Adventures of Derek and Amy Ch. 05

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Brother, sister and friend have date, threesome, anal.
13.2k words
4.7
18.1k
27

Part 5 of the 6 part series

Updated 06/11/2023
Created 07/17/2022
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Jill left Amy and her brother Derek sleeping, as she made her way downstairs to the kitchen.

She found their mom finishing a bagel and drinking coffee.

"Good morning, Amy's mom!"

"You can call me Claire, if you like."

"I like," she answered coyly. "You're up early." It was part statement, part question.

"I have to go to New York." She was professionally dressed in a white skirt and light blue top. She had her overnight carry-on leaning against the island.

"Ah right, gotta secure the new job," Jill winked then gave the appropriate index-finger gesture of a gun and clicked with her tongue.

"Still have to play the game. Coffee?"

"Thanks," Jill was tired and sat at the island counter.

"How do you like it?" Jill had momentarily lost her thought and was a little surprised at her directness.

"Any way I can get it," she smirked, remember the night before.

Claire looked at her for a moment. "I meant your coffee dear." Jill looked up to find a coffee mug had been filled and placed in front of her. She was being offered milk or cream.

"Oh, creamer thanks." Jill took a sip. It was hot and she was clearly tired.

"Seems like you all had a late night," Claire asked.

"Yea, we had a fun time."

"I'll say," Claire responded.

"Tequila will do that," Jill played along.

"And hormones, I think." Again, part statement and part question.

"What?"

"I heard a certain young lady really enjoying herself last night," Claire said playfully, smiling at her knowingly at the same time putting stuff back in the fridge.

"I don't, um..." Jill stammered. Was it that obvious? Did she make a scene?

"Sorry, don't mean to embarrass you. I got up to use the restroom late at night, and the bedroom noises were, um, discernible. I didn't realize you and my son were that far along - are you dating?" She prodded for information. These were her kids in her house, and she had a vested interest.

"What makes you think he and I..." she left the question hanging there.

"You're wearing one of his t-shirts, dear."

She looked down and tugged at the shirt - it was his. "Oh, I just got this from the dryer. I mean, I wasn't planning on spending the night."

"Relax. This isn't the 1950's. I just asked if you are dating." Another statement and question.

"Well actually... we're, um, not exactly..." she didn't know what she wanted to say.

"Sorry to put you on the spot. It's OK," she looked over from the fridge. "What you two do in private is fine, you are consenting adults. And I was your age once. All I'm saying is keep the noise down."

"The thing is," she felt compelled to set the record straight. "That wasn't me..."

"I know a woman's voice when I hear one."

Jill sat there, quietly sipping her coffee.

"And the only other girl in the house was my daughter."

Jill quietly took another sip, her silence confirming something but not explicitly what.

"But that would mean," she had a look that went from shock to disbelief.

Jill decided it wasn't time to blindside her new playmates by outing them. And she was feeling just a little bit underestimated.

"What," she asked playfully. "You don't think I could get her to make those noises?"

With a strange sigh of relief, Claire looked at the young woman sitting opposite the island from her.

"I just, um - oh dear! Now it's my turn to be embarrassed," Claire said, trying to compose herself. "Well, this is certainly a new development. I mean, I didn't exactly realize she was into girls. Not that there's a problem with that mind you." Claire pointed and made sure she was heard.

"If it's any consolation," Jill replied sincerely. "I do think she prefers guys." That much was true, she thought to herself.

"From the sounds coming out of her bedroom last night, I don't know if I would agree."

"Well," Jill recalled the previous night's frivolities. "A good lover pays attention to their partner's needs. And I gave her my full attention." She smiled and put the empty mug in the sink.

"Lucky girl," Claire said staring off into nothing.

"Are you jealous Mrs. C?" She asked playfully, slowly walking around the island to her position.

"Whatever do you mean?"

"I noticed you were checking me out yesterday, by the pool." Jill played her hunch.

"You are a beautiful young lady," Claire replied. "I was going to say that it seemed like you were showing off for Derek."

"Would it surprise you to learn part of that was for you?"

Claire contemplated this for a moment, wondering if she was serious or not.

"And what about you and... my daughter?" She tried to change the subject.

"I gave it my shot. Sort of one sided. Left a bit frustrated, actually." All true, Jill thought to herself.

"Sorry to hear that," Claire said a little disappointed, but also intrigued.

"Are you?" Jill wondered. She walked up to her from behind, close enough to smell her. "Would you like to know how I did it?"

