Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/1790542.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/John_Winchester, Dean_Winchester/Sam_Winchester, John
      Winchester/Sam_Winchester, Dean_Winchester/John_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester, John_Winchester
  Additional Tags:
      Feminization, Insecurity, Angst, Makeup, Daddy_Kink, Wincest_-_Freeform,
      Weecest, Anal_Fingering, Kissing, Crossdressing_Dean, Rimming, Blow_Jobs,
      Cock_Cages, Dirty_Talk, Anal_Sex, Praise_Kink, Sex_Doll, Sammy_is_a_Doll,
      Objectification, Wall_Sex, Rough_Sex, Panties, Punishment, Whipping,
      Paddling, Spanking, Gags, Bondage, Bondage_and_Discipline, Sex_Toys, Cock
      Rings, Aftercare, light_bloodplay, Guilty_Dean, Caring_John, Nipple_Play,
      Parent/Child_Incest, Sibling_Incest, PWP, Plot_What_Plot/Porn_Without
      Plot, no_regrets
  Series:
      Part 9 of Holidays_with_the_Wincesters
  Stats:
      Published: 2014-06-15 Completed: 2014-06-19 Chapters: 5/5 Words: 11353
****** Daddy's Girls (A Wincest Father's Day) ******
by MothMeetsFlame
Summary
     There are three things John wants for Father's Day. Dean and Sam are
     more than willing to provide them.
     Ch1: Getting Ready (Plot)
     Ch2: Pretty Girl (PWP)
     Ch3: Baby Doll (PWP)
     Ch4: Bad Daddy (PWP)
     Ch5: Aftercare (Porn, hint of plot)
Notes
     I had some problems getting this written. My imagination took off
     when I thought about all the things I wanted to have the boys do, and
     the list got waaaaay too long, so I narrowed it down to three. I have
     to say that, from looking at my list, I am one kinky motherfucker.
     Who knew?
     Fem!Dean is something I've been wanting to do for a while now, but
     the plot went on forever. My logic: Sam and Dean don't have anyone
     but their dad, so he deserves a few days to celebrate. Plot for day
     one, porn for days two, three, and four, then more plot to finish us
     off on day five (which kinda turned into a little porn as well).
     Comments are celebrated with happy dances of extreme joyfulness! If
     you have anything to say, I'm all ears.
     WARNING: Underage. Sam is 13 for this fic, and Dean is 17. Also
     contains incest. Lots and lots of incest between two boys and their
     father. There's also crossdressing, an underage human sex doll, and
     bondage/whipping/punishment/slight bloodplay/nipple play. If you
     don't like this stuff, don't click on it. I'm totally serious. Read
     the tags. I think I tagged everything, but if I didn't, you get the
     gist.
     Enjoy ;)
***** Getting Ready *****
It was harder for him than he'd ever admit. He wasn't like Sammy. Sam could
wear a burlap sack and make it sexy—had, in fact, but that was another story
altogether—with his slim hips, and floppy hair that, mixed with his still-baby
cheeks and wide eyes, gave him a feminine figure to put real girls to shame.
His round ass and dime-sized rosebud nipples were just the icing on the cake.
Dean wasn't like that. He was too tall, and large in all the wrong places. His
butt was pert, but not cute with little dimples that were the perfect target
for the right tongue, and it was too firm, too large, and too rough for his too
wide hips. His eyes were the brightest jade green he'd ever seen, but other
than that, there was nothing else he could see that could justify his father’s
and brother's attraction to him.
It was even worse after Rhonda.
She'd opened the door to a whole new level of self-hatred.
It was the panties that did it.
They were frilly, soft and tight in all the right places. It had been in his
head ever since Christmas Eve when Sammy had gotten three—three!—pairs of
pretty lace panties that started his collection.
He was happy for him. Really, he was. Sammy looked great in them, in anything
really. When he'd come out of the bathroom in those heels with those panties
and that makeup, Dean's cock screamed with the torture of having to wait.
He was so caught up in the moment that he hadn’t realized until the next day
that Sammy was the only one who's gotten them. Sure, their tastes were pretty
different when it came to sex, but... was that really the reason their father
hadn't shown a hint of wanting that from Dean? He knew he wasn't as pretty as
Sam, but he was still pretty, right?
He studied his reflection in the changing room, noting every imperfection with
dismay as he tried on the grey, then white, then pink, green, blue panties over
his boxer-briefs.
They were amazing. Even though every line of his half-hard cock showed through
them, they just felt... right. They drew away from the shoulders that were too
bulky from grave-digging, the scars from being tossed around like a rag doll by
poltergeist after poltergeist, the hard glint in his eye from all the evil he'd
seen. He didn't have to be hard in these. He didn't have to be a Hunter. He
just had to be pretty, not that he was doing all that great with what he could
see in the mirror.
He wanted everything, though, not just the panties. Makeup was a must if he
wanted to cover the few blemishes only he seemed to be able to spot in the
mirror. Maybe some gloves to smooth over the calluses? A slip would work
wonders for his masculine figure, transform it a little.
Then the thought crept back into his mind: what if he doesn't like it?
It wasn't all that difficult to imagine the thinly veiled skepticism John would
have when he showed him his new purchases. Dean wasn't Sammy. His feminine
qualities had gone right out the window around puberty. He knew his dad liked
that. He liked Dean hard, liked the rugged quality of his voice when it was
thick with sex. He said so, and Dean believed it wholeheartedly.
But what if that was all John liked? What if he didn't like that sometimes Dean
dreamt about the feel of silk panties and mascara running down his cheeks while
he gagged on his father's cock? He did have two boys, after all, and Sam was
the only one of them who looked even halfway decent in anything that wasn't
jeans and a t-shirt.
Dean pulled up the image of his father wearing the pair of panties that he
currently held in his hand and shivered at the thought. The image definitely
wasn't something that would hoist his anchor.
What if it was the same? What if John didn't like it?
Dean groaned in frustration and quickly checked out at the register before he
lost his nerve. He ran for the bus, heading toward school, bags tucked safely
into his backpack. If he was there when he planned, neither Sammy or John would
know he’d skipped to go shopping.
He just wondered whether it was worth it.
 
===============================================================================
 
"Oh my god, Dean!" Sam gaped like a fish at the sight in front of him, more in
shock than anything.
Dean blanched and grimaced, a flash of shame crossing his face before turning
the look into anger and yelling at him. “Don’t you ever knock?! Get the hell
out!”
The door slammed in front of him, and Sam still couldn’t do anything but stare
and try to wrap his head around what he’d seen. He wanted to laugh, but at the
same time, he wanted to smack Dean in the head for not asking him for help.
“Dean?” he called, knocking on the door a couple of times like Dean had asked.
“Go away!”
“It’s not that bad,” he said through the door. “Promise.”
“I said, go away, Sam.”
“I can help you fix it. I mean, I know how to do it right, and I could show
you, if you want. C’mon, Dean. Open up! I promise I won’t laugh.”
It took a few seconds, but Sam heard the door unlock and he breathed a sigh of
relief that Dean trusted him with this enough to let him in.
Still, it was hard not to laugh at the sight Dean made sitting sullenly on the
lid of the toilet seat. He wasn’t in anything but a pair of boxer-briefs, but
the sour look on his face was perfectly accented by his futile attempts at
applying makeup. There wasn’t anything that Dean had tried that he hadn’t
royally messed up. His lipstick was ten shades too white, his eye shadow so
dark it looked like two black eyes, his eyeliner too long, too thick, and too
crooked, not to mention the foundation and blush which were both so gobby and
concentrated that it would have been better suited in a carnival than on Dean’s
face.
“It’s not so bad,” Sam said, grimacing to hide his smile.
Dean, however, wasn’t fooled. “It’s horrible.”
“I can fix it.” He left the bathroom and shuffled through his duffle bag for a
few seconds before he was back. “Here,” he said. “Wipe all of that crap off.”
