Date: Sat, 3 Dec 2022 08:20:22 -0500 (EST) From: ShortStories@PlayTime69.e4ward.com Subject: Guiding the Children This story is 100% fiction and is for mature readers only. If you are under 18 please leave now. Please note that all my stories are written for enjoyment only and not intended to give anyone ideas on what to do, what to try, or who to do things with. The actions taken in my stories should stay in your mind only and not expanded to real life situations. This story is a fantasy involving two families with children. You can see a list of all my stories on the authors page under the author, Playtime69. All comments are appreciated and can be emailed to ShortStories@PlayTime69.e4ward.com. Please identify what story you are talking about when you send me a message. Even though I do not respond to all emails I do read them all and have used some of your suggested ideas in my stories. I also will write new stories with your suggested ideas. Just send me your ideas to address above with as little or as much information as you want to tell me including names, ages, sexes, positions, relationships, and what section on Nifty you want the story to go, etc. I will see what I can do with it. If you want to name the story that is fine too. Just make sure the information is yours and not from someone else's story. Thanks for reading. Please, find it in your heart to donate to nifty at https://donate.nifty.org/ without them we would not have a safe place to deposit and read such great stories. This story's general idea and part of the information came from one of my readers. I took their information and worked it into the story you see here. I hope you enjoy this story about how two families guide their children into early adulthood. Guiding the Children by: Playtime69 "Bobby! You have slept in long enough. Time to get up." I loudly said as I barged into my son's room unannounced. "Mom! Really? Can't I have some privacy?" He chimed back. I looked at my son in bed as he complained of the way I entered his room and noticed what he had been doing as I told him to get up. He was up. At least part of him was up. Luckily he was still covered by the sheet so I saw nothing but a protruding lump where his dick would have been. I did not want to make a scene or embarrass him so I pretty much ignored the situation and continued to prod him out of bed. "Well I know it is Saturday but you cannot stay in bed all day. Don't you have a baseball game today?" I was saying as I opened the window blinds to let some more light into his room. "What time is it?" My son asked as he tried to hold his hard dick down until it deflated. "It is a little after ten so let's get a move on it." I demanded. With that I walked out of the room and closed the door behind me. Once out of the room I leaned against the wall to keep from falling down. How could I do that to my son? The last thing I wanted to do is to embarrass him or to make him feel that touching himself was bad but I just did not know how to talk to him about sex. My son, Bobby, was an only child. He was 12 years old almost 13. He was my baby and I loved him with all my heart. I just wanted to protect him from any and all that might take advantage of him or teach him things that was not true or good for him. Part of my overprotection was due to his small size. Bobby was only 4'9" tall and weighed just under 80 pounds. This was not to say he was sickly or anything. It was just that small size ran in my family and he just seemed to get caught up in it. Bobby was a very good baseball player so size really did not matter much to him anyway. Another reason I was so protective of him was it was just him and me. His dad died when he was younger due to a undiagnosed heath issue so ever since the untimely death we have been very close with the one exception, sex. I really did not know how to tell him about sex, masturbation, or even what to expect as he entered puberty. I had always assumed his dad would teach him and now without him around it was up to me. I knew I had better figure something our soon or he was either going to learn it on the streets or even worse, not at all. I knew he had started puberty mainly because I was finding cum stains in his underwear and on his bed sheets. He was taking longer showers and was spending more time in his room after school. I knew that whatever I was going to say was going to have to be said soon or else. I pulled myself together and headed to the kitchen to get his breakfast ready while he finished doing what he was doing when I broke into his room. Bobby strolled into the kitchen not long after I set his food on the table. We said our good mornings and he sat down to eat. "Oh, Mom. I forgot to tell you that I have a double header today so I will not be home for lunch. The coach is provided food for us all. I will be home for dinner but am spending the night at Jerry's house." Bobby was telling me in between bites. "Guess I will not get to see you much today then. When is your first game?" I asked. "First game is at 11:00. Second game is at 2:00. I should be home to eat about 5:00 and Jerry's mom will pick me up here at 6:30." He was saying as he finished breakfast. Bobby was a good kid and I was not worried about him getting into trouble. He did not have many friends and matter of fact Jerry was the only one he ever spent the night with. Jerry was also a good kid but was a year younger than my son. Funny though, they were about the same size. I also figured Bobby was not getting any sex education from Jerry either. "Love you Mom." Bobby called out as he walked out the door. "Love you too. Good luck with both your games today." I yelled back. I spent the rest of the day cleaning up the house and doing the laundry. With me working all week long I did not have much time to really clean much. I was just about done with the cleaning and laundry when my good friend and neighbor called. "Hello." I said as I answered the phone. On the other end I heard a voice say, "Hi, Kim. This is Jason." "Oh, hi Jason. How are things going with you and Tina?" I said back. "Well you know. Good days and bad days." He replied. We chatted for about fifteen minutes when he finally asked what I was doing that night. "Nothing. Bobby has a double header today and will not be home until 5:00. Then after he eats dinner will be going to spend the night at Jerry's house. So I will be open all night." I explained. Then I asked, "And you?" "Oh. I am not so lucky. I am having to fight with Tina to get her to clean her room. That will take most of the day. Then we have to go grocery shopping, and after dinner, I too get a break because Tina will be spending the rest of