I get to fuck my best friend’s mother and his sister.
Fbailey story number 221
I am fourteen years old and the youngest child in my family. I was what they call a change of life baby. My mother and father are over sixty-five and retired. Most of my five older brothers have children older than me. I am the only child still living at home too. 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 Billy. He is the oldest in his family with two younger sisters that are thirteen and ten. His mother is very pretty and not married any more. My mother is sixty-six-year-old while Billy’s mother is just thirty-three. Hell my youngest brother is thirty-four years old.
We chose to pair up in science class for a project. That Saturday morning I went to Bill’s house to start work on it. His mother made sure that we had drinks, snacks, and that the two girls left us alone. By lunchtime we were finished.
As we ate lunch Billy’s mother asked me if I would like to spend the night. Every Saturday was movie night. Billy said that right after dinner they all get ready for bed and eat popcorn while they watch the movie. That night 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 thirteen-year-old was Julie and she was kind if cute. She was quite mature for her age and I enjoyed being around her. The ten-year-old was Tina and she really was a little girl. I kept a close eye on Billy’s mother whenever she was around. She was so pretty that she could be a movie star or a model.
Eventually Billy’s mother started dinner and we all offered to help her. We also knew that ‘movie night’ would not be to long off. She let Julie and I help her and sent Billy to look after Tina. Julie and I got to fix a tossed salad while her mother did everything that was hot on the stove. Julie 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. Billy’s mother caught me looking down Julie’s top and she just smiled at me. I took that as if she didn’t mind so I kept looking. Julie didn’t even seem to notice.
Dinner was very good and Billy’s mother was a lot better cook than my mother was. She should open up a restaurant. When Billy’s mother sat my desert in front of me I looked down her top to see the swell of her breasts in her bra and she stayed like that for a long time as she smiled 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 Julie 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 small breasts very nicely. Once again Billy’s mother saw me staring and just smiled when I made eye contact with her. When we were done with the dishes Billy’s mother asked me to unhook her bra for her so that she could go up and change too. 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 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. Soon Billy was 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 Tina talking to her mother as I walked by and looked in. Tina was just wearing a pair of panties and I could see her slightly budding breasts. Billy’s mother 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 Billy’s bedroom and removed my clothes.
Billy’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 that I couldn’t help but cum way too quickly. She sucked my cock clean, kissed the head, and then pulled my underwear back up for me. Then 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.
Billy and his two sisters lay down on the rug in front of the television on their bellies. Billy’s mother had me sit up on the couch with her. I looked at Tina’s panty covered ass and then I looked at Julie’s panty covered ass. Julie’s ass looked so much better.
I couldn’t believe it when I saw a naked woman on the screen. Then I saw the MA mature rating. I had never seen a movie like that before. It was a romantic love story complete with all of the nudity and sexual action. I watched as the girl on the screen masturbated and then as Julie and Tina masturbated in front of me on the floor. Julie had her hand in her panties and she was really going at it too. I looked over at Billy’s mother and she too had her hand in her panties. As the scene on the screen unfolded Billy’s mother put my hand in her panties and moved my finger to her clit. As the girl in the movie had her orgasm so did Tina, Julie and their mother.
The next scene had a guy and a girl making love. Billy and Julie acted out what they saw on the screen. I watched as Julie slipped off her panties and her shirt, as Billy slipped his cock into his sister’s pussy, and as they started fucking. It wasn’t their first time to fuck either. Billy’s mother stroked my cock and then she told me that I could fuck her if I wanted too. Oh yes, I sure wanted too. Billy’s mother removed her transparent panties and then she started to remove her negligée top but I stopped her. I removed my underwear and then I got into position between her legs just like Billy had with his sister Julie. I slipped 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 Billy fucking his sister. I was so excited that I filled her pussy with my cum just as Billy filled his sister’s pussy.
Then the screen changed to two girls. Billy’s mother kissed me and thanked me for fucking her. Then she got on the floor over top of Julie as Billy and I watched them. Tina was watching them too as she fingered herself. I got on the floor closer to Julie’s pussy and watched as Billy’s mother licked it. Tina was close to me so I reached out and removed her panties before sticking my finger in her pussy. Tina moved my finger up to her clit. I rubbed her as I watched her mother and her sister go at it. I occasionally looked at the television but mostly I just stared at Billy’s mother’s tongue slipping in and out of her daughter’s freshly fucked pussy.
When I moved Tina came with me. We went around to the other end so that I could watch as Julie licked my cum out of her mother’s pussy. Tina liked that too especially as I fingered her clit some more.
The next scene was of a girl with two guys. Billy’s mother told Billy and I to use Julie. 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. Julie put me on my back and then she sat on my cock. Her pussy felt just as good as her mother’s pussy had felt. She laid her tiny breasts down on my chest and let Billy 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 tiny breasts. As I looked over at Billy’s mother there was Tina cradled in her arms sucking on a breast like a baby. She appeared to be asleep already. Then Tina’s mother carried her upstairs to her bedroom.
After the movie ended Billy’s mother asked me if I wanted to sleep with her or sleep with Julie and I picked her. Billy 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. Billy’s mother 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 and 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 Julie was on top. I reached around and held her swinging breasts in my hand as I fucked her rectum. When I started to cum in her she fucked back at me giving me more encouragement.
We dried off and laid 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 and she said that she had figured that out. I told her that she had been the first naked woman that I had ever seen nude. Then I told her that cumming in her mouth, her pussy, and in her rectum had been my firsts too. That was when she suggested that I nurse on her breasts, tongue her asshole, and eat her pussy to complete my firsts.