“Seriously, dude?” Dean asked incredulously. “Baby wipes?”
Sam just shrugged. “They work.”
It took Dean a while to get it all off, but five minutes—and four wipes—later,
his face was clean and ready for Sam’s genius.
He grabbed the makeup bag and took out the foundation, mixing it to suit Dean
who was two shades darker than he was. Before he could even touch his brother’s
face, though, Dean pulled back and looked at him skeptically.
“I don’t know if I wanna do this,” he said.
Seriously? Dean was an idiot. “Says the man who spent who knows how long locked
in the bathroom trying to do this—wrongly, I might add. Now that you have
someone here who actually knows what he’s doing, you don’t want to do it
anymore? I don’t think so. Sit,” he ordered when Dean tried to stand.
Dean sunk back down on the toilet seat, frowning, but not moving against Sam
when he started applying the foundation.
“What is all this?” Sam asked, motioning to the three bags sitting on the sink
counter.
“I wanted to dress up for Father’s Day,” Dean said quietly.
Sam smiled, happy to know that he wasn’t the only one who had the weird
feminization kink. He’d been starting to wonder if something was wrong with
him.
“It’s just…” Dean trailed off.
“Just?”
“I don’t know. It’s hard. It’s… not like it is for you. I mean, you’ve been
doing it for as long as we’ve been doing it. It never bothered you, but… I
dunno. It’s hard.” Dean shrugged.
Sam finished with the foundation and rummaged through the bag for the eye
shadow and his brush set. “You’re stupid,” he said plainly. “Seriously.”
“What?”
“Close your eyes.”
Dean did as he asked, and Sam dipped the eye shadow brush into the cream-
colored container, getting just enough on the tip to do the base. He brushed it
on quickly and chose another color, concentrating on his brother’s eyes while
he spoke. “I never dressed like that before Christmas Eve.”
Dean scoffed.
“No, seriously. I mean, yeah I wore, like, girly stuff sometimes, but it was
all dress-up stuff for Easter or Saint Patrick’s Day or something. I was a
bunny, then a leprechaun.” He switched colors and kept going. “I was even Cupid
one year, but those were just costumes. Christmas Eve was the first time I ever
wore any of that stuff when it was regular clothing. It was totally different.”
At least Dean wasn’t scoffing this time.
Mascara. Eyelash curler. More mascara. “Okay,” Sam said, stepping back
slightly. “Open.”
Dean opened his eyes, and Sam nearly gasped at how freaking green they were.
The pink and gold really defined them and, holy crap, just imagining what Dean
had bought…
He was well on his way to getting hard.
“Well?” Dean asked. He cast his eyes down self-consciously, something Sam was
decidedly against. Those pretty eyes should never be covered up.
Sam used the side of his finger to lift Dean’s chin until their eyes met.
Slowly so he could savor the moment, he brought their lips together. It was
tender and sweet, slightly wet though he didn’t use tongue. Dean’s lips were
thick and soft, the sweetest Sam had ever felt. When he pulled back, he was
surprised to find himself pulling in a ragged breath.
“Needed to do that before the lipstick. We wouldn’t want it to smear,” Sam
said, voice shaky. He took in another breath and righted himself before dipping
back into his makeup bag for the next set of supplies. “Hold still,” he said,
brandishing the lipstick—pearl; he didn’t really want to overdo it. “And no
talking.”
Foundation—check.
Eyes—check.
Lips—he wiped the thin line that went beneath the bottom lip—check.
Cheeks—
Sam grabbed the blush brush and set to work.
“I was terrified,” he continued. “I knew Dad liked it, or else he wouldn’t have
got ‘em for me, but I almost didn’t come out of the bathroom because I was
scared of what you’d think.”
“Me?” Dean asked, shocked.
Sam nodded. He glanced up and made eye contact with Dean, loving the way his
green eyes sparkled with confusion, then understanding.
“You didn’t think I’d approve,” Dean surmised.
He shook his head in agreement. “It freaked me out at first that you wouldn’t
like ‘em. It’s something that could’ve ruined everything, you know? But then I
realized that I had at least one person who approved, and I thought, if Dean
doesn’t like them, he can suck it.” Sam smirked. “So I wore ‘em. And I liked
it. And Dad liked it. And you liked it.”
Dean sighed. “But that was you.”
“So?” Sam asked, stepping back to admire his masterpiece, deciding it was
perfect, and putting all of his stuff away.
“So… I’m not like you. I’m not…”
“Pretty?” Sam finished for him.
Dean grimaced and looked down again.
Sam brought his chin back up and looked him straight in the eye. “You’re an
idiot,” he said. “Trust me. If Dad doesn’t like you all prettied up like this,
he’s an asshole.” Then he added. “I’d kiss you if it wasn’t for the lipstick.”
Dean smiled, still not completely convinced, but well on his way.
“C’mon,” Sam said. “It’s time to show me what you bought.”
 
===============================================================================
 
Father's Day.
John shivered at the implication, cock hardening in his pants through no force
of his own when he thought about all of the possibilities. It was a
tradition—inasmuch as two years could be called a tradition—that both boys
surprise him with something unexpected.
Usually, that meant sex in many shapes and forms.
Last year, he popped his bottom cherry. The year before was Sam's first DP.
This year… whatever it was, it was sure to be good.
They were all pretty active in their sex lives, most of their fetishes and
kinks already out in the open. He didn't think there was a single thing that
they could really surprise him with, though he wouldn't be surprised to find it
risqué. Considering he was a mid-thirty-year-old man who slept with his two
underage children on a regular basis, there wasn't really anything that could
compare in the risqué department, though he had a few ideas.
He was two days out when he started making a list of everything he wanted for
Father's Day.
He was one day out when he'd narrowed that list down to three things: a Sammy
doll, a nice whipping scene, and cross-dressing Dean. For all they'd played
around, those were just a few of the things they'd yet to try.
He wasn't so sure he'd get any of them though. Sammy was too expressive to be a
doll. There was no way he was going anywhere near his boys with a whip—and they
probably wouldn’t feel comfortable whipping him, though the idea was strangely
appealing. And Dean wasn't into the whole fem kink thing. They both loved Sammy
when he dressed up for them, but Dean wasn't that kind of kid. He was too
mannish for that. Sure he had the perfect lips for it, and the subtle curves of
a women, but John didn’t think that Dean would get any satisfaction from it,
and if Dean wasn’t really into it, there was no real appeal for him either.
At six hours before he reached the house they were squatting in, John called
the boys to let them know he was close.
“Hey, Daddy,” Sam said happily into the phone. Thirteen years old, and he still
called him Daddy.
John wasn’t loath to admit that it turned him on.
“You almost home? Dean and I have a surprise for you.” His smile could be heard
through the phone, and John’s anticipation grew.
“Six hours, give or take. You boys staying safe?”
“Yep. Pastor Jim called yesterday and told me to tell you about a Hunt in
Indiana, but I told him you were going to be busy for the next few of days. He
said he’d call Caleb.”
“I’m gonna be busy?” he asked.
“Mmm-hmm. You, me, and Dean are gonna need some time to recuperate.”
And fuck if that didn’t have his imagination in shreds with the implications.
It didn’t take him the full six hours to reach his destination. Four and a half
hours later, he pulled into the driveway of the somewhat-decent house he’d
found for him and his boys to squat in, far from prying eyes, and walked the
dozen paces to the front door. It was reminiscent of his cabin in North
Carolina, and he had a sudden flash of fucking his youngest hard and deep
against the back porch—something that was definitely going to happen before
they left.
He didn’t knock, just unlocked the front door and went inside, stomping the mud
off of his boots and flicking the light on before making his way to the
bedroom.
Shock. Betrayal. Anger.
Emotions flitted through John, fast as lightening at the sight before him.