the weekend with her Junior Girl Scout Troop." Jason told me. "Funny." I commented. "What's that?" He questioned. "I have a 12 year old son that keeps his room as neat as can be with everything in its place all the times. You have a 10 year old girl that just tosses stuff where every then complains that she cannot find anything. Just seems reversed." I giggled. "I never thought of it but you are right." He then agreed. After a slight pause Jason then asked, "How would you like to get together for a movie and some talk tonight? Say 7:00?" "That sound great. My place or yours?" I asked. "Um...Yours?" He asked in a hopeful tone. "Sure sounds good. See you here at 7:00." I replied in an energetic manner. Jason was a single father of an only child like I was. Only his was a 10 year old girl named Tina. Tina was also a little small for her age but being 10 she had plenty of time to catch up. Tina was about 4'4" tall not even weighing 70 pounds. She was as cute as a bug. Her fairly long straight light brown hair was always tied back into a ponytail. Her light blue eyes and thin lips was set off by the cute smile that normally was glued to her face. She always seemed to be a happy child but just seemed not to care about neatness. Being only 10 years old she naturally had a flat chest with tiny breast buds that had just began to spout. Her cute butt was another story. Not that it was overly big but it did make her look older than she was. I could just imagine the problems Jason was going to have once she got older and began to date. It was then I was happy I had a son. Jason was like me and got thrown into single parenthood all of a sudden. His wife was killed in a freak car accident several years ago and he like me just never found anyone else. Jason and I were really good friends that could talk about anything. Well, most anything that was. We never seriously talked about sex. We would joke from time to time about something on TV or a movie but as for us every doing anything together, well, that was just not going to happen. I did find him attractive and I too was not all that bad to look at. We just hit it off as friends and I guess neither of use wanted to jeopardize that friendship by getting serious. So this "Movie Date" was normal and I expected nothing more. That evening Bobby came home a winner. They won both their games and he was really excited. He quickly showered while I got dinner on the table. We ate as we talked about his games and what all happened during them. Before I knew it he was out the door and I was hurriedly cleaning up to get ready for Jason to show up. Just as I finished Jason rang the bell. I let him in and we soon were sitting in front of the TV with drinks and popcorn watching a movie. The movie was good but I could tell there was something on Jason's mind. I too was consumed by my thoughts of earlier that morning when I walked in on my son masturbating. I wanted so badly to ask Jason what I should do about talking to my son in dealing with the topic of sex but I just was too afraid of what he might tell me I should do. The more I sat there the more distant I got from the movie. It was not long before both of our distractions would be out in the open. I was startled by Jason calling my name unexpectedly. "Kim?" After a little jump I answered, "Yes?" "Are you really watching the movie?" He asked. "No not really." I said not wanting him to find out what I was thinking about. "Can we talk a bit?" He kind of pleaded. I turned the volume down a bit so we could talk easier but so that there was still some background noise and something to look at if it got to the point I did not want him to look into my eyes to see what I was thinking. "Ok. Shoot." I kidded. Jason kind of cleared his throat like he was trying to get up the courage to have a serious conversation. I was completely taken off guard with his next question. "Um. How old does a girl have to be to get her period?" He cautiously asked. I laughed inside because I wondered why he had asked such a simple question. Then I thought about him being a guy and having a daughter and probably was having problems with her like I was having with my son. "This might just work out nicely." I thought to myself. "Well, average is around 12 but normal age would be between 10 and 15 or could be as early as 8 or as old as 16." I explained. "Like that helps a lot." He grumbled. "So between 8 and 16. Like that really narrows it down." He complained. Laughing I replied, "It is like puberty. All kids are different and that could happen about anytime. Girls getting their period is part of puberty so it is really hard to say." "Sorry. I was just hoping for some hard numbers so I could prepare myself." Jason calmly added. "I know the feeling. Got to remember Tina is probably also wondering and confused. There will be a few signs and by what I have seen, I would guess you have a little time but maybe not much." I tried to tell him but think I made it worse. We talked about the signs and the order girls' bodies went through when they were going through puberty. I told him how old I was and the feeling I was having as my body changed. Slowly I was able to move the conversation to boys and what I might expect from Bobby's changing body. Jason pushed further and asked if Bobby had began to shoot cum. I was a little embarrassed with this line of questioning. It could have been because it had to do with sex and my son or maybe it was because I knew more than I should have. I told him that he was but I did not know much else. He gave me some pointers about how to find out stuff without him knowing or embarrassing him. I did the same with him learning about his 10 year old daughter. The movie ended and we worked our way to the kitchen. We had some more drinks and a snack as we sat at the table and openly talked about our kids. It was almost like we were married talking about our two children. The conversation sure was helpful but also was causing me to do a lot of thinking. Slowly the conversation moved to more about the sexual act than about growing up sex. I could tell he was not trying to get me to bed and that it had nothing to go with us even kissing. I could not tell where he was trying to take the conversation but I was intrigued so I just let him continue on the path he had chosen. Finally he got to his destination and asked, "So how and when did you learn about sex." It was not something I expected to be asked but what I did know was, what was good for the goose was also good for the gander and if I was going to answer the question I was going to ask him the same thing. Bravely I took a deep breath and began to spill my guts. I was 11 when I began