The Boss Gets Her Groove Back

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My name is Laura, and I am the Owner/CEO of a distribution company that my Husband founded many years ago. He passed away three years ago and rather than sell at a bad time I kept the business and continue to run it. I worked for my Husband at the company for many years as the Personnel Manager so I am very familiar with the operation and things are going well.

I put in a lot of time at the office, and that combined with the loss of my Husband has played havoc with my social life. All of a sudden I was the extra person in a group of couples who we had been friends with and the invitations stopped coming.

My sex life has suffered even more. I have male friends and acquaintances but I have discouraged any romantic approaches. Originally that was because of how much I missed my Husband and still loved him. But lately there is another reason too. I just turned fifty-five, and as I am sure you know your body changes as you get older.

Intercourse would now be very painful since I have ‘dried up’ as they say. I hope this isn’t too much information but it is necessary for you to understand the rest of this story. My vagina is now a dry, tightly closed slit and it stays that way even if I am feeling horny for some reason.

I believe I am still an attractive woman and I always try to dress stylishly and I have regular appointments for haircuts and coloring, manicures, pedicures, etc. My hair has gone gray but the salons efforts keep it looking like it did when I was young.

I have a membership at an athletic club that is a perk from the business, and I work out regularly with a personal trainer there. I maintain a slender figure and I am in pretty good shape for my age. This may sound vain but I think I look at least ten years younger than my actual age.

All of that being said, I haven’t had sex or even a real date in the three years I have been a widow. I confess that I occasionally masturbate to take the edge off. I fantasize about being fucked into ecstasy but I did not see how that was going to happen.

Let me get to the heart of this story. One afternoon I was taking a walking tour of the building and I climbed up the stairway to a storage area on what is actually the roof of the office enclosure. I was looking for a sample of a product in the dusty rows of boxes but I didn’t find it.

As I walked toward the stairway to go back down I saw a man down on the warehouse floor sitting in a slouch and leaning against the wall. He was in an area that is surrounded by high shelving and isolated. I looked carefully at him and recognized him as John, one of the fork-lift operators.

Then I was shocked to notice that he was masturbating while he looked at a magazine in his lap. Some kind of porn, I suppose. I stood still so he would not look up and see me and I could not help but notice that his penis was very long.

I knew that I should either call down to him to cease and desist, or else I should walk in the other direction to avoid him. I did neither; I was transfixed and curious and I could not take my eyes off of him.

In a few minutes he finished his task and ejaculated, and it shot up in the air and came down on the open pages of the magazine. It was an amazing amount of semen; it just kept squirting and squirting into the air. How very convenient, he did not have a mess to clean up; he just folded up the magazine and threw it in a nearby trash can.

I waited until he left before I went down the stairway and made it back to my office. I looked him up in the Personnel system and learned that he was twenty-five years old, not married, and had been with the company for two years.

I had mixed emotions about what to do next. Should I call him to my office and fire him on the spot? I couldn’t decide so I did nothing.

I went home and all I could think about all night was the sight of him stroking his long, large penis and ejaculating up into the air. I fantasized that it was my hand that jacked him off and I was covered in his semen when he finished. As I lay in my bed london escort I masturbated and gave myself an intense orgasm. Then I fell into a deep sleep.

The next day I decided what to do. I used the intercom and paged John and told him to report to my office. He knocked on my door promptly and I invited him in.

He asked why I wanted to see him so I cut to the chase.

“What were you doing yesterday afternoon in the corner of the warehouse?”

“Nothing” he answered with a guilty look.

“I wouldn’t say it was nothing. More like eight or nine inches of something.”

He was startled and he looked like a kid that got caught with his hand in the cookie jar.

I continued “Let’s not beat around the bush. In fact, speaking of beating I think you were doing what some people call beating your meat.”

His face was red as a beet, and he just looked down at the floor.

“I would like an explanation.”

With a lot of hemming and hawing he stammered though his explanation.

“It gets boring running around on the forklift all day. I have a strong sex-drive and I just needed some relief. Susie in shipping and I get together sometimes . . .”

He stopped short, realizing that he was just getting in deeper.

“So you take little Susie back in that corner and have sex with her?”

I visualized this petite young woman being impaled by his meat-pole, and receiving the kind of load he produced by masturbating.

I said “Look, we all get bored, and we all have needs. You are not the only one. But you realize that I would be fully justified if I fired you for this.”

