John my boss.
When I had just turned 22 years old I took a job in an office environment working in administration. It was a small office with a boss John , three older ladies and myself. Occasionally there was another assistant manager or partner I’m not sure of his title, but he did not work in the office much. The office itself was small located in one of those two story business parks. There was one office for John and one for the assistant and us four women worked out in the main area. Where we greeted public answers phones and conducted business. The business was security related and they hired and provided security and loss prevention for large chain stores in the Bay Area.
John my boss was a handsome man in his mid to late fifties. He was married for a longtime and had a daughter a year or so older than me.. He was six foot or so and had a nice fit build. Still had his hair and looked generally younger than his actually age. He worked out and it showed.
I’m 5′ 2″ I have long brown wavy hair. I am fit as well weighing about 105 pounds. I’ve always been a runner and into physical fitness. I am of mixed Hispanic decent so I have olive skin. Guys have always been attracted to me even with my extremely flat chest. I guess you would call me a tiny top.
Since this being my first serious job, I was into looking nice and dressing nice, but because of my small build and flat chest, I had difficulty finding clothes. Mostly, I wore tank tops under a loose fitting blouse, short skirts and heels. This way I felt sexy. I didn’t wear a bra much at all because I was so small (A cup), and they were hard to find that fit me right let alone looked good when I wore them. When I did find one it was embarrassing mostly from the children section of stores. Although I was flat chested I have rather large nipples which always seem to be showing poking through whatever it is I’m wearing. They always seem to attract male eyes and some disapproving looks from women, including my fellow female office workers.
Soon after I started there, John would call me into his office to take instructions, read his calendar and give him messages. Now the entire office was always freezing cold I guess the ladies liked it cold. John’s office was no exception and most mornings I would catch John staring at my nipples poking out, and standing tall or looking at my skirt. My skirts probably would not be considered office appropriate being as short as they were. My longest one was several inches about my knee and most of them were shorter mini skirts.
As time went on I did this each morning with John and I got to know him pretty well. One day he had items on my normal chair that was across from his desk so he had me sit beside his desk on a stool. This stool was taller than his desk, so I was seated above his sitting position. The stool would cause my legs to be off the ground because it was so high. I never was comfortable sitting on it because my legs didn’t reach the floor or have anything I could rest my heels on without my knees being higher than my waist. As I sat on this stool in my short skirts, I had to be very careful to not expose myself to him, as his head was right at my waist level at most four feet away. These stools had a hard surface and were pretty uncomfortable and sitting there for extended period anyone would start to shift body weight. I caught him looking directly between my legs on many occasions. I think the stools were used for the security personnel to sit on but not be comfortable. Believe me the seemed to work for that purpose.
Each morning when I entered his office the chair across from his desk was always cluttered with items, so he would instruct me to sit on the stool. The meeting started to become longer in duration each morning. Soon he had me getting him coffee or retrieve items which always caused me to step down and inadvertently give him a show. Oh, I forgot to mention that I have always only worn thong style or micro bikini style underwear. I have never liked the panties style.I also have been completely shaved since I turned eighteen, I just liked the look and feel better.
As time moved on each morning, it became routine for the first hour or so to be these meetings, I wasn’t ever to bring him coffee in the morning until after the meeting started. then he started having me close his office door but only after I had been in the office for a period, if I tried closing the door upon entering he would always say to leave it open then a short time later tell me to please close the door. I began to realize this was so that I would have to step down from the stool and flash him my choice of panties. I was becoming less careful with being ladylike as well, I knew what he wanted to see each morning and enjoyed teasing him with flashes here and there.
We became pretty close with him telling me about his family, about whatever current guy his daughter was dating that didn’t meet his standard and me telling him about whoever I was currently dating. One morning I wanted to tease him, so I worn my shortest mini skirt and barely there micro string thong. It hid nothing. This skirt was so short it just covered the bottom on my butt as I walked, it no doubt didn’t do that very well. I also wore my tank top and an open button white blouse. It being so cold in that office my nipples were in full view through the thin material.I arrived early that morning and was seated at my desk when John arrived. After a few minutes, he called me into his office for our morning meeting. You should have seen his eyes when I walked into the room that morning. I hopped up onto the stool. Sitting like that in that skirt well it didn’t leave much to the imagination. He couldn’t keep is eyes off me. I was for all purposes naked. So when John asked for his morning coffee, I shuffled some papers I had been holding and reached behind me to stack them on the shelve behind me. Doing this I had to stretch my right leg down to push off on the stool leg. I turned and twisted my body and this caused my legs to be wide open. I hesitated acting like I was having a problem putting the papers down so I could stay in that position for serval seconds.I made sure he was watching that I had his eye and I let my legs stay separated pretty far as I stretched to place the papers down and I slid off the stool. I caught him looking directly at what he desired so long to see. There was no doubt he had direct sight between my legs of my barely covered pussy, just a few feet feet away from his face. He looked up at me. I blushed and left to get coffee. Our meeting was extra long that morning.
