Hot Mom's Sissy Honeymoon Sweetie 6

~~~~~ Week 3: Truths Revealed ~~~~~~

The night that Ava finally let her son Ashley cum by eating his ass while vibing his chastity cage and balls was a turning point in their relationship. As they entered the third week of enjoying what was meant to be Ava's honeymoon with her ex-fiance Greg, the simmering sexual tension that had built between them finally started to boil over more regularly. Of course the dominant and submissive roles which they'd naturally developed continued, augmented by Ava always carrying the key to Ashley's chastity cage around her neck, and so while Ava allowed much more sexual contact between them now, she remained firmly in control of what they did and how far they went. Non-negotiable hard limits were still in place. First, Ava's pussy wasn't for Ashley. He could see it of course, he could hardly serve his mother in all the ways she required if he couldn't, but touching it was strictly forbidden. Second, and similarly, Ava wouldn't touch Ashley's cock, although the fact that she always kept it locked in it's flat chastity cage made keeping that rule easy for her. After some consideration she decided that Ashley's exposed balls were technically fine for her to play with, largely because she enjoyed the feeling of power watching her son squirm gave her. The classic loophole in all of Ava's rules for sexual conduct between her and her submissive sissy son was that anal didn't count.

One example of this sexually enhanced dominant/submissive dynamic was in the regular footrubs which Ava continued to demand from Ashley. The most common situation in which she summoned him to her feet was still while she sat at the makeup take in their suite. So common, in fact, that they started keeping a cushion under the table for Ashley to kneel on. But the act of service gradually became more overtly sexual. Ava had been putting her feet into Ashley's mouth for a while, hooking a big toe into his cheek or even forcing the whole front of her foot into his mouth, but now she was going further. Instead of holding her foot still and allowing Ashley to peacefully suck on her toes while massaging the rest with his hands, Ava started pumping her foot in and out of his mouth forcing him to slobber and drool on her foot as she fucked him in the mouth with it. From her seat above him she would even cheer him on, telling him to "suck Mommy's toes like a good girl" or to "give Mommy's foot a blowjob." Soon the footrub itself became an afterthought, as Ava started deriving more and more enjoyment from the delightful feeling of Ashley sucking and gagging on her feet.

One day while Ava and Ashley were tanning on the beach at a slightly secluded spot around a promontory where the helpful staff had set up a semi-private umbrella with two beach chairs for them, Ava rolled over in her chair and said in a calmly commanding tone, "Feet, dear."

Ashley got up from his lounge chair and kneeled in the sand at the foot of his mother's as she kicked off her sandals. He naturally reached out to begin massaging her feet, but Ava had other ideas. She expertly hooked her left foot around the back of Ashley's head, pulling him suddenly forwards and down with her powerful leg muscles, forcing his open mouth onto the toes of her right foot, which was sitting angled upwards on her lounge chair. Ashley's eyes rolled back in his head as his tongue wove between Ava's delicious toes while using the toes of her left foot to grab Ashley's blonde ponytail, Ava started forcing her son to bob his head up and down. If anyone had been watching they would have seen what looked like a pretty young girl in a coral bikini giving passionately sloppy head, but Ashley was so enamored with Ava and her beautiful feet that he didn't even consider the possibility as he sucked and slobbered with abandon.

Ava soon realized that her foot behind Ashley's head was unnecessary, as her good little girl was happily doing just as she was supposed to, so she pulled it back and slid her left leg down in front of Ashley's kneeling body instead. She knew how excited Ashley got when sucking her feet, and even if she wasn't going to unlock her, she didn't mind letting her have her fun as well.

As usual when given the opportunity, Ashley seized Ava's leg and squeezed it to his body in a tight hug, putting Ava's knee on his chest and her ankle to his crotch. His muffled moans of delight were music to Ava's ears as he started humping her ankle, rubbing and crushing the balls hidden in his bikini bottoms against her foot and ankle. Ava never understood foot fetishes before, thinking it was a little weird, but what had started as her simply enjoying her son's happiness being at her feet and the feeling of power that came with it had gradually evolved. His tongue flicking between her toes and sliding up and down her sole felt so good, it was as if her feet had developed new nerve endings in response to his constant attention, or the old ones had been awakened and rewired. Either way, Ashley's sloppy head on her foot had Ava worked up in a way that demanded attention. She slid one hand down the front of her bikini bottoms and began playing with her clit and fingering herself while teasing her nipples through her bikini top with the other.

Ashley looked up from Ava's foot as he continued to bob his head up and down while sucking on it, making eye contact with her, but also seeing in his periphery that she was openly masturbating on the public resort beach. His eyes darted back and forth, scanning to check if anyone was watching in their semi-private area. He couldn't see anyone, and he couldn't take his mouth off Ava's foot to turn his head and check more thoroughly, she wouldn't like that. So he continued on, sliding himself further up Ava's leg as he humped her more aggressively with his balls in response to her fingering herself, each impact sending twin bursts of pain and pleasure shuddering through him.

Ava felt Ashley's increased fervor and it gave her a wicked idea. She hooked the toes of her left foot upwards, searching for the fabric of Ashley's bikini bottom and pulling it to the side. Then she started tracing her big toe in slow circles around her daughter's hole, knowing from experience just how sensitive it was, before suddenly forcing her toe up Ashley's twitching ass. The shock made her start to pull her mouth away from Ava's other foot, but her mother was having none of that, pressing her right leg forwards to keep her toes in Ashley's mouth while forcing her to sit deeper onto the foot penetrating her.

Unable to escape, Ashley was forced to commit, grinding even harder into Ava's ankle as his ass was fucked by Ava's toe and his mouth was fucked by her other foot. His tearful eyes looked pleadingly up at Ava, wordlessly begging for permission, but her eyes were closed as she frantically chased her own pleasure at an increasing rate. Ashley fought with everything he had to hold back, until finally Ava climaxed and in the throes of her passion she cried out, "Cum for me now!" Ashley careened over the edge before Ava had even finished speaking, his ass spasming around Ava's toe as he spurted again and again through the flat head of his chastity cage into his bikini bottoms. When his orgasm finally subsided, Ashley slumped forward, spent, still holding Ava's foot in his mouth and lazily sucking on it until she pulled it away, along with her other leg, and gestured to Ashley to come up to her.

Ava scooched over to make room as Ashley crawled up and laid down next to her, snuggling cozily into one chair although they had two, laughing quietly at what they'd just done and feeling grateful that either nobody saw what they were doing, or if they did they'd had the good sense to leave them alone and not interrupt. Eventually after they'd basked in the afterglow of comfortable silence together for a time, Ava pulled Ashley's face up to her own and they lazily made out for the rest of the afternoon as they soaked up the Caribbean sun's rays.

After that, giving Ava footrubs became the primary means by which Ashley was allowed to cum. It wasn't as if he needed any additional incentive to serve at his mother's feet, but with that added bonus he was insatiable. Ava didn't always masturbate while he humped her leg, nor did she always work her toes up his ass, but she did always tell him when he was allowed to cum. Sometimes she let him go quickly, other times she tested how long he could hold back before finally granting her blessing, but either way she did require him to lick clean any of his mess that made it's way on to her when he was done.

Another new treat which Ava allowed herself was having Ashley worship her ass. Before the night when her jokingly telling Ashley to kiss her ass had unexpectedly turned into so much more, Ava had never really experienced that kind of attention back there. She enjoyed anal of course, especially as part of a double-stuffing with another partner in the front, but had never been with a man who wanted to kiss and lick her booty the way her precious daughter did. As it turned out, she loved it, even more than a juicy cock in her backdoor. So a quick and proper kiss on her ass soon became the standard way for Ashley to show her respect to Ava. While they'd grown quite informal with one another over the weeks as they lived together in the Honeymoon Suite, Ava didn't think it was proper to discard all formality between them as she was still Ashley's mother. So to remind her daughter of her place beneath her (and honestly because she enjoyed it), Ava made a habit of making Ashley kiss her ass throughout the day.

While taking their shower together in the morning Ava often snapped her fingers and pointed to her backside, signaling Ashley to take a quick break from washing her to kneel and show her devotion. Another common time was right before bed as they were wrapping up their day. Ava would snap and point as she started brushing her teeth, letting Ashley have one last taste of her ass before going to sleep. One day after Ashley finally beat Ava in a tennis match and crowed about her victory a little too much, Ava decided a public humbling was in order. She snapped and pointed as she stood on the court, causing Ashley's eyes to bulge. When her daughter hesitated Ava angrily snapped and pointed to her ass once more, leaving no doubt as to what she expected. Mortified in the knowledge that other couples playing tennis on the nearby courts could see him, Ashley still hesitantly obeyed, crawling behind Ava and pushing his face up under her tennis skirt, hungrily kissing her ass and inhaling her deliciously musky, sweaty accent through her built-in shorts. That soon escalated to the point where they had to take it to the showers, where Ava kept Ashley buried in her ass the entire time, teaching her respect as she was waterboarded in heaven.

