Hot Mom's Sissy Honeymoon Sweetie 4

~~~~~ Day 6: Setting Boundaries ~~~~~

The next morning Ashley woke up with a smile on his face. After five days without a chance to rub one out, after five days of living in close quarters with his smoking hot mom, after watching live the hottest sex scene he'd ever witnessed and not being able to touch himself. After all of that he'd finally gotten his rocks off, and it had been with Ava milking his cock between her perfect tits. It was a storybook ending to their third date, and he couldn't wait to turn the page and see what was next for them. He slid one hand down under the blankets of their shared bed, lifting the hem of the beach cover-up he was still wearing from the day before, to play with himself while reliving last night in his mind. But instead of soft flesh between his legs his fingers brushed against pitiless cold steel. It took a moment for his sleepy mind to process what he was feeling, then his eyes snapped wide in shock. Somehow he was locked once again in the chastity device Ava had received as a gag gift at her bachelorette party. He looked frantically around the room and saw that Ava was up already, sitting in the chair across the room from their bed and wearing a full length silk kimono-style robe as she watched him from her perch.

"Hey that was something last night," Ashley said, trying to match the smooth confidence he'd seen in movies even as his voice cracked. "What do you say you unlock this and we pick up where we left off?"

"Very funny Ashley," Ava replied sternly, "But we crossed a line last night, and it can't happen again. That's why I locked you back up while you were sleeping."

"Crossed a line? But you were the one that came on to me!"

"I know," Ava admitted seriously, "and I take responsibility for that. That's why I'm taking responsibility to make sure it never happens again."

"Can't we just pretend it never happened and let things keep going as they are?".

"No dear, I've done some thinking while you slept, and there are two options. Option number one is that we call off the trip, go home early, and do our best to go back to our normal lives."

Ashley's face was crestfallen as Ava paused for a moment.

"Option number two is that you locked, and I keep the key, and we can continue our stay her at the Pink Lotus for the rest of the month."

Ashley thought long and hard as he pondered his response. A part of him couldn't believe that he was even considering going along with being locked in chastity by his mother for the rest of the month. But a much greater part of him couldn't imagine giving up the rest of their time together on Ava's honeymoon trip and going back to their ordinary life. Finally curiosity got the best of him.

"So.... If I do this and let you keep me locked, what does the rest of our time here look like?"

Ava fought to keep a smile from her face. She'd wanted more than anything to stay and continue their vacation together, but she couldn't let Ashley know that or he might try to take advantage of another moment of weakness on her part.

"Well, in a lot of ways the same as the past few days. We can keep enjoying all the wonderful amenities of the resort, have a good time together, relax, and deepen our bond. Of course we'll still need to share a room since we're still on the Honeymoon Package."

"So if we're sharing a room, does that mean still sharing a bed?

"Well I'm hardly going to make you sleep on the floor," Ava said with a laugh.

"And what about getting changed in the room," Ashley asked cautiously. "You said before it was too much bother to be modest all the time, would we still be casual about all of that?"

"Well it is such a bother to duck around the corner for every outfit change..." Ava paused as she thought. "I suppose if you behave yourself then we don't need to be too fastidious about it. Although we should really try to at least wear our panties around each other to maintain a little bit of decency."

"What about going on dates together?" Ashley asked hopefully. "I think I could still use some practice if you don't mind."

"I... don't think so," Ava finally forced herself to say. "You're quite the charmer and I think I've taught you all you need to know. We'll still have dinners together on the beach of course, but let's keep that casual, okay sweetie?"

"Yeah, yeah, totally casual. I can do that."

"Good. Is there anything else?"

Ashley thought for a long moment, building up the courage to ask his final question.

"What about... Is it okay if we still kiss? Sometimes?"

"I really don't think that's appropriate, do you?" Ava answered. "I mean, probably not, right? Although I suppose that in some cultures they do that, so maybe it could be okay?"

Ava looked at the hope blooming behind Ashley's eyes, and she just couldn't find it in her heart to tell him no, even as her head told her she was crazy.

"Maybe sometimes," she finally admitted. "Just little kisses. But it stops there, and only when I initiate it. If this is going to work, then I have to be the one in charge and you need to follow my lead. Deal?"

"Deal!" Ashley answered enthusiastically before Ava could change her mind.

Ava smiled at her son's obvious enthusiasm and waved him over. He hopped out of bed and quickly walked over to her as she stood up from her chair and extended her hand with an air of ritual formality. Ashley took it and shook out in his own, matching her serious vibe, so he was taken completely by surprise when Ava pulled him forwards by his arm, wrapped her other arm around the back of his head and leaned in to give him a quick peck on the lips.

"We're going to have such fun together," she said with a mischievous wink. And Ashley knew that she was right.

With their difficult conversation out of the way, Ava told Ashley that she wanted to go check out the tennis courts. She loaned him one of her tennis skirts, which she pointed out had built-in shorts underneath making it not too girly, and told him that he could just wear his sports bra up top. Then Ava shed her silk robe, dropping it to the floor and went to pick out a similar outfit for herself. Ashley tried not to stare too obviously as Ava walked around the room in her panties, remembering her instructions to behave himself, but even then he still got an eyeful of her perfect curvy body. Then to make things fair, Ashley stripped out of yesterday's bikini and put on a fresh pair of the boyshort panties Ava had bought for him, finding excuses to hang around her for a bit before getting dressed. He might have been imagining it, but Ashley thought that he might have caught her checking him out once or twice, and the idea of being that attractive to her gave him goosebumps in spite of the warm weather.

