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My name is Gwen and ever since I can remember, I’ve always been shy, modest, and lacked selfconfidence. I was never a risktaker although there were times I wished I were. I was the good girl growing up who hardly ever got into trouble. While other kids were going to parties, drinking, and experimenting with drugs and , I spent most of my time with other kids who didn’t fit in. We’d watch scifi movies, read books, and study.
Deep down, I wanted to try at least some of the frownedupon activities other kids were doing but I didn’t have the confidence to break out of my shell. My parents didn’t have much money so I never wore the most fashionable clothes but was lucky enough to have a cheap cell phone. My attire consisted mostly of jeans, loose sweaters, or hoodies.
It was unsettling for me to leave the security of home and go away to college, even if it was only fifty miles away. I was out of my comfort zone by being forced to meet new people and have an entirely different set of friends. I did a workstudy in the library that helped me become more comfortable talking to strangers and I joined the school newspaper so I could make new friends.
I had body image issues growing up, especially in my teen years. I’m 5’7″ with 36C breasts. I think my butt is too big but I’m not overweight. I never did much with my hair and usually had it pinned up and I wore glasses. While other young women around the college campus were wearing clothing that accentuated their figures, I was wearing clothes that mostly covered up my body. I heard some people referring to my clothing as frumpy. My older sister even tried to get me to modernize my wardrobe by telling me I dressed like a nun. However, I resisted most of her efforts and wanted to remain prim and proper.
When, on rare occasions, I would go to a beach or pool young men would seem to check me out in my onepiece suit but I never thought I was y or attractive. Some of my friends tried to get me to dress more stylish and wear more makeup but I wasn’t confident enough to change my appearance.
I lost my virginity in college to a nerdy guy, Roland, who had a crush on me. My goal was to save myself for marriage which, up until then, was pretty easy because there weren’t too many guys trying to have with me anyway. Oh, I had kissed some guys, made out with a few more, and even let them touch me but I never felt attracted to them enough to have with them.
It felt good to be desired and Roland and I ended up in a longterm relationship. Once you start having , it seems like you want to keep doing it again and again. We experimented with oral but I wouldn’t let him try anal. We had a wonderful time until he changed schools after our junior year. Once you start having , it’s hard to stop and I ended up sleeping with a couple of guys in my senior year who I dated.
After graduation, I used my business degree to get a job as an assistant to an executive in the clothing industry. It was a midsize company that was trying to expand their market share. I figured that being with a smaller company was a way to better learn the internal operations of a business. I didn’t want to get lost in the shuffle of a larger corporation.
My boss, Matt Berger, took me under his wing and I rewarded his faith in me by being a hardworking, loyal employee. I wasn’t afraid to work long hours, even on the weekends to help him and the company progress and I did it without complaining. It’s not like I had much of a social life anyway. I got to the point where I could anticipate his needs and I kept him organized. I had either completed tasks before he asked me or I had all the information he needed at my fingertips. The more he relied on me, the better I felt about myself.
Working long hours sidebyside also brought us closer together on a personal as well as professional level. When Mr. Berger began to have marital problems, he would sometimes confide in me. His wife didn’t understand how much effort it took to keep the company running successfully and how difficult it was to expand on what they had already achieved. He suspected his wife may have started cheating on him.
I didn’t understand why she would do something like that, after all, Mr. Berger was a handsome man in his early forties with dark hair and some graying around the temples which made him look distinguished. He had a wry sense of humor. He had captivating dark eyes and a smile that would warm your heart. He worked out at the gym almost every morning before work. In case you were wondering, yes, I had a crush on my boss, even though he was twenty years older than me. I guess I was attracted to him physically as well as to his charm and power.
I guess when you work that closely with someone it’s only natural to develop some attraction towards one another but we always kept it professional. Besides being improper, I figured there was no way he would be attracted to a nerdy woman like me anyway. That didn’t stop me from thinking about what could be or from having uncontrollable improper dreams about my boss ravaging my body.
