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62

William and Ann - 5
by Jack831 (address withheld)

***

William and Ann go on a date. (mf-teens, youths, inc, 
mast)

***

Chapter 6

Saturday morning arrived and the kids were eager to get 
started on their official first date. Larry gave Ann 
$200 in cash and William $30. He told them to spend it 
wisely and enjoy their outing. He'd be waiting at home 
anxious to see what she got. Ann gave him a hug and 
kiss on his mouth. 

Larry, not wanting to waste the moment, returned the 
hug and gave her a little more than a "fatherly" kiss 
in return as his lips opened up and attempted to taste 
his daughter's bottom lip in his mouth. Ann didn't seem 
to care that her father was mildly molesting her. It 
was the least she could do for him after he just gave 
her $200.

Will knew what his $30 was for and was ready to make 
the purchase. Feeling like he was on a date, he opened 
the passenger door to his 1977 Nova as his sister 
entered. He then got in and took off like a bat out of 
hell down the block trying to impress her with his 
driving skills. She squealed like the school girl she 
was as he sped downtown to the mall. She grabbed his 
hand partly out of fear, but also partly because she 
liked how secure he made her feel with his big hand 
holding her little one. 

When they got to the mall parking lot, he jumped out 
and ran around to open her door. She felt like a 
princess as he held her hand to help her out of the 
bucket seat. They shared a kiss as she stood up and he 
put his arm around her as they entered the mall. No one 
could have wiped off the grins on these siblings. The 
first stop for Ann was to find some jean shorts. 

They went to three stores before she settled on a pair, 
but after standing outside the dressing room for the 
first store, Will got bold and followed her in to watch 
her undress and squeeze her pubescent hips into the 
shorts. After she modeled them deciding if they were 
what she wanted, he would tug them down off her and 
give her a loving smack on her panty-clad butt. 

They stood in the dressing room locking lips with the 
shorts down around her ankles. Ann's fingers ran over 
Will's crotch as he traced her butt crack with his 
fingers over her underwear. She whispered into his ear, 
"Just wait until I get my swimsuit." The mere thought 
mixed with her lingering fingers on his cock caused 
William to groan with anticipation.

They went to the music store and bought a tape of 
"Appetite for Destruction" and the soundtrack for 
"Dirty Dancing" so they could have something to listen 
to later. Ann hooked her hand inside her brother's back 
pocket and he had his hand resting on her tit as his 
arm wrapped around his little sister's neck. Ann felt 
so grown up and William felt like a regular guy now 
that he had a "main squeeze" to escort him in the mall. 

As they jumped on the escalator, Ann was aware of a 
group of her friends sitting on the bench who had 
walked to the mall to hang out. They looked up and 
noticed Ann's hand in the back pocket of a boy who was 
taller and looked older than her. They also noticed 
that the boy's fingers were making small circles on her 
tit as they stood on the escalator. The girls decided 
to go snoop and see what Ann was up to and who this 
mystery guy was.

William and Ann, in complete bliss, continued to stroll 
past stores until they got to Macy's where Ann could 
find a nice selection of bikinis, underwear, and other 
shirts that were more revealing than some other stores 
geared to her age group. She went to the Junior's 
section and had Will hold the clothes she wanted to try 
on. Standing by the racks in the Maternity section 
stood her friends spying on them from a distance. 

One girl, Belinda, recognized the guy as William, but 
didn't think Ann would ever act like that around her 
own brother. Ann hardly ever acknowledged him when 
Belinda visited her and never gave her any indication 
that she would be seen with him in public. However, 
Belinda didn't say anything until they saw the guy 
sneak into the dressing room with Ann. That's when she 
spilled the beans to the rest of the group. 

None of the girls believed it and said it had to be 
another guy. Ann wouldn't date her brother. They 
decided to wait until the siblings came out and act 
like they just ran into her. That would give them a 
better look at her date who shouldn't have been in the 
female dressing room with her.

Meanwhile, behind the dressing room door, Ann was 
stripping down to try on her choices. She was standing 
in her lace-trimmed and slightly padded bra with her 
pastel panties that had a Strawberry Shortcake on them. 
She knew she was supposed to be mature, but she still 
loved to dress up like a little girl on occasion. 
William was fascinated with the view and the ease into 
which she got undressed around him. Ann told him to get 
undressed, too, so she didn't feel alone. He was down 
to his socks in no time flat. 

