Coming out of my cage and I've been doing just fine

Holly noticed that Nick was in a good mood when he returned to the Master’s Suite. That was a good sign. She would cook him something extra nice to celebrate.

“Did you enjoy your date with Rose, master?” She asked cheerily. “She’s a bit of an odd one, but I know she means well!”

Nick nodded. “Yeah, it was… very interesting,” he said. “We went to see a couple of Hallmark movies.” He didn’t tell her that Rose happened to be the star of those movies. Judging by her attitude that was probably something she didn’t want other people to know.

Holly snorted. “Her? She watched Hallmark movies? That must have been ****!” Even Holly, who liked wholesome romances (most of the time) thought those films were mindless schlock.

Nick just smiled, wishing he could tell her how right she was.

“Something weird happened though…” Nick mused, stroking his chin. “Holly… I think Rose might be developing feelings for me.”

Holly blinked. “Oh, really?”

“…You don’t seem surprised,” he noted.

“Well, of course not!” She rolled her eyes. “Master, you’re the most amazing man who ever lived! Countless women the world over would be throwing themselves at your feet just to have a chance of sucking your dick, are you honestly shocked that Rose is one of those?”

Nick could definitely see how the nonchalant way Holly worshipped him could get addicting. But he had enough sense not to fall for it.

“Rose isn’t like that, though,” he said, shaking his head. “I don’t know, the way she was acting on our date… I expected her to try and seduce me, you know? She might have turned over a new leaf and become more sincere, but she’s still playful and flirtatious, and I didn’t see as much of that tonight, not as the date went on.”

“Rose not being flirty, huh?” Holly tapped her chin thoughtfully. “You’re right, it does sound kind of weird. But on the other hand, when we were working together on that challenge, I saw a lot of sides to her… she’s a very sincere person, when you look past her playful demeanor. Maybe she was trying to show a different side to you tonight.”

“Maybe so,” Nick agreed. The purpose of his date with Rose was to get to know her better, and he felt like he’d succeeded. But at the same time, he couldn’t shake the feeling that there was more he wasn’t seeing. It really felt like she had a crush on him, with how often she got flustered and embarrassed.

He sighed. “I guess I just don’t want to make the same mistake again…”

“…What mistake?” Holly asked quietly.

“You know, thinking that because a girl is friendly to me, that means she must have feelings for me. I’ve gotten burned on that too many times,” he said, shaking his head. Even though he was having regular sex with multiple gorgeous women, he couldn’t get over the inherent fear brought on from his years of self-doubt.

“Nick, come here,” Holly said, leading him over to the couch. She sat him down and began to give him a back rub. “That feel better?”

“Yeah, actually,” he said, looking over his shoulder and smiling.

She smiled back. “I’m glad. I just wish I could help you get over all this trauma of yours.”

“Trauma? I’m not traumatized!” Nick objected. Then he rethought things. “…Okay, well… I am. My best friend died, my mom died when I was a little kid… my dad died young, too… yeah, you’re right, I have a lot of trauma.” He sighed again. “…But a back rub and a pep talk isn’t going to help with that.”

“There’s that stuff, too, but that’s not the trauma I’m talking about.” Holly shook her head and increased the pressure on his shoulder blades. “I meant your trauma about women.”

“Wh-what do you mean?” He asked.

“Nick, what you just said… about how you were afraid of ‘getting burned’ again… that’s part of your trauma. You’re doubting Rose’s intentions, because you keep associating her with the other girls in your past. Dawn, Dani, Carly… even me. You thought we liked you, and when you got rejected… it hurt.”

“That’s ridiculous,” Nick snorted. “That’s not trauma!”

“It is!” Holly insisted. “Look, I’m not a psychiatrist, but I’ve been in therapy for a long time. And anything can be traumatizing. That’s what my doctor said. The only thing necessary for trauma is for a past experience to fundamentally change the way you approach something. In this case, your past experiences with women have changed the way you approached them. You’re cautious and guarded, and second-guess yourself! And I think it’s because you’re afraid that if you let yourself open up to someone without being certain how she feels about you, she might reject you. And that scares you more than anything.”

