The Hottest Ass on Highway 50

Do you remember 'Rester's Roadhouse? Outside La Junta, back in the eighties? You might remember the sixteen beers we had on tap. Or you might remember our famous fried chicken. But if you're a red-blooded man you surely remember the hot-ass waitresses. And the hottest of them all was the boss lady, Sherrilyn. I thought so and I sure wasn't the only one.

It was my name on the sign but the roadhouse was Sherry's baby. She set the menu and managed the wait staff. She decorated and kept the books. Her brother Jim ran the kitchen while I tended bar and kept the peace. Dinner service wound down after eight and then it was just Sherry and me until midnight, every night.

Sherry had some pretty ladies working for her and she knew they were a big attraction for truckers and the local boys. But she wanted to keep the place family friendly and insisted the flirtation stay strictly "G", at least until they knocked off for the night. What they did after that was their own business.

Sometimes strangers would set their caps for the boss lady. Who could blame them? She'd shut them down pretty quick, though. Well, most of the time she did. There was that one night, a quiet Tuesday night, when I saw she was paying a couple of guys a little too much attention. One was an old guy in an expensive suit. The other was a beefy young guy with a fresh crew cut. I didn't think they'd been in before but Sherry was treating them like old friends.

You wouldn't have noticed much, not unless you watched her night after night, knew her habits. She let them order food right at eight which pissed off Jim in the kitchen. I saw her lean over the old guy while he pointed at something on the menu, letting him glance down the neckline of her shirt. While she talked to him she'd stand close enough to the young guy that the back of her skirt kept brushing against the front of his jeans as he leaned on his pool cue. Yeah, something was up.

"Old friend in tonight," she explained when she came to exchange their empties for full ones. "He wants me to do a big favor. You mind?"

"How big a favor?"

She fanned out a handful of hundreds on the bar. Wow. That was a lot of dough back then.

"That's a big favor. You trust them?"

"I knew Bill back when I was dancing. He's a good guy. His nephew Eddie just graduated boot camp and he's never had a girlfriend."

"Whelp, you took their money already so I guess it doesn't matter if I mind or not."

"Thanks, baby," she chimed and skipped away with the beers on her tray.

*****

I locked the door at a quarter 'til. Then went around and closed the blinds while Sherry posed for polaroids. Nothing dirty, just her sitting on their laps and showing a little cleavage. She loved having her picture taken and was really hamming it up. Once her skirt rode high enough that you could see panty I collected the camera for safe-keeping.

When the party moved to the private room I turned down the lights and brewed a pot of coffee. I took the receipts and register tray and sat down where I could see the three of them through the door. I didn't really want to watch them screw but I had Sherry's back. She said she trusted them, but even nice guys can get ugly when pussy's involved.

She was fun to watch. I had to give her that. She let Bill pull her blouse off and Eddie reached under her skirt and came out with her panties. They must have been pretty wet by now. He took an enthusiastic whiff and offered them to his uncle to do the same. That little piece of fabric would end up a trophy, I figured. Sherry danced over to the jambox and put on her favorite hair metal band. Out of her overnight bag she produced a pair of condoms.

The two men looked glum when they saw the rubbers but they cheered up when she put one in her mouth and applied it to Eddie's cock without using her hands. They were flavored. Sherry got them at a sex shop in Denver. She unrolled it a little at a time with her lips as his dick pushed deeper and deeper in her mouth. I thought Bill's eyes were going to bug out of his head when her nose finally touched Eddie's hairy gut.

She jacked off Eddie while she gave Bill the same treatment. Once she had his rubber all the way on she just kept blowing him, pushing him down in a chair and directing Eddie to get behind her. She stood and bent at the waist and Eddie took hold of her hips. He lined up and sank his shaft in one brutal stroke. That boy had a lot to learn about women. But no doubt Sherry was wet and ready so no harm done. Still, she had to pause sucking Bill's cock for a moment while she got used to it.

Eddie started fucking her like a mad man and she could barely keep Bill in her mouth. He wasn't complaining though. I think he was enjoying the situation as much as the blow job. She rested her forearms on his thighs and managed to get her head going in an up and down motion while Eddie pounded her mercilessly from behind.

Bill unhooked her bra while she slobbered on his knob and freed up her hoots. They weren't huge but they were real nice and I paused my counting to admire the way they swayed in the rhythm. Just then Sherry stood bolt upright and spun around to face Eddie. He held up his hands and looked like he was apologizing. He must have slipped out and poked her between the cheeks. No sir, that's against the rules.

