The Tomboy Blues free porn video

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 there.

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 knocked.

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 you’re nothing.”

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 left.

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 money.”

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 chest.

Wow.

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 favorite shirt.

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 room.

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 ready.”

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 instead.

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 her.

“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 yelled.

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 with.

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 certainly are.”

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 address?

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 important.”

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 mouth shut.

“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 cheeks.

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 firmly.

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 waved.

“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 to hurt.”

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 all.”

“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.