Part 7 of a story about a peeping teen boy. In this chapter he and his best friend Matt dress up in his sister’s undies and play with her dildo’s, then they both get caught peeping on her as she has sex with their mother’s boyfriend Brian.
After Matt and I were finished playing video games I told him that tomorrow I would be home alone in the morning and that he should come over to play with my mother’s and sister’s dildos. He told me he would be over. I left Matt’s house and went back home. It was late and my sister and mother and both of their boyfriends were home. They were all sitting on the couch watching a movie. I sat down, attempting not to make eye contact with anyone. I felt a little uncomfortable sitting in the room with my sister who I had just fucked, her boyfriend Jake who participated in a 4 way with my sister and her best friend Jena, and my mother’s boyfriend Brian who let me watch him fuck his ass with my mother’s dildo and who also fucked my 15 year old sister and made her fuck him wearing a strap-on. My mother asked me if everything was alright. As I replied to her that I was just tired I caught Brian’s eyes looking at my crotch. He subtlety grinned then looked at my sister. I followed his eyes over to my sister Kristen, she caught Brian’s glance and then looked over at me and grinned, then she winked at me and licked her upper lip. I felt my cock start to stir as I remembered those same lips and tongue sucking my cock while I was dressed in her panties. After about 15 minutes of the movie I decided to go to bed.
I slept in the next morning and by the time I got up everyone was gone. I got some breakfast and took a shower. I was just getting out of the shower when I heard a knock on the door. I wrapped a towel around my waist and went to the door. As I expected it was my 14 year old best friend from across the street. We greeted at the door then he came in. He asked me how long everyone had been gone for. I told him that we had a couple of hours. We wasted no time. I took him into my mother’s bedroom and opened her dresser. I pulled out her purple dildo and a bottle of lube. I handed it to Matt. “Wow,” He said, “It’s bigger than your hard dick.” I smiled and said, “There is more, follow me.” I took him upstairs into my sister’s bedroom. I opened her panty drawer and pulled out her strap-on and a couple of pairs of panties. I handed one to Matt and told him to put them on. He nodded as he stared at the strap-on dildo; it was a little bigger than my mother’s. He started taking off his clothes; he asked me if I had tried the strap-on in my ass. I told him yes, still not letting him know that it was my sister that had fucked me with it. I dropped the towel that was around my waist. My semi hard cock was almost fully erect, but my foreskin still covered most of my cockhead. I started putting on a pair of my sisters panties. After Matt and I both were wearing panties I pulled out a couple of bras and 2 teddy’s. Matt and I slipped into the attire, stuffing the bras with socks and panties until we both had a set of tits then slipping on teddy’s. I told Matt to look at himself in the mirror. We both laughed as he posed, looking at his own body dressed in my sister’s undergarments. I noticed his erect cockhead poking out of the top of my sister’s panties. I stood behind him and grasped his hips. I began grinding my hard cock between his butt cheeks, only my sister’s slutty panties separating our flesh. He responded by grinding back and grasping at his new breast. I whispered in his ear “Do you like being dressed up like a tranny slut?” He nodded, then said, “I want to feel you’re mother’s dildo in my ass.”
I walked Matt over to my sister’s bed. He climbed onto the bed on all fours, his ass facing me. I grabbed my mother’s purple dildo and lubricated it. I then pulled the panties Matt wore off to the side, revealing his tiny asshole and his cock and balls. I reached between his legs with my lubricated hand and grasped his hard cock, stroking it briefly. Matt moaned with pleasure. I then began to fondle his balls with one hand. With the other hand I lubricated my fingers and began circling his tight hole with one of them. I did this for a minute or two but it seemed like an eternity. Matt’s butt hole relaxed and then began to slightly gape open. I placed the head of the dildo at the opening and while still squeezing his balls inserted it. It was by no means huge, but it was longer and thicker than either of our cocks. Matt gasped and squirmed a little as he adjusted to the new intrusion in his 14 year old body. I slowly started pumping his ass with my own mother’s dildo. I let go of his balls and started stroking his 5 inch penis. Soon we had built up a good rhythm and Matt was rocking back and forth and moaning as I fucked his ass. He grasped the stuffed bra he wore; I could tell he really enjoyed what he was wearing. I began pulling the dildo all the way out of his ass then ramming back in. The first few times I did it Matt cried out in pain. But soon he was crying out in pleasure. Matt told me to stop after a couple of minutes and said, “I want to suck you’re cock while I fuck your ass with a dildo.” I grabbed the strap-on and lubed it up for Matt. Then I took off my sister’s panties and told Matt to lie on his side. I lay down on my side the opposite way. Matt and I were in a 69 position. I started sucking his cock, and then I pushed one of his legs up and slid the purple dildo into his ass. He did the same to me. I cried out in pain as Matt shoved the strap-on into my ass, he began viciously fucking my ass with it.
