Teaching a Young Cheerleader
Author: nonono69 <nonono69@hotmail.com>
https://www.asstr-mirror.org/files/Authors/nonono69/www
Date: 21 Apr 2000


Part 1.

This happened when I was in 12th grade, only a few years ago. I was a
big jock on the high school basketball team and was well liked by most 
the girls in the school. I had no problem getting dates with just about 
any girl I wanted.

My younger brother mike was in 10th grade and was trying hard to date 
this cute 10th grade cheerleader. She was very cute but very nieve and 
innocent at the same time. As the year grew on, she became more and more 
stuck up and treated my younger brother very badly.

One night she finally told him to drop dead and not bother her anymore. 
He came and talked to me about it and told me how she idolized me but 
always avoided him whenever she could. He was really broken up and I told 
him I would get even with her one way or another. All night I thought 
about how I could revenge my little brother with this young and stuck up 
cheerleader.

Then the plan hit me. I would act like I was attracted to her, get her to 
be my young little cheerleader slave and then humiliate her in front of 
everyone. The next day at school I started things off by telling a few of
my buddies she was she was a cutie. It didn't take but about two hours 
before I got a message back that she would like to talk with me. Her name 
was Cindy and I sent a message to her to meet me in the lunchroom at 
noon.

When the time came I met her at the lunch room and we talked and laughed 
for a full hour. Then I had all my senior friends tell her in the 
hallways how lucky she was to be able to have a senior basketball star 
interested in her. They made her feel really special and she now knew she 
had to be my girlfriend.

That night I called her at home and we talked for about 45 minutes on the 
phone. I then asked her to the school dance this weekend. She didn't 
hesitate, she jumped right on it and said sure. I told her I would pick 
her up at her house around 7 p.m. Saturday night and we would go eat 
dinner before the dance.

Saturday night came and when I picked her up she was dressed in a cute 
little skirt outfit and nice sweater. She looked very nice and 
respectable. I took her to one of the most expensive restaurants in town. 
The waiters waited on us and gave us their utmost attention. I could tell 
she was impressed. We then headed for the dance and I introduced her to 
all the big basketball and football stars.

You could tell she was star struck. I made sure she had a great time and 
I made sure everyone I knew came up and congratulated her on her catch. 
She was a very happy girl that night. My plan was right on schedule. 
After the dance I took her home and gave her a goodnight kiss at her
door. I wasn't sure but I think that was her first kiss with a guy. I 
went home and started planning part two of my plan.

Monday at school I ignored Cindy all day. Tuesday more of the same. 
Wednesday, she finally caught up with me and asked while I wasn't talking 
with her. I told her all my friends thought she was too young and too 
immature for me and I shouldn't hang out with her. She immediately went 
defensive and said she was not too young or too immature.

I then said that the girls I date are usually more mature and do things 
differently than the young girls do. She said she was as mature as them 
and all she wanted was a chance. I told her I would think about it then 
tell her tomorrow. I got all my friends to be sure to chat with Cindy 
sometime that day or night and tell them how sorry they were to hear I 
was breaking it off with her. I knew this would only drive her more to 
doing whatever I wanted.

That day after school I saw Cindy at her cheerleader practice with the 
other girls on the squad. This then gave me the final part of the plan I 
was looking for. The next day I found Cindy and told her I had made my 
decision. If she could act like the older girls would, and prove she 
wasn't immature, she would be my girl for the rest of the school year. 
BUT, if she couldn't, I would drop her right then and there and there 
would be no more chances. She was eager and ready to go. She wanted to 
know how to start. I told her to meet me at burger king tonight and I 
would discuss this more.

That night around 8pm I showed up and she was there drinking a coke. I 
sat down and we began to chat. I told her I expected her to do things I 
wanted her to do and go with me dressed like a older girl would dress. We 
would do thinks mature people would do and anytime she said no to my 
plans she could just find someone else. She agreed and I then started 
treating her really nice again.

