Chapter 24B
by Ole Crannon
Wednesday night (continued)
"My God, I just can't believe she can take it. And that you do it with her like that. But it seems that she does like it, so I guess we should try. I just hope I like it as much as she does," Annie said.
"Don't worry Anns," Sissy said, who'e been listening. "Dad's the best. Believe me, you'll like it."
Annie smiled and nodded. She reached down and lightly stroked Rob's limp cock. "How long will it take for you to be able to do it again? Is there anything I can do to help?" Annie asked.
"Honey, let's give you some time to relax and take in everything so far. That'll give me some time to get ready again. There's no hurry. We've got all night," Rob explained. "And I'm sure Sissy and my sex fiend wife will be able to come up with something to entertain us or keep us occupied." Rob grinned at Annie then at Sissy.
"God, I don't see how you can get that thing into Kari's little holes. She's so tiny!" Annie finally exclaimed.
Sissy pulled Kari up and gave her a little kiss. "Thanks, squirt. That felt good. Makes your kisses taste yummy, too," she told the toddler who loved it and started kissing her older sister back to share the tasty kisses with her. "Let's show Annie how Daddy can fit inside you? OK?" Kari stopped kissing and giggled, unceremoniously plopping herself down on the bed between Sissy's legs and splaying her own legs wide so that Annie could see both of her holes.
Pointing to her cunt then ass, Kari said, "Like it in me, here. And here. Fee's soooo good. Get tingows."
Sissy laughed and said, "Yeah, kid, we all get the 'tingows' from Dad's cock." She reached down to pull her little sister's labia apart so Annie could see the toddlers small hole and cuntal membranes. "Use a little lube and put your finger in 'em, Anns. She likes it. Just like we all do." Kari giggled and muttered a little, happy to be playing these games with her big sis and Annie.
Rob put a good drab of lube on Annie's finger and the young girl leaned down to gently run it around the toddler's cunt. Kari giggled and sighed at the nice feeling, mumbling about 'tingows' and 'good'. Sissy reached down and held onto Annie's wrist to guide her finger into her little sis's hole. Annie marveled at the feeling as Kari squirmed with pleasure. Then Sissy took hold of both Kari's legs and pulled them up so her little feet were beside her ears, doubling her over and exposing both immature holes to Annie.
Slowly pulling her finger out of the toddler's cunt, Annie gently rubbed around the little puckered asshole, incredulous. When Kari giggled and muttered some more, Annie tried to push the tip of her finger into that little hole. As it slipped in, Kari sighed contentedly, nodded and said, "Do mo'".
"See, all us girls here love our asshole being used," Sissy said, laughing. "If Dad was ready to go again, she'd take him in either one." Kari giggled and nodded, not only understanding what her big sister said but wanting it to happen. The little girl was totally addicted to hot, sexual feelings. She had no negative preconceived notions about any of it and just went with what felt good to her.
Annie marveled at the feel of her finger in the tiny asshole. Sissy held up two fingers together, indicating for Annie to slip another one in. Annie hesitated, then tried to gently add a second finger. When Kari only sighed contentedly, wiggled her ass and asked her to do more again, Annie was amazed.
"She can probably take four, at least. That stretches her about as much as Dad's cock does. I know I've gotten four in her before," Sissy stated.
Rob looked at his older daughter and asked, "When do you do this?"
"Oh, sometimes when we play. She's a slut for sex and she likes her ass done as much as her cunt. Just like her mother and me," Sissy said with a giggle.
"I do hope you're careful," Rob said admonishingly.
"Oh, Dad. You know we're always careful. We keep clean and don't do anything that will hurt her. I love playing with my little sis," Sissy said, leaning down to give Kari a full tongue kiss, which Kari happily accepted and enjoyed. She loved doing absolutely anything with her older sister. And kissing was always a nice feeling.
Lynn came back in the bedroom and sat on the bed. She tweaked Sissy's nipple and gave her a kiss.
"Everything OK with Monte and Albert? Or Storm?" Sissy asked, smirking.
"No, Miss Perv, I was checking in with Sarah. Apparently Karen has gone to babysit with Bert so Amanda and Nelson can go out. As planned," Lynn said quietly, although Annie tore her attention and fingers away from fingering Kari's asshole to listen.
"Bert! What? What's going on with my parents? And Bert?" Annie asked. "I didn't know anything about that."
"I know, honey. When I talked to your mother today about having you stay overnight, she mentioned that if they could get a babysitter for Bert that they might go out with some friends. I called Karen and arranged it to help out. It's nothing major," Lynn told Annie.
"Oh," Annie said. "OK."
"Honey, do your folks go over to friend's places very often. Maybe getting dressed up a little? Like a little sexy?" Lynn asked.
Annie thought and said, "No, not really. They have me stay home with Bert once in a while when they go out..." She paused and then her face lit up. "Oh my God! You mean, like, doing things with others? Like sex things? Oh my God!" Annie's free hand flew up to her mouth.
"You said they were pretty cool with things and open minded. I know you said they hadn't done anything sexual with you kids, but could they be, maybe, having some special friends that they get together with?" Lynn asked.
