Hot Mom's Sissy Honeymoon Sweetie 3

~~~~~ Day 5: Third Date Locked In ~~~~~

The next morning Ashley woke up first with Ava still laying half atop him. He did his best to remain still, not wanting to disturb her and not wanting the feeling of her body pressed firmly against his to end. Ava's words the night before about him being the one she'd come home to echoed in his mind. He wasn't sure exactly where their relationship stood. Clearly it was growing into something much more intimate than a traditional mother/son relationship, but they hadn't put a label on it and for every taboo they broke there was an excuse as to why it wasn't actually a big deal. Sure, they cuddled together in the same bed every night, but that was just because Ava got lonely. They walked around the room wearing nothing but panties, but Ava insisted that boobs weren't really sexual, so it wasn't a big deal. They'd been on two dates, but those were just meant to be practice. They'd kissed but... well, there wasn't really an excuse for that. They'd kissed and as inexperienced as Ashley was he felt sparks in their kisses that went far beyond platonic.

As Ashley was considering all of this, he felt Ava's leg that was resting over top of him slide up. Her steady breathing made it seem as if she was still asleep, just shifting, but the motion dragged her exposed thigh over the soft satin fabric of Ashley's pink romper shorts. A surge of blood flowed into his nether regions as Ashley's body responded naturally to the stimulus. Then Ava's leg slid back downwards, triggering a further response that left Ashley stifling a moan. Before he had a change to recover, her leg slid up one more time, pausing to rest and press it's weight against his struggling erection. Then Ashley heard an amused snort beside him and turned to see Ava eyeing him with a bemused grin.

"What's the matter sweetie, are you trying to push my leg away for some reason?" she asked innocently.

"What? No, I just, it's just, a little sensitive," Ashley protested.

"Awww, Mommy's little guy is sensitive?" Ava asked in a teasing voice as she used her hand to squeeze Ashley's chest, pulling the swollen flesh outwards until she was pinching his puffy nipple in her fingers and twisting it roughly.

With that Ashley wasn't able to stifle his moaning any longer and his erection surged from halfway stiff to painfully hard. But then with an exertion of will Ava forced herself to let him go and slipped out of bed.

"I'm going to go take my shower sweetie, why don't you take care of that morning wood while I'm in the shower, I can give you a little privacy."

Ashley couldn't believe his ears as Ava walked away. Had his mom actually just told him to jerk off? And had she been deliberately teasing him? Whatever, he was horny, he was hard, and he needed to cum. Ashley waited a moment for the sound of the shower to mask his fapping, then slid the shorts of his pink satin romper to the side to free his aching cock and balls and started to stroke. After days trapped with his hot mom without cumming he should have been rock hard, but for some reason he was having a hard time maintaining a full erection. It still felt good, but as he frantically rubbed his half-chub Ashley worried that he might not be able to climax without additional simulation. Fortunately Ava had shown him just the trick he needed when teasing him, and Ashley ran his free hand along his chest, circling his fingers lightly around his still-hard nipple before pinching and twisting it. Again it had the same effect, instantly turbocharging his erection and sending waves of pleasure through his body. That gave Ashley a wicked thought. It was Ava's fault he was so backed up and horny and it was her responsibility to take care of it. He didn't have the nerve to try actually walking in on her in the shower, but he could at least peep on her while he took care of himself.

Ashley quietly got out of bed and carefully tiptoed around the corner, his hard nipples tingling at the sensation of his romper top sliding against his skin. He was rewarded with the perfect view of his mother dripping wet in the shower and facing away from him, water running down her body as his eyes locked on the fat tits he could see bulging out on the sides even from behind and on her beautiful curvy ass. He started jerking off again, imagining being with her, touching her, kissing her, making love to her. But then suddenly in his mind's eye Ajani was there as well, and Ava's focus was turned towards him. It shouldn't have been surprising that that's where his mind went after watching primarily Blacked porn for as long as he could remember, but the shock of that mental image still rocked Ashley, causing him to stumble backwards a step and crash once again into the stupid nightstand he'd bumped into the day before.

"Ashley sweetie, done already?" Ava called out without turning around. "That's great, I could use your help in the shower if you don't mind."

"You could what?" Ashley asked in total shock, weighing that dream scenario against revealing that he hadn't actually managed to finish yet.

"I don't have a scrub brush and with my tits it's just so hard to really wash my back," Ava explained. "Don't worry, we've already seen most of each other at this point, it's not like it really matters. Now don't make me tell you again, strip down and get in here before the water gets cold."

Moving as if in a dream Ashley obeyed. He still hadn't managed to get off, but that hardly mattered compared to the opportunity for a shower with Ava. He slipped the straps of his romper over his shoulders and let it slide down his body, working it over his wide hips and letting it fall to the ground next to Ava's. Then he stepped forward hesitantly, as if worried that this was too good to be true, but no objections came as he stepped into the shower behind Ava, marveling at her beauty up close as he stared at her shimmering wet tanned skin. He was only snapped out of his reverent state of worship by a soapy loofah being handed back over her shoulder.

"Here sweetie, take this and get to work. I haven't been able to give my back a proper wash since we got here."

Ashley did as he was told, gently scrubbing in little circles on Ava's back, feeling the soft touch of her warm skin under his fingertips, starting up at her toned shoulders and gradually working his way down her back, to her narrow waist, and to her curvy hips. His eyes were fixed on her ass, which looked huge up close, especially compared to his still-twitching erection. All it would take was a little half-step forward and he'd be buried between her lush cheeks. Inches from paradise, Ashley continued working his hands downward, sudsing up the top of his mom's booty while working his hands onto her hips, mentally preparing to take the plunge. But just as he worked up the courage, Ava turned, rinsing off her back in the shower as she faced Ashley.