Things progressed from there and one day I mentioned that my current boyfriend had complained about me only wanting to give him head and not sex. I told John that I loved giving blowjobs to men and had since I gave my first BJ at 12 to a high school senior in a park. This is when it happened John said my boyfriend was lucky that his wife never sucked him. I told him that I would love to do it for him. Seconds later I was on my knees between his legs getting what I had seen erect in his pants during morning meetings for months. He has a really nice cock good length and thick with a nice strong vein on the underside. I was sucking him and I heard him say something about me being a tease and how long he desired this. He stopped me as I thought I was getting close to making him cum and he said he wanted to see me naked. I wasn’t wearing much as it was but I stood up stared into his eyes and removed my blouse first than my tank top. I mentioned something about my small breast but he said they were beautiful and that he has desired to see my nipples for as long as I worked there. I then squeezed out of my skirt and pulled my string thong off as well. there I stood naked in front of this man more than 30 years older than me. He pointed towards the floor and I knew what he desired. I got back to work and in no time he was blasting my mouth with cum.
John is one of those guys that cums a lot he was really pumping my mouth full. Most guys can cum enough to cover my tongue but John was coming and coming, and moaning. I started to worry about the girls in the office hearing and walking in. When he finished I knelt back tilted my head back to show him all his cum in my mouth. He started to hand me his coffee cup I guess to spit it out into, but I shook him off and swallowed it all. I licked my lips, showed him it was gone, and went back to sucking him again. His head was sensitive and I just smiled up at him, as I licked any cum still dripping out. I thanked him several times to which he laughed. I told him how much I have desired to do that for him for so long.
I offered to do that for him whenever he wanted it. He didn’t want me to get dressed right away, we composed ourselves and he had me stay naked and sit on the stool. I did as he instructed. I sat there on the stool with my legs spread to give him a clear look. The rest of that I day I kept walking into his office to give him a smile or lick my lips I didn’t want him thinking I would cause him any problems. I enjoyed our morning meetings and I always looked forward to going to work.
From that day forward each morning “Get some coffee” had a new meaning between us. If John said that. I knew that as soon as I returned with his morning cup I would shut the door and get my morning treat. I was addicted to his large doses he would give me. Most mornings I never eat breakfast so this was my nourishment the only thing I had until the afternoon each day. I would walk around the office having conversations with cum breath and I was rather proud of that actually.
Soon, he started to take me on afternoon business calls with him. John would introduce me as his assistant to the clients. I think he really enjoyed displaying me in my short skirts to all the clients. On those days we would stop on the way back at the San Mateo County Fairgrounds or Fashion Island Mall, where I would give him an afternoon BJ in the parking lot in the back seat of his car. He always demanded I be completely naked to suck him off, it became a thing he would not let me start, unless I was nude. He also never pushed me for more than a BJ, I guess since the President Clinton episode, a BJ wasn’t to be considered sex, so he wasn’t cheating on his wife. I don’t know. I didn’t care. I just loved how the man made me feel so sexy and desired. How he nourished me. On these days we often didn’t have time to eat and all I would have from morning to night was John’s cum, I know he loved that, too.
On occasion, clients would visit the office, well John started having me in the office during these meeting. The client would sit in the chair and I would stand until John pointed to the stool and instructed me to sit. I think he liked to show his authority over me to clients. Doing so always seemed to have the client sit up straight in his chair and it seemed to increase their interest in the conversation. One guy in particular seemed to come around more frequently once, I started sitting in on those meetings. I was always careful to be as ladylike as possible, in whatever it was I was wearing, no matter how difficult that was.
This went on for a little over two years, hardly a workday went by without me getting at the least my morning dose and often two doses a day of pleasure. He came in one day and discussed his plans to move his family to Utah. I was heart broken, although I knew it was never to be more than it was I loved it as it was. I looked forward to work during the weekends and how many people can say that. It still took months for him to finish up and move and I made a promise to him that before he left I wanted him to have sex with me. He was reluctant but I convinced him that I would give him anal as well, something he told me he had never experienced with his wife. I was experienced with anal sex. Most guys always desired it from me, and I always felt, since I was so flat chested that I had to do more than other girls to make guys happy.
In his last week working there, we started the day like normal with his morning blowjob . Then at lunch he told the girls he was going on to say goodbye to some of his longest clients and was taking me along. Well, we went directly a motel and spent the afternoon. He didn’t want straight sex he wanted my ass and I wasn’t going to say no. We spent the entire afternoon with him enjoying the fruits of his labor. If he wasn’t pounding my ass, I was sucking his cock. It was a wonderful afternoon, one I will never forget.
Thank you John
Lydia
