Tell Me if I Need to Stop: Prologue [F20’s,M20’s,M20’s,M40’s] [Slow Burn] [Cheating] [Boss] [Cuck] [Business Trip] [Humiliation] [Dirty Talk]

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**Author's note**

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This is a just the prologue to a muti-part series (not that nothing happens in this installment). The main thing to know is that some of the tags applied are more applicable to later installments, but I wanted the audience to have an idea of what they were in for. Please upvote if you like it.

-LV

Prologue

 

Spring was finally spelling the long sloppy end of winter and, for the first time in a long time, Kyle enjoyed his walk from the subway to the little condo just outside of Bushwick. He strode the sunny sidewalks in one of his nicer suits. Working in finance, there was tremendous pressure to dress well, even if he could barely afford it.

He stopped at a busy intersection a couple blocks past the station and saw her at the opposite corner. She was flawless, clad in tight black jogging shorts and a bright, loose tank over a sports bra. Dripping with sweat and breathing heavily, she paced the sidewalk to recover from her daily run. She looked up and noticed Kyle checking her out from across the street, but he wasn’t the only one who noticed her. A man walking a dog came to a stop alongside her.

“Hey girl. What’s your name?” asked the confident stranger.

She shot Kyle a devious grin before answering, “Harper.”

Kyle saw the interaction but couldn’t hear what was being said. Harper seemed flirtatious at first, but then, she clapped a hand over her mouth and Kyle thought she might be crying. She wasn’t. Harper doubled over and laughed hysterically. Crossing the street towards Kyle, she gave the stranger a playful shooing gesture.

“What’s going on?” asked Kyle.

Harper was laughing so hard that her eyes were bleary with tears. “Hey dear.” she said. Harper took Kyle by the hand and dropped her voice. “I noticed you right before that guy came up to me and, because of that thing you like, I thought I’d play along a little. But when I told him my name, he said that it was same name as his dog and I — I couldn’t –” she broke out laughing again.

Harper and Kyle were good friends since almost the beginning of college and started dating during their sophomore year. Kyle got his degree in business, planning to stay in the city and try for a career in finance. Harper was math focused but wanted a path with real career opportunity and ended up getting her degree in economics. 

Six months after graduation, the two of them were married and living in the city. Kyle worked crazy hours in his first role at an investment bank, and Harper scored a position modeling economic projections for a rather prestigious fund company. Things were going pretty well, in spite of the high cost of living. Harper’s pay was significant, and between her and Kyle’s salaries and a little help from her parents, they were able to afford a place that wasn’t a terrible commute downtown. The building was old, and not in a charming way, and they had some annoying neighbors, but it was theirs.

Harper spent most of her days working at home, their second bedroom was converted into her office. She worked long hours but, outside of the twenty percent required travel, she had a pretty flexible schedule. Kyle had the opposite experience.  Face-to-face was everything to his employer, and the more hours he put in the better. Most of the crop that was hired in with Kyle had already washed out, as was expected, but he survived his first year. It was still too early in his career to expect success, he needed to put in the time and not screw up, but things were starting to look promising.

 

“Stop, stop, stop. I don’t want our neighbors to see.” said Harper, as she quit fumbling with her keys to swat Kyle’s hand away from her butt. “Besides, I’m all sweaty right now.” 

“Maybe I like you all sweaty.” replied Kyle.

Kyle already had his key out and unlocked the door but didn’t open it immediately. “Come on. I have to pee.” complained Harper. He held the doorknob firmly, deliberately not opening it. She glanced around and, as always, the inescapable woman next door was in front of her house, pretending not to stare at the young couple. Harper shook her head in annoyance but relented, giving Kyle a quick, perfunctory kiss on his lips.

“Make sure you don’t turn into an asshole.” said Harper, stepping inside and slipping off her damp tank top and tossing it in the hamper.

“Sorry, I didn’t mean to make you mad.” said Kyle.

“No, I know. It just reminded me that you hang around those Wallstreet dude-bros all day and I want to make sure that you don’t turn into one of them.”

“I take your point.”

He was listening but Harper was fully stripping in front of him, and it was hard not to be distracted by her body which glistened with a sheen of sweat. She turned and stepped into the bathroom. Kyle followed her automatically. 

