Mixed Bag Ch. 02: Mixed Harder

"Baby, I'm close..." He tried to warn her.

Ashley didn't slow. Quite the contrary, she picked up the pace, bouncing her head faster and faster, becoming a blur over his dick. Derek moved his hand from her shoulder into her silky hair and groaned again, curling his fingers against her scalp as he began to cum. Ashley moaned as she felt his warm, salty spunk splash over her tongue. Only then did she slow herself, swallowing every last drop before finally sitting back on her heels and giggling, wiping her mouth with the back of her hand.

"Thank you, baby," Derek said, taking a deep breath.

"We're not done yet, daddy," Ashley said coyly, quickly standing up.

She sat on the edge of his desk, hiking her skirt up around her waist and pulling aside her white cotton panties, revealing her tight pink slit, already moist.

"Fuck me before you get soft, daddy, please," she begged, batting her eyelashes.

"Anything for you, baby girl," Derek said, standing from his chair.

He stepped forward and kept Ashley's panties held aside so she could place her palms on the desk for balance, before slipping his still-hard cock inside her. Her tight, wet walls sucked in every inch as he slid within, making him groan with absolute pleasure. Though Julie and Jenna were tight, they had nothing on Ashley's vice-like grip.

"Ooohhh, fuck me daddy," Ashley repeated, digging her sparkly-pink nails against the desk as her father began to thrust inside her.

Despite his first orgasm, Ashley's tight, wet cunt kept him hard as can be as he pumped his hips, driving his thick shaft deep inside her each and every time. She began to moan, and Derek kissed her passionately, muffling her noises.

He rested his forehead against hers after the kiss, continuing to thrust into her oh-so-tight crevice, whispering as he did.

"Have to, mmmm, stay quiet, so no one hears us, okay?"

"I'm sorry, daddy. Mmmm...you just...feel...so...GOOD," Ashley said, the last word intentionally louder than the rest.

He kissed her again to quiet her once more as he continued to thrust into his daughter. Her inner walls clenched him upon every entry. They both moaned into the kiss, exchanging hot breaths as their tongues danced together and Derek pumped faster.

His movements became erratic as he neared completion. Their kiss grew even more passionate as his thrusts became harder and more primal. Ashley nearly screamed against his lips as her entire body shook with climax. Her nectar trickled down his cock, over his swaying sac as he gripped her thighs tightly.

Her inner walls clenching him even tighter sent Derek over the edge. With a few final, powerful thrusts, he shot several jets of cum deep into his daughter, before finally breaking the kiss, panting. Both of their chests heaved as they fought for breath.

Derek slowly stepped back, sliding his soaking wet cock out of his daughter as she carefully slid off the desk. She slid her panties back into place and brushed off the front of her skirt before kissing Derek's cheek and smiling sweetly.

"Thanks, daddy. I'll see you at home,"

Before he could say another word, she skipped out of the office. He flopped down into his chair, shaking his head, but still smiling all the same.

---

Ashley wasn't the only daughter feeling incredibly horny. After she'd finished her classes for the day, Jenna went to see her favorite professor, Melanie Monroe. Melanie was a shemale with jet black hair, green eyes, and the perfect combination of tits and a cock. Jenna had first had sex with her just after Ashley began seducing the family. After that, she included Melanie in the family fun with her siblings, even dressing up Charlie as a sexy girl named Charlotte for her to have fun with.

Jenna knocked on the door of Professor Monroe's office. She shifted her weight from one foot to the other while waiting. As it was a fairly hot Spring thus far, she'd dressed herself in only a pair of denim short shorts and a tight red tee with the Kit-Kat logo across the front.

"It's open," came a familiar voice.

Jenna smiled and quickly stepped inside, closing the door behind her. Melanie was seated behind her desk wearing an olive green blouse, black pencil skirt, black thigh high stockings, and sensible black heels. As she looked up from her paperwork, a huge smile crossed her face.

"Well if it isn't my favorite student."

Jenna laughed as she locked the door and then approached the professor's desk.

"Here to see her favorite teacher," she said sweetly.

"Well aren't you just the most thoughtful pupil," Melanie laughed as she settled her papers and stood up, brushing down the front of her skirt.

"I've missed you. And I'm not the only one," Jenna admitted. "Ashley and Charlie have too."

"Mmm, how is Charlotte? I've missed you and Ashley too but that was quite the experience," Melanie said thoughtfully.

Jenna pouted.

