Standard disclaimers apply.
I'm Madison, Chapter 4. Friends
The next month after meeting Jo was a lot of fun. While there wasn't a repeat of the blow job I'd given her on our first meeting, we had a lot of fun, just as girls. Learning to wear women's clothes properly, learning to apply and remove make-up for several occasions, learning to walk like a woman, and how to walk in heels. These brought daily giggles, and some bruises. I bought several wigs, in different styles and colors. My own hair I got cut shorter. It went most of the way down my neck in back, and was an even length that I could wear in a bob or styled in a wavy, wild look. Mostly, though, I wanted longer hair, so my hair was the foundation for a lot of bobby pins. My weight was now down to my goal weight, and I had no unsightly body fat. I'd gone to the mall and gotten my ears pierced in three places, 2 on each earlobe and one at the top of each ear. With Jo's help I picked out several sets of earrings. I fell in love with one pair that had little gold oval drops in a mesh that dropped half an inch from the stud on a gold chain. I wore them most of the time, along with simple gold studs in the other earlobe piercing and the one at the top of the ear. At the end of that first month, I saw that Jo was right. I looked really good! I still didn't think I'd fool anyone, but I wasn't afraid to go out anymore. I even had my voice down. I was a natural tenor, so talking higher than men was easy. I worked on softening it just the right amount. I added a bit of a breathy quality to it, but not too much. I didn't want to be Marilyn Monroe! Madison Taylor was good enough for me! And I was proud of my myself and the changes I'd made. Still, though, I only dressed inside. To go outside, I wore jeans and t-shirts, and removed the earrings. The only outside concessions I made to Madison were my hair, which I styled in a wavy bob that drew a few stares, and my gold ladies watch.
My place was starting to change as well. Fortunately, I didn't need to buy any new furniture. A few slip covers worked to change the look of my sofa and love seat, some lace doilies under the lamps, and my living room looked very different. A few well chosen pictures added to the look. They were kind of quirky. No landscapes or floral paintings. There were a couple of portraits, one of a canal in Venice. I bought some older black and white photos of women and men to spread around the house. All in all, very nice. Jo said they were me, and I was indeed proud of it all. I bought nice floral curtains that went with the sofa. I added some lamps for more light. I had gotten used to my place being dark over the years. It felt oppressive, I wanted my place to be bright. It was optimistic. I loved it! My bedroom I decked out in pink and lace. If I was going to be a woman (and I had pretty much decided I was), I wanted to live it. My bathroom looked different as well. Pink bath rugs, body wash, shampoo and conditioner, facial cleanser, perfumes, women's deodorant (strong enough for a man - giggle), hair remover, razors by the sink and in the shower. Finally, nail polish, hair curlers, and make-up kits. Inside, the only concession I made to Taylor was the 2nd bedroom, which I called "Taylor's Man-Cave". It help my home office, video games, PC, etc.
My appearance and apartment showed the most obvious changes. The others were internal to me, but Jo helped with those as well. We talked about my feelings during that first blow job.
"I really thought it'd feel sexier," I said.
"I understand. You'd built it up in your mind for so long you probably thought you would cum by sucking another man's cock."
"Yes," I laughed, "that's exactly it. And it wasn't that great for me."
"Really, Madison, why do you think it should be? Blow job' even has the word job' right in it!"
Giggle-snort. "I know. Like you said, I'd built it up."
"Well, now you know an important truth."
"I guess I do. Sometimes I'll blow guys in order to get what I want."
Jo's smile dropped a bit, and she looked at me like I was only getting half of that important truth.
"Listen," Jo said, "I think you're in danger of getting too cynical about this. Yes, sometimes you'll have sex when you don't really want to, in order to get what you want. But sometimes, most times, you'll do it just to hear your man's moans. Just to make him happy. And you'll look hot doing it. You looked hot sucking mine, and you still looked like a guy then. And when you're down on your knees in front of a guy you like, and you look hot, and see him looking at you like you're Queen Shit, you'll feel hot, and horny. And you'll love that cock in your mouth."
"Thanks," I said. "I think I really needed to hear that."
"Just remember, no matter which way you feel, you're in control and putting on a show. He's the audience. You'll love some performances you do and hate others. Others you'll just do because you know you need to. Just stay safe and sane, and you'll do well."
I considered this for a moment, then changed the subject.
"I think I want to date," I said.
Jo smiled. "I think you're ready. How do you want to meet people? Clubs, bars, blind dates?"
"I don't know," I admitted. "I think I'd like a blind date at first. Do you think I should go online?"
"You can," Jo said. "The only problem there is all the time wasted on guys who just want cyber sex. Married men can be so hot, but they can also be big time wasters, you know?"
"Well, not yet, but you did just warn me."
Jo laughed. "Let me ask around. Are you only looking for men?"
I'd thought about this a lot. "Right now I'm open to anyone."