“I have a call with the Asia group in twenty. So, no fun right now.” said Harper, catching him staring in the mirror while she waited for the shower to heat up.

Kyle assumed he must have misjudged or misunderstood the situation. He thought she mentioned ‘that thing’ he liked and ‘playing along’ after talking to the guy with the dog. Kyle’s presumption was that Harper was deliberately flirting with the stranger because of an earlier admission of his. Kyle occasionally fantasized about his wife with other men. He assumed, that’s what she was referring to. But now he second guessed what happened. He had a reputation for occasionally misinterpreting interactions and thought that he might be guilty of it again. He could have asked Harper directly but, because of the awkward circumstances surrounding Kyle’s admission of his fantasy and how it related to an uncomfortable aspect of their relationship, neither Harper nor Kyle were good at communication on the subject.

It started a few months before the couple’s wedding, Harper had a ‘potentially serious’ issue that she needed to discuss with Kyle. There was a discrepancy in the timeline of their relationship that she needed to talk about before getting married.

Through college, the two of them were in the same group of friends long before they dated and, because of that, they would regularly hang out. Once or twice a month, Harper and Kyle would go to the movies with their friends. They even had a regular group text about it. When Kyle finally made his move to ask Harper on a date, he did it in a way that seemed clear to him, but Harper misunderstood the invitation. It happened when the two of them were talking during a particularly boring movie and Kyle mentioned that he wanted to see a new comedy coming out the following week. He wondered if she’d go with him. Harper assumed Kyle was talking about a typical group outing and not a date. When Kyle texted her to confirm the details, it never crossed her mind that his message wasn’t in the group thread.

The one-sided date included several small occurrences that left Harper unwitting to the fact that Kyle saw it as a date. When they met up, Kyle said ‘just the two of us’, referring to the surreal circumstance of going without their other friends, but Harper assumed he was letting her know that the rest of their group bailed on the evening. Kyle paid for her ticket, but mentioned he had rewards that would expire anyway, and she assumed he was only making a friendly but practical choice. The situation would have been made clear at the end of the night, but Kyle chickened out and hugged Harper after their long walk instead of giving her a kiss.

It wasn’t until Kyle sent her a text later that night, saying how much he enjoyed their date and that he would love to take her to dinner next time, that Harper understood the confusion. She did like Kyle and eventually texted him back to say that she’d love to go to dinner with him, and that’s how the relationship that led to their marriage began. But she didn’t text him back right away, because she was occupied.

After her unclear first date with Kyle, the phone buzzed in Harper’s room. She was already in her pajamas getting ready for bed when she picked it up. It wasn’t Kyle. It was a typical late-night message from Seb.

Harper downloaded Tinder on a whim the year prior to help coax a friend out of the gloom of a bad breakup. The two of them sat up all night on their phones, judging the local crop of men. Harper did not intend to make a connection but inevitably matched with Seb. She swiped right on him at the urging of her friend. Seb was shirtless in his profile pic, confidently displaying his cut, gym-rat physique. She played it off as casual, but appreciated how Seb looked, his firm of his body. When he messaged her, telling Harper he thought she was cute and would love to show her around his apartment, she couldn’t help but reciprocate.

She never had any illusion of a meaningful relationship with Seb. He was open about an on and off girlfriend whose life would always be entwined with his. But when he and the girlfriend were on the outs, Seb would message Harper, and the two of them would do what they did. The night of Harper and Kyle’s first date, when Kyle was wracking his brain over how he should word his follow-up message to his future wife, she was Alone with Seb in her apartment, doing those things she did with him.

At first, the confusion over when Harper and Kyle started dating felt minor to her, making it a ridiculous notion to ever tell him about the late-night hook-up. It first struck Harper that the situation might be a problem when Kyle began to romanticize that specific evening as the couple progressed in their relationship. The movie they watched retroactively became Kyle’s favorite and he would regularly talk about small details of the night, weaving them into the mythology of their relationship.

As Harper started to fall in love with Kyle, the reality of her secret hook-up turned from a superfluous detail into an uncomfortable reality that bothered her often. Then suddenly, they were engaged, and she was so happy and busy with the end of school and job interviews and her internship that the issue was forgotten. Things eventually quieted down in Harper’s life and she and Kyle spent more and more time reminiscing on their relationship as their wedding drew closer. 

