I am fourteen years old the youngest child in my family. I was what they call a change of life baby. My mom and dad are over sixty-five and retired. Most of my five older brothers have children older than me. I am in the ninth grade and have a niece in the twelfth grade that calls me ‘Uncle Brian’ whenever she sees me in the halls.
I have a fourteen-year-old best friend called Jim. He is the oldest in his family with two younger sisters that are fifteen and twelve. His mom is really hot and not married any more. My mother is sixty-six-year-old while Jim’s mother is just thirty-three.
We chose to pair up in science class for a project. That Saturday morning I went to Jim’s house to start work on it. His mom made sure we had drinks, snacks, and that the two girls left us alone. By lunchtime we were finished.
As we ate lunch Jim’s mother asked me if I would like to spend the night. Every Saturday was movie night. Jim said that right after dinner they all get ready for bed and eat popcorn while they watch the movie. Tonight was ‘chick flick’ night and the next Saturday was going to be ‘action adventure’ night. He assured me that ‘chick flick’ was not all that bad. So I called my mother and it was okay if I wanted to spend the night.
We played around after lunch and let his sisters join us. The fifteen-year-old was Megan she was kind if cute. She was quite mature for her age as she must have had a 34c cup breasts and I enjoyed being around her. The twelve-year-old was Susan she really was going to be quite a hottie when she got older. She too had well developed breasts.
Eventually Jim’s mom started dinner. We also knew that ‘movie night’ would not be to long off. She let Megan and I help her and sent Jim to look for his youngest sister. Megan had on a loose top with a scoop neckline and every time that she bent over I could see most of her bra and some of her breasts. Jim’s mother caught me looking down Megan’s top she just smiled at me. I took that as if she didn’t mind so I kept looking. Megan didn’t mind as she knew I was looking at her. She would push her tits up when her mom wasn’t looking to give me a better view.
Dinner was great his mom could open up a restaurant with her cooking. Jim’s mom sat my desert in front of me I was looking down her top to see the swell of her breasts in her bra and she stayed like that for a long time just smiling at me. After dinner was over she asked me to help her with the dishes while she sent her children up to their rooms to get ready.
Shortly Megan came down to start the popcorn in a hot air popper. I was absolutely amazed to see her in just a skimpy pair of pink panties and a tight white sleeveless T-shirt that clung to her breasts very nicely. Jim’s mom saw me staring she smiled when I made eye contact with her. When we were done with the dishes Jim’s mom asked me to unhook her bra so that she could go up and change. I hadn’t ever unhooked a bra before and I didn’t know what to do so she removed her shirt so that I could see the tiny hooks. I just looked at her standing there in just her bra. I looked at her large heaving breasts as she breathed. I managed to get the bra hooks undone but her bra stayed on her breasts as she walked out of the room. Jim came down and told me to go up to his bedroom and get ready for movie night. He was just wearing his underwear and I could see the bulge of his privates.
So I walked up the stairs to his bedroom passing his mother’s bedroom on the way. I heard Susan talking to her mother as I walked by and looked in. Susan was just wearing a pair of yellow thong panties and a yellow bra I could see her breasts and nipples. Jim’s mom was completely naked and holding her nightgown over her head as she put it on. I stood there looking at her bare breasts and her neatly trimmed pussy. As the nightgown came down over her face she looked directly at me and just smiled. I watched as she shuffled her top to get it over her heaving breasts as I watched. Her gown was transparent and I could see her breasts quite clearly even with them covered up. Then she turned to pick up the matching panties and showed me her bare ass at the same time. She looked right at me as she pulled her transparent panties up her legs and adjusted them into her crotch. When the show as over I went into Jim’s bedroom and removed my clothes.
Jim’s mother was waiting for me to come out in just my underwear. I had a huge erection because of her and she just smiled at me. Then she asked me if I could take care of it by myself or if I would like her to help. I was absolutely speechless so she pushed me back against the wall and got on her knees right there in the hallway. She pulled my underwear down, grabbed a hold of my cock, and then sucked my cock into her warm wet mouth. That was my very first blowjob. Her mouth felt so good I knew I couldn’t help but cum quickly but wanted to hold out as long as possible. She sucked on my cock licking the head while messaging my nut sack She had her lips on the head kissing it as I exploded in her mouth. She sucked until nothing else came out. She pulled my underwear back up for me and we joined the other kids downstairs. The popcorn was ready, the sodas were poured, and they were just waiting for the okay to start the movie.