to wonder about my body and why things were starting to feel funny. I was too afraid to ask my parents and they did not seem to be able to take a hint so I just let things go. I figured someday I would figure it out. My best friend and I would spend about every other weekend together. Sometimes I would stay at her house and sometimes she stayed at mine. It had been like that for quite some time. We thought nothing about sleeping in the same bed together and we even changed clothes in the same room. Normally we did not see each other naked but when it happened it was just a quick look and usually of their butt as they slipped up their panties but again it was no big deal. Nothing we had done was of a sexual nature. We did not even talk about boys that much either. Well I remember the night like it was just last weekend, I was staying at my friends house that weekend and she had just taken a shower and returned back to the bedroom wrapped in a towel. I was sitting on the bed waiting for her to get done so I could shower. She walked in and without much thought she dropped the towel while standing right in front of me. Without thinking of what I was saying I blurted out, 'You have hair down there.' Now keep in mind she was older than I was but only by about 9 months but that 9 months really made a difference between our bodies. Not only did she have a pretty full bush but she was spouting some little mounds on her chest and compared to my flat frontal region she had monsters. She asked me if I had hair and I told her a few but not much at all and you had to really look to see them. She giggled as she told me to shower then I could show her when I got back. Thinking nothing about it I took a quick shower paying close attention to my privates to make sure they were especially clean. When I returned I dropped my towel and showed her my mostly hairless private area. I told her how fluffy and soft her hair looked and asked if I could touch it. She told me I could if she got to touch my hairless slit. I agreed and soon we were touching each other. It felt amazing. The harder I rubbed her the harder she rubbed me. Our fingers slipped just inside each other's lips as we played and soon we were both feeling really good between our legs. That night we slept closer together than normal not know why but that was what we both wanted to do. This went on for a month or so then one night she asked if I wanted to try something new. Instantly I told her I did. She got between my legs and before I could ask what she was going to do she had shoved her tongue into my crack and was playing with my clit. She sucked and licked my slit and my clit until I thought I was going to explode. I guess I did because I began to shake with my first little orgasm and as soon as it began it ended. I did the same to her but I noticed a little liquid being pushed into my mouth as her body shook. I asked her if she peed in my mouth and with a giggle she said 'No' that it was cum and that when I got older I too might squirt but not all girls do it. This too went on for a month or so until once again she wanted to know if I wanted to do something new. Well, I had been having so much fun with all the new stuff that I was not going to turn down learning more especially since my parents were not going to teach me anything. My friend then pulled out a big dildo she had swiped from her sister's room. I asked her about it and she told me that her sister had it hidden but that she had walked in on her sister one time while she was using it so my friend knew what to do with it. By now I was 12 and my friend was 13 and we just knew we knew as much as anyone did. My friend had been playing with the dildo off and on and so her pussy was already stretched out enough that it went in. It was a tight fit but still went inside without much pain. I figured if she could do it then I could too. I lubed myself up and began to work it inside. I could not get it to fit no matter what. It was not a big monster size but for a little girl it sure looked to be huge. My friend then told me I just had to push harder but before I could do anything about it she took hold and jammed it up inside me ripping me in half. I rolled up into a little ball and began to cry from the pain. Eventually the pain went away bit I soon found out why she had me put a towel under my butt. There was blood and other fluids from where she had popped my cherry. We continued to be friends but not like we were and very seldom did any more experimenting. It was not long before she moved on and began having sex with different boys. When I turned 13 I was allowed to date and it was not long before a 16 year old asked me out. He took me to a movie and on the way home we parked. Before I knew it he had my panties off and had his dick inside my hole. He was pretty small so did not hurt but he only lasted about five minutes before he came. Soon as he came he pulled out and took me home and never called me again. I felt so used that I did not go out again until I was a senior in High School. I went out a few times before I found someone special. I did have sex a couple times and was a lot nicer. I thought I was in love but things did not work out. We stayed friends but that was it. When I got to college I met the one I married. He was the first one that seemed to care about me more than anyone else. I guess what made the whole growing up thing so hard was my parents did not seem to care or maybe it was just they did not know how to deal with me growing up." When I finished my story Jason told me he was sorry about what I had to experience when I grew up. He told me he needed more to drink so I told him to get what he wanted. I noticed a wet spot in his pants when he got up. I am sure he did not know it was there because he did not try to hide it. I just wondered what made him so excited that he wet his pants with pre-cum. Was it thinking about me as a little girl? Was it that he wanted to have sex with me? Maybe he was wishing he could have seen what I had done with my best friend? I did not know and I was sure not going to ask. He got a drink and handed me some more too. We also had another snack as we continued to talk. We chatted some about the kids but nothing to do with them and sex. He did seem at avoid talking about his sexual growth as a child. I figured I had just told him things that no one else ever knew and it was only fair he do the same for me. I gave him every chance to tell me and when it looked like he was not going to tell me I simply asked. "So how was it with you? What was it like for you growing up and having to deal with sex?" I point blank asked. With an uneasy look on his face