{ASS} Youthful_History {by: Mr_Ed} (bg, mg+, 1st, cons) Disclaimer: This is a story of siblings growing up and having opportunities to explore each other's bodies at different stages in life, and these results in first time experimentation. If this is not of any interest to you, do not read it. If you take offense, then do not read it. If you are not an adult (or have not obtained the age of majority) then this is not the place to learn about sex. Find a trusted adult and talk to them, even if it is not your parents. Should this be necessary, be careful not to get yourself into any position that could lead to the compromising of your safety and privacy. Youthful History by: Mr. Ed _*Six*_ Even after the first time she did anything with a boy that could be considered sexual, Karen came to her brother to tell him all the details of the experience. That was the time she played house with the boy that lived next door, and they both got undressed for bed while playing over at his house. She had been six, and he was only a couple of months older when they each spent a long time exploring the naked bodies of each other, but were unable to achieve penetration with anything more than his finger, for he could not get his penis to become hard. Encouraged by his sister, Bruce accepted an invitation of a young girl that lived around the corner from his house, and he too had the same experience of seeing her naked, touching her as much as he wanted, while he permitted the same things to happen to himself. When it was all over, he came home, and told Karen all the details of what had happened, just as she had told him of her experience. _*Nine*_ The next event took place for Karen when she was nine years old, and came from three boys trapping her in a corner of the school hallway, and lifting up her skirt to see her panties. She was still upset when she got home, and told Bruce of the event. He knew the three boys, and when they were identified for him, he called on each, and invited each outside to be thoroughly beaten in a fight. Actually two of the boys were beaten before an adult intervened, and was told of what they had done to his sister. Each was taken in by their parents for a additional punishment as he headed to the home of the third. By the time he got there, he could hear the smack of a belt and the cries of the boy, for the information had gotten to his parents before he had arrived. That event was the beginning of Bruce having a reputation as a fighter to be avoided, and his stature in and around the school, and his home area became greatly enhanced. The best part about it was that he never had to get into another fight with anybody during the balance of his early school years. _*Ten - Bruce 12*_ Almost a year later, Bruce was present and a participant at Karen's next experience. She had climbed a tree, and several of the guys with him had started looking up her skirt as she moved about up on the branches. Even after she came down, and the show was apparently over, she decided to go back up, and gave them all another look. Since it was clear she was doing it on purpose, when she came down this time, Bruce actually helped pin her to the ground, while her skirt was raised, and her panty butt was looked at as well as touched. He was the one that lifted the waist of her panties, and looked down to see her bare bum, and when she didn't object, he pushed them down so she lay there, with four boys looking at and touching her bare ass. They had remained there for quite a few minutes, possibly over five before her panties were pulled up and the group all dispersed in different directions. As Bruce was walking Karen home after that event, he said, "That's the first time I remember seeing your bare ass since we were babies. It sure is sweet, the way it is so nicely rounded. Are you upset that we did those things to you?" "I wanted you to do that," she admitted. "I wasn't thinking when I climbed the tree at first, but when I realized what I had done, I wanted it to happen. That's why I went up the second time, so it could be looked at again." "I just wish it had lasted longer, for I was really getting a good feel and look at your butt, even though the other guys kept getting in my way for a little turn. Oh, well, that's the way it happens, sometimes." "When we get to my room, you can have a longer look if you want, Bruce," she told him. "I wouldn't mind, you know." "If you are willing then I'm looking," he told her emphatically. "How long will you let me look?" "Long enough," she assured him before they were racing to the door of their home. She had taken the lead, but even with her head start, he arrived just a fraction of a second ahead of her, giving them both a good laugh as they searched for the keys to let themselves in. In her room, Karen slipped her panties off from under her