My social life remained dull even though I tried dating several men. I wouldn’t even consider having with anyone unless we dated for at least a month if not more. More often than not, I masturbated to relieve my ual frustrations but that is never as satisfying as the real thing. My horniness fueled my fantasies about being with my boss. The fact that he was unattainable also made Mr. Berger a safe object of my ual thoughts. We seem to covet what we don’t or can’t have. I knew it was only a silly crush but it was fun at the same time.
After I had been working there for almost two years, the company was in the position for a major expansion, due mostly to the leadership and business acumen of Mr. Berger. The more responsibility he took on, the more he relied on me and I was more than up to the task.
At the end of a long day or an especially long week, it wasn’t unusual for Mr. Berger to have a drink from a bottle of Scotch he kept in his desk drawer. I would often join him in his office but wouldn’t drink. I couldn’t handle my alcohol but I would sit with him for a relaxing chat. Then, he would tell me what was going on in his personal life.
Mr. Berger was convinced that his wife had a lover but he couldn’t blame her after all the time he spent at work. It bothered him but he knew it was only a matter of time before they split. They didn’t have any children so no one else would be hurt if or when they got divorced. He asked me about my personal life and I confided I didn’t have much of one. I dated men but there was no one I was serious about.
“That’s too bad, Gwen. You’re a lovely young lady. You deserve to have someone special in your life. It’ll happen when you least expect it.”
I nervously laughed and replied, “I haven’t expected it for a long time so I hope you’re right.”
There were times when Mr. Berger and I would have our afterhours chats and I’d sip a little bit of Scotch with him. The first time I tried it, I winced at the taste which made my boss smile and I could see him fighting back his laughter.
“Scotch is an acquired taste, Gwen. Take little sips at a time.”
I didn’t drink with him all the time but would have some once in a while. I was getting used to it but I had a low tolerance for alcohol and couldn’t handle too much anyway. It seemed to bring us closer together too which I enjoyed. He would confide in me about his personal life and I would share bits of my boring life with him.
I felt extremely sorry for him when he told me his wife wanted a divorce. She had, in fact, found someone else who she had been seeing for a while. He was hurt but it wasn’t a complete surprise.
“I knew someone had to have been her because it sure wasn’t me.” He went on to say, “I’m sorry, that was too much information, wasn’t it?”
“That’s alright Mr. Berger. It’s probably better that you are getting divorced if she doesn’t appreciate what a great guy you are.”
“You’re too kind, Gwen.”
My fantasies for Mr. Berger only increased after I found out he was getting divorced and hadn’t had with his wife for a long time. I dreamed of being in his bed with him but I would never, ever attempt to bring those dreams to life. He was my boss and probably didn’t see me in a ual manner anyway. I thought I noticed him looking at me differently but I figured it was just my imagination combined with wishful thinking. I probably would have panicked if he made a pass at me anyway.
The company had spent considerable time and resources developing a line of midpriced lingerie and swimwear they could market to department stores in several areas around the country. They wanted to start with smaller regional stores before expanding to national chains.
I spent a lot of time with Mr. Berger and our marketing team looking at data and trends to determine which items different demographic groups are buying. I was devoting a considerable amount of time to pouring over spreadsheets and graphs.
One evening after everyone had left for the day, Mr. Berger and I were sipping Scotch in his office. He was running some ideas by me but he was really thinking out loud. He needed someone to listen to him.
We started talking about some of the data and I went behind his desk to look over his shoulder at what he was looking at. I didn’t know it at the time, but a button on my blouse had come undone and when I leaned over to look at the data, my blouse came open exposing my bra and a good portion of my left breast.
I did notice that when Mr. Berger was talking to me, rather than looking me in the face, his eyes were drifting toward my chest. I realized it at the end of our conversation and discreetly buttoned my blouse. I was embarrassed but I also got a warm feeling in my pussy knowing that a man was looking at my partially exposed breast, a man who I had a crush on too.
