Venturing Out

I walked into my office past the display cases of liquors and wines I imported and dropped my backpack by the desk with a thump, getting the attention of my coworkers for my announcement. Kurt was doctoring his coffee while Chris was checking emails.

"Good morning, gents!" I said, starting the day's conversations. "I've decided it's time to try online dating!"

"No shit!" Chris exclaimed, forgetting his emails.

"You da man, Doug!" Kurt agreed with a huge smile. "You know you have to keep us up to date with how this goes."

"Of course! We're a team and it'll be more fun if you're along for the adventure."

Kurt came over to my desk as I sat down. "Got a profile yet?"

"Nah, I still need to pick which app to use."

"You're what, 42 now?" Chris asked.

"Yeah, what's that got to do with it?"

Chris shook his head. "You're lost in the woods already. Lucky for you, we'll help guide you to the woman of your dreams!"

Kurt stopped with his finger in the air. "Wait. You are after a woman, right? I want to know we're on the same page before we ride off in the wrong direction when trying to get you a hook-up."

Chris and I laughed. "Yes, I am after a woman. One that isn't a conversion or needs a gender reveal party."

"Alright!" Kurt exclaimed, clapping his hands together and rubbing them. "Let's get going. You're not old enough for the seniors app, and you'll probably only get girls with daddy issues on the kiddy apps like Tinder and Bumble."

Chris nodded his agreement. "Yep, stick to the most common apps like eHarmony or Match."

"Match works for me," Kurt pointed out. "I get enough attention that I'm not single for too long between meaningful weekend relationships."

"And," Chris added. "Match rhymes with snatch for a reason!" We all laughed as I brought up the website and created a profile. We picked some pictures from my social media accounts and stopped when we reached the self-description paragraph.

"Hmm, I hate these things. Any suggestions?" I asked the team.

"Avoid the boiler plate thing about how great you are and what sort of person you're after," Kurt advised. "Everyone does the same thing, and it's boring."

Chris' face lit up with an idea. "Oh yeah, and never ever reference that pina colada song. It's a major party foul." We all laughed at his evaluation.

"I'm sure there are a few women who like that song."

"Doug, just don't go there. For the love of everything good and pure, avoid that temptation."

I started typing away, putting down the first thing that came to mind. "What do you think?" They looked over my paragraph, looked at each other, and nodded.

"Go live!" Kurt encouraged me. "We want you to get hooked up right away!"

Chris laughed again. "Yeah, it might help you unwind after that messy divorce."

I put my hands on my hips, trying to look indignant. "Are you saying I'm too uptight?"

Chris and Kurt looked at each other, then back to me. "YES!" they said at the same time.

*****

I looked at the clock, fifteen minutes until we were free for the evening. A few of the women I'd shown interest in had occupied my thoughts all day. Each of them had left me with fantasies of passionate sex that would need help from Literotica to release the pressure when I got home. I checked the online account for the fourth time, hoping for some activity. Kurt watched me, a shit-eating grin on his face.

"Any takers yet?" Chris looked up from his spreadsheet when Kurt brought up our favorite subject.

"As a matter of fact, yes!" They abandoned their desks and rolled over in their chairs to have a look. "HikerBabe88 is interested." We all started scrolling through the profile pics. "Umm," I said, not impressed with the images.

"My opinion," Chris offered. "If she needs to add 'babe' in the profile title, that's a red flag."

Kurt grunted his agreement. "It makes me think of that pig, not a beautiful woman." We laughed at the comparison.

"I'm sure she has a wonderful personality," I said, swiping her away and bringing up the next profile.

"Ooh, she's nice!" Kurt said, inspecting her closely. "Let me get the profile name if you're not interested. 1ButterFlyer. Cute."

She wore a red shirt, yoga pants, and roller blades in the first pic. The second had her next to a fire pit holding a drink with other people cropped out. Her shoulder length light brown hair had blonde highlights that framed her tan skin and fine features. "Actually, I think she's worth looking into. But keep her info on file if it doesn't work out for you. I want to try her if you fail."

Kurt looked up, one eyebrow lifted. "How much do you think this will work out? Sure, it'd be nice to find someone special. It's frequently called the dating hamster wheel for a reason. Get together, get off, get annoyed, get out looking again. That's the cycle, and many of us are in it for years. You need to know that, so you set your expectations at a realistic level right from the start."