After a pleasant morning walk across the resort, Ava led Ashley to the front desk of the Athletic Center and asked for equipment for her and her daughter. That made Ashley do a double take, but she smiled and didn't say anything until after they'd gotten their racquets and balls and were heading to the courts.

"Your daughter?" he asked incredulously.

"Oh don't get your panties in a twist," Ava said as she gave Ashley's hand a loving squeeze. "It's just that given the way you look right now, isn't it just easier to let people think that's what you are instead of having to explain it all the time?"

"Maybe I guess, but it still feels kinda weird."

"You'll get used to it, trust me. Besides, being a girl is loads more fun, and there's some perks too."

"Like what?"

"Well when we're done playing we can both just use the Women's locker room to freshen up, won't that be nicer?"

Ashley made a non-committal grunt as they took to the court and began to play. Tennis had always been the sport Ashley did best at, as his smaller size was less of a disadvantage than in contact sports and he didn't have to deal with bullying from bigger teammates. Ava had played in high school as well, but that was years ago, so while she held her own and made a game of it, most of the points in their warm-up games went to her son. So when they paused for water before starting an actual match, Ashley was feeling confident as Ava made her pitch.

"What do you say we make this a little more interesting? First one to six games wins and if I win..." Ava paused as she considered her wager. "If I win then you have to use the women's locker room with me afterwards without fussing about it."

Ashley thought for a moment, he didn't think there was much chance of losing, and honestly going to the women's locker room and checking out all the hotties in there didn't sound like the worst thing.

"And what do I get if I win?" he asked, subconsciously flicking his eyes down to Ava's cleavage where the key to his chastity cage was still safely attached to the heart pendant he'd given her for Mother's Day.

"Not that!" Ava said with a laugh, tugging her necklace with one hand, "That is off the table for you. What else would you like?"

"How about.... five minutes of making out?"

"One minute, and you keep your hands to yourself you naughty little boy."

"Three minutes, hands stay outside of clothes," Ashley countered.

"Two minutes, and you may have your hands on my back, final offer."

"Done! Get ready, because you're going down Mom!"

The thrill of competition with a friendly wager on the line made tennis even more enjoyable for the pair, and they were soon laughing and playing together without a care in the world. Ashley won the first two games handily, breaking Ava's serve, but then they should the next four with each of them holding their own serve, putting the match score at 4-2. In spite of being twenty years older, Ava was still in great shape, but the real difference maker as she started to win some games was Ashley dealing with the changes to his body. His hips were definitely wider and his ass felt a little thicker, throwing off his stride every so slightly. Plus while he'd never been a power hitter, his arm strength seemed a little less than he recalled. But what really threw him was the feeling of his budding boy boobies bouncing on his chest as he ran back and forth across the court. It hadn't been too bad when they were warming up, but as the level of competition increased and he started playing harder, it became more noticeable. Thankfully the sports bra Ava had purchased for him helped keep things in place, but the soft fabric also rubbed just right against his nipples with every bounce, and a quick look down confirmed that he had twin headlights poking out through the fabric.

In the next four games Ava managed to break Ashley's serve once as the constant stimulation of his nipples was now triggering another distracting response as his caged cock struggled to get hard in the flat chastity cage she was making him wear. That put the score at 5-5, and when Ava defended her serve in the next game they were at 6-5, with Ava needing to win just one more to seal the match. Ashley took a deep breath and tried to focus in as he prepared to serve, but on the other side of the court Ava started to play dirty. She reached into her sports bra, cupping one of her tits and lifting it halfway out, then repeated the process with the other. Her sports bra had done it's best to contain her massive breasts as she ran and jumped around the court, but now the elastic pulled in hard, pressing the large expanse of cleavage she'd just revealed up like a shelf. As she bounced from foot to foot in readiness for the serve Ashley was treated to the perfect view down her jiggling chest as he did his best to focus. The first two points he double faulted. The next he managed to serve inbounds, but got burnt by a hard return down the sideline, setting Ava up with match point at love-40. Ashley tried to take a long breath to calm down and managed once again to serve inbounds, but after a quick volley back and forth Ava was able to press the advantage of her momentum, taking the net and finishing Ashley off with a smash.

Accepting his defeat magnanimously, Ashley congratulated Ava on a great match and followed her into the women's locker room to clean up as agreed in their bet. Even with her leading the way he was nervous and worried that somebody might call him out for not belonging. The irony of being worried over being identified as a boy after years of stress over being mistaken for a girl was not lost on Ashley. But as they entered there was no cry of alarm or protest, one of the ladies inside even complimented Ava and Ashley on their cute matching outfits. As Ashley's stress started to wane his eyes started to wander. The women in the locker room weren't exactly parading around in the nude, but they also weren't bothering to cover up, and although he was dressed in a tennis skirt and sports bra and his cock was locked in a flat chastity cage he was still a man and couldn't help but get excited. These were the first women that he'd seen naked or at least partially undressed besides his mother, at least in person, and although none of them matched her body, they weren't hard on the eyes either. Ava noticed Ashley's wandering eyes and felt a surge of jealously. He was hers, and she didn't like the idea of any other woman stealing him from her.

