The Tomboy Blues
Megan was my next door neighbor, and that was both good and
bad. I watched her grow up, and she was a delightful girl, though until she was
fourteen you could hardly tell she was a girl at all. She was the
quintessential tomboy. She was an only child of parents killed in a car crash,
when she was about six or seven, and it was then she'd come to live with Alice,
next door. Alice was her grandmother and she tried hard to take care of Megan,
but was alone in the world herself. As a result, Megan gravitated toward boy
things because that's where the power and acceptance was. She could hit a
baseball as far or farther than the boys. She could run like the wind and climb
the toughest tree. She was always scraped up, usually covered with dirt, and
just a delightful child.
My own parents had died too, also in a car crash, and I'd
inherited the house when I was in college. After school I was able to start a
home based business, so I moved back into my folk's house. That's why I got to
watch Megan grow up. That was the good part.
But she eventually grew up and changed from a tomboy to a
woman. That was the bad part.
Megan loved to come over to my house when her friends were
busy. After all, I had tools. And I had a garage full of ... well ... stuff. My
Dad had been a packrat, and there were all kinds of things in the garage (and
attic and basement) that I had no idea what were for. Megan would come over and
ask permission to go on a treasure hunt, which I usually let her do. It got to
the point where she rarely knocked any more. She just barged in like she lived
Which was how I got embarrassed. Well, maybe she was the
embarrassed one. I don't know. I had met a woman, and one thing had led to
another. She had come over during her lunch break and we were hotly engaged in
a middle-of-the-day fuck when Megan wandered into the house. Janet, the woman I
had met, wasn't on any birth control, so she asked me not to cum inside her.
She had a thing about being squirted with sperm and loved to rub it all over
her body. Anyway, I was feeling the tingling in my balls that said it was time
to pull out when Megan walked down the hall. My bedroom door was open. When you
live alone, all your doors are open all the time.
Anyway, I think she got a good look at the last couple of
times I boned Janet and I know she was standing there when I pulled my
immensely satisfied prick out of Janet's pussy and began squirting cum all over
her stomach and tits. Janet was yelling and had one hand on her clit while the
other hand was spreading my spunk all over her. I heard a gasp and turned to
see poor Megan staring at us like we were little green people from Mars. She
turned and ran.
I didn't see her for a week or two after that. Small wonder.
Then I needed my Skil saw back - she had borrowed it
- and I went over and knocked. When she came to the door, she couldn't look at
me and was blushing and everything. She was stammering about how sorry she was
and I stopped her.
"Look, Megan," I said. "It was no big deal,
okay? I'm not mad. Janet didn't see you, so no harm done, okay?"
The funny thing was what she said then. "Her
name was Janet?"
Anyway, I didn't think anything about it then, and things
eventually got back to normal between Megan and me. That was the kind of
relationship we had. If there was a bump in the road we hit it, jerked around a
little, and then things smoothed back out.
Of course, being a guy, I noticed as Megan reached the
various milestones of feminine maturity. I noticed when she started wearing
bras. I also noticed when she started leaving them off. She had a special
hiding place for them. I was upstairs in my computer room one day and saw
movement in her back yard. She had come out of the house and was stretching and
pulling at her shirt. She looked back at the house and then went to the garden
shed in their back yard. She pulled her arms inside her shirt, did that magic
thing girls can do to undo a bra, and pulled it out from under her shirt. She
put her arms back out the arm holes, wadded up the bra and stuffed it in a can
in the shed. Then she ran off to play, or do whatever teenage girls do when
they've just ditched their bra. I saw her on another day retrieving the
undergarment and putting it back on before she went in the house. It was
obvious that Grandma was making her wear them and she hated them.
But that's what made me notice her growing little nipples.
Whenever she came over to my house her teenaged breasts were always bare under
her shirts. I knew this at first because of the garden shed. But then I noticed
her nipples sticking out, and after that I had a hard time ignoring them.
Another thing was that there came a time when I noticed she
wasn't wearing her belt. She had this unique belt she'd made it at some camp or
another, and had tooled it herself. It was her pride and joy. She always wore
it, whether it was on her cutoffs, or regular jeans or whatever. She had to
hitch up her pants a lot because they kept trying to slide off her slim hips.
Then one day she was digging through some boxes in the garage and I noticed she
wasn't wearing the belt. It was so odd I even mentioned it.
"Megan, what happened to your belt?"
She stopped digging, stood up and turned just her upper body
around. Her pony tail swung wildly through the air. "I don't need it
anymore," she said simply, and went back to digging. I looked closer and
realized she was right. Her hips had swelled and she had an hour glass figure!
Now she could fasten the waist and it wouldn't slide over those hips.
Well, by the time she was a senior in high school, Megan was
quite a woman. She still competed with boys though, and dressed like one too.
She had a favorite shirt. It was actually one of my favorites too, because it
had all these holes in it. She had worn it for years and had snagged it on
fences, torn it on tree limbs and just flat worn holes in it. It was an
extremely sexy shirt, though she didn't seem to realize that. I loved it
because it was too small and showed lots of skin. Her grandmother had finally
given up trying to make her wear a bra when she was seventeen, and now she
never wore them. So, Megan in her favorite shirt was welcome at my house any
time, whether there was a Janet there or not.
Usually there wasn't. Most of those women were only
interested in my big house and how much money I was making.
Anyway, it was the summer Megan would turn eighteen when I made
the three terrible mistakes.
