In Praise of Janet Ch. 01

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A game turns real.
9.7k words
4.34
36.1k
14

Part 1 of the 2 part series

Updated 10/16/2022
Created 11/26/2013
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Momstheboss
Momstheboss
3,114 Followers

It was a rainy evening and after dinner my wife decided she wanted to buy groceries. I complained Friday night was usually the busiest night, next to Saturday. Argument lost. As she did not like driving after sundown, especially in the rain, it meant I was going too.

I eyed the clock; 6:30 -- without any unforeseen hang-ups we would be home easily by 8:30, 8:45 at the latest.

There is one bright side to buying groceries, which is ......girl watching. I like most all women, but redheads in particular because I married one, natural of course. A collar matches cuff thing!

Now! At 64, not getting enough pussy, my self-esteem sliding into oblivion, I had years earlier started playing a game: Select a woman whom appealed to me and catch her eye and elicit a smile from her as we passed on any given aisle.

It's well documented that a person can detect when, or if, they are being watched. My game required tact and stealth. Tact, in not to appear staring and make the "look" friendly and happenstance. I have been playing this game so long that I could write a small book on the times it has worked. I am not a particularly handsome man, though my wife thinks so but she's prejudice, but I do have blue eyes, white hair and a warm knowing smile.

And lets not forget; the stealth not to get caught by my wife by knowing where she is at all times.

On this rainy Friday night there was an abundance of the fairer sex but few that appealed to me. I still gazed at their attributes but found little to cause my heart to thump.

Then I saw her at the far end of an aisle coming my way.

Shoulder length dark hair, almost black, about my height 5'9", maybe 5'10", khaki pants and dark long sleeve sweater.

At a distance, her hair appeared to need combing but now, as she came nearer one could tell it was slightly curly. Letting my eyes wander, my wife 6 feet or more behind me studying foodstuff, I noted brown eyes and strong features, modest sized breasts that were pointed and a belly so insignificant it barely registered a notice. I could not deem her pretty or cute, just sexually attractive with a serious, unsmiling presents. I aged her in late 30s, maybe 40-41.

As she passed, I turned slowly catching sight of my wife first in my peripheral vision. She still picking an item, I considered the lady's posterior. I compare all female's ass to my wife's perfect ass. The lady in question was a bit wider and flatter but I deemed it perfection.

On the next aisle, my wife in front of me, I looked straight at the lady when she was about 25' from me, shifted my eyes away, then, straight at her at about 10', holding for a long moment. I felt certain she was aware of my interest. On the next aisle, my wife barely a half step ahead to my right, I waited until the woman was no more than 7' away. I gazed straight at her. This time she met my eyes and she smiled an acknowledgement. I returned her smile. My wife was looking down to her right.

Mission accomplished! My ego brightened!

On the next aisle my wife was quite a distance away getting hamburger. I waited a third of the way down the aisle. I saw the lady coming but turned away to view my wife. The woman stopped her cart across from me and crossed the aisle stopping at the front of my cart. She said to my back, "You seem interested? Would you like to talk price? " Not quite in a whisper.

I turned partially to see her studying the soup cans. Her voice was pleasant enough but it brought to mind the high-pitched voice of the dark-haired model in the Victoria's Secret commercials. They never should have let that girl speak on camera.

"Yes. I certainly would." I reply softly.

"Call me." She said, placing a piece of paper on top of a can. "My name is Janet."

"My name is Press. Short for Preston."

The woman continued on past me, as I looked for the location of my wife. I assessed her backside one more time. Not seeing my wife, I quickly retrieved the piece of paper from the can and stuffed it into my pocket. I looked for Janet through the next three aisles but did not see her again in the store.

Monday I called the number between the hours she had written on the paper.

"Hello."

"Janet?"

"Yes."

"This is Press. Is this a good time?"

"Do you always stare at women in stores?" She said nonchalantly with no challenge in her tone. "With your wife so nearby?"

"One stares at something unusual or odd. One gazes on something lovely or appealing.

"I can't argue with that reasoning, I suppose.

"Did I make you uncomfortable?" I queried, wanting to know if I needed to change something in my game.

"No. Not really. I knew your eyes were on me. I knew you wanted me to return your look." She replied.

"I don't really know how to express this." I began. "Are you an escort?"

