Training Big Brother
- 2 years ago
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Training Big Brother V free porn video
Surprisingly, after going to bed late, Tom was up bright and early the
next morning. He quickly emptied the dishwasher and waited for Karen to
come down. It was Monday, a gym day, so he had another chore.
"Don't forget my bed," she said to her brother.
"Yes ma'am. I was waiting for you to come down." He hurried back
upstairs, made her bed then grabbed Becky's homework.
"Here Karen. I finished Becky's homework. Would you please give it to
her?"
"Let me see," she said, taking the folder. It was thick with pages.
"This looks like it took awhile. What time did you get done?"
"About one in the morning. And," he added with a small smile, "I've got
the sore fingers to show for it."
Karen smiled. "But you now know how to address Miss Becky. So I think it
was a good trade off." She put the folder with her books. "Don't forget
you're to head straight over to Becky's house after school. After you
change, of course."
"Yes ma'am," Tom replied.
School was uneventful, except for his lack of homework. He grudgingly
took his F's for not handing in his school assignments. He'd handed in
the important ones to his new taskmistresses. But he was happy to be
wearing underpants instead of panties, if even for only a few hours.
After school, Tom got off the bus and hurried home. His sister wasn't
home but he didn't give that a second thought. Becky was expecting him
and he didn't want to be late. He knew she planned to punish him and he
didn't want to make her any angrier.
He changed into his panties and a bra, selected a T-shirt and put it on.
The bra straps were quite visible beneath the shirt and he prayed he
wouldn't run into anyone he knew on the way over.
He felt very self conscious when he stepped out the front door. He was
quite aware of his bra and, looking down, could make out the outline of
its cups under his T-shirt. He hurried over to Becky's house, thankful
he didn't run into anyone he knew.
Becky answered the door, opening it partway. "Lift up your T-shirt. I
want to see if you've got your bra on."
Oh Christ. Not outside! "Miss Becky! Please! Can't you see the straps
under my shirt?"
"Oh Tom. I see you've still got a lot to learn. Of course I can see the
straps but I want you to show the world you're wearing a bra." She
answered sweetly but then her voice turned sharp. "Now lift up your T-
shirt before I get angry!"
Tom gulped. "Yes Miss Becky," he hurriedly replied and pulled his shirt
up, exposing his bra. Becky, little brat that she was, waited a full
thirty seconds before allowing him entry. When she finally fully opened
the door for him, he scurried inside, pulling his T-shirt back down.
"You're looking cute, big bro." Karen smiled at him from the kitchen
doorway. Tom realized of course she'd be here. "Ok. Now get out of those
clothes."
"Yes ma'am," Tom replied. Why couldn't he keep his boy clothes on over
his girl underwear? Oh well. He undressed down to his bra and panties.
Becky scooped up his clothes which he'd placed on a chair.
"We'll just put these out of the way for now." She went through the
kitchen and out the back door, returning a few minutes later, empty
handed. "Don't want you running away," she said with a laugh.
"I gave you a break last night," Becky continued. "But you're still
going to be punished for not getting my homework done on time."
"Yes Miss Becky," Tom replied with lowered eyes.
"You're going to get a spanking."
Oh Jeez! Spanked? By a thirteen year old girl? Christ! Tom felt his
penis twitch at the thought.
"It's either that or I will share those pictures of you. So what's it
going to be?"
Tom gulped. Great choices, he thought. No way did he want those pictures
out in public. "The... the spanking, Miss Becky."
"I thought that might be your choice. Follow me." She led him into the
kitchen where a barstool was standing. "Bend over that," she directed.
Oh Jeez! But Tom didn't have much of a choice. He approached the stool
and bent over it, his feet touching the legs and his hands gripping the
bottom rung. God this was humiliating! Even more so when Becky yanked
his panties down, exposing his bare bottom.
SMACK! ... SMACK! ... SMACK! Becky's hand came down hard.
Geez that hurt! "OWWWWWW!" he cried, involuntarily bringing his arm up
to protect his rear.
