Chapter 2: Ana Takes the Plunge and Joins the Family

That night Ana lay awake, unable to sleep. She was scared, scared of what she was becoming.

Since first witnessing the Harris family making love a week ago, Ana thought of almost nothing but sex. She enjoyed sex and had no problems or hang ups about it, but it didn’t consume her life. And over the course of this past week that’s what sex had been doing to her. She thought about it constantly. She patrolled the house, hoping to catch the Harrises going at it. Watching television in her room, she found that she wasn’t paying attention to what was on the tube, but was thinking about sex.

She figured that there were three ways this would play out. One, she would turn into a sex-addled maniac. Two, she would come out of this hyper-sexed state and return to normal once the novelty wore off. Or three, she would have to quit her job.

She didn’t want to quit. Not only was the money great and the work light, but she liked the Harrises. It wasn’t just the sex; they were nice people and good bosses. Not stuck up or condescending like so many of the rich people whose homes she had cleaned.

Then she thought that maybe her problem was that watching all that sex was getting her worked up, but she wasn’t getting the right kind of release. Masturbation was fine, but it wasn’t the same thing as flesh on flesh, that surrendering of control to another person. When she touched herself, she was in control, able to bring herself to orgasm or prolong it as she wished. But with another person, you were never in total control, and that made all the difference. It wasn’t planned or mechanical; it was uncertain and very human. That made it more exciting.

But she knew that she couldn’t very well just dive into bed with all five Harrises. That would be too much too quickly. She wouldn’t know what to do, and while that dom-sub play was fun to watch, she wasn’t sure if she’d enjoy actually doing it, like that time her boyfriend and she had tried anal sex. Sometimes the idea of doing something is more enjoyable than actually doing it, especially when you don’t know how to do it right.

So no group sex and no dom-sub stuff, at least not to start. Maybe she could invite Tanya back to her bedroom. The cook had all but said that was willing to sleep with her, and it wouldn’t be like fucking the boss. But she didn’t know the first thing about pleasuring a woman. And face it, while she was open to the idea of sex with a woman, she wasn’t naturally inclined in that direction. She was firmly in the attracted-to-men camp. So no Tanya. And that also meant she wouldn’t be hitting on Mrs. Harris or Amanda, at least not at first.

That left Mr. H and Ryan. Both were hot. But Mr. H was the boss and married, and despite all that she had seen there was still the irrational notion floating around her brain that she would get fired if she fucked the boss. Ryan was closer in age—his eighteen to her twenty-seven—unattached, and less intimidating.

So she resolved to pay a visit to Ryan’s room the next night. And with that, she drifted off to a sleep filled with dreams of being fucked by a couple of manly Harris studs.

The next day the Harrises were all out, so Ana had the house to herself. Tanya was there, and they chatted a bit over coffee, but Ana couldn’t bring herself to tell the cook of her resolution. What if she chickened out and couldn’t go through with it? Eventually, though, Tanya needed to go grocery shopping and begin to prepare dinner, so Ana left her alone. She tried to watch television in her room, but found she wasn’t paying attention.

What was wrong with her? It was just sex with a guy. She hadn’t been this worked up over sex since high school. She wandered the house again, and found that Ryan had just returned. He was walking down the hall to his bedroom when Ana saw him.

Ana almost let him pass before saying anything.

“Ryan?”

“Yeah.”

“I was wondering...” She found she just couldn’t say it.

“What is it, Ana?” asked Michael when it was clear that she wasn’t going to speak.

“I was wondering if you, if you wanted to sleep with me.”

“Oh, yeah. Of course. I’ve wanted to sleep with you since I first saw you. I would have asked, except Mom said to let you join us in your own time.”

A wave of relief swept over Ana. “Well come on, then. Let’s go back to my room,” she said, taking his hand and leading him back to her apartment. Ryan followed happily.

Once in the apartment, she closed the door and leaned against it. She didn’t think any of the other family members would come into her room, but she didn’t want to give the appearance of inviting them in. For this first time she wanted it to just be Ryan.

She looked into Ryan’s eyes, and the boy took the hint. He leaned in, and they began kissing. It was almost chaste at first, just a brushing of their lips together. Then he pressed a bit more firmly, and she opened her lips just a bit. His tongue swept across her lips, not quite entering her mouth. Then unable to stand the teasing anymore, Ana grabbed his head and pulled him hard into her, plunging her own tongue into his mouth and wrapping one leg around his body, pinning herself between the door and his body.

