The Confession Pt. 06: The Regular

The Confession Part 6: The Regular.

"Is Larry back?" I nuzzled Donna's neck.

Larry is Donna's boss, and sometimes lover. She has a hall pass from me to have fun if she wants. She has used it a few times, notably with her boss, Larry. Their relationship had gotten too intense after a weekend at his island cottage where her personal limits were pushed hard when Larry invited a friend along. They both agreed to cool the relationship and Larry went to Florida with his family.

Today she'd come home from the diner smelling of French fries and eager for sex. I'm always happy to oblige. Her eagerness suggested someone was paying her special attention at work.

After she rode me to a screaming orgasm (I screamed and she screamed), 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 attract your interest, today?"

"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. Donna sat back on my hardening cock and blushed. "That was insane. 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 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 closed her eyes and moaned as her pussy clenched my cock.

"Is this the first time...?"

Donna ground harder. "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 drive deeper. Donna groaned and pounded me with enthusiasm. She loves riding me cowgirl and I love letting her, but sometimes she just gets wild. I held onto her hips, so I didn't slip out and get us both injured.

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. "Larry put a price on sex 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 harder. "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."

"It's more than that. It's the business with the landlord."

"You were more than bit naïve about that. What he did was pay you for sex, even if he didn't say so. Quid pro quo is just a way of getting around calling it what it is."

She sat upright with a storm on her face and my cock twitching hard in her pussy. "You're saying I was a whore."

"Not the word I would use." I struggled to hold her from running off on me. "You were paid for sex."

"That doesn't make me feel any better. Mac basically pimped me out."

"When you put it that way it doesn't sound very good."

"And you're hard as a rock while we talk about me selling my ass..." She slapped me this time. I deserved it.

"I'm sorry. It's my fantasy. You shouldn't do it. Not to please me. Not for the money. Not at all if you don't want to." I stroked her face. "I really want you to have fun and make decisions because you get a thrill out of them."

She started rocking on me again. "Well, maybe I like the idea that he offered me money because he wasn't going to get my attention otherwise. It's not like I'm doing this all the time."

"It's up to you. But you should only do it for fun." I thrust deep into her. "I think it puts a nice distance between sex and relationships. You and Larry were getting pretty close. He was having sex with you more often than I was and I know it wasn't about the money."

She leaned in and hugged me hard while she rode my hard cock. "I had a stupid crush. I'm sorry."

"I know... It's all right. I enjoyed your crush right along with you. And you banging two guys at once. That was wild."

"Well, so if he calls me on this bluff, do I go?"

"Do you want to?"

"I... maybe... Ohhhhhh...uhhhhh...ohhh..." She came hard and so did I.

****

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. I hadn't known what I was going to say until it came out of my mouth. "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.

Dave's hall pass gave me permission to be bad if I wanted to, but I really am not a bad girl. I love him. But my whole life had been about trying not to be bad. I didn't want anyone to think I was a slut or a whore or anything that made it sound like I enjoyed sex.

And my late husband convinced me that I hated sex because sex with him was demeaning. Then the landlord's deal, money to give to my husband if I cheated on my husband. So I became a whore, but didn't want to enjoy it.

Sex with Dave showed me it was OK to like sex. Dave said I should have sex on my own terms and with whoever I wanted to. My choices, and when I wanted to. Dave's fine with it. Better if he gets to watch.

So, I have strayed on a couple of occasions, most notably with Larry, my boss. I told Dave about my adventures, 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 to help him off of a roof.

But this was really different. John offered 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 after he left, 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 was the only reason to have sex with this guy. I mean he was nice enough and attractive, but if he hadn't called my bluff with cash in hand I wouldn't have agreed.

Now I had thrills running up my spine while I worked, knowing I was intentionally going to do what had revolted me with the landlord. I was a slut and a whore. Dave might accept me, but I felt bad. And I felt the thrill of being bad like when I was with Larry on his boat, or with Chet, or Larry and Doug, or Robert.

I liked being bad.

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 on my own time that I'd enjoy sounded very good. I hid my red face with a long sip of hot coffee.

I bussed my last table and tipped out. I grabbed my coat and went to my car in the employee's parking lot. The drive to the Holiday Inn was barely fifteen minutes.

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.

John gave me his room number. I walked in like I belonged there and knocked on his door. I'd been nervous when I walked through the lobby, but the only kind of working girl I looked like was the one that gave you your coffee, not a five-hundred-dollar hooker.

I was a prostitute.

Taking money for sex.

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 didn't step back but sniffed me as I walked into the room.

I picked up the wad of money and wrapped it around the first $250. I faced him in the little hallway that led to the bed. "I don't do this. I'm not a whore. I'm a happily married woman. I just wanted you to stop thinking you were going to seduce me."

"Then why are you here if you're happy and you don't need the money?"

"The money says you value me enough to pay for my time. You've spent a lot of money and time trying to get me to go on a date with you and now you've got me here." I pulled at the scrunchy that held my hair back and let it down with a shake.

"I guess I do. So now what? Do you want to go down to the bar for a drink?"

"Not really. You brought me here for more than conversation, right?" Was he going to bail on this tryst? Did I want him to?

"No, you're right. I can talk to you at the diner for a damn sight less money." John nodded. "Let's get you out of those clothes first."

"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 white bra and granny pants. "You said come straight from work, so nothing special..."

John kissed me with an open mouth, and mine opened to greet his tongue. We got more passionate as he unhooked my bra and rolled 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. If I was going to charge for my services, then 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 looked at the money on the counter. It meant I owed him good value for his money. He wasn't forcing me or trapping me. This was my choice.

The shower ran for a few minutes. John 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.

We stood there, me leaning against him trying to swallow his cock, and him with his hands in my hair trying to fuck my face. I dug my fingers into his buttocks for control but he let me stop to catch my breath and control my gag.

I sucked him harder until I felt his cock swell.

John groaned. "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. "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. He was talented with his tongue and fingers. I might get off if he worked at it and he was enjoying himself, but I could feel myself disconnected from the act. I didn't feel naughty for enjoying the sex, just from getting paid for 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 John's 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 alright?" 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.

I leaned my forehead against the door as she ran the hot water out. The thrill of her having done what I'd fantasized about faded quickly. It was my fantasy, not hers. Had I hurt her?

The sound of the water stopped, and the curtain swooshed back. I stepped back from the door, afraid I might creep her out more. 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." Her voice was flat, echoing my thoughts.

"I'm sorry. I should have told you to forget about it." I ached for her.

"No. I should have said no." She poured a cup of coffee and sat, hair wet and towel wrapped at our kitchen table.

"Why didn't you?" I put my hands on her bare shoulders and kissed her neck.

She sipped her coffee and stared out the window for a few minutes. "I asked myself the same thing and the answer was the money made the thing exciting. He wasn't a crush like Chet or Larry. I don't think I'd have had sex with him just 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." I patted her head and tried not to think about my fantasies. My selfishness made her do a thing she didn't want to do.

"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." She looked up at me with moist eyes. "But the money makes me feel valued, and I like being bad and it's so confusing..."

"Well, you're in a better situation. You don't have to take money. And you can be choosy. You can just say 'No.' 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." I kissed her. "I know this was my fantasy. I hate that I talked you into it."