Chaperone

"Do you think you can do that again?"

"I'm broke. Buying Kelsey's clothes took almost everything I had in savings."

Grandmother waved that away as unimportant.

"Can you do it again or not?"

I looked at Kelsey and considered. She really did need another pair of slacks and a blouse if she got the job at the bookstore. I'd get paid before she needed them so I could probably get them for her after that.

"Not for Kelsey, for someone else." Grandmother brought my attention back to her.

"Someone else?"

"Kevin, can you do that," she waved at Kelsey again. "For someone besides Kelsey?"

"I don't know. Maybe. If I met them. Why?"

That got another one of those Lord, please give me strength looks heavenward.

"Kevin, can you do it for me?"

I looked at my grandmother and considered for a moment before I turned toward the computer and opened my browser.

"Slacks or a dress?" I asked as the computer connected online.

"Either." Grandmother's tone was bland and it made me look at her. She pointed at the computer in a clear command to get busy.

"For work or play?" I ignored her command. I needed more information.

"Either." She made another finger point at the computer.

I opened my mouth to ask formal or informal then thought better of it. She'd just tell me the same thing. Grandmother didn't care what I found, she just wanted me to find it.

Twenty minutes later I had an array of things I thought she'd look good in. Gabardine and lightweight wool slacks, blouses in both silk and cotton, three or four dresses in various fabrics, styles, and colors. Finished, I turned the monitor around far enough that she could see it.

"All of these mesh with your skin tones, your general facial and body features, and your hair color as well as the impression you want to give when you're on your visual stage." I clicked on one of the items. "I made some selections for both business and casual so that all the bases would be covered because I didn't know what you wanted."

"Visual stage?"

"That's what I call it. I don't know if there's an actual term but it's what you meant when you said to own the look."

Grandmother just looked at me like I was speaking a foreign language. I lifted my hands. She's the one who told me about it, I'd just put it together with what I thought she'd look good in.

"What about sizes?" She turned back to the screen after giving me a longish stare.

I shrugged again.

"These are all in size six so they should fit you. If they don't, you can send them back for a different size. Most of them have the next half size up or down available."

Kelsey opened her mouth but grandmother beat her to it.

"How did you know my size?"

"I guessed." I shrugged one shoulder as I said it. "You're not a four and you're too slender to be a size eight."

They both looked at me.

"Marjory." I leaned back in my chair and folded my hands at my waist. "I've seen you without any clothes on. You think a man won't remember what a woman looks like when she's naked? Especially when she's as beautiful as you are?"

She gave me a stunned look for a moment then visibly shook herself and went back to asking questions about what was on the computer screen.

"What about accessories?"

I clicked a couple more items to enlarge them on the screen.

"Shoes?"

Another click with the mouse and some really pretty medium-to-high heeled pumps appeared on the screen.

"These are Italian leather and are available in black and ivory so they'll work with both of the dresses as well as the heathered wool slacks." Another click and the screen filled with an image of some flats with little gold plated bows as accents. "These color match with the dark rose slacks and the pastel rose silk blouse. A thin gold box-style chain worn on the outside of the blouse would tie the shoes to the rest of it. I didn't look but I'm pretty sure you could find nail polish to match or come really close. If not, you could always go with a clear polish."

NINE

Grandmother looked at the screen, then to me, then back to the screen.

"Twenty minutes." She whispered the two words and then repeated herself. "It only took twenty minutes."

"Grandmother?"

The front door opened before she could reply. Less than ten seconds later both granddad and Helen were in the office with the rest of us.

"My heart." I stood up immediately and opened my arms.

Helen made a beeline straight to me. She smelled like sex and looked slightly mussed. Those two things caused my cock to start oozing with precum the moment she was in my arms. Scooping her up I headed for the stairs. Kelsey could be the gracious hostess tonight, right now I wanted nothing more than to ravish Helen.

"Goodnight everyone. Thank you Greg."

"Kevin, would you wait just a moment please?"

"Yes grandmother?" I paused to look at her.

"How much do you want?"

"Grandmother?"

She pointed at the computer screen and the things displayed on it.

"How much do you want for doing that?"

"I don't understand. Doing what?"

