Chapter 03: Becky's Family Meets Lisa

Story Info
More with Cheryl. Lisa shakes up Jack's family.
7.4k words
4.68
13k
16

Part 3 of the 18 part series

Updated 12/06/2023
Created 07/20/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jimplx
jimplx
167 Followers

Becky, Cheryl, Sam Plan Vacation

Thursday, almost a week after the first big event, Becky invited Cheryl over. She chose Thursday because Sam did not have classes that day. Since they decided on inviting the kids along, Becky figured she needed the input from a teenager. She obviously had her prurient interests in a repeat of Cheryl's last visit. Sam's enthusiasm indicated Sam knew this would be a continuation.

When Becky called Cheryl to confirm the date, Cheryl excitedly asked if Sam could be there. This gave Becky some concern. It seemed Sam and Cheryl were a bit too excited. "Who am I kidding?" Thought Becky. "Yes, Cheryl enjoyed the sexual experience with Sam, but so did Sam and so did I. I got on with Cheryl, without Sam, too. We all three shared the bed. Am I jealous of Sam getting attention from Cheryl? Am I jealous of Cheryl getting Sam's attention? I need to give this up. We are all just playing around. We can all enjoy each other and not get possessive. I do enjoy seeing the pleasure my daughter gets being around Cheryl and vice versa."

Becky confirmed that she invited Sam. Cheryl was overjoyed.

They were all wearing shirts and shorts, as usual. They poured the wine. Becky told how things had progressed all week. Cheryl took her shirt off when Becky described the naturist decision. She was pinching her nipples. Sam took off her shirt and copied Sheryl's actions.

Sam's nipples were a bit sensitive and she asked Cheryl "Does pinching them cause them to hurt? Mine are sore."

Cheryl said, "Yes, a bit. If I do it a lot, it builds up. Even with the pain, it gets me excited. Maybe the soreness is part of it."

Sam asked "Can I try to soothe them?"

"Of course."

Sam leaned over and took one of Cheryl's tits in her mouth. She licked the nipple and aureole causing Cheryl to moan loudly. That was enough for Becky. She came over and took the other tit.

Cheryl's hands were now free. She used her left hand to pull her shorts to one side. Her right found her pussy. After moistening the forefinger, she began circling the base of her clit, occasionally rubbing across the top of it. The intensity of the clit rubbing and her best friends' nipple play brought a very fine orgasm. It concluded with a satisfied moan.

Becky said "That was nice. I am not sure how titty sucking works with the masturbation rules. This is the first time any of us has touched another person. It has all been self-stimulation."

Sam said, "Yes, it is the first time I've sucked any woman's nipples. I liked it. Obviously, the rules do not apply to Cheryl, she not family. I want to suck your nipples, too, mom, but maybe the incest rules apply to us."

Sam's question definitely got Becky excited. She wanted to ask her daughter to suck on them, but was not sure how to say it. Cheryl let her off the hook by asking "what are you talking about?"

Becky explained the rules and the "not incest" logic.

"So, if I come over when the whole family is here, I can see everyone naked. Erect dicks and boys jacking off?"

Sam said "We really have not discussed guests, just family. This can get complicated. Jack's girlfriend is coming over Saturday. We will all be dressed and on proper behavior. Let's talk after that. Right now, I want to see your pussy."

Cheryl pulled her shorts off, laid down and spread her legs. Sam took off her own shirt and shorts. She then said "mom?"

Becky took off both garments, laid on the floor, and spread her legs. Sam understood her mom's non-answer about nipple on play and started on her mom with nipple pinching. In the meantime, Becky started rubbing her own pussy. Becky's moaning started a bit later. Cheryl got up on her knees, straddling Becky, and started kissing Sam's nipples. Her mom was looking directly at Cheryl's pussy just a few inches from her eyes. The musky aroma of her recent orgasm was intense, giving Becky feelings she had never had. She was tempted to lick Cheryl's pussy, but was afraid of the lesbian implications. She felt it was definitely out of bounds by engaging so intimately with another woman with her daughter here. Cheryl started massaging Sam's clitoris. Both of Becky's hands were busy on her own clit. Sam inserted her hand under Cheryl's for her final stimulus. Sam came first and watched her mom come shortly after. Cheryl rolled onto her back on the floor and finished herself with a flourish.

With the sexual tension reduced, it was time to discuss the vacation. Becky said, "Cheryl, we have a nice nude beach we used to frequent in San Diego. We thought about renting a house for the week. The house is quite large and it is isolated. They advertise it as a 'naturist retreat.'"