"Oh, God! Mom has this, like, really hot black number that she'll wear occasionally. Looks really hot. Short leather skirt, leather bodice, black stockings and super high heels. Usually she puts a coat on over it so we don't see, but I've gotten a peek at her in it. God, I didn't ever think of them doing anything like that!" Annie exclaimed. "I just thought they did it for Dad. You know, with each other!"
"Well, if they're a little open minded, maybe we can get them doin' some things so, like, they can't say anything about you doing stuff," Sissy said. "And maybe doin' stuff with ya."
All Annie could say was "Oh my God!" over and over again as the idea sunk into her mind.
Lynn said, "I told Karen to maybe feel them out a bit on things and find out just how open minded they are. And you know Karen. So we'll probably get an update late tonight or tomorrow and we'll know more."
Annie knew Karen, having met her at Sissy's once or twice. What she didn't know was how totally twisted and perverted the young teen was. But Annie was in awe of Karen's seemingly effortless beauty, hot figure and totally revealing clothes. She could just imagine what her father would think when he saw the sexy teen. All kinds of thoughts raced through Annie's mind unbidden and hard to ignore, based on what she'd just learned about her best friend and her family.
"My God!" Annie exclaimed. "Am I the only one that doesn't know what's going on and hasn't been getting into all the sex stuff?"
"Not at all dear," Lynn said, trying to soothe Annie's angst. "You now know at least some of what we do. We do have friends that we 'play' with too. But we've been keeping it a secret for the longest time. Sissy just couldn't let anyone know about what we do. And I think you can see why. Some people just don't understand and make it difficult for others who just want to enjoy themselves and be left alone. Now, from the conversation I had with your mother, I think that they might be a bit more open minded about some of the kinky things people do. Probably not family stuff, as that's been quite taboo for the longest time. So they may have to be eased into things. I have a feeling that that's what Karen may be helping along tonight."
"Anns, Mom and I've discussed some things and we're OK with helping you get your family involved in, well, some stuff. You know, sex stuff. With you. And Bert. You know how we've talked about me doin' yer dad, so he couldn't get all bent about you doin' stuff. Well, I guess Mom got the opportunity to put some of that in motion. Just not with me," Sissy said. "It's gonna be so kewl to find out what Karen did. She could get that Dave guy, the statue, to do her." Sissy laughed.
Lynn couldn't help but correct her daughter and explained to Annie, "Michelangelo's David, hon. You know, the famous statue. But I agree with Sissy. If anyone can convert your folks, it would be Karen."
"Yeah, the chapel guy. The one that did the big church," Sissy said teasingly, laughing. "The Sistine Chapel, Mom. I know that history stuff. But from what I've seen, Dave couldn't fuck me with his cock. Now maybe if he could move a teensy little bit, ya know," Sissy said.
"Karen might be able to get him to manage that," Lynn said with a laugh. "And I know you know that stuff, dear. I just never know when you're serious or making a joke like that." She gave her daughter a kiss.
"So what do we do?" Annie asked. "Just wait until they say they're ready to do it with Bert n' me? God, I can't believe I could actually have Daddy do it with me. I mean, really have, uh, sex with him." She looked at Rob and said, "If it will be anything like you, I think I'll die and go to heaven. Or hell. Or wherever perverted sluts who do it with their dads go."
"Annie, it's not evil or sinful to make someone feel good. And show them you love them," Sissy exclaimed. "You won't go to hell for doing that!"
Lynn broke in and said, "Honey, you've got to be careful in what you do and say, so the wrong people won't get an idea and try to punish you for things like we've done. You know, it really wasn't that long ago here in the United States when kids eleven and twelve were getting married, having kids of their own and starting a family. So it's not unnatural. There's just people that want to control everyone else. And often you find that they're doing the very things that they rant and rave about and pass laws against. Nowadays, they just brush that off as a little 'scandal'. But if you're careful and have friends who like the things you do and don't pass judgment, then you can have fun. Like we've had tonight."
"Oh, I want so bad to get Mom and Dad to doing things. What did Mom tell you they did? How did you find out?" Annie asked.
"We haven't showed you everything we do yet. There's plenty of time for that. Once you get used to things, then we can, but when I talked to your mom, I sort of let her think that we did some kinky things and she was very interested in it. That outfit you described sounds like it fits well with what they may be doing with their friends. But just because they do that, doesn't mean they would be totally for having sex with you kids," Lynn told Annie seriously. "Different people like to do different things."
"Wow! It looked like one of those hot mistress outfits that I've seen on some of the vids Sissy and I've watched," Annie said, putting her hand over her mouth. "OMGOD, Mom's a bondage slut!"
"What do you think of that, honey?" Lynn asked quietly.
"I never thought about it. At all. Like, I figured that they, like, ya know, did it but I didn't know what. But putting what was on the vids together with my Mom, it's totally kinky!" Annie exclaimed.
"Yes, dear, but what do you think of it? What do you think of them doing things like that?" Lynn asked.
