Hot Mom's Sissy Honeymoon Sweetie 5

~~~~~ Week 2: Chrysalis and Clarity ~~~~~

In many ways the second week of Ashley and Ava Addams' impromptu "Honeymoon" at the Pink Lotus Resort after Ava and Greg had abruptly called off their wedding was much like their first. The rhythms of their days were similar. They spent their time throughout the day enjoying the amenities of the spa, doing couples yoga or getting massages and of course getting Ashley's daily coconut cream indulgence; or engaging in friendly competition on the tennis court before cooling off together in the locker room; or simply relaxing and tanning at the beach. In the evenings they often invited some of their acquaintances among the resort staff to join them for dinner, though sometimes they kept it casual with a simple meal with just the two of them.

On 'Date Nights' Ashley would always help Ava to dress and look her best, and she would always press Ashley to join her in the fun, although he still held out as tempting as it was. After dinner Ava made a habit of asking Ashley for some time alone, either taking their dinner date(s) back to their suite or texting a booty call to one of her growing stable of boyfriends among the resort staff. There was Ajani, the lithe yoga instructor who had held helped Ashley and Ava grow more comfortable with new positions together in his sweaty studio. There were Leandro and Dejuan, the talented masseurs from the spa who had worked their bodies over from head to toe. There was Kemar, one of the waiters who served their food that Ava had insisted join them for dinner. And there was Tafari and Shavell, the burly twin porters who Ava had requested come to the suite to help her rearrange a few things.

Regardless of whose company Ava requested, the evening routine was remarkably consistent. Ava would summon one or two of the hung black men on staff to their suite and get her brains fucked out while Ashley hid and watched from his spot at the window, unbeknownst to anyone inside. During their dinners he found he was now focusing more on the men Ava invited than on her, imagining what they would look like, stripped down with their toned muscles glistening from the sheen of sweat on their rich dark skin as they fucked his mother with their massive, girthy cocks. Ashley had grown quite proficient in fingering his ass, easily lubing it up with spit or precum gathered on his fingers, then dexterously fucking himself and tenderly stroking his sensitive spot deep inside. That maddening sensation combined with teasing his nipples and watching the real-life blacked porn happening right in front of him was enough to get him right to the edge of cumming. In some ways it was infuriating, to be so horny and so close but unable to climax, but at least rubbing his special spot milked the precum from his swollen balls, providing some relief as it oozed out the front of his flat chastity cage and into the convenient liner in his panties.

Once the men had finished with Ava and left and everyone but Ashley had been satisfied, Ashley would rejoin Ava. As frustrating as but being able to cum in chastity was for him, it was still his favorite part of the day. For one thing, it was the main time he got Ava all to himself, a sweet reminder of the strength of their relationship that when the other men who came and went were gone, his arms were the ones she curled up in to sleep. But the second reason was even better. When laying down the boundaries of their new relationship after the first night he'd secretly watched her get laid, then gotten a surprise titjob, Ava had told her son that they could maybe kiss sometimes, but just a little. And during the day she generally held to that, sticking to quick pecks on the lips or the occasional more affectionate kiss. But in the evenings, after getting her blood pumping with a good roll in the sheets, Ava couldn't help herself.

Sometimes it started with a welcome back kiss as Ashley came through the door of their suite minutes after her lovers had gone. Other nights she had the self control to wait until their goodnight kiss once they were both dressed in their satin rompers and tucked in. But whenever it happened, Ashley's horny mother just couldn't resist his soft, full lips, and before long the two were engaged in a hot and heavy makeout session. Ava took the lead, pouncing on Ashley and usually pinning him to the wall if they were standing, or rolling atop him if they were already in bed. She liked to pin his arms above his head to keep him from getting too handsy as she nibbled and sucked on his plump lower lip, making him moan with need until she quieted him by plunging her tongue into his waiting mouth.

