Double Dating With Brother

by Lubrican

Bob Randall was an average guy with average intelligence, who was just trying to raise his two kids without their mother being around. There had been a messy divorce when the kids were two and three, at which time his wife had decided that she didn't like children, but liked doing what made them ... with lots of other men. Custody hadn't been an issue, since she wanted nothing to do with her son, Mark and his older sister Cindy, even though she had insisted on those names. She had disappeared off into the political world of Washington D.C. and the kids had never seen her since.

Bob, doing his best, had brought the kids up to have respect for their elders, to obey their teachers and study hard, to work for what they wanted, and to love one another. He just didn't expect them to love one another quite as much as they actually did.

He didn't find out just how much they loved each other until Mark was sixteen and Cindy was seventeen. Here's how it happened:

Bob, being a guy who more or less hated clothing, didn't wear much around the house. He didn't make the kids wear much either, and both of them grew up with a streak of his nudist mentality in them. All of them knew quite clearly that other families didn't run around naked in their houses, and if the kids or their dad were going to have visitors, good communication was required to ensure that no one got embarrassed.

That worked fine for the first ten years, but at one point or another, Cindy was going to start menstruating and Bob didn't quite know what to do about that. He enlisted the aid of a woman he worked with, who came in and gave Cindy all the information her mother would have given her, had she been around. She also gave her a box of pads, being a woman who didn't think tampons were appropriate for a girl that young.

That was fine. When she was twelve, Cindy duly notified her father that she was "a woman now". She also grew breasts and hair in places that had never had hair on them before. She assured him everything was fine, but she had to start wearing panties around the house. Pads require panties.

Things sort of perked along, more or less normally. But, girls being girls, and talking about the things girls talk about, Cindy learned about tampons, which were a lot less troublesome than pads.

And so it was, when she was almost fourteen, Cindy came to her father and said she needed some help. It seemed that she had tried to shave her legs, she cut herself and she wasn't about to try under her arms until her father showed her how to do it safely. That's why she had a brand new razor with her when she asked Bob for help.

She also had a box of tampons with her.

Bob, thinking he was equal to the task, set about instructing his baby girl how to shave things. He shaved under one of her arms, and then supervised as she shaved the other. That went very well, all things considered, except that Cindy was wearing only panties at the time and Bob was put on notice just how much she'd grown up since the last time he actually LOOKED at her budding breasts. She now had real ones, the size of small grapefruits, and her nipples, instead of being just smears of color on the tips were pronounced and sat on top of areolas.

Bob had the uncomfortable feeling of blood migrating to his penis, which it wasn't supposed to do when he was looking at his daughter's breasts.

Then she held out the box of tampons. "Pads make a bulge in my clothes, and the girls all make fun of me," she said sadly. "I got these, but I can't figure out how to make them work."

Bob opened the box. There was one tampon missing, and the 'installation tube' as he thought of it, wasn't there either. "Honey, there's a cardboard tube ..."

"Oh yes!" she said. "It's in my room." She ran to her room and brought back a somewhat bedraggled looking tube that was bent a little and partly crushed. "I did like the instructions said, but I couldn't get it to go in," she said. "It hurt too."

Bob, of course, knew what the problem was. His baby girl was a virgin. Not that that was a problem, but it definitely interfered with the use of tampons.

Briefly Bob thought of the traditional means of removing a girl's virginity.

Then he mentally smacked the back of his head and told himself: "Behave, boy!"

Then he cast about in his mind for something that could be used instead of the traditional means. He looked at his hand and realized his middle finger was probably the perfect size for the job. He also knew his daughter would probably freak out at what he was going to propose.

"Sweetheart, do you masturbate yet?" he asked.

Cindy turned white and stuttered. "Well, um ... I ... I ... uh I don't think so Daddy."

"You don't think so," her father repeated.

"Well, sometimes in the shower, when I'm washing ... down there ... it ... ah feels nice."

Bob thought for a minute. "OK. See, here's the thing. For you to use tampons, we're going to have to tear ... um break your hymen. You know what that is right?"

She nodded. "That's what makes me a virgin."