Jim and his two sisters lay down on the rug in front of the television on their bellies. Jim’s mom had me sit up on the couch with her. I looked at Susan’s panty covered ass and then I looked at Megan’s panty covered ass. Megan’s ass looked so much better.
I couldn’t believe it when I saw a naked woman on the screen. Then I saw the XXX rating. I had never seen a movie like that before. It was a incest story complete with all of the nudity and sexual action. I watched as the girl on the screen masturbated. Megan and Susan started masturbating in front of me on the floor. Megan had her hand in her panties she was really going at it. I looked over at Jim’s mom she too had her hand in her panties. As the scene on the screen unfolded Jim’s mom moved my finger to her clit. As the girl in the movie had her orgasm so did Susan, Megan and their mom.
The next scene had a guy and a girl making love. Jim and Megan started acting out what they saw on the screen. I watched as Megan slip off her panties and her shirt, as Jim put his cock between her pussy lips and rubbed up and down as to get her moisture on his cock head. Then he slipped his cock in his sister’s pussy. They started fucking slowly; it wasn’t their first time fucking and they knew how to enjoy themselves. Jim’s mom stroked my cock and then she told me that I could fuck her if I wanted too. Oh yes, I sure wanted too. Jim’s mom removed her transparent panties and then she started to remove her negligee top I stopped her. I removed my underwear I got into position between her legs just like Jim had with his sister Megan. I rubbed my cock head on her swollen pussy lips, and clit. Slowly I pushed my cock into my very first vagina then I rested my chest on her breasts and enjoyed the feel of the silky material between us. As I slowly fucked her I watched the couple on television and I watched Jim fucking his sister. She pulled me close her face next to my ear. “Fuck me hard baby, I need it bad”. I was so excited I started pounding her for all I was worth. She was moaning and thrashing her hips to meet my downward strokes. She started to shutter, clamped her legs around my ass. I felt her pussy contracting around my cock. My god I started filling her pussy with my cum.At that moment we heard a soft scream of pleasure, Jim and Megan were cumming, he filled his sister’s pussy with a big load of cum.
Jim’s mom kissed me and thanked me for fucking her. Then she got on the floor over top of Megan as Jim and I watched them. Susan was watching them as she fingered herself. I got on the floor closer to Megan’s pussy and watched as Jim’s mother licked it. Susan was close to me so I reached out and removed her panties before sticking my finger in her pussy. Susan moved my finger up to her clit. I was rubbing her clit as I watched her mom and her sister go at it. I occasionally looked at the television but mostly stared at Jim’s mom’s tongue slipping in and out of her daughter’s freshly fucked pussy. Her face was covered with Jim’s cum.
I moved Susan came with me. We went around to the other end so that I could watch as Megan licking my cum out of her mom’s freshly fucked pussy. Susan liked watching too, she especially liked it as I kept fingering her clit which now was rock hard..
The next scene was of a girl with two guys. Jim’s mom told Jim and I to use Megan. I couldn’t believe that the girl on the screen had a cock in her pussy and another one in her ass at the very same time. Megan put me on my back and then she sat on my cock. Her pussy felt just as good as her mom’s pussy had felt. She laid her breasts down on my chest and let Jim slip his cock into her asshole. She told me not to worry because he had butt fucked her before. She said that it was her very first time for double penetration though. As we got going I just watched the expression on her face turn to pure pleasure and then I stared at her breasts swaying. Our cocks were both in Megan, our cock head were together in her separated only by her membrane. The feeling was electric. As I looked over at Jim’s mom there was Susan in her arms sucking on a breasts while Jim’s mom was rubbing her clit quickly. She appeared to be ready to cum. Then Susan moaned and her mom kept rubbing as she had an orgasm. Megan moaned, she was having an orgasm. Jim pulled her deep to him and started cumming in his sister’s ass. The sensation caused me to erupt in Megan’s pussy as she moaned with delight.
After the movie ended Jim’s mom asked me if I wanted to sleep with her or sleep with Megan I picked her. Jim got to sleep with his sister that night.
It was only about eight o’clock at night and I wasn’t at all tired but I still went to her bedroom with her. Jim’s mom took me into the shower and asked me to wash her all over inside and out. So I got to wash her big tits, her firm ass, and her great pussy then I got to slip my fingers into her pussy and into her ass. She had me slip my fingers into her mouth too so as to leave no stone unturned. I thought about sticking my fingers in her nose and ears but I didn’t.
