Cherry Pop
As a man, he had always been helplessly horny. As a woman his torment
was greatly relieved through distraction by his concern for the pleasure of
others. In the terrible days before he found his Mistress, before he was made
by her into the beautiful and seductive woman he would become, his cock was
almost constantly hard and almost never satisfied. He watched pornography
endlessly and masturbated several times a day, watching more and more disgusting
porn in an effort to find the satisfaction that eluded him. He had no trouble
finding beautiful, young girlfriends and always had more than one at once. He
needed sex awfully and even though he screwed his many girlfriends constantly he
found no relief. Often, he could not even loose his erection when he needed to
piss.
The only thing that seemed to calm him down was when he paid a
dominatrix to whip him and call him names. This made him loose his erection.
Then she would try to make him get hard so that he could cum during the session,
but he could not. She would laugh at him even more for this, wasting all his
money and not even being able to get hard. After these sessions he would feel
relaxed and be able to think about other things besides sex for days at a time.
It was on one of these visits with his dominatrix that she introduced
him to her friend Mistress Zoe. While he was blindfolded, unable to get hard
even though he had been hard all week, he heard two female voices laughing at
him instead of just one.
"Look how small his cock is!" said the new voice, "It looks like a
little boy's cock."
"I know," said his dominatrix. He goes around with all his little
girlfriends, acting like such a player, but he goes soft at the mildest
challenge to his ego."
He felt her unfamiliar hands run over his shoulders and down his stomach
to grasp his soft dick firmly. Even when she spit on it and then stroked him
with wet and slippery hands, he just shriveled up further. Then he felt a wet
finger rub at his asshole. He had tried penetrating his anus with dildos and
other toys when he looked at porn, but he could never get much inside. It was
so tight, only his fingertip would enter. But now the strange woman was sliding
her index finger smoothly into his asshole. It felt awkwardly uncomfortable.
She took off his blindfold and he looked at her. She was wearing jeans and a
tight black T-shirt. Her breasts were large and she wore no bra. Her hair,
reddish brown, fell around her face as she looked into his eyes steadily and
said. "Your cock is hard."
She abruptly withdrew her finger and the two of them walked into the
next room talking in soft voices. When they returned his dominatrix told him
that she was moving out of the area and wouldn't be able to see him any more,
but that Mistress Zoe would accept him not as a paying client, but as a personal
domestic servant. This would be for a trial period of four weeks, after which
he would sign a contract and become her property if he desired to stay. They
told him to think it over, if he was interested he should meet her in one week
at a restaurant he knew of, with one suitcase of only his belongings.
This was something he had never considered before. He wanted to know
more about Mistress Zoe, but he wasn't sure he could live as a submissive all
the time. His cock was still hard that afternoon after her stimulation of his
ass, and he called his latest girlfriend for a date that night. Sarah was the
last girl he had as a man, before Zoe changed him. She was 22, pretty and
blonde, with long skinny legs and pert little breasts. That night he fucked her
furiously, and she came and came on his cock as he worked at her, trying to cum
and to be satisfied. She wrapped her arms around him, telling him what a great
lover he was, being able to stay hard so long. She tried to suck him off, but
she couldn't make him climax. She even put him in her ass and moaned and came
again as he screwed her tiny asshole. "I don't know what's wrong." He finally
said. "Maybe you don't really like me." She replied.
His usual recourses weren't working. He couldn't cum watching porn and
jerking off, and he couldn't cum during sex. He called another professional
dominatrix who did his preferred routine of whipping and humiliation. He lost
his erection, finally, and had no desire to orgasm. As soon as he left the
session he got a hard on right away and tried again to cum watching porn and
putting a finger in his ass that night. By rubbing his anus quickly in and out
with his finger until it was raw and red, he finally was able to cum. His cock
was hard again half an hour later. It was time to pack his suitcase, he knew.
Mistress Zoe was waiting at the restaurant bar when he arrived, sipping
a glass of scotch. She ordered him a Shirley Temple and the bartender looked at
him, amused. "A fitting drink for a little lady," he smirked. There were five
cherries in the bottom of the glass.
He was thirsty and drank it all, leaving the cherries. Then Mistresses'
hand was on his leg, resting lightly on his hard cock head. "You're pathetic."
She said. "Follow me." She picked up his glass with the cherries inside and
strutted on loud boot heals to the ladies room. She held the stall door open
for him and entered behind him, locking it.
"Take off your pants."
When they were removed she pulled some pink stretch lace panties out of
her pocket and helped him put them on. His hard cock pushed hard against the
lace. "Pull your panties down over your bottom, but leave them up over your
cock, and bend over," she ordered.
He obeyed and soon felt the wet finger in his bottom again. He moaned.
Then he felt the cool, soft fruit being pushed inside him. The first one went
in deep. She was stuffing them in one by one. The last she didn't put it all
the way in, just left it stuck in the opening so that it was held tight by his
sphincter. She pulled up the panties and abruptly opened the door. He hurried
to put his pants on and to follow her as she strode out of the restroom and
towards her car. The fruit squished in his butt as he rushed after her.