Ann was thrilled to see he was sporting wood as he 
gazed at her. She put on a few shirts and asked how she 
looked. The cleavage of the shirts plunged down below 
her bra. She was happy knowing her dad was allowing her 
the freedom to get whatever she wanted and seeing the 
effect her choices had on her poor big brother sitting 
on the dressing room bench with nothing but socks and 
stroking his dick. Obviously, she was going to get 
those shirts. She removed the shirt and then her bra 
and dropped her panties as she reached for a two-piece 
swimsuit that had less total fabric than the Strawberry 
Shortcake panties she was wearing. Ann told William she 
needed help getting the top tied. 

He had a hell of a time standing up, but that was the 
point. Ann reached behind her and stroked his cock as 
he attempted to secure the top. She then had him sit 
back down on the bench and bent over to get the bottoms 
on. As she did, she backed into him, putting his face 
just above her ass. He leaned forward and gave her 
protruding pussy lips a kiss. She moaned in silent 
ecstasy. 

Her pussy was dripping wet from all the teasing she had 
done and the thought of her brother's cock entering her 
again. She sat down on him and wiggled her ass until 
his erection was fit snuggly in between her labia. 
Slowly, she sank down burying his bone into her hot 
teen snatch. Knowing the dressing room door was the 
only thing keeping them from being in public was an 
erotic thought. William was reminded what Larry said to 
him about using a condom, but considering the 
unexpected moment and the fact that Ann initiated it, 
he was willing to take his chances this time. 

Just a few yards away, Ann's friends were lurking. 
Belinda decided to go the next step and get a closer 
look. She grabbed a shirt off the rack next to her and 
walked into the dressing room next to where Ann and 
William were fucking. She shut the door and looked 
under the wall between the changing rooms. She saw two 
pair of bare legs touching and knew something was going 
on. She then quietly stood on the bench of her booth 
and peered over the top. It took every ounce of 
restraint in her to keep from squealing out. 

There in the booth beside her was her friend, Ann, 
wearing a "barely-there" bikini sitting on her 
brother's lap. Will was staring at the back of her 
bouncing hair and had his hands clamped on her fabric-
covered tits with her nipples squeezed between his 
fingers. Belinda couldn't see Ann's face from her 
angle, but she could tell she was enjoying herself by 
the moaning coming from her throat. 

Just as silently as she entered, Belinda backed out and 
left the dressing room to go report what she saw to her 
other friends. When she arrived back to them and said 
what she saw, Susan and Kelly screamed in disgust, but 
Belinda and Natalie were laughing. The screams weren't 
muffled, though, and were loud enough to get the 
attention of Ann and Will. 

Ann got up off Will and told him to hurry up and get 
dressed. Sadly, he was so close to coming that he 
couldn't possibly do anything until he finished, which 
was just seconds away. He jerked himself for five more 
seconds as Ann was shedding the bikini and getting back 
into her own clothes. He blasted his pent up cum out 
which landed on the carpet behind Ann. She looked back 
over her bare shoulder and smiled at him. Ann loved 
having such power over a boy. 

She didn't bother putting on her bra, sticking it in 
her purse and tossing her blouse back on. Ann dashed 
out of the dressing room leaving William to deal with 
his cum-coated hand, which he wiped off on the bikini 
bottom Ann left on the floor. He was getting dressed 
again while Ann went to see who had screamed. 

Sure enough, there was Belinda, Susan, Kelly, and 
Natalie standing together ten feet from the entrance to 
the dressing room. Once again, it was clear she had 
gotten caught in the act of fucking her brother. They 
looked at her and giggled. Ann, being unashamed of her 
situation, walked up and greeted them with a wide 
smile. 

"So, Ann, what's your brother up to? Or should I say 
'who's your brother up in?" asked Kelly.

"He's IN me, and I love it, Kel. You wouldn't believe 
how good he is. We're going out, and I have to tell you 
it is better than I would have ever thought. He knows 
how to treat a woman."