Eventually Ava would lose herself a little to the throes of passion, letting her grip on Ashley's wrists slip as she worked her hands down his body, exploring the delicate expanse of his neck, or the growing curves of his chest, or the smoothness of his flat tummy promising pleasures just beyond... But then he'd inevitably lose control and try to sneak his hands down, running them past her cheeks, down her neck, and into the sweet, soft expanse of her large breasts. Or stroking her luxurious dark hair, then tracing the curve of her back until his hands rested on her wide hips or her thick ass. It was one of her firm boundaries, and behavior she'd scolded him time and again was inappropriate for a mother and son, even ones as close as they were. And so with a playfully exasperated sigh she'd find his wandering hands, lock her fingers around his wrists, and pin his arms up above his head again before continuing to make out with him. Eventually when she'd had enough Ava would release Ashley, having slaked her post-coital thirst for his sweet lips and leaving him a shuddering mess of blissful gratitude and unsatisfied desire.

Ava and Ashley's regular evening makeout sessions weren't the only change they saw in their second week at the Pink Lotus. There were many others, some small and subtle and others obvious and dramatic, all adding together into an ever evolving relationship between the inseparable pair. One of the subtler, but nevertheless significant, changes enacted unilaterally by Ava was in Ashley's pronouns around the resort. Ever since their first visit to the tennis courts when Ava had introduced Ashley as her daughter for the convenience of using the women's locker room together, she'd continued to use feminine pronouns for Ashley.

The well-trained staff of the resort were swift to pick up on the change and professional enough to not comment on it, so within the warm cocoon of the resort it was as if Ashley became a girl overnight at Ava's whim. His feelings on the matter were complex. On a surface level, it obviously made Ava happy, and it made it easier to spend as much time with her as possible, which made Ashley happy. But on a deeper level he'd been struggling his whole life against being misidentified as a girl, given his technically androgynous name and his feminine features and build. Just letting it slide as everyone around him casually referred to him as one rankled at first, but graduate and in imperceptible degrees it became less of a bother, until by the end of the second week he hardly noticed. Of course Ashley still thought of himself as a boy, at least most of the time, his painfully swollen balls tucked away in his panties and his locked away cock pushing futilely against the flat metal head of his chastity device didn't allow him to forget what he was beneath the cute clothes Ava preferred to dress him in. But it really didn't matter much to him in the end how those around him referred to him.

Truthfully, Ashley had to admit that he couldn't blame anyone for identifying him as a girl. His blonde hair had been an unruly mop approaching shoulder-length when they'd first arrived at the resort, and in the two weeks since then it had seemingly grown a couple inches. Apparently the climate or something in the food agreed with him. He hadn't really bothered with styling it, until Ava had signed them both up for a trim at the spa and chosen a new haircut for him: an airily textured bob that emphasized the natural waviness of his hair. Ashley didn't understand how having a bit of hair cut away had suddenly made him look like he had more, but the magic of layering gave him a chic look that framed his face beautifully.

He'd always had vaguely feminine features, but with the new haircut the face he saw staring back at him in the mirror was downright girly. His blonde hair swept over his forehead, pulling attention into his widely set crystal-blue eyes. Even without the makeup that Ava continually encouraged him to try, his naturally long and curly eyelashes and naturally thin and well-shaped eyebrows were lovely. Below them he had a cute button nose, the naturally pink bow of his lips, and a narrow chin with a sweet little dimple of a cleft in the center. One day as Ashley inspected himself in the mirror he got the nagging sensation of recognizing his reflection not as himself, but as someone else that he knew. He racked his brain, trying to tease out the elusive connection until suddenly it snapped into place. It wasn't someone he knew per se, but someone he'd watched for countless hours. He looked eerily similar to one of his favorite pornstars, Elsa Jean. He'd watched her videos on Blacked more times than he could count, marveling at how she managed to take such massive black cocks into her tiny body and aroused by the combination of her apparent innocence and her obviously insatiable hunger.

