Babysitting A Diva

Stephanie is a young woman, in her mid-20s. She has always been “daddy’s
little girl.” What others fail to realize is that Stephanie STILL lives at
home with her parents when they are not traveling. She still has her own
little room, still sleeps in pajamas, and still calls her father, “daddy”.
One more thing you probably didn’t know… Vince always thought of Stephanie
as “his baby” and really never treated her her own age. During college, she
always had a 10 PM bed time, and was sheltered from peers her own age.
Several years ago, when Stephanie was starting college, and not on TV yet,
Vince STILL didn’t let her go. He hired
a babysitter to watch over his 20
year old daughter. Sound strange? Well this is just the beginning.

(Flash back to before Steph was the ECW owner.)

Scott was a few years younger than Stephanie at the time. So when Vince
looking for a babysitter for Steph back then when she was in her late teens
and early 20s, Scott was barely 18, if that. He was just about to enroll in
college, and need a job FAST. Scott couldn’t find a damn thing in the
newspaper, and going door to door asking for applications was not cutting
So a female friend of his said she was hired for a babysitting job, got
hired, but couldn’t do it on certain days because she also had another part
time job. So she referred Scottny-boy for the position and he told her that
would do it. She kept assuring him that he was “house” sitting, as opposed
babysitting. Scott knew she was just trying to ease his mind and his manly
(Male babysitter? He HAD to pay the college fees though.) That’s when she
told Scott who it was for. He nearly crapped his pants when he found out he
would be babysitting Stephanie McMahon… he knew the name, but not really
who she was…. but she was OLDER than Scott! Wow. Scott tried to play it
and prepared for his trip to the mansion.

Scott made his way to the lush mansion and knocked on the door. A maid
answered the door and let him in, then showed him around the large estate.
Room after room, Scott could not get over the sheer size of the house. The
took him to each one of the 3 floors and showed him everything.

“Now Scott, here’s the rec room… here’s the workout room… here’s the
bathroom… here’s Stephanie’s room….”

Scott peeked in Steph’s room and saw the busty beauty in simple shorts
a tank top, laying on her stomach, legs curled up, reading a book. Stephanie
looked up and made eye contact with Scott, smiling and waving. Scott got an
instant hard on, waving back, thinking ‘she fucking HOT!!’ as the maid
continued the tour of the house.

“I must be running along now Scott. If you need anything just page me or
tell Stephanie. Linda, Vince, and Shane are all on a business trip at the

She moved in to Scott’s ear and started to whisper.

“Stephanie doesn’t know a whole hell of alot about the business… so she
just stays here. She is so damn immature that she can’t watch the house by
herself so that’s why you’re here…”

Scott nodded at the brutal honesty and cracked a smile as the maid said
goodbye and exited the house.

Scott settled into his room, right next to Stephanie’s, then headed for

As he passed Steph’s room, he didn’t see her on the bed any more. He was
going to say hi, but instead just went about his business. He showered and
shaved in the enormous bathroom, getting ready for the evening of a whole
of nothing.

Stephanie was immature, but old enough to take care of herself. She was
fucking 20 years old! Geesh! Older than he was! So he wasn’t babysitting
after all, just taking up space.

Scott was about to get in the shower when he forgot to get his towel in
room. He put on just his boxers and walked across the hall to his room and
came back in the bathroom with his towel. As he was shutting the bathroom
door, he caught a glimpse into Steph’s room. She was on her bed again. Not
having his contacts in at the moment, he squinted at Stephanie and saw her
facing away from him….with her shorts and panties around her ankles.

Laying on her bed on her back, Stephanie was rapidly rubbing her clit and
holding her left breast under her tank top. She must had thought Scott was
already in the shower! Scott closed the bathroom door most of the way,
a little crack opened so he could peep on the sexy Steph. She was really
getting in to it, rubbing her index finger on her clit, legs bent and open
wide, toes all scrunched up. He could hear little “uhh… uhh…” noises
her. Scott’s boxers struggled to contain the monsterous growth that
was unknowingly causing. Suddenly the door Scott was behind creeked, making
loud noise, and Stephanie jumped up and moved out of sight. Scott held his
breath and mouthed the word “FUCK” as he slowly closed the door and got in
the shower. He made sure it was a cold one. He couldn’t help but remember
image of Stephanie Mcmahon half naked and playing with herself. He thought
‘was she thinking of me? of a guy? of a girl? what?’ as his cock stood
straight up in the shower. It had been almost a week since he jerked off
because he was just too busy and was always sleeping over at someone else’s
place or doing something. He decided that this was not the right time for

When Scott got out of the shower and got dressed, he opened the door to
Stephanie’s light was shut off. It was about 9:45 PM or so, and he
Steph’s bedtime was about then.

“Ha! 10 o’clock bed time for a 20 year old.”