"Eyes on me in the locker room sweetie," she said under her breath as she stepped in front of him. Ashley followed, doing his best to glue his eyes to Ava's swaying backside as she led them to the showers. There was an open shower area with a couple of women already as well as a few private shower stalls, but only one was available. Ava debated what to do internally. The open shower was clearly out, and she didn't trust Ashley to behave himself in the locker room without her direct supervision. That left only one option.

"We can use the private shower together for a quick rinse-off I suppose," she said casually.

"Are you sure Mom? I don't mind, I just don't want to get in trouble, you said we needed to be a little more decent around each other."

"I know, but really we've both seen it all already so the pussy is out of the bag, don't you think? Now strip and get in there before I change my mind."

Ashley complied, pulling off his sports bra, then turning to face the wall before pulling down his tennis skirt and panties just in case anybody was looking in their direction. A minute later Ava joined him in the shower, also nude from head-to-toe. Compared to the shower in their suite the spa shower was much smaller, clearly being designed with one occupant in mind, not two. That meant that their bodies were in near constant contact no matter how they tried to position themselves as they washed, so before long they gave up trying to avoid one another and accepted that it was going to happen, and they might as well enjoy themselves. Ava decided that if Ashley was going to shower with her he might as well be useful, and put him to work washing her hair and scrubbing her back. The combination of his soft hands working her scalp, shoulders and back with the hot water to her front was divine, and she started to wonder about having him take showers with her as a general rule. So long as he was safely locked away there wasn't too much risk, he seemed to be enjoying it, and she deserved a little pampering, didn't she?

"It was hard work beating you on the court," Ava said teasingly after Ashley had finished with her hair and back. "My muscles are all sore, be a dear and give me a massage."

Ashley didn't hesitate, sliding around her and dropping down to his knees, then reaching for one of Ava's feet and pulling it up into his lap, remembering when she'd had him rub her feet at the beach yesterday. As he set to work massaging it, Ava looked down at him in wonder. He was so pliable and easy, not even a word of protest at kneeling under the spray of water and serving at her feet. The sense of power was intoxicating, and for a moment she considered taking him by the back of the head and pressing his pretty little face directly into her crotch. It would be so easy, she knew he wouldn't resist her, and that sweet tongue of his could be put to work between her needy legs.

"Ashley," Ava finally said as she looked lovingly down at him, "I meant my shoulders, though if you want to give me a footrub later that would be welcome too."

"Oh, sorry," Ashley said sheepishly as he let go of Ava's foot and stood back up. "It's just that you said earlier if this was going to work then you had to be the one in charge. And I really want this to work mom."

"You're precious sweetie, I want this to work too," Ava said as she caressed Ashley's cheek. Then shifting her voice to playfully commanding she said, "Now get back there and massage my shoulders!"

"Yes Ma'am!" Ashley replied with mock seriousness as he slid back behind Ava and set to work massaging out the knots from her shoulders as she continued to enjoy her shower.

A while later, freshly washed and dressed, Ava and Ashley headed back into the resort to decide what to do with the rest of their day. Ava left it up to Ashley, and after a moment of thought he suggested that maybe they could go to the spa for a bit.

"Are you wanting to spend a little more time with that beautiful man Ajani?" Ava asked, "Or just have another one of those silly coconut drinks you like so much?"

The mention of Ajani immediately threw Ashley's mind back into watching through the window as the hung black man had fucked Ava all over their honeymoon suite, and he struggled to hide the strange mixture of shame and excitement he felt at the thought.

"The drinks are amazing," he finally managed to say, "you should try one!"

"Well that does sound nice," Ava admitted, "and perhaps after we can schedule a couple of masseurs to work us both over. Your massage was lovely, but I need a man with stronger hands to really give me a deep tissue massage."

At the spa they had Ashley's accustomed coconut cream drink waiting and ready, and it took them just a moment to go to the back and come out with another for Ava. Ava stayed at the counter for a moment to book their massages, while Ashley found them a place to sit and enjoy their drinks. By the time Ava had joined him, Ashley had already gulped down half of his drink and was forcing himself to slowly sip the rest and savor it. He looked eagerly to Ava's face as she tried hers, but it while she says it was nice, she definitely didn't have the same reaction he did. He was a little upset, but she told him not to worry about it and that different people having different tastes is normal and good. The two enjoyed light conversation together as they finished their drinks until they were called back for their massage.

In the room they were led to there were two massage tables ready for them, soft candlelight, and gentle music to create the perfect relaxing ambiance. While Ashley was taking it all in, Ava started removing her clothes and setting them neatly on a small table. By the time Ashley turned back to her, Ava was sliding her panties down and picking them up from the floor.

"What are you doing?"

"Why getting ready for my massage dear, you don't think they can work on us with all these clothes in the way, do you?"

"I uhh, guess not," Ashley replied, but doesn't that mean that they're going to see us naked?"

"It's all very professional, you have nothing to worry about. Besides, we'll be laying down on our tables with towels over our backsides, so it's not know they'll really see much anyways."

