Chaperone

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Let's try there." I headed for the next shop.

SIX

I spent half my life savings in less than an hour. And that was before I bought lunch at a little outdoor eatery called The Rookery. The decor was birds on birds on birds, but the only birds anyone was really interested in were the women shoppers who occasionally landed there.

We entered the patio dining area and I scanned the available tables. Two seemed suitable, one in the sun, the other in the shade, but I couldn't decide which would be better so I lifted an eyebrow toward Helen. She had more practical experience than I did at this.

She looked at the one in the sun and nodded smoothly once.

"What was that all about?" Kelsey started to plop down in a chair but I stopped her by pulling out a different chair and clearing my throat.

"Kel . . ." I wiggled the chair a little.

Kelsey looked at me, then looked at Helen who stood by a different chair and then back to me. With a sigh, she allowed me to seat her. Pulling out the other chair I did the same for Helen.

"It's about advertising." I repeated myself as I sat down. "Think of you being in a spotlight of your own creation. No one else gets inside the circle of light and you always have the spotlight centered on you. Everything you do is based on you staying on stage and in the center instead of letting the spotlight be empty or stolen by someone else."

"I don't understand why that has anything to do with where I sit."

"Look in the window." Helen said quietly. "If you sit where you were going to, you cannot see the reflections in the window and you would have missed it."

"Missed what?"

"Look in the window."

The window reflected the scene of an entire row of men seated at the bar counter who were looking at us. Or, more exactly, the two of them.

"It's about advertising. All you have to do is advertise how beautiful you are and they will watch you. Which is the actual goal here because you're not interested in either catching them or letting them catch you. To do that you have to have feedback as to whether you're doing it right or not." I nodded at the window reflection. "Check out the bartender behind the bar. Not the guys, the bartender."

Kelsey flicked her eyes toward a window where she could see the reflection of the men at the bar. Behind the bar was a woman with a double D sized bust wearing a low cut halter top. She was giving us the evil eye. Kelsey watched for a few more seconds then the corners of her lips curled upward slightly.

"Control yourself." Helen told her as soon as the first traces of the smile appeared. "Gloating is very bad form."

"Mother," her tone was remote as she wiped the smile off her face. "I have absolutely no idea what you're talking about."

"Exactly that." I waved my hand for someone to come take our order. "That attitude is right on the money. You're not shopping, you're advertising. If you came here every day for several weeks and got to know the bartender a little bit, she'd be doing her best trying to get your secrets while still thinking you're a slut because you'd be stealing all her admirers without needing to be half undressed like she is to do it."

Kelsey looked at me then Helen.

"Never tell. Not even your best friend." Helen smoothly turned her head to look down the mall at the same time. "Others will believe that you're a slut because they know they either cannot have you, or cannot compete with you, so they must say bad things about you. Telling them that you're doing it intentionally will only reinforce the image in their mind. Never tell."

I could see the light switch on inside her head.

"Some people who don't know any better will think that anyway even after they know different."

She looked at me.

"Tabitha is not a slut."

Kelsey looked down for a second then back to me.

"But do you think she's pretty?"

"You, are beautiful." I left it at that.

She just looked at me while Helen used the menu to gracefully fan her face with it a few times. Several men who were passing by, turned their heads to look directly at her.

"Advertising." I quietly used a finger to point out the reason behind Helen's use of the menu as a cooling fan. "If you're not getting seen, do something innocuous but which still makes them look at you."

"I don't want them to look at me." She shifted in her chair.

"Dear heart, don't lie." Helen stopped fanning her face. "Especially to yourself."

Once we got back home I let Helen help Kelsey put her new things away. From what I'd seen when I hauled it all upstairs, she was going to need to toss a lot of her old things but I would let Helen handle that. I didn't need to get involved and I certainly didn't want to start a fight over telling my sister to throw out clothes she thought were pretty. Even if they weren't.

Instead I went into my office and turned on the computer. Searching for accessories and necessities I clicked on a few items and used them to reduce my quickly dwindling bank balance even further. I was undecided over a pair of thigh high stockings when the two of them came back downstairs.