he commented, "I guess it is my turn to give my growing up story." I smiled and shook my head as he paused his speaking. It was not long before he began and like me he did not stop until his whole sex life was out in the open. "I guess I was somewhat like you in that my parents also did not want to discuss sex. Dad commented that I would learn the same way he did which was basically saying he did not know much about it. Mom was to embarrassed and said I would learn in Sex Education class. So pretty much I was on my own. I was 12 years old almost 13 when a new family moved in down the street. It was a father, mother, and two children. They had one boy age 13 and one girl age 12. Their father and my father became friends which made it easy for me and the boy to become friends even though there was almost a year's difference in our ages. We quickly learned that we both like camping so we got a tent and would set it up from time to time out in the yard and would sleep outside. Sometimes in my yard and sometimes in his yard. It was one of those camping nights that things got started. He asked me if I shot. Not having a clue what he meant I said, 'Shot?' To which he asked a different way, 'Yeah, you know, bop your bologna, choke the chicken, beating the bishop.' And with each term he use I just looked at him with a stupid look and shook my head in confusion. Finally out of desperation he said, 'Jack off? You know shoot your cum?' Finally, I got it and admitted that I did not know. I explained that I rubbed it some but did not know how to jack off much less cum. Once he stopped laughing at me, he asked if I wanted to learn. I was too scared to say 'No' because I figured he would call me a baby or something worse. He told me I would have to get naked which I did. Frankly I was terrified. I had no idea what was about to happen. He took hold of my 3" limp penis and began to rub it. A few minutes later it really began to feel good and shortly after that it began to grow. It grew and grew and grew. I had never seen it so big and wondered how big it was going to get before it blew up. By the time it finished I was super hard and measured 5.5" long. I knew it was that big because he told me that I had a really big one and was curious so he measured it. It was not only long but it did have some thickness to it also. After he measured it he went right back at stroking my shaft until I began to get a feeling. I began to push up and pull back as I tried to make it feel even better as he did his thing to it. Not long after that I erupted. I blew a good sized load for a 12 year old and luckily he aimed it to the ground and not on my sleeping bag. I was coming down from my orgasm when he said, 'Yep. You shoot. Not bad either.' Now that he got me started I wanted to see how I compared so I asked him about his. He told me that if he took his clothes off and I laughed he would beat me up and that I had to jack him off like he had done me. I agreed and soon he was naked. He was almost a year older than me, was more experienced, but yet his dick was a lot smaller. His measured 4" and was not even as thick as mine. I kept my promise and did not laugh mainly because he was a lot bigger than I was and knew he could beat me up easily. I jacked him off like he did me but when he came he exploded with a massive load. It was at least twice as much as mine and shot twice the distance. Well our jack off sessions continued for several months until I guess he either learned more or wanted more action. One night he asked if I knew what a blow job was. I told him I had heard the term from an older guy that made a comment about how his girlfriend could really give great blow jobs. Other than that I had no clue. We were already naked and our dicks were already hard. I guess he was really wanting sex bad because without asking he lowered his head to my lap and began to suck me off. At first I was a little afraid but it soon began to feel really good and when I felt the cum beginning to flow I tried to pull out. I warned him I was about to cum but he latched on even tighter and I had no option at that point. I blew my load down his throat as he drank every drop. I laid back on the ground panting from one of the best orgasms I had ever had when all of a sudden I felt his dick pushing on my lips. I opened my eyes to see a dick and balls as they tried to force their way into my mouth. I knew I had no choice so I opened my mouth and took his small member down my throat. I sat up some to get comfortable as he pushed his dick in and out of my mouth. I sucked his shaft as me made love to my face. A few minutes later he blasted one of his massive loads that took me by surprise. I drank what I could but there was just too much and some ran down my face and some ended up spurting out into the grass. He laughed a little telling me that over time I would learn to drink the whole load. That was not something I wanted to hear. I mean, it was ok to do it once and would not mind doing it every once in a while but sucking dick was not what I wanted to do all the time. Well over the next several months we sucked each other and jacked each other off but once again he wanted more. This time he asked if I had heard of anal sex. I had finally moved on and was 13 years old and taking Sex Education in school. There I had learned about anal sex but was not interested in having something shoved up my butthole. I told him I knew what it was but was not really interested. Once again he basically threatened me by saying he would tell everyone I loved sucking dick if I did not let him cum in my ass. Without a choice I allowed him to lube me up and I watched as he lubed up his now 4.5" thicker dick. He had me get on all fours and without much warning and with no gentleness at all he rammed it inside my hole. It was a good thing he was not as big as I was but it still hurt a great deal. He lasted a good ten minutes as I could tell he was just taking his time. When he blasted his load I could feel it splashing around inside. I have to say it did feel good when it came but getting to that point was not worth it. Once he pulled out I figured it was my turn. He laughed at me as he said he was never going to let my monster inside he tight hole. He did suck me off so at least I got to cum. He did it to me a few more time but I guess he was ready to move on and found a girlfriend. From then on I was on my own. I had never been on a date. I had no experience with girls and was totally lost. It was not until I was 17 before I actually had sex with a girl and pretty much she was my first girlfriend. That did not last long and like you I did not meet the love of my life until