He was about 50 if I remember correctly. I had been dressing in my mother’s underwear and dresses for a few years and found it so sexy, I had not co...sidered myself gay or bi, I just knew I belonged in female attire, it made me happy and felt natural. The thought of pleasing this man made me excited, terrified and scared, but very excited. I could tell from my little clitty. After chatting for a few hrs he wanted to meet me?I had never met anyone before; no one had ever seen me dress before? But. That Friday evening I had reservations at our favorite restaurant. Andrea got all dolled up. Again I ordered a medium rare steak, a lobster tail, and a shrimp cocktail finished off with a cherry cheesecake and three beers. Andrea ordered four shrimp cocktails and a cherry cheesecake. I drank three beers and she had Pepsi. We had a great date and agreed that maybe we should do this one a month instead of once a year.On the way home Andrea asked me to get her a bottle of Champaign. She wanted to. Quite naturally my hand gently lifted and stroked my cock which rapidly grew to an even bigger and harder stage standing at attention like a proud army soldier. Once fully hard and grown I took my hand away and showed her the result: my colossal 10 pounder proud cock standing up straight on its larger pedestal of balls, hard and long. Sylvia seemed to be impressed as she loudly remarked it to be incredible and asked me if she could touch it. I could see she was scared by the giant size of my. Minutes pass, you are the other side of the room, I am still suspended and my arms are really hurting. ‘Master?….’ I call out and feel once again the sting of the cane. As I cry out I realise that now there will be trouble, you bring a ring gag and force my head back so you can secure it, you step back and cane me between my legs, it stings my lips and I groan loudly. Again and again you sting my pussy and I get wetter and wetter, the pain is awesome and you know it. You are bringing me closer.