I took her to the mall and bought her some things then drove her home. We 
parked down the street from her house and made out for about 30 minutes. 
She didn't resist when I tried to feel her chest but I didn't go any 
further that night. By the way, she did not have very big breasts at that 
time in her life. Saturday, I told her we were going to a movie around 
2pm at the mall and she was to wear a nice short skirt and cute sweater.

When I picked her up, true to words, she had a very short skirt and white 
sweater on. I took her to a movie that wasn't supposed to be very good 
and we sat in the very last row. She didn't object and after the movie
started I started on her. At first it was just my arm around her, then it
was kissing, then I was slowly rubbing her leg and moving my hand up her 
skirt.

I could tell she was very worried and once she put her hand on my hand 
like she was going to try to move it, but she must have thought about it 
and moved her hand back away. Within five minutes my hand was rubbing her 
cunt thru her cotton white undies and I could tell she was very wet and
very nervous. I whispered in her ear that she was much more mature then I 
thought and then started back working on her.

I slowly slipped my hand under the top of her undies and could feel the 
very fine hair that covered her pussy. I looked around and saw there was 
nobody near us so I told Cindy to close her eyes and not to open them 
till I told her. I said it again, but I put more authority in it and said 
please don't disappoint me.

After her eyes were closed I moved down between her legs, push her skirt 
up a little and grabbed the sides of her undies. I started pulling down 
on them and Cindy jumped a little and said no, not in here. I told her to 
trust me and act like she was a mature woman not a young kid. She closed 
her mouth and didn't say another word. I slipped her undies down off her
legs and then pulled her skirt back down and got back in my seat.

While I was down there I noticed her pussy had fine blond hair on it that 
was just barely visible. It turned me on a lot but I had other plans 
first. After I was in my seat I had Cindy open her eyes and I showed her 
I had her undies in my hand. I tucked them into my pants pocket and then 
started kissing her again. This time when my hand went under her skirt I 
felt her hot soft young cunt and it was soaked all over.

I started slowly rubbing around her slit and found her clit. I then
started massaging it. She never opened her eyes once. Within a couple 
minutes she was squirming all around and then she came with a start. She 
fell back even more in her seat and finally opened her eyes. She just 
said that was fantastic and hugged me for the next 10 minutes.

The movie was as bad as I thought it would be so I said lets go get a 
bite to eat in the mall. She said ok. As I started getting up she pulled 
me back down and asked if she could have her undies back. I said no, I 
would give them to her when I was ready. She then got up with me and we 
went to the food plaza. Her skirt was pretty short and I know it bothered 
her she didn't have any undies on, but this was part of a greater plan.

Monday at school I made sure all my friends spent time with Cindy as if 
she was now part of the gang. She was eating it up. I knew Wednesday we 
had a football game and Cindy would be cheerleading at it. I had a great 
plan for that night. Monday night and Tuesday night I took Cindy to 
different places and made sure each time she wore a skirt. As soon as she
would get in the car I would have her give me her undies and then 
sometime during the night out I would give them back.

Wednesday during school I told Cindy I would pick her up to take her to 
the football game. She thought that was great. When I showed up she came 
out, got in the car, and we took off. I told her to hand me her undies 
and she had a funny look on her face. I said with authority, "hand me 
them NOW or I will just take you back home. Your choice." She slowly
took off her cheerleader bottoms then her undies she had on under them. 
She started to put back on her cheerleading bottoms and I told her no.

She said there was no way she could do her cheerleading stuff without her 
bottoms. I said, "I know that but I will give them to you before you have 
to do any of that." She didn't fight anymore but I could see that worried 
look.

If you remember back to you high school days, the cheerleader skirts are 
very, very short and don't stay down very nicely. As we arrived at the 
football stadium I opened my door and went around to open Cindys door. 
She asked again if she could have her cheerleaders bottom.

I said, "for the last time, don't ask me again. I will give them to you 
when I am ready." Unknown to Cindy, I told my brother about what I was 
going to do and he was to wait till we got there, then film everything
with his VCR camera. He was to stay out of sight and not let Cindy
know at any time he was filming everything. I told him I would take her 
up to the top of the bleachers and for him to be under them filming as we 
went up. We walked very slowly as Cindy was afraid her skirt would fly 
up.

