The Long Road
  • Author - M L
  • Rating -   
  • Site Rank - 1488 of 2955
  • Story Codes - M-f, chastity
  • Post Date - 1/12/2020

Part 1

Kaylee's 18th birthday was coming up soon, and she was looking forward to it. She'd been in a long term relationship with her highschool sweetheart, who was four years her senior. It hadn't been hard to sweep Kaylee off her feet during her freshman year for Charles. The girl had been eager to start dating, as her parents hadn't let her do so before high school.

At first their relationship was courtship, Charles wooing her with gifts and charm. She could hardly believe what was happening half the time; why would an upperclassman like Charles be interested in her? Kaylee didn't think much of herself, much shorter than others in her year. She did however feel grateful that her body seemed impossible to put weight onto, though this too had its drawbacks. Now turning 18, she hadn't grown as tall as others her age, standing at only 5'1", nor had she developed much in the way of breasts, to her disappointment. What little fat she did seem to manage to gain ended up in her butt, so she tended to wear tighter fitting pants and shorts to show it off. Her tan skin was mostly clear, save for a few freckles around her face and shoulders. Kaylee's hair was light brown, often tied back into a low ponytail.

Charles on the other hand, was tall and fit, 6'3", blonde and blue-eyed. To Kaylee, he looked straight out of a romance novel. In school he dressed pretty average, but was well kept and always smelled clean. Compared to the other boys in her own grade at the time, Kaylee couldn't imagine anyone stacking up. Since graduating, Charles still kept Kaylee close, taking her on dates and giving her rides to and from school every day. Her family loved him, and they quickly got over the age difference between them.

After the courtship and wooing, which lasted two years, Kaylee finally started to get sexually frustrated. The friends her age were all making progress in their relationships physically, but Kaylee and Charles hadn't done anything past cuddling and kissing. And not for lack of desire. Kaylee could clearly see Charles' arousal while they were cuddling, but would always ignore it and direct the topic elsewhere. Eventually he explained to her: "Kaylee my dear, I'm several years older. You're 16 and I'm 20. Legally, I shouldn't do anything until you're 18. Understood?" She'd pouted and argued, but eventually conceded to him. Since then, he'd redoubled his efforts to keep her happy, treating her to more kissing and massages, physical contact within the acceptable parameters to him. This was good enough for Kaylee at the start, but as the years went on, she felt like she was being left out, that Charles didn't really want to be physically close to her... but he finally gave her the promise she'd been waiting to hear: "When you turn 18, you can move out from your parents place, and live with me. Then things can be different... okay?" Kaylee had held onto this promise for the whole year, and in a few days she'd finally be 18 and could move in with Charles.

And, she did. Her birthday party was a fun time, and she let her parents know she was moving out. They were more than happy to let her, Charles could support her and let her parents get some alone time. He even helped her pack and transport her stuff to his house. Because he'd moved far into town, she'd only been to his place a few times thus far. But now she would be living there! It was exciting, for both of them.

Arriving at Charles' house was a bit nerve wracking for Kaylee. She'd been thinking about it for days now. Imagining him whisking her up in his arms and finally giving her that physical contact she'd been craving for so long. Kissing her... taking her clothes off. It all seemed so romantic in her head. He lived in an apartment, he'd said, but was surprised when they got into the elevator and he pressed the penthouse button.

"Are you excited to move into the next chapter of your life, Kaylee?" he said, smiling down at her. It really did feel like a romance story, everything more wondrous than she could have imagined.

"Yes! I'm so ready... I hope you have more plans for me tonight than just sitting around and watching TV..."

"Oh I have plans... don't you worry your cute little face..."

The elevator dinged, opening into the small hallway to the penthouse doors. Charles walked up, carrying Kaylee's bags still, and tapping his card on the handle of the door, a whirring click, and it opened automatically. "Welcome to my home... OUR ... home." He smiles and gestures into the lavish apartment. Walking in, she was blown away by the decor, and how clean and tidy it was.

"Come down the hall, Sweetie. I'll put your bags away, and then run you a bath... how does that sound?"

How did it sound? It sounded wonderful to her. After exploring the living room and kitchen briefly, she hurried down the hall to the bathroom, which was larger than she expected. There was a separate bath and shower, a floor length mirror, and all sorts of different soaps and supplies. Charles was already here, sitting on the edge of the large bathtub, hot steaming water filling it.

