The Regular.
“Has Larry been behaving himself?” I nuzzled Donna’s neck. Larry is Donna’s boss, and sometimes lover. Their relationship had gotten too intense at work and with weekends on his boat so she’d cooled it down. She had a hall pass from me to have fun if she wanted to but her personal limits were pushed hard when Larry invited a friend along on one of their boat trips.
Today she’d come home from the diner smelling of French fries and eager for sex. I’m always happy to oblige, though she is more interested when someone is paying her special attention at work.
After she rode me to a screaming orgasm, I pulled her close to my chest so I could feel her warm breasts and keep my softening dick in her a bit longer. “Anyone else attract your interest?”
“No… Why?” Donna pushed herself up so she could search my eyes for some hidden meaning.
“Just wondering. It’s been a while since you pulled the plug on Larry.” I pulled her nipple to my mouth.
Something crossed her face. A flash of emotion, guilt, or shame, I couldn’t tell. “Larry was too much. I didn’t like what I was doing, even though the sex was great.” Donna sat back on my hardening cock and blushed. “Especially with his friend Doug… That was insane. But I don’t want to be that girl.”
“It’s all right. You don’t have to be anyone but you.” I held her hips and thrust deep into her hot pussy. “Anyone flirting with you at the diner?”
Donna bit her lip and rocked gently on my cock. “Well, there is this one guy who says he knows you from your work. I think he’s one of the contractors. His name’s John, he’s in his fifties and he keeps teasing me.”
“What does he do to tease you?” I grinned. I had no idea who she was talking about, but it didn’t matter.
“He sits in my section and talks to me. He keeps asking me to go out with him.” She looked away.
“Is this the first time…?”
Donna ground her pussy on my cock. “No… He tips me $20 for a cup of coffee so I let him talk.”
I groaned as my cock became as rigid as it could get.
“He tells me that he wants to do things to me if we go out.”
I grabbed her nipple in my teeth and tried to pump her harder. Donna groaned and started pounding me harder. She loves riding me cowgirl and I love letting her, but sometimes she just gets wild. Our orgasms peaked nearly together, and I filled her already sloppy pussy a second time.
As we were catching our breath, Donna continued. “He’s been getting a little more ‘friendly’ this week. Nothing much really, just touching my hands while I’m sitting at his table making out my slips.”
“You sit with him?” I grinned. She was definitely up to something here.
“He tips well when I do. I don’t ‘do’ anything.”
“So, he pays you so he can make sexual advances?” I kissed her.
She blushed hard. “That makes it sound dirty.”
“He’s talking about sex and giving you money. Yeah, it does sound dirty. Hot and dirty.”
A tear leaked out of her eye turning the discussion in a different direction than I’d anticipated. “He makes me feel cheap.”
“Tell him he can’t afford you.”
“Yeah…” Donna blushed a deeper shade of red. “I did that…”
“And?” My poor abused cock twitched.
“He said ‘How much?'”
The rush of being on edge of bad flowed through me. “What did you do?”
Donna put my hands on her breasts, to distract me, I think. “I… I told him $500. I figured he would laugh, and we’d be done…”
“But…” I shivered with anticipation.
“He said he’d see me tomorrow,” she whispered.
“So? If you’re not interested just tell him no.”
“I… I… of course not.” She stammered and looked away. “That’s what Larry tried to do and I don’t like it. Why do men want to pay me for sex?”
I moaned into her neck as my poor sore cock twitched again. “Maybe they figure that’s the only way to get you in bed? You wouldn’t want them lining up out the door because you were giving it away.”
She hit my shoulder lightly. “You said I’m not a slut.”
“You aren’t. You’re exploring your sexuality. If you make some money while you’re having fun, that’s fine with me. Just tell me what happens.”
****
Donna:
I work two to ten at the truck stop diner. The food is shitty, the customers are either rude or lovable, and the boss is a shithead. Sexy, but a shithead. That’s another story.
It was about 7 when John came in. I pointed to an empty table on my side of the diner and brought him his coffee. He ordered a hamburger and fries which was about the only dish on the menu the girl cooking tonight didn’t screw up. I sat down with him to add up my tickets after I’d checked on my other tables.
“Busy night?” he said.
“Not really.” I scratched out the ticket total and added the tax to the last ticket. When I reached for my coffee, John’s hand found mine.
Before I could extricate myself, John said, “I’ll give you 250 now, as earnest money the rest after.” He pushed a bankroll across the table and into my hands. “I’m in room 216 at the Holiday Inn.
“I… I…”
“This money is yours whether you show up or not,” he smiled at me and patted my hand.
“Tonight?” I squeaked.
“Yeah. Is that a problem?”
My brain froze, but my mouth kept going. “No… I… I… I’ll be there after my shift ends.”
“Don’t change.” John handed me another twenty for his meal, got up and left.