skirt, before she stretched out on her bed, and allowed her skirt to be raised over her back. For over half an hour, she laid there while her brother kneaded and caressed her butt cheeks, spread them open to look at her asshole, and she knew he was able to see down between her legs, until where the slot disappeared around at the front. It was not a thing she could prevent, for the space between her legs was wide enough, she could not hide the view, so it became a part of what he got to see. "Did you like having the other three guys touching your bum, Karen?" he asked during his time playing with it. "It was kind of kinky having four guys looking at my ass at the same time. I wonder how many saw the slot down at the front?" "Everyone, for Herby pointed it out to the other guys to see," he informed her. "I'm going to have to stop wearing skirts outside for awhile," she said. "They will all think they have an invitation if I wear a skirt again too soon." "I guess that means this will be my last chance to see your sweet round ass," he observed. "That's too bad, for I'd like to see it other times." "I still wear nightgowns, or pajamas at home, so you could take a peek sometimes," she offered. "Not everyday, though." "Fair enough, and thanks," he told her. "I'm going to have to quit now," he added. "Okay, Bruce," she said. "Go do your thing in the bathroom, and have fun." "Having you know what I'm doing is embarrassing but I still have to!" he declared. "I came twice while you were rubbing my butt, so I've had my good time sooner than yours. Just have fun, and I'll not say anything to anyone, even though I'll think about it myself when I go to bed tonight." "Sometimes you are really neat to have as a sister," he said. "Thanks, Karen." "See me when you are done, Bruce," she said, "in my room." Five minutes later, Bruce came to his sister's room door, and said, "That feels better, so what did you want to see me about?" "Sometimes you say the nicest things, just like you did before you went to jack-off. Because of what you said, I have something special for you, so unless you are planning something to do, come on in, and see what it is." "I have no special plans other than I'm still thinking about your sweet round ass," he told her. "Doing that to you for so long was super nice, Karen. Thanks again." "You are welcome," she replied. "This time you can have the front of me just as long, if you are interested." "I'm interested, but that's not fair to you, Karen," he stated. "You are doing all of the giving, and I'm taking advantage of you." As he spoke, she had moved over to her bed, and stretched out down the middle. Lifting her skirt to expose her vulva, she said, "Take advantage of me then. You made me want to let you, and I get to come again!" "Don't mind if I do, then," he told her as he came to sit near her legs. Karen drew her legs up, and spread her knees apart, giving him easy access to her crotch, and he took full advantage as he leaned forward and placed both hands on the offering. "Are you going to let me feel you up?" "Only as far as my cherry, please Bruce," she said. "I don't want you to break it on me yet." "Yet?" he asked. "Do you expect me to be the one to break it one day?" "Yep!" she confirmed. "Probably in the next couple of years, I suppose." "You are really something else, Karen," he told her. His finger slipped inside her slowly but purposefully, going in as far as the second knuckle before he came up against her barrier. She made it clear by her moaning and open mouth that she liked the feeling it gave her, as her legs went even further apart. While he turned his finger around inside, he used the fingers of his other hand to play with the fold of skin that was her clitoris, and the moans became even stronger. A minute of this, and then her cries were almost loud as during her climax, and wet up his finger even more. "Sometimes you are so quiet when you come, while other times so loud," he told her. "That was the best time ever for me, Bruce," she admitted. "Would you mind if we stopped? If you keep doing that, I'm going to end up with you fucking me, and I want my breasts to be larger first." "Sure we can stop," he told her. "Before I do, though, there is just one thing I've really got to do, because I dream about doing it all the time, and want to actually do it for just once." Without another word, he leaned forward, and placed his lips on the opening to her vagina, and kissed her firmly for several long seconds. When he got up, he said, "Thanks, Sis. You taste as good as you smell down there." Then he left her room, and returned to his. Two minutes later, Karen was in his room, came up behind him, and smacked him on the side of his head. "What in the hell was that for?" he demanded as he turned on her and rose to his feet. "Because you are so good, and I love