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Rosies First Date


Keywords: Mg Author: Wizard Title: Rosie's First Date

Rosie’s First Date


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- - - - - - - - - - Standard Disclaimer. This is a work of fiction for
adults only. If you are under the age of eighteen, please immediately do
what I would have done when I was your age. Which is, delete this story from your hard drive and/or leave this internet site. I know you've left
now like the good little boys and girls you are. But if you haven't or for
the rest of you, enjoy.

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Teaching high school was the pits. I really wanted to teach fifth or
sixth grade, when kids are still partially human and haven’t mutated into
teenagers. But there just weren’t any openings this year in Florence and I
didn’t want to move. I Liked the Oregon coast too much. But there were a
few advantages. I was teaching creative writing and drama which were
elective courses so the kids in my classes wanted to be there. If I’d
gotten stuck with basic comp or Freshman english I think I would have tied
my teaching certificate to an arrow and set it on fire and shot it at the
superintendent’s office.

Most of my students, while teenagers could at least pass for human when
they tried. And some were a pleasure to teach. And more than a few were
definite sightseeing attractions. And I wasn’t that much older than these
kids, six or seven years that I couldn’t appreciate a foxy cheerleader in a
short skirt.

One of my favorite students was Rosie Callaghan. Rosie was the kind of
student that teachers remember all through their careers. She was bright
and responsible, she always had her homework finished and turned in on
time, if there was extra credit to do, she did it. And what made her
really special, was that she listened. She rarely made the same mistake
twice. With most kids, I’m still red penciling the same mistake on their
final paper that I marked on their first.

And Rosie wasn’t bad on the eyes either. She wasn’t a cheerleader or a
fox. But she was cute and had a great body. About one notch below fox in
my opinion. She had strawberry red hair and a pretty unblemished face.
She was a little shorter than average for a freshman and her tits were a
little too big for her body. If she’d been about eight inches taller they
would have been perfect, but maybe she’ll grow into them. She had a great
ass, full but firm. And she liked to wear tight jeans that showed her ass
off wonderfully. Her legs were just a little stubby, if they grow a little
bit then she might rate a perfect backside award. She usually had a great
tan, though it was a little faded right now. And it wasn’t a fake tanning
bed tan, it was the real thing because she spent so much time outside. She
ran cross country in the fall and track in the spring. During the summer
she was on the swim team at the outdoor community pool. In the winter she
rested and that’s why her tan faded a little, it was almost Christmas

Rosie and I had become good friends. Sometimes she’d stay after school
to help me with projects or come to me with some of her problems, usually
about one of her six brothers. As an only child, I figure just having six
brothers would be a problem, they wouldn’t have to do anything. Rosie
lived two blocks from the school, which made it real convenient when she
wanted to stay after.

Today, she’d stayed after to help me set up the stage for the Christmas
show. Excuse me, the holiday show. We don’t have a Christmas show
anymore, it might be seen like supporting religion at school. Anyway she’d
been helping me set up the stage and now we were finally done. I walked
back into my classroom and collapsed in my chair. Rosie followed me in,
closed the door and took a seat in the front row of desks.

“Rosie, from the bottom of my heart, thank you. If you hadn’t been
helping I would have been here all night.” I said. “Remind me to give you
an ‘A’.”

“That’s no fair, you’re already giving me an ‘A’. I earned it.”

“That’s true, “ I admitted. “How about if I buy you a hot fudge sundae
some time.”

“Deal.” She said quickly. “Can I talk to you about something?”

“Anything. You know that.”

“Well, this isn’t about school. Or even my dumb brothers.”

“That’s okay. Just say what’s on your mind.”

“Well...” One strand of hair had fallen down just to the side of her
face and she toyed with unconsciously. “I’ve kinda got a date tomorrow.”

“How do you kinda have a date?”

“Well I have a date.”

“Good. Who’s the lucky guy?” Now I sounded like a mom.

“Joey Reid.”

“A sophomore, that sounds good.” Good as long as you keep your legs
closed. According to the gossip, Joey had already laid half the girls in
school. “What’s the problem?”

“Well, it’s kind of embarrassing.” Oh God, she’s going to ask me for
birth control or something.

“Go ahead.”

“I’ve... I’ve... I’ve never gone on a date before.”

“You’re kidding.”

“See, mom wouldn’t let me date until I got to high school. Then I got
here and I was busy with classes and cross country and stuff, and... and
this is my first date.”

“I see.” Her first date was with Joey Reid. That was like giving a kid
his first driving lesson in a formula I car. “What do you want me to do?”

“Well, what am I supposed to do? What is he going to do? I just don’t

“Shouldn’t you discuss this with your mom. Or maybe one of your older brothers.” Rosie was right in the middle of her family. Three of her
brothers were older and three were younger. Of the older ones, one was a
sophomore, one was a senior, and one was just finishing collage.

“I can’t talk to them about this. I just can’t.”

“Okay, what do you want to know?”

“We’re going to the movies. What do I do?”