She noticed my erection and asked me which of her holes that I wanted to fuck. I chose her asshole and she just bent over in the shower and offered her ass to me. I put extra soap on my hand and lathered it up around her asshole before slipping my cock into her. As I butt fucked her I told her that I wanted her to get on top of me and fuck me the next time we made love. She laughed and said that she had expected that after watching me when Megan was on top. I reached around and held her swinging breasts in my hand as I fucked her rectum. My pace quickened, she was moaning with animal pleasure. I pulled her as close as I could. When I started to cum flooding her bowels she fucked back at me giving me more encouragement.
We dried off and lay in her bed together. She cuddled me into her breast and asked me about my evening. I told her that I had been a virgin she said that she had figured that out. I told her that she had been the first woman that I had ever seen nude. I told her that cumming in her mouth, her pussy, and in her rectum had been my truly wonderful. I told her I would like to suck on her breasts, tongue her asshole, and eat her pussy to complete my firsts sexual experience.
I told her that I had never kissed a girl either. Jim’s mom rolled me over and planted her lips on mine. We kissed and kissed for several minutes before she crawled up to slip a breast into my mouth. After a while she changed breasts then she turned around into a sixty-nine so that I could taste her pussy while she sucked my cock. She wouldn’t let me cum but she moved to give me better access to her asshole and I liked it. Jim’s mom then got on top of my cock and rode me as I looked at her bouncing breasts I played with them with my hands. She told me to roll her nipples between my fingers and to pinch and twist them too. Her breasts were fun to play with and she didn’t seem to care. I was close to cumming again. She covered my face with her breasts whispered “Fuck me hard baby”. I was cumming in two seconds for the last time that night as I felt completely drained. Jim’s mother suggested she put on her panties to let my cum stay in her. I agreed as she told me this way in the morning we could both see the stain. Then we cuddled and talked until we fell asleep.
In the morning Susan came in and woke us up. Megan had told her that my cock had felt better than Jim’s cock had felt inside her pussy. Jim’s mom confirmed that my cock did feel better than her son’s cock had felt in her pussy too. Susan wanted to feel it in her pussy too but her mom told her that she would have to wait a couple more years until she was fifteen.
So I kissed Susan, sucked on her nipples for a little while, and then I fingered her pussy like I had the night before.
Megan joined us in her mom’s bed. We were all naked and I was openly fondling the three girl’s pussies. They seemed to be enjoying it as much as I was. Megan told her mom that she wanted me to fuck her before I went home. Her mother smiled and replied that she wanted me to fuck her too. That was when I watched Jim’s mother do a Russian Split where her legs went straight out to the sides exposing her pussy very nicely. I had never seen such a thing before. Her pussy lips opened up being spread out wide like that and I could see her clit and her open hole plainly. Megan got on her back on top of her mom’s belly and opened her legs up into a Russian Split too. I was looking at two very open pussies at the same time and just inches apart. Megan told me to fuck both of them at the same time. Wow!
I got up close to them on my knees and leaned over Megan. I sucked on her nipple as I slipped my cock into her mom’s pussy. I stroked her a few times as I sucked both of Megan’s nipples. Then I went up further to kiss Megan on her lips as I slipped my cock into her pussy. I leaned over to the side and kissed Megan’s mom as I continued to fuck Megan. My mouth went from nipples to lips as my cock went from pussy to pussy. It felt incredible. Fucking two girls at the very same time was more than my cock could handle. I sank my cock balls deep into Megan’s mom’s pussy and started to cum. I knew in my own mind that I had done more in the last twenty hours than most men had ever done in their whole lives. Susan and I watched the two girls slide into a very sexy sixty-nine position so Megan could gobble up my cum from her mom’s pussy.
Jim finally got out of bed and joined us in his mother’s bedroom. Megan and Susan told their brother all about the threesome that we had just finished. At first he thought that Susan had been involved but his mother set him straight.
We all showered and went down to the kitchen for breakfast. No one got dressed because there was no need too. After all we were just going to start having sex again after we ate anyway. Jim was talking about fucking his mom and his sister in that Russian Split like I had. But Jim’s mother talked about me ‘tit fucking’ her next to round out my education. I told her that I would love to tit fuck her after all she was already all of my firsts. She was the first naked lady that I had ever seen, she gave me my first blowjob, I fingered her pussy first, I fucked her first, I anal fucked her first, my first sixty-nine was with her, and my first threesome with two girls was with her too. Megan was my first double penetration with another boy but fucking Jim’s mom was what it was all about.