We continued this way for another five minutes before I felt Matt spit my cock out of his mouth. He gasped for air then cried out, “Uuuhh yes, oh fuck my slutty ass, ooohhh yes I am cumming.” His cock erupted in my mouth, shooting load after load down my throat. He then told me to cum in his ass. I flipped him onto his back and threw his legs over my shoulders. I slipped my cock into his warm boyhood. Soon I was fucking him hard, our skin slapping. His balls were bouncing around and his semi hard cum drenched cock lifelessly flopped back and forth. Before long my load was building up. I grunted as I started cumming in Matt’s ass. I shot six or eight loads into him. I fell down on top of him and we both laughed. He looked at me and said, “That was fucking awesome.” I agreed and got up.
Just as I began to clean up my sister’s room I heard someone come into the house. “Oh shit!” I exclaimed to Matt. Quick grab the strap-on.” I grabbed the purple dildo and my sister’s panties that I had been wearing. I heard my mother’s boyfriend Brian call out, “Anybody home?” He started walking up the stairs toward my sister’s bedroom. “Shit, hide in the closet.” I told Matt as he picked up the lube and pulled the panties up so he could walk. We both hid in her closet, it was a tight squeeze, but we managed. I left the closet door slightly open, but I could not see out of it, only Matt could.
Brain entered my sister’s room. I could hear him walking around. “What is he doing?” I whispered to Matt. Matt told me he had a small book bag and that he noticed my sister’s panty drawer open and started looking at them. Then I heard Matt gasp. “He just dropped his pants and he is rubbing your sister’s panties on his cock.” I heard the front door slam shut downstairs. Someone else just got home also. The person came up the stairs and I heard the bedroom door shut. Matt whispered, “It’s your sister.
“Looks like we are home alone baby girl.” I heard Brian say. “Want to play a little, I brought over my bag of toys?” I heard my sister moan in response, “Mmm, okay daddy.” I was turned on thinking about my sister and my mother’s new boyfriend having daddy daughter fantasy sex. A minute went by and I noticed Matt was rubbing his cock through the pair of my sister’s panties he was wearing. I asked him what was happening and he didn’t respond. I pushed my elbow into his side to break him out of his daze. He told me that my sister and Brian were both naked and making out. After another minute I heard a zipper followed by what sounded like items being emptied out of the bag. “Mmmm, hot,” My sister moaned, “look at some of those toys, I bet daddy likes fucking his ass with them.” Matt gasped. He had no idea my sister and my mother’s boyfriend were fucking, not to mention that Brian was bi. I heard them get onto the bed. Matt’s eyes were wide open, he was really enjoying himself. I heard the click of a cap, I guessed it was lube. Then Brian said, “No, use the biggest plug.” My sister responded with, “Wow, okay, if you say so. She giggled. About thirty seconds later I heard a grunt. Matt whispered to me, “Holy shit, she just put a huge butt plug into his ass.” I heard Brian say, “Your turn baby. Oh no, I think you should use one bigger than the small plug. How about this medium one.” My sister sighed and replied, “I don’t know, I guess so.” About a minute later I heard her crying out in pain. After thirty seconds or so her cry abruptly ended with a high pitch whimper. Matt told me that he finally got the medium plug into my sister’s ass, he also told me how hot my sister was.
By this time I was dying to see what was going on. I asked Matt if they were looking over here. He told me that they couldn’t see us. I pushed the door open a little more until I could see them. My sister was sitting on the edge of her bed, her bra was still suspending her D cup tits, I could see her erect nipples pointing threw the material. I could see all of the “toys” on the bed now. Brian had a few more butt plugs of various sizes and shape as well as a few dildo’s, some of which were huge. There also were anal beads and a butt plug that had a hose and pump.
