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                 K R I S T E N' S    C O L L E C T I O N
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Little Bobby's Problem
by Hansel (dougcolman@btconnect.com)

***

An 18 year old boy who's not been allowed to grow up 
(except in one obvious way) is repeatedly 'treated' - 
first by his stepmom, then by a variety of 'medical' 
methods. (FFM, nc, mast)

***

CHAPTER ONE: 

THE RISE AND RISE OF BOBBY NUPPENDAUN

This story really began when 18 year old Bobby 
Nuppendaun was in his stepmother's bedroom, in the 
middle of one of the countless masturbation sessions he 
enjoyed each time she went out. Except on this occasion 
Ellen Highwater chose this exact time to come back to 
the house, to collect her forgotten pocketbook. 

As she climbed the stairs, she suddenly heard Bobby's 
voice – coming from her bedroom, it seemed – as the boy 
talking to himself, quite obviously in a state of high 
excitement. In actual fact he was nearing ejaculation, 
his stepmom's bed squeaking in time with his pumping 
hands, as he panted and jabbered away, oblivious to her 
approach. 

"Oh – those – big – boobies - how - I – love – them!" 

'I don't believe the size of that' she said to herself 
as she stole closer to her room, fascinated. The boy 
was clearly in another world as she peeped round the 
door and saw for the first time the huge cock that 
Bobby's endless masturbating had built. 

I should explain something at this point. Bobby was – 
shall we say - a little naοve. Oh heck, he was very 
naοve. This was not altogether an accident: since 
moving in with his stepmother eight years before, he'd 
had little or no dealings with the world outside. His 
stepmom had never been able to have children, and 
decided early on that Bobby would be her special 
'baby'. She even took it on herself to teach him at 
home, so the lad would never need to be exposed to the 
big, nasty world. 

Until she had him ready, of course.

Bobby had long fantasised over his stepmother's 
enormous, torpedo-shaped breasts. Although he had never 
seen them uncovered, never even seen into the 
bottomless canyon of her cleavage, his waking (and 
dreaming) hours were more and more crammed with images 
of the two monster mammaries that her tightly buttoned 
tops must contain. 

Ellen Highwater was a majestic 6'3" tall with a 
perfectly proportionate build and wide shoulders. They 
had to be wide or she could not support the massive 
breasts she did indeed restrain in a tight fitting FF 
cup bra. Since the demise of her late husband some ten 
years earlier, Ellen always kept her giant breasts 
tightly confined and totally covered. 

There were good reasons: Being so big, they would 
otherwise wobble and bounce so much that they would 
interfere with her balance. And, if they were allowed 
to move freely, the friction of her clothing against 
her big nipples would cause Ms Highwater to be 
constantly aroused and horny. Keeping them tightly 
bound just felt so right. There was another reason. Due 
to a biological imbalance, Ellen Highwater had been in 
a constant state of lactation for the last twenty 
years. Rich, heavy, lactation. So huge, tight 
brassieres were essential, except when she was faced 
with the task of emptying the tankers harnessed within.

One of her huge brassieres was currently wrapped round 
the stiffened monster in Bobby's hands, being used as a 
sheath with which the boy was so rapidly pumping his 
penis. Bobby knew from experience that orgasm was 
approaching, and speeded up his hands, his speech 
slurring in passion. 

"Oh Mummy. Uurgh, ahh, ahh, mommy, aaarhhg, 
yourenormousboobies'rejustoomuch, I'm cumming...!" 

The matronly figure at the door stood rigid, as thick 
gouts of semen began erupting from her stepson's 
monster penis – and just kept on and on, spurting out, 
arcing down onto the sheet of polythene that the boy 
had thoughtfully placed under his naked body. 

Ellen just managed to keep from shouting out at the 
erotic spectacle before her. Her massive bust was 
heaving, her breathing was getting ragged, her fingers 
white as they gripped the doorframe. And still the boy 
came, his obscenely big penis spewing seemingly endless 
strings of cum. Finally the titanic flow subsided, and 
the boy lay back on the sticky polythene, gasping for 
breath. 

"Don't worry, mummy," he murmured, "I'll pump out some 
more with your big bra as soon as I get my breath 
back," and after a very few seconds he started to jack 
his already re-stiffening cock once more! 

The forty-year old, huge-busted matron caught her 
breath: she had to find somewhere to calm down, a place 
where she could take some deep breaths before she 
fainted clean away with emotion - she needed time to 
think. She crept downstairs and out of the house, an 
idea already formulating in her warped, lascivious 
mind. 

So, her sperm-filled stepson really liked her big tits, 
did he? Over the next two and a half hours, in a bar a 
few blocks away, the super-sexed woman drew up her 
plans. Little Bobby stayed at home during the day as 
Ellen preferred to school him herself, so what she had 
in mind was going to be easy...