"Did what?" Claire asked from over her shoulder, not wanting to turn and face the young seductress.

Jill whispered in her ear. "Would you like me to touch you the way I touched her?" Jill put her hand on her waist. "Would you like to lose control, to feel an orgasm as strongly as she did?" Jill pressed her breasts into Claire's back.

"I, uh..." Claire wasn't sure how to respond. But she wasn't moving away from Jill either.

She tilted her head back as Jill reached around and massaged her breasts, gently kneading them.

"Oh, yea..." Claire liked her touch.

"D's?" Jill asked, still whispering in her ear from behind.

"Double," Claire replied.

"They're awesome. No wonder the guys like you so much," Jill added.

"And some girls apparently." Claire said playfully.

"Your daughter was curious, but in the end too shy." Jill was toying with her now. "But you, I bet you sleep with guys to get what you want. But secretly you prefer women - who know how to give you what you need." Her hands traced up and down her sides, feeling the contour of her body.

"But I haven't..." her voice trailed off.

"Lately? How long as it been since you've been with a woman...4, 5 years?" Jill nibbled on her ear. With her other hand she softly caressed Claire's ass through her skirt. Jill went in for the kill. She was going to seduce her, right there in the kitchen, with Amy and Derek asleep upstairs.

"Yes..." she tried to resist, but urges buried in her long ago were coming to the surface again. And this time she was the object of desire. "How did you know?" she asked helplessly.

"Oh, I can tell." Jill blew hot air in her ear, causing her legs to buckle. Memories of forbidden love and sexual adventure made Claire excited. Yes - how she missed the touch of a woman!

Claire pushed back into Jill, just enough to convey that she was interested and a willing participant now.

Jill grabbed her by the hips pulling them together. Her hand on Claire's ass snaked around to her front.

"Uh... I can't..." Claire was about to give in when her phone alarm went off. She had to reach her phone on the far counter to dismiss it.

"Saved by the bell?" Jill asked playfully, seeing that Claire was visibly aroused. She straightened her skirt and her blouse.

"I would gladly take you upstairs and see where this goes," she looked at Jill hungrily. "But for two problems."

"And what are those?"

"My kids are home. And I have a flight to catch."

"Leave Derek and Amy to me," Jill said without explaining further. "You go. If you get the job... I'll be your reward. I'll service you all day, anything you want."

"And if I don't get it?" Claire asked playfully, raising an eyebrow.

"Same, but anything I want."

Claire thought about it, looking at the confident, beautiful, young woman in front of her. Propositioning her. Clearly skilled at seduction. And Claire desired what she was offering.

She grabbed the handle of the carry-on, and her cell in her other hand.

"I'll be thinking about what I want you to do to me as I'm signing the contract."

And with that Amy's mom left for New York.

--------------------

Derek came down in the late morning, finding his sister Amy in the kitchen. She sat at the counter in one of his Nirvana t-shirts, quietly starting into her phone.

"Hey, sis." He noticed she was on the verge of tears. "What is it?"

"I blew it. We blew it." She looked up at him and started to cry.

"Hey now..." Derek came over and wrapped his arms around her in brotherly support. "What's wrong?"

"Jill's gone," Amy pointed to the obvious absence of their friend. "And she's not answering my calls."

"Really?" He was disappointed too.

"I've texted her like 20 times." She held up the phone like evidence, then set it face down.

"Well..." Derek knew the girls lived by their phones. He remembered being on the plane and Amy just had to have the internet package, so the girls could text each other.

"Am I selfish?" she said looking into his eyes.

"What? No. Why do you say that?"

"It's just... She got me off, twice! And I did nothing for her." She used her sleeve to wipe a tear from her eye. "I just wasn't ready."

"Now that I think about it, I didn't exactly do anything for her either..." he replied.

"That was me too. I didn't want you to fuck her. She was right, I was so worried about you liking her more. I couldn't see past that. And now she's gone."

Just then her phone rang.

"Is that her?" Derek asked, hopefully.

"No," Amy said dejectedly. "Unlisted. Third time too. Telemarketers sure are persistent." The number wasn't in her contact list, and Jill's definitely was. Amy declined the call, sending it to voicemail.

"I'm so sorry, sis." Derek didn't know what else to say. He just held his sister as she cried into his chest.

--------------------

Amy and Derek spent the day cleaning their rooms and doing chores around the house. Derek did some yard work and cleaned the leaves from the pool. Amy helped by running towels through the laundry.

