Coach Wendy

All characters are 18 or older.

This collection of stories is set at St. Benedict's and can be read in any order. Categories will vary from story to story as appropriate.

St Benedict's is a rich kid boarding school where lost-cause rich kids go to be babysat. They are bad students and grades don't matter. The teachers and staff are equally bad, with low expectations.

The unofficial motto is: "Where rebels thrive and trouble is the norm"

****

Wendy opened the door of the bathroom to an inch of water on the floor of her motel room. She had been getting ready for her shower after a blowout game against district champs, Romango High. Her guys had put in a valiant effort, but lost by 3 three runs in the last inning.

She looked around in shock. The roof caved in and water streamed in through the hole. Storm clouds showed through the hole.

Everything she had was completely soaked from the rain streaming in. Her bag with all her clothes was under the pile of rubble. The bed was destroyed. Even if it too wasn't soaking wet, it wasn't supporting anyone now.

Even her phone was soaked. It wouldn't power on at all.

Two of her players, Bob and Roger rushed over to her room and looked in.

"Hey guys, I seem to have a little water in my room," she said sardonically. "Everything I have is soaked, my phone is dead, and all I have to wear is this towel."

They looked at her, wrapped in the chintzy motel towel. Her 6-foot form towered over both of them. It barely covered her. She had to hold the ends together to stop from flashing them. If she moved too fast, she'd be exposed to them.

"Come to our room, Coach, I might have something that'll fit you," said Bob, the taller of the two.

"I'll grab your stuff," Roger said. He brushed by the coach, to clear away the roof debris.

She followed them as Bob rifled through his bag. "You can try these."

She took the shirt and shorts and went into their bathroom.

"Jesus, what a mess," she said to the mirror. She took the shirt and shorts and tried them on.

Bob was a couple inches shorter than his coach, so his shirt rode high, showing several inches of her belly over the top of the shorts. Her B cup breasts would have to go unsupported since her bras were sitting in her room drenched. She wasn't really worried about that, but her nipples poked through the shirt. She usually wore padded bras to avoid this very situation. Everyone who saw her would know she was braless.

"At least it's only for a little bit, until I can get a new room."

They stood when she came out. "Thanks for the clothes, Bob. I'm going to the front desk."

After she left, Bod said, "Holy shit, Roj, did you see her nips? I had no idea they were that big."

"I know, right? Fucking awesome. Sucks about all her stuff, but worth it for how she looked in that towel. She's got legs up to her neck."

Roger opened the door for the coach when she knocked. She stomped in, annoyed.

"What's up coach? Are they putting you in another room?"

"Ugh, no!" She paced back and forth. "They are all booked up and don't have any open rooms. They called around and no one else has any vacancies nearby either."

Bob and Roger shared a look. "You can stay here, Coach. We have two queen beds here," Bob said.

"Yeah, Coach, it's no problem. We'll share a bed and you can have Bob's." Bob glared at Roger.

She saw Bob's look and grinned. "You don't have to do that. Like you said, it's a queen. Lots of room for two."

"Are you sure? I don't mind sharing a bed with Roj." His face said the opposite though.

"If you can behave yourself, we'll be fine. I have this to wear to sleep in." She waved her hand at the ill-fitting clothes. "Before that though I'll hang up some of it and maybe it'll be dry by the morning."

They got her bag and she proceeded to hang her clothes up wherever she could. The bathroom looked like an old washwoman's room when she was done. Her underwear hung from the line in the shower and her shirts and pants over the rod.

"So, guys, what did you have planned for tonight?" She asked when she finished hanging.

"You're pretty much looking at it," Roger said, laid on his bed, TV on.

"Really guys? Young studs like you were just going to sit around and watch TV? That's not very much fun."

"Pfft, I don't know about stud," Bob said.

"Come on, I know you guys have fans. I see them in the stands during home games," she said. "You're telling me that you haven't had some groupie action?"

Bob blushed, and looked down. "Coach, Bob is like really shy around girls. He couldn't close the deal if his life depended on it." Roger laughed at his friend's discomfort. "Me? I do just fine with the ladies."

"Roger, that's not nice." To Bob, she said, "You are a good-looking guy, you just need to practice. I have an idea, how about you practice on me."

"On you? What do you mean?" Bob asked.

"I'll be your practice dummy."

****

In the shower, Wendy thought about Bob's bumbling practice at flirting. She smiled at his awkward attempts. He was sweet, but almost terminally shy. It was curious how confident he was on the field, but he couldn't talk to a woman. Roger on the other hand, he was a shameless flirt. He knew how to talk to women, and didn't hesitate to do so.

As she soaped up her body, she thought about her missed chance to play with herself. She had planned on a quiet night in her room reading some erotica from her favorite site, but she couldn't do that with her phone dead, and certainly not in the same room as them.

