Fiction, Anal, Asian, Bi-sexual, Black, Blowjob, Boy, Boy / Boy, Boys/Teen Female, Cheating, Cum Swallowing, Domination/submission, Female Domination, First Time, Gay, Incest, Interracial, Male / Female Teens, Male Solo, Masturbation, Oral Sex, Teen Male/Teen Female, Toys, Transvestite, Virginity, Voyeurism, Young
Part 5 of a story about a peeping teen boy, in this chapter he finally loses his virginity, sucks his first cock and his sister catches him dressed in her bra and panties…..
After leaving Jena’s house I went home. My mother and Brian were there, she told me to mow the lawn. It took me a couple of hours, when I finished I went inside to get a cool drink and relax. I was watching some TV when my sister and Jena came in. They pretty much ignored me, but when my sister wasn’t looking Jena winked at me and licked her lips. That gave me an instant hard on. I was only hours ago that her lips gave me my first blow job ever.
The next day my sister and mom went out shopping. My mother gave me some chores to do while they were gone. I finished the chores and went upstairs to play some video games. About an hour later there was a knock on the door. I went downstairs and too my surprise it was Jena. She was wearing a tight pair of jean shorts and a skimpy blue blouse. She asked if my sister was home and I told her that she and my mother were out shopping. Jena smiled when I told her that. “So this means you are home alone?” she asked. I nodded. She came inside and shut the door behind her. Before I knew what was happening she was French kissing me. My cock was hard in a minute. She broke the kiss and said “I bet you enjoyed it when I sucked your cock?” I told her I did. “I know you are still a virgin too, you probably would like to go all the way….” After she said that she grabbed my hard dick through my shorts and squeezed it. She kissed me again. “You need to loosen up,” she said, “don’t be afraid to touch my body.” With that being said I started caressing her round ass through her shorts.
She grabbed my hand and brought me over to the couch in the living room. She pushed me down onto the couch and started to undress. She took of her shorts, revealing a sexy and skimpy pink thong, I recognized it instantly, it was one of the thongs I had found in her hamper and rubbed on my cock a few days ago, it was tight on her giving her pussy a camel toe. Next she took off her top, she undid her bra, freeing her 15 year old B-cup breasts. Next she undid my shorts and pulled them off as well as taking of my underwear. She laid on top of me and continued to kiss me. While we kissed I began rubbing her breast with one hand, her nipples became erect. With the other hand I grasped her round and firm ass. After a minute or two of this she began to grind her thong covered crotch on my hard cock. This felt great; as she did it she began to moan. After a few minutes of grinding Jena got up, I could see her pink thong had a wet spot on the front of it from my pre-cum. She grasped my hard uncut cock, stroked it a few times then started sucking it. She paused for a minute, “make sure you tell me before you cum.” I nodded. I was in heaven as her hot lips worked my 14 year old cock again. Waves of pleasure swept through my body for the next 5 minutes as very slowly I felt my climax approaching. Right before I was about to cum I told her to stop. She smiled and got up. “Your turn.” She said.
She pulled off her pink thong showing her shaved pussy to me. She sat on the couch and spread her legs. “Eat my pussy.” She begged. Her pussy was almost perfect. I had seen a lot of pussy on the internet over at my friend Matt’s house, and hers had all the qualities I liked. First it was shaved smooth. She had large and plump pussy lips and her clit was larger than most girls, it peeked out from between her lips.
I had never eaten a pussy before so I was a little nervous. I got down onto my knees on the floor in front of the couch and wrapped my arms around the outside of her spread legs. As my mouth got close to her pussy I could smell her musky scent. It kind of smelt like body odor, I instantly fell in love with the smell. I started to kiss her pussy, which made her giggle. Then I started to lick it. I was tasting her love juices and I liked every minute of it. Soon I was getting the hang of it. I was licking up and down her wet pink slit and circling my tongue around her clit. Occasionally I would suck her hard clit into my mouth and lick it with my tongue while I sucked on it. She seemed to really enjoy that, every time I did it her legs would twitch. While eating her pussy one of my hands caressed one of her firm young breasts. I used the other hand to grasp her butt cheeks and finger her pussy. I slipped my middle finger in and out of her hot vagina. As I continued she breathing got heavier and heavier until her legs started to really spasm and she closed them trapping my head between them. She cried out in pleasure as she came. As soon as she was finished cumming she yelled “Fuck my pussy, Fuck my wet pussy.” I didn’t hesitate. I mounted her and slipped my cock into her depths. I slid in with no problems and I began thrusting it in and out of her. She moaned and cried out as I plowed her. This was it, I was finally fucking a chick, and it was the hottest chick in my little world. I grasped her tits, pinching her nipples as we fucked, her hips matched my thrusts as my balls slapped her ass.