I shrugged. "That doesn't surprise me. I'm going to message her and see how it goes." Chris was busy making notes on his own phone. "What are you doing?"

"I'm between ladies right now, so despite the red flag, I'd like to look into HikerBabe88."

Kurt punched him playfully on the shoulder as I sent a greeting through the app. "Lowering your standards? I thought you needed to be single for a few more weeks to go there."

"It doesn't hurt to add her to the statistics. Contact a lot of ladies to get the interest, and only a few of them will even meet you somewhere. Only a few of them will be interested in sex in the first few weeks of dating, so spreading those wild oats is part of the game."

I leaned back in my chair. "You're not painting a bright picture for dating."

"It's always been that way," he explained. "Online dating simply speeds up the process and makes it possible to meet more women than you ever could in person at old-school single's bars."

"I signed up for a single's function tomorrow night," I pointed out. "Any bets on how that goes?" At the sound of a gambling challenge, my friends perked up.

"Five says you get at least two contacts!" Kurt wagered. I looked at Chris.

"Alright. I'll say you only get one. You must get an email or phone number. I'll put a bonus fiver if you get a selfie together."

I shook my head. "And you talk about lowering the bar. What's the bonus if I score?"

Kurt scoffed at the idea. "Sure, it's statistically possible. I'll pay ten if you score, fifteen if you get two other contacts."

Chris waved me off. "Don't get your hopes up. I'll take those odds, but that means you're paying us both when you come home empty-handed. Trust me, ladies can tell when you're desperate and won't have any interest in that."

"Time will tell," I replied. "But 1ButterFlyer has already replied she'd like to get to know me more." They looked up and moved closer to the screen again. "Wow, time to go! You'll have to wait for tomorrow to learn more." I closed the screen and smiled as they protested. "I'll chat while on the bus home. Have a nice evening!" I waved as I walked out the door, leaving them fuming. My thoughts were on her shapely figure in those tight clothes.

*****

I boarded the regional travel bus out to the suburbs, settling into a tall, comfortable seat halfway back and pulled out my phone. The bus wasn't crowded, so the seat next to me was empty, giving me more privacy. Seeing a message from her made the world around me disappear.

"Nice to meet you. I'm Michelle," the message read. "I'll be commuting home tonight and able to chat. If you can meet me online, it might be fun." She finished with a kiss emoji.

"Hi Michelle," I wrote. "My ride home takes half an hour on average, so I'm here if you're online." I looked around as the bus drove away from the station. A little less than half full, so private enough for online flirting. A reply arrived, keeping my excitement level high and making this the best ride home in ages.

"Our profiles say we live in the same suburb. What are your favorite places to eat?"

I thought for a moment. "My favorites are Mexican and Italian, so Blue Agave near the mall and Locatelli's on 19th."

"I like the Hitching Post on 33rd. They have a great draft beer selection."

I had to look that one up on Maps. "What's your favorite drink? I'm into Fat Tire ale." After I sent it I panicked that it was a pretty cliche line. A reply showed up soon after, soothing my fears.

"That's a nice one. I enjoy Dry Dock Apricot Blonde. Do you like blondes?"

Uh oh, a set-up question. I needed to handle this one with finesse. "I prefer darker drinks, but I can enjoy a blonde, too. Do you ever enjoy anything stiffer?" As soon as I sent it, I panicked again. Stiffer? I was trying to flirt, but damn dude, don't go for the jugular so fast. The mental face-palm went into a full panic as the reply arrived.

"I've swallowed stiff drinks. They can be tasty on my tongue. Are you capable of making something impressive?"

Holy shit! After my ice queen of an ex, this was boiling hot. But now the bar was climbing higher with each message. What should I say next? Focus, Grasshopper! Wait, that's it! "I make a version of the Grasshopper that gets rave reviews. It's creamy, salty, sweet, and stiff enough to please." Damn, this sounds like a frat house pickup line contest. I looked around the bus and saw traffic was slower than usual, meaning more time for flirting.

"You're confident. I like that. Want to meet soon? I think it would be more fun to flirt in person while we get to know each other."