"Put that arm back down," Becky exclaimed angrily, giving Tom time to
comply before bringing her hand down onto his bare bottom again. SMACK!
... SMACK!
"OWWWWWW!" Tom yelled again. Christ! That hurt. His arm went back up to
cover his rear again.
"Ok Tom!" Becky exclaimed, stepping back. "It seems you can't keep your
hands down where they belong. We'll just have to help you do that." She
picked up a roll of duct tape, which she'd earlier placed conveniently
on the counter, and motioned Karen over.
"Karen's going to tape your feet to the stool legs," she explained,
ripping off a two foot length of duct tape and handing it to his sister.
"I'm going to tape your wrists together." She tore off another length of
tape. "Hold your arms out."
Oh Christ! "Wait... Wait!" he cried.
"No Tom," Becky said. "We're not waiting. Either put your arms out or
those pictures are going out."
Oh Jeez! Those damn pictures again! He held his arms out in front of
him. A moment later Becky had the tape wrapped tightly around his
wrists. Meanwhile Karen had his right ankle taped firmly to one stool
leg and was ripping another length of tape to attach his left one. That
ankle was quickly attached to another leg.
"Get back down over the stool," Becky commanded. Tom complied and she
dropped to one knee with the roll of tape. After positioning his wrists,
she taped them to the bottom rung with several loops of tape. Tom wasn't
getting free anytime soon.
Becky winked at Karen. They'd planned to tie Tom down all along. Now his
real punishment could begin! She stepped over to the sideboard and
picked up her mother's riding crop. When she'd shown it to Karen, her
eyes had lit up at the idea of using it on her brother. Now she would
get her chance.
Swoosh. SMACK!!!
"YEOWWWW!" Tom yelled, bucking frantically and almost tipping the stool.
My God! That stung!
Swoosh. SMACK!!!
"YEOWWWWWW!" Tom yelled again. "PLEASE!" he cried. "That really hurts!"
"And it's going to hurt some more. This is what happens when you don't
do what I tell you. Swoosh. SMACK!!! Swoosh. SMACK!!!
"OWWWWWWWWWW!!!" Tom screamed, almost in tears.
"Becky... Becky," Karen interjected. "He's way too loud. The neighbors
might hear."
"Good point," Becky replied. She grabbed the roll of duct tape and
placed a length of tape over his mouth, wrapping it several times around
his head.
"Mmmmmmppphhhh!" Tom tried to speak but nothing intelligible was coming
out. He was in deep water now!
Swoosh. SMACK!!! Swoosh. SMACK!!! Swoosh. SMACK!!! Becky was back at it.
"MMMMMMMMMMPPPPPPHHHHH!!! MMMMMMMMMPPPPPHHHHH!!!" Tom bucked frantically
as best he could but the duct tape held. Karen held him so he wouldn't
tip over while Becky continued to spank him. It wasn't long before he
was sobbing uncontrollably while screaming into his gag.
"Next time I tell you to do something I don't want to hear any excuses.
It wasn't Karen's fault you missed my deadline." Swoosh. SMACK!!!
Swoosh. SMACK!!!
Finally, after five slid minutes of solid spanking, Becky stopped. Tom
was in tears, cursing that he'd ever gotten himself into this
predicament. Unfortunately it wasn't over.
"Your turn," Becky said, handing the riding crop to Karen.
Oh God! What had he done wrong? He'd finished her homework!
Swoosh. SMACK!!! Swoosh. SMACK!!!
"MMMMMMMMMPPPPPHHHH!!!" Oh God! That hurt! Becky steadied him so that
his frantic thrashing didn't tip the stool.
"You do not! I repeat. You do not dress up in my underwear without
asking permission. Do you understand?"
"MMMMMMMMPPPPPPPHHHHH" Tom said, nodding his head furiously.
Swoosh. SMACK!!! Swoosh. SMACK!!! Swoosh. SMACK!!!
"You have your own bra and panties now. That's what you wear. Not mine.
Understand?"