"That sounds great. I am sure Bill is game. When I suggested we might have a naturist get-together, he was all in. I will ice it with him tonight. I will not tell you why he likes the idea" she said with a little laugh.

Cheryl continued "I have a problem, though. I did not give him the full rundown on what we did last Friday. I am a bit worried he will find out that I was not entirely truthful. I left stuff out mainly because I did not want to give out secrets about you two without permission. I want to protect the privacy of both of you. I was also concerned that he would not understand the sex parts."

Becky said "Yes, that could be a problem. I know the three of us can be mute, but I told Tom quite a bit. I only told him the three of us got off."

"Mom!?" Squawked Sam. "I cannot believe you told him about me."

"He only knows of one set of orgasms. No backyard and no sleeping together. Oops, maybe I said three orgasms. Oh my god he sure came a lot when I said the three of us got off together." She said excitedly. She gave Sam her best smile, then to both of them, said "Sorry," regretfully.

Sam replied "It's alright. He hasn't seen me rub or come yet. Maybe I should fix that."

"Only if you really want to. He has been okay with just looking and jerking so far. Neither one of us has done it in front of Jack, yet. I like the status quo."

Cheryl's eyes popped open wide and said "I am starting to understand what is going on behind the masturbation rule. Maybe I can backfill Bill with one jill session from last Friday. No one say anything about nipple sucking, okay?"

They all agreed and Cheryl headed home. When Bill came home Cheryl led him to the bedroom once again and said "Watch." She pulled off the two garments and Bill stared.

"No underwear?"

"Watch."

Cheryl laid down, started on her pussy. No cunnilingus, just her fingers. He removed his clothes fast, never losing sight of her fingers. He was rapt. After her orgasm, she asked if he liked it. His erection provided the answer, but he also said "Yes. An unassisted female orgasm is a beautiful sight."

"I agree."

"You've seen one?"

"Yes."

"When?"

"Last Friday."

"You saw Becky masturbate?"

"I did."

His hand gripped his erection. She kept her eyes on his hand. "How did that happen?"

"I mentioned that they are naturists, right? I told her we were, too. We both decided to get comfortably naked. It was not sexual at the time. I mentioned she wanted companionship, too much wine, girl talk. Of course, a lot of girl talk is about sex. We both got turned on and we got ourselves off."

He was starting to take rapid breaths.

"That is a serious turn on. You did not mention it last time. Did you help her?"

"No, we each did ourselves. You understand, this was all new to me. I was a bit frightened. I wanted to protect Becky's privacy. I didn't want you to think I was kinky, or a lesbian, or cheating on you. I am sorry for leaving out that detail, especially if it turns you on. Am I in trouble?"

"Absolutely not. It was not cheating, you were just playing around, right?"

"Yes, it was not planned, it just kind of happened. I love you."

"Yes, I get it, trust is important. You know I will keep it a secret. I appreciate that you changed your mind and told me, you did not have to do that. And, yes, it obviously does turn me on. Has it happened again?"

His hand was a blur. She was enjoying his show. He apparently enjoyed her attention to his dick.

"Yes, today. I found out that they have adopted a naturist lifestyle for the family and they are planning a naturist vacation. They want us to join them. I went to discuss the vacation. Becky wanted to masturbate again and asked me to watch, so I did. Yes, she does have nice tits and a nice pussy. Am I forgiven?"

His cum shot out of his head as she watched.

"Yes, you are forgiven. Especially if you share the stories with me. That is why no underwear."

"Yes, makes it easier to 'share.'"

"You did not tell me if you did it, too." His dick rising again.

"Share and share alike." She replied with a smile. "Do you want me to do it with her again?" she asked with a twinkle.

"Yes, but I do not know how much more I can take." He began stroking again, half-heartedly and with little hope of finishing.

Sheryl texted Becky "I told him we did it on Friday. I did not mention Sam. If he calls me on it, I can tell the truth, that she wanted it kept a secret. He wants me to do it again! I can't wait!"

More Vacation Planning

Sheryl and Becky got together the next day, ostensibly to discuss the vacation. Becky said "I am just too horny to think straight, should we get the first round out of the way first?"

"Definitely. The planning needs to get done, but I am mostly interested in satisfying Bill's request." She said with a wolffish grin.

This time they laid on the sofa facing each other. Their feet were facing the others' shoulders and heads propped up so they had a clear view. They did it simultaneously.

