
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/213157.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      F/F
  Fandom:
      Gossip_Girl
  Relationship:
      Jenny_Humphrey/Blair_Waldorf
  Character:
      Jenny_Humphrey, Blair_Waldorf
  Additional Tags:
      Underage_Sex, Fingerfucking, Virginity, Alternate_Universe_-_Canon
  Stats:
      Published: 2011-06-19 Words: 875
****** Jenny.... ******
by merryghoul
Summary
     AU 1.05. Blair convinces Jenny to stay at her annual sleepover and
     discovers something in the process.
When Jenny arrived at Blair's penthouse after getting detained by the police,
she was greeted with darkness; the lights in the foyer of the penthouse were
turned off.  Blair awoke and showed Jenny her bed right beside her, on her left
side.  Blair's other minions were asleep.
"Well done, Little Jenny Humphrey.  Here's your bed."
"Thank you, Blair, but I'm not staying.  I'm going home."
Blair had a look of disbelief on her face.  "No one leaves the Waldorf
sleepover early.  No one."
"Well, I am, Blair."
Jenny headed to the elevator.  Blair quietly slipped out of her bed and stopped
her as soon as Jenny pressed the down button to the elevator.  She grabbed her
hand. 
"Usually I don't associate with people of a lower social status than I am.  But
you did so well tonight, Little J.  I want you to stay.  I have a nightgown you
can wear."
"I don't care, Blair.  I'm still leaving."
Blair frowned.  She was upset. "Please stay.  You don't have to sleep on that
uncomfortable portable bed anyway.  You can sleep in my bed."
Jenny thought for a moment.  She shrugged.  "Okay." 

Blair, standing behind Jenny, slid a white see-through slip over Jenny's
frame.  She grabbed the slip and pushed it down with her hand over Jenny's
hips.
"It fits you perfectly!"  Blair squealed.  "It's Agent Provacateur.  Don't
sweat in it or Dorota may not be able to get it out."  
Blair's hand grazed Jenny's cunt.  Jenny shuttered. 
"Did I do something wrong?" 
 
"No, Blair, you grazed my private parts."
"That was an accident, Little J.  Can you breathe in the Provacateur?  I don't
want to call Dorota at four in the morning to get you out of that slip."
"Yes, I can breathe in this slip, Blair." 
Blair's hand grazed Jenny's cunt again.
"Little J?"
"What?  I wasn't gasping, Blair."
"I think I know what you need."
Blair led Jenny to her bed and laid her down.  
"I'm about to perform something I've never done in the history of the Waldorf
Sleepover: make out with a girl in my bed."
"But what about Nate?"
"What about him?  I'm still a virgin as long as I don't get penetrated by
someone else's cock."
"Aren't you still cheating on him?"
"I've told him about the Waldorf Sleepover.  He knows I have fun with my girls
here like Nate has fun with Chuck, his whores and his herpes simplex at Chuck's
Lost Weekend.  I've done this before with Serena.  It's nothing, Little J." 
Blair kissed Jenny, laying on top of her.  The kiss started off as a peck, then
became an open mouth kiss before finally leading up to a French kiss.  Blair
kissed under her neck, slowly moving to her breasts.  She kissed the tops of
them, not daring to slide the straps of the slip down Jenny's shoulders.  Jenny
looked up at the ceiling, unsure what to feel or say but letting Blair
continue.
The slip that Blair spent moments sliding down Jenny's torso was pushed up
towards her breasts.  Blair kissed Jenny's stomach up and down, covering it
with kisses.  She French-kissed Jenny's belly button.  Then she saw Jenny's wet
panties.    A devious smile appeared on Blair's face.
"Have you ever been fingered?"
"Fingered?"
"You've been living with guys way too long."
Blair removed Jenny's panties.  "Well, have you ever masturbated?"
"No, Blair.  It's kinda hard to when your brother and your father are watching
you like a hawk."
"I'm going to be the first girl that fingers you."
Jenny gasped.  
"Don't be afraid.  You'll feel things you have never felt before, maybe even
say some things that won't make sense while you're getting there.  Let it all
out."
Blair stuck her finger in Jenny's vagina and used Jenny's wetness to stimulate
the length of her clit.  After a few minutes she would touch the tip of Jenny's
clit.  Blair repeated this a few times.  Jenny moved her hips counterclockwise
on Blair's bed in appreciation.  
"You like that, don't you, Little J."
Jenny let out a moan.
When Jenny was wetter Blair stuck her index and middle finger inside of her. 
Jenny gasped as Blair entered her.
"You're so tight.  I could barely get inside of you.  Are you okay?"
"Uh-huh."  She let out a moan.
Blair stroked her G spot, gradually increasing the pressure and speed in which
she stroked the spot.  Jenny began to breathe heavily.  Her hips still moved in
time to Blair's stroking.  Blair removed her fingers and then stroke Jenny's
clit again.  Jenny let out a bigger moan.  Her eyes rolled back in her head. 
She soaked Blair's hand with her wetness. 
After Blair stroked her clit and G spot alternatively for a few minutes,
Jenny's body gave out.  She shook all over Blair's bed.  Blair quickly pulled
out of stroking Jenny's G spot.  She licked Jenny's wetness off her fingers. 
"You don't taste too bad, Little...."
Jenny's first orgasm put Jenny to sleep.  She had curled up in a fetal position
and had fallen asleep on Blair's bed, her slip still hiked up over her bare
ass.
"Maybe I'll be back in the morning."  Blair left her bedroom.  "Or maybe not." 
She returned to the sleepover beds in the foyer.
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