Related Free Sites Related Free Sites
All Me | Teen Stories | Taboo Stories | Porn Stories

Back to more "Virgin" and "First time" Sex Stories

Teen Sex Stories
Virgin Stories - First Time Sex Situations

Welcome to the TOP Teen Sex Story Sites!

Archive-name: First/yungstf1.txt


Archive-title: Young Stuff - 1

Chapter 1 - The Approach

     As  he hurried back toward the hotel, he looked  for  Debbie

along the sidewalk in front of him.  As he waited for a light  to

change,  he finally spotted her standing on the opposite  corner.

At least he thought it was her - he wasn't expecting Debbie to be

quite  so  'dressed up', so he wasn't really sure it was  her  at

first.  He stared across the street at the girl.

     The  brunette  he'd spotted was wearing a  blue  dress  with

puffy  short  sleeves.  Although the dress had  a  fairly  modest

neckline,  the hem was very short, barely reaching to the  middle

of  her thighs.  She wore white stockings, black high-heels,  and

didn't  look like she was just 16.  He quickly concluded that  it

was Debbie and he yelled across the noisy traffic at her.

     "Debbie!   Want a ride to the office?" he asked,  waving  to


     She  looked  up, smiled and shouted something back,  but  he

couldn't hear what she'd said.  He watched her check the  traffic

light and stride deliberately across the street toward him.   She

didn't look just 16 up close either.

     "Hi!"  he  said, as she joined him on  the  sidewalk.   "I'm

going  to check-out of the hotel and get my car.  Do you  want  a

ride to the office?"  He explained that her mother would meet her

there later.

     He  suspected that she was trying hard to act  disinterested

in being seen anywhere with someone almost her mother's age,  but

Debbie soon smiled and agreed to accompany him back to the hotel.

They  filled their two-block walk with small talk on  nothing  in

particular,  although  he  did manage to tell her  how  nice  she

looked.  She looked damn good and he tried not to look at her too

obviously, but found his eyes dropping fairly frequently to steal

a glance at her legs.  They were very shapely and looked terrific

in white stockings.  He had to remind himself repeatedly that she

was only a high school junior; definitely young stuff.

     As  they  waited  for the elevator in order to  get  to  the

second-floor  lobby, he remembered that the last time  he'd  seen

Debbie,  he'd concluded that in an effort to look  grown-up,  she

wore too much eye make-up.  As a result, she'd looked even young-

er  and  a little on the slutty side.  He was glad  she'd  either

changed  her make-up style or had forgotten to put it  on  today.

Her  shoulder-length  hair was naturally wavy and  her  skin  was

clear  and smooth, adding to the illusion of her age.   They  en-

tered  the elevator and he noticed she stood closer to  him  than

was really necessary, since there was no one else in the car.  He

also noticed that she smelled good.  Neither said anything  until

the doors opened on the second floor.

     "Listen, I'm going to go check out and then run upstairs  to

pack my stuff up," he explained.  "If you want, you can just wait

here in the lobby and I'll meet you when I'm done."

     He  gestured  toward a small reception area  in  the  lobby,

filled  with several low couches and tables.  He turned and  went

to  the front desk to settle his bill, leaving Debbie by  one  of

the couches.  When he turned from the front desk to head back  to

the  elevator, he saw Debbie had sat down on one of the  couches.

The  seat was so low that her knees were almost higher  than  her

shoulders.  By walking across the lobby at just the right  angle,

he  got a decent look up her legs beneath her short dress.   When

he got close to her and started to walk past her, Debbie stood up

and  started  to follow him.  Somewhat startled, he  stopped  and

looked at her quizzically.

     "I don't want to sit here all by myself," she said.   "Can't

I come upstairs with you?"

     "Why,   sure,   sure  you  can,"  he  answered.    "I   just know, it would be boring..."

     "It  would be boring to just watch you pack!"  Debbie  said.

"That's why I'll help you pack."

     Thoroughly startled now, he stammered something incoherently

and  headed for the elevator with Debbie close behind.   Once  in

the elevator, she stood even closer to him than before, until the

doors opened and he led the way down the hallway to his room.  As

soon  as he'd unlocked the door, she slipped past him and  walked

into  his room in front of him.  His eyes watched her  hips  sway

back  and forth as she moved into his room.  Before he could  say

anything,  she had walked to the dresser, pulled open  a  drawer,

and  reached  into  it.  Fishing out a handful  of  clothes,  she

turned toward him.

     "Is this drawer all your dirty stuff?" she asked, holding up

her hand.  "Where do you want it?"

     "Yes,  that's what it is, all right.  I'll get  that  stuff,

Deb," he replied, stepping towards her.

     "That's OK, I want to help," she said.  She reached into the

drawer  again and fished out another article of  clothes.   "Say,

these are cute..."

     Debbie held up a pair of 'used' jockey shorts and smiled  at

him.   She  dropped  the other dirty clothes on the  top  of  the


     "Really,  I think they're cute!  I thought older  guys  wore

boxer  shorts instead of these!  I mean, I didn't mean  that  you

were that old, but...well, you know..."

     "I guess I am that old..." he muttered.

     "No,  really....I don't think you're old," she  said.   This

time,  she was the one who was slightly embarrassed.  She  looked

at the shorts again.  "Say, these have sort of a...a pouch on the

front  of  them,  don't  they?  I've never  seen  one  like  that


     "Seen a lot of men's underwear, have you?" he teased,  going

on the offensive for no particular reason.  He began stuffing his

toothbrush and cologne into a travel bag.

