Mature Secretary’s Blowjobs

This is intended to be a single short story as I do not expect to add to it further. It developed as I sat at my desk and allowed naughty thoughts to enter my mind. I hope you like it and please let me know if you did, or if you have any constructive criticism. Enjoy.

Chapter 1

I looked at the corner of my computer screen at the time, 9:51 am. I still had a full 9 minutes before my 10:00 am call, but the idea of being late for the call did temporarily reduce my enjoyment. The call was a series of weekly check-ins on a large reorganization that had been going on for months, with the aim that everything would be finalized and executed by the end of Q4. I moved my mouse and opened the last version of the structure chart that would be the focus of the call. 9:54 am. Suddenly I felt it. The metaphorical wave that builds, as the tide starts to pull back from the sand, building slowly until the wave grows bigger and more powerful, cresting right about to explode. I tried to hold off for as long as I could, knowing that each second would make the climax that much more glorious. I clearly had shown my anticipation, perhaps I had moved my legs too much or tightened my thighs but the intensity picked up and I couldn't do anything other than close my eyes and contain my moans as I felt the first rope of cum shoot out, followed by several more spurts. The intensity shifted to much more of a slow deliberate motion focused on milking every final drop of cum out of my now quivering member. I slumped in my office chair. 9:57 am. I felt a slow kiss on the tip of my dick followed by hands pulling my underwear back on. I kept my eyes closed as I heard the familiar sounds followed by the now familiar sensation of a big, wet kiss on my lips. I had grown to accept the kiss on the lips, even though every now and then I could taste my cum being shared back with me. "9:58. You have a call in 2 minutes. Should I come back this afternoon at my regular time?"

"Yes, this afternoon would be great. Thank you, Mommy."

Chapter 2

It was my first day starting at one of the most prestigious law firms in the country. Sure I had summered there but now I was a fully licensed attorney. I had graduated law school in the spring, gotten married to the love of my life in the summer at a small ceremony on the West Coast and was now living in the City in an apartment that was perhaps a bit too nice and too much money for now, but I assumed I would grow into it as my salary increased and bonuses started to flow my direction. For my wife's part she has been nothing but supportive of my entire journey from applying to law school up to this point. I hope it is ok but I don't want to share too much else about my wife, as this story is not about her.

My law firm was in one of the more historic skyscrapers in the City, and with a headcount of just under 500 lawyers and 10 floors, the office was like a small town. As I approached the building after exiting from the subway, I made my way to the elevator bay, taking it up to floor 52, which was the main lobby for the firm so I could be shown my new office. I was also very excited to meet my new "Personal Assistant". Often they were young perky 20 somethings who were not hard on the eyes. I had developed some innocent crushes on a few of the PAs while I was summering at the firm. Nothing happened with any of them as I was at the time engaged to my now wife but it is still fun to sometimes flirt and chat with a good looking girl who is a bit younger than you (I am currently in my early 30s).

Someone from HR greeted me and told me my office would be on the east side of the 51st floor. We took a set of internal stairs down together and made chit chat about how excited I was to start, how nice the weather had been as of late, the usual.

"and this will be your new office and Margaret will be your Personal Assistant!"

Margaret's desk was directly outside my office and while I was not shocked, I candidly was a bit disappointed. There were still many Personal Assistants that were well into their 50s and 60s who had been doing this job for decades. They often had attitudes and were not the best with technology, not exactly a great combination.

Margaret gave me a short hello and welcome and seemed to go right back to whatever she had been working on. I stepped into my office, put my bag down and started up my computer. I looked out the big windows at the City down below. There were several annoying orientation and HR programs I needed to do before I could start work in earnest. I had been watching an anti-harassment video for a good 35 minutes when I did not even notice Margaret had entered my office, only realizing it when I heard the door click shut.

"Do you have a few minutes to chat? I always like to get to know the new attorney I will be servicing to ensure I know what they like and dislike."

She sat down into the chair across from my large wooden desk. The desk was an L-shape, with part of it against the wall which had the computer screens on it and the larger L portion acting as a barrier between myself and whomever was sitting across from me in my office. I turned and took in Margaret for the first time.