"Well... let's not waste any time... I've been all too eager to get you here for this, Dearest... Undress..." He bit his lip, and looked well excited.

This kind of desire and want was exactly what she'd been craving all along, so it didn't take much hesitation to start undressing, taking her pleated skirt and button up blouse off, folding them neatly before casting a glance at Charles hungry eyes. She only had a sports bra on, as she didn't need much support on her chest. She smiled cutely before starting to slip her pink bra and panties off, leaving all her clothing in a neat pile. She'd anticipated this would be the first time she'd be naked in front of Charles, at least, soon after moving in with him. But it was a battle of what she wanted, and her embarrassment. Her want won, of course.

"You look lovely... Are you nervous? Maybe you should be. You don't know what you're getting yourself into." He smirked. - It was true, she was completely inexperienced in the matters of sex. Still a virgin, she'd only really pleasured herself manually with her fingers, not even brave enough to have bought any kind of toy. She had used a few assorted vegetables to try penetration more than a finger, and she'd had wonderful success. Not only did she find her wider hips allowed the larger shape to fit, but that it felt amazing. She did cease this quickly, however, as she wanted her first time with Charles to be special... Still, masturbation was all too frequent for her in the last years, Charles always leaving her hot and flustered.

"A little bit, yea... but... you make me feel safe, Charles... I'm so excited for this... all of it. With you~" She stepped forward, the motion making a slight drip slide down her inner thigh. She blushed harder, hoping that Charles couldn't see it. She walked up to the bathtub, and he slid his hand around the small of her back, pulling her closer. Her legs hit his knee, which parted them.

"Yes, I can see you are excited, Kaylee..." Before she could even realize it, Charles slid his hand between her parted legs, just gently touching her folds, sending harsh shivers through her body. "You're wet before you've even gotten in the bathtub..." She wanted so much more, but he pulled his hand away and stood up, towering over her. "No reason to be so dirty... better get in and wash up, my dear..."

She let out a shuddering breath and nodded. Best to clean up, if that's what he wanted. She was still a guest here... right? At least, it still felt that way. Kaylee stepped into the bathtub, the hot water a bit of a shock, but not too hot to get into. She climbed in, sliding down as the hot water rose around her hips and waist.

"Feel free to use that liquid soap there for your body. Don't both washing your hair, just your body. Understand?" She blinked, the specificity of the words catching her off guard.

"Yea, okay Charles. Thank you."

"I'm going to unpack your clothing and such... and then I'll be back for you. Hehe." He picked up her clothing that she'd taken off in the bathroom before leaving the room, closing the door.

She giggled with glee. This was what she'd always dreamed of... living with a handsome guy who was well off and romantic, and made her swoon all the time. Her dreams were all coming true. And so were Charles'...


The bath was lovely, and the soap smelled ... good, but strong. It was extremely slippery and tingled her skin slightly as she scrubbed herself. She made sure to wash between her legs too, which was difficult. Mainly because her body was still so on fire, so ready for Charles... ready for more.

Eventually she felt she was done, and drained the bathtub, climbing out. Noticing her clothing wasn't there, she grabbed at towel, drying her body off. As she did, she noticed that the soap left her skin feeling a bit more sensitive, probably was just some kind of deep cleaning formula, which would make sense why he didn't want her using it on her face or head. After drying off, she wrapped the towel around herself and left the bathroom, finding her way into the master bedroom. Opening the door, she was surprised to see Charles sitting there in a chair, waiting. She didn't see her bags anywhere, he must have already packed them away and such.

"All clean, Mister... Hehe."

"Good... why don't you come over here, but leave the towel..." - She bit her lip, nodding and smiling wide. The towel dropped to the ground, revealing her fresh cleaned body, her wide hips and generous ass, thin waist and nearly flat chest.

"Are you going to get undressed too?"

"When the time is right..." She stepped right up to him, standing in front of him as he glanced over her body greedily. "You'll let me take the lead on this, yea? I have a little surprise for you."

She nodded hurriedly. "Y-yes please. I don't even know what to do.. Haha..." Kaylee blushed deeper, trying to temper her breaths.

"Close your eyes then, my dear." She did, and she suddenly felt something soft being pressed over her eyes. "Just relax, you're safe with me..." A blindfold? She blushed further, and came to the realization that if Charles had any fetishes or kinky interests, she didn't know about them, since all their interactions before this were non sexual. Part of her was nervous, but the rest of her just got more excited. "You trust me, right Kaylee?"

