Maestro Ch. 02

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Katie goes on the worst date of her life.
3.3k words
4.54
15.3k
7

Part 2 of the 10 part series

Updated 06/08/2023
Created 08/07/2016
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Yambler
Yambler
36 Followers

Previously:

- Katie's past interest in bondage destroyed her most dear relationships and has kept the interest a secret ever since.

- Lilly, Katie's only friend, is fixated on trying to find a guy for Katie.

- Katie discovers the online bondage community Cuffed and makes her first post with hopes of trying bondage for the first time.

Katie did not finish the first draft of her proposal until almost 7:00 PM Saturday evening. She quickly brought up Cuffed to see if she had any responses. To her surprise, she already had 15 messages waiting for her. Katie was thrilled to see results from her post so quickly. Katie opened the first message, only to be greeted by a guy looking to hook up for sex. Only somewhat discouraged, she quickly moved onto the second response finding a similar message. By the time Katie had read the fifteenth response, it was clear that the men on Cuffed were not as serious as some of the authors of the other posts she had read.

Katie threw her laptop aside to prepare for her elegant evening of a microwave dinner. Before she could leave her small bedroom, Lilly's number popped up as an incoming call on her phone. Katie stood there for a moment, debating whether she wanted to hear her go on about her boyfriend David.

"Hello", Katie said picking up the phone ready with an excuse to hangup if needed.

"Katie! If you can pull your self away from work tonight, David has a cute friend who is free for dinner." Katie could tell through Lilly's voice that she had clearly been scheming since breakfast.

Katie paused for a moment, with her mind racing. She knew that Lilly would never let her live this down if she said no.

"Oh, really?", Katie said hesitating.

"Yes! I met him a few times. He is a nice guy. His name is Kevin. The three of us are hanging out at my apartment and talking about you. He said he can swing by your place in an hour or so to pick you up for dinner if you are open to it."

Katie paused. She couldn't believe her life was being picked apart by three other people. She really didn't feel like getting ready for a blind date on such short notice but knew Lilly would not take no for an answer.

"Fine. Tell him to come by in an hour."

Katie quickly hung up and raced to get ready with the little time she had. She was not very thrilled about the date, but thought if the guy was not half bad looking, she might get to have sex for the first time this year. In her closet she selected a thin, draping, red dress with spaghetti straps. It was low cut and showed off a fair amount of cleavage. She slipped on some black heals and quickly finished with her hair and make up just as her phone started ringing. A number instead of a name showed up. Katie figured Lilly had given Kevin her phone number.

"Hello, this is Katie."

"Hey. This is Kevin. Lilly and David's friend. I am here to take you out to dinner."

The phrase 'Lilly and David's friend' echoed in her ears almost becoming painful. "I'll be down in a moment."He should have used a couple name for them,Katie thought.Lavid, or Dilly.Katie chuckled to herself. Katie grabbed her clutch, threw her phone inside, and headed down to meet Kevin.

Katie exited her apartment building and saw the guy who must have been Kevin, waiting patiently. He was the typical, tall, dark and handsome. She could tell by the shirt and tie underneath his pressed and flawless looking navy suit that he was the young lawyer type that was very common in DC.

"Hey Katie. Nice to meet you. I'm Kevin."

"So wonderful to meet you Kevin. How did you know it was me?"

"Oh, Lilly showed me a picture of you."

Katie rolled her eyes. "Shall we get going?"

Before Kevin answered, he looked Katie up and down, lingering on her cleavage. Katie already knew if she wanted to use this as an opportunity for sex, she would have no problem.

"Uh, yeah. Have you been to that new French restaurant down the street? I thought we might give that a try."

"No, I actually haven't. That sounds great."

They walked side by side as they exchanged information on their professional careers. Kevin was in fact a lawyer at a small law firm in the city. Katie quickly shared the gruesome world that was her job. Katie tried to keep the conversation going, but after career talk all his responses became one word answers. The sun was low, paining a brilliant orange across the sky. The amber street lights began there slow flicker to illuminate the sidewalks.

"I love how there are no tall buildings here, it really lets you appreciate nights like this," said Katie as she looked up towards the vivd streaks of light from the setting sun.

"Oh, yeah. Me too." It was clear Kevin had never given this topic any thought.