you so much," she said as the tears burst out of her eyes. "I didn't mean to hit you so hard though," she said. "I'm sorry!" "Hey, kid," he said as he pulled her against himself. "No tears now," he said quietly. "Everything is all right!" "Everything is wonderful," she cried out. "You're hugging me, and you are so perfect in everything." "That's not true, but thanks anyway," he responded. "If you think I'm so perfect, why are you crying?" he asked. "Because you make me so happy, I have to cry," she said. "Girls do silly things like that you know." "Definitely weird!" he declared. Leaning over he kissed her full on the lips, a kiss she returned. "Don't tell anyone, because it is a secret...I love you too, Karen!" "You see?" she demanded. "You see? Always so perfect. I was going to wait for these to get bigger first, but I can't wait for them," she declared as she held her blouse up to expose her two little breast bumps. "You can have me anytime you want, including today!" "They really have started, haven't they?" he said about her chest bumps. "We are going to wait, Karen," he said. "You may still decide a different guy from your brother is the best one to break your cherry, so let's wait just like you first said." "There you go again, being so damn perfect," she said as the blouse dropped down to hide her breasts bumps. "I really, really do love you, Bruce," she declared. "My parts are there for you anytime you want them, so just help yourself when you are ready." With that, she turned and left his room, heading to her own bed to masturbate alone. A week and two days later, Bruce came home with a big smile on his face, something Karen noticed immediately. "What makes you so happy, Bruce?" she asked of her brother. "You remember Francine, the girl I played house with when we were about six years old?" he asked. When Karen nodded, he said, "She let me have a feel of her titties today, and they were so sweet!" "So did you play house with her, and get it into her?" she asked. "No," he admitted. "She was too scared to do anything more, so I told her it was okay. I thanked her for the feel up of her breasts, and told her that maybe, some other day, we could do it again. She said she'd like that, and was sorry she didn't want to do more today. If I play my cards right, I bet I will get into her one day." "Would you fuck me first, before you do her?" asked Karen. "What if she offers before you are ready to do it?" he asked. "You expect me to wait?" "No, but you can do me tomorrow," she declared. "There's not enough time before Mom gets home today." "What is so important that you will agree to do it before you are really ready?" asked Bruce. "I would love you just the same, and be ready to do it with your when the time is better for you." "I want to be your first," declared Karen. "Once you do it with me, then you can go and have Francine, or as many girls as you can get, but I want to be the first one to feel your cock inside!" "The chances are Francine would not be willing to do it for some time yet, so you don't need to do it with me tomorrow. I will even promise that if I see signs of her being willing, I will come home and do it with you before I go all the way with her. Would that make you feel any better about it all?" "You'd be willing to do that for me?" asked Karen. "Do you see why I love you so much? You are so good to me, even through I know I can't have you for myself when we are older. We can't marry so you have to have others, but I just want to know it went into me first. Please, Bruce! It's important to me!" "Then that's the way it will be," he assured her. "I will learn what it is like with you, before I get into any other girl I am lucky enough to find." At that point the conversation was put aside due to the arrival of their mother. When their mother left the next day, Karen was nowhere to be found. It was not that Bruce was looking for any specific reason, but he just wanted to be close to her for some reason, and assure her that all was okay. Somehow her expressed wishes had made the closeness he usually felt even closer, and he wanted to make her feel comfortable, and remove the pressure to act that she must have been feeling. While his first time with an into a girl was important to him, it was just a little scary as well, so putting it off was not such a bad thing for him. There was no way she was in the house, so he settled down to play one of the more challenging games he had on his computer, determined to master the game. He was able to get almost a full hour playing, and had improved his standing two grades when he heard Karen coming into the front door. When she called out his name, he responded by telling her he was in his room. A moment later, she appeared at his door, but was not alone. Of all the unexpected events, Francine was with her, and both were