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This work is copyrighted to the author © 2009.  Please
don't remove the author information or make any changes
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Tiffany Prepares
by Old Bill (address withheld)

***

When her mother insists that she apply for a job as the 
company slut, a young girl has to get ready so she 
calls for expert help. (mf-teens, 1st, oral, anal)

***

"Tiff, come here," her mother called after hearing the 
girl's boyfriend leave the apartment. They had been 
down in her room for more than an hour with the door 
closed.

The girl came into the kitchen, smiling and raking back 
her long, blonde hair with her fingers. The top snap of 
her shorts was undone and her t-shirt was on inside-
out.

"Have fun?" her mother asked.

The girl nodded and licked her sore lips. She was still 
breathing hard.

"Sit, we have something to discuss."

Tiffany sat down and crossed her long legs, feeling her 
pussy bulging and pulsing after a long session of 69ing 
with Butch Filmore and his talented tongue. The boy's 
cock wasn't much but his jism was tasty, and she had 
made him squeal when she sucked his balls.

"They let me go," her mother said, looking very 
serious, "let ten of us go today including Mandy, the 
resident slut. I got two weeks pay. I don't know what 
she got, probably a mink or something."

Tiffany blinked her heavy-lashed eyes and crossed her 
legs the other way, squeezing her pudenda pleasantly, 
wondering what her mother was talking about. She was 
still thinking about the curved shape of her 
boyfriend's hot appendage, wondering how she could 
swallow it.

"I want you to go and see Mr. Baker and apply for the 
job. It pays well and it's really not such hard work, 
maybe five or six guys a day."

"What job?" her daughter asked, confused.

"Slut, dear. You ought to be good at it since you 
practice almost every day, and you are certainly pretty 
enough; you know that, don't you?"

"Mother!" Tiffany squealed. "Come on, we're just 
playing. I'm a virgin and I plan to stay that way." She 
sniffed. "At least until I get to college."

"You can forget college, sweetie, unless we start 
making some serious money, we'll both be out 
streetwalking. In fact, right now you can forget school 
altogether. You just dropped out."

"But you promised..." She pouted, one of her best looks 
she knew.

"You may not have noticed; there's a recession or maybe 
a depression going on, whatever it is, it's bad, lots 
of people out of work. And we have been living on my 
pay week after week, nothing else, just getting by. And 
now that's gone. Our rent is paid until the end of the 
month, period. Now it's your turn, sweetheart. I got 
two weeks severance, and we owe most of that on the 
credit card."

"But I can't be a, a you-now, a slut or something. I'm 
fifteen." She sniffed but produced no tears so she 
pouted. She refused to admit that the idea excited her.

"Not any more you're not. I changed your age in the 
computer at work. You are a fine and healthy seventeen-
year-old high school graduate, and as far as your 
cherry is concerned, if you still have one, I'll get 
Steve to take care of that tonight; he's got eight-
inches of rock hard cock, and he just loves little 
girls."

"Oh no, uh uh," Tiffany said. "Not Steve, please, maybe 
Georgie whatshisname, that geek. I gave him a handjob 
and his thing is about the size of my thumb."

"I'll think about it," said her mother, "but tomorrow 
morning you and I are going down to see Mr. Baker 
before he finds somebody else, and you can bet he will 
want to give your little pussy and your sweet ass a 
test or two. So if you've still got a hymen, you'd 
better pop it. You can use that wooden spoon or my 
plastic dildo. Oh, and grease up your asshole in the 
morning."

Tiffany sobbed, ran to her room, sat on the side of her 
frilly bed, sniffed as she pushed two or three inches 
of a blunt-nosed Sharpie into her tight-lipped vagina, 
wiggling it until it found the right place, the oval 
hole, squeezed down on it and finally picked up her 
phone and punched Billy's numbers. If she was going to 
have sex with somebody, she wanted the very best.

"Yup," he answered.

"Busy?" she asked.

"Nope, zup?"

