Note: This story was dynamically reformatted for online reading convenience. Disclaimer: This is a work of fiction. I do not condone sex with a minor for any reason. The story is written purely for enjoyment. Code: mm, Fmm, FFm, incest. Caught By My Best Friend's Mom My earliest real sexual experiences began with my best friend Bob. Around the age of 12 we discovered how good it felt to get hard and cum. Probably not a real cum but the early clear cum young boys can have. Bob and I talked about how things made us hard and found we had a lot in common. As time went on we evolved into going into Bob's bedroom and getting naked together and jacking our young cocks off. It was just mutual masturbation at first, until one day Bob found a Playboy in his Dad's shop. A whole new world was open to us. Miss May 1965 was the turning point of my life. Her full tits with large areolas and slightly hard nipples, a fine mist of water droplets on her tits made it even more erotic. She was wrapped in a red towel around her shoulders which covered her pussy, since Playboy did not show bush in those days. This made me into a harden sex fanatic and jack of fiend. Bob and I were enthralled by this Playmate and jacked off together many times to Maria. This also caused us to get more curious sexually about things, and since we were nude together it happened. Bob reached over and touched my hard cock as I was stroking to Miss May. The surge of sexual energy was amazing. I came almost instantly and my cum got all over Bob's hand. We were like "Oh, Gross!" But Bob asked me to stroke him. I reached over and and wrapped my hands around his hard cock and moved my hand up and down. Bob seemed to be able to hold out longer, but finally exploded getting cum all over my hand and arm, as well as it landing on Miss May's face. We both tasted the cum by putting our fingers in it and putting it to our mouths. Neither of us liked it, then panic set in, there as a huge blob of cum on Miss May's face. We tried to wipe it up but soon found out the evidence of Bob's cum was clearly there to stay. His dad would soon find out. Our solution, I am ashamed to say, was to get $1.50 out of Bob's mother's purse and convince and older friend to buy us a new May issue of Playboy. Unfortunately, June was on the shelves and he couldn't replace the May issue. So we carefully returned the issue to his dad's shop and hoped for the best. Bob's father did talk to Bob about three days later, and Bob told him he just couldn't help himself when he found it in the shop. He said nothing about our mutual masturbation. His dad scolded him and grounded him for a week. So a week of solo masturbation followed for me. Then I got curious and started searching my house to see if my dad had hidden issues. He didn't but found my older brother had about 20 issues of Playboy in his desk. I was able to sneak away an issue and he never noticed. Soon as Bob was ungrounded I took an issue over to his house and we retired to his room. I thought I was being very cleaver sneaking the issue under my shirt, but clearly Bob's mother noticed and smiled and said, "Have fun" to me as I entered Bob's room. We opened the Playboy after we got naked and began stroking to a lovely set of tits on the page. Then Bob reached over and began to stroke me, and I reached over and grabbed his rock hard cock. As we enjoyed the feeling and the magazine Bob's bedroom door open and in walked his mom holding a laundry basket. We both froze a second then tried to cover up. She shouted, "Don't move you two perverts!" We knew we were doomed. But to our surprise she walked over and sat down between us, and encouraged us to finish. She held the held the magazine in her lap and watched us jack off. As we stroked she ran her fingers over the tits in the picture and talked about how sexy they were. We both came exploding cum all over our hands. She patted us on the legs and told us we should have locked the door. But then added, "Bob if you ever lock your door when Henry is here you are grounded, got up, picked up her laundry basket and left the room. Bob and I were like, OMG did that just happen? Which made us hard almost instantly again. This time Bob told me to lay on the bed on my stomach and he rubbed his hard cock on the crack of my ass. He did not penetrate me but came on my back as he rubbed his cock on my ass crack. He then got up and tucked his cock between his legs to look like a girl's pussy, or so we thought. He told me to rub my cock on his tucked in simulated pussy. My hard cum filled his belly button. About a week passed before Bob and I could get back together in his bedroom. He was doing a tennis camp and was away. Needless to say I was very excited when he returned. We immediate went to his room that Monday morning. As we got ready to lock the door. Bob instead left it slightly open. We got out a Playboy I had taken from my big brothers stash and we stripped. Then as we hoped, in walked Betty, Bob's mom. She smiled and said. "Oh Good! I was hoping you to would be playing." She had a magazine rolled up in her hand as she entered and sat down between us. We had Miss August. Lannie Balcom spread out for us to enjoy. She had a great swim suit line and her perky tits were very pronounced, because her white skin stood out against her tan. Bob and I were already hard and his mom walking in made us both even harder. Then Betty opened the French magazine that