Changing Times
Copyright© 2026 by dawg997
Chapter 8: DJ the Manager and Kit the Cheerleader
Erotica Sex Story: Chapter 8: DJ the Manager and Kit the Cheerleader - Lennie and Samantha continue their unique relationship, along with the other girls in the story. But nothing stays the same, and things are changing. Does Samantha remain loyal? Can Lennie, worth only a fraction of those other men, handle his emotions about his girlfriend's many billionaire suitors, many of them in love with her?
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual Romantic BiSexual Heterosexual Fiction High Fantasy Gang Bang Group Sex Orgy Polygamy/Polyamory Swinging Black Male White Female Anal Sex Cream Pie Double Penetration Enema Exhibitionism Facial Oral Sex Voyeurism Prostitution
Lennie was alone in the early afternoon, enjoying more nonsense that people were posting on X, his favorite social media site. His cell phone, lying next to him, started ringing. He looked and saw Dorothy Jean’s smiling face on it and picked it up.
“So, Lennie, I’m just checking in with you. How have your encounters with the housewives been going? You appear to be on schedule perfectly. I have to ask you, what did you think of Alexis?” DJ had long ago given up on Lennie typing in his own comments on any sessions regarding who he was with, even though she had shown him how to do it if he wanted.
Lennie smiled to himself, knowing that DJ was in her office on the first floor. She seemed to always be buried in her computer, formerly his computer, talking on the phone, watching the SES app, and attending to company business.
“You know, DJ, you could walk upstairs and ask me in person,” Lennie snickered.
“But Lennie, I may miss a call from a client, and that would cost thousands,” she pleaded. “I care about my job. Besides, I have the same great view that you do of Puget Sound, so it’s not like I’m holed up in the basement. I love my job, and I also enjoy sitting in my own office. I feel like I’m in control.”
“How busy can you be, DJ? A phone call here, a tap of the app there to enter a date and a sentence—it can’t take much time away from your day.”
Lennie couldn’t see it, but DJ had a hurt look on her face. Obviously, Lennie didn’t realize the importance of her job to the success of SES. Lennie needed a lesson in how complicated her job was.
DJ went from feeling hurt to fuming mad. “Lennie,” she growled, “there are eleven housewives and your six girls in the stable. Right now, two of the housewives are on their periods and out of action, and two more are a day or two away from theirs, so they aren’t feeling in the mood right now to be with a man. So instead of eleven girls, I have seven to work with to fill the date requests.”
Oh man, did I just step in it or what? He gulped.
“And your girls have the right to control their own schedules. Taylor is in Cabo with God knows who, Kaylani is in Hawaii with the Victor Twins, Sam is with Jackson in New York—no, wait, they left last night, and they are in Ibiza, Spain—and Maria is in Vegas for another two days and then is flying out to be with Sam and Jackson for a week on his yacht. Have you seen a picture of how big that damned thing is? Anyway, Lori wanted to do a limited schedule to get back in the swing of things after being with her now-departed sugar daddy for so long, so that leaves only Fiona for me to utilize in the line-up. I have every girl with at least two dates each day for the next three days, and I still have five more good clients who want some love tomorrow and the next day. I have to convince some of the housewives to take a third date, which is completely up to them. Most of them have been working two or three date nights for months now, covering for your girls when you all were partying and carrying on last summer, and believe me, I hear the complaints.”
“Sorry, DJ, I never really thought about the ins and outs of your job.”
She kept going, her anger still strong. “And for every date, I have to do a pre-date call to ensure they have the details correct and a post-date call to make sure everything went right, and when they are coming home. Oh, and let’s not forget the client calls. The clients will call in at any time, day or night. Sometimes they wake me up from a deep sleep, and I have to sound like I’m awake and alert. I take every one of them and have to keep them happy with an alternate girl when the one they requested isn’t available. Additionally, if it’s a new client or one we haven’t seen in a while, I’ll need to coordinate with Rick for a background check or address any other security concerns that may arise.”
How do I end this without her tearing my head off? He pondered.
“We aren’t simply an escort service, Lennie, where one warm body can be replaced by another warm body. Although there are numerous advantages to offering GFE, one drawback is that clients become attached to a specific girl, and trying to steer them to another, especially at the last minute, is very taxing. I am constantly selling a client his second or third choice, and believe me, keeping them happy takes a lot of cajoling and manipulating.”
Lennie could sense the hostility in her voice, loud and clear. He realized he really stepped in it this time.