She was in her late 50s or early 60s, and was on the larger side. Sitting across from me she had on dark pantyhose and a beige skirt that went past her knees. She was quite large both in terms of the size of her thighs and her ass was large given it seemed to be pouring over the wooden seat she was in. She had on a white blouse and a black sweater over it that tried its best to cover her clear belly and love handles. She did have massive breasts, something I had not noticed when I first met her (perhaps they were hidden from her computer screen). She had a plain "older woman" face, not too much makeup on, black rimmed glasses and a big head of silver hair. She was not a cute 22 year old blonde however she was by no means ugly and had a somewhat mature attractiveness to her. I had to admit that her massive boobs would be fun to look at on a daily basis.

"Sure, happy to chat. What would you like to know, Margaret?"

Chapter 3

The conversation was quite bland. She asked what time I planned to arrive every morning, how I wanted to be addressed (I told her my first name was fine), whether I'd enjoy having a cup of coffee waiting for me every morning, how I liked my emails filed. She asked about dry cleaning. She asked if I was married and I said I was. We wrapped up our conversation and as she got up I turned my attention back to my computer.

As she was about to open my office door, she turned back. "Oh, one more thing, do you want your daily blowjob in the morning, afternoon or both?"

I froze, assuming I had misheard her. "Sorry, Margaret, what was that last question?"

"I've been doing this job a long time, I understand times have changed in many ways but what has not changed is the level of stress you attorneys are under on a daily basis. It is my job to help you in any way I can and I am not only quite skilled in this department but I've grown to really enjoy it. I do have some rules but we can talk about them once we confirm your preferred schedule."

The manner we were speaking in made it seem like we were discussing how to staple documents and not oral sex and I got instantly uncomfortable.

"No, that will not be needed, Margaret. Thank you."

"Ok, understood. You're a young man happily married! No need to make me feel bad. If you change your mind do let me know and we can discuss further. Until then please do me a favor and do not think of me in a sexual way. Think of me as your secretary and in many ways your office Mommy." She winked and opened the door and seemed to accentuate her walk which shook her big ass from side to side before she shut the door.

I was again alone in my office, confused at what the hell had just happened, and why I had an erection.

Chapter 4

The first week of work had gone well. A few minor hiccups but nothing problematic. Everyone at the office had been very nice and ignoring the bizarre ending to our first meeting, Margaret had been very helpful to me. In speaking to other junior attorneys, some of whom had younger Personal Assistants, I actually was quite lucky as Margaret was willing to do things other PAs were not. Not everyone would have a warm cup of coffee on their lawyer's desk for them in the morning and no one else told me their PAs would drop off and pick up drycleaning. I did not tell anyone about what Margaret had offered to me and chalked it up as a joke or some sort of weird test which I assumed I had passed. The trouble started in my third month of work. At the time I was working on several matters that were crushing me, I was working from the early morning well until the early hours of the next day with little sleep. My fitness routine had fallen off drastically and I could sense I was losing muscle while simultaneously gaining weight. Our building had a gym in it just for members of the firm that was open all hours of the day. I started to use the gym more for workouts to help with stress. Typically the gym was not that busy. I had seen a few attorneys I recognized and on occasion a Personal Assistant or two. Today it was Thursday morning at 7:45 am. I had come in early to get a solid workout in before the start of my day. Exiting the men's changeroom the gym seemed empty. I got on an exercise bike and put on some music. I was 10 minutes into my workout before I noticed that of all people Margaret had entered the gym and was using the stair-master directly in front of me. She had on black yoga pants that did a bad job of hiding her massive ass and a tight pink track jacket zipped up to her neck. Her hair was in a silver bob on the top of her head. I did not intentionally start to look at her but as she got into a rhythm her big ass started to sway side to side, each cheek being pushed up and down as she walked up the stairmaster. A few minutes in she must have gotten a bit warm as she unzipped her track jacket so her white sports bra was showing. It was harder for me to see her massive breasts swaying as she climbed but I was able to see a bit by looking through the mirror on the front wall of the gym. I looked up and for a brief moment felt like I made direct eye contact with Margaret. I continued to ride my exercise bike but before long realized that I had a raging erection in my shorts and given how small they were it was not very discreet. I flipped my dick up into my waistband and slipped into the men's locker room. I headed into the shower and with almost a hypnotic force started to jerk off. Out of nowhere I pictured myself naked in the gym on my knees, shoving my face in Margaret's sweaty ass. I pumped my cock faster as I sniffed deep breaths of her sweaty ass and even licked up and down her covered crack trying to lick up some of her ass sweat. I pictured her turning around and smiling and encouraging me, whispering "good boy you are doing such a good job jerking yourself off for me! Keep sniffing my ass I know you love the smell." I started to jerk off at a frenzied pace, thinking of her putting her hands on the back of my head and pushing my needy face deeper into her fat ass. "Go ahead and let out all that stress for your office Mommy!" With that, my load shot across the shower stall onto the tile wall. I opened my eyes in a panic as I caught my breath. It had been the best orgasm I had felt in months. This felt bad. I am sure it was not great that I had just jerked off thinking of shoving my face in my secretary's sweaty ass, even worse considering the broader circumstances.

