Whatever It Takes

by Ben Boswell

  I gasped at her. "Jesus, Jessi, I can't be part of that."

  She sighed. "Oh, grow the fuck up. You don't think they paid me to come up here just to shake my ass and tease them, do you?"

  "I... I... I don't know," I stammered.

  "Come on, Danny, this is the last time. I swear." She softened, forced a smile. "Look, consider it collecting contributions toward my college fund."

  I wanted to say no, walk away. But I was already in so deep. I shrugged resignedly.

  "Great. And make sure to get a thousand for the show."

  I nodded. She disappeared into the bedroom.

  I took a deep breath and somewhat sheepishly approached the guys who were standing in a circle, and looking over toward us. I managed to get out her quote sheet, and the best man counted off bills.

  "Okay, dude, here's the grand and three to get the groom started with a bareback hummer."

  He then clapped Vinny on the shoulder and said, "Go get her." He shoved his buddy toward the bedroom. Then turning to me, he said, "She better swallow it all, or we get our money back."

  "I... I'm not sure..."

  He laughed. "Relax man, just busting your chops."

  I forced a laugh.

  The guys flipped on the TV and tuned to an MMA match. They were pouring scotches, offered me one, which I took. They were also cutting lines, which I declined.

  It was a crazy scene. Six of us sitting around watching two maniacs beating the crap out of each other on TV, while in the next room my sister-in-law was turning tricks.

  After about three minutes, Vinny walked back out to cheers and taunts. "Did you even get it up? That was quick! Yeah, tell us about it, quick-draw!"

  He laughed and shrugged, then stooped over the desk to do a couple of lines. "What can I say, she's good."

  "Good enough for me," replied the best man, slipping five hundred into my hand.

  Jessi had given me no real instructions. I guess she was worried that it would freak me out. I was flying blind. What had he just bought? Bareback straight sex? Was I supposed to confirm it with him? Let her know what was being paid for? What if a guy gave me money for a blowjob with a condom and then had unprotected sex with her? How long would I go to prison if we were busted? And how fast would Kris divorce me if she found out?

  These were the sorts of questions that ran through my head as I continued to collect money and Jessi continued to fuck men in the bedroom. They all took at least one turn, a few of them two. All of them chose to pay the bare backing premium.

  The best man approached me again. "Alright, bud, got a special request. We've been saving her backdoor for the groom, but we want them to do it out here."

  "I don't think that's an option."

  He slapped me lightly across the face. "Don't think. Just ask the whore how much."

  I blushed a deep red and quickly excused myself, bristling as their laughs filled the room.

  I opened the door to the bedroom.

  Jessi was naked, of course. Wearing just her heels. The last guy had paid for sex, so she was wiping down her pussy.

  When she heard the door open, she called out, "Hey baby...." But then she saw me. "Oh, it's you."

  She continued to towel herself off, completely shameless in her nudity. God, she looked so hot. The fact that she was such a complete slut made it that much more erotic. She'd taken almost a dozen loads already, and she was still ready for more.

  She threw her hands out in annoyance. "Well, we done or what?"

  I shook my head. I explained the request.

  She sighed. "Okay, fuck, whatever. Tell them fifteen hundred and a nice bump.... Oh, and if any of the others want to cum on my face while I’m getting fucked, that a hundred a pop," she added as an afterthought.

  "A bump?"

  She tapped her nose.

  I nodded. I was past any desire to resist. I just wanted this evening to end. I communicated her terms. They agreed enthusiastically. It occurred to me that she could have driven a harder bargain. And I groaned at the realization that I was so far through the looking glass that I was actually thinking about ways to best pimp out my wife's sister rather the recoiling in horror at it all.

  Jessi threw open the door to the bedroom dramatically.

  "So, I hear you perverts want to watch a girl get fucked up the ass?"

  Cheers. Hoots. Someone snapped off the TV.

  She ambled over to the desk and hoovered down some lines. Then she crossed the room and bent over the back of the sofa, giving me a perfect view of her amazing ass, her puffy pussy.