she told us her husband kept in a very private place, not with the Playboys. She opened to a black and white photo of a fully nude woman. It showed it all including a very neatly trimmed pussy. Betty asked me if I had seen that before and I said, "No" and then she asked if I knew what it was called. I stammered around looking for a word then blurted out, "It is her private parts." She laughed and said, "No, we call it a pussy or a cunt." Then she insisted Bob and I both said Pussy and Cunt to her. She then told us to stroke our cocks as we looked at the nice cunt. As we stroked Betty would lean into my arm and press her large tits against me. Then over to her son Bob and did the same to him. Then she would lean in and touch her clothed boobs to the tip of my aching cock. We both exploded again, but this time I sort of aimed toward Betty in hopes of getting some on her. It worked and my cum landed on her shorts and leg. She laughed and said, "Oh my, you gave me a treat!" Took her finger and scooped up my load and put it in her mouth and sucked. She smiled and kissed me on the cheek and turned to watch her son shoot his load. Most of it landed on Bob's legs and she took it and tasted it with her finger again. Smiling and saying, "You two really need to lock this door. You never know what might happen." And she left the room but left the French magazine behind. The next day I rushed over to Bob's around 10 a.m. after I did my morning chores that my mother insisted I completely before I go play. Bob already had the French magazine open and stroking his cock as I came into the room. I dropped my pants and joined Bob on his bed stroking to the beautiful French women fully nude. I was a bit disappointed I had not seen Betty as I came into the house, but was enjoying the amazing cunts in the magazine. As we stroked each other we heard the door close. It was either Betty or Bob's sister Kay. Fortunately, it was Betty who walked in the room. She said, "Oh good, I was hoping I didn't miss you two today." She came and sat down between us again, as was her habit. But this time she did something that completely amazed me. She slipped off her shirt and bra and smiled at us. She told us it was time we saw what real tits looked like. Then without warning Betty took our two cocks in her hand and began stroking. She had my cock with her right hand and her son's in her left. She told us to lay back on the bed and enjoy. She pulled my cock up and down slowly, as she did the same to her son. After a while of stroking she asked if we would like to touch her titties. We both sat up immediately and said, "Yes!" Betty smiled and said, "There is a price for doing this." I know we both would have agreed regardless of what it was. But we really didn't expect her price for touching her amazing large tits. But we both said, "OK what you want us to do?" Betty explained that as one of us felt her up, the other had to suck cock. Bob and I both looked at each other, then to Betty's tits and agreed. I was first to feel the amazing tits, as Bob got down on the floor between my legs and took my cock in his mouth and began to suck and stroke me. I said, "I am going to cum!" and Betty said, "Cum in my son's mouth." I squeezed her hard nipple with my right hand and shot a load of cum into my best friend's mouth. Then without words Betty pushed me to the floor and pulled her son up to the bed. I know what I had to do to pay the price of feeling her up. I slowly grabbed Bob's hard cock and took it into my mouth. I really didn't know much about sucking cock, but figured I would learn how that day. I looked up at Bob who was smiling and fondling his mother's tits. Betty gently reached down and pressed my head into her son's cock. As I sucked Bob came hard into my mouth, then Betty ordered me not to swallow, but to kiss her. I stood up with my mouth full of cum and leaned in to kiss the older woman. She pressed her tongue into my mouth and took most of her son's cum into her own mouth. Then she leaned to her son and kissed him pushing most of his cum into his mouth and ordered him to swallow his own cum. Bob did obediently. Betty got up and turned to the door, where her daughter was standing, and said, "That is how you suck cock, I hope you enjoyed seeing that." Then she turned to Bob and me and said, "You two should really lock the door." Bob left the next day with his sister Kay on a trip with his Dad to Denver. I was walking down the street wishing my best friend and jack off companion was around. As I walked in front of Bob's house I heard Betty calling out a bedroom window, if I could come in and help her do something. I said, "Sure" and headed toward the front door. As I approached Betty said, "The door is unlocked, come on in." I walked in and heard Betty call out, "I am in Kay's room." I walked down the hall toward the 11 year olds bedroom and open the partly closed door. There was Betty full nude and standing on a step ladder by the closet. She asked me to hand up a box on the floor so she could put it away in the top shelf. As I handed her the box Betty turned toward me and I came face to face with her hairy cunt. She took the box and placed it in the closet then turned back to me and said, "Give it a lick." As she stood on the step ladder I moved my face close to her pussy and stuck out my tongue. Betty opened her legs best she could on a step ladder to allow me to lick her wet cunt. I pulled