Ashley hesitated, his fingers hooked into the waistband of his skirt. Beyond just the normal fear of nudity in front of strangers, he was concerned about his cage being spotted and the odd questions that would accompany it.

"If you're not comfortable with that you can always leave your panties on," Ava offered helpfully, "but personally I prefer to bare it all so they can really work on my glutes"

A few minutes later both were stripped and ready, laying face down on the massage tables with soft towels draped over their backsides. Ashley elected to keep his panties on, although the additional coverage didn't make him feel that much more secure at the prospect of being seen by two strangers.

"Good afternoon ladies," a deep voice said as the door to the room opened, "welcome to the Pink Lotus Resort Spa, I am Dejuan and this is Leandro, we will be your masseurs today."

Ashley's eyes shot open as he turned to And in surprise and stage whispered "Mom, they're men!"

"Of course they are sweetie, I told you I needed a set of stronger hands on my body."

"But, I thought we'd be getting massages from women, this is kinda weird."

"If there is a problem then we can address it," Leandro offered. "The comfort of our guests is paramount."

"No, there's no problem," Ava said as she looked the masseurs up and down while biting her lip. "Ashley will be fine. Lay down and close your eyes sweetie, you're going to enjoy this."

Not seeing any other choice, Ashley relaxed into his massage table and tried his best. Dejuan poured warm oil over his back and set to work, forcefully working his large strong hands into Ashley's back and shoulders with a touch that was somehow both firm and soft. Any reservations that Ashley had felt quickly evaporated as his body melted into a warm puddle under the masseur's masterful touch. It felt like his body was being molded and reshaped, and every kneading touch made him feel better and better. All he has to do was lay there and take it as the powerful black man above him worked his body over with authoritative care.

As Dejuan moved on to working on his legs Ashley faced a new problem. It wasn't as if he was physically attracted to Dejuan, although he had to admit that the powerfully built man was quite handsome and there was something about the way he touched Ashley that stirred up butterflies in his stomach, but the massage felt so good that he could feel his penis straining to get erect inside his cage. His problem was made worse by Ava, who was also having her legs massaged by Leandro, and was moaning along in pleasure. He was happy that his mom was enjoying herself, but those moans sounded almost sexual and made it even more difficult to cope with his strange arousal in the moment. He was confused, unsure of how much of his arousal was due to Ava's breathy moans and how much was due to Dejuan's magic hands working their way up the smooth skin of his calves.

As the massage progressed Ashley's situation got harder. Dejuan was now working on his thighs, and the thicker flesh there was fertile ground for his hands to play in. With every sliding, oiled squeeze of Dejuan's hands as he worked them higher and higher up Ashley's thighs, he felt a drop of precum ooze from the front of his cage. It was embarrassing, but he couldn't help it as it felt like he was being milked. Looking at Ava's table only made matters worse, as Leandro was now working his hands under her towel and her moaning was reaching a more fevered pitch. A part of him wished that he'd forgone his panties so that he could have been massaged in the same way, his hips had been sore recently, and he was sure Dejuan could make them feel better. He was just about to ask when the masseur completed his final touch and stepped back. Disappointed and relieved at the same time, Ashley lay there feeling the small puddle of precum dampening the front of his panties.

"That was wonderful, you two are magicians with your hands," Ava exclaimed as she took her towel and wrapped it around her body, covering at least most of her curves.

"You are too kind," Dejuan responded with a bow. "It is our pleasure to work with two such beautiful bodies."

"You have to join us for dinner tonight, we have a private table on the beach," Ava offered, "and we've really been enjoying getting to know the local culture."

"I suppose we could," Leandro agreed, "so long as we aren't intruding."

"Not at all," Ava answered, "we were just going to have a casual dinner together, but with the two of you it will be like a double date! It'll be fun, we'll see you tonight."

The rest of the afternoon Ava and Ashley went back to their suite to relax and prepare for their double date. Ashley made a few casually snide comments asking why they needed to invite strangers to their dinner, but Ava reminded him that they were going to be keeping it casual from now on, so if he really wanted to practice his dating skills then he'd need to do it on someone else.

Ava tried on dress after dress for their date, asking Ashley which one he thought the boys would like best. He enjoyed watching the show, but felt a little uncomfortable at how eager Ava seemed to impress their dates. Eventually with his input she settled on a bright yellow halter top mini dress that hugged her curves and showed of her tits perfectly, just skirting the edge of what was acceptable to wear in public. She tried to convince Ashley to wear another of her dresses, or to at least let her touch up his face with a little makeup, but he steadfastly refused. The idea of dolling himself up for a date was just a step too far. Ava took his refusal in stride, careful not to push him too far, but told him that if he was going to be obstinate the least he could do was to give her a footrub while she did her makeup.