Tom nodded his head up and down. It was all he could do. His bottom was
beyond sore now but his sister kept at it. His spanking was far from
over.
The girls kept going, alternating about every five minutes or so. Tom's
bottom went from pink to red to crimson. The riding crop repeatably left
its mark on his sore cheeks. Finally, after twenty minutes they stopped
and stepped out of the kitchen, leaving him bent over the stool sobbing
uncontrollably.
"What do you think?" Becky began. "Your brother wasn't expecting a
spanking like that at all."
"Well it's about time. He's been a bit of an a-hole lately. That is up
until I discovered he'd been dressing in my undies and got those
pictures. Since then he's been a lot nicer. I think a spanking every so
often will serve to remind him that he's to obey me from now on."
"Let's leave him bent over the stool like that for awhile," Karen
continued. "And let's not to forget to take some pictures." The two
girls laughed.
"What's next?" Becky asked.
"Makeup? He needs to get started. How about some lipstick?"
Meanwhile, Tom remained in his uncomfortable position with his mouth
taped shut, sobbing quietly. His bottom stung like it never had before!
He couldn't believe his little sister and her friend had done what they
did.
When Becky had said she would still punish him for failing to get her
homework done on time, he'd never expected this. And Karen laid into him
just as bad. God! The girls really did a number on his butt. And
unfortunately because of the embarrassing pictures, they could do it
anytime they chose. Christ! He needed to be very careful not to make
them angry. He wasn't going to disobey his little sister ever again!
A half hour later the girls came back, their phones out. They snapped a
number of pictures, including several of his sore red bottom with
stripes where the riding crop had cut into him. Karen sent one of those
to Tom's phone so he could see the damage they'd done. It would be a
reminder of what could happen again.
"So Tom," Karen began, picking up the riding crop. "Shall we continue or
are you going to do what we tell you?"
"Mmmmmmmpppphhhh," Tom answered, shaking his head violently. Of course
he didn't want to continue his spanking! Unfortunately, what he was
doing could be interpreted either way.
"Oh? More spanking?" Karen brought the riding crop down hard onto his
already sore bottom.
"MMMMMMMMMMPPPPPPPPHHHHHH!!!" Tom screamed into his gag. Oh God! He
couldn't take any more of this! The tears started flowing again.
"No? You don't want me to spank you?" she teased. "Would you like Becky
to spank you instead?"
"Mmmmmmmpppphhh," Tom shook his head. He didn't want to be spanked at
all!
"Here Becky," she said, handing the crop to her friend. "I think he
wants a swat or two from you."
"Mmmmmmmmppppphhhh!!" Tom was shaking his head frantically.
Swoosh. SMACK!!! Swoosh. SMACK!!!
"MMMMMMMMMPPPPPPPHHHHHH!!!" Oh God! How could he get them to stop?
"Shall we keep spanking you or would you like to go upstairs to Becky's
room so we can teach you how a girl puts on makeup?"
Tom shook his head up and down violently. Makeup! Please let's do
makeup!
"What's that? More spanking?"
NO NO NO NO NO! Tom shook his head.
"You want to learn how to put on makeup instead?"
YES YES YES YES YES! Makeup! Please! Tom bobbed his head up and down.
"Ok," Karen said. "We're going to remove the tape but if you give us any
trouble, your pictures are going viral. Understand?"
Tom nodded and the girls freed his ankles and wrists from the stool,
although his wrists remained bound together. Then, somewhat gently, they
untaped his mouth.
"Oh God!" he cried when he could finally speak. "That hurt! That really
hurt! Please don't ever use that... that whippy thing on me again!"
"That whippy thing is my mother's riding crop," Becky explained. "And we
will use it again if you don't get upstairs."
"Yes... Yes Miss Becky." Tom immediately headed for the stairs. He
wasn't taking any chances.
The girls smiled at the sight of Karen's older brother scampering up the
stairs, afraid of another spanking. His wrists were still taped together
making it difficult to pull up his panties, but he managed to get them
over his bottom by the time he reached Becky's room.
