Straight Male / 26
My Boss's Daughter
The guy that owns the company I work for is a total twat. Big headed, aggressive, thinks he’s God g*ft to mankind and a narcissist. I hate the sight of him and his equally arrogant wife.
Over the summer the owner brought his twenty year old daughter into the company to work. She was given a schedule of accelerated training taking her through all of the departments quickly. Imogen is a lovely girl and I’m staggered that Mr & Mrs Obnoxious could produce something as beautiful and lovely, both on the outside and inside. As I’m only five years older than her, she kind of latched onto me. I really liked her company but thought it could do my career the world of good if I dated the bosses daughter. My boss noticed the attraction and told me in no uncertain terms if I touched her I would be fired.
I told Imogen to stay away from me. About three weeks after I started to avoid her, she grabbed me as I was leaving work, and told me that she knew what her father had said to me. She was angry that I had been treated this way and asked if we could go for a drink, our secret. We had a lovely night, even having a meal together.
A week later I’m nailing Imogen at a local Travelodge Hotel. She was no virgin and one of the best fucks I’ve ever had. We always met in secret which made the sex more naughty and enjoyable. I really liked her, dare say even loved her towards the end.
The reason why I’m confessing this is there was also a dark side to the relationship which I’m deeply ashamed of. Although, there was real affection between the two of us; there was also a part of me that enjoyed fucking my bastard boss’s only daughter. When I was fucking her doggystyle there was an element of aggression and hard fucking relating to who her father was. I loved the moment I came in her mouth, not just because she gave fabulous head (which she did) but also that I was using my boss’s daughter’s mouth as my personal cum bucket.
She went on a weekend course to London and I went with her. The hotel Daddy had paid for was excellent, and the room quite high up over looking central London. I wondered what my boss would think if he knew I had made his tipsy daughter stand nude in front of the window as I turned the room light on exposing her to any pedestrian or motorists passing by, or that whilst she was exposed I came up behind her and started fingering her as she was exposed. I also wonder how mad he would be if he knew I’d made her travel back commando whilst wearing a very short denim skirt; or that a couple of truckers got an eyeful of Imogen’s pussy as I fingered her whilst she was drove. We stopped at a service station for lunch (I know we should have known better) I went to the loo and on returning I was shocked that on my approach to the table I could see Imogen’s partially exposed pussy due to the shortness of her skirt. I wonder how many men had seen my boss’s only daughter’s pussy as we ate? I also fucked her in the car park of the same service station in broad daylight; in other words I turned my boss’s only daughter into a dogger too!
The worst point was at the end of our relationship when we were both drunk, and we did anal. It was the first time for both of us, but again there was that element of enjoyment that I was fucking my boss’s daughter up the ass. I was both ashamed of these thoughts and emotions but they also generated some brilliant sex.
In the end the relationship fizzled out, after three months she returned to University that’s hundreds of miles away; we spoke every week for the first month and then less until neither of us contacted each other. I really enjoyed myself though, and would have loved it to become something more; however, that dark element both bothered and pleased me. On a couple of occasions my boss has been ripping into me for something and nothing; during these rants I just imagine his daughter in that hotel window, or exposed in the service station, or my cock sliding up the ass of his little princess. He even asked during one tantrum why I was smiling? If I ever leave the company I will tell him.
Over the summer the owner brought his twenty year old daughter into the company to work. She was given a schedule of accelerated training taking her through all of the departments quickly. Imogen is a lovely girl and I’m staggered that Mr & Mrs Obnoxious could produce something as beautiful and lovely, both on the outside and inside. As I’m only five years older than her, she kind of latched onto me. I really liked her company but thought it could do my career the world of good if I dated the bosses daughter. My boss noticed the attraction and told me in no uncertain terms if I touched her I would be fired.
I told Imogen to stay away from me. About three weeks after I started to avoid her, she grabbed me as I was leaving work, and told me that she knew what her father had said to me. She was angry that I had been treated this way and asked if we could go for a drink, our secret. We had a lovely night, even having a meal together.
A week later I’m nailing Imogen at a local Travelodge Hotel. She was no virgin and one of the best fucks I’ve ever had. We always met in secret which made the sex more naughty and enjoyable. I really liked her, dare say even loved her towards the end.
The reason why I’m confessing this is there was also a dark side to the relationship which I’m deeply ashamed of. Although, there was real affection between the two of us; there was also a part of me that enjoyed fucking my bastard boss’s only daughter. When I was fucking her doggystyle there was an element of aggression and hard fucking relating to who her father was. I loved the moment I came in her mouth, not just because she gave fabulous head (which she did) but also that I was using my boss’s daughter’s mouth as my personal cum bucket.
She went on a weekend course to London and I went with her. The hotel Daddy had paid for was excellent, and the room quite high up over looking central London. I wondered what my boss would think if he knew I had made his tipsy daughter stand nude in front of the window as I turned the room light on exposing her to any pedestrian or motorists passing by, or that whilst she was exposed I came up behind her and started fingering her as she was exposed. I also wonder how mad he would be if he knew I’d made her travel back commando whilst wearing a very short denim skirt; or that a couple of truckers got an eyeful of Imogen’s pussy as I fingered her whilst she was drove. We stopped at a service station for lunch (I know we should have known better) I went to the loo and on returning I was shocked that on my approach to the table I could see Imogen’s partially exposed pussy due to the shortness of her skirt. I wonder how many men had seen my boss’s only daughter’s pussy as we ate? I also fucked her in the car park of the same service station in broad daylight; in other words I turned my boss’s only daughter into a dogger too!
The worst point was at the end of our relationship when we were both drunk, and we did anal. It was the first time for both of us, but again there was that element of enjoyment that I was fucking my boss’s daughter up the ass. I was both ashamed of these thoughts and emotions but they also generated some brilliant sex.
In the end the relationship fizzled out, after three months she returned to University that’s hundreds of miles away; we spoke every week for the first month and then less until neither of us contacted each other. I really enjoyed myself though, and would have loved it to become something more; however, that dark element both bothered and pleased me. On a couple of occasions my boss has been ripping into me for something and nothing; during these rants I just imagine his daughter in that hotel window, or exposed in the service station, or my cock sliding up the ass of his little princess. He even asked during one tantrum why I was smiling? If I ever leave the company I will tell him.
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