I was puttering around, trying to make some flowers grow
when I noticed that there was more paint on the ground around my feet than
there was on the sides of the house. It had all flaked off over the years and I
had never thought to do anything about it.
Naturally I thought of Megan. She did all the man things
around my house, or at least anything that involved tools. I went over and
She came to the door in a white T shirt with bright blue gym
shorts on. The shirt was tucked into the shorts and her hair was, as usual,
pulled back in a long pony tail.
"Hey Bob! What's up?" she said brightly.
I didn't say anything, because at that very moment I
realized just how much growing up Megan had done. I could see her dark areolas
through the shirt, because the sun was shining right on her chest. And they
were mounted on a pair of breasts that were a baby's dream. Usually she wore
button down shirts that had been her grandfather's years ago, and they were
always loose and usually checkered - that kind of thing. It occurred to me the
only other thing that clung to her was her favorite shirt, and I hadn't seen
her in that for probably a year.
"Bob? Earth to Bob!" she said, giggling.
I came back to earth and looked up. She was staring right at
me, a smile on her face. It would have been obvious to a blind man what I had
been looking at.
"Oh!" I squeaked. I was starting to blush. "I
was ... uh ... thinking about something."
She giggled again. I blundered on. "No! I mean ... um
... I was thinking about nothing."
With a completely straight face she looked down and
addressed her glorious breasts: "Well, boys, I hate to say it, but he says
Now I was truly flustered. "No!! That's not
right! I mean they're not nothing ..." I stopped to think about what I had
just said. There was no way on earth I was going to come out of this with any
dignity. "I need my house painted!" I growled, and turned around and
She was kind. She gave me half an hour to regain my
composure. And she changed shirts. When she came over she had on an old plaid
shirt with the arms cut off. It was nice and baggy. The only problem was that
the arm holes were for a man, and her slim arms didn't come close to filling up
all that empty space. That left a lot of room for dirty old men to peek
through, trying to see her braless breasts.
I tried to control myself.
We talked about painting the house. She said she'd do it,
but I'd have to help, because otherwise it would take too long. When I
mentioned how much I was willing to pay her, her jaw dropped.
"Bob ... I can't believe it. That's a lot of
I reminded her that I hadn't gotten her a present for her
eighteenth, and how unforgivable that was. Then I said I'd have to pay somebody
to do it, and I'd rather it be her than some stranger.
She was effusive. "Bob! With my savings, that gives me
enough for my first year of college! Oh! I get to go to college!"
She started jumping up and down. That didn't help my
composure, because her braless breasts, though they were quite firm, still
bounced a little. Then she hugged me and those twin beauties pressed into my
Not even Janet had ever affected me like this. Instant
hardon. Thank goodness I was wearing jeans.
She said she wanted to get started right away and that she
was going to go get her painting clothes on. She stood back and looked at me.
"You'll want to change into something you don't care about," she
said. "You can't paint without getting it on you, so whatever you wear is
going to be the color of your house."
I mentioned that I
didn't even have the paint yet. She looked crestfallen and then brightened.
"I'm, going to have to do some scraping and prep on some parts of the
house, so while I'm doing that, you go get the paint.
That worked for me, and by the time I got back it looked
like there was no paint on the house at all any more.
She was on a ladder, scraping around an upstairs window. I stood there, looking
up, and suddenly realized I was looking at Megan's pussy.
She was wearing a different pair of gym shorts. These were
too big for her, like she had gotten them for a gift and couldn't return them
or something. They gaped around her legs a good four inches. And they were
white, which meant they didn't cause shadows. She was blond in all the right
places and wasn't wearing any panties. She also had on her favorite shirt. My
Bam! Instant hardon.
She looked down. "Just in time. I only have this window
to do and we can start painting. Go change. Remember, you'll get paint on you.
It can't be helped." I leaned forward so she couldn't see the evidence of
my dirty old man-hood and hobbled into the house. I was going to have to beat
off before I could go back outside. Wow! I hadn't had to do that for a while.
I went to my closet and found I didn't have any clothes for
painting. I mean I never did anything like that, you know? So I picked a T
shirt and some gym shorts I didn't use for their intended purpose anymore (who
wants to work out anyway?) and stripped down. As my eight incher popped out (I
know, I know. Let a guy dream a little, OK?) I thought about Megan. I started
stroking and smiled as I thought about what I'd seen. It didn't take long
before I was ready to blow. I realized I didn't have anything to catch it in,
and looked at the bed I'd left unmade that morning.
It was time to change the sheets anyway.
So I turned toward it and seconds later I was shooting
streams of cum three feet onto the bed. Wow. She was good for a fantasy.
I wiped it off, wadded up the sheets and threw them in the
laundry basket, got dressed and headed out to be a painter.
It wasn't until I rounded the house and looked back up at Megan
that I realized the "last window" she was doing was the window to my
She was still scraping, but she looked a little stiff. And
if she'd seen me she would have gotten down, right? I figured everything was
okay. "Okay, I'm back. What do I do?"
She looked down and said "Well, first we stir the paint
and then you can start high and I'll start low and we'll meet in the
middle." So she got down and did all these things with the paint. She had
made buckets for us to pour a little paint into, so we didn't have to hold a
whole gallon while we worked. She showed me how to use a brush and all that and
then she sent me up the ladder.
Four hours later we had about a quarter of the house done.
It didn't look all that bad. I looked at my watch. "It's about supper time
Megan. Why don't we take a break? Your grandmother probably has dinner
She kept painting. "Nope. She's gone for the weekend.