After breakfast we all went up to Jim’s mom’s bedroom for my tit fuck. She applied very little lubricant between her breasts and had me sit on her ribcage. As I held my hard cock flat to her chest she pushed her tits together from the sides. It formed a tunnel that I was to fuck. Actually it felt a lot better than I had expected. It was just as good as my hand but not as good as her three holes had been. I smiled as she licked my cock head as it came out of her smashed together tits near her chin. Megan and Jim cheered me on until I was pumping furiously. As my cock twitched I started cumming on their mother’s face. Jim’s mom caught some in her mouth but I hit her hair, one of her eyes, and her nose too. She was quite a woman.
I noticed that Jim’s mom didn’t let Jim fuck her while I was there so I asked her about it. She told me that she thought of him as her son and not as a lover but that occasionally she would let him fuck her when she was really horny. Mostly she encouraged Megan to take care of her brother’s sexual needs. Megan took very good care of his sexual needs and her own, practically twice a day every day. Susan was just too young and her pussy was just not developed enough for sex yet, but the poor kid really wanted to join in whenever she could.
Jim’s mother invited me to come over after school every day to fuck her if I wanted too. I told her that I would love too.
That Monday at school my niece Tonya the senior said hello and called me Uncle Brian. I introduced her to my best friend Jim then I asked her if she had ever thought about a threesome with two boys before. Then my niece Tonya smiled at us both and said that she had thought about it before the thought really turned her on too. Jim told her that his house was available that day after school if she wanted to give it a try. Tonya just smiled sweetly and said that she would meet us out front right after her last class. Tonya had teased me before over the last few years so I really wasn’t expecting her to come through.
When the last class ended Jim and I rushed outside to wait for Tonya. We thought that she had stood us up when we finally saw her coming out. She was with a girl friend. They laughed and walked toward us. Tonya told the girl that she was going to baby sit us and grabbed us both by the back of the neck and marched us away. About a block away Tonya started laughing and told us that she had just done that to cover up what we were actually going to do. She said that it was none of her girl friend’s business as to what she was going to do with us.
Jim had called his mom and told her what was up with Tonya so when we arrived there was a note on the front door letting him know that she took his two sisters shopping and that she had left him and I a snack in the refrigerator. It ended with see you in two hours.
Tonya seemed really happy to know that we had the house to ourselves and that we hadn’t been screwing with her about it. We escorted Tonya up to Jim’s bedroom. First she wanted to know if we had ever had a threesome together and we replied that we had. Then Tonya wanted to know whom it was with. Cautiously I told her that it was with Jim’s fifteen-year-old sister Megan. Tonya wanted to know who was in her ass Jim said that he had been. Then Tonya wanted to know if I had ever had anal sex. I told her that I had. Of course she then wanted to know with whom. Bashfully I told her that it was with Jim’s mom. She didn’t believe me. She didn’t believe Jim either. So Jim called his mom.
Tonya listened as Jim filled his mom in on what had taken place so far then handed the phone to Tonya. She talked to Jim’s mother, listened to what she was saying, and then asked questions. Soon Tonya handed the phone back to Jim and said that his mother was coming home.
While we were waiting we went to kitchen and ate the snack. I couldn’t help but wonder what Tonya was up to. One moment she was all for double penetration and the next moment she wanted to know everything about Jim and I and our sex lives.
Finally Jim’s mother arrived with Megan and Susan we sat in the living room to talk. Susan was sent up to her room to play. Jim’s mom and sister then told Tonya everything that she wanted to know. Tonya was very curious indeed. Especially about what it had felt like to Megan to have two cocks in her at the same time. After a little bit of talking Jim’s mother suggested that Tonya find out for herself. So we then went up to his mother’s bedroom. Jim’s mom and sister got undressed quickly and Jim and I followed suite. Tonya eventually undressed too. She was probably my prettiest niece. She was tall, slender, and physically fit. She jogged every day and watched what she ate. She had long blonde hair, a nice firm ass, and her tits were as big as what Jim’s mother had. At eighteen she was a real knock out. Megan volunteered to go first and Tonya let her. This time Jim got on his back and Megan sat on him. Jim’s mom greased up Megan’s butt and my cock then slipped in her butt. After just a minute Jim’s mother told us to stop before we cum. Then she asked Tonya if she wanted another demonstration. She said that she tried not to let her own son fuck her but that she encourages him to fuck his sister.