They made their way to the restaurant and were seated promptly. As they both tried to force a conversation out of thin air, Katie kept noticing his eyes glancing over her breasts. She clearly saw that there would be no chemistry with this matchup and decided that sex would have to be enough for tonight. She pushed her arms against her breasts and leaned forward to purposefully give him a better view. Kevin stopped mid sentence of the next meaningless question he was about to ask her.

A painful hour and a half later, Kevin paid the check and they were off.

"Shall we go to your place?", Katie asked.

"Oh!, Yeah, sure. This way.", he said, sounding surprised she was taking the evening in this direction.

A short 10 minute walk and an elevator ride later they were at the front door of his studio apartment. His place was picture perfect, looking like it was out of a home furnishing catalog, despite the grays and muted colors. Everything was neat and in its place with strange modern artwork on the walls who's only purpose was to explain he had money.

"Something to drink?", Kevin asked looking toward Katie with the refrigerator open.

"No. I am good thank you."

Katie walked across the square room to his bed and sat down on the edge. She came for one thing and intended to get it. Kevin grabbed a beer and walked towards her sitting on a couch directly across from the bed. Katie leaned forward again, showing off her cleavage, hoping to speed things up. With a cliche seductive tone and a raised eyebrow, Katie asked, "So, what are you into?".

"Uh. Oh, you know. Basketball, my job, going to the movies. I listen to a lot of NPR." He took a sip of beer to indicate that was the end of his answer.

Katie could not believe how hard Kevin was making this. She thought back to the Cuffed post, wishing he was the experience dominant looking for a submissive. She wanted him to take control. Katie stood up and let the straps of her dress slip over each shoulder, letting the flowing dress fall to the floor. Kevin sat there frozen with his mouth hanging open. She reached back and unhooked her bra, letting him finally see her most perfect asset. She hesitated for a moment and then pulled off her matching thong. She let him get a quick glance at her perfectly shaved and smooth pussy, before lying down on his bed. She was hoping he could do the rest.

Kevin quickly stood up fiddling with his belt trying to solve what seemed like a toy puzzle. She couldn't believe how unsexy he looked with his pants and underwear down around his ankles like a little kid as he hobbled over to the bed. She could see his somewhat small, but fully erect cock pointing directly at her. Without even taking off his shirt and tie, he crawled on top of her jamming his wet tongue deep into her mouth in the most unpleasing fashion. With one hand supporting his weight, his other went directly for her breasts, squeezing them repeatedly as though he was kneading dough. Without any foreplay, she felt the head of his cock knocking on her pussy. As he continued to push his overly wet tongue into her throat, he pushed down hard on her pelvis, entering her abruptly. He immediately began thrusting as fast as he could.

Katie could not believe how bad this guy was at sex. Sex with an actual jackhammer would have been more pleasing. The one part of the evening she was looking forward to was now ruined. Katie tried to enjoy the feeling of his cock filling her as he repeatedly flailed on top of her. She tried to make the best of it, by imagining that she was in fact a submissive and this guy was having his way with her. She closed her eyes and spread her legs, pretending that each ankle was bound to the soft bed. She then spread her arms, above her head, imagining they were bound in a similar fashion. He took no notice of this as he continued to grope her breasts. She fantasized that in this moment, her body was to be used for his pleasure. As the thoughts ran through her head, she could feel her orgasm coming on. She focused hard on the image of being bound, and with another thrust, her body shuddered as her pussy repeatedly contracted around his cock. Her body tingled to the satisfaction of the fantasy in her head. Within seconds, Kevin had pulled out, got up on his knees and started stroking his cock vigorously. He was quickly moving towards her face, clearly wanting her to suck him off. She again, had to indulged in a fantasy, imagining that she was instructed to swallow his load. She propped herself up on her elbows quickly took his cock into her mouth. She felt him instantly shove it to the back of her throat, nearly causing her to gag. Leaning forward, she folded her hands behind her back pretending they were bound. He grabbed onto her head pulling himself deeper into her mouth. Without warning, she felt the his warm load hit the back of her throat. She quickly started swallowing as it continued to flow out of him.

Once the last drop had left him, Kevin pulled himself out of her mouth and got off the bed with a huge smile.

