Im Madison

Standard disclaimers apply.

I'm Madison, Chapter 8. Madison's First Date

I was loving my new car as I drove home from the dealer. I drew looks from other drivers as drove around town in my new, pink car. Guys were honking at me, and girls looked jealous, but mostly I drew smiles all around. I pulled into my space in front of my apartment, and went to the door and unlocked it.

"You never quit, do you?" said a voice behind me.

It was Doris, my neighbor. We hadn't spoken in months; not since the first day I met Jo. When I saw her, she frowned. She also didn't bring any mail to me anymore. That was OK, since I was paid and paid all my bills electronically. Besides, who writes letters anymore?

"What do you mean?" I asked.

"You dress as a woman. I mean, always dress as a woman. I've even seen you in a t-shirt and pink short-shorts!" she exclaimed.

"Oh? Been watching me work out? Like what you see?" I inquired in a too-innocent voice.

"I don't think it's decent!"

"Why?"

"Why?! You're wearing WOMEN's clothes! Now you're driving a GIRL's car!" she said, her face getting red. To be honest, I always pictured her as quiet. This was...interesting.

"Are you jealous of my new car?" I asked calmly.

"No! I'm outraged that you think you can just live as a girl!"

"Why?" I asked again.

"Because you're NOT a woman! You're a man! You don't fool anyone!" she was really getting out of control.

"Well, I'm not out to fool' anyone. You don't have to call me Madison'. You don't have to speak to me at all, but if you try to speak to me and call me anything but `Madison', I won't answer. We haven't spoken for months, so I think we'll be OK."

She was speechless, which was funny. I hadn't had this kind of experience since that first time at Becky's store. I turned to go inside, then had a scary thought.

"Oh, Doris, by the way, my car had better not get any scratch marks on it. You know I work in IT, right? I have a camera hooked up to a DVR with extra space. It can record that spot of mine for up to a week at a time." I went inside and shut the door, hearing her slam her door behind her. Geez, what was her problem?

I made a mental note to go buy a DVR, an extra large hard drive for it, and a camera, and went to the bathroom to brush my teeth and use some mouthwash. I wanted to get the taste of cum out of my mouth, and I could swear I still had one of the manager's pubic hairs stuck in my teeth.

A few days later, I had my parking spot covered by 24 hour surveillance. Out in public I still worried about scratches, dings, etc, but I was damned if I was going to worry about my car at my own home. I was furious with Doris, and for the first time since I moved, started thinking of buying my own house. Still, I had 6 months left on my lease, so I was stuck unless I wanted to pay out the nose. She'd apparently decided to pretend I didn't exist, which was fine by me. She was kinda pretty, in a mousy sort of way, but I prefer bold people as a rule.

I was starting to get nervous. Officer Bill hadn't called, and it was getting close to mid-week. Why hadn't he called? It had been three days since we'd last spoken. Had he lost interest? I was tempted to call him, but I decided to give him more time. I called Amy instead, who laughed at me.

"Really, Madison," she giggled, "you're getting as bad as a girl, worrying `why hasn't he called?' Just relax. He'll call."

It was good advice, because he called later that evening.

"Hi Madison," he said in greeting.

Play it cool, girl, I thought to myself. It was funny, I thought to myself in a panicked sort of way, being confronted by a bitchy neighbor didn't faze me. Being on the phone with a stud did!

"Hi Officer Bill," I said back.

He laughed, seeming to enjoy my flirty teasing, "So, I was wondering what you liked to do on dates?"

Get naked and nasty...

"Oh, I don't know. I open to anything."

"Good. How about dinner and dancing?" he asked.

"I'd love to!" I said, unable to conceal my pleasure.

"Great! Pick you up at 7 Friday evening?"

"That works for me," I said. "Where are we going?"

He named a nice restaurant and a club I hadn't heard of. Not surprising since I'm not really a club kind of girl, but I really wanted to spend time with Bill. He could have asked if I wanted to clean up dog shit in his back yard and I would have said yes. I gave him directions and hung up.

First, I called Amy.

"See?" she said, "Told you so!"

"I know. It feels funny being on this end of the 3 day wait rule."