I was in college. I have never told a single person what I went through as a boy, not even my wife. I was just too ashamed to tell anyone." Jason said as he finished his long story. By then we were both thirsty so he got up to get us some more drinks. Again I noticed he had a wet spot and wondered if secretly he really did enjoy having boy on boy sex. I was surely not going to ask. I did not even allow him to see that I had noticed. By the time we had both finished our stories I know we were both in the same boat. We did not want our children to grow up like we had but yet neither of us had a clue about how to talk to them about sex. We must have talked for an hour or so more as we tried to figure out what to do about our difficult problem. I could tell he was getting as frustrated as I was but then he began to ask some questions that eventually led to a solution but not for many more months. "You like Tina don't you?" Jason asked me. Being a little surprised about the question I answered, "Like she was my own child." "Well I feel the same about Bobby." He then quickly said. This began to worry me a little. When they first moved to the area, I was Tina's first babysitter. I actually had become attracted to Jason but when the feeling was not apparently mutual I dismissed the idea that something might become of our friendship. Now Jason was scarring me a bit. I was worried he was now wanting to get something started and as of then I had too much other stuff to deal with. "I know." Was the best I could come up with to say at that point. After a long pause Jason sheepishly asked, "Do you think Bobby likes Tina? You know, like does he think she is cute?" I knew exactly what he was wondering even if he was not asking it the right way. He wanted to know if maybe my son liked his daughter enough to be interested. That was a good question and really I did not know. Bobby was not allowed to date yet and as best I knew he had not even kissed a girl. This thinking then made me worry because he had been sleeping over at Jerry's house quite often. "Good question. I really do not know. He never mentions anything about girls. All he talks about is baseball and Jerry." I told him. Jason gave me a look like it reminded him of his childhood. That part I had already thought of and, yes, it did worry me. We chatted a little longer but when we noticed it was after two in the morning we decided to call it a night. I knew his shorts had pre-cum spots and my panties were soaked but I figure that neither of us knew why. He went home and I went to bed. I am sure both of us worried the rest of the night about our children and how to take care of the problem. It had been a few weeks or so when Jason called me up and asked if I thought his daughter needed to start wearing a training bra. I gave him my thoughts and eventually he invited me to go shopping with him and Tina. It was now close to Summer and with the warmer weather going to be happening soon he figured she needed some new summer clothes. As we talked I found out more of his plan and found it interesting to say the least. I was to go shopping with them to help pick out some clothes that might make her more interesting to Bobby. Some sexy skirts, shorts, panties, etc. were some of the items on the list. Bobby was busy with baseball so he was not going to be around anyway. Then over time we were going to do things together like movies, dinners, and other family things but with two different families. We would be closely watching the children to see if they were interested in each other. If we found any interest at all we were going to build upon it to see if we could nudge them closer together. At least this way we could make sure each would have a good partner to learn with. I just was not sure how much we were going to guide them on this journey. The shopping trip went well and I was able to help Jason pick out some really cute clothes for his daughter. I found a cute little skirt that was so short that if she bent over her panties showed and of course I had to match that up with a really cute pair of panties with lots of ruffles and a bow. The top was plain but cute with a few ruffles and under the top was a cute frilly training bra. Among the other clothes were more cute sexy panties another skirt or two but not so short and several pairs of shorts some of which barley covered her butt cheeks. Tina was sure happy with the clothes but had no clue of her father's plan. I just knew one thing. If my now 13 year old son did not start drooling over this little 10 year old girl than I knew he was only into boys or there was something seriously wrong with him. The plan was to start out slow. Tina was dressed in some basic shorts and top to play outside. I would make sure that Bobby saw her dressed in her cute outfits as often as I could without making it too obvious. After a few days of teasing him Bobby and I were invited over for a cookout at Jason's place. There the plan progressed and Tina wore even shorter shorts. It was funny watching Tina tease my son, especially since she had no clue of what she was doing or why. This then led to an invitation for them to come have dinner with us. This time Tina wore a skirt and top. It was a cute outfit but not the short one. Jason and I watched as Tina paraded around showing off her new clothes. We also noticed that Bobby was trying to catch some glimpses of her panties which did not happen. Just the attempt was putting me more at ease about this plan working. The next step was dinner out. This then required an even shorter skirt and one that with a little prodding caused Tina to have to bend over just at the right time allowing my son his first look at her pantied butt. Paying close attention to his crotch I noticed a bulge beginning to grow once he had seen her panties the first time. This also led to him trying harder to get more peeks at her panties. I even found myself trying to do things to cause her panties to be viewable. We had spent a good month or so to get this far and with time running out we knew we had to increase the heat a bit. Over the next few weeks the shorts got shorter and her shirt got tighter showing off the training bra just at the right time. Just as an incentive Jason left some of Tina's panties in the bathroom where when Bobby had to go he had to have seen them. The first trip he made was quite lengthy and I even wondered if he had to do a quick jack off session but eventually we figured he was just enjoying the view. Summer was just about over but we had been able to tell that Bobby's attention toward Tina had crossed over to the more interested side from the non interested side. Tina's interest