And the similarities between Ashley and Elsa didn't end there. When he inspected his body in the mirror dressed only in his panties (Ava's preferred uniform for him when they were just relaxing in their suite), he saw that his short and slight frame had been continuing to grow out, but not in the way he'd always hoped growing up. His already narrow waist seemed to have pulled in further, maybe as a result of their regular yoga sessions with Ajani, while the strengthening of his glutes had filled out a tight little ass that was now threatening to break out of the panties that had fit him well just a short time before when Ava had bought them for him. He wondered about asking her to please buy him some thongs, as those seemed like they'd be more comfortable. And up top his boy boobies probably matched Elsa's A-cups now, no longer general swelling in his chest region but rather two well-defined palmfuls with perfectly pink nipples that precisely matched his lips. He knew from looking up her measurements that at 5'3" she stood an inch taller than him, but he had a bit of weight on her, mostly in his thicker thighs and ass. Honestly he could have been mistaken for her younger sister, so how could he protest when the tall, bulky black men on the resort staff with their yummy-looking bulges in their tight shorts treated him and looked at him like he was a girl?

Concern over his growing breasts did prompt Ashley to seek help in the middle of their second week. It wasn't so much that he minded having them, they were honestly kinda fun to play with, especially his sensitive, puffy nipples, but he was concerned as to what might be causing their growth and whether they were going to keep going. It was all well and good while they were at the resort, and they made his bras and tops from Ava fit far better, but in a could more weeks they'd be going back home and he'd finally be dressing as a boy again, and he was worried that if his boobies grew much more he'd have a hard time hiding them, even under baggy boy clothes. So he made up an excuse to visit the resort doctor, feigning slight illness to Ava. Out of concern for her "precious little girl", Ava tried to join Ashley in the doctor's office, but he insisted that he could handle it on his own.

Doctor Johnson nodded sagely as Ashley expressed his concerns with his growing breasts, then instructed him to remove his top. Ashley was wearing a pair of low-rise cutoff jeans shorts and a pale blue Cami with little red hearts that Ava said complimented his eyes, so he carefully lifted his shirt over his head, exposing his breasts to the doctor and awaiting his judgement. It was cool in the air conditioned office, and Ashley embarrassingly felt his nipples gradually harden into painfully sensitive points as the large doctor leaned down to inspect them. Without warning, Doctor Johnson placed one of his hands on each of Ashley's breasts, gently massaging the tissue, his palms sending sparks cascading through Ashley's body as they rubbed against her hard pink nubs. His hands were surprisingly soft, yet strong. While he shared a similar build to the other Jamaican men Ashley had seen at the resort, positively dwarfing his slender 5'2" frame, his hands were the dextrous tools of a doctor in spite of their large size. Ashley stared down at them in shock, squirming a bit in his seat as he felt a little precum oozing from his cage into his panty liner, realizing that this man's hands were the first to touch her boobs other than her own and her mother's. His boobs. They were his boobs. Sometimes these days Ashley got so used to been called a girl that he forgot it was just an act to keep Ava happy. Finally the doctor completed his inspection.

"Your breasts seem healthy for a girl your age," he pronounced in a deep, authoritative voice. "And if I'm not mistaken they are in active growth. I wouldn't worry, I'm sure with time you'll grow a beautiful set of breasts just like your mother's."

Ashley froze as he reached for his Cami, realizing his mistake. While he'd told the doctor that he was concerned about his breast growth, he'd never mentioned the small little detail that he was, in fact, a boy.

"No, I'm so sorry Doctor Johnson, the problem is that I'm a boy."

"Ah, I see," he said with mild confusion that evidenced he didn't. "I know that many girls your age are interested in transitioning, and of course as a medical professional I must support your choice to do so, but as a man I cannot understand why such a pretty little thing such as yourself would want to become a boy."

"No!" Ashley said with growing exasperation, "It's not that I want to be a boy, I am one, and that's why I shouldn't be growing breasts!"

The doctor took another look down at Ashley's heaving chest, then fixed his eyes in a hard stare.

"There's no need to be hysterical or throw a fit young lady," he said sternly. "I told you as a medical professional that I would support your choice to transition, but if you honestly want me to believe that you were born a boy you'll have to stand up and strip out of those shorts so that I can inspect you properly."

"No, no, it's fine," Ashley said meekly as his face blanched. "I was... just joking about all of that, that won't be necessary, sorry. Thank you for your time Doctor."

Ashley quickly got dressed again under the doctor's watchful eye, then scurried out to the lobby to reconnect with Ava and continue on with their day.