"I bet it does," she said.

"What is this club, by the way?" I asked.

"Oh, it's a gay club. I've heard it has a TV night once a week, but I bet it isn't on a Friday. Better watch yourself."

"Please," I responded, "I'm 6'4", 6'7" with heels, and Bill is about that height flat-footed. We'll be fine. I'll be fine."

Amy laughed, "By the way, I was wondering if I could ask a favor."

I figured I owed her one for her advice and the night she'd given me the other day.

"Sure."

"Well, feel free to say no. I know you're still a virgin with men, technically."

This was an odd way to start to ask for something...

"Go on..." I said uncertainly.

"Well, I have a group of friends, outside our normal group, that meets once a month for some group activities."

Group sex? Really? I was being to invited to a group sex club? This was wild! I was about to say "yes" when a thought occurred. A few thoughts, actually. I let her continue talking, hoping she'd answer my questions without me asking.

"Well," she went on, "Tony Reid is in it, but he's the only one from our group of friends."

Tony Blue Eyes was in this group sex club? This was getting better.

"Anyway, I'd like you to come as my...date," she said.

"I'd like to, " I said, "when is it?"

"Two weeks from Saturday. But there's something you need to know, before you come. It's important."

"What's that?" I asked, intrigued.

"It's a BDSM group."

Well, that changed things. I had a feeling Amy wasn't asking me to Dom her and her friends. I said as much.

"Yeah, I'm not. I know we talked about this is regards to what James tried to pull, but this isn't like that at all."

"Why not?" I asked.

"Because you'd be with me," she said. "I'd be your Mistress for the night, but we'd review what your limits are beforehand. And you could always stop everything with a single word. We'd work that out beforehand as well. It should be a fun evening for you to explore a side of you that you've shown me flashes of, but never explored or embraced."

"What's that?" I asked.

"Your submissive side. I think you'll really like this, as long as you remember you're always in control."

"I'll think about it. Can I tell you after my date with Bill?"

"Sure, honey. If you decide to do this, I think you'll have a blast. Tony's been wanting at you, and this is a cool way to make that happen."

We hung up, and I called Becky to start planning what to wear for my date with Officer Bill.

"Dinner and dancing?" she asked. "What do you want to wear?"

"I don't know. Nothing slutty. I want a dress, but one that says I'm sexy without being a total sexpot."

"Despite what happened last weekend?" she asked in a knowing voice.

"What did Amy tell you?" I asked, more amused than shocked. Amy did tell me she was going to brag to Becky about taking my anal cherry.

"Oh, everything," she laughed as I joined in.

"Well, I'm not looking for anything like that, although if Bill wants me, he'll probably have me."

"Madison!" she exclaimed in mock horror. This was getting sillier and sillier!

"So what are my choices?" I asked more seriously.

"Well, if this was a bit more casual, I'd say a nice blouse and low-cut skinny jeans."

"Maybe some other time," I said.

"Yeah, but for dinner and dancing...Hey! Do you have a Little Black Dress?"

"You've sold me everything I own," I said. "You should know I don't."

"Well, that is a serious oversight," she said. "That's what you should wear. I wonder if we have one in your size..."

"I'll come by tomorrow. I hope you do. If not, I'll try something else."

"You should be able to find SOMETHING," she laughed again. "I swear, I think you've bought half the store at one time or other."

"Is my saleslady complaining?" I asked.

"Not at all," she said. "I make a big chunk of my commission on you!"

Laughing again, we hung up and I went to my closet to pick out some back-up outfits.

The next day after work I went straight over to Becky's store. As usual, heads turned to see the tall "woman" enter the store and greet the saleslady like an old friend. The staff all smiled to see me. Becky hadn't been kidding. I spent a lot of time and money there, and was a good tipper.

Becky had some dresses laid out for me. Luckily, it seemed she had some selections in my size, making me wonder how many other girls were like me out there.

"Oh, a fair few," she replied to my question. "Plus there are some females who are really, really tall."

Huh, I thought as took the dresses to the employee bathroom to try on, I guess I need to go this club's TV night sometime and see my competition.