was a bit less obvious. Then again Tina was still only 10 years old. Her birthday was coming in a couple months but even at her increasing age she had not shown a sexual interest yet. Jason and I decided to go for broke. He dressed Tina up in her shortest skirt she had along with the cute matching panties, training bra, and cute frilly top. They were to come over for dinner and a movie. We were not sure what was going to happen but we were going to push the best we could. Dinner was good and with Tina's short skirt showing off her panties Bobby seemed to be more interested than ever before. Jason and I kept a close watch on Bobby to see what his intentions were as the night progressed. After dinner we all moved out to the living room to watch a movie. We picked one that had a hint of sexual content. It was not real obvious but just enough to make a 13 year old boy wish he was alone so he could please himself. Jason and I sat side by side on the couch that gave us a good view of the love seat and the TV. Bobby and Tina sat side by side on the love seat. They had a good view of the TV but were not able to see Jason and I without turning their heads. The set-up was a good one. Now to see if it was going to pay off. The movie had not quite made it to the midpoint when the first signs of success crept in. Out of the corner of my eye I caught Bobby glancing over to see If we were looking in their direction. When he saw we were not he turned his head back to the TV. This was important because Bobby was on the couch closest to us with Tina on his right side. With the TV more in front of Tina than the rest of us meant that Bobby had to actually turn his head or his body to check to see if we were watching. This gave us a warning to turn so he could not tell we were actually watching what they were doing. With that first hint I then watched closely to see his next move that came pretty soon. I watched as Bobby reached over and took Tina's small left hand. At first I figured they were just going to hold hands which I thought was really cute. They did but for only a minute. I guess Bobby was just checking to see if she would cooperate. When she did not pull away he went further and gently pulled her hand to his lap. Opening up her fingers he placed her hand palm side down on the growing budge he had between his legs. At first she tried to get away but he held her hand down until she figured she could not get away. She went to pull away again so Bobby leaned over and whispered something in her ear. I could not hear but she quickly put it back and never tried moving it away again. I watched as he 'taught' her how to rub his hard dick even to the point of grabbing hold of his shaft through his shorts. She was not jacking him off though. She simply was rubbing some and letting her hand rest between his legs some. I gently elbowed Jason to get his attention. He looked at me and I kind of nodded towards the kids so he could see what was going on. When Jason figured out what they were doing he looked back at me and smiled. I smiled back and we both paid more attention to what the children were doing. When Bobby had managed to get Tina's hand where he wanted it he moved on to the next step. My son then bravely took his right hand and put it on Tina's privates. He was wise enough to do so on top of her skirt. Surprisingly enough, Tina did not fuss. She even spread her legs a bit allowing my son's fingers to find their way into her pussy slit. I watched as he rubbed her pussy up and down making it obvious they both were enjoying their playtime. This lasted a good 10 to 15 minutes and both Jason and I had completely quit watching the movie. The kids still faced the TV but I really did not think they had a clue what was going on. Jason and I had about given up on any further excitement and Jason was just about to guide them into the next step when all of a sudden we saw Bobby making his next move. I will say that my son was really taking it slow with Tina. Could be he did not want to scare her or maybe he was afraid she would make some noise that would get our attention. Finally, Bobby slowly began to pull Tina's skirt up. Still using one hand he would pull a little skirt then go back down. He did that several times until his fingers were back inside her pussy lips but now the only thing between his fingers and her skin was her thin little sexy panties. The more Bobby stroked her pussy lips the wider her legs got until if it were not for her panties he would have been finger fucking Tina's pussy. I could feel my own pussy getting wet but was not sure why. I mean this was my son I was watching. I should not be getting excited by watching my son toying with a girl's snatch, especially since the girl was only 10 years old. I looked down at Jason's lap and saw he had a huge bulge and knew if he was not totally erect he sure was close to it. This made me feel a little better. "Was my son going to slip his fingers into her panties? Was he going to persuade Tina to slip her small hand into his shorts and underwear? Was he going to get Tina to stoke his dick?" Were all questions that raced through my mind. By now the movie was almost over and we were not any better off than when it started. If Bobby did not make his move soon it would be too late. This was when Jason did something I had not planned on. "Bobby." Jason called out. He said it in a loud but non threatening way. He then quickly followed it with, "Kiss her." "Tina. Kiss him back." He soon added. I could just imagine what went through their minds when they heard their names called out. It even made me jump so it was no surprise that they both jumped, pulled their hands back, and sat up all within a second or two. Now taking the lead I said, "It is alright kids. We just want to guide you through this very awkward sexual process of growing up. Now put your hands back where they were." They looked at each other and not knowing what to say or do, They did as I instructed. It took a minute or two before my son's fingers were under Tina's skirt but eventually they were back like they were. From then on I figured they would do as Jason and I said. "Good. Now...Bobby, lean over and kiss Tina on the lips." I instructed. "Tina...Kiss him back. Do not be afraid to let your tongues enter the other's mouth." Jason added to the kissing part of the session. I heard Tina let out a quiet sexual moan which led me to the next bit of information. "Good. Do not be afraid to moan, purr, or use any other vocal noise or comment. This helps your partner know what you like and what you do not like. Be as open as you wish. We just want this to be an experience you both will remember the rest