasn't there and had seen the disappointment and frustration on her face.

"Hey, since Jim isn't here, maybe I could help you with something," he said with a stupid grin on his face.

Becca looked up slowly from her phone, caught the guy's eyes and said, "You wish fuck face," and turned around and left. Jim's schedule had him busy all afternoon. She needed it right then but didn't know what to do. That was when she remembered Rachel had mentioned buying some kind of dildo to practice with after taking the large plug. Rachel had passed out last night and hadn't shown Becca the new toy but the idea got stuck in Becca's mind. She decided since Jim was occupied she might have to pay that new toy a visit in Rachel's room.

**

Rachel let Brandon into her room and closed the door behind her. She was excited everything was out in the open and that he was willing to help her prepare. She knew it would be better when the time finally came for her to make good on that promise if Brandon was well versed in anal play. She walked across the room toward him and went to her dresser.

"Okay, so I need to show you something and explain what I've already done to prepare. Kind of catch you up on everything," she said.

"Okay," he replied.

One after another she started bringing out her toys she had purchased including the Anal Twist and set them on the bed. She turned and saw Brandon's expression.

"I know it's a lot but I had a plan. Small, medium and large," she said pointing to each. "With the girls helps I've managed to accept the small and medium plugs. We were going to try the large one next. As you can see it's really wide."

"Yeah, wider than me," he said.

"Yeah, so that's good, right? If I can handle this I can handle you?"

"Makes sense," he said, adjusting his growing cock. It was unavoidable.

"Exactly so that's the next challenge but I need to tell you some things before we try."

"Okay, so what's the long one for?" he asked.

"That's for after I manage the large plug. You're not shaped like a plug nor will you just stay still inside me, so hence the long toy," she ginned at him.

His cock lurched in his pants. He knew it was official then for sure. He was definitely going to fuck her ass, no questions about it.

"So what do I need to know before we get started?" he asked.

Rachel explained what had happened when Julie got to anxious and the pain that she had felt. She told Brandon exactly what had happened and how to avoid it.

"It's all about making sure I'm ready, there is nothing fast about it."

"I understand, I'll be extra careful now and in the future," he said.

"Good, I'm so glad we talked about this and you're going to help ahead of time. You ready to start?" she asked.

"Sure, if you are."

She started taking off her clothes in response and was soon butt naked in front of him. It was then he started rethinking this little idea. How was he not going to fuck her, would it be physically possible?

She climbed on her bed and laid among the toys and lube. He just stared at her, afraid to move, suddenly not trusting himself.

"Well, come on... come get me ready."

**

Becca entered the dorm, passing her own room, heading directly to Rachel's and Sam's. She didn't even knock, opening the door and rushing in only to find Brandon fully clothed with his head between Rachel's legs, munching away at her, surrounded by the toys.

"Fuck! Becca what the hell!" Rachel screamed.

"Oh shit, sorry... I didn't expect you to be here!" Becca said, already turning to leave.

"What did you want?"

With her back to her, Becca said, "Jim's in classes and I'm really needing some. I came for that dildo thing you mentioned."

Rachel started to laugh, "Wow... going to use my new toy before me huh? You must really be in a state."

"I am, but I'm leaving... I'll figure something out," Becca said closing the door behind her.

**

Brandon had paused temporarily when he heard the door open behind him. He heard the exchange between Rachel and Becca, as brief as it was. When the door closed he said nothing, just proceeded to suck Rachel's clit back into his mouth and tease it with his tongue.

"Can you believe that?" Rachel began, "she came looking for my toy. Was just going... to take it for... herself... oh yessss, that's... so... good."

Brandon grunted a reply before proceeding lower to start licking Rachel's little puckered asshole. His cock was extremely rigid in his pants, surely making a huge mess as it oozed from his excitement. He told himself that as long as he kept it in his pants he'd be able to keep from fucking her and more importantly, cumming.

"Mmm, I'll deal... with her later... keep doing what... you're doing," Rachel struggled to say, falling back down on the bed and enjoying the tongue easing into her ass.

Brandon soon had as much tongue as he could inside her, wiggling it around and out and in for a few minutes before she spoke again.

"Now use your finger... You're doing great, sweetie."

He'd never put his finger in a girls ass before. His heart was racing from the excitement but he knew he had to go slow even in his eagerness. Slowly, he eased the tip of his index finger into Rachel's wet hole. It went in easy with all his saliva and he was soon up to the second knuckle without any issues. He pulled back out and eased it in again and again, fucking her with his finger. His cock throbbed in his pants like no other.

"Yes, that's perfect... lick and suck my clit as you do it," Rachel said.

He lowered his head and started sucking on her clit again as he fucked her ass with his finger. It only took a minute before Rachel was wigging out.

"Oh my gawd, yes... I'm ... fuck... I'm going to cum... Shit! Like now!" Rachel screamed as her orgasm took hold of her body.

Rachel's ass clenched down on Brandon's finger as the convulsions began. She squirmed and shook as each wave crested over her, so much so he was forced to stop sucking her clit but managed to keep his finger deep inside her ass as it repeatedly clamped down over and over. He couldn't believe how quickly she was cumming from the anal and oral play.

Rachel felt her ass clamping on his finger and wanted something bigger, knowing how good it could feel. She struggled to talk among her climax, begging Brandon to find the medium plug. He found it easy enough and removed his finger, placing the tip of the plug in its place. He pushed slowly, watching the clear rubber start to disappear into his hot girlfriend's pulsing ass. It was an image he'd never forget for the rest of his life. Slowly, inch by inch, Rachel took the medium plug, stretching her ass until it popped past the widest part and into her body.

"Yes!!" she screamed as the plug seated against her cheeks as her climax continued.

Brandon had never seen anything like it before. He watched the plug's end cap move out and in as her ass continued to contract on the toy. Secretions oozed out of her sex and her clit was rock hard and easily visible, pressing out amid her flushed folds.

Minutes later, Rachel finally began to come down from her climax, breathing heavily and falling limp on the bed. The plug was still tightly in her ass.

**

"Fuck! Now what am I going to do!" Becca grunted under her breath as she entered her own dorm room.

She checked her phone for the time. Not much had passed since she left Jim's dorm, it was like time was mocking her and Jim was an eternity away from being out of class. Sure, she could undress and play with herself with her hands, probably have a little climax but for some reason she wanted a cock, she wanted something big inside of her and now all her options had disappeared. She looked around her dorm room but couldn't find anything larger than a pencil or toothbrush. She never needed a toy of her own, not until right then anyway.

Getting desperate she started going through Julie's drawers and nightstand, a big no no, but desperate times made a girl do things she normally wouldn't. Still no luck. Julie apparently didn't need a toy either. Becca was sure Rob had something to do with that. In her frustration, Becca actually considered going back to Jim's roommate, but quickly brushed the idea out of her head. Then she saw it. The six inch oval footboard post on both her and Julie's beds. She wondered why she hadn't thought of it before. She could easily squat over it and fuck herself good and hard. The post was wider than any cock she'd ever had but that was exactly what she was craving.

She locked the door to her room, quickly removed her clothing and laid down on her bed to prepare herself for something so big. She wasn't surprised to find herself very wet already but she took some more time to make sure she was well aroused before attempting to take the post into her body. She traced her fingers around her sex, gently caressing her lips and brushing the folds hiding her clitoris. Her nipples hardened as she began to get more aggressive, pulling the skin up with one hand to expose her growing nub to her other hand. Licking her finger she moved back and forth across her sex organ with her index finger, biting her lip in the process. She was highly sensitive and couldn't believe how horny she was.