"Anyone?"
"Yes, anyone. I could give you 50 reasons why, but I'll settle for: I just want to get laid."
Jo was laughing hard now.
"OK. I'll ask around. I do think you'll fit in well in my little group of friends, if you'd like to meet them."
"I would! Are they all like us?"
"No, it's a good mix of us who get together for drinks at a bar near my place. Some girls like us, some women, like Becky. A few guys, one I think you'd like, but he's out of town for a few months. He's bi, and likes girls like us a lot. There's a couple of gay guys. Even a few straight folks who like to hang out with us. How about I introduce you to the group and see anyone likes you."
"You're not afraid of a relationship going bad and ruining the group?" I asked.
"No. This isn't a TV show or or movie. I've slept with most of them. Everyone has. Even Becky, and she swears she's a Lesbian. Well, she wouldn't be the first Lesbian to sleep with a guy, but she apparently liked it well enough."
It was my turn to laugh. So Becky was a Lesbian! Or a very confused bi-sexual. Well, I hadn't exactly figured everything out yet either. It'd be nice to be friends with her.
It would be nice to have friends, period. Then I realized that I had one: Jo. It had been so long, since the early days of my now-dead marriage, since I had friends. And I don't think I'd ever had a closer friend. Surely never one I'd sucked off! My eyes got a bit watery, and I said to Jo in all seriousness, "Thank you so much for everything. You've given me so much of your time and knowledge, and gotten so little in return."
"Oh stop, Madison. It's been really fun, and I think you'll like the group. We girls can never have too many friends."
She'd said that like it meant something really important.
"What do you mean?"
Jo got really serious.
"Madison, it's important that you remember what you are and what that means. Mostly you look like a woman. Until someone really sees your height, or really looks at your hands. Or notices your Adam's apple. You're face won't give you away instantly anymore, which I consider a huge victory, but if someone looks carefully, they won't be fooled. And most men are shocked and angered by us. So are most women. Oh, a larger percentage of women than men will be friendly to you, and a small percentage will want to be friends with you, but bi-sexual men are looked down on by some even in the LGBT community. And bi-sexual cross dressers get looked down on most of all. If 10% of men are gay or bisexual, there are maybe 10% of them who like girls like us. That's 1% of men who might appreciate you the way you are. And some of that 1% will only like you for the sheer thrill of a `chick with a dick'. Not as someone to have a relationship with. When you go out, you'll get some stares, frowns, and outright hostility, and coolness from some who should support you. This is not an easy life. It's fulfilling. Scratch that, it's glorious, because it's who we are, but it's also scary and lonely at times. I need you as a friend just as much as you need me. And my group of friends are a wonderful bunch of people who will support you, and yes, maybe even sleep with you, but at the end of the day, they're people who are on this most amazing journey with us. Some because they're like us. Some because they like us. And I love them all for it."
I was crying now, and a little scared. Jo was crying too. We hugged for what seemed like forever, two souls who found comfort with each other.
Finally, we broke off and Jo said, "So what are you doing tomorrow night?"
"Nothing."
"Good. Wear something casual tomorrow night and meet me at the bar at 9."
"Thanks, see you there."
I walked Jo to the door and watched her go. Then I cleaned up my face and went to pick out something to wear to the bar.
The next day I had trouble staying focused on my job (I still telecommuted, of course), but I pushed through. It was getting really weird to be "Taylor" at work but "Madison" the rest of the time, but if only my boss knew I was on the phone with him in a pale pink blouse, khaki full length skirt, long wavy brown-haired wig, and progressively more make-up through the day!
Finally, it was time to go. I stepped into my opened toe sandals, grabbed my purse, and stepped out into the night for the first time, fully, as Madison.
By the time I got to the bar the sun had set and the city seemed alive with electricity and possibility, or maybe that was just me. As I walked in, I saw Jo and Becky sitting at a round table in the back corner. They waved me over, and with a smile, I walked through the bar and over to the group. From Jo's description, I expected upwards of 20 people, but there were only 9. I ordered a white wine and settled down next to a pretty girl in her mid-30s with brown hair and a short, slender bald guy with startling blue eyes. I introduced myself, and everyone gave me their names. The brown-hair girl was named Amy, and the blue-eyed guy was named Tony. The evening was a blast. Seemed everyone had heard of me, and liked the way I looked. Becky exclaimed that she couldn't believe the transformation I'd undergone.
"All thanks to Jo," I said as I raised my glass. Everyone raised their glass to Jo, who looked proud. I really felt like I was fitting in with friends for the first time in a long time.
As evening deepened, Amy started flirting with me. I flirted right back as best I could, and by 11 we were leaving for her place. Jo looked thrilled for us, and the rest of the group whistled and cat-called as we walked out together. I whispered in her ear, and as we left we shook our hips as much as we could to the group's laughter. Her place was a short drive away, which we took in separate vehicles. I was still driving my old pick-up, which I started to think would need to go away in favor of a more fun vehicle.
