Sissy for Mommy's Nipple Cream Ch. 05

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tried to leave that persona behind, Julia launched a desperate gambit to get him addicted to "BBC Cream" to preserve her special relationship with her "daughter". It had worked perfectly. Before Jim realized what the BBC Cream really was he was hopelessly hooked, and Julia wielded his addiction with surgical precision, entrapping him further and further into a new role as her submissive sissy daughter. Jaime now dressed en femme anytime she wasn't in school, and even then she always wore panties and a bra under her boy clothes. Even worse, she'd been forced into wearing an electrified chastity cage for the past month, ultimately leading to the humiliating anal milking at Julia's hands now replaying again and again in Jaime's mind. Every detail was seared into her mind to the rhythm of her still pulsing asshole as she gradually cried herself to sleep.

The next morning Jaime dutifully completed her daily ritual of applying her makeup and dressing in a cute skirt and blouse, trying to lose herself in the routine. She made her way down to the kitchen nervously, hoping that Julia would just let what happened last night slide into memory without mention. Julia appraised her daughter carefully before nodding her approval, then parted her robe, spread her legs, and snapped her fingers before pointing under the kitchen table. Relieved, Jaime wordlessly obeyed, crawling under the table and breathlessly servicing her mother's sweet pussy. Lost in the ecstasy of service and submission, Jaime was slightly shocked when Julia finally pushed her head away and beckoned for her to follow her to the couch.

Again Jaime tried to subsume herself in the routine as Julia opened her jar of BBC Cream and scooped out two healthy handfuls, smearing globs of the decadent treat around each of her prominent nipples before firmly grasping the back of Jaime's neck and pulling her face into one of her swollen breasts. Jaime eagerly latched on, greedily sucking in the sweet mixture of her mother's milk and her black lover's cum. Invasive thoughts buzzed around her. Comparisons between the rich flavor of the BBC Cream and the watery puddle of her own cum she'd licked up the night before. Memories of watching Damien plowing Julia with his impossibly large cock before spewing loads of this very cream. The straining of her shrunken clitty in its little cage as her closeness to Julia's amazing body registered in the male remnants of her mind. Through it all she struggled to block it out by focusing on the simple mechanical motions. Lick. Suck. Swallow. Lick. Suck. Swallow.

It wasn't until Jaime was half-drunk on milk and cum and transferred to Julia's other breast that Julia finally broached the subject of the night before.

"I want to make something very clear to you sweetheart," she started in a firm matronly tone. "You will never try to put your little clitty inside me or any other woman again."

Julia reached down to caress Jaime's caged package with one hand while pressing her face firmly into her breast with the other to forestall any protests.

"From now on when mommy's little girl needs release it will be like a proper young lady, just like yesterday. Is that understood?"

Julia's gentle caresses of Jaime's balls turned harder and harder until she frantically began nodding her head while she nursed.

"That's my good girl," Julia beamed. "Now, I want you to know that I take my share of responsibility. I've been enjoying our feedings and your tongue so much these past weeks that I fear I've coddled you. No more. I'll pull a few things together while you're at school today and we'll start the next stage of your training once you get home.

Julia relaxed her hold on Jaime's neck, allowing her daughter to release her dripping nipple from her mouth before pulling her head up and locking her in a deeply passionate kiss. Their tongues danced back and forth in the residual breastmilk and BBC cream for a few breathes before Julia finally broke away.

"Now run upstairs and get ready for school sweetie, you don't want to be late!"

Jaime did as instructed, quickly stripping out of her skirt and blouse before putting her boys school uniform on over her lacy panties and bra. She didn't have time to wash off her makeup or restyle her hair in a more masculine fashion, but truth be told she felt better this way and she'd been going to school like this more often than not recently. After the initial wave of teasing from being caught wearing panties had died down she'd managed to slip back into the background and pass mostly unnoticed. There may have been a few long stares from classmates and teachers at the contrast between her cascading blond curls and not-so-subtle makeup and her clothes, but she was so preoccupied with Julia's words from that morning that she would never have noticed. Next stage of her training? She'd assumed up until now that Julia was just making things up as she went along, but that phrasing implied a definite goal. A goal which was slowly coming into focus in Jaime's lust-addled mind.