my tongue from bottom to top several times tasting the first pussy I ever had licked in my life. Betty finally said, "This isn't working very well." and got down from the ladder and laid down on her daughter's bed. She pulled her knees back to her shoulders and said, "Try licking my cunt now." Her slit was wide open and she pulled her legs apart for me to have good access. I pressed my tongue deep inside her hole and savored the taste of my best friend's mother's cunt. Betty began to make noise as I worked my tongue inside her. Betty instructed me to put a finger in, and push it deep inside her. I did as I continued pressing my tongue against her clit. Betty squirted an amazing liquid out of her wet pussy as she shouted some unintelligible word. Betty then told me to stand up and I obeyed. She began to undress me, first the T-shirt came off and she kissed my nipples. That really tickled but was very exciting as well. The she pulled down my cut off shorts and underwear. She lowered her head and sucked my cock. Betty rolled her tongue around the tip of my cock, then would take the whole 13 year old cock into her mouth. She repeated it again. Pulling away she said, "Need to not do this long because I want your cum inside my hot cunt." I was clueless what she meant since the whole scene was almost beyond my comprehension. But I soon figured out Betty intended for us to fuck. She laid back and spread her legs telling me to fuck her. I took my hard cock in my hand and aimed it toward the older woman's open slit. There was little resistance to my cock pushing inside her. Betty was incredibly wet and smooth. I remember how amazed I was how good her cunt actually felt around my cock. Sadly, I didn't last long and came hard inside her. She smiled and said, "That is OK, we have all day." We went to the kitchen and Betty made me a sandwich, since it was near lunch time. I mentioned my mother probably had lunch for me. And she said, "No problem, I will call her." I sort of froze in the middle of a drink of milk as Betty moved to the kitchen phone. She called my mom and told her, "Your son is having lunch here with me today, then I am going to fuck him again. If you want you are welcome to come over." I actually spit the mouth full of milk out of my mouth and shouted. "WHAT!" as Betty hung up the phone she turned to me and said, "Relax, I have been fucking your mom since junior high. She knows all about this summer." I fidgeted nervously when I heard my mother knocking on the door. Betty answered the door completely nude. My mother was a tall woman with 34 C breasts. Betty kissed her and pulled her dress off over her head. I was amazed that mom actually had NO underwear as the two woman stood nude. Betty told me to come be nice to my mother. We spent the rest of the afternoon fucking. I did my mom first. She had a nicely trimmed pussy and a pouting clit that stood out from her pussy when she was excited. Betty slowly licked my ass as I pumped my cock inside of my mom. I said I was about to cum and mom told me to cum inside her. As I recovered from my second cum of the day. Betty and mom fucked each other. I was amazed what a great cunt licker my mom was. Then Betty took her turn on my mother, licking her pussy from bottom to top then pressing her tongue deep inside my mom's cunt. My mother pulled my head close to her stomach and told me to watch. I grew instantly hard as I watched the two women fuck. Finally, they both noticed I was hard again and Betty positioned me on the bed and they both got between my legs. I got a double blow job from my mother and my best friend's mom. As Betty sucked on the tip, mom would suck on my balls. Then they would reverse the position and mom would take the tip of my cock in her mouth looking up at me smiling. The Betty pushed me back on the bed and straddled my hard cock, as my mom straddled my face. The two women rocked back and forth with Betty fucking me and mom rubbing her hot cunt on my mouth. They were facing each other and I assume playing each other's tits. I was too busy to really know for sure. After the third fucking mom said, "Well it is time for us to go home." I was ordered to not tell their husbands or even Bob about today. It was our secret. Mom and I returned three doors down the street to our house as we talked about how natural sex is and she wanted me to learn about it from safe people. She told me she had known I was stealing Playboys from my brother and even knew about the French magazines. I said, "I was sorry" and she scolded me saying, "Do not be sorry, this is our secret and is going to be a lot of fun". Much to my disappoint, when Bob returned from his trip with his dad, they announced that Charlie had gotten a good job in Denver and they would be moving immediately. There was no time for another jack off session with my best friend, and no time to fuck Betty again. They left within two weeks of their return. I was sitting pouting in my room the next day. My mother walked into the room and sat down beside me. She asked me, "Why are you so sad?" And I told her I was going to miss Bob and Betty. She hugged me and said, "I understand, but you always have me." Then she smiled and whispered in my ear, "Everyone is going to the city tomorrow, you want to go with them or stay home with me?" I looked at her oddly, "Stay with me and fuck you silly boy!" "And be sure to not lock your bedroom door when they leave tomorrow!"