Where it happened: Boss's Office
Langauge: English
Sex: Female
Rating: 5
Category: Straight
When I was eighteen my first job also led to the first time I had sex. I was a secretary in a small business and my boss was a very nice older gentleman I believe in his 60’s at the time. It wasn’t until the first few months went by when he started flirting with me. He wasn’t rude in any way only flattering. At first I was a little shy but after awhile I loosened up and even flirted back. After awhile longer when I dropped off files at his desk he would caress and touch me in some way and to be honest, I liked it. One afternoon after I dropped off some files in his office he held me by my wrist before I turned to leave raised up and kissed me. I was a little taken back at first but then he said his flirtation was due to his liking me. I admitted to him that I liked him as well and he kissed me again. He fondled my breasts and I felt like I never have before. He told me he wanted to make love to me right then and there but I told him this wasn’t the place and we should wait until we could go to a hotel after work. I also told him I was still a virgin and not on birth control and knew he didn’t have a condom and I told him I didn’t want to get pregnant. He told me he couldn’t wait and had fell in love with me and said nobody would come in and locked his office door. He said nobody would know and not to worry about getting pregnant because a man his age couldn’t produce any more children. He started hugging and kissing me and I couldn’t take it and hugged and kissed him back. He sat in his chair and had me sit on his desk. He slid off my heels and held my feet up to his nose and sniffed my feet and then sucked my toes through my stockings. At first it was a little weird but I just went along with it. He then stood up and took down his slacks and boxers. He took my stocking feet and rubbed them all over his penis until he got really hard. Once he got hard he told me to straddle him while he was sitting in his chair. I was a little nervous at first because I figured my first time would be different and couldn’t believe this was happening. I stood there at first staring at his hard penis and he begged me to get on top of him. I walked over to him and lifted up my dress and straddled above his penis. I slid my panties to the side and slid his penis inside my vagina. He moaned and took the top of my dress and my bra down to expose my breasts. He hugged me and lay his head on my breasts. He told me to start riding him. I told him I was going to have to go slow because it hurt a bit. I didn’t say anything of course but it helped that he didn’t have that big of a penis and after slowly riding him a few minutes later the hurt started to turn to feeling good. After a few minutes more I started riding him a little faster and he started moaning louder and said, “yes!” over and over again. I couldn’t believe I was losing my virginity and wrapped my arms around his head holding him. I noticed I was moaning as well and it felt so good having his hard penis inside my vagina. We were both getting sweaty and kept moaning and I hoped he was doing alright being as old as he was and as young as I was. Then it happened, I felt the feeling building up more and more and I started having a orgasm. I have masturbated and used dildos on myself before this time of course and the feeling I was having while having sex with my boss I felt those times when masturbating and I was so happy it was happening the first time I was having sex. After I was done and caught my breath I noticed he was still hard, moaning and kept wanting me to ride him so I knew he hadn’t finished yet. A little worry crept into my mind after my moment had past. As I kept riding him I was still nervous about his bare penis being inside me and even though he said he couldn’t have children at his age, I still worried that eventually when he finished it would be inside me and even though we were already more than half way into sex I didn’t want to get pregnant at my age at the time. It may have also been a sign but as I was riding him I stared out the blinds of his window and watched as two different women walked with their children on the sidewalk. I couldn’t take it any longer and jumped off of him and his penis slid out of my vagina. He yelled at me as to what I thought I was doing and begged me to get back on him. I just stood there in a bit of shock and he moaned and cried out no while he grabbed his penis and started masturbating. After a few seconds he ejaculated in the air and all over his office floor and I just stood there watching his penis spurting out his semen. After he was done he started yelling at me that a woman should never do that to a man and be it we were already full into having sex I should of kept going and let him ejaculate inside my vagina. I started crying and I positioned my panties back in place and pulled my dress down. I ran out of his office in my bare stocking feet and didn’t bother grabbing my heels and only grabbing my purse on the way out and I never went back there again. I couldn’t believe I had just lost my virginity and in that way. I did feel guilty for what I had done to him and knew I was at fault for letting it happen in the first place. I also felt guilty for having a orgasm on him and not letting him have a orgasm in me. In the end I was relieved I never did let him ejaculate inside me and possibly getting pregnant. I even took a pregnancy test to make sure there wasn’t a chance I got pregnant from his pre-cum and thankfully the test turned out negative. After awhile I just figured what was done was done and moved on. After a few years had past I hadn’t really thought about it much until I was reading the newspaper and saw in the obituaries that he had past away in his sleep of natural causes. He was in his 60’s then and was in his 80’s now when he passed and the memory had come back to me as it was yesterday. I felt bad again for what had happened all those years ago like I had robbed him of such a pleasurable experience and now he had died without having had that pleasure and would never be able to have made up for it with me and now never will. I went to his funeral and when I saw him in his coffin I felt sorry for him and wished I had let him ejaculate inside me and if I had gotten pregnant then I would of just had the child but I didn’t let him and what is done is done and I can’t make up for it for him now. It was awhile before I never thought about it as much as before but needless to say my first time was a memorable one.
Processing your request, Please wait....
