Fiction, Anal, Ass to mouth, Bi-sexual, Black, Blowjob, Boy, Boy / Boy, Consensual Sex, First Time, Gay, Hardcore, Masturbation, Oral Sex, Teen Male / Teen Male, Teen Male/Teen Female, Threesome, Toys, Transvestite, Virginity, Voyeurism, Young
Part 6 of a story about a peeping teen boy. In this chapter he catches Jena’s younger sister and her friend Tanner plating doctor and joins them to give them a few pointers. Then his ass is finally deflowered by his best friend Matt. This story is not for everyone because it involves younger kids and bisexual/gay experiences.
The next day I decided to sneak over to Jena’s house and see if I could spy on her and her new boyfriend fucking again. Like usual I snuck through Jena’s neighbors back yard. I was walking past the shed when I thought I heard something coming from inside it. I paused and could here Jena’s little 11 year old sister Mandy giggling. After playing doctor with Mandy a few days ago I wondered if her and Tanner were doing the same.
I snuck around the shed and went into the back door. I snuck quietly up the stairs and spotted Mandy and Tanner both naked fondling each other’s privates. My dick began getting hard as I watched the two 11 year olds play with each other. After a minute Tanner caught a glimpse of me. He jumped with surprise and began to get red in the face. Many laughed and said, “Hi, did you come by to play doctor with me and Tanner?” I nodded and walked up to meet them. Tanner was a little shorter than Mandy, he was a cute boy with blonde hair and brown eyes. He was naked and I could see his little pre-pubescent penis. It was hard, uncut and a mere 3 inched long. He had no pubic hair and a cute little ball sack. Mandy came over to me and held my hand. She walked me over to a cot that was set up in the loft. I admired her little naked body, her flat chest and bare pussy. Mandy sat me down on the cot and put her hand on my forehead. “Hmmmmm,” she said, “It feels like you have a fever. You should take off your clothes. I smiled thinking about the last time Mandy and I played doctor, how she let me play with her little bald pussy, then she had stroked my cock until I came. I also thought about how that was before I had fucked her sister and lost my virginity, and how I had also fucked my own sister, and let her fuck my ass with a strapon.
I undressed for little Mandy. I looked over to see Tanner shyly standing in the corner watching, his little cock was now limp, his cock head concealed by his foreskin. I took off all of my clothes except me underwear. Mandy told me to stand up and I followed her instructions, after all she was the “Doctor”. She told Tanner to come over, he did as she asked. “Do you want to see his pee-pee, it is really big and he has hair down there, and he shoots a lot more semen than you do. I laughed, Mandy did also. Mandy pulled down my underwear, revealing my semi-erect cock. Almost like a pro Mandy grasped my cock with her small hands in the middle of my shaft and pulled back my foreskin to reveal my head. She giggled. I said “Mandy, why don’t you try sucking on my pee-pee, put it into your mouth.” Mandy gave me a funny look, “Ewwww, how do I know you won’t pee in my mouth or something?” I promised her I wouldn’t and she reluctantly obliged and knelt in front of me. She kissed the head a few times, while I ran my fingers through her curly brown hair. I started to guide her head down onto my cock. As my dick slid into her small mouth her blue eyes meet mine. She didn’t really know what to do, so I grabbed her hair and using gentle motions bobbed her head up and down onto my now hard cock. After a few times Mandy gagged and coughed. I pulled out of her mouth. I knew that Mandy needed a lesson.
“Mandy I will show you how to suck a penis and make a boy feel really good. Tanner come over here.” Tanner did as I asked. I sat him down on the cot, he was nervous. I told Mandy to watch closely. I spread Tanners legs and started playing with his little hairless ball sack. I then grabbed his limp dick with a couple of fingers and started stroking it. After a minute Tanner was starting to get hard. He kept looking at my cock, and then he would look at Mandy’s pussy. I pulled back Tanners foreskin and started sucking jus the head of his cock. Then I would pull it out of my mouth and flick my tongue across the tip of his head. I could taste his salty pre-cum. Soon Tanner had a full blown erection; his dick was only about 3 inches long. I told him not to cum, to tell me when to stop. He nodded. I stroked my hard cock while I started sucking his whole penis in my mouth. While giving Tanner a blow job I fondled his tiny balls. Mandy masturbated her pussy while she watched Tanner and I in awe. Before long Tanner started to grunt and he pulled out of my mouth.