Ass-kisses were sweet and a good reminder of Ava's dominant position as Ashley's mother, but there were also times when she needed more extended treatment back there. Sometimes she'd simply pull out a book, lay down on her front, lift her dress, and tell Ashley to eat her out while she read. She'd trained Ashley well, impressing on her daughter that she was only to lick Mommy's ass, not her pussy, and so she could get lost in her book, largely ignoring Ashley and not worrying about her misbehaving as she buried her face between her cheeks. Sometimes after an hour of reading Ava would feel done, thanking Ashley and going on with their day. Other times the steady pleasure of having her ass passionately eaten put Ava in the mood, and she'd toss her book to the side and finger herself to orgasm while Ashley continued.

With the physical barriers between them eroding, other barriers slipped away as well. When it gradually became clear to Ava that her nightly lovers were an open secret to Ashley, she started discussing them much more openly. Truthfully she was thankful to have someone she could indulge in 'girl talk' with, and as Ashley helped her get ready for their dates with the staff each night they'd talk about their opinions on the different men, comparing notes on their looks, their bodies, their swagger, and even their bulges. Ava didn't go into details of what happened in their suite while Ashley was away, not knowing that he knew full well as he spied on her through the window every night, but she did ask Ashley to help her pick out the outfit and lingerie that he thought each date would enjoy most.

Through it all Ashley found himself slipping further and further into thinking of himself as a girl. Ava continued to refer to him as her daughter all the time, even when it was just the two of them, and dressing as a girl in borrowed clothes from Ava plus the growing wardrobe of his own girly clothes that Ava bought for him took a toll as well. He wasn't sure if his body was gradually becoming more feminine, or if it just looked it because of the clothes Ava made him wear, but either way dressing like a girl, walking like a girl, talking like a girl, being called a girl, and as Ava loved to remind him cumming like a girl gradually day by day made Ashley think of himself more and more as a girl unless he put a deliberate effort into remembering who he was underneath it all. That effort was becoming harder and harder to muster as Ava made her preference for feminizing her daughter clear. She booked Ashley and herself for another skin treatment at the spa to ensure that he stayed hairless and smooth below his head, and also signed them up for manis and pedis, picking out bubblegum pink nail polish for Ashley's fingers and toes.

One night near the end of their third week Ashley and Ava had a dinner date with Ajani, their yoga instructor at the spa. While at their first date with Ajani a couple weeks ago Ashley had acted the part of a spoiled brat, throwing a fit over having to share Ava, but tonight she played her role in their three-way date with grace. Ajani picked the girls up at their suite, taking one on each arm as he led the way to their table on the beach. As they walked Ashley marveled at Ajani's muscular, but not overly bulky arm, tracing her bubblegum pink nails over his dark skin and biting her lip as she looked forward to watching him with Ava tonight. Of all her lovers he was easily her favorite, although she knew that Ava probably preferred the masseurs or the twin porters to keep more of her holes filled at once. But Ashley liked the way Ajani treated her mom, making love to her tenderly as he moved her smoothly from position to position even though he could have power-fucked her with his strength and his massive cock. As Ajani held out Ashley's chair for her to be seated she turned her head to take in the perfect view of his bulge, prominently displayed in his tight shorts, and for a moment she was tempted to nuzzle into it, begging him to make love to her the way he made love to her mother.

The moment passed and Ashley's self-control held as he shook his head. He was a boy, why was he looking at another man's bulge and wanting him to use it to make love to him. He didn't want that, right? It was natural for him to want to watch Ajani's beautiful black body as he fucked Ava, and of course he was looking forward to fingering his ass and playing with his little titties while he watched a real man having sex with his hot mother through the window of their suite, but he had to remember that he was a boy. A boy wearing a bikini top and cutoff jean shorts over his bikini bottoms, with long blonde hair gradually going platinum in the tropical sun, and a cute little 5'2" body with growing curves. A boy who looked just like Elsa Jean's little sister and had developed an appreciation for the powerful black men he was always surrounded with. But still a boy, dammit!

Dinner, as always, was delightful. The food was amazing, the view of the ocean ahead and the resort behind from their beach side table was stunning, and the champagne and conversation flowed freely. Ashley joined in fully in the evening, laughing along with Ava at Ajani's jokes and listening with rapt attention to his stories. Time flew by in a pleasant whirl, and before long the sun was setting before the horizon and it was time to move on. Ashley reached across the table, squeezed Ava's hand, and told her to have a nice time back in their suite, and that she'd need out on her evening walk. Then Ashley watched as Ajani walked Ava back to her room, waiting a bit before following them to her usual perch.

Ashley arrived just in time to see Ajani holding Ava upside down in front of his body, eating out her pussy while her head bounced up and down on his cock. Ashley struggled for a moment not to be jealous, for all the times Ava had let her eat out her ass, she'd never once let her have the tiniest lick from her pussy. She could only imagine how good it would taste, how the velvety soft skin of her labia would feel on her tongue, on her face. Ashley slid down her jeans shorts and pulled her bikini bottoms to the side, reaching around behind herself to start fingering her pussy. She was so focused on the scene inside, daydreaming about what her mother's sweet pussy must taste like, that she didn't notice the footsteps behind her until it was too late.

"The fuck you doin'?" a gruff voice from behind Ashley asked as a set of strong hands grabbed her by the shoulders. "Shit, you're Ava's little girl, whatchu doing out here?"

"N... Nothing!" Ashley protested as he snapped out of it and saw the he was being lifted and held by Kemar, one of the waiters and a member of Ava's stable of lovers. He hurriedly pulled his fingers from his ass, but worried that he'd been too late.

"Who's out there?" Ajani's voice called from inside the room.

"It's me, Kemar, brother," Ashley's captor replied, "And wait until you see what I caught."

Ashley squirmed helplessly as Kemar carried him inside, unable to even pull up his shorts or readjust his bikini bottoms to cover his ass. He was just grateful that he hadn't started playing with his nipples yet so at least he wasn't flashing his tits. As Kemar held him up for Ajani's inspection, Ava didn't even notice that anything had happened, continuing to sloppily suck on Ajani's big black cock until he finally pulled her away, turned her right side up, and set her down.

"Ashley?" Ava asked uncertainly, wobbling a bit as she got her bearings back.

"Ummm, hi Mom," Ashley replied sheepishly.

"But what are you doing here?"

"I caught her outside watching at the window," Kemar explained, then he gave a nod down to Ashley's disheveled lower half. "She was having a good time, looks like."

A hard glint entered Ava's eyes as she took in Ashley's embarrassed blush and her disheveled state.

"Is that what you want?" she asked accusingly, "To watch your own mother get fucked by real men? Fine, sit in the chair in the corner."

"But Mom, I..."

"I said. Sit. In. The. Chair." Ava enunciated each word with brutal precision. "And don't touch yourself either, you naughty girl. You just sit there and watch."

Ava turned back to face Kemar and Ajani then, her face softening along with her tone.

"Now then, where were we? Ah yes, I believe you two were just about to fill me up with your beautiful cocks. Shall we?"

Ava's lovers had seemingly had no compunctions regarding fucking her in front of her daughter, so Ashley was forced to sit in his front-row seat and watch as they worked his beautiful mother over in every hole, trading places and switching positions as each of the powerfully built black men made the woman who had Ashley wrapped right around her little finger into their willing bitch. The worst of it was that even there, humiliated and forced to watch, Ashley wanted nothing more than to play with himself in hopes that the taboo heat of the situation would be enough to push him over the edge into orgasm. But in every position Ava found a way to stare him down, keeping her eyes on Ashley as she satisfied two big black dicks. He couldn't disobey and play with himself under her withering gaze. Finally Ava's moans built to a climax as she was sandwiched between Ajani and Kemar. It could have been his imagination, but as Ashley stared back into Ava's eyes and smiled with genuine happiness for her at her orgasm, he thought he saw the hard look she'd fixed him with soften before her eyes rolled back in ecstacy. The rippling clenching of Ava's ass and pussy as she came triggered her lovers to climax as well, pumping her full of their thick loads of rich, creamy seed. From where he was sitting Ashley could actually smell it, a rich nutty aroma that made his mouth water in a surprisingly familiar way.

