Author: Zoe

Summary: A desperate man finds what he doesn't even know he needs: a Mistress to guide his initial sissification and anal training.

Part 1

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.

Part 2 Girlfriends Forever

Nicole woke the next morning to the sound of rustling in one corner of his room. Light filtered in from the edges of the blindfold and he stretched uncomfortably, his arms and legs tethered to opposite ends of the four-poster bed. He heard Mistress Zoe's voice saying. "Yes, those will be fine, just hang them in the closet." Sets of clicking high-heal shoes walked up and down the hallway while his Mistress gave directions. Then the voices were gone. Where was Mz. Zoe? His bladder felt full and he needed to be let up to use the bathroom.

Then she was sitting on the bed, her cool voice murmuring into his cheek. "You were one tired little baby! How's my sleepy baby this morning?" The covers were pulled down revealing his plugged bottom still exposed by the pajama bottoms left down around his knees last night. His hard penis was still pressed against the satin sheets. "Just as I left you, hard as a rock. You're far too excitable. Look how big your clitty is, Nicole. It's not very ladylike." The blindfold was swept off gently. Nicole squinted in the bright morning light, to see Mz. Zoe sitting in bed beside him, dressed in a simple but form-fitting black sleeveless dress. She pulled a necklace out from between her breasts. Several keys were on it, and she turned and used one of them to unlock Nicole's ankles. Nicole admired his Mistress' curvaceous but small-waisted figure from behind as she bent forward to unlock him. Turning the opposite way she unlocked his wrists while her breasts brushed his face through the cloth of her dress. He felt her large, hard nipples pressing against his skin.

His wrists were only unlocked for a moment before she had them locked together again behind his back. "Do you need to pee honey?" she asked in a low, kind voice. He nodded. "Ok, up we go!" She helped him up out of bed and walked him down to the bathroom, his PJ's still around his knees, his cock still hard, and the ball-shaped end of the buttplug still wagging between his cheeks as he waddled behind.

In the bathroom, Mz. Zoe pushed him down on the toilet, reminding him that "Ladies don't pee standing up!" and she stood there rubbing his shoulders and told him to "start pissing honey." His dick was hard and though his bladder hurt nothing could get through. He could feel the large, round ball end of the buttplug inside his ass pressing against his cock inside his body. It made him feel like shitting, but the pressure was also very sensual and arousing. He tried to relax and get his mind off it, but he had enough trouble loosing his hard-on to piss without that thing in his butt.

"Honey!" Zoe said, "I can't wait here all day. You must either get this over with now, or wait till I come home at lunch." Nicole pushed again, but was still to hard to let any pee out. "Nicole, now, I want you to be honest with me, are you having trouble pissing because you enjoy the buttplug filling your rectum?" Nicole just nodded silently.

"We can't have this. You'll have another accident before lunch if you don't go now! Stand up." She was pulling a plastic ruler out of the drawer. Mz. Zoe held her hand around his throat firmly to keep him from bending over to protect himself, and took the ruler to his sensitive pink cock-head. She whacked his cock as if she was swatting a fly or other noxious pest. Tears sprang to Nicole's eyes immediately. His penis stung and shriveled. Even after it was small, Mistress kept slapping it until she had given twenty even strokes.

He was prepared to sit down and begin pissing, but she stopped him. Fishing in the drawer again, she pulled out a little leather pouch attached to some black straps. It was about 2 inches deep and not very wide. It was a very tight fit but Zoe took his cock in her hands and pressed him firmly, stuffing him inside. At the tip was a little round opening and she made sure his urethra was aligned with it. A thin leather strap extended from the tip of the pouch, near the opening. The other straps wrapped around his hips and had metal clasps that clicked into place in the back of the harness. Zoe pushed him back down on the toilet, holding the pouch with the strap wrapped in her hand, so it didn't fall in the bowl. "I will have to hold you when you pee now, so that you wont let your strap fall in the potty." She informed him. "Now, start peeing honey."

After a few moments of hesitation, he could finally relieve his sore bladder. She pulled and milked the pouch with her hand while he did it, and his cock strained to become hard, but could not in the very tight container it was given. "You defecated last night, so you won't need to go again until later. You will, for sanitary reasons, need your plug changed for the day."

Nicole was ordered to bend over and rest his chest on the counter next to the sink. His hands were still locked behind his back, so his skin rested directly on the tile, cold against his nipples. "Now honey, push the ball out of your bottom!" Zoe said cheerfully.