"Are you kidding, Ann? How could you be screwing your 
own brother?" injected Susan.

"Easy. He wanted me, and I realized I wanted him. We 
fit together perfectly, Susan. Besides, I don't have to 
worry about him dumping me. He's my brother and will 
not leave me."

"Ann? Do you let him squirt his stuff in you?" asked 
Natalie.

"Yeah, but I don't mind. It feels good when he does, 
and he said it makes me look sexy when he watches it 
come out of my hole. What's the big deal?"

Natalie replied, "The big deal is that he could get you 
pregnant, Girl. Do you really want to have your own 
brother's baby in you? That's gross."

"I don't think it'd be gross at all. We love each 
other, and besides, I don't think I can get pregnant 
yet."

Just then, William emerged from the dressing room 
holding the clothes Ann handed him earlier to try on. 
He recognized the girls as Ann's friends who had come 
over to visit her on occasion. They all looked up at 
him giving that look of "I know a secret". He moved 
behind Ann and put his hand on her waist. She was 
satisfied knowing he wasn't going to be afraid of her 
friends and still show his affection toward her. Ann 
leaned her head back and kissed him fully on the mouth 
right before her group of friends. 

"Wow, you guys! That's amazing," said Natalie. 

"Thanks, Nat." Ann thought she was making her friends a 
bit jealous since she had an older boyfriend who was 
intimate with her while her friends were probably still 
virgins and hadn't gotten past second base with a boy.

"Well, we have to go pay for these clothes. I'll catch 
you all later. Come on, Will." She took him by the 
hand, and they walked to the counter to purchase the 
shirts and bikini that was still wet from Will's wiped 
cum. 

The group of girls watched them leave and couldn't wait 
to get home and on the phone to share the news. They 
were in shock that Ann didn't seem at all embarrassed 
or ashamed of herself. In fact, she seemed proud of 
herself. She didn't ask them to keep it a secret, but 
maybe she figured it didn't matter to her and she knew 
her friends couldn't keep it under wraps anyway, so why 
waste her breath asking them to do so.

After paying for the clothes, they went to the food 
court to look for something to eat. While they were 
sitting eating their Chinese food, Ann decided she 
wanted to tease her new boyfriend. She seductively took 
her egg roll in her two fingers and licked the end 
before giving it a wickedly tantalizing blowjob as Will 
watched in awe. Ann's eyes told him he would have his 
chance soon enough. She gently grabbed it with her 
teeth which gave him goosebumps. He grabbed her 
chopsticks and told her he had plans for those later, 
sticking them in the bag of clothes and tapes. William 
then said they had to stop for some rubbers at the drug 
store or gas station. 

That reminded Ann about her tampons and pads. She told 
him that it would make her feel better if he would go 
with her to get some. William was unabashed at the 
thought and said he would be happy to help her, but he 
wanted to see how a tampon worked. When she told him 
she hadn't ever put one in, he quickly offered to 
assist. He told her she could help him put on a condom 
since he'd never put one on, either. She was pleased to 
do her part.

They left the mall with $60 left from the $200 they 
came with and the $30 still in William's wallet. Ann 
had gotten a few nice outfits and a bikini. She wanted 
to go to Victoria Secrets, but William said they were 
overpriced and she looked hot enough that she didn't 
need to spend her money on worthless things from there. 
He said he would take her somewhere else where she 
could get sexy clothes at a cheaper price.

William peeled out of the mall parking lot and drove 
over to Walgreens to get their necessary supplies. 
Choosing the condoms was fun because there were several 
choices, but oddly enough they were displayed directly 
next to the pregnancy tests. Will thought that it was 
too late for condom sales if you are needing to take a 
home pregnancy test. Ann chose a box of Trojans which 
had ridges for "her pleasure" on them. William wanted 
to get a box of Magnums, but Ann said she didn't think 
he was quite ready for those yet. 

They turned around and looked at the large selection of 
sanitary pads and tampons. Since Ann hadn't ever 
purchased them, she decided to go for the small sizes 
and hope they worked. William was looking forward to 
seeing how a tampon compared to a penis. They got back 
out to the car and ripped into the package of condoms 
and tampons to read the directions. William didn't want 
to go home yet because he knew their dad would be 
waiting for them, so he decided to continue their 
"date" by taking his sister to see a movie. 