smiling at him. "Good morning, my two favourite girls in the whole world," he greeted them with a smile. "If I had known you were coming, I'd have made up my bed before now," he stated. "Why don't you let us make it for you?" asked Karen as she led Francine in and over to the bed. All Bruce could do was stare in fascination as his work was done for him, taking advantage of the opportunity to look at the two girls, dressed in short skirts, and narrow tops over their chest. The midriff was bare for both of them, and looked sexy, while the act of making the bed gave him a look under their skirts when they bent over. As soon as the bed was made, they sat down side by side facing him, giving him another flash look up their skirts as they sat down, and before they could close their legs. "Thanks girls," declared Bruce. "I can't imagine why you two are here, and willing to make my bed for me, but thanks anyway." "You act dumb even though I know you are not, Bruce," stated Karen. "We have been talking, and worked out things between us. Today is your lucky day," she concluded. "This sounds like I'm about to be attacked or something," he said. "Both of us love you, Bruce," started Karen. "We have been talking, and both want you to be our first lover. Francine is still afraid, but she has strong feelings for you, and knows she will be letting you go further the next time you are together, no matter how scary it is. She knows how I feel as well, and how I have always wanted you to be my first lover. So what we worked out is that I will do it with you today, and let Francine watch. When she knows what it is like, maybe it won't be so scary, and will make her feel better about giving it up to you next. How does that sound to you?" "You aren't a little scared yourself?" Bruce asked of Karen. "Yea, but I'll still do it!" she declared. "Then you should know that I'm a little scared myself," he admitted. "I'm not sure I'm ready to do it, especially with one girl watching. What if I mess up things?" Karen and Francine looked at each other, before Karen said, "We never thought about our big man being scared. Damn, it makes me feel like I want to do it even more than before!" "Me too," declared Francine. "You really are the nicest guy I've ever known!" "You've had both of us naked, and know exactly what we look like, Bruce," Karen went on. "We know that you wouldn't mess up anything so I don't see where you should be afraid. As a matter of fact, we should be able to guide you past any doubts you have." "But the two of you would see me at the same time," he observed showing a little embarrassment. "The handsomest boy around, worried about us seeing him," observed Francine. "We can strip our things off first for you, Bruce, and make you feel better. I still remember what you looked like the first time, and it was just fine!" "But I couldn't even get it hard then, but it is hard almost all the time now!" he declared. "It's different! What if it isn't big enough?" "Trust us," said Karen. "We've got a pretty good idea of how big it is, and it is big enough to be part of what scares us. You are just fine for size!" "How would you know?" he asked. "We've seen it hard inside your pants, and how close it comes to your belt. Trust us, for it is maybe too big for us." "That's embarrassing and flattering at the same time," he admitted. "So would you like us to get undressed for you?" asked Karen. "Never mind, Karen," said Francine. "Let's just do it and we will be able to get his interest." At the same time, both the girls kicked off their sandals they were wearing, and then reached for their tops. On the count of three, both pulled them up and off over their heads, exposing their chest for him to see. Francine was definitely larger than Karen, but even Karen's looked bigger than what he had seen a couple of weeks ago. They were definitely growing now, and both of the girls looked good...real good!" When they stood, and both pulled their panties down from under their skirts, Bruce knew that this was definitely going to be the day, and so began removing his own shirt. The girls had paused to watch him once their panties had been slipped off their feet, and continued to watch as he removed his shoes and socks. "The next step is the scary one," suggested Bruce. "Do you want we all finish on the count of three?" He received nods from each of the girls, and while he undid the fastenings of his belt and jeans, they undid the fastenings of their skirts. "Okay," he said, "on three, we all take off the rest of our things." "You still have on briefs," countered Francine. "I'm pushing them down at the same time," he said. "One...two...three!" All three were now exposed, and looking at each other, even as the final removal took a few moments longer. "You are both so perfect!" he exclaimed as he stared at them. "And