Madison Cums Out of Her Shell

I first saw Madison across the room at a party my friend Simone was hosting. I didn't know half the people there and wasn't even sure why she'd invited me. I'm very shy and not a party person. The reason I was attracted to Madison was that she didn't seem to fit in either. That, and her incredibly good looks.

Madison is tall, but on the petite side, with long blonde hair, a round, kind face with wonderful blue eyes. She has large breasts with some cleavage showing through her white satin blouse, and maybe a little of her nipples pushing out. She wore a short red skirt and heels, which showed off athletic legs. Too lovely for this group of people. Maybe too lovely for me too.

"Hi, I'm Megan," I said, sitting down on a couch next to her that was a bit out of the mainstream of people.

"Madison," she replied, glancing at me briefly.

"Some party, huh?" I said, not sure how to even start a conversation with someone so beautiful.

"Not really," Madison said, looking back out and looking bored.

"I'm not really into the party scene either," I said, also gazing at the rowdy crowd dancing to some song I didn't know.

Madison glanced back at me, her eyes piercing right through me.

"Then why are you here?" she asked.

"Simone," I said.

Simone was an old friend, and we had a special connection. We'd gone to middle school and high school together, among other things. It had been a year since graduation and none of us had any idea what we were going to do. Simone was well connected and always the life of the party. I wasn't much like her, but she seemed to like me, and want me.

"Ah, Simone," Madison said, crossing her gorgeous legs. "Seems we have someone in common then."

"You know her too?" I asked, trying not to stare at those smooth legs.

"Summer camp," she said. "Years ago. We hung out and became friends. I thought we'd drifted apart because ... well, I guess I was wrong. She reached out and wanted me here, so here I am."

I felt suddenly sad for Madison. She had this aura of solemnity, of quietness. Like she was some sort of lost soul.

"I never went," I said.

"Went where?" Madison asked.

"To summer camps. My folks couldn't afford it. Did I miss much?"

At this, Madison chuckled. "Nah. Mostly a bunch of girls and boys trying to one-up each other and get in the most popular cliques."

"Ah," I said. "Sounds lovely," I said, sarcastically.

"One thing I did like," Madison said.

"What?" I asked.

"The stars. Late at night I used to love to sneak out of my cabin and walk under the stars. I loved spotting the constellations and watching for shooting stars. Sometimes Simone would come with me. Keep me company, you know?" Madison paused. "Did you know that shooting stars are really tiny specks of space dust burning up in the atmosphere?"

"I didn't know that," I answered.

"That's how I feel sometimes," she said, looking down. "Like a tiny speck of dust, flying through space, waiting for a planet to swallow me up and flame out!"

"That's kind of dark, don't you think?" I said.

Madison turned to face me with those eyes. "You're right. Sorry about that. I've just had a bit of a tough time lately. But how about you? What'd you do instead of summer camp?"

"Fishing," I said. "My dad. He'd take me fishing up to these lakes in the mountains. I was never very good, but it did give us a chance to bond."

"Sounds fun," Madison said, that solemn look returning. "My dad left when I was a baby. My aunt raised me."

"Oh," I said.

"Don't get me wrong. She's wonderful. Best thing that ever happened to me. I love her dearly!"

We sat there for a few moments, watching the dancing and drinking. Feeling out of place.

"Want to see if they're out?" I asked.

"If what's out?" Madison said.

"The stars. You said you liked to see the constellations and stuff."

Madison looked at me and smiled. That smile totally lit up her face and changed her. No longer a sad puppy, but a beautiful woman.

"You know," she said. "I'd love that. Let's get out of here!"

We stood and made our way through the crowd. I noticed Madison's breasts bounced just a little as she walked. They looked good. The front door was wide open, so we stepped out on the porch, then started walking down the street.

"Too bad for the lights," Madison said, looking up at the night sky. "The streetlights ruin everything. Hey, I know a place without all that glare. Want to go there?"

I'd just met Madison, but felt a kinship, a comradery. "Sure. But I'll drive."

Madison directed me up to the top of a nearby hill. There was an observatory there and a wide-open space all around it. We got out of my car and strolled through the grass. The heat of the summer day had dissipated, and it was getting cool.

I shivered slightly.

"Here," Madison said, taking off a sweater she'd brought and putting it around my shoulders.

"Won't you be cold?" I said, glad for the kind act.

"I'm fine," Madison said. "I usually run hot anyway!"

We both laughed and continued walking.