     "Well," Debbie blushed, "I have seen a few pairs...

     "Well,  they  have a pouch that only well hung men  need  to

wear..."  he teased, a wide grin on his face.  "You  know,  keeps

everything neatly arranged....kind of like a bra..."

     Debbie  eyed  him for a moment before examining  the  jockey

shorts again.  She put one hand inside the underpants and  filled

the  pouch with her fist.  Holding them up closer, she  tried  to

sniff  without him noticing, but he had already noticed  and  was

fascinated by what she was doing.

     "These  are really cute," she said.  Apparently  pleased  by

whatever her nose had detected, she smiled at him.  "You know, if

you've got time...."  Her voice trailed off in mid-sentence.

     "What's that?" he asked, tossing a pair of sandals into  his


     "Oh, nothing really," she said, blushing again.  "I was just

wondering....if you don't have to get out right away...."

     "Oh,  come on," he groaned.  He faced her with his hands  on

hips.  "What is it?"

     "Well...I  was sort of know,,"  Debbie

stammered        nervously.        "To        the     think     is...uh...well

hung..." she stammered nervously.

     He stared at her in disbelief.  It was one thing to lust  in

his mind after a 16 year-old, and quite another to have the  same

little  cream-puff  asking straight-out for him to take  off  his


     "It's OK!" Debbie blurted out.  "I'm....uh...I'm not  exact- virgin...and...I've seen them before, but I'd kind of

like to see...what you think is 'well hung'?"

     He continued to stare in silence at Debbie.  She was holding

his  underwear  with  both hands in front of her  chest,  and  he

noticed her sniffing at them again.

     "Hey,  I  know!" she said.  "Would you like to see  my  bra?

I'll show you my bra and then you can show me your, uh, you know,

pouch.  Kind of underwear for underwear!  That sound fair?"

     His mind raced at the prospect but he called himself back to

reality by recalling her age.  Pretty or not, she was  definitely

under-age.  She must have read his mind.

     "Look,  I know I'm only 16, but I'm not a little  kid!   Who

would  believe me claiming you tried to get it on with  me?   How

about  it?  Look, I'll make it easier - I'll show you my bra  and

then you decide, OK?"

     Without  waiting for a response, Debbie reached  behind  her

shoulders  and  popped open a few buttons on the  collar  of  her

dress.   With a few small shrugs, she quickly slipped  her  puffy

sleeves off her shoulders.  Pulling one arm completely out of her

dress, she easily pushed the bodice of her dress down, uncovering

her bra-clad chest.

     The  bra  was  cut low and made of  light,  silky  material,

leaving little to his imagination.  Gazing at her, he was  amazed

to see how developed her tits actually were.  The bra pushed  her

breasts  together and up, creating cleavage not often seen  on  a

girl  of 16.  Even so, it was obvious that Debbie was  very  well

endowed, and the sight was not just the creation of the bra.   It

was a very pretty sight.

     "So?  What do you think?" she asked, quietly.  "Do you think


     "Debbie,  you're  very  pretty, but I  don't  think...."  he

started to protest weakly.

     "Oh,  come on!" she frowned.  "I wanted to show you my  bra!

Would  you like to see more?"  He realized with an inaudible  (he

hoped) choke that she was serious.

     Debbie  reached  behind her back again and  quickly  slipped

open  the  back-strap  of her bra.  With one  fluid  motion,  she

shrugged the bra-straps off her shoulders and brought her fingers

around the bottom edge of her bra beneath her armpits.  With  two

tugs, she pulled the bra cups down, baring her developing breasts

for  him.   He stared at the small,  rosy-colored  nipples  which

tipped  each  of her firm, pointed breasts.  She  was  no  longer

close to gorgeous - she was gorgeous.  Her breasts rose and  fell

as she breathed and her nipples looked as though they were  actu-

ally beginning to harden under his gaze.

     "How's  this?" she murmured.  "I've never really

know,  practically  torn off my clothes like this  before!   I've

been  told  I have a nice figure...and some guys I know  like  to

squeeze my breasts...when I let them!  What do you think?"

     "I think," he began, his voice very low and tight.  "I think

that you are a very beautiful girl.  I think you have a beautiful

figure.   And, I think you are too young to be undressing  in  my


     "Really?   You think I'm beautiful?"  Debbie slid her  hands

over  her  breasts, covering her nipples.  "I told you,  I'm  not

exactly...a virgin.  I've seen 'them' before, but I would  really

like to see yours..."

     "What does 'not exactly a virgin' mean?" he asked.

     She  blushed and looked down at the floor for a moment,  her

hands motionless over her naked boobs.

     "Well...I...I've never'know, been laid..."

she murmured, her voice barely audible and her hands still cover-

ing her nipples.  "But I don't have my...uh...'cherry' anymore."

     "Try that again?"  He was fascinated by the girl's  uninhib-

ited behavior around him and her revelations about her sex life.

     "I've  never  actually  been laid, but  I  got  my  'cherry'

popped..." she replied, her voice very low.

     "How's that?"  He was in no mood to stop this conversation.

     "I'm  not exactly sure...." Debbie began, running  one  hand

through her hair.  He stared at her uncovered nipple.  "I lost it

either  when a boy, um, y'know, used too many fingers....or  when

I...I tried girlfriend's...y'know...her vibrator!"

     "Her what?!" he blurted out in amazement.  " mean  a


     "Yeah.  You know, a plastic thing..."

     "You don't know if a boy did it or your girlfriend's dildo?"



See All Our Feature Hardcore Sites!
Taboo Stories | Porn Stories