Loading...When I saw Mrs. Crowley at the supermarket I had to smile.
The woman who worked down the hall from me looked as good in her recreation clothing as she did in her business attire. That was quite a compliment, because she was always impeccable with her work clothing. Prim and proper, nothing out of place, everything put together quite nicely.
She was in the produce aisle when I spotted her. Her beautiful behind looked just fine as she bent over to inspect some beefy cucumbers, eying first one and then another before picking one out. Just her hands caressing the vegetable brought a stirring to my pants.
I guess you could say I lusted after the woman. I really did, as in more than two years of working down the hall from her I’d watched that perfect ass sway to and fro as she went from her office to meetings or to the cafeteria.
Mrs. Crowley was in a high middle management position, a powerful woman with a large staff. She was known as a good boss, one who listened to her employees and made sound decisions. She had a wonderful home in the suburbs, a husband with a good job of his own, and two smart, athletic kids.
Some figured she was in line for a Vice President’s office, others thought that might just be a stepping stone to a corner office on a higher floor.
All I knew was that she had a wonderful ass.
I’d lusted for that ass for the entire time I had known her, and looking at her in the produce aisle I had to smile. You see, for the last three months I had been secretly seeing the women 10 years my elder on the side.
It wasn’t planned — how can you plan such a thing? But it was real.
I sauntered down the aisle and stood next to the woman as she had moved over to some long, thin carrots. “Do you like any of them?”
Startled, the woman looked around, and then smiled. “Not as much as yours!”
“Oh, Mrs. Crowley, you are so bad. Here I thought you were planning out a salad when you were really looking for, uh, bedtime company.”
The woman smiled a smile that could brighten a room.
We had not planned on meeting at the supermarket, we had to be very discrete in our meetings, but it was an innocent meeting that wouldn’t draw attention. Just a chance meeting by co-workers at the store, right?
How we got together was equally by chance.
As mentioned, I had ogled the woman often at work. I thought I had been careful, although I had mentioned to my friend Rick that Mrs. Crowley was indeed the Cougar of the building, a MILF who was the object of my night time obsessions.
Apparently, though, I wasn’t as careful as I had thought.
When I came to work one morning there was a note for me to see Mrs. Crowley. As it could only happen, I was a half hour late that morning.
I sped to her office and her secretary waved me right in.
“Close the door, Mr. Robb.”
I did, and stood in front of her desk.
“Sit down.”
I did.
“Working half days, are you?” said the woman. “I thought Mr. Dawkins ran a tighter ship over there.”
My boss must not have noticed my lateness, but I mumbled my excuse. “Car trouble, mam, I had car trouble today.”
She smiled, and I noticed for the first time how it brightened the room. That smile I could never tire of.
“It’s okay, it happens,” she said, pausing for a few seconds. “I guess you are wondering why I asked you in today?”
“Yes, mam.”
She looked at me, this time without the smile.
“Last week I was in the conference room, working on tidying up some papers for my speech next week. I dropped some papers and picked them up. I rearranged them. Do you remember?”
“I uh, I, well, I um,” I stammered.
Of course I remembered. I was standing outside the room. Staring at her. Lusting for her. Thinking how good she’d look bent over the conference room desk.
“Stop stammering, Mr. Robb. You do remember?”
‘Uh, no.”
“So you weren’t voyeuring — she said the word in a dirty way — me? You weren’t staring at me?”
“Why no, Mrs. Crowley.”
She looked at me in disgust. “I don’t like liars, Mr. Robb. You know, it’s like when a guilty party asks the judge for forgiveness, throwing himself at the mercy of the court.”
I was confused.
“There is a mirror in the conference room, Mr. Robb, and when one, uh, bends down a little a looks up, well there is a perfect view of the conference room door.”
I was positively busted.
We looked at each other. Stared at each other. Eyes fighting each other from across the desk.
“I am so very sorry, Mrs. Crowley, I couldn’t help myself,” coming clean to the woman. “You looked, well, so very nice, and I couldn’t help watching you.”
“You watch me a lot, don’t you, Mr. Robb,”
I nodded my head yes.
“Does your wife know?”
This time I nodded no.
“Would she like it if she knew?”
Another no.
“Then why do you do it?”
I didn’t know what to say. So I kept quiet.
The woman looked at me and smiled that smile. “Look, Mr. Robb, nothing is going to happen here. You aren’t in trouble, okay? You can leave right now. I just find it interesting that you would be, uh, looking at an older woman the way you do when there are so many young girls with better figures, more voluptuous, around the office.
“I mean, if you like looking at girls, there are a dozen beautiful ones working here. I know the guys in the office look at Jenny and Stephanie and Nancy as if they are sex goddesses. I heard a couple guys talking inappropriately about Allison’s great, how did they put it, pair of melons?
