Mixed Bag Ch. 02: Mixed Harder

"Roll over," she ordered hungrily.

Charlie did so without hesitation, rolling onto his stomach. In just a fraction of a second he felt Melanie crawl between his legs, spreading them out with her own fishnet-covered limbs. He could feel as she slid a newly-lubed up finger inside his asshole slowly. He winced slightly at the initial discomfort, but the more she fingered him, the easier it got, and soon she was pumping three fingers into his tight tunnel, before they suddenly disappeared.

He then felt her breasts press against his back as she lay atop him and a moment later, her cock began to work it's way into his lubed up asshole. He could feel that she'd lubed herself up as well and in no time she was buried deeply within him, causing him to groan into the pillow.

"Just as tight as the first time...fuck Charlotte, I love your cute little ass so much," she whispered, biting his earlobe as she began to pump into him.

Charlie gripped the sheets as Melanie fucked his ass, thankful for the pillow to muffle his loud moaning. It felt just as good to feel her thick shemale cock thrusting into him as it had when he was inside her. No matter what they were doing, Charlie realized he liked being Charlotte no matter what.

"Fuck baby girl, your asshole feels so good...and your cute little dolled up face looks too clean..." She whispered into his ear in a sinister tone. "I'm gonna cum all over that pretty face."

"Oh yes, please!" Charlie begged, wanting it just as much as she did.

Her hips slapped lewdly against his cheeks as she pumped harder and faster. A sheen of sweat was beginning to form on both their bodies as she thrust as deep as she could, burying her cock in Charlie's tight ass time and again until she felt her balls begin to tighten.

"Roll over!" She barked out, quickly withdrawing from Charlie's hole.

He happily obeyed and she crawled up, sitting on his chest as she pumped her cock, still shiny with lube. Charlie opened his mouth wide, wanting to again taste Melanie's salty spunk, and got his wish as it began to spray out over his face. One jet landed perfectly between his lips and he swallowed it quickly. Finally drained, she lay down on him and kissed him passionately, tasting a bit of herself on his tongue.

"That was so amazing, Charlotte. I can't wait to do this again," she said, panting.

"Me either," Charlie sighed happily.

Act III: Further Firsts

A short while later, Melanie dropped Charlie back off at home. They shared one last passionate kiss before Charlie headed inside, carrying the pink heels slung over his shoulder. It was fairly late; the house was quiet and everyone seemed to be sleeping, so he crept as steathily as he could up to his bedroom. After slipping inside and closing the door, he found Ashley laying on his bed in nothing but a pair of gray boyshort-style panties. She sat up, crossing her legs and smiling.

"Finally back? Jenna told me what you were up to tonight."

Charlie's cheeks turned pink again and he set the heels down on the floor, sitting on the bed next to his twin sister and absentmindedly picking at the hem of the cute pink dress.

"I really like being Charlotte," he said quietly

Ashley climbed into his lap, her smile growing wider as she lay her arms on his shoulders.

"You do make a sexy sister," she whispered, leaning in to kiss him softly.

Charlie moaned against her lips and returned the kiss, parting his own just slightly so that their tongues met ever so slightly. Charlie wrapped his arms around his sister's waist as they shared a loving embrace. As Ashley broke the kiss, she leaned over next to his ear and whispered.

"Charlotte...would you fuck me in the ass?"

Charlie's eyes went wide.

"W-What?" He asked in disbelief.

Ashley raised her head, gazing at him with her trademark pouty look.

"Mom and you both like it...so it has to feel good. I want to try it too...and I can't think of anyone better to try it with than sexy Charlotte."

"Are you sure?" Charlie asked quietly, even though he desperately hoped she'd say yes. His panties were already tight again. "It hurts a little at first."

"I don't care, Charlotte," Ashley said sternly, leaning over and nipping his earlobe before whispering hotly into his ear. "I want you to fuck me and get nice and wet, then I want to feel you in my ass."

This was all the invitation Charlie needed. They kissed again, this time more aggressively, just as he and Melanie had done earlier. Their tongues entwined as if in a battle to see who could claim the most territory within the other's mouth.

Ashley crawled out of his lap, shedding her boyshorts quickly. She pulled Charlie up by his hands and slid his dress off just as fast. He followed suit by sliding off the thong, leaving him in just the cute pink bra and thigh high black stockings. She eagerly crawled up onto the bed on her hands and knees and wiggled her behind at him invitingly.