  To Vinny she asked, "So, you want me to suck your dick first?"

  "Hell yeah," he growled, approaching the sofa with his dick out.

  She sucked him deep into her mouth as the other guys teased him not to come too fast. He gave them a cocky "I've got this" smile and grabbing, her head with both hands, began face fucking her roughly.

  While the others were mostly focused on Vinny pumping his cock past her lips and her loud slurping sounds, I had an even more erotic view. Even as she was getting his cock hot and wet, she was fingering her own ass, plunging first one then two of her slender, painted fingers deep into her own bottom. It was mesmerizing, the lewdest thing I'd ever seen, even in porn.

  After a few minutes, Vinny moved around to the other side of the sofa. She looked back over her shoulder, her hair now a mess, her lipstick smudged. We were looking right at each other, but our eyes never made contact. Hers were glassy, distant. I didn't know whether it was the drugs or just her retreating to some place emotionally to get through this.

  Vinny spanked each ass cheek once, firmly. Then without any further preliminaries, he pressed his cockhead into her anus and thrust in hard.

  Her eyes went wide and she clearly stifled a scream. I took a quick step forward as if to intervene, but immediately felt a strong hand on my shoulder holding me back. The bodyguard was looking at me, shaking his head.

  I was about to protest that Vinny was being too rough, when I heard Jessi's voice. "That's it baby, give it to me hard. Fuck my tight little ass."

  The bodyguard gave me a smile as he felt me relax.

  Vinny was really ramming her forcefully, showing off for his friends. He wrapped some strands of hands around his fist and yanked back hard, forcing her to arch her back. He was fucking her balls deep, his thighs slapping her ass loudly with each thrust.

  "Oooh, that feels so good," she exclaimed, her voice high and tight. "I love your big cock in my ass. You're going to make me come."

  "Fuck, she's hot," Vinny growled. "Come on guys, come on her face," he moaned insistently. It was obvious he wasn't going to last long.

  The fat guy with the big watch stepped up first, whipping out his cock and stroking it in her face. She took over for him, spitting in her palm, and expertly stroking his shaft.

  "Come in my mouth," she moaned. "I want to taste it."

  That was too much for fat boy and he came with a shudder as she closed her lips over his cockhead. One of the blond frat boy types was next. Then the skinny Euro dude. Each got the same treatment and finished equally fast.

  Finally the best man stepped up. "I'm gonna paint you white," he growled. Unlike the other guys, he slapped away her hand, instead stroking himself, aiming his cock right between her eyes. He came hard, three or four thick streams splashing on her forehead, nose, and cheeks.

  "Fuck yeah," he exclaimed as the others cheered.

  "Look at me," Vinny ordered.

  She looked back at him, her face a complete mess, covered in jism which was now running down her chin and dripping on the sofa as her head jerked back and forth in time with his hard thrusts.

  "Come in my ass, baby. I want to feel your hot come in my ass."

  That was too much for Vinny. With a loud growl, her buried himself fully inside her and shuddered.

  After a few more slow thrusts, he pulled out, her once tight little ass gaping open obscenely for a few moments until she pushed herself into standi
ng position.

  "I'm gonna get cleaned up if you want more," she said heading toward the bedroom.

  But it was obvious the guys were done. They were sheepishly averting their eyes from the spot on the sofa she'd recently occupied and were instead making plans to go back out to an underground poker game.

  I shook myself out of my trance and went about collecting final payments. Several of the guys threw in tips as well. By the time she emerged in her trench coat, having concluded that there'd be no more business, I had packed up rest of her stuff and was clutching a thick wad of cash. We left after a few quick goodbyes.

  _____

  In the car, driving home, we sat initially in strained silence. Since I'd packed up her lingerie, I knew that she was naked beneath her coat, which was oddly titillating even though for the past two hours I'd seen her completely naked, taking a dick up her ass.

  She cleared her throat, "So, um, how much?"

  I reached into my pocket and handed her the money. She counted it beside me. $7200 in total.

