Date: Wed, 27 Oct 2010 16:23:15 -0400
From: Rebecca Denise <rebeccadenise4@gmail.com>
Subject: "Curiosity Killed the Boy, but Freed the Girl" (TG)

Author's Note:

I am 25 now, but this story takes place when I was a teenager. This is
autobiographical, and 100% true. The only names used in the story are my own.
This is my first story, so feedback from readers would be greatly appreciated!


Curiosity Killed the Boy, but Freed the Girl


I have the internet to thank for my journey into femininity. Walking my
long road in high heels began in 1997 when I was but 12 years old. At the
time, AOL had several text-based games, and one of them was a mystery game
set on a tropical island. The players had the option of going into a store
and changing the clothing their characters were wearing. Being 12 and a
huge fan of Monty Python, I thought it was the absolute pinnacle of
hilarity to put a miniskirt and heels on my character.

Naturally, this got me curious, and I thought about trying it for real. So
the first time my parents said they were going out for the evening, I went
into my parents' room, opened up my mother's dresser, and pulled out the
first bra and pair of panties I could find, and quickly stripped off my
t-shirt and jeans. Trembling with a strange combination of fear and
excitement, I stepped into my mother's panties, and I immediately felt
wonderful. A feeling of incredible comfort and pleasure washed over me. It
felt so amazing to be in women's underwear. Next I put on the bra, which is
a garment that I had always dreamt about taking off a woman, and I now
found myself putting one on. I tried to do it the way I saw women do it in
the movies - I put my arms through the straps, and reached behind me to
fasten the hooks. I already felt so feminine simply reaching behind my back
to grasp the hooks; I couldn't begin to imagine the exhilaration I would
feel when I finally got what would become my favorite article of women's
clothing fastened and in place around my chest. I only had a modicum of
difficulty in putting on the bra, thanks to my smaller frame and boyish
flexibility. Nowadays I need to use the old
'hook-it-in-front-and-spin-it-around' trick.

I stood there, looking down at the beige soft cup bra wrapped tightly
around my 12 year-old chest and back. I looked down at the two small cones
of flesh I had on my chest poking through the nylon cups meeting the seams
but otherwise barely able to fill the cups out. I had been teased by the
boys at school for my chubby little boy boobs, and I had heard on more than
one occasion that I needed a bra. Now I was finally wearing one, and I had
to agree - I did need a bra. I needed as many as I could get! I was now,
forever, "hooked" (and I do so love that bra pun!). I cupped my chest flesh
in my hands over the bra, and I admired myself in my mother's full length
mirror. For the first time, I was happy with my body. I loved the new
feelings I was getting from my mother's clothes.

I kept dressing in secret every opportunity I could. Eventually I moved on
to wearing my mother's skirts, blouses, and dresses. I dove deeper into her
lingerie drawer, and tried on pantyhose and slips. As soon as my parents
were out the door, I was in a skirt, sitting at my mother's vanity,
experimenting with makeup. Also, I started to explore crossdressing
online. I found message boards, newsgroups, and chatrooms - which I had
been going into for some time already. I had some excitement in cybering
with women, but after I started dressing I got the idea in my head to cyber
AS a woman, as Rebecca. I created a new screen name on AOL, created a new
password, and within seconds I was getting IMs from men. I had never done
anything for real with a man, I had never even thought about it before, but
here I was sitting at my computer pretending to be Becky and flirting with
men. Flirting turned into cybering, and I loved it. Here I was, 12 and 13
years old, pretending to be a busty 20-something girl saying that I was
sucking their giant cocks. None of these guys knew I was really a young
boy, just as I'm sure no one online is really 8 inches when they say they
are. It's all fantasy, and I loved it! I still do.

At the same time I also had a screen name for my genuine, crossdressing
self, who I also decided to call Rebecca. I used that screen name to chat
with other CDs who knew how I felt and to make friends. Of course, I also
found men who were very interested in young CDs, and before I knew it I was
cybering with them not as a character I had created but as myself. I found
myself getting very turned on when I would type things like "I drop to my
knees and kiss the head of your cock," or "I flip my skirt up and bend
over, waiting for you to take me." By age 14 I was seriously questioning my
sexuality, and I was going online almost daily to find men who wanted a
cyber session with Becky. I had also by this point stolen a small wardrobe
from my mother that I kept hidden in my room, and I pumped several loads of
cream into those panties every time I put them on and played online as
Becky. I also had a cheap digital camera that I had gotten for Christmas,
and so I put on AOL and Yahoo some pictures of the 14/15 year-old sissy
that the men of the Internet loved to chat with.

