Date: Sun, 17 Jun 2007 11:30:02 -0700
From: Clint Dear <clint@dogomania.com>
Subject: Girly boy meets his perfect lover

When I was a young boy I loved to dress up in my mother's
clothes. My little boner would rise with anticipation as I
would search for treasure in her hamper. Once, when I was
home alone from school I added makeup to my play. I had
panties and a bra, a girdle, and a copy of Cosmopolitan to
guide me. I sat at my mother's make up table and began to
learn about myself. I experimented by copying as best I
could the make up on the models in the magazine. When I was
done I realized that for the first time in my life, I had
made a decision as to who I wanted to be.
One day as a teenager, as I wandered around the house in my
feminine persona dressed in mother's baby doll and satin
robe, I noticed as I walked by my brother's room I would get
turned on. My face would flush and my nipples would rise and
become tender as my little penis would stiffen. There was
definitely something dark, foreboding, and sexual about that
room that made me feel aroused. As my curiosity led me
inside, I was greeted with mysterious odors of masculinity
so unlike my own - mixtures of sweat, testosterone, and
sperm. I felt an unmistakable vulnerability to masculine
power, and yet it drew me closer, calming me with sexual
purpose. I truly felt like a little girl in a big man's
world. As I stood there soaking in the vibrations of power
and sexuality left behind by this mature male, I picked up
my brother's sweaty tee shirt and brought it to my face. My
heart beat faster as I closed my eyes and deeply inhaled his
scent. I felt warm and calm as a rush of sexual arousal
spread throughout my body making me starkly aware how much I
craved the sexual attention of a man. Intrigued, I found
some more treasures to experience until finally I found his
underwear and brought the musk of his ball sack to my face
and inhaled. I immediately surrendered to this new awakening
and began to rub my stiff little penis as I explored the
wonderful sensations in my nipples. My senses were alive as
my inner girl began to reveal her true power over me, as I
closed my eyes and imagined being chosen by a powerful man
to be his mate as I reached a powerful climax.
As I got older and moved out on my own, I gravitated from
crowd to crowd. Being a young and single 20 something
presented me with lots of room to explore. I went to one
pretty tame party where same sex attachments weren't totally
off limits, so I found myself able to relax and to begin
checking out the boys. There were a couple of obviously gay
guys who I thought might try to hit on me so I made a point
to be chatty and friendly with them, hoping they would sense
I was available. I was flattered at the attention and tried
to return it, but they just didn't pursue me even though I
warmed to their hello and goodbye hugs, and looked forward
to the occasional sneaky kiss on my neck, as if they were
teasing my growing hardness. I'd hold their embrace hoping
to generate some interest but they'd always just let go. I
wanted their companionship, to be one of them except they
didn't seem to be interested in me even though I made my
yearning for them painfully obvious. I felt defeated and
decided it was time to get creative if I was ever going to
have a boyfriend.
When I prepared for the next party I decided I would
experiment and try some mascara to make my eyelashes longer
and prettier. I liked the way it turned out so I added a
little light gray highlighting above my eyes, and a bit of
rouge on my cheeks. It would be pretty much invisible unless
you were very close to me. I was alone and unattached. I
wanted to feel sexy and I didn't see anything wrong with
wrong with that. I wasn't very masculine anyway at 5'7" 120
pounds. My face was naturally very pale and feminine and I
wanted to accentuate my pretty face with a little accent
here and there. I was blessed with delicate features and
more hips and chest than many girls my age, and the rosy
cheeks and the long eyelashes I created helped me decide
that maybe I should just be myself and forget the roles and
labels.
Intrigued with my appearance, I decided to spend some time
grooming my feet. I started by shaping my toenails and
removing any hair and calluses, and worked the cuticles to
increase their attractiveness. I smoothed and polished my
toenails until they glistened. Next, I added a subtle pink
polish and whitened the ends of my toenails to give myself
the best French manicure I could.
So as to show off my toes in a quietly sexy way, I put on my
low-rider bell-bottoms without underwear for a smooth
appearance, and the extra length allowed my cute little
piggies to peek out from under my cuffs. I finished them off
with a toe ring for each foot. I could not resist the
temptation to slip into a pair of girl's sandals I got in
the young women's department at Walmart. My pretty feet
deserved that.
I put on a thin white top that was snug enough to show my
boy-boobs if I let my thin jacket fall open for the right
guy. Looking in the mirror I could see my areolas and
nipples quite easily with a hint of a bust line. I combed my
longish hair back into a ponytail and captured it with a
pink scrunchie.
I walked the short distance to the party, getting used to
the new me. The "me" that had decided it was time to find a
boyfriend and see if that was what I was lacking in life.
All they way I was wondering, exactly what do boys and boys
do together? I'd love to hold hands and kiss a handsome boy.
I arrived at the party, and chipped in my ten bucks and
bought myself a wine cooler and decided to try to stay calm
and get used to the action and most of all get used to being
"me".
As the music played my instincts took over as I moved my
hips to the music in a distinctively feminine sway as I
absently checked out the guys. I noticed many of the couples
were of the same sex, which helped put me at ease. It wasn't
long before several guys were hovering around me trying to
catch my gaze. I accepted quite a few dances from quite a
few handsome boys, all showing their appreciation by not
stepping on my toes while they rewarded me with jabs of
hardness to show their interest. I was shocked and
embarrassed at the shamelessness of some of these boys, yet
they made me feel so small and powerless. I had never felt
so desirable in my life! Yet, I felt powerful knowing I had
affected boys this way. They wanted me and it showed. As
they advertised their desire, they suckled my earlobes and
breathed with hot shallow gasps. I could feel my resistance
fading as I absorbed the pheromones of the males I had
aroused and I found myself pressing back against their
hardness, inviting their stimulation, knowing this was the
night I had been waiting for. I decided it was time to find
a mate out of all these restless suitors competing with one
another to make me surrender and become theirs to love.