Charlie crawled up onto the bed behind her and easily slid his cock into her pussy. She was dripping wet with excitement, so even as tight as she was, it was no challenge getting inside. Her pink muscles still clenched him perfectly as he began to slip in and out. Ashley groaned with pleasure, her nails digging into the sheets.

"Oh baby...your girlcock feels so good, Charlotte," she purred. She loved her new sister just as much as her brother, and couldn't wait to feel her in her ass.

Charlie was in heaven as well. Looking down, the sight of the pink bra and black stockings still clinging to his figure, as well as his throbbing cock pumping in and out of his sister's juicy cunt, was enough to drive him close to orgasm already. Sensing it though, he slowly slid out of her, taking a deep breath and waiting for the sensation to pass.

Once he'd regained his composure, he placed the head of his cock, shiny and wet with Ashley's nectar, against her asshole.

"Are you ready?" He asked quietly.

"Fuck me in the ass Charlotte, pleeaaaaase," Ashley begged in a singsong voice.

He very carefully and slowly began to push inside. Ashley grunted and he halted his advance, but when she said nothing, he continued to push forward. After a little work, the head popped in, and Ashley gasped.

"Fuck...it feels so big back there, bigger than usual."

"Are you okay? Should I keep going?"

"Yes, please don't stop."

Charlie placed his hands on Ashley's hips, pulling her back as he pushed forward, sliding another inch inside her. Again she grunted, but made no effort to stop in. He continued his advance, sliding another inch in, giving her time to get used to the feeling, before pushing even more. Finally, with one tug on her hips and thrust of his own, he was buried balls deep in his sister's tight ass.

He remained still for a moment, savoring this feeling. If her pussy was tight, it was nothing compared to this. It was almost painful, the vice-like grip around his throbbing cock. Ashley couldn't wait however, and slid her hips forward. Charlie watched in awe as she slid her asshole along his cock until only an inch or so remained inside and then slid all the way back, taking the entire thing back inside her tight ass yet again.

Charlie gripped her hips a little tighter and began thrusting himself now, slowly at first, groaning as he fucked his sister's ass.

"Oh god Ashley...your ass feels fantastic...nnnnhhh!"

"And your cock feels so amazing, Charlotte. Pleas keep fucking me, don't stop, please," she begged again.

As Charlie began to increase his pace, he held tightly onto her hip with his left hand, but carefully moved his right between them, and began to rub her clit in smooth circles. Ashley bit her lip to keep herself from moaning too loud, not wanting to wake up their parents.

"Oh my god Charlotte, you fucking slut, fuck me, rub my clit, ooooh god yesyesyesyesyes!" She rasped excitedly.

Charlie gripped her hip tighter to hold on as she thrust her hips back, meeting every one of his thrusts and driving his cock deeper inside her ass. Her anal walls contracted around his shaft, making him moan louder and pump faster, watching each and every time he disappeared into his sister's ass. He still couldn't believe how incestuous and kinky he'd become. He'd fucked both sisters and his mother, and dressed up in cute feminine attire and fucked and been fucked by a gorgeous shemale professor. How could things possibly get any kinkier, he thought.

The sight and feel of his dick disappearing into Ashley's puckered hole coupled with the thoughts in his head brought him to the brink or orgasm. He began rubbing Ashley's clit even faster as he thrust into her ass with every ounce of strength he had left before groaning loudly. With a few final, rough thrusts, he felt as if he came with the force of a shotgun, depositing his sticky seed deep in his sister's ass. Almost simultaneously, Ashley's body shook and her toes curled as she came as well, her juices dripping freely over his fingers.

Charlie slowly slid out of Ashley's ass and lay down on the bed on his side. Ashley rolled onto her side and snuggled up against him, spooning with him so that his sticky cock was cradled between her asscheeks. She reached back, pulling his arm to drape it over her, interlacing their fingers.

"Thank you so much Charlotte. That was amazing," she said sweetly.

"Anything for you, Ashley," Charlie smiled, kissing the back of her neck lovingly.

The two drifted off to sleep, snuggled up as lovers.

---

A day or so after Ashley's first anal experience, Derek and Julie were finishing up a long day of work. Julie didn't mind so much, because she had a surprise in store for her loving husband. On the way to the car, Julie fished the keys from Derek's pocket and kissed his cheek with a little giggle.

"I'm driving. I have a surprise for you."

"Oh? What kind of surprise?" He asked.

