One Hell of a One Off

Chapter 1. Hell in a Bucket

"I'm so fucked. He owed me fifteen grand!" I was sitting with my good friend Al at our Wednesday table in the corner window of Fink's Fine Foods on a foggy San Francisco morning. I sat with my back to the window, slumped down in the seat with a hoodie down over my eyes, oblivious to the street action we so often snarkily commented on. "I need ten thousand like tomorrow. I'm two months behind on rent, my credit cards are maxed out, and I have a box of graham crackers and a jar of peanut butter in the fridge."

"That's a lot. Wouldn't your parents would loan you that?"

"Probably. I can't ask them."

"Won't."

"I've cost them so much money. They're retired. My Dad was a bus driver. I just can't." Al knows my entire history: overlooked middle child, hormonal avalanche in middle school, precocious, then promiscuous in high school, majored in partying at community college. It took an arrest and two whacks at rehab to learn how to tolerate myself. I got sober, started running, dropped twenty pounds, finished college, got a career. I didn't want to ask anyone for the money.

"Maybe I should sell my body," I said sourly.

"Do you mean that?"

"Maybe. Beats a second job cleaning offices overnight."

Al gave me a very strange look. "I know men who'd pay to sleep with you."

"Sure you do."

"I do," he said, "for sure."

"Seriously? Real guys you know right now?"

"Yes. At least two."

"Who would pay $10K to sleep with me?"

"You'd need a few guys, and a few days. I could," he said, in a tone that implied he didn't quite believe what he was saying, "organize it for you."

There had been a time when the only thing that felt good was sex. And vodka. Strip poker at the parties, blowjob contests in the living room, pairing off in dark corners, the night Katie pulled a ten-man train. At least I had my guys one at a time. "OK. Theoretically, if I did it, what would it take to make that much?"

"Well," Al said, "I'm just improvising here, but maybe a long weekend with four guys? $2500 each for a few days of unlimited access?"

"And you have two already?"

"Three."

"Didn't you just say two?" He looked steadily at me. I got it.

"You," I said. "You would pay to fuck me."

I met Al when he sat down next to me in my first class on my first day as a reentering sophomore at UC Davis. He was the first guy in ages who didn't hit on me within the first five minutes. We both were older, me out of rehab and on probation, going to meetings, working as a sales clerk at Macy's; him out of the Army after a tour in Afghanistan. His parents, both only children themselves, had died in a car accident the year before, when he was over there. They told him in the field, gave him two weeks bereavement leave, then discharged him before he came back. He lost his parents and his buddies all at once. We both needed a friend more than a lover.

"Yes," he said. "Yes I would."

"Could that destroy our friendship?"

"I'd think the opposite—you trust me, I could watch out for you. Get you water. Guard your consent."

"Why do I have to fuck you for the money?"

Al pulled a check out of his wallet, made it out for $2500, signed it, and pushed it in my direction. "You don't. But if you fuck anyone . . ."

I stared at the check sat on the table. "When I was drinking, and angry," I said, "and fucking everyone I met, I thought about becoming an escort. Tested it out. I got money from guys I would have slept with anyway. I was talking with an escort service when I got arrested." In rehab I couldn't wear the miniskirts and skimpy tops that used to be my uniform. Turns out I had a lot of sex because of those clothes, as if the sex proved I had right to wear them. "Now it's come back again, all these years later."

"A weekend isn't a career. You are a woman men desire."

Like most women I saw myself as a misshapen amalgam of flaws, but it was true that men liked the way it all came together.

"You'd really pay to fuck me?"

"Yes." He pointed to the check. "I'd also loan you this money and not fuck you."

"Why haven't you ever tried to fuck me before?"

"When we met you were still on hiatus. It was more fun to have a real relationship with you than it was to try and get into your pants."

Four guys. Three days. I have had one boyfriend and two briefer dalliances in the five years since I completed probation. Sex didn't drive my self-esteem anymore. "There was a night once, that summer after senior year, before everyone went off to college and adulthood, when I slept with my boyfriend and his best friend. It happened really naturally and I really liked it. They each came like three times and I lost count for myself. My rehab therapist assumed I had been coerced, but I felt worshipped."

"Worship," Al said, "would be doable."