They decided it was easier to just not think about it too much.

So, there was with a little surprise when they heard a car door in their driveway around 6 pm.

"Did you miss me?" Jill happily greeted them, giving each a hug. She put large red paper shopping bag down near a table in the foyer. "Don't look please. It's a surprise, for your mom."

"I'm confused," Amy's body language indicated she wasn't thrilled. "You left without saying anything. I figured you were mad, and it was over." It was part statement, part question.

"I had to go to work. You two were sleeping soundly and looked so happy, I didn't want to wake you."

"But you didn't answer my calls. I texted like 24 times!" Amy held up her phone, demanding an answer.

"Yay! You did miss me!" Jill was giddy, hugging her new girlfriend who was still confused. "Sorry, I didn't realize until I got to work that I left my phone here. It probably ran out of juice too." Jill added. "I tried calling you from work, like 3 times, but you didn't answer. Did you check your voicemail?"

"What? No." The unlisted number! "Wait, where's your phone?" Amy asked her.

"I don't know, probably on your nightstand. You know, right next to the bed we all slept in..." Jill offered, trying to ease Amy's fears. "You know, I don't just do that with everyone. Even with tequila!"

"Speaking of which," Derek chimed in. "I'm sorry we didn't give you more, um... attention."

"Don't worry about it," Jill replied. "I mean, would I have liked an all-night, everything goes romp with you two? Absolutely."

"You're not, upset?" Amy was shocked that she misunderstood the situation.

"A little um, frustrated perhaps." Jill was honest if nothing else. "Look, we all have to be comfortable with what we're doing, and who we're doing it with. So, que sera, sera."

Derek raised an eyebrow, not knowing the phrase (nor Spanish).

"Whatever will be, will be."

Amy tried to explain: "It just all happened so fast. We were drinking and fooling around and next thing I know things were getting out of control..."

"Yea, that was awesome!" Derek chimed in. Amy punched him.

"Hey!" Derek grabbed his arm.

Jill looked at her, seriously. "Amy, I like you, in case you couldn't tell. I like you both," she looked over at Derek to ensure he wasn't left out. "But it's a free country. I won't make you do anything you don't want to do. So, if that's not your thing, and we all end up being just friends, then so be it."

"Just friends?" Amy wasn't sure what she wanted. She didn't know how to convey her feelings properly.

"I respect that Derek can't just do whatever he wants."

"Do I have a say in this at all?" He asked, more than a little disappointed.

"I mean, I wouldn't want my brother to just screw any girl he wants either. Not without my approval. Or my involvement." Jill pulled down her sunglasses and looked at Amy alluding to last night.

"Speaking of which," Derek added. "Our mom's not here, so we could go inside and um..."

"Down boy," Amy looked at him.

"Yea, your mom went to New York," Jill responded. "I saw her this morning. We had a nice, um, chat."

"So, what now?" Amy asked.

"Well," Jill looked at them. "Derek, is it true you're no longer grounded? Let's go have some fun and get some food. Anyone down for the boardwalk?"

--------------------

When the sun goes down, that's the boardwalk comes to life. There were rides and games. Big neon signs with flashing colorful lights advertised various food vendors and tasty treats. A local band played music next to the food pavilion.

Derek, Amy and Jill spent a couple hours playing various carnival games - contests of skill where people played to win prizes - mostly stuffed animals. Most seemed quite difficult to master. They tried their luck at the ring toss, throwing darts at balloons and even trying to knock down stacked milk bottles.

Their favorite was the game where you try to pop the balloon by shooting water into the clown's mouth. They could all play at the same time, but there were eight total players and a young boy down at the end kept winning. Try as Derek might, winning a prize for his lady friends so far proved elusive.

Then the girls got distracted by the cotton candy machine.

Derek took his shot with the game operator.

"Hey, how much would a guy normally spend trying to win a couple of those bears?"

"You'd have to master the shot *and* beat all the other contestants... you could probably spend $40 before you would win a couple of times."

Derek started pulling out his wallet.

"But the bears are medium prizes, and to get those requires two wins apiece - so that's four total. Eighty and I'll let you pick the colors."

Derek looked up at him. But he decided not to make anything of it. He slipped him the cash. "A pink and a blue please."

He caught up with the girls, surprising them each with one.

"Are you trying to get lucky with us?" Jill asked playfully.

"Can't blame a guy for trying!"