I made eye contact with a particularly cute guy. He was a
big, tall, twenty something guy and he smiled back at me and
winked as I beamed and returned his smile. It was still a
little scary to be looked at sexually by another guy, but I
was getting my courage up, and I really hoped he would come
talk to me. I was imagining just how happy I would be if I
could land a hunk like him for a boyfriend.
As I was daydreaming watching all of the couples dancing and
having fun, the cute boy who winked at me came up and sort
of loitered near me. He was at least 6'4", well built, and
seriously manly at the age of 20 something! He was making me
a little apprehensive as I realized he was drifting toward
me. I felt my heart beating more rapidly as I sensed him
closing in. Thinking to myself, I wondered if this was such
a good idea, until I realized it was too late and I have
done what I hoped to do: I had attracted the sexual interest
of a man. Since I'd had seen him around before and he always
met me with a friendly simile, I felt fairly safe and I
quickly decided to follow my instincts as he slyly moved
into my space.
"Hi there. What do you think of the party?" He asked.
"So far, it's been fun watching the people. How is it going
for you?" I replied.
"Boring. I haven't seen anyone I know or am interested in
knowing."
"What's that supposed to mean?" I quizzed.
"I didn't mean you. I'm sorry. I've seen you around and
wanted to get to know you and see if you'd like to hang out.
I'm Kenny, buy the way."
"Ok, I'm fine with that. Pleased to meet you, I'm Carl." I
replied as we shook hands. I kept my handshake weak and soft
and he held my hand longer than a simple handshake. We were
practically holding hands when he startled me by putting his
arm around my shoulders and moved me away from the action.
"I feel like a little kid next to you! You didn't think I
was a girl did you? It's happened before, I'm ashamed to
say." I teased as I looked up into his eyes.
"No, if I thought you were a girl I wouldn't have hugged
you." Kenny said.
I smiled sweetly and replied, "Tell me more!" I cooed.
"Can I hug you again?" He asked? Before I could answer, he
pulls me to him and holds me against him. I though he was
going to try to kiss me, and I lifted my face to accept! But
instead, he zips me up in his jacket with my face just below
his chin! I was freaking out inside as my heart raced as I
realized I was zipped up inside a man's jacket with him in
it! I didn't know what to do with my arms, so playing my
role as his captive, I relaxed and decided to play along and
wrapped my arms around his muscular torso. Then I began to
get hard. Real hard, thinking uh oh, he's going to feel it
and kill me!
"Now isn't that nice and cozy?" He asked?
I didn't know what to say but it was definitely warm and
cozy, as well as musky and manly, and I could feel my gentle
giant getting a hard on against my stomach. Here I am
trapped and squeezed to his body and he is happy I'm a guy.
Is this how it happens?
Kenny put his arms around me and maneuvered me into a
corner. Then he squeezed me to him and asked, "Do we have
something in common, sweetheart?" As scary images flooded
into my mind about men and their sexual arousal, I realized
something was different here. I actually liked being touched
by Kenny this way, and we were both turned on as he pressed
his hardness against me. It was scary to feel him poking
into me with no shame, but I wouldn't have run away if I had
the choice. My stomach was full of butterflies and my heart
was racing, but I knew this was special. He made no effort
to hide his arousal as he pressed it against my stomach, and
arrogantly leaned into my lips with just a peck at first to
see if I was receptive. I closed my eyes and tilted my head
to let his tongue glide into my mouth as I shivered with
anticipation as I received my first kiss as Kenny slid his
warm hands inside the back of my pants to caress my butt
cheeks. I was steaming with lust!
"Would you like to go somewhere quieter and meet someone
with me?" He asked as he slowly unzipped his jacket to free
me.
"Yes, I think I'd like that." I replied with a grin. I was
smiling inwardly at the world's oldest pickup line until it
dawned on me that I just agreed to be "picked up" as Kenny
made a cell phone call. I was wondering what was going on,
but whatever it was he was smiling as he was talking, so I
didn't think I was being measured for cement boots.
So we eased ourselves out of the party to Kenny's
motorcycle, and he told me to "hop on". I didn't know what
to do since I'd never been on one before.
"Put your arms around my waist so you don't fall off and
lean against my back so I know you are still there. You need
to lean with me as if we are one person. There. Squeeze
tighter, and put your hands under my jacket to keep the wind
from going up your sleeves making you cold."
I did as he asked thinking, is this really necessary? Is
this some "guy" trick? But then I realized maybe this is how
boys flirt with boys who they have just kissed. I struggled
with the ins and outs of why Kenny is interested in me and
why I actually let him kiss me. I was having second thoughts
as to why I left alone with him as we roared off on his
motorcycle. I was trembling with fear and holding on for
dear life with my cheek planted tightly on his back as I
ruminated on just what sex with a man would entail and how I
would act when faced with the reality of actually doing it.
He must have thought I was crying but I was laughing about a
tee shirt I saw once that said: "If You Can Read This, The
Bitch Fell Off!"
We're almost there! Hang in there." Kenny said as I giggled
to myself for cracking a funny. He reached under his jacket
and gently covered my hand with his to reassure me of my
safety. Bravely, I opened my legs wider and pressed myself
closer to him as I held on tighter and smiled warmly to
myself as I realized my hands were resting on his denim-
covered penis. I wondered if he could feel my hardness
pressing against him, but I was beyond caring. I decided He
was boyfriend material and I had to see where this led.
