So, me, and my brother were playing dressup, while mom, and dad were out on a date. My name’s Penelope, but everyone calls me “Penny,” and I was 11 at the time. My brother, Pauley went right to mom’s side of the closet, and got it out of the box, underneath her shoes.
“Check it out,” he turned around, and waved it by the dong, so the pink plastic straps waved around.
“Ew, you know where that’s been?” I giggled, but I didn’t know if he knew about it. Honestly, he was almost 15, and in high school. It was a little weird him still playing dressup with me, and I was starting to think he might be gay, but I never asked him about it, because how do you even start a conversation like that?
Well, it turned out that he started it, by suggesting we go play dressup, and getting out mom’s strapon. “Put it on.”
“Okay,” I kept laughing, because it always looked rediculous. Even on mom, when I walked in on them getting kinky, I laughed, and then she had to pull out to explain to me what was going on.
I was just careful to only touch the straps, knowing where it’s been. Up our dad’s butt, he loved bending over, and taking it up the butt, while mom dressed up in a shiny plastic uniform. As a cop, but not like a real police woman. More like a sexy cop on Halloween, but she kept the outfit, and even added some stuff to the hollow plastic baton, and the padded handcuffs.
Oh yeah, she had to unlock the handcuffs, so dad could take the ball gag out of his mouth, and go use the bathroom while she explained it. “I’m just going to slip into something a little more comfortable.” Pauley joked, and pulled his shirt off first, but he kept looking over at me.
With my leg up, so I could tighten one strap, and then the other to get that side. That made it bounce, and swing, like a great big purple boner, which just made me laugh even more.
“This is silly.” Then, I covered my mouth, and stopped laughing when Pauley dropped his pants, and turned around with a full hard-on. I didn’t think, well. I probably didn’t even want to think that’s where he was going with this. That he planned it all along, and he was just as kinky as dad.
“I know.” he picked up a pair of crotchless panties, and pulled them up, then stuck his fingers to pinch, and pull his balls out. With his dickhead sticking out the wasteband in front, and his butt crack showing through the hole in back, because these weren’t mom’s panties. They were dad’s lacy fuck me panties, with a hole in the back, for the strap-on dong.
“Here,” I grabbed the side drawer, and pulled it out to get a rubber. “I better put one of these on.” I grabbed the bottle of lube, from the drawer, and just threw it on the bed. I couldn’t force myself to say he better butter it up, but I didn’t have to. All pretense of just playing dressup was gone, and my giggles went with it, but now I was so excited!
By the thought of nailing a boy, any boy up the butt, I just never thought that Pauley swung that way, or he would be my first. Well, my first boy, I showed some of my friends, and we took turns putting it on, putting it in, and screwed around. Playing “The boy,” but really, this was even better. The boy being my brother, and the one pouring lube on his fingers, to get them nice and shiny, then pulling down the kinky underpants to slick it in his butt, and finger it to loosen up.
“Oh!” He moaned, and made a face, but it wasn’t just sexy, and blushing. He was also concentrating, on feeling around, and wiggling his fingers so his tight butthole got looser, and looser.
“You better suck it first. Yeah, get down on your knees, and suck my dick. Huh, you look so sexy, finging your ass. Don’t stop.”
“Finging?” He grinned up at me, confused.
“Yeah,” I laughed, “What else does a finger do?” He laughed too, but then I started swinging my hips, so it swung like a bat, and slapped him around so he grabbed it, and stuck it in his mouth.
Of course, I couldn’t feel anything, through the fake ass plastic dick. No matter how realistically it was molded, with a soft comfort tip, shaped exactly like a dickhead, and vein like ridges for extra stimulation. I still had my pants on, and the base strapped tight over the crotch of my underwear, but I was getting hot.
“Huh! Uh!” I had to pull my top real hard, to untuck it from the belt. “Suck it, yeah, suck it good, and hard.”
“Uh guh guk!” I didn’t even try to fuck his face, he deep throated it all on his own, then pulled it out to cough, and spit. Stroke it so it got wet, and slippery one handed, while the other finged his rear end down the back of the panties.
I finally got my top unbuttoned enough to take it off, but I left my training bra on, because honestly, it was a pain to stretch it, and pull my shoulders through. If I had a real bra, then I could just unhook it, but I wasn’t even up to A cups yet, and I remember uhm. I guess it had been a couple years, since we were the exact same sizes, and I got my first training bras, so he could try them on too.
