BDSM Library - Love in Cathedral Heights

Love in Cathedral Heights

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Synopsis: unique love story involving chastity, teasing and denial between a young man and an older woman.
Love in Cathedral Heights
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PART ONE
"Where IS she?" Gerry moaned...It's been
forty-five minutes... My dick hurts, I can't
stand it!
*************************************************




Danielle, owner of the salon where Helen was a
stylist often remarked that her star employee
sounded like an art historian and dressed like
Joan Jett..."Must be the cute young lawyer who
rents from you, huh?" Dani kidded...Helen looked
great today outside the coffee shop, spiky red
hair, tank top (no bra) and
tiny leather miniskirt. Her new fishnet stockings
looked great too...Gerry had hooked the garters
that morning, trembling...It's great that I still
can do that to him at nearly fifty,she thought.
One of Helen's ivory hands, the long nails
colored the same flaming red as the hair and
lipstick, absently stroked a collie's ear, the
other held a bottle of Johnson's Baby Lotion,
purchased twenty minutes before at that awful CVS
drugstore a block down. 
Gerry preferred Astroglide, but this would do.
She'd been gone an hour now, what with coffee and
shopping...was Gerry all right? If anything
happened after all, he couldn't move. Helen
smiled, and sipped some of her latte. Strange to
worry this time, after fourteen years of this.
The stove was off, the door locked. He must be
squirming.
***********************************************

Gerald David Morin,33-year old patent
attorney and first year partner at Gideon,
Shapiro and Burling tried to stretch his
arms...no, he couldn't move them, not an inch.
Jesus, I curl 175 but Helen makes the ropes
fuckin' tight. Why isn't she back? Gerry lay
spread eagled on Helen's four poster bed, his
broad chest taut, and hands and feet tied by
tight nylon cord to each wooden bannister.


Naked as always, his pierced dick struggling
in its weird loop, the cockhead attached by a
ring to a tiny padlock in another ring just above
the scrotum. Impossibly, precum seemed to be
oozing across his ball sack. Helen had just been
going to unlock it when she realized they were
out of lubricant. It had been more than an
hour...where the hell was she?

Though it had been Gerry who begged that they
switch him from the chastity belt to pierced
rings in '98, he sometimes regretted it. He had
to sit down to pee, like a girl.Had'nt used a
urinal in five years. And now his dick really
hurt right now, and looked ridiculous in its
constant tremble...trembling because its natural
instinct was to stick straight up, not to be
hooked to his balls...stick straight up and wait
for Helen's wandering fingers. 
"Do you want to go with a bunch of us to
Great Falls this weekend?" Marsha, a summer
associate in her early twenties had asked on
Friday..."I'm going to be wearing cut-offs and
splashing my feet after all the work on this
case."
Gerry had imagined she'd look good in
cut-offs... His penis had struggled against the
ring then, making a teeny tent in his Brooks
Brothers summer trousers. "I can't." He tried to
smile. "Gerry NEVER goes out with us. Wasn't even
at the Christmas party." Ann, a second-year
associate with bouncing auburn curls who'd
flirted with Gerry since her first day at Gideon
interrupted." I think he has a curfew or
something...Look! He's BLUSHING!" 
The womens' laughter had tinkled cruelly...but
Ann was so close. Not a only a curfew but a
BEDTIME. Thirty-three years old, and he'd never
seen "Law and Order" because it was on after
eight-thirty. Sometimes he could stay up til nine
if Helen felt like a little cunnilinguis or a
massage, but usually she got that BEFORE dinner. 

Helen loved him, and she knew best...Gerry's
reverie was interrupted by the door opening. For
a minute he panicked...What if it were the old
Miss Hall from the dog park? Did she have a key?
Oh Shit. "Hello, sweetie, I'm back." came the
familiar lilting Southern tones...Oh, thank God.
Helen came into the room, tucking in her
tank-top,which of course made her chest
balloon..."What have you been doing?" An old
joke, they both laughed. She sat on her stool by
the bed, and took the key off the bedside table.
"Ooh, it's purple...you don't need me." 
Helen smiled at his agonized look, and
unlocked the tiny padlock between the rings.
Gerry's penis shot up to attention. "Like one of
my daddy's recruits at Fort Benning." Helen, a
former army brat said, laughing, and took the
lotion out of the bag. Seeing Gerry's
disappointment at her purchase, she cocked her
head. "What did you want me to do Gerald, drive
down to the Pleasure Chest?"
"God you're beautiful, Miss Helen" Even
after he'd discovered they both had subscriptions
to "Leg Tease" after he'd rented her basement his
sophomore year at Georgetown. "You're a cutie
too, my Gerald" Helen began gently rubbing the
lotion into the underside of his now furious and
quite violet member..."Thank you ma'am...ooh
that's good...I'm Sooo horny..." A sharp flick of
a fire-engine nail on the cockhead "er- I mean
aroused" Though she'd left Vanderbilt after her
first year Miss Helen was still an educated woman
and frowned on slang.
Gerry had never really felt comfortable going
to a first-name basis with Helen; but she'd
allowed him to go from Mrs. O'Neill to Miss Helen
on their fifth anniversary; when he'd signed over
his first Gideon paycheck. After rubbing and
stroking his penis for about five minutes, Helen
stood up, and Gerry caught a flash of the garter
attaching her net stockings. 
God, I'm glad I bought her that miniskirt,
her legs are better than Ann's. "What...what's
wrong? Why are you getting up?" It was feeling so
good, too..."Sweetie, I have to go in the kitchen
and feed Victoria and Albert...I'll be back..."
His penis wagging like a metronome, Gerry tried
to smile. A tantrum wouldn't work, being trussed
like this. Not to mention that Miss Helen could
lock him right back up again, as she'd done in
the past when Gerry had summarily ordered her to
keep stroking...
As Helen only gave him a "teasing" every other
Sunday morning, with release averaging about once
every 90 days ("So you have something to look
forward to, Gerald; remember, an expectation is a
resentment waiting to happen") it behooved the K
Street law community's patent and trademark
expert to keep his remarks prudent. "Aah...take
your time, Miss Helen. I'll bathe the dogs for
you later on." If he kissed up enough, maybe
today would be cum-day...maybe.
Helen smiled, gently pushed a fluffier pillow
under her captive's head, and she left the room,
her derriere twitching in the skirt as the door
closed. Gerry sighed and bent his chin on his
chest to watch the juices flowing from his
miserable, enthralled and utterly unsatisfied
"wee-wee"
A fortnight earlier, Helen had made the shaft
of it buck, supported by Gerry's hips, as she'd
alternated for five hours between her glorious
fingers and an ostrich feather that she'd picked
up at the Georgetown flea market.
After about 20 minutes of feather-rubbing the
area just under his cockhead, Gerry had burst
into tears, begging Helen to quit, and she'd
immediately, to his chagrin ceased the entire
tease, icing his member til it was flaccid for
the evil padlock. "No, don't stop COMPLETELY..."
he'd begged, tears and mucus running down his
cheeks...but she'd locked him, untied him and put
him to work scrubbing her five bathrooms..."A
more productive occupation anyway, Gerald for an
enterprising youngster on a weekend afternoon."No
cumming for another two weeks. Damn! DAMN!

He'd primed himself to be ready for the
feather's ministrations today, but Helen's mind
was fertile with surprises...in fourteen years
he'd never been able to predict her next move! 

Gerry had interrupted a deposition last
Wednesday to duck into a restroom stall to uh,
prep for the upcoming Sunday feather, when he
remembered again as he had several times in the
past decade that, although he could stimulate his
cock as long as he liked, lubing with that vile
pink soap the firm had, it was to no
avail...though he averaged five bathroom trips a
day for this sordid purpose. With the evil
padlock there was NO RELEASE. Back to the meeting
he'd trudge, ball sack leaden. 
"Don't you ever give up?" Miss Helen often
asked, arching one eyebrow. "Just use the
lavatory for its correct purpose, Gerald." as she
clucked over the scabs the cheap pink liquid left
on his unsatisfied erections. Once when he threw
a tantrum over wanting the padlock removed before
cum-day, she'd replaced it with a steel ball
hooked to the rings, and batted it between his
legs with a spoon as Gerry writhed in pain.
It didn't help that nearly every night, he
was giving her gorgeous 36DD breasts a scented
oil massage, and spending two hours or so (before
dinner)between her legs...He was hornier, and she
was fine! A few weeks ago Gerry'd begun crying
when he realized he was licking someone's semen
out of her vagina...his penis had certainly never
been down there, and she soothed him..."Just an
old friend I saw..."

It's worth it though, he thought now, bound
to the bed, Bring on the feather, I'm ready. "I'm
back, Gerald." Helen swished back in..."Victoria
is really enjoying the leftover bacon...Did you
miss me?" Gerry nodded weakly, and watched Helen
sit down and prop a plastic box of dental floss 
on her fishnet thigh.
"Miss Helen has a surprise today..." She
smiled, and pulled a bit of floss out of the box.
Was she going to tend to her teeth, before
bringing out the horrible feather? Snapping off a
piece of floss about seven inches long Helen then
squirted a bit of lotion in her left hand, and,
floss in her right, rubbed both hands together.
What was this? 
Helen then took the greasy strand between the
fingers of both hands, and looped it around
Gerry's straining cock, in that sensitive area
just beneath the head where the feather had
visited two Sundays before. And then holding the
ends between the crimson tipped thumb and
forefinger of each hand, Helen began pulling the
string baack and forth... 
END OF PART ONE


Love in Cathedral Heights-PART TWO 

Gerry lay rigid, feeling the delicious tingle
of the lubed dental floss that Miss Helen was
rubbing around his straining, drooling erection.
First she'd stick right below the pulsing now
violet cockhead, and then pull up and down the
shaft.
Miss Helen was a beautiful Southern redhead,
and as she pulled the string back and forth round
the shaft, her breasts jiggled in the snug
tank-top...At forty-seven Helen's tits might not
ignore gravity, but they winked at it a
little...Gerald just couldn't take his eyes off
them. When the floss became dry, Miss Helen would
re-immerse it in the lotion...
It'd been an hour of this, puncutated by
brief, no release handjobs..."Miss Helen, Please
I don't want to complain the way I did about the
feather torture..." "What did that get you,
Gerald?" Miss Helen dragged the floss further
downt he shaft, pullling it back up towards the
purple mushroom..."Answer me!" 
"You locked me back up for two weeks...the
floss is okay...Just...I'm soo...uh..." his dick
felt like a missile ready to go off. The light
touch of the greasy floss, further inflamed by
his excellent view of Helen's balooning cleavage
straining against the tank-top as she bent over
to pulll the string just a little more.
When he'd met Miss Helen Gerry was a confused
and somewhat pudgy trust-fund baby,whose ambition
was to drum for Metallica. His adolescence had
been a myriad of prep school expulsions, wrecked
Mazdas, pregnant girlfriends, and methadone
maintenance. 
Hell he'd only gotten into Georgetown because
Uncle Will was a generous alumnus; and had moved
to Miss Helen's because he'd been kicked out of a
frat for hazing too hard..."Only A I ever got was
when I cheated on the exam..."was one of his old
yearbook quotes,..."Scary Gerry" was ashamed of
nothing except his kinky fantasies...Ooh, the
string is driving me MAD! 
Finally she tossed the strand into a
wastebasket and began casually stroking the
underside of his cock with her crimson tipped
fingers. "There is a large purple vein,
Gerald...IF you took up drug addiction again this
would be the place to inject...Ooh your juices
are soaking my finger...Lick it off, please." 

