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- 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
- her.
-
- 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
- thought....you 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
- dresser.
-
- "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
- before...."
-
- "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
- suitcase.
-
- "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 curious...you know, to...um," Debbie
- stammered nervously. "To see...how the
- pouch...um...works...what...um...you 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
- pants!
-
- "It's OK!" Debbie blurted out. "I'm....uh...I'm not exact-
- ly...um...a 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
- I'm...um...pretty?"
-
- "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 just...you
- 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
- room."
-
- "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 actually...um...y'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 out...my girlfriend's...y'know...her vibrator!"
-
- "Her what?!" he blurted out in amazement. "Oh...you mean a
- dildo?"
-
- "Yeah. You know, a plastic thing..."
-
- "You don't know if a boy did it or your girlfriend's dildo?"
-
- --