Venturing Out

I walked into the office to find my co-workers waiting with a bottle of champagne and three glasses. Kurt threw me a party popper before I could set my backpack on my desk. Paper streamers and confetti flew over the office as Chris fired four poppers together.

"All hail the conquering hero!" Kurt cheered as Chris clapped. "Come on and dish! How did it go last night?"

I laughed and held up a hand to stop their questions as I sat on the edge of my desk. "It was fun, and I'm looking forward to a second date."

"There has to be more details than that vanilla explanation," Chris commented.

"It turns out we were on the same bus, so we went to the Hitchin' Post for dinner," I recalled. "We had a fun time and will get together again soon for a second date."

Kurt crossed his arms across his chest. "That's it?" Chris raised an eyebrow as he frowned.

"She's a great kisser, and has a tight body," I added. "There's a few concerns, but we'll see where that goes."

"A few concerns?" Chris quizzed. "So what's wrong with her? Nobody's perfect, but she seemed good to go."

I bit my lower lip, choosing my words. "I felt uneasy at times, so maybe it's just me. I'll run with it for now and see how it plays out."

Kurt sat back into his chair. "So, if Michelle's a 'maybe baby', then we're back to swiping and looking for another!"

"Open the app!" Chris cried, moving behind me.

I put my hands up. "Hang on a minute! I'm not paying you to dig through the dating app for me. Let's get those orders covered and then we can have a look."

"Who made you the boss?" Kurt asked, over emphasizing his indignation with his hands on his hips and a comical hurt face.

"I did, when I bought the company!" We laughed as we settled into our desks. As I connected my laptop to the dock and started it, I sent a text to my brother asking if he was available for lunch.

"Remember, if you bail on Michelle I get the next chance," Chris said.

"You don't think that'll be a problem if she's already dated me?"

"Nah. Meaningful overnight relationships don't need much to stand on. Alcohol is usually enough to grease those wheels."

Kurt grunted an agreement. "Alcohol. Helping ugly people get laid since antiquity." Chris snickered. "Good thing it's around to help you, Chris."

Chris smiled as he entered his password, then the smile left his face. "Wait a second!"

I entered my favorite downtown restaurant, the Trieste Arches, and found my brother Phil sitting in a booth. He stood and we shared a quick hug before I sat down across from him. The server was already waiting.

"Welcome to the Arches! Would you like something to drink?" Her soft voice was framed by glossy lips in a warm smile. Her rounded nose had a diamond stud on the left that matched the twinkle in her eyes.

"Iced tea, please. Unsweetened, with a lemon is ideal."

Phil leaned back, placing an arm across the top of the seat. "I thought that being the boss, you could have a drink at lunch if you wanted."

I barely heard him as I watched her walk away. Her black pants hugged her shapely legs and hips while the white shirt accented her wavy black hair. "I drink if I feel like it," I said, thinking about drinking her instead. "But, that's not the reason I wanted to get together today."

The corner of Phil's mouth curled into a smirk. "Is my little brother actually asking for my advice?"

Our server returned with our drinks. "Do you want to order yet?" Our eyes held contact as she spoke.

"Ruben and fries," Phil announced, breaking our reverie.

"Cheesesteak and fries," I added, glancing at her bare ring finger.

"I'll get those started!" She winked at me before turning for the kitchen.

Phil took a swig while watching us. "I think you'd like more than a sandwich from her."

I shrugged as I squeezed the lemon into my tea and stirred the mixture. "Are you saying you'd turn her down, if you weren't married already?"

"She's attractive, no doubt about it. Catherine is everything I could want in a woman, so that makes everyone else eye candy, which is fine with me."

"I met a nice lady last night, but I have some concerns."

Phil raised an eyebrow, waiting to hear more, then voiced his opinions. "Look, I'm not going to say I know everything about relationships. I will say that you're very likely to talk to and date a lot of women before you find one that does fit your life. When it just works and feels right, you'll know. Until then, enjoy the journey. And if you want some dessert after lunch, I'll cheer you on." He stopped to let the advice sink in. "The biggest trap you can fall into is forcing a situation. If it doesn't feel right, then keep looking no matter what. Does that make sense?"

I stirred my iced tea for a few seconds. "Yeah, I get it. I have to decide if a sticking point is a problem or not."