Satisfied for the night, Ajani and Kemar thanked Ava and left, each giving Ashley a knowing smile on their way out. After thanking them and waving goodbye, Ava turned to look at Ashley, who struggled to read his mother's face. It looked as if waves of conflicting emotions were doing battle, and so he sat still and silent in his seat, awaiting her judgement. Finally Ava broke the long silence with a single word.

"Heel."

Ashley practically jumped from his seat, hurrying to kneel at Ava's feet, hoping to forestall whatever punishment he was due by giving her a footrub. But his mother had other ideas. As he started to reach for her feet, she reached down and grabbed a fistful of his long blonde hair on the top of his head, tilting it back so he was looking right up at her. Then without a word she stepped forwards, straddling him and bending her knees slightly so that her pussy was directly over his face. He looked up at her in anticipation, his eyes tracing up her gently curved tummy, past her massive underboobs, and up to her beautiful face starting down at him. It was like kneeling at the feet of an avenging angel, beautiful and powerful. For a moment Ashley thought that he might finally get to touch his mother's holiest of holies, the forbidden fruit and the one part of herself that she kept off limits to him while giving it so freely to her many lovers. But as he tried to rise to meet it with his mouth her grip on his hair tightened, painfully forcing him back down, inches away from his heart's desire.

Then the first drop hit his lips, a mixture of his mother's sweet juices and Ajani's salty cum. Ashley instinctively licked his lips, tasting the exotic mixture with the tip of his tongue, and without conscious thought he opened his mouth wide. It was fortunate that he did, because that first drop was followed by a steady stream, oozing and dripping from Ava's freshly fucked pussy as she flexed her pelvic floor and gradually forced it all out. Ashley had no choice but to swallow, quickly gulping it down so that he could breathe, then opening his mouth again to catch the ongoing stream. He thought about the moment before dinner when he'd almost nuzzled into Ajani's bulge, processing the reality that although Ava had been the one who got fucked, he was the one swallowing down the load that had been churning in the powerful black man's balls at that moment, waiting for release.

When the flow of mixed juices from Ava's pussy slowed and finally ceased, she let go of Ashley's head and turned, bringing her thick booty to bear. Her well-trained son knew instinctively what was expected of him, tilting his face upwards at just the right angle to meet her ass as she sat on his face, using him as her human stool. Buried between Ava's cheeks, Ashley licked hungrily at her hole, thrilled to still be allowed this honor after what he had done. As his tongue scooped out the first glob of Kemar's cum, he swallowed it down and went digging for more, grabbing Ava's thighs with his hands to pull her down even harder on his face. But she quickly swatted him away, grabbing his wrists and pulling them off of her legs, making it clear that she was in charge, and Ashley's role was to receive. Still, as Ashley continued to eat she sat more fully, until most of her weight was bearing down on his pretty little face. Eventually his licking revived the flames of her passion, and Ava masturbated herself to orgasm while he continued his ministrations to her rear.

When Ava finally stood and turned back to look at Ashley, his face was streaked with sweat and cum, but his eyes looking up at her were filled with loving devotion. Her heart melted as she looked down at her little sissy sweetie.

"Mom?" Ashley asked, "Do you think that I could maybe have a turn to cum now?"

Ava's soft expression shifted back as she was reminded of exactly why her depraved daughter was in this situation.

"You get caught peeking on your own mother having sex and the first thing you do is ask if you can cum?" Ava asked incredulously. "The nerve! You don't deserve to cum, you deserve to be punished!"

Ava moved one of her legs between Ashley's knees and hooked her foot under his balls, dangling below his flat chastity cage. It wasn't quite a kick, but it wasn't a soft touch either, and Ashley winced in pain as Ava pressed her foot upwards, crushing them against his body.

"But this isn't even really punishment for a slut like you, is it?" Ava demanded as she increased the pressure. "I bet if I kept this up and started grinding my foot back and forth you'd spurt your little load all over me, wouldn't you?"

Ashley nodded, admitting the truth that even in the pain he was impossibly aroused.

"Well then, we'll need to find a different punishment for you," Ava said as she pulled her foot away. "Follow. If this was good enough when you were little, it's good enough now."

Ava walked over to the chair where Ashley had so recently sat and watched her with her lovers, sat down, and had him lay across her lap. Then for the first time in years she started spanking him. When he'd been younger Ashley's spankings had been brief, a few hard swats to teach him his lesson, sharp pain that soon faded. This was radically different. The first few swats of Ava's cupped hand didn't hurt too badly, Ashley had grown up and his pain tolerance was much higher as a young adult. But Ava didn't stop at a few swats, she continued on, working both of Ashley's cheeks, expertly distributing her strikes around the lower portion of his jiggling bubble butt and his upper thighs. Blood gradually flowed into the area, enhancing Ashley's sensitivity as repeated swats started to land in the same locations. Ava wasn't swinging any harder, but she also didn't show any sign of slowing down, and soon Ashley was whimpering in pain with every stroke. Oddly the pain didn't make him resent Ava at all, instead it made him feel oddly affectionate. What he'd done was wrong, he knew that, and his mother was working so hard to help him, to correct him. He knew that she was doing this only out of love for him, and so when one particularly painful swat drew the first tear from his eyes, he cried out, "I love you Mommy!"

Ava continued her punishing assault on Ashley's ass, spanking him with a regular rhythm.

"I... I love you... So much..." Ashley continued to cry out between swats. "I'm sorry... please... forgive me... I just want... to be with you..."

The tears were now flowing down Ashley's face as the pain clarified all the confusing thoughts that had been flying around his head, simplifying his world. Ava paused for a moment, replying, "I know you do Sweetie, and I love you too, you're my daughter after all. That's why I need to do this."

Ava resumed her spanking, forcing Ashley to continue spilling out the truths that he'd finally realized deep within between the ongoing bursts of elucidating pain.

"No... not like that... I mean... I love you... as my mother... but it's more!"

Ashley paused for a moment, taking a few more strokes and gathering his breath before revealing his heart.

"I don't just love you... I want to be your lover... I'm not a girl... I'm a boy... your boy... and I'd do anything to be yours!"

Ashley's declaration shocked Ava into finally stopping her spanking. She took a moment to process the unexpected words she'd just heard, gently rubbing her hand in soothing circles over Ashley's burning backside.

"You mean, you've been pretending to be a girl this whole time just to get closer to me?"

"I'd do anything to be closer to you!" Ashley swore emphatically. "You seemed to like me as a girl, so I went along with it, but I don't want to be your daughter, I want to be your boyfriend, like when we went on those practice dates. Please Mommy!"

Ava sat in silence, terrified at what she had done, what she had pressed Ashley into, the Pandora's Box she'd opened. But did she dare to snap it closed, or did she leave it open and pray that hope for the future finally came out.

"Go get your pajamas on," she finally said in a flat voice devoid of emotion, "it's time for bed."

Ashley and Ava both dressed for bed in silence, quickly moving through their evening routine while avoiding one another as much as possible. While Ashley wore his lacy babydoll, Ava dug around the bottom of her bag until she found a pair of plaid cotton pajama pants and soft old tee. Ashley tried to move in to cuddle Ava once she joined him in bed, but she held him gently back, telling him that she needed some space to think.

As Ashley drifted uneasily off into sleep, Ava wracked her mind to see where she'd gone wrong. The two of them had done so much and come so far in the past few weeks, falling into it naturally one small step at a time. She'd tried over and over to set boundaries and limits, not trusting herself or Ashley to resist the strange chemistry they'd unlocked between them, but every time she found herself slipping further and further until there was only one true limit left between them. Through it all she'd taken comfort in Ashley transitioning into a girl, thinking that all the strange things happening between them were a part of him discovering who he truly was, and proud of herself for supporting him as a good mother should. But when he'd revealed that he never really saw himself as a girl, and had done it all to get closer to her, she felt hurt and betrayed. Had she pushed him too far because she'd assumed that's what he wanted? Or because of her newly discovered attraction to soft femboys? Or because she'd always wanted a daughter?

But the scariest thing for her was the uncertainty in how she'd handle Ashley's declaration of love. Before that she'd been able to convince herself that they were just a couple of girls having fun, and that as long as they didn't actually have sex it was all just harmless play that didn't have to mean anything more. But with Ashley's admission that he did want more and had developed real feelings for her she was faced with the ultimate conundrum. Would she let him down gently? Or would she be unable to resist the growing feelings in her heart that echoed his own? What she needed, Ava decided as she fitfully drifted off, was space to think.