“Well, he’ll pick you up. You’ll probably walk to the movies since he
doesn’t drive yet. You’ll go inside, he’ll ask if you want popcorn or
anything. Tell him yes or no...”

“I know all that.” She said with exasperation. “What I mean is, when
we’re watching the movie, in the dark and everything. What’s he going to
do, and what should I do.”

“He’ll probably start out by putting his arm around you, rubbing your
arm a little, then maybe the side of your ribcage. He might try to kiss

“But how is he going to do that. What’s he going to do?”

“But I was just explaining that...”

“But, show me, please.” I’ve always had trouble saying no to cute girls.

“Okay, we’ll have a trial date.” This was nuts. It had been years since
I dated a fourteen year old. But, what the hell. I pulled two chairs
together and set them in front of the blackboard. Then I walked over to
Rosie and pulled her to her feet. I took her hand, it was warm and just a
little sweaty. We walked to the back of the classroom. You’ll get to the
theater and walk in, he’ll probably hold your hand.” I walked her to the
front of the class and we sat down in the two chairs, with Rosie on my
right. “You’ll probably just sit and talk until they turn down the house
lights and the movie starts.

“Probably after the trailers end, hell put his arm around you like
this.” I put my arm on the back of her chair so that I was just barely
making contact with her. “So guys pretend they’re stretching, but that’s
pretty hokey and been done to death. He’ll start to move closer and put
his arm more on you.” I leaned over toward her a little bit and slowly
transferred my arm from her chair to her shoulders. “The thing is timing.
Some guys will take a whole movie just to do this much. Others will be
here before the end of the credits.”

“What about Joey?”

“I have a feeling that he’ll move pretty fast, but I don’t know.”

“If he moves fast, what next.” I started rubbing her arm and then put my
hand under her arm and rubbed her side along her ribs.

“He’ll probably rub you something like this. Then he might try to kiss


“He’ll turn his head toward yours and lean his face in close to yours.”

“Show me.”

“I can’t kiss you. I’m a teacher. You’re a student, a freshman.”

“You’re a teacher, and you’re teaching me how to act on a date, what to
expect. You want me to be safe and happy.”



Like I said, I never learned to say no to cute girls. I leaned a little
closer, turned my head and leaned my face in real close to hers. She
turned toward me a little, and I pushed my lips on hers. She didn’t pull
away. I broke the kiss after a few seconds. “If you haven’t stopped him
yet, he’ll probably try to feel you up next. But you’re going to stop him,

“I don’t know. How can I know what to do if I don’t know what’s going
to happen?

So I kissed her again. And as we kissed, my right hand moved forward
toward her breast. I could feel the side of her bra as my hand moved up
the slope of her breast. I couldn’t believe that she wasn’t stopping me.
Was she really going to let Joey have a handful of tit on her very first
date. My hand cupped her breast and I rubbed her nipple through her shirt and bra with my palm. “And you’re going to stop him before he gets this
far right?” I asked.

“I don’t know, what will he do next if I don’t?”

“Well, there’s no manual for this sort of thing and every guy has there
own style, but probably he’d try to get inside your shirt.” And even as I
said it, my hand moved down to her waist and the bottom of her t-shirt. I
slipped it inside and started the journey back up until my hand again
cupped her breast, only now there was only a lacy bra between my hand and
her nipple.

“Then what?” she asked breathlessly.

I kissed her again and slid my left hand over onto her thigh about
halfway from the knee. My other hand slid across her back and undid the
clasp for the bra. I kept telling myself that this was an innocent girl and she was going to stop me any moment. My hand slid back across her back
to the bottom of her bra and then I slipped it inside. The skin of her
lower breast felt wonderfully warm and smooth and I knew she say stop any
moment. My hand kept going until I could feel the nipple. She fat a big
fat nipple, I took it between thumb and forefinger and started rubbing it
back and forth. My left hand kept inching higher and higher on her thigh
until it was only inches from her crotch. I opened my mouth and inserted
my tongue into hers. She seemed surprised but not upset.

I broke the kiss and asked “You’re not really going to let him go this
far are you?”

“I don’t know, what would he do next?”

I kissed her again and moved my hand up her thigh until it covered the
crotch of her jeans. I couldn’t feel much because of the heavy denim
material but I knew she could feet me. I rubbed and massaged, softly at
first but then harder and harder. My other hand slid down her belly to the
bottom of her shirt and lifted it up along with her bra until her huge tits were exposed, I broke the kiss and lowered my mouth to her left nipple. I
sucked it into my mouth and played with it with my tongue and gently
nipping at it with my teeth.

My left hand left her crotch and found her hand. I took it and pulled
into my own lap, laying it on the bulge in my own jeans. I gently molded
her hands until they were wrapped around the tentpole in my pants, then I
put my hand back on her crotch. I found her zipper and slowly started to
pull it down. She had to stop me.

“You can’t let Joey do this on a first date.” I exclaimed after taking
my mouth off her beautiful tit.