of your life." I told them both. Jason then becoming as excited as Bobby, put himself into my son's shoes. He then told my son what to do like it was what he would have done in that same situation. "Slip your fingers into my daughter's panties. Tina you need to work on undoing Bobby's shorts so you can grab hold of his penis." Jason commanded the children. I was sure that set of instructions were hard to grasp for the children. It is not every day that the father of a 10 year old girl tells a boy to stick his hand inside his daughter's panties so he could play with her pussy. But, we were not ordinary parents. We had been through a very rough childhood and we wanted own children to have it better than we did. Tina struggled some but eventually was able to get her little fingers wrapped around Bobby's hard shaft. I still had not seen his size and did not even know if he had hair around his dick. I figured he did but could not be certain. Bobby wasted no time and he not only slipped his fingers into her panties but he even was rubbing inside her pussy lips. Now that they knew we were watching and that what they were doing was alright with us, Jason and I moved in closer so we could see better. With just a little more help, Bobby learned how to play with a girl's clit and how to make her really feel good. Tina was moaning up a storm and I figured anytime now she would be having an orgasm. They had broken off the kiss because they were having difficulties breathing. They were really going after each other but in the position they were in I figured they would be more comfortable in a different location...and naked. "How would you two like to move to Bobby's bed?" I politely asked. "Good idea." Jason added. Now for the first time since the movie started the kids finally spoke. "You mean we can keep doing this in my bed? And you do not care?" Bobby confusingly asked. "Right...Might even be more fun if you help each other off with your clothes before getting into bed." Jason then suggested. The kids just looked at each other like we had lost our minds. Well, I guess we had but this was the only way we could think of to help them grow up easier than we did. We made it to Bobby bedroom and with Bobby and Tina standing beside the bed, Jason and I sat down in a couple of chairs to guide them on their way to the best night of their lives. "Tina, why don't you start by removing your shirt first. Bobby while Tina does that you go ahead and take your shirt off too." Jason told them. With them both shirtless I told Bobby to help Tina take her bra off. He had never done anything like that before so Tina had to actually tell him what to do. To some extent it was comical to watch two little children undress each other. With them both topless I suggested they give each other a long hard kiss. I added that they should hold each other tight so they could feel what it was like to have a naked chest next to theirs. They began to kiss but before any other instructions could be said, Bobby began to pull Tina's little skirt down. Tina not wanting to be out done, worked on removing my son's shorts. They were still kissing as they held each other while only wearing panties or underwear. I took a glance over at Jason and his dick had risen to a massive size. If he was not totally erect at that point then I was afraid of how big it would end up being when finished. I could feel my own soaking wet panties as I sat and watched two small adorable children slowly get ready for their first sexual experience. Just as we were going to tell them to finish stripping, they broke their kiss. Bobby stepped back a step so he could get a good look at the little girl he was about to push his hard cock into. If not for a strong interest in waiting to cum, Bobby would have filled his underwear up with boy cum as soon as he saw Tina standing there only in panties. I too was excited seeing her almost naked. Without further instruction, Bobby stepped up and with one hand on each side of her body he grabbed the lace waistband of her panties and slowly pulled them down. She wiggled her hips to help them slide down easier but soon as they were down and off she did the same to Bobby. The problem she had was that his dick was so hard and big that she had to work to get them off of him. Bobby looked closely at Tina's slightly puffy nipples, flat stomach, sexy belly button, and almost totally hairless pussy. I could hear him moan in anticipation of what was about to come. While he looked at Tina, she too took the time to closely look at the boy that was just about to take her cherry. Funny but this was the first time I actually got a chance to see my own son naked since he was a little boy. He now had a nice mound of hair around the base of his shaft but little to none around his balls. His circumcised dick had grown from a 4" soft penis to over 6" when it turned rock hard. It was not all that thick, but fuck it was long for a little 13 year old boy. I worried if it would go in Tina's little 10 year old pussy without serious damage. I could see the same concern on her father's face as he too looked at my son's massive meat stick. I grabbed a towel and laid it on the bed to catch the blood that was definitely about to be spilled as Tina's cherry was ripped apart. I grabbed some special lube that was supposed to be really slippery so it would make penetration easier. "Help Tina into your bed then come over here so I can talk to you." I told my son. I then handed the lube to Jason and told him to have a talk with his daughter as he lubed her up. He stepped up to the bed and began to put a lot of lube in and around her tight almost hairless pussy. He told her how this was really going to hurt and if at any time she wanted to stop to just let us know. He explained how if she just relaxed and thought of something else until he was inside her that she would not feel it as much. He kissed her on the lips and told her that he loved her and that doing this now would make future sex a lot more pleasant. While Jason took care of Tina I worked on Bobby. I took some lube and lubed up his long hard cock and also explained that with him being so big that he was going to have to go slow and to be as gentle with her as he could. I told him not to be in a hurry and not to rush her. I also explained that if she ever wanted to stop that night or any other night and for that matter if any girl ever wanted to stop at any time then he had better stop and that he should never force himself on any girl or boy in the future. He told me he understood and with that, I too kissed him on the lips as I allowed my 13 year old son to get into bed with a 10 year old girl for the