Blank Spaces

Tyler Matthew’s sat his desk, Italian leather shoes on his desk, leaning back in his chair enjoying a McCallan 18 on the rocks. He looked out his 20th floor window overlooking the city below, smirking at the deal he just brokered. Another takeover finalized today, giving him a nice hefty bonus for his troubles. Sure, the company would be liquidated and the 150 people laid off. But that’s their managements fault that they couldn’t run a business. Does a wolf feel bad when the deer he’s hunting has a lame leg? No, and neither does Tyler.

The take over already took the backseat to thinking about what girl he was having over tonight to celebrate. Tina, the petite brunette from the coffee shop was always fun, but her liberal ass ideals got tiresome. Sure, she was great in bed, but who cares about welfare and universal healthcare? It’s the real world and the real world only the fittest survive. And last time she wanted to take him out to an “alternative” club, aka a gay bar. She said it was fun and had a blast the last time she went. Nothing against gay people, live your lives, but just leave me out of it. And don’t go shoving your “lifestyle” in my face. No chance Tyler was heading there with all those queers.

There was Amanda, a fucking bombshell blonde with great cans. Typical plastic Barbie type, fake lips, fake tits, BBL, Botox every other month. She didn’t need it at 25 years old but she looked incredible. Always wearing some short and tight. But she was basically brain dead, couldn’t hold a real conversation of any depth. But that didn’t stop her from chattering away incessantly. Clothing, make up, celebrity gossip, which of her other bimbo friends was cheating on their husband. Couldn’t care less. And she liked all those drag race shows too. Even got him to watch it one time with the promise of a blow job. Sure, some of those poofs looked pretty decent with all that make up and padding and shit, but it’s still a fucking guy underneath it all! He couldn’t believe these “men” were prancing around on stage in dresses and heels making a fool of themselves. Act like a man for chrissake! Amanda kept going on and on about how amazing they looked and how crazy a little make up and padding could make a guy look like that. Well she kept going on and on until he had her head in his lap just to shut her up. It was weird getting a BJ when watching fags mince around on stage, so he quickly turned it off.

Deciding neither of the two would do tonight, not wanting their bullshit in his life, he decided he’d just go to the bar and find some hot young thing looking for a guy with money. And money he had plenty of. At 29 years old, Tyler was doing extremely well for himself. Taken on by the firm right out of college, he’d made a name for himself for his ruthless tactics. Quickly rising the ranks, he’d made junior partner at only 26, with the promise of full partner in the next couple years if he kept things up. And he definitely wanted to keep things going up.

Checking the Rolex on his wrist, he downed the last of the scotch before standing up and straightening his tailored Italian suit. He looked at himself in the full length mirror in his office. Standing at 5’6”, he was always a little self conscious of his height growing up. But that just made him more cynical and mean. Napoleon complex had to come from somewhere, and he used his height to fuel the competitive fire inside him.

His Armani suit fit perfectly over his slim frame, trained from hours in the gym. While never packing on too much muscle, his upper body still showed muscle definition. And his washboard abs were an easy way to get a girl to bed, and if that didn’t work then his money sure did. His legs were nice and toned from peloton classes, as was his butt. While his “package” wasn’t porn star worthy, his 6” dick never failed him. At least he thought it didn’t, but he wasn’t necessarily a considerate lover in the bed room, normally finishing well before his date had a chance too.

Combing over his longish brown hair, he made sure the $300 haircut still looked good, he looked at his face. His 5 o’clock shadow was just beginning to show on his handsome, pretty boy face. Blue eyes gleamed under masculine eyebrows. Not a blemish to be found on his clean skin. Giving a cocky wink to himself in the mirror, he grabbed his briefcase and walked out of his office.

Outside sat his pretty secretary Charlotte. The pretty 24 year old brunette was sitting staring at the computer trying to figure out where to reschedule the new client on Tyler’s schedule. The man constantly changed things on the fly and expected his secretary to figure it out. It was infuriating, but with her low on the totem pole, she had to play the game. At least Tyler was good at his job. She was hoping he would drag her along the corporate ladder, which is why she dealt with all his bullshit.

