Maddy's Surprise

We stumbled up the last flight of stairs to her apartment, giggling and heady with excitement.

She led the way to her place, my hand squeezing her ass all the way. My arms looped around her waist as we reached her door, my face nuzzled into her neck, and my erection pressed between her buttocks.

We crashed into her hallway, she turned, and I kissed her mouth. My tongue explored hers, my hands slipping from her back downwards.

Our third date, and my heart thundered at the possibilities ahead. I felt bold, and my hand began to cup underneath her buttocks, slipping dangerously between her thighs.

She broke the kiss. And held me at arms length, her stare suddenly serious and sober.

"I think we should go to the living room, sit down, and have a talk."

This was a change of gears; my cock was almost bursting out of my jeans it was so hard.

It was ok though; it's a big next step; let's have a chat if it makes her comfortable.

She directs me to the armchair, then takes a seat on the sofa opposite.

"Listen, Marty, I've been having a lot of fun with you, but I'm not sure we're going to work out?"

"What? Where's this coming from? We've been getting on great, I've been having such a great time with you?" I move to the edge of my seat, pleading in my voice.

"Marty, you don't even know me." She turned her eyes from mine.

"I know that, but that's why we've been doing what we've been doing for the last two weeks!

"The restaurant? Talking till they threw us out?

The picnic? All day trying to get to know you?

And tonight, we've had fun? Was it my dancing? Is that what's put you off?"

I try some humour and a smile to ease the tension. I had not seen this coming at all.

"It's not that, Marty; I've had lots of fun too, I've had the time of my life, but... I have to tell you something now. Something I should have told you sooner, but I didn't know how."

This was ominous. Kids? Married? She was young and pretty, but things happen when you're young and stupid.

She brushed her long, dark hair behind her ear with one hand and stared at me with wet, vulnerable eyes.

The tension was unbearable as the silence lengthened between us.

"Just tell me, Maddy." I broke; I couldn't take the not knowing.

"Marty, I'm not what you think I am."

Shit, she was on the game?

"I.. I wasn't always like this," she gestured to her body. She looked gorgeous, short summer dress barely covering her pert breasts and hardly long enough to cover her firm white thighs.

"You mean you lost weight or...?"

"Marty, there's no way to sugarcoat it; I'm just going to come right out and say it."

She didn't.

"Maddy, come on?" I beseeched her.

"Marty... I was born a man."

"Fuck off." I started laughing. Her serious look cut me off.

"No way, you're... and you got those... and you're not..." The questions wouldn't form in my brain; it was impossible. We'd just been kissing; I had had a hand on her ass... she couldn't?

I shot to my feet confused and shocked.

Maddy flinched in fright and lifted her leg up defensively, arms covering her head in fear.

Her apparent terror and vulnerability overtook my confusion, and I went to her side to comfort her.

"Maddy, it's ok, it's ok. What did you think I was going to do?" I soothed.

Tears close to forming in her eyes, she said, "I thought you were going to get angry, you were going to hit me? It wouldn't be the first time."

My heart breaks for her. I bring her close to my chest, a protective nature taking over.

She used to be a man.

Feeling her warmth in my arms and remembering the fun we've had... it doesn't repulse me.

Did she still have... it though? Did that repulse me? I wasn't sure.

We stayed locked in that embrace for a time, neither of us sure what to do next.

I began to move my arm up and down her back.

I feel her arm start to search up my chest.

It reaches my cheek, and her eyes follow.

Our eyes meet, and I am electrically charged.

I kiss her. I don't care, she's still the same person I've enjoyed being with, who made me laugh, who made me feel special.

I kiss her fully and passionately, one arm around her mind riff, the other moves down on her bare thigh.

We break our kiss, and I stare into her face.

Is her chin a bit square? Her eyes not so soft?

I can't see her neck from here, but there'd be an Adams apple, wouldn't there?

Did it matter?

"What are you thinking?" she asks.

"I'm thinking I want you, Maddy," my mouth has answered before my brain has processed the question, my body knowing what I wanted before my consciousness.

She looked into my eyes quizzically, assessing my truth.

"Wait here." She told me.

In her absence, I assessed my truth myself.

I had been on three dates with the most amazing person. Things were hotting up, I fancied her, and this is what I wanted.

I'm not gay, though?

Did that matter?

She was beautiful; her body was slender and delicate; her eyes were hazel and alive; her lips soft and inviting.

Her breasts looked fucking hot too.

What about her dick?

What a crazy sentence.

Would she want me to touch it, get her hard?

