Straight Male / 28
On a rainy day, between calls for my insurance business, I ducked into an upscale lounge/bar downtown and spotted a truly handsome woman smartly dressed in a suit sitting at a table, where I had perched myself on the bar and ordered an Irish coffee. She had a leather portfolio on the chair next to her. We first friendly-glanced at each other then I got up the nerve to walk up and ask if I could join her. It turned out that the lady, Amelia, is an attorney for international shipping companies. At 40 years of age, she was over a decade my senior and she fascinated and intimidated me. I'm no wimp but highly intelligent women with more life experience than I have just intimidate and fascinate me.
Amelia was divorced and not looking for any type of relationship with anyone, she said. On our initial meeting, we had a great chat and when I asked if we could stay in touch she responded affirmatively. I saw Amelia as a friend for about a year and I began to want her sexually. However, she did not offer the slightest hint that she was so disposed. I determined to bring up the subject indirectly and so, our sex talks began. As it turned out, Amelia had a lover by the name of Carrie. In time, I met her. She was a beauty, closer to my age. Yet, by that time I knew Amelia was not a lesbian. At first, Amelia kept her at a distance from me. The feeling that Amelia might be jealous of my interest in Carrie passed through me mind.
Then, Amelia began to talk about various lifestyles and sexuality. Amelia wanted to take me to a fine restaurant for my birthday and I was happy to accept. I had no problem accepting Amelia's generosity because I knew she was very well off from her home and its furnishings and the high end Lexus she drove. Oddly enough, she asked if I would mind Carrie joining us and, of course, I responded positively.
We went to a very expensive club and before we ordered had several drinks. It was then that I was informed that Carrie was a tranny, a shemale. All I could think of saying was, "That's very interesting." However, Amelia seemed to have a shift in personality and began to regale me with a full disclosure on her sex life with Carrie, in front of Carrie, who reacted in a bubbly, happy mood. After dinner we all went to Amelia's large home and Carrie went into the kitchen to make some coffee for us. While there, Amelia suggested that the three of us have sex. Until that moment I had not yet determine how I was going to approach Amelia for sex but suddenly, there it was. The problem was that the idea of dealing with a penis, tranny or not, was a mind-blower for me. As it turned out, it was all-said, amazing.
I suppose this is not so much a confession than it is a suggestion. My patience and open mindedness was rewarded by the most extraordinary sexual experiences I ever had. Not that my history is overflowing with it but these two are taking me to far away, dreamy places.
Amelia was divorced and not looking for any type of relationship with anyone, she said. On our initial meeting, we had a great chat and when I asked if we could stay in touch she responded affirmatively. I saw Amelia as a friend for about a year and I began to want her sexually. However, she did not offer the slightest hint that she was so disposed. I determined to bring up the subject indirectly and so, our sex talks began. As it turned out, Amelia had a lover by the name of Carrie. In time, I met her. She was a beauty, closer to my age. Yet, by that time I knew Amelia was not a lesbian. At first, Amelia kept her at a distance from me. The feeling that Amelia might be jealous of my interest in Carrie passed through me mind.
Then, Amelia began to talk about various lifestyles and sexuality. Amelia wanted to take me to a fine restaurant for my birthday and I was happy to accept. I had no problem accepting Amelia's generosity because I knew she was very well off from her home and its furnishings and the high end Lexus she drove. Oddly enough, she asked if I would mind Carrie joining us and, of course, I responded positively.
We went to a very expensive club and before we ordered had several drinks. It was then that I was informed that Carrie was a tranny, a shemale. All I could think of saying was, "That's very interesting." However, Amelia seemed to have a shift in personality and began to regale me with a full disclosure on her sex life with Carrie, in front of Carrie, who reacted in a bubbly, happy mood. After dinner we all went to Amelia's large home and Carrie went into the kitchen to make some coffee for us. While there, Amelia suggested that the three of us have sex. Until that moment I had not yet determine how I was going to approach Amelia for sex but suddenly, there it was. The problem was that the idea of dealing with a penis, tranny or not, was a mind-blower for me. As it turned out, it was all-said, amazing.
I suppose this is not so much a confession than it is a suggestion. My patience and open mindedness was rewarded by the most extraordinary sexual experiences I ever had. Not that my history is overflowing with it but these two are taking me to far away, dreamy places.