"That!" She stabbed her arm at the computer. "Do you know what you just did?"

I looked at the screen and then back to her. I had no idea what she was talking about. Seconds later she made that heaven help me look upward again.

"Kevin, what you just did in twenty minutes would have taken me weeks if not months to do by myself."

"And?"

She gave me another one of those eye lifts to the sky.

"Do you realize that women will pay you to do that? Lots and lots of women. Women who will pay you lots and lots of money."

"My love . . ." Helen turned my face toward hers and stretched slightly so she could kiss me as a reminder that she had needs which required my immediate attention.

"Talk to Kelsey about it." I bounced Helen lightly in my arms and headed for her bedroom.

"Wait, what?" Kelsey sounded startled. "Kevin!"

I put Helen on her feet as soon as we reached her bedroom. She had a thing about not touching her bed with the clothes she'd been wearing while being serviced by other Males. I could understand the symbolism, in her mind she wasn't clean. Not that I cared, the fact that she'd just had sex with another man only made her more desirable in my eyes.

Helen stepped out of her clothes and left them on the floor. Again, it was something she did every time she had sex with one of her Males. When she was naked, I slipped my arms around her from behind and nuzzled her neck behind the ear.

"Mmmm . . ."

She hummed and stretched her arms overhead, arching her back as my hands drifted upward on her stomach to cup her breasts. Spreading her feet, she braced herself by putting her hands on the wall and waited for me.

"Fuck me sir."

I took her. Roughly shoving her forward against the wall, I unzipped my pants and drove my cock deep into her. Angling my aim, I thrust deep again.

"Yesss . . ." Helen tipped her hips so I had an even better angle. "Fuck me sir."

I kept thrusting until Helen pulsed and shoved herself back into me. Her thighs started quivering and she held her breath. Another stroke and she gasped. I grabbed her hips and slammed full length into her, lifting her to her tip toes with the power of my thrust.

"Yes! Fuck me, Sir!" She clawed at the wall as I powered into her again, once more lifting her up on her toes.

Another stroke and her eyes rolled up in her head and she started quivering all over. One more deep powerful stroke and she started to pulse rhythmically around my cock.

I used my weight and strength to press her harder against the wall and kept pumping into her as her pussy kept pulsing while she held her breath and tried to gouge the plaster off the walls with her fingernails. Eventually she went quiet and let me continue stroking in and out. Rather than finish for myself at that point, I pulled out, lifted her in my arms, and gently placed her on the bed.

Undressing first, I crawled on all fours between her legs and positioned myself. Hot hands held me for a moment then bent my cock down and aimed the tip at her cleft. Smoothly I thrust forward as her hands slipped along my shaft until I was fully inside of her again.

"Take me, my love." She whispered in my ear and held me tight as she lifted her legs and curled her toes. "Make me yours."

She had two more orgasms before I finally had mine. Helen rocked me quietly as I rested on top of her and caught my breath.

"I love you Helen."

"Shh, my love. Sleep."

I woke when Helen slid out of bed in the morning. I rolled onto my back and watched her disappear into her bathroom. Seconds later the bedroom door eased open and Kelsey peeped in. Seeing me alone, she slipped in, closed the door with a small click, and squirreled herself underneath the covers with me. All she had on were tiny green panties.

"What are you doing?" I asked softly.

"Nothing. Yet." Her eyes glinted with humor as she snuggled against me and laid her cheek on my chest. "You do realize that out of all the people who were in the house last night, and who all know what everyone was doing all night long, and with whom, I'm the only one who didn't have any fun."

"You could have used a vibrator."

"Nope, not allowed." She shook her head.

"Huh?"

"They destroy sensitivity and desire. As does masturbation." Helen came out of the bathroom. She had her bathrobe on.

Bending she kissed me lightly, cupped Kelsey's face for a moment then headed for the bedroom door, tacitly granting Kelsey permission for the morning even though it wasn't one of Kelsey's scheduled days with me. Not that it was all that unusual, Kelsey occasionally made love with the two of us if Helen invited her and it was a toss up which one of them wound up servicing me.