"I dunno. Before tonight, I only dreamed of maybe doing some of the stuff we've done. I didn't know that much. Now, I'm seeing things, like, totally diff. And if Mom was into really kinky sex things, then I'd like to find out more and see what she does. And how they do it," Annie said thoughtfully.
"Well, we don't want to put you into overload, so we don't want to dump more on you than we already have, but maybe you and Sissy could go watch some special vids and then we can talk about them. And maybe by that time, my pervert husband will be charged up again enough to see how much you like it- as Kari says- 'inna butt'," Lynn said.
Kari had been quite contented, having had several orgasms, including one 'inna butt' and had played 'spinker', but she now heard her name mentioned and her favorite thing and said to Annie seriously, "Daddy do inna butt. You wike it. Fee's good." The little girl nodded, smiling and patted Annie on the leg closest to her. Everyone had to laugh.
"See, it's so good even Kari likes to share," Sissy said, laughing. Then she looked at her mom and asked, "Which vids? Like the tit ones? The critters?"
"Maybe both of those if you think Annie can handle them. You haven't showed those ones to her yet, have you?" Lynn asked.
"Not those ones. Those'll be good. I think Anns can handle it. If not, I'll just finger fuck her to get her in the mood," Sissy said, laughing. Annie gasped in embarrassment, blushing.
"OK. Well, let me know if she has a problem," Lynn told Sissy.
"What is this?" Annie asked. "How bad could they be after what you've all showed me tonight? I mean, you already told me that you fuck the dog. How much worse could it be?"
Sissy got up off the bed and took Annie's hand. "Let's go see. And we can try to figure out what to do with your mom and dad too." Annie got up and the two girls left the bedroom.
Lynn smiled at Rob and asked, "Well, how was the eleven year old virgin cunt? I could hear her screaming all the way down in the kitchen, so you must have done something right."
"She's pretty orgasmic," Rob said. "And quite a squirter as you found out. I'm glad you put the rubber cover on the mattress or it would have been soaked all the way to the floor. God, that little cunt could fill a swimming pool, I swear. How'd she taste?"
"Nice. I love young, untouched cunt. Well, right after my loving husband has 'touched' them," Lynn said, leaning down and blowing a raspberry on little Kari's tummy. Kari broke out into peals of laughter and Lynn said, "Especially this little one who's been fucked more than some adult women have. God, I do love our kids. I don't regret a minute with them."
"Unlike a few weeks ago when you were guilt tripping all over, worried about how they would take their newfound slut mom stuffing snakes and mice in her and having needles skewering her tits," Rob laughed. "Like none of those regrets?"
"Hon, I was just being an emotional mom. Hormones, you know. After having met Ben and Sarah and finding out that people are doing all kinds of things that put us to shame, I'm just so tickled, and relieved, that the kids are taking it so well. And enjoying everything," Lynn explained.
Rob laughed and said, "Well, good. If this little slut here and Annie hadn't worn me out already, I'd see what I could do for you. But I still have to get it up for Annie's fine, young ass."
"I'd love to have you do something too, but tonight's Annie's night, so we'll make sure she enjoys it all. Any regrets about doing her?" Lynn asked.
"No. And from what you say, it's possible that we might have another couple to play kinky sex with. Not that we don't have enough to keep us going for a few years already. But if Annie could enjoy having her father make love to her like this little sex fiend here and her sister," Rob said, rubbing Kari's little tummy, "then I guess it's worth it."
"I'm really anxious to hear what Karen finds out. And you know Karen," Lynn said, laughing.
"Very well," Rob said. "None of us could keep up with her and her sexual appetite."
"Well, I, for one, can't wait to hear from either Karen or Amanda. Either way, it should be interesting," Lynn said, grinning.
"You know, Sissy has talked with me about them and her doing something, sort of plotting the downfall of Nelson, for a while. And if she actually tried, or tries, to do anything, you know Nelson wouldn't even stand a chance. No matter what his feelings are about doing young girls. She's going to be a lady in waiting or a competitor of Karen's. And I don't think we want to see them competing."
"God, 15th street whores would have a battle on their hands!" Rob said laughing while stroking his youngest daughter's soft butt. Kari wiggled a little, appreciating his caresses. Although she really would like his nice cock in her ass again. She always liked that.
In Sissy's room, the two girls sat in front of the computer, Sissy opening video files and playing them, Annie just watching in almost silent awe. Once in a while she'd utter "ewwwww" or "Oh my God!" but she never took her eyes off the screen.
Sissy had started with some pretty vanilla piss videos to show Annie that it wasn't that bad and could be so sexy. Then she showed one that had a guy with a huge cock fucking the asshole of a very petite young girl. He really sawed into her ass and got his cock a bit covered with her brown shit. Then he pulled out, grabbed the girl by the hair and had her suck his cock clean of her shit. The girl seemed to really enjoy all of it, moaning loudly with pleasure as the huge rod jammed into her ass, then mewling lightly as she happily licked and sucked her shit off it.