"Helen?" I called when I heard their voices.

"Yes, my love?" They both appeared in the office doorway. Both had changed out of their other clothes and were wearing something more comfortable. Kelsey in jeans and a T shirt while mom had her yellow sundress on.

"What do you think?" I gestured at the screen where the stockings were displayed. "Do those actually stay put or do women have to pull them up all the time?"

She came over to perch on my knee again and look at the screen. The stockings were a pastel lavender which would accentuate the deep violet of the dress Kelsey had just worn but I didn't know if thigh high stockings were workable under actual wearing conditions.

"Those are pretty." Kelsey settled on my other knee like she had earlier. She ran the mouse over the screen and zoomed in on the lacy uppers of the stockings.

"If they're tall enough they won't move as long as you don't go jumping off of things." Helen looked at the description.

Seemingly innocently, her hand dropped to caress my inner thigh as she leaned forward toward the computer screen. Heat immediately flooded my groin and Helen froze for a fraction of a moment before continuing as if nothing was going on. If I hadn't been so attuned to her, I'd have totally missed it.

"If they're too short they won't stay up without a garter even if all you do is sit."

Kelsey made a face over Helen mentioning garter belts.

"They are necessary accessories." Helen's caress moved higher on my leg. "Some Males have a fetish for them. There are females who do as well. If that is who you are trying to attract, you must use the bait they prefer."

Kelsey looked at her then down to me to get my reaction to what Helen had just said. Noticing what Helen was doing caused her to shift like she was going to get up but Helen placed one palm flat on my bulging crotch while reaching out to take one of Kelsey's hands in hers. Slowly Helen slid off my lap, drawing Kelsey down with her until they were both on their knees under the desk. Together they unzipped my pants. Two sets of hands worked together to pull my stiffening cock out until one set of lips slowly slid over the head while a hand started to pump up and down my shaft.

They changed lips and hands frequently. I spread my thighs to give them as much room as possible but my pants were getting in the way. It wasn't long before they were undoing my belt and making me lift my hips so they could yank my pants down around my ankles.

"Stockings. Sir." Helen reminded me what I'd been doing once I was able to sit back down in the chair again.

I reached for the mouse and tried not to groan as hot lips once again engulfed me. I throbbed as they swapped once more and new lips starting working up and down on my cock My hands shook so much from tension that I had trouble keeping the cursor where I wanted it while I futilely clicked everywhere except where I needed to.

"I'm going to come." I warned them as I throbbed again and my balls tightened. They just swapped lips and hands without changing tempo.

"Uhh." I thrust my hips forward and started to come. I didn't look to see who was getting a mouthful, I'd been serviced by both of them, individually and together like this, many times and right now I just wanted to come. Seeing them both being so desirable all morning had made me horny enough that I just needed to come. I'd even thought about masturbating to release some of the need but hadn't because it wouldn't have been fair to Helen if she'd wanted me later.

Somewhere in the middle of my orgasm, they swapped lips and hands again so that I finished coming in a different mouth than the one I started in. When I was done throbbing, a pair of hands squeezed my shaft to get the last few drops before letting me slide out of her mouth.

They sat back on their heels and looked at each other. Both of them licked their lips. Kelsey hesitated for a moment then leaned over and kissed Helen on the mouth.

"I only have three stars." Helen reminded her daughter when the kiss ended.

Kelsey looked down.

"I know. It's just . . ."

"Just what?"

"I felt so happy right then that I couldn't help myself."

"Dear heart," a finger lifted her chin until Kelsey's eyes met her mother's. "Never be ashamed of your need. If your need is for another woman, then satisfy it."

"I'm not lesbian." Kelsey shook her head. "It's just . . ."

We waited for her to finish.

"You looked really wonderful and I just wanted to kiss you all of a sudden." She climbed out from under the desk and up to her feet.

Helen got to her feet as well. Stepping close she slid one hand behind Kelsey's back on her shoulders. Another step closer and their lips touched for a brief moment then parted.

