The long delayed end of the series. In case a refresher is needed, here are links to the first, second, third, and fourth parts.
Hot steam filled the small bathroom as Chris ran conditioner through his hair, sighing contently at the warmth of the shower. It was late at night, well past 1AM, but with work somewhat early in the morning and him not quite ready to lay down, it made more sense to wash off now and get a few extra minutes of rest in the morning.
As he worked through his practiced routine, his mind drifted to the draft of the story he was currently working on. He had recently taken up writing erotica again, and had done a few short stories in the last few months. He was happy at the progress, though a certain emptiness gnawed at his creativity. He was attempting to branch out with his current story, writing about a completely different situation than he usually did, with a very different kind of girl as the female character. However, the longer he worked on the story, the more frustrated he found he got with it. It wasn't necessarily that he couldn't write from a different perspective, in fact he somewhat enjoyed the change up in scenario from his usual fare. The problem was rather that every time he attempted to write about this new character, a familiar face started to work her way into his mind instead.
A beleaguered sigh escaped his lips as he lathered the soap under his arms and reluctantly his mind slowly crept down a familiar train of thought. It had been over a year since he had last seen Ally, the memories of that day playing through his mind more often than he would like to admit. Though it was the last time they had seen each other, it was not the last time they spoke, although it was only through a late night phone call, and Chris seldom liked to think about that night. Being yelled at over the phone for little reason, then having his responses ghosted was hardly the parting words he hoped for, and over the past year she had made no indication that anything else was forthcoming.
He knew that, logically, he had every right to hate her for what happened. Or maybe at the very least look back at their time together with the dejected apathy of hindsight. That is certainly what people expected of him at least, and to their credit he certainly tried. But he could never keep up the farce for very long. To be sure he was certainly angry with her, and he knew that he would be justified in not forgiving her after everything she put him through, not only in their recent spat but in numerous years since they've met. But he just couldn’t bring himself to wear the veneer of the jilted partner, and he found he respected himself far more when he accepted his honest feelings on the matter over a more convenient response.
That’s not to say that he wasn’t doing fine without Ally. He had lived many years without her; it was not too difficult to live more. His days went on as it always did, and over the past year he had made steady improvements to his life. But still he carried with him a pit in his chest that assailed him every now and again. Though he felt in his heart he had done all that could be expected of him, he still occasionally questioned if any of it had been his fault, if there was somewhere or someway he misstepped to create this outcome.
Chris exhaled in frustration, angry at himself. This was hardly the first time he had journeyed down this mental path, and he knew it certainly wouldn't be the last. It had gotten especially common when he picked up writing again. But while he would not lie to himself about his feelings, he also owed it to himself not to constantly second guess his own actions, or focus on what could have been changed.
Desperate to extradite himself from this worn inner dialogue, he rinsed the soap and conditioner off of himself, then reluctantly turned the hot water off. Stepping out of the tub he wrapped his body in the hanging towel, then threw another around his hair. He exited through the small hallway and into his room, turning down the TV and opened his laptop to check his blog. It was something he often did right before bed. He scrolled through the posts while he brushing his hair, almost a therapeutic ritual to wind down the night and ready himself for the new day.
After a few minutes, his hair was thoroughly detangled, and still warm from the shower tiredness started to assail him. He reached for his phone, face down on the end table next to him, intending to double check that the morning alarm was set before laying down. In his growing exhaustion, he almost ignored the three messages on the lock screen. It wasn't until his head hit the pillow that the name belonging to the texts registered in his addled mind. Immediately, the fog of his mind cleared and he quickly opened the messages, trying to ignore the pit of nerves in his stomach.
The texts must have been sent while he was in the shower, as the first one was delivered at 1:33. It contained only a single word.
Ally: Hey…
The next message was a longer one, sent at 1:38.
Ally: I know you’re probably asleep, and it’s probably better if you are. I just wanted to let you know that I’m sorry for what happened between us. Things got intense and confusing and I needed a clean break. I felt like you wouldn’t have accepted things as we left them last time I saw you, so that's why I tried to forcefully put an end to things the way I did. But you didn’t deserve how I acted that night, and you didn’t deserve how I treated you through the end of our “thing,” even if I had my reasons.