I looked around the diner. My coworkers weren’t looking my way. No one noticed the wad of cash. I pushed the money into my apron and cashed John out at the till before I delivered the rest of my tickets.
I spent the rest of my shift in a state of numb disbelief. I liked Dave’s hall pass. He gave me permission to be bad if I wanted to, but I really am not a bad girl. I love him. I have kids and responsibilities. And I don’t want to be sneered at by the girls at the diner. I think some of them know about the abusive arrangement my ex-husband got me into with our landlord where I was effectively whoring myself out to the landlord so my husband could have drinking money.
I’d agreed with Dave that I wanted to have sex on my own terms. My choices and when I wanted to. Dave’s fine with it. Better if he gets to watch. And our sex is great afterwards so I guess a little naughtiness is alright.
Larry had tipped me after sex, but he had wads of cash in his pocket all the time and always tipped people who did things for him. Larry had given me fifty bucks for helping him off of a roof.
But this was really different. John gave me money to show up and have sex. Why did I take the money? I hadn’t actually done anything. I could always just give him the money back and it would be no harm no foul… But when I counted my tips, I had $40 in dollar bills and change not counting the money John gave me. $500 would put a dent in the credit card bill.
My pussy was swollen and wet. I had to call Dave. I used the phone in the back knowing full well the shift manager, Shelly, would be listening.
Dave picked up on the second ring. “Hello.”
“Hi honey. I need to stop in town after work.”
“Oh… are you…”
“Yes,” I cut him off. “I’m calling on the diner’s phone.”
“Got it. I’ll see you when you get here.” Dave hung up.
I took a deep ragged breath and hung up the phone on the receiver.
“Everything all right?” Shelly stuck her head out of the office cubicle.
“Fine,” I said, and I returned to the front to finish my shift.
Everything wasn’t fine. I was whoring myself out. My choice, I guess, because I didn’t have to. Dave only cared that I was enjoying myself. Being honest, the money made me hotter than the idea of having sex with this guy. Getting paid for what guys had done to me for free my entire life seemed empowering.
I pushed through the rest of my shift on cruise control. When I cashed out I didn’t count the $250 John had given me in my tips. My night’s wages at the diner worked out to $76.35 including the $18.00 tip from John’s coffee. $500 for a couple of hours work sounded very good.
John had said, “Don’t change.”
I had to assume he just wanted me in my waitress uniform, not that it was a real uniform, just white shirt, black slacks and the black apron. I smelled like the diner and it was pretty disgusting.
He had a room at the Holiday Inn. I walked in and knocked on his door. I’d been nervous when I walked through the lobby. But dressed for work I wasn’t sexy so no one would think I was a prostitute.
I was a prostitute.
Taking money for sex.
I hesitated at the door. I almost turned and ran, but John opened the door.
“Hi, Donna. I didn’t think you would come.” He held the door open for me.
I slipped into the room. “I almost didn’t… I should shower first. I smell like the diner.”
“The rest of your money is on the dresser.” He said.
I picked up the wad of money, and wrapped it around the first $250. “I didn’t mean to actually sell myself. I’m not a whore. I wanted you to stop thinking you were going to seduce me. I’m a happily married woman.”
“Then why are you here if you’re happy and you don’t need the money?”
“I need the money, alright? But I’m here because my husband has given me an open-ended hall pass. If I want to, I can fool around with anyone that attracts me. All I have to do is tell him about it. And I like telling him.”
“So, you’ve done this before?”
“Yes. Not really for money but…”
“Not really for money but you got paid?”
“It was my boss. He tipped me when we did it.” Every time we did it, I remembered. I had liked the sex, but the idea of being paid for sex bothered me then and bothered me now.
“So, I’m going to leave this money here,” I put the roll on the dresser. “This is for fun. Your fun, my fun, my husband’s fun.”
“Let’s get you out of those clothes first,” he started to untie my apron.
“OK, I’ve got it.” I stepped back and stripped off my apron, shirt and pants. I pulled off my shoes and socks. Finally I stood there, shivering with nerves in my bra and panties. “You said come straight from work, so nothing special…”
John stepped up to me and kissed me on the lips while he pulled me to his chest. I hesitated at first but then I kissed him back. I felt clumsy. Where do I put my hands? Am I doing this right?
He kissed me with an open mouth, and mine opened to greet his tongue. We got more passionate as he unhooked my bra and pushed down my panties. I pulled at his belt and pants until they slipped off of his hips to the floor. When his rigid cock broke free I trapped it against my stomach while we continued to kiss.
“Do you suck cock?” he said into my mouth.
“Not usually.” I thought of the five hundred he’d paid. I supposed I could lick his dick. “Go wash it and I will.”
He kissed me, squeezed my tit, and retreated to the bathroom. I rethought leaving the money on the counter. The shower ran for a few minutes. He took the whole ‘wash it’ thing to a new level. I liked him a little bit more.