Her hands fell to her sides and she stepped back. If Nick was going to get upset with her, then so be it. Holly was just a sex ****, she didn’t have any right to condemn her master like that.

But she felt she needed to say something.

“You only had sex with Gina, Carly, and Dakota because they threw themselves at you,” she whispered. “And Dawn had to arrange an entire 24 hour date to get you to be with her. But when it comes to you… I don’t know, okay? But what I do know is that you keep spending a ton of your time up here with me, instead of pursuing anybody.”

Nick rose from the couch and turned to face her. “…Holly…”

“Yes, master?” She winced.

“You might be right,” he admitted. “As much as I hate to say it… back when Sylvia was my therapist, she said the same thing.”

“Oh, well that’s a glowing recommendation.”

“But she’s not wrong.” He approached her, and cupped her cheek. “You’re right, you know. I was too afraid to make any moves. I got my heart broken so many times, that at some point… I didn’t want to bet on something that wasn’t a sure thing.”

“…Well, you have me.” She reached up and placed her hand over his. “And I’m absolutely a sure thing. But you can’t just stay with me forever up in here, letting the girls come and service you. Isn’t there someone else you want to be with, master? Or multiple someones? People you love, that you’re willing to take a chance on?”

Nick smiled, and his eyes twinkled. “Well… what if the person I wanted to pursue was a sure thing?”

Holly giggled. “Well… in that case, you should still get out more and take some of that charm to the other women, master.”

“Oh, I don’t think I ever said I was talking about you.”

Holly’s mouth morphed into an “O” and she held her hand over her heart. “Ah, master! You’re so cruel to me! And so kind! You know just what to say to turn me on most!” She squeezed her legs together and shook.

Nick just sighed in exasperation and shook his head while thinking about their conversation. He couldn’t deny he’d been proactive. Whether out of fear of hurting the people he cared about by taking advantage of their transformations or out of worry from his trauma of past rejections, he’d been taking things slowly and going at the pace of whatever girl approached him.

But maybe it wouldn’t be so wrong to press the envelope himself, a little. To try and be more proactive to see what they were comfortable with?

He wouldn’t be able to do that with someone like Carly or Gina, though, he would need someone with limits.

That’s when he realized that the perfect person for that purpose was actually coming to his suite tonight.

“Holly… tonight’s my night with Dawn,” he said, turning to his sex **** maid. “I think maybe… you could be onto something. I’ll try and be a little more proactive.”

“That’s great, master!” Holly’s face lit up with glee. “Dawn is the perfect choice! After all, it was her rejection of you in elementary school that began this storm of trauma in the first place!”

Yep. Holly was a sure thing alright. He could always count on her to bluntly hurt him with her unintentionally insensitive words. And he couldn’t even be mad about it.

A knock on the door shook him out of those thoughts and he went to go greet her. But Holly stopped him before he could.

“One more thing, master.”

“Yeah?” Nick stopped with his hand on the knob and turned towards her. She looked surprisingly serious.

“About your trauma… it’s important to keep in mind that you weren’t wrong about most of them,” she said. “Dawn likes you. She might have even dated you, if it hadn’t been for her other issues. Dani is a lesbian. It’s not your fault she couldn’t date you. And as for Carly, she liked you, remember? And so did Mary and I…”

Holly held her heart and gave him a swelling smile. “Rejection, perceived or otherwise, must have stung. I’ve faced it myself. But just so you know, what you read from us, our feelings for you… at least my feelings, and Mary’s… you weren’t wrong. We really do love you, master. So keep in mind that with Rose, or Dawn, or whoever it is you’re after… maybe you aren’t misreading this time, either.”