After she'd cleaned him good, he still had hold of her hair and started pissing in her mouth. He used his free hand to guide his cock, spraying pee all over her face, wetting her hair and filling her mouth. Before he was finished, he stopped his yellow flow and pushed the girl back down, straddling her head. Putting his cock right at her nose, he started pissing directly into one of nostrils. He alternated nostrils as the girl seemingly happily took it all and Annie could see her throat swallowing the guy's piss, which drained out of her nose into her throat.
Once he was finished, the guy jammed his cock into the young girl's mouth and started face fucking her hard. She wrapped both hands around his huge cock and helped stroke it as he did that. When he was ready to cum, he said something and pulled his cock out of the girl's mouth. Again, aligning the opening of his urethra with one of her nostrils, the camera got close as his first jets of cum spurted into it. After a few spurts, he moved to the other nostril and filled it up also until he was finished cumming.
"Oh, God! That's unbelievable!" Anne exclaimed when the video finished with the girl smiling into the camera, drenched with pee. As cum dribbling out of her nose, she used her tongue to lick it as it drooled down her upper lip.
"Yeah, people do all kinds of things that you've never even thought of before. I hadn't either until I started trying to find extreme vids like this. And when Mom started doing some especially pervy stuff," Sissy said, laughing.
"What stuff?" Annie asked, not sure she was going to want to actually know, but really turned on by everything so far.
"Well, maybe like this," Sissy said, starting another video. On the screen a good looking woman was lying on a bed with a three foot long python on her. She petted and handled the snake a little, then scooted up on the bed and spread her legs. Slowly, she started working the snake, tail first, into her cunt. Annie gasped and her hand flew to her mouth.
"Oh no! She can't!" Annie exclaimed, but kept her eyes frozen to the screen.
"Oh, yeah. She can," Sissy said, laughing. "And does. You'll see."
Annie watched in amazement as more and more of the snake disappeared into the woman's cunt. "How can she take that?" Annie asked softly as at least half the snake was inside the woman.
"Just watch," Sissy said, aroused and really wanting to feel Albert inside her now, doing the same thing the woman in the video was. But she knew that this was to be a learning experience for Annie and wanted her friend to know and enjoy all of the things that Sissy and her family did.
On screen, the woman had finally gotten almost all of the three foot long serpent into her cunt, with only the head and a couple of inches remaining outside, it's tongue flicking out and in. After a short time, the woman flipped up from lying on her back to her knees and then reached down between her legs and pushed the rest of the snake all the way inside her. Annie gasped.
"Kewl huh?" Sissy said, grinning. She'd watched this particular video numerous times and had done much the same thing with Albert. She loved the absolute lewdness of the feeling.
"Oh. My. God!" Annie finally exclaimed, letting out the breath she'd been holding. She still hadn't taken her eyes from the screen. "Won't it suffocate inside her?"
"Snakes can hold their breath for quite a long time. They don't seem to have any problem with it," Sissy said, matter of factly.
"How do you know this?" Annie asked, then her eyes widened. "Oh my God! Bobby's snake! You don't!" she exclaimed.
Grinning, Sissy nodded her head. "Not just me. Mom started it. That's why we got her her own snake, Monty. With two, we can both do it at the same time. Neat huh?" Sissy teased.
Annie was just overloaded with this after everything that she had done and had been shown and told about. Sissy felt a little sympathetic for her friend being overwhelmed, but she had decided that it would sort of be like ripping the band-aid off quickly. Overload her at first, then let her process everything from that point. Sissy put her arm around her friend and gave her a soft kiss. She didn't say anything, letting her friend absorb and think.
Finally, after some time thinking, Annie said, "I can't believe all this. I mean, I can because I've just seen or done it. But... I dunno. Jeez."
"Yeah, I know it's a lot to take at once. We've sorta been eased into it over time. But it's so hot. And erotic. Everything we do is just so absolutely sexy and pervy. I just love it," Sissy said quietly.
Annie took a deep breath and asked softly, "What else do you do? I mean, isn't this all enough? Jeez."
Sissy reached down and ran her finger through Annie's dripping slit. Literally dripping. The girl was so turned on, she was juicing so much it was running out of her and pooling on the seat under her.
"Looks like you like it all, though," Sissy said, hugging Annie to her. She could feel Annie shaking slightly.
After the two held each other for a while, Annie asked, "So you do the dog. And snakes. And girls. What else have you been keeping from me?" Both of them had to laugh at that.
"You know, I wanted to tell you about all kinds of this stuff, but we've had to keep it really secret. I mean, now that you know, what do you think would happen if people found out what we do?" Sissy asked.
"Oh God! I don't even want to imagine," Annie said quietly. "And yeah, a lot of it does turn me on. I really wish you'd been able to at least tell me about these things."
"I know. And it's been like torture to not tell ya. But we decided that maybe it was time. So whadda ya think. Really kewl, huh?" Sissy asked grinning.
"It's a little much. Is there more? Oh, God, knowing you, I'm sure there is. I don't know if I can take any more," Annie exclaimed.
"I know it's a lot. So you ready to take it in the ass? Find out how great it feels?" Sissy asked.
"I don't know. I'm sorta scared. I mean, your dad is really good and I've never felt anything like this before. But does it really feel good?" Annie asked.