A shorter, final message followed at 1:40.
Ally: You don’t have to forgive me, and I don’t really expect a response. I just wanted to let you know that I’m sorry.
Chris set down the phone and rubbed his eyes, fighting to calm the swirl of emotions in his chest. Before he let himself overthink his response, he forced himself to pick it back up to send a reply.
Chris: I…. don’t really know how to feel about that. There’s a lot of things I want to say to you, and none of them I want to send over text. I’d like to see you.
His response was simple and honest. He was not sure how to take her abrupt apology, especially after a year of complete radio silence. Still, his desire to see her and talk personally about what transpired between them outweighed any anger or trepidation he felt about speaking to her again.
He waited for a few minutes, then a few more, and then a few more before the hour of night started to outweigh his desire for a response that would likely not come tonight. Sighing to himself, he set the phone back down and drew the gray blankets up around him. Despite his turbulent emotions, the warmth of the comforter lulled him to unconsciousness quickly and into a fitful sleep.
Her response took longer than he anticipated. It was deep into the following day, during a late lunch break, that his phone buzzed in his pocket. Chris set aside his sandwich and pulled up the message, unsure of what to expect.
Ally: Are you sure that’s a good idea?
Leaning back in his chair, Chris chuckled to himself, and quickly typed an honest reply.
Chris: Not at all. I just know it’s what I want.
He waited a few minutes for an answer, attempting to distract himself by absentmindedly chewing at his lunch. Finally, the phone buzzed again.
Ally: I’m off tonight. Is that alright?
With a calming breath, he texted back.
Chris: I’ll be done work at 4; any time after that works for me.
Ally: Okay, I’ll be there around 5 or so.
He stared down at the message. Just like that, it was settled. It was a very confusing feeling. Being a Friday afternoon, he had nothing else to worry about for the next few days. He knew that overthinking things would only lead to him stressing out, so he forced himself to put down the phone and finish his meal. In a few short hours he would be done work, and it would be time for an unexpected reunion.
Ally knocked on the familiar apartment door, her own mind a whirl as she heard the footsteps approach the door. Despite herself, she shuffled from foot to foot, both impatient and nervous for what was to come. On the drive over, she had considered rescheduling for a different day, to give herself more time to prepare for this meeting. But with no real reason to delay, and her own curiosity peaked, she resolved to see this through.
Her mind flickered back to the days when she would be standing in the same place, wondering whether she'd be sent home with a red bottom. Those days were far in the past, and yet she found herself missing it. Ever since that night with Chris, and the resulting fight, her life had been a rollercoaster, full of ups and downs. She had finished school, had moved out and into her own apartment, gotten together and subsequently broke up with her ex, and that's only scratching the surface. It was a turbulent time, and she thought back to when she had Chris as a grounding force in her life, willing to turn her ass red when she acted up, and felt a bit of longing creep into her chest.
Her reminiscence was broken when the handle clicked and the door gently swung open, and for the first time in a year she found herself face to face with her friend and former disciplinarian.
Not wanting to show her nerves, she put on a casual smile, muttered a quick “hey,” and slid past him at the doorway into the living as if it were her own. The place looked much the same as she remembered it, though certainly tidier than in their last meeting. She plopped down at her old spot on the couch with a satisfying thud, and turned her attention to the man following behind her.
Chris looked much the same as he often did; clad in a t-shirt and sweatpants, even expression, with a slight polite smile. However, despite his efforts she could tell that there was a wariness in his eyes, emotion hidden under an expression of welcome. He sat across the table from her in a small chair, and for a few moments there was a pensive silence, a tension neither wished to outright break.
Unable to take the awkward quiet anymore, Ally spoke, not looking at him.
"Sooo, yeah...." she started lamely.
"Yeah" Chris echoed softly.
Another heavy pause filled the room.
Ally clicked her tongue. “Sorry; I don’t want to start off by being rude, but I've kind of already said my piece. You’re the one that wanted to talk in person, so….”