Although she acted like it was meant to be a punishment, Ashley was more than happy to take his place at Ava's feet. She scooted her chair back from the dressing table to make room for Ashley and he slid underneath. It was a little tight, but fortunately he was rather small so he had plenty of room to sit and work while Ava did her makeup and fixed her hair. Ava sat with her legs crossed so one of her feet rested on the floor while the was raised and offered to Ashley. He took it eagerly, running his fingers along her sole and over her toes before really settling into the massage. They didn't speak, as each was engrossed in their work, but the occasional moan of happy approval from Ava meant more than words ever could to Ashley. As he worked he kept his eyes fixed on the hypnotically bobbing foot in front of him, wondering if it would be okay to kiss it. He'd kissed Ava's toes during their beach footrub the day before and she hadn't minded, but there were other things they'd done yesterday too that she said couldn't be repeated. He finally convinced himself that one little kiss couldn't hurt, and so as he finished his massage he held her foot in both hands like a prince kneeling before the offered hand of his queen and leaned in to place one delicate kiss on the top of her toes.

Ashley pulled his head back, unsure if he'd overstepped, but was instead met with Ava's leg extending until her foot was directly in front of his face. Ashley took his cue, lavishing her sole with kisses until she finally pulled it back, set it on the floor, and lifted her other foot. Ashley again followed Ava's lead, beginning his massage on her other foot, but while she'd had her legs neatly crossed for the first one, now she was sitting in a more relaxed fashion with her legs spread wide. Combined with her short dress, that meant that Ashley was in the perfect position to see her ass and pussy, covered only by a black mesh thong. Between their showers, and clothes changes, and of course secretly seeing her get fucked by Ajani last night Ashley had technically seen all of Ava's perfect body already. But there was something different about seeing it this close and from this angle, he could even make out her pussy lips through the mesh....

"No daydreaming down there, you've got a job to do!"

As Ava spoke she pushed her foot once again towards Ashley's face, but this time she didn't stop when she made contact, gently feeling around with her toes until she found his mouth then hooking her big toe into his cheek and pulling his head down. Ashley quickly snapped to work, massaging his mother's foot with both hands. His line of sight up her dress was blocked now by her calf and it was difficult to pull his eyes up from her foot with her toe still hooked in his mouth, so he did his best to ignore the glimpse of paradise he'd just been given and to focus on the task at hand. As he continued diligently working Ava gradually relaxed the toe hooking his cheek, but instead of pulling it out of his mouth she slid it over, encouraging her son to suck on it, which Ashley did with relish while continuing to massage her foot. His devotion to his task only increased when he felt Ava's other foot sliding slowly between his kneeling legs, not stopping until her toes were brushing up against the bottoms of his balls through his skirt and panties. They didn't stroke or rub, and Ava didn't give any indication that she knew where she was touching him, but her lower foot remained there in soft contact.

After several minutes Ashley felt Ava's big toe being gradually pulled back and away from his mouth. He sucked harder, wanting to continue, but Ava gave him a gentle tap to the balls with her lower foot, causing him to open his mouth in a mixture of shock with a little pain, then took advantage of the opportunity to pull her foot back. Ashley was about to protest his loss, but before he could Ava pressed her foot forwards again, this time forcing all five toes into his mouth. Ashley couldn't help but release a groan of satisfaction as Ava forced her toes in deeper, until the ball of her foot was in his mouth as well. He continued his massage, working his tongue between each of her toes while continuing to rub the rest of her foot with his hands as his saliva gradually dribbled down. Eventually Ava gave Ashley's balls another gentle tap with her foot, this one slightly softer as she knew she had his attention, and he obediently opened his mouth, allowing her to withdraw. She scooted her chair back and stood, and Ashley crawled out from under the table, taking the hand she offered down to help him up. It was like having an angel reach down from the heavens. Ava was beautiful even without her makeup, but now she looked radiant, with her face and hair perfectly made up.

"You look.... amazing mom," Ashley finally managed to say as he found his feet.

"Thank you sweetie, you know, we can always be a little late for dinner if you want to touch up a bit. I can get you in a dress in no time and put at least a few touches on your face. Your eyes would be so pretty with just a little shadow."

Ashley really thought about it. Earlier he'd rejected the idea out of hand, but as he looked at Ava and wondered what it would be like to look like that, to be beautiful like her he hesitated. Especially if that's what she wanted him to look like. He knew that she was into men, and from their time at the resort he was starting to think that her type was big, hung, and black. But what if she was trying to nudge him in that direction because that's what she wanted? He could do that for her, if that's what it took. But for now he was still unsure.

"No thanks Mom, but I appreciate it, I really do. Maybe another time? Besides, I'm sure the guys tonight will be staring at you anyway, there's no chance they'll be looking at me."

"Suit yourself then," Ava said. "Kiss for luck?"

Ashley smiled as Ava leaned in and gave him a quick peck on the lips, then the two of them held hands and left for their date with Dejuan and Leandro.

Their dates were waiting for them at the table when they walked up, still wearing their Pink Lotus uniforms: white polo shirts with a pink flower embroidered on the chest and a tight pair of short linen shorts. Ashley had been too distracted during their massage to notice, but as they stood to pull out the chairs for him and Ava he saw that like every other male staff member at the resort they were packing. Previously he'd wondered if something about the cut if the shorts was making the bulges look bigger, but after seeing Ajani in action the night before he knew that was definitely not the case.