When Tonya asked her why, Billy’s mother simple replied that it was because that was the way that she was brought up. Her mother wouldn’t let her own sons fuck her but she encouraged them to fuck their sisters. Jim’s mother had two sisters and three brothers so it worked out pretty even. All three of her brothers fucked her for years and kept her sexual satisfied.
Tonya told me to stick my cock in Jim’s mom’s ass so that she could watch. Jim’s mother didn’t care and just got on her hands and knees on her bed while I stood behind her. She said that I was lubricated more than enough for her so I just pressed my cock into her sphincter. She relaxed and I slipped right in. After a minute Jim’s mom told me to pull it out and save it for my niece. It was clearly Tonya’s turn now. Apparently she had been stalling because even though she was intrigued by anal sex and double penetration she was an anal virgin.
Tonya placed Jim on the center of the bed and climbed above him. We all watched as she lowered her pussy into his rigid cock and settled in for a long comfortable ride. Jim’s mother greased up Tonya’s asshole for me and re-coated my cock. I watched as she slipped one and then two fingers into Tonya’s asshole making sure that her sphincter muscle was nice and loose. I knelt behind my beautiful niece and placed my cock at her entrance. I could see Jim’s cock in her puffy pussy. I pressed slowly and she relaxed until the head popped just inside of her and then she had me stop. A few moments later she had me proceed again. Inch by inch and moment by moment I eased my rock hard cock deep into her virgin rectum. I could feel Jim’s cock right up against mine as if we were in the same hole. Megan asked Tonya if she felt full and she said that she did. Megan asked Tonya if it felt good and she said that it did. So Jim and I double fucked my eighteen-year-old niece Tonya. Megan got on one side and stimulated one of Tonya’s breasts and nipples. Jim’s mom got on the other side and stimulated that breast and nipple while she kissed Tonya. The four of making love to Tonya was more than she could sexually handle. Tonya fell into a series of non-stop screaming orgasms. It was her very first multiple orgasm ever and it rocked her world completely. When Tonya regained emotional control Jim was pumping hard he started to cum in her pussy and that sent her into another series of screaming orgasms. I held off for as long as I could finally I pulled her deep I started to cum in her ass in her virgin ass while she experienced yet another few screaming orgasms. Tonya collapsed on top of Jim in an unconscious state while I pulled my cock out and rolled over near Jim’s mom. I couldn’t believe that I had just butt fucked three different women in less than an hour.
I helped to roll Tonya over so that Jim could get out from under her. Susan joined us and we took turns playing with Tonya’s nice breasts while she was still out. We kissed them, sucked them, and we pinched her nipples all that we wanted too. Eventually Tonya came around. She was delirious with pleasure and asked us to do it to her again right away.
That second time I got on my back and watched her climb on my cock. I felt Jim’s cock slip into her ass and then I watched Megan suck on one of her nipples. Jim’s mom started kissing Tonya right there in front of me. Soon the three of us were trading off kisses and each of us kissed the other two. Jim’s mother asked Tonya how it felt. She said that she still had the full feeling, that her butt was getting a little tender, Jim was a lot more aggressive in there than I had been. Megan told Tonya that Jim was always aggressive when it came to sex. Tonya started to get that wonderful feeling again and then she closed her eyes and rolled through a whole series of multiple screaming orgasms as the four of us stimulated her body. With a cock in both of her holes, both of her nipples being pinched and twisted, me caressing her back with my fingernails, and Jim’s mom French kissing her Tonya didn’t stand a chance. She sexually overloaded and twitched she spasmed and then collapsed on top me. That time we just roller her over, covered her up, and started dinner.
When dinner was ready we took our plates and Tonya’s plate up to her. We all sat on the bed and ate while Tonya told us how much she loved having Jim and I double penetrate her body. She asked Jim’s mom if she could come back again. Tonya was told to come home with Jim and I after school at least three times a week. She agreed.
So for the rest of the school year Jim and I got to double penetrate Tonya three days a week and Megan two day a week. Other than that I got to fuck his mother the rest of the time and Jim got to fuck Megan.
Tonya started to introduce Jim and I to all of her girl friends. It seems that her Uncle Brian was the talk of the girl’s locker room thanks to Tonya. Senior girls were asking me out. They could all drive and they all wanted me to fuck them. We didn’t go to dinner or movies we just went to some secluded place to fuck in the back seat.
Every day after school I went home with Jim. With his mothers help I learned just about everything that I could possibly learn about sex.
When Tonya graduated I was there. I had had sex with at least twenty-seven of the girls in that graduating class. I was already planning to do better with the next graduating class.