She bent over again and took Eddie in her mouth this time, pulling him toward her so she could back up to Bill. The old man looked pretty delighted to have her sweet ass in his face and she lowered her pussy onto his dick and started grinding. She straddled his legs and put one hand on his knee to support herself, wrapping her other hand around the base of Eddie's cock. Bill rested his hands on her butt cheeks and just enjoyed the fuck, his head lolling back.

Her mouth bobbed on Eddie's cock while he cradled her head in his hands. She could get half of him in without effort and occasionally took him deep enough that her lips met her hand, turning her head from side to side on the end of the downstroke. She looked fucking spectacular getting stuffed at both ends but the two guys looked ridiculous, spoiling the effect. I lit up a smoke and just watched out of the corner of my eye.

Bill didn't last too long like that. He came to life with a grunt and clutched at her hips while he filled up his condom. Sherry sat on his lap and brought her other hand up to cup Eddie's balls. She slowed the pace of her sucking and concentrated on taking him deeper. The combined sensation of her gullet on his head and her hands on his scroat proved too much for him. He held her head and fucked her mouth as he busted his first nut inside a woman.

*****

It'd have been nice if that was it but I knew for that kind of money there would be a round two. I dropped the deposit in the safe and finished cleaning up. The guys pulled on their pants and stood at the bar drinking coffee and smoking while Sherrilyn got changed. After a while she emerged from the back room wearing a skimpy pair of cutoffs and a halter top, tottering on high heels. I guess she just keeps things like that on hand.

They went back in the private room and Sherry put on some slow dance music. She danced seductively around the room, pausing as she passed each man to let them feel up her cheeks and nuzzle her cleavage. She backed up to Bill and rubbed her ass on his crotch while she danced. His hands ran over her stomach and cupped her breasts. Her head went back on his shoulder and he nibbled her neck.

She danced over to Eddie and pressed her denim-covered crotch against his. She felt his chest and arms like he was a muscle man while she stroked herself up and down on his bulge. She undid his pants and he did the same for her. She put a fresh condom on him, using her fingers this time, and had him sit in the chair. She climbed on his lap, facing him, and slowly sank on his dick. She started rocking and grinding on him, still dancing to the music. Dude might learn something if he paid attention.

He pulled off her halter and started sucking on her tits. Sherry pushed them into his face with her hands, first one and then the other. She leaned forward to whisper in his ear and played with his nipples too. I couldn't help but admire her shoulders and back and perfect ass. She looked so beautiful and nasty, riding that cock. Bill also was gaping at her, mouth hanging open like a dummy.

Eddie said something to her and she climbed off. He got to his feet and she took his place on the chair, kneeling on it so her ass was sticking out toward him. He started fucking her from behind, slowly now, eyes closed in rapture. Sherry pushed back, clearly enjoying it. He put his hands on her shoulders and her back bowed as he pulled her toward him.

I figured it was safe to get a fresh pack of smokes from the vending machine and make another pot of coffee. When I got back to my vantage point I saw he had her on the table, on her back with legs in the air. Her ass was hanging over the edge and he was pounding that pussy for all he was worth. She was moaning. He was groaning. Bill was standing near, watching with wide eyes. Eddie went faster and faster and then boom. He filled up another rubber.

When the dust cleared, Eddie came out and sat at the table with me. "Damn, she is red fucking hot. Uncle Will was right about her. You ever get a piece of that?"

"Oh yeah, I get a piece of that," I replied, only half paying attention. Sherry was sitting in the chair now with Bill standing in front of her, his dick somewhat erect. She had her cutoff shorts back on and her tits still hanging out. She was trying to get a rubber on the old man and he was having some trouble, as old men sometimes do. Maybe he was thinking he'd do better without the latex. And maybe Sherry might be soft-hearted enough to let him. But that's against the rules.

She started stroking his cock and squeezing his balls with one hand. With the other hand she worked the condom onto the head of his cock and managed to get it rolled halfway down. She took his head in her mouth and held it while she continued to twist and stroke his shaft, now with both hands. I couldn't tell from this distance but certainly her tongue was working some magic. This got Bill's engine going and I managed to relax a little.