They’d talked about bringing another person into the fold—sometimes a man,
often a woman—but it was too risky. Not only that, but the thought of having to
share his boys with anyone else, man or woman, had his possessiveness flaring
to life in ways that endlessly satisfied his sons. To think that Sammy had gone
against him, especially on today of all days, hurt him in ways that he couldn’t
even comprehend.
“Hi, Daddy,” Sam said, lifting his head from the woman’s neck. She made a small
whimpering noise and fisted her painted hands in the sheets as arousal flushed
through her. “Wanna taste?”
John didn’t know what his face looked like, but the way Sam’s expression went
from lustful to fearful in the space of a few seconds would have been comical
had it not been for the rage flooding through him.
“What the hell do you think you’re doing?!” It was pain, knowing that Sam would
do this. They weren’t exclusive or anything. Both Dean and John slept with
other women, sometimes other men. Sam had had a couple of experiences also, but
bringing someone here?
“I-” Sam floundered for a response.
John saw a flash of movement behind Sam and took another look at the woman on
the bed, now curled around herself, tucked into a ball, shivering with fear,
and felt a pang of guilt for scaring the poor girl. “Shit,” he said. She was
young and pretty, with light brown hair waving around her delicate face. The
sleek negligee was something he would have found insanely attractive in any
other set of circumstances. “Fuck.”
“Fuck you,” finally came the reply from his youngest.
Sam’s anger matched his in its intensity, and John reeled back in surprise
before setting himself firmly against him. Sam was the one who was wrong in
this situation, not him.
“What did you say to me, young man?” John said, voice hard, giving his son the
opportunity to correct himself.
“I said, fuck you.”  He spat the words.
“That’s it, I’m gonna—”
“Will you both please stop it!”
John blinked, taken aback. He hadn’t noticed Dean anywhere, but that was
definitely his voice with its familiar tinge of apprehension.
“I –I’m sorry. It’s my fault,” Dean continued, while John glanced around,
trying to find his son. “Iwas the one who did this, not –not Sam.”
Holy fuck.
“Dean?” John asked, staring skeptically at who he’d assumed to be some strange
woman in his bed.
“I wasn’t sure if you’d like it,” he whispered. Fuck, the boy sounded
heartbroken, and Sam glaring daggers at him made sense now.
Dean’s legs curled under him, and he glanced away, absentmindedly chewing on
his bottom lip. Unlike Sam’s put-on innocence, this was real, completely
genuine. Dean was shy for christssake. How the hell had he managed to screw
this up so completely?
“I’ll… go change.” Dean didn’t look at him as he crawled out of bed, heading
straight for the bathroom.
“You’re not going anywhere,” John said, wrapping his arm around his son’s
slender waist and pulling him down so he was sitting right on top of John’s
stirring cock.
“You –you don’t have to…”
“To?”
“To like it. I mean, it was just something to try, not like it really means
anything.”
John scoffed. Of course it meant something. That Dean had kept it from him for
so long pretty much guaranteed it.
Thinking that the scoff was aimed at him, Dean flushed and looked down in
shame.
“Settle down, Sam,” John said, when his youngest looked like he was on the
verge of pulling Dean away from him and tearing his eyes out. “Just listen for
a minute. I think we all got a little mixed up.” Then it was his turn to blush.
Now that he thought about it, it seemed kind of stupid. “I, uh… Well…”
Sam glared. “Get on with it.”
John ignored his snarky attitude and continued. “When I walked in, I thought
you decided to go ahead and add a fourth person, like we’ve been talking
about.”
Sam’s brow furrowed in confusion. “But you said no.”
“I know. That’s why I was upset.”
It took a second for Sam’s brain to catch up, to realize where everything had
gone wrong, but when it finally did, John was surprised to find him laughing.
“Sam?” Dean asked, still sitting awkwardly in his father’s lap.
“Dad… he thought…” he said between chortles. “he… Dean… he thought… you were a
girl.”
“What?”
John rolled his eyes at Sam’s amusement, and turned to face his eldest. “I
wasn’t mad because of this,” John said, trailing his finger down the thin lacy
nightie Dean had on, and dipping it underneath to toy with the front of his
soft panties. “I thought Sam brought home a girl for us to play with.”
“Really?” The hope really made Dean’s eyes sparkle. Damn, he was pretty.
John nodded. “You know I don’t like sharing you, especially when you’re all
dressed up for me.” Dean gasped when John’s finger found its way inside of him.
“Your pussy’s all wet for me, baby,” he whispered in Dean’s ear. “You been
waiting like a good girl for Daddy?”
“Yes,” he squeaked breathlessly, and fuck if he didn’t sound like a girl in
that moment.
With his other hand, he pulled Dean’s chin toward him and brought their lips
together. Cherry and lipstick and Dean assaulted his senses in an arousing
sensation that sent lust coursing through him.
Sam was right, they were going to need a few days.
***** Pretty Girl *****
Chapter Summary
     Dean's a slut for Daddy's cock.
Chapter Notes
     And a bit of porn to tide you over until tomorrow :) Here's cross-
     dressing Dean with John.
See the end of the chapter for more notes
Dean was still trying to wrap his head around everything when his father’s
voice echoed in his ear.
““Your pussy’s all wet for me, baby. You been waiting like a good girl for
Daddy?”
I, uh, I… “Yes,” he squeaked. It was the same voice Sammy had been teasing out
of him every since he’d dawned the wig.
Holy shit, De, he’d said. So pretty.
And Dean had seen his cock tenting his pants then as he adjusted the wig on him
so it would stay in place. He’d seen himself in the mirror, and… Sammy was
right. He was pretty.
The finger inside of him crooked, and he yelped in surprise at the sudden rush
of pleasure as someone finally paid attention to his prostate.
Dean’s eyes slipped closed. His mouth parted. His hips rose of their own
volition.
“That’s right, baby girl,” John continued, oblivious to Dean’s meanderings.
“Let Daddy take care of you.”
His other hand trailed down his front, hesitating at the hem before lifting it
enough to toy with his nipples. John was thrilled at the harsh panting noises
he was eliciting from his son at the movement, but it wasn’t enough. He wanted
his girl practically writhing.
“C’mon, princess,” he said, pinching hard and loving the low keening it
produced. “I wanna taste your pussy.”
Sam gasped from behind them, shocked at the abrupt change in the room. Not
thirty seconds ago, he was ready to tear his father’s eyes out. Now all he
wanted was his father to hold him up against the wall and fuck him into
oblivion.
“You coming, Sammy?” John asked, looking at him while he flipped Dean back on
the bed and absentmindedly parted his legs. “Your sister’s waiting.”
John turned back to Dean, and sucked in a shocked breath when he caught sight
of his second surprise: a tightly-fitted cock cage.
They’d talked about it. A lot.
Neither of the boys really showed much interest, though John thought he might
try a chastity device when they were a bit older. Just seeing it on his eldest
drove him crazy.
The pink plastic hugged his straining cock in its confines, keeping it from
hardening with any degree of success.
A small hand touched his shoulder—Sam, getting his attention—and it wasn’t
until then that he realized he’d been staring slack-jawed at Dean’s caged form.
The small hand wrapped around his shoulder and pulled him in for a kiss, hard,
wet, and steaming, breaking his line of sight. Sammy’s tongue twisted its way
inside his mouth, assaulting his senses in the best of ways.
John lifted him by the thighs and nearly wept at the sensation of Sam’s lithe
frame against him, canting his hips up to rub their clothed cocks together, the
stimulation perfectly frustrating in its intensity.
Sam was the one to pull back first. With a small smile, and a lick of his
swollen lips, he parted their kiss, laughing when John looked at him grumpily.
“Here,” he said, holding out a small key.
John was confused at first, but realization dawned on him.
“De said that, if you don’t like it, to let her out.”
A thrill ran through John at the word her.
“She won’t be mad.”
Then Sammy was off of him and ducking into the hall without so much as a
backwards glance, leaving him alone with Dean.