She said nothing on the drive to her place. His cock was still hard and
tight inside the panties, and his anus was wet and a bit irritated from the
acidity of the fruit. Had his asshole pinched the last cherry in two? It felt
so mushy and strange.
At her apartment she immediately made him strip down to his panties and
stand in the center of the room. Mistress' hands caressed his cock and ass
through the panties. He felt her push on the mushy bits of fruit caught in his
anus. "you've left a red stain on your panties." She told him. Did you get
your period?."
"What?"
"Did you get your period little girl?"
"Um, no."
Mistress yanked down the panties roughly, snapping his cock
uncomfortably as they came down around his knees. "Spread your legs, baby."
Mistress Zoe pulled his ass cheeks apart to inspect him. She pushed at his red,
drippy anus. "Do you like having objects put into your asshole?"
"Um, yeah. I guess so."
"Tell me that you want to have your asshole stuffed full."
He told her. Then she was leading him roughly by the arm into the
bathroom. Mistress Zoe told him that before he had anything else in his asshole
he would have to make some room for it. Then, on his hands and knees on the
floor with his rear end in the air and his panties pulled down over his thighs,
she told him to "push the cherries out of his bottom."
He tried, and managed to get his asshole to flex a little. "Come on,"
Zoe coaxed sweetly, "Come on baby, just push it out of your behind like you're
pooping."
Pushing harder, he felt a piece of something roll down his thigh and
fall into the panties. "That's it" She crooned "Poop it all out honey." He
pushed harder and felt more of the sticky, crumbled fruit fall out onto the
floor. The juice dripped down onto his balls. She was rubbing his cock now,
her touch gentle and seductive. "That's a good boy. Keep pushing, you're doing
great." Closing his eyes he was lost in the stimulation on his cock head as she
encircled the tip of his penis with her spit covered palm. He opened his eyes
and looked down on the floor. There were a few bits of brown shit on the floor
and inside the panties. His cock began to go limp in her hand.
"Oh baby!" Mistress said as if she were talking to a little child. "Did
you have an accident? Do you need to go to the bathroom honey?"
"I'm sorry Ma'am. I didn't know-"
"Honey." She interrupted firmly. "If you have to go to the bathroom you
need to tell me."
"I'm sorry."
"Get on the potty baby."
He did, with his panties around his ankles.
"Now you can finish going to the bathroom." Rubbing his shoulders she
continued, "Come on. I know you have to go."
After a few minutes of her embarrassing encouragement to finish while he
strained and pushed, she began to get irritated at him. "Okay baby, I'm getting
tired of waiting for you. You'll have to learn to do what I tell you in the
future, Okay hon?" He nodded. "Until you learn how to go to the bathroom when
you're told, I'll have to help you." She held his hand and lead him over to the
wall, wrapping his fingers over the towel rack. "Sweet heart? I want you to
hold still while I help you go to the potty. Can you hold still? Or do I need
to help you hold still?"
"I can hold still."
"Alright, but if you can't hold still by yourself I'll have to help
you."
He heard the water running behind him as she filled up a red two-quart
enema bag. It was hung on the rack next to his hands. He felt her finger
suddenly in his anus. "I'm just going to use some Vaseline on your butthole,
honey, so this won't be so uncomfortable." A few smears of thick, cold Vaseline
were pushed into his ass. Then something big and hard pressed against his anus.
One hand left the towel rack involuntarily to defend himself against it. "I
don't know-"
"What don't you know sweet heart?" Mistress asked, rubbing his slick
asshole and poking her fingertip into it.
"I don't know if I can do this."
"You don't have to, honey, you can leave right now." Her finger was
suddenly all the way in his ass again.
"Do I get to decide what I do or don't do, if I stay?"
"No honey. If you're here it's because you understand that I know
what's best for you. Honestly honey, it looks to me like you're in need of my
help." The finger in his anus was sliding in and out, pausing to rub his
prostate gently. His cock had become hard and the tip was touching the cool
bathroom tile wall.
He was quiet for a moment and then said quietly, "I'll stay."
"If you don't enjoy living at my house baby, I don't want you here
acting all mopey and babyish."
"I'll stay, thank you so much Miss." He said and tried to smile down at
her while she poked her finger in and out of his butt and his cock positively
ached.
She withdrew her finger and got some handcuffs out of the drawer by the
sink, attaching both his wrists to the bar in front of him. She also attached
each of his ankles to a buckled cuff at either end of a long metal bar. She
slapped the inside of his calves to get him to move his legs further apart to
buckle him in. His feet were so far apart that he was lowered much closer to
the ground. He gripped the towel rack for balance. The thick, cold nozzle
pushed again at his asshole.
"Come on baby, loosen up." She said, slapping his bottom gently. She
worked the nozzle into him firmly. It was shaped like a buttplug and his ass
closed painfully around the narrow part. She released the water into him
immediately and it felt warm and quite sensual as it flowed into his rectum. As
more and more water filled him, it became very heavy and his ass felt full of a
heavy, sloshing pressure. Then a strong cramp hit him and he felt almost sick.
