by Ben Boswell
I gazed at her heaving breasts. “So are you.”
In a rush of excitement, she reached behind her back and unsnapped her bra.
“Oh God,” I sighed.
I reached out. She flinched slightly, but didn’t pull away. With my fingertips, I traced a line from her throat into her cleavage. She shivered and locked eyes with me, her pupils widening. I leaned forward to kiss her.
She put her hand up to stop me. “Your turn.”
“Huh?”
She laughed. “Truth or Dare? Remember, we’re playing a game here?”
I suppressed a frustrated groan. She didn’t move to put her sweatshirt back on, so I knew she was just messing with me, dragging it out.
“Uh, dare.” I hoped she’d dare me to take off my pants.
She didn’t. Instead, she smirked and drew her fingers across her stiff nipples. “I dare you not to look at my tits for a full minute, but you’re not allowed to close your eyes or look away from me.”
“That’s easy,” I said. I locked eyes with her, but immediately felt the draw of her boobs. And that was before she began to tempt me.
“Have I ever told you how sensitive my nipples are?”
My dick was rock hard. I forced a chuckle. “Uh, no, you’ve never mentioned that. Not sure why it didn’t come up when we were studying for Evidence.”
She ignored my comment. “It’s true though. When I touch them like this…. Mmmm…. I get all tingly.”
I wanted to make a joke in response, but none came to mind. Nothing came to mind actually, except this overwhelming desire to look down and see what she was doing to herself.
“But you know what I really love? I love sucking my own titties. Would you like to see me do that someday?”
It was a physical struggle to look her in the eyes. It felt the same as when you hang from a chin up bar, and after a while, you can feel your grip failing, and you know you’re going to fall.
“Or maybe you’d rather suck them yourself? Would you want to take my plump nipples into your mouth? Make me moan and squirm until I beg for you?”
I looked down at her perfect boobs and hard, dark red nipples. She laughed.
“What? That was at least a minute.”
“Thirty seconds at most.”
She laughed again. “We’ll use a stopwatch next time. So, my turn, I guess. Truth.”
I tore my eyes away from her breasts. “Okay… tell me your deepest, darkest, sexual fantasy.”
Bingo. She turned bright red, and I knew I was in for something good. She looked away and seemed to think it through, weighing options.
“And don’t lie. I’ll know.” I told her.
“How?”
“I just will. So, Ally, spill it.”
She looked back at me, her face still flushed. “I can’t do that.”
“Ha, you lose.”
“I guess I do.”
She lifted a heavy breast and sucked her nipple into her mouth. I gasped.
“So, George, looks like to the winner goes the spoils. What are you going to do with me?”
I wanted to tell her I was going to fuck the hell out of her, but I couldn’t get the words out. Instead, I leaned in and kissed her hard, first on the mouth, then on her tits, and when I finally got her tight jeans off, right on her tight, wet pussy.
Chapter Three: Preparations
I stared at the door. Then sat on the bed. Then rose to stare at the door again. It was almost one in the morning. Where had she gone?
I tried to remember what had happened before she left. Had I crossed a line? Was it asking her for reverse cowgirl? Maybe it was when I teased her anus? Maybe I didn’t hand over the tip fast enough? I wracked my brain. It didn’t make sense. We’d played this game before. Many times. Not quite this realistically, but I thought I understood the rules.
I reflected back on our day and evening for clues.
* * *
I’d played cards while she had a spa treatment. Then we met back in the room to prepare for our night out.
As we had before, I helped her plan her outfit.
She modeled dresses for me. First a black, floral midi wrap.
“Sexy, but it doesn’t say Vegas to me,” I said.
She grinned and yanked on the sash, letting her dress fall open and exposing her gorgeous naked body. “Easy off,” she said. “Could be convenient.” I thought of another sash dress she’d worn on a night out, and how easily it had come undone.
“I thought you were the kind of girl who took a guy back to his room, not offered up a quickie in a bathroom.”
She shrugged. “Why not both?”
She turned and walked back into the bathroom. When she returned, she was wearing a very short, black dress. Contoured to her body, it was textured and glittery, and the cowl neck dipped down into her cleavage.
“Fuck, that one is hot,” I said.
“Not too short?”
She turned. It hardly covered her ass. She bent at the waist, just a little, but it was enough for me to see the bottom of her bare cheeks. She reached back and gave them a little scoop. My dick screamed, yes, yes. My mind, though, had second thoughts.
“Maybe a little. Could you even sit without….”
“Flashing my cha cha? Probably not.”
“Seems inconvenient.”
She shook her ass at me. “Not for grinding up against a hot guy in a night club, but that’s not really the plan.”
I nodded. The fantasy was being a working girl, not just picking up a guy on the dance floor.
She subtly drew up her dress a little and headed back to the bathroom flashing me most of her naked ass as she did. I adjusted myself in my pants.
Next, she came out in that blue dress. Painted on, cut low, it went to mid-thigh, and matched her eyes. It made her look sexy and available, and would surely get men thinking about how much of their bankroll they might be willing to part with in order to peel it off her.
“Yeah,” I said.
“Yeah?”
She approached me slowly. “You think it will make men want to pay money to fuck me?”