Luckily, there was a matinee showing of three crappy 
movies, and it wasn't too crowded since there weren't 
any blockbuster shows out that week. Because of Ann's 
age, they had to go to a PG movie, so they got tickets 
for "Nuke 'Em High". The movie didn't matter as long as 
they had time alone. The movie was ninety minutes long, 
so they had at least that time to be together in the 
dark to play with their new purchases. Since reading 
the instructions in the car, Ann was ready to try 
putting a condom on Will. They went to the very back 
row and sat in the far right corner away from anyone 
who might actually come to see the movie. 

Before the previews were over, William had his shorts 
back down to his knees. Ann was tugging on his prick 
and had her new jean shorts on, but also pushed down 
below her knees allowing Will to massage her clit with 
her legs slightly spread. Will was carrying a tampon in 
his shorts pocket. He also had read the directions for 
proper tampon insertion and thought it might go in 
easier if she was wet, though it mentioned it's easier 
if the girl is standing with a foot up on the edge of a 
tub or something. Besides, she wasn't really in need of 
one right now since she wasn't having her period yet, 
but it didn't matter. It was just for experimentation 
purposes.

Ann decided to give her brother that promised blowjob 
since they were currently all alone in the theater and 
quite hidden from view in case others showed up later. 
She got on the floor and told him to close his eyes. 
Having practiced on the egg roll less than an hour 
earlier, she was ready for him. She began by rolling 
her tongue over the glans of the penis, sticking the 
tip of her tongue into his slit. Then, she slowly 
started to bob her head taking gradually more of his 
dick into her mouth. 

He was in heaven as he felt the warmth and wetness of 
her mouth engulf his penis. She held him deep in her 
mouth and started to suck him like a vacuum. It was 
incredible! Ann released him now that he was at full 
mast and opened the wrapper, pulling out the coin-sized 
rubber. She stuck it on the tip and tried to unroll it, 
but as often happens, it was the wrong side, so she had 
to flip it over and try again. 

According to the package, if you do that, you're 
supposed to throw it away and get another one, but she 
thought that was dumb and a waste of money. This time, 
it went down smoothly to the base of Will's shaft. She 
made sure to pinch the top like the picture showed to 
collect the ejaculated semen. The tightness squeezing 
on his cock was awesome. It felt just like Ann's tight 
pussy. Ann sat back up in the chair and told him to put 
that tampon in her. 

It didn't take long for him to get into action. William 
pulled off the wrapper of the tampon, looked at the 
missile-looking contraption, and remembered that it had 
to go in at a slight angle from the back to the front. 
He positioned the tampon with a shaky hand. He was 
nervous and excited as he moved it to the entrance to 
her young twat. He got on his knees and used his left 
hand to spread her lips apart. The flickering lights of 
the movie gave off an unexpected amount of light. He 
saw the glory hole she so willingly offered to him and 
inserted the rounded tip of the tampon into her. 

Her pussy was so wet that it slid in an inch without 
any problem. It was far more slender than his cock, so 
he knew it wouldn't hurt her. Then, he plunged the tube 
and pulled it out, exposing the string from her vagina. 
It was quite an erotic scene for him. He had never 
thought he would get to see something like that from 
his sister, especially while he was wearing a condom 
and they were in a back row of a movie theater. 

Ann was impressed at Will's skill of tampon insertion. 
She kept her legs spread and fingered her clit, 
reaching down to feel the string hanging out from her 
opening, and closed her eyes to masturbate thinking of 
Will. Will stroked his rubber-covered dick as he 
returned to his seat and looked over at his sister 
giving herself a nice rubbing. Her nipples hardened 
beneath her blouse. He took his free hand and gave a 
loving tweak of the nipple closest to him. She opened 
her eyes and told him, "Kiss me right now, Will."