"Look, you know I spent four years dating before I found Catherine. It takes time, and a near miss is the hardest part of dating. Everyone bitches about bad dates, but they don't take long and you can laugh about them later. When you spend months with someone and decide it isn't right, that's when it gets messy. Those breakups can be as bad as it gets."

"Nothing like a great outlook on what's ahead."

Phil shook his head. "This is reality, you should know what it's like."

Our server returned with the sandwiches. "Here you go, is there anything else you need?"

I decided to go big. "Um, I would enjoy knowing your name and number," I said, looking up with a coy smile. "I'm Doug, and here's my info if you're interested." I handed her my business card with my company logo.

She picked up the card, then looked up at me. "I'm Sherrie, nice to meet you."

"My pleasure."

"I'll text you later when I'm on break. I'm off at four, if you don't work late."

I winked as I dipped a long fry into ketchup. "I'll be done at four, if I get a text."

Sherrie slipped the card into her pocket. "I'll come check on you gents in a minute." I watched her walk away, then glance back before she reached another occupied table.

"That was smooth, bro," Phil approved, lifting his ruben.

I bumped my cheesesteak against his ruben. "Is this a toast?" We laughed as we dug into lunch.

The clock turned to 3:30 and my phone was silent. Kurt stood and stretched with a yawn, causing a ripple effect in Chris.

"I think it's time to review some new candidates. I think some swiping will be a good change from orders and customer support."

I looked over my task list and dropped my pen on the desk. "Agreed! Grab some refreshments and let's see who's a contestant today on 'the swipe is right'."

Chris groaned and shook his head. "Don't plan on your jokes winning anyone over."

Kurt rolled his chair over with three beers from the breakroom. "Who said you could drink during working hours?"

He rolled his eyes at me. "You did, boss."

"Good point, hand one over."

Chris turned his chair around and straddled it, resting his arms on the tall back. "Start scrolling already, we've waited long enough. Who's interested in you?"

I logged into the app on my phone and started casting my screen to the display on my desk. The first lady who appeared looked to be twenty years older than me, and she didn't go to the gym either. "Hmm," I said, scrolling through a few of her pictures.

"Yep, great personality," Kurt declared. "Swipe on to the next candidate."

"How do you know she's not?" I asked, turning to look at him.

He shrugged and took a swig of his beer. "Sure, there's no way to know without meeting her. But, in the jungle that is the dating world, the matronly figure isn't in high demand. Some guys are into that, and I hope she meets one she likes. She's not what you're after, so move on to the next lady."

I brought up the profile for the next lady that had shown an interest in me. We all stopped and time stood still as we tried to grasp the image on the screen. BuffedNRuff was wearing a tank top and spandex shorts while working out at a crossfit gym. Muscles rippled along her arms and legs as she carried concrete blocks.

"Day-um," Chris said in awe. "She's amazing, but I'd be afraid she'd rip your dick off with her pussy muscles when she came." Kurt and I laughed at his assessment.

"My dick is strong enough for a man, but made for a woman," I stated as we continued laughing. "She's going to be living at the gym to achieve that level of fitness. I'm not sure I want to spend every evening there, so I'll keep Buffy the cock slayer as a maybe." I clicked for the next profile as more beer went down the hatch.

A text message appeared, displaying across the top of the screen. "I'm covering for someone running late. Want to meet at Los Locos at five? Sherrie."

Chris and Kurt lost their shit. Chris jumped to his feet while Kurt threw his hands in the air. "Who the fuck is Sherrie?" they asked together.

I put a hand up to stop the revolt. "She was the server at Philly's where I met my brother for lunch today," I explained. "I gave her my number, but she hadn't texted back yet so I didn't know if she was legit until now."

"Come on, you have to report these things to us!" Kurt protested.

"If I tell you about every woman I meet we'll never get anything done here, and you won't get paid."

"I think you're better at multitasking than that," Chris groused. "We're trying to help you. Don't keep secrets like this. Do you have a pic?"

I shook my head. "Nope, it's not like I could ask her for a selfie while she's working."

"Then we're all going to Los Locos!" Kurt declared. "You've got two flies on the wall as punishment for holding out." He and Chris fist bumped in solidarity.

I couldn't help but laugh. "Alright, sure, I'll give you that much. You're on my tab too. We'll get there early enough to try and grab a pool table so you can be discrete little voyeurs."