"No need to worry about down there sweetie, I was able to wash that before you came in," she said. Then Ava looked intently at Ashley for a moment before breaking into a laugh. "See, it's not like we had to worry about you seeing anything new joining mommy in the shower, you've already seen my tits and I don't think there's anything that could pry your eyes away from them now."

"Sorry Mom! I didn't mean to stare, I just... you're just...."

"It's fine honey, it's sweet really, you enjoying your old mom's boobs when I'm sure you've seen plenty of girls your age with nicer perkier ones."

"No, yours are the only, I mean, the best, I mean, you're beautiful mom," Ashley said sincerely as he pulled his eyes up to meet Ava's and stared into hers brimming with emotion.

Ava stood under the water staring back into Ashley's eyes for a long moment, his hands were still on her hips from his aborted attempt to try for something from behind and she rested hers on his shoulders.

"Oh Ashley, I'm so glad to be where we are with nothing separating us now, not just physically, but on a deeper level too. I feel as close to you as a mother can be to her child."

"Thanks mom, me too," Ashley answered before finally breaking the soft eye contact they'd held for so long. "I guess I can go ahead and wash myself now if you're done showering."

"Oh nonsense, you washed me, the least I can do is return the favor!"

Ashley tried to protest, secretly hoping that Ava would give him some much needed privacy to finish the deed he'd started earlier while secretly watching her, but she would not be swayed and insisted on 'washing her little boy just like she used to'. At first it was frustrating, as all Ashley could think of was how hard he'd be beating his meat after seeing Ava naked in the shower if she'd only leave. Then it was erotic as Ashley processed that this beautiful woman he'd spent the past several days obsessing over was touching him all over while he stood naked in the heat and steam. Then finally it was tenderly sweet as Ashley realized that while Ava's touches were without boundaries, they weren't intended to arouse, instead gently caressing him in a way that could best be described as platonically romantic. As if they were fully intimate lovers without ever having made love.

When they shower finally finished and they started toweling off Ashley's only consolation in his disappointment was that at least Ava hadn't seemed to notice the erection he'd maintained throughout. Consolation that was dashed to pieces by her next remark.

"My goodness, your little stiffy may be on the smaller side, but it just doesn't seem to ever go down even after you masturbated," Ava said with a laugh as she wrapped her hair in her towel and reached for her robe.

Ashley started to protest that he hadn't managed to finish, but then decided against sharing that personal detail.

"I didn't... I mean, it's not little Mom.... is it?"

"Oh sweetie, I'm sorry, I forgot how sensitive you boys can be about that. Forget I said anything, it's quite the cute little thingy, and you know there are girls out there who like all kinds of different sizes. But do you have this problem often where it won't go down after?"

Ashley demurred and mumbled a noncommittal answer, walking back to the main area to get dressed while Ava did her makeup. He spent a few minutes pacing around, debating what to do. His erection wouldn't go down, not after what he'd just been through, but he also couldn't very well jerk off with Ava just around the corner doing her makeup. He tried putting on a pair of panties, but that only made him more excited and the light fabric had no chance of containing his erection. Finally he did the only thing he could and sat down on the edge of the bed, waiting and hoping for the swelling to go down.

Fifteen minutes later any minor softening Ashley had managed was wiped away in an instant when Ava walked in, her makeup finished, wearing nothing but a thong and a smile.

"I know you saw it all in the shower anyway, but I thought I might as well go on wearing panties around the room and..." Ava paused as she saw Ashley still nude and suffering from the same affliction as before. "Still honey? We have to get dressed and get on with our day, can't you make it go down?"

"No?" Ashley answered uncertainly. "Maybe I can just stay in while you go have fun."

"Or maybe..." Ava paused for a long moment pondering, "I could help you make it go down?"

For the second time that morning Ashley couldn't believe his ears, but Ava continued looking at him as if awaiting an answer, and so he nodded his head.

"Wonderful, I have some experience with problems like this and I'll take care of everything. You just stand up, close your eyes, and give mommy and minute and I'll take care of you."

Ashley stood and closed his eyes tightly as he'd been told, imagining Ava giving him a handjob, or maybe even taking him into her mouth. He heard some rustling sounds in the room and wanted to take a peek, but didn't dare risk ruining his chance at this. After a minute he thought he could hear Ava returning to stand in front of him, then going down to her knees. He felt one of her hands tracing lightly down his thigh, then the other take hold of his still-erect shaft by the base. He couldn't believe she was touching him there, and braced for the warm, wet feeling of her mouth wrapped around his member. But instead what he felt was the pins and needles sensation of sudden shocking cold. Ashley's eyes shot open and looking down he saw Ava gripping the top of his junk and forcing his cock and balls down into an ice bucket filled with sloshing cold water. He tried to pull away, but her grip was too tight and fighting it made her nails dig into his sensitive skin. In a few minutes it was all over, and Ava released her grip while lowering the bucket. Ashley looked down and given that he couldn't feel a thing he was relieved to see that everything was still there, although shrunken smaller than he'd ever been before.

"What the hell was that?"

"You said you needed help getting it down," Ava answered evenly, "and that certainly did the trick. Look how small and soft it is now."

"So that was your big plan, to try to freeze my dick off?"

"No, that was just phase one sweetie, if we leave you like that you'll just pop another erection soon, and I've been dying to put on our swimsuits and hit the beach. That's why you're going to wear this."

Ava produced a small metal contraption in the palm of her hand, and Ashley blushed with shame as he instantly recognized what it was. A few times when he'd gone deep down the rabbit hole of Blacked porn he'd ended up jerking off to videos where the beta white guys had been locked up in chastity, but in his wildest dreams he never thought anybody actually used those things in real life.