The water had not stopped yet. He looked at the bottle next to him as it emptied
and his ass twitched and cramped. As soon as it was empty, she started pulling
the nozzle out.
"What are you doing!"
She stood up and looked at him from above. "I'm helping you go to the
bathroom since you were having a problem pooping." He gasped as more cramps hit
him and he tried to hold his ass closed around the slippery nozzle and squirmed
against the restraints.
Mistress Zoe went back to her task of pulling the nozzle out. It popped
out suddenly leaving a trickle of water behind it. He clenched his cheeks
quickly as she slapped his ass hard. "Don't be a baby. You'll have to learn
not to have these accidents!" she scolded. His cock softened again. Sweat was
running down his sides and his belly was sticking out. She fished a small
buttplug out of the drawer and pushed it quickly into his ass. It was a little
bigger than the nozzle, not very big at all, but it was still the largest thing
he'd felt in his hole. He was temporarily distracted from the cramps in his
belly by the pain in his anus itself.
"There now honey. Pinch your ass closed around that buttplug. It will
help prevent you from having accidents." She pulled the pink panties up again.
They were still dirty with little bits of the cherry and the shit from his
earlier accident, moist and crumbly against his balls in the lacy crotch of the
panties. His cock was getting hard inside the panties as he clenched his sore
anus over and over again on the plug, trying to keep it from slipping out.
"Miss, Miss, I need to use the toilet, please..." he begged softly.
"Nonsense. To work properly an enema must remain in place for at least
fifteen minutes. That's the minimum."
"Ma'am, Please, I'm afraid I can't hold it. I have to go. Please."
She got a large ball gag out of the drawer and wrestled it quickly into
his mouth and strapped it behind his head.
"Enough of this. I'm going to get a glass of wine. I'll be back in
twenty minutes."
He squirmed and twitched while he waited. Looking down, he could see
his cock bulging in the tight panties below his round belly. Waves of cramps
wracked his body.
Twenty minutes later, Mistress returned in a silk kimono-style robe,
glass of wine in hand. He stood still, trying not to displease her so she would
help him.
"Honey. Are you ready to go poop now?"
He just nodded.
She unlocked his ankles and wrists, but cuffed his wrists together once
they were off the rack. The gag was left in as she pulled down his panties and
sat him down on the toilet.
"Oh honey. Look, your cock is so hard. You do like it when I put
things in your ass, don't you?" She reached into the jar of Vaseline again and
pulled out a large dollop and deposited it on his cock head.
"There you go honey. That will help you. Now, get to work rubbing your
pee pee. He gratefully covered his cock in the jelly and began jerking off.
Another hard cramp hit him and he gasped and tried to grip the plug with his
anus again. Mistress Zoe grabbed his hand and moved it over his cock and
commanded him to continue. He doubled over in pain while he kept rubbing. The
cramp passed and he felt ready to come. She reached under him and popped out
the plug and dirty water ran out of his ass.
"Now. Time for your cum sweetheart." She said sternly, like a mother.
"Have a little cum for me." The orgasm came over him and his ass spasmed,
releasing the dirty enema in loud spurts while his cock shot cum. His ass felt
disgusting and sensual. She did not allow him privacy but stood there,
supervising his orgasm.
When he was done she had him clean up the little bits of fruit and shit
that he left on the floor earlier during his "accident," wash his panties in the
sink to get the stains out, and then finally he was allowed to get into the
shower to wash off. She handed him a razor and a hand mirror and told him to
get all the hair below his neck off of his body.
An hour later he had managed the task with only a few cuts. She brought
him some flannel Pajamas with pink hearts on them. The cloth was so soft
against his smooth skin. His pink slipper-covered feet padded behind her
clicking high heal mules as she walked him down the hall to his room. A four
poster bed with a white lace canopy was on one side of the room. A small
dressing table with a round vanity mirror was in the opposite corner, and a soft
chair was in another corner. The comfort of the feminine room was in stark
contrast to his earlier agony, and he crawled under the fluffy pink covers
happily. Mistress pulled open the drawer on the nightstand and took out wrist
cuffs and ankle cuffs, softly padded, with a matching pink blindfold. She put
on the blindfold and gave him sips of water before locking his hands to one of
the top corner posts, and his feet to one of the bottom ones. He felt sleepy.
Zoe stroked his hair and said, "As long as you live here, your name will
be Nicole." He nestled down into the bed. Mistress then lowered the blankets
and gently pulled down the waistband of the pajamas. Nicole's cock was
semi-hard. Turning him on his side, Mistress parted Nicole's asscheeks and
exposed the smooth, tight hole. She opened a tube of lubricant and with her
finger, wiping it over his anus.
"So you don't have any more accidents in bed." She said, inserting
another buttplug into Nicole's bottom.
This one had a small comfortable "neck," but two rather large round
balls that sat on the inside and the outside of his body, plugging the hole
tightly and eliminating any danger that it would slip either in or out during
the night. Nicole knew better than to protest. Mistress Zoe gave him one
lingering soft kiss on the lips as she turned out the light, leaving him to
squirm in bed trying unsuccessfully to rub his cock to orgasm against the pink
satin sheets.