The next morning when Ashley woke up Ava was already in the shower. Eager to make amends, he quickly stripped out of his babydoll and panties and went to join her. However, as he approached the walk-in shower Ava turned away, using her hands to cover up her crotch and her tits as much as possible, and told him that she'd manage on her own, and that he could take his shower after. Ashley turned away as if he'd been physically struck. He couldn't recall the last time Ava had covered herself in front of him. The grim reality of just how badly he'd screwed up started to set in. By the time Ashley finished his shower and came out, Ava was already dressed in a flowing red sundress and on her way out the door.

"I'm off for the day," she said casually, "It's Tafari and Shavell's day off, and they invited me to visit the village with them. We should be back by evening, so I'll see you for dinner."

And then she was gone. And just like that Ashley was all alone for the first time in what felt like forever. His first thought was to chase after Ava and beg her to unlock him before she left. Although she'd allowed him to cum plenty of times in the past week, she still hadn't unlocked him from his chastity cage in over two weeks, and taking out his frustrations by actually beating his meat for once sounded great. But he second-guessed when he thought about how Ava would take it. She already thought he was a pervy slut after he'd been caught watching her have sex, what would she think if he followed that up by asking her to unlock him? Maybe the safest thing was just to stay locked and let her spend the day out and about with the key securely around her neck. In either case, by the time Ashley finished internally debating Ava was long gone and so his decision was effectively made.

With jerking off off the table, Ashley wondered what to do for the day. Eventually he decided to go to the spa, as he didn't know what else to do and drowning his sorrows in one of their delicious coconut cream drinks sounded good. Without Ava to guide him, he dressed as androgynously as he could, given the limited wardrobe he had to work with. He picked out some of Ava's yoga pants, and debated going commando. He didn't want to have any panty lines showing, of course, but he wanted his package to be tucked away a little more securely. Finally he decided to raid his mother's pantry drawer, picking out a nice thong for himself. The thin strip of fabric felt nice between his cheeks, rubbing ever so slightly on his sensitive hole as he walked, and he noted with satisfaction that he didn't have any panty lines showing after he pulled on his pants.

That only left a top. He thought about the various camis and crop tops Ava had dressed him in when he wasn't just wearing a bikini top or sports bra, but he really didn't want to go that girly right now. Eventually he picked up her discarded tee shirt she'd worn as pajamas last night. It still smelled like her. Ashley pulled it on and made himself ready to leave, then paused. His boy boobs jiggled whenever he walked, and he was worried about the attention they'd bring. He decided that the manliest thing to do was to go ahead and wear a sports bra under his shirt to at least contain them. Besides, it was way more comfortable that way. Once he'd taken care of that, he set out for the spa, happy to be in what he thought of as "boy mode".

While Ashley may have thought of himself as being in boy mode, the staff at the spa certainly didn't, as they continued to refer to him using female pronouns. Once that would have sent him into a rage, but now he took it with a friendly smile and didn't bother correcting them. After two weeks of going publicly as a girl under Ava's direction, he didn't want to confuse matters further right now. Besides, they had a coconut full of his special drink ready and waiting for him, and it was still warm. Ashley took a quick first sip, then asked if it would be possible to make a few more. The receptionists eyes widened a bit at his request, but she said she'd put the staff hard to work preparing them as fast as she could. Ashley expressed his gratitude and took a seat in the atrium to enjoy his drink.

As usual the coconut cream settled into his stomach and sent a warm fuzzy feeling through his body, like he was floating on a sweet pink cloud of cotton candy. He sat there with his eyes closed, simply enjoying the sensation until the receptionist appeared at his shoulder with a second drink to replace the one he'd finished. Ashley thanked her, and she told him that it would likely be an hour or so until the staff could make him another. He tried to make the second drink last longer, but before he knew it he was scooping out the creamy dregs from the bottom of the coconut and licking his fingers clean. Ashley felt warm, especially around his chest as his skin tingled under his sports bra. He needed to get up, to move, to do something with the heat burning inside of him.

Just then he saw Ajani walking into the spa atrium. He should have known this could happen, Ajani was the spa yogi after all, but Ashley had been so distraught at Ava's departure that he hadn't thought it through. He couldn't face the powerful man after what he'd been through the night before, not with him knowing that Ashley had been peeping on him and Ava. He saw his opportunity to escape as Ajani turned to greet another guest, rushing from his seat towards the exit. But just as he was nearly there, Ajani turned, and he had to divert down the hallway, ducking into one of the side rooms to hide. He quickly shut the door behind him, then turned and saw Leandro and Dejuan staring at him quizzically.

"Good afternoon Ashley," Leandro said after a moment, "Just you today? You're in luck, we're both free for the next hour, so we can both give you a massage. Just strip down and hop on the table and we can begin."

Ashley froze. He hadn't been planning to get a massage today, but he needed somewhere to hide from Ajani, and at least the masseurs didn't know that he'd been secretly watching them fuck his mother. And he knew from experience how good they were at their jobs. Their strong hands were like magic, and with the heat emanating from his belly being touched by them to release the energy inside sounded amazing. With all the massages that Ava and Ashley had received from the pair he didn't feel too awkward as he stripped out of his shirt and yoga pants, then tossed his sports bra to the side, leaving him wearing only Ava's borrowed thong which he'd thankfully worn. Blushing a little at the realization of how casually he'd just stripped down to nothing but a thong in front of these two men, Ashley hopped up facedown on the table, grateful as one of them placed a towel over his exposed backside for modesty.

While Leandro started working on Ashley's legs from the bottom up, Dejuan set to work on Ashley's shoulders and back from the top down. He'd only ever had one of the masseurs working his body at a time before, and the combination of all four strong hands kneading and working his soft flesh was amazing. With the oil they spread over his smooth skin their hands glided easily back and forth, teasing out all the tension he was holding in. Leandro told Ashley that he would continue working his way up her legs until she told him to stop, and he murmured his assent, wondering if he'd ever want it to end. Time passed and Leandro finished with Ashley's calves and started working up his thighs, and the sense of perfect relaxation Ashley had felt grew into something more. Perhaps it was because he was still sore from Ava's spanking the night before, but the squeezing and pulling sensation of Leandro's strong hands on his legs felt so good, and the heat in Ashley's belly felt like it was melting inside him.

He knew he should stop the masseur once his hands reached the bottom of the towel, but he kept thinking he would just let it go on a little longer. Soon Leandro's hands were under the towel, working the sore lower cheeks of Ashley's ass. He felt the melting liquid heat inside of him at the same time as he felt something warm and firm press against the soles of his feet. Not fully thinking he moved them back and forth a bit, trying to figure out what it was. It grew even harder, throbbing against Ashley's feet like a heartbeat, and he suddenly realized that he was playing footsie with Leandro's growing bulge. He froze, but it was too late, and the masseur took Ashley's flirtation as an invitation and began slowly grinding himself in. Ashley wanted to call for him to stop, but the liquid heat inside him was boiling to a crescendo and he needed Leandro to keep going. He tried to ignore the hardening cock rubbing against his feet as the hands squeezing his ass finally pushed him over the edge, triggering him to ooze a slow, throbbing orgasm from his cage and into his thong. Fortunately Leandro took Ashley's involuntary moan as his signal to stop, and he professionally removed his hands and stepped back.

Ashley thought he was done and was hoping Leandro and Dejuan would leave so he could clean up the mess he'd made in his panties, but they insisted that since the two of them could work twice as fast together that Ashley stay for the full hour and let them massage her front as well. He couldn't think of an excuse and their hands felt so good on his body so Ashley agreed, rolling over onto his back.

Leandro continued working Ashley's legs, starting again from the bottom and gradually working his way up. He didn't resume grinding himself into Ashley's feet, which left him feeling a strange mixture of thankfulness and disappointment. It wasn't as if he'd ever ask the man to do it, but maybe if he'd just done it then it wouldn't have been too bad. At the very least Ashley wouldn't have complained about it. But the more pressing issue was what Dejuan was doing. Ashley hadn't fully thought through what a massage of the front of his upper body would entail, but apparently it meant having his chest massaged. And apparently that felt really good.

Ashley suddenly realized how he must look to Leandro and Dejuan. They'd only ever known him to be a "girl", and with his chastity cage leaving his thong smooth in the front and his balls tucked back away between his legs, Dejuan didn't think he was massaging his chest, he thought he was massaging his breasts. The fatty tissue that Ashley had discounted as weird swelling for weeks had never been touched the way Dejuan was touching it now. Sure, Ashley had played with his nipples watch watching Ava fuck, and she'd even teased them a bit herself sometimes. But he'd never had a man take his breasts in each hand and work them the way Dejaun was. He focused his touch around the outside, gradually working his way into the center, pulling Ashley's soft tits in towards the nipples in the center that were hardening as they cried out for attention. The coconut cream drink always left Ashley's chest feeling warm, and two full servings in he was on fire. As Dejuan continued to work in painfully slow circles it almost felt like Ashley's breasts were growing even more under his forceful touch, as if he were loosening the tissue underneath his skin and allowing it to swell to it's full size.