He pushed, but it was much bigger than the cherries that had been in last night. The ball on the inside of the plug was just as large as the ball on the outside, about two and a half inches in diameter. "Nicole! Don't be a baby. I don't want to have to do everything for you. It is very important in your training that you be able to manipulate all the muscles of your anus. Therefore, when I tell you to hold your bottom closed, I expect you to be able to do that, and when I tell you open your anus, I expect you to do that also. When I tell you to work an object into your hole, you must learn to do that, and when I tell you to expel an object, you must be able to do that too. Now, push very hard and expel the ball from inside your rectum."

Nicole's penis hurt inside its tiny cage. He was very aroused, but his penis was confined to two inches in length. He pushed and pushed for a good five minutes while Mistress Zoe coached him, until finally the rubber object fell to the floor. She snapped on a latex glove and inserted a lubricated finger inside. "Just as I thought," Mz. Zoe concluded, "Your bottom is still clean from last night." She pushed a glob of Vaseline into Nicole with her finger, and fished out a slightly longer and thicker plug from the drawer. It was shaped like a penis, with a realistic flesh color and veins. It was about 4 inches long and an inch and a half thick. Nicole had never had anything so big in his bottom before, but that didn't stop his Mistress from pushing it all the way, gently and smoothly, but without hesitation. It had a ring on the end of it, and Mz. Zoe promptly pulled the leather strap attached to the tip of Nicole's cock-pouch through the ring, tugging his tiny penis neatly between his legs and securing the plug snugly against his anus as the strap clicked into place in the lock that rested at the base of his spine. The key-necklace jingled again as Zoe locked the harness closed.

Standing up, Nicole saw himself in the bathroom mirror. Mistress Zoe stood behind him. "See, you look more lady-like already!" She said encouragingly. His penis was invisible in the tight constraints, tucked away. His balls were pulled back as well. But fell slightly over the sides of the strap that went between them. It all felt very tight down there, his balls pressed, his cock constricted, his ass stretched to its limit and stuffed fuller than ever before.

Zoe unlocked his wrists and allowed him to dress himself in his room. The closet was full of new clothes. "The only rules for your dress day to day," she had said, "are that you must wear clothes from this closet, and you must always have the proper underwear on. You are to wear stockings, which attach to straps on your corset, which you must also wear daily. You must also become accustomed to high heal shoes and sandals. Get yourself dressed and ring the bell when you are ready to have your corset tightened for the day. Then you may put on your dress. I am going to eat breakfast."

Alone, Nicole opened the closet. He had never worn female clothing before. "This isn't my thing" he thought. I should leave at the end of this month-long commitment. I'm not one of those sissy-crossdressers." So far everything she had done had embarrassed or had been uncomfortable, but nothing was unbearably painful and he did enjoy the eroticism of her approach. He confirmed mentally that he would continue going with her plan to see what it felt like, because he could always stop if he really didn't like it.

Nicole found a white cotton corset in the underwear drawer. It looked rather like a straitjacket, only with some stretch lace across the bust. He put an arm through each strap and hooked up the front of the bodice. It was still loose, with laces flopping untied at the back. He slid one white stocking over each shaven leg, and fumbled with the snaps that attached the garters to them. Then he sorted through the drawer and realized he was supposed to put on panties first. He had to unsnap all the fasteners to put them on. They were white satin, and his constrained male parts fit smoothly inside the ladies panties, forming a female appearing mound. He tried to hurry up as he fastened some pink, high heal sandals onto his feet. Looking in the closet, all the shoes left for him had heals of at least four inches.

Briefly flipping through the dresses, he pulled a pink one out that matched the shoes. It had short sleeves and a white daisy print. It had a low back and a halter top, and was short and clingy, the type of thing you might see a teenager wearing to the beach. He didn't like the outfit, but he hoped that Mistress Zoe would approve of what he chose. Laying it out on the bed to wear after the corset was tightened, he rang the bell to let her know he was finished, but she didn't appear for a few minutes. He sat down on the bed and was instantly reminded just how long the object in his ass was. When he was standing his movements tugged at his private parts and wiggled the buttplug, but when he was sitting there seemed to be no relief from the pressure inside his panties. When he sat forward, it stretched the pouch downward and tugged uncomfortably, but when he sat up straight the plug was pushed deeper into his hole. His balls were crushed in just about any of the positions he took. He felt like they might be slipping out the side of the panties, and looked under his dress to check. There, under his skirt, appeared a surprisingly feminine sight. His silky, shaven, pale, thighs were very becoming with the satin panties nestled between them. The balls, pressed between his legs by the strap, formed two tight ridges between his legs that looked like full pussy lips stretching against the satin. The penis formed a firm pubic mound and the satin was cut full enough to contain his voluptuous pussy while slipping into a near-thong between his buttcheeks.