She looked at him expectantly, patiently waiting for him to begin. He sat there for few seconds with an inscrutable look, then responded.
“That's fair. I've thought a lot about what I've wanted to say to you, even before your message last night. I guess the main thing I wanted to ask was why?"
Ally gave him a quizzical look, not sure of what was meant.
“I don’t mean the why of your actions.” Chris explained, “We've discussed that in too much length before. What I mean is, why does this continue to happen between us? Why do I always seem to get no consideration from you, and despite giving you all of mine?”
Though his face did not show it, Ally could hear in his voice that he was holding back emotion. She began to offer an answer, but he continued.
“I mean, I get it. I have feelings for you that you didn’t want to reciprocate, things were in an awkward place for you, the timing was bad. If that was the extent of it, I wouldn’t be mad. It’s the fact that every time our friendship or relationship, whatever 'this' is, becomes inconvenient for you, your first instinct not to talk things out rationally, but to instead burn that bridge to the ground, and hope that I forgive you somewhere down the line.”
He rubbed the bridge in irritation, clearly trying to find the right words.
“And to your credit, thus far I have. Because no matter how many times you pull this shit, no matter how poorly you act towards me, as of yet I just can’t find it in me not to forgive you. There is, for better or worse, something within me that is inexorably drawn to you, and I know you well enough to usually understand your underlying motivations aren’t truly malicious.”
“But I'm not your emotional punching bag. One day, enough might actually be enough. More than that, even if that day never comes, I don’t deserve to be treated that way. I give you too much of my respect and understanding for you not to give me a little bit of the same in return.”
He leaned back and looked at her silently, his gray eyes studying her reaction. Ally sat quietly for a second, thinking over his words, and tried to give an honest reply.
“Like I said, I’m sorry. You’re right; I’ve often made mistakes in how I've handled things. But to be fair to me for a second, we have a strange situation that makes being friends when I’m otherwise involved... kind of awkward. I know how you feel about me, and I don’t want to hurt you if things don’t turn out the way you want them to between us. Which they very well might not.”
“If that happens, then we can always talk about it like adults.” he answered.
"But can we really? Even if you said told me that you were fine just being friends, or not talking for a bit while I deal with personal drama, would you really mean it? I'm not trying to be a dick, but I know from experience just how hurt you get when I've spoken about other boyfriends, or have had to put our relationship to the side for a while. I'm not saying I'm not at fault for snapping at you and making things toxic, but it's because I don't want to hurt you in the long run."
“But when you take things into your own hands and act out of emotion, you end up not giving me the chance to prove otherwise. And often end up causing me more pain than if we just talked things out without all the drama. That's not for my benefit; that's for your convenience."
“….. True enough.” she conceded. She wasn't going to pretend as if she often didn't make rash and often destructive decisions, even if she had somewhat good intentions at heart.
“But I get it." he said. "I do care about you deeply, more than as a friend. If that develops further, then obviously that’s great. If it doesn’t and things remain platonic, that’s fine too. I just like you as a person, and I don’t want to lose this bond.”
Ally thought about those words for a few moments. She certainly enjoyed his company, and their connection was something she couldn't deny. But she knew herself well enough to know it was often not that simple, and she didn't want to end up in another situation where someone had to get hurt.
"Okay, but I just want you to know that I'm still not really sure what I want from this. I mean, when we first met we were kind of a thing, then we were sporatic friends for years. Last year you were my disciplinarian. Obviously we have a good vibe, and it's clear there's some connection here. I just don't know how deep that connection goes, and I don't want you getting upset over that."
"That's fair" he replied. "But whatever form that bond takes, you need to trust me and respect me enough to talk to me, honestly; not just take things into your own hands and ask for forgiveness after the fact."