Ryan’s mouth was sweet, and he was a good kisser. As they kissed, Ana could feel him growing hard against her belly.

She broke the kiss, pushed him away, and began unbuttoning her blouse. Again Ryan took the hint and enthusiastically shed his clothes. As soon as the two were naked, Ana threw herself into Ryan’s arms. He swept her up, carried her into the bedroom, and deposited her on the bed, throwing himself down next to her.

From there the pair took it more slowly. They started kissing again, more gently but still insistently, as their hands explored each other’s body. Ana shivered at the feel of his hard body. It was so good to feel a naked man next to her. It had been weeks. She let the back of her hand brush against his semi-hard cock. Then she took it in hand, and gently started to rub it into hardness. It grew to full length, almost eight inches and nicely thick. His mother was right, this was indeed a very nice cock.

For his part, Ryan ran his hands over her breasts, circling the nipples with his finger. That felt delightful to Ana. Then his hand drifted south, gently caressing her belly before finding its way to her sex, which was already glistening with a hint of wetness.

The pair stayed locked in embrace. Ryan broke the kiss for a while to suck on Ana’s nipples, before returning his attention to her mouth. Ana did the same for him, noticing that he shivered as she flicked her tongue across his nipples. Evidently, he liked it.

The eighteen-year-old’s inexperience, or perhaps it was his experience as a sub to his mom and sister, showed. He didn’t move to the next level. Ana was used to the guy taking charge during sex, but she suddenly realized that she was almost ten years older than the boy and that she would have to take the initiative. She already had his cock in her hand, so she positioned it at the opening to her vagina, rubbing the head back and forth along her lips to lubricate it with her juices. Ryan took the hint and pushed forward, entering her.

Ana gasped. She wasn’t used to anything this big. The teen stopped, fearing that he had hurt her.

He hadn’t. Ana grabbed his buttocks and pressed him closer, forcing him further inside. He slipped into her sheath fully, down to the hilt. Ana marveled at the fullness. Just having him all the way inside her was a pleasure. Then he started sliding in and out, and Ana experienced a pleasure that she had never felt before. Ryan’s cock wasn’t so big that it was uncomfortable having him inside her, but it was big enough that it stimulated her clit with each stroke. No other man she had been with had done that for her. She closed her eyes, bit her lower lip, and let him rock her to orgasm. It was a pleasant journey that took a while, but the pleasure slowly mounted with each stroke until after some ten minutes she could take it no longer. Pleasure like burning fire stabbed through her with every stroke, then she went over the edge.

The pain of the pleasure became unbearable. She shoved Ryan away from her, unable to be touched down there, and convulsed as her orgasm rocked her. Usually Ana liked to touch herself throughout the orgasm, maintaining the stimulation until she was done, but she couldn’t touch herself now. She tried to touch her nipples, but they were too sensitive as well, as if a wire ran from her clit to her nipples and then straight into the reptilian pleasure-center of her brain.

When she was through convulsing, Ana thought about climbing on top of him and riding him to his climax, but she was still too sensitive. So she slipped down and took his cock into her mouth. She was a bit worried that she wouldn’t be able to get much into her mouth, but was surprised that she could get about two thirds of him in. She thought about pushing it further, but then thought that gagging on the first blowjob probably wasn’t wise.

She pulled back, flicking tongue around the head and around the ring of his retracted foreskin, then dove back down, taking him as deeply as she could. That was all that Ryan could take.

“I’m coming,” he said.

It was nice that he gave her warning, thought Ana, but she didn’t mind the taste of spunk and persisted in her sucking, and a moment later her mouth was filled with salty goo. At that she started to gag a little and had to withdraw. Spilling cum all over his cock and shaved pelvis, which she then promptly vacuumed up with her lips and tongue. It tasted good, salty and clean.

The pair lay there cuddling, not speaking, with Ana’s hand still on Ryan’s penis, slowing coaxing it back to life.

Ana was enjoying just being held and could have lain there like that for hours, but the boy’s cock began stirring. Young men were amazing, the rebound was so quick. She flipped herself around, pushed his foreskin back, and began sucking him again.