Ashley and Ava took the offered seats across from one another and sat with Dejuan and Leandro taking the seats between them. He knew now what to expect from a dinner with Ava when there were other men present, so he wasn't surprised when the conversation quickly became a threesome with him on the outside looking in. Ava flirted, and they both ate it up, casually resting their hands on her arms or legs as they laughed and talked. While struggling not to feel jealous of them, Ashley started idly wondering what it would be like if he were the center of attention. If he'd let Ava dress him up and do his makeup would he be laughing and talking with Dejuan right now? Would he be the one feeling Dejuan's strong, yet gentle hand grasping his thigh? He realized with a start that he suddenly wasn't feeling jealous for Ava's attention, he was feeling jealous of the attention she was getting.

When the meal ended and the four of them stood from their seats, Ashley was looking forward to a quiet evening back in the honeymoon suite with Ava. Unfortunately she had other ideas.

"Ashley darling," she asked, "would you mind terribly taking another walk tonight? I have some tight spots that really need to be worked out, and I think it will take Leandro and Dejuan both to take care of me."

"Ummm, sure Mom," Ashley replied, trying to keep his eyes going wide as he realized what she was planning. "If that's what you'd like."

"It really is, thank you sweetie. Enjoy your walk, we should be done in an hour or so."

Ashley lingered by the table and watched as Ava led the two men down the trail back to their suite. She stood a full head shorter than either of them, and Ashley couldn't imagine how she was going to handle both of them at once, but he was definitely going to watch and find out. After waiting a few minutes, he quietly walked back down the path and to his spot at the window, where he found that Ava and her two dates had wasted no time in getting down to business.

Ava was on her knees in between the towering, now naked black men, stroking one of their big cocks in each of her hands while alternating back and forth sucking their bulbous heads in her mouth. She was moaning in appreciation for them, and with each transition between the two Ashley heard a quick string of thankful wonder spill from her lips at the feast she'd been provided. The chocolate rods she sucked on weren't just long, they were girthy; Ashley could see her fingers couldn't even fully wrap around the throbbing shafts. He slid a trembling hand down the waistband of his tennis skirt and started rubbing the sensitive area behind his balls with his fingers, causing his palm to naturally plap against his dangling sack with each cycle in a pleasant dual sensation.

It was like watching some of his favorite scenes of Blacked porn back home except that he wasn't able to jerk off to it. However, that failing was more than made up for by being able to see it in person and the fact that his mom was so much hotter than all those white girls he'd watched get plowed by hung black bulls. As Ashley watched and rubbed himself he thought about how much hotter Dejuan and Leandro were than the male performers he was used to watching as well. Dejuan was powerfully built with a solid, stocky frame, while Leandro was a bit taller and leaner with more of a swimmers build. Maybe it was just that he hadn't paid as much attention to the men when watching porn, or because the cameras had focused on the women getting railed, but he found himself if not attracted to them, definitely at least appreciating their masculine beauty.

As Ashley watched Ava let go of the twin cocks she was servicing to lift the halter top of her yellow dress over her head then let it fall, allowing her large breasts which had been straining against the imprisoning fabric to spring free. As she resumed stroking and sucking their cocks, Leandro and Dejuan both leaned over and reached down to start pawing at her tits. Ashley knew that Ava insisted they were "just boobs" and not actually sexual, but clearly the men fucking her didn't agree. Ashley found himself absentmindedly lifting his sports bra up and over the swelling on his chest that he'd started internally thinking of as "boy boobies" after Ava had called them that. He massaged the tender flesh, working it from the outside in towards his puffy nipples which were now fully erect with hard, sensitive nubs at the center. It felt good, but he wondered how much better it would feel to have Dejuan's or Leandro's skilled hands working them over, relieving his persistent soreness, twisting his nipples between their dextrous fingers carefully, but with just the right pinching hardness to send shivers down his spine.

Eventually the men fucking Ashley's mom were ready to move on from the appetizer to the main event. Ashley watched as Dejuan lifted her to her feet and set her on the bed on her hands and knees. He ripped off her panties, then placed his strong hands on her hips and leaned in to start eating her out from behind. Ava naturally pressed her face down into the bed and thrust her ass high in the air to give the man pleasuring her the best access she could, so Leandro moved in, positioning himself in front of her and pulling her head down onto his cock with both hands. While Leandro forced Ava to gradually deepthroat more and more of his cock, Dejuan stood up and lined himself up with Ava's offered pussy from behind, thrusting hard into the wet hole he'd prepared with his mouth. Ava's ecstatic groans of pleasure we're muffled by Leandro's cock, but even then Ashley could tell from his vantage point just how much she was enjoying herself. He felt his own excitement rising as he continued to play with his nipples and rub his hand behind and around his balls. Clear precum was oozing from the front of his flat chastity cage onto his wrist. It seemed like that was happening more and more now, as if his body was adapting to not being able to climax by releasing it's fluids just from getting sexually aroused. He worked some of his juices into his finger tips, using it as lube to help him glide more quickly back and forth over his sensitive perineum.

Ashley heard the growing moans of excitement from the threesome he was watching and thought that they might finish with Ava getting fucked from both ends, but then she lifted her head up from having her nose buried in Leandro's abdomen, letting the full length of his ten inch cock slide out of her throat and mouth, and said "I want you to fuck me in the ass."

