The neighborhood I grew up in was all single-family houses that were all lined up together, all close together, and I'll never forget the night I first looked out my bedroom window and saw the girl next-door, Cheryl Matthews, in her bedroom. She pulled the shade down, I was pretty sure she hadn't seen me and I quickly went outside and tried to look up under her shade which wasn't quite lowered down all the way.
I couldn't fully see into her room so I put the toe of my sneakers on the little ledge on the house's foundation and peered up into her room. She wasn't in there and I let myself down to wait a minute or so, then hoisted myself back up. Still no Cheryl. So, I waited a bit more, then went up for another look.
Damn. There she was, a towel wrapped around her head and a blue robe over her. She walked over to her mirror and slipped the robe off and stood there looking at her naked body just as I was. Only I was seeing her backside which was still quite wonderful.
Her hands came up to her boobs as she cupped her hands over her breasts and rubbed them then twisted her nipples between her fingertips. Soon, one hand dropped down and I knew she was playing with her pussy as she watched in the mirror. Right then, my foot slipped and I went ass-backwards, rather noisily, onto the ground. As I was getting up, I saw the shade rise about a foot as her head peered out into the darkness.
I made it back into my house and quickly got in my room, leaving the light off, and went to bed to jack-off twice in the darkness.
It was the next day when it all happened.
I was coming up the street from being let off by the school bus when I walked in front of Cheryl's house and there she was sitting on the front porch steps.
"You, Simon, come here, I've been waiting for you," she barked at me angrily. She was in high school, a Catholic high school, and I was still in eighth grade in a public middle school. We both had uniforms on, mine was a blue teeshirt and khaki pants, hers was a white blouse and a dark navy blue skirt and black and white saddle shoes.
"I'm telling your mother what you did."
I just stood there as she towered over me, up on her porch, as I stood on their front walk.
"You were looking in my bedroom, weren't you, you little pervert? I'll get you in a ton of trouble."
"I ... um ... I ... I didn't mean to, it was an accident," I claimed lamely knowing as soon as I'd said it that it wouldn't fly.
"Oh, it was an accident that you fell down on your sorry ass but I know what you were doing. You were looking at me, at my naked body, weren't you? Tell me."
She was so forceful that I admitted that was what I was doing. She turned and went to her front door, saying back to me, "Come here, come inside. We're gonna talk about this. You're in big trouble."
I followed her inside and she told me, "You're in deep shit, you know. I'll tell your mother and you'll get hell for what you did."
"Don't tell my mom, please don't do that. I really didn't mean anything bad," I gasped.
"You were looking at me naked, Simon. And I caught your ass. Deep shit, Simon, you're in deep shit."
"Just please don't tell, please, it was a mistake," I begged.
"Come upstairs, we'll talk about it," she said as she went up as I followed her, knowing that, indeed, I was in deep shit.
We turned and went in her room.
"Sit down, Simon. You like to watch me, don't you?"
"Um, I guess, but I won't ever do it again. Not ever, I promise."
"Well, maybe you can convince me not to tell your mother about you spying on me."
"I'll do whatever you want, anything, just don't tell, please."
"Okay, let's see how serious you are. Take off your clothes."
I looked at her standing over me as the words circled inside my head.
"You want me to take my clothes off?"
"If you don't want me to tell. You saw me naked, now I get to see you. Go on."
I stood up and slowly pulled up my teeshirt and put it at the foot of her bed.
"Pants next, come on," she hectored as I undid my belt, zipped down my fly, kicked my shoes off, pulled my socks off and dropped my pants to the floor.
I was really trying not to have a hard-on, I couldn't even imagine that I would have one under the stressful circumstances, but there it was poking out my white briefs as I stood there.
"Underpants, Simon, let's see it, come on, get 'em off," she barked at me as I hesitantly slid them down.
"Oh, look at you. Cute little dick. Bet that got real hard last night looking in my window. Ran home and jacked it off, didn't you?"
"I don't remember," I lied.
"Bull shit. You remember, all right. Tell me. Once, twice, three times? How many times did you beat-off?"
"So, little Simon jacked-off twice after seeing me naked. Does little Simon like seeing me naked? Huh?" she said pushing me down on her bed. "Do you, Simon, do you? Answer me, do you?"
"Yeah" I squeaked out.
"Well, then I'm gonna let you, okay?" she said as she made me stretch out on her bed as she kicked off her shoes, pulled her socks off and reached under her skirt and pulled her panties down and tossed them at me.
Then she got up on her bed, faced the foot of the bed, swung a leg up over me and squatted down with her bare pussy, under her skirt, just a few inches from my face.
Her hand reached under and she began rubbing her pussy with her fingers as I watched from beneath her skirt.
"You like what you see, you little pervert? You like my pussy? It's what you wanted to see?" she said as my hand went down. I wanted to play with my dick after all, but she barked, "No touching yourself, you little pervert. Leave your dick alone or I'll bite it off."
I really didn't think she'd bite my dick off but, well, I loved my dick and would never do anything to lose it so I kept my hands at my side.
"Mmm, feels good, my pussy's feeling real good. You like watching me get off? You like my pussy?"
"Yeah, I never thought you'd let me watch you doing something like this," I told her.
She took her fingers away, then suddenly squatted onto my face and rubbed her wet pussy all over my face then lifted back up and resumed her masturbation.