"Yes... of course I do..."

"Yes what?"

"Y-..yes... Sir?" She wasn't sure what he was looking for, but it just felt right to give him that kind of respect. Though she couldn't see it, Charles smiled wide as she said it. She could hear him moving around a bit, reaching behind the chair to grab some other things. What did he have in store for her? She couldn't wait to find out.

As she stood there, she felt Charles pull her legs apart slightly. Was he going to touch her again? It took a lot of effort for her to not reach out and pull his hand there. But she kept her hands clenched at her sides in anticipation. Instead, she felt him pull her arms out too, on either side of her. "Hold these here. Just going to put a little something on you, okay?"

She nodded again, breathing faster. Soon, she felt a cool hard feeling press against her back, at the small of her waist. Then it wrapped around to her front. Some kind of waistband? Some kind of kinky lingerie? She couldn't tell, and even if she opened her eyes now, the blindfold obviously was to keep her guessing. Then she felt another cool hard press on her body, this time at her neck. A collar? It must be. Kinky indeed...

Charles seemed to fidget with both of them a bit, but they both fit so perfectly. She thought about this for a bit, until she remembered a month ago, when he helped her measure her body for some custom made clothing that he gifted to her... "Lower your arms now."

"What is all---"

"Shhh... Listen. Kaylee... do you want me to put something inside you...? I know you've been wanting it..." She gasped, nervous but wanting. She was already wet again, and just wanted him to shove her onto the bed and take her right here and now.

"Y-yes. Please. I want it, Charles..."

"Good... Then relax... And do not speak until I'm done... moan if you need to~" She felt some more movement, but a slick phallic shape suddenly pressed against her already moist opening. "I'm a little big, Darling... so I'm going to have to work you a few sizes up until you're used to such a thing, okay?"

She bit her lip hard. She'd always seen his large arousal in his pants but she realized she never really saw how big it was. This was him being nice. He didn't want to hurt her, obviously. "Okay... Sir."

Slowly he pushed in the lubed dildo. It wasn't huge, but not tiny either. It easily fit, and Kaylee easily moaned. Slowly pressed all the way in, then shifted around slowly. Too slow. Fuck, she wanted more. Then, he slowly removed it, and another one came, slightly bigger. Several of them, each time, he just moved slowly in, held it there, testing how deep it could go, how much movement it could get. It was torture. "Mrmh...rmm... Charles.. P--"

"Ah ah... not another word. Or I'll stop, and we can just watch TV."

She bit her lip even harder. Moaning was okay, but no talking. Okay. She focused on the feeling more than the thinking, so she couldn't ask questions. It was so hard to tell how big these dildos were, without looking. She figured he must have gone through seven or eight of them before she started feeling really tight. "Mrmhh...mmm..."

"That's about the max, I guess... more than I thought. Good... " Instead of removing it, he left it there for a bit, to get her accustomed to the size. And while it was there, she jumped as he suddenly started to do the same work on her rear passage.

"Ahh!!" She covered her mouth quickly to not say anything. Charles just giggled to himself.

"It's okay, Dear. I want to make sure I can have the most fun with you, that's what you want, isn't it?" She nodded quickly, her face beet red. This part of it was less comfortable, never having tried anything anal before. To her surprise, as he worked up the increasing sizes in her ass, it didn't feel as bad as she thought it might. Eventually she could feel the larger dildos shifting her insides around slightly, the vaginal one still held inside.

"There we go. Very impressive, my dear... I'm proud of you... Now, are you ready for the real thing? The only thing that should be inside your lovely body?" Oh gods yes, she nodded and breathed quicker. She needed this so bad, her body was ready to explode. Slowly, he pulled the dildos out, leaving her feeling almost empty.

Instead of bringing her to the bed however, she felt another tug on the tight band around the small of her waist. Then a pressure against her ass. Another dildo? It was slightly larger than the last one she'd felt, sliding slowly in. This one however, flared out wide, making her gasp in pain before it popped in, the tapered end sliding into place as her muscles contracted around it.

Then, another pressure against her pussy. Another dildo, this one however, was textured, little nubs and feelers all over the head of it. It was lubricated heavily, but parts of it felt harder than others, like some of the nubs were metal, the rest silicone. In it went, pushing in like the others, this one wider, filling her up completely. As it came to the base, however, she realized that it was connected to the anal plug too... and they were both connected to the waist band. Her brain flashed with warnings, piecing together what it was that Charles had been putting onto her. She felt the metal band they were attached to pull up between her legs from behind, and Charles connected it to the front of the belt. Several clicks, as the band between her legs got tighter and tighter, pulling both plugs up deep inside her, but perfectly sized, not pinching or painful. - Charles had put her into a chastity belt.