"Sit," Becky directed, pointing to the stool in front of her makeup
table.
"Yes Miss Becky," Tom replied and proceeded to sit gingerly on the
stool. "Eww," he moaned, shifting when his sore bottom came into contact
with the stool. "It... It hurts," he said.
"That's too bad," Becky said. "Now we're going to start with lipstick."
From the table she selected a lipstick and pulled off the cover. Then,
motioning Tom to hold his head still, she proceeded to apply a deep
shade of red to his lips.
"What do you think?" she asked Karen.
"Not bad," came her response. "Do you like it Tom?"
No dammit! He was a boy! "Yes ma'am," he replied quickly, not daring to
disagree.
All of a sudden they heard the front door open. "Becky... Becky. Are you
home?" It was Jill.
Tom gulped. Oh Jeez! Not Jill again. His penis twitched at the thought
of being seen like this by Becky's sister. Again.
"We're up here," Becky replied. "In my room."
Tom heard the rumble of feet on the stairs and wanted to disappear. His
penis though, had a different idea and he became instantly erect. Then
Jill was in the doorway.
"Oh my god!" she exclaimed, eyes wide as she took in Tom in his girl
underwear. "How's our little sissy boy?"
Tom's face turned a bright red. He wasn't a sissy! The girls were making
him wear these things!
"Our little sissy boy just got his bottom spanked," Becky said, somewhat
proudly. "Show Jill your bottom," she said to Tom.
"Yes Miss Becky," Tom replied, standing up to pull his panties down. It
was a little difficult since his wrists were still taped together in
front of him. He managed though, pulling the front way down. Eventually
the rear followed and his sore, red buttocks were exposed to Becky's
sister.
"Oh! You certainly did a number on him," Jill exclaimed.
"Yup. Mom's riding crop worked like a charm." Becky laughed. "We even
had to tape his mouth shut, he was yelling so much."
"Is this all because he didn't finish your little homework assignment on
time?"
"Partly," Becky said. "Karen also worked him over for dressing up in her
underwear without permission."
Tom stood there listening to the girls, ashamed and humiliated. His
erect penis though, was not ashamed at all. It pointed stiffly in front
of him.
"Turn around, Tom," Becky directed.
"Yes Miss Becky." Tom did as he was told. 'Yes Miss Becky' was becoming
automatic for him.
"Oh that's so cute," Jill exclaimed now that Tom was facing her. "He's
got a little baby boner. Just like in that picture you showed me."
Tom wanted to die. Jill had obviously seen the picture with the ruler.
Christ! Who else had seen it? This was so embarrassing! His penis
twitched excitedly then twitched again. Oh God! No! But he couldn't stop
himself. He began spurting in front of the girls.
"Oh my God!" Jill exclaimed. "He's cumming!"
Poor Tom. He tried covering himself with his hands but he kept
ejaculating. On the one hand he was mortified that this was happening in
front of the girls. But it felt so good! He couldn't help it and began
rubbing his erection with his taped hands.
The three girls watched in awe as the milky white liquid spurted from
his very aroused penis, landing on the floor in little puddles. "Oh
Jeez, Tom! You've made a mess!" Becky exclaimed angrily when it was
over.
She stepped to her nightstand and grabbed a bunch of tissues. "Here Tom!
Clean up your mess!"
"Yes Miss Becky," a mortally embarrassed Tom said, dropping to his knees
to begin wiping up the little puddles he'd made. Not wanting to take any
chances by angering her further he apologized. "I... I'm sorry Miss
Becky. It won't happen again."
Jill smiled and nodded at her younger sister. "I like the way you've got
him trained. Having him call you 'Miss Becky' is a nice touch."
"But," she continued. "He shouldn't be allowed to cum like that. Spewing
his jism all over the floor... it's just not proper." She smiled
impishly. "I think he needs to be taught a lesson about that."
"Throw those tissues away Tom and get over here." Jill sat down on the
stool and waited. Tom came over and she pointed to her knee. "Lie down
over my knee," she directed.