"It was a gag gift from one of my bridesmaids at the bachelorette party, 'just in case Greg was disappointing', you see it goes on your penis and..."

"I know what it does Mom!" Ashley sputtered, "But there is no way you're putting that thing on me!"

Ava stood slowly, looking ever so slightly down into her son's eyes as he struggled to maintain his composure and keep his eyes looking up and away from her tits.

"You know I was really looking forward to our third date tonight," Ava offered, "and I know you were too. But if we can't get you dressed then we can't go, and you can't wear any of your new clothes with that thing sticking out. Just do this for me and I promise we'll have a great time together tonight. Please?"

Ashley knew in that moment that he was well and truly over a barrel, and his resistance quickly melted into resignation. There was very little he wouldn't do for Ava at this point, especially with the all-important third date on the line. Ava read her moment of opportunity and dropped back down to her knees, deftly slipping the base ring around her son's still cool balls and pressing his limp cock back behind the flat front until it clicked in place. Then looking up at Ashley with a happy smile, she placed the key in the lock, turned it with a quiet click, and stepped back to admire her handiwork.

The deed done, Ashley stood still for a moment unsure of what to do next. Sensation was returning slowly to his chilled bits, so while he couldn't exactly feel what had happened he was able to pick up on a vague sense of tightness, which was unsurprising as the flat-fronted cage pulled everything back into a nearly smooth line with the downward curve of his abdomen. His first thought was to wonder what new clothes from Ava's wardrobe he'd be and to pull off now that he was effectively tucked away, imagining how he'd look and the reactions he'd get walking around the resort. Ashley was so wrapped up in his dream world that he didn't even notice Ava had stepped away to her dresser until she returned, holding a pendant necklace in one hand and the key she'd just locked his chastity cage with in the other. He recognized the necklace at a glance, it was a Mother's Day gift from a couple years ago with a silver heart-shaped pendant inscribed 'A Mother is her Son's First Love', but he wasn't sure what she was doing with it. More pressing was the question of what she was doing with the key.

"Okay, we did it," Ashley said, "Now give me the key and we can get dressed."

"No, I don't think so sweetie," Ava replied, her voice soft but firm, like a mother telling her child that he couldn't have dessert. "You know how you're always losing things, and besides, it's technically my key anyways, right?"

As Ava spoke she threaded the head of the key onto the necklace chain, letting it slide down until it rested in the center next to the heart pendant Ashley had given her.

"Wait, you're going to keep it? So I'm going to be stuck in this thing?"

"Oh, it's not like that Ashley," Ava said as she reached back to fasten the clasp and let the pendant and key fall into her cleavage, "I'll let you out when you really need it, although that shouldn't be for a while since you just took care of yourself. And in the meantime, your key will be right here, safe and sound, where you can keep an eye on it."

Ava winked mischievously as Ashley stared at the key and the heart he'd given to his mother, both nestled safely between her breasts. Ashley tried to think of the words to protest, but as wrong as the situation seemed he felt a deep instinctual desire to support Ava and to put her needs and wants before his own. Surely she knew what was best for him, even if that meant wearing her silly chastity cage, and as long as she was happy, maybe he could be too.

With that matter settled, Ava and Ashley started trying on swimsuits together so they could finally hit the beach. As Ashley watched Ava model one swimsuit after another sensation gradually returned fully to his caged cock, but for all the excitement he felt watching her parade around for him nearly nude, everything stayed securely just where it was meant to be. He could feel the blood rushing and himself trying to get hard, but the cage was so tight that it didn't even let that process start, sparing him the agony of dealing with an erection. There were other signs, like the sudden pointy hardness in his newly puffy nipples, but that was far more manageable. Finally Ava settled on a turquoise leopard print string bikini and declared that it was Ashley's turn. It took a few tries to find one of Ava's suits that was modest enough to hide the reduced but still present signs of his manhood and that had a top adjustable enough to handle his mostly flat chest, but eventually they settled on a cotton candy pink polka dot bikini with a halter top and a matching sarong. Ashley still wasn't sure about wearing it out until Ava pushed him in front of the full length mirror and forced him to take a look.

He was hot. Like, legitimately hot. Ashley had never had the most boyish figure, but something about the recent changes had pushed his body past androgynous and well into feminine. His skin was still smooth and soft from the accidental spa treatment, and his long unruly blonde hair suddenly looked less like a gamer dude's unruly mop and more like a brat tomboy's. His face seemed to have grown a bit rounder and fuller, but the real change was in his body. He'd always had bigger hips and had been teased in school for having a 'bubble butt,' but it somehow looked even wider now and his waist seemed thinner, emphasizing that he was honestly looking pretty thick, especially from behind. And as for the swelling on his chest, even though they were nothing compared to Ava's, he had to admit that he had a perky set of little boobies.

"Mom," Ashley asked as he turned in shock, " What's happening to me?"

Ava stepped in close and took Ashley's hand in her own.

"I don't know sweetie, maybe this is who you've really been all these years and you're just now seeing it. But I love you, and right now I just want to enjoy our day together."

With that the pair finally left their suite and took the walk to the beach, walking hand in hand. Ashley was growing more used to being looked at, and after checking himself out in the mirror he had to admit that if he saw a girl walking by looking that way then he'd be looking too. Even at the beach where other guests of the Pink Lotus Resort were showing off some skin in swimwear of their own, Ashley and Ava pulled far more attention than most as they looked around a bit before selecting a pair of chairs set up under an umbrella in front of the gently lapping waves of the Caribbean. Once they'd settled in, Ava announced that they'd need to apply sun lotion to avoid burns, pulling out a bottle of SPF 30 and instructing Ashley to lie down so she could apply it.