We pulled up to a nightclub and disentangled ourselves from
the motorcycle and Kenny led me into the club, opening the
door for me like a boy on a date and guided me in with his
hand on my lower back letting his fingers gently glide down
cupping my ass before he removed his hand. Finally we found
a table and sat down and a tall, strong looking girl came up
and sat down next to Kenny like she was a girlfriend or
something. Oh oh, I'm thinking.
"Hi baby!" She gave Kenny a little hug and I began to feel
the blood rush to my cheeks.
"Hi Mary! meet Carl. We met at a party across town. Excuse
me while I get us some drinks."
Thanks for abandoning me Kenny dear. Shit. What am I suppose
to say?
"Hi there. I'm Kenny's sister. How are you and Kenny getting
along?" she asked, smiling.
I blushed red as a radish. "Fine. He seems like a real nice
guy."
Staring right into my eyes, she says, "Yes he is. And you
are the first boy I have ever seen him with. He doesn't seem
to like girls, but I do think he likes girlie boys!"
Oh great. My heart is in my throat with cold fear. "I can't
help it if I'm smaller than most guys. I mean I'm really not
that way." I squeaked.
"Really? Kenny called me before you two came. I know he
likes you and I know why." She said smugly.
I gulped, "Why?" I asked stupidly.
"Because he is gay, but doesn't like men. It took a long
time for us to figure it out let alone for him to find a
nice person to even hope to begin a friendship with. He
called me because he trusts me, and he's excited to have me
meet you."
My eyes were as big as saucers.
"Tell me about yourself, my dear." She reassuringly put her
hand on mine and looked deeply into my eyes.
I began with the usual stuff and Mary held up her hand and
said, "Stop!"
I stopped mid sentence, mouth agape.
"Carl, are you gay?"
There it was in plain view.
"I don't know."
"I think I see makeup, am I correct? Answer me."
"Yes, Ma'am."
"How long have you wanted to be a girl, so to speak?"
"Ever since I can remember, but recently I've decided I want
to meet someone and find out what it's like to have a
boyfriend. I don't feel any sense of equality around men.
They are strangely different from me yet this difference
seems to create a sexual attraction in me. So I decided to
listen to my inner feelings and see what would happen, and
that's why I tried some make up. I decided to see if I have
what it takes to attract a guy. So, when life gives you
lemons you make lemonade!
I felt like I was being tortured like a mouse by a cat, and
yet somehow I trusted my torturer to lead me in the right
direction. I bared my soul to Mary. I felt we were in sync
and she understood. Mary put her arm around me, and pulled
me to her and whispered, "That's ok, sweetie, I think you're
a wonderful person and will make my brother a great
sweetheart. He wants you to be his girl in his relationship.
I think if you can just be yourself, you two will get along
fine, and I'll be happy for you!"
I guess she saw the relief in my eyes that the inquisition
was over. She leaned back into me and asked me, "Honey,
would you like me to touch up your make-up? Just a little
pinch would be cute. I'll bet Kenny would love it! You have
wonderful features. I'll bet your mother was beautiful!"
Not daring to say no to this woman, and at the same time
realizing I may have reached a place I've always wanted to
go with someone I trusted, I agreed.
Mary took me into a unisex bathroom and locked the door. She
brushed my longish hair out and styled it a little. She put
some rouge on my lips and covered it with shimmery pink lip-
gloss. It looked and felt great, but wasn't thick like
lipstick. She used some more rouge on my cheeks to brighten
them up a little, and put the slightest light gray on my
eyelids. Next she took a tissue and gently brushed the
powders until they were nearly invisible, mere hints and
highlights. She opened the top two buttons of my shirt, and
pulled out the tails I had tucked in and tied them in a
knot, to show off my midriff. Then she pulled my low riders
down even lower, almost to where my downy pubes were
showing. I learned to trust Mary. She had no plans to make a
fool of me. She stood behind me as I looked in the mirror,
and caught the radiant smile on my face as I saw her
handiwork. She smiled with me and said, "How long have you
been a girl?" as she dabbed a tiny bit of perfume on my neck
and gently kissed me on the top of my head.
I smiled a wide smile and replied, "When I met Kenny!"
Finally Kenny disengaged himself from his buddies and came
back over.
"Hi Princess, how are you and sis getting along?" as he slid
into the booth and put his arm around me. He brought me a
rum and Coke, and Mary a Coke.
"Just fine." I replied as we both smiled.
"I can tell. You look ravishing Carl. Can I call you Carla?"
he asked.
Oh boy. Why do I have to make all of these decisions right
now, I wondered?
"No, I think I'd like you to call me Cherie." I replied. I
had no more fight left in me.
"Cool. Will you dance with me?" Kenny replied as he pulled
me up by my hand.
We danced a nice slow dance like lovers should. He held
himself against me as I put my arms around his neck and
again I could feel him hardening against me again. I was
pleasantly surprised to have such power over such a big guy,
as I rested my head against his chest ass his hands caressed
the sensitive flesh of my back. As the song ended he turned
me so his back was to Mary, and ran his hands gently down
inside my pants and caressed my ass cheeks and kissed me
gently as I stood on my tip toes to get as much of him as I
could.
"Will you come home with me? I promise I won't attack you.
You can sleep on the couch if you'd like. It would be
wonderful to have breakfast together."
We returned to our booth and Kenny told Mary we were going
to get going. Mary sweetly smiled at me and responded, "I
think she should come home with me. You kids have had enough
fun for one evening. Besides, we are still getting to know
each other. Come over in the afternoon after work, ok
Kenny?"
