Boo Club

There's sitting at a bar by yourself drinking a tequila soda and then there's sitting at a bar by yourself drinking a tequila soda while stuffed with a butt plug.

You can guess which type of night I was having.

It was supposed to be book club for my wife and the rest of the ladies in her newsroom--thoroughbred dime-piece reporters and anchors of varying races talking about whatever book was trendy that month. What separated this book club from just about every other book club in the world is that it transitions into the women pulling out strapons and pegging me--the innocent husband of the 10 pm anchor. It all started with a surprise in which they caught me, ahem, experimenting solo in my own home. Last month, they played strapon roulette with my ass, laying me on a spinning ottoman and taking turns pounding me while the rest watched. Needless to say, I'd begun to look forward to book club much like the rest of the group.

However, my wife assured me there'd be no funny business tonight. The news director was coming. For those not in the know, the news director was the boss of the newsroom and almost always a 50-year-old white guy.

"So why am I even going?" I asked as we walked into the bar, a hip Asian-Mexican fusion joint with lots of purple and blue lights and peculiar things hanging on the walls as decor.

"Because I like showing you off," Jess leaned over and kissed my cheek. "You know they're all jealous they can't fuck you."

Her warm breath on my neck sent a chill through me. I put my arm around her and pulled her against me. Her arms followed suit, wrapping around my waist. She wore a jean jacket atop a tight white shirt and a pair of leather pants that might as well have been painted on. She looked good and she knew it.

Before we left the house, Jess inserted a neon pink plug the size of a cone-shaped ping pong ball into my ass. It took some finagling and a lot of lube but once it eclipsed my puckered asshole I gasped a four-letter word that rhymes with duck. She said only if I was a good boy.

So like a good boy, I sat at the bar solo watching some Mexican league soccer game and drinking tequila while my wife and her friends laughed and shrieked about god knows what from across the restaurant.

"Can I buy you a drink?"

I looked over my shoulder for the person belonging to the offer.

"You can," I said. "But I must confess my wife is sitting just over there."

"I know."

"You know?"

"I better. I hired her."

Then it clicked.

"You must be Toni."

"And you Ben. Great to finally meet you."

"You as well. I've heard a lot of good things."

"I can say the same for you. So what're you drinking?"

"Hornitos and soda," I said coolly.

"Oh alright," Toni said with a grin. Toni was also most certainly not a 50-year-old white dude. She was maybe 40, Hispanic with long, jet-black hair and thick lips. She wore high-waisted jeans that showed off her hips and highlighted a very voluptuous figure while her yellow and black plaid shirt nearly burst at the buttons trying to conceal her breasts.

"Do you have money riding on this game or something?" She asked.

"No, why, do I look like a gambler?"

"You're just fidgeting on your stool a lot."

I felt a wave of panic crash into me. Did she know? How much did she know? Was that an I-know-what-you-like smile or just a smile? I fought off the question avalanche with a rushed sip of tequila.

"Nope. Just nothing." I mumbled.

"Gotcha."

"So Jess was saying you're kind of one of the owners here?" I said with wavering confidence.

"Something like that. The actual owner is a good friend of mine and a few years back asked me for some help--vision-type consulting."

"Vision?"

"If you're going to open a tequila bar, you probably should consult a Mexican."

"Fair enough. So the artwork is all you?"

"Yes and no. I picked out a few pieces."

"Oh yeah? Which ones?" I craned my neck to look around the room. Toni nodded up at a massive mural above the bar that spanned the length of it. It depicted some scene from history except all of the people were skeletons and the scene itself looked cartoonish. Almost like a fever dream.

"Very cool," I said, secretly trying to make sense of it.

"Want to see something really cool?" Toni said with a sly grin.

"Sure."

"Come with me. Bring your drink."

"Okay, let me just tell Jess."

"You're good. I already told her I would steal you away."

"Oh alright. So where to?"

Toni led me into a long corridor lined with bright paintings of jungles and lizards. We passed by a set of restrooms, one for Caballeros the other for Damas, a constantly swiveling door leading into the kitchen, and finally a set of stairs up a narrow corridor. At the top was a solid black door with a keypad and the words: Managers Only stenciled across in small letters at eye level. Jess punched in a code and popped the door open with her hip.