"There's one!" Madison said suddenly, pointing to the north.

I looked up and saw a bright light streak halfway across the sky. "Beautiful!" I said. "If that's just a speck of dust, it sure dazzles on the way out!"

Madison laughed again. And that smile returned.

"I like you, Megan," she said. "Always seeing the best in things."

"Thanks," I said, shyly. "I, um, I like you too. You have a great smile when you use it."

We hung out at the mountain park and shared more of our life stories. She too had graduated a year earlier and wasn't sure what the future held. It was a summer of decisions.

"I'd love to do this again sometime," I said after dropping Madison off at her car. "Or something else."

"Me too," she said. "Call me."

I stood in front of my mirror as I prepared to meet Madison for coffee two days later. My curly brown hair, down past my shoulders, showed off my face - small nose, full lips, and light-brown eyes. My boobs weren't as large as Madison's, but okay. I wasn't as tall as her, but my legs looked pretty good in shorts. Was I dressing for a friend, or something more?

Madison met me at the door to the coffee shop. She wore white slacks and a black clingy knit top that outlined her incredible breasts perfectly - like two large globes. I tried not to stare.

"Sorry I was so morose the other night," Madison said as we sat at a private table with our drinks in hand.

"No worries!" I said, secretly glad she'd come out of her dark mood.

Our conversation was much livelier this time. We found we had some common interests - jazz, old movies, and history. A couple of nerds, I guess.

I found myself staring at Madison's face as she talked. When she waxed eloquent about Coltrane, her face lit up, that smile dancing across her lips, clear-blue eyes widening. And when she'd make a point, she'd wave a hand in the air, causing her breasts to jiggle just slightly. It was mesmerizing.

"I like hanging out with you," she said on our fourth "date" to an indoor botanical garden where we sat on a bench, surrounded by luscious plants.

"Me too. I think you're great!" I said.

Madison reached over and touched my hand, her fingers playing gently on mine. It sent shivers all through me, and especially into my crotch. That feeling reminded me of Simone. She was my first, and only, sexual experience - but what an experience! Simone knew a lot about sex and had brought me to some incredible orgasms with her fingers, her mouth, and even a strap-on that she used on my pussy, and even my asshole!

I hadn't thought Madison was interested in taking our friendship to another level, but that didn't stop me from fantasizing.

"What're you thinking about?" Madison asked, breaking me out of my naughty thoughts.

"I don't know," I said, lying. "I guess I was just thinking about spending more time with you. Getting closer to you."

"I'd like that too," she said.

I turned to her, and she leaned in slightly. Madison was going to kiss me! I tilted my head to the side and leaned in. When our lips met, I immediately felt aroused. Her lips were so soft and supple.

"Wow!" I said. "You kissed me!"

"Was that okay?" Madison said, shyly.

"Okay?" I said. "It was wonderful. I, I wasn't sure if you wanted to, um, sort of take things further than just friends?"

Madison smiled and then I saw a darker expression in her eyes. "I do, I really do. It's just that ..."

"What?" I asked, putting my hand on her arm.

"I'm a little embarrassed to say," she said, looking down, that I'm totally inexperienced when it comes to this sort of thing."

"You've never had a girlfriend or boyfriend?"

Madison looked up into my eyes. "I've never been with anyone."

I reached over and cupped her cheek. "That's perfectly okay. We don't have to do anything you don't want to do."

"Thank you, Megan," she said. "You always make me feel so comfortable."

She leaned over and kissed me again. This time I could have sworn I felt a tongue touch my lips. I opened up just in case and felt Madison's tongue flick ever so gently into my mouth. I was thrilled and felt a dampness between my legs. I let her explore my mouth and tongue a bit before swirling my tongue on hers.

"Mmm," she murmured. "That felt ... I ... that felt wonderful!" she said, adjusting her hips on the hard bench.

Maybe she was getting damp like me. No, I was more than damp. I was getting downright wet.

I stroked her arms gently and she put a hand on my upper thigh. We kissed again, more passionately - our tongues trading mouths. I felt her hand move up my thigh just slightly. I felt warm and tingly. I had this funny rush in my belly and my heart started racing. I was having a hard time thinking of anything but Madison's amazing body, and me kissing it all over.

Nothing else happened on that date, but I invited Madison over to my place for dinner the next night. She agreed.

I had no idea what the evening might turn into. I dressed hoping for the best in a white silky dress that was very short. The dress was a little see-through, so my bra, and my nipples, showed just a bit. I could also just make out the outline of my thong underneath. I hoped it wasn't too suggestive in case Madison wasn't really interested in moving to the next level.