Gerry sucked the precum off his landlady's
long fingernail as if it were a dildo, and
withdrawing her finger, Helen opened the end
table drawer and tok out some Scotch tape. "Do
you like what I do to your wee-wee Gerald?"?
Helen wrapped a bit of tape around Gerry's
foreskin...."Yes ma'am...The teasing is so heavy
sometimes." 
"It's what you begged for, remember?" Helen
wrapped more tape around the shaft gradually
working her way down the frenum. "You begged to
for it, remember? Dumped your little sorority
girlfriend, quit running with your friends for
the TEEASE, Gerald..."
At first she'd teased the excited nineteen
year old for only short periods, his hands bound
behind...she always let him cum within an hour or
two sometimes twice if he brought helped to clean
the house,..then one night, no cumming. 
"What's wrong?" Gerry had asked. "There are
rewards and punishments, Gerald..." The house
was to be spotless,the ponytail and beard would
be replaced with a crewcut and clean shave; 500 
daily chin ups,push-ups and situps for Gerry; a
mile a day of running with Miss Helen shouting
encouragement from her car window; turning over
his allowance and credit cards for her to manage;
and STUDYING. 
Every test or quiz score over 95 would be
rewarded by long, heavy teasing and then orgasm;
85-80 resulted in long,LONG teases ending with
horrible ice dropped on his swelling scrotum;no
release..."Why oh why can't you do better
academically, Gerald? Don't scream darling, the
ice isn't that bad" and below a score of 79 there
was no teasing; just fifty with the strap and two
nights in the closet...with all this effort there
was no time for parties anymore.
One day "Gerald Morin" was on the dean's
list! And the tennis team? His former friends
were astonished...Not only did he look great and
was summa cum laude...but for the first time
since his twelfth year, "Scary Gerry" was
addicted to nothing--no tobacco, booze or drugs,
and needed no methadone or support groups. All he
was addicted to were his landlady's wandering,
lubricated fingers--and that was a secret. 
College and then law school professors, and
finally employers said the same thing "That boy
is DRIVEN!" The last time, this compliment came
from a firm partner, as the brilliant young
associate limped by, butt swelling, and confined
erection overloaded, because the firms aging
trademark expert had lower standards for a
well-written brief than Miss Helen did...
But he'd endured it, and now..."Is the tape
irritating you, Gerald?" Helen smiled, Gerry
could see her nipples poking through the tank
top..."Its all right sweetie..I'm sorry about my
temper over the feather incident..." Mollified,
the trusting prisoner complained a little. "Well,
the tape is really sticky and my dick is so
hard." It had been Gerry's suggestion, fourteen
years ago, that he purchase a good chastity belt,
selling his Harley-Davidson to order several
different European models,with Helen holding
keys, of course... 
"Oh, sweetie...I'll take the tape off...it'll
be all better, my precious boy." Then one night
was it she or him? who proposed,good grades or
not, a month of total chastity belted celibacy,
with thirty evenings of frustrating no-release
milkings..." Thank you Miss Helen for removing
the tape...YEAAGH! YOU DIDN'T HAVE TO RIP IT
OFF?" Crying now, Gerry's cock was scalding from
the quick er, removal of the tape...Helen was
laughing..."It's not (Sob!) funny! IT HURTS!" 
Helen instantly quit laughing and looked quite
annoyed. Tossing the crumpled tape into the
trash, she arched her back, breasts rising
majestically. "You seem to complain at the end of
every tease-day now..first whining over the
feather, and now the tape...I think I'll quit,
you obviously don't WANT to orgasm..." No, NO.
"Please, Miss Helen" Gerry wailed. "I can't take
it...it's been over a hundred, hundred and five
days now...I won't complain!"
Though he used to get milkings daily, with
orgasms each day, eventually Miss Helen who
needed her hands to have energy for her work as a
stylist, had limited the sessions to twice a
month, on alternate Sundays...
This happened after Gerry had made partner,
and was habitually a hard worker.."Gerald, the
whippings will remain if you falter in work or
housework, or even if your Saturday rugby team
loses too many games, but the rewards will be
fewer, a good bloodhound needs nothing but the
joy of the hunt."with Gerry, having discarded the
chastity belt to wear a cock piercing of two
rings, one at the tip and the other at the
scrotum, which locked the penis in a
non-masturbatable arc.
Gerry could get aroused playing with it, but
no cumming...And any excuse on these play days
would cause Miss Helen to re-lock the poor boy
back up for another frustrating two weeks...it
had been well over three months now...couldn't he
mollify her somehow? "Please Miss Helen (sniff) I
won't complain anymore. Please don't stop
now..."his voice broke, watching her get up off
the bed and walk out the door. "I'll consider it,
Gerald...I'm going to get some tea now."
*************************************************
It was nearly four o'clock, Miss Helen had
taken about two hours to have her tea. Gerry was
attempting to waggle his penis with his torso,
hoping vainly that he could make it squirt...but
no go! It might have been easier if he didn't
have the desires of a compulsive masturbator, and
the semen was certainly built up...Water had been
running in the bathroom...Would she come back?
About seven years ago, he'd decided to leave
Helen for a while; sick of the early bedtimes,
teetotaling, no partying and no "fun" He wanted
to date a few girls his age, dammit! After about
six weeks in a cocaine drenched love-triangle
with a nineteen year old waitress and a gorgeous
blond paralegal, both of whom had dumped him for
his strange desires...he'd called Helen,crying
from a detox ward..."Coming home,
Gerald?"Forgiveness came readily, but he'd not
squirted for an entire summer! Now, thinking
about it, he'd been such a fool, though the life
here could be tough. Where is she right now? 
"Well, how have you enjoyed your respite?"
Helen wandered back in. She had taken a long
bath, changed her tank top to one of her little
t-shirts that accentuated the boobs and exposed
the midriff, and some white short-shorts..."I
couldn't tell whether you wanted me to quit or
not."Giving him a mischevious smile, Helen sat
down on the bed and placed a manicured forefinger
on the tip of his cock. "You seem so emotional."
"I'm calm now,Miss Helen, really I am...please
let me cum today!"
"Whine, Whine...I think you need to get out
of this bed..."Gerry panicked inside, wondering
if he would be locked for another fifteen days,
and relegated to more housework. Helen undid his
hands and feet, and pulling out some handcuffs
from the drawer. Motioning the naked attorney to
stand up and turn, she cuffed his hands behind
his back, and led him out of the bedroom by the
head of his burgeoning penis.
Following her, Gerry's arms and legs felt
quite stiff, as befitted someone who had been in
four-point restraints since the early morning.As
they cme into her old fashioned "sitting room" he
noticed the grandfather clock. Four thirty! No
wonder he could barely move, he'd been in bondage
for hours...
They sat on the familiar couch where Helen had
given him so many over the arm-rest bare bottom
razor stroppings...The couch where he was allowed
to watch one football game a year-the
Superbowl.He had to earn it, though-- This year
he'd viewed the game wearing a frilly oversized
pink dress with a little-girl bow in the
back,something out of the 1920's...complete with
big flowery hat, white socks and Mary Janes and
white parasol-since his hands were cuffed it was
propped next to him for the duration of the game.

He'd worn no panties since his butt,
blistered from a pre-game stropping, housed a
cucumber the size of a Louisville Slugger, it
seemed. "I got it at the Farmer's Market,
Gerald...your regular dildo is getting chipped." 
The Superbowl fine til she'd blindfolded
Gerry for the last 10 minutes of the game..."I
polished all the siverware in this dress so you'd
let me see the whole game, Miss Helen!" Tears
coming down from the kerchief..."Don't whine,
Gerald, this is to test your listening
skills...the announcer will tell you how things
are going, he isn't as irritating as Howard
Cosell."
Now, she looked over at him. "I think you
should get off the couch, Gerald...Kneel on the
hassock right next to it...It'll help you
stretch." She smiled mischeviously.
He obeyed, climbing on the hassock on his
knees. Immediately, Miss Helen reached over and
began stroking his cock. She was so close that
she could do this without having to lean over. It
was quite comfortable for her..."Kneel up
straight, dear as we did at the eight a.m. Mass."
Gerry straightened his naked body. This was even
harder than the bed--he had to balance his
handcuffed form, knees pressured, staying ramrod
straight while Miss Helen tickled his throbbing
member with her nail tips...what if he fell over?
The phone rang. Helen reached for the phone
next to the couch with her left hand, the right
still making poor Gerry crazy. "Hello, oh hi
Miguel..."Her tongue was between her lips,
arousing her straight soldier further. Miguel?
Not the firm's most arrogant mailboy who he had
dispatched to change the oil and wash Helen's
hot-pink Austin Healy 500, a present from Gerry
last spring, Gerry had ordered Miguel to do these
chores or be fired, as the little creep had used 
the firm's courier service to pay a late bill.
Let him know whose in charge, you know?
That was two months ago, Miguel'd been over 
since then to rake leaves...But I was out of
town..."Motley Crue? I love them!" Helen giggled,
leaning into the phone. But I was whipped for
buying their CD, Gerry thought. "Try a little
Brahms, Gerald."she'd said. But now, "God, I'd
love to go...Miguel, you're so sweet"She squealed
like a schoolgirl.
She reached a long nail under Gerry's scrotum
and began toying with his full balls. Propping
the phone on one shoulder Helen took her o ther
hand and began manipulating the shaft, shooting
Gerry a warning look as his shoulders seemed to
be losing posture. His butt was falling towards
the backs of his legs as well. "Mr. Morin? He
can't stay out that late, he's in bed by eight."
Gerry's face burned. Does she have to tell the
world I have the bedtime of a nine-year old?
Helen was massaging faster as the conversation
grew hotter "Do you think a lot about me,
Miguel...you can tell me...I'm your sweetheart!"
She pumped the shaft, and Gerry felt a wonderful,
surging in his granite-hard cock as he hadn't
felt in a hundred five days...oh, this is worth
it all, I love her...His hips began shaking
violently, and he closed his eyes...now,
now...NOW...yes, please...Gerry dropped his head
to his chest, and waited for the blast.
Suddenly Helen dropped his genitals as if
they were a hot potato...she swung her legs over
into a lying position. She lit a Marlboro, and
smiled at his face.."Why should I quit smoking if
you won't?"he asked years before."Adults can
smoke, Gerald, but you'll always be a sniveling
schoolboy."was the answer.
Now she puffed away, talking kittenishly into
the phone "Oh Miguel, of course I enjoyed
Thursday. You told Mr. Morin you were sick? I
won't tell...the picnic was nice, and I didn't
mind paying for the room at that little inn...Mr.
Morin's platinum card can be very generous." 

Helen watched Gerry, crushed at the sudden
cease of the near-orgasmic experience, about to
slump on the hassock. She put her hand over the
phone. " Keep kneeling with good posture, that's
right straighten up or you won't cum til Labor
Day...remember, Gerald, the Fourth of July isn't
even here yet." She stopped her hiss to chuckle
at the tear rolling down the now straightened
Gerald's cheek. She went back to her
conversation.
Gerry was in bad shape. His penis was in pain
from suddenly not squirting, and still quite
engorged, he had a serious need to pee, his legs
were cramping from kneeling nearly forty minutes,
and there was the unbelievable conversation...
"No, Mr. Morin's never told me I performed
fellatio well, Miguel, it's not a part of our
relationship." She sucked the little bastard's
cock? "He's very rigid, Mr. Morin is...Sweetie,
call me tomorrow and we'll plan for the concert.
We can spend the night at the little Inn again.
Goodbye."