"Awww, you like Charlotte better than us?" She asked playfully.

"Oh shush," Melanie snorted and closed the distance between herself and Jenna, wrapping her arms around the other's waist.

"All three of you are perfectly kinky little sluts. But there's something about Charlotte being so feminine and accepting of that that makes me quiver."

"Well Charlie does make a pretty hot girl. I guess I can't blame you," Jenna remarked with a smiled.

"You should set up a date for us, just me and her this time. What do you say?"

"What do I get out of it?" Jenna asked with a grin.

"Aha, she likes to bargain, eh?" Melanie smirked.

The professor sank to her knees, quickly unbuttoning Jenna's short shorts. She tugged them down along with her panties, leaving them around her knees as she licked her crimson-painted lips.

"This is what you get out of it," Melanie said with a wicked smile.

She sank her teeth into Jenna's thigh, which made her gasp and place a hand on the professor's head. This made Melanie giggle, before she kissed a trail up to her warm, waiting slit. She flicked her tongue out across Jenna's clit and then planted a soft kiss upon it, smiling up at her student seductively.

Jenna moaned and gripped her fingers in the professor's jet black hair. Seeing the gorgeous shemale look up at her was so incredibly sexy. Just the glance alone made her knees buckle.

Melanie wasn't content to make her happy by a quick peek alone though. She drove her tongue deep into Jenna's heated pussy, savoring the nectar as it washed over her tongue. For as much as she loved to see a man feminized, she also loved women just as much. Being transgender herself, she didn't care who she was with; in the end, as long as it felt good (and tasted good, in this case,) it didn't matter to her.

She slid her tongue through the soft, moist folds. Jenna had the perfect bittersweet flavor and she couldn't get enough of it. She wriggled her pink muscle to and fro, collecting every last drop of moisture she could, enjoying the heat that washed over her face as she worked between Jenna's perfectly toned thighs.

Jenna's knees were trembling now as her sexy professor worked her magic. Her nails scratched over Melanie's scalp as she moaned, nibbling her bottom lip to stifle herself so she didn't grow too loud.

Melanie dragged her tongue through the wet, pink slit up to Jenna's super sensitive clit, wrapping her lips around it when she knew her student was near. Jenna thrust her head back, golden strands billowing over her shoulders as she groaned loudly and her entire body shook. She grew wetter as her orgasm struck, and Melanie hungrily lapped up every bit of the juices offered to her, before licking her lips happily and standing up.

"Was that acceptable payment for a date with Charlotte?" She asked, her chin shiny with Jenna's cum.

"Payment in advance, I like it," Jenna laughed, stepping forward to kiss Melanie passionately, tasting herself upon the other's lips and tongue.

"Want me to return the favor?"

"My panties are pretty tight, but I'll be a good girl and save it for Charlotte."

"Awww, alright then," Jenna pouted again.

"Don't you worry. I won't forget about you and Ashley," Melanie smiled, reaching behind Jenna and giving her a firm swat on the behind.

Jenna jumped and laughed, finally reaching down to pull up her panties and shorts.

"I'll give you a call when I talk to Charlie, then."

"It's a date."

---

Jenna practically rushed from college back to the Reynolds' family home. Though she stayed at a dorm on campus, she wanted to see Charlie personally over the matter. When she finally arrived, she found her brother studying in his bedroom.

"Hey Charlie," she said sweetly, entering his bedroom and closing the door behind her.

"Oh hi Jenna," Charlie said, setting his pencil down and rotating in his desk chair to face her. "What's up?"

"Remember my professor, Melanie?"

Immediately Charlie's cheeks turned pink.

"How could I forget her?" He asked breathlessly.

"She wants to see you again. Just a little date, her and you...as Charlotte. What do you say?"

Charlie pondered for a moment. Before that fateful night, he had never once considered dressing up, becoming a girl or being with anyone but a woman. But he thought back to how entirely hot the whole ordeal made him. Everything from wearing soft, feminine clothing, to getting fucked and fucking a gorgeous shemale in the ass made his cock twitch. He nodded his head rapidly.

"I'd like that," he replied, somewhat shyly.

"Great!" Jenna said excitedly. "How about tonight?"

"T-Tonight?" Charlie asked, not expecting it to be so soon. "I guess so."

Without another word, Jenna slid her cell from her pocket and called Melanie, who answered after only a few rings.

"How's my favorite student doing?"

"Excellent! Charlotte is so ready to date you, and tonight, too. How's that for results?"