Went to visit my Great Aunt Sophie up in Buffalo." She stood up and
stretched her back by bending backward.
Boy howdy, I loved that old shirt of hers.
"Well, then, let's finish this section and knock off
for the day," she said.
I had to move the ladder, but I'd only have three or four
feet to cover, so I'd only have to move it once. I'd just filled my pail, but I
could always pour the unused part back into the can. I climbed up and put the
pail on a wire hook Megan had fashioned to hang on the side of the ladder so I
didn't have to hold the can all the time.
Only I missed the hook.
I realized it about the same time as I let go and lurched to
catch the handle. Instead I hit the rim of the pail with my fingers. I watched
in horror as the pail gracefully turned on its side and a half gallon of white
paint spilled out and became airborne.
Megan was right under me. She heard me yell and looked up,
naturally. She had a split second to see it coming, which is the only reason
the pail didn't hit her square in the face and bounced off her shoulder
But every drop of that half gallon of paint splattered all
over her. Face, hair, chest, the front of her shorts and legs, even her shoes.
She squawked just like a pelican I heard when I was visiting
a friend in Santa Barbara and began using her fingers to pry the paint out of
her closed eyes. I hurried down the ladder, but what could I do?
"Megan?" I said.
She started laughing! "It's okay, Bob, it's latex. It
won't burn. But I need to get it off of me before it soaks in. It's water based
and should all wash out, but we need to hurry." She had me lead her to her
house, at which time we found the door locked. She hadn't brought the key with
her. That was fine, she said, because she knew three or four ways to get into
the house, but not covered in paint.
That's how she ended up in my shower.
I led her back to my house and up the stairs into my
bathroom. I had an oversized shower, so she just got in dressed and turned the
water on. She did her face first, so she could see again and then started
stripping off her clothing. I was standing there with the door open, staring at
"Here," she said, yelling over the sound of the
water. "Take these and get them in the washer right away. That's my
favorite shirt and I don't want it ruined."
It didn't seem to occur to her that she was stripping naked
in front of a man. Well, not at first. At one point she had given me all her
clothing. I had it in this sodden mass, dripping inside the shower and was
still standing, staring at her unclothed beauty.
She turned and saw me.
One hand went to her breasts and the other to cover her
golden pussy hair.
"Bob!" she yelled. I started and my head jerked
up. "Hurry and get those in the washer!" she yelled again. I left,
leaving a trail of milky water all the way to the utility room.
Now I was a mess. The floor was a mess. Megan probably hated
me. My whole life was a mess. I pulled off my own wet clothes and threw them in
the washer with hers.
"Bob?" I heard her yell. " Baaaaaahb!"
I padded back upstairs and stopped at the open bathroom door.
"Yeah?!" I yelled.
"I need help!" she yelled back.
"What's wrong?!" I yelled.
"It's so thick in my hair, and I can't see it. I need
someone to help me wash my hair so it doesn't stay around the roots!" she
I was standing in the doorway, dripping, naked. Great.
"Give me a minute!" I yelled and started to turn around and go find
something for both of us to wear.
She opened the door to the shower and leaned out "Bob I
need your help now or it's going to be too ..." She petered out, no
pun intended, as she saw me standing there naked, covered in diluted white
paint. I must have looked like a ghost.
She laughed! "Come help me," she finally said.
"I need to get something on!" I yelled back.
"And something for you."
"She was still looking at me. "No time. This stuff
comes out, but only if you get right on it. Bring a comb. Besides, all you'll
be looking at is my head, right?"
Yeah, right. What the hell. I went.
She was right. It was matted deep in her hair and it
was a bitch to get out completely. You had to scrub with soap and comb
and scrub some more and comb some more. It took half an hour to get her clean
to the scalp.
And for that entire half hour I was hard as iron.
There wasn't a damn thing I could do about it. It stuck out
and banged into her legs, and her hips, and her buttocks. Once I was standing
right in front of her and she was bending over slightly, so I could see her
scalp. She had to be looking right at my boner, not two feet away. It took
every fiber of self control I had not to rape her right then and there. I even
managed not to rub up against her. I was so proud of myself.
I'd have made it out of there a complete gentleman, except
that when I pronounced she was done she reached her arms around me, molded the
front of her body up against mine and kissed me on the lips. I went into
hyper-sensation. Her breasts were pressing up against my chest. Her pussy was
pressing up against my dick. Her lips were soft and warm and loose. I went weak
from the stimulation.
Well everywhere except for one place.
Finally she backed her lips off with this half lidded
expression on her face.
"Wow," she said. "Even better than I
hoped." Then her eyes cleared and she pushed me away. "Thanks for
doing my hair. I'd have never gotten it all out by myself. We'd better go find
something to put on."
With that she opened the door, grasped me firmly by my rock
hard cock and led me out like I had a special handle just to be led around
I know she led me down the hall and into my bedroom, because
that's where I came back to earth. She could just as easily have led me out
into the street. All I was thinking about was the taste of her kiss, the warmth
of her lips, and the feel of her body up against mine. And, oh yes, the feel of
her hand on my prick.
She must have picked up some towels on the way too, because
one was slung over my shoulder. I was standing in my bedroom dripping. I
started to dry myself off and heard noises in the closet.
Megan yelled "By the way, Bob, the cost of painting
your house just went up."
Oh shit. Here it came. Blackmail. She could press charges
for indecent acts, attempted rape, pain and suffering. She could take me for
all I had.