Brian was standing in front of my sister, she was sucking his cock. I could see the rectangular end of the butt plug nestled between Brian’s muscular ass cheeks. With one hand she stroked his cock while she sucked it, and her other hand caressed his balls. Brian moaned, “Mmm Kristen, your mouth feels so good, mmmmm…” He undid her bra and pulled it over her tits. He grasped at her firm tits. After a couple of minutes Brian told my sister he wanted to eat her pussy. She obliged and laid back onto her bed spreading her legs. Brian got on the bed and put his head between her legs. His ass was up in the air. He ate my sister’s 15 year old pussy, she moaned and put one of her hands on the back of his head. He squeezed one of her breast with one hand and stroked his cock with the other. They were building up a nice rhythm, both moaning in ecstasy. Brian stopped pinching her nipple and reached down and pulled the plug out of my sister’s tight ass. She cried out in pain and pleasure as he rammed it back in. He did it again, out of pain my sister cried out and her ass jumped up from the bed. Brian rammed it back into her bowels. And her ass hit the bed again. He continued doing this to her until she was crying out with pleasure. Soon she was cumming. “Ohhh fuck yes, Suck my clit, fuck my ass daddy, oh yessss..” My sister’s legs started convulsing as she climaxed. Brian stopped stroking his cock and instead reached around and grabbed the base of the plug in his ass. He pulled it out, his ass gaping open and then began fucking his ass with it. Matt and I were both in awe.
All of a sudden Matt’s footing slipped and he stumbled, knocking over a shoe rack in my sister’s closet and also knocking the closet door open. Brian and my sister both stopped and got up to see what the noise was. They saw Matt and I, both of us still wearing my sister’s teddies with stuffed bras. He was holding the strap-on and the lube; I was holding a pair of my sister’s panties and my mother’s purple dildo. Matt was still wearing my sister’s panties, and his cock was hard and sticking out of the side of them, my cock was also erect. “Well, well, looks like we are not home alone after all.” My sister stated. Brian followed with, “I think these two young girls need to be taught a lesson, you girls have been very naughty.” Matt was totally red in the face. His cock limp already from shock. Brian sat up on the edge of the bed. I wasted no time. I went over to Brian and threw the panties and dildo onto the bed next to my sister. I stood in front of him, my cock in his face. He smiled and started stroking my cock. “I have been waiting to fuck you for too long.“ He said to me. “I know you were peeking on me when I fucked your mother, and that you also watched me when I put on that show for you, remember? Remember how I fucked my ass, I heard you cum.” My sister giggled and looked at me. “You are the biggest little slut I know. Peeping on mom!” As she said that Brian took my balls into his mouth and began sucking on them.
My sister told Matt to come over to her. Matt did as she instructed. She also sat up on the edge of her bed, next to Brian. Matt stood in front of her, she grabbed his balls and started sucking his limp penis. Before long Matt was moaning in pleasure, My sister sucking his now hard cock. After a minute Kristen stopped and said, “What were you boys doing with these toys.” She suspiciously eyed the strap-on and our mother’s dildo. I responded by moaning “We were fucking out asses with them while we sucked each others cocks.” My sister lubricated Brian’s hand and then hers, she then began sucking Matt’s cock again. Brian began sucking my cock and he slipped his middle finger into my ass. I gasped with pleasure. My sister did the same to Matt. Soon I saw my sister grab a small butt plug and shove it into Matt’s rectum. He gasped in pain. Brian did the same to me, the plug he stuck into my ass was a little bigger than the one my sister used on Matt. I felt it pierce my hole and stretch my tight ass as it slid further in. Brian held it still once it reached it’s widest point. I whimpered in discomfort. It was the widest thing I had ever had in my ass. Brian then slapped my ass cheek really hard, startling me and causing my rectum to clench shut. The plug snapped into place as I moaned in pleasure. It now filled my ass stimulating my prostate. Both Brian and my sister continued sucking our cocks. I was almost ready to cum, so I pulled my cock out of Brian’s mouth and got onto my knees.