Once inside her house, Amy wasted no time in getting me undressed, and I returned the favor, ripping off her blouse and jeans. As she unzipped my skirt and slid them to the floor, she glanced at my panties and frowned, just for an instant, before pulling them off, too.
Then, bliss. I lay back on her sofa while her warm moist mouth found my hard cock. Yes, it was nice to be on the receiving end of a blow job. I ran a finger lightly through her hair as her head bobbed up and down. The sensation was one I'd never felt before, her lips on my almost completely hairless cock. My pubic hair I had shaved away except for a small, heart-shaped patch above my cock. Her lips slid on it over and over again. I could feel my orgasm building and grabbed her hair, but not forcing her lower. After my gagging episode, I didn't feel that was right. Finally, I exploded in her mouth. She started to stand up without swallowing. Seems she was a spitter. I pulled her up to me and kissed her, my tongue probing for my semen. She seemed to understand and pushed it all my mouth, which I then swallowed.
"That is so sexy," she said.
"Why didn't you..." I started.
"Swallow?"
I nodded.
"I don't know. It's never been a turn on for me."
This was confusing. "Then why was it sexy for me to swallow my own cum?"
"I like seeing other people swallow. I just don't like doing it myself. Is this a problem?" She seemed nervous, and maybe a bit hurt, and I realized that I'd indeed hurt her feelings.
"I'm sorry. It's actually been very rare for women to swallow my cum. It's just that I like to, so sometimes I think everyone does."
"Not me," she grinned. I grinned back, "Spitter rhymes with quitter, you know." We were laughing again, and before the moment passed I pulled her close again, kissing her deeply. My hands explored her breasts and sides, working gradually down to her panties, which I slid down for her. I kissed her nipples as my finger traced her moist, shaved pussy. I started kissing my way down to it, my tongue exploring her skin and belly button. Finally, I was licking her pussy.
Her hands found my hair, and wasted no time in grabbing big handfuls of wig hair. I worked her toward an orgasm, her breathing becoming deeper and deeper, her legs at times clenching around my head. Finally, she lifted her ass off the sofa and pushed my face in her crotch. I kept licking for all I was worth. As she came, she pulled my wig, taking it off.
I stood up, my hair pulled back and under a piece of hose I used to keep it in place. My cock was erect again. I didn't know what to think about my wig, but I knew I wanted to fuck her. Right now. I reached in my purse, grabbed a condom, and ripped it open. I rolled it on in practiced motions. She spread her legs while I was doing this, and when it was on, I grabbed her legs and threw them over my shoulders and slammed my cock all the way in her in one motion. She smiled at my roughness, so I started pounding her hard. In no time she was cumming again, but I wasn't finished. I kept pounding her pussy as hard as I could, a whole year's worth of sexual frustration fueling my actions. I wanted to break her in half. She was so small, and so slender, I couldn't believe I wasn't splitting her in two!
Finally I was getting close. I started using extra long, hard strokes, grinding my cock against her clit, concentrating on feeling every second of this bliss. Then, finally I came hard, filling the tip of my condom. I collapsed on the couch next to her. I reached down and grabbed my wig and started to put it back on, when she grabbed my hand. My eyes asked my question for me.
"I like you looking like a man."
Well, that sucked. A year of effort, meals skipped, hurt knees to run extra miles, hour-long aerobics and yoga sessions, learning about make-up and clothes, and shoes, and accessories. Today, hours of preparation to look as much like a woman as possible, and what did I get for it? "I like you looking like a man."
I kept my voice neutral,but with a definite girls tone, and said, "I'm sorry you feel that way, Amy."
"No, I'm sorry! I don't mind men wearing women's clothes. I don't mind them being bisexual. You can do those things if you want. It just doesn't do anything for me, you know?"
"Then why am I here?" I asked, still angry.
"Because you look hot. As a girl, yes, but also as a man. I really wanted to know you better. Like this. Without the clothes and wig."
My voice didn't change. It was cool, but high and breathy, "Amy, you're entitled to desire what you want, but I can't be that person. I'm not very far on my journey as a cross dresser, but I know I want to stay on it."
"OK," she said, a bit sadly.
"I'd still like to be your friend," I said.
She smiled, "I'd like that too."
She helped me clean the condom off my cock, then asked if I would let myself out. Apparently she was still embarrassed. I hugged her tightly, and she laughed and said she needed to quit dating women if she wanted a man. I agreed, but told her if she ever wanted a good time with no strings, her friend Madison would be there. We kissed again, which felt more...chaste somehow, and she went to her room.
I started putting on my clothes and wig, and headed for the door. I'd been tested in an unexpected way tonight. I could have turned aside. Amy was pretty enough for any man, and I'm sure she could have made Taylor Madison very happy.
But I'm not him.
I'm Madison.
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