Part 3 of a story about a peeping teen boy, in this chapter he breaks new boundaries, playing with his first pussy, also experimenting with anal sex, using his mothers dildo, cross-dressing and more……
Thursday night after dinner my sister and Jena asked if they could go to the movies. My mother agreed and soon they all left, leaving Brian and me. My mother would be gone for an hour, so I went up to my bedroom to play video games. I was just getting settled into my first game when I saw my mother’s bedroom light turn on, the light shining up through the heat vent. I wondered what Brian was up to so I paused my game and went over to the vent. I saw Brian, naked he had a bottle of my mother’s lubricant and her purple dildo. He came over to the wall right under the vent, his cock was hard. I couldn’t believe what he was doing. I knew he was putting on a show for me. He was standing facing the wall and he lubricated the dildo and started rubbing lube on his ass. He started fingering himself. My cock was now hard and dripping with pre-cum. I started stroking, still not believing what I was seeing. After fingering his ass for a minute he placed the head of the dildo at his rectum. He slowly slid it into his ass, gasping. He began sliding it in and out, slowly then faster. Brian continued for a minute or two then he spun around, leaning his back against the wall, still standing and still fucking his ass with the dildo, I began stroking my cock faster. He started stroking his cock with his free hand. I felt my climax approaching slowly. I was so turned on and yet caught off guard, I felt the impulse to let him know I was there. I started moaning as my orgasm came closer. Brian looked up through the vent, catching my peeping eyes. He began vigorously jerking off his 7 plus inch dick as our eyes met. My orgasm rushed over me, I grunted as I shot a huge load. Brian Moaned as well and thrust the dildo into his ass holding it in, he shot his load, it sprayed all over my mother’s bedroom floor. I went back to my game after and I could hear Brian tidy things up in my mother’s bedroom and a within a few minutes I saw the light shut off. The rest of the night was uneventful.
The next morning at breakfast I heard Jena mention that her mother might go shopping and that Jena was going to have to watch her younger sister Mandy. After I finished my chores I snuck out headed for Jena’s house. My sister was still finishing her chores and my mother was at work. It was about noon and I decided to slip into Jena’s back yard, I wanted to see if maybe I could get a peek at Jena. I slipped through the neighbor’s back yard and hid in a large shrubbery on the edge of Jena’s lawn. I could see that Candy’s car was gone and Jena’s father was at work. I was about to make a run for the back of the house where I left the basement window unlocked when I saw Mandy come around the corner of the house. Mandy was about 11, she had log curly brown hair, blue eyes and freckles. She was wearing a dress with flowers on it, it came down to just above her knees. She walked through the back yard, looking bored and mischievous. I tried to remain still, but she still spotted me. She called my name and ran over to the bush. “What are you doing in there?” she asked. I told her I was playing hide and seek with Matt. She crawled into the bush with me, sitting across from me. She told me how she likes to hide in this bush. Mandy sat across me she had her knees up and her arms wrapped around her legs, I could see her little white panties and her beautiful ivory legs. “Do you want to play house in the shed?” She asked. “Sure.” I replied.