Ryan began to push her legs apart, so she positioned herself on top of him in a sixty-nine, and he began licking her pussy. He was quite good at it. His mother and sister had taught him well. He sucked on her clit for several minutes, before switching to plunging his tongue into her vagina and sucking on her lips, and then moving to flicking and swirling his tongue around her clit. Each time he kept at it long enough for Ana to really enjoy the sensation and start to build toward orgasm, switching before it became monotonous or she went over the falls.

She began to emulate him, taking the head and upper shaft of his cock into her mouth for a few minutes, before switching to licking the underside, and then taking his balls into her mouth, swirling her tongue around them. Ryan grew rock hard, and if it were possible, even bigger.

Eventually Ana decided that she needed him inside her again. In the past, she would have opted for cunnilingus over intercourse any day of the week. But the sensation of that large cock inside her was too new and too tempting. She slipped off Ryan and got on her hands and knees. Ryan may have been reluctant to take the initiative, but he was no fool. He got the hint and entered her from behind.

He filled her with one, slow thrust. It felt so good. In keeping with the tone of the session so far, he thrust back and forth slowly, gently. But Ana needed and wanted more.

“Faster. Take me hard,” she ordered him.

He complied immediately, picking up the pace and slamming her hard. God, that felt really good! She had to dig her fingers into the mattress to keep from being pushed off the bed.

Her first orgasm came rather quickly. Then there was a lull where she just enjoyed the pleasure of his pounding, then the second and possibly a third orgasm. She wasn’t sure if it was two or just one extended one. Not that it mattered. Then as she came down from the heights, she felt Ryan stiffen and groan as he came inside her.

They collapsed next to each other, both sweaty messes.

“That was great,” said Ryan. “I’m so glad you finally decided to join in the fun, and especially glad you started with me.”

“Frankly, I was really nervous; I still am. I’ve never done anything like this before.”

“It didn’t seem like your first time,” he said smiling.

“You know what I mean. I’ve had plenty of sex before, but never anything kinky like you and your family are into. I picked you for my introduction because, in addition to being good looking and having a nice, big cock, you were the least intimidating. Your dad is my boss, and I’ve never been with a woman before. Besides, your mother and sister seem rather ... aggressive.”

“Yeah, they’re really into the dom thing, but don’t let that fool you. They’re very considerate. They won’t push you into anything you don’t want to do.”

“How long have you and your family been having sex together?” She finally got the burning question out there.

“Amanda and I have been going at it for years. Pretty much as soon as I figured out that I liked girls.”

“I mean most brothers and sisters don’t do it with each other.”

“Yeah, I guess it was growing up in this house. Mom and Dad have always been real casual about sex and nudity. They’re not nudists or anything, but being naked was never a big deal around here. I mean, it’s not like they were having sex in front of us when we were little, but we were always seeing them naked, and I’ve always known they were swingers. Even before I really knew what sex was, I knew they were having fun in their bedroom with friends. And Amanda and I knew what was going on back home whenever they shipped us off to a friend’s house for a weekend so they could have a sex party.”

“Wow. That must have been a wild childhood.”

“Not really. We didn’t know anything different. And when I was thirteen, Amanda and I started having sex. We knew we weren’t supposed to, that incest was bad, and we thought we kept it hidden from Mom and Dad, but of course they knew, almost from the start. But they never said anything. Turns out that Mom had been having sex with her brother since she was a teenager. She still does.”

“Oh my God!”

“Yeah. My aunt and uncle and cousins and us are one big sex family. You’ll meet them.”

“Wow. So when did you start having sex with your mom and dad?”

“That’s actually pretty recent. They waited until I turned eighteen. They started with Amanda when she turned eighteen, but kept that a secret from me for an entire year. I should have figured it out, but I didn’t.”

“So on your eighteenth birthday they just grabbed you and took you into the dungeon?”

“Sort of, although the dungeon is new. It used to just be a regular basement. It was a couple of days after my birthday when Mom came into my room. She was just wearing a robe, which wasn’t unusual, that’s how she usually dresses when she’s just hanging around the house, and she said she wanted to talk and told me that she knew what Amanda and I had been doing.”

“You must have been terrified.”