I remembered, and my cheeks burned. "I'm not saying yes, but it would have to be out of town, someplace luxurious. I get my own bedroom and bathroom. I get my fee, and all expenses. Nice dinners. And a generous tip." I was aware that my grammar had suddenly gone from conditional to declarative. My body was tingling; half-shaped memories of cocks and chests and tongues flashed. I haven't had wild-ass sex for a long time.

"A tip is fine. So what would actually happen?"

"I could probably get each of you off twice a day for three days." After all, I'd gone on all weekend more than once with various boyfriends.

I saw him do the math. "Nope," Al said, "that's over $400 each time. It's gotta come down to around 200, 250."

I did that math. "Forty-five times over three days—I don't think I could have done that at even my sluttiest. "

"So five days?"

"Too long. I'd get bored. And mean. So I need to provide additional services. How about this? For an extra 200 you can watch me fuck someone else."

"Just sit there?" he said. "Fifty."

"You pay more than that to see a play. A hundred."

"Deal." He wrote it down. "What else?"

"For 500 I'll masturbate for you."

"No," he said. "I can just have you do that during one of my six times with you over the weekend."

"You misunderstand. I'll do a strip and masturbation performance for all of you."

"With lap dancing?"

"Never done that before. I'm not the greatest dancer."

"I'm sure," he said dryly, "you can figure it out. Use a dildo with that?"

"Really? Okay."

"Okay," he said, making a note. "Can I pick the dildo?"

"Don't push your luck, buster."

"I'd pay you extra for a threesome," Al said.

"You give me an extra 500 and I'll do a threesome."

"200."

"200 per guy, and it counts as one encounter for each guy."

"200 per guy," he said, "up to all four of us a once."

"Really? You'd gangbang me?"

"Yes," he said. "Yes I would."

"I'll do that once, for an extra 1000 flat fee. Just don't beat up on me too badly."

"I'm glad," he said, "you're an athlete."

"Yes, well, we know how to suffer."

"Please, Jess. If this actually happens? No suffering, okay? Okay?"

"Okay, Al." Overcoming suffering is part of the pleasure, but it wasn't time to tell him that.

I opened Google Sheets on my phone: $4800 base fee, $1600 worth of threesomes, $1500 for a strip show and gangbang, $1000 for watching, plus a 20% tip. Came to $10,700.

"Check this out. That gets me my ten thousand," she said.

"To be really clear: if guys are paying, they're going to want what they want."

I made the Girl Scout salute. "I promise to fuck and suck with enthusiasm," I said, "and I'll be willing to please, but no one gets to go on forever. Maybe like half an hour each?"

"That's a guideline," he said, "not a regulation."

More math ensued. "12 hours fucking out of 72."

"Could be 16," he said. Probably not more than that."

"I'll take 24 cumshots, but someone might just get a handjob if I'm too beat up. No anal, no forcing, no foul language. I'll do what we agree, but no means no and stop means stop."

"Agreed. No forcing," he said. "Is money your motivation, here?"

"Yes. Why else?"

"We could make more money," he paused; I could see him forcing the words out of his mouth, "with a film about a woman who gets into financial trouble and fucks her friends for a weekend to make the money back."

"A porn film? Starring me?" Al had been writing movies since before we met. His shourt films were clever and well shot, but he still made his living doing corporate training videos and having unsuccessful meetings with producers.

"There could be an art-house version and a hardcore version. You could color your hair something really different and we could do stuff with makeup to disguise you. Temporary tattoos, or something."

"High concept: It's a documentary of this story. The actress is anonymous. I front the film as producer. People won't think the star and the producer could be the same woman. Who does camera?"

"Me and Steve," he said, "but also whoever's not fucking you, with their phones."

"Your friend Steve? From college? He's one of the guys?"

"Yes. We've been making movies together since high school."

"The guys would have to sign releases and work for free."

"They're not working for free," Al said. "They're paying."

"Good point," she said. "But they have no financial interest in the film."

"We should pay them back if we make money at it."

"That's fair, I guess. One thing though. If you want me to do this, its mine to control."

"Its my film," he said. "I want it seen."

"If in the end I don't want to distribute video of myself having sex, I shouldn't have to."

"Okay, we can figure it out." Al said. "I trust you not to screw me."

"Screwing you is exactly what I'll be doing!"

We laughed. He studied me. What does he see? "You'll help me, if I need it?"

"Yes," he said. "I promise. Whatever you need. I won't push. If you need to bail at any time, I'll support it. You just get less money."

"Okay," I said. "Set it up."