After having felt Leandro's bulge earlier with his feet Ashley was acutely aware of the similar bulge beside his head as Dejuan continued. All he had to do was turn slightly, and perhaps he'd start to grind his manhood into Ashley the way his companion had. It was so close, he could smell it, could almost feel it. He was about to give in to temptation when the clock chimed the hour. Dejuan gave one final flourishing touch, squeezing each hand until Ashley's nipples were each pinched between his fingers, then twisting them gently as he released. Leandro executed a similar final flourish on Ashley's legs, then they both excused themselves from the room to allow him to get dressed in privacy. It took a full five minutes of slow breathing exercises for Ashley to calm down enough to even stand, and he wobbled on his feet as he got dressed and walked to the spa exit, gratefully taking a third full coconut on his way out. He wondered as he made his was back to the Honeymoon Suite if he should really drink it, the buzz from the first two seemed to be affecting his behavior and he wasn't sure what he'd do after a third. But it smelled so yummy and there wouldn't be any bulges to tempt him back in the suite, so he figured there wasn't any harm in it and polished it off before he'd reached the door.

It was late afternoon and Ashley knew that before too long he'd need to start getting ready for dinner, but first he needed to take care of a few things. The heat blossoming in his chest renewed with his third drink, and he could swear that his sports bra was fitting tighter than it had that morning. He stripped out of his top and bra, tossing them to the side, and let out a sigh of relief. Stepping over to the mirror and hefting a boob in each hand, Ashley inspected himself from every angle. They certainly looked bigger than he recalled, and instead of being generally swollen all around they were now a bit rounder on the bottom and sloped downward on the top. He certainly hadn't had underboob before, but as he bounced them up and down in his hands he saw that he did. A part of his mind wanted to panic at the thought, but that part was muffled by the warm pink cloud in his head, and another part of him giggled. Boobies were kinda fun, and he had his own set now that he could bounce and play with. He wondered how they'd look in a dress...

But before he went there, there was something else he had to take care of. The leak from his chastity cage had soaked through his panties and was now showing through the front of his pants. He peeled them both off and was and to throw them in the laundry bin when he paused. He looked down at the still wet puddle of cum in his thong. For weeks Ava had made him clean up his own messes whenever she allowed him to cum, and even though she wasn't there he felt an odd compulsion to do so knowing it would make her happy. He lifted the thong to his face, took one tentative lick, then stuffed it into his mouth, sucking out his cum and wondering if any of the flavors swirling in his mouth came from Ava's sweet pussy.

Once he'd finished, Ashley was naked and needed to choose a new outfit for dinner. He considered grabbing one of his pairs of panties, but really wanted to continue wearing a thong. So he raided her panty drawer for the second time that day, picking out an all-lace black one with scalloped trim he thought looked cute. After admiring his ass in the mirror, Ashley considered what to wear on the outside. He didn't really want to wear a bra, as the sports bras Ava had bought him were too tight now and hers were far too big. As near as he could figure his breasts were probably a B-cup, far short of Ava's H-cups. And he had wondered how his boobs would look in a dress...

Ashley paced the room, struggling to think clearly with three doses of coconut cream making everything feel warm and fuzzy. He knew Ava was always pressing him to dress up a bit more for dinner, to try wearing something more feminine or perhaps to try a bit of makeup. He thought that she'd always done that because she wanted him to look good for the men they were going on dates with, but after her response last night he wondered if she really wanted him to do it for her. He knew he had to do something to win her back, maybe this was his big chance?

Ashley tore through the closet on a mission, examining each of his mother's dresses to find the perfect one for him to wear. Most had no chance of ever fitting him due to the size of her breasts, and he kicked himself for not letting her but him a dress all the times she'd offered. Finally he found one that he thought he could make work. A little black dress that he had to imagine she would have been spilling out of, but which he could maybe pull in a little more tightly in the straps to more or less fit him. He stepped into the dress the way he'd seen Ava do as he watched her getting dressed, pulling the tight fabric up and over his hips, then working the spaghetti straps over his shoulders. Nervously he stepped in front of the mirror and checked himself out. He nearly cried.

After all the energy he'd spent fighting it, maybe he really was meant to be a girl. Ava's little black dress fit him far better than it had any right to, the ruched fabric hugging and accentuating his curves and the short length showing off his legs. He'd tightened the straps as much as he could to make the top kinda sorta fit, and he had to be careful if he leaned forwards at all or his tits would be on display for anyone in front of him. But he looked great. The only thing missing was makeup. He raced to Ava's table, quickly applying lipstick, eye shadow, and mascara. He'd seen her do it enough times to have picked up the basics, so although it wasn't perfect, it would have to be good enough. With his preparations running long he was worried about being late, so he didn't have any time to second guess himself as he slipped into a pair of black heels and wobbled out the door.

Ashley was running late, so he walked as quickly when the path to the beach as he could in heels. Even he emerged from the trees he saw Ava sitting alone at there table, still wearing her red sundress from earlier and looking beautiful as ever. She glanced at him, looked away, then whipped her head back to stare at him.

"Ashley?" she asked incredulously, "Is that really you?"

"Hi Mom," Ashley replied sheepishly as he waved. The additional motion upset his precarious balance and he toppled over with a high-pitched yelp.

"Oh sweetie!" Ava exclaimed as she leapt from her seat and ran to Ashley's rescue.

Ava took Ashley's hand and helped him back to his feet. As she did, he couldn't help but notice that she was leering down the loose front of his dress, taking advantage of the situation to check out his tits in the midst of making sure he was alright. They stood in silence for a moment, looking into each other's eyes and unsure of what to say.

"Do you like it Mom?" Ashley finally asked, gesturing broadly at his face and his dress and nearly causing another tumble that made him cling to Ava for support.

"I adore it," Ava replied warmly, reaching up to brush Ashley's hair back from his face. "Did you do all of this for me?"

Ashley nodded quickly, then said, "I think I kinda did it for us."

"Darling, that's so precious," Ava answered, wiping a tear from her eye. Then she leaned in slowly for a kiss, closing her eyes and slightly parting her lips. Ashley met her partway, unwilling to believe that this was really happening until their lips finally lightly brushed against one another. A pause, and then they brushed together again, slightly more firmly this time. Then another pause before they connected a third time, and this time they held, and held, and held, as though the world would crumble to dust before they let themselves be separated again.

Ava and Ashley had kissed many times by now. They'd shared quick pecks on the lips, hungrily lustful makeout sessions, sleepy kisses goodnight, and playful kisses good morning. This kiss was none of those things, it was something new and beautiful. It was the joyful kiss of two lovers reunited, the patient kiss of long-held love, the oblivious kiss of a couple for whom the whole world fades away. Their lips and tongues played together in a slow, sensual, intimate dance until finally Ava pulled back and whispered, "Let's sit and eat sweetie, I have something I need to tell you."

As they ate, Ava finally explained the events that had led to the cancellation of her wedding and her and Ashley embarking on the honeymoon together. Her ex-fiance Greg was a kind, decent man, and they really had been in love. But at her bachelorette party her friends had gotten her a stripper, a powerfully built 6'4" tall black man with the stage name Jack Hammer. It was all just harmless fun, until some of the girls got into an argument over where Jack's bulging "Hammer" was real, or the result of stuffing. He offered to let the guest of honor be the judge in a private showing, and the slightly tipsy Ava had agreed. She'd heard rumors about the size of black men's cocks of course, but had never experienced one for herself. What started with looking soon escalated to touching, then sucking, and before Ava paused to think she was being fucked to the best orgasm she'd ever experienced by Jack's 10" love hammer. The rest of the girls played it cool when they'd returned from the private side room, but it was clear that they all knew what had happened. Ava had stayed up all night after getting home, wondering what she should do and masturbating a few times to the memory. Finally when morning came she did the only thing she could, and called Greg, explaining that she still loved him, but that she couldn't be with him, and that the wedding was off.

"Wait, so you're the one who called it off?" Ashley asked as Ava finished her story. "I thought it was Greg."

"No, it was me sweetie. I knew that I couldn't give up on big black cocks, even after just one taste, and so there was no way I could be with Greg."

"Okay, but why are you telling me this now?"

"Because these past few weeks... I've been falling for you too Ashley. That's why I was so scared when you said you loved me last night."

