HouseKeeping

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Older man wants entertaining housekeeper.
5.8k words
4.75
125.9k
115

Part 1 of the 14 part series

Updated 06/07/2023
Created 03/26/2015
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FLSr5r
FLSr5r
195 Followers

The doorbell rang and it took me a few seconds to answer it. When I opened the door, I was very please with what I saw. She seemed to be about 45 years old, as promised in my phone call with her two days ago, but she was smoking hot. She had a face that was sort of long, with dark brown shoulder length hair that formed an oval around her face, and just enough make-up to tell me she was wearing some. Her eyes were dark brown, almost black, and seemed so deep I could fall into them and drown. She was wearing an overcoat in spite of the fact that it was warm outside that hid her figure, but even the coat could not disguise the fact that she was slim and shapely. I smiled widely and invited her inside.

"You must be Kelsey," I declared with certainty. "I am Todd. Welcome to my home."

"It sure looks beautiful from the outside, Todd, and it is probably just as beautiful inside." Kelsey was politeness itself.

"Come in, Kelsey, and let me tell you a little more about why you are here." She had a beautiful face with an alert expression, but laced with just a hint of apprehension. She wore some pale pink lipstick, and what might be some blush on her high cheekbones. The colors around her eyes highlighted her eyes rather than covered them, making them the dominant features of her face. They were dark brown and seemed to be pools of liquid, and they showed so much life they exuded excitement. All told, she was even more beautiful than the pictures she had sent to me by email. I led her to the family room, and sat on the couch. She sat near me, but not next to me. She still wore her coat, and I did not offer to take it from her at this point.

"As you can see, Kelsey, I have a large and beautiful house. I have designed it myself, and furnished it according to my tastes. And also, as you can see, my tastes are most decidedly masculine. I have lived alone since my divorce almost 20 years ago, so I can decorate how I want to. And it is almost 4,000 square feet, a large house for just one person, I am told by my two sisters constantly, and by my friends regularly. But I like it. A lot. Still, it is a big house. I have no problem keeping the kitchen clean, and my office is for me alone. But the rest of the house sometimes needs a little touch up here and there, and this is where you come in.

"I explained my ad to you the other day on the phone. Now I want to go into a little more detail. I need two things that I stated in the ad. First, I need light housecleaning. You know what I mean - sweeping, dusting, vacuuming, and maybe a little mopping every once in a while. If this works out, and you get to know me and my house, maybe you can straighten up here and there, put things away, even wash dishes once in a while. I want the bed linens to be changed every week, and the bathroom towels to be washed with the sheets. Only what I believe to be light housekeeping. Once a month, I expect to find someone to do the serious cleaning, but that is a separate issue. If you are at all interested in that, we can discuss it later." I paused for a few seconds, to make sure I had covered everything I wanted to say about cleaning. I couldn't think of anything else, and she jumped into the silence.

"And the other thing you need?" Kelsey inquired softly, almost gently. I noticed that her smile was so warm and engaging that I took a moment to bask in it, yet it was just a little hesitant.

"The other thing I need, Kelsey, is a little entertainment. I have been alone for too long. I hate the bar scene, and I simply am so out of touch with the dating scene that I don't know what to do once I enter a bar. Yet I absolutely love feminine company, and I miss having a sexy woman around. I have more than enough money to enjoy life, but I have no one to enjoy that life with. So I decided that it was time for a change. As I stated to you over the phone the other day, I want someone to clean my house who is scantily clothed. A classic "French maid" outfit is just fine, whatever you believe that to entail. Or beautiful underwear is even better. Whatever is tantalizing to me and fun for you. But at no time will I ask or expect you to be fully nude. I promise I will not touch you in any way while you are here. On the other hand, you may touch me if you choose. And you may touch yourself if you want. It is most important that you relax and enjoy your time here, because I want to be teased. If you are not enjoying yourself and your time here, I will know it, and I will not be as teased and excited as I would be if you were enjoying yourself.

