Date: Tue, 3 Jul 2012 17:17:23 -0500
From: Amanda Saunders <ams.dca@gmail.com>
Subject: Maddie's Date

Disclaimer: All characters appearing in this work are fictitious. Any
resemblance to real persons, living or dead, is purely coincidental. All
characters portrayed are consenting adults - so, please be one yourself and
don't read this if you're under the age of majority or consent in wherever
it is you live or happen to be reading this. If you like it, the author
welcomes feedback. If you don't like it, at least send helpful feedback.

-----

After my wonderful lunch with Alan, I hurried back upstairs and got back to
my desk.  Not more than 5 minutes later, I got a text from Alan: "Given
that lunch was good, how about dinner?"

"Tonight?" Was my response - I hope I didn't misunderstand his intentions,
but instantly I had butterflies in my stomach (and lusty thoughts in my
head).

My phone rang. "Tonight." He responded. "I was thinking Italian - would
that suit you? I know a great little place that's totally out of the way"

I wasn't sure how to play this one. Every naughty bone (err, hem... part)
of my body wanted to say "YES!" but I knew I wouldn't have time to go home
and I wasn't really dressed for a nice date....

"How about tomorrow? I really want to, but I'm afraid tonight just doesn't
work for me - I need to stay a little later at work tonight", I lied.

"Well, how about just a drink then, after work? I can't quite get you out
of my head" he persisted.

"Okay, I guess I could do a drink.  Meet me in the lobby at 7:30?", I
offered.

"It's a date".  I almost giggled when he said that.

I was on pins and needles - but then panic set in... it was a date. A real
date, with a tall, dark-haired, handsome man... the same man I'd been
fantasizing about for the last month! A date and I didn't quite look as hot
as I wanted to... thankfully, I had my favorite bra and matching thong on -
not so much so that Alan would see it (not tonight, at least) - but because
I know they're there. They did make me feel sexy - but to complete it, I'd
need some stockings.

I told my boss I had to take care of something and slipped out for a quick
trip to Victoria's Secret - thank goodness our office was just two blocks
away from one of their flagship stores.  I found a sexy pair of lace-top
thigh-highs.  Enough to tease him and make me feel just a bit more risque.

I was back at my desk by 2:30 and I struggled to keep my mind on work until
it was time to meet Alan downstairs.  Just before 7:30, I went to the
restroom and slipped on my stockings, pulling them up under the edge of my
business-appropriate, but sexy black skirt... which I hiked up just a bit
so that the lace edges might peek out just a little bit.  God, I was so
turned on...

I rushed to the elevator and right as I stepped into the lobby, Alan came
in through the revolving doors.  When we met, he took my hand in his and
raised it up as he bent to gently kiss it. /swoon/.

Alan led me out of the building and a few blocks over to one of the bars
that had become really popular in the last few months.  Walking in, past
the line, Alan greeted the hostess by name and with a smile, she led us to
a private booth towards the back of a smaller room off of the loud main bar
area - I was glad because wanted some privacy but I really wanted to be
able to actually hear Alan without shouting.

I may be a beautiful woman through and through, but I still have a man's
taste in liquor. I love a good glass of scotch.  I surprised Alan by
ordering a Glenlivet Nadurra. Complex, strong, yet smooth and a little
sweet - much like my date. He took it in stride and I think it was a bit of
a turn on for him.  Still, one drink - and that was it.  I wanted to keep
my wits about me...

But one thing led to another and Alan talked me into a glass of wine and
then another. And before I knew it, I was somewhere between tipsy and
drunk... but more importantly, our hands were all over each other -
somewhere in the middle of the first glass of wine, Alan's hand found its
way to my leg, and slowly it worked its way up my to the top of my
stocking.  Each inch was electric.  I had to stop him before he discovered
my secret - I certainly didn't want to have to tell him about that in some
bar - but I knew we had to talk about it soon.  To get his mind elsewhere,
I began to stroke his leg with my hand, eventually brushing against what
started to feel like quite a wonderful cock in his slacks. Each time I let
my hand linger a little longer, teasing him with my fingertips... we were
both torturing each other, yet pretending like nothing was going on, trying
not to miss a beat in conversation.