Inside was a large office. Oak desk, artwork on the walls along with a small living area. It reminded me of a suite at a baseball game where you could sit on the balcony and watch the game or you could sit on a leather couch eating chicken tenders and watch another game on a giant tv. But as I walked in I noticed along the back wall there was a long window. I walked towards it, soon realizing that it provided a view down into the bar, like a foreman overlooking their warehouse.

"I didn't even notice this window down there," I said without looking at Toni.

"You wouldn't. It's actually the mural."

"Wow. That's pretty cool."

"Thought you'd like it?"

"How'd you come up with it?" I still looked out it, trying to locate Jess and company. They were still hooting and hollering from their corner booth.

"Oh definitely," Toni said. She sounded distracted. Or at least busy. "This way I can always keep an eye out for loners at the bar betting on Mexican soccer games."

I turned from the giant window to find Toni standing in the middle of the room--a crimson leather harness over her dark jeans and a black strapon dangling between her legs.

"Whoa."

It's all I could think of.

"What do you think?"

"I'm not sure what to think."

"Well, do you like?"

She did a little twirl. The harness cupped her ass sublimely, the straps pressing ever so slightly into the meat of her upper thighs. It warranted a firm slap. The opportunity for such a gesture twirled away, however, replaced by a long, thick, silicon cock swinging between her legs.

"Looks good," I mumbled.

"Which part?"

"All of it."

"That's what I thought."

We stood there a beat, me trying desperately not to stare and her making no bones about tracking my gaze.

"Do you like?"

"I'm not sure this is a good idea."

"Oh no?"

"No."

"And why's that?" Toni said with a little grin. She began to walk towards me and the strapon swung with her hips. She stopped just in front of me and put her hands on her hips, her tits jutting out and straining to stay in her shirt.

"I'm not sure Jess would approve."

"But she approved of the other girls having their way with you?" She said knowingly and teasingly.

"That was different," I said.

"Was it?"

"Yeah. This just doesn't feel right."

"Oh yeah?" Toni reached her hand towards my pants. Her hand immediately found the outline of my cock through my jeans. It was firm and growing against my best wishes. "I think it feels just right. And somebody else agrees."

She began to undo my fly but I stepped back.

"That's what makes this so hard."

"You don't say."

"Yeah. You're obviously smoking hot but, I love my wife and this isn't what I want."

I expected my declaration to deflate her a little bit but if it did, she didn't show it.

"Fair enough. But I think you're making a mistake. Jess told me you'd be down."

I weighed this. What if Jess was giving me the green light here and I was blowing it?

"Well, maybe some other time," I said with a sigh. "But I think I better get back down to the bar."

"Fine. You win. You know where the door is." Toni kept her hands on her hips while nodding back towards the door. I didn't hesitate and made a beeline for the exit. If this was really green-lit by Jess and I squandered it, I could live with that. I couldn't live with the alternative.

As I got to the door, I slid the deadbolt back and turned the handle.

And there she was.

Arms folded.

I froze. No words came to mind so instead I stared dumbly at Jess, hoping she couldn't see her boss standing behind me wearing a massive strapon.

She could.

"What's going on?" She asked firmly.

"Uh, nothing. Nothing. I was just leaving."

"Is that right? You guys have some fun?"

"Nope. No fun."

I tried to usher her out but instead, she put her hand on my chest and guided me back into the room. I peered over my shoulder at Toni, waiting, imploring her to say something to bail me out.

"Okay, okay. Before you say anything else, Jess, I have to put an end to this. You've got a good one here."

"Is that right?" Jess said without taking her eyes off me.

"I came at him with everything I had. And he turned me down. Said it wasn't right without you."

I blushed for some reason but I really just wanted to be someplace, any place else.

"Really?" Jess said. "My boss doesn't turn you on?"

"No."

"What?!" Toni chimed incredulously.

"I mean yeah, she's obviously hot."

"And?"

"And she looks unreal with that strapon but, I don't know, she's not you."

"Awww. You really did hit the jackpot with this one, Jess."

"I think you're right, Toni," my wife said, with the faintest bit of a smile.

"And if I can't fuck him, you better."

"What?" I said.

"He definitely passed the test. I think it's time he got his reward."

"Test?" I asked. "You knew about this?"

"Of course I did. Do you think my boss would really just try and fuck you the moment she met you while I was in the other room?"

Hearing it laid out plainly really helped expose the insanity of it all.

"I guess when you put it like that."

"So I just wanted to be sure."

"Be sure of what?" I asked.

