Jeff stopped in his tracks and turned to me. "What did you just say?" He asked. "You heard me," I replied. "I dare you to let me come back here next Saturday evening. I want to see what it would be like without you at my side." Jeff just stared at me with a look of disbelief in his eyes. "So, you're saying you want to come back here to have sex with other men? Do you want them to fuck you?" "I don't know if I would go tha...

My wife and I have been married for twenty-three years. Our only child was now in college. Our sex life had become more than a little stale recently. To spice things up a bit, we started giving each other small dares to perform for each other. They started simply. A flash of her breasts as we cooked dinner. A quickie in the shower. An unreciprocated orgasm for her. A blow job for me in the car on the way to the park. We w...

Make-up perfectly applied with shadowy eyes and bright red lipstick - check. Dressed in a beautiful long dress of cool white satin and lace - check. Not a hair out of place. Styled and pulled back with a satin ribbon - check. Underneath, a matching set of white lace bridal lingerie, including a sexy garter belt attached to incredibly sheer white stockings - check. My pussy, still gaping and dripping with the cum of the be...

I was so excited. I had signed up for an excursion in a hot air balloon over the Napa Valley in California. Having never been in a balloon before, I was counting the days until my adventure would begin this coming weekend. I woke early on Saturday. My stomach was already filled with butterflies as my excitement continued to build. I just knew this adventure would be memorable. Positive it would be a day to remember that I...

The following week passed in a haze with a whirlwind of thoughts filling my mind. Would my new friend in the building across from me repeat her performance? Did she really want me to take the lead this week? Could I really expose myself in such a public, intimate way? My wife could not help but notice a difference in my behavior. Several times she asked me what was bothering me. She often caught me with a far-away look in...

It was late on a Friday night, and I was the last person in the office. I had my lights dimmed so I could completely focus on finishing the last of my spreadsheets before heading home to my wife to start the weekend. The sun had already set, and darkness had started to settle in for the evening. Only the light from my laptop was brightening the room I was in. Looking up, I saw that there were no lights left on in the buil...

All of my recent travel for business was getting out of hand. I was now an executive at an accounting firm, having risen through the ranks over the many years I had invested in the company. I had just turned fifty-two. The divorce from my ever-wandering husband was now finalized. It felt good to have the burdensome weight of a dying marriage off my shoulders. The trip to our offices in Denver had been very productive. Sev...

I sit in front of my vanity, carefully applying my makeup. Finishing with the bright red lipstick my husband loves so much. I shift in my seat, feeling the garter straps tugging softly against the tops of my sheer black stockings. My husband's favorite lingerie set. I stand, sliding my feet into the five-inch black pumps my husband loves me to wear. My black silk dress slides into place over all my curves. My husband alwa...

The weeks since my birthday were a whirlwind of emotions. Julie and I were starting to get very comfortable with our new reality. I was now exclusively wearing women's panties, most days personally selected by Julie. All of my old male underwear had been thrown into the trash. Lara had joined us for a second round of play a week or so after my birthday. Julie was really getting into the intense sex we were now having with...

We collapsed together as we both continued to ride out the last of our orgasms. Julie giggled to herself. She slowly lifted her head, placing her forehead against mine. We were both still panting, trying to fully grasp what we had both just shared. Julie looked up. Her eyes locked with mine as she smiled broadly. “Well, my dearest Emily, how did you enjoy my little birthday surprise? I have so much more in mind that we ca...

The office Christmas party was scheduled to start in an hour. I had no intention to attend, having experienced the past three years' versions at my work. Mundane chatter, mostly just about work topics, as well as all the fake holiday cheer. It was not something I wanted to endure again. I looked up as my boss walked into my office with a determined look on his face. "Leslie, I have a big favor to ask of you. I invited one...

My cross-dressing journey started when I happened upon a pair of my then girlfriend's panties that she had mistakenly left in my college dorm room. They were pink nylon bikini-style panties with pretty white lace accents. She had worn them a few nights previously when we had gone out on a date, returning to my room afterward for some wild, passionate sex. I remembered with a smile how she had looked so incredibly sexy wea...

My life seemed so perfect. I was happily married to the love of my life. Married for twenty-three years with two beautiful teenage girls. I was a business professor at our local college and was well respected at work and within my community. That all started unraveling the first day I saw Rebecca. The spring semester was just beginning. I was walking across the quad to my mid-afternoon marketing class when I saw her. At f...

A weekend getaway with my best friend, Alyssa, was just what the doctor ordered. Things at home had become a little stale lately, and honestly a little boring. Sam has been working so many long hours at his job recently. When he got home, he was always very tired. He started going to bed earlier and earlier each evening. He would then get up at the crack of dawn the next day, and start the same cycle all over again. The f...

The move to my family's new home was now complete. We all agreed it was a new starting point in our lives. I had completed my transformation, and was now living my life fulltime as Emily, with the full support of my mother and sister. All of my male clothes had been discarded, and I only wore dresses or skirts now. I did not even own a pair of pants, not even a pair of women's pants. One day, not long after we moved, my m...