Eventually, I couldn't take it. I had to ask Alan to take me home.  Ever
the gentleman, he obliged. As I stood up from the table, the alcohol hit me
and I slipped just a bit.  I ended up right in Alan's arms - and it was a
bit of heaven.

We made our way to a cab, Alan holding my hand the whole way to make sure I
didn't slip again. I insisted that I was fine - really, I felt okay. Alan
insisted that I hold his hand, nevertheless and he asked if he could walk
me to my door when the cab pulled up to my place.  I knew I should tell him
I was okay... but something in me blurted out "yes" before I could convince
myself that I was getting myself into trouble.

Alan walked me to the door as I found my keys in my purse. Alan leaned in
for a kiss.  I kissed him - and told him to give me just a second, but that
I didn't want the night to end.

With a loud "click", the deadbolt snapped open and the heavy wood door
swung into my apartment. I put my keys down on the table in the entryway,
slipped off my heels and tried not to slip as my stocking covered feet
carried me across the gleaming hardwood floors. I almost floated down the
hall while Alan waited in the entryway.  I rushed around my bedroom, trying
to make it presentable.  After a quick clean-up, I floated back to Alan,
still standing in the entryway.

Upon my return, he pulled me close to him and I kissed him even more
passionately than our elevator adventure earlier that day. When we both
broke off for a little bit of air, I was still buzzing - the alcohol was
still hitting me and the making out had really done something as well.

I took Alan by the hand and pulled him through the doorway into my living
room - no bedroom just yet.  First, we needed to talk.  I was scared, but I
knew if this was real, I had to be my real self to him.

I sat Alan down on the couch and asked him if he trusted me.

"Of course I do", he answered, "maybe you've missed it, but I think we have
an amazing connection, mental and physical and of course, I trust you".

"Can I trust you with a secret?"  Was I really about to out myself as
transgendered to this amazing man?

"Of course."

"Alan - I know this is quick, but I feel myself so amazingly attracted to
you... but you need to know something about my past", I continued... this
was really hard, but I trusted him to at least not hurt me, even if he
completely lost interest in me.

"Alan, I was born as 'Adam', but I'd always known I was really a woman.
Ever since I was a little kid, I knew I was a girl."  The words just kind
of hung there, in the air.

Alan took a second and said "Maddie - I've had my suspicions for a
while. Don't take that the wrong way - you're amazing and totally feminine
to me, but when we kissed earlier today, I felt something press against my
leg.  That, along with your bashfulness under the table made me wonder."

I think I turned a few shades of red.

"It's really okay - kind of hot, actually", he said, as he gently took my
hand.

My heart was still beating quickly - a mix of passion and fear - an elixir
like no other... but before I knew it, I was crying just a little bit - the
tension of it all, mixed with fear and yet, somehow relief.. and a bit of
alcohol just made me cry a bit... "Are you sure?", I asked, trying to hide
the tears.

"Yes, I'm sure", he said, putting his arm around me and lifting my chin
with the other hand.

I could see that he meant it as he looked me straight in the eyes.
Nervously, I reached out and gently kissed his beautifully lips.  He kissed
me back.  Gently at first, but soon it was passionate once again.  His
hands were all over my body - one around my back, keeping me close, the
other gently caressing my breast. I could feel my nipple getting hard under
his expert teasing.

Somehow in all of this, I decided that we needed to move to the bedroom. I
slowly pulled myself back from his embrace and took him by the hand,
leading him down the hall to my bedroom.

Was I really doing this? The bedroom, on the first date?

Yes. Yes I was.  I wanted him - and I was starting, just maybe, to fall for
him... but if nothing else, I wanted him to be my first, just like I'd been
fantasizing about.