"Does my pussy taste good, Simon? You like it? Tell me," she demanded as I felt her hand take hold of my cock and pinch it.
"Ow, that hurts," I cried out.
"Well, answer me, dammit."
"Yes, I liked it."
"Want some more, Simon. Some more of my pussy?"
"Uh-huh," I moaned as she pushed back down on my face rubbing in circles round and around, then lifted back up.
"Feels good when I sit on your face, Simon, you're nice to have around," she moaned as I watched her fingers rub then stroke in and out and rub again.
"Mmm, oh, yeah, I'm gonna cum, little peeper-boy. I'm gonna cum. Oh, yeah, UUH, UUH, UMMM, MMM, mmm, oh, my pussy feels so good. I like you watching me get off. We're gonna do this every day after school, Simon. You're gonna get to see me a lot, a whole lot. Like seeing me like this?"
I wasn't quite sure what to say but I decided to be truthful, "Yeah, I love it, you're the sexiest girl in the world, Cheryl."
She squatted down again and rubbed over me again and, this time, didn't get back up, she kept rubbing around on my face until she got off again.
She rose up, swung around and knelt down next to me.
"Oh, look at your wet face. All covered with my pussy juice," she said as she bent over and kissed me as I felt two things: her tongue slipping into my mouth and her hand taking my dick and pulling it up and down.
I immediately shot my cum all over her hand and my legs as she hooted, "Look, little peeper-boy shot his cum all over my bed. Look at all that baby-making juice. You really shoot, Simon. You're a horny little bastard. Well, all this should make you happy. Now go home and jack-off some more. I'll see you tomorrow," she said and I quickly dressed and left, my head spinning.
I did as she suggested, I jacked-off; twice, actually.
Then, the next afternoon, there she was sitting on her steps as I came down the street.
"Hello, Simon, how was school today?" she called out as she swiveled toward me, spreading her legs open.
There it was, her pretty bare pussy, glistening in the afternoon sunlight.
"Come over to see me, Simon? Like what you see?" she taunted me as my dick swelled.
"Oh, I can see something, Simon. You do like what you see. Come inside and you can see some more," she said as she got up and I followed her to her room.
"Don't just stand there, Simon. You know the routine, get naked," she ordered and I was soon standing there with my dick standing tall.
"Oooh, he's all excited. Here's what you've been wanting, Simon," she said as she unbuttoned her blouse, reached around, then took off her bra as well.
"Nice, huh? Aren't my titties nice?" she asked as she pushed off her shoes and socks.
Her boobs were really nice, not real big but just perfect with light pink nipples.
Her skirt came down and she stepped out of it as we both stood there naked looking at each other.
"Down on the bed, Simon. You know the routine," she said and I got down and she squatted over me again and began masturbating right over my face.
I automatically led my hand over onto my dick and she barked, "Get your hand away. No feeling yourself. If anybody touches that it'll be me. No touching."
I could see that she was very wet underneath her as her fingers flew back and forth across her pussy lips.
"Mmm, feeling good. Like watching me? How about it, Simon? I'm really making this hard, aren't I?" she said as she took my dick and squeezed it ... almost too tightly.
"I love looking at you like this, yes," I moaned as she masturbated right over my face.
"Mmm, here, have some hot pussy," she said as she pressed down on me scooting all around my face then back up to finger herself some more.
She had two fingers up inside fucking in and out as she moaned and panted while I tried to stay still under her so she wouldn't get mad at me. Then, she started to go off.
"Ooooh, uuuuh, mmmm, oh, yeah, cum, pussy, cum," she cried out, "CUM, CUM, CUM," as her body shook over me, her pussy glazed with shiny juices that also were smeared all over my face. I planned on leaving it on my face until right before my parents got home; it was like a proud mark that I wore.
"Okay, peeper-boy, that's all you get today. Get your clothes on, I'll see you tomorrow."
And, that's just what happened the next day as well. She took me to her room, made me strip and get under her while she masturbated over me totally naked but still denied any touching of her or myself. I would run home and try to jack-off twice before my parents got home.
She wasn't on her front porch every day; it was more like three days each week and this went on until one day about a month after the first afternoon, she was sitting there in her usual spot and there was another girl sitting next to her. One I didn't know. Surely she wasn't going to make me go up to her room today, I thought as I said hello trying to walk on by her house.
"Hey, Simon, hold on there, little buddy. This is Audrey. Why don't you come in and get acquainted?" she said nodding back to her front door.
"Um, you sure?" I asked hesitantly and she said she was sure, very sure so I figured I'd better do what she said and followed both girls up to Cheryl's room.
"Okay, Simon, get 'em off, let Audrey see what you look like," she ordered.
"Do I have to?" I pleaded and she told me I did so I pulled my shirt off and began taking off my shoes and socks. "She won't tell anybody?" I added and the new girl said she wouldn't. I stood there in front of them bare-assed with my dick hard.
"See, I told you, he's got the cutest dick, right?" Cheryl said.
Her friend, grinning at me, told her, "Oh, yeah, it's nice. Have you sucked it?"
"Nah, I don't let him touch me, drives him crazy, he has to run home and beat-off his little dick. He says he does it several times after I send him home."
"Can I touch it?" Audrey asked and I nodded as I watched her hand reach out and her fingers wrap around to softly squeeze. "It's really warm. How little is it when it's not excited? When it's soft?" she asked and I held my fingers apart about an inch and a half.
"So it really grows when you get excited?"