"You can change you mind anytime, Jess."

I pushed the check back across the table toward him. "I won't."

"No," he said, tearing it into quarters. "I imagine not. This is going to be fun."

We shook hands. I may be going to hell in a bucket, I thought, so I'd better enjoy the ride.

Ch 2. Doing that Rag

Now that she knew he was going to be fucking her, Jess would have been amenable to taking Al to bed beforehand.

He is my pimp,

she thought.

You'd think he'd want to try out the merchandise.

Instead, he sent her hotel pages from Tripadvisor and restaurant suggestions and helpful tips about managing debauched weekends from some blogs he found. Jess picked a luxury hotel in Monterey, a three-hour drive from San Francisco. Four payments of $1250 soon appeared in her Paypal account. She paid her back rent and put the rest toward her credit cards.

I'm committed now.

Over the next two months she put twelve pounds she knew she could lose again onto her normal 110, enough to soften her runner's body, give her breasts a little more weight, create some hips a man could grab onto. She put a durable temporary tattoo on her back, and another one on her right hip. She dyed her long, wavy light brown hair a funereal black, had it straightened and shaved all the hair off of everywhere else. She glued a birthmark to her cheek and another on her neck. She went to her stylist friends at Macy's and had fun experimenting with make up to find a style opposite her usual one. She went through her closet—if it was short, skimpy or sheer it went into her suitcase. Each one had a memory attached.

This is what I was wearing when I abandoned Katie that night. This got me fucked in that bar parking lot. I won the blowjob contest in this one.

With the extra weight her tiny black bikini fit her perfectly again.

This is the body I had as a drunk. Fitter. Prouder. Sluttier.

The night before they left, she did herself up and studied herself critically in the mirror, naked.

Just enough deniability.

She threw on one of the dresses and Facetimed Al. "If I didn't have your number programmed into my phone," he said, "I wouldn't know it was you." She hoped that was true.

Jess chose a blue cotton shirtdress

with cap sleeves that snapped up the front for the travel day.

I can't imagine,

she thought,

that it will stay on me for very long.

Al had rented a brand new white Suburban, with deeply tinted windows and top of the line luxury interior.

"Awesome pimpmobile," she said.

"Thank you. I thought I should play the part."

"Do you have a white suit and a fedora in the back?" He was wearing shorts and a t-shirt.

"The drycleaner lost them."

"Where are the guys?"

"We're picking them up at Steve's hotel. I figured they didn't need to know where you live."

That was thoughtful.

"Are you nervous?"

"Terrified," she said. "Determined."

"Beautiful," Al said. "Sexy."

"The extra weight is weird. It doesn't feel sexy."

"I like it. You were too skinny before."

Jess absorbed that. Only your friends will tell you . . .

She patted his thigh. "You like the look?"

"A little too goth for me; I like natural better. But it gives you deniability, if we do the film."

"I'm going to have to touch it up every night."

"Woe is you."

She punched his shoulder. "Don't be cynical," she said. "I have a role to play."

"Who's being cynical now?"

But that's how I survive this, playing my role.

The guys were waiting at the curb.

"This is Jess," Al said. There was a round of introductions.

"I remember you," said Steven. "You look fantastic. Sexy. Didn't your hair used to be a different color?"

"Maybe," Jess said.

Everyone is good looking, she thought. Clean-shaven. No big bellies.

When Al got on the freeway, she unhooked her seat belt and knelt, elbows on the seat back, to face the men. She felt her dress ride up and shifted her hips a bit to send it higher, for Al.

"So," Jess said, "everyone understands what's going on here, right? You paid the base fee, but I'm expecting each of you to ante up more over the weekend for more extensive depraved acts, which I will provide. You're paying a lot, and I respect that. I'll do what you want me to, but ask for what you want. No anal, no forcing, no foul language. No means no and stop means stop, but I like sex. I'm here to cooperate, not capitulate. Understand and agree?"

There were murmurs of assent.

"Okay, then. Let's get started."

Jess climbed over the seat and plopped down between Ed and Jack. "Would you like a blowjob, Ed? And you guys can watch."

"I don't want to cum before it's my turn," someone said.

"If you cum watching me," Jess said, "it counts."

"Think about your grandmother," Steven said.

"My grandmother was a bikini model," said Jack "I used to jack off to her photos.".

"TMI!"