He looked back at his son on the bed, the one he had to try to find beneath the
cover of makeup and lingerie. John glanced back at the key in his hand,
suddenly overwhelmed with the responsibility he was given. It was one thing to
mess around with this orgasm denial stuff, quite another to go this far into
it.
“You sure this is what you want?” he asked
Dean bit his lip—wetness showed on his lips; ohGod that was hot—and nodded,
looking up at him between thick lashes.
“One week,” John said.
The relief on Dean’s face was enough that he knew he’d made the right choice.
“Maybe longer, if you don’t behave.”
The smirk that played on his son’s face was one hundred percent Dean in that
moment, and it held a promise that that one week would almost definitely be
extended. But then the smirk turned a little unsure—something Dean never was in
bed—and he looked down, hiding his pretty green eyes beneath his carefully
tousled bangs.
“None of that,” John ordered. He sat on the edge of the bed beside Dean and
lifted his chin until they were eye to eye. Then he crushed their lips together
in a bruising embrace while Dean whimpered beneath him. “Keep your eyes open. I
wanna see them when I fuck you.”
John didn’t miss the goose bumps that crawled down his arms, but Dean’s eyes
held his obediently, even when he crawled over Dean and pulled his thighs down
until they were flush against his.
“Told you I was gonna take care of you, pretty girl, and that’s just what I’m
gonna do.”
He fingered the tight pink cock cage, smiling at the small grimace that showed
on Dean’s face as his cock tried its hardest to swell. Then, without preamble,
he shoved two fingers inside of his boy.
Dean yelped loudly and struggled to get away from the intrusion, but John’s
hand held him in place while he explored, dipping his fingers inside,
scissoring and stretching the clenching muscles until Dean was adjusted and
ready for whatever John had planned.
“That’s a good girl,” John whispered when his baby had loosened up for him.
“Your pussy’s all slick and wet, just waiting for me to take you. You want
that? Want me inside of you?”
Dean couldn’t hold back anymore. “Daddy?” he squealed. “Daddy.”
“Shhh,” John soothed. “Settle down, baby. Tell Daddy what you want.”
“Want –want you in me Daddy,” Dean whispered shyly, his voice soft and
feminine. “Want you to taste my –my pussy and…”
“And?” John prompted.
Dean blushed, but pressed on, his eyes swimming with tears of complete
embarrassment. “I want you to fuck me.”
“I don’t know,” John teased. “I didn’t hear my baby girl ask nicely…”
“Please?” Dean squeaked desperately, not even an attempt at keeping his
composure. “Please, fuck me? Please? Daddy!” Dean screamed when John pressed
firmly against his prostate, teasing spurts of precome from his flaccid cock.
“Please, Daddy, please…”
“Of course, baby,” he said, smiling. “I love it when you’re all dressed up for
me. You make your daddy proud, you know that?”
Dean nodded, suddenly shy again. “Am I… am I a good girl?”
John leaned down and licked across his lips, not caring that he was ruining the
careful lines of lipstick he’d drawn on. “You’re a very good girl, princess,
the best for me.”
He was rewarded with another spout of precome that he promptly licked up,
pulling another cry from his boy.
“And good girls are sluts for Daddy.”
Dean’s eyes went wide, but he was up and out from under him immediately,
pushing John down onto the bed and straddling him.
If there was one thing that Dean was, it was a slut for his daddy’s cock.
He pressed his lips chastely against his father’s, then lowered himself until
he was eye level with the bulge of his father’s cock. Working quickly to
release it, Dean ran his tongue over his lips in anticipation.
He groaned at the salty taste as he suckled the head of his father’s cock,
smiling when he pulled off and caught a trace of lipstick around it. The sight
fueled his arousal and he took his father again, sucking deeper and deeper
until the cock was pressed back against his throat, but it had been a long time
since it was sensitive to touch. This time, the muscles that contracted were
his own doing, and he flexed them proudly to force the keening moans from his
father as it stimulated the sensitive nerves.
Spit gathered in his mouth, slicking his way as he bobbed his head up and down,
the friction just enough with his lips latched tightly around his father’s
shaft. He loved the ache in his jaw as his mouth was stretched past the point
of comfort, they way his eyes watered as the thick cock assaulted his gag
reflex, the way he struggled to pull in a full breath of air as he shoved his
father further and further down his throat, but the thing he loved the most was
the moment when his father wasn’t able to hold back anymore, the moment when
John tangled his fingers into his hair and fucked himself into his mouth.
With a hard pull, John yanked Dean off of him, meeting his son’s glazed over
expression with his own. Only seconds away from orgasm, he gripped the base of
his cock tightly, stubbornly holding it off.
“Want you…” Dean’s voice was rough with sex, but still soft in a way that
surprised John. “Want you to fuck me, Daddy,” he said. “Please come in my
pussy.”
The shy expression was back on his face, and how the hell was he supposed to
say no to that?
“Of course, princess,” John whispered, twisting Dean underneath him and parting
his son’s legs with his own.
He lined his cock up and teased the rim with his head, loving the way Dean
gasped and twitched with every pass, his hair flinging out wildly around him
and his nightie riding up to show his well-toned abdomen. He dipped down to
taste the flushed pink skin, heated with sex.
“Da –daddy?” Dean gasped in shock as John’s tongue slithered his way into his
belly button, leaving cold wet trails down his stomach.
“Yes, baby?”
“What are… Are you gonna fuck me?”
John smiled and pressed a kiss at his naval. “Not yet,” he said.
He took his time as he licked and kissed a path to Dean’s scrotum. Then he took
the swollen sack into his mouth and suckled it until Dean was canting further
into the touch, moaning a steady stream of pleasefuckmepleaseDaddyplease.
“I wanna taste your pussy, baby,” he said when Dean tried to pull him back up.
He let his tongue lick at the tip of his son’s soft cock, still caged and
confined, one last time before going lower and plunging his tongue through the
loosened ring of muscle.
“OhGodfuckDaddyplease!”
He licked his way past the skin of his son’s taint and dipped his tongue in and
out, watching as the muscle opened and closed to encompass him. With his two
thumbs, he held Dean open and blew on his sensitive hole, filing away the
scream Dean let out as the cold air assaulted him.
John ignored his baby’s cries and ate to his heart’s content. It was a
different taste than usual—vanilla instead of cherry—but it suited his son
well. Sex and vanilla and a wisp of perfume combined to compliment Dean’s own
natural scent and, coupled with the taste of his son’s gleaming wet pussy,
John’s cock wanted nothing more than to fuck into him hard and fast.
But he didn’t want to hurt his baby.
 
John spit, warm and wet, into his son’s now gaping hole before plunging three
of his fingers inside, all wet with lube.
Dean yelped and pleaded—fuckmepleaseDaddyfuckmeplease—as his prostate was hit
repeatedly by John’s unyielding fingers, overwhelming him to the point of
incomprehension.
Then the dreaded—amazingly wonderful—fingers were gone, leaving him empty and
gaping, his need building up as his anticipation grew.
“You ready, baby?” John asked.
Dean nodded, eyes wide and glued to his father’s face like he’d been told. It
amazed him more than anything else that he’d been able to keep his eyes open
throughout all of his father’s teasing. “Yes,” he panted.
“Yesyesyesyespleasefuck.”
John smiled, leaning down to nuzzle his neck while he pressed inside of the
tight heat of his baby’s pussy, slick and wet for him.
“Daddy!”
“Fuck! So tight for me, baby. Such a good girl.”
He thrust in steadily, hilting himself in one move while his son screamed and
writhed beneath him. It wasn’t a scream of pain, but of pleasure, so John
didn’t even pause, choosing instead to pull out to watch his son’s hole quiver
as it was suddenly emptied before thrusting in again, hard and unrelenting,
filling his boy up with his thick cock.
Dean’s inhibitions were released then with the feeling of his father’s cock
inside of him, and the extent of his vocabulary was finally realized as
colorful expressions flew past his lips, filth spilling from his pretty little
mouth.