Besides the changes to Ashley's body, the other prominent change in Ava and Ashley's second week was in the hierarchy of their relationship. They'd never exactly been equals, with Ava in the position of natural authority as Ashley's mother and her natural assumption of the typical dominant male role in their practice dates, but as time went on the slid further and further into a domain where she was lovingly dominant and he was sweetly submissive. This modality subtly affected all of their interactions throughout the day, but there were some times in particular when it showed through the most.

The first was when Ava showered. After trying it a couple of times she'd found it quite pleasant to have a shower attendant to wash and scrub her body, and as Ashley was always available she soon made it clear that her baseline expectation was for her to serve her whenever she bathed. Yes, it was perhaps a little much to allow Ashley to see her fully nude, but Ava had gradually been shifting her perspective from a repressed attitude of "I really shouldn't" to an empowered attitude of "Why shouldn't I?"

She'd already shrugged off the restrictive strictures of society on women by building our a personal harem of half a dozen hung black lovers to satisfy her needs, and she was in the process of helping Ashley to transcend the expectations of society on him from being born a boy to blossom into something beautiful and new. So why shouldn't she do what felt right to her and enjoy herself along the way? Besides, Ashley was always safely locked in her little cage, so even though she clearly enjoyed washing Ava's body, then standing obediently behind her and giving a scalp massage as she washed and conditioned her hair, it wasn't as if anything would actually happen between them, so what was the harm? Lots of girls showered together, Ava remembered some wild times in college doing just that, and as she came to think of Ashley more and more as a daughter, it just seemed right.

The other major shift towards a service-oriented dominant/submissive relationship between Ava and Ashley was centered around Ava's feet. Like many women Ava's feet were often sore by the end of the day due to the fashionable heels she liked to wear. So of course a footrub was always welcome, and a partner who was willing to provide them was a major plus. But she'd never been with anyone as willing, and even eager to spend time at her feet as Ashley. Ever since that first footrub on the beach Ava had caught Ashley staring at her feet nearly as often as she caught her staring at her tits, and it only took the barest invitation for Ashley to happily kneel or sit in front of Ava and carefully begin to massage the knots and stresses out of them. Eventually the behavior became so engrained that all Ava had to do was nod downward or say something like "heel" or "down" and Ashley would drop whenever they were and begin to lovingly serve.

As wonderful as the physical sensation of having her feet massaged felt (and that was substantial as Ashley rapidly learned just how Ava liked it), the emotional rush of seeing Ashley's loving adoration was far stronger. Sometimes Ava would nearly ignore Ashley as she worked below her, continuing to read a book or apply her makeup, but other times Ava couldn't help but look down in love as she watched her sweet daughter fully focused on serving at her feet. Truth be told, having her feet kissed or her toes licked and sucked on didn't really do anything physically for Ava, but the emotional rush that came from Ashley's response as she doled out those rewards for good service was intoxicating. The feeling of power from casually saying "kiss" as she read and then feeling a shower of kisses on her soles and toes along with mumbled expressions of gratitude was breathtaking. Similarly, seeing Ashley's whole body go tense with desire as she wordlessly pushed a toe or her whole foot into her pretty little mouth was flattering in the extreme.

Ava didn't know, though she may have secretly suspected, that this casually dominant treatment had accelerated Ashley's feelings for her from animal lust when they'd first arrived, to an uncertain crush after their practice dates, to full-fledged love. Ashley had honestly thought that he'd never have a chance with any woman, at least not one he wasn't paying to be with him, and certainly never imagined that he'd be the closest companion of a woman as beautiful as Ava, with her gorgeous face, immaculate style, thick curves, and breasts the size of his head. And yet here he was, spending nearly every waking moment with her and cozily sharing her bed every night. He'd always loved her in one way as her son, so while it was odd at first their suddenly deepening relationship into something more also felt like a natural extension and growth rooted in many years spent together. And given that context it made sense that she naturally took the lead role. For years she'd been the primary authority figure in his life, and although as he grew up that dynamic had faded, as their relationship grew in unexpected new ways it resurfaced stronger than ever. In a way it felt weird to be so completely submissive and subservient to his mother as an adult eighteen year old man, but it was also incredibly freeing to not have to worry about making any decisions for himself, knowing that his loving mother would tell him whatever he needed to do.

