Date: Sat, 18 Feb 2023 08:07:31 -0500 (EST) From: ShortStories@PlayTime69.e4ward.com Subject: Grandparents Inc. - Chapter 6 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 grandparents, their young teenage grandson and pre-teen granddaughter. During the different chapters there will men and women of many different ages interacting with the grandchildren. 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. 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Table of Contents (Players-Age) Chapter 1 - The Beginnings (Jim-57 and Barbara-53, Jasper-13 and Missy-11) Chapter 2 - Testing the Waters (John-80 and Joann-79) Chapter 3 - Quest for Fun (Chris-30 and Lisa-29) Chapter 4 - Gay Adventure (Rob-65 and Gary-62) Chapter 5 - Lesbian Fun (Heather-30 and Mary Ann-32) Chapter 6 - Exploration (Neil-28 and Ashley-9) Chapter 7 - The Ordeal (Patrick-23) Chapter 8 - Needing a Break (Theresa-61) Chapter 9 - Please Help (Brad-21 and Becky-18) Grandparents Inc. Exploration by: Playtime69 This week was going to be interesting for sure. We had spent a considerable amount of time going over the possible clients for the weekend and the ones we picked were done somewhat on the basis of compassion. This weekend's clients were a father and a daughter. The father, Neil, was 28 years old. He was about 5'9" weighing about 130 pounds. He had short brown hair and brown eyes. His dick was also on the shorter side at 5.5" and not much thicker than Jasper's dick. He was a kind gentle person and as best we could tell very loving. His daughter, Ashley, was only 9 years old 4'2" tall, which was just a few inches shorter than Missy. She weighed a mere 60 pounds which was about 20 pounds less than Missy. She had light brown hair that went half way down her back and was tied back into a ponytail. Her face was cute and her lips looked full of love when she smiled. She had hazel eyes that seemed to be pleading for acceptance when you looked into them. Her chest was as flat with two small cute nipples marking where her breasts would be when she got older. Her pussy was free of any hair and it was not because she shaved it was because of her young age she just had not grown any yet. Matter of fact she was completely hairless except for her head. She did have a light dusting of small light baby hair over her legs but unless you looked close you would never notice. Overall she looked like a cute little doll that could be put in the chair and played with when needed. Her pussy slit was tight with her lips touching each other. It was a cute little pussy slit that would make any male want to beg to enter. Ashley was a virgin which leads to why the father and daughter was visiting for the weekend. Neil's wife was killed in an automobile accident about two years back and Neil had been raising Ashley on his own. She was a good kid but very quiet and skittish. She did not have many friends which made things worse. Her daddy was her world and she was his. They did things together and when Ashley was with him she felt safe. She was always afraid that if she was not with him something was going to happen. She worked hard around the house with cleaning and cooking. She wanted so badly to make her father happy that she did not even think about herself. One day she came right out and told her daddy she wanted to do everything her mother did so he would be happy. They had an in depth conversation and it came out that Ashley even wanted to make him happy in bed. She did not have any idea what to do or how to go about doing it but she wanted to learn. Neil was afraid of sticking his hard cock into her without her having experience and even though he was not all that huge he was still afraid. Neil wanted to be in the room when it happened and was even willing to work with them to make her open up more but was not going to come right out and say he wanted to fuck her even though that was what he really wanted to do. Jasper was quite excited about getting to fuck a little 9 year old girl. Missy on the other hand was a little jealous. On one hand she wanted to help Ashley learn how to fuck but she did not like the idea of Jasper popping her cherry. Jasper had fucked women of all ages but when it came to a cute little girl younger than herself Missy was a little concerned that her brother would find her pussy not as much fun any longer because it was too old for him. Knowing she had no choice she decided to make the best of it. The weekend came and they began to get ready. Friday night they checked everything to make sure it was clean and ready. They laid out the toys that might be used during this different training lesson. They were not going to plan on using too many toys because they knew they were going to have enough just dealing with her being a virgin as it was. They did lay out some assorted dildos and vibrators. They also were pretty conservative with the clothing they would be wearing when they first met. Jasper picked out a pair of underwear with cartoon prints on it and Missy picked out a pair of panties with a similar print. As a family they decided to lower the cost to just that of a single person. They figured that they would not be as used and fucked as normal plus it was still unclear if Neil would actually fuck Missy or Jasper. It might turn out he only fucked his own daughter. All things considered they knew this weekend would be more fun than work like the other weekends had been. With everything ready they watched some TV and relaxed until the next morning came. Saturday morning arrived and after we had eaten Jasper and Missy showered together while I helped Barbara in the kitchen. It was not long before Barbara and I were in the living room waiting on the new clients. Jasper and Missy were dressed and waiting in the office until they were told the room was ready for them. A few minutes later there was a knock at the front door. I opened the door and saw the two that matched the pictures so I invited them into the living room to get better acquainted. Ashley was super cute and super shy. She hung onto her daddy like a leaf holds onto the tree. We talked a bit and noticed that Ashley said very little even when she was asked questions. Neil went to pay and I asked Ashley if she really wanted to do this and that it was completely up to her. She looked up at her daddy with a sad scared face but said nothing. "It is up to you Baby. We can leave if you want but if you want to take Mommy's place then we will need to go through with