"Ok, Mary. I'll see you tomorrow. Bye Cherie. I'll see you
tomorrow, too." Kenny replied a little dejectedly as he
leaned in for a peck on the lips, and Mary sat by and
studied me as Kenny headed out the door, and we headed for
her car.
"Cherie, would you mind if we made you up into a really
pretty girl tomorrow? I think it would be fun, and we can
hang by the pool and talk about girl things. What do you
say?"
"Yes ma'am." I spoke as if I was a child or something.
We arrive at Mary's house, and she points me into a bedroom
and says "Good night, sweetie. I'll see you in the morning"
Morning arrived and I lay in bed and began to wonder if I
was doing the right thing. It seemed that Mary was
definitely in charge. I wondered why Kenny didn't argue with
her, but then I realized that maybe she was trying to
protect me. I still hadn't come to terms with the idea of
having sex. I wanted to on an emotional level - it was all I
could think about, but I was drawing a blank on the physical
part. In short, I didn't know what to do or what to expect.
I decided to get up and face my new world and see where it
took me.
Mary was sitting at the kitchen table with a cup of coffee,
and gave me a bright smile. "Come sit down with me and have
a cup of coffee." as she took our cups into the living room
and put them both on the coffee table next to the couch.
"Cherie is a really pretty name. Where did it come from?"
She asked.
"I thought it up one time when I was dressed up listening to
music and reading."
"How were you dressed?" she asked. I was getting nervous
again.
"Come on, you can tell me. I'm like your big sister. I want
to help you be Kenny's girl. That is what you want, isn't
it?"
"Yes, it is." Surrendering again, I replied, "I was wearing
a gray nightie with seamed black stockings. I had on some
mascara and some lipstick, and some blush on my cheeks.
That's how I noticed how pretty my eyes looked with longer
lashes. I decided to polish my toenails and the color I
chose was cherry and that led me to think of myself as
Cherie. "
"Would you like to try some new things today, honey?"
"What about Kenny?" I asked.
"He'll be home this afternoon. I'll bet he'll go wild if I
can make you pretty for him! How about it?"
"Ok, I'll try it. It sounds exciting!"
"First off, you have to understand that to be a girl you
need to look and act like one. And for me to help you, you
need to let me see your body. Take off your clothes."
I hesitated.
"Come on, sweetie. I wasn't born yesterday. Strip. I want to
look at you."
"Yes, ma'am."
Too soon I was standing before Mary naked as a jaybird, but
thankfully my penis was oblivious to her presence.
"My, what a cute little body you have. Have you ever seen a
girl naked?"
"No, not really." I answered.
"Well first of all, you are very lucky. You have a nice
developing chest, probably an easy "A" cup, maybe even close
to a "B", and your nipples are nice and puffy and much
larger than boys. Your nipples are wonderfully full like a
woman's should be and your areolas are a good inch and a
half across. That's really special, did you know that?"
"I always thought my boobies were a little big for a boy,
but then I've always just accepted it as me."
"Well, first lets get all of the hair off of you. Go into
the bathroom and start the shower."
Mary returned with a bottle of odd smelling goo. She put it
all over my body, my legs, between my legs by butt crack,
under my arms, everywhere. It felt tingly as it did it's
work.
"OK, get in the shower and wash it off an be sure to shampoo
your hair and use conditioner."
When I got out, Mary dried me off and rubbed wonderful
smelling lotion all over my body. I was in heaven with the
unique sensation of no body hair. Then she gently pinched
one of my very erect nipples.
"Oh!" I cried. "Be careful, they are really tender!"
"Lucky you! Nipples are a valuable erogenous zone, and you
are very lucky to have nice ones that respond properly.
Here, let me try something." Mary said, as she gently rubbed
the tops of my nipples with her fingertips. My little penis
began to rise as a wonderful sensation began to course
through my body.
"Cherie, you are truly a special young lady! When you are
making out with a man, he's going to want to rub them and
suck on them as if he's a baby, did you know that?" She said
as she looked into my eyes.
"No, I hadn't really thought about that!" I said, biting my
lip with worry.
"And he is going to want to rub your leg, as he tries to get
you aroused. You can really turn him on by letting him feel
your bare flesh. When he holds you tightly, you should try
to get your shirt and his to ride up without him knowing so
he will feel your bare skin against his. That's why you want
to wear shorts and a blouse with a bare midriff. You can
feel nearly naked with him and still protect your self."
"Protect yourself?" I gulped.
"Yes. He is going to want to have sex with you, silly.
That's what men do. It's your job to decide if you want to.
It's not something you have to do, it's something you only
do when you know you are in a relationship and your guy
actually loves you." Mary smiled.
I blushed red as a beet, "How will I know he loves me?" I
stammered.
"You can't always be sure. You just follow your instincts.
There may come a point where you are so turned on you can't
stop yourself and you give yourself to him. But you only
want to do that if you are sure he wants to stay with you
and won't try to find other girls. There are options. But
never, ever allow yourself to have empty relationships."
"Options?"
"Yes. You can give him a hand job, and as long as you have
your clothes on, you are pretty much in charge. Later on, if
you feel for him enough, you can maybe give him a blowjob as
long as it is your idea and not his. When you are finally
committed as a couple, you may decide to let him into your
pussy. "
"My pussy?"
"You know what I'm talking about. Men want you to carry
their seed, and they are less likely to stray if you remain
available to them whenever they feel the need, which will be
frequently. And always keep their sperm in you; don't let
him see you let it out. It shows lack of respect for him
choosing you as his mate. By climaxing in you he gave you a
part of himself for you to nurture. You need to be grateful
you are carrying it. Understand?"
Blushing I answered "Yes. I think I'd like that someday."
"Have you ever done that?"