She arrived back home at 3pm, as she'd earlier told 
Bobby she would, and of course, all evidence of his 
(two hour!) wankathon had been cleared up. The boy 
jumped to attention when she walked into the lounge. 
She wore a tight red cardigan over a peep-hole 
brassiere that she had bought especially, which was 
bulgingly, alarmingly full of her heavy tits - even 
Bobby had never seen them thrust out like that before. 
They jiggled heavily just from her walking and her 
areolae were so hard that he could see the little bumps 
standing out on them, even through the wool of the 
cardigan.

"Hello Bobby," she began, nipples hardening still more 
as she thought of what she'd planned for the boy. 

"What have you been up to since I left? You've not been 
too naughty, I trust." She purposely unfastened a 
couple of buttons on her cardigan, and watched as the 
boy's gaze was drawn up, until it rested on the canyon 
of her cleavage, fully aware that he'd never seen even 
an inch of her naked bosom before. 

"Bobby!" she glared at him. "Pay attention, I'm talking 
to you!" The boy tried to focus on her words.

"Sorry? Oh, erm, yes, I mean no, I haven't been 
naughty, mummy." 

"I hope not. Indeed I hope not." His eyes had not left 
her cleavage, and Ellen noted with rising passion the 
growing bulge in the boy's shorts. She moved closer to 
Bobby, deliberately deepening her breathing, until she 
stood right in front of him, her vast bosom heaving up 
and down, the boy's nose mere inches from the perfumed 
valley between her breasts. 

"You know, I think this daydreaming habit of yours is 
becoming a real problem," Ellen began stroking the 
boy's hair disarmingly, easing his head even closer to 
her. Despite his mammary obsession the boy was 
startled, and tried to move back. Ellen Highwater was 
having none of that. 

"Keep still, Bobby. You're always fidgeting. Fidgeting 
and daydreaming." The boy stiffened (in more ways than 
one) as his stepmother drew his face actually into her 
cleavage. 

Ellen Highwater was into the plot now, elaborating and 
adding details as she went.

"When you're naughty, it – it upsets me so." 

She pressed the back of Bobby's head between the slick 
inner surfaces of her huge hooters.

"When I get upset, my body starts doing strange 
things," she went on.

When he heard what his stepmom said, Bobby drew back, 
somewhat dazed from his close proximity to the objects 
of his obsession.

"What strange things, mommy?" He said. 

Ellen mentally rubbed her hands together.

"Well, most noticeably, when she's upset, mommy's 
nipples start to grow bigger." 

Bobby couldn't believe his ears. 

"Really? Your n-n-n..."

"Nipples, Bobby, say the word, nipples, nipples, 
nipples."

"Your n-nipples get bigger, errr, how much bigger?" The 
boy was staring openly at her pointy nipples now, 
elongated as they were both by her state of mind and 
the peep-hole brassiere.

"That depends on how upset I am," said his stepmom, 
"but if they get really big, I have to take steps."

"Wh-wh-what kind of steps?" enquired Bobby, almost 
afraid to ask.

"Well, you know if you feel faint I open a window for 
some fresh air?" The boy nodded, on familiar ground for 
the first time. "Same thing applies with my nipples - 
the first thing I do is get some fresh air on them."

"Are they really big at the moment, mommy?" The boy 
could see just how huge the twin teats were, as they 
tried to force their way through the woollen stitches 
of the red cardigan.

"Well, just look at them, have a good close look."

Bobby stared, his eyes out on stalks, but that wasn't 
exactly what his stepmother wanted.

"Good boys do as they're told," she scolded, forcing 
his face deep between her massive mammaries once more, 
"and if they start being naughty, they go to Doctor 
Lessmilker's clinic!" 

Bobby couldn't know that Ruth Lessmilker had been 
thrown out of the USMA, or why... but he would. Oh my, 
how he'd know. Ellen Highwater waited to see if her 
words had registered. After what seemed like an 
eternity, the boy mumbled from deep inside her 
cleavage. 

"Dnctrh Whmm?" 

"You see, now you're not listening to me. If these 
problems persist, I can see you being booked for a very 
long series of therapy sessions with the good Doctor!" 
Bobby couldn't hear properly, of course, because of his 
mammary earmuffs, and once again it was a while before 
her voice registered on the stunned child. 

"Mmmwlppphh." He mewled, ands she felt his hot breath 
forced around her gigantic jugs. She allowed him to 
wallow a few moments, then, albeit reluctantly, she 
eased his flushed face from within her bosom. 

"Bobby, Bobby, Bobby," she shook her head. 
"Daydreaming, fidgeting, and now – you ignore me!" The 
helpless boy opened his mouth to speak, but Ellen 
silenced him with a finger to her full lips. "Don't add 
interrupting to the list." Bobby was again focussed on 
his stepmother's cleavage, a sight further enhanced by 
the accidental popping of more buttons by his chin as 
she gently drew his head backwards. 