Nick nodded. Now that she mentioned it, Dani might have been the only real rejection he’d received due to the girl’s feelings. That did go a long way in alleviating the pain in his heart. “I’ll keep that in mind.”

With that, Holly stepped aside and Nick answered the door.

Instantaneously, all his thoughts about being a charming, proactive guy trying to sweep Dawn off her feet went out the window.

“Wuh… buh…” He stammered, running his eyes up and down. “What happened to you?”

Dawn’s face was red. “Don’t… it’s complicated.”

Nick took a stab. “Dakota?”

“Dakota,” she confirmed with a sharp nod, walking inside.

He needed time to process this. “So you wanted her to give you Dani’s feminizing transformation, then?”

“Something like that,” she muttered, too embarrassed to look him in the eye. “Except I didn’t ask. She just sort of… kissed me. And then… whoomf.”

She waved her hand to emphasize her larger breasts and curvy hips. Meanwhile, Nick was stuck with the image of Dakota and Dawn making out.

“Look, don’t get mad at her. She knew I wanted something like this,” Dawn insisted. She finally looked him in the eye, and he saw the emotion watering within the pools of chocolate on her face. “I just wanted to be… better. For you.”

A silence hung over the room. A silence interrupted only by the shuffling sound of Holly’s legs rubbing against one another.

“As I’m sure you know, I was the one responsible for that transformation you got,” Dawn sighed, hanging her head. “After our horrendous last night together, I felt… inferior. Like the other girls could give you something that I couldn’t. I don’t know, it just… it flared something up in me, that stupid competitive urge to do better. I wanted to show you that I could handle you too, so I… I wrote it down.”

“Yeah, it was pretty obvious,” Nick nodded.

“Are you upset?” She asked.

“A little,” he admitted, causing her to wince. “But not because you gave me that transformation. I’m upset that you thought you needed to.”

“Wh-wha?” It was rare for Dawn to be at a loss for words.

“Dawn… I care about you,” Nick said, approaching her slowly. He reached up and brushed her bangs out of her eyes. “And I told you, it didn’t matter to me at all that the way things went… wasn’t ideal. You didn’t need to change me in order to please me.”

“I know, that’s why-”

“And you certainly didn’t need to change yourself,” he added, glancing at her curvy figure. “Although the maid outfit was a nice touch.”

“So… you don’t care that my body is so… frail?” She whispered.

He snorted out laughing. “Dawn, your body is a lot of things, but ‘frail’ is not one of them. I might not have your perfect memory, but I still remember how much I watched you in P.E.”

“Fair enough,” she laughed, brightening a little.

“I don’t care if you have big boobs, or no boobs, or one boob,” Nick assured her. “You’re just fine the way you are.”

“…Thank you?” Dawn was flattered, but at the same time, one boob? Maybe pushing it a bit.

“Master!” Holly hissed from her cage. “Be! Proactive!”

He glanced at her for a second and scowled. She didn’t need to remind him!

“Besides,” he added, turning back to Dawn, “with the other girls, I can’t do this!”

“Whoa! Hey! Whoa!” Dawn didn’t know how to react; before she could say anything, Nick scooped her up into his arms and carried her over to the bed. He let her down gently like a princess, leaving her completely flummoxed.

“Holly was going to make us a nice meal,” Nick explained, climbing on top of her. “But I was always the kind of guy who ate my dessert first. “If you’re okay with that, I mean.”

Dawn’s heart was pounding too fiercely to know if she was okay with that or not. “W-Well… it’s not like… it’s not like I have a problem with it or anything…”

She’d heard that Rose had taken Nick on a date tonight. She must have teased him quite a bit to get him this worked up!

Nick decided to take a page from the advice book he’d given to Kim, and go after what he wanted. And what he wanted right now was Dawn. While maybe not his first love, she was the first girl he ever seriously pursued, and the first girl to ever reject him. And now her she was, splayed out on the bed before him, face red, ears twitching, and eyes wet with submissive desire.