“Fuck! Fuck my pussy, Daddy. Hard. Yes! Fuck. Oh, God. Need you, Daddy. Need
you to fill me up, fuck me harder—uh—there, Daddy, right there. Want you to
fill me up, stuff me full of your come. Want it leaking out of me, please. Ah!
So good. I’ll be such a good girl for—fuck—for you, Daddy. Please. Want your
come. Please, Daddy? Can I—uh—can I have it?”
With that question, John couldn’t hold it in any longer. He slammed in hard and
came with a grunt deep inside his son’s tight ass. The rolling orgasm took hold
of him and made his head float while Dean screamed in victory beneath him.
His hips absentmindedly thrust him through his orgasm, waves of pleasure
shooting through him with the movement until his cock was completely spent of
every last drop of he was capable of producing.
John moved to pull out of his son, but Dean grabbed his hips tight and held
them.
His baby bit his lip, changing from the cockslut who screamed for his daddy’s
come to the shy boy who demurely asked his father if he was pretty.
“What’s wrong, princess?” John asked.
“Nothing,” Dean said quickly, but the hands that stayed firm on John’s hips
told a different story. “It’s just, um… Can I –can you stay in me, Daddy? I…”
John smiled. “You wanna be my little cockwarmer?” he offered. “Wanna stay
stuffed full of Daddy’s cock?”
Dean nodded, still shy.
“Look so good when I’m filling you up.”
Suddenly, John flipped them over so Dean was straddling him, their chests
pressed tightly together, John’s cock still inside of his son’s leaking ass.
Dean blushed again, his cheeks pinkening, blending perfectly with his soft
green of his eyes.
“Um, Daddy?” he asked quietly.
“Yeah, princess?”
“After this, can we… Will you play dolls with me?”
John’s confusion was plain, but that didn’t keep him from muttering, “Sure,
baby. Anything you want.”
Dean’s smile was brilliant, showing off the straight whites of his teeth.
“Thank you, Daddy.”
“No, thank you, my pretty girl.”
John lifted his head to capture his son’s bottom lip between his teeth.
Already, he could feel his cock twitch, wanting to be able to fuck into the
velvet heat of his baby’s ass.
Later, he thought, biting down hard and licking his way into Dean’s parted
mouth.
There was still plenty of time to play.
Chapter End Notes
     Check back tomorrow for the next chapter, featuring Sammy and John
     (and possibly some Dean on the side).
***** Baby Doll *****
Chapter Summary
     John promised to play dolls with Dean. It's too bad Dean has
     something else to do. Oh well. Looks like John will have to play
     alone.
Chapter Notes
     Sorry! So, so, so sorry that it's late :( My internet has been out
     since Monday night, and it's STILL NOT WORKING!!! I invite you all to
     join me in my rally against the phone company. Time and place TBD.
     Anywho... Here's chapter three of the fic, brought to you by my
     bestest friend in the whole universe (thank you, Sarah!!) who has
     allowed me to borrow her kitchen table and her internet to post porn.
     Doubly sorry for the lateness. Enjoy ;)
See the end of the chapter for more notes
Will you play dolls with me?
John was more than a little confused at the question. Obviously, he knew what
dolls were and how to play with them—that wasn't why he was confused. The
confusion came from why Dean wanted to play dolls in the first place.
Traditional toys were never something his boys really had, and this was
different in a hundred ways, but something about the tone Dean took—the tone
that wasn't self-conscious and shy, and fuck sexy as hell—said there was
something really big he was missing.
If he really thought about it, he could certainly see the appeal in role
playing.
Watching as Dean played in a cute outfit with his tiny little dolls, dressing
them in tiny little outfits, while his slim waste and wide hips showed the
natural curve of his ass in tiny little panties, cock cage shaking every so
often as he scoot across the floor, hair done up in pigtails, curling down and
framing his face with wide green eyes and sex-swollen lips—oh yeah, there was a
definite appeal.
Then John would say, why don't you come sit on Daddy's lap to play?
And Dean would bite his lip and look up at him with those green eyes and pink,
embarrassed cheeks and say, okay, Daddy.
And he would crawl onto his lap, pert ass rubbing right against his rapidly
hardening cock, wiggling and shaking as he played with his dolls.
John's cock was nearly hard now, still nestled deeply inside Dean's ass. His
baby could feel it, John knew.
"Daddy? You ready again?" Dean asked in a small voice.
"Yeah, baby."
"But..." He trailed off and looked up with pleading eyes that made John want to
give him the world. "But, you said you'd play dolls with me."
John held in his sigh. There was a time and a place for role playing, and now
was not the time. That particular fantasy was a slow-burner. It took time and
time and more time to get going, nice and slow so he could play with his
princess the way she should be played with.
Now, though, he wanted nothing more than to slam into the wet pussy that
surrounded him and pound his baby's ass until he screamed for more.
"Not now, princess. We'll play later. Now, Daddy wants to use you up, hear you
scream while you ride me like a good little girl."
Dean pursed his lips, and the look that followed was so contrary to his
previously demure one that John was nearly sure he'd imagined it. Dean smirked,
eyes sparkling with mischief.
"Oh, I think you'll be happier playing dolls with me, Daddy. ‘Sides you
promised." He pouted, bottom lip jutting out in a way that made John want to
pull it into his mouth and bite it.
So he did.
"Okay, baby," John answered as Dean sucked the soon-to-be-swollen lip into his
mouth. "Let's play."
Dean grinned and led him out into the hallway, passing his own bedroom and
heading straight to Sammy’s. The glance before Dean opened the door was
nervous, and it filled John with apprehension.
…which completely went away when he realized just what playing dolls meant.
Sammy lied perfectly straight on his bed, his own makeup much more subtle than
his brother’s. There was a slight sheen to his cheeks, which were pink with
blush, and his hair had been fixed so it fell on either side of his face in
perfectly straight lines until it touched the sky blue baby doll dress he’d
gotten for his birthday. He was still, so still that John was sure it really
was a Sammy doll—until he made out the subtle fall and rise of his chest.
“You like her, Daddy?” Dean asked, no longer shy now that it was Sammy on
display.
John’s cock hadn’t gone down any since he slipped out of Dean’s hot pussy, but
even if it had, it would have been back now. “I love her, baby,” he said, voice
rough.
Then Dean was right in his ear, whispering so softly that it tickled and sent
shivers down his arms. “Sammy’s your own personal fuck toy, Daddy, a hole for
you to use however you want. Baby doll is soft and ready for you, so don’t
worry about breaking it.”
John felt wet tongue on his neck.
“I’d try the mouth, Daddy. It parts just right for your thick cock, no gag
reflex to trigger or anything.”
The heat of Dean’s breath was gone then, and John was left wondering what the
hell he was supposed to do.
“Wait,” he said when he heard the door open. “Where are you going?”
Dean smirked. “I’m getting your other present ready, Daddy. You have fun with
your new doll.”
Dean left, and the closing door seemed too final for John’s liking.
“Okay,” he whispered, stroking his cock once, twice, until it was at full mast.
He crawled on the bed and straddled his doll’s stomach, using his fingers to
part its hair. The face was pretty and perfect, and John wanted nothing more
than to try what Dean had suggested.
But first…
John felt the nipples through his doll’s dress and rubbed them slowly, pinching
so he could hear—
Damn.
John chuckled at himself for forgetting already as Sam staying perfectly still
through a movement that would have had him whimpering any other time.
Sammy was his doll, which meant that he wasn’t going to react. It was a little
strange to accustom himself too, especially after his tryst with Dean in the
other room.
John got off of the bed quickly and pulled his doll towards him, setting him up
how he wanted him. Sammy’s head dangled helplessly over the side of the bed,
face up to receive John’s cock.
Without any warning, John grabbed his chin and thrust into the wet heat of his
doll’s mouth.
