Jennifer Ch. 1

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Successful man finds a 'Supplemental Relationship'.
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Part 1 of the 2 part series

Updated 10/02/2022
Created 12/20/2001
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Steve9502
Steve9502
10 Followers

"What the hell is the matter with you?" I thought to myself as I scanned the classifieds. "You're 42, own a successful business, have 2 beautiful kids, and you're taking a chance on throwing it all away!! You must be out of your damn mind, you moron!!"

Yes, I was married, and scanning the classified ads didn't seem the proper thing for a married man to do, I thought to myself. But, since I had gotten "The Word" from my wife some months ago, it just didn't seem to matter. After my most recent and unsuccessful attempt to make love with her, she turned to me and said,

"Look, Richard, she said, it's not that I don't love you anymore, but sex is just not a priority for me. We're both too old for that nonsense, and we have too many other things to do. If you want sex, you're just going to have to look elsewhere. Just don't do anything stupid". And with that, she rolled over and went to sleep. "Too old", she said. Sigh. I was 42.

It's not like I hadn't seen it coming, but I just chose to ignore it. We had been married for 15 years, and always got along ok, but all the spark was gone. We didn't have fights, or argue, but neither did we kiss, or hold hands, or do any of the things that make a relationship worthwhile. It was just... moribund. For the last 6 or 7 years, the sex was at best, incredibly boring, and at worst, (as was most often the case) non-existent. It had degenerated to the point where our lifestyle resembled a couple of roommates, more than that of a married couple. The kids were growing up, and were out more then they were home. All of these things were swirling around in my mind when I saw the ad:

Wanted: One intelligent, witty, professional, reasonably attractive, well-mannered and married man for "supplemental relationship" with married woman. I require you to be 35-45 years old, married and physically fit. Sense of humor a must, with extra points if you make me laugh. I am college educated, (advanced degree) employed in upper management of a large firm. I am financially and emotionally secure, and you must be too. To qualify for consideration, you must be able to identify the following things (without using a reference):

"All Things Considered"

Thomas Paine

Alpha Centauri

Dorothy Parker

Tritium

If these requirements sound stringent, it is because they are. I know what I want, and more importantly, what I don't want. I'm far too busy to spend time sorting through replies from morons, losers, alcoholics, and the "emotionally challenged". If you think you qualify, send an e-mail reply to Jennifer@xxxx. com

Good Luck.

I laughed right out loud as I read the ad. "Wow!! This is definitely a woman who knows what she wants!!" I thought, "and I like that in a person, especially a woman!! She reminds me of me!!" I said, still laughing. Then it also occurred to me that she might also be one of those women who goes from zero to bitch in 2. 1 seconds, and the "bitch switch" sticks in the on position!! Hmm... decisions, decisions. Then I mentally chastised myself. "Why is it that whenever a woman is the least bit assertive, men automatically classify her as a bitch? Stereotypes abound, I guess. Well, only one-way to find out. Maybe I'll send her a note. Let's see what she has to say about this", I thought, and I smiled to myself as I started to type.

"Hello Jennifer: Saw your ad, and though your requirements are quite specific, I'm more than qualified. But the question is, do you measure up to my standards, and are you interested in finding out?" I smiled and thought, "Take that, sweetheart!!"

"I'm 42, and quite fit, I swim a mile or more a day. I still have all my hair and teeth, neither of which was purchased from a store. I run my own consulting business, and have a MBA from Columbia. I'm married, and secure emotionally, financially etc. By the way, in reference to your little quiz...

National Public Radio afternoon news show.

Famous author, who, during the Revolutionary War, wrote the hugely successful pamphlet, entitled "Common Sense", which was a treatise in support of American independence.

Nearest star to our own galaxy.

Famous woman writer and satirist of the 20's and 30's. (She was the one who coined the phrase, "If all the girls who attended Yale were laid from end to end, I wouldn't be a bit surprised!"

A radioactive isotope of hydrogen, sometimes used in the production of nuclear weapons.

Checking to see if your applicants are well versed in several disciplines are we? Interesting strategy. It's clear from your ad that you're intelligent, witty and focused. But the question remains, do you think you're the ONLY person with those qualities? I'll be interested to see your reply. If you think you're up to meeting an equal, you may call me, or e-mail to Richard@xxxx. com.

The phone rang the next morning promptly at 9:30.

"Good Morning", I answered, Richard Callaghan speaking. "

" Good Morning Richard, a voice said, this is Jennifer... you answered my classified ad?"

"Well, this is a surprise, I replied, I was wondering if you would call. "

"How could I dare not to reply to a challenge like that?! You're a real wise guy, aren't you? She said. But I like that. Do you think you're up to all of this?"

"As are you, I'm sure. "

"Free for lunch?"