I said, "let's go sit down for a few minutes then I will give you the 
bottoms." She liked that part so she didn't object. We started walking up 
the metal bench seats and I could barely make out my little brother down 
there filming. I made sure to distract Cindy so she wouldn't look down 
under the bleachers.

After we got to the top, we sat down and I told her how proud I was of 
her. If she wanted to walk back to the car with me, I would allow her to 
put her bottoms on. She said let's go, and she got up immediately and 
headed down the stairs. I knew my brother was getting great shots with 
the stadium night lights on overhead.
~~~~~~~~~~~~~~~~~~

Part 2.

As I was walking Cindy down from the bleachers her gym teacher called and 
asked her to come over with the girls. Cindy said she would be right 
there in a minute but the gym teacher said no, right now. They had to 
prepare for the routine. Cindy had a frightened look on her face. I told 
her go for a couple minutes then break away and I will bring her bottoms. 
Of course I had no intention of going and getting her bottoms.

As she walked away holding down the sides of her skirt, I could still 
make out the bottom lines of her ass cheeks. Her skirt was much shorter 
than even I thought. The girls all talked for about five minutes then 
they ran out onto the field. They started jumping up and down and yelling
as both teams were now coming out on the field.

Cindy was keeping her arms at her side trying to hold her skirt down. 
Anyone watching could easily see the white Globes of her ass every time 
she walked. I wondered where my brother was then I spotted him lying on 
the ground near where the cheerleaders would return to. He Was pretty 
much hidden if you weren't looking for him.

As the cheerleaders came back over near him, he was filming everything 
from a great vantage point of the things that Cindy was doing. I finally 
went out, got Cindy's under garments, and called her over. I gave all
her stuff in a paper bag and she went in to the girls room to put them 
on. My brother left right after that, probably to go home and see what 
his video camera caught.

I stayed for the game, then grabbed Cindy and got in the car. We
had won the game and she seemed to have forgotten about the earlier 
incident. Or at least she wasn't talking about it. As soon as we started 
driving I told her how proud I was and I wanted her to meet my family
sometime this month. She had such a big smile and cuddled right up to me.

I then put her back down by telling her to give me her panties again. She
started to ask why as she thought we were going home. But, she didn't 
speak up and handed me her cheerleading pants. I drove to the after 
football game hangout where all the jocks would come after each game. 
Cindy walked in with me but was very nervous. To me it was very easy to 
tell she wasn't wearing anything under her skirt. I don't think she knew 
how short it really was. In the front of the skirt, it looked good. But 
in the back, it was maybe half an inch below her cheeks. Many heads were 
turning as she walked by.

I found a booth and we sat down waiting for my friends to arrive. When 
they arrived they had a bottle of booze hidden in their clothes. We 
ordered cokes and turned them into rum and coke. I made up Cindy's but 
she said she has never drank before. I reminded her not to act immature 
so she thought about it and then took a drink. I made hers twice as 
strong as everyone else's. She said it tasted bad but I had her drink the 
whole glass within about 30 minutes.

I ordered her another large coke and while it was on the way she said she 
had to go to the rest room. When her coke Arrived, I poured half of it 
rum, the other half coke. I knew she was starting to get wasted from just 
the first glass. I also ran and called my little brother and told him to 
get his camera here fast. When Cindy returned I reminded her to keep 
drinking with the rest of us. I could tell she didn't really like the 
taste but she would drink whenever the rest of us would.

30 minutes later we were just finishing our second drink. Cindy was just 
about passed out. She kept resting her head on my shoulder. But I would 
push the glass to her every time we drank so she could drink with us. Her
glass was now empty and at the same time, my brother walked in carrying 
his camera. Cindy was just about to the pass out at this point.

I slid away from her for a second and she put her head down on the table. 
I got up, told my brother my plans, then sat back down with Cindy. I put 
her head back on my shoulder and asked her how she was doing. She just 
mumbled fine and closed her eyes back shut. I reached under the table and 
started playing with her legs. Her eyes didn't open and she didn't move 
at all. I then put my hand under her dress and onto her little, near bald 
cunt and watched to see what she would do. She didn't move or open her 
eyes. I knew I had her now.

I slowly had the guy on the other side of her pull Cindy's leg toward 
him. She still didn't move with the other guys hand on her leg. I then 
pulled the leg on my side towards me. This opened her legs up wide for 