That never happened on the nights after Helen came home from servicing one or more of her Males because those nights were reserved for me being alone with Helen. The morning after was a different story. As my sister well knew. The only issue was if Helen objected to sharing or not. That wasn't the case this morning.

After mom left I looked at Kelsey for the explanation about vibrators.

"Vibrators are bad?"

"Vibrators can make you numb or less sensitive. I used to use one but since mom gave me the pink book I haven't because it explained why not to."

"And?"

She squirmed until she got her underwear off and then straddled me. Sitting upright she positioned me where she wanted me and slowly lowered herself onto my hard on, wiggling her hips the whole time until I was fully inserted all the way to the base. Dropping onto my chest she looked me in the eyes.

"It took a little while but I'm not numb anymore. Since I'm not allowed to masturbate either, there's really only one other option if I want to be satisfied. And with you right here I don't need to find someone else or go back to relying on an inert chunk of plastic that can't really do for me what you can."

With that she sat back up and started riding me up and down. Arching her back, she tipped her pelvis so that my cock started plowing into her pleasure button each time she pumped her hips. Several orgasms later, she dropped flat on my chest again. Her hair was plastered to her temples and she was breathing fast and deep. I could see her pulse beating in the hollow at the base of her throat too.

I ran my fingers up her spine as she rested and relaxed on top of me.

"Mmmmmm . . ." She wiggled her hips and hummed into my chest. "Better watch it Kev, I know you haven't come yet."

"I'm fine." I stroked her back again.

"But I need another orgasm. Or two. Maybe three. What do you think; does four sound like a good round number?" I could feel her smile as she said it.

At that point mom opened the bedroom door.

"Kevin, mother is here."

"And?" I looked at her while Kelsey sat up and twisted on top of me to do the same.

"She wants to talk to you. About clothes."

"Nooooo . . ." Kelsey whined as she dropped flat on top of me again.

"Off." I pushed at her.

Rather than do what I said, Kelsey started pumping her hips with the serious intention of having one last orgasm. Mother watched for a bit then closed the door, she'd tell grandmother what was going on. Grandmother would wait for awhile, but if we took too long she'd be the next one to open the bedroom door.

If that happened I couldn't predict what the outcome would be. Neither Kelsey or I minded anymore if either mom or grandmother caught us in the act. We'd had sex with the both of them so often that we'd lost any self consciousness over being seen together by them. Granddad might make Kel miss a beat, because as far as I knew they'd not slept together, but I wasn't sure about even that. No, the real problem was that this time I didn't know if I'd be scolded before or after I satisfied grandmother. Or both. Or even worse, neither.

Kelsey held her breath, pulsed, and slammed her hips down. I thrust upward, straining to come at the same time she did. Together we pumped and pulsed until we both were done and Kelsey sprawled bonelessly on top of me.

"Mmmm . . ." A few breaths later she pushed up high enough to kiss me.

"Thank you, sir."

"You know you don't have to repeat what Helen and Marjory say just because you think I expect it."

"I'm not. I use the same words but I'm not just saying them because I heard mom and grandmother say them. I say them because I mean them, just like they do. I say them because, if I don't, how else would you know how much I enjoyed what we just did? Besides the obvious multiple orgasms." She looked down at me.

"Kev, you're not just someone to have sex with; I love you. I like sleeping with you even when we don't have sex because you make me feel safe and warm and loved in return. I like the sex we have together and I like the fact that you want to have sex with me because it means I'm special to you. But most of all when you come it makes me feel complete. When you come I know that I did my part to love you and make you happy. I also know that you did your part to love me back because you want me to be happy too. And trust me big brother, the orgasms you give me definitely make me happy. I'll even bet that if you ask mom or grandmother they'll tell you that they don't say it to their Males after they service them. Just you or granddad, which ought to tell you something."

She bent and kissed me again.

"So. Thank you, sir."

I looked up at her. Gently I cupped her behind her head and drew her down for another kiss.

"You're welcome dear heart." I kissed her for the last time and let her go.

She grimaced as she lifted herself off of me. She always hated that part because she said it made her feel empty.

"Sure, that's what you say now but what about me?" She stretched out alongside my body and traced designs on my chest with her fingers. "Here I am all sweaty and sticky from the mess you made yet I'm left without you."