"Need your help. Can you come over now or after 
supper?"

"Be there in ten minutes," he said and closed his 
phone. The boy stood, smiled to himself, put three 
Trojan Magnums in his pocket and went out to his old 
car. He had been trying to get into the hot girl's 
pants for more than a year, but she always had excuses. 
She never would yield. And she was one of the cutest 
girls in school with a great rack and a tight ass. Her 
long legs were an invitation to fuck and the way she 
walked was very, very, very stimulating. The right word 
for her pace, he had decided, was undulating.

Tiffany met him at the door wearing his football 
jersey, just his football jersey, the one she had 
earned with a deep-throated blow job he still 
remembered, and her high-heeled slides. Her mother was 
out at the neighborhood tavern with Steve, her current 
part-time lover. She looked hot and they both knew it.

At the door to her room she came into his arms and 
hugged and kissed him, kissed him hard and open-
mouthed, her tongue exploring. His left hand grasped 
her bare ass and his right slipped up her back finding 
only skin. She led him to her turned back bed on which 
she had spread an old beach towel.

"I want you to take my cherry," she said quietly, "and, 
and, well, teach me how to do it, you know how to 
please men. My mother wants me to become a slut down at 
this lawyers' office, to do it for money. She got 
fired, laid off."

Billy sat and pulled the girl down on his lap, cupped 
her full breast and kissed her deeply as his other hand 
searched her slit and found her tiny clit. He probed it 
out with his thumb and then teased it with his 
forefinger. It was a bigger than average once it was 
erect, and he watched the girl react, eyes wide and 
mouth open as he pinched it gently between his fingers, 
stretching it.

"Oh," Tiffany sighed, writhing as Billy yanked the 
jersey over her blonde head and tossed it aside while 
he slipped a finger into her dripping pussy. Her full 
breasts bounced as he put her down on her back, 
snuggled beside her and sucked one prominent nipple 
into his mouth while her finger fucked her gently, 
finding her hymen and pressing it firmly, discovering 
that one side was barely attached while the other side 
was pretty thick and would take some effort and cause 
some pain and a bit of bleeding too if he was going to 
get it all out of the way. Oh well, he thought, it 
isn't going to hurt me.

Tiffany was not Billy's first virgin; in fact she was 
not even his twentieth virgin. He had long since lost 
count of the number of girls he had popped open and 
wished again that he had written them down somewhere. 
He had been a very active stud for almost three years, 
fucking many of the young matrons whose lawns he cut as 
well as dozens of high school girls and a few that were 
younger. 

Through diligent practice and Kegel exercises he had 
gained a lot of control of his big cock and his 
insistent sex drive and could now usually climax three 
times before he needed a rest and hold back an 
ejaculation almost at will. On most summer days, he did 
two lawns and two grass widows.

"You're going to quit school?" he asked as he got his 
two middle fingers into her very tight vagina rotated 
and probed, hooking them upward where some girls seemed 
very, very sensitive. He wasn't sure he believed that 
there was really a G-spot, but she writhed and snorted 
under his poking.

The girl moaned and arched her back. "Do it, do it," 
she sobbed. "I'm dying for it." She could feel that she 
was becoming both warm and wet. He could feel that she 
was juicy and ready.

Billy stood and quickly stripped, and Tiffany gasped 
and put her hand to her mouth as his massive manhood 
jumped loose and began to fill and rise like the bucket 
of a front-end loader, high and higher, bigger and 
bigger, strong and massive, frightening and exciting. 
He grinned at her and bounced it in his hand, smacking 
it loudly.

"Please don't hurt me," she begged, her voice 
quivering. She stared and could not believe what she 
was seeing. It will never fit, she decided feeling her 
heart beat rise.

"Spread your legs and hold your lips apart," the boy 
said with a smile, bobbling his huge phallus, stroking 
it in his hand. "Are you on the pill?"