When I got home that evening, I undid that button and leaned over in the mirror to see what Mr. Berger was looking at. I was stunned at how much of my breast he could see. I got undressed and masturbated to the thought of exposing my entire bare chest to Mr. Berger and even going further to allow him to see me naked.
While I was shoving my vibrator into my pussy and playing with my nipples, I closed my eyes to pretend it was Mr. Berger’s dick penetrating me. It was a shame that his wife wasn’t having with him because I found him to be extremely attractive and y.
On another occasion, I wore a tight pencil skirt I had recently purchased. It came to just above my knee but when I sat down, the skirt rode up, exposing more of my legs than I usually am comfortable with. That evening Mr. Berger had me stay late with him and while I was sitting across from his desk, I noticed he was looking at my legs.
Emboldened by the alcohol I had been sipping, I casually crossed and uncrossed my legs in front of my boss to see if he truly was checking me out. Each time I crossed my legs, my skirt would ride up a couple of inches more and I could tell that Mr. Berger was definitely looking at me.
I never felt attractive to men and it sent chills through my body directly to my pussy to know that I had caught the attention of a sophisticated man such as Mr. Berger. That night when I got home, I sat down in front of a mirror and began to cross and uncross my legs so I could know what my boss was looking at.
I was shocked to learn that he might have gotten a few quick glimpses of my panties as my skirt rode further up my legs. It was unintentional, of course, but knowing a man had seen my underwear made my pussy moist and I ended up masturbating again with part of me fantasizing about exposing myself further. I didn’t have the courage to do it, but I thought about what it would be like to not wear any underwear and let Mr. Berger see my bare pussy.
One Friday evening, Mr. Berger and I were working late again. This time I wore a white lace plunge bra underneath my blouse and left an extra button undone before I went into Mr. Berger’s office. I always thought that my Ccup breasts were my best feature and I wanted to see if my boss was trying to look down my blouse.
While we were looking at some data, I leaned over the front of his desk to point out some things I thought were important. I had checked myself in a mirror at home so I knew exactly how much cleavage I was showing. If he looked long enough, he would be able to make out the dark brown areola of my nipples.
Sure enough, I could see his eyes darting from the charts in front of him to my hanging breasts. I could feel my nipples harden as Mr. Berger left no doubt that he was looking down my blouse. A warm, wet feeling engulfed my pussy. I had no idea what I would do if he made a pass at me. I might have gotten scared and rebuffed his offer but part of me was hoping he would at least try to seduce me.
It was difficult to read the charts upside down so I came around his desk to make it easier to see what I wanted to point out to him. As my blouse gaped open, I could see his eyes looking at the mounds of my breasts. There was an unmistakable ual tension building in the room.
When he looked up into my brown eyes, I was giving him a telepathic message to him. “Go ahead, kiss me. Take me in your arms and kiss me. I’m all yours if you just ask.”
Mr. Berger was staring at me and I could tell he was contemplating what he should do. Instead of kissing me, he seemed to uncomfortably break our stare and made an excuse to end our afterhours meeting. I stood up straight and agreed that I needed to leave because I had a date. I met a guy online and we were going on our second date that I would have loved to have canceled for an opportunity to be with Mr. Berger.
My pussy was on fire when I met Cal for our date. I met him at a place downtown for a casual dinner and drinks. I was so horny that I readily agreed to go back to his place so he could fuck me. He wasn’t the greatest looking guy and was slightly overweight. He wasn’t the best lover but he ate my pussy until I orgasmed and he fucked me twice. The entire time his dick was plunging into me, I had my eyes closed while imagining it was Mr. Berger that was me. When I was sucking Cal’s dick, I was wondering what my boss’ dick would taste and feel like. It wasn’t the greatest I’ve ever had but it was just what I needed. Cal served his purpose.
I wasn’t proud that I slept with a guy after only our second date and I decided I needed to stop teasing Mr. Berger because I was only torturing myself. He was much older than me, didn’t seem attracted to me and besides, he was my boss. I didn’t even want to see Cal again but he kept text messaging me for another date. Nothing went right because of my stupid fantasy.