She came out of the closet wearing my old number 7 football
jersey. It came down to the bottom of her hips. She had my number 01 jersey in
her hand and a pair of sweats I didn't even think I still owned. She could find
the damndest things in my house.
"Oh?" I said lamely.
She threw the clothes in my face. "Yeah. I just thought
of something I need and I can't buy it."
I was still standing there, mostly dry by now, kind of
dabbing at things that allowed me to cover my boner with the towel. She came
over and started helping me put the jersey on.
"Hey," I growled. "I'm a big boy." I
started getting dressed.
I'd swear I heard her say under her breath "Yes, you
But by then she was headed for the door. "I'm going to
see if I can find us something to eat."
Shit, she was taking over already, treating the house as if
she already owned it.
When I got to the kitchen she was banging pots and pans
around, but didn't seem to be accomplishing much. She had a can of ravioli out,
but couldn't find a can opener. I was walking on thin ice here. What did
teenagers like? Pizza! They all liked pizza.
"How 'bout I just call for a pizza and have them
deliver it?" I said hopefully.
She spun around smiling. "That would be great! I love
pizza." Then she frowned. "I should be able to cook. But I
can't. I don't know anything about being a girl."
I was already on the phone telling them to bring me two or
three pizzas. I didn't care what kind. No, I didn't care what kind of crust
either. I was trying to listen to her and talk to some idiot pizza person at
the same time.
Megan came over and took the phone away from me. "One
large meat lovers, thick crust. One large supreme, thin crust. Throw some bread
sticks in too. Yeah." She gave the address. How the hell did she know my
She hung up the phone. It was quiet. She looked at me and
said "Sit down Bob, we need to talk."
Okay. I took a deep breath. Here it came.
I looked at her beautiful face. Wait a minute. When did she
get that beautiful face? Those elfin eyes - they were green - that little pug
nose. When did this tomboy next door turn into a real woman? I knew about the tits
and hips, but this was different. This was a woman looking at me. Come to think
of it, it had been a woman kissing me in the shower too. That's why it
got to me so much. Those lovely green eyes were filling up with tears. Oh shit,
maybe I did scare her.
"I'm sorry," I blurted out.
Her head jerked back. "Huh?" she said.
"I'm sorry. I hope I didn't hurt you. I know I
shouldn't have done that, but..."
"Gee, Bob, lighten up. It was just some paint,"
she said, her eyes wide.
Now it was my turn. "Huh?" I said.
You didn't hurt me. It was just some paint. We got it all
off. It's no big deal, okay Bob? Please, I need to talk to you about something
She thought I was talking about spilling paint on her. But
how could that be? That was just a silly accident. That wasn't the major
thing that had happened in the last hour.
I decided to keep my mouth shut and just listen for a while.
"Okay, shoot. You have the floor."
"Good." She sat there. For some reason she was
looking at her feet. "Okay. Here goes," she said firmly. She raised
her head, looked at me and then back at her feet. "I'm ... stupid,"
she said. She looked back up and her eyes were wet again. "About girl
stuff." She paused. "And I want you to teach me about ... how to ...
how to be a girl," she finished.
Grrrreeeeaaaaaattttt. She wants to know about
girl stuff. Yeah, that's right up my alley. I forgot my vow to keep my
"You're a girl. It comes naturally to girls. You
already know everything you need to know. You were born with it. Along with
your different parts. You know ..."
She looked up at me in disgust. "I know about
the girl parts," she said as if talking to a moron. Actually, she was
talking to a moron at the moment, because when she said "girl parts"
she flipped the hem of the jersey up, baring her blond pussy, promptly lowering
my IQ by 50 points as I salivated over my glimpse of Nirvana. "I don't
know what to do with them. That's the problem. And you have to
help me Bob. You have to. That's what I meant when I said the cost of painting
went up. You have to teach me what to do with my girl parts. Boys ask me out
and I don't want to go because I don't know how to be a girl." She had
large clear tears welling out of her eyes now and rolling down those perfect
Of course you know what guys do when large crocodile tears
start rolling down girl's cheeks.
"Okay, okay," I said. "I'll help you".
Without, of course, giving any thought to what that actually meant.
But I was soon to find out.
"Oh thank you, thank you," she said as she
jumped up, all perky again. Those boobs of hers jumped too, under my jersey.
She came over to where I was sitting, straddled my lap, plopped down and kissed
me. It was a shorter kiss this time. More like what a daughter shouldn't give
her daddy, because there's more in there than just "I love you
daddy". But it wasn't a brain melter like the
one in the shower.
Of course, knowing that her naked pussy was separated from
my boner by one layer of cloth didn't help my IQ go back up either. Oddly, a
thin thread of sanity wafted up from somewhere prompting me to ask "Okay,
now what exactly did you have in mind?"
She frowned again. "I don't know exactly. That's part
of the problem. I mean I know some stuff, of course. Like that time I
saw you and Janet. I know that's what fucking is like, though I didn't really
get to see very much of what was actually going on. And I saw your ... thing
... shoot stuff out on her, and again today, and so I know..."
"Again today?" I interrupted her.
"Yeah, while you were changing into painting clothes. I
was at the window, you know?"
Oh shit. She did see me beating off.
"Anyway, I know that's how to make a boy's penis shoot
stuff, by rubbing on it like you did, but I've never done it, and maybe it's
not as easy as it looks. Heck, the only time I even ever touched one was when
you were getting the paint out of my hair. Well, after that, anyway. So can you
teach me that?"
She wanted me to teach her how to jack off a man.