As usual, Ashley followed Ava's lead, laying back in the chair as she started applying the thick lotion to his upper body. He tried suggesting that he could take care of it himself, but Ava insisted that with his fair skin she wasn't going to take any chances with him getting a bad burn. The high SPF cream was so thick that it took a lot of effort for Ava to fully rub it in to Ashley's skin, but she would not be swayed so he laid back and enjoyed the feeling of her working it in to his slender arms and shoulders, his chest and torso as she carefully worked it just a little under the edges of his bikini halter top to ensure he didn't get burned there, and down to his smooth legs.

"You have the nicest skin now dear," Ava said as she worked the lotion into Ashley's thighs and up under the edge of his sarong.

"Ummm, thanks Mom," Ashley said, not quite sure how to take the compliment.

"You know most girls would kill for skin this soft and smooth," Ava continued as she squeezed and kneaded his supple flesh beneath her fingers, "just begging to be touched and perfectly creamy white. I don't know what was in that treatment they gave you at the spa, but you'll have to ask them to repeat it for you as needed, I want your skin to stay just like this."

Ashley nodded along, not sure that he'd actually do that, but toying with the idea given how much Ava seemed to like it and his much he was enjoying her hands all over him. More pressingly, her bringing up the spa had reminded him that he hadn't had the chance to have his now daily indulgence of a coconut cream drink. There was something about it that was so deeply satisfying and the vitamins or whatever they packed it with made him feel sparkly inside. His throat tickled and itched at the thought of one, and so while Ava finished on his legs he waved down one of the attendants. The man walked over and it wasn't until he was standing right next to Ashley that he realized just how big he was, towering over him as he reclined on his beach chair. He was wearing the usual Pink Lotus uniform, and as was typical for the staff here the bulge in his tight shorts was prominently visible for those who cared to look, and from where he was sitting Ashley couldn't help but look up at it, standing just a for away.

"May I help you ladies?"

Ashley didn't even bristle at his mistake, his throat went even drier as he thought about the ridiculousness of this black Adonis serving him, if anything it should be the other way around. Finally he managed to find his voice, although perhaps due to the dryness in his throat or the uncertainty he felt it was higher and softer than his usual tone.

"If it's not too much trouble could you go to the spa and ask them for one of their special coconut cream drinks? Tell them it's for Ashley, they may have made one for me already."

The attendant left on his mission and Ava had Ashley flip over so she could get to work on his backside. To Ashley's surprise while Ava had lotioned his front while working from the side, for his back she straddled him and used his thick booty as her seat. He was uncomfortably reminded of the way Ajani had sat on him in the same way in their first yoga session, grinding himself in as Ashley helplessly struggled to reach his position. But instead of a barely restrained bulge forcing it's way between his cheeks, he now experienced his mother's warm thighs squeezing them together, emphasizing how much he'd grown back there.

"Are you sure you should be drinking so many of those coconut cream drinks?" Ava asked as she worked the lotion in further and further down his back. "I think they're going straight to your hips!"

"They're fine Mom, I'm sure they're totally healthy, they're from the spa."

"I suppose you're right sweetie," Ava said as she took one of Ashley's cheeks in each hand and squeezed, "besides, big butts are in now, right?"

Ashley felt an unexpected surge of pleasure and an accompanying failed attempt from within his chastity cage to respond. He'd never really thought of his ass as an erogenous zone, but something about the way Ava took hold of it suddenly sent him wild.

"Either way, you should be good to go for a while," Ava said, giving Ashley's butt a playful swat goodbye as she stood and released it. "Your turn to lotion me now."

Ava handed Ashley a bottle of SPF 4 tanning oil, explaining that her dusky skin didn't need as much protection as his, then laid back and told him to get to work. Feeling how runny the oil was compared to the lotion she'd used on him, Ashley squirted some out directly on her chest. It landed near her sternum and started to naturally spread, coating the heart pendant he'd given her for Mother's Day and the key she'd used to lock him in chastity as they sat on full display between her breasts as they flattened in her reclined position.

The sudden urge to snatch the key and bolt seized Ashley's mind, as he started to rub the oil in around her chest and onto her soft breasts which were mostly uncovered by the skimpy bikini she'd chosen. But then he thought about what giving up that freedom had bought him as he sat there on the beach next to the hottest woman he'd ever known, casually rubbing oil onto her tits. And it's not like he'd had much opportunity to use his cock since they'd gotten here anyways, so it might as well be locked up when he thought about it. His fingers brushed against the heart and the key, twin symbols of his devotion to Ava, then continued outward, carefully rubbing the oil into her arms and shoulders, trying to focus on the moment and not think too hard about the control he had willingly surrendered.

Just as Ashley had done, when Ava's front was finished she rolled over so that he could take care of her back. He hesitated for a moment, remembering how she'd straddled him and sat on his backside, wondering if it would be okay to do the same. The back of her bikini was even skimpier than the front, just a tied string for the top and a string thong disappearing far into her crack for the bottom. As he was wavering Ava reached her hands back and loosed the string tie on her back, letting the ends fall to either side, and told Ashley to hurry up or she'd get one of the attendants to help her out instead. That was all the motivation Ashley needed to push himself over the edge, and he sat himself down right on Ava's virtually bare ass and set to work oiling her back. Without really meaning to he found himself naturally rocking slightly forwards and back, pressing himself into his mother's booty, holding for a moment, then pulling back and letting her soft ass jiggle and roll back into place. It wasn't until he'd been doing it for a few minutes that Ashley realized what he'd been doing: humping her from behind like a dog in a heat. He stopped, grateful that she hadn't seemed to notice, and also strangely grateful that he was locked away in the cage she'd given him. If not for that then he'd surely have popped an embarrassing erection by now, ruining the moment. Instead he was free to continue his work, sliding down to sit on her legs as he continued to oil her ass and thighs, relishing in the intimate closeness they were able to share.