"We've done some pretty kinky shit these last few months. I wanted to make sure I was still the one you wanted."

I grabbed her by the waist and pulled her against me. Jess' arms flew up around my neck as our faces came together.

"Of course you're the one I want."

I kissed her and again I heard Toni aww from behind me. I clasped onto Jess' firm ass and thrust her even tighter against me. She could feel how badly I wanted her. I wanted to rip her clothes off and fuck her brains out right there.

"Not so fast, Cowboy." Jess breathed into my mouth. "We've got company."

I peered around at Toni who still stood with her hands on her hips. I cleared my throat.

"Toni, would you mind giving us a minute?"

"Oh, that's cute."

"What is?"

"I'm not going anywhere, sweetie."

"You want to watch?" I asked.

"She's going to do more than watch."

I refocused on Jess. She held a serious grin. "Now take your clothes off."

"I don't follow," I said.

"You will," Toni said from behind me, her voice now much closer. Then I felt her hands brace my ass before reaching to the front. She began to unfasten my belt and pants. Jess stepped back from me.

"Take your clothes off. Time for your reward for being such a good boy."

Jess kissed me softly and turned and walked towards the desk. Her ass swayed sensually as she went and looked sublime in her leather pants. Toni meanwhile had unfastened my pants but backed away and stood somewhere unseen behind me. I peeled my shirt over my head while simultaneously kicking off my loafers. I turned to face Toni.

"Huh huh. Face the wall, sweetie. I like my angle."

I did as I was told and unzipped my pants. I had to maneuver my pants over my rock-hard cock. Then I hooked my thumbs into my waistband and lowered my pants.

"Oh my," Toni said softly. "Jess, looks like you have your man ready to go."

I felt a slight tug on the plug that resided well-entrenched in my ass. My dick jumped.

"You should see it from this side," Jess said.

"Show me."

I turned to face Toni.

"Oh wow. Packing heat and loves to be fucked. Where'd you find this man?"

Toni reached out with both hands and ran them down the length of me. They were small and supple and when she got to the end she rotated and began a slow return trip back. I thrust my hips slightly forward.

"Oh, this is going to be fun. He looks like he's already going to bust." Toni said with a grin.

"Not yet he's not. Where do you keep your toys."

"Bottom drawer." Toni eased me closer by gently pulling my cock towards her. I glanced down to see I was side by side next to her strapon--her left hand still cupped under me while her right did the same to her member, subtly gliding up and down both. If her small hands accentuated me, they had the same effect on her strapon: her fingers couldn't wrap all the way around her cock--a detail highlighted further as she pressed the two dicks together. "Looks like I'm bigger," she whispered. "That gonna be a problem?"

I shook my head no.

"Good," she again whispered to me. "Mind if I get started, Jess? I'm not sure he can handle the suspense much longer."

Toni slapped my ass. It doubled as fun and direction. She wanted me to turn around.

"Go ahead. He should be ready to go."

I turned as I was told. I felt Toni's hand clasp onto my ass. She guided me forward and towards the desk. It was below waist height and I leaned over it, presenting my ass to Toni. She again slapped it firmly. I glanced at Jess, curious if she'd found what she was looking for. Her search had stopped. She simply leaned back against the desk, her arms holding her up. She'd taken her jean jacket off and now her tits stretched the fabric of her shirt. She watched intently, her bottom lip pinned between her teeth.

I heard the click of the bottle of lube open followed by the cool sensation of the jell dripping onto my ass and down my crack. Toni's finger soon followed, caressing the lube around my asshole and the plug already buried inside me. I held Jess' gaze. A few circles and two slight tugs made my legs quiver. Before I could bask in the feeling Toni extracted the plug with one smooth motion, leaving me gaping.

"Ohhh," I shuttered.

As I embraced the new feeling of emptiness, it was immediately replaced by the unmistakable presence of something else: hard, cool, stiff, and with the help of a palm steadied against the small of my back, that new thing pushed inside me. I gasped while my head shot back as Toni slid her cock in.

"That's right, sweetie."

"Ohhh, fuck." I mouthed. I felt a hand rest atop my own and give a reassuring squeeze. I locked eyes with Jess as Toni pulled out. Again the emptiness was short-lived as Toni pressed against me and popped back inside. My moan was as long as her shallow stroke.