It wasn’t what he’d expected, not at all. Gone were the contracting muscles of
his son’s throat. A sucking sensation was but a dream compered to the looseness
of his doll’s mouth. His lips weren’t pulled over his teeth, and the light
scrape on his shaft brought unexpected tingles of pleasure, while still not
being enough.
He wanted, needed more friction.
Instead, he thrust harder.
When Sammy sucked, John could feel when he pressed past the boy’s gag reflex.
This time, though, he could hardly even tell it was there. There was no
struggle for breath when John fucked in roughly, deep in his throat over and
over again while he relished in the looseness of his new doll.
But it was a hollow victory.
It had been a fantasy of his for a while, to have one of his boys as a fuck
toy, but it wasn’t really what he expected. There were no whimpering moans,
gasps, or grunts, no lusty eyes, slinky tongues, or blinks of surprised
pleasure. It was silence and a wet passage. It was just one of the things that
was better in his head than putting it into practice.
He thrust in deep and held it, waiting for—
—there.
Sam’s muscles moved just the slightest, testing to see whether he could
breathe.
John held it.
He could feel Sam’s throat begin to tighten around his cock, struggling now
without air.
John held it.
Sam tried so hard to stay still, John could tell, but his diaphragm betrayed
him, twitching with need.
John held it.
Sam’s tongue moved against his cock—not a large movement, but subtle, so subtle
that John wouldn’t have noticed had he not expected it.
John held it.
And there it was… Sam gagged around him, his muscles flexing in an attempt to
rid himself of the intrusion in his throat.
John moaned in ecstasy and pulled out, letting his boy breathe. When it became
steady and subtle, John continued, trying to tease more slips from his boy.
He trailed his finger down the baby doll dress until it touched the hard
plastic of his doll’s cock cage. He gave the organ a flick, loving the half-
concealed twitch.
Another flick.
Then he bent down and licked the slit of his doll’s soft cock, wiggling his
tongue to tease the silky wet precome from his boy.
Sam’s breathing sped up, but the muscles stayed lax, something John promised to
rectify.
John leaned back and pumped his own cock while he watched his son’s skin flush
with need. It still wasn’t the reaction he wanted, but he had time.
Not bothering to lube himself up—Sammy had always loved his daddy to take him
hard, without much prep—John slid into his doll’s hole and hilted himself
roughly.
He fucked in and out of him, angling to hit his doll’s prostate, liking the
slight clench of the muscles whenever he succeeded. John latched onto Sam’s
hips and pulled his boy against him with every thrust, fucking deeper and
deeper until he was too on edge to continue.
Then he pulled out.
He had a goal. He wasn’t going to stop now just because of his rising orgasm.
Besides, there was something he wanted to try.
“C’mon baby doll,” John panted his Sam’s ear, loving the goose bumps that
formed on his doll’s neck.
John lifted the doll, limp in his arms, and held it tight against the wall,
lowering it until the hot tightness of his doll’s hole was surrounding him
again. He thrust experimentally, loving how the new angle stimulated the nerves
on his cock, and then he was fucking deep and hard, taking his frustration out
on his doll’s ass.
It wasn’t long before could hear the small gasps his son let out, could feel
the small twitches as he begged silently with every fiber of his being to be
allowed orgasm, but John didn’t relent.
He slammed in hard and fast, jarring his boy and making him forget that he was
supposed to remain still and silent. Sammy grunted and moaned, tears falling
from his eyes, and that was all John needed to come.
Hot seed spurted from his cock as he thrust into his boy’s now-clenching hole.
It leaked around him, dripping down his thighs as John continued the punishing
pace. He fucked his boy until he couldn’t and his spent cock slipped from
Sammy’s loose hole.
He looked right into his boy’s swimming eyes, still holding him tight against
the wall.
“Sorry, Daddy,” Sammy said. “I tried to be good.”
“You were the best, baby,” John said, licking his way into his boy’s eager
mouth. He pulled back and nibbled on Sam’s ear, loving the small whimper it
elicited. “Was trying to get you to scream,” he admitted.
“Bad Daddy,” Sammy said playfully, but his voice was thick with lust, and there
was an undertone John couldn’t make out that had his limp cock struggling to
harden. “I think you need to be punished.”
Oh yes, it was definitely struggling.
Chapter End Notes
     Okay, so to make up for my grievous mistake, I will grant a gift fic
     to the first two commenters on this chapter.
     Rules: There are no rules!! Just kidding. Rule #1: Has to be Spn.
     That's it. No more rules. Any pairing, and rating, any kink.
     Sorry again, people. Good news: the next chapter is going up in just
     a couple of minutes :) Stay tuned.
***** Bad Daddy *****
Chapter Summary
     Daddy was bad when he played with his doll. Sam and Dean think he's
     due for a punishment.
Chapter Notes
     Today's chapter has arrived! Here's some PWP for your viewing
     pleasure. Enjoy ;)
See the end of the chapter for more notes
It was another hour and a half before he could get his father’s cock to harden
enough to slip on the cock ring. Dean couldn’t come again for an entire week,
and Sam couldn’t for three days, but John couldn’t come until he’d been
punished thoroughly.
That was a nasty trick he’d pulled, and Sam hadn’t counted on that, but it
really didn’t matter what Daddy had done. Sammy would have punished him anyway.
Oh, he knew John had a pain kink, just as easily as he knew John loved when
they played with his nipples and called him daddy and wore pretty panties while
he fucked their tight holes. John was one kinky bastard. It was just another
quality that happened to run in the family.
He led John by his cock to Dean’s room and ignored the shocked pause his daddy
took in the doorway, pulling harshly to get him to move again.
Dean had done a great job transforming his bedroom into a makeshift dungeon.
They already had the cuffs and holsters in the trunk of the Impala, but
everything else he’d done—cloth-dimmed lamps, spotlights on the stand, and holy
fuck the chains—gave the place an ambience Sam didn’t think he’d be able to
achieve.
Dean was out of his lingerie now, like Sam knew he’d be. It was still a shock
to see Dean. His brother’s caged cock slipped through a hole in his leather
underwear and was attached by small chains to his clamped nipples, his entire
body surrounded by an undecipherable pattern of leather.
Sam absentmindedly thanked Dean for convincing him to do the whole cock cage
thing because he definitely wouldn’t be able to last the entire scene without
coming like he was supposed to. He still didn’t know if he could last the three
days until Dean released him.
“You ready?” Dean asked.
Sam nodded. Time to get the show on the road.
“Good.”
Without warning, Dean grabbed John by his hair and forced him down to kneel on
the stand. Sam came forward and strapped him in—wrists, elbows, knees,
ankles—leaving only his hands free.
Dean lined John’s head up with the cock-shaped gag and forced him onto it while
Sam strapped his head down. He was completely immobile.
John tried to talk around the gag, but Dean silenced him with a harsh look. He
squatted down so he was at eye level with John, making sure to have his
father’s attention before he continued.
“You okay with this?” he asked.
John gave a thumbs up.
“Okay. Give me a run through of your signals,” he ordered. “Slow down.”
John snapped with his right hand twice.
“Good. Remove the gag.”
John snapped alternately with his left and right hands.
 “Good. Stop the scene.”
John snapped with both hands.
“Good. Yes.”
John gave a thumbs up.
“Good. No.”
John gave a thumbs down.
“Good. For the rest of the scene, you will be completely immobile. Unless you
use the signals, we will not stop. Understand?”
John gave a thumbs up.
Dean smirked then. “Go ahead, Sammy.”
That was all the warning he got before a loud crack sounded in his ear,
followed immediately by a stinging pain on his back.
“Sammy’s been practicing. Haven’t you, Sammy?”
“Uh-huh,” Sam nodded.
Three more strikes of the whip and John was panting hard. His back was sore and
red. Welts were beginning to rise on the soft flesh, but John’s cock was rock
hard now and leaking steadily onto the floor, the cock ring holding his orgasm
at bay.