Eventually he'd finished, although he didn't want to admit it, and he continued rubbing his hands along Ava's toned calves, unwilling for it to end. But then the attendant he'd waved down returned, holding a platter with a beautiful brown coconut on top that instantly made Ashley start salivating by repeated association. He quickly stood and took his seat as the attendant reached them, thanking him and taking the offered drink with slightly shaking hands. Although his natural instincts wanted to throw it back and chug the delicious beverage, Ashley had just enough self control to force himself to enjoy it slowly, savoring small sip after small sip as he enjoyed the ocean view, the warm sun, and the cool wind tickling his skin. Somehow he swore that every time he had this it got better, although perhaps it was just a side effect of taking the time to enjoy it properly instead of respectively wolfing it down. The natural sweetness of normal coconut milk was there as the base, but there were complex layers of cream and salt and a hint of acid bitterness beyond that which swirled on his tongue in perfect symphony. By the time he was reaching the end of the drink Ashley was doing everything he could to extend the experience, playing with it in his mouth, rolling it back and forth with his tongue, moving it from cheek to cheek until finally it had mixed with so much of his own saliva that he had to swallow it down and take the next delicious sip. The usual inner warmth it gave him spread from his tummy out to every limb, and when he'd finally scooped out the last bits he lay back to bask in the glow, wondering if it really was going straight to his hips and not particularly caring if it was.

After a while Ashley was awoken from his blissed out state by Ava turning over to tan her front. He saw with mild disappointment that she'd refastened her top, keeping her breasts technically covered by the strips of turquoise leopard print fabric, but he was still riding high on his special drink and didn't feel like there was anything that could bring him down.

"Ashley sweetie, I think you forgot to do my feet earlier," Ava said lazily, "be a dear and oil them up for me."

Ashley moved as if in a dream, happily kneeling down in front of Ava's chair and squeezing more oil onto his hands before massaging it into her feet. Maybe it was the lingering taste of coconut cream on his tongue, or maybe it was just that he'd never been so close to a woman's feet before, but Ashley found himself licking his lips as he stared at them and worked the oil in diligently with both hands. Thinking of licking from her heels all the way up her soft soles, wondering how her toes would taste, what they would feel like wiggling between his lips, inside his mouth. He'd never had a foot fetish, or really understood it before, but as he knelt at Ava's feet slowly working the oil into them under the warm sun with the taste of his special drink still fresh on his lips. She was so clearly naturally meant to be above him, kneeling before her feet felt right, like he'd found his place in the universe. He leaned forwards, eyes closing as his lips pursed, unsure of exactly what he intended to do, until finally he'd closed the distance and pressed his lips against the soft bottom of Ava's big toe, gently depositing a devoted kiss.

From above him he heard Ava giggle uncontrollably as she pulled her foot back. Ashley's heart fell as he cursed himself for getting caught up in the moment, pushing too far and ruining a good thing.

"I'm sorry!" he yelped, "I didn't mean to, really."

"You didn't mean to kiss my to big toe?" Ava said as her laughter stopped and she arched an eyebrow quizzically. "How exactly does that happen by accident?"

"I... ummm... I don't know," Ashley admitted. "I'm sorry you didn't like it."

"I never said I didn't like it sweetie," Ava said with a smile as she extended both feet back down in front of Ashley's face. "You just caught me by surprise and it tickled a little. Now tell me, do you like Mommy's feet?"

Ashley nodded emphatically.

"Good, because I was really enjoying that footrub and it's hard to find a boy willing to really put in the effort down there. You may resume, go a little easier on the oil, and Ashley?"

"Yes Mom?"

"I have nine more toes to kiss before you're done. Make sure they don't get jealous of this one," Ava said as she wiggled her big toe in his face.

Ashley couldn't believe his luck and set to the task with relish, working his hands back and forth over Ava's feet and depositing sweet kisses on her toes whenever she wiggled them at him to signal it was time. As he worked he leaned forward further and further until his field of view was filled by her feet. He was so engrossed in his task that he lost all track of time and didn't even notice that Ava had sat up until he felt her hand tousling the hair on the back of his head, triggering him to look up at her.

"Good boy, that will be all for now," she said. "Let's go for a walk."

The rest of the afternoon the pair strolled and enjoyed the beach together, holding hands as they walked along the line of the surf and stopping in at a kitchy tiki bar for some fruity drinks. After a few cocktails Ava got the idea in her head of going for a swim to cool down, but Ashley was concerned that without his sarong people would see what was hiding under his bikini bottoms. Between the liquid courage of rum and tequila and Ava's pressing he finally relented, pulling off his sarong and walking closely behind Ava out into the water. Once they were waist deep Ashley finally let himself relax, floating, swimming, and splashing with Ava as the two frolicked together under the sun. As sexually charged as many of their encounters were due to Ashley's growing obsession with his hot mom, it was incredibly freeing to simply play together and enjoy each other's company. She was the person he was the closest to in the entire world, and after several days of intense bonding now occupied a strange place relationally, but there was no denying that she was his best friend and that regardless of all the rest she was the person he wanted to be with.