"I'm sorry, Bobby, but you leave me no choice." Bobby 
may have heard, but the acres of bulging bra-cup on 
display seemed FAR more important. Ellen was ecstatic – 
the boy just went on digging himself in deeper. 

"Yes, I fear your only hope is daily appointments with 
Doctor Lessmilker." Bobby stood quietly, obediently, in 
awe of his stepmom as his massive cock throbbed beneath 
his shorts. All he could think of was wanking that 
monster over and over and over in her honour, as soon 
as she left the house again. 

"Have you nothing to say to me?" The boy was already 
mesmerised by her mighty breasts, and her words and 
actions of the previous five minutes had only served to 
push him deeper into his obsession, just as she had 
planned. His young mind was primed for more 
concentrated programming, his body was pumped full of 
testosterone, and his enormous cock was full of 
semen....

Bobby was confused. He knew he must not disobey his 
stepmother – eight years living with her had taught him 
that – but here he was, on the one hand being hushed, 
on the other being asked to speak! The poor boy's 
anguish was evident, but Ellen was certainly not 
letting him off the hook. 

"Well?" she stared at the lad, hands on hips, as he 
tried vainly to divert enough of his mind away from her 
straining, pointed bust, to formulate a reply. 

"Erm, I-I, well, that is..." 

"Day dreaming again!" said Ellen, sighing dramatically, 
causing her huge breasts to bounce alarmingly. 

"No, I mean, sorry, mommy." He finally said, lamely. 

"Now you're contradicting me!" Ellen really enjoyed 
Bobby's discomfort. She reached for the telephone, 
dialling the number even as she spoke. 

"No time to waste, Bobby. The sooner Doctor Lessmilker 
and her staff get their hands on you, the sooner we can 
look forward to them producing more positive 
results...Hello, is that the Lessmilker Clinic? Oh, 
good afternoon. I'd like to book a series of 
appointments for my step-son – yes, daily, please, he 
needs to be refocused, I think, he's losing sight of 
what's really important in his life, and I want my 
little boy to be put firmly on the straight and narrow 
– yes, that's it, all that nasty stuff needs to be 
drained out of him – yes, as many times as it takes – 
starting tomorrow, if that's possible – super, we'll 
see you at 9am. Goodbye." 

Bobby had actually begun to drift back to the real 
world as she spoke on the telephone and briefly found 
himself wondering just what this clinic was all 
about...and then his stepmother replaced the receiver, 
reached beneath her shelf-like breasts, and briefly 
jiggled them. 

"Just look at my cardigan, gaping like that," she 
murmured, her actions instantly achieving the desired 
result of causing yet more swelling of the poor boy's 
penis. "It's a wonder I haven't poked your eye out." 
The 18 year old felt more blood rush into his already 
erect member, as his stepmother lifted his face to look 
into hers. 

"You'll feel better as soon as the treatments start." 
The boy felt her warm breath on his upturned face and 
sensed her massive bosoms looming closer once more as 
she slid an arm around his shoulders. "Poor thing, all 
these nasty problems that need attention!" Ellen 
suddenly pulled Bobby closer to her. 

"Oh! Sorry Mommy!" Bobby croaked yet again, pulling 
back after her sudden movement had caused him to sink 
right back in between her massive mammaries. His hardon 
just kept getting bigger and bigger.

"I think I'd better get my poor, aching nipples out, 
and give them lots of fresh air," said his stepmom, and 
without disturbing the boy she popped the last couple 
of buttons and shed her cardigan.

The sight of her obscenely distended, thick, two-inch 
nipples thrusting through the holes in their respective 
bra-cups either side of his face, was just too much for 
poor Bobby. He felt his pulsating cock lurch, and then 
the wonderful sensation of orgasm washed over his as 
the throbbing hose in his pants began squirting ropes 
of cum all over his stomach. Ellen watched Bobby 
bucking helplessly, panting and groaning.

"Good heavens – is your penis squirting, baby?" Ellen 
couldn't believe the sheer length and girth of the 
monster within Bobby's clothes, as it bucked visibly. 
And he'd cum without even touching it! This just kept 
getting better and better! 

"Did mommy's big nipples make baby Bobby's penis do 
that?" She reached down and pressed the area of his 
pants around the truncheon-shaped bulge, immediately 
rewarded with a loud squishing noise. She could feel 
the cum jetting against the other side of the material. 

"Why, it's still squirting! Pumping out more and more 
nasty, thick, white, squidgy, dollops of semen? I think 
it's just as well you're going to be taken in hand by 
Doctor Lessmilker, Bobby – after all, we don't want you 
squirting all that nasty stuff just any old time, do 
we?" 

Bobby's huge penis finally stopped spurting, and the 
boy fell back into a nearby armchair, shaking. Ellen 
wasn't even properly started with the boy yet, and he'd 
already cum like a fire hose!

***

Chapter 2 to follow shortly - if anyone wants to see it 
- please let me know...

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
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 35