My wife and I get together with our neighbors to play cards to play cards about once a month. We generally have a good time but there are no stakes involved. For a poker player like me who is accustomed to gambling for large amounts of money playing just for fun is a little, well… boring. One night about a month ago, I tried to make the game a little interesting by including some drinking. We started the night playing pit...

This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion of local philanthropist. The annual party raises a significant amount of money for a designated charitable foundation. This year all proceeds were designa...

Every year a city about an hour away from where I live hosts a big charity costume party that coincides with Mardi Gras. I had decided to attend the event as my female persona, Tessa. Since I don’t get many chances to go out in public I decided I was gong to go all out for this event. For the last two months I had been on a strict diet, more like starvation but I knew the results were going to help me with my transformati...

Whenever I would masturbate, which was quite often, I loved to create the most outrageously imaginary fantasies, often losing myself within those fantasies where time seemed to pass at a different rate stretching to an infinite horizon. The actual physical act of masturbating and the fantasy that accompanied it was only a small part the actual fantasy which I had created years earlier and had been continuously adding to s...

When I awoke the next morning sun was shining in through the windows, bathing my golden hair in its rays. I got up quickly, but careful not to wake my lovers. The nice weather made me think that we would soon have to leave the cabin and my taste of life as a girl would be over. Regretting this, I was determined to make the best of my morning with them. I went to the bathroom and once again treated my body with the uttermo...

I do not know how long I sat there gazing into the flames and sipping wine in complete peace. The wind outside was far away in my mind, but suddenly a huge bang broke the silence. The door flew open and slammed into the wall. Rain swept through the small cabin and sprayed me with icy cold droplets. I nearly fainted from shock, and the noise from my pounding heart overshadowed the howling of the wind. Two dripping wet, dar...

I always wanted to be a girl.Every time I saw those pretty girls prancing around the college campus I’d become green with envy. Their feathery skirts caressing glossy thighs. Long, silken hair cascading across bare shoulders. High heels clicking on the pavement as they paraded their fit asses in front of all the guys. They were allowed to be sexy, and no one would stop them. And the warm summer days would convince even th...

I woke up and saw the bright, yellow orb of sun shining in through the broad windows. It was warm, and the thin linen was wrapped around my sweaty body. I was glad I remembered to remove the tight corset before going to sleep, and I was now wearing only the thigh-high stockings and garters. A pair of white panties lay on the floor where they had been hastily thrown. My fake breasts were still firmly attached, and I had al...

The large gown rustled, and the heels clicked loudly as I descended the stairs in my home and walked towards the front door. I would be picked up by my friend’s sister before going to the church. I had never met her before, but he’d assured me that she knew nothing of my secret. It would be nice to have someone to confide in, but I knew being treated as a girl by everyone would probably make this feel more natural in the...

There was something truly surreal about feeling his half hard cock filling my mouth. The salty taste of his orgasm lingered on my lips as his white cream oozed down from my face to drip onto my large exposed breasts. My eyes looked up at him through smeared makeup in pure delightful submission, silently pleading for a sign that he had been truly pleased by the curvy redhead that had been offered to him.The pain in my knee...

I was just entering my prearranged destination. It was 11 pm and just before I paid the admittance fee, I stopped to look at myself in the mirrored walls. Reflected before me was a sexy, if a little sluttish looking woman in her thirties. The only discrepancy being that I was actually a 37-year-old man, happily married and, here at the precise instruction of the woman I loved and was married to. She had returned home a da...

I initially met Richard through a TG Community site and we seemed to hit it off from the very start.   He was very open about his likes and dislikes, about him being a TG admirer, about having had a fair number of encounters and dates, but he never pressured to know anything about me.   Drawn by his gentleness and gentleman ways though I found myself sharing my deepest dreams and wildest fantasies with him through regular...

Finally, I had everything I needed to dress up for a little fantasy today.  I had always thought my neighbor Steven was extraordinarily handsome and sexy.  At six-feet-three inches, Steven is precisely what described as tall, dark, hard tone and muscular.  Tonight, I would finally have my chance to fulfill a fantasy to show him just how much I wanted him.     When I was in my teens, I always heard he was a ladies man with...