Ally sighed. “And I really wish I could promise that; I do, but I'm not quite sure I can. Don't get me wrong; I’m not disagreeing with what you're saying, that's why I'm here. I'm trying to do better, but like...well...” she threw her hands up for emphasis “I am who I am, and you know that. I don’t do it to be a bitch. Life is messy and complicated, and I don't always handle that very well. And I'm trying to do better, like really trying, but I can’t one hundred percent guarantee things won’t be similarly messed up situation somewhere down the road. I'd really like to, but I know myself better than that.”
She shrugged again, not knowing what else to say. Chris stared at her intently for a few moments, before answering in an even voice.
“I suppose that’s the best answer I’m gonna get.”
She looked down at her feet, quietly thinking over their exchange.
“I’m sorry” she said again, truly meaning it.
“I know” was his succinct, sincere reply.
Neither of them had anything else to offer, so again they sat in silence for a few moments.
“Soooo, now what?” Ally questioned, growing uncomfortable at the sudden lull in the conversation and trying her best to disguise her nerves.
Chris leaned back thoughtfully. “Well, that’s up to you. I obviously don’t want you to go, but if you want to leave things at that, you can. Or if you’d like, I’ve got some beer and wine in the kitchen that we can crack open.”
She felt herself smile, grateful at the slight release of tension. “Oh, have I fully converted you?” she joked.
He smirked back. “Hardly. Honestly, I barely touch the stuff unless you're somehow involved. I just picked it up on the way home on the chance that this conversation went well.”
Ally felt her grin grow mischievous. “I see… You know me so well” she mock yawned, before quickly sitting up and racing to the kitchen.
It was a few hours later, and darkness had settled outside. With the wine poured and beers opened, the heavy conversation and atmosphere from earlier turned playful and reflective as inhibitions were relaxed and they fell into their old rapport. Chris smiled as Ally animatedly talked about the last year in detailed recap. It seemed she had been quite busy, and left no detail unsaid. From there, the conversation moved to the stories he had been writing; though she denied it, Chris was pretty sure she had been keeping up with them, but he played along and described them in detail and the thought that went into them.
The TV buzzed quietly in the background, all but ignored. The small table between them held a few empty beer bottles, and the wine was half gone, but neither of them seemed anything beyond tispy. Ally was now describing the vacation she took with Brooke in the summer, her arm gesturing wildly as she described the chaos of the trip. Chris felt himself smile, the tightknit emotion in his chest being gradually unwound by the cadence of her voice. It didn’t really register to him that Ally had stopped talking and was staring at him questioningly until she broke the silence with a question.
“What?” she dryly accused.
“Nothing.” He smiled back.
“Don't give me that 'nothing.' Why are you looking at me like that?” she pressed. “Is my story not interesting enough? Are you tired of me already?”
“Quite the contrary” he chuckled back. “I just missed this is all.”
Ally smiled dangerously. “Oh. Was this the only part you missed, or was there something else as well?”
Chris smirked back. “Now that you mention it, there is one thing…“
Ally flashed him a wry smile, before changing topic. “Anywayyy..... I’ve done a lot of talking about me. How about you? Has there been anyone you’ve been seeing? A year's a long time.”
Chris leaned back, smile growing softer. “There was a girl at work. She was cute, we had a bit of a thing. Got pretty flirty and almost became something, but it flickered out quickly enough and she ended up leaving pretty soon after."
He sighed and shrugged, eyes gauging her reaction. "Aside from her, just a couple girls online and a few brief tries at dating apps, but nothing serious.”
“Hmm.” she murmured with a curious expression. "Interesting…."
Now it was Chris’ turn to question. “And what exactly is interesting?”
“I just thought after what happened with us, you might have looked more seriously for another cute girl to, y’know, do kinky shit with.”
“Well, it’s not for a lack of trying. I just haven’t found anyone I’ve had a connection with yet.” It was a true enough statement by his account, but Ally just frowned.
“Uh huh” she clicked her tongue unconvinced.
"You don't believe me?" he asked.
A noncommittal shrug was her only response.
He sat forward and gave her a self depracating smile.
"I'll have you know that I very much miss being a disciplinarian. Rest assured; if I had a brat to turn over my knee, I would be doing so with much regularity."
Ally sipped from her cup, a smile on her lips. "And yet I'm sitting right here, and nothing's happened..." she trailed off.
