A Resort for Families

A few notes and acknowledgments before the good stuff: Thank you all for your patience! This originally was going to be a one-off, but I decided to make it a little series. I have one more chapter planned for Chris and his family, but I have some other projects I want to work on first.

Lastly, a few notes for readers. This story has a few new kinks that aren't all readers' cup of tea. Specifically, the first sex scene involves a pre-op transwoman, the second and third involve ass-to-mouth, and the third also features pegging.

----

Chris lay in his bed, still trying to make sense of what happened last night. He participated in an orgy, not something he ever thought he would be part of. Additionally, it was all family. He had sex with his aunts, mom, and sister.

While Chris' mind tried to come to grips with the night, his cock had its own mind. Replaying the events through his head brought his member back to life. He slowly started stroking himself, trying to ignore the dull pain resulting from his countless orgasms. He closed his eyes, picturing his mom on top of him. Her breasts were just inches from his face and shaking violently with each of his powerful thrusts.

Alexa stood outside his room, her ear pinned to the door as she listened to her brother furiously jacking off. His labored breaths and the sound of his balls slapping against his hand filled the otherwise silent villa. She bit her lower lip as she thought about her brother's thick cock. One hand slid down between her legs and she could feel how wet she was. She desperately wanted to get off but remembered everyone was already waiting for them at breakfast.

She pulled her hand out of her underwear, tasted herself, and then played spoiler. She threw the door open and abruptly jumped on the bed while Chris furiously tugged at his cock.

"C'mon! Get up! We're waiting for you!" She complained, bouncing on the bed to make his task impossible.

"Goddamn it Alexa!" Chris shouted as he tried to steady himself from her movements. "Fine, fine. I'm up."

"Hurry up, jeez. Didn't get enough last night?" Alexa asked as she looked at his shriveling member.

"That's the problem. I can't stop thinking about it, and once I do, poof. He's at full attention." Chris' cock sprang right back to life.

Alexa giggled at her brother's dilemma, "Well, get dressed. We're all waiting for you at breakfast."

Chris groaned as he staggered over to the dresser. Rummaging through the drawers, he settled on a tank top and khaki shorts. He had half a mind to forego clothes altogether but didn't want to spend his day maneuvering a constant hard-on.

--

"Could you give your favorite aunt a hand here?" Jenny asked Chris as she struggled to unzip her romper.

"Uhh, sure," he replied as he put down the puzzle he was fiddling with.

He walked over and slowly lifted his hands to the zipper, the blood rushing immediately to his cock at the thought of his aunt naked. As the zipper descended her back, her pale and slightly aged skin peered through the emerging gap. Chris had his suspicions during breakfast, but helping her undress confirmed it. His aunt opted to go without a bra during breakfast.

She shrugged the romper off and it fell to the ground, standing in nothing but a thong and her wedge heels. Chris stepped towards his aunt and wrapped his arms around her, grabbing ahold of her massive breasts and tweaking her nipples.

"Mmm, honey. That feels nice," she purred as his cock pressed against her backside.

Hoping for a morning quickie, Chris began to kiss her neck and moved one hand between her legs. She offered no resistance until his fingers pushed her thong to the side and began to dip into her wet folds.

"Hey now, none of that. Naughty boy." She pulled his hand away and turned around to wag her winger at him, giving him a sly grin.

"I can't help it, you're fucking hot," he replied and shrugged his shoulders.

"Oh, you men. You're all the same. You'd just have sex all day if you could," she chided him and rolled her eyes. "Now, if you really want to fuck me, let's have a date. Me and you, spending some quality time together. Romance me."

"Romance you?" He asked, confused by her request.

"Yeah. Be sweet, show me your sensitive side. Even though I'm your aunt, I'm not just some piece of ass. I want you to make me feel special," she replied as she slipped her wedges off and stepped away from his embrace.

She turned around and placed her hands on her hips. Chris stared at her nude form, his cock ready to burst. First, his sister interrupted his morning time, and now his aunt denied him.

"Right now is exactly what I'm talking about. You're ogling over my tits instead of even talking to me. Use your other head."

Chris bumbled for a moment, trying to think of what to say. "Well, what if..." he tried to think of anything that didn't involve bending her over the bed, "what if we go on a hike? We could even have a picnic out there."

She laughed at his suggestion, "Didn't get very far on the trail, did you?"

He blushed as she teased him for spying on her and his dad, "Yeah, the birds and the bees were just too much."