Love in Cathedral Heights-PART THREE

"How many packs a day did you smoke, Gerald?" She
used a nail to flick ash at the young man's
tumescent penis. As he was kneeling naked, hands
cuffed behind him on the ottoman, this was not
taken comfortably...He gasped, and his dick
trembled. Gerry was kneeling, not in a sitting
position but with his butt up, as they do on the
kneeler at church...this had been going on for an
hour or two, and he was beginning to cramp.
As Miss Helen was sitting comfortably on the
couch not seven inches from Gerry's precarious
balance on the hassock, it was only amusing to
her. She was fully dressed, wearing a midriff
t-shirt, tight over her large breasts, and
short-shorts, showing her magnificent
legs...Gerry felt even more nude in this
situation...
"Butt up, Gerald, don't lean on your legs that
way...and answer me!" Gerry's lip trembled...he
had to pee badly. "I don't...remember, Miss
Helen. It was over a decade ago that you
made-helped me quit-"
Miss Helen flicked another, larger spark,
which fortunately missed the cock entireley,
scalding Gerry's inner thigh. "How many (flick)
packs (flick)did you (flick)smoke a day, stop
crying (flick) Gerald, I'm so sick(flick)of your
sniveling...it's not attractive(flick) now about
the cigarettes, I'm not going to stop flicking,
til you tell me, dear..." 
Gerry's crotch was stinging, and he was having
a dear time trying to maintain his balance...his
upper calves ached, as did his back"One, uh or
one and a half, Miss Helen." "My sweet
chain-smoker, I think it was more like three, and
the first day you moved in here, you put a butt
out on my antique cherrywood coffee table...you
were an arrogant young man, weren't you?" 
She flicked one more spark, it hit directly
under the shaft, and Gerry fell off the hassock.
Miss Helen got up and patiently helped him back
onto the evil cushions..."You know, darling, I
only smoke about four ciggies a day..." Helen
said, began rubbing the scorched, but still
throbbing penis tenderly. "Why are you so
addictive?" She asked this as if Gerry had last
smoked an hour ago, instead of back in 1988. 
Picking up a jar of vaseline from the coffee
table in question,(Gerry'd long ago had it
refinished) she opened it and began spreading the
cooling gel all over Gerry's shaft. "Isn't it
nice that we have jars of Vaseline all over the
house like this?" Gerry sighed deeply, the woman
certainly knew how to manipulate her
fingers...(giggle) More Vaseline than most
couples I imagine." 
Miss Helen began energetically rubbing the
underside of Gerry's penis with her long
red-tipped fingers. "Poor Gerald, I went too far
with the cigarette, let me soothe your wee-wee."
She stroked a bit more."Better than before you
bought me the dryer, darling...remember the
clothespin fun?" 
Gerry shivered, and his cock wilted just a
little. He remembered! But he quickly rose again,
his landlady was too good with her massaging.
Precum oozed a bit from his penis tip, and
Helen rubbed it right back in the skin like
ointment, blowing through her full lips. "Ooh, I
need to touch up."
She opened her lipstick, and put a fresh
shade of pink on her lower lip, rubbing the two
together..."Wish I'd use these lips for fun,
Gerald? Fun like Miguel gets?" She was referring
to her lover, the mail clerk in a firm where
Gerry was a partner. Helen put the lipstick away
and pushed her head very close to his straining
cock and after dipping her long nails into the
vaseline jar, began rubbing the foreskin with two
fingers...
Gerry, despite the tiny burns all over his
penis, felt it filling once again with blood,
stiffening and he was incredibly aroused. Miss
Helen's fingers rubbed the head, and then worked
up and down the shaft..."Poor Sweetie, does that
feel better?" She rubbed the shaft more with her
soft, white fingers, causing the semen to rise
once again from the testicles...
Gerald sighed. He was so used to this
Charlie-Brown-Lucy-pulling-away-the-football
treatment that these false alarms shouldn't have
bothered him, coming close to orgasm, REALLY
BELIEVING he was going to cum, and then having
her stop suddenly, and ridicule him. 
Once after an excruciating forty-eight hour 
no-cum tease,which had followed fifty-one days of
the padlock, he'd stolen her key and unlocked the
padlock...she'd caught him, just before he'd
squirted kneeling there on the bathroom floor,
pumping away and clutching one of her brassieres.
Miss Helen had given Gerry a weekend of hell,
starting with the strap, and continuing with full
infantilism treatment..."Wear Depends til you
learn not to squirt without permission, darling."
Now, his cock felt that racing that happened
right before orgasm yet AGAIN Gerry began
trembling, his penis was starting to buck Helen
switched from rubbing to tickling, and then...
Helen suddenly bent down and kissed the tip,
something she'd never done before. She got down
on her knees and kissed it again. "Does that feel
good, sweetheart? Does that help, kissing the
boo-boo?" Suddenly, she seemed to be reverting to
baby talk, and right in the position to give
head...
No! it couldn't happen..."Did my wittle
Ge-wuld's wee-wee burn?" She stroked more,
slathering Vaseline over the purple mushroom
cockhead...
Gerry felt the surging again...His balls
were leaden and he swayed on the hassock, it was
so strange having his Miss Helen on her knees in
front of his burgeoning,suffering penis. Would he
get relief? This would be so ecsquisite, if she
blew him. 
His last orgasm occurred when Miss Helen,
entertaining a group of black male gay
hairdressers had allowed him to masturbate his
cock with his left hand (he was, of course
right-handed) lubricated with Ben-Gay...he had to
cum within ten minutes or no go...
As the queens screamed with laughter at the
naked, blindfolded young attorney pounding his
pud desperately on a rubber sheet laid over the
Oriental rug, Miss Helen blew smoke through her
nostrils and sang "Jimmy Crack Corn..."and timed
Gerry with his stopwatch from the firm track
team...
He'd made it with twelve seconds to spare, and
licked it up while the biggest of the gay
hairdressers hit his ass with a wooden
spoon...humiliating, but it had been an orgasm,
now PLEASE LET ME HAVE ANOTHER A HUNDRED FIVE
DAYS!!!...
Miss Helen suddenly stopped rubbing, to run
her Vaselined hand through his buzz cut "Darling,
aren't you glad we chopped off that blue and
green streaked ponytail when you first moved in,
fourteen years ago?...
Gerry'd been startled by his meek agreement
to her hair change proposal; up til then his
coiff had been a statement..."It's MY HAIR, you
asshole !" this repeated jerimiad had effectively
cowed Dad,a renowned author of family therapy
manuals; hell,Gerry's first trip to Juvie, sixth
grade? He'd tossed a brick at a traffic cop who'd
made fun of his new mohawk...But Miss Helen had a
way about her...
Miss Helen went back down to rub and kiss
his weiner...this continued for a while, til
Gerry was shaking in anticipated orgasm..."Oh,
Miss Helen...PLEASE let me cum...I'll do
anything...oooh I'm so cloose..."
Then Helen sat back, and reached for Gerry's
penis with her patent leather pumps...Rubbing the
top of the cock with her right heel, she caused
friction with the underside by rubbing the top of
her other heel..this went on for about twenty
minutes, and as her legs were up in the air,
Gerry could get brief panty shots under the
miniskirt. 
A former ballet instructor,Miss Helen could
hold her legs up almost indefinetely, and caused
great friction to Gerry's bloated, purple member
rubbing away...occasionally she would stop and
put both her heels together, squeezing the
cockehead painfully, and then return to rubbing
the shoes against the naked, throbbing penis...
Gerry's hips began shaking again,as the semen
seemed to be pushing out, he had to hold back, if
he drenched her new shoes in cum, it would be
fifty with the strap and another twenty-five with
her evil cane, but he was sooo close, was it
worth it? Oh Ohhh....He was so close, he felt it
coming the first one in a hundred and five
DAYSS....

Miss Helen suddenly dropped her feet to the
floor, just seconds before Gerry was to spurt,
and stood up. "Wha--no..." Gerry looked at her in
alarm. Helen helped Gerry off the footstool. "Oh
Miss Helen, thank you for taking me off that
awful thing, my knees were killing me, but what
about my cumming?"
"Don't you love to give orders, little boy."
Miss Helen guided Gerry over to the marble floor
of the fireplace..."Back on your knees..." "No,
it's been hours PLEASE!" Gerry was close to a
tantrum. "My knees and my back are killing me,
god damn..." 
Miss Helen let go of Gerry and went into her
bedroom...She didn't slap me...maybe things are
looking up...Gerry stood on shaking legs...his
penis was shriveling a bit in fear of his
landlady's temper, but was still as hard as a
regulation lead pipe.
"Gerald...sweetheart..."Miss Helen walked
back in and stood in front of Gerry..."You must
learn to obey, and not insist, don't you think I
know more than you do?" Gerry hung his head..his
eyes were open, however and in her hand were five
jacks...the little metal stars that girls used
back in the old days...
"Do you know what these are, Gerald?" Miss
Helen shoved them into Gerry's downturned
face."They're jacks, I left the ball in the other
room... I showed them to you once." Miss Helen
bunched the jacks in her hand and crushed them
against Gerry's balls. the pain was excruciating.
" I played with them as a girl, and you
foolishly told me that you made your poor little
sister swallow one of hers." Helen squeezed the
jacks harder, and the points were searing his
scrotum, but Gerry didn't scream, just bit his
tongue ".But, darling boy, you couldn't take her
to the Emergency Room, because you had a date
that night...you laughed at the memory, Gerald."
Miss Helen let go of Gerry's balls, and he
heaved a sigh of relief. She bent down and put
the jacks on the marble floor in front of his
feet. "Gerald, do you really want to orgasm?"
"Yess...you know I do..." Will you do something
for me...it will be nice and also educational."
"Anything, Miss Helen..." Gerry began brightening
up. "I asked you to kneel before, and now I
insist. Kneel on the jacks, Gerald..." 
Gerry looked down in horror, and Miss Helen
took him by the shoulders and made him kneel
again. His knees, not too well from the hours on
the hassock felt new stings from the little metal
jacks prodding.."Now, Gerald, if you want an
orgasm, I want one first. You haven't eaten me
out since seven this morning, just before we went
to Mass..." 
Miss Helen took off her shorts and panties
and put her shaved vagina in front of Gerrys
tortured face. "Eat, Gerald...give me the orgasm
that you want."
************************************************
It was ten o'clock. Gerry was once again
spread eagled to the bed, after having licked
Miss Helen to about four orgasms, before
collapsing under the pain of the jacks... Miss
Helen had rubbed iodine on the knees, and taken
him back to his prison of the morning... and was
stroking his penis again...using the lotion. True
to form, Gerry was again rock hard, as he'd been
on and off for thirteen hours.
Helen was now in bra and panties, casually
blowing on Gerry's cockhead, and then rubbing up
and down feverishly on the purplish shaft..."I
came over and over, Gerald...it was wonderful..."
She gripped the shaft like a VW bug throttle, and
began rubbing up and down in quick strokes...
Please PLEASE..."
Are you ready, my sweet?" "Yes ma'am..."She
rubbed faster, and Gerry's hips ground and
bucked, and it was now time, Oh, my wonderful
Miss Helen! Suddenly Miss Helen stopped again,
and Gerry felt an ineffable pain in the tip of
his poor, tortured erection..."Sweetie, I have to
go watch the ten o'clock news. I forgot, there's
something about the hairdressers union...I'll let
you come at eleven p.m." 
And she kept her word...two weeks later, on a
Sunday night at eleven p.m., her grateful Gerald
had a wonderful, surging orgasm, that was served
back to him on Miss Helen's manicured fingers...
**********************************************
It was a blustery Sunday,in March of 2020. The
memorial service had broken up, and the fifty-one
year old managing partner of K street's most
powerful law firm thanked the reverend and walked
out into the cold air. A sudden stroke...one day
Gerry'd just come home, and Helen was it
appeared, fast asleep over a Jane Austen novel.
Now, though he was heartbroken, and terribly
terribly lonely for his partner of over thirty
years... and had been crying daily for a week,
Attorney Morin had a new problem. His padlock was
still on, and he hadn't been able to find the
key. Bolt cutters? 
His last orgasm had been a month away, and he
was grieving but horny, jerking off would help
him forget Now, he could do it over and over
again, whenever..."Mr. Morin?" Gerry looked over,
and the attractive young redhead who had been
sitting in the pew behind him was smiling at his
side.
"You're Keri Ann, right? Helen's niece? You've
moved here to finish college?" Gerry smiled at
her. God, Keri was gorgeous, the same figure as
her aunt, but what mischevious eyes! Keri smiled
and handed him a letter. "Read this, please."
"Dear Gerald:
Dr. Towlen informed me the other day that I
have angina, and not long to live. I have kept my
neice, Keri Ann, informed of our life together,
and sent her the many pictures that I've taken of
you in various states. She has inherited the
house, and needs someone to help her with
college, and perhaps grad school tuition. I trust
you can help her. 
I love you very much, and treasure our time
together.
Helen
P.S. Keri Ann has the key"

THE END
WHAT HAPPENED NEXT TO GERRY?
EMAIL justincbenedict@yahoo.com


BOOK TWO

Part One

March 10, 2020

"Dear Gerald

Dr. Towlen informed me the other day that I have angina and not long to live. I have left my niece, Keri Ann, appraised of our life together, and send her the many pictures that I have taken of you in various states. Keri has inherited the house and needs someone to assist with college tuition. I trust you can help her.

I love you very much and treasure our time together.

Helen.

P.S. Keri Ann has the key"

*******************************

Gerald Morin, J.D. re-read the note, trembling...Helen, his landlady and dominatrice of 30 years, had passed away. And she'd told her 19-year old niece! Gerry was astounded that the reserved Helen would share anything of their private life, but she'd always been an enigma.