I swallowed hard. “Yeah.”
She leaned in close, and I thought she might kiss me, but she held back, just inches from me. I wanted to grab her and flip her on her back, get her legs in the air, and ram into her balls deep. I flinched and she placed her hand on my chest.
“Not yet, Tiger.”
I nodded.
“Help me pick what goes underneath.”
She disappeared again into the bathroom. She was in there for a long while. I wondered what was taking so long, but when she reappeared, I could see why. She’d changed into an over-the-top, Frederick’s of Hollywood, full black lace, garter belt and stocking outfit.
“Oh God,” I sighed.
“You like?”
“Oh God,” I said again.
She laughed. “It’s wholly impractical with my dress. But I picked it up yesterday while you were playing cards, and I wanted to show it off. It’s not really for meeting a man, but rather once I have a regular, I could put it on, a trenchcoat over it, and go to his hotel room.”
“A regular?”
“It’s what all of us working girls strive towards.”
“Yeah?”
“Mmm, yeah. A handsome, successful guy, who wants something more than the missionary he gets at home.”
“And that’s you?”
“If he can afford it.”
She turned. I stared at the string bisecting her ass. She sashayed back to the bathroom, and returned a bit later in her blue dress.
“What happened to the show?”
“We’ll be late for dinner.”
“What are you wearing underneath?”
“You’ll find out later.” She smirked. “Unless someone makes me a better offer first.”
We moved toward the door. She stopped suddenly.
“Wait, I forgot something,” she said.
I followed her with my eyes
as she crossed the room to her suitcase. She reached inside and palmed something.
“How many should I bring?” She opened her fist to show me three foils of condoms.
I shuddered. She held my gaze. I wanted to seem worldly. “All of them?”
“I like the way you think. Go ahead and put them in my clutch.”
So I did. I took the condoms out of my wife’s hand, and placed them in her purse so that she’d be ready in case she found a man to pay her for sex. My head swirled, and I was grateful to hold her hand to steady myself as we walked down the hallway.
We went to LAGO, and had an assortment of small plates, all of them a delight of sight and sense. Delicious and unexpected pairing of colors and flavors, an imaginative feast. We had champagne cocktails and shared a bottle of wine. We talked and laughed and commented on the other diners.
Then as we finished our meat course, Ally gave me a little grin. “So, do you think any of the diners looking at us think I’m your paid date?”
I thought about it. Especially dolled up, Ally was a little out of my league. And while she was in a stunning dress, I was in typical man attire, dark-slacks and a striped, button-down Oxford. I was in simple black loafers. She was wearing sexy stiletto lace-up heels. She was lovely and vivacious, earrings glittering, lips and fingernails a lusty, blood red. I had on a Fitbit and simple wedding band. I noticed that Ally had removed hers.
“Certainly possible,” I replied.
She looked around, seemingly enjoying the reproving glances she imagined she was now receiving.
“Happens a lot in Vegas,” she said.
“That’s what I hear.”
“I guess, we’ll see tonight. I’m actually going to name a price.”
I raised an eyebrow. “Oh?”
We’d never gone quite that far in the game. There had been the dressing up, and even Ally sitting at a bar alone getting approached by other men, but she’d never gone beyond vaguely hinting that she might be on the clock.
“How much do you think a man might be willing to pay to fuck me?”
“I… I don’t know.”
“You’re a man.”
“Yes, last I checked. But not one who has done any sort of market research on this.”
“Hmmm,” she said with a pensive nod.
We moved on to Amaretto and coffee with biscotti.
Ally returned to the theme. “I guess it depends on what exactly I am offering and for how long.”
I nodded. “And what are you offering?”
“Everything has a price.”
We’d been married for seven years, and I hadn’t experienced everything . Not by a long shot. I ran through my mental list. Threesome, bondage, anal….
“Everything?”
It felt like she was reading my mind. “Sure, for the right price.”
I shifted uneasily in my seat. She grinned approvingly. Then she said, “Come on, Honey, let’s finish up here, and see what kind of trouble we can get into.”
Chapter Four: Revelations
After law school, we moved in together in a small one-bedroom. We’d both landed jobs in BigLaw, and were making tons of money. That was great and welcome. Neither of our families had ever had much, and we both had huge loans to pay off. But it also meant we rarely saw each other.
For a young associate, in particular, BigLaw hours are brutal. It isn’t so much getting in, which was often around 9:30am, but rather the expectation to work late, late into the evening. Our firms covered dinner, and everyone stayed past 10:00pm every night, even if much of that late-night period was more about bullshitting and pranks than actual work. If we’d been at the same firm, it would have been bad in its own way, but since we weren’t, it often felt like we were at best roommates. Coming home around midnight most nights, after twelve hours at the office, is not conducive to an active sex life.
In retrospect, it is a miracle Ally and I survived as a couple. The hours kept us apart. We both also had a lot of travel. And I know that for me, at least, there was a lot… A LOT… of temptation. I was 28, making nearly 200k a year, often on the road, drinking with buddies, going to clubs, and there are many, many women out there eager to strike up a friendship, or more. There were some close calls, but I never cheated on Ally. In the end, my scruples got the better of me, or maybe I was just scared of losing her.