"You'll just have to wait and see, won't you?" She responded in a cheeky tone.

About halfway there, it became apparent where they were going. Derek raised a brow.

"Honey, are we going to your sister's?"

"She has something she wants to show you."

Derek went quiet for a moment, thinking. He'd always gotten along with his wife's sister. And she was rather attractive, too. Could she mean what he thought she meant? Had she decided to get her sister involved after all? He thought to ask but remained quiet, deciding to take the wait-and-see approach.

After several more minutes they arrived, and Derek didn't have to wait very much longer at all to find out if his ideas were correct. Julie let him in without even knocking, and led him to the bedroom, where Rachel lay on the bed, in nothing but a smile and a pair of black patent heels, one hand already busy at work between her legs while the other worked her chest.

She looked up and blew a kiss towards Derek with a wink, s inserting three fingers into herself, groaning in delight as she did.

"Surprise," Julie said as she began to unbutton Derek's shirt.

"Did you two..." He began to ask, unsure of how to finish his question.

"Eat each other out until we were screaming each other's names? Mmmm, maybe," Julie giggled, excitedly undressing her husband.

Once he'd regained his composure, Derek helped Julie out of her clothes as well, until just like her sister, all Julie remained in were her heels.

"C'mon baby, don't you want a taste of your sister-in-law?" Rachel asked in a husky voice, removing her fingers from her pussy and bringing them to her mouth, where she sucked them clean.

"Anything for family," Derek muttered, crawling up onto the bed between her legs.

Rachel purred happily as she felt Derek begin to eat her out. He wrapped his arms around her thighs as he pushed his tongue through her moist folds. He couldn't help but think that she tasted just like her sister.

Julie wasn't content to just watch however. She crawled onto the bed, nudging Derek to make him prop up on his side as he worked on Rachel's pussy. He was already hard from having a brand new cunt to play with. Julie licked her lips and took his throbbing cock between her soft lips, bobbing her head up and down slowly.

This caused Derek to moan, which carried vibrations deep into Rachel, creating a chain reaction and making her moan as well. She craned her head up, watching her sister's husband ravish her pussy while Julie eagerly sucked his cock. She squeezed her breasts, groaning at the sexy sight laid out before her, pinching her hard nipples between her thumbs and forefingers.

"Your man is just as good at eating pussy as you are, Jules," Rachel giggled, moaning again. "But I want to get fucked," she said, pushing herself into Derek's face.

Derek licked his sticky lips and glanced down to his wife, who released him from her mouth and smiled.

"Go for it babe. Show her how good that dick is."

"Yes ma'am," Derek said happily, as he climbed up to sit on his knees between Rachel's thighs.

She smiled wide, lifting her legs and placing her ankles on his shoulders. He slid forward, slipping his cock into her waiting lips. There was brief, lewd sound as he slid into her tight, sopping wet pussy, but it was overshadowed by the loud moan that escaped Rachel's lips.

"Ooooh Julie, we should've done this a long time ago. Your husband feels so, hnnngh, good!" Rachel groaned as Derek began to pump into her.

"You'll have to thank your niece, Ashley. She's the architect of all this," Julie said as she slid forward on the bed, leaning over and sucking on one of her sister's nipples.

Rachel ran her fingers through Julie's hair as she groaned. Derek had taken hold of her ankles, holding them firmly on his shoulders as he thrust into her roughly. He had been watching his cock disappear into her pussy each time, but now his eyes traveled to his wife. The kinkiness of seeing her suck on her sister's tits drove him wild and made him pump even harder.

"Mmmm, mmmm, fuck. FUCK. Give me that dick, Derek, oooooh just like that baby, fuck that tight pussy," Rachel cooed, egging him on. She glanced to Julie, speaking between further moans. "I'll have to give Ashley, nnnnhhhhh, a special thanks then."

"For now you can thank me for letting you fuck my husband," Julie giggled, as she quickly placed one leg over her sister's body and then slid up to hover just above her face.

"Mmmmm, oooh you slut. I love it," Rachel said, lifting her head and running her tongue along the length of Julie's slit.

"Oh my god.." Derek whispered, having an excellent view of his wife squatting over her sister's face. He watched excitedly, gripping Rachel's ankles tighter as he fucked her at an increasingly erratic pace.

