Standard disclaimers apply.
I'm Madison, Chapter 3. The Move
Another three months had passed. I was getting very skinny, my arms and legs lightly toned by daily aerobics, but not muscular at all. My ass was a little flat, but all in all, I had the body I wanted. I even had a flat belly, with a little definition! I'd taken to wearing lingerie at night, my panties all the time, and was growing out my hair. It was still thinner than I'd wanted; I might have to go with wigs, which I didn't exactly want, but wasn't opposed to either. I'd started shaving my body hair and using hair removal cream. I still wasn't "passable" when I looked in the mirror, but I was proud of the way I looked. It was time to start showing it.
Before I did, I wanted to move. I hated where I was, where everything reminded me of my old life. The life I was still mostly living. I decided to move to the city where I bought my first clothes as Madison. My lease was up, so I wasted no time, renting an apartment and getting moved in. It wasn't long before I was set to get out and about.
I headed down to the store where I'd met Becky. She had helped me find my first lingerie. Now I'd be asking her to help me dress for the world. I walked in confidently, and she smiled in recognition and walked over.
"Hi Madison," she said normally, and a few heads turned my way to see a man (me) answering to a name most commonly given to girls.
"Hi Becky."
"Shopping for more lingerie?"
"No, I think I want some clothes," I said with a smile, "if you have some my size."
She smiled broadly, "Of course we do. I've been hoping you'd come back again. We had such a good time laughing about you and that old bitch."
"Has she come back at all since?"
"Never."
We both laughed as we reached the back room, and Becky asked me what I was looking for. Being new to this, I decided to spend the most time and money on every day outfits, but maybe a couple of outfits for dates, and one or two things for more...adventurous nights. We spent a couple of hours going over things until I picked out a couple of pretty floral dresses, a few pairs of women's slacks, some blouses, and a couple of jackets that went with the pants and blouses. I really wanted some nice skirts, so I bought a few mid-length, a couple of full length, and one mini! We then spent almost an hour trying out shoes! There were so many! We decided quickly that heels didn't make any sense at all for me. I was so tall anyway. So I mostly bought shoes that were flats or with an inch of heel at most. I did buy 2 pairs of heels. One for clubs if I wanted to show my legs, and one for...intimacy. Those were interesting, black, strappy shoes with 4" stiletto heels.
"Lots of guys like a girl wearing heels with lingerie," Becky said.
I blushed, then got nervous, afraid Becky would try to ask about my experience with men, which was still zero. Hell, it had been a year since I'd been with a woman!
But Becky didn't do that, thank God. What she did do was say, "You know, I have a friend you should meet."
"Who is that?"
" A girl like you."
"Oh, I'm not sure I want to meet another girl...like me."
Becky's expression turned serious. "Madison, there are several things about the life you want to lead that no one can teach you, except another girl who lives it. Have you put on make-up? Done your hair? Your nails? Have you learned to walk in heels? What about your voice? Have you practiced talking like a woman? A woman like me can't teach you. I've been doing these things all my life. I think you'd learn better from someone who had to learn too."
"OK," I said. She made sense, but I still wasn't sure. "What is her name?" I asked.
"Jo, " said Becky. "Kind of a boring androgynous name, you think? Still, it fits her."
"How?"
"Well, a lot of girls I help want the girliest, sissiest clothes I can find. Some, like you, seem to want to look more like the women they see at the office or on the street. A few, like Jo, just want to soften their edges. They wear panties, sure, but aside from that, most of the time they don't dress too differently than most guys. I guess you could call them tom-boys."
I laughed at this. Why bother then?
She seemed to caught my unspoken question. "Jo normally wears jeans and flannel, but she also knows how to walk and talk like a woman. She's fooled a lot of guys and girls. She walks a fine line, but walks it better than anyone I know. She's a long time client, and I think she'll talk to you if I ask her. She can help you live the life you've chosen, better than me. Better than you doing it on your own."
Well, who was I to turn down free advice? Especially when I considered, really considered that I hadn't the faintest clue what I was doing? It had seemed so simple. Wear girl clothes. Meet hot guys. Easy, right? And I still hadn't decided that I would be a full-time crossdresser. Not because I was scared (although I still was), but because I still felt like a man. Most of the time. Well, some of the time. The panties sure had a way of changing my mind set.
I agreed to meet if Jo wanted to, we finished with picking out belts and purses, then some nice fake jewelry ("Maybe some guy will buy you the real stuff!"). I left my number for Becky to give to Jo, then went home.
The phone rang that evening. I answered, "Hello?"
"Hi, " said a voice on the line. A voice that was soft and in the alto range, "this is Jo. Is Madison there?"
"Hi!" I said. "This is Madison. It's so nice to talk to you."
"Becky told me you were new in town and looking for some help with things."
That's was a nice, oblique, way of putting things!
"Yes," I said, trying to make my voice softer, like hers. "I thought I was getting settled, but find there's so much to do!"
"I understand," she said. "Tell you what, why don't I come by and see your place and see if there's anything that needs work?"