Jenny chuckled at his comment as she sifted through the dresser for an outfit for their "date." She opted for a simple dark red shirt and a pair of white running shorts that did nothing to hide the black thong she decided on. She didn't plan on anything happening on their excursion, but she couldn't pass up the opportunity to tease her nephew.

"How do I look?" She asked as she gave him a spin.

"Great, even though it's just 'exercise' clothes."

She grabbed her tits through the shirt and sports bra, giving them a firm squeeze, "Ugh, sports bras are always so uncomfortable with the implants. And don't even suggest going braless. I need something to keep you from ogling at me all day."

--

Chris and his aunt made their way down the path towards the infamous spot where he played voyeur and stopped.

"Hey, Aunt Jenny," he asked, looking off into the distance.

"Yeah, sweetie?"

"How did you get involved in this?"

"What do you mean this?" She looked at him puzzled before following his gaze. "Oh, you mean that? Well, it started when your mom and I were in college. As cliche as it sounds, we both went to the same Halloween party and ended up in a threesome together."

"Wait," Chris interrupted her, "you mean you and Mom started all of this?"

"Kinda," she replied and continued her story as they walked along the path, "Neither of us realized who the other person was, and as a freshman with a new sense of freedom, I was curious about having sex with another woman.

"Your mom and Uncle Mark had been flirting pretty heavily all night and since we were on a 'break' he thought the best way to get back at me was to fuck my sister. He just wasn't expecting me to interrupt them, he thought I was going to storm off crying or something.

"I don't know if it was the alcohol or what, but I screamed something about her not knowing her way around a cock and then just joined in. They were both in such shock I don't think they realized what exactly just happened. Next thing I know all three of us are naked and he's taking turns fucking both of us."

"We never did anything directly until a few years later, and that was actually Sarah who opened that door."

Chris was speechless and then everything began to click. That's why they always seemed to have "late nights" during family gatherings. They weren't catching up or whatever excuse they fed him and Alexa. They were fucking each other.

"I bet you want to know that part of the story, but that's where my part ends. You'll have to ask your Aunt Sarah what made her want to cross the line."

"But enough about that, tell me. What convinced you to take part?" She turned the table on her nephew.

"Well, Aunt Sarah kinda forced my hand technically," he replied, drawing a laugh from Jenny.

"That's fair. But once you discovered the truth, you kept going. So, why?" She pressed him again.

Chris paused, trying to think of an answer other than he always fantasized about the women in his family. Their womanly frames always appealed to him, they had shape, not another stick-figure model filled out with plastic surgery. Aunt Jenny was the closest to that, but she didn't have a comical "bimbo" shape.

"I guess it was the idea of being able to explore ourselves, with no judgments. We're all adults, we can decide right and wrong. And if we're all OK with it, then I don't see anything wrong," he replied.

They continued to chat as they made their way through the forest. With just the two of them and no interruptions, no topic was off-limits. Jenny told the story of the first time she shared her husband and the first time she was shared. Chris opened up about his most recent startup failure. He tried to dodge some of her questions, but she knew her nephew too well to let him weasel his way out. She forced him to relive the investigation and how severe the fallout was. Chris almost broke down several times during the retelling, but a soothing hand squeeze settled him each time.

They fell silent for a while. Jenny didn't want to push Chris any further and ruin their date. She listened to the birds chirping and wildlife scurrying off in the distance. Chris didn't need to say anything, Jenny could see the internal struggle of her nephew.

He finally broke the silence, "Hey Aunt Jenny?" he asked.

"Yeah, honey?" she replied.'

"Thanks."

She hugged him, holding him tightly, "Of course. Everything is going to be OK, trust me, honey." She released him and rubbed his shoulders, "Now c'mon. There's a gorgeous waterfall and swimming hole at the end of the trail."

He returned her smile and took her hand, giving it a tight squeeze before they continued down the last bit of the trail.

--

Chris dropped his backpack on the sandy bank and began to set up a little spot to relax. While he laid out the towels, Jenny pulled off her shirt, exposing her large breasts to the bright sun. The rest of her clothes followed and she placed her clothes in Chris' backpack. Busy setting up their little encampment, Chris was completely oblivious to his aunt's state of undress. It wasn't until she stepped into the water and let out a yelp he noticed her.

"Holy shit, that's cold," she cried, quickly retreating from the water, having only made it knee-deep.