Eventually the men wanted more than cyber. They wanted to hear Becky cum
and say their names. That's when I graduated into being a teenage CD phone
sex slut, actually telling men how badly I wanted their cocks in my
holes. Some men told me to get various objects to stick in my ass, which I
was curious about and so I was happy to oblige. I had moisturizer that I
used as lube, and I would insert my hairbrush handle (ribbed, for my
pleasure), my electric toothbrush handle (homemade vibrator!), and even my
mother's curling iron (long and hard, as Becky grew to love!). At this
point in my life I was pretty sure I was at the very least bi, if not
totally gay, and my old friend curiosity started to rear his wonderful head
yet again in my life.

I was 17 when it finally happened. I had been talking to a guy on Yahoo for
about a year up to that point, and he was a frequent cybering partner of
mine. It was late May, my mom was away for a week out west to see friends,
and my father was busy with work almost all the time, so I had a lot of
free time to dress as Rebecca and talk/cyber with every man I could,
including my Yahoo lover. He was in NYC, and I lived on Long Island, and I
told him that I was alone for the day. He immediately asked if I wanted him
to come over. I was absolutely terrified, but curiosity won out and I said
yes. He signed off, and I immediately went to work shaving my legs, and
putting my outfit together. By this point in my life I actually had a
decent sized wardrobe, both "borrowed" from mom and purchased on my own. I
had a crappy, pageboy-style red Halloween wig (I am a natural, proud
redhead and will only ever wear red wigs!), crappy low-heeled mules from
Payless (ah, to be 17 and only a size 12W shoe again), and I put on a pair
of black panties, a black 40D bra I bought from a local discount store,
coffee pantyhose and a knee-length brown dress from mom. I put on my wig,
mules and lipstick, and I paced around the house waiting for my first
lover.

He came in the back door (not in THAT way, you naughty reader!) and met me
in the living room. He kissed me on the cheek, and an electric pulse ran
through my body.  That little peck on the cheek felt wonderful. It meant he
thought I was cute, and that he was happy to be with me as Rebecca. I led
him to my room, and we sat on my bed and watched TV - I had The Kids in the
Hall on Comedy Central, yet some more crossdressing in my life. I was so
nervous - not only had I never done anything for real with a man, I hadn't
done anything with ANYONE! I was a total virgin, never even had so much as
kissed a girl, and here I was dressed as one waiting to be kissed by a man
I had only ever known online. After catching him look at me a couple of
times out of the corner of my eye, the moment came. I turned to look at him
just as he happened to turn to look at me, and he leaned in and planted his
masculine lips onto mine, and I absolutely melted. I WAS Becky! I was being
kissed by my handsome lover, and I couldn't have been happier. I
immediately wrapped my arms around him and received his kisses. After a few
minutes, he slipped his tongue into my mouth, and I was in heaven! I felt
like such a girl. All those years of pretending were just mental practice
for when the real time came, and here it was.

We sat on my bed and kissed for a good 15 minutes. We ran our hands over
each other's bodies. His hands found my legs, and he started to rub them up
and down. My hands did the same on his legs over his jeans, and I reached
slowly up his thighs until I got to his crotch. I could feel his bulge
straining his jeans, and I truly felt desired for the first time in my
life. I felt so proud of myself that I was this man's object of lust, and I
let him know that I was glad by rubbing his bulge through his jeans. He
grunted in approval as we kept kissing, and then he broke our kiss to ask
me the question I both dreaded and anticipated, "Would you like to suck my
cock?" Before I could even formulate a thought or an answer, I was almost
automatically sliding off the bed and onto my knees kneeling in front of
him. He leaned forward and we kissed some more, as I unbuttoned and
unzipped his pants. I couldn't believe I was about to live out one of the
scenes I frequently cybered about. I was afraid about gagging or choking on
his cock, but once I got his pants off I saw that he wasn't all too big,
maybe 5" or so. Perfect for sucking! I tried to remember all the erotic
stories I had read online, and all the cyber scenes I had done since I was
13, and I tried to give him the best blowjob anyone could ever give - and I
succeeded! He held my head, he moaned, he loved what I was doing! I was so
happy to be feminine, giving pleasure to my man. I loved every second of
being on my knees, bobbing up and down on his perfectly suckable penis. I
rubbed his balls as I sucked him slowly, I reached up to play with his
nipples, and I made sure to look up often to see the look of pleasure on
his face. When I felt his testicles tense up and get ready to release my
reward, I was not worried at all. I had tasted my own cum before, so I knew
what to expect, and I eagerly received every drop into my mouth.

The moment the last drop of delicious sperm hit my tongue was the moment
Rebecca was officially born and Richard died. I was so proud to have
pleased a man. I felt so feminine, and so desired. I even thought to
myself, "I'm the happiest girl in the world right now! I just made a man
cum, and he loved it!" He told me I did a great job, and that he'd see me
again. He kissed me on the cheek once more before leaving, and I watched
him drive away from the kitchen window - still dressed as Rebecca. I didn't
care if any neighbors saw me; it's who I was now. I stayed dressed up for
the rest of the day until my dad came home from work. He never knew about
the guest I had that day, nor did he or anyone else ever find out about the
other guests I've had over the years, but those stories are for another
time.