you are big and handsome," offered Karen, "just like I knew you would be." "That sure is bigger than a finger!" exclaimed Francine. "Wow!" They were all standing now, one each was close to the next, separated by only a matter of inches. Bruce lifted up his hands as if to take a feel of one breast from each girl, and then dropped them back to his sides. "Go ahead, Bruce," said Francine. "You've already felt mine, but can have another feel, as long as you feel Karen's at the same time." "I just wish I had more to offer you, Bruce," said Karen. "What I have, you are welcome to feel." "You know what I think?" asked Bruce as he put his hands on the back of each girl's head. "I think I've got to be the luckiest guy alive, having two girls I can feel so special about. I guess this is love, for it sure feels nicer than anything I've ever felt before, at least this strong." Karen was the first to put her arms around her brother, and drew herself up to press her naked body against him, his penis against one of her hips. Francine did the same a moment later, and he was being hugged by two naked girls, each making a sandwich of his penis. Moving his hand from their head, he slipped down their backs until he had his hand just above the waist of each. Karen was looking up into his face when he turned to her, and accepted his kiss when he leaned forward. When he straightened up, Francine put her hand on his cheek, turned his face to her, and they exchanged a kiss between them. "I feel ready for you to take me, so why don't you go and do it with Karen, so I can get my turn," suggested Francine. "What would you feel about that, Karen?" asked Bruce. "I'm still a little scared, but if you are ready, then let's do it!" she responded. "May I taste you like I did yesterday?" he asked. "Would you?" she brightened. "That would be wonderful!" She immediately sat down on the bed once again, but leaned back to lay on her back, drawing her legs up to hold them behind her knees. Bending over, Bruce once again brought his lips to the opening that was offered to him, and the first kiss had her moaning from the satisfaction she felt from the touch. This time, however, that was not enough for Bruce, and he pushed his tongue out, and into the opening, and getting it wet from inside her. The moaning was even louder, as she made every effort to push herself up against his tongue. Francine was now kneeling with her face close to them watching what he was doing to Karen. To increase the pleasure she was getting, Bruce used one finger to play in the top of her vulva slot, and the finger of the other hand to play with her anus. When he pressed the finger into her asshole, Karen climaxed crying out from the wondrous sensations she was having. "I'll never be more ready than this Bruce," declared Karen almost out of breath. "You want to try putting it in?" "Move up on the bed better," instructed Bruce. As soon as she was lying with her head on his pillow, he once again entered her with his tongue, bringing her almost immediately back to the heightened intensity she had experience moments before. Then he got over her, positioned his penis, and pressed down, easily causing it to go in up to the barrier. It was Karen that put her hands on his bum, and pulled him towards her, while she pressed her hips up off the bed, causing the barrier to go down, and his entire penis to be up inside her. "Ouch!" cried out Karen. "That did hurt!" "Just stay still," suggested Bruce. "It hurt going in, but that's going away," she argued. "Pump me, Bruce. It feels good!" Bruce did pull back, causing Karen to squint a little, but when he pressed back down in, her mouth was wide open, and she moaned again, this time from satisfaction. "It's good, Bruce! Do it to me! This is the best thing...ever!" declared Karen. "Fuck me hard, and deep!" The pumping started slow, but did not remain that way very long. With each push in, Karen let out her breath, and a cry of satisfaction at the same time. Francine was close enough to watch it going in and out of Karen, and played with herself at the same time. Reaching out she put her fingers against his shaft each time he drew out, and felt the hardness of it as he returned to the inside, bringing her fingers against her vaginal lips. She pulled away her hand only long enough to taste the wetness she found, and then returned to touching the two lovers at the point of union. Each time he pushed in, his balls came up against the back of her hand. Then, as he started groaning, the pumping stopped, and Karen was being filled up inside with his discharged seeds. "It's better than I ever imagined, Francine," declared Karen even as she was being filled up with the last of his discharge. Thanks for letting me get him first, but you have to try it. It is like it belongs in there, and has been missing all my life." "The