"I've changed my mind," Tiffany moaned, turning her 
face away and pulling up her knees. Billy got down 
behind her and made his hard body conform to her softer 
one, his jutting cock right up between her smooth 
thighs. He had run into this before, even with some of 
the full-grown women, but since he could not help what 
his equipment looked like, he had found ways to deal 
with the problem; generally a little cuddling and 
petting would do the trick. Besides he liked doing it 
spoon fashion and Tiffany's ass was world class, firm 
and shapely.

He nuzzled the back of the girl's neck and slid his 
hand under her breast and caressed it very gently while 
at the same time his big prong explored her dripping 
slit, looking for her clit or her entrance, hungry for 
friction, its big head dripping lubricant. There was no 
way she could stop him now; we was well past the point 
of no return, his balls clamped up at the base of his 
thick shaft, throbbing and tensing.

"Don't Billy," she sobbed. "Please don't. I'm scared. 
It's too big."

His other hand went under her waist and down into her 
groin where his fingers crawled into her vulva and 
opened her lips.

Tiffany sobbed and quivered as he spread her outer 
labia and thumbed her clit.

"I can feel it. Oh Billy, it's so big." He was in; the 
game was over. All that was left was the celebrating. 
"Ahhhh," she sighed. The pressure was frightening, but 
she felt herself opening like a flower.

"Relax, relax," he purred. "I won't hurt you. Just push 
back a little. Relax. It's going to feel great." He 
felt her lips close about his cock head and pressed 
gently upward, squeezing her breast just a bit more 
firmly to distract her, her jutting nipple between his 
thumb and forefinger. She turned her head toward him 
and he clamped his mouth to hers.

An inch or two into her, he paused and exhaled and 
freed her lips and tongue. "There, see," he whispered 
as he stretched her nipple and rubbed her clitoris 
under its hood, pressing firmly. "Doesn't that feel 
good?" He kneaded her warm boob.

"Uh huh," she sighed, and she felt her pelvis move all 
by it self, trying to get more of the huge invader. It 
surprised and embarrassed her. She wanted to be ripped 
open. The big thing in her was throbbing, pulsing, 
filling her, and ravaging her poor little pussy. And 
she wanted it, wanted it all. She sighed and wriggled, 
taking him deeper.

Billy's huge manhood flexed and then jumped all on its 
own, and the boy smiled to himself, ignored her squeal 
and pushed it in another inch until he felt her 
maidenhead, her perforated hymen. "Are you trying to 
relax?" he asked, petting her breast and pushing gently 
but firmly against her membrane with his sensitive 
glans. Her vaginal opening seemed to be small and 
toward her left, and he changed his position slightly 
and pressed a bit harder, feeling it stretch, the oval 
portal opening wider, the wall pulling, parting, 
yielding.

"That hurts," she sobbed, and he backed off and his 
cock jerked again producing another squeal.

"Come on now, that didn't really hurt," he whispered, 
teasing out both her nipple and her clit and then 
releasing them, petting them.

"No, no, but it scared me," she said in a quivering 
voice. "Have you done it? I know you're in there, 
deeper in there. I can feel things pulling apart, 
tearing."

"Almost," Billy replied, pressing again and rotating 
his body slightly, trying to screw his hard corona 
through an opening less that half its size. The 
membrane gave and pulled away from the wall of the 
girl's unsullied vagina and she gasped. Four or five 
inches of the boy's thick, hot, hard shaft filled her 
completely, splitting her, impaling her, deflowering 
her.

"There," he said clearly, holding it firmly within her, 
"there. See, that didn't hurt, did it?" He kissed her 
cheek and tasted salty tears.

She nodded, shocked and unable to speak. She could feel 
it throbbing deep inside her.

He backed off a couple of inches and pressed upward and 
inward again, stretching her a bit and tearing more of 
the thin tissue free, folding it back as her vaginal 
muscles rippled. He rolled her over onto her stomach, 
lifted her at the waist and said, "Get up on your 
knees, head down, butt raised."