When Jaime got home she quickly ran up to her room to change back into her girly clothes. She almost left her room as soon as she'd gotten dressed, but her reflection in the mirror caught the corner of her eye. She took a minute to model in front of her mirror, striking poses at different angles and trying on a series of feminine expressions. Grasping the waist of her skirt with both hands Jaime slowly slid it up a few inches, leaving a scandalous amount of her legs exposed. Bending over in front of the mirror Jaime noted with a satisfied smile that the bottom of her pert ass was now exposed, revealing just a hint of her pink lace thong.

"Jaime darling, stop your primping and come downstairs, I have something to show you."

Jaime quickly obeyed, running down the stairs with her skirt swishing around her. When she made it into the living room she pulled up in shock. Standing proudly on the coffee table in the middle of the room were two of the biggest dildos she'd ever seen. She tiptoed closer to them as if in a trance, gently reaching out with both hands and brushing her fingertips tentatively over their bulbous heads. Her jaw went slack as she struggled to comprehend their sheer size. Each was a solid twelve inches long and bigger around than her wrist.

"Feeding first my dear," Julia teased. "Mommy's tits are about to burst and you'll have plenty of time to play with your toys after."

Jaime obediently hopped into Julia's lap and started to suckle. Julia had skipped applying her BBC Cream before the feeding, so Jaime had to make do with her mother's unadulterated milk. Although she felt pangs of hunger for the savory additive there was something nice about going back to how things had been before and simply enjoying a refreshing meal from her mother's massive breasts. For the first time since Julia had hatched her plan to get Jaime back, Jaime found herself grateful and blissfully lost herself in nursing.

After they'd finished Julia explained the next step in her devious plan.

"Now I'm sure you noticed there was no cream served with your little snack from mommy today. And there won't be any going forwards either until you show real commitment to self-improvement young lady."

"But Mom!" Jaime protested with a feral hunger in her eyes, "That's not fair!"

"No, what isn't fair is you relying on me to keep your greedy little mouth full of sweet black bull cum. So now you're going to start learning to feed yourself."

Julia stood and removed her pants, revealing some kind of harness underneath. She picked up one of the huge black dildos from the table and fastened the base of it into a ring on the harness. Then she turned back to Jaime on the couch, wrapped both hands around the back of her head, and started to pull; slowly but inexorably forcing Jaime's head closer and closer until the head was pressed against her gritted teeth. Her resistance lasted all of a few heartbeats before her inevitable surrender to the her mother's understated dominance.

Jaime had sucked on a similar dildo once before, hiding in Julia's closet while she was out on a date, but this was entirely different. Then she'd been in control, living out the fantasy playing in her mind while working the pretend cock into her mouth at her own pace. Now she was a submissive plaything, looking passively up into her mother's gleaming eyes as she forcefully humped her strapon in and out of her sissy daughters aching mouth. Julia's breasts swung freely with every thrust, triggering a steady dripping of milk from her nipples which mixed with the tears running down Jaime's face.

Finally Julia pulled hard on Jaime's head while thrusting her hips forwards, forcing her strapon cock in until it bottomed out in the back of her throat. Jaime struggled helplessly, but was unable to free herself. Her last thought as darkness crept in from the corners of her vision was that she hadn't realized how strong her mother was.

When Jaime came to on the couch a few minutes later she saw Julia holding a ruler to the dildo while making a series of lines on it with a permanent marker.

"Not a particularly impressive start," she offered with a tinge of motherly disappointment, "but I suppose it's about as good as we could have expected for a novice."

Julia pointed to the first line across the dildo, a couple of inches past the head.

"Here's where you made it to today sweetie, about four inches before you couldn't take any more. But if you're going to be mommy's big girl and get your own cum from big black cocks, you'll have to do much better than that. So if you want mommy to keep sharing her sweet cum with you, then you'll need to show improvement. I think that a week for every additional inch you manage to handle sounds fair, don't you?"

Jaime could only loll her head in shock as she tried to imagine taking down any more of that monster.

"You'll need something to practice with, so I got you your very own dildo just like mine. Have fun dear!"