anyone looking under the table to see. I slid Cindy a little so that 
people on the dance floor would get a great shot right up Cindy's split 
legs.

Then I reached over and pulled the front of her skirt up to her waist and 
I tucked it in her waistband. Now it was like she was sitting there nude, 
legs spread wide, with all to see. I also saw my brother filming 
everything from across the room. I stuck my finger in my mouth, go it all 
wet and slippery, and then started playing with Cindy's pussy. I got it 
very wet within a minute or two and then started fingering her pussy.  
Cindy still had not moved and must have been dead to the world.

Before I went too far I wanted to humiliate Cindy even more. I pulled her 
skirt back out of her waistband. It had been there for about 30 minutes 
and many people on the dance floor would point to her when they saw her. 
I ordered some more drinks, made Cindy another strong one and woke her 
up. She was mumbling something but I told her she wasn't keeping her end 
of the deal. She needed to drink with us as we drank. I picked up her 
glass and put it to her lips and she slowly started drinking again. After
about half her glass was gone, a slow song started and I grabbed Cindy 
by the arm and said I wanted to dance. She was so far out of it, she just 
sort of tumbled out of the table. She never tried to hold her dress down 
or anything.

I pushed it down for her and helped her out to the dance floor. There she 
leaned forward, wrapped her arms around my neck and just closed her eyes. 
Doing this her skirt popped up well above her ass in the back. It was 
just about even with the top of her waist. Everybody was watching and 
everybody was spellbound. The jukebox kept playing as we were far enough 
back that the management couldn't see what was going on. My brother was
right behind Cindy now and was filming about two feet from her ass.
I told him to go select about 4 or 5 slow songs in a row on the jukebox
so we will have music going. When he got back he started filming again.

All the guys were now sitting around the dance stage and watching 
everything that was happening. I pulled up on Cindy a little and then put 
my legs between hers. She was now dancing with nothing covering her ass 
and her legs spread pretty wide apart. I would lean backwards then would 
tilt her towards me giving everyone a great shot of her cunt. Then I 
started feeling up her butt, spreading her cheeks wide apart. Of course 
my brother was there filming it all.

Then I started rubbing her cunt. She was wet from my earlier playing
and I started seeing more and more guys around the dance floor. I started 
slipping a finger into Cindy and then two. I could feel her cherry About 
an inch or two inside her cunt. I called Cindy's name but she would just 
mumble something. As the song ended, I had another great thought.

I told my brother to come over and had him hand me the camera. Then I 
moved Cindy off of me to my little brother. She never opened her eyes, 
the next song started and my little brother started swinging Cindy around 
the dance floor. It wasn't long before he was fingering her pussy also. I 
was filming it all and my little brother was having a great time.

After this song I went and got Cindy and brought her back to our table. A 
lot of guys were chatting and smiling but none came over and bothered us. 
I decided to get Cindy out of there to a more quiet place. I took her to 
my house and snuck her into my bedroom. She was out cold. My brother 
still had his camera and he was letting the film run.

I laid Cindy On my bed and undid her skirt. I wanted to fuck this girl 
soooo bad, but that wouldn't be good enough. I thought about letting my 
brother break her cherry, but decided against that. Then I figured it 
out. We would have her break her own cherry. I went into the drawer and 
got out a dildo that I used  on a girlfriend from last year. It was 
about 8 inches long, not real wide, but had big bumps all up and down it.

I started rubbing the dildo up and down her cunt lips. I made sure it was 
nice and wet. Then I grabbed the dildo and started working it up into her 
cunt. After an inch it stopped and I could tell it was knocking at her 
cherry. I made sure my brother had a great view that showed Cindy's face, 
cunt, and hand.

I grabbed her hand, stuck it on the dildo flat along the back side, then 
moved aside so they couldn't see me in the picture. Then I pushed very 
quickly on her elbow which forced the vibrator deep into her cunt. I 
heard her squeal real quickly but that was about it. The vibrator was 
about half way up her cunt and my brother had filmed the whole thing.

I told him to keep the video camera on her cunt and again I pressed down 
on her elbow causing her to push the vibrator even deeper. Then it 
happened, a small flow of blood came out Of her pussy and onto the bed. 
We both watched as the flow continued for about 10 seconds, then it 
stopped.

I had him turn the camera off, I cleaned up Cindy, and put all her 
clothes back on. Then I had my brother give me the camera and go to bed. 
I told him we would put the next part into action shortly.
~~~~~~~~~~~~~~~~~