hurt wasn't so bad?" she asked. "It was almost nothing," declared Karen. "If I knew it was that little, he would have had me long before this!" "Being scared doesn't make any sense then?" asked Francine. "Not at all!" declared Karen. "Go fuck Francine, because I want it from you again today, Bruce!" "You really liked it that much?" he asked. "It was better than I can even tell you," she declared. "You really are perfect, Bruce, and I love you with all my heart, and body. Maybe with my body even more right now!" "For me it was more than I expected, and wonderful, Karen," he told her. "Thank you for letting me do this with you. I am going to remember this for the rest of my life." "Me too, except for this part," she responded. "I'm loosing you!" "I guess I had better get it out before it is soft enough for you to lock inside you forever!" he said. "Do I wish that could be, but...oh, well, there it goes. Hope you come back soon my wonderful cock. I'll be waiting for you!" "Now that is more like I remember it from the first time, years ago," declared Francine. "I guess I'm not getting it right away, at least." "I usually have to wait a little while before it will get hard again, Francine," explained Bruce. "Then I'm heading for the bathroom to get a drink of water," said Francine. "I'm so dry!" "There is cold drink in the fridge," suggested Karen. "We could all do with something." All three headed for the kitchen, each still naked and no longer concerned about it. They got their drink and sat around the kitchen table to enjoy it. "I had no idea sex was so good," stated Karen. "You could have had me years ago if I had known Bruce." "That's one of the secrets adults keep, I guess," he responded. "It was nice, Karen, and I am looking forward to doing it again with you." "Don't forget I get a turn," interjected Francine. "We aren't forgetting you, Francine," declared Karen. "Don't forget, you were the first to get his clothes off, and his first experience with a girl." "Remember, you got your wish, and he got into you before anybody else," reminded Francine. "Something tells me you will be doing it more with him than I will, especially after you two marry!" Both Bruce and Francine almost recoiled at the idea, looked at each other, before Bruce said, "Maybe! The way I look on things right now, that could happen!" "I'm already going to let you be my first," said Francine to Bruce. "You don't have to talk me into it any more." "I'm not trying to," he said. "That's the way I feel and the idea of marrying you sounds real nice right now. Lots of things will happen as we get older, but I feel that way right now." "If I was in any doubt about my feelings for you, Bruce, you just blew them away! I love you, and hope it does happen, that I'll please you enough that you would want me!" "Finish your drink and we can find out," he said. "You've got me hard again, so when you are ready, then so am I!" The remaining drink remained on the table, forgotten as they headed to his bedroom. Francine took up the position Karen had been in, and was soon thrashing about as Bruce started licking and penetrating her vagina with his tongue. She was no less noisy than Karen had been, and enjoyed it just as much. It only took about a minute to bring her to a climax that way, and by the time she reopened her eyes, Bruce had his penis partway inside her. Karen went behind Bruce, put her hands on his butt, and pushed. Once again, he was fully inside of this girl he had examined when he was only six, and she was no longer a virgin. It may have been his penis, but it was actually Karen that had broken her cherry. "That was mean, Karen," declared Bruce. "It got it over with, Bruce," said Francine. "It's alright!" "You want me to stay still while it stops hurting?" he asked. "What I want is to keep it in there for the rest of my life!" declared Francine. "It feels so full and complete, just like Karen said." "When he starts pumping you, you will enjoy it much more, Francine," said Karen from her side. Bruce pulled back, and pressed in again, Francine accepting the action as a wonderful surprise, and as a pleasure to be repeated. The more he pumped her, the more she wanted it, coming quickly to a climax, even as his pumping continued. She did achieve a second climax just seconds before he released his load, fighting hard to retain his muscle control and hold himself off of her body. He only had partial success, but Francine was not complaining, for she knew he had felt it as deeply as she had. For the next few years, Bruce was tested to see if he had enough stamina to satisfy his two girls, for they both demanded it often, and frequently. For Bruce, it was a test he did his best to live up to, refusing any other girl that showed him any interest. His plate was full enough, and he sought no additions at this time.