After a few minutes she stopped me, and told me to fuck her ass and to cum in her ass. She rolled over onto her belly. I straddled her as she lay on the couch with her legs closed. My dick was dripping wet with her love juices. I found her tight brown hole and slid my cock into it. It was tighter than her pussy, she gasped as I entered her ass. Soon I was fucking her ass like there was no tomorrow, I reached my hands around her to grab her tits. As I fucked her ass I thought about how good it felt when I fucked my own ass with my mother’s dildo. I could hold out no longer as I felt my orgasm coming. I buried my cock deep in her ass as I came shooting a huge load in my sisters best friends ass. I left my cock in her ass as it twitched with after sex pleasure for a few minutes until it was limp, then I pulled it out. We kissed a little more then she got dressed and left. I took a cold shower and went back to playing video games.
I didn’t see much of Jena for the next few days, and then I overheard my sister talking to Jena Jena on the phone about Jena’s new boyfriend. The next day Jena came over but she wouldn’t give me the light of day. This didn’t stop me from going over to Jena’s house when her parents were not around too peep on her while she fucked her new boyfriend. His name was Dave, and the first time I saw his cock my jaw hit the floor. He was black and his cock was bigger than Brian’s cock. It must have been at least 9” long and thick as well. He was uncut and watching them fuck in Jena’s bedroom really turned me on.
The day after I peeped on Jena fucking her boyfriend I went over to my friend Matt’s house. We hung out in his room, surfing porn on the internet. It started with porn of lesbians, then we moved onto porn of women fucking men, and inevitably we ended up watching our favorite type of porn, tranny porn. After a few minutes of watching a hot Asian tranny ride cock while sucking another cock Matt got out the baby oil. We usually would jerk each other off but this time before he lubed up I asked him if I could suck his cock. He seemed a bit nervous but agreed. He stood in front of me and dropped his shorts. I got on my knees and started jerking his 5” circumcised dick. I then started licking the end. He moaned with pleasure. I could taste his salty pre-cum. Next I slipped his cock into my mouth. It felt hot having a dick in my mouth, I tried to mimic what Jena had done to my cock, I sucked on it, sliding it in and out while teasing the head with my tongue. Matt moaned with pleasure.
After a minute or two I stopped and asked him if he wanted to try. He agreed and awkwardly he began sucking mine. Matt was not very good at sucking cock yet but that didn’t bother me. He stroked his little cock as her sucked on mine. I could tell Matt was starting to enjoy what he was doing. I told him to stop and that it was my turn again. I lubricated my cock with baby oil and stroked it with one hand as I knelt in front of him and took his cock into my mouth again. I continued to stroke my cock with one hand, while rubbing his balls with the other and sucking his penis. The Asian tranny began to cum, I could feel that Matt was about to also. I wanted to give him a little surprise this time. So as his climax approached I positioned my lubricated hand on his ass, squeezing his butt cheek and nestling my middle finger on his tight rectum. I felt his dick start to throb in my mouth, I knew he was cumming, I slid my finger all the way into his ass as he came. His cum shot into my mouth and hit the back of my throat. It gagged me at first. Matted and I usually were pretty quiet when we jerked each other off so we wouldn’t get caught by his parents, but this time Matt was overwhelmed with pleasure and he let out a loud groan as he came. His cum tasted funny, but I swallowed it anyway. It was now my turn, I laid on my back and started finger fucking my ass as I jerked off. Matt watched and finally reached out and gave me a hand job until I shot my load.
We cleaned up and Matt told me that when I stuck my finger in his ass it felt really good. I told him about how I fucked my ass with my mother’s dildo, he told me he would like to try it sometime. When I left Matt’s house his parent’s eyed me suspiciously, I am sure they were wondering what we were up to.
The next day I was home alone, my mother was at work and my sister had just left to go babysit. I took a shower and grabbed my mother’s dildo after. I went back up into my sisters room, I picked out a bra, put it on and stuffed it with socks, then I put on a sexy silk teddy. I grabbed a pair of her dirty underwear from her hamper and put them on. I admired myself for a while in the mirror before laying down on her bed to get down to business.
I sucked on the dildo for a while pretending it was my mother’s boyfriend Brian’s cock. Then I lubricated it and started fucking my ass with it. I pulled my cock out of the side of my sister’s dirty panties and started stroking it. I continued for a minute then I heard my sister yell…. “What the fuck! What are you doing in my room dressed up in my clothes?” I was shocked. I froze, lying there on my 15 year old sister’s bed, totally dressed up in her slutty attire, fucking my ass with my mother’s dildo. “Uhhmmmm…” I attempted to say something but I was clueless as to how to explain this situation to my older sister.