"Works for me!" Kurt said, settling back into a comfortable position. "That still leaves some time for a few more profiles. This redhead 1JessicaWabbit looks entertaining."

I followed Kurt and Chris into Los Locos, a popular restaurant and bar near our downtown office. I started a tab at the bar and took an open table near the pool tables before sending Sherrie a text helping her to find me. I checked emails to pass some time when she walked in, then smiled and waved as she made her way to my table.

"You must have been close, I just texted," I said, standing up and pulling a chair out for her.

"Wow, are you this nice after the first date too?" she asked, giving me a polite hug before taking the chair. Despite her hug being only her arm around my shoulders, her tits felt nice bumping up against me and my cock twitched sensing they were close by.

"Calling this a date adds expectations and associated pressures that I'd rather not have around. How about thinking of this as an event?" I offered, getting a curious look as she set her purse on the spare chair. "No expectations, only a chance to relax after work and get to know someone new."

Sherrie settled into the chair. "That confirms you're in sales, if nothing else."

"You're on my tab tonight. What would you like?"

"Moscow mule, please. I hope your tab can handle four of us, assuming your friends at the pool table are on it too."

I had to laugh. "Yes, Chris and Kurt are on it. I couldn't get out of the office without them. How did you notice that fast?"

"I work in a bar. If there's one thing common to dates it's friends trying to look inconspicuous nearby." She turned and waved at them, who both smiled and waved back. "Don't worry, I won't hold it against you."

"Thanks. I'll be right back. The server here is busy and could be a while." I weaved through crowded tables to the bar and waited for someone to take my order.

"What can I get you?" a younger man asked, his scruffy beard and hair the same shade as my favorite beer.

"Moscow mule and a Sam Adams, please."

He nodded and looked up across the room. "You with Sherrie?"

"How do you know her?" I asked as he placed a glass under a tap.

"I work with her three days a week," he explained, pouring vodka into a copper mug. "She prefers her mules a little tart, and stronger than usual. I'll take care of you, don't worry."

I slid cash wrapped around my business card across the counter as I took the drinks. "My friends the Jackson twins say you're the kind of guy I'd like working my official events. Got a card?"

He slid one of his own back with the drinks. "Good to meet you. I'll make sure Julie stops by your table more often."

I gave him a nod and took the drinks back to the table. Sherrie sipped her mule and made happy sounds, squirming in her seat. "Mmm, I love these drinks!" Her tongue slid over her lips, leaving them glistening with saliva. My nuts began to awaken at the site of her tongue dancing.

Her eyes shifted from her drink to meet mine as I struggled not to stare at her exposed cleavage. "What does a fun night out look like to you?" I asked. "I'm guessing dinner and a couple's massage for your legs after a day on your feet."

She stopped sucking on her straw, giving my nuts a break from her luscious lips making that wonderful circle and working the straw. "Sounds nice. I haven't been offered a couple's massage before. Wouldn't that mean we'd have to get naked together before getting on the tables?"

"Yes, but if you're shy I won't look."

She worked the straw again, her lips rocking back and forth as she sucked and swallowed. "It's tempting. What's your closer, salesman?"

"I can arrange for any sort of pampering you'd like. I keep this place stocked with fine drinks so they give me preferred access."

"What if I said I didn't want to be naked with you yet?"

"I'll keep my socks on." She worked the straw again as my nuts began to complain and beg me to work faster.

"Won't you worry about getting massage oil on your socks?"

I shrugged and smiled. "My socks have survived worse treatment, but that's another topic."

Sherrie swallowed hard and giggled. "You're not shy, are you?" I took a drink of my beer as I bumped my eyebrows at her. "What if my idea of a great evening is oral sex?" I struggled not to choke or spit my beer as she continued. "How about I take all three of you back to your office and I drain your nuts?"

I set my beer down, managing to keep my hand from shaking. "That's not the kind of team building I'd planned for them."

She lifted the straw with her tongue, pulling it into her mouth. "I think you'll have a high level of staff loyalty."

I ran my index fingertip around the top of my glass, holding her gaze. "My staff is already loyal. So are those two guys."

She leaked some of her drink, letting it run down her chin before swallowing the rest. "I dare you to invite them."

I took another drink from my beer, trying to decide if she was serious or if I should call her bluff. I decided to go big, and if she was all show it would be fun to see her back down. I set my drink down and waved for Chris and Kurt to come over. They didn't need a second invitation and joined us within seconds.