"Has it felt good so far? Everything? Even the 'ewwww' stuff you felt squicked out about?" Sissy asked.
Annie looked pensive. "Well, yeah, I guess so. It's still a lot, though," she said.
"I know, Anns. But I love you. Your my best bud. Next to my mom, anyhow. And we wouldn't BS ya. Ya know that," Sissy told her friend.
"I know. It's just so much. Does Kari really like it? I mean, like, in her rear. It really doesn't hurt?" Annie asked.
"Well, it can. Like Kari says, 'maybe a widdow bit', but then it feels really good. I guess not everyone likes it in the ass, but the three of us do. And dad will make it good for ya. He's really good," Sissy said.
"God, I guess. He made me feel so good. I can't even think about how great it's gonna feel to do it with my dad. I hope he's as good as yours. But the more I think about it, the more of a turn on it is. I mean, God, doing my own dad!" Annie gushed.
"Yeah, it's totally rad. I love it. Everything we do together. And I just love to watch him do little sis. She gets off so good. Here. Watch this one. This is a vid that I did of us playing," Sissy said as she clicked on the video she'd made when Rob had fucked Kari before.
Annie watched and still couldn't believe that a three year old could take an adult cock in her, despite what was being played before her own eyes. And what she'd seen herself earlier. Watching the video got her even more aroused, if that was possible. By the end of it, she really wanted to have Rob do her anally. She was ready for it. Excited, even.
"I think I'm ready," Annie said as the video ended.
"Great. I'll show ya some of the other things later," Sissy said with a big smile.
"There's more? God, I don't think I could take much more," Annie gasped.
"Oh yeah. Like some of the stuff your mom might do with that leather getup she wears out with friends. You're gonna love it. Or not," Sissy said.
"What do you mean? What do you think she does? I mean, it's just a hot, sexy outfit. You mean, like bondage stuff?" Annie asked.
"Yeah. But prob more than that. How much do you know about that stuff?" Sissy asked, sorting through some of the directories of the video files she had.
"Uh, just, like, ya know, stuff I've seen in magazines. 'N stuff like that," Annie said.
"OK, then you don't even have any idea," Sissy said laughing. "Now, I'm not saying this is what your mom's into, 'cuz I don't know, but here's something my mom has gotten into recently." Sissy clicked on a video file to play it.
The scene opened in a room that had a lot of strange but ominous looking equipment in it. A good looking woman was seated on a padded table type of thing, wearing a black bra and panties. A man entered the picture and helped her remove both of the items, leaving her only in thigh high black patterned nylons and high heeled shoes.
"That doesn't look anything like what Mom wears," Annie said.
"Just watch," Sissy told her and the two watched as the man tied a long rope around both of the woman's large breasts, wrapping it around them until they ballooned out nicely.
"That's doesn't look so bad. She's got nice tits, though," Annie said.
"I know. But just watch what he does," Sissy directed. They watched as the man got a number of med needles, probably four inches long. Removing one from the sterile package, he put the point right at the edge of one of the woman's areola.
Annie gasped and exclaimed, "NO! He can't!" then watched as the needle was pushed all the way through until it came out the other side of the aereola. Annie again exclaimed "NO!"
"'Yup. Keep watching," Sissy said. The two watched as the man put four needles through each of the woman's breasts at different angles. Annie was both cringing and panting.
"This is where it gets really good," Sissy said, giggling.
On screen, the man had gotten an eight inch long spinal needle and the camera moved for a close up of the woman's breast. Annie again gasped and squealed as she watched him put the point of the needle against the side of the woman's bound breast and tapped it all the way through with a hammer. Then he did the same thing with two more of the needles. The woman had only groaned a bit as each of the three needles had been driven through her breast.
Annie exclaimed, "How can she take that?" as they watched the man do the same thing with three more needles through the woman's other breast, ending up with six long needles skewering her tits.
"She's a pain slut," Sissy said. "She likes it. This isn't the first one of these she's done and this isn't even the worst one. There's lots more. But it's sorta kewl, huh? Not that I'm really wanting to do it myself, but Mom has really gotten into it. That's how I found out about the vids. Mom found 'em."
"You mean she watches these videos or has it done to her," Annie asked.
"Both. We love to watch any perverted things like this online, but she's actually done it. With Dad. We'll have to show you some time," Sissy told Annie.
Annie's mind was just overwhelmed. She'd never even imagined something like what she'd just seen, let alone think anybody she knew would do such a thing. Or allow it to be done to her.
"If yer mom gets all dressed up in that black outfit, she's either a mistress or a sub. We'll have to find out which. Then see what we can do," Sissy said.
"My God!" Annie exclaimed for the umpteenth time. She could barely imagine her mother doing anything erotic or perverted.
"So you ready to let Dad ream your ass? Or should he just do Kari again. I know she'll like it," Sissy asked.
"I just can't believe all of this. It's just too much," Annie exclaimed.
"I know, Anns. But c'mon. Let's go see if Dad's charged up and see if you like taking it in ass as much as we sluts do," Sissy said, putting an arm around her friend and hugging her.