Part 3.

I took Cindy to my car and drove her to her house. I couldn't really wake 
her up as she was out like a light. It was late so I opened her parents' 
car door and put Cindy in the front seat. I then closed the door and went 
home for the night. When I got home I put the video tape into the VCR in 
my bedroom and started watching the tape. It was very hot.

It started with Cindy at the football field walking, trying to hold her 
skirt down. You could just barely see her butt cheeks as she walked. Then 
as she walked nearer the stands and started walking up them you could see 
very plainly right up her short skirt. My brother had zoomed in a couple 
times and you could actually see the thin blond hairs covering her pussy 
as she walked up the steps to the top of the bleachers. Then he filmed 
her coming down and being called over by her gym coach. Every step she 
took her ass was barely visible to anyone that was looking closely.

Then the filmed switched to the club. You first saw Cindy drinking
with all the guys. Then the next shot showed her hunched over on my 
shoulder and her skirt pulled up a little. Then you saw her skirt pulled 
all the way up over her waist and me playing with her cunt. Then the 
final great part was me walking her out to the dance floor and dancing 
her around in her cheerleader outfit with no panties on. The end of it 
showed first me dancing with her with her skirt tucked into her waist. 
You could see her entire ass and when I leaned backwards her whole cunt 
would open up. It was easy to see my fingers dipping into her cunt.

Then it showed my brother dancing with her and fingering her also. The 
part at home came out perfect. It showed her holding the vibrator and 
pushing it up into her cunt. Nobody else was in view. Then it showed the 
last little push that broke her cherry and sent her red juices out her 
tight little cunt.

Then the video went blank. I went to bed thinking of how to keep this 
little cheerleader tease at our command.

I didn't see Cindy at school on Monday or Tuesday but Wednesday she 
showed up as usual. She found me and said she needed to talk to me after 
school. I said ok, and we met after the last class. Her parents have 
grounded her for a month because she didn't come into the house until 5 
a.m. They could also tell she was drunk. It's a good thing I had put her 
cheerleader pants back on her when I dropped her off. She asked me what 
happened that night as she couldn't remember much after she started 
drinking. She also said her panties had blood in them and wanted to know 
why. I told her we would skip the last hour of school tomorrow and go to 
my house. Then I would explain what happened. She didn't really want to 
but that was the only way she could get any info so she agreed.

The next day after school I took Cindy to my house and started the VCR 
tape. Her mouth just dropped. I told her not to say a word till the whole 
tape ended or she could get up and leave right then. She never spoke a 
word. Then she saw the part where she danced near naked and let me and my 
brother finger fuck her on the dance floor.

But the next part was the worst. She saw herself shove a vibrator up her 
pussy and break thru her virgin maidenhood. When it was over she started 
crying. Why did we do this to her. She must have the tape. She begged and
pleaded. Then I told her the ground rules. She would do our bidding for 
30 days. Everything I ask she must do. If she doesn't, she will never see 
the tape again, but many others will. If she does, she gets this tape and 
the hidden copy I have stashed in a safe place.

She didn't say yes, she didn't say no. She wasn't saying anything. She
got up and walked out. I just said, "REMEMBER THE TAPE....." That night 
around 10pm I got a call.