“Lennie, I may not be a rainmaker around here, selling my pussy and my people skills to get paid fantastic money, but without my organizational skills and attention to every little detail, SES would lose a lot of dates, and hell, even an incident could happen where one of the girls got hurt, or even worse,” she declared. “Give me some damned credit, Lennie. I think I’ve proven that I’m a valuable part of the company, and dammit, getting slighted like this is hurtful.”
“I had no idea how complicated your job is, Dorothy Jean.” He used her full name to break her sour attitude and to show her respect for her important position. “Again, I’m sorry. What you do is incredibly important. I was just saying that I wanted to see your smiling face in person.”
Lennie realized that she was no-nonsense and didn’t want to rock the boat. “All I was pointing out was that you have a headphone speaker and Bluetooth, so you could do both at once,” Lennie softly said.
DJ paused for a few seconds to replay the last few minutes in her mind, and the tension on her face receded. “Yeah, you’re correct. I’ll do that next time.”
Her attitude immediately went back to her regular, pleasant self. So, how was Alexis?” Lennie was amazed at how quickly her attitude returned to normal, and also quite thankful.
“DJ, the experience with Alexis was amazing. She is certainly her own person, but she also reminds me of a young Cindy. Not just in her appearance, but also in the way she carries herself and how she interacts with me. And oh, yeah, she reminds me of an alley cat in heat. Good lord, she is a sex machine!”
DJ chuckled. “Yeah, I figured you would say something like that. Did she talk about her personal life as well?”
“You mean her husband, Tommy? She did, indeed. She also has two children. I guess it takes all kinds of people to make the world go ‘round.”
“So true, Lennie, so true. Anyway, I wanted to make sure you are aware of your next housewife appointment with Kit.”
He picked up his phone and tapped the app. Another tap, and he was looking at the schedule she had put together. “It says here that the appointment is for 7 o’clock tonight, correct? Anything I should know that isn’t in the app?”
“Maybe, when she starts telling you about her past, remember that it is now behind her and she is emotionally stronger than ever.”
That was unexpected, he thought. “Tell me more.”
“No need to hear it from me, Lennie. She can tell her own story better than I can. She’s been married for only a year and a half, and her husband is fine with her professional activities. She started with SES only about a month before you met Cindy.”
“You’ve piqued my interest, DJ, so I’m going to hang up and go watch her video.”
DJ smiled to herself. “Just doing my job, Lennie.”
Late in the afternoon, he got into his SUV and drove up to Cindy’s condo, nearly an hour away due to the late afternoon Seattle-area traffic, which, as usual, was absurd for a weekday. He entered her condo by tapping the security codes, then went into her office and logged onto her computer, which had a large, high-definition screen. Tapping the app, he found Kit’s name and tapped the video icon.
A beautiful young woman with long, black hair below her shoulders was looking intently into the camera. Her skin was olive, and combined with the black hair, he immediately thought she was of Italian descent. Her brown eyes were easy to get lost in, as was her warm smile. She wasn’t as tall as the other girls, even a bit shorter than DJ or Fiona. She was also noticeably younger than any other housewife he had met.
“Hello, and thank you. I’m so happy your friend or acquaintance has introduced me to you. If you want the youngest girl in Samantha’s Escort Service stable, here I am! But don’t worry, the other girls have taught me how to offer exactly what you’re looking for. After all, SES clients are looking for only the best experiences, and I aim to deliver.” Her smile was a warm and wide grin.
It was obvious to Lennie that this woman was indeed the youngest of his group. Her voice and demeanor were perky and upbeat like that of a younger woman, but she remained stylish and seductive at the same time. What caught him a bit off guard was her deeply southern accent. Before she spoke, she reminded him of a woman who grew up in an Italian neighborhood, like Arthur Avenue in the Bronx, New York City. How wrong initial impressions can be, he thought.
“I’m Katherine, but everyone except my mother calls me Kit. If you have any questions, yes, I am the youngest woman here at Samantha’s Escort Service. I turned 23 just last August.”
Lennie thought to himself that it was October, so her latest birthday was fairly recent. She seemed a bit shorter than most of the other housewives, maybe 5 feet and 4 or 5 inches. She was certainly shorter than any of the girls living with him, but also incredibly sexy in the way she talked, as her eyes conveyed a sultry tone. She was wearing a body-hugging dress that showed off her curves with ease. Her body was curvy and perfectly proportioned, her C-cup breasts perfectly projected. Another thought hit him that seemed out of sync.