Chris, Kurt, meet Sherrie," I said, motioning to each of them as I introduced their names. They all said hello as I took another swig. "She wants us to fuck all three of us in the office at the same time." Chris spit his beer as Kurt's face changed from cordial to a beaming smile.

"Is this going to count against my benefit plan?" Kurt asked me as Sherrie laughed and ran a hand up Chris' leg.

"No, and don't count on any overtime pay either."

"Hmmm," she murmured as she felt Chris' crotch and reached for Kurt with her other hand. "I want to know the quality of the meat before I commit."

"You haven't felt me yet," I observed, swirling my beer and opening my legs a few inches.

Sherrie didn't look my way, busy evaluating Chris and Kurt. "I think you'll all do fine. Chris appears to be the low man on the scrotum pole, but Kurt could be hiding a sock. You guys and your socks."

Chris was ready to protest when I cut him off. "Are you ready to put your mouth where your money is?" Chris decided to remain silent instead of endangering the chance of an office party.

Sherrie stood up, finishing her drink. "I love a good mule in my mouth," she said, setting the copper mug on the table. "Let's go." She grabbed her purse and headed for the door as we trailed behind her.

Kurt was close behind, but Chris leaned closer to me and spoke in lowered tones. "Is she serious about this?"

I dipped my head to the side. "I don't know, but I decided to call her bluff and take her up on the offer. If she backs out, no harm no foul. If she's for real, we're about to have one memorable office party."

"Maybe so, but she comes across a little too direct for me. Maybe even kinda crazy."

"If she's for real, and actually is willing to do this, I doubt we'll be worried about a long term relationship with her."

"Good point. I'd give even odds she backs out."

Kurt talked to her as he guided her back to the office. They evaluated other bars and restaurants along the streets as we walked.

I opened the office door and turned off the alarm system as Kurt showed Sherrie into our conference room with a large oak table and racks of imported drinks on backlit glass shelves around the outside. I adjusted the lights on the control pad, and activated a few other controls. Background music started playing as a video screen turned on. I took my usual seat near the head of the table as she flirted with Kurt.

"So, welcome to my office. I want to stress that you are free to leave anytime if you change your mind about wanting to come here."

She sat back on the table, wrapping her legs around Kurt. "I like it here. Lots of room on this table."

I let Kurt keep her occupied as I whispered to Chris. "No spanking, or anything rough. Let her take the lead on everything and tell us what she wants." Chris furrowed his eyebrows, questioning me, but nodded he understood. "I'll get her attention, tell Kurt." I turned and stepped over by Sherrie, caressing her chin and pulling her gaze to me. "So, tell me what you want. Right now, right here, what you want and why you wanted to come here." I ran a finger down her arm, tracing the seam on her blouse.

"I wanted to come here so I could suck and fuck all three of you together," she said, her voice husky and dripping with desire. "I'm tired of single thirsty guys who think they are God's gift and I should throw myself at them because they can smile at me or leave a good tip. I need good sexual servicing and it'll take all three of you to satisfy that need." Her hand ran down my chest making my dick swell and push against my zipper in a bid for freedom. I saw Chris and Kurt talking behind her.

"We won't disappoint you," I said, unbuttoning her blouse. We began kissing as she pulled at her blouse and a button went flying across the room. She kicked off her shoes as Chris and Kurt ran their hands up her legs. In moments, her blouse was off and she was unbuttoning her jeans. I unsnapped her bra and freed her tits, her aroused nipples standing tall as she lay back on the table. Chris helped remove her panties and Kurt worked to get his own clothes off.

My mouth closed on her nipple, her hand on the back of my head as I teased and kissed. I looked up to see Kurt moving between her legs, descending on her pussy with a hungry and greedy look on his face. He began eating her out as Chris appeared at her head, his hard dick waving over her face as she giggled and moaned. She grabbed him and pulled him into her wet mouth, her lips making the same motion they had on the lucky straw. She inched him in as her jaw moved and her tongue danced around Chris' hard tip.

Kurt was kissing and licking her pussy lips, his tongue working her clit then making a lap around before returning to her joy buzzer. His finger worked into her, searching for her fabled g-spot. Her body jerked when he found it, her moans making Chris squirm as her mouth and throat vibrated around him. Her hand closed around me and stroked my solid shaft as I played with her equally excited nipples.