“I had sex with someone I never told you about. Shit.” said Harper. The discomfort of the secret had been gnawing at her and, during an otherwise mundane conversation with Kyle, it came spilling out.

“Does that make it six for you? Were you trying to save my feelings because I’d only ever been with you and Sky?” replied Kyle, failing to grasp what Harper was saying.

She was scared, but had enough and decided to tell Kyle, even if it risked their relationship.

“Our first — crap this is going to sound bad. I love you and need you to know that our ‘first date’, I didn’t know it was a date.” said Harper.

“I’m confused.” admitted Kyle.

“We went to the movies together, but I thought it was a group thing, like our friend group, but only the two of us showed up.”

“That’s doesn’t… but what does that have to do with anything?”

“After we went out that night, I met up with a guy from Tinder and we had sex.”

It was hard for Harper to finally say it out loud, but she got through it. Kyle was at a loss for words and it worried Harper that he was going to call off the wedding, but he didn’t. He was completely in love with his fiancée. Kyle asked a couple necessary follow-up questions. How long had they been seeing each other? Was it a serious relationship? et cetera. Then, by mutual agreement, the two of them moved on from the subject.

Harper’s sort-of-but-not-really indiscretion didn’t come up again until one uncomfortable night during their honeymoon. Harper surprised Kyle, stepping out of their hotel suite’s bathroom clad in black leather style lingerie. Her corset was laced with belts and silver buckles. The bra and garter were a tight network of straps which ensnared the barely-covered curves of her body. She purchased it on a whim, hoping to add a little excitement to their honeymoon. Kyle thought she looked awesome. His spirit was willing but, for the first time in his life, his body was unable to perform.

Unknown to the couple, the only problem was dehydration because of a long day in the sun. But, because Harper had gone out on a limb to please her partner and, because it went so poorly, she felt self-conscious and unattractive. The newlyweds stayed up late talking about sex and Kyle profusely communicated how attracted he was to his wife. Still, the subject was on the table and Harper wanted to know if her husband had any interests that she didn’t know about. Kyle could tell she was feeling vulnerable, so he opened up to her. 

“I do have one fantasy.” he said. Harper’s body tightened in anticipation. The two of them laid naked and perspiring from their failed lovemaking. Harper still wore the black corset around her midsection — her long dark hair tousled and frizzing from the humidity. “A lot of times, I imagine you with other men.”

“Like having sex?” she asked timidly. 

“Yeah.”

She was going to ask if he was being serious but could tell by Kyle’s manner that he was. Harper trod carefully with the conversation from that point, not wanting to dampen the mood on their honeymoon by bringing up things that were relationship taboos. 

“Like I said before, and I’m not committing and don’t want to do certain things, but I would like to help my husband enjoy his fantasies. How does it work exactly? You imagine me with other people. What specifically does that look like?” she asked.

“So, you’re not grossed out by me?” he asked. 

“No, I’m just curious.” 

“Well, when you leave town for work, I think of you meeting up with some coworker or stranger. Or when you’re out with friends, it’s a similar deal. And there’s –” 

“What? Go on.” she pushed. 

“Seb. I pretend you still meet up with the Tinder guy.” 

It was a wild reversal from what she feared in the past. Her husband was aroused because of her history with Seb. 

“OK, I’m not going to have sex with anyone else but, if we were to somewhat indulge your fantasy, how would we?” asked Harper. 

They talked it through for a while. The obvious answer was role playing, and it was possible Harper might be willing to try flirting with men in the future. In the interim, what Kyle really hoped for were the details of her hook-up with Seb on the night of the couple’s first date. Harper was apprehensive but pushed through. She started with how she and Seb met on Tinder and feared she went too far when by telling how much she liked his body, but Kyle became aroused. Harper felt spurred on by his excitement and the story and its indecent details flowed out.

“We’d been hooking-up off and on for almost a year so he knew the drill. I was wearing my pajamas when I met him in the lobby of my residence hall. When we got to my room, I started by giving him head and then, once he was good and hard for me, I climbed on top and rode him. He liked that position the most.” Harper took Kyle’s erection in hand and massaged it softly. Her words had cured her husband’s earlier issues. “You know how you’re generally nice to me, respectful? Well, Seb never really treated me that way and I kind of liked it.”