I sat back, enjoying the triumph of a successful online flirtation. But there's always the pressure to keep the momentum going. "I'm down. Hitching Post at seven? I'll buy dinner." That's usually a friendly offer. I looked around again and noticed a subtle flash from somebody's phone a few seats up. Who would take a selfie on a bus? The next reply arrived. That was fast.

"That won't give me time to change. If you don't mind dinner in my work clothes, I can agree to your offer. Here's what I'm wearing, so you can recognize me. How about sending a selfie so I can pick you out in the crowd?" I opened the attached picture. No way. What are the odds? She's sitting on a bus seat. Is that actually her a few rows ahead? This was a man or mouse moment. Do I go find out if it's her? Hell yes! I rolled my Yeti drink container up the aisle, giving me the excuse to go retrieve it. Timing was critical, so I let it roll almost to her seat, then chased it down.

"Excuse me," I said, grabbing the container from the floor by her shapely legs. They extended down from her skirt to a pair of sneakers that had replaced the heels on the seat next to her. "Michelle?" I asked, looking up into her eyes, now growing wide in recognition.

"Doug? What are you doing on this bus?"

"Going to the Hitching Post, apparently," I replied with a smile. "But usually I'm heading home." I noticed the driver wasn't happy about me being in the aisle and waved to show I was returning. "I'm sitting a few rows back. Want to come join a live chat?"

Michelle giggled at the invitation. "Sure, go make some room and I'll be right there."

I moved my backpack to the floor as she arrived and slid into the seat next to me. Her skirt slid halfway up her thigh, revealing her tan skin and toned legs. Her perfume was intoxicating, and my world shrank to those two high-backed seats.

"Like the view?"

I gave a Cheshire cat smile. "I love it. You weren't kidding that you spend time at the gym to get results like that."

"Thank you," she replied with a smile. "So you want to buy me dinner? Should I be cautious about your intentions?"

I raised an eyebrow at her insinuation I was only after sex. Of course I wanted to get laid, but a fun evening was also on the list. "My intention is to buy you dinner and have a great conversation full of flirting. I'm honorable enough to offer an evening out without strings or expectations."

"What if I have expectations?" The high-backed seats wouldn't allow for her to turn and put her elbow on the back, so she rested it on my shoulder and cupped her chin. Her proximity was distracting my thoughts, but her disarming smile left me wondering what she was thinking behind those brown eyes and long lashes.

"Then you should tell me what they are," I explained. "My Mind Reader Association membership ran out last month. I'd have renewed it if I thought it was going to be useful." She laughed while I enjoyed the view of her tongue behind glossed lips. Too much of this and I'd have a hard time hiding the effects. My backpack was on the floor and would be painfully obvious if I pulled it into my lap for no reason.

"Well," she started, recovering from her laugh and refocusing that piercing gaze on my eyes. "I haven't had a second date for a while. Most men are after conquests, and they disappear when they find out I'm not interested in being one of their statistics." I nodded my understanding as she explained. "Are you into statistics?"

My eyes rolled up as I thought about my business. "Actually, I have to be. I run an import business and tracking sales gets into details that make my head spin. My business has been my life for a few years and I was hoping for a break from statistics and numbers." Talking about work was inevitable, but better topics were dangling just out of reach until we passed this hurdle.

"Ooh, an importer. What's your specialty?"

"Wine and liquors. I do a lot with red wines from Portugal's Duro region where they make port wines. The only conquests I'm after are more sales." I was trying hard not to look down at her shirt showing off her cleavage.

She pulled her mouth to the side, considering wine varieties. "Can't say I'm that familiar. You'll have to show me why they're special." She paused for a moment, still looking through me with that gaze. "You really aren't after a one night stand?"

I pressed my lips together and shook my head. "Look, I love great sex like most people do. But it doesn't rule my life. You appeal in ways I've forgotten existed, and I think a single night isn't nearly enough to enjoy being together."

"I like your attitude, and I think you're honest about it too. You're even exactly as advertised on your profile, which alone is rare enough."

"I don't lie. My business would fail and I'd lose my friends," I stated. "You can ask me anything." Damn, I needed this conversation to stay off sex because I was struggling to keep my self control.

Her smile turned mischievous. "Anything?" I nodded my consent. "Alright." She ran a finger up my leg, sending ripples of excitement through me and making my nuts quiver in anticipation as my self control began to crumble. Her finger dragged across my arm, up to my shoulder, then moved to the open neck of my polo shirt. "You seem to stay in good shape, too. Can I ask if you do any manscaping?"