"Talk to mom and grandmother about it." I rolled over and sat up.

"They both have the same complaint, sir."

"I'm also limp."

"Sir, you have fingers." Kelsey rolled off the bed and to her feet, snatching up her underwear at the same time. "And a tongue."

With that, she flounced out of the bedroom. Seconds later the bathroom door closed. Sighing to myself, I grabbed my pants and headed for the bathroom downstairs. I passed grandmother on her way up the stairs.

"In a minute." I zoomed by without slowing. "I have to pee."

TEN

The four of us sat in the office as grandmother explained exactly what she thought I should do. She wanted me to start a consulting business in women's fashion and clothing, telling us that what I did yesterday was remarkable. And a rare talent.

"I don't have the money for any of what you're talking about. I don't have any clients either. And that's without considering how I'm going to promote or advertise myself. Especially since I have no experience to tout. I also don't have a website and it can take thousands of dollars to create one of those. I don't even know anyone who could do that kind of thing." I tried to tell them that what they were thinking was impossible.

"Wade might be able to do it." Kelsey tossed that out there about the website. "If he can't, he probably knows someone who can."

"Wade's a gamer, not a programmer."

"So? Does that mean he can't do it or that he doesn't know anyone who can?"

"I don't know. All I know is that I couldn't pay for it anyway."

Kelsey looked at me.

"You're not a slut. Or a bitch."

Grandmother looked at mom with a puzzled expression.

"She means I'm being unreasonable." I explained the reference. "We had this conversation a couple of days ago where a certain someone was being obstinate over behavior she didn't want to admit was wrong."

Kelsey nodded again.

"Tabitha is not a slut."

I threw up my hands.

"I think that if you actually," she paused for a second like it was difficult for her to say it then went on. "If you actually sat down and talked to her, you'd find out that she's really a nice person."

"Like I couldn't have seen that one coming a mile away." I sat back and crossed my arms.

"You might not become best friends, but you'd learn she's really a nice person."

I growled because she wasn't going to give up. Plus the fact that she was right and we both knew it.

"Fine, I'll call Wade and see what he can do."

Kelsey looked at grandmother and mom and smiled.

"One ridiculously obstinate denial down, four to go. This training thing is fun."

Grandmother grinned and reached for her bag on the floor at her feet. Digging inside for a moment she produced a plain white envelope and held it out to me.

"What's this?" I took the envelope.

"I wrote down everything I want from what you showed me yesterday and added it up."

"And?" I looked inside the envelope. Money. Lots of cash money.

"That's what I'm willing to pay you to buy it for me."

"Grandmother." I held the envelope out to her so she could take it back.

She crossed her arms and refused to accept it. I looked at my mother for help.

"Ahem." Grandmother cleared her throat. "I would like a receipt please. Sir."

They waited while I turned on the computer and opened a file for her and started listing all of the things she wanted me to buy that she'd written on a piece of paper and stuffed into the envelope along with the money. Complete with prices. Finished, I printed the list and gave it to her.

"Thank you, sir. When can I expect my first fitting?"

"Your what?"

"My fitting. You don't expect me to just take the clothes and go home do you?"

I sighed again.

"I have work. And school."

She waited patiently.

"What now?"

"When are you available when you're not at work or school?"

A choked off snort made me look at both my sister and mother. They were trying very hard to keep a straight face and not laugh. And not succeeding very well at either.

"Thursday. Afternoon. After three. Thirty." I gave up. "If I buy them for you today, your things should have arrived by then. If not we can reschedule."

Grandmother nodded once.

"I will let Gregory know so that he can put it in my calendar. If there is a conflict he will inform you."

"Wait, granddad keeps your appointment calendar?" This was news to me.

She nodded again.

"He is my chaperone, it is his task to ensure that I am not over-scheduled for all of my daily affairs as well as tracking and managing my social appointments for being courted."

"Courted?"

She looked at me.

"Sir. I hope you do not think that I would accept just any Male who asked for my favors. I am not a whore or a bed slave to be sold or rented to every Male with blue balls and bad breath. Nor am I interested in some useless bastard with no future or manners. My chaperone protects my interests so that none of that occurs."