He thought for a moment, and then said “I think if you were going to do that you would have already done it.”

Good point, I thought. He is pretty smart after all.

He said “Was there something you saw that you liked? Something that you wanted a closer look at?”

He had me. I wasn’t even sure what I was going to do when I called him up here, but clearly that was what I wanted, subconsciously anyway. Now I was the one with the red face.

He said “You must be one of those ‘Cougars’ or something. Well that is OK with me. Take a look at whatever you want.”

He faced me with his arms spread out and a smile on his face.

Years of sexual deprivation and frustration came to a head in my mind. I can’t explain how I got the nerve to do it, but I went over to him and knelt in front of him.

I unbuckled his belt and unzipped his fly, and pulled his jeans and underwear down to his ankles. His magnificent cock bobbed up in my face and I took it in my hand. It was growing and getting hard and it felt thick and heavy.

I don’t know how I got past my shame and embarrassment but I stroked it and kissed it and tried to get as much in my mouth as I could. I was out of control.

I wanted to make him cum in my mouth and swallow it but before he did he helped me to my feet. He said “Life is a two-way street. It’s your turn now.”

I knew what he wanted so I took off my skirt and my shoes, and pulled off my pantyhose. He led me to the side of my desk and I climbed onto it, with my butt right at the edge. I lifted my legs bent at my knees as high as I could and waited.

I color my hair but not my pubic hair which was very gray. I hoped that did not turn him off but clearly it didn’t. He pulled an office chair up in front of me and sat down and went to work eating my pussy. He licked the tight, dry slit and worked his tongue into it and found my clit.

He was very good at it, and I was on my way to an orgasm when he stopped.

He lifted his head and made eye contact and said “I want to fuck you now.”

“John, surely you can tell why that is not possible.”

He didn’t say anything further but he dipped his head down and this time he brushed my asshole with his tongue. It was like a fireworks explosion inside of me. Then he pushed his middle finger all the way up my ass.

I had never had anything up my ass, not my finger or someone else’s finger or Escort Dubai a vibrator or a medical instrument of any kind. I had never even had an enema so the sensation of his long bony finger sliding up in me was a new experience. It was very erotic and I began to think that it might be possible to take his cock in me that way.

We were locked in eye contact but even though not a word was spoken we communicated. He clearly wanted to have anal sex with me, and I tried to indicate with my expression that I wanted it too. To make sure he understood I nodded my head in an affirmative way.

He started to move into position but I stopped him.

“Wait a minute. I will be right back.”

I went into the private bathroom next to my office and I returned with an unopened tube of petroleum jelly. I opened it a smeared it all over the head of his cock, and then put some on the shaft all the way down to his balls.

“Try it now.”

I got back into my position on the desk and he helped to hold my legs up, almost touching my shoulders. He moved in close and with one hand he guided his cock to my asshole. When the tip touched me I flinched in surprise, and then he began to push.

He pushed hard but it would not go in. I said “I don’t think it will work.”

He replied “Just hold still and relax. It is going up your ass whether your ass wants it or not.”

Actually my ass did want it, or at least I wanted it up my ass. He adjusted his position so the angle was better and his cock lined up perfectly with my asshole.

The pressure kept building as he pushed harder and harder and then all of a sudden the head went into me. It forced my anus open and I let out a yelp.

I said “Ow! Stop there! Just wait a while.”

He did as I asked, and I tried to relax and let it happen. I felt like I was dangerously close to ripping or tearing wide open and then I would have the embarrassment of explaining it to an Emergency Room doctor.

Then the tight ring of my anus just relaxed and let go. I am not sure if it was my will power because I wanted more of him in me, or if it decided on its own that resistance was futile.

I said “OK. You can go deeper now.”

He eased it into me carefully, and with each little push I made a little grunting sound. The room was quiet except for me going “Uh. Uh. Uh.” as his cock disappeared up my ass little by litle.

I was still quite tight at the entrance, but further in there seemed to be enough room for his thick cock. There was just the pleasant sensation of fullness as it slid into me, with the beautiful big head exploring and leading the way in.

I was worried that I might have to tell him to stop if it became painful, but that didn’t happen. He just kept pushing it in until the tip was way up in my abdomen, far more than I expected to take.