After being tossed out of a fraternity house for selling drugs, the arrogant, womanizing "Scary Gerry"had been amused to answer the sexy, mysterious hairdressers "Room To Let" ad. But then Gerry and Helen discovered they subscribed to the same tease/denial magazine. And,she'd taken over his life. transforming the drunken sophomore into a brilliant patent attorney in less than a decade. Gerry'd never left..

Somehow, being caned for bad grades, and later, horsewhipped for poorly written law briefs, doing all the housework, having the bedtime of a nine year old, and wearing a chastity piercing wasn't so bad when Helen decided to "treat" Gerry. Every week or two, Helen would tie Gerry naked to the bed, unlock the piercing and tease his cock with her soft, lubed hands and long red nails for hours, stopping whenever it looked like he was close to cumming. Then, she would lock the frustrated, swollen cock back up again...but every 10 or 12 sessions, Gerry never knew when, she would let him have a mind blowing orgasm.

But after Helen had died, a fortnight ago, Gerry realized that he had no idea where the key to his penis padlock was, and wondered how he would get loose, so he could cum, somehow...but this girl had the key! What would he do?

Gerry turned to the amused young brunette at his side. Keri Ann's green eyes were dancing, and the fingers of her right hand were playing speculatively with an errant strawberry curl. Helen's memorial was held on a cold day, but Keri Ann's jacket was open, and her chest was heaving against the snug cashmere sweater in silent laughter. Gerry's penis swelled, and he felt the familiar pain just below the cockhead, where the padlock hung. In the struggle to get an erection, the evil padlock always seemed to win, since Helen had pierced him some 30 years ago, producing the key only for extended teasing and the rare orgasm. And Gerry hadn't had the lock off, this time, in forty-two days. In the 30 years since his landlady put him in chastity as a college sophomore, Gerald had gone longer than that, but at least he always knew he would be coming out of it, but now?

How can I get the key from her? How much does she know? I have to jerk off! After three decades of regulated ejaculations, it would be nice to "self abuse" as Helen used to say. How do I get her to give me the ---? "As the note says, Mr. Morin, I've come to live in Aunt Helen's house, and my bags are with me. Aunt Helen loved you very much and told me that you would be staying on, since you lived with her for so long. Would you drive me back?" Keri cocked her head and raised an eyebrow."Certainly." Gerald managed. "Would you like to have lunch first?"

*******************************

Gerry put Keri Ann's last bag on the floor of Helen's former master bedroom. The previous 3 hours had been arduous. Gerry'd taken Keri Ann to lunch, and advised her on scholarships...For the entire time, he waited for her to mention the key. Did she really know what it was for? Would she give it to him? If she didn't, the little bitch could tell others about it, and he'd probably lose the senior law partnership. He sipped a martini, listening. He'd been drinking a lot. Helen had gotten him sober, and never allowed him to drink again...well, now he could. Smoke and drink. And once he got the key--

Keri came in behind him and sat on the bed, she crossed her long legs and leaned back on her hands, arching her back for a marvelous frontal, and continued discussing her educational plans. Gerry was lost--he didn't know how to bring up the question of the key. Did she know everything Helen's letter referred to? "Pictures in various States"

God, in one of Helen's more graphic Polaroids, back in '04, Gerry was photographed on his back, under a bottomless dining room chair. He was wearing a corset, fishnet stockings and high heels. Helen had sat nude from the waist down, in the chair, and after 2 hours and 5 orgasms from Gerry's under-the-chair ministrations, she'd given him permission to stimulate himself by rubbing his engorged, purplish dick against the legs of the chair above him. Gerry had inched over , elbows bound together under his back, and rubbed his penis against one of the legs, when he heard the flash of Helen's digital camera. "For posterity, Gerald." Helen chuckled. It had gone out as a Christmas card to all the members of their TeaseAmerica website. Gerald winced at the memory, his cock straining against the piercing yet again. I HAVE TO CUM!!

Keri Ann's voice broke into Gerald's reverie "I could do a Russian Lit minor but --Are you all right, Mr. Morin?" Gerry came back. "I apologize, Keri Ann. Since the funeral, I've been a little tense, and --" "Do you want your key?" Keri smiled at him, and reached into her handbag. She looked so great in the tiny sweater and skirt, legs everywhere, sitting on the bed. Keri Ann placed a small padlock key into Gerry's hand. Gerry looked at the key stupidly. He'd never been allowed to hold it. Once, he'd stolen the key to do a quick, desperate whack-off after an extended time, months, of teasing and chastity, but Helen had caught Gerry right before he'd cum, and she'd given a severe whipping. Gerry looked at Keri, and she nodded, slightly." Take it off, Mr. Morin, if you want to, and touch...um yourself."

Touch myself? Unlock the cruel piercing, and jerk off all he liked, date the little paralegal who had been making eyes at him...Gerry had had less than a hundred orgasms in the last three decades, though he'd been stimulated a great deal by Helen...He could do anything he wanted...he could get porn films like "Dr.Fellatio" jerk off all day, find a girlfriend, have his first blowjob in so many years, God knows there were women who wanted him but...

"Gerald? You're crying." Keri Ann used his given name for the first time, the whole name, just like Helen had. "I just miss her so much" Gerry whispered, looking at the key with bleary eyes. Keri stood up, and gave Gerry a big hug, pressing her 34DD breasts against his chest "I loved Aunt Helen too... why don't you give me the key back, baby. I don't think you're ready for it." Gerry dropped the key into Keri's extended palm, thus once again, giving up his freedom. But then he said "Keri Ann, excuse the expression, but I need to cum. I haven't in so long..." Gone was the expert voice of the attorney and college trustee, it was just childish begging now.

Whap! Keri Ann slapped Gerry's face lightly. "Stop with that nasty talk, the day of my aunt's funeral." Gerry hung his head and cried harder. "The first thing you'll do" said Helen, taking off her jacket and tucking in her sweater further "Is call me Miss Keri Ann. And the second thing is you'll strip and bring me Auntie's handcuffs."

*******************************

"Ohh..Miss Keri Ann. Can't I at least sit down with you?" Stark naked, Gerry was standing, hands cuffed behind him in front of a chaise lounge where Keri Ann was lying casually. Keri's hair tumbled around her shoulders, and she was wearing a tight black midriff shirt that barely covered her breasts, and tiny bluejean shorts that made Gerry intake breath whenever she'd turned around. Her legs, beautifully shaped, were encased in fishnet stockings. She was perfectly relaxed, except for one hand, which was reaching out and stroking Gerry's purplish cock. "No. You can't sit down. It's good for your lazy ass, Gerald, to do some standing. In the two weeks I've been here, all I've seen you do is SIT reading, SIT watching television. Stand up!" Keri Ann casually rubbed the underside of Gerry's cock with her forefinger, touching nothing else...He was trying to straighten his legs, but it was very hard."And you whine. It's disgusting, Gerald." Keri Ann added one finger to the rubbing of the underside, and began stroking the base of the cock with her thumb...it looked as if she were wrestling with a child-proof aspirin bottle. "Can I cum, can i cum?" Keri Ann spoke in a whining falsetto. She seemed so sweet at the memorial, Gerry thought."Thought I'd wank you off immediately after the funeral?" Keri now took both hands and began rolling the tip of the cock around. Although Helen had always used lubricant, her niece had the exciting habit of rubbing the dry cock with two or three fingers, alternating spots on the shaft and balls, which drove Gerry crazy. Keri now began jerking him loosely with one hand, rubbing the encircled fingers and thumb up and down the shaft...but there was no friction, just stimulation...it was a handjob in SLOW motion. "The first night, crying and begging on your knees, what a tantrum. As if the death of the woman who changed your life was cause for YOU to have a party." Keri began rubbing with two fingers again. "But then I found Auntie's razor strop, and gave you something to really cry about." Gerry winced at the memory. His bottom still swelled, though the blisters were healing.

"And your drinking, Gerald." Keri tugged at his foreskin, then lightly rubbed the ball of her forefinger under the head of his leaking penis. "Auntie led me to believe that after a few whippings during your first days with her, you'd foresworn alcohol and drugs." "Ma'am, after Miss Helen passed, I...went back to drinking." Gerry babbled. Why didn't she grab his cock instead of toying with it with one annoying finger? Would he never cum? He looked at it. The violet-ish veins along the shaft of his penis looked like they might burst. Keri, as if reading his thoughts, giggled slightly, and her cleavage shifted. Gerry rolled his eyes. "No more gin and tonics for you, young man...warm milk before your 8:00 bedtime." Keri gently pulled Gerry down on the couch next to her, Thank God. She put her arm around his shoulders, and pulled him to her neck. "Kiss it, baby." He began kissing her neck, stealing sly looks down her shirt at the heaving white mounds. He felt his cock lunging, the held-back semen almost pushing to the head. He began kissing her perfumed neck. It was hard for him to reach over, as his hands were cuffed, but Gerry was doing his best. Keri was now rubbing her forefinger and middle finger up and down the shaft with one hand...she pulled her other arm away from Gerry's shoulder and cradled his testicles with the other, red talons casting a peculiar hue on the strained purple ball sac.

"Do you want to cum, sweeheart?" Keri whispered as Gerry kept kissing her neck. God, how smooth it was. These 20 year olds were almost like teenagers...Gerry nodded, and kept kissing madly, hoping he could slip a hickey in there. Keri kept rubbing faster and faster, now fully grasping the penis with her looped fingers, and Gerry began breathing harder. "Just keep kissing my neck, baby." she whispered. Pump, Pump. Her other hand was playing gently with the testicles, lifting them and twirling them around....it felt so good.Gerry kissed Keri's neck, stared down her cleavage and began lifting his hips rhythmically to the stroking. His legs began quivering. Here it came, finally...

"Aaaugh!" Gerry screamed. He had not cum. Keri had clenched her ball cradling hand tightly, and slipped her finger around the base of his cock...there would be no orgasm, Oh, the PAIN....Keri stood up, pulled Gerry off the bed by his hair and threw him on the floor, where he landed on his swelled cock. "Thought you'd squirt on MY HAND? Oh, funny..."

*******************************

Thwack! Tears were streaming down Gerry's face. His mouth was burning. It was too much. There he was, in his ornate office beautifully decorated in mahogany, oreintal rugs and a Monet original, his extensive diplomas and awards on the walls... and yet he was lying over Keri's lap, Armani slacks and silk boxers bunched around his ankles, and his tie over her thigh, as she administered a the last whack of a blistering hairbrush spanking. There was a knock on the door. Gerry's heart stopped. "Mr. Moin?" It was his paralegal. Keri spoke. "Brandon, Mr Morin's resting right now." "I need to see him about the Parfemac brief, Keri." "He'll be available at three." Keri chuckled, as she heard Brandon walking away. "They probably think I'm sucking you...what a joke." Gerry's cock gorged painfully against the tiny cage.

When Keri, who Gerry had hired to do part time billing after her morning classes had exasperatedly ordered him to drop-em and bend over for misplacing a file she needed, Gerry had worried that he might begin screaming as he did when she disciplined him at home. After all, there were attorneys, secretaries and mail clerks milling around in the hall outside. Keri had solved this dillema by taping a wet bar of laundry soap in his now foaming mouth, and this served as an effective gag.

"Okay, Gerald. Let's get up." Gerry felt her unncuffing his hands. He pushed up off her lap. Keri's first week at the firm had been rather painful for him. Yesterday she had closed a metal drawer on his exposed scrotum after discovering his participation in the office football pool. Geri stood in front of Keri,who looked very cute in a snug angora pullover and leather miniskirt. HEr legs were crossed now that Geri's weight had been lifted. Keri had dropped the warm ivory hairbrush on the floor, and was freshening her lip gloss, her mouth an O as she stared into the compact.

Gerry stood at attention, knowing better than to remove the soap or pull up his drawers without the go-ahead. "All right, cutie..you look like rabid dog--no a rabid hamster, really foaming like that. Take the soap out of your mouth." Gerry pulled the tape off, ripping some of his sideburn hair off with it, and took out the soap.His mouth felt like the Bermuda Triangle, and he'd cried so hard during the whipping that his face looked as if it had been beaten with rocks. Sympathetically, his billing assistant handed him a glass of water. Gerry gargled, and spit the remaining soap into the wastebasket, knowing his mouth wouldn't feel normal til tomorrow. Then, as he was about to pull his pants up, Keri held up a magenta fingernail and wheeled the leather chair up to his crotch.