"I love you Kelsey Whitcomb." Helen rested her forehead against Kelsey's. "I have loved you ever since the moment you were born and I will love you until the day I die. You are the most beautiful thing I will ever see."

Kelsey blushed and looked down before noticing me sitting the chair with my pants still down around my ankles. She made a face in my direction..

"Eww."

Helen glanced at me and rolled her eyes mockingly.

"Males! It's all they ever think about."

They both snorted in good humor and left the room together. I stood and pulled up my pants before adding the stockings to my cart. Overnight shipping was taking a huge bite out of my savings account on top of the hit it'd already taken today.

SEVEN

I handed the job application to Kelsey who took it and looked at me.

"Fill it out, borrow mom's car, and give it to Ian tomorrow. He's going to have to hire someone soon so do it tomorrow. Putting it off will mean you'll miss your opportunity window." I sat down on the couch. "Wear the charcoal slacks and gray blouse. Hair up instead of being braided. Think librarian."

"Why are you telling me what to wear?"

"Because you still need to learn how to advertise yourself."

"For dropping off a job application? Are you nuts? Do you know how much time I'm going to have to spend to get ready so I can wear what you want me to wear? Just to drop off a job application?"

"You're not just dropping off the application. You're advertising that you're the best possible candidate without saying a single word about it." I gestured at her with both hands. "A picture is worth a thousand words. Be the picture. Be Ian's Mona Lisa or his Venus de Milo. He won't be able to help himself, he'll hire you because he won't remember anyone else who applied."

I leaned forward and put my elbows on my thighs.

"If you do it right, then however much time it took to get ready is time well spent."

"I have a dinner invitation for tomorrow evening." Helen reminded me of her schedule.

I nodded that I remembered.

"Kelsey will have to do it while I'm in class or already at work." I explained my reasoning. "She shouldn't take the bus unless she wants to be sexually assaulted and I won't be home until almost the same time you and granddad get back. She and grandmother can have a girls evening out by themselves if they want."

We both looked in my sister's direction.

"If they do, grandmother can help with Kelsey's training."

Kelsey sighed.

"I don't need training."

"Dear heart, you have no idea how much more training you need before you finally learn what you need to know."

I was working in the café again the next day when Kelsey showed up to give her application to Ian. My back was to the door but I knew when she walked in. Everyone went quiet and several people turned around to just stare. Looking toward the front counter, I saw her stroll in and stop. Ian glanced over, did a double take, and then magically transported himself to where she was standing.

I watched as they talked for a few minutes then Kelsey turned and strolled her way toward the exit. She glanced at me then switched her eyes away to look at something behind me. Wondering what it was, I turned to see what she was looking at. The two redheads who'd been there the other day were sitting open mouthed as they stared at her.

She smiled broadly at them for a long moment and then walked out the door.

"Wow." Ian showed up at my shoulder.

I just went back to wiping down the table I'd been leaning over when Kelsey arrived.

"Did you see that?" He wanted to know.

I nodded casually and moved to the next table.

"Kelsey's always been kind of pretty."

"You know her?" Ian's voice dropped.

I nodded again and moved to the next table.

"She's my sister."

"That was your sister?" Ian gave me the once over then looked at the paperwork he had in his hand. "Your sister?"

I nodded and went to the next table. The two redheads were watching and listening to us.

"Your sister looks like that and wants to work here?"

I straightened and dropped my voice like I was trying to be hush-hush about what I was going to say.

"She was in a relationship but it went bad and she had to move back home. Now she needs a job so we thought she could apply here because I already work here." I moved to the last table in the row that I'd been wiping down. "If you don't want to hire her because we're related then don't. She's smart so she'll probably find a job somewhere fairly quickly."

"Your sister." Ian repeated himself and looked toward the door.

"That's what my mom keeps telling me." I spoke in my normal tones then looked at the two redheads before pointing at their bottles and paper plates. "If you're done, I can take care of those for you."

As I waited for their answer, Ian wandered off toward his office in the rear of the store mumbling to himself and turning the application pages over and then back again.

"Was she really your sister?" The younger of the two redheads asked.

"Giz!" The older one interrupted with a hiss. "You know better than to talk to strange men."