"That was good", he said enthusiastically. "I could tell you came." He wore the words as a badge of honor with a grin that made her want to smack him across the face.

"Uh, yeah...", Katie said quietly under her breath. She didn't have the heart to tell him it was her fantasy that did all the work.

"I have an extra toothbrush if you want it."

"Kevin, this has been...", Katie paused looking for a word that would not offend him as his taste lingered in her mouth. "I am not going to be spending the night. I also don't think we will be doing this again. You are a nice guy and we had some fun, but I don't think this was the click Lilly had in mind for us."

"Oh. I see.", Kevin said looking slightly disappointed.

"I'm just going to go. Thank you for dinner."

Katie quickly got dressed and left his apartment. As she walked back to her place she saw five text messages from Lilly wanting details. Katie figured she would call and get this out of the way before she got home.

"Hey! "

"Soooooo! How was Kevin? Cute, right?"

"Yeah, he was cute. That is about all he had going for him."

"What do you mean?", Lilly said, sounding dumbfounded.

"Having a conversation with him was tedious. And then there was the sex."

"You didn't!?"

"Yeah. I thought it would at least be a good opportunity for a hook up. Turned out to be the worst sex of my life."

"What?! How come?"

"He had no finesse. It was like he had never done it before and tried to act out what he had seen in a bad porn." Katie cringed as she thought back to the sex.

"Yeah, I don't think he has a lot of experience. He is career focused like you."

Katie could feel her anger starting to boil inside. How could Lilly think that being career focused means a complete lack of sexual experience on the level of Kevin. Katie didn't respond.

I am sorry it didn't go well. You know I am just looking out for you."

"Thanks Lilly. I know. I have to go."

"Okay! We will talk more later. Bye."

Finally home, Katie stepped into her shower, washing herself of the awful date. She felt that she had just reached a new low.

Katie got up early Sunday morning trying to put the previous night's defeat behind her. She quickly ate a bowl of cereal before sitting down to work through a last draft of her proposal. Before starting, she checked Cuffed to see if she had any new messages. Sure enough she had 8 waiting for her. Unfortunately they were all guys looking to hook up again.

Katie was loosing hope. She thought Cuffed might be her answer to exploring bondage, but it was turning out to be a site of guys hopelessly looking for meaningless sex. Her social life had hit rock bottom with the worst date and sex of her life. On top of that, her only friend was fixated on her lack of a love life, something she did not want a daily reminder about. While appreciating the concern, it mostly annoyed Katie.

As a shot in the dark, Katie pulled up the post she had read the day before. It was from a dominate man, by the name of Maestro, looking for a new woman to bring into a submissive lifestyle. While Katie did not have time for a full lifestyle as he was requesting, she decided to send him a message anyway. Katie carefully took the time to craft a message she was sure would be ignored.

Maestro,

I am new here and looking for a little guidance. I am not someone looking to be submissive full-time, but I was hoping you could assist me. You clearly seem to know what is going on here. I am looking to slowly ease into this, just to experience it. How can I find the right people? Most guys seem to only want to hook up for sex.

-Katie

Katie sent the message and promptly returned to her proposal. She had an email from her boss, asking for an update on the report. Katie quickly emailed the draft. As she now worked to turn the draft into a final copy, she wondered how much longer she could keep up her lifestyle of working all the time. She worked so hard in college to land a successful career and didn't want to throw that all away. As the hours slipped by, Katie was confident in her work by the time lunch rolled around. She sent the final draft to her boss. Before making some food she checked her Cuffed messages. She was surprised to already see a response from Maestro. She promptly opened the message and began to read.

Katie,

Thank you for reaching out to me. While there are serious people here on Cuffed, it is not without its problems. I urge you to continue on. I know you will find what you desire. I can help you get in the right direction. I see you are also in the DC area. Why don't we meet for coffee tomorrow?

-Maestro

Katie could not believe it. She had not originally seen that he was also in the same city. She finally had something to look forward to that had nothing to do with awful sex or annoying friends. Katie promptly responded.

Maestro,

Thank you! Can you meet at the coffee shop on 19th and N Street for lunch at noon? I am usually pretty busy, but I can find a half hour for lunch.