Tyler leaned against her desk and gave her the once over, stopping for several seconds at her exposed cleavage. Since she transferred to be his secretary, he enforced strict guidelines for dress code. Very tight and short pencil skirts or dresses, low cut tops, high heels must be worn, as well as make up done perfectly. He said part of her job was to be “eye candy” for clients, put them at ease with the pretty thing serving coffee and taking notes so that he could take advantage of their lowered defenses. With an MBA from Stanford with honors, Charlotte originally thought this was demeaning and beneath her. But she had to admit, the technique worked and worked well. Tyler wasn’t an idiot and knew Charlotte was sharp as well, but he wasn’t going to let a good tool go to waste. If that tool was a pair of legs showing a hint of stocking top as she bent over, he’d use it.

“Char, I’m gunna be out the rest of the day. Gunna go celebrate a bit. You sure you don’t want to come join me this time? Those legs would look great on a bar stool” Tyler looked at her stocking covered legs starting at her blue suede 4 inch pumps, leading up to a very tight black pencil skirt that was just a hair on the side of unprofessional. A pale blue silk blouse was tucked into the high waistline with short capped sleeves. The top few buttons were undone, and from Tyler’s high vantage point he could see the hints of lace on her pale blue bra, hoisting a beautiful pair of C-cups. Charlottes hair was done in a tasteful bun with wisps of hair untucked framing her face in the front. The up do worked to make her look cute but also practical. A “natural look” make up that was anything but natural covered her face, contour and highlighter bringing out her feminine features. Her fake lashes fluttered across her green eyes. Her lips shined crimson from the bright red lipstick and liner making them appear bigger than they were. Thick black glasses hung on her nose as she turned them to look at her boss.

“Not this time, Mr. Matthew’s, and not anytime soon. Go use your lecherous ways on some bimbo that’s dumb enough to fall for them. Congratulations on the deal by the way. The partners are really gunna like it”

Charlotte was used to Tyler’s looks and advances at this point, but she knew he was harmless, at least to her. He would never really try anything with her, he just liked to have a pretty secretary he can flirt with. He liked the game they played more than he liked winning that game. If that game kept her employed and on the rise with him, then she could deal with the lecherous looks and cheap pick up lines.

Tyler laughed and rapped his knuckles on her desk “you’re damn right they’re gunna be happy. And I’m gunna be happy too, once I find that ‘bimbo’ you were talking about. She sounds great. I’m off to find her, so just hold all my calls.” Tyler started walking away and said over his shoulder “oh and I’m gunna be late tomorrow morning so just cancel my whole morning and reschedule”

“But Mr Matthew’s! You have 4 appointments tomorrow I’ve already resched-“ but he was already in the elevator and gone.

“Bastard. Thompson from accounting is gunna be pissed. The bonus he’s gunna give me better be big enough” Charlotte fumed while already typing out the emails to cancel the meetings.

Tyler jumped into his new Audi and started the powerful engine. The engine revved to life, purring as only a high end car can do. Tyler’s phone synced to the car as he put on some relaxation tracks to calm him down from the highly stressful day. While he loved and craved the stress of high value mergers and acquisitions, Tyler needed this time to unwind or else he’d be the stereotype Wall Street broker who died of a heart attack at 40 from stress.

As the track started playing, the screen and sound glitched for a moment. Tyler angrily looked at the scramble on his cars dashboard. “I just got this fucking car are you kidding me??” He said as he slammed on the top of the dashboard. But the scramble went away a moment later with his relaxation meditation pumping through the high quality speakers.

“Yeah that’s what I thought” he smirked as he sped out of the high rise parking lot out into the city streets.

As he drove through the city, the relaxing music calmed down the high powered exec. The familiar sounds of crashing waves and the soft feminine voice relaxed Tyler as he sifted through city traffic. Normally he’d be annoyed by the bumper to bumper traffic, but today it seemed to barely affect him. Tyler let out a satisfied sigh settling into the high class car seat.