Becky said "My head is now clear, let's talk about the vacation before we get side-tracked again."

It was decided to include all six of them, not just the married folks. This was a bit problematic, as Lisa was excluded. Becky would have to work that with Jack.

The weather prediction was checked, the rental was reserved, the route and timing selected. The rental was far larger than they needed, but the promised privacy was well worth it.

They knew everyone would be nude as much as possible. Last item. Casual sex. Both agreed to use the masturbation rule. Any other sex should be behind closed doors. However, everyone was an adult, the rules were flexible, and anyone could say no to anything.

Cheryl said "Time to go tell Bill. I really do not want to leave, though. Can I beg for a one-time rule change?"

"Sure. I can always say 'no.'"

"Can I touch you?"

"Let's see how it goes."

They retired to the sofa. They hugged. While hugging, Cheryl massaged Becky's breasts. She then focused on the nipples until Becky started hugging Cheryl tighter. Cheryl broke the embrace and started kissing Becky's nipples. Becky started rubbing Cheryl's nipples, too.

Cheryl went back to kissing, thoroughly enjoying having her nipples rubbed. She slowly ran her hand down Becky's back to her hip. Across the hip until she reached Becky's labia. She slid her second finger between the folds and rubbed her clit. Through the pleasure, Becky could not maintain the kiss and buried her face into Cheryl's shoulder and neck. The pleasure rode from the labia, into her tummy, nipples, and face. She whimpered as the orgasm crested. She then gave a soft lip-to-lip kiss. She pushed her tongue into Cheryl's mouth.

While kissing, Cheryl moved her own hand to her own mound for a delicious orgasm of her own.

That night she told Bill about the sex rules. He was pleasantly surprised that anyone could masturbate at any time. "This includes Sam?"

"Yes, but even though she is allowed to get off in front of the men, she may choose not to. And, no, I am not going to allow you to ask her to and especially not ask her why she is not."

"Have you ever seen her?"

"I am not going to answer questions about what other people do or do not do in private. Make up a fantasy and jerk off to that." Her salacious grin pretty much confirmed Bill's fantasy.

Bill asked about any other activities between the women. Cheryl said "Becky got naked, but did not masturbate." He was disappointed until Cheryl said she did masturbate for Becky. She did not think it was helpful to let him know that she also did Becky. "Last night you asked if I helped her, is that something you want me to do?"

"Only if you want."

"Does the thought turn you on? Does it cause worry?"

"I don't think you will dump me for Becky. You said it was just playing around."

"Yes, just playing, I'm not a lesbian. You are my life partner."

"Thought of you guys touching each other is a serious turn on. If you can, do it. One condition. You tell me what happened."

Cheryl held back from telling him about getting Becky to come without asking Becky first with "I need to protect privacy, so you may not hear everything."

Disappointed, Bill said "Well, okay."

Bill fucked her with abandon. After that first session, they stayed naked the rest of the night and frequently did oral sex and masturbated to the edge; and finished later with a glorious simultaneous orgasm with Bill erupting deep within her pussy.

Becky's Family Meets Lisa

Saturday came and everyone scrambled around the house and yard, making sure everything was tidy and presentable to Lisa. The only wrinkle came in when mother and daughter got really horny. They chose to avoid their usual masturbation session. They had still not done it in front of the boys and did not think they could get enough private time to do it justice. They did, however, touch themselves when only they could see each other. Sam preferred to push her hands into her shorts and tickle her clit. Mother had developed a fascination with pinching her own nipples. Sam was holding back from soothing her mom's nipples in case they were seen.

They were both so horny that they were pinching and rubbing constantly, it took a long time to finish the party preparation.

The wrinkle came in clothes selection. Both chose thin skirts that were easily seen through when backlit and thin white blouses. Nothing else. The skirts were really not an issue. There were no dramatic color changes around the pelvis because there were no panties and both shaved to avoid visible pubic hair. Lisa might notice there were no panties, but it could be easily explained that they wanted to avoid visible panty lines and it could open an interesting conversation. The men wouldn't notice.

Both women had areola that would show through the blouses. And, of course they bobbled quite a bit. After a very long discussion with the men, both women agreed to wear a bra. In protest, they chose nearly transparent ones. This covered the color and reduced the pokies, somewhat, and eliminated the bounce, but left the men slightly annoyed that the nipples would still be visible; but less than if they were braless. Of course, both men did enjoy watching all four breasts during the costume changes and bra fittings. The girls drug out the costume changes to help get the men to be more agreeable. When debating about bras, they would remove the one they had on first and debate the next choice, topless. The men became more agreeable about exposure as time went on.

