Hi guys, here’s another story from a while back. I was 20 at the time (24 now) and was a college student working part time for a large sales company. On my first day of work I already noticed that my boss had a thing for me and I liked to tease him with it. Things got worse as the months passed, i liked to dress up in the tightest outfits and obviously show off my body when in his office. When I wore cleavage I would purposely drop things and lean over to give him a proper look and I caught him checking out my boobs and ass more than a few times. It was great fun turning him on, but the rest of the job was really lame so after about 6 months I resigned. The day I resigned he immediately asked me if he could take me out sometime. I didn’t expect that he would ever make that move, but apparently he was just being professional by not asking me out while I still worked there. I agreed we’d go on a date, but only if he would take me to Antwerp (for those who don’t know, that’s a large city in Belgium about 2 hrs away where dutch people like to go shopping).
One week later on a Saturday he came to pick me up to go to Antwerp. We would spend the day there together and I also agreed on spending the night in a hotel there. I wore a sexy green dress in which you could see my curves very well because I knew he would be into that. On our way to Antwerp I already noticed he had high expectations, as he suggested we could go to the hotel straight away. But I said I wanted to go shopping first, so he had no choice but to go clothes shopping with me. He didn’t like that, so I made him go to A LOT of stores. Probably about 10 to 15, and in each one I wanted to try on some new clothes, showing him everything I tried on, teasing him with some sexy stuff. He paid for everything I wanted to buy. In the meanwhile he was trying to have a flirty conversation with me and trying to get a bit romantic, but I completely ignored that and just used him as a carrier and wallet. He was clearly getting upset a bit, since this was not what he hoped for on our date. After shopping we went out for dinner. He only wanted a main course but I ordered a four course meal and made him sit and wait in that restaurant for hours. He still tried to flirt with me a bit, but I did not react to that at all, I just ignored him for the most part of the night and enjoyed my dinner. He was sad, angy, and disappointed. I had the time of my life.
Back at the hotel, I said I was tired and wanted to sleep. All his high hopes were gone now, he was broken and upset with how today has been. But what he didn’t know was that I was roleplaying him all along. When he was in the bathroom I quickly removed all my clothes and waited on the bed for him barenaked. I sat on the bed with my knees up and my legs slightly apart so he would have a clear few of my freshly waxed pussy. When he got back in the room he was shocked and started to stutter something. I thanked him for spoiling me all day and told him it was my time now to spoil him, while I made a beckoning sign with my finger. He moved over to the bed and a few moments later, his rock hard cock was sliding down my mouth. This took him out of his state of shock and into a state of pure horniness. He later told me he had been saving up all week and had a serious blue balls issue all day in Antwerp already. He also told me he fantasized a lot about me since I started working in his office and regularly masturbated while thinking of me. This was his dream coming true, the girl he desired so much was now sucking his cock. In no time he couldn’t hold it back any longer, took it out of my mouth and exploded all over my face and boobs.
I wanted to go clean up in the bathroom now, but he stopped me and ordered me to stay in bed. He wasn’t done with me yet, he said. His dominant side clearly took over now, which intrigued me and so I did what he told me. He started eating me out for a bit but as soon as he was hard again he made his real intentions clear. He climbed on top of me, pushed my legs up till my knees almost hit my shoulders and pushed his big old cock in my soaking wet pussy. Seeing him enjoy this so much, seeing his fantasies come true, turned me on a lot. I came hard while he fucked me like that and he started to dirty talk to me. Calling me a slut and a spoiled brat and saying I finally got what I deserved. After about ten minutes of intense hard fucking he unloaded in me, all the while his first load of cum was still all over me. I felt so dirty and used by this man, at the same time feeling very good and still so horny about the whole switching roles thing.
At that moment I expected him to be out of stamina and wanted to shower and sleep. But again, he told me he wasn’t done and that I was not allowed to clean up yet. He walked up to his suitcase and I found out this man was a lot kinkier than I had ever imagined. He took out handcuffs, rope, lube and some toys. He planned a wild day of sex with me, then thought all day nothing would happen, but was now planning on doing all the stuff he ever fantasized about. He handcuffed me to the bed, arms and legs all apart, face down. It was hot, I acted like I did not like it, but in fact it drove me wild and I think he knew that. He started fucking me again, this time from behind. In the meantime he started lubing up my asshole and pushing his thumb in and out at the same pace his cock went in and out my pussy. It was clear he wanted to fuck my ass too and because my horniness completely took over I just let him do whatever he wanted. He started filling my ass up a little but it was not so comfortable for the both of us at first. He switched back to my pussy and alternated a bit between them. It was hot, the anal got easier and we started to enjoy it both. Not so much later I had my first ever orgasm from getting anal fucked, and it felt amazing, almost unreal. He kept switching between my holes, he took a long time for this but eventually came too. Before cumming he pulled out and unloaded over my face again. This time I couldn’t avoid any of it, since I was still handcuffed to the bed.
After his third load was all over me and I felt dirtier than ever, he made me admit that he was still my boss. I told him what he wanted to hear, and he uncuffed me so I could finally have my rewarding shower. Our horny minds and bodies were satisfied now, we cuddled a bit and went to sleep. Next morning he tried to seduce me again but I went into spoiled brat mode again and basically ignored all his desires. That made me wet, but I did not tell him that. This experience definitely taught me how much I enjoy roleplaying and the extra dimension it can bring. In the months afterwards I hooked up with him a few more times, but eventually the flame died out and we lost contact.
Hope you enjoyed reading this, let me know.
Love, Lotte
Source: reddit.com/r/gonewildstories/comments/pq11jy/fm_i_f20_teased_my_boss_m47_for_6_months_before_i
Such a hot story! 🥵🥵
God I’d love to punish you after a day like that