Dejuan happily obliged, pulling out of her pussy and using her juices that were dripping from his cock to force his head into her tight asshole. Even lubed up it took some effort to work it in, and Ava's cries were a mixture of pain and pleasure as she frantically rubbed her pussy while her ass was reshaped to accommodate big black cock. Meanwhile Leandro moved from his spot in front of Ava to stand next to Dejuan as he realized this was his opportunity to fuck more than just Ava's mouth and throat. At his urging Dejuan lifted Ava from the bed, the two of them working together to hold her up with her legs spread wide, giving Leandro the perfect angle to push his slobbered knob into her eager pussy. Once he was in, the two men gradually lowered Ava down, forcing her ass to take all of Dejuan's meat as she buried her face in Leandro's muscled shoulder and whimpered in incoherent pleasure. Finally both men were fully inserted, stuffing Ava front and back, the fullest she'd ever been.

Ashley couldn't believe the amount of cock that Ava had managed to fit inside of herself, although as the two men sandwiching her started pumping in and out while she flopped helplessly suspended between them he realized that at this point she didn't have much of a choice in the matter. She'd invited these men on their double date, flirted with them and encouraged their advances at dinner, and invited them back to their suite. What was happening now was the natural consequence of those actions, and like an avalanche she was powerless to stop the natural conclusion of the chain of events she'd set in motion. Not that it seemed she wanted to. Her mixed cries of pain and pleasure that had started when she first struggled to take the large black cock invading her ass had morphed into sheer ecstacy, and she was now breathlessly encouraging them to pound her holes even harder. Seeing how much his mother enjoyed having her ass fucked made Ashley all the more aware of his own. He could feel it puckering and loosening in rhythm, as if it were longing to be filled, and he remembered the strangely beautiful sensation when he'd finally slipped a finger into it for the first time while watching Ava the night before. He thought about how wet with Ava's juices Dejuan's cock had been when he'd forced it into her ass and wished that he had some lube of his own, then realized the solution was right in front of him.

Ashley pulled down his tennis skirt for better access and started plapping one hand against his balls as hard as he could bear while holding the fingers of his other hand gingerly in front of the hole on the front of his chastity cage. As he hoped, it wasn't long before he had a small puddle of clear, sticky precum coating his fingers. While watching the ongoing scene in their suite, Ashley worked his lubed fingers around his twitching hole, imagining what it would feel like to be Ava in that moment, then plunged his fingers in. Whether due to the lube, the practice, or something else, it was far easier to finger himself now than it had been last night, and in his first thrust Ashley was shocked to find that he'd managed to take three fingers all the way to his second knuckle. Fortunately he was ready for the wave of knee-weakening pleasure this unleashed, and he was and to restrain himself from moaning too loudly and risking being caught peeping.

He continued working his fingers in as Ava's cries of abandoned ecstasy and Leandro and Dejuan's deep grunts of excitement approached their climax. When he'd gotten his three fingers fully inserted he felt a hard nub inside him under his fingertips and began experimentally rubbing it, taking his pleasure to a whole new level. It wasn't quite enough to make him cum, but he found himself riding the edge as he frantically plunged his fingers in and out of his ass while watching both men blow their loads deep in his mother's holes while she gasped in a matching climax of her own. As the men tenderly set three very satisfied Ava down on the bed, Ashley kept fingering his ass for a bit, but gradually slowed and then eventually pulled his hand away as the moment passed. He hadn't been able to reach climax, but the steady stream of precum that had oozed out had at least relieved the swollen ache in his balls, and he felt pleasantly content, if not fully satisfied. He knew that sometimes girls didn't climax even after sex, but that didn't necessarily mean they didn't enjoy it, and he wondered if this was how they felt, no big crescendo, but a generally warm fuzzy feeling.

Suddenly away of how exposed he was and thankful for the cover of darkness, Ashley pulled his panties and skirt up and lifted the front of his sports bra back over his boy boobies, careful to stretch the fabric over his still hard and sensitive nipples. Then he watched as Dejuan and Leandro dressed and left the suite while Ava continued to lay on their bed, her bright yellow dress only half-on. Not wanting to intrude, Ashley sat quietly against the side of the building, giving Ava some time to recover as he caught his breath as well. Finally when he thought it had been about an hour since they'd left dinner, he walked around to the front door and knocked. Ava answered after a moment. She'd changed into her pajamas, a forest green satin romper, and the sheen of sweat from her exertions was gone, but her tangled hair and messed up makeup still testified to the wild time she'd had. She pulled Ashley quickly into a warm hug and told him to go get dressed for bed, clearly excited to see him even after just an hour apart.

Ashley did as he was told, happily settling into their normal nighttime routine. He pulled out his pink satin romper, laid it on the bed, then started stripping out of his daytime clothes. Normally he'd just toss his clothes to the side, but with Ava obviously watching him out of the corner of her eye as she moved around the room taking care of small things, Ashley decided to put on more of a show. He hooked his fingers into the waistband of his tennis skirt, but instead of shrugging it off and letting it drop to the ground, he wiggled his hips as he worked it over his ass, then bent down at the hips as he lowered it all the way to the ground. He smiled as he heard a sharp intake of breath from behind him, giving his panty-clad ass another wiggle as he stepped out of his skirt before finally standing back up straight. Next he stripped out of his sports bra, lifting it gracefully over his head with both hands, then dropping it to the floor and giving his chest a quick rub after releasing it. Then Ashley casually walked over to the full length mirror, turning slightly to check out his ass while pulling up his panties a bit further, exposing a bit more of the bottoms of his plump cheeks. Finally he walked over to Ava, who pretended as if she hadn't been watching his every move, and innocently asked if he should change into a new pair of panties because his were a little damp in the front. She smiled as she struggled to control her reaction, and told him that was normal, and that one of the benefits of wearing panties was the cotton liner that could absorb a little dampness. So Ashley went ahead and stepped into his romper and told Ava he was ready for bed.