Tom gulped but was afraid to object. Following her directions, he lay
down across one knee. She immediately hooked her other leg around his,
holding him in place. Down came his panties, exposing his red and sore
bottom.
"Ok Tom. This little spanking is to teach you it's impolite to squirt
your jism all over the place." SMACK!... SMACK!... SMACK! "Understand?"
"OWWWWWW!... OWWWWWWW!... Yes! Yes! I understand!... Please! That
hurts!" Tom cried. God! His sister, Becky and now Becky's sister were
all taking turns spanking him. What he didn't know was that both Becky
and Karen had their phones out and were videoing his latest spanking.
Jill did though and she tightened her grip on him before letting go with
several hard smacks to his bottom.
"OWWWWWWW!... OWWWWWWW!" Tom cried out in pain. "Please Jill! That
really hurts!" He squirmed vainly as Jill not only had his legs
trapped, but also had one arm wrapped around his back, pressing him down
onto her lap. "I'm sorry!.. Please stop spanking me!"
Becky and Karen were having a tough time containing their giggles as
their phones continued to video him, laying over Jill's knee being
spanked and begging her to stop.
"OWWWWWWW!... OWWWWWWW!" Jill was ignoring his frantic pleas, continuing
to smack his bottom with relish. "Please stop! ... Jill! Please
Jill!...OWWWWWWW!... Oh Jill! Please! That hurts! ... OWWWWWWWW!"
Finally Jill gave one last resounding SMACK and stopped. Tom had given
up trying to hold back his tears and was now bawling like a baby. "Ok
Tom. Get up," Jill said, pushing him off her lap.
Tom managed to stand up, wishing he could rub his sore bottom.
Unfortunately his wrists were still taped together in front of him.
Instead he grasped the front of his panties and pulled them back up.
Becky looked at her bedside clock. "It's getting late," she said. "Mom
and Dad ought to be home soon."
"Yeah," Jill replied. "Mr. Sissy probably should get going." With that
the girls headed downstairs, taking Tom with them.
Karen had collected her purse and was by the front door getting ready to
leave, saying her goodbyes to Jill and Becky. Tom was still in just his
bra and panties.
"Karen... I can't go home dressed like this. I need my clothes back."
"I don't have them," she replied. "Becky took them."
"Becky," Tom began, turning to his other tormentor. "Can I Please have
my clothes?"
She scowled at him and with one finger pointed to the floor in front of
her. "Do I have to give you another homework assignment?"
Tom gulped, realizing what he'd forgotten. It was humiliating to do it
with his sister and Jill watching but he did not want more homework. He
dropped down onto his knees. "Please Miss Becky. Please would you give
me my clothes back?"
"I ought to make you go home like you are," she said somewhat angrily.
"I... I'm sorry Miss Becky. It won't happen again," Tom said, hoping to
appease her. She glared at him for another moment before muttering 'all
right' and heading off to get his clothes.
She came back several minutes later with his clothes and a pair of
scissors. She first cut the tape around his wrists. Relieved, Tom
quickly pulled on his pants. He reached behind to unhook his bra when he
was stopped by his sister.
"You wore it over here. You can wear it home."
"But... but mom might be home. She'll see it," Tom protested.
"Then you'd better hurry home before she gets there," Karen said.
"Yes ma'am," he replied sensing it was useless to argue. He grabbed his
T-shirt and put it on knowing it didn't do much to hide his bra.
Finally, with his shoes on, he and Karen left for the ten minute walk
home.
"Well, that was an exciting afternoon for you, wasn't it?" Karen said.
"Not... not really," Tom replied. "That riding crop really hurt."
"I'm sure it did. That's why we used it on you." She smiled. "And we'll
use it again the next time we decide you need to be punished."
Oh Jeez. The crop really hurt. He didn't want to be punished again. God!
How had this happened? Spanked by his younger sister and her friend.
"Please don't," he said, hating that he was so powerless to defy them.