The one difficult bit for Ashley in reconciling with their new relationship dynamic was his feelings regarding Ava's ever-expanding stable of lovers. Here he was a tangle of strong conflicting emotions. In one sense it made him proud to see the proof of how sexy and desirable his mother was in so easily pulling so many young black studs into her bed. He could only imagine how many girls the strong, muscular, and hung black men Ava seduced had throwing themselves at them, trying to ride their beautiful cocks, but no matter the circumstance Ava was always able to promptly summon them to the Honeymoon Suite to make love to her. In another sense Ashley was just happy to see Ava happy. Her smile was infectious, and as much as he knew she enjoyed their time together throughout the day, he never saw her happier than when she was pulling one of her lovers chocolate rods out to suck on. She deserved to be happy after all the long years of work she'd put in raising him as a single mother, and if she was happy, then he was happy too.

The only problem in this happy situation was how desperately Ashley needed to cum. His anal fingering and playing with his breasts as he watched Ava and her lovers through the window took some of the edge off by making him ooze out precum, but day after day the pressure in his swollen balls demanding a full release grew. Every night he was watching a real life version of Blacked far better than the usual porn he'd watched back home, but then at least he'd been able to jerk himself off. He knew that he could never actually be with Ava in the way that her lovers were, and that while she seemed to enjoy making out with him, and cuddling together, and showering together, and having him worship her beautiful feet, there were boundaries, and it wasn't like she'd ever actually be into a guy like him anyway, she clearly had a type. But he wished that she'd at least unlock him once in a while so that he could jerk himself off. And maybe if he was really, really good she'd even help him a little? Not a titjob like she'd given him the last time she'd allowed him to orgasm, Ava had been clear that that was a step too far, but maybe just a quick little handjob would be okay? Or even if she unlocked him and have him a few minutes to take care of himself while they cuddled at night. Just something to let him cum while feeling connected to her instead of sending him off to the bathroom to handle his business. That pressure finally came to a head at the end of their second week at the Pink Lotus.

It was late in the evening and Tafari and Shavell had been Ava's lovers for the night, following her eagerly back to the suite after dinner. They weren't Ashley's favorites within Ava's harem, the twin porters were bulkier then the others and tended to work in concert to fuck Ava more roughly than the others did. He preferred the leaner and more graceful bodies of the spa employees, who tended to make love to his mother in ways that he felt were more artful and respectful, but in the end she seemed just as happy to be on the receiving end of the rougher sex, and so Ashley was begrudgingly content. As usual he played with himself as he watched secretly through the window, and as usual he wasn't able to reach orgasm with his cock locked away within his body behind his flat chastity cage. When they'd left and he'd given Ava a respectful amount of time to make herself presentable, he approached their front door and knocked to be let in. He always felt a little silly knocking to be let in when it was his suite too, but it felt right.

When Ava answered the door she was still nude, as Tafari and Shavell had ripped away her clothes before having their way with her. Usually Ava pulled back on some clothes before Ashley "came back from her walk", or at least tossed on a robe or her pajamas, so Ashley was slightly taken aback by the sight. It wasn't as if seeing his mother's amazing body in it's naked glory was new to him, but she had a look of feral hunger in her eye and had taken no efforts to conceal the fact that she'd just been well-fucked. Her dark hair was wild and unkempt, a sheen of sweat still covered her body, there was a trail of love bites down her neck leading all the way onto her breasts where her erect nipples betrayed her continued arousal, her ass was marked with multiple large handprints from the spankings she'd received, and a mixed ooze of her and her lovers' juices ran from her inflamed pussy down both of her legs. Moving like a lioness, she pounced on Ashley, pulled him into the room, slammed the door shut, and forcefully pinned him against it. His cry of surprise and pain at her rough handling was muffled as she mashed her lips against his, going straight to an open-mouthed kiss as she rammed her tongue into him.

