Standard disclaimers apply.
I'm Madison, Chapter 5. The Disaster
After that night with Amy, I really settled into my life as Madison. On top of staying dressed as a woman at home, I now went out exclusively as Madison. The only times I responded to and acted as Taylor Madison were when working or doing something legal. Even then, I still dressed as a woman.
My job telecommuting simply enabled me to live the life I wanted, which was nice. Talking in my old voice on the phone instead of my newer, normal voice was getting weirder and weirder, but not too awful.
My new driver's license photo was fantastic, though, and getting it was a hoot. Amy went with me for "moral support", although I think she just went to laugh at people's reactions. The lady behind the counter looked like she was brought in from Central Casting to play the role of the judgemental lady from Hell who couldn't tell me what she really thought, but tried to convey her feelings of rage with half-glares and limiting her responses to grunts and "uh-huhs." When it was time for my picture, I checked my make-up and teased my hair in my little make-up mirror. Then I smiled as sexily as I could for the camera. Yeah, I looked like a slut, but it's my favorite license photo ever!
After a couple of months my group of friends now numbered around the 20 Jo had described. I still hadn't slept with any of the guys yet. A couple were interested, but I wanted it to be perfect for my first time. I wasn't really angry with Jo for forcing that first blow job from me the first time we met, but I was a bit resentful at how rushed it was. I had several criteria for my deflowering, and I was going to hold out as long as I could.
For my first time, I wanted a good looking guy (naturally) who didn't know me (in case it went badly) who was only in the city for a few days (so he would leave and I wouldn't have to see him again), and would accept me for who I was, not as a freak show.
I'd communicated this to the group, and they all started taking bets on how long I'd cave before hitting up one of the guys in the group. I did kinda nurse a crush on Tony Blue Eyes, as I called him, and he was interested, but I really wanted to try a...test run, in a way. It would be easier to stay in control of the situation with someone I didn't know. This was very important to me. They all told me they'd look for candidates, and, amazingly enough, it was Amy who came through.
"His name is James Keith, and he's really hot!" Amy exclaimed.
An alarm bell went off inside my mind. I knew a James Keith from work. He was an engineer who worked on a different account than me. He was good looking, and married with kids. I hadn't spoken to him in a couple of years, but I knew him pretty well, and he knew me. I didn't want to act nervous over what was probably nothing, so I tried to act casual.
"Really? Do you have a picture?" I asked.
"No, but he's around 6' tall, nice build, brown hair and eyes."
Wonderful, that only described most of the men on the planet. I should stop this now... "I told him all about you, and he said he'd love to have dinner with you tomorrow."
"What?" I gasped.
"Tomorrow. He wants to spend tomorrow evening with you at his extended stay hotel. Just a quiet night of dinner, and who knows what else?" She smiled at me, sharing my supposed excitement.
Jo stepped in here, "Madison, he sounds perfect. What have you got to lose?"
"Nothing I guess. I'm just a bit nervous."
"Don't be!" Amy put in here. "He's married, likes girls like you, and won't stay long. You'll have a blast!"
I managed to talk myself into thinking that there probably a few million James Keiths in the world, and what were the odds that this one was the one I knew? After all, he lived on the west coast, and here I was on the east coast. I agreed to the date, and got the directions to his place. I was excited, but terrified at the same time!
The next morning I started getting ready. I took a long, hot bath in the whirlpool garden tub, finger opening my ass so the warm water went inside. Once I was relaxed, I used an enema to clean myself out, in case things progressed as I hoped. Finally, I filled a small syringe (with no needle of course) with lubricant and filled my ass. Once that was ready, I applied my hair removal cream to my body and shaved the rest of the way. Once I was hairless except for my heart shaped pubic hair region, I started to apply my make-up. That took forever, but at the end, I looked really really good, and a little bit slutty, which was what this evening was about!
Once my body was ready, I started putting on my clothes. I wanted this James' eyes to pop when he saw me. I put on a black leather corset that included a leather choker for my throat, as well as garters to my black thigh high hose. It cinched my waist, making my figure as perfect as it could be. Above the garters went a pair of lacy black panties. On top of all this I wore a red blouse that matched my lipstick and nails, a mini skirt that barely covered the tops of my thigh highs, and my super-sexy strappy stilettos. I put in my red hoop earrings, and gold studs in the other piercings, and I was almost ready! Finally, I pulled on my wig for this night: long, luxuriant curly red hair.
There - after only about 6 hours of prepping and primping, I was ready to go. I grabbed my purse and headed out. As I left, I nodded to Doris, who had just gotten back from somewhere. She gave me a small frown, shook her head, and went inside.
The drive to James' was supposed to take 30 minutes, and I was leaving more than 15 minutes late. I started speeding to make up time, while thinking positively dirty thoughts about what might happen in just a few minutes. Would we eat first? Or would we just jump in the sack? Would he have a huge cock? My mind was wandering with these thoughts when I saw flashing blue lights behind me.
Shit!
I didn't know what I'd done, but I pulled over.
The officer stepped up to the car. He was tall. Very tall. Taller than me. Good build too. He was Hispanic, with tan skin and thick brown hair. I rolled down the window as he approached.
"Yes, Officer?"
"Ma'am, did you realize that you failed to stop at the last stop sign?"
"No, did I?
"Yes, I'm afraid I'll need to write you a ticket. Can I see your driver's license?"
Well, shit. I handed it to him and expected him to start calling me "Sir". This could get ugly fast. He went back to his car for a few minutes, then walked back.
"Going on a date?"
"Yes." Well, duh, Officer Sherlock.
"Well, I don't want to spoil your evening. Drive more carefully, ma'am."