He was in sweats and a shirt as he brushed his hair in front of the
with the door open. His attention was deverted by a whispering sound. He
looked in the hall way and saw Stephanie standing there. She had a smirk on
her face and was wearing the same little tank top and short silky shorts.
was standing with her legs crossed. “Can I pee real quick?” she said with a
bit of a giggle. “Yeah, let me get my things out of your way.”

“I can’t wait,” Stephanie said as she simply pulled her shorts and
down to her bare feet, bent over, and sat on the toilet.

Scott couldn’t help but see her do this, catching a quick flash of her
bare ass. Stephanie just sat there for a minute as Scott pretended not to
gathering his towel, brush, etc. Then Stephanie looked right at him, stood
half naked, and slowly non-chalantly pulled up first her panties then her

“False alarm,” she said in a cute voice.

Scott could feel his cock growing again. He hadn’t had any ‘release’ in
past week, being so busy with life in general, and his cock was really
sensitive. She was still staring at Scott in a seductive sort of way, until
cell phone rang loudly. “Hello?”

“Scott? This is Vince.”

“Oh, hello sir.” He mouthed to Stephanie ‘it is your father’ to which she
smiled and rolled her eyes.

“Scott I forgot to tell you. Stephanie’s bed time is 10 o’clock SHARP! It
now about 9:50. Where is she?!” Vince said, sounding mad.

“Uh, sir, she is right here, I mean she is using the bathroom, she…”

“LISTEN Scott! I am paying you to watch over my daughter. My little

“But sir she is like 20…”

“Do you know who I am?! Listen up pal! If my daughter is not in bed in
minute or two, I’ll fire your ass! I’ll also make sure you NEVER work again
for ANY DECENT COMPANY or BUSINESS! I have connections ya know…. !” he
on and on.

Stephanie was still staring in a horny way at Scott, not being able to
what her father was saying.

“Look sir, what am I supposed to do exactly? I mean…”

“Scott, I have equipment all through that house that lets me know if
Stephanie is in her room and at what time. I am going to hang up now. If she
is not in her room in bed soon, it’ll be your ass pal!”

“Sir but…”

“DO WHAT YOU GOTTA DO! If she doesn’t listen, punish her.”

“What do you mean?”

“I mean yell at her, unplug her television…. OR spank her ass, that’s
what I do!”


“It seems to work. She may be your age, if not OLDER, but in the McMahon
household, she is still my little girl. So do what you have to do, GOT IT


“What did he say?!” Steph asked, still flirting with her smile. “Well…
he said that now is your bed time… and you have to go to bed now,” Scott

“Too bad! I am staying up all night!” she snorted.

“Stephanie. If you don’t go to bed, I’ll get fired… and Vince said I
would NEVER WORK AGAIN! I need money. I don’t have your luxury!”

“Well too bad for you I guess,” she said looking right in his eyes with a
large smile.

“Look, I feel dumb saying this but… your father said I could punish
I’ll… (he thought about a different approach).. I’ll… I’ll just tell
dad when he gets back and you’ll be in deep shit.”

“Oh, please, I am NOT EVEN scared of my daddy… I am his little girl,”
she continued, standing up proudly like a brat, eyes closed, smiling,
“whatever I say… he will believe… cause I am his PRINCESS.” Her last
words were emphasized and Scott got pissed.

“You know what?!” he firmly grabbed her arm and pulled her in the
“you are going to bed NOW!”

“Hey… HEY…” she pulled away from him, running down the hall. Scott
sprinted after her and dove for her leg, grabbing a bare foot. Stephanie
tried to run with Scott hanging on her leg, but gave up and sat on the
kicking away at him. Scott blocked all of her kicks and wrestled the
clad future Diva. Her shirt rode up even more and her bra was exposed, her
shorts wedged up her ass showing much upper thigh flesh. Scott had her
on her back, his hands on each of her wrists, and somehow he got in between
her legs. His cock was pressing right on her pussy on accident. She wiggled
and wiggled, rubbing his cock, not even knowing she was doing so. Scott
to block the feeling out as he kept her still. She panted over and over as
just held her there.

“Chill… chill out Steph,” he gasped, trying to catch his breathe, “just
go in your room, I don’t care WHAT you do, just don’t get me fired! PLEASE!”

Stephanie caught her breathe and pouted, still having a bit of a naughty
grin on her face.

“Fine!” Stephanie waited for Scott to release her, then she slowly got up
and walked towards her room.

“Finally…” Scott said still trying to breathe. Stephanie started

“HA! HA! JUST KIDDING!” Then she sprinted for Scott’s room. “Son of
Scott shouted, giving chase to Stephanie.