Ashley could smell Ava and the sex on her, the sensation mixing with the sweet taste of her tongue and the tangy, salty flavor that he'd come to realize was the taste of other men's cocks from their regular evening makeout sessions. He breathed deep, savoring all of it as Ava ran her hands all over his body. Slowly Ashley started to bring his own hands down from over his head where Ava had pinned them in her first furious assault. He brushed back her wild hair from her face, then continued downward, eagerly exploring the naked, sweaty body pressing him into the door. Twin blooms of sudden pain stopped him in his tracks as Ava bit down hard on his lower lip and reached up under his skirt, fiercely clutching his tight little sack in her hand and squeezing in with her nails. His arms shot out to the sides in defensive submission as Ava continued to mercilessly squeeze his swollen balls while releasing his bloodied lip.

"Keep your hands up where they belong like a good little girl," Ava growled, "You know you're not allowed to touch me when we're kissing." Without waiting for an answer the dominant MILF leaned back in to continue taking her pleasure from Ashley's lips.

Ashley continued to squirm and writhe trapped between Ava's naked body and the door, but he did his best to keep his hands over his head and Ava didn't have to teach him again to follow her rules. Eventually Ava was cooled off enough from the sexual high her lovers had left her in and her kisses with Ashley grew more tender and sweet, gentle nibbling explorations instead of hungry bites. She still kept her body pressed firmly against Ashley's, but took her hands from exploring his soft body and laced her fingers through his, holding his hands until their final kiss.

"Thank you sweetie, you know how much I miss you in the evenings, even though Mommy needs her private time," Ava said with none of the primal ferocity from earlier, just a quietly understated authority. "Now wash up and get ready for bed."

Ashley slumped against the door and watched as Ava turned and walked away, her bare ass swaying seductively. Her needs may have been met, but his had only been inflamed, and his poor balls hurt from more than just her vicious squeeze. He hurriedly stripped, put on a new pair of panties that he hadn't soaked through yet with his juices, and pulled on the light blue babydoll Ava had given him while his pink satin romper was in the resort laundry. It was a very different feeling than his old pajamas, as the lace and mesh top was elastic and hugged his chest and torso closely, while the flaring skirt at the bottom was both see-thru and more open than the built in shorts of his romper. Even though the babydoll was a more boyish color, Ashley didn't like that it was closer to a dress, but in the end Ava liked how he looked in it, so it was what he wore.

After he'd brushed his teeth he saw that Ava had dressed as well in her red lace chemise and was seated at her makeup table. She turned and saw he was finished, and simply said "Heel." before returning to removing her makeup and applying her nightly routine of lotions and moisturizers. Ashley quickly scurried under the table and set to work massaging his mother's feet, but she had a different idea. Ava reached under the table with one hand and pulled her kneeling son's head forwards until his cheek was resting against the outside of her bare thigh, then she lightly rested both her feet in his lap. As Ava continued her nightly routine with one hand and lovingly stroked his hair with the other, the realization struck Ashley that if he hadn't been locked in his cage right now then his erect cocks would be resting right between Ava's beautiful feet. Squeezed between her silky soft soles. He wrapped his arms around Ava's legs, hugging them close, and couldn't resist starting to ever so slightly hump her feet like a dog in a heat, even though he knew that he wouldn't actually be able to feel anything from it. Ava continued stroking his hair, but started to press down more firmly with her feet until he felt it in the trapped balls between his thighs. Understanding her displeasure, he obediently stopped, holding himself as still as he could, serving as her footstool as she stroked his hair like a beloved and devoted pet.

Once she'd finished, Ava stood and walked to their bed, not looking back as she issued a single command, "Come." Ashley obeyed, crawling out from under the table and following her into bed, although the irony was not lost on him that her command was the one thing he wanted to do more than anything else. After a week of being locked without release, spending every day with Ava or watching her get fucked, and then having her force herself on him like she did tonight then make him sit at her beautiful feet, always close, always near, never able to touch her in the ways he so desperately wanted and not even able to touch himself in the way he wanted, Ashley finally snapped.

"Mom?" he asked hesitantly as he lay cuddled up next to her with his head on her shoulder.

"Yes sweetie?"

"It's been... a while. Do you think that maybe I could be unlocked for a little bit to take care of myself?"