She couldn't believe it, reaching up and pulling the blindfold off quickly. "What the fuck is this?!" She reached down to the belt instantly, tugging and pulling. The whole thing was beautiful, polished surgical steel with rounded silicone edges. It wouldn't budge an inch, perfectly made for her body.

"My my, what sort of language is this, Kaylee? You'd always been so polite before..."

"Well, I... I didn't expect something like this..." She continued to try to test the bounds of the belt, trying to stick her fingers under the front of it, under the waistband... nothing would fit. "W-why am I wearing this, Charles?"

"Because you wanted to be mine. Now you are." He held up a key on a thin chain. It was already around his neck. Kaylee's blush deepened, realizing the implications. He held the key to her pleasure.

"W-well... I mean... I just expected we were going to have sex? D-don't you want that? I mean. You always seemed like you did..."

"Oh, don't get me wrong, my dear. I do want you. I feel an overwhelming amount of desire and lust for you... I just have... my own particular tastes. And, knowing that you were still a virgin, never having really felt the pleasure of something real... How could I resist?" He stood up, his height somehow seeming even more imposing, him still clothed, while she stood there wearing nothing but the tight, fitted bands of steel that held the two large plugs deep inside her.

"W-well... Am I just supposed to wear this from now on? And you unlock me when you feel like... u-using me?"

"Oh no... nothing so simple as that. You see, I desire you more than just sex, Kaylee... I want you to be my wife. I want to marry you." As he said this, he went down on one knee. Despite being naked, embarrassed, and afraid, Kaylee was also extremely aroused and wanting. This sent a huge flush through her body. She'd never thought about marriage. Not seriously at least. She'd fantasized about a pretty wedding and living together and such, but you didn't need to be married to live together...

"M-Marry me?"

"Will you? Marry me, that is."

"I... I mean is this r-really the appropriate time to a---"

"I think it's the perfect time. Because I need to know something. I know you'd been wanting to have sex with me, Kaylee. But I ... I have some old fashioned ideals, I guess. About my bride being pure, and remaining as such until our wedding day. But I know how much desire you have in your heart and body... so. I think it's important that you'd know, if we are to get married, you would have to remain in chastity until our wedding night." He nodded slowly to himself, as if this was a difficult task for him to set forth.

It was rather storybook, the chaste girl saving herself for her husband on their wedding night... but she never expected it to be so ... enforced. Or... Arousing? She shifted her legs slightly, the plugs moving along with her.

"Charles, I don't... I mean I don't know if that's ... I mean, w-what if I'm not okay with this ... um. Belt."

"Then that's okay. I can take it off you now. But... " he looked away and sighed. "I don't know if we could really accomplish what I have envisioned. I don't know if I can marry you."

It felt almost as if he was blackmailing her. But, it was simply a proposal. Literally. She didn't have to accept. But if she refused, would she lose her relationship with him altogether? Could she risk that? If she were to accept, she would be locked in this device until they were wed. How long between engagement and wedding is it for most couples? A few months? A year? She dreaded the thought of anything close to a year. She couldn't do it. No matter how good the promise of sex would be. But she'd gotten so close... her body was on fire and full of want for Charles. She wanted to be his, and the submissive side of her was caving hard.

"I... I will. I accept. I want to marry you, Charles..." Her face was red, mouth open slightly as her body needed to pant.

"Good... Let me get the engagement ring..." He stood up, reaching into the open drawer beside him before turning back to her. Again, she was slow on the reactions, thinking too much about what she'd just agreed to, as Charles wrapped a ring... around her neck. It was two parts, banded steel like the belt. And also like the belt, it was a snug fit as he pulled the two halves together, the two pieces clicking together.

"Ah! Ngh... Charles! What is this?!"

"It's your engagement ring. You are mine, my dear. Make no mistake about that... besides. It's a fashionable necklace. And unlike your other accessory, it's plated in white gold." He smiled, rubbing her head gently. "I love you, Kaylee."

"I ... I love you too, Charles..." She let out a shaky sigh, leaning against his body, her hip feeling the firm, hot, eager arousal in his pants.





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