this. Do you want to stay or go?" Neil carefully asked his 9 year old daughter. Looking up at him she quietly answered, "Can we stay, please?" "Certainly." He replied. Neil handed me the money and I took them on a quick tour of the house. I gave the money to Barbara to put in the safe as I took the clients into the playroom. I went over some final things as Barbara went into the office to tell the kids to get ready. A few minutes later Barbara came into the playroom and sat down on our bed beside me so we could enjoy the show. Neil sat on the bed closest to us after he had his daughter sit on the edge of the bed closest to the door. Not long after we were all ready there was a faint knock on the door. Neil told Ashley to let her new playmates come in. She hesitantly did as told and not long after she opened the door she was back on the bed waiting for what was to come. Jasper took one look at the little girl and for a split second lost track of what he was supposed to say. I watched as Missy made a face about her brother's first reaction to the little girl on the bed. I knew this was going to be a challenge in several ways and again wondered if we were doing the right thing. When Jasper got hold of himself he finally made his normal speech. "Hi Neil." Jasper said then instantly moved his eyes to look right at Ashley as he continued. "Ashley. You sure are a pretty little thing. My name is Jasper and I am 13 years old. This is my 11 year old sister, Missy." Then off the script he asked, "And how old are you?" I figure he was just trying to make her more relaxed but I am sure Missy took it as he was flirting with her. Ashley looked down and with a shy quiet voice she answered, "I am 9 years old." "Well Ashley, we are here with you this weekend to make you feel good and to teach you a few things. Do you like what you see?" Jasper said as he got back to the script. They slowly turned around so Neil and Ashley could get a good look at their butts and how they were dressed. Neil was mainly looking at Ashley to make sure she was doing ok with what was going on. Ashley was being very bashful. She was looking but said nothing. The smile on her face told it all. This time Jasper had on a pair of cartoon printed underwear Missy had on a pair of panties that looked similar to her brother's. They both looked really cute, and dressed as they were they looked even younger than they actually were. It was now Missy's turn to get involved. "So how would you like to get started by taking your clothes off so we can get a better look at you." Missy suggested. Ashley backed up on the bed like she was scared someone was trying to get at her. She turned and looked at her daddy to see what she should do. "It is ok. They are not going to hurt you. Would you like me to come over and help you undress?" Neil asked his daughter in a calming tone. "Ummm...Hmmm..." Ashley whispered as she shook her head. Neil got up and looking at me to see if it was ok walked over to his daughter and pulled her little shirt up and over her head. With Ashley's little pink nipples now exposed Jasper's dick began to raise. Hate to say it, but mine did too. Ashley then laid down on the bed and raised her butt up so that her father could then remove her shorts. He then checked with her again before he pulled her tiny little pastel printed panties off. Now with her naked not only was Jasper's cock pushing out his underwear but Missy was taking swipes at her pussy trying to get it to calm down. Neil went back to his bed even with his daughter's complaints. Now it was up to the kids to get things going. "Would you like me to take my panties off too?" Missy asked Ashley. "If you want to." Ashley quietly answered. "What about me?" Jasper quickly asked hoping she wanted to see him naked. Giggling, Ashley answered, "I don't know. You have a thingy like my daddy and I don't know if I should look at it." She then turned to her daddy and asked, "Should I have him take his underwear off too?" "I think you should." Neil answered. "But I want to see yours too. Are you going to stay dressed?" Ashley asked her father. "Would you like me to strip naked like you are?" He then asked his daughter. Ashley giggled a really cute girlish giggle and nodded her head but said nothing. Jasper getting tired of waiting said, "So? I guess you want me to drop my underwear?" Ashley again giggling and being really shy, hid her face in her hands and then nodded her head, "Yes." A few minutes later she peeked through her fingers to see who was naked. When she saw Missy was naked and standing close to her bed she pulled her hands from her face and said, "You do not have any hair down there. Why not?" Missy without question, answered, "I have shaved it all off. Just like my brother, see." Ashley turned her head and saw Jasper's cock sticking straight out and just like Missy's privates were hairless. Ashley's mouth opened and commented on how Jasper's cock was big and hard. She then looked at her daddy and saw he too was hard but he had hair, but it was just trimmed really close to his skin. "Daddy...it is so big...and hard..." Ashley giggled. Now with them all naked Missy decided to take command by asking Ashley if she would like to touch her pussy. Missy stepped right up to Ashley so that all she had to do was reach out to be able to touch her. Jasper knew how skittish Ashley was so was not going to be as forward as he normally would have been. Ashley closely looked at Missy's pussy slit and noticed how the lips had a slight part to them unlike her own pussy. She also saw that it was moist looking in between the lips where Missy had been excited and was beginning to excrete some slippery pussy lubricant. Ashley starting to get use to Missy's naked body finally reached out and gently ran her fingers over Missy's pussy lips. It was almost like an electric shock. Missy gasped from the pleasure she received by having a young girl's tiny fingers running over her pussy. Ashley pulled back because she thought she had hurt Missy. "No...Please...Do it again. It felt really nice...Please..." Missy begged as she reached out and tried to pull Ashley's hand back to her pussy slit. Ashley gave in and rubbed the outside of Missy's pussy as Missy began to moan. Looking over I noticed Neil's cock was drooling pre-cum as he watched the show. By now, Missy was really getting hot and needed to be fingered so she took hold of Ashley's little hand and pulled it into her pussy making sure she quickly learned