We snuck out of the bush and half way across the back yard to the shed. Once inside Mandy ran up a set of stairs that led to a loft. “This is where I play house and sometimes doctor too.” Mandy said. “Who do you play doctor with?” I asked. “Myself and sometimes Tanner from next door.” Mandy answered. Tanner was about her age. “I like playing Doctor Mandy, but you have to promise not to tell anyone.” Many agreed. She then asked me if I was feeling alright. I played along and told her no. She said “Well let’s have a look, take of your shirt and shorts.” I did as little Mandy instructed, I was now down to just my briefs. Mandy came closer to me, and pulled down my underwear. “You have a lot more hair down there than Tanner does.” She said looking at my penis. “It can also get much bigger than Tanners,” I said, “But you have to let me have a turn playing the doctor. Now take off your dress.” Mandy pulled her dress up over her head and threw it on the loft floor. She was now naked except for her little white panties, my dick started to stir while I stared at her flat chest, with two little pink nipples on it. I touched her forehead. “Feels like you might have a fever you might want to take off your undies as well.” Mandy slipped off her white panties. She stood in front of me completely naked. Her crotch was totally bald, her pussy lips were smooth and I could just barely make out her tiny clit peeking out between them. By now my dick was growing quickly. “Wow,” Mandy said looking at my semi hard dick, “It sure is bigger than Tanner’s.” She reached out and grasped it with her small hand. My dick twitched in response to her touch. She was the first girl to ever touch it. I was soon fully erect. Her hand felt soft, she squeezed my cock after it was fully hard. “The first time I touched Tanners pee-pee he shot out sperm.” Mandy admitted. “It was really sticky and smelt funny.” Mandy let go of my dick and put her hand on her forehead, pretending to be light headed. “I don’t feel well doctor, I think I need to lay down.” I played along and helped her lay down on the loft floor. I knelt by her side. “Let me check you’re heart beat,” I said. I put my ear on her chest. “It sounds a little off. Spread your legs for me.” Mandy did as I ordered. I ran my hand across her chest, stopping to caress each nipple, then I moved my hand across her belly. I didn’t stop there, Mandy giggled as my fingers touched her bald pussy, I was feeling another girl’s pussy for the first time. “What is the clear stuff dripping from you dick?” Mandy asked noticing my cock oozing with pre-cum. “Are you going to shoot sperm like Tanner does?” She said. “If you want me to,” I replied. By now her little pussy was starting to get moist. I now had my finger exploring between her pussy lips. She reached out and grabbed my dick again. This time she started gently stroking it. I told her to stroke it harder and faster, she did. Soon I was cumming, shooting my load all over Mandy’s hands. After that we both got dressed and she went back home. I did the same.
I got home around noon to find my sister was not home. I figured she was probably out with her boyfriend Jake. I was still horny after my encounter with Mandy. My mother wasn’t going to be home until after five. I decided to take a shower. I went to the bathroom and undressed, and hopped into the warm shower. My dick was still semi-hard. I couldn’t get the thoughts of Mandy’s cute little pussy out of my mind. As I washed my body with soap my hands came to my ass. I soaped up my virgin asshole with my fingers. Rubbing it with my middle finger in circular motions felt really good. Now my 14 year old cock was fully erect. Subtle waves of please crept though my balls and cock. I was thinking of my mother’s boyfriend Brian’s show for me, how he fucked his ass with my mothers didlo. I went a step further and slipped a finger into my virgin ass. I felt kind weird at first, almost like I was pooping or something. I fucked my tight ass with one finger for a while, then inserted another. Soon I had squeezed three fingers in and was fucking my ass with slow motions. My fingers could feel the walls of my tight ass and soon enough they discovered a hard lump, my prostate. After a minute of messaging the gland I was moaning in ecstasy, waves of pleasure were rolling through my crotch. I noticed pre-cum slowly leaking from my cock. This was really turning me on, I felt like a tranny slut. That gave me a kinky thought, dressing up in some girl’s cloths and finishing this with my mother’s dildo.
I finished my shower and dried off. I wrapped a towel around my waist and went into my mother’s room. I grabbed her dildo and some lubrication that was in the drawer. I relished holding the fake cock. After all it had fucked my sister and Jena, my mother and her boyfriend. It was about eight inches long and almost twice as thick as my own cock, it was shaped like an actually dick and had a vibrator. I looked through my mother’s panties and bra’s for a few minutes. I then went upstairs to my sister’s room. I found a sexy pair of black silk panties in her dirty basket. I slipped them on, looking at my sexy 14 year old ass in her mirror. I next put on one of her bra’s, this took me a few minutes to figure out, once on I stuffed it with some of her clean socks. I threw a tank top on and stood in front of her mirror. I looked sexy, I waved my hips around, imitating a girl, I was thinking about how I would probably turn on Brian and Matt, and how they would love to fuck my ass. My dick was again hard; its head was peeking out of the top of the panties.
