My favorite thing about the holidays is that I can freely shop for lingerie without feeling nervous. Plenty of guys buy sexy underwear for their wives and girlfriends so there is always a feeling of freedom at this time of year to shop and take my time. I could really spend hours in Victoria’s Secret looking at all of the pretty, lacey thongs, boy shorts, bras, and garters. On this trip I wound up with a new sexy pink tho...

As an introduction, my wife introduced me to a whole new world many years ago. It all started shortly after she broke up with her girlfriend and started dating me. I guess she really missed certain parts of her old relationship. For Christmas one year, I received a Victoria's Secret box. It had two sets of lingerie. I thought she was going to wear it for me but she convinced me to put it on with a couple sexual favors. It...

Jamie tugged on the short whiteskirt, desperately trying to get it lower. Giving a whimper when he realised that as soon as he stood back up and put his hands on the bar, his skirt gently slid back up and revealed more and more of his smooth long brown legs. The skirt barely stopped before reaching his plump ass sticking back as he leaned up against the bar. With a quick hand movement he pushed his short black hair away f...

I remember slipping out of Mr. and Mrs. L’s bed that morning after the Christmas Party, getting dressed and going downstairs. No one was awake yet so I found my panties, jeans and pullover in the room off the kitchen. I got my coat and gloves from the hall closet and quietly left the Dean’s home. As I walked home I was trying to understand just who I was. Am I still the sissy I love being or am I bisexual now that I've fu...

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring...

I was invited to Ben’s house for dinner Saturday evening and spent the day getting ready. His wife Susie was looking forward to meeting me again and getting to know me better. I was unsure how the evening was going to go, but I decided that I was going to try and enjoy it as much as possible. I spent the afternoon getting ready, and shaved smooth all over, hoping that Ben and I would get to be together again. I moisturize...

I got a call from Ben Monday morning, and he needed to talk to me urgently. His wife was going to be coming to the proposal meeting that he had talked about and she was looking forward to seeing me there. Ben asked if I would be able to be free for the day on Thursday. My work schedule was light, and the thought of going to a business meeting with them seemed interesting, so I accepted. Ben promised that if everything wen...

I had been cross dressing for years but only in private. I had also had a thing for bondage for a long time. A couple of years ago, I met two other cross dressers who were into bondage. We had been getting together every couple of months and playing bondage games with each other. We would take turns tying each other up and taking photos and videos. But, it was always clear that the other two were completely straight and n...

I had been chatting with Ben online for a while and we had talked on the phone several times before I decided to meet with him. I had met him through Craigslist so he knew what I was all about from my ad. We arranged to meet at restaurant for an early dinner so there would be plenty of people around. That Saturday, I spent my time getting ready. I showered and shaved smooth and used a nice lotion to make my skin super smo...

Christmas break at the Boarding School. It was December 15th, the dorm was empty and I was alone in my room. My parents sent me away to an all-male College/Boarding School in the Northeast, USA. They suspected I was Bi or Gay and wanted me out of sight and out of their way. They informed me I would be in school until the summer break. My name is Timmy. I am eighteen years old. I am green eyed, five foot ten, one hundred f...

I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if I spend all this time and ef...