Chris laughed incredulously. "Ok, what exactly is that supposed to mean?"
“Noooothing.” She mirrored his previous reply, her smile growing coy.
He stared at her, trying to decipher her intent, but she merely blushed and turned towards the TV. “You do remember that lying was once a spankable offense” he joked warningly.
“Oh, it used to be, but isn’t now?” she responded innocently, still not looking at him.
He looked at Ally, then leaned in and grabbed his beer off the table. “Unfortunately that seems to be the case” he said.
She sighed in mock disappointment. “Huh. What a shame…”
He leaned back in his seat with his beer in hand. "Disappointed? Would you like to change that fact?"
Ally shrugged again, before taking another sip. "Perhaps."
Chris took another swig from his glass. "I thought that you didn't want that anymore."
"I don't remember saying that" she answered slyly.
"Really? Please, elaborate" he said with mock exasperation.
"Well, like we've talked about, I broke things off last year because things were getting intense, my life was insanely busy, and I was getting involved with my ex again. It was the wrong time to be involved in a kinky relationship with you. Buuuuut, we're friends again now, and neither of us are currently involved. So what's the harm, exactly?"
Chris smiled at her words. "Well, that sounds like the wine talking to me."
"Maybe a little, but not enough that I don't know what I'm saying" she answered. "I meant what I said earlier; I don't know exactly what this is between us. That doesn't mean we can't have a little fun in figuring that out in the meantime."
Chris was quiet for a few moments, gathering his thoughts. What she was saying was true enough, and he would be lying if he wasn't intrigued by her proposition.
"Do you not want to?" she questioned, looking a bit self conscious.
Chris gave her a reaffirming smile. "You know very well that I do. I just don't want you to think that because I'm no longer your disciplinarian, I won't beat your butt bright red."
"I should hope so" she cheekily replied, squirming almost inperceptively in his seat.
Chris looked away and at the TV. He would like to think that there was any moment of consideration, but in truth he knew his answer the moment the question was posed. Putting on his old authoritative voice, he turned to her and gave her a playfully stern glare.
"Well then, young lady, it seems you are again in dire need of a bare bottom spanking. One that I am more than happy to administer. Maybe if you behave yourself, I might find it in my heart to give you a little pleasure as well, if that's what you want of course..." he smirked, looking expectantly at her, awaiting her assent.
Her blushing grin told him everything he needed to know.
Ally's pulse quickened with adrenaline as Chris roughly led her into the bedroom, slapping her ass hard at the doorway. She turned back to face him, but was quickly turned back around as his hand peppered slaps on the seat of her leggings.
“Face forward. Arms up” he growled in her ear, as his hand lifted at the hem of her shirt.
She bit her lip and complied, feeling the fabric pull up her body and over her head. She went to lower her arms, but Chris’s hands gently grasped her wrists and placed them behind her head.
“Keep those where they belong” he teasingly commanded, his hand ghosting across her exposed stomach and towards the front of her bra. His fingers traced around the edge of the fabric, under her arm and to her back, and she felt a slight tug and he worked at the hook.
With a pop, her bra fell free, and prying her hands apart for a brief moment Chris threw it to the ground. Ally bit down on her tongue as his hand found it’s way back up to her bare breast. His fingers teased and pinched at her nipple, while his other hand returned to her bottom with a hard slap.
Her leggings were the next to go, and Ally groaned as she felt the slightly chilly air kiss her exposed thighs as her pants were pulled to her ankles in a smooth motion. A quick step later, and they too were tossed across the room.
With her now mostly naked, Chris put his hand behind her back and led her towards the bed, taking a very familiar seat at the edge. Hands still on her head, Ally felt a surge of adrenaline and lust as he pulled her in front of him, memories flooding back.
Only a tiny piece of fabric prevented her from being totally exposed to him, and she was both grateful for and frustrated by that fact. She bit down on her tongue as his hands explored her bared legs, and one hand started to rub her pussy through her panties. She looked down at him, only to immediately avert her eyes in embarrassment when they met his stare, amused and questioning.
