Chaperone

Copyright 2020 by HisArpy. All Rights reserved.

The events and characters depicted in this work of fiction are derived solely from the author's imagination. Any similarity to any real persons, places, or events is purely coincidental.

Tags: Loving wives, Taboo, Incest, Family, Brother, Sister, Mother, Son

This story is 31,094 words long. Please don't forget to rate the story when you're done reading.

ONE

"Mmmmmmm . . ."

Kelsey hummed to herself as I ran my fingertips down her spine while she rested on top of me with her face tucked into my neck and shoulder. Reversing course, I moved my fingers lightly upward on her back making her lift her head and look down at me with dreamy eyes.

"Keep this up conquest boy and I'll never go back to sleeping in my own bed."

"Like you've been in it lately anyway?" I joked at her.

Whether we were just sleeping or not, she'd been in my bed almost every night since she and mom had talked after Kelsey had figured out what was going on. Even when I was sleeping with Helen or Marjory in theirs, she kept my bed warm while I was away. She said she liked the way my bed smelled more than her own. What that really meant is that my scent on my bed was more comforting than her own bed which didn't smell like me.

"It's not my fault." She wiggled her hips a little bit. "Blame mom."

"Why mom?"

"She and grandmother taught you too well." She gave me another hip wiggle. "You're addictive."

"Right now I'm limp." I pulled her down and kissed her.

"Mmmmmm . . ." Kelsey hummed to herself again and licked her lips.

"Off." I pushed gently with both hands. "I need to get up and go to work.

She gave me a little moue but lifted herself, frowning even more as I slipped out of her. It was her usual complaint after we made love. No matter how many orgasms she had, she wanted more. And then another one just to top them all off. And one for dessert. And then one to keep her happy until the next time we could get together and satisfy what she called her needs.

Between my sister, my mom, and my grandmother, my free time whenever I wasn't in class or at work was often not my own. Not that I was complaining, having sex with three beautiful women on a regular basis was a man's fantasy come to life. The fact that they all knew, and sometimes joined in with each other for two, or even three, on one, made it all the sweeter, if tiring on occasion.

As her weight shifted to one side I rolled onto my elbow. Kelsey stretched out next to me and closed her eyes while I ran my fingers through her hair and behind her ear to cup her jaw in my palm.

"I love you Kelsey."

"Liar." She snuggled deeper into me. "I heard you say the same thing to mom just yesterday. And I bet you even said it to grandmother the last time she slept with you."

"Well, maybe I did say it then, but I really mean it this time; I love you." I kissed her once more and then rolled out of the bed and to my feet. She reached for me with both hands.

"Noooo . . ."

"Yes." I skipped away out of reach. "I have to go to work or I'll get fired."

Crossing her arms she grumped at me.

"Be nice." I bent and gave her a quick kiss on her lips then stepped back out of range again before she could grab me and pull me down on top of her. I wasn't stupid, it had only taken eight or nine times of me getting tumbled back into the bed for another round of pleasuring her before I learned about that maneuver.

Kelsey, mom and grandmother must have talked to each other about it because they all seemed to have the same trick up their sleeves. So that was eight or nine times, each, before I figured it out. Of course the reward for getting tumbled was pretty fantastic so that may have had something to do with why I seemed to be a slow learner. I also somehow seemed to backslide into forgetfulness on occasion too.

"Kev . . ." Kelsey called as I headed toward the bedroom door and ultimately the bathroom down the hall.

I stopped and looked back. She was holding up her arms in a big V.

"I love you."

Reversing course I went back and kissed her one more time.

"Liar." I blocked her quick grab attempt and stepped away again.

"Can't blame a girl for trying." She grinned up at me. "It's your fault anyway."

"I thought you just said it was mom's fault."

"Nope. Your fault."

"How is it my fault?"

"Because it is."

I rolled my eyes at that and left. I really did need to clean up and get to work.

Helen and Kelsey were both wearing bathrobes and sitting at the table when I came down after showering and getting dressed. They had their heads together over one of my mom's ubiquitous puzzle books, a half eaten donut on a plate nearby told me that Kelsey hadn't even finished her breakfast before getting engrossed in the puzzle. They were two of a kind in that respect now. Kelsey hadn't been a puzzle fan before she started sleeping with me, but apparently the puzzles satisfied a need she hadn't known she had.