They finally located the pizza parlor, splitting a medium pie, eating happily as they watched the crowd.

"So," Jill said after eating two slices. "I learned two things when I spoke to Claire this morning."

"Claire?" Derek asked, curiously.

"Your mom," Jill teased him.

"I know her name. I didn't realize you were on a first name basis."

"Apparently," Jill continued, "she heard a woman screaming in the throes of passion last night."

"What?" Amy asked incredulously.

"She brought it up, not me."

Yea, um, I guess someone had a really good time." Amy blushed.

"The point being," Jill continued. "She thought it was me - with Derek. She asked if we were dating."

"Well, that would be a convenient explanation," Amy suggested.

"You'd think. But follow it through," Jill countered. "Then she'd expect us to actually go out on dates. And to see normal boyfriend to girlfriend behavior." She looked at them, but they just looked back - they weren't getting it. "You know, PDA?"

"Well, I can play the part," Derek said. "If I had to."

"Down boy!" Amy punched him again.

"Ouch!"

"That wasn't hard," Amy teased her brother.

"That's four times in the same spot!"

"Look, I don't want to play a big charade. Plus, I already have a boyfriend. So, I said it was you Amy, which was true." She let that sink in. "But that meant either you were screwing your brother..."

"No..." Amy was beside herself.

"Or that I made you scream like that."

"You didn't!" She thought she outed them to her mom.

Jill just looked at her.

"OK, so you did!" Amy giggled as she threw her napkin at her.

"Tell the truth whenever you can, that's my motto. This way, I don't have to worry about which stories I've told, or to whom."

"Oh my god, I'm so embarrassed," Amy put her hand to her forehead, trying to hide her face.

"Relax, this isn't the 1950's," Jill replied using Claire's words.

"Yes, but I wasn't thinking of telling my mother. She's such a prude!"

Jill looked at her a little more seriously. "Which brings me to the second thing. Your mom has slept with a woman before."

"What?" Both Amy and Derek asked in unison.

"I suspect she slept with my mom actually," Jill said thoughtfully. "Did you know they were college roommates? Last time was a few years ago I think."

"Holy crap!" Derek replied, his eyes wide.

"No, she's not like that," Amy said totally convinced she knew her mom better. "She's totally straight."

"Are you so sure? I nearly broke her down this morning."

Amy looked at her, shocked. She had to ask. "You didn't..."

"Can't blame a girl for trying," Jill said taking a sip of her soda and looking up playfully from the straw.

"I can't believe this," Amy was beside herself.

"What, she's a total MILF!" Jill said flirtatiously. "You've never thought of getting some of that?"

"No!" Amy threw another crumpled napkin at her.

"Your brother has," Jill replied.

"What the!" Derek said as they both looked at him for different reasons.

"I could tell by the way he watched her by the pool. Oh, he's a tits and ass man for sure."

"Well, she is beautiful," Derek replied. "And in that bright yellow bikini... oh man!" He shook his head, recalling the beautiful sight.

Amy hit him again, on the same arm, in the same spot again.

"Stop!" He laughed but it also really hurt.

"You're such a pervert!" Amy said to her brother.

"Says the girl who helped suck her brother off, then got pleasured by a woman while said brother fucked her from behind." Jill drove her point home.

"Sshhh! Not so loud!" Amy pleaded with her, looking around hoping nobody heard the exchange.

"Who wants ice cream?" Jill said as they rose and cleared the picnic table.

They walked towards the desert stand and waited in line for some soft serve. Jill went first, placing her order and paying the concessionaire.

Derek thought he heard some other young adults behind them.

"That bitch is such a tease." One said to the other, trying to be quiet but also trying to be heard.

"What did you call me?" Amy angrily confronted the college aged guy.

Derek and Jill turned and found Todd with a couple of his friends.

"The tease that won't put out."

"There's no need for that!" Derek countered Todd verbally.

"Out with your sister and her slut friend I see."

"Hey! Real men don't talk to women that way." Derek's voice grew firm, but he was still trying to not get into a physical altercation.

"Speaking of which," Todd retorted. "Becca says she's happy to finally have a real man."

"He's ten times the lover you'll ever be," Jill shot at him while clutching Derek's arm.

"Nobody's asking you, slut!"

"I'm so glad I broke it off with you. You're such a fucking asshole!" Amy threw the last of her diet coke at him. Todd had soda all over his face and his shirt.

"You bitch!" He was fuming and made a step forward with his arm raised.