I told her that I had never kissed a girl either. Billy’s mother 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 so I licked it and I liked it. Billy’s mother then got on top of my cock and rode me as I looked at her bouncing breasts and 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. When I cum for the last time that night I felt completely drained. Billy’s mother suggested that we just let my cum crust onto us over the night. Then we cuddled and talked until we fell asleep.
In the morning Tina came in and woke us up. Julie had told her that my cock had felt better than Billy’s cock had felt inside her pussy. Billy’s mother confirmed that my cock did feel better than her son’s cock had felt in her pussy too. Tina wanted to feel it in her pussy too but her mother told her that she would have to wait a couple more years until she was thirteen.
So I kissed Tina, sucked on her tiny nipples for a little while, and then I fingered her pussy like I had the night before.
Julie joined us in her mother’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. Julie told her mother that she wanted me to fuck her. Her mother smiled and replied that she wanted me to fuck her too. That was when I watched Billy’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. Then Julie got on her back on top of her mother’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. Julie told me to fuck both of them at the same time. Wow!
I got up close to them on my knees and leaned over Julie. I sucked on her nipple as I slipped my cock into her mother’s pussy. I stroked her a few times as I sucked both of Julie’s nipples. Then I went up further to kiss Julie on her lips as I slipped my cock into her pussy. I leaned over to the side and kissed Julie’s mother as I continued to fuck Julie. 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 started to cum in one and then finished cumming in the other. 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. Tina and I watched the two girls slide into a very sexy sixty-nine and gobble up my cum from the other’s pussy.
Billy finally got out of bed and joined us in his mother’s bedroom. Julie and Tina told their brother all about the threesome that we had just finished. At first he thought that Tina 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. Billy was talking about fucking his mother and his sister in that Russian Split like I had. But Billy’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. Julie was my first double penetration with another boy but fucking Billy’s mother was what it was all about.
After breakfast we all went up to Billy’s mother’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 had to smile as she tried to lick my cock head as it came out of her smashed together tits near her chin. Julie and Billy cheered me on until I was cumming on their mother’s face. Billy’s mother 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 Billy’s mother didn’t let Billy 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 Julie to take care of her brother’s sexual needs. Julie took very good care of his sexual needs and her own, practically twice a day every day. Tina 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.
Billy’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 Billy and 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 and that the thought really turned her on too. Billy told her that his house was available that day after school 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.
However when the last class ended Billy 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.
Billy had called his mother 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 Billy’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 Billy’s thirteen-year-old sister Julie. Tonya wanted to know who was in her ass and Billy 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 Billy’s mother. She didn’t believe me. She didn’t believe Billy either. So Billy called his mother.
Tonya listened as Billy filled his mother in on what had taken place so far then handed the phone to Tonya. She talked to Billy’s mother, listened to what she was saying, and then asked questions. Soon Tonya handed the phone back to Billy 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 Billy and I and our sex lives.
Finally Billy’s mother arrived with Julie and Tina and then we sat in the living room to talk. Tina was sent up to her room to play. Billy’s mother and sister then told Tonya everything that she wanted to know. Tonya was very curious indeed. Especially about what it had felt like to Julie to have two cocks in her at the same time. After a little bit of talking Billy’s mother suggested that Tonya find out for herself. So we then went up to his mother’s bedroom. Billy’s mother and sister got undressed quickly and Billy 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 Billy’s mother had. At eighteen she was a real knock out. Julie volunteered to go first and Tonya let her. This time Billy got on his back and Julie sat on him. Billy’s mother greased up Julie’s butt and my cock then I slipped it in her butt. After just a minute Billy’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. Billy’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 Billy’s mother’s ass too so that she could watch. Billy’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 Billy’s mother 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 Billy 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. Billy’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 Billy’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 Billy’s cock right up against mine as if we were in the same hole. Julie asked Tonya if she felt full and she said that she did. Julie asked Tonya if it felt good and she said that it did. So Billy and I double fucked my eighteen-year-old niece Tonya. Julie got on one side and stimulated one of Tonya’s breasts and nipples. Billy’s mother 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 orgasms. It was her very first multiple orgasm ever and it rocked her world completely. When Tonya regained emotional control Billy started to cum in her pussy and that sent her into another series of orgasms. I held off for as long as I could then I started to cum in her ass while she experienced yet a few more orgasms. Tonya collapsed on top of Billy in an unconscious state while I pulled my cock out and rolled over near Billy’s mother. 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 Billy could get out from under her. Tina 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 Billy’s cock slip into her ass and then I watched Julie suck on one of her nipples. Billy’s mother 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. This time Billy’s mother asked Tonya how it felt. She said that she still had the full feeling, that her butt was getting a little tender, and that Billy was a lot more aggressive in there than I had been. Julie told Tonya that Billy 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 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 Billy’s mother French kissing her Tonya didn’t stand a chance. She sexually overloaded and twitched and 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 Billy and I double penetrate her body. She asked Billy’s mother if she could come back again sometime. Tonya was told to come home with Billy and I after school at least once a week. She agreed.
So for the rest of the school year Billy and I got to double penetrate Tonya one day a week and Julie one day a week too. Other than that I got to fuck his mother the rest of the time and Billy got to fuck Julie.
Tonya started to introduce Billy 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 Billy and made to his mother. With her 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.