I finished getting ready and headed to my office. Margaret was sitting waiting for my arrival and a cup of warm coffee was waiting for me at my desk. Clearly my morning masturbation session had gone on longer than I realized. "Did you enjoy your workout this morning?" she asked innocently. "Yes, it felt great," I said as I closed my office door.

Chapter 5

I tried really hard not to but following my gym session jerk off I had developed a naughty habit of thinking of Margaret every time I jerked off. Even worse was that I pitcured her when I fucked my wife. Sometimes it was as if I was fucking Margaret but other times I pictured her standing over me as I fucked my wife, with Margaret encouraging me to finish and look her in the eyes as I blew my load. "Good boy, pump all that cum into your wife as you look at your office mommy!" It was so fucked up. My wife was so much hotter in every way but I could not stop thinking of Margret's big fat ass and massive tits as I came.

This also had made me much more attentive to Margaret in the office, what she wore, sneaking peaks at her body. I even went full psycho and sniffed her seat one time when she went to the washroom. I pretended to drop my pen behind her desk and bent over and shoved my nose deep into her chair and inhaled. The scent was strong and intoxicating and I am ashamed to admit I proceeded to go straight to the washroom and jerk off. This time I pictured Margaret bent over my desk with her skirt hiked up so I could sniff her ass and lick her panties as I jerked myself off behind her. I came instantly and worried I had been a bit too loud in the washroom.

I could tell that I was headed down a dangerous path but I felt like I couldn't change directions. It all came to a head during our firm's holiday party one Friday night in December. The firm had booked out a massive ballroom in one of the nicer downtown hotels and everyone was dressed in ball gowns and tuxedos. It was an unofficial tradition that all first year attorneys could not refuse a drink if offered one by a partner at the dinner. The result was that I was quite drunk before the main courses arrived. The room was fully spinning by the end of the meal and I decided to head back to the office to grab my apartment keys and go home early before I said anything or embarrassed myself. The office floor was dark as I tumbled down the hall, I found my office and sat down in my chair. I had a half-full can of diet coke on my desk and drank it greedily.

"Are you feeling ok?"

I jumped and spilled some of the coke on my pants. Standing in the doorway to my office was Margaret. She had on a floor length black dress that covered her curves but still reflected the fact that her ass and breasts were massive. The neckline went down just enough to show the start of her heavy cleavage. Her silver hair was down and framed her face nicely. She had on more makeup than usual and looked quite beautiful.

"Oh.....yea.....I just felt and I needed some air.." I tried to string together a few words but could tell I was not making a ton of sense.

"You know, I am a bit surprised we have not had a talk, you and I" Margaret said as she entered my office and shut the door behind her. "Tell me, why were you so quick to dismiss my offer on your first day? Was it because that was before you started to be so turned on by me?"

I tried to focus but was struggling to look at anything besides Margaret's big tits as she had leaned over my desk so they hung down fully.

"Oh....Well....We work together and so it would be..."