"Come on in!" I said as I opened the door.

"Thanks," Madison said, casting her eyes around my apartment. "Great place!"

"I love it," I said, closing the door. "It has a great view of the park and feels very private."

Madison handed me a sourdough baguette. I touched her fingers as I took the bread. She was wearing a short dress as well, though not as short as mine. It was powder blue and lovely. She was made up, like this was a special occasion. I hoped it would be very special. The dress gave me a lovely view of the tops of her boobs.

"Nice dress!" Madison said as we walked into the kitchen.

"Thanks!" I said, twirling around. The dress came up just enough to reveal my thong. I hoped I wasn't being too suggestive, at least not yet. "I love yours too!"

Madison helped me finish dinner. We stood side by side cutting vegetables. At one point I put my hand on hers and she turned to me. We kissed and I started feeling that itchy feeling in my crotch again.

A chime from the oven broke the mood.

"Dinner's ready!" I said, breaking off, though not wanting to.

Madison seemed uneasy as we ate, she hardly touched her food.

"Does it not taste good?" I asked.

"Oh no," Madison said. "It's great. I'm just a little nervous."

"About what?" I asked.

Madison paused, looked down, then back up with those wonderful blue eyes piercing right through me, melting me.

"That you might not like me if we, well, if we do more with each other."

I laughed softly. "Oh Madison, there is zero chance of that!"

Madison relaxed, but only slightly.

"Let's clean up and sit by the fire," I said, getting up and clearing dishes.

Although it wasn't that cold outside, The fire seemed to add a romantic touch. The flames crackled and snapped and cast a flickering glow around the room when I turned off the kitchen light.

We sat together on the couch, and I laid my hand on Madison's upper thigh. She did the same and we leaned in and kissed. I felt an urgency in her kiss, and she held my neck to pull me in close. We tilted our heads side to side to explore new areas of our mouths.

"I love kissing you," Madison said when we'd broken off. "It makes me feel tingly inside."

"Me too," I said, stroking her cheek. "It makes me tingly and other things down there too," I said, looking between my legs.

"Oh!" Madison said, following my gaze.

I had this feeling like I wanted to pee, and I knew from my time with Simone that my pussy was wet. Sure enough, a dark stain was spreading through my panties.

"Have you ever touched another girl's breasts?" I asked, causing Madison to look up, adjusting herself slightly on the couch.

She shook her head.

"But you've touched yourself, right?" I asked.

"I have," Madison answered. "My nipples are very sensitive."

"Mine too," I said. "Do you want to touch me? I sure want you to."

Madison hesitated for a moment and then nodded. "I'd like that."

I reached over and pulled her hand to my chest, pressing her palm into my right breast. It felt amazing as she compressed my nipple, sending new chills into my crotch.

"Mmm," I said. "Use your other hand to squeeze my nipple. See how hard they're getting?"

Madison used her right thumb and index finger to gently squeeze my left nipple. Oh, wow did that feel good!

"Harder, Madison, squeeze it harder. Ah, yes. Mmm, so good!"

Madison used both hands to squeeze and fondle me. It was only the second girl to ever do that, and I loved her gentle touch.

"Can I, um, can I touch yours?" I asked as I watched Madison's fingers at work.

"You can. I'd, I'd like you to," she said.

I looked at her lovely breasts, so full and round. Her dress pressed in on her boobs so that her nipples and areola showed through. I carefully reached over with both hands and fondled them. They felt so firm.

"Oh!" Madison said. "Thanks for being gentle. That feels really amazing!"

"I'd love to kiss them, if that's all right," I said, looking into her eyes.

Madison nodded and I leaned over to plant a gentle kiss on each nipple. This caused Madison to jerk slightly and raise up her chest towards me.

"Wow!" she said. "I didn't think I could feel that way there."

"I know this is going to seem very forward, but I would so love to see your breasts. I can take off my dress so you can see mine too, if that helps!"

Again, Madison paused. Then as if she'd come to some sort of decision, she pulled her dress over her head. Beneath was an absolutely gorgeous body. Narrow waist, flat tummy and slender arms. Her breasts were barely held in by a sheer black bra. She had on matching panties.

"You are so beautiful, Madison. So beautiful!"

Madison blushed slightly. "Do you really think so?"

I nodded. "Want to see me?" I asked.

"I would love that!" Madison said.