As they walked back onto the beach Ava handed Ashley his discarded sarong, and he took it thoughtfully. Looking down at his bikini bottoms he could barely see the outline of his chastity cage and behind that the dainty bulge of his balls tucked back between his legs. If he didn't know what he was looking for it was unlikely he would even notice, and a quick scan of the faces of those on the beach nearby, several of whom were checking them out, confirmed that either nobody noticed, or nobody cared. So Ashley held the sarong in his free hand and walked beside Ava, happy and without a care in the world.

As evening approached the pair headed back to the honeymoon suite to prepare for their third date. Ava went to the closet and dug around for a moment before emerging with a pair of beach cover-ups. One was a flowing piece of white linen fabric loosely shaped as a flowing dress or tunic with wide three-quarter length sleeves and a series of bright flowers sewn into a Y pattern running around the collar and down the front. The other was a blue knit crocheted dress with an open pattern and bits of lace detailing throughout.

"No time to get changed into something new, but we should at least put on some cover-ups over our suits to look a little more presentable at dinner," Ava said as she held the two dresses out. "I think you'd look cuter in the blue one, what do you think?"

"I think it looks like a dress, I'm not wearing that!" Ashley responded.

"Why not sweetie, don't you want to go on our date tonight?"

"Well yeah, but can't I just wear this, or the other clothes you've given me? Even if they're a little girly tops and bottoms seem at least a little closer to what I should be wearing than an actually dress."

"Do they? Really?" Ava asked as she looked up and down Ashley's bikini-clad body.

"I don't know," Ashley said, exasperation creeping into his voice, "It just seems different, and I don't want to."

"Well if you really don't want to then I suppose that's alright," Ava said as she started playing with the pendant on her necklace. "I just know you were looking forward to our third date so much, and I'd hate for such a little thing to spoil the mood."

Ashley froze as he saw Ava's fingers dance around the key to his freedom, combining that understated display of dominance with her implications regarding their third date. Was she actually planning to release him and do something together after? Was she threatening to keep him locked if he didn't do what she said? It was difficult to parse, and he didn't want to ruin things by asking too many questions, so he decided that he'd best just go along with what she wanted. Besides, it was just a dress.

"No, it's fine, I'll wear one. But I want to wear the white one, it's more like an oversized shirt at least."

"Okay dear, that's fine," Ava said with the practiced tone of a mother dealing with her child's tantrum. "You'll look adorable in the either dress, I just want to make sure you understand the importance of dressing up and looking your best for a date, even if it's just with your old mom."

It may have been more like an oversized shirt, but as Ashley pulled it on over his head he could still clearly tell that it was a dress. What he hadn't been expecting was how strong the urge to twirl in it would be. The light fabric flowed freely as he walked and he knew it wouldn't take much for him to get the whole thing spinning around him. He waited into Ava was in the bathroom touching up her makeup, then finally gave in and took it for a whirl in the bedroom. The feeling of freedom as the beautiful dress splayed out around him was exhilarating, and Ashley found himself suppressing a giggle that made Ava ask if everything was alright. Ashley just smiled to himself and called back that it absolutely was. A few minutes later Ava came out wearing her cover-up, the knitted fabric stretched and straining around her curves as the gaps expanded and the knotted threads sank slightly into the soft skin of her tits and ass. Somehow it was more beautiful and more erotic than seeing her in the bikini she still wore underneath, even more than seeing her nude. Ashley's jaw dropped.

"See sweetie, it's worth it to get all dolled up for a date," Ava said smiling. "Now let's go out to dinner."

Dinner at their private table on the beach was wonderful, as always. The food was delicious, the champagne was cold and refreshing, and the company was electrifying. After having their evening meal crashed by Ajani the night before, Ashley was ecstatic to have Ava all to himself again, pulling their chairs close together as they talked and laughed. He didn't know exactly when it had happened, but at some point Ava had apparently kicked off her wedge heels under the table and started gently tracing her bare feet over his own. A thrill ran through Ashley as he remembered massaging and kissing those same feet earlier in the day and now felt those same soft soles sliding affectionately up and down his leg.

Ashley had never been on a date before his first practice date a few days ago with Ava, but he'd heard all sorts of things about what happened after third dates, once both parties knew well enough if they were interested in taking things to the next level. He'd already crossed so many boundaries in his developing relationship with Ava, and he felt a real chemistry there that he hoped she felt too, could tonight be the night that they took things all the way? Those thoughts echoed again and again through Ashley's mind as they finished their meal and continued their conversation until after the sun had set. When the words gradually ebbed away they sat together in comfortable silence, enjoying each other's company even without words. Then without saying a thing Ava slid her wedges back on, stood, and offered her hand to Ashley. She led them silently side by side down the sandy path back to their suite and Ashley gently rested his head on her shoulder as they walked. Finally they reached their destination and turned to face one another. Ashley wondered what he should say, what words would seal the deal on the perfect evening they'd had together, but before he could speak and ruin the perfect moment of silence Ava cupped his chin in her hand, tilted his head up to face hers, and kissed him.

The kiss started gentle and soft, two pairs of lips meeting silently in the darkness, sliding against one another in muted need. Then her hand slid down from his chin to his chest, brushing against his nipples as her other hand wrapped around and cupped his ass from behind, lifting him on his tiptoes and bringing him closer to level with her elevated height. His hands followed suit as his body was pressed into hers, racing up and down her growing familiar body, squeezing, gripping, pawing, needing. Her kiss grew more insistent, her mouth opening slightly in invitation. His mouth followed, opening just a crack, which was enough for her tongue to go darting in, pressing against his own and dancing together with it. She brought one hand up behind his head, taking him by the neck and pulling him in closer as her mouth opened wider and her tongue pressed deeper. He tried to return the gesture by pushing his tongue back into her mouth, but was repelled by her own pressing against his, making it clear that she was the one kissing him and that his role was to receive. So he closed his lips around it and began to suck on her tongue, willing it deeper into himself as their bodies writhed against one another. Then as quickly as it had begun, it was over. Ava pulled back, releasing her grip on Ashley's neck and taking a step away.