Mz. Zoe cleared her throat in the doorway. "Honey, are you playing with your pussy?" That's for naughty girls. You are not to touch your private parts except when directed to, in this house. Is that understood young lady?"

"Yes Mistress."

"I want to make sure you understand. Please repeat after me. I will not play with my pussy without permission."

"Mistress, I will not play with my pussy without permission," Nicole repeated.

"Good, later we will work on your voice, but for now we must work on your figure."

Mistress Zoe brought out the handcuffs again and made Nicole stand and hold his locked-up wrists high in the air as she tugged the laces of the corset tight behind him. He watched in the mirror on the vanity table as his waist became tighter and tighter, forming a classic hourglass shape.

After she had fastened the laces securely, Nicole was allowed to lower his hands in front of him. "There is one set of rules we have not discussed yet, baby" Zoe continued. In this house all ladies, including myself, must live by special rules that keep us as beautiful and feminine as possible. The clit must remain small and dainty unless under my direct orders. Mine is naturally small and pink, so I don't need a device such as yours. The pussy hole is to be wet and stuffed full and the nipples are to be pert and erect at all times. These simple rules make a girl so much more attractive and pleasing, I'm sure you'll agree. To help you comply with rule number three, I'm going to attach nipple cups to your breasts. Over time the vacuum suction inside the cups will enlarge your nipples and make them much more fitting for a lady like yourself."

Zoe directed Nicole to sit down at the vanity. "Sit up straight, display your breasts like so..." she directed, pulling his shoulders back, "and cross your legs. We have to get you in the habit so you don't go flashing your panties to the whole world!"

Nicole felt like he had a rod in his ass, and his balls were pinched painfully with his legs crossed. He tried to sit still, wincing and perching stiffly on the seat. Zoe opened a box on the vanity which contained a little gun-shaped object, with a small trigger and several little plastic cups the size of thimbles. She attached a small cup to the tip of the device, explaining that it was a pump that would provide suction to Nicole's nipples. Pushing the stretch lace panel below one breast at a time, Zoe attached the cups. Pulling the trigger on the pump three times, she soon had Nicole's tiny nipples sucked fully into the little chambers. It was painful, but not terribly so. The lace was pulled over the cups, and Nicole was helped into her dress.

"Untill your hair grows out, you're going to need a wig." Zoe opened a cabinet door up high in the closet and took out a strawberry blonde wig. It had bangs in the front and two long braids in the back. Except for flat chest and make up, Nicole was almost completely feminized once Mz. Zoe had slipped the wig on his head. Nicole was made to stand up to see his full reflection in the mirror. He felt so attracted to the girl in the mirror that his tiny penis throbbed helplessly in his panties. Two pointy nipples poked against the dress, as if it was a very cold day, and the dress clung to tight, exaggerated curves. She made him raise his arms as she tugged the dress up slowly revealing creamy thighs and then the defined pussy lips stretching against the panties. He could see the bulge of the penis straining to get hard. Zoe caressed it through the layers, saying "Oooh! Honey! Your little clitty is hard!" she let him pull his hands down to feel it, and indeed, it was firm, if only two inches long.

"My clitty is small and hard too! Do you want to see my little clit, Nicole?"

"Yes, please, Mistress!" Nicole could not believe his luck. He had never been allowed to see a Domme's naked body before.

"Well, since we're both girls I think that would be alright, don't you?" she breathed, close to his ear.

Mistress Zoe raised her dress. She wore black silk panties, which she wiggled out of. Her pussy was unshaven and she pulled the dark silky hair aside to reveal a sweet, pink clit that poked out from under its hood in a tiny erection. "Don't you want a closer look? Get down on your knees so you can see it," she giggled.

Nicole eagerly did as he was told. His penis was tingling, it was pinched so tightly. Zoe spread her pussy lips apart to show him the red opening of her vagina. "I want you to help me get ready for the day, Nicole. I need to follow the rules too and we have to help each other, right hon?"

"Yes Mistress Zoe."

Nicole was then asked to put her finger inside Mz. Zoe's vagina to see if it was wet enough. Awkwardly raising both cuffed wrists to get a finger inside the deliciously silky and warm little hole, Nicole tried to follow the instructions she was given to probe the whole vagina to see if it was wet. "Pull your finger out. Is it sticky? Or juicy?" Nicole thought it looked sticky. Moist, but not really wet. "Put it in your mouth and taste it. You must learn to identify when a woman is turned on by the taste of her pussy." It tasted a bit bitter and kind of tangy.