"I will pay you $300 for two hours of your time. At the end of two hours, I will pay you cash and you may leave. If you want, you may clean up here, or take a shower, or whatever you decide. And once I have paid you, if you choose, I would like to take you to dinner. To a nice restaurant, where you may dress up and show off how beautiful you are. As I expressed to you the other day, inviting you out to dinner is entirely my option. If I find I enjoy both your conversation and your company this afternoon, I will invite you out to dinner with me tonight. If I enjoy our time together, I will ask you to make this a long-term contract - twice a week, on Monday and Friday, if it were my choice, but how often would be your choice. Each time will include dinner, but only if you choose. It is entirely possible that you will enjoy the housecleaning and the spending money, but not wish to participate in dinner. That will be entirely up to you and will have no impact on the more pragmatic side to our relationship." Again I paused to think if there was anything I left out.

"In the ad, and then again in our phone conversation, you mentioned the possibility of additional money; I think you called them tips. What did you mean by that word?" She seemed slow to inquire about what I meant by "tips," perhaps even a little embarrassed by asking. I smiled.

"Yes, tips." I paused, trying to put my words together. "I consider the stated fee to be the equivalent of the cost of dinner. It is fixed by the menu. But I have always tipped for good service, and even more for special service. And the only time I have tipped as low as 10% was when I was not happy with the service. If I am happy with the service, I tip my server anywhere from 15% to as much as 50%. To be more specific, I want you to enjoy your time here. If you do, I will almost certainly enjoy myself even more. And the more I am teased and excited, the more I will tip. But I am talking about being teased and entertained. I am not talking about you stripping naked, as I already said. Being properly teased is as much a mental thing as it is a visual thing. If I invite you back, and if you decide to come back, over time you will understand what teases and titillates me and my unique tastes. As you implement that knowledge, the tips will increase. Do you fully understand what I want from you? Do you have any questions for me at all?" I believed I had been a clear as possible, but I had no idea what her response to the offer was going to be. I hoped that her presence here implied a positive response, but my description of what I wanted was more detailed this afternoon than it had been a couple days ago on the telephone. I looked into her gorgeous eyes and waited to see if she was interested in the offer. Her response was quick in coming.

"So, you want me to clean the house to the point that it looks and smells clean. And you want me to be sexually entertaining while I do it. But you are not asking that I strip naked for you. And you are not asking that I have sex with you. And the indescribable balance between uninspiring and titillating is left undefined, but the amount of my tips will rest on my finding and exceeding that balance. Right so far?" I found that I really liked her ability to grasp and then to verbalize. I suspected this one was a keeper.

"Right so far," I nodded. "But I still hear a question in your eyes." I chuckled when she raised her eyebrows, those sexy almost black eyebrows.

"Yes, I have one more question. Why in the world would you ask for a 45 year old woman when we both know you could have a list of hot young women lined up at your doorstep to do this?"

"I told you I want to be teased and tantalized. That requires that we work together to develop a fantasy. And a fantasy works only as long as it seems possible. If I can't see the possibility of this fantasy ever coming true, then the fantasy collapses. There are hundreds of 20-something women who would go for this. Hell, there might be several thousand of them in the area, I don't know. But that fantasy could never come true. I could get sexually aroused by a young and sexy woman, but I could never get properly teased and tantalized by a fantasy involving a woman that young. I wanted this to work with a woman more my age. And before you say anything, I need to tell you that there is no such thing as a perfect body. And even if there were a perfect body somewhere, I am not convinced it would be encasing a 25 year old woman. I wanted an older woman that was more mature - it is just that simple." I sat back, confident that I knew what I wanted and what would be the most exciting image for me to build this fantasy. And since this was my fantasy I was pursuing, I didn't want to start out with something that I knew would fail in the long run.

She paused for a few seconds, and then nodded.

"So I guess the next thing would be for you to decide if my body is good enough that you might want, and be able, to develop your fantasy with me." Her voice was clearly a monotone, almost unmotivated, and her expression was unreadable. Did I detect a little anxiety in her?

I replied with, "Yes, I think that is the next step." I had absolutely no idea what her body looked like, but I found myself getting aroused at the possibility of seeing it the first time.