"Seems like I owe you a little more than one orgasm the next time, then. How about I pick him up at seven?"

"I'll have him all dolled up for you."

Jenna hung up and slipped the phone back in her pocket with a huge smile spread across her face. Charlie was still sitting in his chair, blushing at the thought of dressing up and being with Melanie again.

"She really likes me...huh?" He asked quietly.

"She does. You make such a gorgeous Charlotte, who wouldn't?"

Charlie's cheeks went a deeper shade of red but he said nothing.

"Go have a shower and a shave; let's get you nice and pretty," Jenna said with a smile.

Charlie did as instructed, taking a nice hot shower and making himself silky smooth before returning to his bedroom, where he found that Jenna had already laid out clothing and makeup for him across his bed. He shyly slid the towel off and hung it on the back of his desk chair, and Jenna giggled, reaching out to cup his dick and balls.

"If you didn't need to save yourself from Melanie, I could so fuck you right now."

Charlie's cheeks turned pink again and this made Jenna laugh again.

"Even with everything we've done, I can still make you blush?"

Charlie nodded his head as he stepped closer. Jenna had picked up the first article of clothing; a sheer black stocking with a four inch lace top. Charlie lifted his leg and she carefully rolled it up, until it fit snugly around his thigh. Already feeling the soft material on his leg, his cock gave another twitch, and Jenna laughed again as she began rolling up the second stocking.

"You really like becoming Charlotte, huh?"

"It feels good..." Charlie responded quietly.

Jenna smiled as helped him slide up the little pink thong she'd picked out for him up his legs, letting it fit snugly between his cheeks and over his cock and balls. He was nearly fully erect now, feeling the silky material against his shaft.

"I'm gonna have to enjoy some time with Charlotte myself, sometime. I hope you don't mind," Jenna cooed.

Charlie nodded his head eagerly as she slid the straps of a matching pink bra over his shoulders, clasping it in the back. It was fairly well padded, giving him the appearance of a very small but perky chest. Finally, she helped him slide into a cute pink a-line dress with a ruffled skirt that went down just above his knees.

Jenna took Charlie by the hand, leading him to the bathroom and letting him look at himself in the mirror briefly before applying makeup. She applied just a touch of pink lipgloss and blush to match his outfit, then finished with just the right amount of smokey eyeliner and shadow. Then she styled his hair into a cute pixie style to give him an even more feminine appearance. For the second time in his life, Charlie looked in the mirror and saw not himself, but the gorgeous and virginal-looking Charlotte.

"I'm so beautiful..." He said breathlessly.

"Yes you are, Charlotte," Jenna smiled.

They both headed back to the bedroom, where as a finishing touch, Jenna helped him slip on a pair of three-inch patent pink heels.

"Now be a good girl. No touching yourself until your date with Melanie," Jenna laughed.

Charlie whimpered. His thong was already stretched taut.

--

Finally seven o'clock rolled around and Melanie arrived right on time. Jenna saw Charlie out the door, giving him a pat on the behind as he clicked his heels across the driveway, carefully holding the hem of his dress as he sat down in the professor's passenger seat before closing the door.

"You look so lovely, Charlotte," Melanie said sweetly.

Charlie looked over Melanie. She was dressed in a sexy little black dress that barely covered her thighs, as well as thigh high fishnet stockings that he could easily see the tops of, as well as the links leading from them that surely led to a garter belt. On her feet were strappy five inch stiletto heels. She leaned over and gave him a soft kiss, before putting the car in drive and heading towards her home.

He couldn't stop staring at her thighs, seeing the hem of the oh-so-short dress and the tops of her stockings. He licked his lips excitedly, and Melanie laughed, seeing this from the corner of her eye.

"Don't be shy, Charlotte. Go on, if you want," she offered in a gentle voice.

"R-Really?" Charlie asked, gulping.

"Really," Melanie reassured him.

He reached over, running his fingertips along her stocking tops, nibbling his bottom lip shyly. It only took a few moments before he grew bold enough to slide her dress up though, finding a black lace tanga stretched tight around her thick bulge. He carefully slid the garment down enough for her sizable cock to spring free, and then wrapped his fingers around it and begin to pump lightly.

"Oooh Charlotte, that feels nice," Melanie purred happily, clutching the steering wheel a little tighter.

Charlie smiled, feeling a little more bold as he began to pump it faster. Precum trickled over his fingers and he eagerly lifted his hand to his mouth, licking them clean. This made Melanie laugh again.