"Yeah, she's fucking hot," I agreed, picking up the thread of conversation. "She doesn't take customers very often these days or even at all, really. So it's lucky she and your uncle are old friends. Do they keep in touch, do you know?"

"No, he says he stopped in here last year just by chance and there she was. He says she was kind of a star and since we were coming this way he thought he'd take a chance."

"Well it worked out this time, so congratulations. But like I said, she doesn't take customers very much these days. Keep that in mind next time you come this way."

Eddie went quiet and I went back to watching Bill fuck Sherrilyn in her mouth. She was out of the chair and on her knees and her head was bobbing the inch or so that the half rolled condom would allow. Her hand was a blur on his dick and he had two handfuls of her hair. I started to get out of my chair in case things got out of hand when he bellowed and let loose. Sherry ducked to the side, her hand still working his cock, as the condom came flying off and his old man jizz came oozing out on her breasts.

*****

The last part I liked the least. It was a special treat of Sherry's since Eddie was a cherry boy. Bill and I sat on the bench behind the building while the other two "necked" in the front seat of Bill's car, a Chrysler Imperial. It was dark and the windows fogged up pretty quick so there was no way to be sure what they were getting up to in there. Sherry told me what would happen and I have no reason to doubt her.

She had changed back into her work uniform. No panties of course and she left her bra in her bag. She said they would cuddle, hug a little like they were on a date. Then when he got good and worked up she'd give him a hand job so he could feel some bare skin on his johnson. After what they'd already done this sounded practically tame. Still, not being able to see them made me uneasy.

Bill and I smoked and pretended not to notice the subtle movement of the car or the muffled sounds that came from it.

"She's pretty amazing," he said, not looking at me. "Eddie said she doesn't take customers these days so I'm lucky she did this for us."

"Yeah, lucky."

"She's wearing a wedding ring now. That's new. Maybe that's why she quit."

"Yeah, she's been married almost three years now."

Bill pulled out a fresh cigarette and lit it from the butt in his other hand. He dropped the butt and ground it into the gravel with his heel. "Does her husband know... that she, uh...?"

"He knows who she is. Don't fret about that."

"Well I suppose he'll find that thousand bucks to come in handy."

I flicked my own butt across the alley. "He doesn't really need the money, to tell the truth."

"Oh yeah? What does he do?"

"He runs this restaurant," I replied, gesturing up at the unlighted sign at the entrance to the parking lot.

He read the name out loud, contemplatively, "'Rester's Roadhouse."

"It's short for 'Forester'," I explained. "Like the author, C.S. Forester."

"I see," he said and fell silent.

The sounds from the car got louder. I could hear Eddie grunting and Sherry murmuring encouragement. Then one last grunt followed by feminine laughter. Finally, it was over. We stood as Sherry got out of the car and strutted over to us.

"He's all yours, Bill." Sherry told him. And to me, "I need to wash my hands. Be right back."

I walked Bill to his car. He paused at the driver's side door and looked me in the eye. "I'm sorry, man."

"Don't be sorry. Be glad. You and your nephew had a good time tonight. You should celebrate that. I don't mean to make you feel bad about it."

"That's a generous attitude."

"Bill, Sherrilyn didn't screw you for a thousand bucks. I mean, not directly. Sure, it stokes her pride that you're willing to pay that much."

"Worth it, and more."

"You don't have to convince me. What I think is more important is that she told me you were a good guy. I know for certain there weren't too many good guys in her life back then. You must have done her a good turn and she feels like she owes you."

"You... that's a pretty good assessment."

"I appreciate whatever kindness you've shown her. But we're trying to make a new life here. It's hard to do that when the old life keeps popping up. So you do something for me?"

"Yeah?"

"Next time, let Sherry buy your dinner, pour you some beer on the house. But don't ask her for any more favors, OK?"

"You got it." He held out his hand and I shook it.

The tail lights of his Chrysler were a dim red dot on the horizon when Sherrilyn came back out. We walked side by side across the parking lot to our little four-roomed house. Her hand found mine and our fingers intertwined. "Thank you, honey. You are the best husband."

"I think I'm the worst husband, to let you do that."

"Well I... I appreciate you understanding." We got to the door and I opened it for her. She paused in the doorway and touched a finger to the back of her thigh. Slowly, she drew the finger upward, pushing the hem of her skirt up to expose a beautiful bare butt cheek. "I saved something for you. Want it?"

"Damn, girl, you always know just what to say."