Annie enjoyed the closeness of her friend, now even more that she'd learned all of the outlandish and perverted things the family did. She couldn't get the snake and tit torture scenes out of her mind. She went along with Sissy though and they went to find Rob and see if he was ready for the Annie's next sex adventure.
The two young girls walked into Sissy's parent's bedroom to find Lynn and Rob lying on the bed, kissing, fondling and talking. They both looked up and Lynn said, "I've been keeping him hard for you, dear," smiling at Annie.
Annie almost licked her lips as she looked at Rob's cock but also felt the apprehension she'd felt before about whether something that large would fit into her nether hole.
Rob held out his hand for Annie to join them. As she did, Lynn asked, "Would you feel more comfortable if Sissy and I left you two alone?"
Annie had to give that a bit of thought. On the one hand, she felt very comfortable with her best friend Sissy with her, and even Lynn now. But she also felt a twinge of embarrassment at what she would be doing and didn't know if she wanted an audience.
"Either way, I guess. I've seen and learned so much tonight with you guys that I guess it really doesn't matter," Annie finally said.
Lynn got up and gave Sissy a hot, very non-motherly kiss and said, "I'll go find something to do. You can help Annie and Rob have fun."
"OK, Mom. Go stuff a snake or sumthin'," Sissy said grinning. Annie almost choked, then tried to look serious.
"Well, I don't know about that, but I assume you showed Annie one of those," Lynn said to Sissy.
"Yup. She's totally blown away," Sissy answered.
Lynn smiled and left the room. Sissy climbed on the bed and found the lube. She kissed Annie and had her roll over onto her stomach. "You ready for this?" Sissy asked.
Annie's reply of "Mmmm-hmmmm" was muffled by her face in the pillow. Sissy spread her friend's legs and started to apply the lube to Annie's asshole. Rob watched with a smile on his face. He wanted to make it good for Annie but he also was anticipating the feeling of fucking her tight little asshole. He wondered if it would be as tight as Kari's.
Annie groaned into the pillow as Sissy put her two index fingers into her friend's anus and started stretching it. Rob added some more lube as his daughter worked two fingers of each hand into Annie. Sissy had a big grin on her face, thoroughly enjoying playing with Annie's ass and getting it ready. She really wanted to watch, close up, as her dad's cock slipped into Annie's ass. It was going to be a glorious sight!
As his daughter held Annie's sphincter open, Rob moved forward and put the tip of his cock at the stretched opening. Sissy pulled apart a little more as Annie beat her fist on the bed and moaned. Neither of them knew whether it was pain, discomfort or pleasure that Annie was feeling, but she hadn't complained yet nor asked to stop.
Rob inched forward and let his cock slip into the wide open hole that his daughter had made of Annie's asshole. With all the lube and the manual stretching, his cock head slipped between Sissy's fingers and into Annie's sensitive hole.
"It's in, Anns. How do you like it?" Sissy asked, pulling her fingers out of Annie and letting the sphincter close around her dad's cock.
"It's in me?" Annie exclaimed. "Oh my God! It's in me!"
Rob remained motionless, letting Annie's ass get used to his cock. But he was glad that the young girl hadn't experienced any pain yet from his penetration. After a short while, he started to push gently, getting a little more of his shaft in through Annie's tight, virgin sphincter. The young girl let out a long moan.
Sissy leaned down and kissed Annie, rubbing her friend's back as Rob's cock slowly slipped into Annie's ass.
"Oh God! It's in me! Oh God!" Annie exclaimed loudly.
"It sure is, Anns. How's it feel?" Sissy asked.
"Oh, God, I don't know. I mean, it's odd. Different. Oh my God! It's IN me!" Annie repeated.
Sissy grinned at her dad. Rob figured that if Annie wasn't complaining or screaming about how much it hurt, then it couldn't be too bad for her. He gently pushed another inch of his cock into the young girl's ass.
"Is it IN me?" Annie asked, incredulous. "Actually in me?" She reached around and tentatively felt for Rob's cock with her hand. She felt only the base of his shaft between them. She couldn't believe his cock was actually in her ass.
"Oh. Oh. Oh," Annie exclaimed, panting.
Sissy leaned down and said, "Feels good, huh? Different but good."
Annie nodded slightly, eyes tightly closed. She felt like she had to take an enormous shit. But at the same time, it was starting to feel good.
"Ready to feel really good, Anns?" Sissy asked, rubbing Annie's lower back. Annie only grunted slightly. Sissy nodded to her dad and Rob pulled his cock slowly back until just the head was inside Annie's tight sphincter. Then he slowly pushed back in, ready to stop if Annie showed any discomfort. This time he got at least another inch of his cock into the virgin ass before stopping and slowly pulling back again. Annie groaned, this time more with pleasure than anything else.
"You like?" Sissy asked. Annie could only nod her head, her teeth clenched and her fists grabbing the sheets, white knuckled.
"Just relax, Anns. It hasn't hurt yet, has it?" Sissy asked.
