Pushing the Boundaries

Pushing the Boundaries

Joe E Hartley

May 2021

Emily came home from work with a lot on her mind. She really needed to talk about what had happened with her husband, but Kyle wasn’t due home for another couple of hours and this was not a subject she could talk about on the phone and especially not with him at work. She wasn’t even sure she wanted to talk to him at all about this. She needed a drink and time to figure out what to do.

She poured herself a glass of wine and stepped outside onto their backyard patio. She sat at the table and relaxed in her garden with the sounds of her water feature soothing her mind. She often spent time out here when she needed to think.

She actually wasn’t upset, quite the opposite in fact, but she was confused and unsure how to proceed. Some small voice in her head knew what she wanted to do, but she had to reject that idea. The rules she learned as a small girl and reinforced by the adult society where she lived, overruled any desire that small voice wanted.

That should settle the question in her mind, so why didn’t it? Could it be that Kyle spent so much time at work trying to get a promotion and more money, that they stopped doing fun things together? She knew he’d have to put in long hours when he took this job and she agreed that he should. She also knew that she had to also work to help supplement their income, not to mention the fact that she’d be bored out of her head if she had nothing to do.

She loved her job and her boss was great. She did not have the complaints so many did about having an unreasonable boss. He’d even offered her a raise today and that was the source of her dilemma. The raise came with some extra duties, but she didn’t have to accept the raise and there would be no further discussion about it. Why hadn’t she just said ‘no’?

Maybe because the small voice in her head wanted to take on the extra hours. She had asked for a week to think about it, and her boss agreed. He again told her there would be no repercussions if she said no; she would still have her job and would report to her same supervisor just as before. The new position would require her to report directly to him.

Kyle was due home in another hour. She could put this out of her mind for the evening, and think about it tomorrow. She got up to start dinner.

She prepared a dinner of Swiss steak, mashed potatoes, and green beans. The table was set just as Kyle walked through the front door.

“Something smells delicious,” he announced.

“Hi honey,” Emily answered walking over to kiss her husband hello. “How was work?”

“One of the managers said I was doing a great job on his project. I might be getting close to being promoted to supervisor,” he said excitedly. “How was your job today. Is it getting any easier?”

“I think I’m getting the hang of it. Today was much easier than yesterday,” she answered.

They sat down to dinner; it was actually one of Kyle’s favorites. She had decided not to tell him about the decision she would have to make in the next few days, but later on tonight she might get an idea of how he would respond if or when she decided to tell him.

Later Emily washed the dishes and they both watched a bit of TV before heading up to bed. Kyle was in a good mood and that normally meant in was also in the mood for sex. Emily came to bed naked, knowing what was coming.

He squeezed her breasts a few times then climbed on top of her. She knew how to get herself in the mood, since she had a repertoire of fantasies to call on. Tonight that small voice inside her head offered another.

Within a few minutes he rolled off of her and that’s when she asked her question.

“Tell me about your fantasies. What would you like for me to do that I haven’t s far?” She asked.

“I’ve told you before that my biggest fantasy is for you to be with another man, but you have always seemed reluctant to do that,” he shared.

“I know, but maybe that’s because I don’t understand why you’d like that. I always thought that having the wife cheat with another man belittled her husband,” she probed.

“It would not be cheating if I knew about it and encouraged you. Are you seriously thinking about doing it? That would be so hot.” He asked testing her interest.

“I’m just trying to understand. You have suggested this before and I’ve been taught that is not what ‘good girls’ do,” she replied.

“Bad girls are more fun,” he said again grabbing her breasts.

They soon tired of the conversation as no plans were being made tonight and each rolled over and went to sleep.

The next morning Kyle and Emily shared their coffee and kissed each other goodbye before heading off to work.

Emily walked through the building, said hello to her supervisor and took her position at her desk. No one commented on her conversation with their boss. It was as if no one knew about his proposal to her the day before. She didn’t even see him. It was just as he said, the decision was hers and he would apply no pressure. She had several days to decide, but though-out the day, that small voice in her head talked to her.

