Mixed Bag

"Ohhh fuck you two, I'm about to cum," Melanie announced, pumping faster.

Ashley and Jenna looked at each other, and in tandem, they found themselves saying what their mother had earlier. "Cum on our faces."

"Oh shit," Melanie moaned, this making her even hotter. As she felt herself on the brink, she slid her dick out of Ashley's tight cunt and pumped it with her fist until jets of hot cum splashed across Jenna and Ashley's faces. The sisters kissed, cleaning each other off before they took turns slurping Melanie's dick into their mouths, cleaning it off as well. The three of them collapsed on the bed, spent, snuggled together.

"Fuck, you two...just...fuck," Melanie said, unable to think of anything else to say.

They all lay catching their breath for a long time, before Ashley wondered aloud. "I wonder if Charlie would like her."

Jenna rolled on her side to look at Melanie and Ashley. "I dunno. It'd probably be weirder for him than it is for us."

"To be honest," Melanie spoke up, "I kind of have a thing for crossdressers. I'm bi but I lean more towards girls, but guys in drag get me worked up too. Especially the believable ones."

Ashley giggled. "Charlie does have a pretty petite figure. I bet we could convince him to join in."

"You guys fuck your brother too?" Melanie asked, surprised.

"And mom too. We're a very close family," Jenna laughed.

"I suppose so. But hey, if all this can continue, you won't find me arguing."

"Then it's settled. We'll talk to Charlie. Come over again tomorrow night," Ashley said excitedly.

---

Julie and Derek had plans to drive out to visit her sister on Saturday, so Ashley knew the three siblings would have the house all to themselves again. She waited until their parents had left, gotten together with Jenna, and together they entered Charlie's room. He was as usual sitting at his desk, studying. When he heard them come in though, he closed his books and spun around in his chair.

"Well if it isn't the two best sisters a guy could ask for," he said sweetly.

Ashley and Jenna looked at each other and grinned.

"We're so happy to hear you say that," Ashley chimed.

"Why? What's up?" Charlie asked, raising a brow.

The two girls came over to him and knelt down, each rubbing one of his thighs teasingly.

"Well we have this friend who likes boys in drag...she'd just love to get with you."

"D-Drag? You want me to dress like a girl?" Charlie said, fidgeting in his chair as his sisters continued to rub his thighs. His cock was already getting hard and pressing against his pants.

"You used to let us play dress up when we were kids. It wouldn't be so different. And you get to fuck all three of us. Doesn't that sound hot?"

"It...it does actually. I guess we could try it," he agreed.

"Great!" Ashley exclaimed happily. "I'll get him ready, you call Melanie," she told Jenna.

Jenna left to go to her room and Ashley brought Charlie to hers. She had Charlie strip out of his clothes as she gathered things for him to wear. Being twins, although not identical, they were still about the same size. Charlie's body was mostly hairless and he had a lithe figure, so Ashley knew it wouldn't take much work to turn him into the hottie Melanie was expecting.

First she had him put on thigh high white stockings. She realized how sexy they were, seeing Melanie in a black pair, and had loved the feeling of them against her body. She helped him slide them up his legs. She then had him put on her white lace garter belt, which she clipped the stockings to.

Charlie unexpectedly enjoyed the feeling of the stockings on his legs. Seeing his sister dressing him up in her clothes made him feel even kinkier than before, and he couldn't help but get hard. Ashley giggled and jerked his dick only for a moment before patting his stomach. "Not yet bro, we gotta save it for our friend."

Ashley then gave him a little blue thong and matching bra to put on, which he did. He even managed to get the bra on with no problem, which surprised Ashley. "You're a natural," she quipped.

After this she gave him a teal sundress, which he easily slid on. It fit perfectly. She took a moment to stuff the bra with tissues to give him the appearance of a decent set of breasts. The outfit was coming together very well, she thought. She giggled though, seeing Charlie still rock hard, his erection pressing against the thong.

Finally she dug out a wig she'd worn for a play at school a year or two earlier. It was blonde, almost perfectly matching Charlie's hair color, but was a little past shoulder length and just slightly curled at the ends. She fitted it on him carefully, then had him sit at her desk while she applied makeup.

She applied just a hint of blush and mascara, as well as pink lipgloss. She finished with a touch of dark eye shadow before finally giving him a pair of two inch teal heels that matched the dress. He put them on and stood up. He wobbled around briefly before finding his balance and before long he was walking in them comfortably. Ashley stood him in front of her mirror and he gasped.