Chris looked up at her cry, his gaze immediately fixating on her large breasts bouncing freely with each step. His cock stiffened as he watched her, paying particular attention to her hard nipples and well-trimmed bush. Relishing in this new era of familial intimacy, he freed his cock from his shorts and began to stroke it.

Jenny rolled her eyes as she made her way to her nephew and laid out on the blankets. "You're insatiable," she commented and closed her eyes to bask in the sunlight, "I'm just naked, not even doing anything sexy."

Chris shrugged and continued to stroke his cock, "You're hot."

Jenny propped herself on her elbows and stared up at him, slowly spreading her legs. "It's not like I'm sitting here, my legs spread open for you." She shifted onto her left arm and slid her right between her legs and continued to egg on her nephew, "Rubbing my clit, getting my pussy all wet and ready for my nephew's big hard cock." She closed her eyes and dipped her middle finger in, drawing a low moan from her.

While the two lovers played, another hiker wandered into the area and quickly spotted the two. Not wanting to disrupt the pair, she ducked behind some bushes to play voyeur. In her rush to hide, she stepped directly into a bramble of twigs. A loud snap caught Jenny's attention, interrupting her tease for a moment. Jenny could see the edges of the woman's hat peeking outside the edge of the bush. She regained her focus and escalated her teasing.

Jenny sank two fingers deep into her pussy and began to finger herself in earnest, "Mmmm, just imagine that big hard cock buried deep in my pussy."

Chris groaned as he watched his aunt feverishly masturbate in front of him, "Oh fuck yeah Aunt Jenny."

"You like watching your aunt give you a show?" Jenny moaned, letting their spy know her cover was blown.

"I do. You're so fucking hot," Chris replied, unaware of the other participant.

Jenny stopped fingering herself, and pulled her fingers out of her pussy, "It's OK, honey. You can come out," she shouted towards the trailhead.

Chris whipped around to see a petite woman emerge from behind a bush and quickly tried to tuck his cock back into his shorts. It didn't help much as his throbbing cock still pointed straight out forming a massive tent in his shorts. Jenny continued to lay there, undisturbed by the voyeur who slowly and sheepishly made her way over.

When she was close enough, Jenny broke the silence, "Enjoy the show?" She asked as she wiped her pussy coated fingers clean on the blanket, not bothering to cover her nude form.

The intruder's face was beet red, "I-I-I'm sorry," she stammered, "I didn't mean to"

Jenny cut her off, "You're just enjoying a hike, you couldn't have expected to see the birds and the bees in action. You don't have to apologize."

The woman smiled and met Jenny's eyes for the first time. "I-I'm Lilly," she said, getting her nerves back.

"Nice to meet you Lilly, I'm Jenny and this is Chris." He managed a nervous wave as he continued to hide his boner from the stranger. "That's a pretty name, by the way. So what brings you out here, Lilly?" Jenny asked before sitting up and crossing her legs.

"Oh, I just wanted to go for a hike today. It's gorgeous here," Lilly replied, her bright and bubbly personality beginning to show.

"It really is. Come, take a seat with us and hang out," Jenny patted an empty spot on the blanket. "You too Chris. Yes, your cock is hard. Big deal. Not to be presumptuous, but I assume you've seen a hard cock before?" Jenny asked.

Lilly giggled and nodded her head as she took a seat near Jenny. "Many times. If I'm here, I'm staying at the resort."

Chris shrank into himself a bit as he joined the women, doubly embarrassed.

"Funny you mention the resort, but you're out here alone," Jenny commented as she dug around the backpack.

"Oh, my..." Lilly paused, "boyfriend is back at the resort. He likes to hear about my day. Especially once I'm 'warmed up' as he likes to put it."

Jenny gave her a knowing look, "You're into older men aren't you? Old enough to be your dad?" Jenny emphasized "dad" and then turned her gaze to Chris, who perked up at his aunt's subtle accusation.

Now, it was Lilly's turn to shrink in embarrassment, "And older." She admitted as she pulled the straw hat off and tried to hide her bright red face behind it.

Jenny gave her an assuring pat on the leg, taking notice of the collections of tattoos, "Oh, those are nice."

Lilly looked down while Jenny traced her finger over the outline of her tattoos. She started at the floral that began on Lilly's foot and ran up her shin. "Oh, that tickles," Lilly commented.