Cindy asked, "do you promise to give me all the tapes if I do what you 
ask?"

"Yes, you get both the tapes and I won't copy them. That I promise. I 
will even make up a little paper between the two of us that says after 30 
days, you get both copies of the tape and I will not make copies of it." 
She said she agreed, but only after we signed the letter. That night I 
typed up a quick little letter that says I will give her the originals
of the video and wont make any copies. And for this she would abide by
everything I ask for 30 days. I know she would never let anyone see this 
so I signed it and gave it to her the next day. I told her our 30 days 
would start as soon as she was off restriction.

For the next 4 weeks we didn't talk at all. After the four weeks were up 
and I knew she was off restriction, I sent her a note to meet me at the 
mall at noon on Saturday. Don't be late. That night I watched her video 
again. Myself and my brother must have watched that video a 100 times 
since we made it.

My brother wanted to show it to his friends but I wouldn't give it to him 
because I was afraid Cindy would find out and call off our deal. I told 
him we would have much better video to watch in the future. Saturday at 
noon Cindy showed up right on time. We went to the food court and sat and 
talked. I asked her if she was ready for to keep her deal. She started 
trying to talk me out of it. I got up and walked away without saying a 
word to her.

She ran after me and said, "ok, ok, just keep your promise."

"For the next 30 days, you will do what I want or I will pass out that 
video. Is that understood?"

"Yes."

"Then let's go shopping." We went to one of the young female stores and I 
picked out things for her to buy. Short skirts, white see thru tops, and 
a long sweater that came down about 2 inches below her butt. I think she 
thought this was to wear with one of the skirts but I had other ideas. 
Then we went to the local nightwear shop and I bought a few items like 
fishnet stockings, 4 inch heels, and a nice black sleeping blindfold.

I took Cindy home to my house and we went up to my bedroom. She was 
nervous as all get out. I told her to lie down on my bed and close her 
eyes. When her eyes were closed I pulled out the blindfold and put it on.

I said, "don't make a sound or next time I will buy you a gag. 
Understand?" She shook her head yes. I got up opened the door to my room 
and waited for my brother to come in. It took about a minute but he came 
in quietly and had his camera running. I slowly started to undress Cindy 
and I could hear her start to cry. I finally had her down to her bra and 
panties and flipped her a little so I could unclasp her bra. She was not
that big in the breast area.

Next I started pulling her undies down over her hips. She sobbed a little 
more and a little louder. I told her to knock it off or else. She quieted 
down some. I pulled out some baby oil and slowly started rubbing it all 
over her body. Every time I got near her tits or cunt, she would jerk 
real badly. I rubbed oil all over her body and started rubbing it into 
her cunt. Her whole body was a slippery mess. I then had an idea.

I started rubbing her cunt and stroking her clit. At first she showed no 
emotion, but after about 4 minutes I could see her cunt getting wet from 
her own fluids. I then grabbed her hand and put in on her cunt and told 
her to finish the job.

She asked, "you want me to rub myself in front of you?"

"Yes, and now." I started her hand to moving over her cunt and after a 
couple seconds she started rubbing herself. At first it wasn't much and 
she didn't try very hard. I would keep moving her fingers over her clit 
and rubbing with her. Finally she gave up fighting and started rubbing 
her clit for real. After a minute or two her rubbing changed from near 
nothing to a very quick all around motion.

Then it happened, her butt came off the bed and I heard her let out a 
very high moan. She rubbed and humped for about 10 seconds then slowly 
stopped. The great part was we had all that on film. I had promised her I 
wouldn't make copies but I never stated I wouldn't make any new films. I 
motioned for my brother to leave and he did. I slowly shut my door then I 
walked back over to the bed and took the blindfold off Cindy. I told her 
she did great for day one and to go home till tomorrow. I wanted her here 
tomorrow by noon. She said she wasn't sure if she could make it.

I told her in no uncertain terms, "you will be here to keep your 
promise." She got dressed and left. My brother came in and we watched the 
film. It was great. It showed her fingering herself to orgasm with nobody 
in the picture but her... The perfect start.


  
youngcheerleader