I nodded agreement with that. It was a good policy for most women even if, as my mother had explained once, it complicated things for them later in life. The girl looked at the older redhead and then back to me.

"My name's Giselle but everybody calls me Giz. You work here, I've seen you before."

"You're right, I do work here. I'm Kevin."

"Was that really your sister? She doesn't look like you."

"Yes. Her name is Kelsey."

Giz looked at the door then back to me.

"You done with those?" I asked again about the empty bottles and plates.

"Let's go Giz." The older redhead stood up abruptly. Gathering her things she started for the exit without waiting for her sister.

Giz stood and then looked at me.

"Lucy's my sister. She thinks she's the boss of me. Your sister is pretty."

"GIZ!" The older redhead stopped at the door. People turned to look at her at the shout.

"Bye Kevin." Giz grabbed her bag off the back of her chair and hustled toward her impatiently waiting minder.

I had a package on the doorstep when I got home, Kelsey's things had apparently arrived while everyone else was out. Opening the box I checked the contents. There were two pairs of the lavender stockings and four other pairs of hosiery that were so alike in color and style that they could have been the same if not for the different brand labels.

Apparently I'd ordered similar items because I hadn't been keeping track of what I'd already bought. Which was mostly likely caused by the hands and lips of the two women who interrupted me to make sure I was happy with them.

Sitting at the computer I began creating a spreadsheet starting with the clothes from yesterday's shopping trip and ending with the smaller necessities like socks and stockings. I could update the list as things changed but I now knew what she had and could easily get more if something got damaged or torn. As I finished the list, I realized that having multiples of things like hosiery was good because stockings and pantyhose were easily damaged and in most cases if they were part of a matched outfit that meant the entire outfit was unwearable until replacements arrived. So the multiple necessities buying spree actually turned out to be a good thing.

"Kevin, we're home." Kelsey's voice came from the foyer as soon as the front door opened.

"In here." I called. Both Kelsey and grandmother came into the office. Kelsey was still wearing the charcoal and gray from earlier and grandmother was dressed in a very conservative peach and cream.

"What are you doing?" Kelsey came in and perched on my lap again. I gestured to the screen.

"It's a file of everything you have that I just bought for you. I screwed up somehow and started buying the same things over and over so I needed a better way to keep track of your new clothes and stuff instead of trying to keep it all in my head. It's just too confusing."

"Kevin?"

"Yes grandmother?"

"Did you choose that for Kelsey?" Grandmother gestured at Kelsey who looked back in surprise. Apparently Kel hadn't mentioned anything about how she'd gotten her new clothes. Probably because she hadn't wanted to get into the how's and why's behind it.

"Mom helped. Well, Helen actually, but I found it."

"You picked it out. Yourself? Not Helen or Kelsey?"

I nodded.

"It's not that hard. Once you told me how it all worked, I realized how easy it actually is."

Grandmother looked at Kelsey then back to me.

"Kevin."

"Yes?" I saved the file and stood up.

"Doing that." She pointed at Kelsey again. "Is not easy."

"Sure it is." I looked at Kelsey for confirmation. "It took us, what, an hour?"

She nodded. I looked back at grandmother and lifted my hands.

"See, easy."

Grandmother swapped looks between us.

"It took you an hour to put that outfit together?"

"Actually, it took that long because we ended up looking until I found five new things for Kelsey to wear. Why?"

"Five? Just like that? In an hour for all of them, or an hour for each one separately?"

"Well, two are dresses so that made it faster because I didn't have to coordinate pants and tops, but it took about an hour to find all of them, although I did spend almost another hour ordering things like pantyhose and stockings and stuff like that online. It shouldn't have taken that long but I got distracted." I caught the flash from Kelsey's grin out of the corner of my eye when I said that. "Why?"

Grandmother raised her eyes like she was praying for strength.

"Grandmother?"

"Kevin, most women I know, including me, take days to find just one outfit to wear. And that's if we're lucky!"

I looked at her then Kelsey and back to her. I didn't know what to say, it wasn't that hard.

123456...9