"Hmmm..." Ava said as she paused and thought for a long moment. "I don't think so sweetie. It's too late, if you wanted to do anything that you should have asked earlier. Mommy's tired now."

Ashley let the silence hang for a minute between them, the conversation apparently over as far as Ava was concerned, his request for release casually denied, just like that. But he was too horny to take no for an answer.

"Please Mom? I've been really good, and it will only take a couple of minutes. I just... really have to cum. Please unlock me?"

Without really thinking about what he was doing Ashley started reaching for the key to his chastity cage, which, as always was dangling from Ava's necklace between her breasts, next to the engraved heart he'd given her for Mother's Day. She brusquely swatted his hand away.

"I said no Ashley," Ava said in a serious and much more awake tone. "You will be unlocked when I want to unlock you, do you understand me?"

"Yeah," Ashley mumbled.

"I said, do you understand me?"

"Yes Mom," Ashley answered more respectfully.

"That's better."

A minute of tense silence passed as Ashley fretted that he'd spoiled his chances for a release and would have to sleep another night full of desire and pent up cum.

"Well I'm awake now," Ava finally said. "How badly do you really need to cum?"

"So badly Mom, you can't even imagine. It hurts!" Ashley begged, any pretense of dignity forgotten.

"Show me. Get out of bed."

Ashley obeyed, sliding out from under the sheets and walking around the other side of the bed where Ava stood.

"If you want to cum so badly, then you can start by kissing my ass to apologize for waking me up as I was dozing off."

Ashley looked back at Ava for a moment, struggling to gauge whether she was serious or this was all an elaborate joke. But her arched eyebrow and impatiently tapping foot told Ashley that she was serious and that the clock was ticking. With one last glance at the key to his freedom hanging between his mother's tits, Ashley quickly walked around behind her, dropped to his knees, and rolled up the hem of her red lace chemise to fully expose her ass. He'd seen it before, of course, but never this close, and the distance let him truly take it in in all of it's glory as it fully filled his view. He reverently placed one of his hands on each of Ava's hips, unsure if exactly where I'm the fleshy expanse she wanted him to kiss. Ava was just having second thoughts about what she'd asked Ashley to do on a whim, thinking he'd never actually go through with it. She was about to tell him to stand up and that he could have his release, when suddenly he worked up his courage and leaned in, pressing his face firmly into the center of Ava's right cheek and planting a kiss on it. Then another. Then another. Then a dozen in rapid succession. Then a longer kiss that was more akin to a love bite, opening his mouth slightly and sucking part of her ass into his mouth, scraping it against his teeth as he licked and bit down gently on it. That one tentative first kiss exploded into an unstoppable avalanche as Ashley lavished his mother's perfect ass with affection.

Ava moaned, thinking that she really should put a stop to this as Ashley moved from her right cheek to her left, but it just felt so good. Plenty of men had grabbed her ass, spanked her ass, and even fucked her ass, but nobody before had ever kissed it, and her sweet little Ashley was kissing it for all she was worth. Ava tried half-heartedly to push her away, but Ashley would not be dissuaded, gripping harder onto Ava's hips and dropping her head lower and lower around the curve of Ava's ass to avoid her loosely swinging arms.

Ashley's trail of kisses continued as he moved his head down, sinking lower onto his knees as he devotedly worshipped. Ava's moans reached a new pitch as he began to nibble and kiss at the sensitive junction between her upper thighs and her lower cheeks. Her response only spurred Ashley on to greater intensity, licking and biting at the cleavage below her ass.

Ava was going out of her mind. Half the reason she took lovers from the resort staff every night was to keep herself from taking advantage of Ashley, but if she kept going like that then Ava was going to do something rash. She knew that she had to stop it, right now, but in the heat of the moment she instead leaned slightly over, resting her hands on the edge of the bed, wordlessly giving Ashley both the permission and the access to go deeper.

He took it. Pulling her cheeks further apart with his hands, Ashley kissed and nuzzled his way from under Ava's plump ass towards the middle, slowly, so painfully slowly making his way inwards, until finally his face was fully buried between Ava's cheeks and within their warm embrace he gave one, final kiss, tenderly pressing his lips to her clenching asshole then firmly pressing his tongue into her.