I guess they’re really transvestites, and not gay at all. Pauley, and our dad, I wonder if they had a talk like me, and mom, did, but now he was too broad shouldered to really fit anything that wasn’t too baggy on me. My hips got too big, so my undies hung off his, the last time he tried them on, and it’s odd that he never got a boner before, but then when he stopped, and got up.
It was gone, and just curled up with his balls in the bottom of the extra roomy crotch. He had to pull them in, when he pulled the back out to butter up his rear end, but then he took me by the shoulders. Gently, and looked me in the eyes. “You ready?”
I nodded, and braced myself, but I had to ask. “Are you?”
“Yeah, I can”t wait. Get on the bed.”
“Okay,” so first I layed down, and he tried to do it with the underwear on, but that didn’t work. “Take them off,” so we had to take a break while he climbed off, and pulled them down his legs. His hairy legs, he doesn’t shave them, or anything, and they don’t look like girl legs at all. I kinda liked that, and even reached out to feel the hairy skin, the tight muscles, just to remind myself this was really happening.
This wasn’t some girl, in 6 grade, with no tits, pretending I’m a boy to fool around with mom, and dad’s dong. This was a boy, a real one, and my brother. “Paul, Pauley?”
“Pauline, or Paula?” He smiled, and asked.
“Uhm?” I thought, and shook my head. “I don’t know, which one do you like better?”
“I don’t know, that’s why asked you, you’re the girl.”
“I like Pauley, like I always liked to call you Polly? Like Polly Pocket.” I can’t for the life of me remember where I’d put those playsets, because it had been years since I put them away, but that reminded me of how this all started. First with dolls, and taking their clothes off. Then, playing dressup, he showed me how he peed, standing up. Then, I got up on the toilet, and he bent down to watch the pee trickle out of me, but he never got a boner, so I thought that it wasn’t really sexual.
Now that he had trouble keeping it up, I was starting to wonder. Maybe that’s not the best way to tell, but then he got on the bed again, and straddled me. “Can I suck it?” I just blurted it out, but there it was, just dangling right in front of me, and hanging over his balls.
“We don’t have a lot of time,” he looked at the bedside clock.
“Real quick, I bet I can get you hard again, if you let me suck it.” I argued, even though I just wanted it in my mouth, just to see what it tasted like, and finally have a boy’s dick in my mouth.
“Huh!” He looked up, “Okay.” It’s just weird, I never thought that any boy would need to be talked into getting head, even if I am his little sister. I know, I’m young, and only in 6th grade. I don;t have a whole lot to push out my training bra, but I have great hips? I always prided myself on that, even though it all went to my hips, instead of my tits, and no boy hardly noticed, because all they care about is boobs, but not my brother, Polly.
“Huh!” He pulled out, “There, you happy?”
I nodded, even though I wanted to suck him off, and feel his cum shoot right in my mouth, so I could taste it fresh from the source, my first time. I did get a chance to feel it grow, and swell, and get hard so when it popped out, it stood straight up.
“Yeah,” I held the thick hard dong, “You ready to get fucked up the butt?”
“Yeah,” he took the top of it, and put his foot up. So, He could squirm, and wiggle it in slowly, but I couldn’t hardly see it stretch, with his balls in the way. So, i reached out, and played with his balls. Held up his dick, and even felt it go soft. Shrivel up, and shrink in my hands, while the bright purple plastic head squished, and stretched up his greasy butthole.
Then, he sighed, moaned, and relaxed. So, he sank down, and sat on his hips, but I didn’t realize what that would do, when I lay down. “Uh, ow. Stop, get up, huh!” It pulled up off my crotch, when he started pulling it back out. Slowly with a grunt, and his butthole stretched out, before slipping back, and he moaned again. “Oh, what’s wrong?”
“You’re too heavy, and it crushed my clit.” The pressure on my pubes made it squeeze out, and swell so big, it felt like it was going to pop, and while I know that sounds sexy, it actually really hurt! “You better bend over, and let me nail you doggy style.”
“Yeah yeah yeah!” He did, with his legs hanging off the bed. Real excited, and he held still while I aimed it. Pressed it against his butthole, and pushed it in slowly. “Ooooh, fuck!’ he moaned, “Ooh fuck, that feels good. Feels so good fuck me. Fuck me good and hard!” So, I started pumping my hips, and bumping the base, so it hammered in inch by inch, but not too hard.