I needed his 7 ½” uncut cock in my mouth. His cock was hard and dripping with pre-cum. His foreskin was still completely covering his cock head. I grasped his balls with one hand and with the other I grasped the base of his cock and pulled back his foreskin. His cock head was a huge mushroom cap. I started sucking just the head of his cock. I noticed Matt was watching. Matt started to moan, his legs quivering. My sister noticed and stopped sucking him. She slapped him in the face and forcibly grasped his balls. He cried out in pain and shock. “You don’t cum until I say so little girl.” My sister scolded. “Now eat my pussy you little slut.” She grabbed him by the hair. She lay back onto the bed and spread her legs and forced his head down between them. Matt began to eat his first pussy. By now I was sucking Brian’s huge cock. Taking as much of it into my mouth as possible. Brian grabbed the lube and handed it to me. He got up and told me to sit on the bed. I did and he put his cock in front of my face. He slapped my face with his cock. I began sucking him again, sucking the same cock that had fucked every hole in my mother’s and sister’s body. He moaned and told me to fist his ass. I lubricated my hand and with his cock in my mouth I reached between his legs and pulled the plug out of his ass. I formed my hand into a fist and began applying pleasure to his gaping hole. As my fist entered him he grimaced in pain. My fist stretched his sphincter so much I thought he was going to split open. Finally my fist slid all the way into him. I could feel his ass clench around my wrist. My sister yelled to me, “Ohhh yes, fuck his ass with your fist.” As she held Matt’s head between her legs. I did as she instructed, it felt really funny but Brian seemed to get off on it.
After a few minutes my sister told Matt to start fucking her. Matt mounted her spread legs, the butt plug still in his ass and maneuvered his hard penis with his hand to the entrance of my sister’s 15 year old vagina. Matt slipped it into her dripping wet cunt, losing his virginity. His primal instincts took over instantly and he began plowing her pussy with his 14 year old cock. He grasped her huge tits, pinching her nipples. I could tell Brian was close to cumming so I stopped sucking him and asked him to fuck me. He smiled and nodded. He cried out in pain as I clenched my fist inside his ass and then yanked it out if him, replacing it with his large butt plug. I laid on my back next to my sister Kristen and raised my legs into the air then spread them. Brian mounted me and pulled out the butt plug in my ass, then he placed his large cock head and my rear entrance. I looked over at my sister. She gave me a devilish smile. I noticed we were both lying in the same position. Brian began to slide his cock into my tight ass. His cock was the thickest thing I had ever had in my ass, it even had more girth than the plug he had just pulled out. I moaned in pain as he slid it into me. He rested a minute to let my anal wall accept it’s fate then he began ramming my ass. His cock hurt at first bit then I was overcome with waves of pleasure, my legs became weak. Brian began pulling all the way out then ramming his rod deep into me. My hard cock bounced around on my belly, leaking pre-cum. I looked over at my sister. She grabbed the back of my head and pulled me towards her lips. We began making out, our tongues dancing. She reached down and started jerking me off. This put Matt over the edge. He yelled, “Uhhh, OOhhhhh Kristen, I am cumming. He pulled his 5” cock out of her. It was dripping with her pussy juices. He gave it a couple of strokes and started cumming. The first rope of cum hit my sister in the face, the next two hitting her tits, and the rest of it landing on her belly. This put me over the edge as well. My sister got up and took my cock into her mouth. She sucked me as I braced for another climax. I cried out that I was cumming and held my sister’s head on my cock shooting load after load into her while Brian rammed my ass. After I was done my sister told me to eat her pussy. She straddled my head and I began licking and sucking on her hot clit, it was dripping with sex juices from Matt just fucking her. Soon she began to cum, bucking violently and screaming and moaning. This put Brian over the edge as he continued to fuck my ass. “I am cumming too” He said. He buried his cock deep into my rectum, I could feel load after load empty from his huge cock into my bowels. My sister was still cumming, she began to spray a lot of cum all over my face. I had heard of women who can squirt and seen videos of it on the internet. Her legs went into seizures and she lifted her hips up pulling her pussy away from me and started rapidly swiping her fingers across her clit. She screamed and cried in pleasure as her cum sprayed across the room and all over my body. After she finished she fell limp next to me. We decided to clean up and Brian told Matt and I that he would like to do this again. My sister mentioned that Jena’s new boyfriend was bi-sexual, and that the six of us should have an orgy. That sounded fine to both Matt and I.