how to finger fuck another girl. While Ashley was finger fucking Missy's cunt, Ashley's legs began to spread. Missy, taking notice, slowly sat down on the bed beside Ashley and began to rub her pussy. She slipped a few fingers inside the outer lips but did not penetrate her pussy because she knew Ashley was still a virgin and was going to leave that part up to Jasper. Even though she really did not want Jasper's cock inside this little girl Missy knew she had no choice than to allow her brother to fuck another little girl's pussy. They played with each other for a half an hour or so while all the dicks in the room were throbbing and pouring pre-cum from their tiny slits. Missy took it upon herself to see if Ashley knew how to kiss. She leaned over and planted her lips hard onto Ashley's tender lips. Ashley kissed back but when Missy opened her mouth and tried to French kiss the little girl, Ashley got confused and pulled back taking her fingers with her. Missy explained what she was trying to do and soon Missy and Ashley were French kissing each other. Their tongues exploring each other's mouth and their fingers returned to play with the other's pussy. When Missy and Ashley took a break to catch their breath, Jasper asked, "Ashley, would you like to touch my dick?" "I do not know." Ashley said while looking down at the bed. "It is easy and fun. Look." Missy stepped in saying. Missy moved around and took hold of her brother's cock and began to rub and stroke it. Missy told Ashley to give it a try and with a little more persuasion, Ashley reached out and grabbed hold of Jasper's hard shaft. With some moaning from Jasper, Missy began to stroke him until he had her stop because he was about to cum. I think that was her plan. If she could make him cum then it would be longer before he was ready to cum again which put off him forcing himself on the little girl. It did not take much more talk and Ashley was touching and stroking Jasper's hard dick. He again had to have her stop before he shot his load. Jasper leaned over and gave her a kiss telling her how good she was and how nice it felt to have her little hands playing with his big hard cock. They French kissed for a while and soon she was back to playing with his dick. The three children took turns touching each other while kissing for an hour before the comment about sucking cock came up in the excitement. "Yuck! You mean you put that thing in your mouth?" Ashley asked Missy. Missy with for sexy giggle said, "Sure. I love sucking of cock, especially when it squirts cum down my throat." Ashley just had a blank look on her face as Missy was telling how she loved sucking on cocks of all sizes and ages. She did say she preferred shaved ones but would suck on anything if given the chance. While Ashley was contemplating dick sucking, Jasper asked, "Well what about pussy licking? Would you lick a pussy?" "No! That is gross too!" Ashley quickly said. "What if I lick your pussy? Would you lick my pussy?" Missy brought up the option. Before Ashley could respond, Jasper added, "Once Missy licks your pussy then I will lick your pussy. After that, I bet you will want to lick Missy and suck me too." "I do not know...Daddy?" Little Ashley looked to her daddy for guidance. Neil wanting her to suck his dick knew this was a good start with the main goal of the weekend. They had been kissing for months so for with the exception of them being naked and the kids all fingering each other there had really been no progress made. He knew what he had to tell her. "Baby it is up to you but I think you will like it once you do it. Would you like me to lick your pussy first?" Neil stepped out on a limb by saying. This took us all by surprise. This weekend was to help Ashley become more of a woman so they could have father daughter sex. If he was going to do things before anyone else then why were they there? Luckily Ashley declined his offer but did agree to let Jasper and Missy lick her pussy then she would see about licking Missy's pussy. She really was not too sure about sucking dick yet. Jasper was more than willing to lick this tender young virgin's pussy and in no time he was between her legs with his tongue shoved between her pussy lips. Ashley was moaning as she begged him to do more. Ashley had never been licked between her legs before and the pleasure was driving her crazy. Her arms were flailing around with her hips bouncing up and down as she tried to get as much pleasure out of Jasper's tongue as she could get. Jasper backed off allowing Missy to jump in for some fun. Missy's tongue was not as long or big as Jasper's but she knew just were to lick and nibble to send any female into an instant orgasm. Missy teased all around the little girl's clit darting her small tongue deep into Ashley's pussy hole. Missy took her as close to an orgasm as she could before backing off. Doing this three times in a row was all Ashley could take and Missy knew it. Missy then timed it just right and taking Ashley to the edge the fourth time was going to be the last time. At the right time Missy was going to bite Ashley's clit which would send Ashley into an orgasmic frenzy. "Oh...Oh...Oh...Yes...Yes...That feels...soooo...goooooood..." Ashley was yelling just before she got the famous Missy nibble which caused an immediate unnatural response from Ashley. "FUCK!!!..." Ashley yelped. At that point Ashley collapsed to the bed and Missy pulled her wet face from the little girl's pussy. Unfortunately Missy's wet face was not from girl cum because Ashley was not old enough to excrete cum yet. There was some pussy lubricant but was mostly from spit from both Jasper and Missy as they licked and sucked the little girl. When Ashley came to her senses, she knew what she had said was a bad word and that she was definitely going to be punished for saying it. She also knew there was no way her daddy had not heard that word come from her mouth so she being embarrassed looked over at her daddy and said, "Sorry, Daddy. It just came out." "It is ok, Baby. But do not use that word out in public. Only say in while in private and having sex." Neil told his daughter. Now with Ashley calmed down from both her orgasm and from saying that dirty word she looked down at Missy's pussy. She did not say anything but just looked. It was almost like she was trying to decide if she should like it or not. Missy noticing Ashley looking at her pussy slit came right out and asked if she wanted to lick it. Ashley nodded