She then without saying a word started undressing. She took of her shirt and bra, revealing her firm and plump D-cup breasts. This must have been turning her on because her nipples were erect. She then slipped off her shorts and underwear revealing her pussy, with a strip of blonde pubic hair neatly groomed. She came over to her bed and without a word started sucking my cock. I moaned. She stopped for a minute and said “I never knew you were this much of a slut, dressing up in my panties and fucking your ass with mom’s dildo.” She continued sucking then grabbed the dildo and started working it in and out of my ass. With my free hands I grasped her huge breasts. She moaned as I pinched her nipples. “Ohhh Kristen,” I moaned. “Ever since you showed me your pussy I have wanted to fuck you, even if you are my sister.” She stopped sucking my dick and smiled at me, then she shoved the dildo as hard as she could deep into my ass. Pain shot through my body, I had never put the whole thing in me before. I winced and jerked in pain. My sister gave me a devilish smile while slowly sliding the dildo out of my ass and said “I bet you want to fuck me, but first I have a real surprise for my little gay cross-dressing brother, I am going to give you a little fuck first.” Again she slammed the dildo all the way into my ass, pain shot through my ass again.
She got up leaving the dildo in my ass, it slid out on it’s own. She went over to her dresser and rummaged through the middle drawer and pulled out a strap on dildo. It was flesh colored and it was bigger than my mom’s purple dildo, in fact it was just about the size if my mother’s boyfriend Brian’s cock, about 7 ½” long and thick. As my sister put it on she said “This was a little present mom’s boyfriend Brian gave me the other day, don’t tell mom but he and I have fucked a couple of times, and last time he had me fuck his ass with this.” Wild thoughts ran through my mind of Brian and my sister Kristen fucking as I lay on my sisters bed. She told me to get in doggy position so I followed her instructions. I knelt on all fours on the edge of her bed. She got behind me and lubricated the strap-on. She moved the panties over to the side, exposing my butthole, then she slowly teased my ass by rubbing it’s head around my ass. Next she slowly slipped it in. It really hurt because it was much thicker than my mother’s purple dildo. Once it was in she started fucking my ass. It hurt for the first couple of minutes then the pain started to go away and it started to feel really good. Soon I was rocking my hips matching my sister’s thrusts. The strap on kept sliding in and out of me, stimulating my prostate and causing my hard cock to leek pre-cum.
After a while she stopped and told me to lie on my back. She spread my legs and stated fucking me again. She used one of her hands to stroke my cock, while I grasped her bouncing tits with my hands. It wasn’t long before I started cumming, shooting my load all over as my sister stroked my cock and rammed my ass. It was the best orgasm I had ever had.
After I finished my sister said “I am not through with you yet, you little whore.” She took off the strap-on and she crawled on me backwards. I was now staring at her pussy right above me, I knew what she wanted. She buried her wet pussy in my face and told me, “Eat my pussy like you ate Jena’s, she told me all about the two of you fucking, she said you were pretty good at eating pussy for a beginner.” Her pussy smelt different that Jena’s, more of a sweet smell. I began lick her crotch. My sisters had a smaller clit that Jena, I nibbled and sucked on it. She took my half-erect penis into her mouth and sucked it until it was rock hard again while rubbing my balls with one of her hands. We both moaned as we pleased ourselves in a 69 position. After a while I could tell my sister was getting close to cumming. She got up off me and turned around. She startled me, grabbing my dick and lining it up with her pussy. We looked into each other’s eyes as she sat down onto my cock. She felt looser than Jena, that might have something to do with Brian’s fat cock fucking her, it was still unbelievably hot to feel my cock slide into my sister’s pussy. Soon she began rocking her hips back and forth, slowly at first then faster and faster. I grasped her huge tits as they bounced around, pinching her nipples. She began to breathe heavier and heavier before she started to yell “I am cummmminggggg, uh, uh……oh ya….” After she calmed down I pushed her back onto her bed and straddled her chest. I held her big tits together and started titty fucking them. She started fingering her clit and climaxing again. My sister was apparently very vocal when cumming, she continued to scream and moan as multiple orgasms rushed through her, causing her legs and hips to violently thrust around. She grabbed the purple dildo with her free hand and started fucking my ass with it again. It didn’t take long before I felt another climax coming. I shot my cum all over my sisters face and blonde hair.
After we were done I told her she was a bit of a slut too, we both laughed at that. Then she told me to give her clothes back to her and to stay out of her room. She left after that to go over to Jena’s, I am sure she was going to tell Jena about what just happened. I didn’t see my sister again until the next morning, She acted perfectly normal as if nothing had ever happened.
Part 6 coming soon. In it he gives Jena’s younger sister Mandy and her friend Tanner a sex lesson, Brain catches him and Matt fucking and joins, and his mother walks in on a 7 way orgy!