"But Mom, this is amazing!" Ashley exclaimed, his face lighting up. "If you feel the same way I do, then we can be together, like really be together!"

"Honey, you weren't listening to my story. I can't go without big cocks, not after my experience with Jack and especially not after all the men I've enjoyed here at the resort. I have needs that have to be met, and if Greg couldn't meet them, then you certainly can't either."

"You don't know that!" Ashley protested, "We love each other, we'll find a way to make it work."

Ava reached across the table and took Ashley's hand. "Sweetie, look at yourself. I love the way you look, and I love that you dolled yourself up tonight for me, but you look more like my daughter than my lover."

"But you like this, right? I saw you checking me out before. I know you love fucking big black cocks, I've seen plenty of proof of that, but you clearly have a thing for me too. Love finds a way, we have to try!"

Ava thought about it, the memory of their kiss still lingering as she appreciated the beauty of Ashley's face with a hint of makeup. She knew she'd never forgive herself if she didn't at least try.

"Fine, back to our suite, right now. And try not to tumble over until I throw you onto our bed."

True to her word, five minutes later Ava had thrown Ashley onto their bed and was crawling on after him. They didn't bother stripping out of their dresses, Ava simply slid Ashley's up past his wide hips, then roughly pulled his borrowed thong down over his feet, slinging it across the room. Then she leaned back in over his crotch and used the key dangling from her neck to remove his chastity cage for the first time in over two weeks. It was a shock, to say the least, for Ashley to look down past his newly grown boobs and see a soft little nub poking out between his legs instead of a flat metal cage. He willed himself to get hard, he was so very horny and he wanted to show Ava that he could satisfy her so badly, but there was no response. And even soft his penis looked smaller than it had before? What had wearing that cage done to him?

Ava started to rub her son's little nub between her fingers, then started sucking his softy into her mouth. She was used to any man near her being hard in an instant, so it was a strange new sensation playing with a floppy little dicklet, but even through he struggled to get hard her sweet little boy's moans as she slurped his little noodle were immensely satisfying. When it became clear that it wasn't working, Ava let Ashley's cock out of her mouth with a soft pop and began to rub it again with her fingers.

"What's the matter sweetie, don't you want to fuck your mommy?" she asked in a teasing tone, trying to provoke him to man up and take her.

"God yes, please," Ashley answered desperately, "I don't know what's wrong with me, try something else, I'm begging you."

Ava considered, then licked the fingers of her other hand and lined up her third and fourth fingers with Ashley's twitching hole. They went in all the way on the first thrust, and as Ava started pistoning in and out she smiled as she saw the first signs of life from Ashley's cock. She continued for a few minutes, cooing soft encouragements as he finally reached half-mast, then seeing that his progress was stalling out, she decided to up the ante.

While continuing to finger Ashley, Ava asked sweetly, "Does my little girl want mommy to use her mouth again?"

"Please...." Ashley moaned.

So Ava climbed over him and positioned herself to the side, the fingers of her right hand still plunging in and out of his hole, but her palm now plapping against his balls with every stroke. Using her other hand Ava pulled down the top of Ashley's dress and exposing the breasts she'd only managed to catch a glimpse of earlier. His nipples were already hard, poking out in a clear display of his arousal, and Ava couldn't resist treating herself to them. She took one breast in her free hand and squeezed it as she sucked the nipple of the other into her mouth, lightly teething the sides of it as she flicked it back and forth with her tongue. Ashley cried out as he finally managed to reach a full erection, and a few minutes later when Ava finally released his nipple from her mouth with a satisfied sigh he was able to see it again for the first time in weeks.

It stood just a few inches tall. Ashley had never been physically gifted down there, maybe just five inches long on a good day and nowhere near the girth of the black cocks he'd seen so frequently at the Pink Lotus, but this was definitely smaller, even fully hard. For a moment Ashley panicked, knowing there was no way that Ava would want his little dick anywhere near her. But Ava was filled with lust for him and determined to make this work. She slid over the edge of the bed and bent herself over it, presenting her ass with a wiggle.

"I need to feel that cute little cock inside me," she moaned. "Hop up and show Mommy what you're made of sweetie!"

Ashley did as he was told, eager after weeks of waiting to finally fuck his unbelievably hot mom, but more than that, to make love to the woman he loved, and to show her that he would be enough for her. He stood behind Ava and rolled up her dress over her thick ass and her wide hips, seeing for the first time that she wasn't wearing any panties and wondering what kind of mischief she might have gotten up to with with the twins during their excursion. Trembling with excitement, he lined up his cock and slid it between Ava's cheeks.

Ashley had never been with a woman before, and he wasn't exactly sure where to position himself, but in all the porn he watched the guys just slid their cocks right in, so when he felt the soft warmth of Ava's flesh surround him in a perfect cocoon of love, he figured he must have done it right. He started thrusting, careful not to pull back too far and fall out. He tried his best to hold back, but the heat of the moment was too much for him, and after just thirty seconds he let out a girlish cry and began spasming as he shot his load.

"Mom, that was... amazing," Ashley said as he leaned over to rest on Ava's back.

"Amazing? Sweetie, you didn't even make it in my pussy." Ava stood, forcing Ashley to stand behind her, then climbed up on the bed, laying on her back and spreading her legs wide, then beckoning to Ashley. "Come here, it's clear you need to learn another way to please a woman."

Ashley climbed up on the bed between Ava's legs and she took his head in her hands pulling his face into her crotch. She didn't let him go straight to her pussy, forcing his head in circles around it as he licked her clean of all the cum he'd deposited between her cheeks, then finally she pulled him to the center and let him begin to lick her in earnest. It was the first time she'd ever allowed him to touch her there, and he was soon eating her out with feverish intensity, alternating between licking and nibbling on her clit and delving deep into her velvety folds with his tongue. Ava already knew how talented Ashley's mouth was from all the times she'd had him eat out her ass, but this was far better, and soon she was squirming in pleasure. She let go of his head, bringing her hands up to play with her tits and locking her legs around the back of his head to press him in deeper and to never let him go. When her orgasm inevitably came she clamped down so hard with her legs that Ashley thought his head might pop and he might suffocate, but if he did he would have died happy. A minute later Ava relaxed her leg lock, then finally released him. Ashley took one parting kiss, then sheepishly lifted his head and smiled at Ava.

"You see Mom? I knew we could make this work. It was good for you, right?"

"Oh sweetie, it was," Ava said reassuringly, "But there's still something you don't understand. Let me show you."

Ava went to the closet while Ashley laid back on the bed basking in the afterglow of finally getting to lick Ava's pussy, even if he hadn't technically managed to fuck it. When Ava returned she was holding the largest black dildo Ashley had ever seen. The shaft looked to be nearly a foot long, with a bulbous head nearly the size of Ashley's fist, there were knotty veins protruding along the length of it, and at the base were a pair of balls the size of ripe plums.

"The girls got this for me after my bachelorette party," Ava explained as she climbed back up on the bed. "It's a clone-a-willy of Jack Hammer's cock."

"That's... that's massive," Ashley stuttered.

"It is, isn't it?" Ava replied wistfully as she lovingly stroked one hand along it's length. "I wanted your first time to be special, and what could be better than the same big black cock that baptized me?"

"What?!?" Ashley asked, his vague sense of uneasy fear coalescing into crystalline terror.

Ava sat between Ashley's legs and plopped the dildo onto his tummy, dwarfing his softening little package beneath it.

"I'm going to fuck you with this big black cock so you can finally understand what it's like. If you really love me, then you'll do this for me, right?"

"Do... do I have to?"

"Only if you want to show me how much you love me," Ava answered expectantly.

"Umm... okay then, maybe just the tip?"

"I'm going to need more than that sweetie. I need you to ask me to fuck you with this big black dick, or you'll never truly understand me."

"Mommy...." Ashley started hesitantly, than building up steam he said the most fateful words of his young life. "Please fuck me with your big black dick."

Ava rested the base of the dildo on her pelvic bone and rested the tip against Ashley's ass, then scooping her fingers repeatedly into her still-wet pussy, she rubbed her juices up and down the shaft, and especially around the head. Then, lubed and ready to go, she looked deep into Ashley's eyes and whispered, "I love you sweetie."

Ava's first thrust pushed hard against Ashley's hole, but even loosened as he was from Ava fingering him earlier he wasn't able to take the full width of the bulbous head, and even the bit that Ava was able to force in send waves of burning pain that brought tears to his eyes. She pulled back and thrust again, forcing another millimeter in and drawing a cry from Ashley. After a few more probing thrusts with similar results Ava pulled back.