"Holy..."

"You make a very hot little slut," Ashley giggled, kissing his cheek.

Jenna came into the room now, nodding approvingly at her brother's outfit. "Very nice. Now, what should we call you? How about...Charlotte?"

"I like it!" Ashley spoke up. She spanked Charlie's ass through the dress and he, as well as his cock, gave a little jump.

"Mel's on her way. She should be here soon. Let's get ready too. Charlie, you wait here."

"O-Okay," he said nervously, still admiring himself in the mirror. He looked just like a girl, and couldn't believe it.

First he'd fucked his sisters, then his mother, and now he was dressed up like a sexy little slut. Even with all this, he had no idea how much kinkier things were about to get. He went to sit down on the bed and wait patiently, having to fight off the herculean urge to pleasure himself.

After about ten minutes, Ashley and Jenna reappeared, and Charlie's jaw dropped wide open. Both of them were dressed in schoolgirl outfits. Plaid, pleated red and gray skirts, white button up shirts, white thigh highs, and black one inch heels. They giggled seeing his expression.

"Melanie's a professor. We thought this might give her a laugh...amongst other things," Ashley laughed.

Jenna nudged her, laughing as well, and all three went downstairs to wait. It wasn't long before there was a knock on the door. As soon as the trio answered, Melanie could feel herself getting hard seeing the three in their outfits. "Very...nice," she mused. She herself was dressed in a slinky red dress with the usual black stockings and heels.

They led her inside and all headed upstairs, this time into their parents room, as they had the biggest bed. Melanie followed after them, staring at Charlie in his teal dress. "You must be Charl-"

"Charlotte," Ashley interrupted, winking.

"Charlotte. I like it," Melanie replied.

Charlie blushed as they reached their parents room. Jenna and Ashley pushed Charlie down to sit on the bed and stepped back.

"Go on, Mel," Ashley encouraged.

Melanie licked her lips and sank to her knees. Charlie was nervous, being dressed as he was, but it didn't keep him from starting to get hard as Melanie lifted up the teal sundress, revealing the white garter and lace stocking tops, as well as the little blue thong stretched tight by his hardening cock.

"So sexy, Charlotte. I love it," she cooed.

Charlie blushed. He'd been with his sisters and mother now, but never another woman, and here he was for his first time, dressed as a girl. It was all so confusing, but so hot at the same time. Melanie pulled the thong aside, releasing Charlie's cock. She took it first in her hand, and then into her warm, waiting mouth. Charlie moaned, looking at his sisters who were watching excitedly. Their hands were all over each other as they enjoyed the show.

Melanie was an expert at blowjobs it seemed, as Charlie felt himself approaching the brink faster than usual. Seeing that pretty black hair bob as her lips slid along the length of his cock, he placed his hands on the bed for balance and moaned. "I-I think I'm gonna...gonna cum already."

This didn't deter Melanie. She sucked faster and faster until he blew his load with a loud moan. She kept her mouth locked tightly over his cock, milking it dry of the hot cum that came from within, swallowing every last drop, before finally releasing it.

"Fuuuuuuuuuuuuuuuck," Charlie moaned, satisfied.

"We're not done yet. It's your turn now," Melanie said, standing up with a smile. Jenna and Ashley were giggling, though Charlie didn't know why yet.

The insatiable professor slid the straps of her dress down her shoulders and then let it fall to the floor at her feet. As she stepped out of it, Charlie caught sight of a massive bulge in her red silk panties.

"Is...is that...what the..." Charlie stammered.

"Surprise," Melanie said, pulling her panties down and slipping out of them, leaving her in just her stockings and heels. "Oh come on, you know you want it."

She reached down, taking his hand and placing it on her cock. At first he just let it sit there, staring, not knowing what to think. But he was so turned on by the whole situation, he began to jack her off, gripping her cock and jerking it. "It...you're so pretty though," he stammered, clearly at a loss for words.

"So are you, Charlotte," Melanie laughed, running her fingers gently through the hair of the blonde wig. Charlie could feel himself getting hard again already. First incest, then crossdressing and a shemale. He was in such disbelief that he thought his brain might be broken.

