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.