“So with all that female, uh, talent in the office, why are you spending time looking at my old rear end?”
Again I stared at the woman.
“Do you really want me to answer that?”
“Uh huh.”
“No repercussions?”
“You have total dispensation, we are not having this conversation. I just can’t figure this out,” said the mature woman.
I took a deep breath, wondering what this revelation might do to my career. I decided to come clean.
“It’s because your backside is so very beautiful. It’s, well, the best ass, err, backside, in the building. It’s sexy, sensual, and when you wear tight skirts it is red hot.” I couldn’t believe I said what I said, but hell, she asked.
The woman smiled and said I had made her day. “You are a bad boy, but I think I will let you go. Sometimes a woman likes to hear such things. But, I have to say, it’s probably not a good think for you to be staring at my ass during the day. Someone might notice, someone no me, and it would be very embarrassing for you.”
I nodded my head.
“Now get to work Mr. Robb.”
I exited the room with a hard on.
Over the next few weeks I held my eyes in check, evading Mrs. Crowley’s swaying as much as I could. I didn’t know what to make of our little meeting. I think it was merely a warning for me to be careful and not become known as someone who is constantly stalking or voyeuring a person of the female persuasion. There are policies against such things, as you can imagine.
Still, I loved to sneak glances when I could at the women. I particularly liked it when she wore a flared tartan skirt with stockings. It was a modest skirt, to her knees, but it accentuated her ass and I loved the way it flowed from side to side when she swayed down the hallway. I wondered if she wore pantyhose or thigh high stockings.
My imagination, late at night in bed, had her in a garter belt and stockings and wanting me to inspect and kiss her ass before bending her over her office desk and taking her hard and fast. That’s how my orgasm came, hard and fast from thinking of her in such situations.
Almost two months to the day I was moping around work. My wife had gone to visit her mother for a week, and I was bacheloring around and a bit lonely. Sitting at my desk late one night I attempted to finish up some things for the next day when I was startled by a sound from down the hall.
It was Mrs. Crowley, and she was swearing.
Hurrying down to her office, I asked if I could help.
“It’s this damn printer. Jammed again. I need this report first think in the morning and, well, shit …”
I examined the faulty machine, trying everything I knew. Nothing seemed to work until I pulled apart one piece of the overhang and shut it. Voila, it worked!
“You are a lifesaver, Mr. Robb! Thank you.”
It was at this time I noticed the woman was simply lovely. She must have come back to the office after having gone home and changed, because she was in a stunning black cocktail dress that featured a plunging neckline which accentuated her breasts. She was adorable.
“You are staring again, Mr. Robb, I thought I talked to you about that.”
“I can’t help myself, you look so beautiful.”
The woman shook her head. “You are incorrigible.”
Sometimes the stars are aligned, sometimes lightening strikes. Who knows why?
On this night the planets were in perfect order, I rolled seven sevens in a row. I hit the lottery and a jackpot at the same time.
“My husband said I was fat.”
“My wife said I will never amount to anything.”
We looked at each other and laughed. “He’s so wrong,” I said. “So is she,” said Mrs. Crowley.
My co-worker, an executive of the firm, looked at me for a minute, and then said quietly, “I need a hug.”
What’s a guy to do? I hugged her.
That hug lasted a minute, at which time my hands started slowly down her back. I felt like a kid in high school in the basement with a girl for the first time. Slowly my hands crept down her back, waiting to be stopped. Waiting for her to push me away. Waiting for her to remind me we were married and that while a hug was nothing, that wandering hands was really something.
Mrs. Crowley began pulling away. She looked into my eyes, smiled that smile and then moved toward me again. I kissed her, locking lips, exchanging tongue lashes while my hands began their downward travels. Soon I was cupping her ass while passionately kissing the woman I had been dreaming about.
We kissed for a few minutes while I explored her ass with my hands. It was incredible, firm yet soft. I remember wondering what kind of panties she had on under the dress. Soon, though, she broke the kiss.
“We shouldn’t be doing this.”
“I know.”
“But I have been thinking of you, your staring at my ass,” said the woman.
“Mrs. Crowley…”
“Brittany.”
“Jon.”
“Close the door.”
I walked over to the door, looked around, closed and locked the door to her office. Striding back I gazed at the beautiful woman who was leaning against her desk. Again we kissed, and my hands went right back to her ass.
This time, though, they were on a more important mission. This time I started not only feeling her ass but also lifting her dress. Inch my inch I moved the dress up her thighs. While I couldn’t see anything, I did bunch up the dress as I moved it up. Soon, I had the hem in my hands.
The kisses continued as I held her dress up in one hand and reached down with the other.