purpose of sex. I was so hot that if I even touched my pussy I would have exploded. I wanted to go grab my vibrator to take care of myself as I watched my son but figured that was a bit out of line. Bobby climbed into bed and kissed her gently on the lips like we told him to. He then turned the kiss into a hot French kiss as they each shoved their tongue into the other's mouth. Tina instinctively parted her legs to allow more room for Bobby as he began to lay down on top of her. Jason called out for him to lick and suck her nipples and belly button before he began. Doing this helped relax her so that it might not hurt as much. Bobby followed the instructions and soon was back in position. Tina's legs were pulled up as Bobby looked into Tina's soft blue eyes. We continued to give guidance as he got closer and closer to inserting his hard shaft into the girl's tight virgin hole. Jason and I closely watched Bobby's dick as it bobbed up and down with his heartbeat. He moved in closer and closer until the tip of his greased up dick head made contact with Tina's greased up pussy slit. He kissed her with a light tender kiss as he lowered his small thin muscular body down to her even smaller lighter framed body. They both let out a moan of pleasure as Bobby's dick finally made contact and entered her outer pussy lips. Bobby began to give her a harder kiss and he began to push his dick head into her hole. I could see on Tina's face a look of pain. I had my son pull out a bit and slowly push back in. After a few time of this, Bobby knew what to do and when. He worked his dick head inside until it hit something that was blocking the passage. Jason and I both knew my son had run across Tina's hymen and at this point there was no getting around it. Bobby was going to have to ram his cock hard and fast into her pussy busting her hymen open. While he was in a waiting position we tried to explain the best we could. Jason took on the responsibility of this part. "Tina, Bobby is going to have to do something that is going to hurt. The best for you to do it to follow my instructions. I will tell you when to take a deep breath and hold it. I will tell Bobby when to push and he will then shove his dick hard and fast into your pussy. This will pop your cherry. He will then need to stay still inside you until you are ready to have sex. When you are ready just start thrusting your hips up and down. That will tell Bobby he can start and from there the two of you can fuck until you both cum. I do hope Bobby takes his time and allows you to cum but it is not as easy as it sounds. Ok. Ready?" Jason wondered. The kids said they were ready and with that Bobby continued to slowly work is way in and out. When Jason thought the time was right he said, "Ok. Tina, take a deep breath and hold it." She did as told and when he figured it was time he said, "Bobby, shove your cock into my daughter's pussy, NOW!" Bobby rammed his dick as hard as he could sending the little 10 year old girl into instant shock. She screamed out in pain as her eyes filled with tears. Jason told Bobby to now wait for Tina to get use to it. Jason wiped the tears from his daughter's eyes and cheeks as she continued to cry from the pain. She wanted it out but we all knew that would only hurt more and in the end would be even more of an issue later. It was about ten minutes later when the crying stopped and Tina found it was not as bad as it was. She began to push up giving Bobby that sign he could start. He started off slowly but was not long before he was pumping his hard shaft in and out of the little girl's pussy. It did not take long and Tina was enjoying being fucked by my son's cock. She pushed back and soon they were fucking each other, begging each other to pump harder and faster. They both screamed out they were cumming as they exploded with a huge orgasm at the same time. Bobby pumped a load of cum into Tina's hot pussy that most men would have been jealous of. Their bodies shook until they both were totally exhausted. When they had finished Bobby pulled out and instantly was worried when he saw all the blood on his dick, towel, and all around the girl's snatch. We explained that was from the hymen being ripped open. We told them that was the cherry and being popped meant she was no longer a virgin and that it would never grow back, meaning it would not hurt like that again. We cleaned them up and talked quite a long time about why we did what we did and allowed them to do it together. It was getting late and we asked the kids if they had any questions. "Do you have to watch when we do it next time?" Bobby asked. This question took us by surprise. It had never crossed our minds that they would want to keep doing it. With her only being 10 we just figured they would move on to other children in the future. Jason and I went into the hall and discussed it. When we came back inside the room I told them what we had decided. "As long as sex does not get in the way of your schoolwork then it is ok to do it when you want. But! You are never to tell anyone what you two are doing and if someone finds out do not tell them that your parents taught you what to do. Make sure you never do anything that the other does not want to do. Do not force the other to do it when they do not want to. Jason will take Tina to the doctor and get her on birth control so we do not have any babies running around. And one more thing, in one month we will watch you do it again to make sure you learned the right way and are not doing anything dangerous." I told the children. "Can we sleep together all night sometime? Tina asked. With a questioning look on his face, Jason said, "We will see. You are only 10 years old. There will be plenty of time to sleep with a boy in the future." A month later we watched the kids fuck and they were really loving and good to each other. We allowed them to sleep together one weekend a month which soon turned into two weekends a month. Tina was put on birth control pills which eased our minds on that issue. By the next summer they slept together every weekend once at my house then once at Jason's house. Then back at mine. When Bobby turned 18 he proposed and when Tina turned 18 they were married. Neither of them ever knew another partner and really had no need. They were perfect for each other and because of our guidance they knew just how to please each other. Over time they had children and I just hope that they teach their kids like they were taught. Jason and I never did have sex, even though we wanted to. We just felt it best not to. This way we knew we would stay friends. I was happy and was sure Jason was also happy the way it turned out. The End