her head, "Yes" and instantly Missy and Ashley switched places. Ashley looked down at Missy's vertical slit and licked her lips. Missy reached down and pulled her lips apart telling Ashley to give it a taste. Ashley bent over and sniffed her pussy like a cat checking out its food. Then also like a cat she extended her tiny young tongue and gave it a swipe. That one swipe was all it took. She noticed that it was not disgusting and that it smelled rather different. There really was not a taste to it so she went in for a second swipe. Digging in deeper she got a taste of what little girls tasted like when they began to produce girl lubricant when they got excited. That she liked and instantly wanted more. Digging in she shoved her little tongue as far into Missy's pussy as she could get it. Missy began to moan with pleasure as she was being eaten out by a little 9 year old girl. Missy had never had sexual relations with anyone younger than her and did not know how much she was missing until it happened. Missy soon placed her hands gently on the back of Ashley's head and guided her around hitting the important parts of her sex organs. Ashley soon had Missy on the edge of an orgasm and was not letting up. Missy had been teased so much the past few hours that it was not going to take much to finish her off. Missy worked Ashley's face and tongue around and when she was just about to cum she moved her face to her clit. Soon as Missy was ready and Ashley was in place, Missy said, "Nibble my clit. Bite me but not hard." Ashley doing as told but not knowing how hard to bite she bit down on Missy's enlarged clit. She bit a little hard but that might have been the start of something new. Soon as Missy's clit had been bit she instantly shot a stream of cum into Ashley mouth as she screamed, "OH FUCK!!!" Missy's hips thrust up as the cum stream left her pussy and splashed into Ashley's young open mouth. Ashley drank it all down not knowing what else to do. That flavor was even better than what she had been tasting and instantly began to lick and suck up all the juice she could find. Missy collapsed as her heart raced and her breathing was labored. Ashley just looked at her hoping she had not hurt her new little playmate's pussy. "That was fabulous Girl! You can lick my pussy anytime." Missy panted as she tried to catch her breath. Jasper with his pre-cum covered dick said in a hopeful voice, "Me...Next?" Ashley now looked at his cock in a different light. She sweetly nodded her head and soon she had her small thin lips wrapped around his entire 5" dick. She thought back at what she had seen Missy do to it and tried to do the same. At first she was doing so very clumsily but with a little work and help from both Missy and Jasper she finally caught on to what to do. Ashley licked the sides of his cock before sliding it in and out of her mouth several times. She then licked his tender hairless balls and sucking each nut into her mouth one at a time. She then went back to the shaft. Ashley continued this process many times as she took time to lick and suck down as much pre-cum as she could get him to produce. Just like Missy, Jasper had also been teased for several hours and he was not going to last much longer. He began to pump his dick in and out of the little 9 year old girl's mouth while she was sucking on his shaft and dick head. "I am about to cum!" Jasper moaned as he could feel the cum beginning to take the path from his balls to his dick head. Japer grabbed the back of Ashley's head and pulled her tight against him to make sure she did not escape his massive cum load. He soon was blasting streams of cum into the girl's mouth. She took what she could but soon began to choke. It was her first time and Jasper did not want to make her scared to try it again so he released her head and allowed the rest of his cum to splash all over his belly, cock, and balls. Ashley soon recovered and liking the taste of his cum began to lick some up from his shaft. Missy not wanting to get left out decided to lick some up off of his smooth belly. The girls did not stop until they had him all cleaned up. Ashley then put his limp dick back into her mouth and sucked his shaft dry, which caused Jasper to let out a moan of pleasure. Barbara had snuck out while the kids were playing with each other and fixed lunch. When it was ready she came back in but with them in the middle of the oral sex lesson she decided to just let it sit there until they were finished. Now with the oral sex out of the way they all stopped to eat and then the required break. The kids all wore panties and underwear out to eat and so Neil did not feel left out he too went in just underwear. When the break was over they all quickly headed back to the playroom. Barbara cleaned the kitchen and started dinner which was also now going to be late while I went with the kids back to the playroom for the next round. Neil gave his daughter a loving hung and then removed his underwear and laid down on the bed he had been on before lunch. I went to my bed and got comfortable for more of the show. Missy and Jasper dropped their panties and underwear but Ashley just stood there. "Want some help with your panties?" Jasper graciously asked. Giggling Ashley replied, "If you want to." Jasper smiled, gave her a kiss to the lips, and without any delay pulled her panties down in one try. Ashley stepped out of them and Jasper tossed them in the pile with the others. All three of the naked children then climbed into the bed together. Jasper's cock now beginning to rise to attention asked Ashley if she would like to find out what it was like to have sex. Going back to her bashful style she looked down and asked if would hurt. This is when Missy stepped in. "The first time you get a dick shoved into your pussy it is going to hurt some. It will depend on how big it is and if the guy knows what he is doing. Some guys out there just want to shove it in and cum without any love or gentleness. Some know how to take their time and make you feel good. It also depends on how big they are. Take grandpa's, his would really hurt a little pussy like yours because he is so big. I like it though because he knows how to use it and how to make me cum. Once your cherry has been popped then your pussy will stretch out and you can take big cocks and have fun with them." Missy explained to Ashley. "But...But...But...Jasper's thingy is really big too. So...it will hurt a lot the first time...right?" Ashley