“Yeah, I thought we were totally busted, but then she told me that her and Dad had known about it for years and that she had fucked her brother, so it was okay. We weren’t in any trouble. Then she just put her hand on my crotch and said that it was something that boys and their moms could do too.”

“You must have been floored. Was it a fantasy come true?”

“Yeah, I didn’t know what to say. I said something; I don’t remember what. I’d never really fantasized about it. I mean, I’d wondered what it would be like to fuck Mom, especially after I’d started fucking Amanda, but it wasn’t like a fantasy of mine or anything like that.

“Anyway, she just started to unfasten my pants and took my dick out and started giving me a blowjob. I blew my load like right away. She just swallowed it and said that if I wanted more, to stop by her bedroom that night. Then she left.”

“What a way to leave an eighteen-year-old boy hanging,” said Ana.

“Don’t I know it. I couldn’t do a fucking thing the rest of the day. It’s all I could think about. I was so horny.”

“I’ll bet,” she said, turning and snuggling up to him. “So what happened that night.”

“I waited around until I was pretty sure that Mom was in her room, then I took a shower, put on a robe and went to her room.”

“Were you wearing anything else?”

“No. I could hear the shower running in the master bath, so just opened the door. Then I realized that Dad was in there too. Mom was in the shower, but he was just laying on the bed watching a porno on the TV with the sound turned down. I’d forgotten all about him.”

“You must have been freaked out.”

“Majorly. But he just said that Mom would be out in a few minutes, and that I could just get on the bed with him. I realized that he must know, but it was weird. We didn’t really say much. We just lay there watching the porno. After a couple of minutes I heard the water turn off and a little later both Mom and Amanda came out of the bathroom, naked. They were giggling and still drying themselves.”

“All four of you. That must have been a surprise to see Amanda there.”

“Yeah, but instantly I felt better. It all fell into place, and I figured out that it was all cool. Mom said that now I was here, we could begin. Mom and Amanda hopped on the bed and started giving Dad and me blowjobs, Mom with me and Amanda with Dad. Then we ended up fucking every which way. I don’t know how many times I came, but we didn’t quit until two or three in the morning.”

“Did you and your Dad fuck too?”

“Not that night. Later that week he sat down with me and told me he was bisexual, and if I wanted, the two of us could fool around. But he said that same-sex stuff was different for guys than for girls, and if I didn’t want to that was fine.”

“Are you bisexual?”

“I dunno. Maybe. I’m not really into guys, but if something happens, I’m cool with it. It can be fun, but I’m not like Dad. He’s into both guys and girls, and he’s got some guy friends he has sex with on his own. But the two of us don’t fuck, not unless it’s part of a group sex thing.”

“Do you like it when fucks you in the ass?”

“Yeah,” he smiled as he said that. “It feels really good. I liked to be pegged too. Amanda is really good at that. She’s death with a strap-on. Better than Mom. You should try it with her.”

“I dunno. The one time I tried anal, it kind of hurt.”

“Had the guy ever done it before?”

“No. We were both totally new at it.”

“That’s where you went wrong. We could try it, but I’m still kind of new at giving anal. And Dad’s kind of big for a first time, so you should ask Mom or Amanda. Especially Amanda. Just tell her that you’re an anal virgin, and she’ll treat you right. It won’t hurt at all, that is unless you want it to.”

“I’m not really into pain.”

“Are you a dom?”

“I don’t know. That’s the kind of thing I’ve never tried. I wouldn’t know how to be a dom. I might like it though, so long as it’s not painful. I do like rough sex, but I draw the line at actual pain.” Ana found Ryan really easy to talk to. He seemed eager to talk about it too. He probably didn’t have any opportunity to talk to anyone about this.

“That’s cool. You’ll figure it out. Just be sure to tell Mom that you don’t want pain. Dad is a sub, and Amanda is more into psychological dominance. But Mom has a sadistic streak, but she won’t do anything you don’t want, so don’t worry about that so long as she knows your limits.”

“This is all so new to me. It’s kind of intimidating.”

“I’ll tell you a secret. You know how Mom seems so self-assured, dominant, and in control?”

“Yeah. I’ve noticed.”

“The other night when you watched us, we were snuggling after sex, kind of like you and I are doing now. Anyway, she told me that she was terrified of you.”