"Do you think I would ever tell anyone else? Wouldn't I be fired?"

That was a fair point. We likely both would get in trouble.

"I'll try and explain where I am coming from if that helps. I started at this firm in the 1980's as a young 20 year old. At that time, female attorneys were rare at this firm so it felt so special getting a job in a fancy law office. My first boss was a middle aged man who was quiet and brilliant. He would be in the office day and night. The stress of the job would get to him and I could tell he was starting to lose it. One morning, around 10:00 I slipped into his office while he was on a work call. I didn't say anything, I just crawled under his desk and slowly undid his belt while making eye contact. He froze, and was shocked at my advances but did not stop me. He watched as I took him in my mouth and slowly rolled my tongue up and down his shaft as it grew. He was quite small so I had no problem taking him fully and playing with him. In addition to being quite small he also had difficulties lasting very long. Neither of these bothered me and before long I felt his load burst into my mouth. I slowly milked him using my hands and when I was done, I stood up, kissed him softly and left his office. It was never explicitly discussed but we developed a rhythm of a morning blowjob every day. I was shocked at how much his mood improved. He was happier, more confident. He even married someone and had a family. None of this changed our dynamic and for years I looked forward to swallowing his morning load 5 days a week. When he retired after 20 years of working together, during his retirement speech in front of the entire firm and his family, he broke down into tears and thanked me for being the most important person in his life who helped him with his career. I was shocked. It made me feel so special knowing that I helped this brilliant man.

My next boss was very different. A hot shot who I had been told was known for hitting on secretaries and cheating on his wife. He needed two blowjobs a day, one right when he got to the office and one in the afternoon. They calmed him down and his cheating subsided and he became a much nicer person to everyone he crossed paths with, especially his wife. I always assumed she had an idea of what was going on but honestly she was nothing but kind to me. I tell you all of this so you understand me a bit more. For decades I have swallowed loads on a daily basis and I truly have grown to crave it. So you can imagine how shocked I was when you seemed uninterested. Perhaps I should have thought better. I'm old now, fat, chubby. I don't have the same sparkle I had at 34 let alone 24. So you tell me, are you still very sure you don't want my...attention every day?"

I had become rock hard listening to Margaret talk about all of this. In my drunken state I candidly wanted to fuck her on the table but I worried I would vomit all over her.

"I....I would enjoy your attention to my privates...." I slurred.

"I am so happy to hear that. I just have one rule. The rule is a bit...unique but I require after every session a kiss on the mouth and you to thank me and call me Mommy. Does this seem acceptable?"

"Yea...yes yes they are super accepting can we start right now?" God I was so drunk this was embarrassing.

Margaret stood up and smiled. "No. You are very drunk and I don't want our first time to be while you are in your current state. That being said, I would never leave you unattended. I am going to step outside your office and press my body against the door. I want you to take off your pants and jerk off against the door so I can hear you. I want to feel your urgency as you wank yourself for me on the other side of the door until you blow your load all over your door. Do not worry about cleaning it up, I will take care of that."

I watched as she stood up, turned and slowly walked to the office door, turned, smiled, and closed it.

I was alone in my office, late at night, with a raging hard cock, and just drank enough to give into this temptation. I stood up and walked to the door, undid my pants and proceeded to stroke my cock violently. I leaned against the door and could hear a faint whisper from Margaret on the other side.

"You are doing such a good job, sweetie. Are you picturing my big ass pressed against the door?"

"....yes"

"Good boy. Keep going and keep thinking of my big mature body. Do you like thinking of my big, saggy breasts?"

"....yes.." my tempo picked up.

"I want you to cum for me, all over your office door. Can you do that? Can you do that for....your Office Mommy?"

I exploded all over, cum shooting out as I collapsed into the door and let out a drunken moan. I fell back onto the floor of my office and saw as Margaret opened the door slowly, standing over me with a warm smile. I watched as she closed the door, and slowly got on her knees and began to lick my cum off the door. It was so fucked up and so fucking hot. Once she was done, she stood up and wiped up the last piece using her finger and looked at me as she licked the last piece of cum up off of it.