"Just like your sister...you're such a little cumslut, Charlotte."

Charlie decided to prove how true this was. He carefully leaned over in his seat, slipping his head beneath Melanie's arms and wrapping his lips around the head of her cock. She moaned loudly, her knuckles turning white as she struggled to concentrate on the road.

Charlie slid his lips down further, swallowing as much of Charlotte's girlcock as he could, loving the feel of the smooth skin and salty precum on his tongue. He pushed his pretty pink lips up and down as much as he could comfortably take, messily drooling over the gorgeous shemale's rod.

"Your mouth feels just as good as I remember it Charlotte...oh baby, I won't last long if you keep that up," she warned.

This made Charlie even more excited. He was eager to taste her cum again, and so he bobbed his head faster, wincing and trying to suppress his gag reflex so he could feel her even deeper in his throat. His spit trickled down his chin and over her cock, down through her tanga and over her smooth sac as he worked his head rapidly.

"Oh baby, here it comes!" Melanie announced, nearly swerving off the road.

She thrust her hips up from the seat, pushing her cock deeper into Charlie's mouth as she began to cum. Charlie excitedly accepted the spray of salty spunk into his throat and across his tongue, swallowing all of it down. He sat up, adjusting Melanie's tanga and dress before wiping his mouth and smiling happily.

"I'm going to ravage you so much you're going to limp home," Melanie remarked with an evil grin.

Charlie just smiled happily.

After a few more minutes they finally arrived at Melanie's place. The two locked lips before they ever even made it to the door, kissing passionately and running their hands all over each other's bodies, carefully walking across the drive on their heels and to the front door. They didn't even halt their make out session as Melanie struggled to put the key in the lock. Once she'd managed to do so, the door practically flung open and was slammed behind them as they quickly made their way to her bedroom.

Their tongues intertwined every which way as they carefully maneuvered over to the plush king size bed. When they finally reached it, Melanie shoved Charlie down onto the covers so hard he bounced slightly. He gasped, looking up at her as she quickly moved to the nightstand. His eyes widened as she shed the little black dress, revealing a sexy black corset with lace trim and the garter belt her fishnets were connected to. As she grabbed a bottle of lube from the nightstand, he quickly followed suit, shedding his dress, leaving him in just his thigh highs and the pink bra, thong, and heels.

She moved to the foot of the bed now, excitedly slipping out of her tanga, letting her cock spring free, which had already hardened again from their heated kissing. She then grabbed Charlie's thong, sliding it down his legs and carefully over his heels, dropping it on the floor with her own panties. With both of their dicks now free, she climbed up onto his thighs and squirted a good amount of lube into her palm, before wrapping her hand around his cock and pumping it up and down a few times.

"I want you to fuck me first this time, Charlotte. I'm so worked up after that perfect blowjob you gave me, I need to feel you inside me," she commented, noticing his eyes widen when she began to lube him up.

Melanie closed the cap on the bottle of lube and set it on the bed next to them, slipping one finger, then another into her ass to use up the remaining lube on her fingers and loosen herself up for Charlie. After a few seconds of this, she slid up his thighs, making both of them moan at the wonderful friction created by their stockings rubbing together. She carefully positioned his cock at her entrance and then slid down slowly. They again moaned in unison as his cock disappeared inch by inch into her tight backdoor.

Finally she came to rest with him buried fully inside her. She smiled down at him, reaching up and pulling down the top of her corset to reveal her breasts. He eagerly reached up, cupping and squeezing them in his palms as she began to ride his cock, sliding all the way up until he nearly popped out before lowering her hips to take the entire length back inside. Her anal muscles clenched his cock so perfectly and tightly, Charlie knew it wouldn't be long before he came.

His mind was in an overload of passion. Her breasts felt so soft in his palms as he continued to grope them, although her nipples were hard as could be. As Melanie began to bounce faster on his throbbing cock, he began to roll her nipples between his thumbs and forefingers, arching his back off the bed with a loud moan.

'M-M-Melanie," he whimpered.

"Cum for me baby. Fill my ass with your cum, Charlotte. Please baby, mmmm!" Melanie moaned shamelessly.

Hearing these lascivious words were enough to send Charlie over the edge. He arched his back again as he began to cum, true to Melanie's words, filling her ass to the brim with his hot, thick cum. Once he stopped pulsating, she slid off his cock and shook, her knees still shaky.