Jenny smiled and caught a glimpse of Chris out of the corner of her eye. He continued to sit in silence and took a back seat to the plan she put in motion.

"How many tattoos do you have?" Jenny asked, her fingers dancing across a mandala accented with mystic symbols that covered the entirety of Lilly's thigh and beyond. Lilly's shorts covered the remainder and blocked Jenny's fingers.

"I lost count, maybe 12-15? But a few of them are big," Lilly purred.

"Can I see them?" Jenny asked, tracing her finger up the woman's leg and picking at the hem of her shirt.

Lilly looked at Jenny's fingers sliding under her shirt and lifted her arms, allowing the mature woman to peel the shirt off. Jenny saw the pattern continue up Lilly's ribcage as she peeled the young woman's shirt off. Sitting there in just a white sports bra and her shorts, the last of Lilly's tattoos were uncovered: a space-themed sleeve on one arm and a nature-themed sleeve on the other.

Sitting across from Lilly, Chris gestured to her chest, "Oh, and there's more too." The white material did little to hide the dark outline of her areolas and her nipples. At the center of each, a small stud pressed against the material.

Lilly blushed and pulled her arms over her chest to cover them, "That was supposed to be a surprise." She hooked her thumbs in the elastic and pulled the bra up, freeing her massive breasts. Her breasts had the same perfect roundness as his aunt's, leading him to assume her "boyfriend" got her implants as some kind of gift. Chris could only gaze at her nipples, the pink enamel bulbs on each end contrasting against Lilly's olive complexion.

Jenny crouched back down next to her and kissed her immediately. The sudden engagement caught Lilly off guard who froze in the older woman's embrace. Jenny used the opportunity to hold the younger woman's head in place as she pressed her tongue into Lilly's mouth. Their tongues immediately began to wrestle, each of them moaning as they embraced.

While they kissed, Lilly reached out to tease Jenny's hardened nipples. In response, Jenny released Lilly's face and broke their kiss. Instead, Jenny kissed her way down Lilly's neck and chest until she latched onto one of her nipples. She used a free hand to clasp onto the other nipple and tweak it.

"Oh, mmmm! Yes!" Lilly moaned out as Jenny assaulted her overly sensitive nipples.

Chris stood there in awe as these two gorgeous women embraced in front of him. His cock regained its full rigidness and threatened to burst through his shorts. He quickly stripped down, leaving his clothes strewn about the area as he hastily tossed them aside. Wrapping his fingers around his thick member, he started slowly stroking it.

Lilly looked over to see Chris, biting her lower lip as Jenny continued to tease her nipples. "Mmmm, it looks like Chris wants in too."

She used the distraction to free herself from Jenny's grasp and began crawling on her hands and knees over to Chris. "Want me to help you with that," Lilly asked, positioning herself with his cock inches from her face.

Chris stopped stroking his cock as a massive bead of precum dripped out and fell on the blanket. "I'd love it," he replied.

Lilly needed no other encouragement as she grabbed the base of his cock with a firm grasp and guided the thick member into her mouth. She held the head of his cock just past her teeth for the first few moments, flicking her tongue against the sensitive dome. Each time she pulled her tongue across the bottom, his cock twitched and rewarded her with a small spurt of precum.

"Oh fuck yeah, Lilly. This feels so good," he groaned and placed his hands on the back of her head, forcing her to take more of his cock.

Her hand on the base of cock stopped him from pushing her head down to the base. Lilly began to bob her head up and down on his cock, drawing a sharp groan from Chris. Lilly let go of his cock as he rewarded her by pressing her head further onto his shaft.

With her nose buried in his hips, Chris began to thrust his hips to eagerly fucking her face. Lilly opened her throat to allow Chris to assault her face. His balls slapped against her chin adding to the sounds of Lilly's sputtering.

Feeling left out of the action, Jenny crawled over to the pair, wrapped her hands around Lilly's bare chest, and began to pinch and tweak the young woman's pierced nipples. Lilly shifted on her knees at the new sensation and tried to moan around the thick shaft hammering the back of her throat.

Seeing his aunt join the fun, Chris pulled his cock from Lilly's mouth. Jenny let go of Lilly's nipples to wrap a hand around Chris' spit-covered cock and began stroking it. Lilly scooted out from in between the two to give Jenny room to take her place. Jenny wasted no time impaling her mouth on the thick tool of her nephew. Using her free hand, she vigorously rubbed her clit at the same time.