It had been a few months since she'd been with a man to take care of her needs, so she took her pleasure in her own hands, and vibrator. She thought of her little waterproof vibrator sitting at home. Tomorrow night she'd be home and could take care of herself then. Until then, she'd just have to do without.

She emerged from the bathroom drying her short hair. Back in her borrowed clothes, her nipples poking through the material. Neither of the boys missed that fact.

"Okay guys, we should get some sleep. It's been a stressful day all around."

Bob was already under the covers, and she got in facing away from him. She was asleep not long after the lights went out.

****

Wendy woke up with Bob pressed up behind her. His hand squeezed her breast under the shirt.

"Bob," she whispered. "Hmm," he moaned against her back.

Then she felt him press against her butt. He was hard and pushed up against her.

His hand squeezed her breast, her nipple between his fingers. When he pinched her nipple, it sent shocks directly to her pussy. Her body loved having her nipples played with, it was a surefire way to get her wet and ready for fucking.

He pulled her shorts down, ass exposed. A jerk of his hips pushed his cock between her thighs. It felt like she could feel his heat through her pussy lips.

She lifted her leg to help him and for better access. After he shifted, his cockhead pressed against her lips. She just had time to spread her lips when he pushed forward and drove into her.

She gasped. While she was excited, he entered her dry, and the friction was uncomfortable. Each push coated him with more of her juices and after a while his cock was fully lubricated by her pussy, and slid in easily.

"Hmm, Bob, that feels good."

He whispered, "Your pussy is so tight, Wendy. I feel you squeezing me."

"Keep doing that."

He fucked her slowly, pushing into her, and dragging himself out, until just the tip remained inside her juicy wet pussy.

They continued for a while, languidly fucking, but her excitement was building. She didn't want to wake Roger.

"Fuck me, Bob. Make me cum on your hard, fucking cock."

He sped up, jackrabbiting in her pussy. His long cock filled her.

Her moans increased, growing louder, until she heard Roger shifting. Wendy tried to hold her moans, but Bob kept sliding his cock in and out.

He got out of his bed and walked over, standing over her and Bob.

"Well, well, well, what do we have here?" He pulled his shorts down to reveal his cock to her.

"Holy shit Roger, what the hell is that?" She asked. She'd never seen a dick that thick before, it looked like a soda can.

He chuckled, and knelt on the bed so his monster cock was right in front of her face. He pulled her to his crotch so she could take him in her mouth.

She stared at it as it came closer to her face. It scared her. How was she going to do anything with it?

It filled her mouth like nothing ever had before. There would be no finesse sucking his dick, she focused on cramming as much as she could in her mouth and hope that she didn't dislocate her jaw.

The head barely fit but she was at least able to swirl her tongue around the tip.

Meanwhile, Bob had kept up his fucking. His cock sawed into her pussy, driving her closer and closer to an orgasm.

Wendy hadn't been spit roasted since college. Then it was her boyfriend and his roommate after a night of drinking and partying. She taken them both until they emptied their cocks in her.

Roger held her head while he tried to push further into her mouth. Able to get a little bit more, she reached the limit she could take him in, before she had to tap his thigh to not go any further. She looked up at him and he nodded his understanding. That didn't stop him from sliding his dick in and out as much as he could. She was getting fucked from both ends and loved it.

Wendy felt her orgasm approach. The feeling built up, until she crested the wave and the pleasure washed over her. She had to pull Roger's cock out of her mouth before she screamed, letting them both know she had just come.

"Bob, stop for a minute, I'm really sensitive."

He pushed into her, and soaked his cock, not moving, while her pussy clenched and unclenched around him.

She laid there covered in a sheen of sweat, too sensitive to do anything else.

"Oh god, it's been too long." She pulled herself off Bob's still hard cock, and turned to kiss him.

He grinned at her. "Your pussy feels great."

"You didn't cum though. We'll have to take care of that."

"And Roger, what the fuck is that? I could barely fit it in my mouth." She worked her jaw, and laughed.

He smiled, and said, "wait until you feel me fucking you with it."

"I gotta be honest, I don't think it'll fit."

"You might be surprised. You know Ashley, the gymnast?"

"No fucking way! She's about five foot two. You'd split her in half," she said in shock.

He had a shit-eating grin.

"I've seen it, Wendy," Bob said. She took it like a trooper and asked for seconds."

"Wow. Well, Roj, you'll have to take it slow then," she said, with a twinkle in her eye.

"Come on over here," Roger said, as he laid back on the bed.

She crawled to him. His thick cock was hard and glistened with her saliva. She shivered at the thought of being impaled on his monster, and a gush of pussy juice leaked out.

She hucked her leg over and positioned herself over him. His soda-can penis pushed against her pussy. "Go slow, Wendy. It'll fit, I promise," he said, encouragingly.

She sat down and he entered her. "Oh, Jesus Fuck! It's too big."