"Mary, I have never done anything. Kenny was even my first
kiss!"
"You're a sweetheart." She said as she gave me a hug and a
kiss on the cheek.
"Well, lets do your face and try on some things shall we?"
Mary sat me at her makeup table and applied some mascara to
my lashes, and some eyeliner. Next she applied some blush to
my cheeks then applied some pink lipstick to my lips
followed by shimmery lip-gloss. Next she got a little table
and went to work on my nails. She removed my old polish and
re-did my nails again with a richer shade of pink that I
used before. She used a little guide to give me a genuine
French manicure. My hands looked long and sleek, and truly
feminine.
I melted into her touch as she combed my hair and got her
curling iron and curled it. Next she combed the front down
and got her clippers and created some bangs. Then she got
some tweezers and shaped my eyebrows just a little, and
lightly darkened them with an eyebrow pencil. Finally, she
finished me off with a dab of perfume. Looking in the
mirror, I was shocked to see a pretty girl staring back at
me.
"Ok, sweetie. Let's get you dressed." Mary showed me some
pale blue panties that were high cut on the sides, with
little bows and then kneeled down and told me to step into
them. Like a little girl, I put my hands on her shoulders as
I stepped into them as she moved them up my legs. Next I
stepped into a pair of thin white short shorts and she
pulled them up over my hips. Luckily, I had true hips and a
fleshy butt like a girl so they fit really nicely. What used
to embarrass me I now realized was a part of my girlish
self, and a prideful part of my body. Like my boobs, my
feminine features were always there and I never appreciated
them. Next she had me raise my arms and slipped a thin,
loose white half top over me that came down to about the top
my stomach, just below my boobs. I felt a thrill feeling the
breezy fabric on my skin.
"Now wiggle yourself a little, honey. That's it. Now gently
bounce up and down for me. Oh, sweetie, you have bounce in
your boobies did you know that?"
"Yes, but I never thought much about it. I just figured I
was just chubby there."
"Oh my! That top is perfect. It's a bit see though, and I
can see your nipples poking out. If you only knew how lucky
you are! How are you feeling so far, Cherie?"
"I feel really good. In fact I feel like I've found myself.
I think I have been living in the wrong world. My heart is
beating a mile a minute and I feel sexy!" I exclaimed.
Mary smiled at me. "Now you need to learn how to `show a
peek' as we girls say. Colored panties with white shorts are
nice when you want to tease your guy. You want him see your
panties, and you want him to notice your nipples. Guys are
very visual creatures. You need to show them little things
here and there to keep them interested so they don't go
drifting off. You have to keep reminding them you are sexual
and available. And even if you aren't available, you are
definitely sexual. You want him to want you and no one
else."
"It's complicated, but men are insecure creatures. Sometimes
they are afraid to make the first move. You have something
they want and you have to show them you might be interested
in letting them have it. They need to feel they are in
control, but in reality you control the pace by accepting
their attention bit by bit. It's a give and take. He flirts,
and you warm to him a little more each time, as you two get
used to each other. Give him a gentile touch, casually
whenever you can. It won't be long until he is panting with
lust. You just need to play dumb and pretend nothing is
wrong and enjoy the attention, knowing he is checking you
out every chance he gets. When you are sitting across from
him, open your legs a little so he can peek up your pant
leg. Do not try to catch him looking. You can be sure he is
looking. Just provide him little peeks to keep his mind on
you. Now that loose top you are wearing? When you bend over
to let him admire your pretty butt, you can give him a
glimpse up your blouse from the back so he can see your
titties. That will keep his mind on business. Just act the
part of the innocent little schoolgirl who would never dream
anyone would look at her cute little butt, let alone peek up
her blouse in a moment of carelessness. The shamefulness of
men!" Mary exclaimed as we both giggled conspiratorially.
"Every now and then sneak a peek at his crotch to see how
you are doing. If he is getting hard, you need to decide to
pull back or keep going. You will get turned on turning him
on, trust me. Cherie, you are gorgeous and hot! You are
going to have a tough time keeping Kenny off you!" She
exclaimed.
"Should I?"
"Should you what?"
"You know. If Kenny wants to kiss me some more and gets all
heated up and tries to do things with me. I mean I liked it
a lot when he kissed me and I like the way he keeps touching
me. It was as if he was afraid I'd leave if he let go. But
from the beginning he was turning me on in a way I've never
felt before."
"Well, you are going to have some decisions to make then,
won't you honey. Remember, you can be in charge, or you can
let it go. It's up to you to follow your heart. Now lets see
your sexy walk. I want you to work on keeping your hands and
arms loose, and move gracefully and more slowly than a guy
moves. She took me by the shoulders, and said, "Do this. I
want you to bend your right knee, and at the same time,
thrust your left hip out. Then bend the left knee, thrust
the right hip. Practice with me standing still. You have to
leave your inner male behind to let your real girl shine
through. Men walk to get someplace. You walk to be seen and
appreciated by Kenny. There is no other way but to think and
act like a woman, keeping in mind that your are a sexual
creature and you want him to be sexually attracted to you.
In fact, my senses tell me you are kidding yourself if you
think you are boy. You aren't. You are a girl who was raised
wrong. Accept it and be it. You are as feminine as any girl
I have ever met. You just need to let it come to the
surface. I never had a chance to be as pretty and sexy as
you. You are truly gifted." Mary said looking deeply into my
eyes.
"Yes ma'am." I replied smiling as I practiced my walk around
the room.
"That's good sweetie, but don't exaggerate too much. You'll
look like a hooker! Move slowly so you don't outrun your
man's eyes! You can be sure he will have sex on his mind as
you walk with a sway to your hips. " She said as be both
giggled.