I definitely found out why Mom likes to do this so much, and it’s not just because dad likes it so much. Just to please him, but hearing Polly’s moans, and seeing the pleasure on his face was a big help too. I didn’t count on the pleasure of it bumping my pubes, and bulging out my little hard in, so it slipped out of the hood like a foreskin. “Uh, pound it, pound it in and out uhn! UHN!” he squealed like a little girl, and it was so funny, I started laughing out loud.
So loud that i didn’t hear mom and dad come in, until mom called “Kids?”
“Ihn!’ Polly grunted, and gasped, then he slid off. Panting, and trying weakly to get up off the floor, but I was too busy feeling for the straps. Trying to pinch the D rings apart to loosen them enough to slip it off, and thanking goodness that all I took off was my blouse, but it was too late.
“What are you doing in?”
Dad stopped in the door, and pushed mom out of the way to get in front of her. “What the fuck?”
“Uh, it’s not what it looks like, dad!” Pauley caught his breath, and managed to turn over, on his knees, and covering up his fresh fucked butt, but it was too late to make excuses. All he had to do was look around at me, still trying to loosen the belt, and his sexy panties with the holes in them on the floor, the bottle of lube leaking sideways on the bunched up bedspread, and Pauly naked on the floor, trying to hold in the shit I churned up with lube only moments before.
“Uh!” he half crawled, then got his foot down to dive for their bathroom. Then, we heard the toilet seat, a gush, and he grunted.
“Huh!” I shook my head, hiding my face in both hands. “I’m sorry.” I tried, but it barely came out.
“It’s okay,'”mom came and held me. “Now, I know you’re curious, and you must be confused.”
“But we told them to stay out of our things!” Dad protested.
“Oh, come on. Sweetheart, I love you, but try to be realistic. You know as well as I do that if you forbid them to do anything, it just makes them even more curious.”
“Dad?” Pauley didn’t even flush, let alone put the lid down, he just got up in the door. “Is that why you do it, with mom?”
“What?” He looked around, shaking his head, as if he’d find something that would make this all make more sense.
“You know, it’s forbidden, and kinky.”
“Huh!’ he sat down, holding his head in his hands. Right next to me, so i hugged him, and mom hugged him too, over my shoulders. “No, I don’t know. Maybe in the beginning, I just. Liked it? I love the way it feels, and I’m not ashamed of it, but. This isn’t what I wanted for you two, and Incest?” He held me out and looked at me, “Seriously?”
“Uh, it just kinda happened?’ I looked at Paul, and lied for him. As if this wasn’t all his idea, but he didn’t make me do anything I didn’t want to, right away. Honestly, he just had to ask. “Well, it’s not like I’m going to get pregnant, or anything that way. I didn’t even take my clothes off.”
“You better put something on.” My mom picked up my top, and handed it to me.
“Why? It’s not like I have anything to cover up, and I kept my trained bra on. God, he’s stark naked, and getting a boner again.”
“Uh, Penny!” He covered it up, but too late since I pointed it out.
“Sorry, but still. How come he gets to run around topless all the time, and I have to cover up, as if you haven’t all seen me naked before, because you’re my family.”
“Huh, it’s not that.” Dad moved over, and turned around the corner, to face away. Then, I realized that he had his legs crossed, tight. Almost like a girl being modest in a dress, so I guessed that he had something to hide, too.
“A boner!” I laughed, “You got a boner, looking at Polly!”
“No?” He sounded so much like a bullied 4th grader, it was hilarious.
Mom got up, and went around, to rub his shoulders. “What is it, then?”
“It’s because he caught us fucking. Me and her.” Pauley seized the chance. “Not just fucking, but fucking Butt Fucking!” We both laughed, and mom looked up, so shocked, but then she couldn’t keep a straight face, but she didn’t laugh out loud. She just got a dirty little grin, and held dad’s head down.
“You better go,” she pointed at the dong, between my legs, and waved off for the door. “I’ll take care of him, go on.”
I looked down, and held it up, in both hands. I didn’t ask her, if she ment for me to take it off, and leave it, or take it with us, but the way she grinned, and nodded, she told us exactly what she ment.
Go fuck your brother, while I fuck your dad.
“Okay!” I grabbed Pauley’s hand, “Cummon,” and dragged him off. He grabbed the door, and pulled it shut, but before it closed, I saw dad looking back, over his shoulder, and the same dirty look on his face, when he saw I still had the strapon.
I can go on…