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Wedding Gift
Date: 10/26/2016, Categories: First Time Shemales, Taboo Author: annav
... He’d left the outdoor centre and set up his own company which was doing quite well. I was embarrassed that he was doing so well and I was going nowhere. I decided I would be too ashamed to contact him so forget about it. But a couple of days later he paid a visit and insisted in taking me out for a night out. I couldn’t believe how good he looked after all these years. He still had the athletic look about him but he’d added a smoothness to go with it. I could imagine that he still had his choice of women and I knew that he’d be able to show them a good time. So we went out for a meal and it was just like old times. Everything felt so natural and by the end of the meal it was like we’d never spent any time apart. Doug was telling me about how well his business was doing and told me that if I ever wanted a job, it was mine. Well, I’m a proud man, but not a stupid man. I took him up on the offer just until I good myself back on my feet. And so I started working for Doug. I started as the office junior – setting up meetings with customers and suppliers, planning his daily schedule, looking after his diary, but was soon his right hand man and was talking to customers when Doug wasn’t around. Eventually Doug made me a partner. Of course if we hadn’t been old school friends, I’m sure he wouldn’t have done this. Life was good. My confidence had returned. I had a couple of semi-serious girlfriends but nothing too serious. Despite being one hundred percent heterosexual to the outside ...
... world, I still enjoyed dressing up in sexy underwear and exploring my bisexual tendencies. I’d even given myself a new feminine name – Anna. None of the women I dated were important enough to me to share my other side with. So I was resigned to the fact that I’d stay single and keep Anna in the closet. In the mean time, Doug was living the life. As I was taking on more of the workload, he was becoming a bit of a playboy. He had a string of stunning women which he dated. Everyone one of them was classy, well connected and the sort of woman you’ve be proud to take home to the parents. I still found myself attracted to Doug, but realised that our one time together when we were younger would remain that – a one off. As part of his new lifestyle, Doug had the money to spend on property. He had a lovely house in our home town but had bought a flat in Brighton for when he needed to visit town. As we were now business partners and good friends again, I had a key for the Brighton flat and used it when I knew he was away. I loved the flat as it had stunning views of Brighton yet had privacy. Whenever I used the flat, Anna’s wardrobe would come with me. I would spend the weekend dressed from underwear through to my favourite dresses. I’d be shaved from my eyebrows down, paint my finger and toe nails scarlet red, be in full make-up the whole weekend and take a selection of wigs. Absolute heaven! I always made sure that Doug wouldn’t be coming to town and that I’d leave no trace of what I ...