I started wearing dresses and skirts that came below my knee and loose sweaters that covered most of my body. I still had a crush on Mr. Berger but I fought my desire to be with him. It wasn’t realistic and I started to focus my attention on online dating, not that it was going that great for me either. My love life sucked, to put it mildly.
Meanwhile, at work, Mr. Berger and his design team settled on several items of swimwear and lingerie they thought would be good sellers. They identified a target market and the retailers they would approach to market the line to. But first, they had to have samples. In order to refine the lingerie line, the company hired a model so they could see what it looked like on a live person.
They scheduled the model after lunch one day and it was my job to have her fill out the paperwork so she could get paid. Even though she was getting paid with an electronic money transfer, there still had to be some documents signed for the accountants.
When the model, Sharon, arrived she wasn’t the supermodel type I was expecting. She was about my height, rather thin with smaller boobs and ass. She wore heavy makeup but wasn’t as pretty as I expected.
As she was filling out the paperwork, I asked her, “How did you get into modeling and how do you find the courage to model lingerie in front of strangers?”
“I was running short on cash to pay my bills and I contacted this agency that advertised online. It wasn’t easy at first, I mean most women feel their body isn’t perfect.”
“Ain’t that the truth?”
“But, you have to act confident no matter how nervous you may be, and to be honest, it’s kind of a turnon to be on display like that.”
“Really? I don’t think I could ever do it.”
“Sure, you could. It’s not hard.”
Sharon used Mr. Berger’s office to change into the outfits because it had its own bathroom and was connected to the conference room. The office manager, Millie, would assist her in changing.
There were several people gathered in the conference room from the design team and marketing department, both men and women. The modeling began with a couple of items of swimwear from one piece to bikinis. They were modest but showed a good portion of Sharon’s ass cheeks and a bit of cleavage. She then modeled the lingerie line that started with some conservative gowns to more revealing baby dolls and chemises.
The outfits got more risque as the modeling continued with people making notes and comments as Sharon moved along. I could see the men’s eyes scanning her body, pretending to be professional but I knew they were also checking out her tits and ass. The final outfit was a sheer white gown that left nothing to the imagination. Sharon’s bald pussy was visible as well as the rest of her private areas.
I marveled at her confidence and found my pussy getting a little damp just from watching her put herself and the lingerie on display for everyone to see. As she was modeling, I wondered what it would feel like to exhibit my body like that and have a roomful of people looking at my partially clad body. I could only wish that I had the confidence to do it myself.
Sharon came back a couple more times after modifications to the clothing design were made and the company felt it was ready to show it to prospective clients. They naturally hoped to convince the clients to carry the line. If they could establish themselves in smaller markets, they could then move on to larger, national stores.
I helped Mr. Berger plan a small reception for the clients and he had the conference room arranged similar to a small runway that you’d see in a more prominent fashion show. The entire team was nervous as the clients started arriving and began to socialize over some light finger foods and drinks. This was a big day for my boss and the company.
Fifteen minutes before the presentation was supposed to start, Sharon sent me a text message telling me she couldn’t make it. My eyes widened and I quickly pulled Mr. Berger aside to show him the text.
“Call the agency and see if they can get someone else here, ASAP.”
I went into his office and called the agency, and then I had to deliver the bad news to my boss: “They said they were trying but couldn’t find anyone on such short notice.”
“Great, what the fuck do we do now?”
He called everyone into his office for a quick meeting. They were all in a panic trying to figure out what to do. They could present the line without a model but it wouldn’t have the same effect. As they were scrambling for a solution, words popped out of me that I never thought I’d hear myself say.
“I’ll do it.”
Everyone stopped talking and stared at me. They looked puzzled.
“Do what?” Mr. Berger asked.
“I’ll model the line for you.”
They all looked at one another, waiting for Mr. Berger to say something.
“I can’t have my assistant modeling for us. Human Resources would go crazy.”
Millie then said, “We don’t have many options right now. Besides, we all heard Gwen volunteer. It’s not like anyone asked her or forced her to do this.”
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