“Weapons practice has been a lot more enjoyable, I’ll tell you that much,” Dean
said. “How many does he get?”
“Fifteen,” the boy responded.
Dean quirked an eyebrow and Sam shrugged. They’d decided on ten to start.
“He kept trying to make me react when I was his doll. Flicked my cock and
everything.”
Dean’s cock pressed itself against the walls of his cage at the image in his
mind. Damn, he wished he was there for that. “Add five more,” he said instead.
“What for?” Sam asked, genuinely curious.
The whip struck again, and John grunted with the pain, his cock shooting
another wad of precome onto the floor.
“For trying to talk earlier. Daddy knows that he’s not supposed to talk with a
gag in his mouth.”
Sam smiled. The whip struck in rapid succession, and Dean hungered at the
sight.
“Ten,” Sam said, bringing his arm down again.
Dean signaled Sam to pause while he ran his fingers over the raised flesh of
his father’s back. John hissed around the gag at the prodding, but Dean didn’t
stop. “Daddy’s been so good for us. Don’t you think, Sammy?”
“He still has ten more, Dean,” Sam reminded him.
“I know. If we don’t finish his punishment, he’ll never learn his lesson.” But
Dean knelt down on all fours and took the swollen cockhead into his mouth.
Sam took John’s whimper as his cue to continue.
He counted each whip out loud, making sure not to strike hard enough to break
skin. When he hit fifteen, John’s back was a crisscrossed array of sensitively
swollen welts, pink with heat and glistening with sweat.
Sam set the whip down, taking a quick break to tongue at the sensitive flesh.
It was hot and bumpy, and the small trails of sweat were salty under his
tongue. He lubed up his fingers and shoved two inside of his father’s too-tight
ass.
John yelled against the gag, but his hands remained clenched so Sam continued,
forcing them in roughly, twisting and turning and scissoring them until he was
loose enough for a third.
John screamed when he added another.
“Hush,” Sam ordered, using his unoccupied hand to scrape lightly against the
welts on his back. “I don’t think Daddy’s learned his lesson, Dean,” he said,
thrusting the three fingers inside, hard and fast, while John whimpered
quietly.
Dean pulled off of his father’s cock, licking the slit once before standing. “I
think  you’re right. You almost done?” he asked.
Sam nodded.
“Good. I’ll finish his whipping.” Before Sam could protest, he continued, “Grab
the paddle. If Daddy thinks his ass hurts now, he’s in for a huge surprise.”
Sam kept up the brutal pace, fucking his fingers into his father’s ass until
the whimpers had died down and the muscle was loose and pliable. One last rub
against his prostate and Sam pulled out completely to retrieve the vibrator
they’d bought just for today.
It was larger than any of their cocks at a whopping ten inches, and its highest
vibration setting would have had Sam’s teeth chattering just holding the thing.
As it was, he had some trouble getting it past the stubborn muscle of John’s
ass. It was too large and John was too tight, but Sam forced it, adding more
lube as he went, until it slid in much more easily.
John’s muscles were all rigid while he accustomed himself to being impaled. He
didn’t bottom often, but when he did, he remembered just how much he loved the
stretch of his ass and the stimulation of his prostate, even with the large
amounts of pain both boys were intent on giving him. It merely added to his
pleasure.
“Don’t lose it,” Sam said once it was all the way inside. Then he turned the
vibration onto the lowest setting and stood back to watch as his father bucked
against his restraints, trying to find some kind of friction.
He was so entranced with his father’s wanton display that he forgot about Dean
until the telltale sound of a cracking whip broke his concentration. It was
barely deep enough to break skin, but unlike Sam’s previous blows, this one
drew a small drop of blood that had Sam wishing he could come.
They’d both agreed on this earlier, but Sam didn’t have the guts to make their
father bleed.
Dean seemed to enjoy it, though. All five strikes broke skin, tingeing John’s
back with red blood. Sam had a sudden urge to lick it up, but settled on
readying his paddle instead.
“Such a good Daddy,” Dean praised, running his hand down John’s leaking back.
“Staying quiet through your punishment. Still more to come, though.”
Sam took aim and waited for Dean.
Dean quickly unstrapped the gag from behind John’s head and pulled the phallus
from his mouth.
“Tell me, why are you being punished?”
John looked down in shame and answered. “For talking and yelling through my
gag,” he said.
“Eyes on me,” Dean ordered, his voice angry.
John’s eyes shot up of their own accord.
“Why are you being punished?” he asked again.
“For talking and yelling through my gag.”
Dean nodded. “Count. You have twenty-five.”
John jerked hard against his restraints as the paddle came down, easily hitting
both of his cheeks and jostling the plug inside of him. He groaned long and
loud, his prostate sending spark after spark of pleasure up his spine.
Dean’s hands pulling his hair got his attention.
“I said count,” Dean emphasized as Sammy brought the paddle down again.
“Two!” he yelled.
“No. You don’t get to continue when you didn’t count on cue. Start over.”
Sam wound up and brought the paddle down as hard as he could on his father’s
ass, loving the pained sound that came from him when he screamed, “One!”
“Good,” Dean praised. “And that’s ten more for disobeying an order. You have
thirty-five.”
John whimpered, but obediently counted, “Two!” when he felt the paddle again.
“Three… Four… Five…”John gasped, trying to breathe with haggard lungs. “Ten!”
“You’re doin’ good, Daddy,” Sam said, switching out the large paddle in his
hand for a different one. It was just smaller than a ping pong paddle, but
squared off and a slightly longer.
This time, John heard the whistle of air as the paddle smacked his bare
thigh—“eleven!”—before it moved immediately to his right—“twelve!”
It was more painful than the previous paddle, though he could tell it was much
lighter. It sliced through the air, the smacks stinging, leaving a burning
throb that made the skin so, so sensitive.
His back tingled with every movement from the whipping; his ass and thighs were
going to be bruised for days; his wrists, elbows, ankles, and knees were nearly
rubbed raw from his struggles; and his lungs were struggling to pull in air as
he sobbed from the pain.
Still, he couldn’t deny his arousal with his cock hard and leaking, ignored by
his boys, but straining against the cock ring with a need to come. The phallus
inside of him jerked with every hit, slamming into his prostate with its
vibrating head, sending shivers of pleasure throughout his body, masking the
pain.
No part of his backside was left out, the paddle making its way thoroughly
across both of his cheeks and thighs.
“Twenty-five!” he nearly sobbed, tears already coursing down his face to drip
on the floor beneath him.
The hits stopped then, and relief coursed through John at the knowledge that
they were giving him a short reprieve before continuing his punishment.
“Doin’ so good for us, Daddy,” Dean said. His hand came up to toy with John’s
sack, rolling it between his fingers.
Sam hummed in agreement, his small footsteps coming closer until he came into
view. He passed Dean the paddle and dropped to the ground beneath John. A small
smile was all John could see before he closed his eyes in ecstasy as Sam took
him into his mouth, sucking and moaning for all he was worth.
“You could’ve come by now,” he paused to say. “But you had to be bad.”
John couldn’t even think of a response as the wet heat of his boy’s mouth found
and suckled his head. He barely even remembered to count—“twenty-six!”—with his
brain malfunctioning as Dean let the paddle fly directly against the phallus in
his ass.
“Good, Daddy,” Dean praised, surprised that John was still able to count.
One after the other, the remaining nine strikes were taken out on John’s ass,
each one harder and quicker than the last.
“Thirty-five!” John screamed, thrusting as much as he was able into Sam’s mouth
while the boy moaned his appreciation.
Dean was at his ass then, grabbing the phallus and fucking it in and out of
John’s ass, making sure to angle it just right to have him writhing against the
bindings. His other hand skimmed his father’s back and thighs, slipping beneath
to tug at his sack—Sam’s signal.
John felt Dean scratch lightly at the heated flesh, nails dragging against
sensitive skin, and then the dreaded cock ring was gone, his rising orgasm only
held back by sheer force of will.