"I'd like that," I said, and gave her directions and the address. We agreed she'd come by Saturday afternoon. It was early Spring, and it was too cold to do much anyway.
That week went by slowly. I kept trying on different outfits. I also tried to use some make-up I'd purchased. I still didn't look good at all. I decided that when Jo came by, I wouldn't wear make-up. I was hoping she'd show me how to wear it. I practiced walking in women's shoes. The flats were easy. The heels, impossible!
I was so nervous about the coming weekend. I almost called Jo to tell her, in my manliest voice, that I no longer needed any help, then throw everything away and go back to being a straight man. But I didn't! I stayed brave. I know, it's not too brave for a CD to meet another CD, but hey, it was damned site braver than I'd ever been. It was braver than I felt, too. As the week went on, I realized only part of my nervousness was about being dressed in front of someone else. It was also that I hadn't had sex a long damned time, except by myself, and that didn't count. Well, it did, since it was me getting used to myself, but still, it was solo. What if I thought she was cute? What if she thought I was? I didn't know what to do. Finally, I decided to just go through with it.
Saturday finally arrived, and I decided to dress as best I could on my own. Black pants, a turquoise blouse, black flats. If I went out, I had a black sweater. I stayed with my decision to wear no make up, but I pulled my hair, now past my shoulders, into a pony tail, and made sure I was clean shaven. I wore a bracelet on my right wrist, a ladies watch on my left. Finally, I wore a thin gold necklace with a pretty pink rose pendant.
I checked the mirror. A man in woman's clothes looked back. Well, I was trying, damn it.
Finally, there was a knock on the door. She was here! I was very excited and ran to the door and opened it.
It wasn't Jo.
It was my neighbor, a woman named Doris who lived across the hall. She was mid-40s, petite. Dirty blond hair and brown eyes. Looked like a mousy CPA or something. Apparently divorced, but I didn't know. She went out about as often as me. Her brown eyes widened at the sight of me.
Oh, shit!
Shit, shit, shit! We'd never talked. Just said hello. But damn it, she knew me. She looked faintly embarrassed. Well, fuck it!
"Hi Doris," I said.
"Umm, hi."
"I'm Madison," I said confidently, smiling. She knew my legal name was Taylor Madison, thanks to some mis-sorted mail.
"Hi Madison," she smiled back. "So, are you going to a party or something?" Oh! She was either trying give me a way out of this, or trying not be embarrassed herself any further.
I wasn't backing down, though.
"No. Just getting ready to meet someone."
"Oh. I brought some mail by for you."
"Thanks."
She left and I closed the door. Ha! Hahahahahaha! Yeah, she was a little nerdy looking girl, but I had stood my ground! Yes! I felt really good!
A few minutes later, the doorbell rang. I answered it again. This time it was Jo, and I saw immediately why Becky said the name fit.
She was shorter, about 5'10", not skinny like me, but kind of slender. She was younger than me, too. Early 30's it seemed. Her hair was a nice lush brown, straight, pulled into a pony tail too. If she wore make-up, it was subtle. Her clothes, well, they were jeans and a flannel shirt. But her shoes were a nice, brown leather, open toed shoe that showed her painted nails. Her fingernails were painted, too. Hmm - I couldn't figure out what made her look feminine, exactly, but there was a definite air that she was.
Jo introduced herself and I invited her in. She quickly scanned my apartment, noting the mismatched furniture and lack of pictures or art. She gave me quick once-over, and I invited her to sit down. She sat on the couch. I sat across the room in the easy chair. She seemed to gather her thoughts for a moment, then started changing my life.
"So, Madison, have you decided how far you want to take this new life?" Wait, that her first question? I thought she was here to make me pretty!
"What do you mean?" I asked.
"Well, I mean that your place looks like a man's place. You just bought some clothes, but you're not wearing make-up, which I know is because you don't know how. In short, you seem like you're on the cusp of wanting to be a woman, but holding on to being a man. I want to know, how far are you going with this? Do you want to live as a woman, or a man, or something in between?"
Wow. That was direct. And true. I hadn't exactly figured out what I wanted. Wear women's clothes. Meet hot guys. That was as far as I had thought about this, really. I said as much to Jo.
"Well, let me ask you something, in all seriousness. Do you really want to be with men?"
"Yes," I said.
"Really?"
"Yes."
"Well, what about now?" Well, that was an interesting question.
"What do you mean?"
"I mean, right now." My heart was really beating.
"With who?"
"Don't be stupid. You're not, so don't act like it. I gathered from Becky you had never actually been with a man. How do you know you want to?"
"I just do."
"Really?"
"Yes!"
"Then come suck me."
What?! Just like that? I was terrified again. I didn't know if I was ready for something like this. My eyes were wide, and my mouth agape at this.
"Madison, listen. I bet you have a great fantasy life, but you're taking steps to actually live as a woman, and you don't even know if its something you want to do. You think it is, but you don't know. I won't make you. I doubt I could. But you need to know before you take more steps and start living in a way that you'll regret. I will help you, but I don't want to spend my time with someone who chickens out once he gets to the real point of all this. Besides, as first times go, it can't get more non-threatening this."