Reaching out to twiddle the cock cage, she chuckled again. "That thing was a bitch, pressing into my thighs during your walloping." she murmured."I have good news for you, Gerald. Dan came back today." Gerrys legs began trembling and his cock pressed painfully against the bars of the cage. His poor wee-wee was a little raw, as it hadn't been out of the cage in six long weeks. Keri had promised then that Gerry could jerk off to orgasm if he gave her hairdresser Blaine, and his two friends from the Gay Men's Chorus a blowjob, and drank a fishtank of their accumulated urine. But after this horrible, degrading task was completed, Gerry found that Keri had left her key on the same ring as the key to Gerry's Mercedes, which she had lent her brother to take a month long trip cross-country. Really, it was an honest mistake.

Dan had stayed a little longer than he intended... and so not only could Gerry not cum, but he hadn't even had the cage removed for sessions with Keri's teasing fingers...the "milkings". She had done quite a few sessions with a robin's feather through the bars of the cage, but this caused too much pain, as Miss Helen, Geri's now deceased former mistress had had the cage built just a little too small for a full erection. "So you can focus on the important things, Gerald." shed said, laughing. For the last few years before Helen's death, he had been in a cock-lock piercing, but Keri had pulled the old cage out, as she thought piercings were "unhealthy" but actually, Gerry suspected that she knew that a hard cock in a cage would be so much more painful...Maybe not...she has such an innocent face!

"So Dan's back, Miss Keri? Can we take the cage off, please?" Gerry's heart was pounding. Gerry hadn't cum since a month before Keri moved in, and it was now close to five months. Keri released the cock cage, laughing, and grasped Gerry's scorched,still-bare buttocks from behind. Embedding her nails in his welted cheeks, he burst into fresh tears from the pain.

*******************************

Gerry lay, once again cuffed and naked on the queen sized bed in the Mayflower Hotel. He rarely got to lie down on queen beds, Keri had the master bedroom, and Gerry usually was in his little single bed in the guest room, though of course it was his house. He had to meet Brandon at 3:00 this afternoon, but he was so excited that the key was back in Keri's hot little hands, that he'd begged her to go with him to the Mayflower to get the cage off, just for a little while. Would she let him cum?

Keri sat on the side of the bed...She'd pulled off her sweater, and was now only wearing a violet demibra with little flowers on the cups. Her cleavage was heaving as she laughed, taking the horrid little dungeon off Gerry's now wounded bent erection. Free! Gerry looked over his gut at his member, now waving in the air. Keri ran her finger up the tip, and it immediately hardened. "So, big boy...want some action?" Keri laughed."I bet you think we're going to have squirtie time today, aren't you?...and what have you done to deserve that, may I ask?"

"B-but Miss Keri, " Gerry blurted. "Before you accidentally gave your brother the cage key, you promised--promised I could cum."Gerry choked back a sob. "And-and since then, I've performed between your legs every night, even licking out your boyfriend's semen...I've cleaned the house daily naked, paid your tuition, and given you a huge allowance in addition to your salary at the firm." Gerry's lip trembled. Keri's fingernails were dancing up and down his shaft, flicking and then rubbing the underside of his trembling cock...oh, the pain... She then encircled the tip with her fingers and thumb and began squeezing it slightly, and then moved down to the base...and continued squeezing, dropping her little finger to move about the foreskin. Gerry thought he was going to die.

His butt still felt like boiled cabbage, and he had really hoped, in vain, that Keri might just let him wank when they got to the hotel. She owed it to him!

"Poor Gerald..."Keri spoke ina sing-song voice...I haven't let you cum once since I moved in after Auntie Helen's death...have you ever gone this long before?" "Once" Gerry sighed. "She found a condom in my jacket that one of my partners put in as a joke, and suspended orgasms for six months, with daily two-hour teasings." "No kidding?"Keri asked. "So this five month period isn't a record? That's a shame. I wonder if you could go without for a year." Keri began rubbing her thumb back and forth against the terribly sensitive nerve just below the tip of Gerry's penis. The cock began throbbing and dancing about like a Mexican jumping bean. Precum was already beginning to dribble out, and he'd not been tied down for more than ten minutes.

Keri's nails were long and perfectly manicured...a deep purple, almost matching the shade of Gerry's cock. He paid the bill every month to Elegant Nails Co., and so he knew how expensive they were, but certainly it was worth it...Both Keri and Helen had never needed false paste-ons, because their nails never got any hard work...no cleaning, lifting, or even back scratching...all done by poor Gerry's capable hands.

She leaned over further, and her breasts seemed to be tumbling out of the demibra, the areola of one nipple showed for a moment, and she pulled the bra up slightly, and smiled. Gerry had never seen Keri naked--she always kept a top on, and only let him lick her when he was blindfolded. This was incredibly humiliating, as he was forced to walk about nude at home, and often to partially undress at work for disciplinary reasons. "Look at it, it's practically Old Faithful." Keri said, as she rubbed the precum into the tip of Gerry's penis. She then looked at him. "Are you sure you want to cum, sweetie?"

"Oh, oh yes ma'am...please." Gerry looked up at her with tears in his eyes. His balls were full, and the cum kept surging up the shaft...the sperm cells were miserably rebelling against the torture, pounding against the tip over and over again, as she tapped her fingers around the tip. "Well...I hope you'd make more of a sacrifice. That blowjob business you did to get cum privileges is old now...expired. It's not my fault you haven't cum...you should've reminded me to check my keychain before I lent it to Dan."

Keri's forefinger was now rubbing the bluish vein on the underside of his cock up and down...her other hand was tickling the scrotum. This went on, and Gerry's cock began to surge forth again..He raised his hips to meet her hands, pushing his cock into her ministering fingers....he was getting closer...CLOSER...Keri dropped his penis, and used her other hand to shove his hips down. Getting up off the bed, she went to the hotel closet, Gerry watching the globes of her bottom bounce in the blue thong panties... "Oh, what's this?" Keri turned around, holding a clothing iron. "Jesus for $450 a night, you'd think the Mayflower would have laundry service."

Why is she fiddling with an iron? Gerry thought. I need to GODDAM CUM! His cock was now waving helplessly in the air...as rock hard as if Keri was sucking it. Was it healthy to have this much backed-up cum? Keri came back and sat down on the bed, looking at the iron carefully. She reached over and plugged it in, watching it steam, while absently twiddling with Gerry's cock...Suddenly she reached over and pressed the tip of the iron onto Gerry's nipple and he screamed in pain.

"Oh, come on...just for a second." Keri shook her head. "You've had stuff done to your nipples...I had moustraps on them this morning." "Noo-thing like that." Gerry was once again sobbing, perhaps for the tenth time since his spanking in the office two hours before. "Well, enough of this," Keri looked businesslike. "Do you really want to cum, would you do anything." "ANYTHING...Miss Keri...do you want another diamond bracelet." Gerry looked hopeful. Kerry smiled, pulling Gerry's foreskin over the tip of his penis. "How about the iron on each of these nipples...for just ten seconds each?" "No...Mistress, not that.."Gerry looked miserable. Keri began jerking his cock madly, and once again the precum was spilling out. In spite of the pain from the iron, and his still blistered buttocks, Gerry began hurtling his cock into Keri's dancing fingers...it was so close...."Do you want the iron?" Keri asked..."No, Mistress..." "Well, I want you to go limp within forty seconds." This was a worse offer than the earlier one. Keri began waving the iron over and back around Gerry's nipple area...He thought of baseball scores...her fingers were still playing....Anything..what will make it droop? Keri's aereola was again showing over the bra. Gerry closed his eyes and thought about being naked in a snowstorm..."Thirty six thirty-seven thirty-eight seconds...ooh, it drooped." Keri was now holding a limp cock in her hand. "Congratulations!" Keri smiled and put the iron down on the table. "So, really, if you can't even maintain an erection, why do you need to cum?" For the twentieth time in four hours, Gerry burst once again, in tears.

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The leather hood was especially hot on a sunny August day, and the central air conditioning did not reach the cellar of Gerry's summer house. Gerry hadn't seen light for nearly an hour. Except for holes for his nose and mouth, the hood completely covered his head and eyes. August! Jesus. It had been November when he met her...

Nine months Ker had been living with him, teasing his poor cock daily with casually lubricated fingers, and still he had not had an orgasm. "Mistress, it's probably not healthy for my testicles to have all this backed up semen." he'd protested last week. Keri had laughed, and suggested that she massage his prostate, releasing the sperm that way. When Gerry looked horrified, Keri said "Don't worry, Gerald, with all the pre-cum that's leaked from your bulbous wee-wee, it can't be too congested."

Keri's rule was far more grueling than Helen's--Keri's sexy, youthful body tempted him much more, and though Helen had monitored his work life by reviewing his briefs and cases, administering heavy whippings for mistakes she'd spotted, Keri had taken off the semester to work full time as his executive assistant, which meant Gerry's butt and nipples were blistered almost daily for the minor administrative mistakes he'd made.

And at least twice a week there were long, unfullfilled milking sessions at the Mayflower, where Keri would massage his naked cock ten strokes slow, then ten fast, followed by one finger up and down the shaft--when they'd return to the office, Gerry would be wobbling, and though incredibly stimulated and titillated, completely unsatisfied. His cock, re-caged, would be pressing horribly against the nasty little chicken wire... Certainly, Helen would keep Gerry celibate for as long as six weeks, but Keri's 9 months with no orgasm was almost unendurable.

And now here he waschained to apillar in the cellar of his expensive country house, hands cuffed behind his back, cock raging, as always stark naked except for the horrible hood.He hated being unable to see. A month ago, when he'd brought her here to show Keri the summer house for the first time,Keri'd told Gerry she was so grateful he'd exposed the house to her,he was going to cum, and stripped him naked, chained the hands and blindfolded him in the kitchen upstairs...masturbating him slowly...and then she began hitting him with a vacuum cleaner cord, he'd run around blindly until he'd fallen down the cellar stairs. Oh it'd been awful, he'd fallen right on his struggling, wee-wee...and now...Wait? What's that poking through the mouth of my hood? Oh my God!

*******************************

Well Jesus, how long's he been lying there?" Alyssa lookd at Keri, and then back down at the hooded, prone figure. Gerry's penis was pointing to the ceiling, a brilliant violet, Keri kept prodding it with her high heel, and it jumped at every stimulation. "He's been down ehre since early this morning, and he;ll be here a while." KEri was wearing a black midriff shirt with "I just Fucked Your Boyfriend" emblazoned on it in silver block lettering, skin tight cutoffs that squeezed her bubble but to the point that the IGA clerk down the road had dropped a carton of eggs as she brushed by him towards the Pepsi liter bottles.

Keri's feet were in black leather spike heeled sandals, and the right one was keeping Gerry's crotch area quite busy. Alyssa surveyed her friend with interest. Since her friend Lalani and her husband Cary had introduced her to the "scene" Alyssa's life had changed, she'd met a successful architect, David, who'd been with Lalani's group for some time, and he'd shamefacedly given her the keys to his chastity device about a month before...David came into the room just then,stark naked, except for his cock cage...and of course the cute bracelets keeping his wrists snug behind his back.

"Did you tell him?" Keri asked."Oh, yes...David hasn't had a squirtie in almost two weeks, and he won't get to squirt unless he does it in the hood, right, Davey boy?" David looked miserable.

"But Miss Alyssa, I'm not gay...please let me cum, it's been 9 days!" Keri laughed. "Gerald here hasn't cum in 9 months! And in the last 30 years that my late aunt was training him, he came about once every month and a half if he was really lucky! And you're just getting your dick sucked....Aunt Helen told me once that she made him "--Keri motioned at the hooded, naked figure on the floor--"go out in full drag, lip gloss, wig, fishnets, and suck off truckers on the waterfront for ten dollars a piece...she said she'd let him cum if he came back with fifty bucks, but she changed her mind, and when he came back with seventy, she wouldn't take the cage off...Gerry threw a fit, and Auntie pulled his panties down over his fishnets, and bent him over the couch and gave it to him with the buckle end of a nasty, nasty belt she had...and then didn't let him squirt for another month for whining."