"A housewife." She answered. "A happily married housewife, but my husband is having a little financial troubles in his construction business. A very close girlfriend told me a few weeks ago how I could make money on the side. I love my husband very much but I'm tired of not having any spending money. I have this "to do list". There are school clothes and items that are big-ticket items. I know things will turn around soon but it's still going to be some time before I can asked him for a large amount of money to throw away on things."

"And you thought a married man would be the smart way to go? Do you have a thing for older men?

"To be honest, I was scared to death, but yes that's what my girlfriend suggested. You and your wife seem to be a loving couple. I saw her ask you for a kiss. I am aware of how my mother treats my father. According to her, she's not much interested in sex anymore. Are you happily married?"

"Very much so. But I'm not getting a whole lot of pussy as you rightly surmised. Have you done this before?"

"No, like I told you, my girlfriend only just said something about it a couple of weeks ago. I was complaining about my list. I had actually dismissed the notion until I saw you staring, I mean, gazing at me. Have you ever been unfaithful to your wife?"

"No. Not in 40+ years. I play a game like I did with you. I have gotten a lot of women to smile at me but not a one that did what you did. So, how much do you think your worth and what are you offering? "

"My girlfriend charged $800. I'm a little flexible with that, but I will admit I saw you getting out of a late model Cadillac. I don't like oral sex or would ever consider anal and a condom is preferred, I suppose." She answered. "Positions etc. are entirely up to you."

"A little clarification. You don't like giving oral sex and you don't like receiving it!" I quizzed.

"I love getting it, of course."

"Is this acceptable? I love giving oral. If you have never been unfaithful and I have never been unfaithful the chances of either of us having something is very small. I have been snipped so lets do away with the rubber. And, since we are being honest, Janet, I haven't had any pussy in about four months. Occasionally, I have had trouble keeping it hard for any length of time. The last time it worked fine. I may never get it in you. So, if we are of one mind so far, I have one last question. Do you like sex? Are you going to be passive? That's two, isn't it?"

"Yes. I like sex. And when the lights go out, Press, I even like to fuck."

"I'm sorry, a minor thing. You gave me a spread of five hours to call you --

10 o'clock to 3 o'clock. I don't know where you are but the motel is about 45 minutes from the grocery store. Taking in the same amount of time to drive back, 45 minutes to shower and dress, that's approximately 3 hours time and effort. Does that sound agreeable?"

"Certainly. But you make it sound so cold, but I guess it is just business, isn't it. How about I meet you at the motel at 10 o'clock."

"Then young lady I would say, with nothing else to go on except that I like you and find you very attractive, I think you'll be underpaid. Shall we set a date and time? I know of a place."

The agreed-upon day was Wednesday, a day away. I gave her directions to the motel, telling her that the room would be around back, hence, there was no chance of our vehicles being seen. I called her back an hour later to give her the room number.

Before hanging up I asked if it was possible to wear what she had on in the grocery store.

"Do you have any preference in color of underwear?" She asked with humor in her tone.

"I'll leave that to your discretion, dear lady." I answered chuckling.

Every Wednesday I drove to Carolina with a friend to have lunch. Canceling lunch with him was easy enough.

I left my house at 9 o'clock Wednesday morning. Hitting the interstate, I knew it would not take me 45 minutes to get to the motel. I had failed to ask her what type of car she would be driving, so I wanted to get there a little early. Commando under my jeans, I squeezed my crotch often with anticipation. I felt firmness, which was a good sign. I thought about her comment about me making the time table sound so cold and her decision to meet me at the motel at 10 o'clock. I took that as a good sign.

I took no erection pills, as I did not feel like I had a problem. With my wife, it would have been like having a tuxedo on with nowhere to go. It had become very difficult to know when she might give in. I could not have gotten any pills in time even if I had wanted. It helped, that I had confessed to Janet, so there would be no embarrassment there. I would send the lady home happy one way or the other, as was always my main concern.

I backed my Caddie into the parking space off to one side of the motel door.

At five after 10 o'clock, a white late-model Impala came around the corner of the motel and pulled in next to me. Janice smiled warmly. As she exited the car, I threw the four small breath fresheners into my mouth. She retrieved a small travel bag and I studied her posterior once more. She had indeed worn the same clothes she was wearing in the grocery store. And I guessed at the color of the underwear she had decided to wear - light blue.