I felt bare ass cheeks and slowly stroked the ass of my dreams. She was wearing a thong, so I had complete access to her backside and I used this opportunity to caress her ass like none before. Soon I reached down with my other hand, holding the dress with my wrist, and used both hands to play with her soft ass.
My fingers danced up and down her ass crack, playing around and around, before one of my hands slipped around to the front. There it found a damp patch of panties.
Throughout all of the finger action below was the swapping of spit above. The women could sure kiss, and I used the opportunity to exchange kisses in a way I hadn’t since Betty Ann and I were making out behind the grandstands years before.
Brittany was an outstanding kisser. I would have never guessed that the woman who was destined for stardom in our company was a good kisser. It was as if I thought the higher one went up the corporate ladder the less sexual they became. That was not the case, as the woman was a passionate, sensual kisser.
While we continued our kissing my fingers were playing with her pussy, and soon made their way inside the elastic bands and directly onto her wet snatch. I played with her clit before slipping inside her while my other hand was playing with her ass crack.
“I want you, Jon, I want you in me right now.”
I wasn’t going to argue with her authoritative tone.
I turned the woman around, bending her over her desk. That’s when I looked down and noticed the thigh high stockings which caressed her legs. Slipping down her thong, I began kissing the ass I loved so very much for months from afar. All the while I continued to finger her pussy.
Somehow I unhitched my pants, lowering them and my boxers and unleashing my cock. I don’t think it ever had been larger. Maneuvering behind the woman, I began rubbing my dick up and down her slit before finding the hole and slowly slipping my dick inside her.
It was marvelous. It was incredible. I thought I’d cum so I started thinking about Sister Theresa Joseph in school. That dulled my sensation in my mind, anyway, and I was able to continue to screw Brittany from behind.
“Oh that’s good, fuck me Jon, fuck me hard.”
If nothing else, I am good at following instructions. I stood behind the woman, hands on her ass cheeks, dick inside her pussy. I banged in and out of the woman bringing grunts and groans from in front of me.
My hands slipped around her for better positioning and I was able to make perfect contact with her. We humped each other like long lost lovers, as it seemed like I knew the body I was fucking for the first time.
Moving her slightly away from the desk I moved a hand around and began fingering her clit from the front while fucking her from behind. Soon I heard her gasp and shiver.
“I’m coming, I’m coming,” was all she said before she collapsed onto the desk.
I continued fucking her, slower now, as she recovered from her orgasm. My own orgasm was imminent, but I held back as I wanted her to be fully back with me before I busted my nut in her.
Coming down from her orgasm she sort of purred how good it felt.
“Oh, Jon, that was incredible.”
“You bet, Brittany, you feel wonderful,” still not believing I was banging the beautiful woman right over her own desk.
I rocked in and out of her as I marveled at how wonderful it felt. Slipping in and out of her sloppy pussy I couldn’t help thinking about how erotic it was to be fucking a big shot of the company in her own office. That thought brought a bouquet of sensations to my dick.
“I’m going to cum,” I groaned loudly.
Mrs. Crowley — Brittany — gasped, “NO” and pushed back, pushing me away. Startled, I continued rocking but had left her cunt.
The woman pushed some more stood up, then slithered to her knees and somehow grasp my cock while doing so. She stroked once, twice, then opened her mouth just as I began shooting my pent up sauce.
Blast one hit her face, blast two was into her mouth and the rest poured out of me into her sucking mouth. The woman sucked on my cock like it was the lifeline to the fountain of youth. Her face looked beautiful while her mouth milked my dick. It was so very erotic watching the powerful woman relegated to wanton cocksucker on her knees in her own office. It was especially hot watching my cum cascading down her face while she milked me dry.
Brittany continued her blow job long after my orgasm had subsided. It was so very erotic watching the older, mature woman work on my cock. I had half expected her to be more like my wife and suck it until it was ready to cum then pull it out and shoot to the side. But it wasn’t the case. Brittany sucked with a special passion that seemed solely to the point of me enjoying myself.
I certainly did enjoy myself. I couldn’t remember a blow job even half as good as my older co-worker has just given me.
Positively sated, my dick shrunk in her mouth. Satisfied, she rose and we kissed. While never a fan of cum, I could taste myself on her tongue as we share a passionate kiss. We exchanged my sauce, but ultimately she swallowed the majority of it.
That was the first of many encounters with the mature, married co-worker formerly of my dreams.
I had to smile when I saw her in the produce aisle of the supermarket. I was supposed to be getting a handful of things for dinner, but seeing the woman brought other ideas to mind. As we exchanged pleasantries I marveled at her infectious smile.
We both had to get home soon, I knew, but there was time for a quickie of some sort in the parking garage.
“Mrs. Crowley, if you hurry I could walk you to your car. I think we could work something out better than a carrot.”
The woman smiled. “I like the way you think.”
But that’s a story for another day.