All men have two heads. We have our big head, and our little
head. They both have brains in them, commensurate with their size. My little
brain caused me to speak up.
"Yes! Yes I can teach you that Megan," I said
She immediately got up off my lap. "Oh goody, can we
start right now?"
Who was I to disappoint a bright, curious young woman? I led
her back up to my bedroom and lay back on the sheet-less bed. Her casual
attitude about showing her body and touching mine suggested that I had been way
too conservative in thinking about how she might react to things.
So I threw caution to the winds and just jerked my sweats
down to my knees.
She stood there, eyes wide as my boner bobbed and
"Doesn't that hurt?" she said.
"No, not unless it stays hard a long, long time. Then
it gets a little uncomfortable. But if we do what you want to learn to do, it
will feel very, very good. Now, come on over here. You should probably get down
on your knees." She did and tentatively reached for my pole. "OK,
now, grasp it about half way down." She did. "See that skin up at the
end? That's called a foreskin. Now slide your hand down, but don't let go of
the skin." She did and my glans was unsheathed.
"Wow," she breathed. "That looks completely
different than when it's covered up."
"Yes," I said. "Not all men have a foreskin.
Sometimes it gets cut off at birth."
Her hand squeezed hard as she said "Ow! That has
I came back. "Well, when you're a baby you don't
remember it. Okay, now if a man has a foreskin, then having that going back and
forth over the head will stimulate him enough to make him ejaculate. Really all
you are doing is moving the loose skin back and forth along his shaft. If he doesn't
have a foreskin, then you'll need some lubrication or something because then
your whole hand has to slide along the skin and over the head. It's sort of
like your hand is a puss..." Shit. I'd almost said pussy.
"Pussy?" she said.
So much for modesty. "Yeah," I said. "Like a
pussy. Speaking of which, do you ever rub your pussy Megan?"
She shook her head. "That time I saw you with Janet? I
went home and my pussy itched then, and I was rubbing it cause that made if
feel better, and my grandma caught me. She whipped me good and said that if I
ever did that again it would make me go blind. It doesn't itch too much though.
Watching you jerking on your ... your penis ... that made it itch, and it
itched again in the shower when I kissed you."
"Oh," I said. "Well, your grandma meant well,
but what she said isn't the truth. It doesn't make you go blind, and it's one
of the things I'll have to teach you. That is your main girly part, after
"Okay," she said. It was obvious that whatever I
said was the truth as far as she was concerned. She leaned closer to my cock
while she jacked it, pursed her pretty pink lips, and started blowing on it,
like it was hot food and she was trying to cool it off enough to put it in her
mouth. I found that thought extremely interesting.
"I heard the girls in the locker room talking about
blowing a guy's cock. Am I doing it right?"
I didn't laugh. I stopped her. She looked up at me
questioningly. "Megan, honey, I need to show you one of the things that
your girly parts are good for. You need to understand this part before we go
on. You know what an orgasm is?"
"Yeah, we talked about it in sex ed. The guy puts his
penis in the girl's vagina," - she looked at my dick again, and shook her
head - "which has to be a crock, because there's no way in the world that that
thing would fit inside my vagina. It's way too big. Anyway, when
he does that they have orgasms and sperm shoots out into the woman. That's what
you did today, right? You had an orgasm?"
"Yes. But that doesn't really explain it. Here's what I
want to do. I want to give you an orgasm. Then you'll understand exactly
what it's like for a girl, and that will give you some idea of what the man is
Sure," she said. "What do I do?"
"You trust me. What I'm going to do will seem very
strange to you, but trust me, Okay?"
"Sure Bob," she said. I got up, sat her on the bed
with her ass on the edge and lay her back. I got between her legs. I told her
to lift her butt and she did, and that let me slide the jersey up to her
stomach. There, in all its glory, was her pretty teenage pussy, all pink and
soft under its crown of blond hairs. I took her legs and hung them over my
"All I want you to do is lay back and feel this,"
I said. "I'm going to lick your pussy."
"You're going to what?" she said, lifting
"I'm going to go down on you. I'm going to give you
a blow job. I'm going to help you have an orgasm. Now just lay there and feel,"
And then I feasted on that pussy. I started by sliding my
hands all over her thighs and abdomen. Most men ignore the millions of nerve
endings in a woman's abdomen because men don't have them. Right over the
ovaries and along the track where the fallopian tubes run there are zillions of
nerves that are really handy at getting a woman in the mood. I pushed every
button on her skin I could find except her nipples. I was saving them for
later. While I did that I licked and kissed the inside of her thighs, moving
closer and closer to her pussy lips. In no time her hips were moving around on
the bed. " Mmm Bob, that feels ... nice. Mmmmm.
Hey! My pussy's starting to itch." Her hand came down toward her vulva and
I slapped it away. "Just feel," I growled. Then I moved my
tongue up between her vulva.
She jerked when my tongue slipped into her vaginal
vestibule. I split her lips apart with my tongue and then widened them, licking
all the way up, dragging the flat of the tongue across the hood sheathing her
"Ohhhhhh," she said, her
head popping up to see what I was doing.
I backed up and looked. Yup, her clit was beginning to peek
out. I went back to the lips. I licked the left, then the right, then stuck my
tongue as far into her as I could. When I couldn't stand it any longer I took
the tip of my tongue and started going in circles around her clit. I started
raking the tip over the clit itself and her hips came up off the bed. "
Ohhhowww!" she yipped. "OH Bob...Oh!