-Katie

Katie promptly started to get her work in order so she could afford to leave work at lunch if he responded yes. She quickly blocked of her calendar for the half hour, so she would not have any surprise meetings. She began preemptively emailing anyone who might request any documents from her Monday morning. Katie felt a wave of excitement as she anticipated what they might discuss. This would be the first time Katie would have a chance to openly discuss her interests without scaring someone important away.

Hours pass with no response. Katie started to become nervous, wondering if she might have been to eager with her wording. As she sat there waiting for either a response from her boss or a response from Maestro, her phone rang, startling her. Katie answered it without even looking who was calling.

"Hello?" Katie said as her heart stopped racing.

"Hey, it's Lilly."

"Oh! Hi. What's going on?"

"Not much. Kevin said he had a great time with you. He really wants to go on another date."

Katie was beginning to tire of this theme. "Did you tell him or David what I told you?"

Lilly paused. "...no".

"Well you should."

"Oh, c'mon Katie. Was it really that bad?"

"Yes! It was really that bad." Katie was impatiently tapping her foot as she did not want to be having this conversation. As Lilly worked to try to convince Katie that she should give Kevin another shot, she saw a response come in from Maestro.

"Hey Lilly? I have to go..." her mind searched for an excuse "...my boss is calling."

"Oh, okay. Later"

Katie opened the response, putting Lilly and Kevin out of her head.

Katie,

That works for me. I have attached a photo of myself so you know who to look for. Until tomorrow.

-Maestro

Katie glanced down at his picture. He had short, dirty blond hair, and the bluest eyes she had ever seen. He had a very strong jaw line with a sexy 5 o'clock shadow, which she found very appealing.Nice AND attractive,she thought. Katie quickly responded.

Maestro,

Great. I will see you tomorrow. Below is my picture.

-Katie

Katie attached the picture she used for all her social media. It was the classic smiling while not looking at the camera pose. She felt it naturally captured her smile while showing her on a good hair day. Just as Katie sent the message, an email from her boss came in bringing her sprits down. It was her proposal full of edits. Just as she was about to plow through making the changes to the proposal her phone rang again with a number and no name.

"Hello?"

"Hi. Katie?"

"Yes. Who is this?"

"Hi. It's Kevin."

Katie purposefully paused to cut out any chance of small talk. She figured that he called due to Lilly's guidance to find Katie love.

"Katie. I was wondering if we could go out again sometime?"

Katie could not stand how bland his words were. "Kevin. I told you when I left that there was really nothing for us to go on."

"But didn't you have a fun time at my place?"

Katie took a few seconds to craft her response. "I really didn't feel a connection or spark between us. Sorry Kevin. The answer is no." Katie promptly hung up to stop any attempts of him trying to get a second date. She went to her contacts list and added his number underDo Not Answer! - Kevin.

Katie saw a new response on her screen from Maestro. With the rolling excitement she felt in her stomach, she opened his message.

Katie,

Very attractive...

-Maestro

Katie blushed as she read his words. Tomorrow couldn't come soon enough.

Yambler
Yambler
36 Followers
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5 Comments
AnonymousAnonymousover 7 years ago
Well done

Your story is nicely written. Love the way you fleshed out the characters so quickly. I'm really looking forward to future chapters. I have one slightly negative comment, however. When you use a word that has multiple meanings and different spellings, use a dictionary or thesaurus. She put on her "high heals"--wounds "heal" and the shoes have "heels." Keep writing!

AnonymousAnonymousover 7 years ago

I am really loving this, please dontt keep us waiting too long for the next chapter....

sub_peachiessub_peachiesover 7 years ago
thank you

For a wonderful story. This is quickly becoming a favorite of mine. I look forward to future chapters.

AnonymousAnonymousover 7 years ago
Brilliant

I've been on literotica for probably nine years, but I've never posted a comment. This is so well written! Most of the time this site is filled with writing to one end only, but reading this was such a change of pace! It's lovely to find something both well written and well paced, not to mention how much this is potentially lining itself up with some of my own fantasies. The start of this is so promising, I couldn't help but say, truly can't wait for more!

AnonymousAnonymousover 7 years ago

The character and plot development these first two chapters have been top notch. This is professional level story telling. I will be eagerly watching where and how you take it.

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Maestro Ch. 01 Previous Part
Maestro Series Info

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