Over the next several days, her internal voice became louder and even reminded her of her husband’s fantasy. She knew she would never leave Kyle, even if he felt his penis wasn’t as large as what he thought she needed. She knew that size isn’t everything, he wasn’t that small, but he really didn’t know how to use his penis.

He was hard working and tried to give her everything she ever wanted. She loved him and sex did not have to be the main thing holding a marriage together. She needed to make the decision by tomorrow.

She stayed late waiting until everyone had left, then she walked towards her bosses office. She needed more information, or rather verification of the information she already had. She knocked on the office door and hear a voice inside say. “Come in.”

She opened the door and said, “Mr. Lopez?”

“Oh, hello Emily. Have you made your decision?” he asked as he stood and approached her.

Emily noticed a growing level of excitement in his slacks. “This is a very big decision for me and I want to be certain I know what I’m getting into, Mr. Lopez,” she said nervously.

“You can call me Jose when we’re alone and as far as your duties are concerned, you will be a personal assistant and be required to do a variety of tasks which cannot be placed into a job description. I might need you to pick up an item for me, or make reservations, or work some extra hours sometimes out of town.” He shared. “Again, if you are uncomfortable with this position, we can just forget about it and act as if it was never offered.”

“If I agree, how soon would I start?” She asked aware of a wetness beginning between her thighs.

“I have an event this weekend that I might need some assistance. If you want to see what is expected, you can accompany me and make your decision after that event. He offered.

“Can I let you know tomorrow?” she asked.

“Sure,” he replied.

Emily drove home feeling just as confused as she’d been when the offer was first made earlier in the week. The voice inside her head now screamed at her. Did she see the lump in his pants when he thought she was there to accept his offer, did she notice her level of arousal just being in the same room as him, did she remember Kyle’s fantasy?

She needed to talk to her husband tonight and see just how serious he was. She already knew she wanted to do this.

She arrived home later than usual and instead of starting dinner, she poured a glass of wine.

Kyle arrived home at his usual time, but did not smell dinner cooking; neither did he see his wife. He yelled out, “Are you home?”

A response came immediately, “Out back. Grab a glass of wine and join me.”

Kyle knew something was up; Emily never failed to have dinner waiting for him. He poured a glass of wine and headed out into the back yard. He saw his wife seated at the table with half a glass of wine.

“Did something happen at work today? You weren’t fired were you?” he asked full of concern. They needed both incomes at least until he got his promotion.

“I was not fired, but something did happen that we need to talk about,” she started.

“What happened?” He asked with a bit of relief, but still concerned.

“I was offered a promotion.” She said.

‘That’s great,” he announced.

‘There’s more,” she added.

‘Yes?” he questioned.

“You know that fantasy of yours you keep telling me about?” She hedged.

“What has that got to do with you getting a promotion?” his brow furled trying to reconcile the two things.

“My boss asked me to be his personal assistant.” Emily announced.

‘That’s great,” Kyle reacted still not getting the implication.

“That means I’ll be working late with him and joining him on some out of town business trips,” she tried to clarify.

She looked over at her husband who seemed to slowly put the pieces together. She watched the emotions roll over his face; first there was intense concentration, followed by the ah-ha moment, and finally the broad smile indicating he understood that his fantasy was being offered to him.

He tried to get his jubilation under control, “what do you think? Do you want to do it?”

“I’m seriously thinking about it, but I want to know what you think. This could be the fantasy you’ve been asking about for the last year. I asked you on Monday if it was still a fantasy of yours because that’s when he made the offer. I need to give him my answer tomorrow and the first assignment will be this weekend at some event he need to go to.” She informed him.

“This is my biggest fantasy and I’d love to have you accept especially if you tell me all about it after.” Kyle shared.

“I’m actually glad you said that, because Jose Lopez is hot. I got wet this evening when I asked for another day to decide. He seemed eager to have me start right then and there, but I needed to talk with you first,” she said. “I don’t want you to think I’m cheating so we need to talk about the ground rules. What am I allowed to do with Jose and where do I have to draw the line?”