David looked miserable at this. He had been able to cum every two or three days, after heavy teasing, but Miss Alyssa seemed determined to follow her friends lead here...and the poor Gerry guy. Keri was rubbing the heel of her pump against Gerry's purple cock absentmindedly as she spoke, and the dick looked lavender...it was sooo ready to cum! And Gerry couldn't even see how beautiful Keri looked because of the hood! "Okay, it's time!" Alyssa looked at him, pursing her lips."Do you want to cum, or wait another thirty days...and then just come right back here...you're going to cum in this hood, or not at all." "But Miss Alyssa...I've gone down on you nightly, given you sponge baths, bought you jewelry and clothes.."here David's voice cracked. "Can't you just give me a break? I l ike this tease/denial thing but...OW!"

Alyssa had hit David in the face with a flyswatter she'd seen on the kitchen table."Shut your mouth!...if you want to, we can go back to being boyfriend girlfriend,but if I'm your mistress, it's like this...I can go home and suck your dick,you can cum whenever you want, go back to sleeping in the bed you paid for with me instead of the broom closet, but no more whippings, no more tease/denial...you can live comfortably with me, do what you please...but you can't have both. I can suck your dick if you give it up."Alyssa hit David again."Or you can let him suck yours!" David thought for a moment..."No, Miss Alyssa, I'd need your discipline."his voice shook,and he began welling up," and the closet--and the chastity..." David dropped his head to his chest.

Alyssa winked at Lalani, and unlocked David's cage...as his cock sprung out she ran her burgundy nails across the tip, and it sprang up like a Marine at attention. Keri and Alyssa gently guided David to the hooded figure, and Keri opened the zipper around the mouth. Alyssa began hitting David's butt with the fly swatter, as Keri pushed his dick into the hood...David felt heavenly sucking...he hadn't had a blowjob in years. Was it a man?

Well, he knew how to use his tongue, that's for sure...must've learned from the truckers..Whack! That was no flyswatter, David looked around, and Keri had a bamboo cane in her hand. "David, Miss Alyssa is going to undo your cuffs..I want you to grab Gerry's hooded head in your hands and jam it onto your cock,and then pull it back...I think you fraternity boys call it skull-fucking!" Gerry heard this, and began trying to pull his head off the cock, moving frantically away from it..."Baby stop it." Keri said. She held his shoulder. "Mommy's going to rub your wee-wee while you get skull-fucked...you might choke to death, but you might cum, too..." Within a minute, Alyssa was witnessing an interesting phenomenon. Her husband, eyes closed, was jamming his cock into a hood with a man's naked body under it, while Keri,squatting, was rubbing the hooded man's cock energetically with Vaseline. As David slammed the cock in and out, she could hear gagging and coughing from inside the hood, and once David screamed that he'd been bitten....but it went on until he came...Gerry's cock was about to spurt in Keri's hands, his hips were pushing off the floor with no support from his bound hands, but Keri, just at the edge of Gerry's orgasm, pulled her hands away dramatically.The cock blindly thrust into air, and then Gerry realized he'd been rooked again, and began crying in the hood just as David was pulling his cock out.Kerri gave David a piece of sandpaper to wipe off the cum...David looked horrified, but Alyssa hit him again...and then sent David out to sit in the backseat of the car, naked and waiting for her to drive him home. Then Alyssa's boss, and her neighbor, also naked and cuffed, came into the room...and Gerry had to start up again.

*******************************

Keri helped Gerry upstairs, Alyssa laughing and following her... "Poor thing, you just have had so much HAPPEN in the last few hours...You had to suck off three slaves, and I promised you that you could cum...and here you are, and they're all in Alyssa's car...your boss is in the trunk, isn't he?" Alyssa laughed. Keri opened the cellar door into the kitchen of Gerry's attractive summer cottage. He had had it built ten years ago for Helen's birthday...and they'd had quite a time there until her death...Crops in umbrella stands in every room, and a hook in the ceiling of her Florida room.

Finally Keri took Gerry's hood off, and led him into the living room...Gerry was blinking in the light, his hair, soggy with perspiration was damp on his head. His dick was purple and dripping, and his balls were just congested with frustrated semen. Gerry looked blearily at Keri and then Alyssa, who he hadn't seen before, though she'd just spent two hours teasing him, and forcing her various slaves' wee-wees into his mouth through the hood. She was quite something, Alyssa. 34DD breasts cinched in red tube top, leather short-shorts, and high heeled pumps. Gerry, realized he was naked in front of a perfect stranger, hung his head. Alyssa laughed, and chucked Gerry's chin. "Cheer up, Gerald" Alyssa smiled. "This hurts us more than it hurts you." The two girls doubled over in laughter.

*******************************

Gerry poured the last drop of coffee into Alyssa's cup. "Thank you, sweetheart" Alyssa reached over with a crimson nail and flicked the purple cockhead. This was rare--Gerry's cuffs had come off, and the cage was not yet on! Keri had put him on the honor system. "You know if I can trust you not to wank your wee-wee, sweet dumpling, there might be a surprise for you later...we're two hot chicks. Why don't you make us lunch now?" Invigorated, Gerry had made Alyssa and Keri a caeser salad and a vegetarian lasagne and served white wine...now they were relaxing over a mocha coffee in the living room.Keri was telling Alyssa about their visit the other day by the village sherriff. Their first day in the country house, Keri had mistakenly thought that Gerry had cum during his weekly shower with the cage off.

Usually Keri did the bathing herself, scrubbing the area thoroughly while Gerry stood under the spray mutely, hands cuffed behind him. He would get intensely aroused as she'd tease him a little after, til his cock resembled a soapy Louisville Slugger,but then Keri would switch the temperature to freezing to "calm you down." But Keri was distracted putting dishes away, as they'd just arrived for the month of August, and left Gerry to clean himself on the honor system. She'd walked in on Gerry as he was washing himself a little too enthusiastically down there, thinking she saw semen in the bubbles in his crotch, Keri lost her mind. She'd laid Gerry on his stomach on Miss Helen's footstool, hands and knees tied to the legs, "And you should've seen that hassock dance!" Keri said, laughing. "He made it crab crawl away from me as I beat his ass with a thorn branch I'd cut from a rosebush outside, and then I turned him on his back and re-tied, and lit into his bare crotch, and the screaming brought the sherriff. I showed him Gerry, lord of the manor, tied to the hassock naked, and Hank, the sherrif laughed...Gerry hadn't paid any of his speeding tickets the year before...So Hank hit Gerry a lick or two also, and he's taking me out to dinner tomorrow night, while Gerry's locked in the closet, isn't that a riot?"

After listening to this horrible story, Gerry took the coffee pot back intot he kitchen. Absently he reached down and touched his suffering penis. That was one hell of a cleavage that Alyssa had...tube tops were great, he hadn't seen one since 1980. He leaned against the sink and rubbed. "You're touching it, Gerald" came Keri's strident tone "Hands off...keep them busy by doing the fuckin' dishes" Gerry's heart sank, but he began washing the kitchenware he'd used as well as the dishes and plates, and thought about his reward. Would they maybe fuck him? Never. But perhaps they might whack him off, after nine miserable, frustrating months...As he leaned over the sink, his cement-ish cock hit the counter painfully. Or maybe, they'll let me jerk off, and belittle me while I do it...I wouldn't object to that, even if I have to lick it up...His heart rose. That's what it'll be. Keri's a sweet girl, really she is! He finished the last of the dishes and cleaned the entire kitchen, and then went back into the living room, where the women were looking over a copy of "Elle" Gerry knelt in his most submissive position, cock out like a Crusader's lance....this will impress them, I am a good boy. They'll give me a break. After ignoring him for about twelve minutes, Keri looked up. "All cleaned up, sweetheart? That was a lovely meal." Gerry bent his head "Thank you, Miss Keri. I tried my best...you said maybe we might have an adventure now? I've been so good...please." Gerry's head was lowered to the floor, and he didn't see the wink that Keri gave Alyssa. "Oh honey.."Keri smiled "You're absolutely right. It's time for you to have a treat." She stood up and motioned Gerry to stand. God she has big breasts...I've never been allowed to see them bare or the nipples even ONCE, but I've seen quite a bit of them...OOh I want her..." All right, sweetie, let's cuff the hands..." Seeing Gerry's face fall, Keri smiled "Honey...you know you can have fun without your hands..do you want to do all that work?" Keri handed the cuffs to Alyssa, who locked Gerry's wrists behind his back. Gerry looked up at Keri, who began massaging his poor penis, on the sensitive vein beneath the head. Quickly she would run her thumb back and forth, and it made him quiver...Alyssa came around and began rubbing the head. OOh. Two beautiful,small white shapely manicured hands were doing quite a travel around his purplish member...They smiled. "What do you want, Gerry?" Keri asked. She'd never called him Gerry before. "I want to cum...please...couldn't I just jerk off, Miss Keri?" He looked with pleading eyes. Keri smiled up at Gerry. "Well, it's about three o'clock, and I think Alyssa has to take her boys home, and I have to do some shopping...and it's time for you to take a nap." Gerry's lip began to tremble. "No whining..." Keri led Gerry into the bathroom, and she and Alyssa made him lie in the bathtub on his back. Keri whispered into Alyssa's ear, and the girls both giggled. Alyssa stood with one foot outside the tub, and one on Gerry's cock, straining with the frustration of 9 miserable months. Keri stood in front of her, and put a stockinged foot on Gerry's mouth. Alyssa began rubbing the penis, and Gerry's hips began shaking. "At last, Gerald..."Keri looked down at her poor slave. "Now?" he asked. "Wasn't it worth the wait? Doesn't that foot feel good?" As Alyssa rubbed her toes on the cock tip, Gerry's hips again began to tremble. He kissed Keri's foot madly in gratitude...here it came..closer and closer...precum began seeping through Alyssa's toes as she rubbed and he pushed. HE WAS ABOUT TO CUM....Gerry looked once more at the beautiful woman giving this exquisite treat, and closed his eyes, thinking of Miss Helen, and what a legacy she'd left him...here it came...

UGH! WATER! All over him! Alyssa's foot was off his cock, right before he spurted, Keri's toes were no longer on his mouth, he opened his eyes, and they'd turned the shower on, freezing cold...the girls doubled over in laughter, Alyssa sitting on the commode, and they left the lavatory, assuring Gerry they'd be back to turn off the water in an hour...Gerry lay in the freezing drench...and sighed.

PART TWO

Gerry was tired... his heels were killing him. Stilletos just weren't made for a six foot five, one hundred ninety-five pound man, even heels specially purchased at the Tranny Warehouse. And it was drizzling rain. How do women do this every day, he thought. Walk around on these ghastly things. They felt like they were pounding into his feet. And it was drizzling rain, two in the morning. Gerry looked down at his hand holding the tiny purse, one of the bright magenta paste-on nails was falling off. Only half a block, he'd be home. It was a good thing he'd hitched a ride from the Waterfront back to Cathedral Heights, though the guy had demanded a freebie...

When Keri had sent him out to the waterfront the night before, Gerry had begged her to let him drive, or at least take some money. "No, no, Gerald." She'd laughed. "You're not going to get the car stolen in that awful neighborhood. If you want to earn cab money back over the target amount, that's your business. Here is a bus token to get there... remember, if you don't bring home at least one hundred dollars... no squirtee!"

Gerry had first approached the dockworkers outside of Mike's Grill with offers of a blowjob for fifty dollars. They'd laughed at him. One had shoved him, saying "Look, if you think I'd pay fifty bucks to a drag queen -- " "No, I'm a girl." Gerry had used a miserable high voice. As the guys doubled over, laughing, Gerry's shoulders sank. Former rugby players rarely look like Marilyn Monroe, even with a blonde wig, heavy make up and gold lame dress.

Starting from eleven-thirty on, he'd managed to give seven five dollar blowjobs and three ten-dollar ones, kneeling in the alley. No one had wanted to take poor Gerry back to their place. The last time Keri'd sent him out, that time to a truck stop, one black custodian had sodomized Gerry over a sink in the men's room and at least he'd gotten twenty dollars, but then someone else had stolen Gerry's fox fur, and Keri had beaten him with a straightened coat hanger for what seemed like hours. This time, at least, all his clothing and paraphrenaila had remained intact.