His balls pressed up against me and his black pubic hair intertwined with my gray bush. He whispered “There” and I knew I had it all.

He began to fuck me in a very considerate way since he knew it was my first anal experience. He slid in and out gently with a rocking motion. I had expected him to be rough and insensitive but I was wrong. I suppose I had stereotyped him as an uneducated blue-collar guy who would just pin a woman down and screw her. He fucked me in a way that I can only describe as affectionate and caring.

He supported my legs with his strong hands so I was comfortable and I surrendered to him. I lost any real track of time but it seemed to last for quite a while.

Then I noticed his breathing change and he quickened his pace. I remembered the geyser of semen he produced when he jacked off and I prepared myself for it.

He stopped with his cock all the way up my ass and I felt a series of spurts and squirts go way up in me. I lost count but I think there were six or seven separate spurts as he emptied himself into my stomach. A twenty-five year old man is at the height of his sexual development and it showed.

I did not have an orgasm but I was very close. independent escort girls I had never felt a man cum like that, and especially I had never felt a man cum in my asshole.

He pulled out of me as slowly as he pushed it into me and I felt empty. He sat back down on the chair and dived back into my crotch. He licked my clit expertly and I did have my orgasm then, grunting and squealing.

I tried to get to my feet but I felt weak and dizzy. He helped me to stand up and then hugged me. This wasn’t supposed to be romantic, it was just a command-performance fuck but it was nice of him.

We struggled to get dressed, him just pulling up his pants and me putting on my tight pantyhose and skirt.

“My god, I never knew that was possible. You stretched me wide open. I was afraid you would injure me. But after the discomfort of the first moment passed and I relaxed I liked it. I never expected it to go in me that far. I really liked feeling you cum in me.” I felt myself blush as I whispered “There was so much of it!”

He replied “So now you know that you can still be fucked. You will have to take it in the ass but many women prefer it that way and I think you will too. By the way the stretching is permanent. It will be much easier next time.”

That seemed presumptuous so I said “What do you mean, next time?”

In a calm voice he told me.

“You just committed sexual harassment of an employee. I could report it and get a big settlement. You wouldn’t get fired because you own the place, but you sure would be embarrassed. I intend to come up here whenever I feel like it and fuck you. If you ever refuse me I will call a lawyer.”

I didn’t like being threatened, but why in the world would I ever refuse him?

I said “All right, you win. Just call me before you come up, I don’t want you barging in when I am in the middle of a meeting.”

So we agreed on that. For the next couple of weeks he came up every other day. I guess he needed a day to recover. He was right about the next time, his enormous cock slid right up my ass, no problem. After a few days we didn’t even need the petroleum jelly any more.

I thought about what I was doing and I knew it wasn’t right, but I couldn’t help myself. How could I have reached the age of fifty-five without ever experiencing anal sex? My dear departed Husband was not very adventurous about sex, it was pretty routine with him.

More than anything now, I wanted to make up for lost time. If John wanted to see me every day I would love it. I ordered an executive couch for my office, an over-sized leather model. I thought leather would be best because fabric might accumulate semen stains.

The couch was more comfortable than the edge of my desk, and once we playfully tried something different. I sprawled face-down over the back of the couch with my face on the seat cushions and my butt in the air, and John stood behind me and shoved his stiff cock up my ass. He reached a new record depth that time.

One other day I asked him if it would be alright if I sucked him off instead. He agreed and I gave him my best blow-job. When he ejaculated it hit the back of my throat so hard I struggled to control the gag reflex. I got it under control and I swallowed several mouthfuls of his thick, creamy cum.

I finally felt like a sexually fulfilled woman. All of my inhibitions had vanished and I wanted to try everthing. Once we decided to have some fun and John asked me to get completely naked. I did and he tied me up face-down on the couch and told me I was a prisoner in a Turkish jail. I played along with the fantasy and squealed and begged him to stop as he pretend-raped me anally.

We got a little too playful I guess because my secretary must have heard some of the noise we made. It’s a good thing that I lock my office door during these sessions because I heard her trying to turn the doorknob. We almost got caught in the act.

John seemed to enjoy the role-playing once in a while, but mostly he just wanted to fuck me deeply up the ass. He probably thought he was demanding sex from me and I was just acquiescing. Far from it, I wanted it more than he did. One day I almost paged him and made him report to my office for a session but I controlled myself. I knew he would call soon.

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