She might have rejected him once (or, well, three times give or take) but she wasn’t rejecting him now.

He leaned down and captured her lips for himself, while trying to get her out of the costume Carly had dressed her in. It may have looked modest compared to when the other girl wore it, but the bagginess added a strange charm, like someone inexperienced trying to look their best for their first date.

“Wait!” Dawn stopped him before he could get the last laces untied. He stopped, knowing this was an important part of his new attempt at proactiveness.

Dawn shyly glanced over at Holly, who was watching intently from her cage. “…What about her? Shouldn’t you… I don’t know… let her out of that belt?”

Nick glanced at Holly, who stared back at him with needy hope and expectation. She was practically panting like a dog.

She really helped me out tonight. She deserves something nice for that, he decided.

“Forget about her. Tonight’s just about you and I getting what we want,” he said fiercely, tearing Dawn’s costume away from her bouncing body.

Holly squealed, practically squirting in her chastity belt as she watched them kiss again.

“I, um… I couldn’t get a bra that fit,” Dawn said shyly, cupping her hands under her boobs to offer them up to Nick. “But I think they’re maybe Ds?”

“Now that doesn’t sound like the precise Dr. Willowbrook I know,” Nick teased.

She rolled her eyes. “Fine. They’re a 30D, happy?”

“So you actually measured?” This just got better and better.

Her face turned into a tomato. “I-I! It was just curiosity!” She sputtered. “I wanted to know for sure!”

“Well, let me see how they feel then,” Nick said, reaching down and palming them. He gave her chest a firm squeeze, surprised at how soft they were. The transformation hadn’t just boosted her size, this familiar texture was a direct replica of Dani’s silky smooth skin.

Master Touched Her Boobs! +2 VP

Dawn cringed a little, swallowing down the bile that welled up in her throat as she remembered not getting any VP from Nick’s sunscreen massage in the first challenge. So my boobs are finally big enough to count, huh? She thought bitterly.

Those thoughts were enough to keep her from realizing she was being groped for a second. But then the sensations reached her brain, and she squealed.

“Ahnn! Ah… they’re… ANGH!” She moaned, feeling her tail thrash against the sheets. She had, of course, given herself a few squeezes (just to know what it felt like, there were obviously no ulterior motives) and the results had been… nice.

But not as nice as Nick’s hands on her.

I have a… transformation that makes my fingers… feel especially pleasurable, and yet… Nick’s hands are so much more-! Dawn’s brain worked on logic, and this seemed to fly in the face of it. But her brain could take a backseat for now, because she just wanted to lose herself in his touch. And he’s so… aggressive!

This wasn’t the same as that night in the dream. Nick was really hungering for her. In spite of what he’d said, about not thinking about her any differently, it still felt like he was showing way more desire for her curvy figure than he had before.

That recognition stung, but she pushed through it. Instead of resisting, it felt nice, offering herself up to him. For once, I don’t have to think through what I’m doing. I can just let him have his way, and get some real pleasure out of it.

What Dawn didn’t realize was that Nick’s hunger had nothing to do with her body. He was just trying to test their limits together, and be more aggressive. Not necessarily dominating the way he did with Gina, but just a bit more active in sex. The fact that Dawn responded so well only reassured him that he was right.

Once her face was flushed with desire and her eyes were barely open and her glasses steamed up, he decided that he’d had enough of playing with her shortstack body, and wanted a real taste of it.

“I’m going to put it in now,” he whispered. “Are you ready for it?”

“Yes…” She mewled like a kitten, surprising both of them. Her cat ears twitched and she nodded, biting her lip. “Just… please finish outside…”

The last time they’d been together, it had been a dream. She could control things to a certain degree. But this was the real world, and the thought of getting pregnant in a situation like this… well, Dawn thought Mary was definitely nuts as far as THAT was concerned.