I lay on my sister’s bed, on my stomach. I pulled the panties aside and lubricated my middle finger. I rubbed it around my asshole, slipping it in and out. Then I lubed up the dildo. I rubbed its head around my tight hole. I pushed it in, trying to penetrate my virgin ass. Pain shot through my ass, I pulled the dildo out. It took a couple of more tries before I finally got the thick plastic penis in my ass. Once it was in my rectum clenched around it holding it fast. After a minute my rectum relaxed and I started fuck my ass with the huge dildo. It was awkward at first, but soon, my legs were shivering with a whole new pleasure, one my virgin ass had never experienced. I lay on my back and threw my legs up in the air so I could continue to fuck my ass. I pulled out my uncircumcised cock, it was dripping with pre-cum. My mind was running wild, I felt slutty in my sister’s clothes, I was remembering Mandy’s pussy, and Brain fucking himself in the ass like I was now. My climax approached slowly but when it hit me it was unlike any orgasm I had had before. My whole body flushed with pleasure as I thrust the dildo in and out of my tight ass, cum spraying all over my sister’s shirt.
I lay there paralyzed from what I had just experienced for a few minutes. Then I heard the front door of the house open. I could hear my sister and her boyfriend Jake talking, they were coming upstairs! I jumped up and grabbed the dildo and the lube, I couldn’t make it to my room with them coming up the stair, the only thing I could do to not get caught like this was to hide. I hid in my sister’s closet, behind a bunch of hanging clothes. I left the door to the closet open a crack. My sister and Jake came into her room and shut the door. Jake said “Looks like we are home alone sexy, what do you say we fuck.” Jake was a good looking guy, He was 17, he had an athletic build, blonde hair and brown eyes. Soon enough they were passionately making out. As they stood in her room and kissed they undressed each other. Once naked they made their way over to my sister’s bed, the bed I just fucked my tight ass on until I shot cum. I had a perfect view, I could see across the room, and was looking at the foot of her bed. Jake’s cock was already hard, and it was circumcised and about the size of my cock, if not smaller. Jake lay on the bed and my sister started sucking his cock. She looked like she was pretty good at it. I was once again hard and stroking. My sister Kristen sucked Jakes cock for a few minutes, messaging his balls as he moaned. She then lay on top of him in the 69 position. Jake buried his head in my sister’s 15 year old pussy and began eating her pussy. My sister moaned with pleasure. I thought about the pictures of her and Jena, I knew my sister was enjoying herself; I knew she loved getting her pussy eaten. After a few more minutes of this my sister got up and turned around, she straddled Jake and grabbed his cock, she lined it up with her pussy and lowered herself onto it. She gasped as Jakes small cock penetrated her pussy. She started riding him wildly her D-cup breasts bouncing in the air; Jake grabbed one of them with one of his hands, pinching its hard nipple. They both moaned and within five minutes my sister was shaking and began to scream wildly, shaking with an orgasm. Once she settled down Jake pulled her off of him and positioned her on her knees, her ass by the foot of the bed, facing me. I could see her pussy lips were showing a tiny bit of her pink pussy, the whole area was soaked with their sex juices. Jake stood behind her and started fucking her doggy style. I continued jerking my cock, it was now actually sore from all of the erections I had had already today. Jake fucked my sister hard, I couldn’t see much, except for Jakes ass, his balls were swinging back and forth, slapping against my sisters pussy. My sister started cumming again, she screamed in pleasure, this time I could feel my balls trembling. Jake began to cum as well; he gasped and pulled out of my sister’s cunt. He stroked his cock a couple of times and shot a load of cum onto my sisters back and pussy, I came at the same time, shooting cum into my sisters silk panties that I was still wearing. They kissed and then both got up and went downstairs and hoped into the shower. After they went downstairs I slipped out of Kristen’s clothes and put them back into her hamper. I got dressed and put the dildo and lube back in my mother’s dresser. I headed over to Matt’s to see what he was up to. I couldn’t wait until tomorrow, Jena and my sister would be home alone at Jena’s parent’s house, and this might finally be my chance to spy on them…..