eventually got out. "Not to be mean or anything...And, I really love my brother's cock inside my pussy...but...he is not really that big. His will hurt, but not like if your dad used his first. I know you want to have sex with your daddy soon and I think once you get use to Jasper's dick then maybe later you can take your father's. I know Jasper will go slow and we will use lots of lube. I can help you by putting the lube in you and will try to get you ready. You can always have us stop if it hurts too much. Want to at least try?" Missy finished her talk by asking. Jasper now was fully hard and already was ready to fuck this little virgin. He had pre-cum dripping from his tiny pee slit and I knew he was ready to fill this little pussy with his hot cum. Ashley looked at Jasper then looked at his hard dick. She then looked at her daddy and his hard cock. She asked if it was ok to have Jasper go first even though she really wanted her daddy to pop her cherry. Neil told her he understood and knew it was best to have her cherry popped by Jasper's smaller dick. Still not sure if she wanted to go through with it she sat there thinking. "Would you like to see what it is like? I am sure Jasper would not mind sticking it in me so you can see." Missy giggled. "Could I? Wow that would be great!" Ashley said all excitedly. They had Ashley get out of bed so she could walk around and see it from different angles. Missy laid down and Jasper was soon on top of her. Missy was so wet from earlier that she really did not need any lubricant but she put some in so that Ashley could see how it was done. Jasper lubed up his dick and got between his sister's legs. He slowly lowered himself until his dick made contact with Missy's pussy lips. Once he was in the right place he slowly lowed himself until his entire cock had disappeared into his sister's pussy hole. With Jasper's balls resting on her butt he slowly pulled out and pushed his cock back inside. He slowly pumped in and out for a few minutes then switched to a different position. The second position was explained to Ashley as to being the one that Jasper would use on her. This one had her legs over Jasper's shoulder and Missy's butt raised off the bed by a pillow. Ashley was told that this one would make it easier to get into her pussy hole with less pain. Again he pumped in and out a few minutes before moving on to a third position. The third position was said to be the 'doggie style' and was one of Missy's favorites. Jasper was really having fun and began to really pound his cock hard into his little sister's pussy. His balls smacking her ass like he was spanking her in the process. With Jasper getting very close to blasting his load of cum into her cunt they again switched. The last position they showed the little 9 year old was the 'cowgirl' position and in this one Missy took over. She sat on her brother's hard dick and began to pump up and down on it. Every time he got close to spurting his cum she stopped until he got passed the urge to release his load. Missy moved around so that his shaft rubbed hard on her clit and just before he was about to cum the third time she pressed hard on his cock head sending herself over the edge and shot a stream of girl cum from her own pussy. She quickly pulled up and off of his hard shaft before he too shot his load which would have spoiled the whole session. As she pulled off him Ashley could see lots of sex juice pouring from Missy's pussy as Jasper's cock was flopping around completely covered with the same mixture of boy pre-cum and girl cum. "Wow that looked like fun. What was all that liquid? Did Jasper cum?" Ashley questioned. Missy giggle and said, "That was mostly my cum juice. Some was Jasper's pre-cum but I would not let him cum. I was saving that for you. Now are you ready to give it a try?" "Ok...I...Will...Try..." Ashley said. Missy jumped off the bed and Jasper sat up. He then grabbed a pillow and placed it in the middle of the bed. Missy grabbed a towel and laid it over the pillow to catch any blood from Ashley's cherry being popped. The children helped Ashley get into position and Missy put some lube on her fingers and worked it up into Ashley's pussy. She added more lube around the entrance before applying some to her brother's cock. It was not long before Jasper was between the little girl's legs with them up in the air over his shoulders. Jasper lowed his cock down as he held onto her legs. He spread her legs as far as they would go and Missy guided his cock into the little girl's cunt. He pushed in as he wiggled around as he tried to ream out her hole. Little by little it was going inside. Jasper looked into the strained face of the little girl he was in the process of deflowering. He closely watched as she cringed with each little push he made. She was tight. Probably tighter than any girl he had ever fucked before, and at one point, Jasper wondered if he was even going to be able to get his dick inside her. All of a sudden her pussy gave way and the head of Jasper's cock slipped inside. With a sudden gasp and her eyes popping open Ashley wondered if it was over. Jasper told her that his dick head was inside and he had popped her cherry but he still had the shaft to get inside but that the worst was over. Being a little disappointed she closed her eyes again and tried to relax. Jasper then worked on getting the shaft into her pussy but it was not long till he found her pussy still had to stretch out more for him to get his entire cock inside. He knew he should not pull out because that would hurt even more when he went to put it back inside. He told his sister to put some more lube at the entrance and he would work it inside as he pumped his cock in and out of her hole. We all could tell little Ashley was getting tired with her legs being held apart and with a hard cock shoved inside her tight pussy. There was not much that could be done. Either they called it quits and gave up or could keep stretching out her hole. I went up to Neil and whispered to him about the pain she was in and that he might want to see if she wanted to continue or not. Neil went to her bedside and leaned over asking her is he wanted to stop. With tears in her eyes she said, "No Daddy. I want to keep trying. I want you inside me more than ever now." "If you want he can just shove it in all at once. It will really hurt but it would be over with sooner." Her father told her. Jasper looked surprised by what he had said. Jasper