I have taken strap-on's from several different women through the years but the most memorable was many years ago I was friends with a "straight" white female. I say straight because she was divorced but had a lot of masculine attributes and mannerisms. We were hanging out one afternoon and she asked if the rumors she had heard were true, was I a transvestite. I told her I was and for the next 4-5 hours she asked question after question about it, what I liked, how I dressed, etc. By now it was almost 2am and she had to go to work the next morning. Before she left she said she would like to see my feminine self. I asked if she was asking her out on a date and she immediately said yes. I agreed and we decided on a date 3 days later. She said she would take care of everything.
The day of the date she called and told me she had left a hotel key on my car and she would see me later that evening. I got my things together and headed to the hotel, let myself into the room and was greeted by a big bouquet of red and pink roses and a bottle of white wine. I set about getting ready, hair, make up, nails, lingerie and a new skirt and top.
To make a long story shorter...The night was spent with her giving me some of the best fucking I have had (not quite the best but it was right up there at number 2 or 3). We started dating after that, I was her gf and she was my BF. She totally ignored my insignificant little bits and concentrated her efforts on my tight pussy. She was a natural and exuded the masculinity and confidence any woman would look for in a man. Sexually she knew how to take control and didn't hesitate to let me know when and how she wanted me. Sadly she ended the relationship after about 9 months because she was "questioning her sexuality". We had many long and often tearful conversations before ending the relationship but in the end she was worried about her family and what they would say or think.