We quickly made our way to the bed and fell into it as I pulled him down on
top of me. Finding ourselves on the bed, Alan had one of his arms around
me, holding me tight while the other hand found its way to my skirt and
grabbed a handful of my ass, all while he proceeded to kiss me like no
other man had before. The passion was overwhelming. Carnal. I pressed
myself against Alan's beautiful body as his hand found its way lower. As we
continued to make out, Alan's hand found its way under my skirt, caressing
my thigh through the black lace of my stockings. Slowly, expertly, he
worked his way up the back of my leg until he had my skirt pulled up enough
to expose my toned, petite ass, covered only slightly by my gray lace and
satin thong.

With every inch that his hand went higher, my breathing grew heavier - more
excited - and Alan knew exactly what he was doing to me as he continued to
kiss and caress me.

I wanted him. I couldn't take it any longer - I started moving my hand to
unbutton my shirt and Alan got the clue. I started and the bottom and he
took it down from the top. My bra covered breasts eagerly greeted Alan's
exploring hands.  I pushed him back, however, telling him I wanted his
shirt AND pants off, in trade.

My hands found their way to his belt, unbuckling it and moving to the
button and zipper just behind it. Once he had his shirt off, Alan helped me
with his pants, pulling them off and revealing a pair of boxers, nicely
tented, all for me. I reached out and put my hand on Alan's crotch, amazed
by how natural it felt to have his cock in my hand.

Staring into his eyes I said, "Alan, I want you to make love to me. I want
you to fuck me. I want to be your little girl tonight"

Alan grinned and pulled me onto my side so that he could unzip my skirt and
pull it off, one handed, all while kissing my neck and making me wet,
wanting him so. Once he had my skirt off, Alan let me back down and his
hands found their way around my back to my bra. He unhooked it and pulled
it off of me.  Almost instantly, he tried pulling me on top of him.

I had to stop him, for a moment, so that I could pull a condom and some
lube out of the nightstand - I kept a few there to use with my toys and I'm
glad I had one that night. Pulled Alan's boxers off and his cock sprang up
to meet me - it was a thick, un-cut 8 or 9 inch beast.  I wanted it in my
mouth so badly - but I wanted it in *me* even more.  I unwrapped the condom
and slowly unrolled it down Alan's shaft. Once covered, I ran my hand along
his length, spreading a bit more lube on him, saving just a bit for my
waiting, wanting, aching hole.  After I slipped my lube covered fingers
past my thong, I quickly fingered my tight hole - getting myself slick and
ready for my new lover to have his way with me. Not wasting any time, I
asked Alan how he wanted to take me.

"Let's start with you on top - I want to watch you bounce as I fuck you" he
responded.

I quickly straddled him and helped his rock hard cock find my waiting
pussy. I held my ass so that the tip of his cock just barely pressed
against my opening. I took a breath and started to impale myself on his
pole. I pushed out as he pushed up and he slid into me faster than I would
have expected. It hurt a bit, but I loved it.

I breathlessly told Alan that he'd just taken my cherry. That set something
off in him. I felt him get even harder in me, filling my ass even deeper. I
began to pull out of me and then push back in, slowly at first, guiding my
hips with his strong, manly hands. Soon he was moving quickly and I was
matching his pace - we were a well oiled machine and his piston was
pounding into me, working me, deeper and fuller than I'd ever known before.

I was delirious with pleasure, and I started to moan, saying all sorts of
dirty things to my new lover as he drove himself into me from below. After
a few minutes, I couldn't take it any longer - I was in a frenzy, pushing
myself up and down, riding Alan's beautiful cock for all I was worth. Alan
was starting to moan as well and soon he arched his back and I could feel
the warm flood as he came deep within me.

That set me off too, and I came just after he did, covering my slate grey
thong with a sticky white mess.  I felt Alan grow soft within me and he
slipped gently out of me as I collapsed in his arms, spent... and no longer
a virgin.


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Want to hear more? I'd love to get hear your suggestions for where the
story should go next: ams.dca@gmail.com