I grew up in a very catholic family, went to church every sunday, went to an all girls catholic school. You get the picture.
I’m not saying I was the perfect child growing up, but compared to my friends, I was a saint. My girl friends were curious and wanted to try everything, Sex, drugs, alcohol, cigarettes. I won’t lie, I was curious as well, but I could never be as bold as they were. I had my first boyfriend when I was 16, but it did not go too well. I was so shy I refused to even kiss him. Being the horny teenager that he was, he grew impatient and ended up breaking up with me. I was heartbroken and it took me years to date anyone again.
I’m now 22, in college, studying law part time and I also work in a small law firm with a handful of employees. I’m still a virgin. I have a huge crush on one of the guys in my class but he is in a pretty serious relationship, so, off limit. At this point, i’m pretty sure i’ll die a virgin.
I get along with my boss very well. He is much older than I am. Maybe mid 30’s. We don’t have a lot in common but we still manage to find things to talk about (besides work). After a few weeks, our conversation start becoming more and more flirtatious. I’m not sure who started it first, it does not really matter. I don’t know how to stop it either, not sure I want to anyway. He starts to find excuses to spend more time with me. He asks me to stay after work, or sometimes we have lunch together. I’m not sure if my colleagues have noticed anything. We try to be as discreet as possible.
Then it happened. One afternoon, after work, we were alone in the office. We had been flirting, then he had me sit on his lap. I was wearing a pair of black leggings, a green button up shirt and a pair of black heels. He slid his hands in my leggings and started playing with my clit. This was the first time I let a guy touch me there. I had never imagined something like that would ever happened. I was curious to see how far it would go. After teasing my clit, i felt his fingers move towards my opening. I was soaking wet. I felt him push one finger inside me. It hurt.
I was pretty inexperienced when it came to sex, but I still knew what was happening. For the first time in my life, I was being fingered. However, it did not feel as good as I thought it would. In fact, it did not feel good at all. Maybe I was too tight. But I was also very curious and horny, so, even if it did not feel good, I did not stop him.
He told me to take off my leggings, and as I was doing so, he took his cock out. I was mesmerized by it. He was already very hard. His cock was maybe 6 or 7 inches, but so thick! He looked at me, as if expecting me to do something, but as I said, I was very inexperienced. I did not know what to do, so I decided to come clean. I told him I was a virgin. He did not believe me at first. I guess I don’t look as innocent as I thought I did. I expected him to tell me to put my clothes back on, but instead he had me suck his cock.
This was probably the worst blowjob he ever received. I tried my best, but he was so big, I kept gagging and choking on his cock. He grabbed my head in place and pushed his cock deeper down my throat. I felt tears running down my cheeks, trying to fight my gag reflex. I’m not sure if I enjoyed sucking him or I was simply very excited by finally having sucked cock for the first time.
He then had me bend over his desk. I felt him rub his cock against my opening. I held my breath, waiting to see what would happen next. He tried to push his cock inside me, but he was barely be able to. It really hurt, but I did not want to stop him. He kept at it for a while, but I was just too tight for him. He only managed to slide in half his cock inside me. I guess this was not very enjoyable for him because he finally gave up. He told me to get dressed and dropped me home.
He did not give up completely though. On the next day, he had me stay after office hours again. He was determined to finish what he had started. He had me bend over his desk again. That day I was wearing a blue button up shirt, a white pencil skirt and a pair of beige high heels. He pulled up my skirt, pulled down my panties and tried to push his cock in my tight pussy again.
Just like the previous day, he was barely able to fit all of his cock inside me. I don’t know if I was too tight or what, he just gave up and instead, had me close my legs and pushed his cock between my thighs until he came all over my panties. I was feeling very embarassed because I was not able to please him. It was not hurting as much as the first time. I just wish I was able to fit all of his cock inside me.
On the third day it finally happened. I felt him balls deep inside me. I was so proud of myself. His moans only turned me on even more. It did not take long for him to cum. It did not really hurt this time, but I can’t say I enjoyed it a lot. However, I was so happy I had been able to please him!
Since then, he would use me everytime he felt like it. He never lasted long. In fact, most of the time he was done within 5 minutes, but I was so happy to be able to satisfy him.
Source: reddit.com/r/eroticliterature/comments/pjwsi2/becoming_the_best_employee_mf_part_1