Jess ignored the general hilarity and extracted Ed's cock from his pants. She bent over his lap, took it in and rolled it around in her mouth. It was circumcised and warm and fit nicely; she didn't have to strain to accommodate him. He swelled respectably. Once it was hard she pulled off, handling it, rubbing all over, up and down with her hands.

"This is a nice cock, bud."

"Ed," he said.

"Of course. Ed."

"I'm glad you like my cock. Can you please keep sucking it?"

This is my job. When someone asks something direct, I just do it.

"Okay!" she told him. It was fine to do it. It was nice cock, it was pulsing and stiff and her lips and mouth enjoyed its heat. Ed was certainly enjoying it.

Steven, alone in the third row, was leaning over the seatback, watching her. "There's more to see," he said, and she felt the snaps on her dress pop open and hands crusied her legs and over her ass and all the way up to her shoulders. It felt like a lot of hands. Her dress bunched at her shoulders. Some of the hands came down her back, reaching toward her pussy. "Not yet," she said, closing her legs, remembering men's rough fingers on a dry pussy. "Anywhere else is fine." So one hand found her right breast and the other ones roamed her hips and thighs and ass. Ed was really worked up and started to pump her mouth.

I can't take that all weekend,

she thought, so she put an elbow into his hip to hold him down, sucked him to a certain depth and rubbed fiercely with her hand until he convulsed back and came all over her face.

They have to be jerked off to control the mouthfucking,

she noted, while wiping a gob of cum from her eyelid.

How a whore learns.

"Wow, Jess," he said. "Awesome. Jack, you have to try this."

This,

Jess thought. She was a mouth at the end of his checkbook.

"Take a picture," Ed said.

She nestled Ed's spent cock against her cum covered face, smiled coquettishly, kissed the tip as Jack snapped away.

"Hey Jack, you're next!" Jess said. "Open up!" Jack fumbled with the buttons on his pants. "Do you want Ed's cum on my face or off it? Customer's choice."

"She's all business," Al commented from the front seat. Jess had forgotten he was there.

"You can even get frequent flyer miles," Jess said. "What's in you wallet?"

"I am looking forward," Steven said, "to flying you frequently."

"Two flights a day," Jess said, "just like everybody else."

Jess put her mouth around Jack's cock, took it in and out a few times, experimentally.

This cock,

she thought,

is more or less like the other one. Little curvier in the tip. These two won't be a problem.

She went to rub him, but he put his hand very lightly on the back of her head, "Up and down, please?" he asked, and Jess slowed her pace, explored the cock with her lips and tongue, felt it's heat, increased her suction in places, drew all the way off and used her hand for one or two strokes, went back down again.

This is okay, I'll just bring him off now,

so she hummed and sucked and licked and soon he started quivering and his muscles tightened and he shot into her mouth.

When was the last time someone came in my mouth?

Jess wondered absently, managing the bitter taste, containing and swallowing Jack's seed. She sucked for a bit longer. Jack was quaking. "Stop," he bleated. "I can't take it."

Jess sat up and wiped her mouth on the back of her hand. No cum had gotten on her dress. They were just leaving Los Gatos.

"Steven?"

"Jess?"

"Let me take a little breather and I'll come do you, if you're ready."

"I'm ready when you're ready. Come back here now, though. There's more room. I can feel you up."

When she crawled over Jack's lap he took hold of the collar of her dress and peeled it off her arms. When his hand ran past her cunt she arched against his palm and he slid two fingers into her. Jess fucked his hand convulsively.

This is what I have to control,

she thought,

I have to get paid for everything. And I can't get lost in my own pleasure. Can't get used up. I have enjoy all these days.

"Later," Jess said, "when its your turn again," and she scootched around to the 3rd row seat of the Suburban. Steven had taken his clothes off. He was broad chested, hairy, muscular. His cock was thick and already stiff and noticeably bigger around than the other two. She plopped down on the seat next to him, threw her arms over the back of the seat and stretched her chest and shoulders. She spread her legs slightly. He handed her a bottle of water, ran his hands over her breasts. She moved away.

"Two down, she said, Twenty two to go." She took a big gulp.

"That taste okay?" he asked.

"Not bad," she said. "For water."

"Not what I meant."

"It's not about the taste," she said. "Want to try?" She went to kiss him but he pulled away.

"No fucking way."

"Don't be creepy," she said.

"You get to say no," he said. "Me, too. Maybe one of the other guys will want that."