"Nicole, when I made your pussy wet, it was easy, I just used a little Vaseline! Now I want you to pleasure my clitoris with your mouth and help my pussy get wet too, ready sweetie?"

Nicole was happy to help. Soon Mistress Zoe's pussy was visibly wet and slippery. "Nicole, now I want you to put your tongue in my vagina to taste the difference. Can you taste it?" He could. He had never quite noticed that detail before. She was salty and sweet at the same time, there was no hint of bitterness.

"I already fulfill the third rule," Zoe continued, a breathless and girlish look in her eye, "see, my nipples are always hard because of my jewelry!" She pulled the dress all the way off and pulled each black lacy bra cup down over her breasts to show Nicole her nipples. The were quite enlarged and red, and held erect by a pin that went through each of them and rested in a small metal device which encircled the red halos around the nipple, but lifted the nipples away from the breast. "I keep mine stretched like this all the time! Men love hard, visible, nipples. You'll see!" She gushed, leaving her breasts pulled out of her bra.

"It's the second rule I need help with, Nicole. Will you go get the big vibrator in the drawer by your bed? I need my pussy filled!" She practically squealed. Nicole was surprised. Mistress Zoe was acting like some kind of school-girl. He wanted very badly to see her pussy filled, but he wanted to do it with his cock, which was in agony at this point. He tried not to agitate it with his thighs as he went over to get the vibrator.

"The black one!" she called to him. He didn't need to be told. It was obvious which one she meant. It was ten inches long and three inches thick. He hesitated, staring into the drawer.

"Nicole." Zoe snapped suddenly, her serious tone surprising him, "Come here NOW and fill my pussy. Never, never keep a girl waiting! Only men do that!" He turned and knelt again while she flopped back on the bed. "Now, fill my pussy!" she said urgently.

She reached down and pulled the lips apart and spread her legs. Pushing the tip of the toy cock against her hole, he felt tears come to his eyes. He wanted to make love to her so badly. She moaned as he pushed the head inside. The opening stretched and formed little ripples around its edges as the huge tip entered her. "Ooooh! It's so big! I love a big cock!"

He tried not to sniff as the silent tears made his nose stuff up, but she heard him anyway.

"Nicole, what is the matter? I helped you fill your pussy, don't you want to help me fill mine?" Zoe crooned.

"Yes Mistress."

"Then what is the matter?"

"Nothing Mistress, I'm sorry."

"Nicole, you must answer my questions. Why are you crying, princess?"

"I just wish I could make love to you, Mistress, I'm sorry."

"But honey, I need a big cock! Not a little tiny clitty like yours! How can you make love to me with that little thing? Don't be ridiculous." Zoe was leaning back and adjusting her nipple stretchers to make her long nipples even longer while she scolded Nicole. "That's not how ladies please each other! Now, do you want to help me or do you want to sit in the corner and watch me help myself?"

"I'm sorry. I'll help you Mistress." Nicole returned to Zoe's lovely pussy, and obediently fucked her while she squirmed and worked herself on the big cock.

"Turn on the vibe!" She said, "Stuff my pussy full, Nicole! I just love a big cock in my pussy don't you? Ooooh! Fill my pussy!"

Tears ran down his face as she came for nearly a whole minute straight. He had never felt a woman cum on his cock like that. He pulled up his dress to look down at his tiny, nearly-numb, penis as he crouched before her while she screamed in pleasure.

It wasn't over. He was made to fill her pussy with little balls on a string so he could "help her keep her pussy full all day," as she put it. She made him use his tongue to push all ten balls into her pussy and while she moaned and giggled the whole time. Then his handcuffed wrists were attached to a locked collar at his neck so that he couldn't try to free himself from the corset or chastity device. As she left for work she sat him down at the breakfast table where a diet milkshake awaited him. Elaborate housecleaning instructions awaited him on a paper next to his glass.

"Before I get home for lunch, I expect you to have the kitchen and bathroom cleaned. The supplies are stored under the sink. When I return for lunch at one I will help you urinate. Until then you must refrain from using the toilet. This afternoon you are to dust the house. There is a pink feather duster in the coat closet in the living room. I don't care if your hands are attached to your neck. This house is to be SPOTLESS!" Zoe said loudly, transforming from giggling-girlfriend to drill sergeant in a matter of minutes. Nicole sniffed and sipped his milkshake as his Mistress' heals clicked away from him down the hall outside. He shifted in his seat, trying not to sit on the buttplug too hard. He wiggled to scootch the dress up higher to see the panties again. His cock was soft now and looked tiny and flattened. He could still leave at the end of the month, he reminded himself. For now he had better hurry to get everything done before she returned.