Anyway, trying on the dresses was fun, as it always is. I found one I liked for a first date. The neck line was high, about halfway between my neck and breasts, so my flat chest wouldn't stand out. The shoulders were cut a little wider, to show some shoulder and arm. The skirt flared a bit, so I could move while dancing. It would look good with or without black hose. It was classy, elegant, and yes, sexy. I washed it that night, and decided to wear my red haired wig again. After all, he'd seen me in it and liked it last time. I chose a nice pair of black flats. I thought about heels, but I didn't want to break my neck either!

Friday came slowly, but it finally arrived. I didn't think I could get as nervous as I was last week before the disaster with James, but I really was. I got through my work day somehow, stopped early, around 2, and started prepping for the date. I'd stopped eating the night before, so my bottom would be cleaned out. Again, I used an enema on myself and applied liberal amount of lubricant to the inside of my ass. I shaved my face and body hair, taking a shower while doing so. I applied a nice lotion to my legs and arms. I put on my panties, dress and full length panty hose. I stopped at this point and applied my make-up as carefully as I could. Finally, my red curly haired wig.

The doorbell rang!

"Just a minute!" I yelled at the door, hurrying to put on my shoes, my earrings, a bracelet, and grab my purse. I was ready!

I opened the door and flashed a smile, thinking this had better not be that bitch Doris.

It wasn't.

It was Bill. Oh, my God, did he look handsome, wearing a blue button down shirt, tan slacks, and a brown jacket. His shoes and belt matched his jacket. He accessorized! His shirt was open the top few buttons, letting a bit of his manly, strong, hairy chest show. He was wearing a gold chain. His hair was brushed, a part to one side. His clean shaven face was so handsome. And his ass was to die for! He was eyeing me up and down. Did he like what he saw? Did he like me?

He smiled back and said, "Madison you look fantastic!"

Whew!

"You look great, too."

"Thank you," he said. "Shall we go?"

"Yes!"

We took his car, an SUV with lots of leg room, and headed off to dinner first. I was so hungry! His eyes lit up when I ordered a steak and potato meal.

"What?" I asked.

"It just surprised me, that's all. I like a girl who eats."

If only he knew this was the first beef I'd had in well over a year! I almost changed my order to chicken, but I was hungry and hadn't eaten, so I forgave myself and prepared to chow down. Of course, I did try to fill up on salad first.

We talked all during dinner. It turned out he was gay, but had been married for around 5 years before coming out, which was 15 years ago. He liked the way women looked, but wasn't particularly turned on by them. I told him I was bi, which made him raise an eyebrow, but nothing more. He looked shocked when I told him I'd only been dressing full time for a couple of months.

"You look great," he said.

"Yeah, I think you said that before, Officer Bill," I smiled at him.

He rolled his eyes.

He paid the check (yay!) and we left. On the way to club, we chatted some more, and he put his arm behind my seat as he drove. As he pulled into the parking space and put his SUV in park, I leaned over and kissed his neck.

"I'm having a great time," I said.

He looked into my eyes, "Me too."

It wasn't time yet for a kiss, so I turned and opened my door, saying, "Come on! I want to dance."

This was a lie. I couldn't (and still can't) dance at all. It is a fact of nature that tall people can not dance, regardless of race, sex, sexual orientation, religion, or way of life. We just look dumb. Still, I wanted a slow dance with this hunk.

We got to the dance floor, and sure enough, he couldn't dance either! We were so comical! I started laughing and he joined in. Finally, he said, "Let me get us some drinks."

"Oh, no, I'll get them..." I started.

"No, this is a first date," he said. "I'll pay."

We found a place to sit and nurse our drinks, watching the others dance. I was waiting for a slow song, and Bill seemed to waiting for the same thing. The DJ, on the other hand, had different ideas.

Fast-paced driving-rhythm dance song.

Fast-paced driving-rhythm dance song.

Fast-paced driving-rhythm dance song.

Etc...

This was getting ridiculous! Damned gay clubs!

Finally after 45 minutes or so, a slow song came on. Not a bad selection either. We went out on the floor and swayed to the music, my arms snaked around his neck, his hands on my hips.

"You were waiting for a song like this, weren't you?" I asked.