I was really getting into this now. My new walk was fluid
and graceful. My hips were cooperating since I learned my
new movement was more natural for me. I was walking all
around the house practicing everything she taught me. I felt
I was learning things I had already known but had forgotten.
For the first time in my life I was feeling graceful and
feminine and at peace with my self.
I was wondering around the house getting used to my new self
when Mary announced "Kenny's home!" as I hear the growl of
the garage door opening.
I hurried into the kitchen find something to be doing when
he entered. I was washing glasses when he came in the door
and announced teasingly "Who's this?" I turned around with a
blushing smile as he took me into his arms and gave me a
wonderful hug and a kiss on the neck. My arms could barely
reach his shoulders when he leaned in for a kiss and stroked
my bottom.
"I like what I see honey." Kenny said as I closed my eyes as
our lips touched. I inhaled his manliness as I hugged his
chest tightly, my heart fluttering.
"Thank you baby" I replied.
"Kenny, we were just going out to the pool. Why don't you
come on out and join us?" Mary announced and told me to
bring him a soda also.
Kenney came outside and found a seat. I brought Mary her
drink first and leaned over carefully to set it on the low
table. I felt the excitement knowing I was being watched as
I leaned to give Kenny his drink as the napkin skittered to
the floor. Leaning down to pick it up I left nothing to
Kenny's imagination as to what I had under my blouse. I felt
warm and flushed as I glanced down at Kenny's growing bulge
and realized that for the first time in my life I was
playing for keeps.
"Oh, Cherie honey, we forgot to polish our toenails. I'll be
right back out with some colors." Mary announced as Kenny
and I made eye contact again and I smiled sweetly.
Mary returned with red for herself and pink for me with her
clever little nail polish guide to continue with my French
pedicure. "I hope you don't mind if we do this in front of
you Kenny. Do you want us to go inside?"
"No, no you're fine. I'm going to go in and put on my
swimming suit." Kenny replied.
Kenny come out in his trunks and sunglasses, and laid back
in the lounger while I begin to paint my toenails. I was
able to give little peeks here and there; I know he
appreciated me being hard and unable to completely hide my
erection. Kenney's sunglasses were a nice touch. At least he
could pretend not to be looking. But I knew differently as
my heart raced in my chest. He knows and appreciates that
I'm doing my best to be his dream girl, just for him.
As I was lying back letting my polish dry, Mary announced,
"Well, I think we're dry enough. She we put on our suits,
Cherie?" She said as she stood and led me into the bedroom.
She picked out a pale lime green two-piece for me. The
bottom had string ties on the sides showing at lease three
inches of each hip where the ties were, leaving me
practically naked. But Mary thoughtfully had cut a slit in
the liner to provide a little pouch to keep my penis from
slipping out. The top had a loop that went behind my head
and a tie in the back with a clasp in the front, which
exposed nearly three inches between by boobies. I felt I was
hiding very little as Mary smiled at me.
Then to my shock, Mary took off her clothes without even
turning her back as she put on her suit. That was proof
positive she saw no maleness in me, at all. I felt empowered
like never before.
As we went back out to the pool area to work on our tans,
Kenny was laying back on his lounger. Feeling clever, I laid
face down where I might sneak a peek for myself. It wasn't
long before I was rewarded with a glimpse of his semi-
flaccid cock sneaking down the leg of his swimming trunks. I
suspected he was pretty large since I have had it poking
into my stomach since we met, but I really had no idea just
how large he was until this moment. He was as big around as
a silver dollar! I was shocked and suddenly terrified at
what I had gotten myself into. I closed my eyes and forced
myself to understand the impact of what Mary meant by
"That's what men do." In a moment of clarity I finally put
all of the pieces of my life together: I entered this
relationship with the intention of being Kenny's partner,
and I was not going to let myself down now. He was just so
big, it scared me to death thinking I might have to find a
way to get my mouth around it when the time came to become
"me".
"Honey, would you like me to rub some lotion on your back?"
Kenny asked, snapping me out of my trance.
"Oh, please. I think I'm starting to burn" I replied.
Mary said "I'm staring to burn too, but I'm going in to take
a shower and meet up with Jill. She offered to take me to a
concert tonight. You two behave yourselves. I'll be home
around two am or so, unless I get lucky!" She said with a
sly smile.
I was shocked. I didn't expect her to leave while Kenny and
I were here alone.
Kenny sat down and slowly rubbed the cool gel into my smooth
skin as I closed my eyes and considered my situation as the
mechanics of physical love danced through my mind. I felt
decision time had suddenly come much sooner than I expected,
but I was not going to lose this guy over my lack of
courage. I slipped into an erotic daydream as Kenny massaged
in the lotion. He went down my legs and tickled my feet as
he rubbed between my toes and gave my feet gentle kisses as
he massaged each toe one by one. As his hands traveled up my
calves to my upper thighs, his finger tips would sneak under
the leg band of my bottoms to caress a little of my butt
cheeks. I was becoming seriously aroused, unconsciously
lifting my buttocks to meet his hands willing him to go
higher. I hope he appreciated what he was doing to me as I
met each heavenly incursion with a lustful sigh as his
sneaky fingers went deeper under my bottoms. I was panting
with lust when Kenny asked me if it was ok for him to do the
tops of my legs and feet. Nervously, I rolled over on my
back like a trained puppy.