"Come on now, why don't you taste it?" Melanie offered, stepping closer to Charlie so that her cock was only inches from his face. This drove all the thoughts of disbelief from his mind as he gulped nervously. Without another thought however, he opened his mouth and took as much in as possible, going down about halfway before having to pull back. Melanie moaned.

Off to the side, Ashley and Jenna were all kinds of hot and bothered watching the scene, kissing each other passionately, their hands wandering over breasts and between thighs, though they continued to watch the events playing out in front of them as well.

Once Charlie figured out how much he could comfortably take, he began blowing the shemale's cock in earnest, bobbing his head back and forth in rhythm. He was surprised at how much he liked it. The smooth skin on his tongue, and the salty taste of the precum. He was already rock hard once more as he slathered all over this gorgeous shemale's dick.

Melanie likewise was enjoying herself, feeling Charlie's warm mouth wrapped around her member. As she felt herself getting close though, she pulled back, and surprisingly Charlie sighed when the cock was pulled from his mouth. Melanie laughed.

"Oh don't worry sweetie, we're not done yet."

She took Charlie's hand again and had him stand up. Then she turned him around and bent him over the bed.

"H-Hey now, wait a minute," Charlie hesitated as he realized what was about to happen. Ashley and Jenna had stopped in their tracks to watch.

"Sssshhh. Give it a chance, Charlotte," Melanie reassured him.

Her dick still wet from his saliva, Melanie again lifted the sundress and pulled the thong aside. She placed the head against Charlie's asshole and slowly pressed just the tip inside. Charlie winced in pain and gripped the sheets. "Nngh...it hurts," he whimpered.

"It'll feel better, give it a moment," Melanie cooed reassuringly, slowly sliding another inch in. Charlie again felt a wave of pain and this time clenched his teeth. He was still rock hard despite this.

Melanie then slowly slid the full length of her cock into Charlie's tight, virgin asshole. He squeaked in pain once more, but after he had grown accustom to her huge member buried within him, he began to feel a sense of pleasure.

"It's so big," he exclaimed.

"And you're so tight," Melanie moaned, as she slowly began to pump in and out of his ass. She was on cloud nine, fucking this young crossdresser's virgin asshole while his two sister's watched.

Ashley and Jenna were hotter than they'd ever been at this sight, and quickly stripped out of everything but their heels and stockings. Jenna lay down on the bed and Ashley crawled on top of her in a 69 and they began eating each other out in a fevered bout of passion. Each occasionally stopped momentarily to watch their brother getting fucked right next to them.

Melanie continued to thrust into Charlie's ass, savoring the feeling of the super tight channel gripping her hard cock. She watched Ashley and Jenna eat each other out right next to them, and this drove her closer to the edge. She pumped harder, so that Charlie again tightly gripped the sheets. In moments she felt her dick being drained, shooting her cum deep inside Charlie's ass with a long moan. She slowly slid out and smiled, helping Charlie stand.

"Now for being such a good boy, you get to fuck me. I can see you're...up, for it," she giggled, and dropped to her knees, sucking his cock into her mouth once more and slobbering all over it, getting it nice and wet.

After she'd done this, she stood back up, bending over the bed the same way she'd had Charlie positioned. Charlie was a little sore at this point but still feeling good, and didn't hesitate at all before slowly slipping his cock into the sexy shemale's ass just the way she'd done to him, slowly inching into the tight tunnel until he filled her up.

"I've got an idea," Jenna said seeing this.

She crawled off her sister and slid underneath Melanie. Charlie stopped thrusting for a moment, realizing what was going on. Being fucked, Melanie had gotten hard again. Jenna positioned herself below the shemale and she slid her cock into her sopping wet pussy. Charlie began to thrust into her asshole again, so that every time he did, Melanie's cock pumped into Jenna. The three of them were sweating and moaning, their bodies and stockings rubbing against each other.

Ashley climbed up onto Jenna's face, and Jenna again began to eat out her sister. Ashley had a birds-eye view of the three way fuckfest, and she was the first to cum, her nectar making Jenna's entire face wet.

"Oh fuck," Melanie exclaimed, pumping more erratically into Jenna's pussy as Charlie continued to fuck her ass. "I can't hold back!" She yelled, and for the second time today she felt her dick twitch and pulse, depositing its sticky load deep into Jenna's quivering pussy. Jenna came almost simultaneously.