In what seemed like no time at all, Tyler was parked in another parking garage attached to his favorite bar. He looked at the clock and saw an hour had passed since he left the office. He swore it had only been a few minutes since he left the office, but just shook his head. “Long week. Must be getting to me. I need a drink to relax”

Tyler walked into the high class bar, Tony’s. Dark wood covered the walls and pillars of the drinking establishment. The bar itself was made of the same expensive dark wood. Booths lined the walls and comfortable chairs sat in circles throughout. Along the bar were low backed bar stools with soft cushions. The room was only partly filled with similarly well dressed business men and some women, all in business attire. The place was the watering hole of the finance district for the well established youths of the business. Sprinkled amongst the crowd were the reason Tyler loved this bar. The scantily clad women who hung around the bar looking for a rich young exec to hang out with.

As Tyler sat in one of the comfortable chairs, sipping his second McCallan, he spotted one of those very girls sitting on the edge of of barstool. His eyes started at the bottom on a pair of expensive designer peep toe glossy red pumps, her own toe nails a matching red color. The heel had a hidden 1 inch platform with a 5 inch black heel. The back of the heel had a little red bow. Up her legs were a pair of silky nude gossamer stockings, and he knew they were stockings cause he could see the top of the nude welt poking out of the bottom of her dress. She had probably done it on purpose as her red dress was hiked up on the stool, showing off more of her tanned thighs. The red dress was one of those bandage dresses, very tight throughout the outfit. Her hips swelled over the chair, showing off a probably enhanced backside. The tight material showed off her toned stomach, showing an hourglass figure. And an hour glass it was from her obviously enhanced chest almost spilling out of the very low neck line. Obviously at least DDs on a small frame of a 5’ 4” woman, they looked massive. The dress was off the shoulder with little cuffs on her upper arms attached to the bodice. Around her slim neck she wore a simple gold chain. Her bleach blonde hair was done in a center part with waves cascading down past her shoulders. Her make up was dramatic. Full long lashes and an evening Smokey eye enhanced her blue eyes. Her make up high lighted and contoured for an night time look. Blush accented her cheekbones making them look full and inviting. And her lips, clearly had some filler in them but gorgeous nonetheless. Outlined lips with a matte red lipstick matching her dress. She had gold pendant earrings that dangled down as well as several other ear piercings. The girl simply was a knockout.

As she sat on the barstool checking her lipstick in her compact, Tyler caught her eye. She looked at him, seeing his expensive suit and his youthful handsomeness and smiled at him. Closing her compact with a playful click and a giggle, she brushed her hair over her shoulder and did a cute little finger wave at him. Tyler smiled back at the blonde, clearly out for some rich dick, and motioned her over. “The guy is rich and cute? But he calls me over rather than come over to me. Definitely full of himself and He’s gotta be a dick. Oh well, let’s see what he’s got” she said to herself as she strutted over, making sure she put an extra wiggle to her hips and that her expensive tits bounced with each step. “Paid a lot for these puppies. They gotta pay themselves back, with interest! Hopefully a big fat ring”

Tyler motioned to the seat next to him and she gracefully sat down, smoothing out her skirt and crossing her stockinged legs at the knee. She introduced herself and Britney, a secretary over at a neighboring firm. “God I love secretaries, especially ones that call themselves secretaries. The ‘administrative assistant’ title is bullshit. Just call it as it is, a hot piece of ass to make work a little prettier” Tyler thought as they chatted away. Britney clearly wasn’t the brightest bulb out there, sounding like a typical 20-something girl. Lots of “like, totally” “exxxxxaccttlllyyy” “oh my gawwddd! I’m crying hahaha”. Exactly the way Tyler liked his flings. He didn’t need a brain surgeon to keep him company, just a pair of tits, big lips, and a pussy that knew how to use them. They could be vocal in the bed room for sure, Tyler loved good dirty talk, but no need for real thoughts or talking outside of that. But Tyler played the game, making her feel smart and that he listened to her stories about how her hairdresser totally messed up her hair again, but he had already tuned her out and was surreptitiously staring at her chest planning what he’d do to them later.