"My love?" Mom looked up at me when I appeared.

I kissed her cheek and brushed my fingertips gently over the same spot. She closed her eyes and placed her hand over mine to hold me for a long moment.

"Get a room you two." Kelsey rolled her eyes and took another bite of her donut. She looked at the puzzle they were working on together, then took the pencil from mom's hand and wrote something on the page.

"I will think about you all day." I bent and kissed my mother's cheek again.

"Gag. Talk about cheesy pick up lines." Kelsey gave us another eyeroll.

"I will think about you all day too." I kissed her on the top of her head.

"My lips are down here conquest boy." She used a finger to show me where. "More practice equals better aim."

I lifted her finger to my lips, kissed it, then returned it to place it gently against hers. We were downstairs and the window blinds were open where anyone could see us if they happened to be looking toward the house. That meant no kisses on the lips. For either of them. Kelsey knew it too but often pushed the boundary.

"Dear heart," mom addressed Kelsey. "Mind your manners. What would the neighbors think?"

"They'd think Kevin is the world's stingiest brother." She finished her donut and dusted her hands. "I don't know how you put up with him."

"He has his uses." Mom looked at her then up to me with stars in her eyes.

"Yeah, yeah, if you say so." Kelsey went back to the puzzle.

"I have to go." I looked down at my mother one more time then headed for the front door.

Kelsey caught up to me in the foyer. She spun me around and planted one on my lips while pushing me against the wall at the same time as she held my jaw cupped in her palms. Her tongue probed my teeth as I kissed her back while mom ignored us completely.

I was available for her all day under the terms the three of them had worked out when they'd discussed how to sleep with me without overusing me. Basically, she and grandmother each got me for the day I was scheduled into their calendar.

It wasn't a constant swapping around or a rigid schedule. Usually Kelsey was able to sleep with me two or three times each week while grandmother and I only slept together once or twice every couple of weeks. Grandmother had other lovers, plus granddad, because of her membership in the association both she and my mom belonged to. That meant we slept together a lot less than Kelsey and I did because Kelsey didn't have anyone else to sleep with. Eventually she would find another boyfriend and start sleeping with him instead of me, but right then there was only me.

The two of them got me on that limited basis because Helen's needs were primary and she got the majority of my affections. However, both Kelsey and grandmother had needs too and Helen shared me with them on whatever rotation I could keep up with. I wasn't Superman, and there were days when I needed time off because of work and my college classes, but I did my best to keep them all from being disappointed.

Kelsey pulled back after a long moment. Breathing deep she looked up at me as her hands slipped behind the nape of my neck. She had the same sparkles in her eyes Helen had just shown me.

"Thank you sir." She uttered the same words that both Helen and Marjory used after we had sex before she let me go and stepped back. She knew I had to get to work.

"It was my pleasure dear heart." I kissed her lightly for the last time and opened the door.

TWO

"Are you finished with this?" I asked the pair of redheaded girls who were sitting at one of the tables.

I was running the café that was part of the book store today since the guy who was scheduled to do it hadn't shown up for work. It wasn't much of a café, just a self serve coffee machine and some drinks and snacks in a cooler, but customers often sat at the tables to read while they were there. The only rule was that if they sat in the café, they had to order something from the café.

The two girls looked up at me and I gestured to their empty plate and bottles.

"I can take those if you're finished with them."

The older one nodded and went back to the magazine they were browsing through. The younger one looked at me for a second or two longer then dismissed me from consideration as she too went back to the magazine. It was some kind of women's fashion magazine from the bookstore shelf.

"Oh that's pretty." The older one pointed to a picture in the magazine as I picked up their dirty plates and put the empty bottles on them.

I couldn't help myself, I glanced at what she was pointing at; a dress in an advertisement. It actually was pretty. Vibrant red, it would look nice on someone who wasn't a redhead like the pair before me.

I must have done something because the younger girl looked up at me again.