"I keep the garden neat, but I don't mow the entire lawn."

"You don't look like a Wookie. Can I check?" Without waiting for an answer, she slid her hand inside my shirt. Her soft touch sent more ripples of excitement through me, and my nuts woke up to seize the moment. Good bye, self control. "You're not bad enough to need it, and I like a little fuzz on a man anyway." She pulled her hand out of my shirt, brushing my nipple, then noticed the bulge appearing in my pants. "I guess you're enjoying this," she said with a demure smile, running her tongue across her upper lip.

"Turnabout is fair play," I replied, eyeing the buttons on her blouse restraining her c-cups. "Are you up for me to have my turn?" I ran a finger up her leg, onto her skirt, and up her side. I moved up and caressed her cheek before moving back down to the open neck.

"There's a lot of material in the way, but I know you'll manage," she encouraged. Like I needed it.

I ran my finger across the closer nipple, feeling it through her bra. A few circles, then I moved back down, finding the hem on her skirt. I pushed it up as she spread her legs wider. My fingers moved up her thigh and found the edge of her panties, then followed them over the top of her leg down into Joy Valley. The heat was intense, and brushing against the nylon showed she was just as excited as I was. A few more circles as I felt the panties getting wet, and I was ready for more. I knew she was beyond her reservations by the way she was massaging my cock through my pants.

"My stop is the park and ride by the mall. Is that closer than yours?"

Her hand helped my stiff cock into a more comfortable position as it continued to grow. "Yes, let's get off this bus and try to make it to your place." She patted the kielbasa now lying sideways in my pants. "How big does this thing get?" she asked with a wink.

"It is a very comfortable car. I need a nice one to take clients out," I pointed out. "But I haven't made out in the back seat in years."

Michelle's smirk was priceless and made me melt. "I want to save something for a second date. But I would love to see your place as soon as possible." She continued adjusting my stiffening cock as it strained to break free. "I want to see several things." She leaned forward and kissed me. Her lips were soft and warm while the berry lip gloss sent images of those lips around my dick through my mind. We kissed more and her tongue came out, caressing my upper lip. Her grip on my cock grew stronger as we kissed. My hand caressed her tits and teased her nipple into its own erection, poking through loud and proud while begging to be kissed and sucked.

"We're the next stop," I advised. "Can you hold it together long enough to get to my place?"

She gave me another squeeze. "I'm ready, I hope you have some stamina because I won't be happy if you're a one pump wonder."

"Don't worry, I'll put you through your paces." I gave her one more kiss before we arranged our bags to cover the obvious results of our foreplay. We walked off the bus and she followed me down the short steps into the parking garage. My black Grand Cherokee was close by, and I opened her door for her while taking her bag.

"Why thank you. Good to know chivalry isn't dead."

I laughed. "I think you know you've found a good knight." She groaned and shook her head as I gave her a kiss, closed her door, and moved around to the driver's side.

As we drove, we held hands and I glanced over every chance I had. "I don't want you to think I'm like this with everyone I meet online," she said, turning in the leather seat to face me. "I feel a connection with you, so I hope you feel that too, and this might last for a while."

I gave her hand a squeeze. "After twelve years of marriage, and being divorced for four, the occasional hook up hasn't been that satisfying. I'd like to find someone who will want to get playful and enjoy life."

"Your car is pretty nice, would you risk messing it up to get playful in here?"

I glanced over to find her pulling her skirt up to reveal her panties, giving me that sexy smirk as she worked a finger under the damp nylon. "Hell yes! The leather will clean up easily enough if anything runs down your legs." I pulled into the driveway of my condo complex, watching her tits bounce as I drove fast over the speed bumps on purpose. I pulled into my designated spot and shifted into park. "Welcome to my humble home."

We walked through the front door and she looked around as I dropped the keys on the dining room table to the left. The kitchen was just beyond and a living room with a leather couch and TV was on the right. Stairs ahead beckoned us up to the bedroom, but I wrapped my arms around her for another passionate kiss first.

"Would you prefer to go upstairs?"

She began unbuttoning her blouse as I ran my hands up and down her back. "Let's start there, but that couch looks comfy too."