Oh! don't stop, please keep doing that. Ohhhh..." She finally
had to take a breath and while she did I sucked her clit into my mouth and
nibbled on it.
Megan had her very first orgasm. It turned out she was a
gusher. I'd heard of them, but never actually seen one. Her juices actually
squirted out of her pussy like semen would from a man. There was a thin stream
of a milky white substance that hit me on the chin. Then clear fluid began
seeping out. I dove back in and lapped it up, sucking on the lips, her clit,
anything, shaking my head back and forth, letting my lips and even my nose
slosh around between her legs. She was moaning and groaning and yelling and
even laughing. Finally I felt her hands on my head and she was yelling
"Stop, stop, Bob ... I can't take it anymore." I backed up and
her legs fell off my shoulders limply.
Right then the doorbell rang. The pizza was here.
I grabbed a towel, wiped my face, pulled up my sweats and
went to the door. It was a girl! She looked at me and her eyes got wide. I was
patting my butt, trying to find my wallet. Finally I realized what I was doing.
"Just a sec. I'll get my wallet." I turned and bounded up the stairs.
Megan was still lying on the bed, legs spread, chest heaving
as she recovered. One hand was lying with two fingers across her clit. Those
two fingers were very slowly rubbing her clit. I grabbed my billfold and
headed back downstairs. On the way I saw myself in the mirror. Hair going every
which way, area below my nose still wet with Megan's spend. Shit eating grin on
my face. I pulled out two twenties, gave them to the girl, took the boxes and
slammed the door in her face. I was on my way to the kitchen when I realized
that besides what I had just seen in the mirror, the pizza girl had an
unobstructed view, as I patted my ass, of the eight inch tent in the front of
my sweats that my still hard dick was making. I threw the pizzas on the table
and dashed back upstairs.
"Pizza's here," I announced, trying to breathe
normally, like what I had just done was no big deal.
Megan raised her head and looked at me. "Can we do that
I smiled. "Yes. We'll do it again. But not now. There
are lots of other ways to make that feeling happen. You'll want to learn all of
them I imagine."
Her head dropped back down on the bed. "
Ohhhhhhh yessssss," she
said. "I want to learn them all."
I lay down on the bed beside her, on my side, so I could
look at her. I gave her a little more time to recover. "So that's
what a blow job is," I said. "For a girl. When a girl does that to a
guy it's slightly different."
She rolled her head to look at me. "So a girl puts his
penis in her mouth? Right?"
"Right," I said.
She looked thoughtful. "So what happens when the stuff
shoots out?" she said.
"Well, you can catch it in something - a towel or
whatever - or some women like to drink it - swallow it - and some women even
like to let it go all over the place, making a big mess."
"Like Janet did?" she asked.
"You remember that, from so long ago?" I asked
Her eyes went glassy. "I'll never forget seeing
"Well, the answer is yes. Some women like having it
shot on their body."
"And it makes the guy feel like I just did?" she
"I want to make you feel that way," she said.
I pulled down my sweats again and lay back on the bed.
Megan was a fast learner. She crawled over and held my dick,
which was now wet with precum. She dipped her finger in that and stuck it to
her tongue. " Mmm ... salty a little bit. Doesn't
really taste like much of anything," she said.
I was in teaching mode. "I'm told that a man's diet
determines to some degree what his semen tastes like. I don't know about that,
but women have told me I taste different than other men they've known."
Instead of talking, Megan dipped her head and swooped down
on my cock. She seemed to know instinctively not to use her teeth too much. She
used her tongue to play with the foreskin, sliding her tongue along the glans
and almost under the skin. Then she jacked the skin off the glans and sucked
that part like she was trying to drink soda through a straw. She was a natural.
I'm here to tell you. Most men have to be jacked off during
a blow job. It is rare indeed for a woman to be able to bring a man off with
only her mouth. Megan was one of those women. She used her lips, cheeks, teeth
and suction to work my cock like it was some kind of musical instrument. Quite
soon I felt the sweet release I had been aching for for
what seemed like hours.
"Megan," I said, panting. "I'm about to
shoot, baby. Any second now." Now she used her hand. She skinned the glans
clear, locked her lips around the sensitive area just under the glans, stuck
her tongue in the hole that was about to spew and jacked on my cock like she
had seen me do.
I pumped what seemed like a pint into her mouth and she
happily sucked and slurped it all down.
Now it was my turn to lie there, gasping for air, limp. She
rose up on her haunches and looked at me as she licked her lips. "Not bad.
Not bad at all. I'm gonna go get some pizza." And she was off like a deer,
bouncing off the bed and leaping across the room.
Once again I ended up in the kitchen with Megan. She was
bubbly now, euphoric after having had and given her first orgasm. She ate pizza
with relish, talking about anything and everything. She sat on a chair, legs
carelessly open just enough that I could see her treasure. I had left my sweats
in the bedroom and now was dressed as she was, only in a jersey. She glanced in
my lap and stopped eating.
"Bob! What happened?!" she was peering at my
relaxed and happy penis. "It got all ... little! I didn't break it
did I?" she anxiously looked up at my face.
I thought she was kidding. But she seemed serious. "No,
sweetie. This is how it looks most of the time. Did you think it was hard all
"Well, yeah, I guess. I've only seen yours, and every
time I saw it, it was hard."
"Oh, yeah," I actually blushed a little. "The
first time Janet made it hard. Every other time you saw it, you made it
She looked interested. "How exactly did I do
How to explain to this delightfully innocent girl that a
dirty old man had been sneaking peeks through holes in her shirt for years.
