I Love Older Women

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A mature lady admirer speaks of his latest tryst.
2.2k words
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Part 1 of the 3 part series

Updated 10/30/2022
Created 01/28/2008
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I will make a confession right here and now: I love older women.

Ever since I was eighteen and lost my virginity to my next door neighbor who had really given me an education in sex that one could have learned neither at home nor at school, I couldn't think about either going out with or fucking any woman under forty.

I admit I have had sex with a few chicks my own age over the years, but I couldn't really get off with them.

There was just something about a woman so much older that was more of a total turn on for me.

Last summer when I was twenty-seven, I had gotten a good job at an auto dealership, and while my sales weren't mind blowing, I was doing quite well.

At the time I had gotten my job, Herb had been our boss. He had owned the dealership, but he was jovial and fun for an old man, and popular with everyone from the managers all the way down to the clerical help.

When Herb died at eighty two later that year, knowing the fun times with the old man were over, everyone wondered what was going to happen to the business while we attended his funeral.

A couple of weeks later, we got our answer.

Herb's two sons had no interest in the dealership, so the next person to fill the boss' space had been his daughter, Kerry.

While the old man had had a open-door policy and often came down to mingle with both staff and customers, Kerry was a total uptight bitch who only saw people "by appointment only" unless she called one of us up to the office.

Plus she appeared to not really give two shits about the customers; as long as they could afford the car and paid their garage bill, that was all that counted.

In spite of her icy demeanor, I found myself attracted to her.

While most of the sales staff and mechanics wouldn't have minded banging Melissa, the twenty three year old blond office manager, I was secretly wondering about what our ice princess, forty six year old boss lady was like totally naked.

Kerry wasn't an easy person to like, especially when she would rail on most of the staff about the most minor thing, sometimes firing people on the spot.

I don't know if it had anything to do with the hellish divorce she had just gone through or it was her general demeanor, but nevertheless, when some of us saw her coming, we made the effort to steer clear.

Fortunately for me, I was one of only very few that had yet to endure her wrath.

When it came up on my first year anniversary, management positions were opening up and quite a few of the guys that either were old grunts that had been there for years or guys had come there after I did scurried to apply for a promotion, trying to kiss up to the boss in the meantime.

Personally, though I had put in my name, I found the way the other guys had been acting totally pathetic, considering that Kerry was a smart woman and would likely see through their facades.

Thinking that though my sales numbers had been good, she would probably go with "a more mature guy" anyway, so I just kept myself back and went on doing the job that I usually did on a daily basis.

I didn't think anything more about the whole promotion thing; by the time Kerry had called me into her office one day, I figured all the positions had been filled by then.

I had found it odd that she would call me into her office during her usual lunch break, but figuring it was something important, I didn't protest.

Still, I was racking my brain with wondering what the hell I could have done wrong. After all, that was usually the only time she called anyone upstairs.

But when she saw me, Kerry gave one of her rare smiles and beckoned me in, telling me to close and lock the door so we wouldn't be interrupted.

"Have a seat," she added.

"Look, I don't know what I did, so let's cut to the chase," I said as I sat down. "What's the problem?"

"Paul, why would you think you did anything wrong?" she asked, a look of confusion on her face.

"Well, usually---"

She stopped me, smiling again. "Right. I guess I have a rep for being a hard ass, unlike my father. But rest assured, you are not in any kind of trouble. On the contrary, I'd like to interview you for one of the management positions."

Now it was my turn to be confused. "I thought you would have filled those by now."

"I really haven't found anyone that is both personable and qualified outside of Dorothy, and she's way overdue for one of the management jobs. Thirty applications for two jobs, Paul, and I can't find anyone else that is close to being qualified."

"What about some of the older guys?" I asked.

"Those goof offs? If anything, most of them should be fired. I don't know why Dad even bothered to give them jobs, much less let the lazy assholes keep them. It's not like they have great numbers, at least not as good as yours."

"So why keep them around?"

Kerry sighed. "I guess I could let them go. But since we're short on help, I have to keep them around until someone better comes in here."

She then looked at me with those beautiful blue eyes. "Perhaps someone with your work ethic and compassion toward the customers."

"I thought you could cared less about customers."

"Paul, just because I'm not downstairs kissing ass all the time like Dad did doesn't mean I don't care. Those customers are the backbone of this business, and when they go away happy, I'm happy."

"I see," was all I could say.

"You know, I bet you'd make an excellent manager. It's just that I need to see some qualifications outside the fact that you are a good sales person."

"Well, let's see....." I began, before she came over and sat on the arm of my chair.

"Let me tell you," she said, giving me a sexy stare. "You have compassion. I've also notice that you spend a lot of time answering customers' questions, no matter how silly they may be."

"I always try to get a feel what they want," I nodded.

She smiled down at me again. "And you also seem to have a lot of younger buyers, unlike a lot of the guys down there. You take the time to make sure everything is right. Do you know how many times I've gotten complaints about salespeople rushing through transactions?"

"I'm sure you had your share," I replied.

"You guessed right," Kerry nodded, her hand on my shoulder. "But never even one complaint about you, Paul."

"Not one?" I was shocked.