really did not like hurting anyone much less a little 9 year old girl being fucked for the first time. He would do it if that was her decision but he was not going to tell her she had to agree to it. "Yes. Shove it inside me." Ashley begged. Neil took hold of her hand and said, "You heard the Lady. Shove your cock all the way inside all at once." Jasper looked at Neil to make sure he heard right and then in one hard push he shoved the rest of his cock into the little girl's tiny pussy. With a loud scream and a death grip to her daddy's hand it was over. Jasper stayed buried inside her with his balls resting on her ass for quite some time. Being in that position he was able to release her legs so they too could relax. Neil let go of her hand and told her when the pain was gone that she could push up into Jasper. That would tell him that she was ready to be fucked. He then wiped the tears from her cheeks and went back to his bed to watch. It was about 15 or 20 minutes later and Jasper's dick had already began to go limp from not doing anything when she made her first push. A minute or two later she did it again and soon after Jasper's dick began to swell up all over again. He slowly began to pump in and out of Ashley's pussy. He only pulled out a little at first but in not too long of a time span he was pumping in and out of the little virgin's pussy. He was still going slowly when Ashley begin to beg for more. "Can you go faster? It feels really good now." Jasper complying with Ashley's request he began to pump in and out with more speed and added more thrust into her pussy pounding. Ashley, being a young girl with no experience, did not know what to do or what to say. She had never seen porn, the only sex she had ever seen was a few minutes prior with Missy and Jasper, and with this being the first cock that had ever been inside her body she did not know what to do, where to put her hands, or what to say. Her arms out to the side of her flopping around as she tried to get as much pleasure from Jasper's dick as she could. Missy seeing the elementary way Ashley was acting decided to help her out. Missy took hold of Ashley's hands and placed them on Jasper's butt. At first Ashley pulled back not knowing that she could play with a guy's butt like that, but once her hands were returned back to the same spot and Jasper moaned as his butt was being played with she understood. Ashley began to play with, touch, rub, and eventually she spanked his ass lightly as he fucked her pussy. Jasper liked being spanked like that and with each swat he plunged deeper and harder into the little girl's pussy. She caught on quickly and like spurring a horse she swatted his butt to make him go faster and harder. Ashley could not control herself and she began to buck against Jasper's body. Her hands still spanking his already red ass. Ashley had no idea what was going on or why. She just knew it felt good and that she wanted more. "Ohhhhhhh...Mmmmmmm...Yessssssss...Fuck me! Harder. I need it harder...Oh Fuckkkkkkkkkkkkk!!!" Ashley screamed as her body began to violently shake and tremble. Ashley had never played with herself and had no idea that a good hard fucking could feel this good. This was only her second orgasm. The first being when she had been eaten out by Missy and Jasper before lunch. Now with Ashley's orgasm nearing an end, Jasper deposited his huge load of cum deep inside her tender body. She felt the jets of cum splattering the inside walls of her pussy causing her to open her eyes in surprise. "It is ok. That is just my cum being deposited inside you lovely pussy." Jasper said with a smile. She smiled back before closing her eyes to relive her first fucking. Jasper left his dick inside her pussy until it completely was limp and was about to fall out anyway. When it fell from her hole, Ashley moaned in disappointment. Jasper tenderly kissed her small soft lips before taking her into his arms. He held her tight as he laid beside her. Dinnertime was coming soon and since showering had become the normal thing I suggested Missy shower alone. She was not only upset because her brother had just fucked the stuffing out of a girl younger than her, but now she had to shower alone. She wanted a cock inside her cunt and since she knew that was not going to happen before dinner she headed to the shower alone. Neil was next. Like Missy, he too wanted to cum and was really not wanting to shower alone but eventually he gave in and showered. Last but not least, Jasper and Ashley showered together. Jasper taking care, helped clean up little Ashley's pussy that had been abused and was now red and sore. He gently washed her pussy before he did her back, arms, and legs. He then washed his own body as she sat on the seat and watched. When finished he dried her off then himself. Once back in the room he had her get on the bed and he lovingly put some cream on her reddened pussy which made it feel better. They all dressed and headed to the dining room for the nightly meal. After dinner we went to the living room. Barbara stayed in there while I showered and then when I got back she went to the kitchen to get it all cleaned up. When the rest time was up we went back to the playroom. Barbara finished the kitchen, took a shower, then joined us just as things were getting good. "Daddy can you do me now?" Ashley begged. Neil walked over to her bed and pulled her pussy lips apart. He noticed how red she was and took some lubricant and began to slide a finger inside his little daughter. She pulled back saying that it hurt. He then told her that she had better not do any more tonight. I suggested that they sleep together and then in the morning after breakfast they might and try it again. They both liked that idea but then asked about what they might do before bedtime. Chuckling I suggested, "I know Missy is as horny as can be and she really wanted to be fucked. How about you two watch Jasper fuck his sister?" "Can we? That would be fun. I want to see what it is like for him to shoot his cum into her...um...you know." Ashley giggled. With everyone agreeing, Neil got into bed with Ashley and held her tight. Their naked bodies making contact at many important places as they watched Jasper and Missy get into the other bed next to me and Barbara. They discussed it and Missy wanted to be fucked 'doggie style.' Jasper liked that position more than the 'cowgirl' position so he quickly agreed. Missy jumped into bed. Her butt sticking up in the