What?! I looked up at him for the first time since handing him my license. He was smiling down at me, with perfect white teeth. He really was gorgeous! I noticed his eyes were drawn to where my mini skirt failed to cover the top of my hose.
"Well, thanks so much Officer!"
"Call me Bill." What a nice name. A manly name. I liked it, too.
"Thanks Bill," I smiled at him.
"Before you go, here's my number, in case your date doesn't go well."
Now I was flirting, "Are you asking me out, Officer Bill?"
"No, just giving you my number. In case you need it."
"Why would I need it, Officer Bill?"
"In case you want to go out."
I was smiling now, but needed to get moving. Beside, I felt like being a tease, "OK, have a nice evening, Officer Bill!"
"Don't make fun of me, Madison. I have handcuffs!"
I laughed with him and winked, "Don't make a girl too many promises!" Then I sped off.
Well, this evening was going great!
I pulled into the hotel parking lot and checked my hair and make-up. I spritzed a bit of perfume on me and walked in, my legs working a feminine strut. I was loving these heels! I had his room number on the 3rd floor, and took the elevator. No one was around, so I used the elevator walls, which were mirrors, to check my outfit once last time.
I walked to the room and knocked on the door.
James answered the door.
My James.
I mean, the James I know from work.
What are the fucking odds!
I mean it. What are the god damned mother fucking odds of the one James Keith I know in the world being the same god damned mother fucking asshole who just opened the damned door.
Apparently, not long enough odds.
Shit! Shit! Shit!
My eyes widened and I felt my face pale. I almost fainted! Here I was, looking like a whore, and the guy I was going to meet was someone I worked with!
Still, it had been 2 years since I saw him last. Maybe he wouldn't recognize me. The lighting was dark here. I could just leave.
"Come in," he said. "Amy's told me all about you!"
"Thank you," I managed to get out.
I let him pull me in, despite the fact that I was 3 seconds away from running out. I was ready to fake a family emergency or something. James was looking at my legs (my best feature) and saying he'd really looked forward to meeting me. His eyes continued up my body until they found my face. Then, his eyes widened and his jaw dropped.
"Taylor?"
That's was it. I was leaving. I started walking out without another word.
"Wait, Taylor. Just wait."
Despite myself, I stopped by the door, my hand on the knob.
"Just wait. I'm trying to come to terms with this." He laughed. Nervously, yeah, but still a laugh. I was getting angry.
His eyes kept scanning me up and down, resting for brief moments on my legs, then face. Finally, he spoke again, "So, Taylor, you're Madison! Ha, clever use of your name! Does your wife know?"
"I'm divorced."
"Oh, what about work? Does anyone know there?"
"No, and I'd like you to stop asking questions," I said coldly.
"I'm sorry," he said with that nervous laugh (again!), "but this is really wild. Really, really wild..." his voice faded off.
"I'm not as enthused," I said with a chill.
He seemed to come to his senses. "Well, what's changed since you arrived? You're here. I'm here. We could still enjoy the evening."
No we couldn't. He knew me! I wanted this time to be with someone semi-anonymous! Someone nice! That was important to me!
James, though, was getting excited.
"Yeah, Taylor. I can see it now. You can stay, and I'll make you my bitch."
What the fuck?!
"No."
"No? Taylor, if you're playing with me this is very weird. I know what you want and can give it to you. You know you want it. If you say no, I could let it slip that I saw you in drag..." He went on, describing how he could blackmail me and make me do whatever he wanted.
Meanwhile, I was getting very, very angry. I was humiliated, and he was trying to take advantage! The fucker. I could even kick his ass! He wasn't bigger than me, and I was in good shape. I was nervous about the heels, but not enough to stop me attacking his little butt if this went on.
"So, Taylor," he finished mockingly. "It's your choice. You can leave and pay the consequences, or you can submit to me."
I just glared.
"Come on, baby."
I still glared.
His voice got rough now.
"Come suck it, bitch."
That was it!
"Shut the fuck up, Jim," I said in my old, baritone voice. "You have more to lose here than me. I could lose my job. You could lose your job, and your wife, and your family. Or does she know you like guys too? I have your home number from that project 2 years ago. We could call and ask her if she knows about your `bitches'. Do you think she'll stay? If not, do you think you'll do well in the divorce? Think the judge will grant you much visitation rights to your kids when it comes out that you troll for cross dressers?"
"Well?" I glared at him fiercely.
"No," he said weakly. He seemed smaller now. Small and confused, probably about how the tables had turned.
"So I'm leaving. If anyone from work makes any reference or suggestion that they know about me, I'm spilling the goods on you. And I'll probably sue the company for sexual harassment to boot!"
"I won't," he said.
"Good."
I opened the door and started to step outside.
"Wait," he said. I started to glare at him again. He seemed bewildered, like he was looking at an apparition. In a way, he was. "Who ARE you?"
What a question. The fucker knew me. He was calling me by name tonight. Several times. He called me "Taylor", not "Madison". Then I stopped, one foot in the hall, one still in the room. I had failed tonight. For a the last few minutes I had ceased to be Madison and had become Taylor again. I'd used my old voice. I noticed I had walked across the room and to the door in my old, more manly gait. I was standing there glaring at him with my legs wide apart, subconsciously taking as aggressive a stance as I could.
In short, I was acting like a man in a dress again. This was a failure. Oh, it was James' fault, but the failure was mine. I couldn't leave here as Taylor. I felt if I did, it would become a habit to act as Taylor any time things got tough. I doubled my resolve, and took a deep, cleansing breath. I took a second step out the doorway into the hall, walking in my newly accustomed, feminine strut, and said at the slowly closing door in my now-normal, feminine, voice,
"I'm Madison."
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