Jaime worked feverishly on her deepthroating skills, spending hours every day bobbing her head up and down on her chocolaty toy. Julia would come by her room from time to time and offer pointers on how to open her throat, or release the tension in her jaw. After a few days Jaime proudly informed Julia that she was ready to earn her first week. Julia pulled on her strapon harness and carefully administered her sissy daughter's test, plunging her marked dildo down her throat until her lips crossed the five inch mark. Beaming with pride Julia pulled Jaime up to her feet and into a tight hug, kissing her passionately while her drool-covered strapon knocked against her caged clitty. After their moment of shared joy, the two wasted no time in giving Jaime her well-earned reward: breastfeeding with a generous slathering of cum on each of Julie's tits.

The next few days saw Jaime slack off on her training, but as the week drew to a close she again started frantically training herself, just barely managing to make it to six inches before her time ran out. The week after she was much more disciplined, regularly training herself so that when exam day came she was quite ready to handle a full seven inches. By that time Julia had started to join in with Jaime's training sessions more often, bringing along her own dildo to demonstrate advanced techniques and sometimes showing off by throating the entire thing. This sweet bonding time over shared interests only reaffirmed to Julia that she'd made the right choice in forcibly feminizing her daughter. Even when she had to take a firm hand, it was all done out of love.

While Jaime had been able to progress to seven inches fairly easily, once there she hit a wall. No matter how hard she trained she couldn't squeeze any more of her mother's monster strapon down her throat. A week passed and her cum credit expired. She trained with even greater fervor, but try as she might she didn't see any results. After another week she was desperate, begging her mother for just a drop of BBC Cream at her feedings, but all she got for her troubles was a sharply swatted bottom and a reminder that Julia made the rules. She even tried licking up her own cum from fingering herself like Julia had shown her, but that only made her crave the real thing more.

After another of Jaime's BBC Cream-free feedings she and Julia were engaged in their now semi-regular practice of post-feeding oral practice with Julia seated on the couch and Jaime kneeling in front of her, bobbing up and down on her strapon.

"You know darling, I think I may have found the solution to help push you past your little problem," Julia offered. "You've done so well on mommy's strapon, but nothing can compare to the real thing. The pulsing throbs, the salty taste, the warmth of it spreading through you. I think if we're going to get past this, you're going to have to find a real black cock to practice on."

Jaime tried to pull herself off to protest, but Julia pushed her back down and all that came out was "Mmmfff."

"Wonderful, that settles it. Damien has a younger brother named Darnell who's just your age. I'll set things up with Damien, but I think we should be able to make our date tomorrow evening into a double!"

The next day was Saturday, and Jaime and Julie spent the whole day together prepping for their big double date. They started with a trip to the spa. The girls got massages from a couple of hunky guys (Jaime was grateful that the towel draped over her covered up her cage). Next they went to relax in the sauna, which was filled with other women in various stages of undress. At first Jaime was worried that her throbbing clitty locked away in its cage would give her away, but she quickly sat with it tucked back between her legs as Julia introduced her friends at the spa to her daughter. Much was made of Julia's adorable little girl, and if any of the other women were suspicious they hid their thoughts behind sly smiles. Soon the discussion in the sauna turned back to its usual topics: gossip and sex. Jaime soon lost herself in tittering giggles, relaxing into being one of the girls. Their trip to the spa finished with facials for both along with manicures and pedicures.

After their day at the spa the girls went back home to do their makeup and get dressed. Julia insisted that they wear the matching red halter-top dresses they'd picked out on their last trip to the mall together, saying that they sent exactly the 'fuck-me' message they wanted for tonight and that people might even mistake them for sisters. Once they were both dressed and ready, Julia pulled out her strapon cock for a 'dress rehearsal'.

Jaime awkwardly found her way to her knees in her high heels and dress and dutifully started to suck, loosening her jaw and throat through muscle memory trained in countless repetitions. Meanwhile Julia rested one hand as usual on the back of Jaime's head, while with the other she reached down and began fondling and squeezing Jaime's chest through her dress. Jaime's pushup bra provided at least a hint of cleavage, giving Julia something to squeeze, but there wasn't much there.

"You look delightful darling, but just imagine how much better you'd look if you filled out a little bit here." Julia squeeze Jaime's chest again meaningfully. "Perhaps we'll have to do something about that soon."