"Yeah," he said. "This was how I got my first kiss, with a girl. I wanted it to be this way with you, so I'd have a slow dance first kiss with a girl I'm actually attracted to."

"I'm glad we waited," I said, looking in his eyes.

"Me too."

We swayed a bit longer, just staring into each others eyes, when the song was getting close to the end. Bill leaned in, and I closed my eyes. His lips touched mine.

Bliss!

We stood there on the dance floor for who-knows-how-long, eyes closed, lips locked. After a few seconds, or maybe hours, we parted. I noticed the DJ was back to playing dance songs again.

"Ready to go?" Bill asked.

Hell, yes! I thought. But I simply nodded.

He drove me home and we walked to my door. He kissed me again, and turned to leave. What a gentleman! I wasn't about to be a lady, though.

"Hey Officer Bill," I called. "Want to come in for a cup of coffee?" Yeah, it was obvious. So what?

He smiled widely, "Love to."

I asked him to make himself comfortable, then went to my room to change. A few minutes later I came out wearing a black chemise. It was see-through on the sides, with garters that attached to a pair of black thigh high hose. It had tiny pink bows on the breasts and down where my cock was. Beneath this I wore a pair of all-lace boy shorts. To finish it off, I wore my strappy heels. I'd refreshed my frosted pink lips.

I came out and Bill had removed his coat, and socks and shoes. His shirt was unbuttoned, too, showing his manly chest.

"I didn't think you'd make coffee in your room," he whispered as his eyes drank me in.

"I don't like coffee," I replied, watching the bulge grow in his pants. "I don't even have a coffee maker."

He stood as I crossed the room, swaying my hips and giving him the sexiest look I could.

He embraced me, a little roughly, but mostly assertively and kissed me, not like our first kiss, but deeply, passionately. Oh yes! I opened my lips to let his tongue enter my mouth. My head tilted back as he leaned into me. One hand supported my back while his other grabbed my ass. My hands were exploring on their own, feeling his strong chest and shoulders. I managed to get his shirt off, well, down to his elbows as we continued kissing, standing there in the middle of my living room.

My hands continued exploring, finally rubbing his bulge through his slacks. He moaned, and I knew it was time.

I broke our kiss and kissed his neck, then chest. He let his shirt fall to the floor. I kissed his stomach, my knees bending. I continued kissing down until I was kneeling in front of him.

I unbuckled his belt as he watched me. I knew I looked sexy in my lingerie, kneeling like this, so I took my time. I unbuttoned his slacks, unzipped his fly. He reached down and helped as I took off his pants and underwear at once. Finally, he was naked.

I took a moment to soak in his naked body. He was so gorgeous! Strong. Not too hairy, but with nice chest hair and good looking, manly legs. His cock was hard, a nice, thick, 7" phallus pointing straight out at me.

I leaned and opened my mouth, and his cock slid in. Oh, this was so perfect! He was clean, but salty from his sweat. His musk filled my nose. His pubic hair was trimmed, and he was looking down at me. He moaned a little, the only sound in the room.

I was here! I was finally here! After so much time, preparation, tears, pain, and sweat, I was where I wanted to be. On my knees. In sexy lingerie. A hot guy's cock in my mouth. All five of my senses tuned to and dominated by this sexy man. I wanted his cum. I wanted him to enjoy every second of this; to know he had me as long as he wanted.

I kept my eyes locked with his as I slid my mouth along his shaft, my left hand cupping his balls. I went slowly, enjoying his moans. Suddenly I remembered Jo's advice and how I'd love having a cock in my mouth for the right guy. She was right!

I had a good seal on Bill's cock. As I pulled my head back, the force of suction would slow me down and I'd glide forward on it again. I could feel the big vein on the top of it, the ridge of the circumcised head, and a few various ridges and smaller veins. It felt good in my mouth; felt right in my mouth. I was loving this!

From Bill's moans I knew he was close to cumming, and I so wanted his load. I picked up my pace a bit, and massaged his balls. Finally he groaned, pulled out a bit, and spurted his load into my mouth, where it would pool on my tongue.

"Let me see it," he ordered.

I opened my mouth and showed him his cum.