Nick understood, and nodded. Again, a boundary to respect. As good as it would have felt to cum inside her, he wasn’t going to push that limit.

He pulled back and unzipped his pants, fishing out his throbbing erection. He shifted his hips slightly and lined it up with her watery lips, noting that in spite of her transformations filling her out in other places, her little peach remained small and tight.

When he pushed himself inside her, he could feel that tightness for himself, and it was exquisite.

“O-OH!” Dawn shook, her arms shooting up and wrapping around him. She drove her nails into his back as her walls twitched around him, and he could feel her tail whip up against his side.

“Did-did that hurt?” He asked.

She just mewled again, and shook her head. He didn’t need to be a mind reader to understand her answer.

He pulled back slightly, delighting in the way her insides seemed to cling to him. He pushed in again, a little more forcefully. Before he might have been afraid of hurting her, but a mixture of knowledge of his transformation and the high from his new worldview drove him forward. If it hurt, she’d say so. But all she did was moan with joy.

“S-So big!” She shouted, bucking up against him. She enjoyed the new power her hips had, letting her respond to his thrusts in the perfect way. “I-I can’t… I-!”

She squirted again, squeezing down so tightly Nick felt like his dick had melted for a second. But he kept pushing forward, no matter how difficult it became, and only pulled back when he bottomed out inside her.

Dawn shook again, her glasses actually falling off from the **** of her spasms.

“More-!” She gasped hungrily, wrapping her legs around his waist and holding him down tightly, making sure she was as close to him as possible. Nick wasn’t a big man, but compared to the shortstack he was fucking he might as well have been a giant. And she certainly responded like he was.

They frantically made out as their lower parts smashed against one another, and Nick had to struggle to keep from falling on top of her. He used one arm to support himself while the other played with her breasts, getting as much out of her new body as he could before it was gone. She seemed to relish that, her prior insecurities about his love of her new rack all but gone; if these tits made sex feel so good, she didn’t want to give them back!

“Yes, ungh, please, right there!” She squealed as his cock brushed up against a sensitive spot inside of her. “Again, just… YEEEES!” She had a mini-orgasm as he pushed against her g-spot again, and squeezed down even tighter, with both her legs and her vagina.

Dawn had finally gotten a taste of that thing everyone seemed to want. And it was breathtaking. Her first foray into sex had almost put her off the damn thing altogether, but she was so glad it didn’t. Pleasure like this couldn’t be compared to what she’d received before, and it was firmly, indelibly etched into her brain.

Nick, on the other hand, had never had such a tight fit. While his cock had received a transformation to make it a perfect match for every girl he fucked, that didn’t mean they all felt the same. Dawn squeezed him like a vise, and he could feel the virgin hunger from her even if she wasn’t technically a virgin anymore. He wanted to satisfy her in every way he couldn’t that night; Dawn had seen her inability to properly perform as a failure on her part, but Nick felt just the same as far as he was concerned.

They were both making up for that lost night, and neither had any intention of ending any time soon.

But he couldn’t last forever.

“Dawn…” He grunted, thrusting into her again, and feeling himself go over the edge. “I’m gonna cum!”

He pulled back, intending to finish on her belly, but he found himself locked in place. Dawn’s legs were wrapped firmly around his waist, and he held him there with strength he couldn’t believe she had.

“T-Take it out!” She gasped, using every bit of her genius intellect to just barely remember not to let him finish inside. “Out… outside!”

But while the rational part of her brain was screaming one thing, everything else just wanted this pleasure to keep going. The rationalist that was Dawn Willowbrook was overwhelmed by a sea of ecstasy, and her smoking hot body couldn’t be bothered to listen to what that nerd in her head wanted to do.

As Nick floundered helplessly trying to escape from her depths, Dawn’s legs kept him there. And when they moaned together one final time and reached their crescendo as a couple, in the heat of the moment neither one of them even cared that he was hosing down her fertile insides with a thick wad of semen.