Before that thought could go any further, they were interrupted by the doorbell ringing.

"Well look at that," Julia said as she slid her cock from Jaime's mouth. "You hit seven and a half inches! I suppose the clothes really do make the woman."

Damien and Darnell took the girls out for drinks at a swanky cocktail bar downtown. Darnell was a little shorter and less stocky than his older brother, but still athletically built. The bigger difference between the two was in their behavior. Damien was self-assured to a fault, constantly swaggering and helping himself to rough handfuls of Julia's tits and ass whenever the mood struck him. Darnell, on the other hand, was more reserved, nearly a gentleman in contrast. He still wrapped his arm around Jaime and cupped her ass, but he kept his hands on the outside of her dress and his gentle squeezes and caresses made Jaime feel reassured and protected more than anything else as she navigated this strange new environment. As she downed more and more of the pink fruity drinks the boys kept buying for them she found herself subconsciously sliding closer and closer to Darnell as she looked into his deep brown eyes. She was almost sitting in his lap when Julia tapped her on the shoulder and told her to come with her to the ladies room.

Jaime wobbled a bit as they walked, partially due to the unfamiliar high heels and partially due to those surprisingly strong drinks. She hadn't really been able to taste the alcohol in them, and she wasn't exactly sure of how many she'd had, but she felt a warm buzz through her whole body.

"Well that was a lovely evening," Julia said once they reached the bathroom, "But now it's time for you to seal the deal. Those boys back there have what you need, and if you want it you're going to have to get them back to our place."

Jaime hesitated for a moment before the swirling mix of cum withdrawals, liquid courage, and the gentle look in Darnell's eyes made up her mind. She nodded, then led Julia confidently back to their booth.

"Well boys, this has been a blast, but whaddya say we head back to our place for one last round of cocktails?" Jaime's exaggerated wink and lascivious stare at Darnell's crotch while licking her lips lacked any form of subtlety, but the brother's were more than happy to take the green light and run with it.

They'd barely made it in the door before Jaime and Julia were both on their knees, greedily unfastening and pulling down each of their men's pants. As Jaime pulled out Darnell's cock she paused for a moment, tenderly running her fingers over his shaft. It was big. Far bigger than hers had ever been, even before Julia had caged it, but a little smaller than her training dildo, perhaps only ten inches long. But it wasn't only big, it was beautiful. Jaime handled it with reverent awe as she took in the elegant slope of the head, the hard yet pliant texture of the rippling shaft, the veins throbbing with energy, and most of all the heavy sack at the base filled with her prize.

"Ya know, if you ain't ready for this then you don't..." Darnell offered softly, mistaking Jaime's worshipful pause for hesitation.

"Shut yo damn mouth little brother," Damien shouted back, "didn't I tell you these white bitches would go crazy for us? Just let your shawty get to work like mine."

Jaime looked across at Julia, gleefully sucking down Damien's cock and knew in that instant that she wanted to be just like her. Seizing what she wanted without restraint and earning her sweet reward. She looked straight up into Darnell's deep brown eyes then sucked the first half of his manhood down in one smooth motion. Head bobbing up and down his glistening shaft, Jaime kept her eyes locked on Darnell's for a few minutes, enjoying every moan and shudder she teased out of him while staring into his soul.

Then she really began to push herself, closing her eyes to focus as she used every trick that Julia had taught her to coax Darnell's bulbous head further and further down her stretched out throat. She stifled her gag reflex by imagining his delicious baby batter coating her insides. Her lungs burned as she gasped for air between thrusts, but through it all she never lost her focus, working him in deeper and deeper until she was suddenly stopped by a strange sensation. Jaime opened her watery eyes to find that her nose was pressing into Darnell's abdomen and that the odd feeling on her chin was his pendulous balls smacking into her. She could hardly restrain her glee, and nearly forgot to catch her breath the next time he pulled back before thrusting all the way into her throat once more. Mother had been right, she'd broken through the wall and sucked down a full ten inches. She'd done it for the cum, she thought as Darnell's full balls slapped her chin once more. And for Darnell, she thought as she gazed happily up into his eyes once more.