Kenny began at my feet again, and massaged his way up my
legs while spreading them to get a better angle for my
massage. I felt very vulnerable feeling him there with my
legs spread and him sitting between them with his hands
rubbing lotion dangerously close to my penis. The feeling as
he sensuously went up the inside of my thighs completely to
the leg band was causing me to ache with lust. I opened my
eyes to peek at how he was doing and I was embarrassed to
see my little erection making an unmistakable little bulge
for him to see, while the massive tent in his bathing suit
left no doubt what he had planned for me. He lifted my legs
and placed them on top of his thighs as he moved closer to
massage my arms and shoulders. As he moved closer to me, my
legs spread more widely; his covered penis was touching me
all over. I was excited by the contact and wanted more, but
I was afraid of where we could be heading if I didn't regain
control as Kenny leaned in and kissed me again deeply.
"Let's take a dip in the pool, ok baby?" I declared as I
slowly sat up and put my arms around Kenny's neck with my
legs spread over his thighs. It was an awkward way to face
your boyfriend when his cock is ready to bust out of his
trunks! I smiled and leaned in for a kiss and with a smile
and a wink, making sure my groin kept contact with his penis
and asked him sweetly if we could go for a swim.
The water was pretty cold at first and I was conscious of my
nipples showing though my top. I tried to hide them but
Kenny came up and moved my arms and kissed me deeply as he
carried me into a deeper part of the pool. I had no choice
but to wrap my legs around him as we kissed passionately as
I felt his naked skin on mine. I could feel the strength of
his manhood thrusting into my covered crotch as I held him
tightly as he kissed me deeply. I reached down and felt
Kenny's hardness pressing against me through his suit. I
reached inside his trunks and for the first time felt his
naked hardness as Kenny took it as a clue to remove his suit
completely. Further emboldened, he unsnapped the front of my
top and exposed my breasts. Gently he lifted me in the water
and began to suck and lick my nipples as I felt his cock
touching my bare skin. I was breathing heavily now as he
probed for an entry into my suit. Not to be detoured he was
soon running his cock under the fabric between my butt
cheeks dragging himself across my pussy pushing me toward an
untimely orgasm. He was alternatively licking and sucking my
nipples and kissing my neck, ears, and lips as I squirmed in
beautiful agony as his naked cock rubbed across my naked
pussy. I was in sexual overdrive way beyond my experience as
he began to search for the right string to pull to release
the bottom of my bikini. I needed to slow things down and
quick before I climax right then and there.
"I think we need to take a break before I make a mess." I
whispered.
"Oh honey, I'm going crazy." Kenny replied.
Teasingly I responded, "I'll bet you say that to all your
girls! How about we go in my room and I'll rub some lotion
on you?" I asked as I planned to give my first hand job.
"You are my first, last, and only girl. You know I was in
love with you at first sight." Kenny said.
"You're so sweet. Now come lie down with me and maybe we can
calm down if you promise not to try to take advantage of me.
How would that be, honey?" I asked Kenny.
"Great. I'd love it."  He says.
I took off my wet bottoms and dried myself off the rest of
the way, and slipped into a silky purple bathrobe. As I
looked around for some panties and a top to wear, Kenny
comes in wearing a bathrobe and slithers in-between the
covers wearing only a pair of boxers. "Hop in honey, I'll
warm you up. I'll be nice. I just love to feel you against
my body."
Against my better judgment, I slipped off my robe and slid
into the bed next to Kenny wearing only my fresh panties. It
was exciting to feel like a normal person. I felt a
connection to all the women who snuggle in bed with their
men. I relished the warmth and comfort of lying next to a
man I can call my own. I smiled at the sense of security and
safety I felt lying next to Kenny as I snuggled close to him
and put my head on his arm and breathed deeply of his
protective manliness. Kenny always smelled good to me, and
his masculine scent kept me fully aroused. I didn't know why
and I didn't care, but I know I had found love. I pondered
the idea of what it would be like to have an actual
boyfriend. But to keep a boyfriend I have to give back, but
what's in it for me? I asked myself until I realized
everything I've ever wanted is lying next to me: Comfort,
protection, security, passion, and love. All I have to do is
be myself and let it happen.
As I lay there in Kenny's embrace I decided that I wanted to
give Kenny a hand job since he was being such a sweetheart.
I quietly got out of bed and went into Mary's room to fix my
make up and add a tiny touch perfume.
Kenny stirred as I slipped back into bed, naked.
I gently worked myself back into his embrace and put my left
hand on his stomach and slowly worked it down under the
waistband of his underwear. As I touched him, he let out a
cute little moan letting me know he was awake as his
erection began to grow in my hand. He rolled a little more
toward me and felt my nakedness as he rubbed the globes of
my ass cheeks as he thrust into my hand. I felt my nipples
grazing his chest making me more determined than ever to be
the most wonderful girlfriend in Kenny's world. He brought
my lips to his and kissed me deeply as he brought his free
hand up to my breast and gently massaged my nipple and
whispered, "I want to suck your clittie honey.". He said as
he removed his boxers and reversed me around on top of him
as if I was a feather. I was suddenly face to face with my
lovers naked 8" cock. It was as they say, "In proportion" to
the rest of his body - big and thick.
Suddenly I became aware of a warm sensual feeling as he took
my little cock in his mouth and began to suck and work it in
and out as he used his tongue with practiced precision. I
was beside myself with new feelings of passion as I worked
up the courage to officially christen my new sexuality.