Now HE nodded. "Right, but it gets in the way of the tampon. So we have to break that. That's why it hurt when you tried to put in the first one. And it will hurt when we break it. And I think you need to know this ... so you can decide if this is really what you want."

She thought for a minute. "If it hurt when I tried, why didn't it break then?"

"I guess because you didn't push hard enough. Some girls' cher ... er hymens are pretty tough."

"How would we have to break mine?" she asked.

He held up his finger. "This is about the right size. I'd have to push it inside you and it would break your hymen. I'd sort of recommend that we ... well ... that we sort of masturbate you a little bit when I do it. I mean because that will make it less painful I think."

She looked at him. "That sounds pretty weird, Daddy."

He gave a nervous cough. "I'm aware of that baby, but I don't know of any other way to do it without it being pretty painful. I mean it's dry in there now, but if we rub you a little, it will get slick and then I think things would work better. I guess I could always ask Mrs. Jenkins at work to come over and help you with this." Marge Jenkins was the woman who had instructed her on the pads. Part of that instruction was about how never, under any circumstances, should a young girl touch herself 'down there' other than to wipe and wash.

"NO!" barked Cindy. She wasn't eager to see Mrs. Jenkins again. Mrs. Jenkins had a way of making her feel like there was something wrong with her. "I think we should try your idea first. If that doesn't work, then we'll see. OK Daddy?"

Bob wasn't all that happy. The idea of fingerfucking his little girl to get rid of her cherry was both attractive and repellent. Actually, it was attractive, and that repelled him.

"What do I do Daddy?" she said, her trusting eyes on his. She wasn't allowed to date yet, even in groups. She had no experience with a male's hands on her body.

"Well, why don't you lie down on your bed, and I'll lie beside you. Who's your favorite music star?"

She told him, but it was a female. It was the same with movie stars. When asked who she might think about having for a boyfriend, or someone she'd like to go out on dates with she couldn't come up with a name.

"OK, then, just lie back and I'll teach you a little bit about your body. What's going to happen will happen regardless of what you're thinking about."

She lay back, arms at her sides and closed her eyes. Bob told her he was going to take her panties off, and then that he would warn her when he was going to touch her. As he pulled her panties off he got a look at the target of the day.

Her pussy was tightly closed, with plump lips forming a barrier to the hole behind them. her sparse blond pubic hair stopped above her slit. His dick lurched in his pants as he looked at her. He decided to start on her breasts. He told her he was going to rub his hands over her body everywhere and he started on her arms, then sides, then stomach and then her breasts. She sucked in a breath as his hand slid across her nipple.

"Your nipples are very sensitive," he told her, using the flat of his hand to rub across them both. "The nerves there are connected to a system of nerves that includes the ones in your vagina. As I play with your nipples you may feel it down there."

"That feels really good, Daddy," she sighed. "Why doesn't it feel like that when I touch them?"

"After you learn what sexual feelings feel like, it might START feeling like that when you touch them," he told her. "Now I'm going to suckle at your breasts, like a baby would while I rub you some other places." He took one nipple into his mouth and sucked gently, sliding his hand down to her stomach. He let his fingertips trace the area over her ovaries and her hips lurched.

"Mmmmmmm, Daddy, that feels even better. I like this," she sighed again.

"Spread your legs for me baby," he said and as she did he let his fingers drift across her tightly closed portal. She wiggled, telling him it felt funny. He felt just the very beginnings of moisture at the top of her vulva, and he rubbed his fingertip in that, sliding it down and forcing the lips apart. He felt for and found her clitty and began a gentle circle around it, but not on it. Her legs spread further as she moaned.

"Oh Daddy! That makes me feel funny in my tummy," she said.

He kept going, telling her that everything was normal and that what she was feeling was going to help with the pain later.

"It doesn't hurt at all so far, Daddy," she said. He knew it would later.

Finally he began to feel much more moisture as her body reacted to his stimulus. When he felt her slippery juice he let his finger drift across her clit, pressing on it harder. Her legs bent and then straightened convulsively and he sucked harder on her nipple. She was moaning now, lifting her head and letting it drop back to the bed.

"Oh Daddy! Something's happening. I feel so .. so ... like something inside me wants out!"