“Yes, I’m a housewife like all of us at Sam’s, except for the original girls, of course. I’m the newest, having only been married for a year and a half. If you ever wanted to be with a college cheerleader at a major university conference, that’s me! If you are a big college football fan, you’ve seen me for sure when my team was on national television. I was one of the girls they would toss high in the air and then land in the arms of strong men.” Her huge smile and cute dimples warmed anyone watching her video, including Lennie. “And I love the arms of a strong man.” Lennie smiled at the comment. What a sexy hook, he thought.
“I’m firm and tight everywhere, so why not schedule me and find out? I’m going out on a limb saying that you will enjoy what you see. I’ll be waiting!” She flashed, then held her million-watt smile as the video ended.
Lennie had thought about their vast difference in ages, nearly 45 years. Suddenly, he felt old. Heck, if he had gotten married right out of college instead of at 40, she could have been a friend of a granddaughter. Then, he realized this woman was a sexual pro, just like all of the other girls in his stable.
It was 7 p.m., and the knock on the door came right on time. Lennie opened the door to see this compact Italian heritage beauty. She walked into the room, pulled him down to her while standing on her toes, giving Lennie a deep hug and a slow, passionate kiss. She was wearing a form-fitting dress that fell just below her thighs, fitting her tight, young body perfectly. Lennie didn’t know why, but he was taken a bit off guard at the warmth and passion of her embrace. The way she expressed herself made her seem so young.
“Hello, Lennie,” she said with an obvious southern accent. “I’m so happy to finally meet you.”
“You said your name is Katherine, but everyone calls you Kit. Now that makes sense as a nickname, but I thought that one of Sam’s rules was that to protect yourself, you had to use a stage name, right?”
She was caught off guard by his comment, but thought for a second and realized it was a reasonable one.
“Yeah, that’s true, but after discussing it with Sam, we agreed that using Kit may actually be an advantage. Let me tell you about my background, and I think you will understand.”
Lennie nodded, signaling her to continue.
“When I first started working for Sam, I had been led to believe that I would be seeing a few clients a week, maybe three or four, and instead have been dating at least seven or eight men a week, sometimes a dozen or more. What I was led to believe was a part-time job had quickly turned into a full-time one in just a few weeks. I asked my manager, Fiona, about my increased schedule with clients, and she said it was all because of you.”
Lennie was immediately puzzled, and his face showed it. “Me? What do you mean? Honestly, other than meeting you months ago at the company meeting, I wasn’t aware of how our paths crossed.”
“Oh no, Lennie, no complaints, but a month after I started is when you and Samantha started going out together. Your arrival on the scene has meant all of your girls have turned over many of their clients to us wives. Fiona mentioned it more than once. She said she had no idea what the future would bring because of you and Samantha. I am also the youngest girl by four years, so many of our clients want to have their shot with me, being so young and all. Many guys, both young and old, enjoy being with a really young girl. I’ve been working hard. Which, by the way, doesn’t bother me, because I wanted to have many different sexual experiences as well as earn as much money as quickly as I can, so it has worked out well.”
Lennie’s mind recalled all of the events he had shared with the girls living with him. A few months ago, there were days at a time when they would all stay home and have wild sexual experiences with him, parade naked around the house trying to sexually tease him, or go to a big concert with a night of passionate group sex afterwards. It wasn’t all parties and good times, either, that took his girls away from servicing clients. The time when Cindy was kidnapped, the fiasco that Fiona got herself into by being arrested and held in a Mexican jail for a month, and other events completely skewed the normal way of things, as his girls had quit escorting completely during those times. The ten, now eleven, housewives had to pick up the slack, some doubling or even tripling their appointments. Kit was one of those.
“The sex part wasn’t any problem because of my past. My husband has given me the freedom to adjust to my new profession in any way I see fit. But being so busy has generated some communication problems. We haven’t even been married for two years, and in the last six months, he has told me he misses me. That makes me sad.”
“Nobody wants to put a strain on your marriage, Kit. Tell me how we can help you make it better,” Lennie answered, a bit of concern in his voice.
“I suppose it would be best to simply hear my story, Lennie. You see, I attended a major university in the Southeast Conference, a sports powerhouse, particularly in football, but also in all other major sports. Last year’s men’s basketball winner was from the SEC, as was the national champion baseball team. Five of the last ten national football titles were won by SEC teams. I was a cheerleader for three years. It was a lot of fun in the beginning: traveling, meeting so many new people, and, of course, meeting the players. You see, my folks immigrated from Italy a few years after I was born, and as my father was a physicist, he worked on rocket and space technology. We lived in North Carolina and later in Huntsville, Alabama, as both areas have major high-technology centers. I attended a public school, and even though both my parents had heavy Italian accents, my speech patterns mimicked those of my friends, all southern girls. So that explains my southern accent.”