Tentatively I kissed the head as Kenny tried to thrust it
deeper into me. I parried his thrust and ran my tongue along
the side and the bottom hearing Kenny moaning encouragement
as I studied the contours of his magnificent cock. As Kenny
was sending me into euphoria as he suckled on my little
cock, I decided it was time. I opened my mouth and received
him. He was too large to do much with at first, but he began
to gently thrust in and out of my mouth allowing me to get
used to sucking his cock. I quickly learned to use my
tongue, and to tighten my lips on the outstroke. Kenny
didn't get greedy and try to push in too far, as he took his
cues from my hands on his ass cheeks as I worked him in and
out as far as I could. Kenny on the other hand was allowing
me to thrust into his mouth with abandon. He reached down
and began again to play with my nipples as I thrust into
him. Feeling my orgasm approaching. I tried to stop but
Kenny wouldn't have any of it. He tightened his lips on my
clitte, and as he more tightly squeezed my nipples and
rolled them in his fingers, I gave in to the most loving
experience of my life and delivered my seed into Kenny's
mouth and eagerly warmed to him driving his cock deeper into
my mouth as naturally as if I had been doing it all my life.
I accepted my role and finally understood my eagerness to
please him. As my cock softened, he sat up a little and
pulled me to him and placed his lips on my pussy as he
delivered my warm juices back into me. As he gave my pussy a
last little kiss I felt something warm and slippery on his
finger as he gently massaged my virgin entrance.
Turning me around he pulled me up so I was lying on top of
him. He pulled me tightly to him and gave me more deep
passionate kisses. I felt his tentative thrusting as he
probed for my pussy. I lost all sense of fear as my natural
femininity commanded my body to do what came naturally. I
instinctively allowed myself to adjust my position to aid
his tentative unsuccessful thrusts. I reached under to guide
him to my entrance to show my willingness to be his partner
in my deflowering. I felt that even if he couldn't get it
in, it was a symbolic beginning.
Suddenly he stopped his thrusting as he found the "soft
spot" and entered me just enough so that I understood his
gentle message that there is no turning back now: I've
consented to be bred. Gently he pushes again and retreats,
and pushes in again and stops as he senses my surrender
letting me savor the feeling of my virginity disappearing as
my pussy begins to slowly yield to Kenny's gentle pressure.
I breathe in a sigh of passion and squeeze more tightly to
him and receive another loving kiss as I feel him squeezing
to expand himself to gently open my pussy. Again, he relaxes
and pushes ever so slightly and expands himself inside me
again, my breath frozen in my lungs as he pulls out and
gently pushes in again as I instinctively rock my hips to
assist.
"Oh honey. You are so big I can't do it!" I moaned
breathlessly.
"We have all day, my love. And all of our lives." Kenny
sweetly replied as he kept up his gentle probing, in a
little, rest a little as he squeezes himself larger, then
out and in a bit more as he deeply kisses me and hold me in
his embrace as I continue to adjust to his girth. I laid my
head on his chest comforted by his manliness as I sought the
courage to continue our first coupling as he kept up his
relentless, but painless entry into my pussy. Each time he
would embrace me and cover my lips with warm kisses, my
defenseless pussy would open up to welcome just a little
more of him until finally I felt a warm glow as he held me
tightly so I could experience the bulbous head pass my
sphincter and tighten around his shaft. Inch by wonderful
inch, in and out as he began to thrust into me, each time a
little deeper. As I kissed his wonderful lips, I found
myself uncontrollably moving down to help him drive every
last inch into me as I rose up on my arms and began to match
his thrusts as he gently twisted my nipples in his
fingertips. I was beside myself with intense pleasure and as
if a dam gave way, I released my come onto Kenny's chest as
he thrust his hips upward and held himself deeply in me as I
experienced his rhythmic pumping as he deposited his DNA
deep within me. Exhausted, I lay back down on his chest as
he held me and kissed me gently as he continued to work
himself in and out of my pussy as he stiffened and delivered
another load of his precious cargo deep within me.
"Oh honey, that was wonderful!" I moaned.
"We're just beginning, my love"
We stayed in bed and took a well-deserved rest for a couple
of hours. I woke up and felt it would be nice to go back to
the pool.
I put on my loose top, and just to be mischievous a short
skirt I saw in Mary's closet. I felt daring, so I put it on
without panties. I didn't want anything between my lover and
me. I had nothing more to hide.
Kenny came out wearing just a towel, and gave me a nice hug
and a kiss. I could feel him under the towel, wondering if
it was going to be my turn to please him. I lay on the
lounger face down and Kenny asked if he could rub lotion on
me again and give me a little more massage. I readily
agreed. As he massaged my legs and feet again, he noticed my
bare bottom.
He didn't need an answer. We were lovers now and we had
given ourselves to each other. I know he loved my butt. He
loved to touch it, kiss it, caress it, and make love to it.
Teasingly he rubbed the backs of my legs and slowly worked
his hands up to my butt cheeks. It felt delicious as he
rubbed them sensually and occasionally dipped a fingertip in
my pussy. I felt no shame as I made no effort to hide my
pussy from my lover's gaze. I felt no terror as I felt the
head of his penis touching my body. I offered no resistance
as he carefully began to mount me again, entering me in
careful probes taking care not to hurt me. As I rose up to
meet him, he pulled me to my knees as he began to thrust
into me holding me with one arm around my stomach, and the
other toying with my nipples. I was squeezing him as he
pulled out and opening myself as he thrust in. I wanted more
of him. I wanted it all as I asked him to let me see his
face as he makes love to me.
He withdraws and lays me on my back while kissing me and
caressing me as if I'll run away. He raises my legs and
pulls my hips to him and probes for my hole. There is no
need for gentleness this time as he pushes into me without
the slightest resistance. He thrusts in and out of my body,
and then slows his pace so we can look into each other's
eyes as we become one. I tighten as he pulls out, loosen as
he pushes in, over and over as the sweat from his body drips
onto me as he works mightily for another climax. I feel him
swelling larger than ever before as he pumps another load of
himself into me. He lies on top of me and slowly softens as
I smile with the glow of a naked baby knowing I have reached
a new plateau in finding the real "me".