Jess pulled her hand away and went back to looking in the drawers. I tried to watch her selection process but Toni was establishing a rhythm that made it virtually impossible to think. Fortunately, the two of them elected to confer on the decision.

"So many choices!" Jess said.

"I like options. You never know what somebody is going to like."

"Look at this little guy," Jess said, holding a pink member maybe three inches long.

"That little guy gets results," Toni assured her.

"Got any ones that cum?"

"Not here, unfortunately," Toni said with a slight tinge of disappointment. "Let's see if he can tell the difference between the two of us," Toni suggested without breaking her cadence. It remained slow and shallow. I did not object.

"So I'll need a similar cock." Jess pulled out two. One was neon pink and firm, the other was flesh-colored and so long it dangled. "How thick are you?"

"Thicker than his," Toni said with a swift smack of my ass causing a moan to escape me.

"Okay," Jess said. "So no to this thin guy." Jess picked up a black one that was easily as thick as a Coke can.

"Too thick?"

"Definitely too thick," I moaned amidst Toni's fucking.

"What about length?" Jess continued.

"Let's let him guess.," Toni said. "What do you think, Ben?"

Toni's hands slid to my hips as she gently steered herself deeper inside. I gasped with every centimeter as she slid deeper and deeper. Numbers flew through the air. I bit my lip and tried to count as if I was a functioning depth gauge. When I felt her direction change, I threw out a number.

"7 inches." I breathed.

"Not bad! This one's actually 8."

"Wow, look at you!" Jess said.

"Too bad I'm only about halfway in."

"Halfwaaaaaaay?" My question trailed off as Toni proved it, pressing herself deeper inside me. My moan again mimicked her motion. My cock jumped as she began to peel away.

"Balls?" Jess asked unfazed.

"Ben?"

Now Toni again pressed inward with the slow precision of a drill press making its initial mark, but where she'd stopped previously, her hands gripped my hips tighter and eased deeper and deeper and deeper.

"Ohhhhhhhhh." I gasped and trailed off but soon moaned again as Toni writhed against me. Denim rubbed against my bare ass while something else grazed the inside of my thigh. My moan segued into a yes.

"Yes, I have balls or yes you like it when I go that deep inside your ass?" Toni asked tryingly.

"Both." I wheezed.

She finally eased away and again the escaping feeling rushed through me, only to be methodically stuffed back inside. This became Toni's game: running her cock into me until I felt her jeans against my flesh, then sliding out until I could feel the ridges of her strap-on's head but never leaving me completely. Each thrust sent a faint murmur of a moan out of my mouth.

"I think it's getting to be my turn." Jess' words brought me back from wherever else I was. I looked up at her. She'd taken her pants off and wore a harness fashioned into a set of pink boy shorts. Her neon green strapon jutted through the black ring at its center and glistened beneath her hands while she stroked lube up and down it.

"You look amaziiiiiing," I tried to say it smoothly but Toni had taken the opportunity to remind me just how deep she could go. I rested my forehead on the desk and moaned into the wood as Toni removed herself completely. When I looked up, Jess was gone.

Then she wasn't.

Her hand atop my back coincided with her strapon pressing against my asshole.

My asshole put up little resistance.

Jess slid inside me, slowly inching her way deeper and forcing a moan and spasm to shoot through my body.

"That's so good," I said.

"Yeah?"

"Fuck! Yes!" I again moaned in exasperation.

"Oh wow," Toni said. "He definitely just came on my desk!"

I burrowed my head under myself and looked down. Sure enough, Jess had made me cum damn near instantly.

"That is so fucking hot." Toni declared. "Although, it's not as much as I thought it would be."

Toni reached her hand under me and dabbed at the small puddle.

"That's just a taste," Jess said proudly. Her thrusts had slowed and she took the opportunity to squeeze more lube onto my ass and onto her member.

Toni reached upwards and touched my cock.

"He's still super hard."

"Now we can have some fun," Jess said. I didn't need to see her grin to know it was there. "Just don't touch that cock."

Toni pulled her hand away and retreated back behind me out of sight. The ensuing smack across my ass could've come from either of them. The deep thrusts could've only been Jess.

"Oh fuck," I gasped.

"That's right, baby. Show me how bad you want this dick."

I raised my ass and buried my head into my arms. The first moans that escaped my body as Jess began to ramp up her speed were muffled against my forearm.

"These are soundproof windows, sweetie," Toni said matter-of-factly. "You can do better than that."