"We'll see," Karen said noncommittally. "Do what your told and maybe we
won't have to punish you."
"Yes ma'am."
The walked on in silence for a couple of minutes. Tom was afraid of
running into anyone he knew.
"I've been thinking," Karen said. "Wearing girls underwear is great for
during the day but you also should be wearing something at night." She
smiled. "I'm going to lend you something... just until we get to go
shopping again."
Tom looked over to her expectantly, knowing it would be something he
didn't like.
"One of my nightgowns," she said. "When we get home I'll get you a
nightgown to wear tonight and every night until we get to the mall. Ok?"
With the spanking still fresh in his mind (and his bottom) he sullenly
replied. "Yes ma'am."
They walked the rest of the way without speaking. Karen was pleased that
there'd been no argument from her brother about the nightgown. He was
getting accustomed to obeying her. Of course the spanking helped
solidify that. She smiled to herself.
Tom on the other hand, was cursing his predicament with the girls. Those
damn pictures they had forced him to submit to their spanking. And then
Jill came along and joined the party. Christ! She'd done a number on his
already sore bottom. Now Karen wanted him to sleep in her nightgown! And
he'd better do it or he'd be in for another spanking or have his
pictures shared or both! He hated his little sister for this.
Luckily their mother wasn't home yet. Tom hurried to his room to remove
his bra, hiding it in his desk as usual. Karen appeared in his doorway a
few minutes later. In her hand was one of her nightgowns.
"Wear this tonight when you go to bed. Mom won't see you - just stay
under the covers if she comes into your room."
"Yes ma'am."
"And text me a picture of you wearing this tonight. And one again in the
morning when you wake up. Just to make sure you're following my
directions."
"Yes ma'am," Tom replied again. Damn her! He took the nightgown and hid
it under his pillow.
Dinner was uneventful except that their mom noticed Tom's continued
shifting about. His sore bottom made sitting difficult. He just said he
was feeling a bit fidgety and tried his best to sit still.
After dinner he attacked his homework, again shifting about to ease the
pain he felt. The spanking had been quite intense and a look in the
mirror showed the red stripes on his buttocks from the riding crop. He
was lucky there was no bleeding.
He spent more time than usual on his homework, trying to make up for his
missing weekend's homework. Finally at ten thirty he called it quits and
got ready for bed. After showering and brushing his teeth, he was back
in his room. He shut the door and pulled Karen's nightgown from beneath
his pillow.
He slipped it on and it became evident it was not only tight but also a
bit short. It barely came down past his crotch. Karen, at only thirteen,
was somewhat smaller than her sixteen year old brother. He dutifully
took a selfie and sent it to his sister.
'Cute!' Came back the response followed by: "Becky thinks so too."
Oh Christ! She'd shared it with her best friend! How was he ever going
to get out from under his tormentors? Even if he somehow managed to get
Becky's phone and delete the pictures, Becky had her own set. And
probably Jill had a bunch too! No way could he get a hold of their
phones!
And after this afternoon's spanking, he was afraid of angering them.
Becky had wielded the riding crop with a ferociousness he didn't want to
experience again. And Karen caught on quickly too, smacking him hard
right from the get go. He didn't want the riding crop to come out ever
again!
But how the heck could he get Karen and Becky to stop dressing him up
like a girl? It wasn't happening tonight, that was for sure he thought
as he looked down at the nightgown he was wearing.
Becky was a little bitch. He was ashamed that he had to call her 'Miss
Becky'. It was humiliating; after all she was only thirteen. But he did.
He was afraid to disobey her.
And Karen was no better. She was making him dress like a girl and, like
with Becky, he was also afraid to disobey her. That's why he was now
wearing a nightgown. If there was only some way he could get the upper
hand and make the girls stop.
He rolled over to go to sleep and realized he had an erection. Again. Oh
Jeez. The snugness of Karen's nightgown around his chest felt somewhat
similar to wearing a bra. His penis grew more excited and he started
thrusting his hips against the bed. A minute later he began spurting
into the nightgown while having an orgasm.
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