Will leaned over and the two teens were locking lips 
again. She then stood up and said, "I've got to fuck 
you, Will." Moving herself back into the position she 
took at the dressing room. The movie played and anyone 
who would have entered would have only seen a girl 
sitting on her boyfriend's lap, totally unaware that 
her boyfriend's boner was firmly planted inside her. 
His prick pushed the tampon further up into her snatch, 
but she hardly noticed. She was curious to know what it 
felt like to have the condom inside her.

He put his arms around her waist and hugged her close 
to him as he continued his barrage on her vaginal 
orifice. Even through the thin barrier of the condom, 
William could feel the heat and muscular contractions 
of Ann's pussy and the strange sensation of the cotton 
tampon he was pushing into with each downward thrust 
she made into his lap.

Ann was enjoying it and wanted to savor the moment, so 
she rested a few minutes just sitting there on her 
older brother's lap as the movie continued rolling on 
the screen before them. William's hands roamed gently 
up and down the sides of her beautifully contoured 
body. 

An usher poked his head in and saw the empty theater, 
minus the two kids in the corner. Some girl was 
cuddling on her boyfriend's lap and he was stroking his 
cute girlfriend. Nothing was in the violations codes 
about that. They were watching the movie, they paid for 
their tickets, and they weren't tearing up the place, 
so he turned his head and left them alone. Had he 
walked just a few feet closer, he would noticed her 
bare legs which were dangling on either side of the boy 
and her panties and shorts still clinging to her legs 
by her ankles. 

William started to grind his hips again wanting to get 
back into a rhythm. Ann got the hint and began making 
slow small circles on his lap before she lifted herself 
up and gliding back down on his rubbery shaft. Again, 
the gripping action of the contraceptive device and 
Ann's cunt were working together to bring William 
quickly to a climax. 

He tightened his hold on her hips and grunted, 
exploding the contents of his ejaculation into the tip 
of the condom. Ann wanted to see it and got off his lap 
to look. Still slick with her pussy juice on the 
outside of the rubber, she grasped his cock in her hand 
and continued to jerk it until he went soft. Ever so 
gently, as William sat back in the theater chair and 
panted, she removed the condom. Some of his semen had 
dripped down the sides and to the base of his dick 
since she didn't remove it properly. The cool air in 
the theater combining with the wetness on his shaft 
caused Will's cock to jump from the sensitivity. 

Meanwhile, Ann held the rubber upside down in her 
fingers, smelling that bleach-like aroma mixed with 
rubber. What she did next was something William thought 
was too erotic. She turned the condom over and had the 
remnants of it drip out and onto her peach fuzz cunt 
hair. She dropped the used prophylactic onto the floor 
and rubbed his sperm-laden semen through her hair and 
into the crack to lubricate her clit. 

William got down on his knees to see her masturbate 
with his cum. Ann's head was cocked to look down and 
see her brother's slime on her fingertips and groin. 
When she saw him looking at her getting off, she was 
reminded about the tampon. 

"Will, can you pull on the string in me?"

"Yeah. It got pushed up inside you, but I can find it."

He put his finger inside her opening and fished around 
to find the tampon string. He worked it out until he 
could get his thumb on it and started to pull it out. 
Then, he thought he'd do something sexy for her and put 
his head down to pull it out with his teeth. When he 
did, his nose made contact with her clit. He smelled 
his own cum on it as her fingers danced around her 
vulva. Carefully, Will tugged on the tampon string 
using his teeth. 

He was so close to his sister's vagina he could 
actually feel the heat and smell her sweet juices as 
they seeped from her orifice. She was groaning as her 
climax was about to arrive. 

Just as the tampon, still white, but a little moist, 
came out of her, Ann shuttered, then tensed in orgasm, 
jamming her finger inside to replace the cotton wad. It 
was one of the best cums she ever experienced. Will was 
staring at her wondering if the finger she just stuck 
inside had enough remaining sperm that it could wiggle 
free from her finger and swim up into her uterus. More 
than likely, it was dried out by now, but he wasn't a 
scientist, so he didn't know. Besides, he didn't inject 
her with his seed, she would have impregnated herself. 

The movie was about an hour in when the two kids got 
their clothes back in place. They stayed to watch the 
remainder of it as they held hands and kissed in post-
coital bliss. 

To be continued?

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Kristen's collection - Directory 62