“Like what.” said Kyle, trying to hold out until Harper finished her story. She ran her thumb along the underside of his penis spreading the slick precum that dripped from the head.

“He told me what to do and what to say. I let him degrade me for his pleasure.” The moment was finally starting to have an effect on Harper. She liked sex with Seb and her body was began to remember how much fun it was. “He made me tell him that I was his slut. He made me say how much I loved his dick. And I always obeyed. Do you know why?”

“Why.” said Kyle, barely able to get the word out. Harper pumped her hand up and down his shaft faster and faster.

“Because I was his slut loved his dick. After our first date when you were working up the courage to ask me out again, he was inside of me, fucking the shit out of me. His good little slut. Until I came on his dick.”

Harper was caught up and went further than she intended. While Kyle’s semen ran down the fingers of her left hand, coating her new wedding ring, the fingers of her right hand swirled around her slick clitoris. She was ignited. On her honeymoon, with her new husband, Harper found her ecstasy by reminiscing about Seb, the man who taught her to love sex.

Kyle was never more aroused and hoped Harper would continue to satisfy his fantasy, but it didn’t happen. Neither of them knew the rules for broaching the subject. When they returned home from the honeymoon, Kyle would occasionally make allusions to his interest, but Harper didn’t seem enthusiastic to revisit it. Eventually, Kyle pushed the matter directly and Harper told him that she didn’t want sex with her husband to be defined by thoughts of her with other men, but, in time, she agreed they could explore his desires on occasion.

Their life became typical of young newlyweds. Between the growing pains of living together for the first time, they enjoyed the sexual freedom of unfettered access to each other. And, when Harper felt especially safe and satisfied in their relationship, she peppered in a little story to tease her husband. She told him about the time her first boyfriend’s birthday coincided with an antibiotic regimen she was on and, because she forgot about the interaction with birth control, she had a pregnancy scare the first time she let someone come in her.  And she told Kyle about a vacation with her second boyfriend and his family in the Hamptons. How the two of them thought they were home alone but, once they were done, she ran into his father in the hallway. It was extra awkward because she was naked and disheveled and just finished a very loud orgasm

All of Harper’s stories excited Kyle, but without realizing why, he favored the ones about Seb. Aside from Kyle, Harper had had sex with Seb more than anyone else and, in spite deliberate ambiguity on Harper’s part, Kyle suspected that she enjoyed the best sex of her life with Seb. To that point, he was right.

The newlyweds gradually adjusted to their new lives together. Most days defined by the enormous hours each of them needed to put into their new careers. Kyle was usually up before dawn and back late. If Harper was still awake when he returned, it was because she was still working. The two of them made do by catching up between her late night zoom calls. Time passed and their sex life was put on the back burner. 

The pivotal conversation came on Memorial Day. With the market closed and his boss on vacation, Kyle had a rare weekday free. Unfortunately, Harper was working overseas. They talked while Kyle ate his lunch at home. It was the middle of the night for Harper, but her sleep schedule was all screwed up. She’d been in Tokyo for three days and had zero interesting experiences and wanted to know what Kyle was going to do with his day off. He confided that he wished she was home and that he was sexually frustrated.

“We haven’t had a lot of time for us.” Harper admitted. 

“I’m not complaining. I know it’s a crazy time at work for you too.” said Kyle.

“I will be home in a few days and things should be quieter for me. We could do something special.”

“What were you thinking?” 

“We could go out, get a nice meal, somewhere with music. And maybe, as night comes to an end, I’ll find a handsome stranger to flirt with.”

Kyle didn’t believe her and pressed the question. She told him it was a firm maybe. It might not happen, but it definitely wasn’t out of the question. As they talked over the hypothetical, Harper worried most about Kyle’s feelings. If she ever did flirt with another man or went too far with his fantasy, she wanted Kyle to know that he could tell her if he got uncomfortable. He only needed to say so.

“Tell me if I need to stop.” said Harper.

 Kyle still found it incredibly unlikely Harper would talk to another man in that way, but he thought constantly about the possibility. After her abortive attempt with the guy walking his dog, Kyle assumed that was probably the closest they’d ever get to going through with it. That was likely for the best. Neither of them could seriously want more…

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