Steph practically dove into Scott’s room, got up, and tried to shut the
door. It was mostly shut except for about 5 inches, when Scott’s body
it. He pushed up against Stephanie’s strength, which was more than he
she had, as he struggled to keep the door from closing. He finally got it
open enough to slip into the room. Stephanie was laughing and carrying on
very loudly. Any other time, her rough flirting would have given a guy an
instant hard on, but Scott knew he was 2 seconds away from getting fired if
Steph didn’t go to her room. He picked up the laughing Stephanie and hurried
her to her OWN room, tossing her lightly on the bed as he glanced at the
clock. (9:59) it showed. Scott let out a sigh of relief and STephanie still
laughed out loud.

“Hahahaha! Hahaha… don’t worry…I’ll find a way to get you fired
the night is over… hahaha!” Scott was pissed. She was TRYING get him
He would show her.

“You wanna play around?! Huh! You like to play games?! Well how about
this… your ‘DADDY’ told me that I could punish you.”

“S-s-so… so what…?!” she said nervously after a long pause.

“SO! Stand up Stephanie. Remember, I have the authority now! Stand….
up…. now.” Stephanie knew he was serious. Her smile was a normal face now,
still grinning just a little, as she stood up and got face to face with

He noticed Stephanie’s tank top was a bit ripped and he could see that
was wearing a silk pink bra. The nipples were now sticking though the top
that was 3 times too small. Scott sat on Stephanie’s bed.

“Time for your spanking….” he said with a grin. Stephanie whimpered a
little, letting out a whine, then knew what to do. She pulled down her
and took off her tank top, which was already shredded to rags. Scott looked
her in her sexy pink bra and panties. His cock was growing by the second. He
held up his index finger and bent it a few times in a simple gesture telling
Steph to ‘come over here’. Stephanie slowly moved to Scott and started to
down over his knee.

“Wait… huh uh…” he said as he motioned to her panties, “…bare butt.
No panties for your spanking.”

Stephanie’s bottom lip quivered a bit.

“Come on Steph, you had no problem dropping trow when you had to pee, you
horny girl.”

Stephanie let out a little smile, then went back to her nervous face. She
put her thumbs in the loops of her pink panties, then slowly slid them down
to her feet and kicked them off. She bent down a bit and got on Scott’s lap,
bending over all the way for her spanking. Scott tells her to bend over his
with her ass up in the air more and her legs spread open some. Scott takes
the view of the princess Stephanie’s bare butt. Inches from his face, on his
lap, her pooper is exposed. The way she is bent over in the awkward
Scott looks down and sees her shaved pussy lips that have a trace of
on them. Her puckered little butt hole is so pink and clean that he
to hold back from sticking a finger up it. Her long muscular legs are
stretched out and her toes are bent in anticipation. Scott rests his right
on her lower back and rubs it in slow circles as he talks.

“Stephanie… you know you have been a bad girl…”

“Yeah…” she whimpers. He can’t believe he has a 20 year old in this
compromising position.


Stephanie lets out a gasp as Scott’s left hand comes crashing down on her
bare rump.


Another on her left butt cheek.


Now one on her right butt cheek. Stephanie’s butt cheeks flex and crunch
together, but it is no use. Her butt is burning. Half of her wishes she
hadn’t messed around with Scott… half of her is getting aroused. Scott
this too as he sees Stephanie’s pussy lips slowly and gently spreading and
swelling like the petals of a flower.


“Ahhhhhh….” Stephanie lets out a very audible moan.

She shifts her hips a bit, but Scott keeps his hand on her lower back so
can barely move.

“Are you sorry Stephanie?”

“Yessss… I am sorryyyyy….” she whines.

“I don’t believe you….”


“Uhhhh…. owwwww…. my butt…” Stephanie’s butt is now a little red as
Scott continues. “Convince me you are sorry….”


“Ahhhh! OWWW! I am sorry! So sorry! AHHHH!”

Scott *SMACKS* her hard, right on the butt crack. His rough palm brushed
anus and he saw it open a bit.

*SMACK* *SMACK* Same spot. Stephanie is now whimpering like a puppy,
wiggling her big pale butt in Scott’s face. Scott’s cock is hard as a rock.
Stephanie is laying about an inch below it and her stomach keeps bumping it
every few seconds which makes it harder. Scott can see Stephanie’s pussy is
really wet now.

Steph is whining but her ass and pussy is tingling and she wished he
show her what he said he would show her.

Scott stopped spanking her and started rubbing her ass and ran his
down between the opening.

“Stephanie… your pussy is wet…!”

She was silent.

“Is this turning you on Steph?”

Still nothing.

“You know, Steph, I can make you feel really good,” he said, rubbing her
red butt cheeks.

He continued to rub as the other hand went to her pussy and gently spread
her wet folds open.

“Ahhhhh… yes…”

“You like that Steph?!” Stephanie’s butt raised up a bit.

“Yes… please… play with me…”

Scott SPANKED her butt and slid 2 fingers in her pussy at the same time.
“AHHhhhhh yes… yes….”