A quiet minute passed as both labored to catch their breath.

"I had a lovely time tonight," Ashley finally offered. "Should we head into the room now?"

"I.... I don't think that's a good idea sweetie," Ava replied hesitantly as if she couldn't believe the words coming out of her own mouth. "It was a wonderful date, really, and I know you had your hopes up for something, but tonight I think I really need to take some time by myself. Maybe you could take a walk and I could have the room for an hour or so?"

"Uhh, sure, I guess," Ashley answered, unsure of how to handle that kind of answer after a kiss like that.

"Oh thank you so much for understanding Ashley, it means the world to me."

After watching Ashley walk off confusedly into the night Ava entered their suite and slumped down to the ground with her back to the door. She didn't know how it had happened. It had started harmlessly enough, taking Ashley as her companion when she needed comfort and letting him have his practice dates with her. She'd thought she'd be fine since he was very much not her type, and it's not like he'd be into her anyways. But then she'd started having fun dressing him up, and had been surprised to find that the girly look on him was oddly attractive. Especially when combined with his sweetly attentive affection and increasingly obvious infatuation with her. She should have put a stop to it then, but it felt too good to be desired in that way and the truth was that she had been falling for him piece by piece and although she was the one with a key and a heart around her neck, he held hers no less certainly. Tonight she'd almost done it. She'd never been on a date so perfect and that kiss after had set her whole body on fire. Only in the last second had she managed to stop herself from unlocking the chastity cage and having her way with her own son. She knew she had to do something to help her control the urges coursing through her, and so she did the only thing she could. She took out her phone and snapped a hot selfie showing off her cleavage, then pulled out Ajani's business card and texted it to him with the message 'You up?'. A few minutes later the yogi was at her door, ready to help her scratch that itch.

Meanwhile Ashley wandered aimlessly around the resort, wondering what he'd done wrong. He replayed the events of the evening over and over, but couldn't figure out what it could have been. Ava had been the one to come on to him, and he didn't think he'd pushed anything. His only regret was that he hadn't asked her to unlock his cage or give him the key before departing. It would have been a little awkward, but she'd promised to let him out when he needed it, and after that day and that kiss he needed it badly. He considered carefully before finally deciding that she probably wouldn't mind her hour of solitary time being interrupted for a quick request like that, so he made his way back to their suite while working up the courage to ask.

He was unsure what the strange noises coming from the honeymoon suite were as he approached, and for a moment his heart raced as he worried that Ava might be in trouble, it sounded like a man's voice coming from inside! He ran quietly to the window, peeking over the sill to see what was happening, and was met by the sight of his mother on her knees in front of the yoga instructor they'd taken out to dinner the night before. Ashley managed not to yell, concerned that the large black man was forcing himself on his mother, and watched as she hungrily slid down his pants pulling out his big black cock with both hands then licking it from the base of the shaft all the way up to the tip before sucking the head into her mouth.

She didn't look to be in distress, but Ashley couldn't make himself stop watching as Ava bounced her head up and down on the biggest cock he'd ever seen while jerking it with her hands. Her moans were similar to the ones she'd made earlier in the day as he massaged her feet, deeply satisfied, and as she worked more and more of the cock into her mouth and down her throat it became increasingly clear that far from being in danger, Ava was the one driving the action. Ashley marveled at the size of Ajani's cock, even with both of Ava's hands wrapped around the base of it one on top of the other, there was enough meat left for her to gag as she impaled the back of her throat on it. It was so hot, and Ashley was so horny, that he couldn't resist sliding a hand down, lifting up the hem of his cover-up dress and sliding his fingers down into his bikini bottoms. Of course he was still securely locked within, so lacking other options he started rubbing his fingers in circles into his exposed balls, occasionally pulling his hand back to plap them gently. It hurt a little, but it also felt good, and aroused as he was from watching Ava slobbering all over a huge black cock Ashley would take whatever he could get.

As Ashley continued to masturbate while watching through the window, Ava finally stood and stripped out of her dress and her bikini, then crawled up on the bed on all fours and shook her ass back at Ajani. He didn't need a second invitation, stepping forward and taking hold of Ava's ass with both hands mounting her doggy style. From his side-view Ashley could see the first few inches of Ajani's cock plunge into Ava from behind in the first violent thrust. He couldn't imagine how she was taking that girthy monster inside if herself so easily, and his wonder only grew as Ajani started pumping in and out, forcing his cock another inch deeper into Ava with every thrust. She squirmed a bit, struggling for a moment to get away as Ajani's cock was buried deep inside her, but with his hands on her hips she couldn't get away, and soon she'd given up the attempt and was instead throwing her ass back into him, helping to work in the last couple inches. Ajani paused for a moment to let Ava accommodate to his python, then he started pistoning in and out. From his angle Ashley had the perfect view of Ava's swinging tits, hanging low from her body and rocking in motion with each of her lover's thrusts. He reached his free hand up to his own blossoming chest, playing with his own nipples as he imagined what it would be like to have a set of boobs like hers. As he watched he couldn't help but notice that the only thing Ava was still wearing was the necklace he had given her, as the heart pendant and his key were swinging right along with her breasts.