"Hehehe, it never gets old." Roger chuckled. "Take your time."

She nodded and gritted her teeth. Bit by bit she slowly lowered herself onto his cock. Her pussy stretched to accommodate his girth.

After what felt like forever, she sank down onto him. Behind her Bob reached around and held her tits, pinching at her nipples.

He whispered, "It's pretty amazing, isn't it? I've seen him fuck girls and they couldn't walk straight for a week."

The sensations from Roger's cock buried inside her, and Bob's ministrations on her nipples turned her on so much. She started ever so slowly fucking his cock. Up and down, just a few centimeters.

Eventually she was fucking herself on him. Her hips gyrated and she slammed herself down as far as she could.

"That's it, fuck my cock. Your pussy is so tight around me."

Meanwhile Bob started fingering her asshole. "Ever been DP'd, Wendy?" Bob asked.

She shook her head no. She felt so full now, having another cock in her felt like it would be too much.

"You'll love it." Roger pulled down on top of him while Bob spread her cheeks. She looked back at him, and saw that he was squirting lotion on his fingers. His finger pressed into her, inserted into her starfish, preparing her.

His finger slipped out, and she felt his cockhead press against her anal ring. She tried to scoot away, but Roger held her tightly to him. "Shh, shh, it's okay. You'll be in heaven soon. Push out a little while he pushes into your tight ass. It'll help."

She nodded, and pushed, almost like she was trying to poop. It did help, and soon the head of Bob's cock popped in. "Oh Bob, let me get used to that. It's been ages since anyone has been in my ass, and they weren't nearly as big as you."

Bob blushed at her unintended compliment and held there, his cock head just inside her.

He pushed farther in. The tight ring of her anus gripped him tightly. He could feel Roger's cock through the membrane separating her ass and pussy. Her ass felt even tighter than it would normally be.

Finally, he hit bottom, fully entombed inside her tight back passage.

"Oh god, I feel so full, guys. Give me a minute." She took several deep breaths, and said, "Do it now. Fuck me together."

The guys nodded to each other, and both started fucking her. It took a minute to find a rhythm, but they managed to work it so that they alternated, one pulled out while the other pushed in. The sensations drove Wendy wild, and it was all she could do to hang onto Roger as they fucked her.

"Aghhh, shit, I'm cumming!" She yelled out. They didn't slow at all, sawing into her from front and back. She couldn't come down from the orgasm, their constant fucking kept her stimulated with heightened feelings.

"I'm gonna cum," said Bob. He pumped her as fast as he could, breaking his rhythm with Roger.

"Cum for me, Bob. Fill my ass with your hot seed."

He grunted and pushed all the way in. Her sphincter clenched when she felt him blast inside her ass. His cum filled her back channel in pulses. She felt each time his cock spurted.

He sat still, buried inside her. His cock slowly pulled out as she moved on Roger's soda can cock still fucking her pussy.

Bob popped out of her sphincter, dribbles of his cum leaked out before it clenched back up.

Roger rolled her over so he was on top.

"Pound me, Roger. Right into the mattress."

"If you say so," he grinned. He fucked her harder and faster than before. His cock stretched her out more than she thought she could take, but like the gymnast, Ashley, she was loving him filling her up.

After a few minutes, he slowed down. He was pulling out and pushing in slowly. "I'm almost there, Wendy. Are you ready?"

She nodded.

A few quick pumps and he shoved himself all the way inside her. His cock spurted his cream inside her gooey center. Several squirts filled her up to capacity.

When he pulled out, a gush of his cum flowed out onto the bed.

"Oh my god," she said. She laid there exhausted by the unexpected workout.

After she caught her breath, she hopped up and rushed to the bathroom, while she tried not to drip everywhere. Much of it ran down her legs. They heard the shower run.

"Dude, that was awesome." Bob high-fived his friend.

"Fuckin' A, man. Fucking A."

By the time Wendy finished her shower, both men were out cold, dead to the world. She laid down next to Bob again and fell to sleep as soon as her head hit the pillow.

****

*Beep* *Beep* *Beep*

The alarm woke the three sleepers from their exhausted slumber.

Bob was curled up behind her again, his hand over her waist. "Bob, wake up." She sat looking for her borrowed clothes. She'd come to bed naked after her second shower.

"Ugh, five more minutes." Bob rolled over.

"Wake up, fuckhead!" Roger yelled.

In the bathroom, her clothes were still damp. She'd need to wear Bob's clothes home on the bus ride back to the college. There wasn't much choice, she wasn't going to wear wet clothes for the long ride.

"Are you guys ready? We need to check out and get breakfast before the ride home."

Roger said, "Ready for another go? Sure." He laughed and Wendy just rolled her eyes.

"You know guys, why don't we keep last night between us. It'll be our little secret."

Bob asked, "Do you think we could, maybe get together again?"

She smiled, and said, "What happens at away games stays at away games."