A couple drinks later and the couple were now out the door heading to Tyler’s Audi. Tyler had his arm around Britney, his hand resting on her silicone filled butt as it wiggled back in forth. The last thought he had was how great that jiggle would look when he was pounding it from behind.

The next thing he knew, he was in his king sized bed in his city penthouse and the sun was up. He looked over and saw he was alone. Britney must have left. “Thank god, hate the morning after routine. Always a pain getting these bitches out of here” Groggily he sat up, feeling exhausted and hung over. “Holy shit, how much did I drink last night?” Looking over at his phone he saw it was already 9 am and he had a message. It was from Britney:

“Heyyyyy :) I made it home. Thanks for calling an Uber. That was surprisingly A LOT of fun hehe. When we were at the bar i didn’t think you were that kind of guy and i wasn’t so sure about it but it was like sooo much fun lol reminded me of college with my sorority sisters ;) I haven’t cum like that since then!! And you sure came A LOT! Super adventurous, I LOVED it! Anywayyyssss, let me know when you want to hang out again. Oh, and you can keep the panties, they look better on you anyway girlie hehehehe”

Tyler was confused as hell by the text. “Panties? Wtf is she talking about? And what’s this girlie talk?”

Tyler pulled off the covers and looked down in shock, now understanding. He was wearing a pair of lacy red panties! A triangle of transparent red lace just barely covered his junk. Two think black straps went around his hips and connected to a similar red lace triangle in the back, leaving half his cheeks exposed. As he looked down at the feminine garment, he saw in horror that his soft cock started to get hard in the lacy prison. The lace felt so soft on his 6 inch dick as it started to press against it and a low moan escaped his lips at the sensation. Unconsciously, his hand reached forward and softly touched his cock through the panties. Electricity of pleasure shot through his hand into his cock and into his pubic area. He slowly ran his fingers over the lace, moaning at the sensation of the soft fabric on his hard member. The pleasure built and built, unable to stop himself until he exploded into the panties. Shot after shot soaked the garment, leaving the front a dark red and white mess.

Tyler lay there trying to catch his breath trying to figure out what the fuck just happened. Getting out of bed, he walked over to his large master bathroom. The room was shades of grey and stainless steel, dual sinks and a large jacuzzi tub and an expensive shower with multiple heads and even a waterfall shower head. Tyler walked over to the mirror and another surprise hit him. His face, normally sporting a 5 o’clock shadow, was shaved smooth. He knew that he had stubble at the office so he must have shaved Last night. But what really shocked him was the matte red lipstick on his lips! The makeup was overdrawn on his lips to make them look bigger. While slightly smeared, they still looked ok. The intrusive thought hit Tyler that they actually looked…. Good. Well, good on a woman with a cock between them. But Tyler was a man and would never ever do that!

Tyler quickly turned on the faucet and grabbed facial cleanser to wipe off the matte red from his lips. Scrubbing hard to get rid of the feminine color, Tyler finally looked up and saw his lips were back to normal.

“What the fuck did you get up to last night, man?” He asked aloud to himself in the mirror. He saw his normal, masculine self, lean muscles and six pack. But what broke the masculine image was the bright red panties still on his hips, his own cum drying in the gusset. Disgusted, Tyler practically tore them off and threw them in the corner. A real man doesn’t wear that girly shit.

Shaking his head and looking in the mirror, seeing himself again he just laughed. Taking it as a one off crazy night, Tyler hopped in the shower, cleaning off the residue and drunkenness from last night. Cleaned up and feeling much more himself, he got dressed and left for the office with a skip in his step.

What he didnt realize as he left was the pair of red panties, freshly hand washed in the sink, hanging to dry.