"Good morning Janet." I said in greeting, as I opened my door and got out.

"Good morning to you Press. I hope I did not keep you waiting?"

"Not at all."

We walked to the door and I unlocked it, pushed it open and stepped aside allowing her to enter first.

"It's good to see you again." I said, as I closed the door and set the locks.

"Nice room!" She said, dropping her travel bag and looking around.

I turned on a light near the door and closed the curtains on the one expensive window.

She was standing near the right-hand side of the bed and I moved in front of her.

"We are both novice at this. I spent some time thinking, maybe a kiss and I undress you?"

"Sounds like a beginning." She replied. "But from here on out you're not allowed to think." She said with humor.

I moved in close to her, put my hands on her hips and kissed her lightly on the lips. Her hands slipped around my neck and things became quite naturally as our kiss deepened.

I slid my hands under the back of her sweater feeling the warmth of her body. I moved my hands around her sides, up to the sides of her breasts. I cupped them lightly and lifted my thumbs to rub over the bra where I figured her nipples would be. I felt bare nipples! Firm bare nipples!

As I began to lift her sweater, Janice lifted her arms and extricated herself from the sweater.

I stared at a dark blue, lace-fringed bra that had two holes cut out for the nipples to protrude through.

"My Lord woman! Are you trying to give me a heart attack?" I exclaimed.

"Do you like the bra? How about the color?"

"Exceptional on both counts." I replied, as I took her right nipple into my mouth, my hands returning to the small of her back.

After a few short minutes of suckling on her nipples, alternately, I returned to kissing her. I began unbuckling her belt, pulling the side zipper down and unbuttoned the pants. Leaving her lips, I pushed the pants off her hips. Turning her, I sat her down on the bed and reclined her back onto the bed. I removed her flats and then finished pulling her khakis off.

She wore dark blue matching, laced full panties. I might have been expecting bikini type panties. I don't know what I was expecting! But what she had on was exceptional.

As she lay there watching, I began to undress myself, kicking my shoes off and under the bed, no socks, then, the rest of my clothes. I saw her smile softly as I stood before her nude, my erection quite healthy.

I moved to the bed, putting my hands to her flat belly and my nose into her covered mound, moving my nose down to her crotch. As I pushed my nose into her crotch, she pulled her legs back. I scrubbed her crotch with my nose.

After listening to her soft moans a minute or two, I reached to pull her panties off. I noted a dark moist spot in the crotch of her underwear. I gazed upon a waxed, devoid of hair mound and pussy.

"Do you like it?" She queried.

"To be quite honest, I'm not sure." I replied, rushing to turn off the lamp. "Would you position yourself in the middle of the bed, please."

"Do you want me to take off the bra?"

"That is about the sexiest thing I have ever seen. We'll leave that on a bit longer." I replied enthusiastically.

I maneuvered between her legs as she lifted them. As I cradled her in my arms she took possession of my cock and put it to her bare pussy. I pushed into her slowly. She moaned appreciatively and sighed contentedly when I pushed it deep.

I began to fuck Janet slowly and she immediately matched my rhythm fucking me back, her feet off the bed, knees close to my sides at her hands on my upper arms.

After my eyes adjusted to the darkness, I found the room to be not that dark at all. The curtains allow the lot of light filtering through at the edges.

Long, long minutes we fucked without speaking. I smelled her perfume mixed with her womanly scent. I listened to her soft steady moaning, which was accentuated at the end of each deep thrust.

In due course, I slowed and pulled out of her.

I maneuvered to her right side and asked her to roll to her side and back up a bit. Acting instinctively, as we spooned, she lifted her legs and I guided my cock back into her very wet pussy.

Giving my back a bit of a rest, I fucked Janet a while like this, her right hand reaching to stroke my ass and thigh. She moaned very little but her ass was proactive in getting my cock deep into her.

I could not believe my cock. It was hard as a rock and staying there beyond my belief. It must be the strange pussy, I thought, or maybe the willing partner. Not being a professional, I found it hard to believe that Janet could be faking. She said she liked to fuck.

