I nervously sipped my first beer in the Gladstone Tavern in Toronto. I was visiting relatives with my parents and needed to get away on my own for a while. I was very nervous because the legal drinking age in Canada at the time was twenty-one years old and I had barely just turned eighteen, which was the legal age in my State of New York. Also, at that time in Canada, Taverns had a 'Men Only' side and a 'Couples' side. Yo...

I awoke the next morning to Rachel shaking me awake. Startled, I looked down at my comforter to make sure it was covering me since all I was wearing was my mom’s old black lace bikini panty. After a moment of relief that my secret wasn’t revealed, I registered that Rachel already knew my secret. After raising my head, I saw that Kristin and Rachel were in the room wearing their cheerleading outfits. Rachel quickly asked,...

If only I had known how things were going to turn out, I would have been utterly delighted about a road trip with Claude. As it was, I was utterly terrified. It all started when my boss, Mr. Walker, walked into my office on, what had been to that point, a typical Tuesday afternoon at work. “Devin, we’ve got a real mess in Texas. I’m sending Claude down to see what the hell is going on and get things straightened out.” He...

After the rude awakening to my cuckold life and introduction to Crossdressing, my wife decided it was time to go more public with our new arrangement. “Let’s go to the sex shop,” she said to me, “But, put these on under your jeans," my wife said to me passing me a little bag with some clothes in it. I went into our bedroom to put on the outfit my wife has told me to. Inside the bag was a red g string just big enough to fi...

Excited and horny, Lucy got to her feet, grabbed her shoulder bag and Juliette’s hand, and asked for directions to the bedroom. Juliette knew she was going to have her pussy fucked and she was eager to learn what to do and discover what it feels like. One thing she knew for certain — she would savour every second of the experience. On entering the room, Lucy walked to the bed and stood waiting. When Juliette approached, L...

I could see my mom pull into the driveway as I eagerly awaited on the couch. I tried to pretend to watch the tv, but I watched every movement. I could feel my erection stretching the seem of my pants when I saw her pull out a large pink bag from Victoria’s Secret as she exited the car. When she entered the kitchen, she called, “James, come see all the pretty panties I got for you!” I turned red in embarrassment, but at le...

Sabrina knocked on the door to our adjoining suites. I had suspected she was next door getting ready but she had not called or texted and neither had I. I was too busy getting ready. And I may have been too eager to open the door! I was stunned. She was finally in front of me, as beautiful and sexy as the ones on our video chats and through the photos and videos we shared. She was wearing a knee-length sequined pencil ski...

I couldn’t focus on the TV as I waited for my mom and sister to come home. The thought of getting caught jerking off into my mom’s underwear mortified me. As I sat on the couch, worrying about every possible scenario of getting caught, a commercial came across the screen for Victoria’s Secret. My eyes were glued to the TV as the world’s prettiest women modeled the sexiest lingerie. I was definitely attracted to them, but...

My heart was pounding out of my chest as my mom closed the door to drop my older sister off at cheer practice. I knew I’d have at least two hours alone while the two were out of the house. I had been waiting for a chance to be alone for the last five days. Finally, I could execute the plan. Once I saw the car pull away, I ran up the stairs to my mom’s bedroom. I chose my mom’s because I figured if my sister caught me snoo...

I’ve been with my husband for about ten years, but only found out last year he used to CD and be with other men before we ever got together. He’s been hiding that side to me forever I guess, worried about how I would react. And I’ll admit that at first I was shocked and angry, disillusioned maybe. But then I thought about it, how selfish I was being. It had taken a lot for him to come out to me, I know this now. And once...

Brad and I had been seeing each other for over a year when he would come into town. Our meetings started in his hotel suite and progressed over the months to restaurants, walks around town, and trips out shopping. Brad was extremely well off, successful, and more than generous when it came to gifts. In bed, our relationship was fantastic. Brad was a marvelous kisser and loved foreplay. As many sexual experiences that he a...

I was sound asleep and dreaming of being in a six-nine position with a man when I was awakened by my alarm. Rolling over, I put the alarm on snooze and laid on my back for a few minutes thinking about my dream. As I replayed it in my mind, I remember that I had a vagina, rather than a cock. However, my hard and throbbing cock let me know it was only a dream. My panties were hard in the front with the dried cum from last n...

Sabrina and I had come to be friends virtually after running across our respective profiles on some of our mutually favorite sites. We weren’t passable by any means. But being older and wiser in our love of all things feminine, we were comfortable with it and that allowed us to be genuine and graceful. The other thing we shared, we had never been with another person while dressed. And from the moment we disclosed this to...