Annie shook her head no and tried to relax, but she just wasn't used to having something penetrating her asshole like Sissy was. Or even little Kari. And she realized that she WAS getting those really hot, sexy sensations in her cunt and her tummy. It felt like when Rob had been stroking into her cunt before, but this time it was a different feeling. But it was building up, just like it had before.
Grinning at her dad, Sissy nodded to let Rob know to start stroking in earnest, which he did. Annie screamed and clutched at the sheets, biting into the pillow. Her body was tense and she was panting. Sissy kissed her friend on the cheek as Rob continued to stoke in and out of Annie's butt.
Annie's body started spasming and she let out a ear splitting shriek. Then panting, she plaintively pleaded, "Don't stop! Oh God, do it more!" Rob took that as Annie's full assent and pulled all the way out of her ass, then plunged all the way back in, seating his full length in the young girl's ass, getting another ear splitting shriek of pleasure.
"Yes. Yes. Yes!" Annie panted, her little body spasming and shaking. Rob would have been worried that he'd broken the little girl, except he'd seen similar reactions before. So he knew it was really the height of ecstasy that was driving Annie. Her reactions to his pounding cock and the tightening of her anal sphincter on his cock brought Rob to a really good, satisfying orgasm. He felt his cum shoot into the girl and his cock, balls and asshole tingle with the orgasm.
Annie continued to scream and groan, pounding on the bed with her fists, her face red and her breathing short and fast. The bed under her was soaked with her cunt juices.
After he'd jerked and cum into the young girl, Rob held still, savoring the orgasm feelings and the fact that he'd just ass fucked an eleven year old virgin. And from the sounds of her screams and moans, probably had another convert to anal, just like the females in his own family.
Finally, as Annie calmed down a little, Sissy mouthed the words "I want it" to her dad, who grinned and nodded. Sissy moved to Annie's ass and Rob slowly pulled his softening cock out of the young girl. Sissy quickly had her hand around the base of his cock and was sucking everything she could get off of it.
"You really like it dirty, don't you, slut?" Rob asked his daughter quietly. Without taking her mouth off the dirty cock, Sissy nodded agreement.
Once Rob's cock was well cleaned, he moved back away a little and used his thumbs to separate Annie's ass cheeks to expose her gaping hole. Sissy quickly changed from cock sucker to ass eater and had her tongue in her friend's hole, even as Annie was still spasming a little from her orgasm. The feeling of Sissy's tongue on her asshole pushed Annie again into some mini orgasms. Sort of like aftershocks felt after an earthquake.
Rob laid down with his head beside his daughter's, watching her tongue Annie's asshole. He gently pushed her away, then started rimming Annie, getting his tongue in as far as he could. After a little of that, he turned his head to his slightly surprised daughter and pulled her to him in a hot tongue battling kiss.
"Daddy!" Sissy exclaimed after they broke their hot kiss. "You can still surprise me. And I love you for that. Thanks for making Annie's first time so good for her."
"No problem, sweetheart," Rob said. "With a nymph like you, how could I do anything else?"
Sissy laughed. Annie didn't know whose tongues had been working on her, she was just lying there, trying to recover from her many and continuing orgasms. Rob thought to himself that Annie could be quite the orgasmic little wench, getting off on just about any sexual stimulation. He grinned to himself, enjoying that idea.
"Do you do things like scat just because you like it, or just for the shock value?" Rob asked his sexy daughter quietly.
"I like to do 'em 'cuz I like doing 'em," Sissy responded with a smile. "If I don't like something or don't want to do it, then I def won't." She grinned, then said, "But so far, I really haven't found anything I don't like."
"Just as long as you know you don't have to do anything you don't want to," Rob said. "I really don't know how we can arrange you turning tricks or being a porn slut, because of your age. But if you're sure about those things, we'll try to make it happen. Somehow."
"Oh, Daddy! Sometimes I think that I could just be totally happy doing things the way we have been. You know, just our family. I love you doing everything you do with me. And lil sis. But it's so exciting now to find out there's other people like us. I mean, you know, doing sex stuff. Crazy, weird sex stuff," Sissy told her dad.
"I know, sweetheart. I think your mother's gonna need more than just the family. I think it's fortunate that we met Ben and Sarah when we did," Rob said.
"And Karen," Sissy laughed. "Don't forget Karen."
"Who could, sweetie, once you've met her," Rob said laughing. "I just hope you two don't get into more trouble than Ben can get you out of."
Annie was listening to this in her post orgasmic fog and she roused up enough to ask, "Who're all these people you're talking about? And what do you all do? I know Karen, but I guess I don't know that much about her. Other than she's HOT! And I'm a girl and think that she is."
"Yeah, she is. And you don't know the half of it. And this little depraved slut is right there with her," Rob said, pinching one of Sissy's nipples hard, making her jump.
"Well, if we can get Ann's mom and dad into the group, then all of us can have the same kind of fun. Annie and I have a plan to work on her dad," Sissy said.
Rob said, "And I don't have a doubt that he will stand a chance in hell putting up any resistance to you. In fact, I think your mother said that Karen was going to be babysitting Annie's little sister tonight so her parents could have a night out."
"Oh, God. She'll get to him before I do!" Sissy exclaimed, grinning. "That slut!"