The evening was planned so that Jack had something to do a few times so mother and sister each had one-on-one time with Lisa.

The talk with Jack's mom mostly focused on college plans and other safe topics. Becky wisely stayed away from marriage and children. She was quite taken by Lisa and hoped she left a good impression of herself.

Sam ushered Lisa into her bedroom for her discussion to allow more privacy and establish a young-adult vibe. Sam acted the part of the sister who knew nothing of her brother's affairs. She set an early ground rule that everything would stay between them. As Sam was still seriously horny from edging all day, after the "get-acquainted" chat she steered the talk to her favorite subject, sex.

Sam asked "Have you guys done the deed?"

"No."

"Virgin?"

"Yes. How about you?

"Yes."

"Steady boyfriend?"

Maybe this was the opening she needed. "No. There are a few guys I go out with, but nothing steady since I started at State. Too much homework and adjusting to new intellectual approaches. It is so different from high school. I guess my steady date is the little man in the canoe."

Lisa gave a knowing nod to that. Sam was relieved there was no shock at her honest answer.

Sam decided to push just a little. "You do things with Jack, right?" The question did not seem to bother Lisa.

"Sure, we fool around. I think I would like to do it with him, but I am not ready to, yet. So far, he has not been pushy. He seems satisfied with heavy petting."

Sam agreed with Lisa. "I avoid guys who think that intercourse is a given. In my experience, if I can get the guy off, he seems satisfied."

"So, oral, handjobs?" Better, Lisa was now leading the sex talk.

"Yes. I can usually get a guy off with my hands. I kind of enjoy giving blowjobs. They really appreciate it. But it is only one way, me getting them off."

"Don't they give you a diddle?"

"Sure. They sometimes also give me a lick, too. But I don't know about you, but boys just can't take me the last five yards. In some cases, they take it personally if I finish it, so I do not even try anymore."

"I am kind of the same. Jack is great, he is sensitive to my needs, and he gives head readily, but I do need to be hands on at the end. But Jack understands my needs. He likes to watch me finish. It is probably because he prefers to finish himself, too."

Lisa paused for quite a while. "Oh boy, I am really telling tales out of school, aren't I? And about your brother.

"I enjoyed our talk so much, I forgot about that. It was like chatting with my long-time friends. I am sorry."

"Do not worry. No way that knowing he likes to jerk off changes my opinion about him. All boys love jerking off, especially with an audience."

Sam continued, "Girls are not much different."

Lisa smirked, "So, you like an audience?"

"Well, I meant the getting off part, but now that you mention it, it is nice to be watched."

After a few seconds of silence, she continued, "Oops, that did not come out quite right."

Lisa giggled. "I know, we girls are taught that sex is dirty. It is not to be shared, except with a husband, and so on.

"I think most of us have similar motivations, but cannot discuss it. All those taboos about doing anything that looks lesbian. All of that. Heck, guys have circle jerks, and that is somewhat acceptable. Oh shit, now I am going too far. I hope my opinions do not offend you."

"Of course not. Am glad we can talk openly. Sex talk is naughty fun.

"Talking about naughty secrets, mom and I were going to be braless, but Jack and my dad thought you might be offended. I am guessing you wouldn't be, am I right?"

"Absolutely. How about we shock them?"

Lisa unbuttoned her blouse and waited. Sam started on her buttons. Lisa unsnapped her bra and dropped it down her arms. Her breasts were large, with large dark aureoles, and small nipples.

"I guess I am not supposed to say this, but 'very nice.'" Quipped Sam.

"Thanks. Your brother seems to like them." Lisa said with a devilish smile.

"I can see why."

Sam pulled off her bra to reveal her breasts, and, while displaying her tits to Lisa, texted her mom, "We are now braless." She then put on the thin shirt. To Lisa she gave a giggle and said, "We are probably making them wonder if we are lesbians. Let's get out there."

The girls went back to the kitchen where they found the men cleaning up. Lisa's blouse was burgundy colored silk. Her breasts swayed visibly and her nipples were hard and poking through, but her areola were not visible. Becky's mother was pouring coffee. Her nipples were clearly visible through her shirt. Like the other day, she looked nearly topless.

jimplx
jimplx
167 Followers