"Well, if a man sees a woman he likes, or who he thinks is beautiful,
especially if he can see the private parts of her, her girlie parts" - she
smiled - "then he gets hard because he wants to have intercourse with her.
That's how men are made."
She thought about that. "You think I'm beautiful?"
"Oh yeah!" I said. "I've thought you were
beautiful for several years now. You've made me ... hard ... before today.
"And that's because you want to ... to have intercourse
"Yes. I have to admit I have thought of having
intercourse with you."
She shook her head. "But it would never work. I mean,
when you're hard, you're way too big to fit inside me. I put a finger in
there one time and it was tight even for my finger. You'd never fit. I have a
hard time getting a tampon in me sometimes."
Hmmmm she used tampons. That meant either no cherry guarding
her depths. "Well, sweetie, I know it looks that way, but I guarantee you
that, when the time comes, and you want to take a penis inside you, it
will fit, no matter how big or small it is. Mine is probably pretty much a
normal size. Maybe just a little bit longer than some, but not bigger
"But it hurts, right?" She had closed her legs and
was rubbing them together slightly.
"It depends. If your hymen is intact, then tearing it
hurts a little. If the man pushes his penis in you too fast, it can hurt. If
there isn't enough lubrication, it can hurt. You just have to pick the right
guy when the time comes. You need a guy who loves you and will be careful and
do what you need done. Then it will only hurt a little bit, and then
usually only the first time you do it. After that it shouldn't hurt at all
unless he goes too fast."
"So you don't want to be the one who does it with me
the first time?" she said.
"No, sweetie, I didn't mean that. I'd love to be
your first, but it has to be someone you love and want. It's a very
personal thing. Besides, I don't have anything here to protect you ... from
"Oh!" she said. "Pregnancy," she
murmured under her breath. Her legs were rubbing faster now. "Bob?"
"My pussy is getting all itchy again."
We went back upstairs. I grabbed some sheets and we made the
bed. I told her to take her jersey off and she did so without a thought. She
was gorgeous. Her breasts were the upturned kind, with perky pink nipples that
stuck out even when they weren't erect. Each was a little less than two
handfuls. Her flat stomach accentuated those hips that kept her pants up now.
By the time I got undressed my cock was at full mast again. "Oh look!"
she said with glee. "You want to ... fuck me ... again!"
Too true. But instead I told her I was going to give her
another orgasm. We got into bed and I held her against me. I concentrated on
After four or five kisses that sucked the life out of me she
leaned back. "That's why I kissed you in the shower today. I had never
kissed anyone except my grandma. I see the other girls kissing their boyfriends
and I wondered what the big deal was. All it took was that one kiss in the
shower and I understood. And now, I've had an orgasm and I understand that too.
You really can't explain it in words. I really like the kissing. It
makes my pussy itch a lot."
Then she went back to kissing me. I rolled her onto her back
and started sliding my hands all over her body. This time I played with her
breasts. At first I just slid my whole hand across her nipples and then down to
her abs, where all those nerves are. Then I strummed her nipples with all four
fingers, followed by sliding one finger onto her clit and massaging it until
she arched her hips. I was kissing her all the time. Finally I squeezed and
pinched her nipples, tugging them this way and that, stretching them out,
pulling them away from her body and letting then snap back. She was writhing
now and all I had to do was slide my middle finger deep into her pussy and pull
upward, mashing her clit and she went off like a firecracker.
She shuddered and groaned and then made yipping sounds as
the orgasm washed over her like an ocean wave. Her knees flexed and then her
legs shot out straight. With my finger buried in her I wagged my hand sideways
to extend her pleasure. It took maybe 20 seconds before her hand went and
grabbed my wrist, stopping my motion.
She lay there gasping. "Oh ... Oh that ... feels ... so
... good ... but stop ... or I'll just ... die." She gasped again as I
slowly pulled my finger out of her. Her juices had glued it in place and I
could feel the seal breaking. Then we rolled together. I pulled the top sheet
over us and we drifted off to sleep.
I woke up. There was a warm naked body up against mine.
Megan. Oh yeah. I was so happy it wasn't a dream after all. I had a full Monty
boner and it had insinuated its way between Megan's legs and was nuzzling her
pussy. That part of her was even hotter. I couldn't resist the temptation to
push. There was just enough pressure on the skin to slick the foreskin back and
forth over the glans. That felt so good I just lay there, dry fucking her
thighs and pussy lips for a while. I was going to have to jack off or I'd never
get back to sleep.
"Bob?" she whispered.
"Mmmm yeah, baby?" I whispered back.
"Are you fucking me?"
"No sweetie. It's just touching your opening. It's not
"Bob?" she said again.
"My pussy itches again. And what you're doing feels
really nice. Could you maybe put it in me just a little? Not all the way, but
just a little?"
"I'd love to do that baby, but like I said, I don't
have any protection." The thought of going in her 'just a little' was
entirely pleasurable, except that I knew 'just a little' usually ends up being
more than that.
"What about if you weren't inside me when you squirted
- like you did with Janet? Wouldn't that make it okay?"
Man! She had all the answers. The temptation was great. I
knew I should not do this. Withdrawal is a crappy form of birth control. But
her pussy would be sweet, and it would get my rocks off.
p to this point I had just been stupid. And male.
But now I made my first big mistake.
"Okay. But just a little, and then when I tell you it's
time, then I pull out. You can drink it then if you want to."