He came out of the bathroom with a towel around his waist, smelling of soap. I sat primly and naked on the bed with my feet on the floor. He walked up to me and dropped the towel. His cock wasn’t rigid anymore, but it was only mildly flaccid. I leaned in and gave it a little lick.
It quivered like a live thing. I pulled back.
He laughed. “You woke him up.”
“Yeah, I guess.” I leaned into him and pulled his cock into my mouth. I worked my tongue up and down his growing shaft until his head swelled in my mouth. He dug his hands into my hair and pulled my face onto his cock until I choked.
“Oh gawd… that’s crazy. If you do any more of that I’m going to jizz in your mouth.”
I pushed myself back onto the bed and spread my legs. “Then let’s do something different.”
He crawled between my legs, licking my thighs on his way to my pussy. “Ewww I haven’t washed up after working all day.”
“Doesn’t matter.” His tongue on my inner thighs sent shocks up into my clit. I looked at the hotel room ceiling while he worked on my pussy. It felt good and he was enjoying himself, but I could feel myself disconnected from the act. I didn’t feel naughty. I was enjoying the sex so far. He was talented with his tongue and fingers. I might get off if he worked at it.
I had a choice. I could call a halt to this, give him his money back and tell Dave I didn’t want to use my hall pass this way. Or I could let him use me, take his money and tell Dave I didn’t want to use the hall pass this way.
“Ohhhhh…. Uhhhhh…” The orgasm caught me by surprise. My body hunched up and I tried to jam his face into my vagina while the most gut twisting orgasm ripped through me. “Jeeeeeezus…….”
He pushed back as soon as I could let go of his head and sat back panting. “That was a close one. I thought you were going to make me tap out for sure.”
“I…I’m sorry. That was such a strong one… It caught me off… Oh fuck… Come here…” I pulled him to me, so his cock pushed at my labia. I fed him into my pussy, and he slipped in like he’d been there all day.
He sunk his cock in until we ground our pubic mounds. He hit my clit and the spasms started again. Each stroke brought me up the orgasm mountain higher and higher. I wrapped my legs around him and moaned and cursed in his ear. “Ohhh…. Fuck me. Fuck me Fuck me….”
I lost track of the ceiling and my thoughts as the rolling waves of pleasure hit me with every solid stroke. Finally, his pace picked up and my peak rose higher until he slammed into me like a high-speed hammer while I tore at his back with my fingernails.
I think we both screamed when he pulsed cum into my pussy. I sunk my teeth into his shoulder so the hotel wouldn’t call the cops on us because of my screaming. As the last waves receded, I relaxed my death grip.
“You’re great. I can see why you’re expensive. Worth every dollar.” He rolled over and grabbed some Kleenex to wipe himself. “Maybe we can do this the next time I’m in town.”
I got out of bed and wiped myself with some tissues. I wanted a shower but didn’t want to be in his room any longer. With sex finished, I just wanted to go home to Dave. “I really am not a whore. I might be a slut, but I’m not a whore. We’re not doing this again. I didn’t know if it would be fun or not, but it’s not the fun I want. Sorry.”
I dressed quickly and pocketed the money. “And thanks for the money.”
“Thanks for the great fuck. You’re sure you don’t want more business?”
“Nope. This is between you and me. I tried to bluff you, and you called my bluff. That’s all this is.”
“You were trying to discourage me?” He grinned. “You’re wicked. Glad you paid up.”
“Glad you did too.”
****
Donna came home, dumped her money on the kitchen table and went into the bathroom. I knew she was upset when she started the shower. She knows I like to experience her freshly fucked.
“Are you all right?” I called through the bathroom door. “Did he hurt you?”
“I’m fine. He was fine. I’ve got to shower.” The shower curtain was pulled shut.
She ran the hot water out in the shower. When she came out, she had a towel wrapped around her and threw her clothes in the washing machine.
“I shouldn’t have done that.”
“I’m sorry. Did you want me to tell you ‘no’?”
“No. I should have said no.”
“Why didn’t you?” I put my hands on her bare shoulders and kissed her neck.
“The money made it exciting. He wasn’t like Chet or Larry. I don’t think I’d have had sex with him for fun. But for money I did.” She pushed her face into my armpit and sobbed.
“It’s all right. You don’t have to do anything like that again.”
“But I did it with Larry. He paid. I took his money. Just like with Gerald the landlord. I’m no better than the lot lizards that fuck truck drivers in the parking lot.”
“Well, you are better. And you don’t have to take money. And you can be choosy. And I’m happy with whatever you choose, even if you don’t want to be naughty. That’s your choice.” I kissed her hard. “I can’t say that often enough. You don’t have to do anything you don’t want to do. And if you feel pressured, tell me and I’ll fix it. I promise.”
“I love you, Dave.” She pulled me tight.
“I love you, too.”