“Probably not. But if I do, what’s he going to do next?”

I was trying to protect my student, wasn’t I? My reasons weren’t
completely clear in my own mind anymore. I leaned further over and took
her right tit into my mouth. At the same time I found the button of her
jeans with my other hand and opened it. I pulled her jeans open to a V and
slid my hand inside along the cotton fabric of her panties. I could feel
the lips of her pussy, I could feel the heat. I took my mouth off her tit
and kissed her again.

I took my left hand out of her jeans and quickly replaced it with my
right which continued my explorations. My left hand found hers on my
crotch were she had started rhythmically squeezing. I took her hand away
and unzipped my jeans and opened the button at the top. I decided that
what I needed to do was shock her into stopping this. I took her hand and
pushed into the top of my underwear and down until I wrapped it around my
cock. My very hard cock.

My other hand found the top of her panties and slid in. I could feel
the thick curly bush that protected her pussy. I could feel the fat lips.
I rubbed my finger along the crack of her pussy. It felt so marvelously
warm and moist. With my other hand I moved her fist up and down along my
shaft. It had been over two weeks since I’d had any kind of sex and her
hand felt so good. My mind had almost shut down, but somewhere deep inside
was a little voice reminding me that I was a teacher. A responsible adult.

I reluctantly pulled my tongue out of her mouth and my lips away from
hers. I didn’t take my hand away from her pussy. “I can’t believe that
you would let Joey do this.”

“Probably not. But I want to be prepared in case I get carried away by
the heat of the moment.” she gasped. “What comes next.”

I do. I wanted to say as she kept moving her hand up and down my shaft.
I had no idea what Joey would do in this situation, but I knew what I would
have done. I pulled my hand out of her panties, and then I pulled her hand
off my cock. I had to really pull, she didn’t want to let go. Then I half
stood and moved in front of her and down to my knees. I grabbed the top of
her jeans and panties and pulled down, she lifted her bottom so that I
could get them off down to her ankles. Then I buried my face in that
beautiful strawberry blond bush. I licked at the lips of her pussy and
then pushed my tongue as deep into the crevice as I could. Rosie
straightened her body, pushing her crotch further into my face. My tongue
explored every inch of that beautiful valley, until I heard her breathing
shorten and I knew she was on the edge of orgasm. Then my tongue found her

As her spasm subsided, I pulled my face out of her crotch, giving it one
last kiss as I did. I sat back in my chair and pushed my jeans and
underwear down to my ankles. Rosie’s breath was just starting to come back
to normal when I put my hand on her neck and started to pull her head
toward my crotch. I gently guided her until her mouth hovered over my cock
then she opened her lips and sucked me inside of her mouth. Her tongue
explored while her lips moved up and down my shaft. She tried to pull more
of me inside but started to gag as I reached the back of her throat. That
was okay because it didn’t take much to bring me to the best orgasm I’d
ever had. I pumped quarts of cum into her young mouth, She swallowed most
of it, but a little leaked out and dripped into the hair around the base of
my cock.

She sat up and the two of us sat there breathing hard. The student with
her shirt and bra up over the top of her breasts, and her jeans and panties down around her ankles. And the teacher with his jeans around his ankles
and his now limp dick swaying in the metaphorical breeze.

After a minute, “Thank you so much for showing me what to expect on my
date.” she said, hugging me.

“I hope that’s not what you can expect on your date young lady.” young lady? “There’s no way that you should let a boy get that far on a first
date. Or a second, third, or forth date for that matter.”

“I won’t” she said as she stood and pulled her jeans up and fastened
them. “Probably.” She reached behind her and fastened her bra and then
pulled her shirt down. She looked perfectly proper for a student but I
knew there was no way I could ever look at her the same again. I maid a
vow that I would never let anything like this happen again.

I called in sick on Friday. It wasn’t that I couldn’t face Rosie or
anything, I just needed a ‘me’ day. Everyone should play hooky now and
then. I took my boat out on the ocean and fished all day. Caught a
gorgeous salmon that’ll feed me for a week.

On Monday I asked Rosie to stay after when the bell rang. After the
last student had gone and I closed the door, I asked her, “Well, how did
your date go?”

“It was pretty good. We saw ‘Lord of the Rings’.”

“Did you get to see any of the movie?”

“Of course I did. We kissed a little bit, and I had to keep slapping
his hand away from my tittie, but it was a great movie. You should see

“I plan to next weekend. That’s all you did was kiss?

“Of course. What kind of girl did you think I am?” she replied
indignantly. “Well I did let him cop a feel of my butt when we kissed

I swear I will never understand women or girls
Two weeks later I was sitting in my apartment when there was a knock on
the door. When I opened it, Rosie was standing there with another girl.
She was the same height as Rosie, but very thin with only the suggestion of
tits. She had long black hair and a big smile.

“Hi.” Rosie said. “This is my friend Becky. She’s eleven and she has
her first date this weekend. I told her that you’d help her get ready...

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