Would she expect me to suc...?

She re-entered the living room, standing in the doorway, one arm leaning on the frame, one leg bent in front of the other.

She wore a red negligee, lace cups barely containing her breasts, it ran silky smooth down her torso, ending mid-thigh in another delicacy of lace.

She stood, elfin like in the soft light of her lamp, her face coy, her body the opposite.

There's not a man alive who wouldn't have thought she was all woman.

"Are you sure you're ready?" She asked, hesitancy in her voice.

I nodded that I was, too dumbfounded to use my words.

She sighed nervously and began lifting the hem of her lingerie.

She unveiled her cock, flaccid, petite, bald, and...cute?

Was I shocked? Disgusted?

No, I was aroused.

"Come here," I commanded her softly.

She walked to me, her smooth legs whispering under the silk of her negligee.

She fell to her knees so we were at eye level, and our mouths met again, softly at first then progressively harder and hungrier.

I felt her hands at my belt, and my stomach dropped with excitement.

She freed my hard dick and worked it with her hand.

Oh shit! Would I be bigger than her? I thought madly. Why was that important to me?

Her eyes let me know her intentions, so I leaned back in readiness.

Her lips on my tip were an exquisite thrum of pleasure, and I groaned as she took me into her mouth.

My hips moved of their own account, as if gently fucking her face. My hands combed her hair and met at the back of her head.

Her hands moved away, so it was only her mouth stimulating me. I couldn't work out from where, but they came back with a bottle.

She squirted a generous amount in her palms and began working the lube all over my cock, her hands sliding up and down slickly.

She emptied another healthy amount onto her fingers and reached behind herself and began spreading it over her ass.

This was happening.

She stood, and the nightwear came off over her head. Her breasts bobbed freely and were every bit as magnificent as I'd imagined.

She positioned her knees on the sofa, either side of mine.

My mouth hung loose in anticipation.

Maddy took my face in her hands and put her forehead to mine.

"Ready?" She whispered.

I could only nod. She reached down, grasped my dick, and guided it to her hole.

My tip nudged her until her weight began slowly dropping and the exquisite pressure of her tight ass began to grip around me.

With little jerks of movement, I was soon deep inside her, and she began fucking me in earnest.

The sensation of her still quite limp penis and small testicles tickling my abdomen was unusual but not unpleasant, and I relaxed and let the warmth of her body fill me up.

As her rhythm increased, so did my desire, and in no time I was squeezing her boobs and kissing her with unrestrained passion.

I put my hands under her and stood, holding her on my rigid cock.

"Which way to the bedroom?" I breathed.

With a giggle and a nod of her head, she guided me there.

I laid her down on her bed gently, and began building my own momentum. She purred her approval, and her nails dug into my chest.

I looked down and saw her now harder dick bouncing with my efforts.

Should I help her? If she had female genitalia, I'd have happily played with her clit to increase her pleasure.

I grasped her base, and her eyes widened in surprise.

The feeling was familiar but alien, her dick like a disembodied extension of my own.

I started working her up and down, matching the pace of my thrusts. I was, crazily, relieved that I had a slight edge on her in size.

Her back began to arch, and she looked amazing. Beautiful and sexual.

Her palms were pushed into her eye sockets as she writhed and contorted on my cock, hers controlled with my hands.

"Cum in me!" She yelled suddenly, and it was like a command I didn't know I was waiting for.

The immediacy of my orgasm is instant and overpowering. Within ten more deep lunges, I was filling her ass with my seed, every jet a delicious crescendo of ecstasy.

In the throes of my delirium, I was overcome with a desire to give to this girl all the pleasure she had given me, and without a conscious decision being made, I withdrew myself in a wash of hot cum and dropped my head to her lap, taking the head of her cock into my mouth.

It was insane, ridiculous and wildly liberating as I inexpertly began to blow her. My tongue moved crazily and I took as much of her as I could to the back of my throat, the hot yielding flesh filling mouth.

Her fists grabbed handfuls of my hair, and she began urgently rocking her hips, just as I had done, and I felt a stiffening in her that could only mean one thing.

That was something I was not yet ready for, so I disengaged from her cock just in time to watch her own orgasm release over her tummy, a couple of shots all the way up to her breasts.

I used my hands to make sure she was fully spent and leaned over to kiss her again.

Our eyes locked once more, and our sweaty brows again touched in an intimate mutual connection.

"Marty?" She asked in between heavy breaths, "Are you good?"

"In a way I never thought I could be," I answered with a smile.