Finally, Charlie increased his tempo. Seeing his older sister eat out his twin, and his own dick slipping in and out of the shemale's tight asshole while they all wore stockings and heels sent him to the point of no return. He gripped Melanie's hips as he thrust hard against her ass, his hot cum shooting in spurts deep inside of her.

The four of them lay on the bed, sweating and panting, fulfilled by the kinky orgy.

"I can't wait to do this again," Melanie said between breaths.

"Neither can we," said all three siblings at nearly the same time.

Act V: Full Circle

The Sunday before the kids had to go back to school and college had finally arrived. They were all thoroughly happy with how they'd decided to spend Spring Break. Julie and Derek had arrived home very early in the morning and were sleeping in as a result. Julie stirred before her husband, waking up extremely horny. She thought about waking him up, but instead decided to pay a visit to her loving children instead.

Climbing out of bed, she put on her bathrobe and went down the hall, finding Ashley and Jenna's rooms both empty. Finally she came to Charlie's room, upon a sight that made her grin.

All three of them were already naked. Charlie sat on his bed, one hand on his cock as he watched his two sisters standing at the foot of the bed making out, caressing each other's bodies.

"Early birds, eh?" Julie quipped with a laugh.

All three jumped and looked at their mother, surprised to see her.

"Well by all means, don't leave me out."

Julie slid off her bathrobe and moved over to the edge of the bed, getting down on her knees in front of her son. "You two were just gonna let poor Charlie here have to take care of himself?" She asked, glancing at her daughters.

"He said it was really hot watching us so we figured we'd give him a show," Ashley responded, joining her mother in kneeling next to the bed.

"Yeah, we weren't hearing any complaints," Jenna chimed in, kneeling on the opposite side of their mother.

Charlie's eyes had grown wide as he watched his mother and two sisters all kneel right in front of him.

"Well girls, let's really give him a show then," Julie said with a smile. She leaned forward and wrapped her lips around his cock, taking the length into her mouth and sliding up until only the head remained locked between them. As she did this, Jenna and Ashley began licking on either side. Charlie moaned. Never did he think he'd be starting his morning with a triple blowjob by his sisters and mother.

All three girls slobbered over his dick, taking turns sucking it into their mouths and licking along the sides, down to his balls. Charlie was having a hard time holding back his orgasm, and his knees began to tremble. "I-I'm about to...already..." He half moaned, half whimpered.

Julie lifted her head and nudged her daughters. "Well we don't want that yet, do we?"

She looked at her three children for a moment before standing up.

"There's only one cock though and three of us. I've got an idea," she said with a sly grin.

With that she left Charlie's room and crept down the hall, back into her and Derek's bedroom. He was still fast asleep. She sneaked over to her dresser, quietly opening the drawer and pulling out a think, pink strap on. As she tip-toed back out of the room though, Derek stirred and caught sight of his naked wife leaving, carrying the toy. His tired brain could barely process what he'd seen.

Julie came back into Charlie's room, tossing the strap-on to Jenna and Ashley. "You girls should try this out. It's super fun."

Ashley and Jenna looked at each other and fought over the toy momentarily, before Jenna won out. She stuck her tongue out at Ashley and Ashley in turn did the same. They both laughed as Jenna began to put it on.

Meanwhile Julie climbed up on the bed and straddled Charlie's lap, hovering just above his cock, still wet from her and her daughter's saliva. Charlie began to fondle her ass cheeks as she lowered herself onto him. He felt as her pussy opened up around his cock, slipping down the entire length until she came to rest against his pelvis. She savored the feeling of being filled up for just a moment, before she began to buck her hips and ride her son. Charlie lay his head back on the pillow and moaned, watching his cock disappear inside his mother's drenched pussy each time she came down.

At the foot of the bed, Jenna had finally gotten the strap-on situated. She bent Ashley over the bed so that her younger sister had a prime view of their mother fucking their brother. Jenna then bent down, licking and sucking Ashley's pussy until it was nice and wet. Once she'd finished, she stood up and placed the strap-on at the entrance to her little sister's cunt and slowly pushed it inside. Ashley moaned and arched her back. The strap-on didn't feel as good as the real thing, but the fact it was her sister fucking her still made her enjoy it just as much.

So at this point Julie was bouncing up and down on her son's cock, while he fondled her ass and began raising his hips up to meet her motions. At the other end of the bed his twin sister was bent over, getting fucked by their older sister from behind by a strap-on their mother had given them. The sight was still surreal, even after all they'd done to this point.