"Sweetie, this is too much," she said, "I shouldn't have started you off with something so big, I don't know what I was thinking, we can just..."

"No!" Ashley yelled with sudden ferocity. "I want to feel what you felt. Please, don't hold back anymore, and fuck my ass already!"

Ava's next three thrusts were nothing short of ferocious as she slammed the dildo into her son's ass with the full weight of her body behind it, lifting his legs up and back so she could angle her cock down and use gravity to her advantage. Ashley felt as if she were going to split him in two, but finally with the third thrust he felt something pop and a sudden sensation of delightful fullness flooded him from the inside as the wide head nestled inside of his painfully stretched hole. The pain ebbed and was replaced with even greater pleasure as even with just the head in the special spot he'd found inside him while fingering was squeezed, bringing his soft cock twitching back to life. Ava tried to pull out for another thrust, but Ashley was gripping the shaft of the dildo too tightly to let even the slightest bit of the head back out, so Ava settled on the only remaining direction of motion, pressing her weight down to force the dildo even deeper inside him.

Inch by inch Ava worked the entirety of the dildo into Ashley, rearranging his insides and making his eyes roll back in unspeakable pleasure. By the time it was halfway inside his little dicklette was standing at full attention, and when she buried the final inch in his ass the first drops of precum oozed from the tip. Then Ashley's ass finally loosened it's tight grip enough that Ava was able to slide the dildo partway out, so keeping one hand on the base to hold it firmly against herself, Ava started to fuck her sweet sissy son's hole while grinding her clit on the base.

Ashley reached down and grabbed one of his ankles in each hand pulling his legs back to give his mother the best angle possible to plunge her rod of pleasure deep into him. Looking up into Ava's eyes as she plowed into him Ashley felt like he was having an out of body experience. Having sex with Ava (or at least, getting an ass-job from her as it turned out) had been the most intense pleasure he'd ever felt in his life. But it was nothing compared to the full body heat that she felt right now. Laying there, her makeup a mess and her dress askew with her tits hanging out and her panties tossed God knows where, offering her ass wantonly to be destroyed by this black cock as she squeezed herself down on it to feel every blessed ridge and bump along it's length she finally understood what Ava had learned a month before. Getting fucked as a girl by big black cock was the best feeling in the world, and she could never go back.

"Keep fucking me mommy, just like that," Ashley begged, "make your little girl cream on that big black dick."

Those lewd words pushed Ava over the edge as she climaxed for the second time that night, grinding herself into the huge black dildo at the same time as it made Ashley spurt from her clitty. For a few minutes the only sound in the room was their heavy breathing as both came down from the peak, then Ava collapsed onto the bed next to Ashley and before long the exhausted couple fell asleep in each other's arms.

POSSIBLE BREAK POINT

The next morning Ashley woke up first, still mostly wearing her dress from the night before and with a dried sticky spot on her tummy from where Ava had made her cum with that big beautiful dildo. She stretched slowly, then reached her hand down to feel the strange object pressing into her. Her fingers wrapped around something firm, thicker than she could even get her hand around, and she realized with a start that it was the dildo Ava had fucked her with the night before. She marveled at the size of it, amazed that she'd been able to fit the whole monster inside of her as she traced her fingers lovingly over the veiny ridges that had given her such pleasure the night before. She could feel herself getting hard, and for a moment she thought about masturbating herself. Ava was sleeping soundly next to her, and this was the first time she'd been unlocked in weeks. She could pay with herself and cum before Ava woke up and nobody would ever be the wiser.

But somehow the very thought of that felt wrong. So instead she crawled down under the sheets between Ava's legs, slid herself up under her mother's dress, and began to slowly and tenderly lick. Ava awoke slowly from a beautiful dream. She was the beloved Queen of a prosperous country, without husband, but with many loyal knights who served her as she wished with their mighty swords to keep her satisfied. But her greatest treasure was the dear princess her daughter, who sat at her feet in the royal throne room slipping up under her royal gown to please her with her talented tongue whenever her heart desired. As she gradually came fully awake with a smile on her face, Ava's heart leapt as she realized that her dream had come true. She laid back and allowed Ashley to continue, signaling her growing pleasure with increasing moans of appreciation. Realizing that Ava was now awake, Ashley increased her intensity, switching between licking her mother's ass and pussy and gradually eating her out more forcefully until finally Ava's thighs clenched and Ashley went in for the kill, sucking hard on her clit to send her over the edge to orgasm.

Ashley extricated herself from Ava's legs and slid back up from under the sheets, laying on top of Ava in a tired embrace as she rested her head on her shoulder. Ava ran her hand through Ashley's hair affectionately before addressing the elephant in the room.

"That was lovely my dear, you may have to wake me up like that every day from now on, but I have to ask, do you understand now why I need big black cock?

"Oh god yes I do," Ashley answered emphatically. "Mom, when I had that in me I felt... I felt...."

"Like you were complete?" Ava offered.

"Yes, exactly!"

"Trust me sweetie, it's even better when it's the real thing, warm and alive and pulsing inside you. Maybe someday you'll experience that as well."

"Maybe..."

"So are you okay with knowing that I'm going to keep getting fucked by as many black cocks as I can find?

"Mom." Ashley said seriously. "I'd be disappointed if you didn't. Now that I've felt what it's like, how could I deny you? I want you to be happy. You deserve to be the happiest woman in the world, so I want you to have sex with whoever you want to, I just...."

"Yes sweetie?"

"I just want to be the one you come home to every night mom. I don't care who you have sex with, what we have is so much more than that, just please tell me that I can be that for you."

Ava was stunned. Her hope had been to let Ashley down easily, to make him see that it just couldn't work out between them because of her special needs. Never in her wildest dreams did she think that her son would be okay with an open relationship like that, but the idea of it sent a fresh wave of juices flooding into her freshly licked pussy. The thought of having her pick of all the hung black studs she wanted by day, then coming home to her perfect sweet Ashley every night... There was just one problem that she foresaw.

"That... sounds amazing," Ava finally said, "But I don't think it will work. If I'm with you then lots of the guys I want to fuck won't even think about it, they'll be too worried about another man getting jealous, and causing trouble. I mean, I'm sure I could still find some guys who are willing, but I don't..."

"Mom!" Ashley interrupted with a laugh. "It's okay. I think... I think I'm a girl."

"What? Sweetie, that's wonderful, I've always wanted a daughter, and you're so pretty, and... Are you sure? Are you sure this is what you want, not just something you're doing for me? I want you to be happy too sweetie."

"I'm sure," Ashley answered, gaining confidence as she spoke. "I've been fighting it for a long time, but more and more it's started to just feel right, and last night when you were fucking me with your dildo, I had a moment of clarity where I suddenly let go and just realized, this is who I am. This is who I want to be."

"Oh Ashley, I'm so happy!" Ava said, fighting back tears of joy. "I knew there was a reason the universe was changing you, molding you into this, and now we can truly be together."

"Thanks mom, I just have one question for you," Ashley said as she fished around under the sheets and pulled her hand out with the dildo clasped in it. "Do you think you could make a woman of me one more time before we start the day?

Ava laughed and snatched the dildo from Ashley, then rolled her daughter over onto hands and knees and mounted her from behind, fucking her doggystyle until she shot her load into the sheets in a cry of ecstasy.

After finishing their morning sex, the girls hopped in the shower together washing and giggling as they enjoyed one another's bodies. Ava marveled at the sudden growth spurt in Ashley's breasts, and she shared how Dejuan's massage the day before had felt like it was releasing something within as they stretched out. Ava helped walk Ashley through the finer points of get makeup, then the pair picked out coordinating dresses to wear for the day. They were nearly ready to go when Ashley approached Ava with something tucked in her hand.

"Hey mom," Ashley asked as she held out her chastity device, "Are you going to lock me up again?"

Ava toyed with the key still dangling from her necklace and thought for a moment.

"There's a certain appeal, it's fun holding that kind of power, but I also like the idea of having you accessible to play with... maybe we don't have to if you'll promise to behave and be a good girl for mommy."

"I can do that!" Ashley answered emphatically. "What do you want me to do?"

"Here are the terms," Ava answered seriously. "First, I'm the only woman for you, I don't want any other ladies trying to steal my little girl. Second, I get to fuck whoever I want, no questions asked, and no complaints. Third, I want you to practice cumming like a girl, no jerking off. Deal?"

"Deal!"

"Good, then come here and kiss the key and swear it. I'll keep wearing it even if you're unlocked just so we both remember who's in charge."