"Ladies." I excused myself and took the dirty dishes away without looking back.

Reaching the trash containers, I chucked everything into the recycle bin. Going around behind the register I grabbed a wet bar towel and started wiping down tables. Without intending to, I glanced up to see the younger redhead looking at me again. As our gazes crossed she dropped her eyes back to the magazine. I kept on wiping tables. By the time I'd wiped down a few more tables, they were gone and the magazine had been abandoned.

I just picked it up and wiped down that table too. I was heading to the counter to put the magazine in the box we kept there so it could be returned to the shelves in the bookstore when Kelsey's voice sounded from behind me.

"Did you miss me?"

"Kel?" I turned around to see my sister standing in the middle of the café. "What are you doing here?"

She held up some registration materials for the college.

"I thought I'd see about going back to school."

"Oh." I dropped the magazine into the box.

"What's that?" She pointed at the box.

It's where we put the books and magazines that people leave behind."

"Like what?" She looked into the box and lifted out the magazine I'd just put inside. "Fashion?"

"A couple of girls were looking at it. They just left and didn't put it back." I moved behind the register as someone came into the café and opened the cooler door.

Kelsey thumbed through the magazine while the customer paid for the bottled drink before sitting down at a table with a book. He uncapped his drink and opened the book while settling in to read.

"Kel?"

"Huh? Oh." She closed the magazine from where she'd been looking at the same dress the two girls had been interested in. It was difficult to miss the ad, it was full page size and the dress was color saturated so it jumped off the paper. Very striking and eye catching. I'd bet the company that made it sold a ton of them just from that ad alone.

She handed the magazine back to me. I dropped it into the box again.

"Can I wait until you're off and go home with you? That way I don't have to take the bus again."

"If you wait in the café, you'll have to buy something. It's a rule here to keep people from using the café as a reading room and preventing people who want to eat from getting seats."

"Oh." She shook her head. "That's ok. I don't really have any extra cash and I don't want you to pay for it. That's not fair."

"Then do yourself a favor." I motioned toward the front register inside the book store. "Go over there and ask for Ian, he's the book store manager. Tell him you want to apply for a job."

"Why?'

I gestured at the café around us.

"George, the guy who usually works the café, didn't show up for work today. Ian said he didn't show yesterday either so he's probably going to get fired. If so, that means that there'll be an opening. Go get an application. That'll let you sit here and fill it out without having to buy anything."

"Oh." She looked around.

"It's pretty cool to work here. Very low key and all you really have to do is be reliable and be on time."

"I don't know anything about books and bookstores."

I shrugged.

"I didn't either when I started but it's not that hard to learn." I pointed at the front counter. "Ian's the dark haired guy. Go ask him for an application. When you ask, tell him you're going to take classes here. That'll put you ahead of someone who is just looking for any old job because it shows you're doing something to better your future."

She looked at me wondering if I was serious. I just used my chin to indicate the front register.

"Go ask. Don't forget to tell him you're taking classes here."

She went. I watched as she walked to the register and spoke to Ian. He reached underneath the counter and handed her some paperwork. Kelsey smiled at him before heading back my way. She saw me watching.

"Jealous?" She teased me as she sat at the same table the two redheads had used.

"I have no idea what you're talking about." I lifted the box of books and magazine and headed for the bookstore.

Kelsey stopped me and snatched the fashion magazine off the top of the pile inside the box.

"Just looking." She told me as she placed it on the table next to her application.

I shook my head at her.

"It's wrong for you."

She looked quizzically at me but I had things to do.

"I'll be back in a bit." I hefted the box in illustration of what I was talking about. "Just sit there and look like you're filling out the application. I have another hour before I'm off."

I'd finished restocking the books and magazines and had returned to the café when she nudged the magazine at me. It was open to the page with the ad on it.

"So why did you say this was wrong for me?"

"The color is fine. It would look really good on someone with a darker complexion like you have." I stopped next to her table. "The cut is the problem."

"I'd look good in it." She countered.

I nodded.

"You would. You're pretty enough and the dress would enhance your looks because the color would catch the eye and make people look at you." I waggled a finger toward the image on the page. "The problem is that it's not cut right for someone like you."