"What? What are you talking about?" Annie asked.
Sissy got down beside her best friend and gave her a tender kiss. "Nothing. Don't worry about it. It'll just make our job easier if Karen gets to work on your dad tonight. Although, I wanted to get him first. Now that your first has been my dad."
"And it was wonderful," Annie exclaimed. "Thank you again, Mr H. I don't know if I'm gonna recover from this all."
"Don't worry, Anns. You'll be back to craving cock in no time," Sissy said.
"I already do!" Annie exclaimed, laughing.
"Addicting huh," Sissy said. "A dick ting... get it, Anns?"
Annie giggled. "Yeah, I get it. And I'm really glad that I've gotten it," she said, reaching out to grasp Rob's soft cock. Her gentle touch made it twitch slightly. Annie exclaimed, "Oh, that's so kewl! That I can make it do that."
"Annie, you've got a nice little bod. When you start developing these things," Sissy said, running her hands over her own budding titties, "you'll have to fight the boys off with a stick."
"Why would I want to do that?" Annie asked. "I LIKE their sticks. Get it? Their sticks!" The two girls giggled like the young pre-teen school girls they were at Annie's joke.
"Uh, can we, like, do some more tonight?" Annie asked Rob shyly.
"If you think you can take any more," Rob said, rubbing Annie's tight little ass.
"We'll have to let this old man get recharged up first. He can't do it real quick again like Bobby can," Sissy said, smirking at her dad.
"You know, I've never heard you or your mom complain," Rob said laughing and pinched one of Sissy's nipples roughly, getting a little squeal out of her. "And your little sister doesn't seem to have any problem with me."
"I still can't believe that Kari can take it," Annie said, shaking her head.
"She definitely can. And she takes after the rest of the family. She really likes it 'inna butt', as she says," Sissy told Annie. "I still wish you'd started me earlier, Daddy. I mean, I'm perfectly happy with what we've done, but lil sis has it good. She's starting so early. I envy her."
"I can't believe it. And Bert, my sister, is five. Do you think she could... I mean, you know... at five?" Annie asked.
"We'll have to work on it, Anns. That's about when Dad started me, so I'm sure she'd just love it. Especially if it was her daddy who was her first," Sissy said. "Have you two ever, you know, played with each other?"
"Nuh-uh," Annie answered. "Well, not really. We see each other naked all the time, ya know. But I've never really done anything with her. I mean, like you n' me've done. Up until we started doing things, I always thought she was too young. Well, if I ever even thought about it at all. And I guess I really haven't."
"Well, I can tell ya that Kari really likes playing around. Pretty much anything. Right, Dad?" Sissy asked.
"I guess. She certainly hasn't objected to anything that you guys have done so far," Rob said. "And apparently, you and Bobby both seem to, uh, play with her a lot."
"Yeah, I like playing with my little sis," Sissy said.
"I wonder if Bert would want to do something," Annie wondered. "Now that I've seen what Kari does, and likes it, I'll have to, maybe, see what we can do. Together. I've never really thought about two girls doing, ya know, stuff. But I kinda like it."
"Then we've gotta get your dad doin' the two of you," Sissy said, laughing. "Dad, would you like to do a five year old. Bring back memories of when you first did me?"
"As if I've not got enough women to satisfy already," Rob said laughing. But the idea of slipping into a five year old cunt was rather intriguing. Again.
"But you know, I remember that first time with you like it was just yesterday. I was so afraid of hurting you, but I was so supercharged about it. I couldn't love you more and it's only gotten better, kiddo," Rob said, then looked at Annie. "But as much as it might be nice, I think that it would be best if your dad would be Bert's first, at her age. Like Sissy says, I think that would just be so right. If he would want to, that is."
"Awww, that's so nice, Mr. H." Annie said. "I'll never forget this though. You're my first. Thank you so much. Now I'm really gonna work on getting my dad to do me and do my little sis. She deserves it. I hope we can do that."
"Don't worry," Sissy said. "I've got a plan. It may be your mom that we'll have to worry about. I'll check with Karen and see how things went tonight. Maybe she opened the door a little."
"Oh, God, I can't believe that maybe my mom and dad might, like, do stuff with us, ya know. That would be just so kewl!" Annie exclaimed.
Rob remembered Lynn telling him how Annie's mother seemed into BDSM or domination. He wondered what she'd be like strung up downstairs and having a little whipping or torture done on her.
The two girls went to Sissy's room and giggled and plotted for a while. At some point in the night, Annie made her way back to Rob's bed and kissed him awake, shyly asking if he'd, maybe, ya know, put it in her rear one more time. Ever the gentleman and not wanting to turn down a young lady's request, as well as really enjoying assfucking tight little Annie, Rob obliged her. Afterwards, Rob cleaned Annie and they snuggled for what little was left of the night. Rob enjoyed the soft tight feel of the young girl and Annie enjoyed being held in Rob's arms. She did fantasize how it might feel if they were her own dad's arms, though.
[continued in ch 25A]
Did you like this story? Questions, comment? Use the Contact button and let me know.