"That's good, baby, you're doing fine. You're about to have an orgasm. It's going to feel very strange, but I want you to let it happen." He switched his index finger to his middle one, and began sliding the tip in and out of her virgin slit. Each time he brought it out he ran it over her clit. As she got closer and closer to having her first cum he slid his finger deeper until he finally felt the tissue that was proof of her virginity. When she began to babble and toss her head back and forth, he let her get into the orgasm and then he rammed his finger through her cherry in one violent thrust. As she yelled at the pain he cupped his hand and left his finger buried in her while he used the base of his fingers to rub back and forth on her now swollen clit. The orgasm overcame the pain and she flopped as she came. Bob was hard as a rock as she flopped next to him. Slowly she settled back down on the bed, her hips still thrusting. He took the pressure off her clit, but left his finger deep in her.

"Oh Daddy!" she gasped. "You were right! It hurt, but only for a minute. Now it just feels ... full."

"Well, it's going to hurt a little bit when I take my finger out of you. Tell me when you're ready."

She nodded and he turned the finger first, to break the suction on it, finally sliding it out of her. His finger was pink with a light layer of her blood. They both stared at it. "Wow," she said. "That's a lot of blood. It only aches a little bit now. Was that like having real sex?"

He shook his head. "A man's penis is lots bigger than my finger, honey. You aren't ready for that yet anyway. But, in a day or two, try the tampon again. I think it will work then." It was hard to walk away from her naked spread body, but he did it.

That was the first hurdle Bob had to jump. He hadn't gone back to the dating pool after his wife left. Some of that was due to the fact that he was very busy raising his two kids. Part was because he was down on women. Part was because he didn't have much self confidence. The fact was, he went without sex for the most part, beating off now and then to relieve the pressure. He hadn't been with a woman for six years when he fingerfucked his daughter's cherry so she could use tampons.

She started taking longer showers, and when she came out of those showers she was vibrant and beautiful and ... happy. And he knew what she was doing in there. She was doing what he'd taught her to do without actually meaning to. He'd taught her how to masturbate.

Time went by and Bob thought that things were going pretty well. Cindy reported that the tampons worked fine. The days and months swept by and she grew into an even more beautiful young woman. Both she and Mark seemed to be happy most of the time. That they helped each other with homework every night made him proud. Cindy had already taken most of the classes Mark had, so she knew how to explain things to him. He had a quick mind and if she got stuck on something he could usually help her figure it out. Bob just went to work, brought home the bacon and watched his kids grow up.

One Friday night, after Bob fixed dinner, the kids announced they were going to go do homework as usual. It was while he was doing the dishes that Bob thought about how little they had done as a family lately. It was Friday night, and usually, after dishes, he would watch TV while the kids finished their homework. Then they'd watch TV. They still couldn't date yet, and about all they ever did was do homework and watch TV together. There weren't any slumber parties or sleepovers. Bob thought they must be bored out of their minds. He determined that they would go somewhere that night. He didn't know where, but he'd call a halt to the homework and get them out in the car. They could decide then what they were going to do. He headed for Cindy's bedroom, where most homework was usually done.

It was as he approached her door that he heard their voices. Something in the tone caused him to halt. It was hard to hear through the door, but he heard Cindy's voice say, "Ohh Mark ... that feels good." He put his hand on the knob and turned it slowly. Letting the door open just a crack, he peeked through it. Cindy's vanity, with it's big mirror was directly in his view. And in the mirror he could see her bed.

They were on her bed.

They were naked.

He had taught her how to pleasure herself, and he had pleasured her. She had obviously taught her brother how to do the same. She lay there moaning as her brother rubbed her pussy. Her hand was wrapped around Mark's cock and she was jacking on it in a way that made Bob's penis want to spurt.

Should he make them stop?

He watched as she came and then Mark splattered them both with his spend. They lay back gasping, their hands touching. It wasn't like they were fucking.

He closed the door.

Two months later she came to him and said, "Daddy, a boy has asked me out. I want to go. Is that OK?"

"Well, you're seventeen, and that's old enough to date. I'm nervous about it, because I remember what I tried to do with all the seventeen year old girls I went out with." She looked at him patiently. "I'd feel a lot better if you double dated with your brother," he finished.