“Come for us, Daddy,” Dean said, placing a hard smack on his ass.
John was done for.
Harder than he ever had before, John came into his son’s mouth, screaming his
release as pleasure coursed through him, triggered again and again by the
throbbing pain at his backside. His vision swam, and John blacked out by the
force of it.
The last thing he heard before he was completely out was his sons’ voices in
his ear.
“Such a good Daddy,” Sam said.
“The best,” Dean agreed.
And he was gone.
Chapter End Notes
     And wasn't that enjoyable? I know I had to take a couple of /breaks/
     in between writing this chapter. The next chapter will go up
     tomorrow. It will contain the final piece of plot for this fic. Sad
     to see it end? No worries. The next fic will go up July 4th,
     regardless of working internet or not. Worst case, I'll post that
     shit at the nearest Starbucks. Comment your happiness, people! And
     kudos your enjoyment :)
***** Aftercare *****
Chapter Summary
     It's the next morning. Dean's guilty. John's caring. Sam's just
     horny.
Chapter Notes
     Final chapter everyone! It was supposed to be more plot, but it kinda
     ended with some relatively vanilla sex instead. I'd apologize, but I
     don't think those screams are complaints. Do you? If so, don't forget
     to comment them! Enjoy ;)
See the end of the chapter for more notes
When John came to, he was lying on his stomach with two angels surrounding him.
Soft fingertips wound their way through his hair, petting him lightly, while
something soothingly cold was massaged gently onto the skin of his backside.
His wounds were dressed, and his muscles were loose and limber, the ache a
comfortable feeling after such an intense scene—hell, three of them. He would
have been content to stay where he was had his mind not tuned into the hushed
conversation.
“Dean, stop freaking out, okay? He’s fine.”
“He’s freaking bleeding, Sam. I did that. How could—fuck…”
“It’s not even bad. Look. They’re barely more than scratches. Gone in three
days, tops. Besides, it was on his list, remember? You didn’t even go that
far.”
The silence he was met with was enough for John. He blinked his eyes open,
trying to unblur everything around him and settled on rubbing his hand over his
face. He picked himself up onto his forearms and pulled his legs under him so
he could sit on his knees—the only comfortable sitting position he would have
for a while.
“Hey, Dad!” Sammy said, smile blinding.
Both of the boys’ makeup was gone, and the only clothes they had on were their
birthday suits. He wasn’t disappointed in the least at the sight. “Hey,” he
said, sleep still in his voice. He cleared his throat and tried again. “You
boys did so great. I’m proud of you.”
“Do you hurt anywhere?” Dean asked, ignoring the praise.
John almost frowned. “My back stings a bit, but it’s my ass that’s sore. Been a
while since I’ve taken it.” He smiled then, but Dean didn’t respond. “How about
you boys? I was kinda rough with you—especially you, Sammy—but I left my cock
in Dean quite a while. You okay?”
Sam kept the smile on his face. “I’m awesome.”
Dean just nodded quietly.
John fingered Sam’s cock cage, and the boy hissed with a mixture of pain and
pleasure. “Does it hurt?” he asked.
Sammy shook his head. “Just sensitive. I wanna come so bad.”
“How about you, Dean?”
Dean bit his lip. “It feels like it’s got a chokehold on my cock. Can’t get
hard for nothin. I like it though.”
John nodded, completely aware of Dean’s withdrawn disposition. He quirked an
eyebrow and Dean smiled, but his face was tight, screaming I’M SORRY! without
having to speak a word.
“Dean,” John chided.
Dean looked down and John pulled him limply into his arms, cradling his head
and petting him lightly. “You did so good,” he said. “Gave me exactly what I
wanted.”
“You got hurt,” Dean murmured against him. “And I liked it.”
“No,” John comforted. “I got punished, and you liked it. We both did.”
“I went too far.”
Sam scoffed, but John cut off his argument with a quick glance. “Do you trust
me, Dean?” John asked seriously.
Dean looked up at him, confused. “Of course,” he answered.
“Good. And I trust you too, both of you.”
“You shouldn’t,” Dean said sullenly, looking down in shame. “I hurt you.”
John pulled his chin up and pressed their lips together in a comforting kiss.
“If I told you to stop, would you?” he asked, pressing in for another light
kiss.
Dean nodded, unable to speak with his father’s mouth molding itself to his own.
“Then there’s no problem,” John said, smiling and pulling back to look Dean in
the eye. Dean really needed to hear what John said.
“Yes there is!”
“No, there isn’t. If I wanted you to stop—if you were really hurting me—then I
would have signaled you, and you would have stopped.”
“But I liked it,” he forced out. That was the real problem. It was one thing to
draw blood, quite another to want to see more of it.
John smiled amusedly. “You were supposed to like it, Dean. If you don’t like
it, I don’t like it.”
Dean bit his lip again, still conflicted, but not anywhere near where he’d been
before. “You sure?” he asked.
“One hundred percent. Sammy liked it too. Didn’t you, Sammy?”
Sam nodded, nearly bouncing on the bed. “It was so hot, Daddy, seeing you tied
up like that. Sexy as hell watching you writhe for us. I wish I coulda fucked
your ass right then and there, but Dean said I have to wait two more days.” He
looked down at his cage in anger, but there was some heat in the gaze too so
John didn’t read too much into it.
“See,” was John’s response. “Everyone’s good.”
Dean had small smile on his face and John counted it as a minor victory.
“You took real good care of me, boys,” he continued, crushing his mouth against
Dean’s, not holding back like he had before. He slipped his tongue inside,
running it over the slick white teeth.
Dean gasped into the kiss, and moaned his pleasure.
“Such a good boy,” John said. He parted Dean’s legs so Dean was straddling him
from below. “My princess,” he said, kissing deeply once more until Dean’s legs
wrapped around his waist in an effort to lessen the distance between them.
John smirked and pulled back just long enough to line up and slide his cock
into his son’s loose hole, still slick with come and lube from last night’s
excursions. Dean hiccupped in surprise, but immediately set about driving John
deeper inside of him until he could feel his father’s thighs press tight
against his.
John’s eyes rolled at the feel of his boy’s hole on his swollen cock. Unable to
think, just acting on instinct now, he reached out and pulled Sammy in until he
was seated in front of him, chest to chest, straddling Dean’s stomach. He
thrust slowly now, wanting to savor the moment, the feel of Dean’s tight ass
around him.
Sam smirked and latched onto a nipple, causing John to gasp. His fingers came
up to absentmindedly pinch and prod the other one while his brother fucked
himself on their father’s cock. John was gasping and groaning, the slick and
slide of Dean and the sparks of pleasure of Sam at his nipples overwhelming
him.
Sam bit down hard and licked the reddened flesh, relishing in the cry his
father let out at the movement.
“Fuck,” John gasped. His hips stuttered, muscles twitching when his orgasm
caught him by surprise.
Dean screamed when the flood of come sent sparks of pleasure through him in
time with his father’s release, his cock still soft but making a valiant effort
to rise.
Sam continued to toy with John’s nipples as he pulled out of Dean and collapsed
back onto the bed, not caring that he could feel the marks on his back with
every movement.
“Holy fuck, baby doll,” John gasped.
“Your nipples are sensitive, Daddy,” Sam said, tonguing at the one he bit.
John just chuckled. He pulled Dean closer and wrapped them both in his arms.
“Feel better, princess?” he asked.
Dean blushed, but looked at him, eyes sparking. “Much better, Daddy,” he said.
“Good,” John said. “Get some rest. Sammy gave us a few days before another Hunt
comes callin’ and I wanna fill you both up before then.”
Both boys squirmed, wiggling closer, before closing their eyes obediently.  
Chapter End Notes
     And that's it. End of fic. The next "Holidays with the Wincesters"
     fic will come on Independence Day, the 4th of July, 2014. Rain,
     sleet, snow, or lack of internet shall not keep me from posting, so
     tune in then :)
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