"Goody!" she whispered.
Then I made my second big mistake.
"Okay, you get on top of me. That way you can put as
much in as feels okay, and you can jump off when it's time and go down on
Which is how I ended up underneath 110 pounds of horny
virgin with a hard cock that said virgin was about to use to deflower herself
with. She situated herself and reached between us. She grabbed my dick and
started rubbing it around her honey pot. She learned instantly that it could be
used to massage her clit, and did that for a while, mewling softly about how
wonderful it felt. Then she pointed it up into her pussy and began applying
pressure to get some of it in her.
It was a tough go. She was very tight. She hunched and
thrust and the head slid out every side of her pussy mouth. "Relax" I
told her. "If your muscles are tensed up, they make it hard to open you
up. Relax your inner muscles." I reached up and captured her head in my
hands. I kissed her and tried to make it the most tender and sexual kiss I
could. I licked her lips and showered them with little kisses. Suddenly the
head popped through her pussy lips and she gasped.
"Ooooooooo," she moaned.
"That feels huge". She wasn't moving any more.
So I said "Does it feel bad? Does it hurt?"
She responded "No ... it just feels ... strange. I'm
really stretched, but it doesn't hurt. It feels like there isn't enough in me,
though. Like I should push to get more in."
I knew what that was. It was the same thing that was telling
me to push more in. "Sweetie, that's instinct. Your pussy knows
what it was made for and it wants to do that. But you can control that if you
want to. Like I said, just go as far as you want to."
"Okay, she said. "But my pussy still itches, so
I'm going to put just a little more in. I like it when you kiss me."
Very direct, my girl. So I kissed her some more.
That's when I made my third big mistake.
I decided to give her a little assistance by playing with
her nipples. I started rolling them between my thumb and fingers, not pinching,
just playing with them. She moaned into my mouth and started moving her hips.
She wasn't exactly pushing down on my cock, but she wasn't pulling off either.
It occurred to me I had never had my mouth on her breasts. I broke the kiss and
pushed her up enough that I could get to them. I captured her right nipple in
my mouth and I sucked.
Megan squealed and lunged. I felt my cock sliding into hot
butter and I felt her heat all over my cock. All over my cock. She had
impaled herself completely. She made the most amazing and erotic noises I ever
heard. I can't even begin to spell them here. But they made my nuts just go
crazy, because they made it quite clear that she was one very
happy girl. And all the time she was wiggling wildly on my cock.
If she would have just leaned forward she could have pulled
the invading monster out. But for some reason she went sideways, then back, then
partway up, then back down.
The thing I compare it with is when you take a bite of
something too hot, and you can't spit it out, you move it all around in your
mouth, really fast, so it won't touch any one part of your mouth long enough to
burn it. You know what I mean?
Well, she was doing that kind of thing with my cock. Except,
of course, her pussy couldn't get away from my cock. I put my hands up under
her armpits and started to pull her off of it and she let out a wail
that would have waked the dead.
So I thought she was in so much pain that she didn't want me
to move and I let go. Wham she slammed right back down on it, driving it
up into her belly deep. Then that wiggling. Then I figured it out. My cock was
clear up into her cervix and by wiggling the way she was she was making my cock
head massage those inner lips, with their zillions of sexual nerves. Then I
could feel how the tip of my cock was slipping up into that mouth,
peeking into her womb, while my foreskin bunched outside, making a seal around
Remember when I told her that just the foreskin gliding
across the glans could result in an orgasm? Well put that penis inside a virgin
whose cervix is doing the same thing and you have a recipe for orgasm. I felt
the tingle in my balls that heralded just such an event. And of course, right
then, Megan started to tumble into her first orgasm while stuffed with a hard
male penis. "Oh Bob, oh Bob, oh Bob, oh Bob," she chanted.
I said "Megan, honey, it's time to get off, baby."
She said "Ohhhh Bob, Ahhhhh Bob! Oh shit, Bob!"
I said "Now, Megan, Now, baby, you have to
get off now!"
She said " Nooooooo,"
again and ground her pussy down on me even more.
Three bad things I did. And they led to this.
My one-eyed-dragon was peeking into her treasure cavern when
it breathed fire. My prick did the triple "B". It Bulged, Belched and
Backfired, sending long sticky ribbons of my cum not just into her pussy, but
into her womb itself. Not just long sticky ribbons of my cum, but buttery bolts
of baby makers were injected into her like it was a medical procedure. Foreskin
bunched nicely around the lips, sealing them so none of those wriggly little
sperm could get out.
Egg? Meet Sperm. Hope you two live happily ever after.
Well, that's what I was thinking, not that that helped. If
anything, the thought that I might be knocking up this beautiful young woman
made my balls work that much harder to provide another ounce or two of seed to
fertilize her with.
And through it all she was yipping and yelling and her own
juices were squirting out around my cock, soaking everything. At one point she
grunted "Hot, hot, hot, I can feel it hot, wet, wet, ohhhhhhh."
And then she just stopped, frozen.
And, very, very slowly, she bent her arms until she was
lying on top of me, her face in my neck, gasping for air. I had filled her
belly with my spend, and it had weighed her down until she couldn't move.
She licked her lips and whispered in my ear "My pussy
doesn't itch any more, Bob."
"I'm happy for you, baby," I whispered back.
"I've loved you for years, Bob."
I think I loved you too and just didn't realize it," I
She snuggled down, squeezing her pussy muscles around my
still embedded cock.
We fell back asleep that way.
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