“I think it’s beautiful and warm, just like you, Kit, although it is a bit unusual. It does fit you well and is certainly sunny and pleasant.”
“Thanks, Lennie. So what only Fiona, Sam, and my husband know about me is why the sex part of this job isn’t a problem for me. My issue is that I lack confidence in dealing with situations and with others. I have a real problem trusting people. Fiona and Sam have helped me a lot with it, and my husband says he is more appreciative every day.”
Lennie was confused. He waited for her to continue.
“I wasn’t sociable growing up, nor when I got into my university on a scholarship. After making new friends as a freshman, I tried out for a cheerleader spot as a sophomore and was selected for the varsity squad. I had no idea how my life would be altered. My entire life changed: instead of being a shy wallflower, I was now involved in all kinds of social as well as school activities, including cheerleading. I became the girlfriend of the starting quarterback, which garnered me a lot of publicity by being at his side. You see, in the Southeast Conference, being the starting quarterback is a big deal. I immediately became a celebrity of sorts.”
A frown started to form on her face. Lennie could tell she was about to release thoughts deep inside her.
“I was innocent and thought what anyone told me was truthful, and there was no underlying meaning to what I was told, nor was there any reason for people not to tell me the truth. During my sophomore year, I fell deeply in love with him. The following year, he moved off campus into a large house with six other men—all but one played football. After football season, he took advantage of my naivety. He led me to believe that it was expected for the girlfriend of the quarterback to have sex with his friends. I knew it wasn’t right, but I trusted him.”
Lennie had a disapproving look on his face. “No, that’s not right. So he took advantage of your innocent view of the world and his celebrity as an SEC quarterback?” Lennie grimaced at her words.
“Yeah, pretty much,” she said. Relating her memories made her sad and embarrassed. His face turned angry-red, obviously still emotionally affected by what she was telling him. “I hadn’t thought about it in quite a while, but that’s what it was, and I didn’t have the knowledge to interact with people to stop it from happening.”
She looked down at the floor, unable to meet Lennie’s look. All of those horrible memories were coming back. Her look became dourer until she started crying, unable to hold back. Lennie pulled her into his chest, and the waterworks began.
“There, there, Katherine,” he offered, using her real name in an attempt to calm her down.
“Let it out, sweetie. Cry all you want to. I’m here for you. You don’t cry because you are weak. You cry because you are alive and aware. Something is telling you that things are not right for you, but you don’t know where it is wrong. It bothers you, and you react. Your subconscious is strong enough to know, and the crying is its way of telling you what you already know. Trust your gut, trust your hunch. It’s part of what makes you the special person you are.”
The crying slowed to an occasional whimper, and she finally continued.
“Thanks, Lennie. What Fiona says about you is true. You truly care for us girls. Anyway, at first, it was only one boy, a wide receiver who got drafted and is now a pro, and then it was all of the other boys living with him. Well, except for one. That guy didn’t play sports but was a brainiac who was as shy as I was. That was the only reason he was allowed to live there. He helped them with their homework. In fact, they often copied off of his work and turned it in as their own. He saw how they got me to have sex with all of the players and tried to intervene, but they ignored him. He couldn’t object much, as he didn’t even pay rent and was from a poor family. His scholarship paid for his tuition, but not books or housing or living expenses.”
“It sounds like he was the only guy that respected you,” Lennie said. “Sex can be fun, but intimidating a woman to force her to put out is simply wrong. Whatever happened to that guy?”
“That guy was Mason. He is my husband.”
Lennie was now more confused.
“You see, he saw what my boyfriend was doing and objected. When the pushback occurred, he was ignored, but they didn’t give him any grief. You see, he had helped them with their classes, sometimes even doing their papers, and without his help, none of them would have graduated. He felt bad watching me fall into my sluthood, and we began to really get to know each other. After the sex was over, he would be alone with me and console me. We were both taken advantage of, but he was living rent-free in their house because their scholarships and NIL money made his portion of rent and expenses that they covered meaningless.”
“NIL, you mean Name, Image, and Likeness, right?” I’ve heard that some bigger schools offer huge payouts, often in the millions. It has certainly changed since I went to school many years ago. In my day, a player couldn’t even accept a fruit basket or a restaurant meal without getting suspended. Now, some get seven figures a year. It’s out of control.”
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