I then sat on the cot next to Tanner and told Mandy to try on me again. She did much better after her little lesson. She rubbed my balls with her small hand and stroked the base of my cock with her other hand while sucking as much of my dick as she could fit into her mouth. I reached down to her flat chest and pinched and rubbed her nipples until they were hard. I looked over at Tanner who looked so innocent, just sitting there watching his friend suck my cock. He looked really cute and I felt the sudden urge to kiss him. I leaned over and tried, but he avoided me. I assured him it was alright and then he let me. We just pecked at first then I grasped the back of his head and started teaching him how to French kiss. He soon was passionately responding to my kiss, our tongues playing with each other. After a few minutes I told her to stop and she did. “Now do the same to Tanner.” Mandy obliged. She knelt in front of him and began sucking his dick. Tanner moaned with pleasure. Mandy could fit all of Tanners cock into her mouth without choking. I got up and went behind Mandy, who was knelt over Tanner. I ran my hand up the back of her little ivory legs until I reached her pussy. I slid my middle finger between her bald pussy lips, spreading her pussy juice around her little clit. I played with her little clit, she occasionally responded by twitching her legs or I would here a muffled moan. As I fondled her pussy I noticed her little brown asshole. I felt the urge to start licking it. I started moving my tongue in circles around her little brown rectum. She giggled and said, “That feels funny.” I continued to lick her ass while I fingered her, I explored her little pussy more this time, I stuck my finger into her vagina, but there was something blocking me from getting in her with my finger. I knew it was her hymen, that she was still a virgin, but that was about to change.
I told them to stop and they did. “That feels really good doesn’t it Tanner?” I asked him. He nodded and said yes with a big smile. Mandy you should know how good it feels honey. Lay down on the cot.” Mandy did. I knelt down on the cot between her legs. Watch and learn.” I said to Tanner. I spread Mandy’s legs and started to lick her little crotch. Her pussy smelt very much like her older sister Jena’s. I reveled in the thought that I had now eaten both of their pussies. I sucked on Mandy’s tiny clit and darted my tongue up and down between her pussy lips. She moaned, jerked around and occasionally giggled. Tanner watched in awe. I slid my hands under Mandy’s ass; her ass-cheeks were so small that they easily were enveloped by my hands.
After eating Mandy’s pussy for a few minutes I told Tanner to eat her pussy. He knelt down and started kissing her pussy, and soon was sucking and licking it. His rear end was perched up in the air; it reminded me of my mother’s boyfriend Brian’s ass the night I spied on him eating my mother’s pussy. I really wanted to fuck Tanners ass, but I knew it was too small and would need to be worked on for a while. Instead I reached between his legs and started milking his small cock. While I stroked him I started licking his asshole. He moaned and told me that what I was doing felt good. After a couple of minutes I told them to get into a 69 position. They did and soon they were in oral sex heaven. I stroked my cock as I watched them. Again I told Tanner not to cum yet. After a minute Mandy was crying out in pleasure as she climaxed.
After Mandy calmed down I told Tanner to lie on top of her and to put his penis into her pussy. He did as I instructed, but he was having trouble getting his cock into her. They both squirmed around but Tanner couldn’t break her cherry. I finally decided that I would have to do it for him. Tanner got up and I lay down on top of Mandy. I spread her legs and put my hard 5 ½ inch cock at her entrance. I slid my cock up and down between her pussy lips, getting her juices all over my cock head. I told Mandy that this would hurt a little and that she would bleed a little but that it would be alright. I then pushed my cock into her virgin vagina. Her bald pussy spread open as I began to enter her, her lips stretching to accommodate my cock. I finally hit her cherry and with a firm thrust burst it. My cock slid into her virgin depths. Mandy grimaced in pain and discomfort. I let my cock rest in her, not moving until she relaxed. Then with Tanner watching I started fucking his 11 year old friend. Her pussy was the tightest thing I had ever fucked, it felt so good. I looked down at her pussy and watched my cock fucking her bald pussy, it was covered in her virgin blood. After a while I picked up the pace and Mandy began to moan with pleasure. My cock only went about ¾ of the way in her before I would hit her cirvix. I was about to cum so I pulled out. I told Tanner it was his turn. Without hesitations Tanner mounted Mandy and tried to fuck her. Again he was having trouble finding her tiny hole, so Mandy reached down and grasped his penis and guided it into her. Soon Tanner was fucking Mandy with hard thrusts. A couple of times his small cock would slip out and she would guide him back into her tight hole. Tanner began to tremble and shouted that he was cumming. His thrusts stopped and he came in her pussy, his cute face expressed his pleasure. He pulled out of Mandy and I could see his cum oozing out of her. I knelt between her legs and began to eat her pussy. I could taste Tanners cum in Mandy’s little pussy. I sucked on her clit until she began to cum again, the overwhelmed with sexual desire I mounted Mandy again and fucked her tight pussy. I didn’t take me long until I felt my orgasm coming on. As I climaxed I rammed my cock as deep into her as I could, shooting load after load of cum onto her cervix deep within her newly deflowered pussy. After that we all got dressed and I made them both promise to keep our little doctors game a secret. They both agreed. Then I went back home.