With a bit of concern of pulling from her, I pushed lightly on her hips to indicate I wanted her to roll to her belly. She understood and ended up nearly on her belly her left leg outstretched, her right knee pulled in tight, her ass postured upward and her pussy very accessible. The position working on my mind, only made my cock that much harder.

Strenuously supporting myself on one arm, I found I had enough room to slide my hand under our coupling and find her clit with my middle finger.

Her ass shot slightly upward and her moan told me I had found the right spot. With palm up, my middle finger extended the first knuckle slightly bent, I kept my hand motion-less, letting her, so to speak, stroke her clit with my finger.

It took a few long moments, but I found a method, a rhythm, I suppose, of pushing into her when she pushed her ass back, her clit stroking over my finger.

Her breathing was very labored and her moans almost continuous. My breathing was elevated, but my labor was of a different sort, holding myself mostly off of her and keeping my finger positioned without moving. I was soon hoping that Janet would orgasm very soon!

"AAaaaahhhhhhhhhh!" She moaned loudly, as the orgasm gripped her. "My Lord Press! It's good!"

We had been fucking, tops, 40 minutes. Her orgasm left her she held her position.

"I know it hasn't been long Press! I need you now. I need you to fuck my pussy hard!"

I did not have to be told twice. I shifted my weight, supporting myself on two hands and began to hammer at her ass.

"Yes! Yes!" She moaned, inspiring me to disregard my tiredness. "Give me your cum! Please Press! Harder damn you! Harder!"

I thought my whole body was going to explode. Luckily I had a weak point. It was my cock and it released all of my stress, plus a good quantity of sterile semen.

My orgasm gone, there was little I could manage accept to throw myself to my right onto my back to prevent me from dropping all my weight onto Janet. I was breathing hard, my hand on my belly.

Janet turned, then, flopped on her side, to face me. She lay quietly for a few moments smiling at me through the simi-darkness

"What was that you told me about maybe not getting it into me at all?"

She asked, mischief in her tone and eyes. "You are hell on wheels my good man."

"Hey, I'm as surprised as you are." I stated. "I can only attribute it to you being a very sexy woman with a bald pussy. And, you did say when the lights are off you like to fuck."

"I have to confess, and if you do not mind me mentioning my husband, he works a lot of hours and is not taking care of his homework like he should."

"No complaints here." I replied. "Tell me something. You say you have some things you want to buy. What is the total of all these things?"

She rattled off the items she wanted to purchase. "I would say about $5200."

"Then how about we divide that by 800, give or take, and we keep you as pure as possible and less chance of getting caught or a man causing you trouble in your marriage? Let's say we get together every other week?"

"That is very sweet of you Press. I would like that very much." She said lovingly, putting her head to my chest and kissing it lightly."

We talked about 20 minutes about this or that and then;

"Well, unless you want to masturbate in front of me, why don't you go clean yourself up and wake me when you're finished."

"You're a dirty old man!" She said teasingly, then more soberly. "Are you serious? I will if you want me to?"

"I'm playing with you sugar. Maybe some other time though. That could be fun." I replied. "Make sure you wake me up."

When she rolled over to exit the bed, I attacked her ass lovingly, holding on to her for a few moments, kissing and nibbling, making her laugh.

I noted I had dozed off for about 30 minutes when Janet awake and me. She was dressed and all was in order. I picked up my pants and reached for my car keys. Pushing the remote unlock button, I heard the two beep.

"In the backseat, behind the driver, you'll find a bag." I said. "I will call you in a week."

I watched her retrieve the bag from the backseat and clicked the car locked when she closed the door. I watched her drive away.

There was a small box of candy and $1000 in cash in an envelope.

A week later I called her and we set up Thursday the next week for meeting. I asked her to leave her car in the parking lot of the grocery store so I could pick her up. She hesitated, but agreed.

I found her sitting in her car far from the entrance to the grocery store. She left her car quickly and entered mine.

"There are a lot of white Impalas on the road." I assured her and it appeared she put it out of her mind.

"You gave me too much money." She said, as I rolled out of the parking lot.

"Did I!" I replied. "Did you like the candy too?"

"Your terrible! Yes, I liked the candy too."

She wore a skirt as I had suggested. I had made up my mind on one thing, the two of us having a nice lunch, but I wasn't sure how the afternoon would progress. I figured a skirt might make anything easier.

Momstheboss
Momstheboss
3,114 Followers