She gasped but did as he ordered, still feeling his 
hard rod deep within her. Her pussy quivered and 
contracted as he pushed still deeper.

"Good, good," Billy said. "That felt really good. Now 
pretty soon, I'm going to have to put on a rubber, 
understand?"

She shook her head as he drove a full six inches of his 
ram into her.

"A condom. You don't want to get pregnant, do you?"

"No, no," she sobbed, feeling as if her body was being 
split open, "but Momma put me on the pill last year."

Billy pulled back and the thick ridge at the base of 
his domed cockhead pulled her torn hymen free. Tiffany 
screamed and Billy thrust, burying his whole ram in her 
young body, battering at her cervix and producing 
another grunt of pain. "Good, but you shouldn't let men 
do it unless they use a condom, get it?"

She whimpered and nodded as his next thrust went even 
deeper, parting her flesh, threatening her womb.

Billy held her rounded hips with both hands and started 
fucking the lithe girl, using long, firms strokes five 
seconds apart and getting a bit deeper with every time. 
Tiffany was gasping with each penetration, moaning, 
"Ugh, ugh, ugh," as he rammed it into her, deeper and 
deeper. It was starting to really feel good, and he 
accelerated, smacking them together.

"Damn," the boy thought, I really don't want to shove 
it into her womb, but he hated to stop with a couple of 
inches unsheathed. He had buried it once, he was aware 
of that so he knew she could take if properly aroused. 
He slowly withdrew his weapon from her clinging lips 
and flopped down beside the girl who still posed with 
her ass in the air. He fumbled on the floor, found his 
jeans and a Trojan packet. He nudged Tiffany. "Here, 
you do it."

The gasping girl sank down beside him, glanced at his 
rearing member and took the golden packet. She tried to 
open it and failed.

"Use your teeth," he said with a smile, putting his 
hand down on his surging balls. His scrotum was now 
globular and very hard.

She tore it open and took out the disc of latex. 

"Slide it down slowly, carefully," he said, holding his 
ram at its hairy base, feeling his hard pulse.

Tiffany knelt above him and used both hands to pull the 
condom down his thick shaft, stroke it gently and then 
sat back and admired her work. It stood upright, 
gleaming in lubricated latex, a small safety tip at its 
head, trembling. "It looks like a rocket," the girl 
said, giggling.

"OK," he said with a smile, "on your back. Let's do the 
good old missionary."

Once he was in her, the girl wrapped her legs about his 
middle and they merged and fucked, both of them 
grunting and sweating as they neared their orgasmic 
peaks. Billy moved higher on her body, making sure he 
rubbed her whole slit.

"Yah," Tiffany yelled as she came, "Oh, oh, oh damn, 
damn, damn."

Billy reared up above her on fully extended arms and 
clamped down on some deep PC muscles in his groin as he 
did push-ups into her. He shook with lust but held back 
his climax, shuddering and waiting for the urge to 
pass. Then he got her legs up on his forearms and 
started again.

An hour later, Tiffany had sucked him back to rigidity, 
and they had fucked for the fifth time, both of them 
grunting like crazy and enjoying themselves fully, 
Billy's big cock bare again since they had used up all 
his condoms. After she gasped and went rigid, he let 
her flop, pulled out of her sucking hole and got 
dressed.

"Thanks," she said. "I can't believe all the things we 
did."

"See you around," he said with a wave. "It was fun."

A while later when she heard them come in, Tiffany 
joined her mother and Steve in the kitchen.

"Well?" her mother asked.

"I'm ready," the girl said. "He showed lots of 
positions and really stretched me open."

"Did he do your ass?" Steve asked, patting the girl's 
butt.

"Uh huh," she said, shaking her head. "He said he 
didn't like that; said it was un-something, unnatural?"

Her mother went to the refrigerator, got out the small 
tub of margarine and tossed it to Steve. "All yours, 
big boy," she said with a smile. "Ream her out."

Tiffany squealed when he yanked down her shorts.

END

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

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Kristen's collection - Directory 61