But he'd only made sixty-seven dollars... on the last, two dollar blowjob, to a homeless schizo who kept muttering to himself, Gerry's jaws had felt like lead and the john had kept grabbing Gerry's ears and jamming the cock deeper down Gerrys revolted, heterosexual throat. Gerry would've stayed even past two, but there were no more customers, and he was soo tired... but that meant no orgasm.

In the five years that Gerry and Keri had been together, since Keri had taken over training after the death of her aunt, Gerry's beloved Miss Helen, Keri had allowed the cock cage off plenty, for extended teases from her nimble fingers while her slave-boy was tied down -- Gerry was amazed at how such a tiny little hand could make him feel like he had a rioting groin -- but she'd always stopped right before Gerry was about to cum--and had only let Gerry cum -- and that from his OWN hand -- eighteen times. Just a little over two squirts a year---and he always had to pass a test, when his 90 days of celibacy were up... or she'd just give him more time.

In December, Gerry had been orgasm-free, but constantly teased for 90 days, and Keri had given him the "soap test", cutting up five yellow laundry soap bars into little chips, and telling Gerry to eat them all with a fork, within ten minutes... "Such a filthy mouth you have." Sure was tonight. Gerry had begun vomiting after three minutes, and Keri'd given him another thirty days in the cage, before the next test, which involved him doing enough sit-ups and crunches to learn autofellatio -- to bend over and suck his own dick. "Because onanism is so childish, Gerald." But, as good shape as the poor guy was in, even after thirty days of exercise, he couldn't reach his cock with the mouth, and then after another thirty, he still couldn't. After this had been electrical play... then speculum testing... wimped out..

So the last three 30 day extensions had been over Gerry's inability to bring home one hundred dollars for selling his mouth along various seamy avenues... "I'm the worst pimp-ette in the world." Keri remarked ruefully, after Gerry'd come home with eight dollars one miserable night."But if you can't make enough men cum, I'll see that you not cum yourself... been over nine months, honey, get on it." And tonight, if he ever got home, he'd get another horrible 30 days... But could he just get home? Gerry stumbled over a heel, and fell in a mud puddle. He began crying, but stopped himself, and crawled the final twenty feet home.

Oh the house. Finally. Gerry looked through his purse, negotiating the paste-on nails clumsily, for the key... it wasn't there. She had literally sent him out to the D.C. waterfront in full drag, and all there'd been in the purse was a bus token and a lipstick. "To freshen up, Gerald... you know the boys won't want to skull-fuck you unless your mouth looks appealing."

Gerry began knocking, as the rain increased. It was pelting him now. Finally, a sleepy voice was heard on the other side of the door. "Yes, who is it, please?" "It's me, Miss Keri." Gerry tried to use his little-girl voice, as he'd been instructed. "Who?" Gerry could hear the faint chuckle. "Your little trollop Gertie, Miss Keri." "Who?" Gerry begged "Please, Miss Keri, let your little whore in... I've worked hard for you all night." God it was wet. Why didn't they have more of a doorstep? "Did you make your minimum, baby?" Keri didn't sound hopeful... "No ma'am... "Gerry moaned. "My knees are bleeding from kneeling in that alley, sucking those awful men, my fishnet stockings are torn, it's raining -- " "But did you make a C-note, dearest, or not?" "I made over half of it, sixty-seven dollars -- " "Gerald, you didn't even TRY. Sit on that porch til dawn."

Thwack! Gerry was now inside the house, but it was escaping the frying pan into the fire, as it were. Keri had him over the arm of the couch with his panties and stockings at his knees, now soggy lame dress flipped over his back. At some point Keri realized that it was an embarrassing for her and probably traumatizing for passers-by, even at four in the morning ( Gerry'd been out there for two hours) to see a muddy transvestite huddling and sneezing on one of the nicest porches on Macomb Street in Cathedral Heights, the most expensive neighborhood in Washington, DC.

"Well, Gerald?" Keri waited , bamboo cane in hand. "Oh, (a-choo) Forty-five Ma'am. Thank you for (a-choo!) punishing me." Keri raised the cane again, pulling the angora sweater snugly over her breasts "WHACK!" Another landed squarely across Geri's now quite welted bare buttock. "Forty (achoo) six, Ma'am. (a-choo!) Thank you for pun-punishing me." Gerry burst into tears. "Please, no more, Miss Keri! What a night I've had!" "No, you've embarrassed this house by your disgusting presence on the steps." WHACK! "Forty-seven (achoo) Ma'am. Thank you for punishing me. But Miss Keri, you locked me out." WHACK! "You were out there, my dear, because you didn't come up with the minimum $100... I'm a tough pimp... now what do you say?" "Forty-eight, Miss (achoo) Keri... Waah! You broke a blister... " Gerry was falling apart now...

Later, Gerry was naked, spread-eagled to the four posters of Keri's Princess bed... he'd been given a little Robitussin for the sneezing, and had received a delicious bath from his mistress... he was now warm and cozy, physically, though of course he was unable to move. He would've been able to doze off, even, except for what was happening to his groin area... Miss Helen, in her declining years, had been unable to tease Gerry more than once every two weeks, leaving him caged the rest of the time... but Keri had incredible energy, and put him through the paces, it seemed, daily.

"Jesus, Gerald... look at that vein. Close to bursting, I would think" Keri traced a cherry-red nail along the sensitive underside of Gerry's straining cock, very slowly. She'd already jacked him once to where the semen was hitting the urethra, before pulling away her soft fingers... that was ten minutes ago, and she had to be careful now. Very slowly, or else there would be an unauthorized squirtee... and her bullwhip was being restrung right now. Keri lightly rubbed the vein once more, before circling the head of Gerry's cock with her fingers and palm, and massaging, just the head... "Oh, Miss Keri... " Gerry mumbled. "I can't take it... can't you let me cum for honest effort? No one else wanted me to suck them... all the guys laughed at me... one told me I needed (a-choo) a shave!"

Keri began giggling at this... "Oh, God... you do have way too much testosterone for a transvestite... but of course you're not interested in transvestism, Gerald... nor sucking cocks... all for me! Coming in (giggle) lip gloss smeared, stockings torn... with sixty-seven DOLLARS... " Keri was only about a hundred ten pounds, and as she doubled over, thinking of her poor involuntary transvestite, it looked dangerously as if she might fall off the bed. She righted herself, breasts heaving, and squirted some lubricant on her forefinger, tracing it all over Gerry's cock until it glistened. "Looks almost like a missile, baby... " "Please, Miss Keri! I've been so good... and my cock is about to burst! Won't you... what are you doing with the Reynolds Wrap?"

Keri was cutting off a sheet of aluminum foil. Where had she had the box on the bed? Didn't Gerry ever see anything? She began wrapping the foil loosely around Gerry's cock, fitting it down to just above the testicles, so it looked somewhat like the Washington Monument. "What is this? Miss Keri, I'm not going in the oven, am I?" Keri shook her head, giggling, and bent over the head of the tented shaft. She put her mouth around the tip of the foil and began humming... "Hmmm-mmmm-" Gerry's cock felt like it was vibrating... and growing warm. Keri breathed heavily on the foil some more " MMM-MM". The heated vibrations of the foil were tickling Gerry's undershaft. The tickle was driving him crazy! The semen of nearly eleven months was rising to the top, but it didn't seem like there was quite enough friction... almost, but not quite. Gerry began arching his back, attempting to force the foil into Keri's mouth. Closing his eyes, he strained against the ropes... Suddenly he felt anguish. His penis was ripping. Opning his eyes, Gerry saw Keri had taken her mouth off the foil tip, and had grabbed the middle of the shaft with her hand, grasping the foil tightly. Searing pain invaded Gerry's tender skin, as the sharp edges of the foil rubbed the sides of his dick. "Okay, Gerald, you want me to wank you off... here goes!" Keri began pulling the foil viciously up and down the shaft, in a horrific handjob... "This is what you want, this is what you get... " Gerry tried to stand it, he knew he had to empty his balls. If he could just cum! He didn't need to enjoy it, but he had to release..

So sick of waking up in the middle of the night with a boner rubbing the sides of the cage... because he had been having a wet dream about his paralegal, a wet dream which never came off, because he couldn't get a full erection with that goddamn cage on... Could he come now? "No, no more!" Gerry screamed. His cock was being massacred by the sharp foil. "What's wrong Gerald?" Keri asked through her teeth, slamming the foil from glans to balls, again and again "Not enjoying this? I thought you---"AAAUGH!" Gerry was now going limp, thank God. His penis felt like it had been chopped up in a Ginsu commercial... .finally, Keri stopped. Taking off the foil, Keri surveyed the blisters, some of them purple-ish, that covered the glans cockhead and balls. "Honey, I was going to give you a free cum... but you don't want one... so sad.." She left the bed and went to the bathroom, bringing back some iodine and a jar. Gerry looked at the label "Ben Gay". He fainted.

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Thirty days later, Gerry's dick was healed, but relieved, and he had come back with only 33 dollars, and a bleeding rectum from a gang-rape. Spreadeagled again and Keri working on Gerry's cock. She grasped the base of his shaft and rubbed the small base of skin between the head and the shaft, delicately between her thumb and index finger. After about 20 minutes of this, still grasping the shaft with her left hand, Keri took the fingers of her other hand and formed a ring with her thumb and index finger, twisting it around the shaft just where it joined the glans, occasionally bringing the finger-ring up and down the top of his throbbing organ." Ma'am, you're killing me... " Gerry mumbled "The semen is pulsating at the tip " Keri chortled, then placed her fingertips over Gerry's cockhead like a closed umbrella and gently squeezed them up and off the tip."Just calm down, Gerald. You're doing fine... and isn't this more fun than coming in ten seconds anyhow?" Keri's thumbs went up to the head's slit and rubbed alternating thumbs up and down the slit..

Gerry felt himself getting close. Keri would do untold tortures to his cock if he came without permission -- the last time, she'd whipped it with a car radio ariel -- so he spoke up. "Miss Keri, I am about to come... permission?" Gerry was arching his hips up, trying to push his penis into Keri's soft, wandering hands with their long red nails. Keri stopped her ministrations immediately, primly folding her hands in her lap.

"Aaagh" Gerry closed his eyes and fell back on the bed again. His cock and balls felt leaden, and his urethra was hurting at this point. It had been nearly a year. Eleven months ago, Keri had gotten a hairy gay construction worker to jerk Gerry to the point of orgasm, and then made Gerry finish the job with his left hand, cumming all over the guys steel-tipped work shoes... and then Gerry'd had to lick it off, and then use his mouth up at the crotch for "compensation"

After watching Gerry hump air for a while, Keri emptied a vase of roses on his crotch. The thorns burned, but the cold water from the bottom of the vase eliminated some of the erection. Then Keri picked the roses up by the blossom side and lashed Gerry's cock with the thorns until it was quite small. "Thanks again for sending these to me yesterday" Keri said, as she locked on the cock cage and then untied him "... Never thought a dozen cut roses could be so utilitarian. Now change these wet bedsheets!"

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One night Keri told Gerry that they were going to have a nice night out... it'd been a long time since Gerry had been allowed to cum "And tonight, Gerald, I'm going to let you go out without the cage... .You've been doing so well, I want it to be more of a date for us, you know?" She looked really stunning in one of those super tight t-shirts and a miniskirt that was made of the kind of material that was made for the blue bandannas that Gerry wore in high school. God, it was short. She looked good in anything, yesterdays she'd come to the office in a tight pink top, and a white skirt with heels, and spent half an hour crushing his cock with them while the secretary and paralegal took their lunch hour... he'd looked rather ridiculous lying on the floor of the ornate office with all the diplomas and awards... naked in the shag rug with his penis jutting to the side and Keri getting on and off it with her heel... and then she began kicking the penis like it was a Soccer ball... ooh... but then the cage went back on. There'd been no teasing that night, as Keri had had a date with some guy she'd met at the pool... but tonight she'd promised something great... a night out without the cage! A date night, in fact...