"I can be, who's buying?" I said, and I heard her chuckle a bit.

"How bout going "halfsies"? She said, still sounding amused.

"Bella Monte's at 12:30?"

"Deal. How will I know you?"

"I'll get a table in the corner, and have a folded newspaper on the table. " "Hmm... sounds like a bad spy movie!"

"If you order a vodka martini, shaken not stirred, I'll leave!" she said, still chuckling. By the way, you've already passed the "make me laugh" test. See you at 12:30. "

She entered the restaurant promptly at 12:30. I knew it was Jennifer from the way she carefully scanned the room before speaking to the maitre 'd. He guided her over to my table, as I stood to say hello.

"Hello, Jennifer, I'm very pleased to meet you. " I said as we shook hands. She had a nice handshake, I thought. Firm enough, but she was not one of those women who try to make you think they have a set of balls under their skirt by squeezing your hand until it cracks.

"Please sit down. I've taken the liberty of ordering us some wine. "

"Thank you, Richard, she said, as the waiter arrived with the bottle. It's good of you to meet me on such short notice. "

"How could I refuse? I said. You wrote the best classified ad I've ever seen!"

"Well, she said chuckling, it certainly was... specific. I didn't get very many responses to it, and the ones I did get other than yours were usually obscene and mostly anonymous. "

"I'm not surprised. You know, your ad makes you sound like a bit of a "hard ass", and though I don't know you very well, you don't strike me as that sort. Why did you write it that way?" I asked.

She thought about it for a second, and then looked directly at me.

"You're right, it definitely does, and I designed it to read that way on purpose. I've discovered that if you don't know exactly what you want, and are afraid to ask for it, you never get it. I know what I want, and I'm not afraid to ask for it. "

"So I have noticed. For example, your ad specifically requested a married man, rather then a single one. Why is that?" She sort of sighed, and looked out the window for a moment, and then she said,

"I have everything I could want in my little world except decent sex. I love my job, I'm very good at it, and I make great money. I have a great life, and I wouldn't change it for anything in the world. My husband adores me, but he is quite a bit older than I am, and truth be told, he's just not very good in bed. Well, that's not exactly true. He's actually lousy in bed. Maybe he was never taught properly, and I've tried to show him how to please a woman, but to no avail. His idea of great sex is to roll me over once a month, stick it in until he cums, and then roll back over and go to sleep. In all other ways, he's a wonderful man, but sexually, I need more. I wanted a married man because frankly, all I want to do is get laid. I want to get laid well, and often. I don't need to fall in love, or have anyone fall in love with me. If I found a single man, there could be... she paused for a moment, searching for the right word... entanglements that I don't want. I don't need to have him get any ideas that there is any more to the relationship than sex. When you stop and think about it, it's fairly simple, isn't it?"

"Honesty usually is, I said. It's also an interesting approach, and one that I don't see too often. Frankly, I think most men are put off by an assertive woman. I, however, find that a very attractive quality. " I said, looking directly into her blue eyes.

"Well, she said. You are a rare one aren't you?"

"Modesty forbids me from telling you what a jewel I am, I said, laughing. But give me a while and I'll grow on you. "

"Sort of like a fungus?" she asked, laughing.

"Yep. Or maybe kudzu. " And we both smiled.

Lunch was wonderful. Bella Monte is renowned for their linguine, and as always, it never failed to please the pallet. We drank wine, laughed, and talked about everything under the sun. I love old movies, and so does she. As a matter of fact, we both agreed "Casablanca" was our favorite. I was immediately comfortable with her, and found her to be every bit as intelligent and witty as I had hoped. It was about that time that I realized she was beautiful as well. Raven black hair, tall and lithe, deep blue eyes, and small but nicely shaped breasts. I caught myself staring at them a couple of times during lunch, and forced myself to look at her face before she caught me staring at her chest. After a while the conversation started to slow a bit. I looked at my watch, and it was approaching 2:30.

"Say, I said, it's getting a bit late. Do you have to get back to the office?"

She sort of smiled at me and said,

"I was planning on taking the rest of the afternoon off. How about you?"

I grinned and said,

"Me too. I run my own business, and you know what they say, "It's good to be the king".

"I see we think alike. Why don't you see if you can tell me what I'm thinking about now?" I suddenly felt a lovely nylon covered foot working up its way up my leg, and start massaging my crotch.

"Well, I hope you're thinking about having lunch with a man who won't be able to stand up from the table any time soon, if you don't stop that!"

We were both laughing. I left some money on the table.

"What do you think about getting out of here?"

"I think that's a great idea. "

We walked out into the parking lot.

"How about if you follow me?" she said.

"No problem. I replied. Where are we going?"