Then Ashley sensed the energy in the room escalating in the fevered moans coming from both Ava and Ajani. Without warning he pulled out, flipped Ava over into her back, then stepped forward again, reinserting himself. Ava mewled with delight and wrapped her legs tightly around his torso, triggering Ajani to bend down and pick her up in his strong arms, lifting her cleanly off the bed and impaling her fully on his cock. Now fucking face to face, Ava and Ajani started to kiss passionately, and Ashley felt a sudden pang of betrayal. He understood on some level Ava fucking a hung black man like Ajani, but a part of him hoped that it was just sex, not love. Love like they had together, or at least he'd thought they had. Their kiss earlier had seemed like something out of a fairy tale, but now less than an hour later she was kissing some random dude? Ashley had to take his mind off of it, had to do something, get off somehow. Acting on instinct he slid the hand in his bikini bottoms further back, pressing his fingers into the soft area behind his balls. It felt surprisingly good, like somehow he was massaging his trapped cock from below, and the further back he went the better it felt. He kept on pressing while watching Ava and Ajani fuck until suddenly his fingers slipped and he yelped in surprise and pleasure as in his blind excitement he accidentally fingered his own hole. Ashley dropped to the ground, sure that he'd blown his hiding spot, trying to process the strange and powerful sensation he'd just felt while waiting to be caught.

Ava was riding Ajani like a great black stallion, nearing climax when she thought she heard the sound of Ashley's voice. That little bit of connection was all she needed to push herself over the edge, clenching her pussy down on Ajani's cock while burying her head in his strong chest and digging her fingernails into his back. When the shuddering waves of her orgasm finally subsided Ajani was still going strong, so she whispered to him that she wanted him to cum on her tits. He needed no convincing, lifting her off and setting her back onto the ground before she took hold of his cock and jerked rope after rope of thick, rich cum onto her chest.

A few tense minutes later Ashley heard the front door of the suite open and Ajani come stumbling out. He tensed, sure that he was about to be dragged into the room to explain himself, but instead Ajani continued on down the path humming happily to himself. Ashley waited a few more minutes to make sure he wasn't coming back, then went into the room to check on Ava.

He found her laying on her back on the bed, rubbing her tits together. She seemed tuned out, almost like she was high, and in the minute before she seemed to notice that Ashley was standing there he got a perfect view of her dripping wet pussy. When she finally noticed him she made a quick apology, then got up from the bed and searched around for her discarded bikini bottoms, pulling them on to maintain some level of decency, before asking Ashley what he wanted.

"Um, I was wondering if maybe I could have the key back for the night?" Ashley asked tentatively.

"Back? No, I don't think so," Ava replied in a sing-song voice that made it clear she was still in an altered state. "But I can let you out if you'd like. Come here."

Ashley walked up to Ava and she kneeled down in front of him. A thrill raced through his body at the thought that she had been kneeling the same way in front of Ajani when she blew him. Keeping her necklace on, Ava leaned in close, pulled down Ashley's bikini bottoms, and inserted the key into the lock, pressing her tits against Ashley's bare legs as she did so. With a click the device separated into two pieces, and Ava pulled the cage away and set it on the ground. Ashley could feel his penis stretching out after spending all day in the flat cage, but as aroused as he was it remained flaccid as it tried to adapt to being free once more.

"I had such a beautiful day with you sweetie," Ava said as she remained in position in front of him. "I think you deserve a reward. Would you like mommy to help you?"

"He... help me?"

"Yes, help you darling. You like Mommy's big tits, don't you?"

Before Ashley could answer Ava took one of her breasts in each of her hands, spreading them wide then squeezing them together, trapping Ashley's cock between them. It felt warm, and soft, and wet, and in spite of spending all day forced inside his body, Ashley rapidly felt himself hardening. In a few minutes he was fully erect, although his cock still fit entirely within Ava's cleavage, and moaning as his mother pumped her tits around his cock. Ava stood, looking Ashley in the eye, and even though they were almost the same height with her heels off he still felt as if he were looking up to her.

"Lay down on the bed," Ava whispered in a quietly commanding tone.

Ashley laid down, and didn't have to wait long for Ava to position herself on top of his lower half, once again wrapping her tits around his cock and pumping their slick flesh up and down around him. Deep in the throes of pleasure Ashley couldn't help but play with his nipples with each hand, and within a minute of laying down on the bed he was whimpering with joy as he squirted load after load of backed up cum onto Ava's chest. When the last spurt finally dripped out of him Ashley looked down at Ava and said "I love you."

Ava smiled back up at Ashley for a moment before responding. "I love you too sweetie. Thank goodness you're a quick shooter though, I'm exhausted and ready for bed."

Ashley was unsure how to take that, she'd phrased it like a compliment but he'd never heard of being a 'quick shooter' being a good thing.

"I'm too tired to go wash up," Ava continued as she crawled up the bed. "Be a dear and clean up your mess so we can get to sleep."

Without waiting for an answer Ava lay down on top of Ashley, pressing her tits into his face. He reflexively started to suck and lick without even thinking about what he was doing, and it wasn't until he tasted his cum that he paused to think. The idea of eating his cum seemed weird and kinda gay, but surprisingly the taste was a little familiar and not at all bad. And at the end of the day he was licking and sucking on the most beautiful rack he'd ever seen, so what could be gay about that?

Ava started off rubbing her chest back and forth around Ashley's head, giving him the opportunity to lick every nook and cranny clean, but when she saw the excitement with which he took to the task, she rolled over onto her back, pulling his head with her, and let him graze freely over her chest until he'd cleaned every last drop. Ashley was stunned at the amount of cum he'd managed to pump out, attributing what seemed like four or five of his regular loads to his pent up sexual frustration, but he didn't mind it. The more cum there was the longer he got to lick Ava clean. Finally she decided that he'd moved beyond cleaning and into playing, and Ava pushed Ashley's head away from her chest, pulled it to her shoulder to cuddle, and whispered, "That's my good boy. Goodnight sweetie."