"None. And may I add one more thing. I hope you don't find this forward, but in addition to the things I pointed out to you, you are also very attractive. Sure, Dorothy will bring in more of her share of women buyers, but what I really want is someone with a bit of sex appeal that will really draw them in. I think you may be that man."

I cleared my throat and thanked her before realizing her hand was on my crotch.

"But you have to show me that you are that man," she added, not taking her eyes off of me or her hand off my dick as I felt myself growing hard under her touch.

Holy hell, I thought, my boss is coming on to me. Worse, I actually LIKED it!

"You know, Paul, I always found you to be very sexy," she confessed. "But I never acted on it because of going through my divorce, plus I was too old for you."

"Well, while on the subject of confessions, I kind of found myself attracted to you too," I said, barely getting the words out.

"About that age thing, you aren't too old for me at all, Kerry. Actually, I can't remember the last time I dated a woman under forty."

"You can't be serious," she said, eying me skeptically.

"It's true," I nodded. "I love older women. There's just something hot about them. And not to be crude, if it came down to me either fucking Melissa or you, you'd win hands down."

"Ooooh," she purred, kneeling in front of me to undo my zipper, "I think you're very close to getting the second position, Paul."

I could tell that Kerry was dying to give me a blow job as she pulled my cock out of my pants and licked my pre-cum from the tip.

She then wrapped her sexy lips around the head, slowly taking my cock into her mouth inch by inch.

Kerry teased me with her lips and tongue, moving them up and down then off.

She did this until I groaned and pushed her head down, my hands tangled in her dark hair while fucking her face.

My throbbing cock was deep in my boss' mouth and I didn't release it until I shot a large load of cum down her throat.

She licked her lips, showing how much she had enjoyed swallowing my jizz, then got up to remove her clothes.

I too got up to strip, checking out Kerry's body, noting how sexy she was for her age, before bending her over the desk, kissing her neck and ears.

She moaned and moved back against me a little, making me guess that Kerry hadn't had a good fuck since her divorce.

Hell, I couldn't even remember the last time I'D gotten laid, so it was going to be quite an experience for both of us.

I moved my lips down, kissing Kerry's back until he reach the top of her ass.

Parting her cheeks, I licked all the way from her ass to her cunt lips.

She moaned as I began to lick her pussy. My tongue not neglecting any part, I could tell she was on the verge of orgasm.

She came hard, with me licking up every shot of her cum before I stopped, came up and turned her around in front of me, then bent down and kissed her deeply; Kerry took my tongue into her mouth, tasting the juices from her pussy.

"I've never screwed the boss in any job I had before," I said, looking directly at her.

"There's always a first for everything," she replied huskily, leading me over to the couch to finish what we started.

Pushing Kerry back onto couch, I crawled down between her thighs and began to eat her pussy again, making her moan so loudly that I put my hand over her mouth, so no one outside could hear, before she came again.

I turned Kerry over and pulled her toward me, then thrust my cock into her so hard that we both almost lost our balance. I gripped her sexy, full hips with my hands, fucking her harder and deeper.

"Is this what you meant by me having other qualifications?" I growled. "I think you would like to have more of these, wouldn't you, baby?"

And with that, I slammed into my boss' pussy harder. She tried not to cry out too loud, btt it seemed the harder I fucked her, the more we moaned to the point neither of us gave a shit of who heard us.

God, her pussy felt so good; I felt that I could fuck her for hours!

Kerry met each of my strokes, pushing back onto my cock as my balls slapped against her ass. Our bodies joined together in tune with each other's needs as I shoved my dick all the way in to her hot cunt until I was totally buried inside her, wishing this would never end.

But it was about to; I could feel myself about to explode at any moment and slowed down my strokes in an attempt to make the hot fuck I was having with my boss last a bit longer.

Once it appeared that wasn't going to work, I sped up my thrusts again, really putting it to her.

"Oh fuck, baby, I'm going to cum," I panted. "I can feel your muscles around my cock. I'm going to shoot it in your pussy NOW!"

Hot shots of semen filled Kerry up as I pulled her back onto my pole, her box exploding and sucking my cum into her while her own orgasm coated my dick.

Laying in a heap on the couch still inside Kerry, we lay there together for a few minutes until our breaths slowed and I finally pulled out.

I got to my feet to get myself together and we got dressed while Kerry smiled at me, saying that I was very qualified, and to consider the job mine.

Taking my hand and pulling me to her, she then pushed me up against the wall, asking if I wanted to discuss my new job over dinner that night.

I had to be nuts to say no. I knew she would have a lot more in mind that just dinner.

Not that I am complaining.............I do love older women for a reason, after all.

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  • COMMENTS
2 Comments
AnonymousAnonymousabout 16 years ago
Very hot!

Not just this...all your stories are super hot! You really speak to me and my "older woman" fetish! I can't wait to read your next story! Mike

AnonymousAnonymousabout 16 years ago
Nice

A quick stroke story - but nicely done overall. What would have made it more enjoyable to me would have been a build up of tension between him and his boss. You tell us about how she is perceived, but I would have liked to "hear" interactions between the two of them, some sort of interplay before she just abruptly comes on to him. Otherwise, nice quick stroke story.

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