Author's Note: This is a fantasy, please don't be offended by the content or anyone's depiction. I read all your comments and appreciate your feedback.
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FATHER'S BIG SECRET
I always arrive two hours early to the motel room. Every Friday night, I sit on this stool and apply the makeup, achieving a flawless blend. The dark lights will hide any imperfections, but I want none.
Before leaving home, I shave my face, becoming as smooth as I was before becoming a man and get rid of my hairy legs and chest. I chose the clothes I'm going to wear and drive fifteen minutes to this room on the outskirts of my town.
The wig never differs, a blonde bright tone, it always goes well with the rest of the outfit. Then, I pull my fishnets, making me purr in anticipation, and the high heels. One final look, and then I make sure everything else is perfect - you don't want to break the illusion.
It's dark outside. Men text me; it's essentially word of mouth, someone gives my contact to someone else - not my personal number, but a phone I use just for this. This itch.
They never send pictures of their faces. Only from other body parts - I don't care about it. I want names and ages, and sometimes I string them along in an endless conversation to make sure I'm choosing them right.
The last thing I need is another guy beating me up after cuming because they fucked a man like Tony did.
I was still married when I started to cross-dress. It was one Halloween, and I thought it would be funny to dress up like a woman. It was a botched job, but it sparked the flame in my life.
Then it came another Halloween, high heels and fishnets, and lipstick. My wife thought it was a fantastic idea. Ben, my oldest brother, groped me that night, blaming the alcohol.
In secret, I began stealing some items of clothing from my wife. Some bras, some panties. Nothing much. Ben brought that Halloween night up a couple of times. He asked me if I could dress up again - strange request, I thought, which I declined politely.
A couple months before the next Halloween, Miriam, my wife, asked for a divorce. Our marriage had grown cold, and she didn't want to return to an empty bed. Her affair with a guy from her office was going better than she anticipated, and I was left hurt and alone.
Our kids have all grown up now and are out of the house already. Claribel, the oldest, was now twenty-five, and Joe was twenty-three. He reminded me of a younger version of Ben, with his fit body and kind soul.
It was Ben who insisted on me attending the Halloween party at his place. It was he who insisted on a female costume as well. One thing led to the other - I could never imagine that Ben, a straight man, father of three, with a son the same age as mine, married for such a long time with the nicest of the ladies, could want this.
In his garage, away from the eyes of the party, he took me from behind. And he never said a word about it again, but at every Halloween party after that, it became a tradition.
Tonight's date texts me. He's on his way in twenty minutes.
He is late, but I don't judge.
He tells me to wait for him with the door unlocked, ass up and face down. My legs shiver. He's probably the most dominant of the men I've been with based on his communication style. Some alarm bells ring, should I be concerned?
The motel guy installed a panic button in my room after Tony's incident. It's always within reach. I install the hidden camera and start the recording, giving myself one final good look. I'm happy with how I look. Could be more in shape, but after turning forty-five, I stopped caring that much about my appearance.
Lube and condoms are already at the side of the bed. I unlock the door, as tonight's date texts me saying he's parking. With a rush of adrenaline, I can't even breathe but force myself to calm down.
Never been with a twenty-three-year-old. Normally it's older men that hit me up, and I was surprised this young guy wanted someone like me. I sent him pictures, not from my face, and he sent a few pictures of his penis, leaking hard over my photos. It's been four weeks of texting, and I finally accepted to meet him.
Now, the door opens while I'm face down on the pillow, my ass up, covered by the skirt and panties I'm using. Heavy footsteps and the door close behind me. I shiver, it's all in a slumber, except for a couple of bedside lights that give a dim illumination to the room.