“Of me?”

“Yeah. She didn’t know how you would react to all this. She and Dad are nervous as all get out. They’ve never brought someone into the games like this. I mean, Tanya has been here forever, since back when it was all behind closed doors. And with new friends, they get to audition them and work them into games bit by bit. But hiring a live-in was a big step. You have no idea how many people Mom interviewed, and still she was sweating bullets with you.”

“I had no idea.”

“Don’t tell her I told you that. Just know that you’re not the only one a little scared at all this.”

Ana leaned over and kissed the boy again.

“Go tell your mother what we’ve done,” she said, taking a hint from what Amanda told her dad the other day. “Tell her that she, Amanda, and your dad can take me anytime they want, but that I’m still a bit nervous about it, so they should be gentle.”

With that, she got up and went into the shower.

The next morning Ana was having a cup of coffee with Tanya in the kitchen when she told her about sleeping with Ryan.

“Don’t you just love a big dick?” said Tanya, smiling. “Michael’s is even bigger.”

“Yeah, I’ve seen it.”

“But you’ve got to feel it inside you, it’s just wonderful.”

At that moment Mrs. Harris breezed through the kitchen, evidently in a hurry to get somewhere.

“Tanya, have you seen the keys to the Benz?”

“They’re on the hook,” said Tanya, glancing over to the wall where the keys to the various cars the family owned hung.

“Oh, yes. Right where they should be. I’d lose my head if it wasn’t attached.” Then she noticed Ana. “What are you girls talking about?”

“Your husband’s dick,” said Tanya. Ana blushed.

“Oh, my favorite topic,” said Mrs. Harris. “I wish I had time to compare notes with you. But Ana, I’m glad I caught you before I went out for the day. I’ll be back about four, and I’d like to talk to you then.”

“Okay, Mrs. H. I’ll be here,” replied Ana somewhat nervously.

“Don’t worry. It’s all good. See you then.” And she breezed out the door that led to the garage.

“That could be ominous,” said Ana.

“She’s probably just going to have the talk with you.”

“The talk?”

“Yeah, Susan likes to talk about sex with someone before she sleeps with them. She’ll go over what you like and dislike, what turns you on, what your absolute no-noes are. If you’re into S&M or bondage, she’ll discuss a safe word. That kind of thing. It’s a pretty smart idea, but I think she does it to maintain control, or at least the illusion that she can control things.”

“She doesn’t get jealous of women sleeping with her husband?”

“I’ve never seen it. You have to understand, she and Michael are absolutely devoted to one another. To them, sex with others is just rubbing bodies together. Don’t get me wrong. They genuinely like the people they take into their bed, and some, like Ryan and Amanda, they love. But no one is ever going to get between the two of them. They are soul mates. With them it’s true love.”

“I’m not sure I could do that,” said Ana. “I get having sex with someone you don’t love; I’ve done it often enough. But I’m not sure I could share someone I genuinely loved.”

“I know I can’t,” said Tanya. “If I ever got married, I’d have to quit this job.”

Despite Tanya’s assurance, Ana was nervous about the meeting with Mrs. H. But she needn’t have been. They sat down over coffee and Mrs. H. just dove into the topic.

“Ana, since you’ve decided to join in on our little games, I’d like to get to know you a little better, to find out what your turn-ons and turn-offs are, that kind of thing. We don’t want to overstep any boundaries.”

“I understand.”

“First, don’t worry about me getting jealous. I don’t. You can fuck my husband until the cows come home, and I won’t care as long as it’s all out in the open. The only rule that Michael and I have is that there are no secrets between us.”

“That’s what Tanya said, but I’m still a little nervous about it.”

“Of course. After a while that will go away.”

“Now I know you’re into guys, and I assume that you want to fuck my husband too. But are you into women as well?”

“I’ve never been with a woman. I think I’d enjoy it, but I’ve never fantasized about it or anything like that.”

“Would you like to explore that side of your sexuality?”

“I’d like to try it. I’m pretty much game for trying anything.”

“Except pain. Ryan told me that you’re not into pain.”

“I’ve never done any kind of S&M, so I don’t really know. But I don’t think I’d like it.”

“That’s fair. Do you think you’d like to inflict pain? Do you like to slap your partners? A lot of people are uncomfortable about inflicting pain.”