Then there was the pressure. The pressure to bill hours. The pressure to be the best of the associates and get the most interesting work. The pressure to justify those crazy salaries they were paying us.
I loved it though. The camaraderie, the intensity, the sense of being, you know, a hotshot, working big cases for big clients for big money. I worked in finance, with even higher stakes than most practice areas. Ally, however, didn’t enjoy it.
The day we paid off our loans, about a year and a half after graduation, we had a party. We started at a bar, went to dinner, and ended up at a club with all our friends. It was a great time, and when we got home, Ally broke down.
It wasn’t a full meltdown. No hysterics or sobs. I just came out of the bathroom and found her sitting on our barely used sofa, with tears running down her cheeks.
“Baby, are you okay?”
“I can’t do this,” she said.
“Uh… what?”
“I hate being a lawyer.”
I sat down beside her and took her hand. “It’s okay. You don’t --”
“Two-hundred grand, down the drain.”
“No. No. It’s not… what difference does it make? Our debts are paid off. If you hate it --”
“The money is so good,” she said.
I shrugged. “We don’t need it. I --”
“We?”
“Yeah, we. I mean, I don’t know, I guess we’ve never really talked about it in detail, but yeah, I always figured it would be we. Do you want me to get down on one knee and make it official?”
She waved me off but her smile told me she’d been waiting for me to ask. Then she shook her head.
“I don’t want to mooch off you.”
“You’re being silly.”
“I’m serious. It’s not healthy for one person to make all the money, and --”
I eyed her up and down ostentatiously. “I’m sure we can find a way for you to earn your keep,” I said.
She stiffened visibly.
“I’m just kid--”
“What would I have to do to earn my keep? ”
“Ally, I --”
“Would I have to suck your big, fat cock?”
I shuddered and my prick hardened in an instant. It felt like she was launching into a sex game of some sort, but I held back, sensing a trap.
I shook my head. “I didn’t mean it that way.”
She leaned in toward me and palmed my crotch. “You sure, Baby? Because it feels like maybe that’s what you’d want. And it would be only fair. If you’re bringing home the bacon, the least I can do is take it out of your pants and slather it up with my tongue.”
“Ally --”
She kissed me hard. She tasted of the rum and coke she’d been drinking, and she thrust her tongue into my mouth. She worked her hand into my pants and jerked my cock.
“Oh God,” I sighed.
Ally unbuttoned my shirt and kissed her way down my chest. She paused to unbuckle my belt, and I lifted off the sofa to let her yank down my pants. She swallowed me deeply. Her mouth was hot and wet, her tongue swirling around my cock. I ran my hand through her hair as she began to bob up and down.
“Oh, Ally.”
She rose up suddenly, and I was terrified I’d done something wrong. She assuaged my fears by quickly stripping off her tight jeans. She was wearing skimpy, white panties beneath, and my eyes were drawn to her crotch, where the fabric was damp and translucent with her arousal. She climbed into my lap and ground against me. She kissed me with a desperate hunger, gasping into my mouth. Then, reaching between us, she slipped her panties to the side, and impaled herself on me. She was drenc
hed and so excited that it was a little loose, but her rolling hips and passionate moans made up for it. I yanked up her tee shirt, pulled down her bra, and sucked an overripe nipple into my mouth. She hissed and clutched my head. Her pussy throbbed on my cock.
“Oh fuck!” she gasped.
“You’re so hot.”
She bounced on me almost violently, like she was trying to break me.
“Yeah, Baby, fuck your hot little whore.”
“Oh God.”
I began spurting inside her. She sucked on my neck.
“Oh fuck, oh fuck, oh fuck,” she moaned. “That’s was fucking intense.”
I grabbed her head and kissed her hard. “That was amazing,” I agreed.
She leaned back, still impaled on my shrinking cock, our juices beginning to leak onto my balls. She fanned herself. Even though she seemed into it, there was a dark tinge to the sex.
“Are you okay, Ally?” I asked. “That was… crazy.”
She blushed, and I realized it wasn’t just from excitement. “Can I tell you something?”
“Uh… sure?”
“Do you remember our first time?”
I chuckled. “Yeah, you almost made me fail my Torts exam.”
“I’m pretty sure I did fail.”
“Well, it was worth it.”
“Do you remember what we were talking about right before we started, you know…?”
“We were playing a game… truth or dare. I think I asked you, like, a fantasy or something?”
“My deepest, darkest, sexual fantasy.”
I was breathing heavily, wondering where this might go. I nodded.
“Do you want to hear it?” she asked.
My cock, which had been trending toward flaccid immediately reversed course. “Uh… yeah.”
She leaned in and kissed my neck, which also allowed her to break eye contact.
“Promise you won’t think ill of me?”
“Of course.” I wasn’t sure that I could keep my promise, but I wasn’t really thinking it through. “I promise.”
She nibbled on my ear. “It’s wrong… and dirty.”
I was rock hard again. She slowly ground against me. We were so wet and messy that it made a lewd, squishing sound.
“I fantasize about being a whore,” she said so softly it was barely audible.