“Are you getting wet under these panties?” he teased, as his other hand rubbed the outside of her thigh.
“Yes….” she breathed out as his fingers traced over her clit. Because her gaze was focused on the wall, she didn't see his hand snapping at her side, and a sharp pain blossomed on the outside of her right thigh. Her gaze returned to his, and then the realization hit, and suppressing a smile and an eye roll, she repeated herself.
“Yes sir.”
“Good” he answered. He continued to rub her through the cotton. Ally felt herself melting into the touch, already feeling herself becoming more submissive. His voice shook her out of her head. “I want you to ask for it.”
“Ask for what?” Ally breathed, lost in the sensation.
He smirked at her again, sadistic pleasure clear on his expression. “You know exactly what’s about to happen. We both know what you want. So I want you to ask me to take these down and give it to you.”
Ally bit down on her tongue again as his fingers continued to play. She briefly considered playing up the petulant brat, curious what kind of trouble it would land her in. But his hand felt so good through her panties, and she didn't want to do anything that might ruin the chances of her getting off tonight. So she gave him what he wanted.
“Please pull my panties down and spank me” she exhaled. Under different circumstances she would be embarrassed to say such a thing, but the flame of desire in her was burning too hot to currently care.
Chris wasted no time with her reply. In one swift movement, her panties were at her ankles, and Ally barely had time to step out of them before she found herself tipped forward over his knee. She wasted no time in splaying her legs, hoping he would return to touching her now exposed pussy, but a familiar sound rang through the room as Chris’s hand came down hard on her right cheek, followed by another on her left.
Seemingly trying to make up for lost time, Chris lit a fire on Ally’s ass. His hand came down over and over at a blistering pace, and Ally could only groan and bite her inner cheek as what felt awfully close to a punishment rained down on her bottom. The onslaught did not let up for well over a minute, and when he finally stopped Ally could swear steam was rising from her cheeks.
Then she gasped as his hand dipped between her legs and ran along her leaking slit. She involuntarily squirmed and leaned back, but Chris put his other hand on her right shoulder and gently pushed her back into place. His fingers teased the aching flesh, not quite pushing deeper, but instead playing along the length of her pussy.
Ally lost herself in the touch, pushing her ass out and spreading her legs wider to tempt him more. However, just as suddenly as he started, his hand retreated and the spanking started anew. The smacks were not as harsh as before, but they still stung, and for another minute he roasted her ass again, before his finger returned to their ministrations.
And so the cycle continued. Chris would punish her bottom for a minute or so at a time, before briefly giving Ally a reward. Her ass was starting to get very sore, but the hot ache between her legs is what commanded her attention far more. It was torturous; it seemed like every time his fingers began to give her the relief she craved, he pulled away and punished instead, building the need even more.
Ally was not sure how long she’d been over his knee; it felt like nearly ten minutes to her addled brain, when one of his fingers, whether intentionally or not, briefly pushed into her for a moment before retreating. The sensation was too much, and she breathed out a plea.
“Please….”
Chris continued to play with her, his middle finger lingering just at the entrance of her hole. “Please what?”
“Please put them in me…” she earnestly moaned, all illusions of modesty long behind her.
“Oh?” She could hear him smile. “That’s a very open statement that could be interpreted many ways.” As if to demonstrate, she felt his thumb slip between her cheeks and circle the flesh of her anus.
“I don’t care. Pleeease” she whined, gyrating her hips and pushing back against his fingers. She, more than anything, had the need to be filled; she didn’t care what form that took at the moment.
“Hmm” Chris hummed, his fingers pushing slightly against her orifices. “I don’t think you want it bad enough yet. We’ll see if that changes after another round of spanks.”
His hand pulled away and began smacking her again. Ally groaned and wriggled in place, desperate to be touched and frustrated at her denial. She accidentally nudged her head against his left hand, still on her shoulder, and got an idea. Before she had time to consider what she was doing, she leaned over and took his fingers into her mouth and began to suck. She felt the spanks lessen in frequency and severity, but it mattered little as she fervently did the only the thing she could think of to show her need.