The rest of the evening was spent going over what Emily was allowed to do, what she was encouraged to do, and very little of what she was not to do. The only item Kyle insisted she not do was to keep secrets. He wanted to know everything.

Dinner was never made; instead, they called for take out as they continued discussing all that Kyle fantasized about his wife doing with her boss. The more they talked the more aroused Kyle became.

“Have you touched his cock yet?” Kyle asked.

“No, but I did notice a sizable budge in his pants this evening when he thought I came into his office to accept his offer.” Emily answered with a sly grin.

“Did he show you his cock? Is it bigger than mine?” Kyle wanted to know.

“I only saw the budge, but I would guess that yes, he is bigger than you are,” she replied noticing Kyle’s growing erection.

They skipped the TV and went straight to bed after dinner. Kyle was so aroused he came early and Emily fell asleep knowing she would explore a new man this weekend.

The next day at work, Emily was on pins and needles all day and just like the day before she stayed late and after her supervisor had left for the day stood in front of Mr. Jose Lopez’s office. She knocked and after hearing the “come in” opened the door and stepped inside.

“Mr. Lopez, I’d love to accept your offer,” she said without prelude.

“I’m glad to hear that, but I think we should keep to the agreement we made yesterday. This is going to be very new to you and you really don’t know what is involved with this new position. Lets do the ‘trial run’ this weekend and then you can decide. Before we start the weekend event, I need some information,” He handed her a sheet of paper, “Would you fill this out please?”

Emily was expecting a non-disclosure agreement, but instead saw a form asking for her sizes in clothes including bra size and shoe size, plus a few measurements she didn’t know.

“I’m not sure I know my shoulder to waist measurement or my waist to knee measurement.” Emily shared after she filled in the basics.

“No problem,” Jose said as he pressed a button on his phone. “We need a few measurements, please,” he spoke into the phone.

A young woman entered with a tape measure and took the form from Emily. She efficiently took several measurements and entered them onto the form before handing it to the professional man seated at the desk. She left as silently as she had arrived.

“I’ll expect you here tomorrow morning at 7 AM, bring an overnight bag.” Jose announced to the stunned woman standing in front of his desk.

Emily went home again confused, but in a very different way this time. She tried to figure out why Mr. Lopez needed her measurements and why the unusual measurements. Maybe he was getting her some sexy lingerie, or maybe something kinky. Her excitement built the more she thought about what would happen the next day.

She again called for take out just before her husband was due home. She was far too excited to cook. She had a glass of wine and when Kyle arrived home, she poured one for him too before she relayed all that had happened in Mr. Lopez’s office, including the woman who took the unusual measurements.

Both Kyle and Emily were excited about this new adventure and decided not to have sex the night before her step into the fantasy world.

Emily packed a bag and included a few pieces of her sexiest lingerie. She went to bed, but her small voice inside her mind kept her awake playing out one erotic scenario after another involving her sexy boss.

She got up early, had her coffee, and left for her office before Kyle even got up. She did leave him a note saying she’d tell him all about her weekend when she returned home.

Emily pulled into the parking lot at 6:30 and saw Jose Lopez’s car in its normal spot. Glancing around she saw him walking towards the front door. She honked her horn and waved to him, then pulled into a parking stall.

“Good morning,” she said walking towards him.

“Good morning, Emily. I see you are eager to start your new position.” He then turned to finish opening the door and turn off the alarm.

“I’ll just be a minute,” he said heading back to his office. He came back carrying a brief case and walked toward her, “Are you ready to go?”

“Yes,” she replied holding up her overnight bag.

They got back into Jose’s car and he drove them to the airport. They checked their bags and went though security. Airports are always boring and they filled the time with small talk about Emily’s family, school, husband, etc.

Travel is always time out of time; just putting one foot in front of the other. It does need to be pre-planned and Jose had this travel day planned perfectly. The shuttle was waiting, the reservations had been confirmed and the room was ready.

Their bags were placed in the room and the bell-hop had been tipped.

