I grew up with a loving and affectionate mother, but an absentee father. Dad worked all the time, and most of it involved travel. I didn’t learn that he had cancer until after he died. I was eighteen years old at the time. Fortunately, he had a very good life insurance policy and had invested wisely. He left Mom and me independently wealthy. My mother was thirty-six, twenty years younger than my father when he passed. Bec...

I connected with Jim online. Although married, I enjoyed having occasional one-night flings. I’d usually connect with a married guy who came to town on business. I wasn’t interested in anyone local. It was important to get to know the guy before I met him though. The process took a while but always resulted in meeting a nice guy. Over the last couple of years, I’d fucked fifteen very nice and appreciative married men. All...

Mom kissed us both, and left for the office. Jill and I sat and had coffee. “Well?” Questioned Jill. “Well what?” “Geez, girl. You slept with Mom for the first time. So tell me. How was it? “It was very nice.” “Come on. Give me details.” “Okay. When I got in bed with her last night, we cuddled and kissed. I honestly thought that would be it. But, of course, I got aroused. She asked if I’d like her to take off her flannel...

I awoke Sunday morning in my pink nightie. I thought about how much had happened in the previous two days. I was now Jim’s girlfriend. I had sucked off four men and swallowed a quart of semen. I became aroused. I only had to play with my clit for a minute before I started cumming. I caught most of it and fed it to myself. I looked forward to sucking Jim’s huge dick. “You better get dressed, girl,” I said out loud. I did m...

I’m married and we have two houses. One is in a suburb of Chicago and the other is on a lake in Wisconsin. When we first bought it, we went frequently. We became friends with the only neighbors, Jim and Barb. We had a good time with them, but after two years, it became clear that their marriage was on the rocks. Shortly, they got a divorce. After that, the three of us would get together, but it wasn’t the same. Jim is a t...

“I can’t believe I’m saying this, but I like having twin girls,” Mom said, as we arrived home after our nice dinner. “We had a great time, Mom. Thanks. And thanks for letting me have my sister,” Jill happily exclaimed. We got ready for bed. As I was about to retire, I heard a knock. “May I come in, sweetie?” “Of course, Mom.” She sat next to me. I had taken off my dress and was only wearing a black bra and panties. She wa...

We got out of bed, took off our nighties, and took a shower together. It was possibly our last chance to be intimate. We washed each other. We dressed. I casually put on a white lace bra and slipped in my forms. I stepped into matching panties. Finally, a pair of nude pantyhose. We did our makeup together. I took out one of her pencil skirts along with a white ribbed sweater that I had worn that week. “While you look grea...

The divorce was final in two months. I owned only women’s clothing and lingerie. Joann let everyone know about the divorce. What we hadn’t considered was that her other friends, as well as colleagues, would want to fix her up with dates. Besides that, the same friends wanted to fix me up. We put them off but realized that if we didn’t occasionally go out with men, everyone would think we were lesbians. We considered that...

When we returned home from our girl adventure on a Saturday. The next morning, we sat down to talk about what to do next. “Elizabeth, You enjoyed the entire week,” Jo declared. “I am sure we had a better time than we would have if you were Bob. I had a great time. It’s up to you, but I think it’s time for you to be a woman full-time.” “Are you sure, Joann?” I asked. “When was the last time you wore male clothing other tha...

I woke up early Thursday morning and looked at my sister sleeping soundly. Although completely naked, I didn’t look at her as a guy would. I looked at her as my twin sister. I got out of bed and slipped on my panties. I still had a bra on. I grabbed one of her robes. I went downstairs and made coffee. I brought her a cup. Jill was awake and was sitting up, her beautiful breasts exposed. We sat and talked. We agreed that w...

Jillian and I are fraternal twins. As with many twins, we have much in common. At twenty-two, we’re both five feet, eight inches. We have blond hair, blue eyes, and fair complexion. We are even close to the same weight. I wear my hair long, and If I release my ponytail, we have the similar-looking hair. We have also always been very close and hang out together. We have many mutual friends. More than a few times, people ha...

I had reached the point where the only time I wasn't Elizabeth was at work. “I know you hate wearing male clothing,” Joann told me one morning as I was getting ready for work. “It’s like you are cross-dressing as a man. I want you to quit your job so you can live as the woman we know you want to be. We are so much happier as two girls. I want you to be happy.” I knew she was right. I wanted to be Elizabeth, not Bob. That...

We were standing around talking when Susie’s husband Peter, and Patty’s husband Joe, wandered over. I took a deep breath. They had each known Bob for years. Joe said, “What are you girls yapping about?” “Oh, just girl talk,” replied Patty. “Who’s your pretty friend, Joann?” asked Peter. “This is Elizabeth. We are old friends. She is visiting from out of town and may be moving here. We have been friends since college.” “Ni...

After an exhilarating weekend, my life unfortunately returned to normalcy. Bob went back to work. We came home, had dinner, and watched TV. I realized Joann was processing. Duh. I just told her I wanted to dress and act like a woman. I didn’t want to press my luck. By Thursday, Joann seemed to have made a decision. “I know you want to dress, so take Friday off and do it.” She smiled. Joann kissed me goodbye as she left, s...

I steered into the driveway that I had pulled into hundreds of times. This was the first time dressed as a woman. I knew I couldn’t stop what I started. I wasn’t controlling the overwhelming desire to be feminine. It seemed to control me. As a couple walked by, I pressed the remote and pulled into the garage. I watched TV for a while. Though it was late, I decided to try on the lingerie and heels I purchased. After dawnin...