She slowly stood, walked around the coffee table, and turned to face me from about two feet away. I discovered that I was holding my breath.

Slowly, she untied the belt that was wrapped around her full length raincoat. Then, one by one, she unfastened the buttons, allowing her coat to drape open only slightly. I caught a glimpse of white lace, and sat there waiting. I looked up and into her eyes, and was thrilled to see a twinkle there. She was already teasing me, and seemed to be enjoying it. I waited without a sound, amazed at my patience.

After a pause of several seconds, she shrugged her shoulders and her coat dropped to the floor. She stood there for at least ten seconds without a word. Then she turned slightly to the side and bent over at the waist to retrieve her coat, giving me a great profile view. She folded the coat and gently laid it across the over-stuffed chair behind her. Then she turned again to fully face me, making no attempt to hide anything.

What I saw was a fantasy. It was clear that she was 45 years old, based on the slight sag of her breasts and a wrinkle here and there. But before me was a gorgeous woman with a fantastic body. She was at least eight inches shorter than me, standing at no more than 5'6" tall without her heels. She was wearing matching white underwear. Her bra was very lacy, showing only a hint of her nipples and the darker skin of her areolas surrounding them. She was a full C-cup, and maybe a small D-cup in size, and her breasts were barely contained in the cups that seemed to be mostly missing. Her sides narrowed to a slender waist, perhaps two inches more around than some 21 year old "perfect" body, showing by her nearly flat stomach the fact that she worked out regularly and probably frequently. Her waist expanded to full hips, with what looked like a tight yet rounded ass that sagged only slightly. That beautiful ass was only slightly covered by white lacy panties that weren't quite a thong, but covered only a little more than a thong would have covered. And her pussy was almost exposed by the thin material that seemed to cling to her lips and outline them for me to see. Her legs were long and very shapely, and were covered by light gray stockings that were held up on her thighs by a four inch band of elastic and lace of darker gray. I guessed she might have weighed 140 pounds, but only because of her full and rounded breasts and shapely legs. She wore beautiful white sandals with heels about two inches high and straps that wound around her soft calves several times and buckled about four inches above the heels.

I admit that I gasped, and then quickly drew in my breath.

"Kelsey, you are stunning!" I burst out without even thinking. "Damn!" I didn't know what else to say. She sat down next to me, with her hips barely touching me.

"Is this touching too much?" Her smile was infectious, and it seemed like she was enjoying this entirely too much.

"I said I would not touch you, but that you are allowed to touch me." My smile was warm and genuine.

"That's right, you did say that." Her smile was just as genuine, and even warmer than mine had been.

"Okay, now that I have my breath back, I would like to ask you some more questions."

"You may ask me anything you want, but I reserve the right to not answer. This is a job, not a marriage." Her smile was still warm, but her words held a warning. Apparently, there were some things about her life she wasn't ready to share, I guessed. And I really liked her frankness, and the boldness she showed in answering me like that.

"Kelsey, you always have the right to not answer any question, or to not do anything, that makes you uncomfortable. Always. Do you understand that?" I hoped my voice was firm, but I wanted it to be gentle at the same time. She nodded without saying anything, but her smile was still warm.

"I wanted to know a little more about your past, and especially why you responded to my ad for this position. Why would a woman who is gorgeous and clearly very classy respond to my ad for a partially dressed house cleaner?" My curiosity was high - I really wanted to know the answer.

"I liked your ad. You seemed to be honest and straight-forward about what you wanted, and yet you seemed to be a gentleman in how you asked for it. I was curious about you, and about whether or not I could ever do this type of thing." She paused as if she was unsure how to go on. "Besides, I need the money." She paused for several seconds, and then continued.

"I was married for 25 years, and then discovered my husband was having an affair with his secretary. After the divorce, he moved in with her and I decided to evaluate my life. I grew up quite conservative, and I concluded that my conservative nature and dress was not exciting and fulfilling to my husband. Your ad made me wonder if I should consider changing, becoming more adventurous. So I decided to explore showing off my body more than I had in the past. This gives me an opportunity to try it with little risk and no harm."