  "Nice night," she commented.

  I could only grunt in response. Jesus that was more, a lot more, than Kris and I took home in a month, and she'd made that in a little more than two hours.

  She counted off seven hundred-dollar bills. "You want yours in cash or trade?"

  "What?"

  "You get ten percent. Do you want the money or do you want to fuck me?"

  "Are you shitting me?"

  "That's the way it works. And you've seen enough to know I'm not playing. Fuck, I'll suck you off while you drive if you want."

  I shook my head. "Jesus, Jessi. I don't want the money... or the sex. Just keep it."

  "You sure?"

  "Yes."

  She held out the cash. "Okay, going once... going twice... I suck a mean cock," she said temptingly. I held my tongue. "Three times."

  She leaned over and kissed me on the cheek, a surprisingly gentle gesture. "Thank you Danny Dan, I really appreciate what you did for me this evening."

  "You're welcome. I guess. You're done with this, right?"

  She shook the cash; it fluttered loudly. "Yeah, I'm done," she replied as she wistfully contemplated the money. "Just need to take care of one more thing."

  I sighed. "Damn it, Jessi, you promised me."

  "I promised no more stripping. I won't. And I'm done taking cock for money."

  "So what's the one thing?"

  "Let's say it’s an investment in the future."

  "If you need some investment advice, I know some good people who can help --"

  She cut me off with a laugh. "Don't you worry your pretty little head about it, Danny Dan."

  I didn't like the sound of that, but didn't really know how to proceed.

  After a few more minutes of silence, my curiosity got the better of me. "Do you always make that much?"

  She shook her head and clucked her tongue. "Naw uh. Best night ever. Helps that they all went bareback."

  "Doesn't that worry you?"

  "That's why it costs more," she replied simply.

  "Did you even know those guys?"

  "My, you're full of questions."

  "I just --"

  "You just want to know how I can be willing to get fucked bareback by six guys."

  "I guess."

  "No, I didn't know them personally. But the groom, Vinny... I, um, know his father."

  "Dad set it up?"

  She laughed. "Yeah. Guess he wanted to make sure his son had fun."

  "Jesus." Who were these people?

  She chortled again. Was she laughing at my naiveté?

  "What?"

  "Well, I was just thinking that poor Vinny didn't inherit his dad's size. I wonder if he knows." She laughed again.

  I could only shake my head.

  CHAPTER THREE

  I didn't see Jessi much the rest of the weekend. Actually didn't see her at all. At first, I figured she was sleeping in or something. She'd had a long night after all. But as afternoon came around, I wondered if she was okay.

  I went down to the au pair suite and knocked on her door. No answer. I began to sweat the worst case. Had she overdosed or something? She'd snorted a bunch of coke last night. I didn't know enough about drugs to know whether that was enough.

  I opened the door and went inside. For a few moments I wasn't sure what I was seeing. Her blinds were drawn and her room was a mess, clothes, and possessions, all over the place. It looks like a tornado had hit the place.

  I walked over to the bed. There was a lump in the middle. Tentatively, fearing the worst, I reached out and poked at it. It was a relief to find it was just a balled up blanket.

  I pulled the blinds up and the room filled with light. She wasn't there. I checked the bathroom as well, but no, she wasn’t anywhere. She must have gotten up before me and slipped out. Her bag from last night, complete with mini-speaker and balled up lingerie, was tossed in a corner. No sign of the cash, but I was pretty sure a girl like Jessi wouldn't leave that kind of money lying around.

  I shrugged. Weird. Jessi wasn't usually an early riser, and after last night I would have thought she'd be resting. But nope.

  _____

  I was sort of happy not to have Jessi around, not to have to be face to face with her. It was already hard enough reliving the memory of last night. How could I have let myself get involved in that?

  What if the cops had busted us? Drugs. Prostitution. And that was before we got into what any of those guys were into on their own. God only know how much trouble would have come out of it.

