My Boss Jack

My whore of a mother kicked me out when I was 16 years old. I slept rough for a couple of weeks then got taken in by a homeless charity who helped get me on my feet.

I got a job doing at a builders firm. The owner Jack was in his 50s and supported the homeless charity that had got me off the streets. At 17 I had my own flat, job and money, sadly it came at a cost, but one I was willing to pay. Before you judge, try living rough on the streets of London for just one night!

A couple of months after I went to work for Jack he started touching me up. I had taken some letters into his office to sign. As I stood next to his desk I felt his hand go up my skirt. I liked Jack, but was shocked by what he was doing. I let him feel ny legs and panties. This went on for a while with Jack taking it further each time. Eventually he was feeling me with his hand in my panties. He was always grateful and would say things like “Thank love, I really needed that” he also started giving me money on top of my salary. £30, £40, sometimes £50 for allowing him to touch me up. The money back then made a massive difference to my quality of life.

He asked to start jacking him off, I did and got £50. Blow jobs next for which I received £100. I didn’t allow him to cum in my mouth, although he tried. I’ve often asked myself why I allowed this to happen? I think my younger self for grateful to him for the job and fear I could lose the job and end up back on the streets.

I can’t remember when this happened, but eventually Jack was fucking me. As a kid I always imagined losing my virginity to a man I loved in some romantic setting. The reality though was lay on the desk in a builder’s yard with a guy old enough to my father with his sweat dripping on my face. The cash increased though. That was the year I had my first holiday abroad, 7 nights in Ibiza with a friend I’d made in my apartment block. It was paradise, and all paid for by letting my boss fuck me.

I stayed with Jack for over 3 years, he bought me my first ever car and paid for driving lessons too. I met his wife a couple of times, I think she knew. Looking back I was used, however, it allowed me to live independently and enjoy some of the finer things of life. I didn’t hate the sex, there were times I enjoyed it. Towards the end I even had a couple of orgasms. I cried after the first one, it was the first one I’d ever had! I didn’t think I was capable.

I now have a 17 year old daughter and my memories have bothered me, it upsets me what I had to do to get by, the thought of my daughter sleeping rough and having to do some of the things I did makes me angry. I’ve never allowed my daughter to see her grandmother. I’ve never told anybody about what I let Jack do, or that I was well paid to whore for him. I’ve sometimes wanted to tell my partner, but can’t find the words. The only person that knows is me, Jack passed away years ago. I would love to talk to somebody about it, but just can’t. Even writing this confession has been a struggle; I’ve written and deleted it twice, and will probably delete this one too!!!