air as her head and face rested on the pillow. Jasper climbed into bed behind her and moved up against her naked butt. His cock already hard and ready for the day's final fuck session. He placed his dick head at the entrance to his sister's cunt and when ready he gave one hard shove. "Ohhhhh!!!" Missy chirped. "Mmmmm...Now fuck me like a madman." Missy begged. It did not matter that Jasper had just cum not long ago. He was ready to go again. Jasper instantly popped her butt with his hand telling her to get ready for the fucking of a lifetime. He then put his hands on her hips to keep her from being pushed into the wall and began to pound her ass with all he had. His balls being loose and about empty swung loosely between his sister's legs each time he buried his dick deep inside her pussy. While the grandchildren were fucking each other I looked over and noticed Neil was playing with his daughter's little nipples. She was really enjoying his closeness and what he was doing to her. It was not long before he was super hard and had placed his dick between her sore pussy lips. I was hoping he was not going to try to put it inside her but also know it was their choice. "Fuck me big brother! Fuck your baby sister!!!" Missy begged. Jasper continued to pound his 11 year old sister until she gave up and began to shake from a super hard orgasm. He did not stop and continued to pound her like she was still getting close to cumming. Missy began moaning a second time as she began to shiver from the second orgasm. Jasper still not having to cum yet wanted to teach Missy that she should not ever be jealous and kept pounding until she achieved her third orgasm in a row. Being completely spent, Jasper released his load and filled Missy's worn pussy. Soon as Ashley watched Jasper blow his load into his sister's pussy she turned over, hugging, and kissing her daddy. I heard her tell him how much she loved him and could not wait till morning when she could feel him fill her pussy up with his cum. They hugged and kissed a few minutes at the same time Missy and Jasper collapsed into a pile of naked flesh on the bed right next to me. Barbara got up and turned out the lights. She came back to bed finding I had pulled my ragingly hard dick from my sleep shorts. Knowing exactly what to do she faced away from me as she pulled her nightgown up and her panties off to the side. I went to slip it in finding she was super wet and hot. I instantly sank in all the way to my balls. Quietly I fucked my wife in the small bed next to our grandkids. I only lasted three minutes before I filled Barbara's pussy to overflowing. That was one minute after she coated my cock with her own load of pussy cum. We soon were asleep with the others. My own dick spending the entire night inside my wife's pussy. The following morning we woke up first. I pulled my again hard cock from Barbara's warm hole. She got out of bed, got dressed, and fixed breakfast. When it was done she came back and we woke the others up. They all cleaned up and got dressed before heading to the kitchen for breakfast. Ashley wanted to be fucked more than eat but after her daddy promised to fuck her when they got back to the playroom she finally agreed. Breakfast seemed to be extra good that morning. It might have been just because I had dumped my load of cum into my wife the night before or might have been the sexual excitement in the air with Neil going to fuck his own daughter for the first time and I was going to get to watch. No matter why, I was just enjoying it. After breakfast we did our regular rest period then we all headed back to the playroom. Barbara said she would clean the kitchen later because she wanted to watch this very special sex show too. Entering the room, it was like Ashley was a completely different little girl compared to when she first entered the room just 24 hours prior. She was first to pull her panties off as she jumped into bed with her legs spread. My eyes quickly jumped to her hairless little pussy as it laid open on the bed waiting for her daddy to shove his cock inside. My dick also jumped to life as I looked closely at her loving little twat. Missy and Jasper also removed their clothing and got into the bed beside mine. Barbara and I sat up in bed so we could get a good view of the show. Neil dropped his underwear showing off his super hard pre-cum dripping cock. His 5.5" slightly below average thick cock point towards his little girl as he approached the bed she was laying in. Not caring if she got in trouble or not she began telling her daddy what to do. "Fuck my pussy Daddy! Make me cum like I did yesterday. I want to feel your hot cum blast my insides." Not being phased by her comments he quickly got into bed with his naked little daughter. He gently pulled her legs apart and squeezed his body between them until his dick was hovering just over her little baby pussy slit. He leaned over and began to kiss Ashley on the lips. Soon they were into a hot French kiss as her hands were playing with his butt. It was so exciting to see a little girl being so romantic towards her own father that I just wanted to pound my own dick into her pussy. They kissed and touched each other all over their bodies for almost an hour. Neil's dick was dripping pre-cum all over her legs and pussy as he moved around. Ashley would have been sitting in a puddle if she had been old enough to produce pussy juice of her own. A few minutes later I knew things were about to get going because Neil reached over and grabbed the lube. He put some on his finger and gently worked it into his 9 year old daughter's hairless pussy. This time, unlike the previous night, she moaned in pleasure as he slipped his finger all the way inside. Testing the waters more he slipped in two fingers. Again she moaned from pleasure and not pain. When he tried three fingers he found a tight fit and that her pleasurable moaning was more of an uncomfortable moan. Now knowing this was going to be a challenge he still wanted to try. Neil added more lube to her pussy lips and adding more inside her cunt as well. He then lubed up his own dick as he prepared to split his daughter's pussy in half. He was only about a half inch longer than Jasper but the problem was going to be that he was also thicker than Jasper and knowing how hard it was for Jasper to get his cock inside he was afraid of what was going to happen when he tried. Taking a deep breath and giving his daughter one last kiss, he took hold