"It's surprise. "

I followed her down to the oceanfront. We pulled into the parking lot of a hi-rise condominium on the water. As we walked through the door, the doorman greeted her.

"Good Afternoon, Ma'am. " She smiled and nodded as we walked to the elevator. We entered and she pushed the button for the 16th floor. When the doors closed, she turned towards me and said,

"Now's your last chance to back out. "

"Fat chance of that," I said, and reached over and gently caressed her cheek. She looked at me and said,

"Richard, if you don't kiss me this very second, I'm going to die!!"

The elevator ride ended much too soon.

We exited the elevator and walked to her condo. She opened the door, and I followed her in. It was quite lovely, tastefully decorated and as she opened the curtains to the patio door, it revealed a splendid view of Chesapeake Bay.

"Wow! I said. That's a some view you have here. "

"It's lovely isn't it? I sometimes sit out here for hours, just watching the water, and ships as they go by. "

"It sure is. By the way, not to change the subject, but I would really hate to be caught by a jealous husband, and promptly shot, I said. Is it a good idea for us to be here?"

"He doesn't know about this place. It's all mine. I rented it a couple of months ago when I decided to do this. "

"Nothing like being prepared. " I said. You are definitely a woman who knows what she wants. "

"Yes, Richard, I am. And right now I want you to take me to the bedroom and make love to me. " And with that, she took me by the hand and led me back through the living room, and then into the bedroom. It too had a large glass door that opened on to the patio, and she opened the curtains wide. Her back was to me as she opened the curtains. I walked up behind her, wrapped my arms around her, and started kissing her neck. I felt her take a deep breath, and then she started pushing her lovely bottom against my hardening penis. My hands moved to her breasts caressing, then gently pinching her nipples. I started unbuttoning the buttons on her blouse, and she turned around and we started kissing. Deep, wet, glorious kisses that touched each other's souls. Our hands became more and more frantic as we undressed each other. I was unbuttoning her blouse as she struggled to untie my tie. My braces went off my shoulders, and then followed my pants onto the floor. Her blouse came off, and then my shirt, and all went onto the growing pile of clothes at the foot of her bed. She reached inside my briefs, and took my already hard penis in her hand, and slid my underwear to the floor. I unhooked her bra, and slid it to the floor as my mouth found her right nipple.

"Oh my God, she said. Please don't stop... I need this so bad. " I was licking and sucking her nipples like I'd never be able to do it again. She had the most marvelous breasts, firm yet soft. Her nipples stood out a good half and inch from her breasts, and from noises she was making, they were apparently quite sensitive. After so many years of trying to arouse a woman who wasn't interested in being aroused, I was in heaven.

My tongue worked its way down to her panties. I began to lick her through already soaked panties. She reached down and pulled her panties off onto the floor, and lay back on the bed with spread legs.

"Richard, take me now. I need you in me. " She commanded.

"Soon my love, soon. " and with that I buried my face between her legs. I began sucking her, running my tongue deep inside, but then coming up to suck on her clitoris. I turned my head a bit, and soon I had her whole clitoris in my mouth, and I was licking it and running my tongue all over it. She was pulling at my head, and her back was arching against my mouth, it was a wonderful feeling. Her stream of consciousness was music to my ears as she started to orgasm.

"Oh God... Richard... Suck me... Oh yes... Suck me harder... Oh God... Oh... Yes... Now!! Here it comes... Oh God... NOW!! I sucked her hard until she pushed my head away. As she caught her breath, I kissed my way back up to her face, as she reached for my throbbing penis.

"Jennifer... I need you so bad. "

"Oh Richard... put it in me now. Take me hard... please"

As soon as I entered her, it was like we had been together for years, rather than hours. She moved with me, and we writhed with each other hard. I put her legs over my shoulders, and drove as deep as I could. We banged against each other unmercifully, and loved every minute of it.

"Oh God... Richard... I'm going to cum again... harder... harder... oh yes. "

I was pounding her as hard as I possibly could. My balls were slapping her on the ass as we fucked each other for all we were worth. I felt my orgasm start building from the bottom of my balls.

"Oh Jen... me too... I'm going to cum... oh... here it cums... "

" Cum with me Richard... cum now... oh God yes... NOW!!" And I filled her with my cum. We climaxed together, and it was truly magnificent.

We both just lay there for a minute as we struggled to catch our breath.

All of a sudden, she started to laugh.

"What in the world are you laughing about, woman?" I asked. I couldn't believe after the great sex we just had, that she was lying there laughing!!

"Remember when we both said that we thought "Casablanca" was the greatest movie of all time?"

"Uh-huh?"

"Well, to steal a phrase from that movie, "Louie, I think this is the start of a beautiful friendship!!"

I just nodded.

To be continued...

Steve9502
Steve9502
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