  But thinking about the legal consequences was actually a respite. My biggest fear was Kris. If she ever found out, what would I say to her? What could I say? That I had gone to keep Jessi safe? By letting her whore herself out to a roomful of men? Allowing her to snort a bunch of cocaine? Kris would divorce me. That was the best case. Worst case, she would kill me. That was far-fetched, but the reality is that just contemplating her anger was frightening.

  _____

  Kris came home with the kids late Sunday afternoon, basically just in time for us to get a quick meal into them and put them to bed. After, we sat down for a light dinner ourselves.

  "So did you have fun?" she asked.

  "What do you mean?" I asked panicked.

  She gave me a queer look. "I mean, you had a weekend without the kids. You didn't just do yard work did you?"

  I forced myself to breathe. "No. I mean... I did a lot of yard work. But, right, that's not all I did..."

  "Are you okay?"

  I felt so guilty. The urge to confess all, to throw myself on her mercy, was close to overwhelming. It almost seemed worth the certain wrath just to get it off my chest.

  "Daniel?"

  I gasped. "Yes. Yes. I'm okay. Sorry, I was just distracted. To tell you the truth, I didn't do very much. Yard work. Watched some TV," I prayed she wouldn't ask me what, because I doubted I could make up a decent answer. "Slept late. Just relaxed."

  She smiled. "Okay good."

  I breathed a sigh of relief. How could she not see I was dying inside? I forced a smile. "How about you?"

  She laughed. "Oh the usual. My mom doting over the kids, feeding them sugary stuff behind my back. My dad trying ask questions about work even when Susie was screaming about how she hated veggies."

  "We talked about Jessi," she said. Again I felt my insides tighten.

  "Oh?"

  "Yeah. They were just saying how happy they were that we took her in. That finally, she might be turning a new leaf."

  Kill me, I thought.

  "Where is she, by the way?"

  I was panicking, but happily I was able to answer honestly. "I don't know. I haven't seen her today. I slept in and she was gone when I woke up."

  A look of concern crossed Kris' face. "Weird. Oh well, how much trouble can she get in on a Sunday?"

  I shrugged.

  _____

  As guilty as I felt, I was also very turned on all day. Even as
I did chores around the house, I kept thinking about Jessi. About how she'd looked when she stripped for Vinny. I kept fantasizing about what had gone on in that hotel bedroom. All those men, one after another after another. I remembered what she'd looked like when I walked in, naked, in just her high heels, the sheen on her body.

  But mostly I kept reliving the scene out in the main room, when Vinny had fucked her up the ass. I had never seen anything so depraved, so raunchy. Those minutes where she'd blown him while at the same time fingering her butt... just thinking about it got me close to blowing my load.

  I was thinking about that as I climbed into bed with Kris. She was in flannel nightdress. I pulled her close, spooning her.

  "I missed you," I said.

  I ran my hand over the front of her dress, feeling her curves. As my palm slipped between her breasts, she took my hand in hers and held it tight. That was her sign that she wasn't interested in sex; that she just wanted to snuggle.

  "I missed you too," she said. Then came the excuse. "I'm tired from having the kids all weekend."

  I suppressed a sigh. I wondered if Jessi ever turned down sex. She didn't seem like the kind of girl who would. Even right now, she was probably out getting fucked. Maybe she was with her tattooed boyfriend. I pictured her squatting before him, naked, her snatch swollen and ready. I could see her sucking that big cock of his, making lewd smacking sounds with her lips, taking him balls deep until she gagged.

  I could imagine him picking her up, throwing her on the bed. She was the kind of girl who'd spread her legs wide, shamelessly displaying her wet cunt, fingering herself, licking the digits clean.

  "You sure you don't want a little pick me up," I offered gently.

  It was Kris' turn to suppress a sigh. She yawned but released my hand, allowing me to resume my gentle exploration of her body. She pressed back against me, feeling my erection.

  "I guess you did miss me," she said.

  "Hmmm, I did," I replied.

  I gently cupped her full breasts, circling her nipples, prominent even through the thick fabric. I leaned in close and kissed her neck.