My name is Gwen and ever since I can remember, I've always been shy, modest, and lacked self-confidence. I was never a risk-taker 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 sex, I spent most of my time with other kids who didn't fit in. We'd watch sci-fi movies, read books, and study.
Deep down, I wanted to try at least some of the frowned-upon 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 work-study 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 one-piece suit but I never thought I was sexy 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 sex 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 sex with them.
It felt good to be desired and Roland and I ended up in a long-term relationship. Once you start having sex, it seems like you want to keep doing it again and again. We experimented with oral sex 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 sex, 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 mid-size 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 hard-working, 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 side-by-side 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 sex with anyone unless we dated for at least a month if not more. More often than not, I masturbated to relieve my sexual 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 sexual 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 after-hours 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 fucking 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 sex 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 sexual 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 mid-priced 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 sex with him because I found him to be extremely attractive and sexy.
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.