He finger fucked her only for a few seconds then told her to lay back on
the bed. She took off her top and Scott got naked as well. He got up on the
and laid on top of her, kissing her over and over. He ran his hands up and
down her legs, stomach, all over her breasts. He kissed down Stephanie’s
and moved down, taking one of her huge tits by the hand and sucking on the
nipple. Stephanie cried out and begged for more. Scott went at both of her
titties back and forth, as Stephanie bent her legs a bit and opened her legs
with her feet supporting her on the bed. Scott teased and tickled her large
nipples to perkiness as he kissed down her stomach and buried his tongue
right in her pussy.

“Hhhhhuuuuuuhh! Oh yes… mmmmm yeah…. ooooooh lick me…. ahhhhh”
Stephanie wrapped her legs around Scott’s head as he tongued her pussy
and out. He wiggled his tongue in her salty cunt and licked her g-spot,
causing Stephanie to stutter and cry out. Scott flipped her on her stomach
ate her pussy out that way too. Stephanie’s butt cheeks flexed together as
Scott licked back and forth from her pussy to her butt and back. he started
kissing her where he had spanked her turning her from side to side, then he
started kissing her where his fingers had just been in her pussy making her
gasp. His kisses turned to sucking and licking around her clit again, this
time making her cum, crying out “AHHHH-H-H-H-H-H-H….. ohhhh….. ahhhh”

Stephanie moved around and bent down. She started kissing the head of his
cock all over and then opened her mouth real big and stuck it in her mouth.

“Ahhh… baby that feels good… suck it Stephanie….”

She sucked it good, bobbing up and down while jerking his shaft a little.
Scott played with her tits and rubbed the red marks on Steph’s pooper as she
sucked and licked away. Scott could feel the one week’s worth of cum rising
the head, so he pulled away.

“Come here baby….” he said, pulling Stephanie on top of him.

He sat on the edge of the bed the way he did when he spanked her and
hovered over his dick in a sitting position facing away from him. “Sit on my
lap baby… come on… YEAH!!!!”

Stephanie sat back, taking Scott’s cock iin her wet cunt. She gasped out
loud, then began standing and sitting a little, fucking the cock. Scott held
her wide hips and helped her move up and down as he watched his dick go in
and out of her pussy. Stephanie’s legs began to buckled a little and she sat
down all the way, taking Scott’s cock cunt all the way and keeping it there.

“Ahhhh….. mmmmmm……” Steph gasped as Scott hugged her from behind,
letting her get off the cock.

Scott stood up all the way, lifting Stephanie off the ground with a dick
still in her pussy. Scott stood her up and bent her over, but awkwardly
her leg in the air to hit her pussy in the right spot. He started to fuck
hard and fast.

“Ohhhh.. yeeeeeeah.. uhhh….. uhhh…. fuck me…. eeeeeehhh….

Stephanie put her leg back on the ground as Scott fucked her good. He
her head down and held her there so that Stephanie was standing up with her
head all the way down to her knees almost. “Ahhhhh.. ahhhh.. yeah…
mmm… ohhh…!”

Stephanie cried out from the large dick cramming her little wet cunt.
moved her to the bed on her hands and knees and fucked her, not missing a
beat. He pushed her face to the bed so her bed was sticking straight up in
the air as he gave it to her nice and fast. Scott knew he didn’t have much
longer til he came, so he flipped her on her back and fucked her with her
legs spread.

tits some more while nailing her pussy, then pulled out and sat on her
stomach. He told Steph to wrap her tits around his cock and she did as Scott
started the tittty fuck. He fucked her D cups as Stephanie held her own
She playfully giggled, licking and kissing his cock head every time it pop
through her cleavage.

“Oh Stephanie, baby, I am about to cum….”

“Hey, not on my face… wait…” Steph let her tits go and tried to move,
but Scott pinned her with his weight on her stomach. He then moved up and
his knees on her shoulders as she struggled get free. “Noo… wait…
nnnnnn…..” Scott began to whack off, his cock was inches from Stephanie’s
crunched up cute face. Scott’s eyes closed and he started to groan.

“No…. dont……” then Stephanie’s mouth shut tightly as she felt a
thick wad of cum squirt and hit her lip.

“Ewww…. mmmmmmm… noo…. nnnnnnno… yuck….. ”

She whined as another shot out and hit her nose, then her left eye and
down her face. Scott rubbed her face with his cock, smearing the sticky cum
over. Stephanie just let out a long whimper, trapped, not being able to move
away. He got off her finally and grabbed his stuff. “Eww.. gosh… why did
you DO THAT?!”

“I had to punish you some how. Don’t fuck with me again… good night!”
left and went to his room. Stephanie crossed her arms like a brat and

This entry was posted in Cons, MF, Oral, the_next_whiterapper and tagged . Bookmark the permalink.