Ashley solemnly walked in front of her mother and said, "I swear you're the only woman for me," then learned her face down into Ava's cleavage and kissed the key and the heart that rested there. "I swear I'll be happy for you to fuck whoever you'd like." Ashley repeated her kiss. "And I swear I'll only cum like a girl." Ashley repeated her kiss one final time.

"Good girl, Ava said with a broad smile. "Now let's go hit the spa."

At the spa Ashley picked up her customary coconut cream drink while Ava booked them both for a special massage. She kept tight-lipped about what it was until they were in the room, then told Ashley she needed to strip all the way down for this one. She was hesitant, but peer pressure from Ava and the warm fuzzy feeling from her drink soon led to her clothes hitting the floor and her laying fully nude under her massage towel. A few minutes later Dejuan and Leandro walked in and asked if Ava or Ashley had any questions about their Yoni massage. Ava didn't, and Ashley didn't want to let on that she didn't know what was happening, so they got to work.

The massage started out normal, with Leandro kneading his hands into Ashley's thighs just as he'd done the day before. But as he slid his hands up under the towel his thumbs worked their way closer and closer to Ashley's hole as his hands pulled her cheeks apart. She felt nervously unsure, but she also knew just how good Leandro's strong hands could feel, so Ashley said nothing as he worked his oiled thumbs in gradually tightening circles. Then one of his thick thumbs popped into Ashley's hole and back out, resuming it's slow circle of pressure. Then his other thumb slid in, following the warm oily path led by the first, and back out. A rhythm started of repeated penetration and withdrawal, with each cycle pushing more of the warm massage oil into Ashley's ass and each cycle relaxing her and gradually opening her wider and wider. She opened her eyes and turned her head to check on Ava, and saw that Dejuan was giving her a similar treatment under her towel, and that she seemed to be enjoying herself.

As the rhythm of Leandro's thumbs penetrating Ashley's hole grew faster, each thrust also went deeper and slid in more smoothly, and she felt the familiar molten pool of arousal building inside of her. She could feel the stiffness of her little erection underneath her, and guiltily wondered if she was supposed to have that. But Leandro was a man, not a woman, and she wasn't playing with herself, she was just enjoying the massage that Ava had selected for them. She decided to relax and enjoy it just as Leandro lined both his thumbs up at the same time, thrusting them together into Ashley and massaging her from the inside. She squirmed under him in pleasure, but didn't tell him to stop as he worked his thumbs all around but especially into her special spot. She looked over to Ava again, eyes pleading as arousal took her. Ava looked back and saw what was happening and what her daughter needed, and mouthed the words "cum for me", watching with pleasure as Ashley's face contorted in orgasm from a man's touch for the first time. Leandro continued his steady work as Ashley convulsed beneath him, milking out spurt after spurt. Finally Ashley was finished and Ava called Leandro over to give Dejuan a hand with her massage, telling Ashley to run and fetch the four of them drinks.

With a spa robe pulled on, Ashley walked alone back to the front desk, and found there was no receptionist there. She waited for a few minutes and still didn't see anyone, but she did hear voices coming from somewhere in the back through a door labeled 'Employees Only'. Not wanting to disappoint Ava by taking too long, Ashley slipped around the counter and through the door, where she found the most surprising sight she'd seen in her life.

The spa receptionist was there, kneeling on the ground, and all around her were a dozen of the male employees of the Pink Lotus, each with their big cocks out and hard. Most of them were stroking themselves, but one was standing directly in front of Dalena as she jerked him off. Ashley was about to back away when she saw that Dalena was holding a familiar coconut in her free hand. Just then the man she was jerking off came, and she caught each spurt of his creamy seed in the coconut, filling it with rope after rope, then gestured to the next man in the circle. Realization dawned on Ashley like a thunderclap, and she went running back to the massage room. Ava's massage had reached it's happy ending and she was chatting with Leandro and Dejuan as Ashley came barging in and told Ava she needed to come with her right now. On the way back to the front Ashley tried to explain what she'd seen, but her words came tumbling out sideways and so Ava was nearly as shocked as Ashley had been when they burst into the back room. The circle of men stroking themselves was still there, but Dalena had stood and was waiting for them.

"Ms. Addams, Miss Ashley, this area is for employees only, we are just finishing preparing Miss Ashley's drink, if you will wait in the lobby we will have it out to you shortly."

"You see mom?" Ashley yelled wildly, "This is what I was trying to tell you, those men were cumming in my drink!"

Ava had come storming in with Ashley with all the righteous fury of a mother hen protecting her chick, but the sight of a dozen big hard black cocks was short circuiting her brain and making it hard to think clearly.

"These nice young men?" Ava asked uncertainly, "Why would they do a thing like that?"

"Because your daughter was a bitch!" Dalena interjected.

"Excuse me?"

Dalena explained the staff side of events at the Pink Lotus since their arrival. Dalena had deliberately 'lost' Ashley's suitcase because of the shit-fit she'd thrown over being confused for a girl at check-in. She'd meant to give it back, but then there was a mixup and the porters actually lost it and it was too late. Then Ashley had been a bitch about the accidental body hair treatment at the spa, so they'd come up with the idea of having of the male staff jerk off into a coconut milk drink and thrown in a dose of menopause replacement hormones for the 'whiny little bitch' as a joke. But they hadn't expected that Ashley would keep on asking for more and more of the drinks, and the more of them Ashley had the more pleasant she became to deal with. So they'd started recruiting more and more staff to provide their cream, gradually reducing the amount of coconut milk while also increasing the hormonal dose. By the last week, Dalena admitted shyly, each drink they'd given Ashley had been basically pure cum with a splash of actual coconut milk for sweetness, plus about a weeks worth of estrogen and progesterone.

"So... you're telling me that you turned my son into my daughter and got her hooked on cum as a punishment? As a joke?" Ava asked when Dalena finally finished her explanation.

Dalena nodded, bracing herself for a mother's wrath, but instead Ava walked up and threw her arms around the woman, hugging her so tightly she almost dropped the coconut she was holding.

"Thank you!" Ava said, " thank you, you have no idea what you've done for us."

Ava took the coconut cup from the surprised woman and walked it back to her equally surprised daughter.

"Ashley," Ava said as she held out the cup, these men are horny and need to be taken care of. Jerk them all off so you can have your medicine."

Ashley froze. There was no way she could go through with this. Sure, she'd let Ava fuck her last night with a big black dildo. And again this morning. But she couldn't actually touch all these big strong men's actual cocks, could she? She couldn't jerk each of them off into her coconut cup, right? She looked down into the cup, seeing the swirling cream from the first man agreed watched Dalena jerk off. Ashley could almost taste it. She shouldn't need it this badly, not after having a serving already this morning, but somehow that just made her want it more. She wondered idly if that batch had been from the same group of men, or a different one, and if she'd drunk the yummy cum of every man working at the Pink Lotus by now.

Her decision was made before she even realized it. Ashley took the coconut shell from Ava's hand, smiled as she said "Yes Mommy" and set to work.

It took the better part of an hour, and Ashley's arms were burning by the time she finished. Ava made her thank each man for his cum as she jerked them off and wouldn't let her taste a single drop until she was completely finished. The irony of jerking off cock after cock when she hadn't been able to jerk her own since arriving in Jamaica wasn't lost on Ashley, but in a way it felt right. These big beautiful dicks deserved to stroked as often as they desired, and the difference between them and hers couldn't have been more clear. What started as a task from her mother soon turned into a passion, as Ashley enjoyed indulging in the unique majesty of each of the huge cocks she jerked off and strove her best to milk each and every drop of cum from them.

When Ashley finally finished she presented the nearly full coconut to Ava for her approval. Ava took it and held it as Dalena stirred in several vials of hormone replacement medicine and a frothy splash of coconut milk. Ava swirled the drink to mix it, then signaled Ashley to kneel in front of her. She opened her spa robe wide and hefted one of her massive G-cup breasts, presenting it to Ashley, who obediently took it into her mouth, sucking in one of her large nipples. Then Ava took the coconut Ashley had so carefully filled, and began to slowly pour it down the top of her breast. The creamy mix of cum and hormones oozed slowly down her tit until it reached Ashley's upper lip, where her suckling pulled it into her mouth. Bit by bit Ava fed Ashley her medicine, letting her nurse from her nipple as she greedily sucked down the key to her ongoing feminization. When the coconut was finally emptied, Ashley licked her way up the rest of her mother's breast, eagerly cleaning off every bit of residue. Ava looked down at her daughter, beaming with pride, then leaned down to kiss her for a job well done.