I unzipped the side of my dress, stood, and sluffed it off onto the floor, stepping out of my pumps.

"You're gorgeous!" Madison said, eyeing me up and down.

I sat and turned my back to her. "Why don't you undo me so you can see more!"

She unclipped my bra and I let it fall on the couch. Turning to her I saw her eyes fall to my chest, eyebrows lifting, a smile crossing her face.

"Wow!" she said softly.

"Want to touch?" I said.

"Uh huh," Madison replied.

When her fingers touched my nipples, I took in a quick breath. Simone had never touched me with such tenderness (though what she did turned me on greatly!). Madison rubbed my nipples between her fingers.

"They're so hard," she said, staring.

"And getting harder. You're really exciting me, Madison. I, I want you to kiss them!"

"Oh, you do?" Madison said, looking up at me.

"Please kiss and lick my tits, Madison. Please!"

Madison bent over and very tentatively kissed a nipple.

"That's right. Now stick out your tongue. Mmm. Oooh, so wet and warm on my tit. Now suck on it a little. Like that, oh yes. Oh, fuck that feels so good!"

I held her head to my chest as she learned how to suckle a girl's nipple. As she sucked in on it, I could feel moisture come out of my pussy lips. I was pretty sure I was now dripping out of my panties.

As she bent over, I got a look at her wonderful ass, so round and full.

"My turn to see you," I said, stroking Madison's long blonde hair.

She sat back and reached behind, undoing her bra.

"Oh shit!" I said.

Her breasts were two beautiful globes. Her nipples stood straight out and looked so tender and her areola so light-colored.

"Are they okay?" Madison said. "I've never shown them to anyone!"

"Oh Madison," I said. "They are the most beautiful breasts I've ever seen. So big and round. I want to eat them so bad!"

Madison laughed. "Well," she said, offering a nipple to my mouth, "I guess dinner's served!"

I came in and flicked my tongue out, touching her nipple. She flinched slightly but didn't withdraw. I went further and licked around her nipple, taking its hardness into my mouth and sucking slightly.

"Mmm," Madison purred. "Feels nice."

I took my fingers and tweaked her other nipple and then traded back and forth between licking and sucking and squeezing. Her breasts were so firm and the skin so soft.

I came off her breasts and kissed her deeply. Our boobs met and our nipples mingled together between us.

"Would you touch me," I said, breaking off. "Touch my pussy?"

"Really?" Madison said, a surprised look on her face.

"I am so wet right now, and I need your fingers on me!"

I reached over and took her hand. She didn't resist but let me turn it palm upwards and place it right between my legs.

"Oh wow!" I said as her fingers contacted my slit.

"You are wet," Madison said, slowing stroking up and down.

I began to move my hips back and forth, trying to get her fingers to press in.

"You are really turning me on, Madison. I, I want you to put your fingers inside me!"

"Inside, like inside your pussy?" Madison asked, looking at my wet crotch.

"Oh yes. Please! Just go underneath my thong. Just curl your fingers, yes, like that, ooh like that - oh!"

As I felt Madison slip inside me, my body started feeling tingly. Especially in my pussy.

"It's warm," Madison said, shifting herself on the couch like she was trying to get in a better position.

"I know!" I said. "Your fingers feel amazing! Now pull them out and push them in, like you'd do to yourself. That's it. Oh fuck, Madison. Oh, fuck!"

I began moving my hips on Madison's fingers. I felt light-headed and buzzy. I was already getting close. Seeing Madison's beauty and knowing her fingers were fucking my pussy was so amazing!

Suddenly, Madison withdrew her fingers and turned away.

"What's wrong?" I asked, still moving back and forth rhythmically.

"I can't," Madison said, nearly in tears. "I can't do this!"

"I am so sorry," I said, touching her leg. "I didn't mean to make you feel uncomfortable."

"That's not it," Madison said, turning to me. "It felt too good!"

"I'm not following," I said. "Talk to me."

Madison paused but continued shifting on the couch. "I've, I've not been totally truthful with you, and I think it's going to ruin everything!"

"That's not possible, Madison," I said, squeezing her thigh. "You can be honest with me. I really really like you. You can tell me, whatever it is!"

Her eyes got wide, and a tear streamed down her cheek. "Truth is, I haven't always been a girl. I, uh, I was born a boy but never felt at home in my body, until a year ago. Meagan, I'm trans."

"Oh!" I said, completely surprised. "I had no idea. You're one of the most beautiful girls I've ever seen."