“We have a few hours before my meeting, so why don’t you open the blue suitcase?” Jose asked as he made himself comfortable on the bed.

Emily opened the suitcase and just stared at the contents. She thought that she should have been surprised, but that little voice inside her head had already played out this fantasy for her last night. She saw some very erotic lingerie plus some fetish items, she had only read about. There were a couple of items she had no idea what they were.

She pick up a sheer camisole and a pair of matching panties and held them up for Jose. “Should I put these on?” she asked with a grin.

“Yes, please,” he replied and while I’m at my meeting you can try on the other items.

Emily went into the bathroom and within a couple of minutes walked out displaying her body to the man on the bed. Her breasts were on full display only covered by the thinnest of material. The panties she wore were likewise only to hint at the barest of material. Her pubs were only slightly covered and the panties were so small that her pubic hair (which she made sure was neatly trimmed) showed above the waist line of her panties. As she walked into the room the panties started to wedge themselves between her labia giving Jose a very intimate view of her sex.

“Lovely,” Jose acknowledged eyeing her up and down. “While we are in this room, I want you to wear only what is in that suitcase. Can you do that?”

“Oh, yes, I can. I love what I’ve seen in there so far.” Emily replied.

“Fantastic,” he said getting off the bed and walking towards her. He caressed her breasts with the back of his hands and drew them down to the naked flesh of her thighs and using his finger played with the folds displayed by her panties.

Emily started to pant and the thin wisp of panties she wore soon became soaked. Jose stepped back and admired her aroused nipples and pinched each in turn then removed his shirt.

Emily stared at the unveiling of the naked flesh in front of her. Her gaze dropped lower and saw his budge forming. She licked her lips.

“You like what you see?” Jose asked and he unbuckled his belt.

Emily watched intently as Jose lowered his pants and kicked off his shoes. He stood in front of her wearing only his boxers. His excitement was obvious and he noticed that her eyes never left the tent created in his boxer shorts.

Jose took a step closer to Emily and caressed her breasts. “Do you like this?” he asked.

“Yes, very much,” she sighed.

“As long as you accompany me on these business trips, I will want to touch and caress you often. Are you okay with that?”

“Oh yes, touch me as much as you want, and wherever you want,” she answered beathing heavily.

“How about here?” he placed one hand on her mostly bare butt.

“Uh-huh,” she uttered.

Jose then goosed her and she leaped into his arms then relaxed onto his finger. “Whatever you want,” she said.

He lowered his hand from her breast and fingered her wet channel. His fingers explored both of her channels and she voiced her enjoyment. He waited until she stiffened in the throes of her orgasm before removing his hands from her body. He stepped back and lowered his boxers.

Emily recovered from her orgasm and opened her eyes to see Jose’s naked cock staring at her. She dropped to her knees in front of what she considered the largest cock she’d ever seen. She gripped it with both hands and stroked down it’s massive length. The purple head moved closer as if to kiss her. She placed her lips on the head and it surged forward. She used her tongue to flick across the opening and tasted the first drop of the salty fluid. She pushed the entire head into her mouth savoring the smooth texture and taste.

Emily took as much of his cock into her mouth as she could, much less than half of his length, and then pumped him in and out of her mouth. He pushed her away but she came right back and this time licked his cock from his balls to his tip over and over again, treating it like an ice cream cone. She found she loved licking him.

Once he was again under her control, she took his cock back into her mouth. This time she used one hand to stroke this length, her other hand to gently squeeze his balls and her mouth to pump the head of his cock.

Jose stiffened and grabbed the back of her head. He spilt his load into her mouth then pulled back. He knew he was well endowed and most women could not take his full length in their mouth.

They both took a moment to recover, before Jose asked, “Is this something you want to do more often on these business trips?”

“This is better than I imagined. I want to be your assistant on these trips.” She answered enthusiastically.

“That is only a small part of what will be expected of my assistant, but I’m glad you found that enjoyable; so, did I. I have to go to a meeting that will take a couple of hours. Try on the other outfits while I’m away and we’ll play more when I get back.