The three of them were sweating and all in a perfect rhythm. Derek's cock slipped in and out of Rachel's cunt at just the right pace and depth, while Rachel's tongue was finding all the right places on her sister's pussy. Julie was the first to cum. She reached down, gripping Rachel's black hair between her fingers as she trembled and came, her juices trickling freely over her sister's tongue.

Once she'd stopped convulsing, she crawled off of her sister's face, leaning down to kiss her passionately. Derek excitedly watched as his wife's tongue invaded her sister's mouth, knowing full well she could taste herself. This brought him to the brink.

"I'm gonna cum," he announced, his own body beginning to shake with the impending force.

Julie grinned at Rachel and lay down on the bed next to her sister.

"Cum on our faces baby," Julie said hungrily.

"Oh fuck yeah!" Rachel added in.

After a few more hard thrusts, Derek pulled out, finally releasing Rachel's ankles and crawling up between his wife and her sister. He pumped his cock, sticky with Rachel's nectar for only a moment before spurts of hot cum began to escape. He sprayed the first few over Rachel's tits and face, before changing direction and letting Julie have the rest on her face and in her hair. Both women had their mouths wide open, catching a little bit of his spunk eagerly on their tongues. Once he'd finished, they kissed again, sharing what little they were able to capture before the pair licked and sucked his cock clean. Afterwards, the three lay on the bed together, snuggled up close.

"I think it's time to let the kids know what a slut their aunt is," Rachel said, looking between Julie and Derek excitedly, still trying to catch her breath.

"I bet they'd love that," Julie remarked.

"Four women for just two men? I like those odds," Derek chuckled.

Rachel and Julie both giggled.

Act IV: Continuing Education

One of the very few downsides of becoming a willing playmate in his incestuous family's fun for Charlie was that he was missing out on a lot of sleep. Regardless of all the fun he had with his sisters, mother, and even Jenna's shemale professor, he still studied hard for school, and as a result missed out on a lot of rest. And it was beginning to show.

His final class before lunch was one he usually excelled at, but currently his face was plastered to his desk, his mouth wide open as he napped unintentionally. His teacher had taken notice as well, especially when the lunch bell even refused to wake him.

Samantha Newton was kind to her students. At only 29, she was one of the younger teachers at Charlie's high school. She stood at 5'7" and was very curvy. Not exactly fat, but far from skinny as well. She had chocolate brown shoulder length hair that curled just slightly at the ends, and gentle brown eyes.

After the rest of the class filed out to head to lunch, she approached Charlie's desk and gripped his shoulder gently, shaking him awake. His head jerked up as he realized he'd been caught sleeping. Upon seeing the gentle look on Ms. Newton's face though, he relaxed slightly, rubbing his eyes.

"Charlie, you've been falling asleep a lot in class lately. Is everything alright at home?"

Charlie felt a strange pang of guilt hearing this question. Things were great at home of course, but he wasn't about to tell his teacher about how taboo things were in the Reynolds house. Instead he cleared his throat, nodded his head, and tried to sound convincing.

"Y-Yes ma'am."

He stood from his desk, almost immediately regretting it as he realized the sudden thoughts of his family had made him hard. Samantha had clearly noticed as well. She leaned against her desk, gripping the edge with her fingertips.

"Are you having...personal trouble, Charlie?" She asked, her eyes fixated on the bulge in his pants.

"N-No! I uh...it's um...I..." Charlie stuttered, trying to figure out an excuse. He thought of making a run for the door but thought better of it.

"Would you like me to relieve you? Would that make it easier to stay awake and concentrate in class?" She asked matter-of-factly.

"W-What?" Charlie stuttered again.

"You're a very smart boy, Charlie, and you're eighteen. If a little relief is all you need, I'd be happy to provide it. I'd hate to see your grades start slipping just because you're too horny to think."

Charlie gulped. Was this a trap? It couldn't be. She was asking so directly. He shuffled nervously. Samantha had apparently made his mind up for him however, as she walked to the classroom door and closed it, locking it as well.

"M-Ms. Newton?"

She sauntered back over to her student, who still stood beside his desk, in shock. She dropped to her knees and began to unbutton his pants. Charlie just stood frozen in place. First his sisters and mother, then Melanie, and now even his teacher? He was having difficulty believing just how lucky he was. He decided to stop fighting it though and took a deep breath as he felt his pants and boxers pulled down.

"Oh wow, Charlie. You have this nice, big dick, and you can't find someone to suck it for you?" Samantha said, wrapping her fingers around his girth and looking up at him as she began to pump it.