of his enflamed dick and placed it at the entrance to his daughter's pussy. In doing so it brushed across her clit causing a super hot sexual moan to escape from her lips. One tug on his cock released a flow of super slick pre-cum which he smeared just at the entrance to her hot love box. Neil pushed forward just a little to get his cock started in the right direction before pulling his hand back out of the way. Now with his cock started inside her pussy, all he could do was slowly work his dick in and out until it was snuggly inside Ashley's tight grip. He again leaned down and kissed his daughter as he tried to take her mind off of what he was doing to her privates. It must have worked because she wrapped her arms around his neck as she pulled him in tighter for a more loving sexual kiss. While she was paying attention to kissing her daddy, Neil was pushing his cock deeper and deeper into her super tight naked hole. With the head of his penis snuggly inside her hole he continued to push the shaft in next. Ashley either had no clue of what he was doing, she was too excited about kissing her daddy, or it just was not hurting her at all, no matter what the reason, he continued to push and she offered no resistance. Before we knew it, Neil had his big daddy dick all the way inside his tender little daughter's pussy. He then soon began to slowing hump his young daughter with a slow rhythmic stroke. Ashley began to moan as he picked up speed. It was a loving sexual moan and not one to be confused with a painful moan. Going slow but still picking up some speed, Ashley needed more and begged, "OH Daddy! Fuck me!!! Fuck your little girl's pussy!!! I want to feel your balls slapping my ass as you pound my cunt with your big man stick." We were taken back by what she was saying. In only 24 hours this little shy bashful girl had turned into a hot monster of a fuck machine. Not only was her mouth screaming she wanted to be fucked but her tight little body was doing the same. I was tempted to invite her back for a gang bang in the future just so I could get a piece of her ass. Well that thought was just going to have to wait as I was more interested in watching the show in front of me. Neil caved in and began to pound his daughter hard and fast like he remembered fucking is wife when they were first married. As he thought back to his wife he noticed a lot of similarities between his daughter and his late wife. He noticed they both had tight pussies, they both got really excited, and they both lost all verbal control when they began to fuck. The one thing that was not the same, not yet anyway, was that his late wife was a gusher and would spray so much cum that it soaked the bed. He then began to wonder if his daughter was going to be that way when she got older. But as for the time being he was just interested in fucking her to an ecstatic orgasm. Not letting up he pounded her hard and fast as his balls slapped her ass like she was being paddled. They were both moaning and groaning as they fucked each other. She pushed back as he pounded forward. Their kissing had broken up because they could not breath, moan, and talk dirty to each other and kiss at the same time. Their rhythm slowed but became more of a forceful fuck than before. They looked deep into each other's eyes as we could all tell they were about to come to their finale. Saying nothing but staring into each other's loving face, he pounded hard into his daughter's pussy. With each hard thrust he forced the air from both his lungs and his daughter's lungs. The hard expulsion of air then caused them both to grunt. With each thrust the grunt got louder and faster as the thrusts became harder and quicker. Soon it was grunts followed by more and louder grunts. It got to the point I wondered if the bed was going to withstand the pressure. With the bed bouncing, Ashley's pussy being pounded so hard her butt bounced off the bed, and the room filled with moans, grunts and other skin slapping fucking sounds I just knew he was going to blow his cum all the through her body. Ashley began to shake as the orgasm she had been looking for approached. Neil noticing her orgasm was taking over her body he shifted so his hard stiff rod swept back and forth over her clit at a better angle. This not only drove her over the edge but caused it to go twice as long. Towards the end of her second orgasm, Neil blasted a month's worth of cum deep into his little daughter pussy. When she felt it splash inside her eyes popped open just like when Jasper blasted his load hard into the little girl. This new sensation along with her daddy's continued fucking motion tripped a third orgasm in the little girl. It was not as intense but was still more than some women ever have during their lives. Slowly he began to come to a stop. Both of them completely out of energy. The rest of us in the room at a complete loss for words and or actions. We all wanted to fuck but knew this was not the time for that. They needed some cuddle alone time so we all slowly exited the room leaving them alone to cuddle, talk, or kiss. A few hours later they emerged from the room fully dressed and with their overnight bags in hand. Neil reached out his hand to shake mine. He then hugged and kissed Barbara. Ashley kissed both Jasper and Missy on the lips giving them both a big hug. Then as a show of extra thanks, Ashley reached out and gave Jasper a loving squeeze on his cock and balls. They both told us how much they appreciated the help and wanted to know if we would go out to eat with them sometime. We agreed and told them to give us a call when they were ready. Chuckling, Neil said that it might be a while because they had plans of fucking constantly until they could not fuck any longer. We all laughed knowing that they might just actually do that. They left the house and normally we would instantly start cleaning up. Today was different. We all headed back to the playroom and stripped naked. We got into bed together and fucked each other in any hole we wanted until we were all exhausted. We quickly cleaned the house and since we had eaten lunch while they were cuddling we knew we had to hurry. Working together the sheets were all washed and put back the rooms straightened and the kitchen cleaned. We quickly went over the next week's list of possibilities and made our decision. This one was somewhat different and just by looking at the profile we were really interested in what would happen. To Be Continued