He. She said "he". About me. I hadn't had sex with a person in a year, and she wanted me to just drop and blow her for lessons? And to prove that I was a "she". It was kinda threatening. But I saw her point too.
I was breathing heavily now. I was full of adrenaline. I had had small victories. I had convinced myself that this was what I wanted. And Jo was pretty, while at the same time, kinda handsome.
It was decision time. She was right. I needed to know. And this could be fun. Or, this could be a test to see if I was serious. I needed to see this through. There was, however, one thing I needed to know...
"Would you like me to change into lingerie?"
"Why? I'm not trying to see if you look good or not. I'm trying to see if you will suck a cock. You don't need lingerie for that."
Yeah, I didn't need it. It was just the focal point of most of my fantasies for the last year.
Still, a girl didn't need to be in sexy lingerie to blow someone. I didn't either.
Thinking it still might be a test, I stood up, walked across the room, and knelt in front of Jo. I reached up and unbuckled her belt. She smiled down at me, a look of lust in her eyes. I hadn't seen that look in years. I unbuttoned her jeans and unzipped the fly. I was in a state of excited, but shocked, disbelief. In all my fantasies, I never thought my first cock would be from a woman. In the mid afternoon. In my clothes. With the lights on. This was as unromantic as it could get. So why was I so turned on now?
I pulled at her pants and saw her panties. Nice, purple satin panties. Jo may be a tom-boy, but apparently has a nice fem side, too. With her help, I got her jeans and panties down around her ankles. Now I took a moment to examine her cock. Smaller than mine, it was fully erect and hard. It was also clean shaven.
Well, this was it. On my knees with a cock in front me. I had waited and fantasied so long. Now I had passed my fears. It was time to take the next, world-shattering step. I leaned in and opened my mouth, half-expecting Jo to tell me to stop; that this was all a test.
She didn't.
Her cock slid in my mouth. About halfway down the shaft.
And, well, that was about it. To be honest, it was a bit of a let-down. I don't know what I had expected. Maybe that I had special nerve endings in my mouth that would make me cum. Pretty stupid thinking. In reality, here I was, on my knees, with a lump of salty flesh between my lips. It appeared that giving a blow job was a lot less sexy than receiving one. Still, it was exciting in the sense that I had done it! And maybe my let down was because I was blowing someone I wasn't really turned on by.
I started bobbing my head, working to create a seal like I'd read about. It wasn't super sexy, but I wanted to do a good job, maybe swallow someone else's cum for the first time. I still couldn't shake the feeling, though, that this wasn't as good as I'd hoped.
Then she moaned.
Well, that was interesting. Her hands touched my head, putting a bit of pressure on me to go down further. Afraid of gagging, I went a bit further, but not much. Instead I reached up and wrapped my hand around the base of the shaft, stroking her cock as I bobbed my head.
"Yeah. That's it," she moaned.
I discovered something very important in that moment. Blow jobs weren't about me. They were about the guy (in this case, girl) with the cock. It was a gift of sorts. Or maybe, I realized, a way to get what I wanted later.
I reached up with my other hand and started lightly touching Jo's balls. She was moaning more now. My head bobbed a bit faster. I started hearing sucking noises. She moaned louder. Apparently that turned her on! I looked up in her eyes. She smiled down at me, rubbing her hands in my hair. She didn't say a word; just watched me sucking her cock. I got an idea at this point. I pointed to the end table beside the couch.
She understood, and grabbed my cell phone. Opening it, she pointed it at me while I sucked her. Then...
Click!
Click!
She put it down again. And continued watching me suck her.
Finally, her hips started to buck. I kept up the rhythm, and soon she was spurting hot cum in my mouth. Her cock hit the back of my throat and I gagged. Tears in my eyes, I started swallowing to keep from vomit as her cum was sliding down my throat. She grabbed the camera again and took a picture of me, my eyes watery, my mouth open, and her cum on my lips and tongue. To this day I love that picture most of all.
I swallowed again, then giggled. She laughed too.
"That was great!" she said to me. "You're a natural."
"Thanks. I can't believe I did it!."
"Well, you did. I'll help you now. You'll look really pretty once you learn how to do makeup and hair. Becky told me she helped you pick clothes to show your figure, which is really nice. Skinny, but not a stick. You have a waist, which is good. You'll have men drooling."
"I'm too tall."
"Ha! You have long legs. They'll drool."
"Well, maybe."
"You'll see. Now let's get up and get started before I think you're just waiting to suck me again."
I laughed at that and crawled back a step, letting her stand. I pulled her panties up for her, and, giving her cock a kiss farewell, slid them up and on. Then I pulled up her pants.
"Well, that was nice. Thank you."
"I really just wanted to kiss your cock good bye."
She laughed, "Well, I'm not sure if or when we'll do that again. I actually prefer women, but I wanted you to cross that bridge before we wasted our time. Besides, I was horny."
We laughed again, and she took my hand and said, "Let's go, Madison."
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