"Swallow it," he said, and I did, showing him my empty mouth once I was through.

He held out a hand and helped me to my feet, and I led him to my bedroom. Once there, he laid me down and took off my panties. Then he spent a few minutes licking my cock, finally sucking it in his mouth. He was really good, and I found myself spreading my legs for him. He reached down and swirled his finger around my asshole as he continued to suck me. I quickly got close, then came in his mouth. Oh that was good!

He swallowed my load and smiled, rubbing my legs as his face went down lower. I felt something warm and sticky on my anus. His tongue! Soon I was moaning.

He spent a good 10 minutes rimming me before starting to insert his fingers. He used a different approach to anal than Amy, but it seemed to be just as good. After another 10 minutes of his attentions on my ass, I was ready.

This was another moment I'd dreamed about for a long time, and I was enjoying the lead up to the main event. I spread my legs wide, pulling my knees up and out, and Bill climbed on top of me. Oh this was hot! He positioned his cock to enter me, then stopped.

He stopped!

What the hell?!

"Fuck me," I moaned.

His face was right above mine, his body laying on me, and I could feel his cockhead on my asshole.

"Fuck me," I moaned again.

He leaned his head over to the side of mine and whispered in my ear, "I like hearing you say that."

"Fuck me, please," I moaned at this.

"Say my name," he hissed in my ear.

"Bill."

"Say it again!"

"Bill!"

"Now ask me to fuck you," he said as rubbed his cock on my hole.

"Fuck me Bill!"

"That's right. Don't forget my name from now on," he said, moving his face above mine.

"I won't, Bill. Please fuck me!" I moaned in his mouth.

Then he kissed me deeply. I could taste my cum on his breath, loved it, and kissed him back. As his tongue entered my mouth, his cock moved forward into my ass.

"Oh, yes!" I moaned as he filled me. It wasn't like all the times I'd had a dildo inside me. This was a hot, pulsing, throbbing, living thing being thrust in me. It felt so good!

I wrapped my arms and legs around Bill as he started to thrust slowly. Every inch seemed to last for hours gliding in and out, yet only seconds at the same time. Bill was so strong above me. His muscles were bulging and his chest was taut. His thrusts sent shivers up and down my whole body.

This was better than my dreams! This man, at this moment, was totally in control of me in way no one had ever been. This was Earth-shattering!

He was groaning now, and starting to pick up his pace. Soon he was out-right fucking me, his thighs slapping my ass as his cock pounded my hole. I gave myself up to this willingly, only wanting his pleasure. My moans filled the air as he fucked me. Soon, he started tensing up and I knew he was going to cum.

"Oh yeah, Bill, cum in my ass," I moaned at him, "fill me with your cum!"

"You want it, don't you?" he panted.

"Yes! Cum inside me, please!"

His body shook and he slowed down. Finally I felt the liquid heat of his semen fill me.

Oh, yes!

He rested there a moment, his cock still inside me, but already starting to soften. He kissed me again while starting to pull out and I moaned a sigh of regret as it slid out.

We lay there for a long time afterwards, just kissing. Part of me wanted to go wash up, and help Bill clean his cock, but mostly I enjoyed just being there with him. Besides, I wasn't sure if I could walk!

I lay there, kissing Bill, but my mind was racing. I'd done it! I'd surrendered completely to a man. Taken him inside me. It was one thing to fantasize, to dream, to pretend with dildos by myself or with Amy. It was another to have the real, breathing, manly thing in my bed. How did I feel? I'd loved it! Was I gay? No, I still liked women. Which did I like more? I couldn't say. I knew I wanted more of Bill, and would get some more tonight. I'd leave the rest for later. This was where I wanted to be for now.

Then I realized something even better. It was June 7th, one year to the day since I'd decided to become Madison. The road had been longer than I'd thought, but every step of the way I'd learned things about myself. I wasn't ready to stop, either.

I knew then I'd be taking Amy up on her offer. In the last week I'd been a whore, now I'd been a slut. Next I'd be a bitch.

It was going to be fun!

*I enjoy feedback - if you have any, please e-mail me at MadisonTaylorCD@gmail.com.