"Have you ever done anything like this before?" I thought my question was clear, but she showed confusion. "Have you ever taken some or all of your clothes off for fun or profit, for anything other than love?"

"No, never. And I confess I am a little nervous about it."

"Well, I hope this will be both fun and profitable for you. If not, then just say no, and I will pay you what I promised and wish you the best." I looked at her, hoping that I appeared honest and honorable.

"But first, let me tell you a little about me. I was married for one week short of 22 years. My wife left me for her girlfriend." I saw Kelsey look at me closely. "So I know about surprises, believe me. And I am not into one night stands, and never will be. Yet I still have needs, and even interests, that I am still discovering. I made an unreasonable and illogical investment a few years ago, and it made me millions. But I was still alone. Yet I like me. I actually like me enough to be alone with me if it is necessary. So I could handle life alone, but I longed for a relationship with a beautiful woman who was both mentally and sexually stimulating. And I wanted this relationship without any of the problems consistent with a one night stand. Since I didn't want to hang around topless bars, and I didn't want to have a string of prostitutes hanging around, I decided to try this. It is a total experiment with me. I don't know what will come of this. But I do know that I am going to enjoy experimenting. And if you want to try this experiment with me, then maybe we can both have a little fun. How about it?" I shut up and waited for her to respond.

Kelsey stared at the floor for another few seconds and then smiled. And that smile changed her entire presence. She had been hesitant before. Now she sat next to me positively glowing. And as her excitement increased, so did mine.

.

"Who knows?" she almost mumbled. "Maybe I will get hooked on this exhibitionism thing." I smiled in excitement.

"So, how about I show you around my house." I stood up and looked down at her. I reached out my hand and she took it. I helped her to her feet, and began the tour at the place we stood. As we walked through my large house, I couldn't help but notice her awesome ass, especially as it seemed to sway more and more as we walked. Part way through the tour, I suggested a glass of wine. I led her to the kitchen where I kept a supply of different labels. She selected one, and I uncorked the bottle. As she reached to take down the wine glasses, I found myself staring at her body. The tight panties pulled into her butt crack, outlining her beautiful ass and the camel-toe in front. I found myself getting hard, and she noticed.

"Is that for me?" she asked, almost shyly.

"No, that is for me later. But let's get that issue out in the open. Kelsey, you are totally hot, and beautiful at the same time. If you are around me dressed like that, then you will see me get hard frequently. After all, that is what teasing is all about. So you will have to get used to it. Make all the comments you want about it, you won't embarrass me. But get used to it because you will see me get hard a lot. Are you okay with that?" She looked at me with a grin.

"Isn't it part of my job to make that happen?" I nodded in response. "And don't I get more tips if I make it happen a lot?" I nodded again, and added a grin. "Then I look forward to seeing it happen a lot! Besides, it looks great to me. I actually want to see it a lot, and would even if I weren't getting tipped for making it happen. So maybe you need to get used to me enjoying it!" Her expression was one of triumph, and she took another sip of her wine.

Suddenly, I realized that things just might take a turn I had not expected if I wasn't very careful. This whole experiment was based on entertainment without the possibility of my emotions getting involved, and I realized my emotions were trying to get involved. And as that thought began to percolate in my brain, I decided that unexpected events were not always bad. I found myself looking forward to this experiment far more than I had originally expected.

I finished showing her around the house, including where I kept the cleaning supplies. I poured a second glass of wine but she declined hers.

"So, have you decided to take the job?" I hadn't really asked the question, and she hadn't really said yes.

"From the looks of your pants, I think I have already started." Her saucy grin was a joy to behold, in addition to being sexy as hell. I smiled in response, glad to hear her say yes, and also glad that she seemed to be enjoying getting a rise out of me. Her rather saucy attitude was going to make this thing much more fun.

"Okay, sweet lady, you are now on the clock. Your job is over in two hours." My grin was as big as hers.

"Two hours! From what you have shown me, it will only take one hour." She seemed a little confused.

FLSr5r
FLSr5r
195 Followers
12