Unable to bear it anymore Ava screamed, sending Ashley tumbling back onto the ground in confusion.

"Mom, I'm sorry, I thought you wanted..." Ashley trailed off his staccato series of excuses as he fixed his eyes on Ava's ass and debated for a moment diving back in, in spite of everything.

"No, no dear, you didn't do anything wrong," Ava said consolingly as she caught her breath, stood up, and turned around. "It was... wonderful actually, you just caught me by surprise is all. If you still want to cum, lay down on the bed and give me a minute, you've certainly earned it."

Ashley couldn't believe his ears. The truth was he'd completely forgotten about cumming, he'd been so engrossed in Ava's ass, but now that it was actually happening he felt his cock surge against the steel cage, sending it's moment of freedom was at hand. He quickly hopped on the bed, laying on his back and delicately smoothing out his babydoll over his legs. A few minutes later Ava returned from digging around in the closet, holding in her hand a plum purple vibrator.

"If you want to cum, it's high time you learned how to cum properly, like a girl," Ava said with a wild glint in her eye. "Don't worry sweetie, Mommy is here to teach you how it's done, just lift up your legs and hold onto your ankles."

Obedience was so ingrained into Ashley at this point that he responded without thinking, lifting his legs and clutching his ankles, exposing his chastity cage and his ass to his mother. Not that he'd have done anything differently if he'd paused to think, he was too horny and too desperate to cum at this point to even think of doing anything else. Ava approached slowly, like a cat stalking it's prey, thumbing on the switch to the vibrator with a dull buzz. She held it to the flat front of Ashley's cage for a moment, sending him into convulsions as the vibrations transmitted directly inside him, then pulled it back with a wicked smile.

"You're going to enjoy this," she promised, then Ava pressed the vibrator head firmly against the bottom of the cage where it met his balls and leaned her head down to his exposed ass, licking up and down his smooth hole.

Ava hadn't lied. Ashley felt his whole world exploring as his cock inside his body and his balls outside it were both overpowered by vibrations. He'd heard of how much girls loved their vibrators, but he'd never felt it for himself, and now he understood it entirely. It felt like every nerve ending in the most sensitive area of his body was on fire. And to top it all off, Ava's wet tongue was mercilessly licking his hole and punching itself right inside. His ass was already loosened up by his fingering himself earlier while watching Ava with her lovers, but his mother's tongue felt far better than his fingers ever could. Just when Ashley thought he couldn't take any more, Ava thumbed the switch and the vibrator buzzed at a higher pitch, elevating the sensations coursing through him. It could only have been a minute at most, but he was already right on the edge. Ava had to stop, it was too soon, after a week of waiting he wanted to enjoy...

She thumbed the switch again, sending the vibrator into an even higher pitched buzz, like an angry hornets nest, and Ashley cried out in ecstasy. Spurt after glorious spurt of cum blasted from his body, squirting out through the holes in the front of his cage. It may have only taken a minute to get there, but Ashley's orgasm went on and on and on as he cried with joy, tears streaming down his face as he had a near out of body experience. Only when the last shuddering gasp and the last oozing spurt of cum had been milked from his body did Ava switch off the vibrator and stop licking his hole. As she rose Ashley opened his eyes and saw that the vibrator and Ava's face were both covered in ropey strands of his cum. His eyes went wide as Ava started to lick the vibrator clean, maintaining eye contact with Ashley the whole time as she gave the toy a slurping blowjob. Once it was clean, Ava tossed it to the side and crawled atop Ashley, aligning her face with his, then leaned in to kiss him.

Ashley's eyes closed naturally as Ava leaned in for the kiss, then opened again in shock as he realized that she hadn't actually swallowed any of the cum from the vibrator. Using her tongue she expertly shoveled glob after glob of it, mixed with her saliva, into his mouth, forcing him to swallow if he wanted to continue breathing. Once she'd transferred it all Ava pulled back a bit and whispered, "Remember sweetie, when you make a mess on Mommy, you have to clean it up." Ashley obediently started to lick the remaining cum from Ava's face, swallowing it all down before she leaned back in for one final kiss goodnight.