As they lay side by side Ashley rolled over to face Ava, then quietly asked, "Mom, did you have a nice time tonight?"

"I did sweetie, I really did," she answered warmly. "I had a lovely day with you and a wonderful evening as well, thank you."

Her answer resonated inside of Ashley, filling him with deep-seated joy. Of course he would rather have had Ava all to himself at dinner, whether on a formal date or even just casually, and although he'd enjoyed waves of unfamiliar pleasure as he fingered his ass and watched in secret he couldn't help but be acutely aware that of the four of them he was the only one who hadn't been able to reach full climax. But in spite of all that he discovered a hidden truth, which he shared eagerly with his mother.

"You're welcome Mom, and thank you too," he said sweetly. "If you're happy, then I'm happy."

"You are just the most precious little thing, come here," Ava cooed as she pulled him across the bed into a tight embrace.

Ashley basked in it for a moment, then realized the one thing that was missing to make his day complete.

"Mom?" he said as he pulled back slightly, "Do you think that maybe I could have a kiss goodnight?"

Ava thought for a long moment, one hand going to the heart pendant and key dangling from her necklace while the other reached down. She clicked her nails several times against the hard metal of his cage through the shorts of his satin romper, the taps sending shivers down Ashley's spine even though he could hardly feel any physical sensation from them, just knowing how close her hand was to touching him there, even if there was an impenetrable barrier between.

"I suppose that would be alright," she finally said, "so long as we keep our boundaries in place there's no reason to deprive ourselves of a little fun."

Ava cradled Ashley's head in her hand, brushing back his unruly blonde hair, and leaned slowly in to kiss him. Their lips met gently, tenderly exploring one another without the frantic excitement of a first kiss or the desperate need of a sexually charged one. This was the slow, languid dance of love, relaxed and comfortable with one another as each expressed their affection without hurry or rush, knowing that the other would always be there for them. Finally Ava broke off the kiss, sucking Ashley's lower lip between hers as she slowly pulled away, finally letting it snap back into place as they both caught their breath.

"Goodnight Ashley," she whispered so that only he could hear. "I love you."

"I love you too Mom," he whispered back as he took her offered hand, their fingers interlacing as they both laid down to sleep.

As Ashley drifted off he treasured that hand, secure and happy in the knowledge that although Ava had spent the evening with Dejuan and Leandro, he was the one that she came back to in the end.

Once Ashley's regular breathing and adorable little snore told Ava that he was fast asleep, she slid her romper bottoms to the side and started to rub herself with her free hand. Her pussy was still sore from getting fucked by Dejuan and Leandro, although nowhere near as sore as her stretched-out ass, but her goodnight kiss with Ashley, chaste as it had been, had lit a fire in her belly that she couldn't ignore. She avoided actually inserting her fingers, focusing instead on tight little circles of pressure around her sensitive clit. How was that boy so perfect for her? She had been worried that he'd be offended by her asking him to take a walk while she had her private time with their dates, but if anything he'd seemed genuinely happy that she'd had a nice time. It seemed like every man she'd been with was focused primarily on getting a piece of her body, and she knew that Ashley was plenty interested in that, but she would have never thought that her son of all people would be the first man she met that truly cared about her happiness more than getting himself off.

As her fingers shifted from working around the edges of clit to massaging it directly, she thought about watching Ashley's impromptu striptease when getting ready for bed. She'd have thought that after getting plowed by three big black cocks in two nights that her lust would be sated, but there was something about Ashley that was different. Normally she went for big, strong, black men with the biggest cocks she could find. Their swagger and understated dominance drove her wild, and now that she'd experienced the fullness of getting stuffed by them she knew she'd never be able to give it up. But somehow the complete opposite of those black bulls was now getting her just as excited and she was realizing that maybe sissy white femboys were also her type. It was in an entirely different way, as she got to take the dominant role for once and keep the focus entirely on her pleasure. Being with Ashley was almost like being with another girl, especially now that she had him wearing cute clothes and with the strange changes his body had been going through, except that unlike most girls he still had a cute little cock to play with.

It was a good thing she had it locked away, as she honestly didn't think she could trust herself not to take advantage of him if she had easy access to it. It was nothing like the big, hard black dicks that she loved to impale herself on, but it turned out that she appreciated dick in all it's forms. She was honored that Ashley had agreed to let her lock him up to be with her, and as she neared orgasm she fantasized about testing the limits of his devotion, teasing and tormenting him to see how horny she could make him before he broke and begged for release. Maybe even letting him out so that she could play with that cute little cock of his again...

Ava climaxed silently as her hand flew rapidly over her clit, imagining all the things she could do to her sweet little son while carefully ensuring she didn't wake him from his sleep. She squeezed his hand one final time, being rewarded by a contented sigh from his soft lips as he happily dreamed, then she laid back and entered sweet dreams of her own.