She smiled a dazzling smile. "OK, I'll ask him."

They went out a week later. He waited up for them, and when they came in they were both laughing and happy. "How'd it go?" he said, sitting in the dark.

"It was fun," said his daughter. "He tried to kiss me, but Mark wouldn't let him." She swung her purse at her brother, who dodged it easily and grinned.

"Good boy," said their father.

They went off to their rooms. Bob went to bed, but for some reason he wasn't sleepy. He didn't feel like reading, so he just lay in the dark, thinking.

He heard the floor creak, but it was the floor between Mark and Cindy's rooms, and not the floor on the way to the bathroom. They had just spent hours in each other's company. What could one want with the other now?

He thought back to the time he saw them masturbating each other. Yes, the date would have gotten them excited. He got up silently and stealthily went through the kitchen to the back door. He tried Cindy's room first, peeking through the window, but he couldn't see anything. Then he went to Mark's window. A night light was on.

Mark was on his back, naked. Cindy was on top of him, also naked. Her head was bobbing over his groin and his face was buried between her legs. Bob stroked his own erection and when he saw them cumming, he splattered the side of the house.

They double dated every weekend. And every night after they got home, they did with each other what they didn't do with their dates.

Bob couldn't help himself. He loved watching them. Being a man with talent, he devised a set of plans, bought the materials and made each of his children a name plate for their bedroom doors. It was an amazing sort of thing, with their name on the outside. But it required a hole be cut in the door, and it fit in like a window. On the inside you could push a button and a message would appear on the outside. "Doing homework," "Taking a Nap," "Come on In," and "Pouting - Go Away," were the messages. Both kids thought they were nice, if a little strange, but then their dad had been acting strange lately.

What they didn't know was that with the push of a button on the outside, it became a window into the room.

Prom night was a big deal for them both. Again, they were double dating. Their father said they could stay out all night, and smiled to himself when they declined, saying it took too long to recuperate. He told them he wasn't going to wait up for them this time, but he knew he'd wake up when they got home. He heard them come in.

They went straight to Cindy's room.

Quickly, Bob got up and tiptoed to her door. He could hear the murmur of voices through the door. He pushed the button and suddenly he could see them clearly. They had left the light on, and Cindy was already down to bra and panties. With a practiced flip of her fingers the bra came loose and she exposed her breasts to her brother. She did a little dance ... a bump and grind of a sort, as Mark dropped his clothes.

This was the first time there had been enough light to see them both clearly. Mark's erection was something to be proud of. Cindy removed her panties and climbed onto the bed, prowling like a cat. He walked up to her and she sucked his cock while on all fours.

Then she lay back, legs spread, holding out her arms. He bent over and lapped and sucked her pussy for a minute.

Then, so quickly that it took Bob completely by surprise, Mark crawled between her legs, notched his cock into her gaping pussy, and pushed until his balls slapped her butt.

Bob expected to hear her scream.

But she didn't.

He expected to see her face grimace in pain.

But it didn't.

He expected to see her object and push him away.

What he saw was her hips thrust up, onto the invading prick.

They had done this before.

Mark's thrusts were practiced, and Cindy's upward thrusts were timed too well for this to be the second or third or even tenth time they had done this. But Mark was a kid, and he had yet to develop good control. Within minutes, before Bob's amazed eyes he saw Mark's head go back, saw the frozen grimace on his face, saw him slam his cock into his sister and stop, and then saw the clench of his ass cheeks as his penis sent streams of his teenage spunk deep in his sister's pussy.

Bob expected to see his daughter push her lover away, to make him take his dangerous spurting prick out of her unprotected fertile pussy.

But she didn't.

Instead her lacquered fingernails dug into her brother's ass cheeks and she pulled him deeper.

They had done this before too.

Bob witnessed the joys of youth. Mark's orgasm didn't slow him down a bit. He kept going. He fucked his sister for fifteen minutes, and she came four or five times. Then he dosed her again with his incestuous thick seed. When he got up off of her, her open pussy was a mess of gooey cum. She calmly dipped two fingers in it and slurped them clean.

As Bob's own sperm splattered against the door he knew he'd have to do something about this.

He did.

He bought a video camera.

The End