They'd walked through Old Town, Alexandria and bought ice cream, watching the other milling couples. Keri had taken the hopeful Gerry to a secluded bench sheltered by lush trees and bushes and they'd sat down together. "Miss Keri, thank you for holding hands with me." Gerry was so thrilled. She was so beautiful, and her cleavage was practically falling out of the little t-shirt. Keri kissed him lightly on the mouth, and as she licked her sherbert, she dropped her red talons to the crotch of his khakis, and scratched the crotch lightly. Gerry had immediately bulged up, and how free he felt! There were no evil steel chastity cage bars rubbing his shaft raw tonight! As if reading his thoughts, Keri finished her sherbert and unzipped his pants, pulling Gerry's penis out, manipulating it in traditional torture... five quick strokes, ten slow ones. "Toss the Oreo cone away, you're too fat for the second scoop anyway, Gerald. Sit on your hands, so you don't try to take over from me, baby... you know what I do when you try to touch yourself. Don't pout, baby... Look at the big wee-wee! You're trembling, honey. You like it when I scratch the head with my long red nail... it's been a while since you squirted, huh? Maybe I've been too hard on you... you want a little tonight?" v She'd whispered in his ear,making him think of the lyrics from "Bette Davis Eyes"... But then there was a rustle in the bushes, and she'd dropped the now pre-cum sodden penis, and put her hands in her lap primly, and Gerry'd had to stuff his cock back in, seriously singing it on the zipper...

Keri'd whispered in Gerry's ear lightly, making think of the lyrics from "Bette Davis Eyes" ... But then there was a rustle in the bushes and she'd dropped the now pre-cum sodden penis, and folded her hands primly. Gerry'd had to stuff his stiff cock back in, impossible to bend it in the blood engorged state it was in... Ooh... "What's wrong, baby... oh you singed it on the zipper... get it in there, hon, you don't want to get disbarred for indecent exposure."

At the multiplex, they'd bought tickets to the kind of chick flick that Gerry couldn't stand, but Keri had spent the entire movie absently stroking his cock, once again out of the pants but under the sweater she'd brought... He'd gone to the edge five times, Keri kept pulling her hand away to have some popcorn, and then back to the stroke... After they were back outside, his crotch bulging against the too-tight khakis, she'd timidly mentioned that she was running out of shoes, 70 pairs wasn't enough... so they'd gone to a Hecht's and he'd spent three hundred dollars, and she'd played the spike heels across his boner as he'd put them on her... no salespeople needed here!

"Please let's go home, Miss Keri," he'd begged, tonight seemed like it might be Lucky Night, really it did... "Can we go to the Candy Store first?" Keri asked him petulantly. "It's this new fetish place in Chevy Chase." Gerry sped her there, though he was seriously hoping that playing with his big dick had aroused Keri to do something a little more traditional, just for tonight. "Hey there... " Keri flirted with the guy behind the counter. "I know you know where the big canes are, don't you?" Big canes... Gerry's stomach turned. "Don't worry, sweetheart" Keri touched his chin with her forefinger. "I just want to get something for your regular discipline. You've been a good boy today... won't you help Keri." She pouted "Find something here... then we'll go home for the good time?" Keri selected a malacca cane, a South African police baton and two bamboo canes. "Can we try these out?" The sales man looked startled.

"What do you mean?" Keri smiled, dimpling for him. "Well, I was wondering if you had a back room, so I could see how good these are, certainly if I get a little blood on them, I'll pay for those, but I don't want to get something I don't need... " Gerry was quaking now... "Just for you, baby." Keri whispered "Be a good boy and just let me test these... I'm not mad at you." She whispered more in his ear, and casually dropped her wrist across his crotch again. "Come with us, please." The salesman looked startled, but he really liked Keri, and agreed to lock up the store for a few minutes.

In the back room, Keri looked at Gerry "Gerald, take down your pants, please." Her tone was cold now, no more flirting. Miserably, Gerry dropped his pants... he was wearing no underwear, which of course had made all the evening's manual stimulation so great. Why was she mad? "I'm not mad, Gerald" Keri read his thoughts. "I just need to test this stuff for your discipline around the house. " The sales man sniggered. He was about twenty-four, Keri's age, and they looked at each other and giggled. Gerry stood there, his shirt tails not quite covering the tip of his erection. But maybe the kid wasn't noticing that he was so hard. Keri took care of this problem by tying his shirt above the waist. " Bend over that box of dental dams, dearest."

Gerry bent over, and Keri lifted the Malacca cane. "Be a brave boy, Gerald." WHACK! The first swipe nearly ripped the skin off Gerry's asscheek. Malacca was a much thicker wood than the bamboo canes that Gerry was used to. WHACK! WHACK! WHACK! Inadvertently, Gerry grabbed his asscheeks. "Oh Jesus. Do you have handcuffs?" Keri smiled at the clerk, who was alternately looking at Gerry's welted butt scornfully and back to Keri's 36 DD cleavage. He ran back into the store, and brought back police handcuffs. "They sell them now, isn't that wild?" he said. Keri chuckled, and cuffed Gerry's hands behind his back, his naked butt still wobbling over the box "Miss Keri, please. I thought this was our special night." Gerry sniveled. This was awful.

"Isn't he a drag?" Keri looked at the clerk for sympathy. "Jesus, what a loser. He lets you hit him like that?" the sales guy laughed. He had a goatee like Gerry wore in college, before Miss Helen, Keri's predecessor had shaved him clean. "I mean, you are totally hot, but... " "I know, what's your name?" "Mike" "Mike, my arm is sore. Why don't you take over with the South African police baton?" Mike looked alarmed. "Look, I don't want to be prosecuted for like, assault -- " Keri grabbed the kid in her arms and gave him a deep, full, kiss. "Do this for me... Creepo thinks I'm going to take him home and blow him, I think... give it to him a few times, and then we'll take him home after you get off, and I'll teach you to make him dance." Keri leaned into Mike's ear "And then we'll... " Mike grinned, and moved over, lifting the baton over Gerry's bare ass.

Forty-five minutes later, Gerry stood in his ornate living room, naked, with the cuffs still on. Mike was sitting on the couch, watching as Keri ran her fingers over Gerry's penis.. "Look how hard he gets... you really thought I was going to give you something good, didn't you baby... " Gerry was rock hard, and leaking... "Ooh. My hand is wet now... " Keri looked at Mike "Give him a few with the bamboo I bought." Mike looked at Gerry steadily. "Get back from the sofa, freak." Gerry backed up a bit apprehensively. Mike came forth with the bamboo... and began beating Gerry's penis with it... WHACK! WHACK! WHACK! Finally Gerry was lying on the floor, and his penis was shriveled once again.

"Get up honey." Keri was sweet again, and helped Gerry up. "Let me look at that poor thing." She began massaging Gerry's tired, beaten, sore, cock." "Now don't get erect, I'm just trying to fix you up... when you're hard, Mike gets irritable. " She winked at Mike "Damn right!" Gerry was trying not to get hard. At first it was easy enough, but as Keri massaged him, now using some Lubriderm, he forgot himself, and suddenly it was like a missile under her wandering fingers... " "Mike! He's at it again!" Back from the sofa asshole!" Mike moved forth with the cane... Gerry sighed. It would be a long night...

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"Hey, Keri!" Keri looked up from her magazine. Sabrina had just propped herself down in the next beach recliner. "How you been doing, girl?" Sabrina giggled. Five or six years younger than Keri, Sabrina was a lot of fun, and the two were often inseperable. Small, blonde and curvy, Sabrina had met Keri at a tease denial party, and recognized her from their mutual membership at the Mount Vernon pool. "Sabrina! What are you up to? Is that Cecil?" A tall handsome thirty-five year old man, slightly balding came out of the locker room, and waved at the girls. In his navy blazer and khakis and loafers with no socks, he had Groton written all over him. "Bye, baby!" shouted Sabrina. "See you tonight!"

Sabrina was much more exuberant than Keri, and Keri enjoyed having her own quiet nature livened a little, and of course, this was a girlfriend she could speak frankly with. "Ceec looks like he's moving kind of stiffly there, is he chafed, or did he hurt himself?"

Sabrina giggled, and her breasts heaved in her pink bikini. "No, yesterday Cecil had the day off, he's made a big sale, and he took me around four o'clock to have my nails done the way he likes." She flashed her French cut talons at Keri. "Then we went back to his place and I tied him to the bed naked and stripped to my blue bra and panties, and removed his CB-200 chastity belt... and I teased him for seven hours with my new little scrapers here." Sabrina fluttered her nails again, giggling. "Seven HOURS?" Keri asked. "But didn't your hands get tired?"

"Well, we took breaks." Sabrina replied, thumbing her nose playfully at a handsome Peruvian lifeguard. From four to six-thirty, I played, and then I left him to go watch an exercise video for half an hour, then played again til eight, when I locked his crotch up, and he took me to dinner... opening the door to his Miata convertible to let me out... And no Red Lobster, either. He took me to Café Milano." She named the most expensive restaurant in Georgetown. "During dinner he was real earnest, you know, holding my hand and all that good shit, staring in my eyes and telling me how much I meant to him." The two began to giggle again. "Then he took me to Georgetown Jewelers and bought me a nice pendant, and we went back home, and I stripped him, tied him, and played til midnight... and then locked him up again, and drove off to meet Paco." Sabrina and Keri looked at the lifeguard, now flirting with a girl barely seventeen. "He is such a whore, idn't he?" Sabrina's North Carolina tones flared. "Jesus, Pak's probably fucked six women sitting here TODAY. But last night I sucked his cock like there was no tomorrow, and then met Cecil for breakfast... and he drove me here."

"Jesus, Sabrina." Keri marveled. "You've been up all night, and you're not even tired." Sabrina laughed. "Well, I have a pitiful, chaste loser keepin' me in my own place, and giving me a nice allowance, and then I keyhold and tease four other pitifuls... Remember, it's not Cecil who pays the fee at Mount Vernon. He doesn't have the green your Gerry's got." Keri chuckled. "Gerry finally had a squirtee on Wednesday" "No kidding?" Sabrina smiled "Your icy heart finally melted, huh?" "Well, I'd been feather-teasing Gerry as he was hanging from the eye hook in my Florida room, and then LeBaron Williams, the bike courier I'm seeing dropped by with his brother Crawford, who has just been released from Jessup and hit they all three of my holes." Sabrina choked and spat some of her Bloody Mary on her "Self" magazine. "Right there in front of Gerry, too." Keri finished. "Hanging naked from the ceiling, with his pitiful boner twisting in the wind. Gerry began crying, and LeBaron made fun of him... but then Crawford complained about the noise, so I said "Well, why don't you hit him with your belt to shut him the fuck up?"

"Jesus, Keri." Sabrina leaned on the recliner. She was less oriented towards S&M than Keri was, and felt that an eternal tease was punishment enough. "Well, it didn't help, anyway, he kept weeping and kicking his legs in the air, and the three of us took turns with the belt on him til poor Gerald was really marked up -- Crawford pumped some IRON while he was inside... " Keri reflected. "Then I took him into the living room and threaded a cord through his pierced nipples, and tied the ends just a little above chest level across the doorway, so Gerry would have to get up on tiptoe to keep his nipples from tearing, and the Williams brothers and I went bowling and then to their house to ... when I got back, Gerry was in a state from relaxing on his heels and having his nipples strain, and then getting up on his painful heels for relief from the nipples... and I finally said "What the hell, Gerald. It's been sixteen months." And so I unhooked him and took off his cage and let him go at it while I flashed my tits at him... "Keri laughed. "Do I deserve sainthood?"

"You are just so unselfish." Sabrina said solemnly. "Just let that poor man support you in the style most of us would kill for, but that's not enough... you have your OWN Miata... and ... how should he expect more than one or two squirtees a year, what, he's tryin' to bribe you?"

The waiter, coming up with Keri's V.O. was unsure how to handle it, as his customer was so mirthful... Would she take the drink "Ma'am?" Keri looked up and smiled. "Hey cutie your names Brandon, right?... "she took the drink and paid for it. "Want to come over tonight?" Startled, the guy assented... the girl was so hot... "Sure, I'll take you to dinner... " "No, I'll take YOU... and then back to my place..we'll be alone, sort of... ." And Sabrina and Keri's giggles began anew...

The End

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