Later that night Matt called and invited me over to his place to play video games. I went over and we played games for about an hour. After a while I asked him if he had found any new and hot porn on the web. He nodded and we both went over to his computer to check out some hot porn. He showed me a video of a hot tranny bitch getting fucked by a black guy with a huge cock, it was bigger than Jena’s new boyfriends cock by at least two inches. We watched the video for a few minutes as we fondled each other’s cocks. The man fucked the tranny in the ass, her tits bouncing with each of his thrusts. Matt told me how good it felt when I put my finger in his ass and that he had been using a hair brush handle to fuck his ass when he jerked off. I told him about fucking my ass with my mother’s dildo and he mentioned that he would like to try it. Soon he was sucking my cock. I told him to stop after a minute or two and I brought him over to his bed. I told him to lie down. I laid down next to him in a 69 position. I started sucking his hard 14 year old circumcised penis and he did the same to me. This was the first time I had done a 69 with another man, I enjoyed it, the feeling of a cock in my teenage mouth while the pleasure of having mine sucked. I slipped my hand between Matt’s legs and began grasping his ass cheeks. After a minute I licked my finger and then stated sucking his cock again. I began to rub my finger in circles around Matt’s tight sphincter until I felt him relax a bit. Then I slid my finger into his ass. He moaned but continued sucking me. Soon I was finger fucking his ass. We did this for a few minutes and then Matt told me he wanted me to fuck his ass.
I got up from the bed and went over to get his bottle of baby oil. I pushed him over so he was lying on his belly and straddled his legs. I lubricated my hard cock and asked him if he was ready. He said he was. I placed the head of my cock at the entrance of his little virgin boyhole. I started to push it in him. I could tell he was nervous because his ass was tight. I then began to rub my cock head up and down on the outside of his asshole until I felt him relax. Then I again began applying pleasure to his asshole. This time I slipped into his warm body. He gasped in pleasure and pain. I slid my cock ass far in as I could and he cringed and asked me to stop. I did. I told him to relax and finally he did. Slowly I began sliding in and out of his newly deflowered rectum. I could tell it was uncomfortable for him at first, but after a few dozed thrusts he began to moan. I began to pick up my pace and before long was fucking Matt’s ass roughly with deep thrusts. After a while I felt an orgasm coming on so I stopped.
I pulled out of him and asked him if he would like to try to fuck my ass. He nodded and I laid on my back on the edge of the bed. Matt put some baby oil on his cock and approached me. I put my legs up into the air revealing my boyhole to Matt, then rested my legs on his shoulders. This was one of the positions my sister made me get in when she had fucked my ass with her strap-on. Matt placed his cock at my entrance and slowly inserted it into my ass, deflowering my ass for the first time with a real cock. His cock felt really good in my ass, it was much softer than a dildo and warm. I moaned in ecstasy as he began fucking my ass. I could tell that Matt was really enjoying this as well. His cock was smaller than both my sister’s strap-on and my mother’s dildo. He continued fucking my ass, I grabbed his hand and placed it on my hard cock. He got the message and began stroking my cock. I didn’t take long before I began to cum, I bit my lip and moaned quietly so I did not alarm his parents. Soon after I could tell he was about to cum. He made a few grunts and buried his cock deep inside my ass. I could feel him empty his load in my ass. We cleaned up a bit and went back to playing video games.
To be continued……..