She just looked at me in disbelief. I held up my hands.

"Look, I'm a guy. I watch women. It's second nature for me. I see a lot of women who have no idea that what they're wearing makes them look awful."

"That doesn't make you a fashion expert." She looked at the picture again.

"I'm a guy. I know what I like when it comes to what women are wearing. I just go with that."

I headed toward the table where the book reader had been sitting. He'd left his drink bottle on the table. I tossed it into the recycle bin and grabbed the bar towel to wipe down the table. I caught Kelsey looking down at herself.

"You're pretty." I wiped the table top. "You have a good figure with an exotic appearance and guys like that. You know they do. You just don't wear anything to maximize the way you look. Most women don't."

"That's because stuff like that is expensive." She gestured to the magazine. "And it's not that comfortable. Plus what woman wants every loser in the city drooling over her everywhere she goes?"

"You don't have to wear stuff like that all the time." I picked up the magazine and tossed into the box on the counter. "There are other options that let you look your best while also being comfortable."

"But I could." She looked at the box.

"Vanity much?" I teased her. "I just have to go punch out on the time clock and I'm off. Then we can go home."

THREE

"So who would that dress look best on, me or mom?" Kelsey asked as we were on our way home.

I looked at her.

"Kev? Which of us?"

"Both of you would look good in it." I changed lanes and looked left as we passed by my old apartment building. "Tabitha, on the other hand, would look fantastic in it."

"Tabitha?" Kelsey twisted in the seat to look behind us. "Why?"

I waited until she faced forward again.

"The red works with her coloring and the cut would highlight her body and how she carries herself." I gestured vaguely. "You've seen her, you know what she looks and sounds like. It's almost like she's shy or reserved but still needs people to notice her. The dress would accentuate all of that without changing it into something else. The combination would make her so desirable she'd have Males jumping out of the woodwork wanting to socialize with her."

"You mean sleep with her." Kelsey all but snapped out the words.

"First of all she's pretty far along in her pregnancy right now so she can't be having orgies with the entire crew of every ship that passes her way. Other than that a lot of men wouldn't mind just having her on their arm as eye candy in that dress." I glanced at my sister. "And, for your information, I'm not sleeping with Tabitha; I haven't ever slept with Tabitha; I have no plans or intention of sleeping with Tabitha either. I like her as a person, but she's not my type."

"And what exactly is your type?"

I grinned at her for falling into my trap.

"I prefer the type who are easy sexual conquests."

I got an eyeroll for it but I could see her reflection in the glass as she smiled out the window. It wasn't long after that before she sat up straighter.

"Mom does the same thing Tabitha does in the association. You know that." I prodded her over her animosity toward Wade's girlfriend. She was being totally unreasonable about it, and had been from the day she first saw Tabitha. "So whatever you want to think Tabitha is, then by your reasoning mom's the same thing."

She stiffened and didn't answer.

"Kel?"

"Mom's not a prostitute."

"You're right, she isn't." I turned off the boulevard into our housing tract. "Tabitha isn't either."

"She . . ."

"She is Wade's girlfriend. Nothing more than that. You know it." I cut her off about whatever she was going to say. "You do. You just don't like the fact that Wade has someone to love and be with now because it upsets your view of the world."

Kelsey crossed her arms and didn't say anything.

"I think that if you actually sat down and talked with her, you'd like her." I pulled into the driveway and shut off the engine. "Maybe you wouldn't be best friends but I think you'd learn that she's a really nice person."

"I don't want to talk about it anymore." Kelsey got out of the car and went into the house without waiting for me. She also left her application and school paperwork behind. Collecting all of it into one bundle, I followed her inside.

She was steaming to herself on the couch when I got inside. Stopping in the foyer I wordlessly held out the paperwork to her. Kelsey turned her head away.

"Kelsey?" Mom asked from her place in her favorite chair. "What's the matter?"

"Nothing."

Mom looked at me. I held up the sheaf of papers.

"Kelsey came by the bookstore after going to the admissions office at school."

"And?"

There was a magazine with an ad in it about a dress that she likes."