“I’ve never done that. I don’t know.”

“Okay, we’ll leave the hardcore S&M off the table, at least for now. If down the road you think you want to explore that aspect of your sexuality, we can take it slow.”

“Michael and I are both entirely bisexual, as is Amanda,” continued Susan. “We get turned on by both sexes. Ryan is like you. He’s into the opposite sex, but he is, I guess you would call it heteroflexible. He’ll fuck a guy if the moment is right. Ryan also said that you’re not very experienced with anal.”

“I tried it once with a boyfriend, but we didn’t know what we were doing. It hurt. I’ve never tried it since.”

“Would you like to try it again?”

“Do you enjoy it?”

“Yes, I love it. It’s a very different sensation than being fucked in the vagina. I understand it’s different, more enjoyable, for guys because they have a prostate, but us girls can enjoy it too. You don’t cum like you do from clitoral stimulation, but the feeling of having your ass penetrated and filled is powerful. Do you like the feeling of a man inside your vagina? Not just having someone play with your clit, but having him fill you up?”

“Oh, yes. My last boyfriend, he was a total shit, except he and I had this chemistry in bed. Sometimes he would just keep his dick inside me, not moving. That alone made me cum sometimes.”

“Then you’ll probably enjoy anal, just like me. We’ll leave it off the table at first, and when you’re ready just let us know.”

“Ryan said that Amanda was really good at giving anal.”

“She is, and she’d be happy to take you aside and show you how to do it right. Just ask her. Now, you’re not into pain, but do you like rough sex? Hair pulling? Spitting?”

“Yes. I love being taken by a guy, being thrown about or held down. I’ve never had my hair pulled or been spit on. I guess I’m pretty inexperienced.”

“Not at all. This is pretty advanced stuff. Most people have never done anything except oral and vaginal intercourse. You’re a pretty adventurous girl. Don’t worry about that. And all these things I’m bringing up, you don’t have to do them. If you try something, and it doesn’t do anything for you, we don’t have to do it again. If it turns out that all you really want is vanilla, heterosexual sex that’s fine. Michael and Ryan will be more than happy to fuck you vanilla. Where were we? Oh, hair pulling and spitting. Hair pulling, if done right, doesn’t hurt. It’s a way to control your partner. Spitting is a dominance thing too. We can try it when we get rough, and if you don’t like it just say something and we’ll stop. Have you ever done any bondage?”

“No. I’ve had boyfriends hold me down so I couldn’t move, but I’ve never been tied up. And I wouldn’t know how to tie someone up.”

“Did you enjoy being held down?”

“Yes.”

“Then we can try some bondage. Light at first. Just tying your arms to the headboard or maybe handcuffs. None of us Harrises are really into hardcore rope play, but we’ve got a friend who is a master at devising ingenious ways to tie people up. So if you like the light bondage, you’ll have the opportunity to progress further if you want to. Now Ryan said that you didn’t know if you were a dom or a sub.”

“I don’t. I’ve never done any dom-sub play.”

“But from your answers, I’m guessing that you have a submissive streak.”

“That’s probably right.”

“Good. You should know that the men here are also submissive. So it will be good to have a female sub to play with. Amanda and I are both definitely doms. But don’t worry. We both enjoy vanilla sex too and we bottom when the situation calls for it. And the guys will be happy to throw you around and pound you hard when you want it.”

Ana smiled at that.

“Now, the only thing left to ask is, do you want to have sex with my husband, and maybe with me?”

“Very much.”

Mrs. Harris smiled. “Would tonight be too soon?”

“No, tonight would be perfect.”

“Alright then. Why don’t you come by our bedroom at, say, nine.”

“I’ll do that,” said Ana with a slight hesitation in her voice.

“And this time, come into the room instead of just watching from the door.”

If Ana had been nervous leading up to the afternoon interview, the wait until nine o’clock was excruciating. She felt a gnawing in the pit of her stomach, and the delay made her perpetually wet between her legs, to the point where she began to wonder if she would have any lubrication left by the time the appointed hour rolled around. She realized that Mrs. Harris had pulled the same tactic on her as she had on her son the first time they had sex. She had been reduced to a nervous wreck. It really was a subtle and very effective domination and control technique.