Soon she realized his hand was back between her legs, and a wave of pleasure hit her as his fingers finally pushed into her fully. She moaned in response, but continued to put her mouth to work. She fumbled with her right hand, pushing it under her stomach and against his thighs until it found it’s target; his cock pressed against her from within his sweatpants. She heard his breath hitch, and quickly she started to rub her palm against his length, feeling it swell at her touch. Almost in response, his thumb worked it’s way into her ass, and all three of her holes were filled with his fingers.
With her bottom hot and surely red from spanks, his hands pumping his fingers deep into her, and his dick rubbing against her palm, Ally felt her orgasm building. She released his left hand from her mouth and warned him.
“Please sir, I’m gonna cum. Can I?”
“Not yet, you’re gonna earn it” was his cold reply. He slowly withdrew his fingers from her holes and pried her cheeks apart, opening her completely to the air. She gasped and pouted at his answer, her orgasm still close, if only he would just….
“Please” she begged again. “I need it…”
“You need what, exactly?” he questioned, and she felt his fingers creeping towards her exposed holes.
“I need to be fucked, sir” she moaned.
“No” he answered sternly. “You can ask for that when we’re sober. But that doesn’t mean you can’t cum, if you show me your gratitude.”
“I will…” she nodded, rolling her hips in frustration.
There was a brief pause, and Ally felt her weight shift as Chris guided her gently off of his lap and to her knees in front of him. His hands reached for the waistband of his sweatpants.
“Really, you’re lucky that I’m even considering letting you cum, with how bad a girl you’ve been. So show me you can be a good one, and I'll let you have that reward.”
Ally needed no further implication. She helped slide his pants to the ground and with no hesitation took his cock in her mouth.
Chris exhaled sharply as he felt Ally's warm mouth wrap around his dick. He had become quite aroused while playing with her, and her earlier ministrations didn’t help matters. So when she began to suck, a strong jolt of pleasure pulsed throughout his body, and he held back a groan.
Ally seemed to be taking her job seriously, and with him already so stimulated, Chris realized at this current pace he would be filling her mouth in no time. So he tangled his hands in her hair and slowed down her fervent motions.
“Ease up just a bit. I want to enjoy this for a while” he ordered, his voice unusually breathy. “Put your hands between your legs; I want you to play with your holes while you suck my cock.”
Ally dutifully obeyed, and Chris felt her moan of satisfaction travel up his body from his groin. He held fast to her hair, watched her pretty mouth work up and down his shaft, and began to relax into the sensations. He was so often concerned with her discomfort or pleasure, that he often forgot to worry about his own enjoyment. This was suggesting he might have been a little too selfless in his focus.
“Perhaps I should make you thank me more often” he teased, his voice tense with desire. Ally either didn’t hear him, or ignored his jest, but began to draw him in deeper into her mouth.
Even with his hands fingers laced in her hair, she began to pick up the pace again, perhaps lost in her own touch, and Chris no longer had the desire to hold her back. He felt the familiar tingle in his loins, and his grip on her tightened.
“I want you to swallow every drop” he ordered. Ally sat up more onto her knees, and he could see her right hand rubbing vigorously at her clit. The sight pushed him over the edge, and a wave of orgasmic pleasure washed over him as he exploded in her mouth. Pulse after pulse wracked through his lower body, and he closed his eyes and leaned back into the feeling until he was empty.
Ally carefully pulled away from his cock, lips sealed until she had swallowed his load. Chris, satisfied but not done with her, gently but firmly tugged on her hair still laced in his hands, guiding her to her feet.
“That’s quite the passing grade” he smiled wryly. “I suppose it’s time to give you what you begged for." Ally nodded vigorously, her hand still between her legs.
With a gentle push, Chris laid Ally back on his bed, then walked over towards his closet. He unzipped the travel bag hanging on the left side, and quickly retrieved the two items he had in mind. When he turned around, he saw Ally curiously watching him, and her eyes travel to the Hitachi vibrator and pair of handcuffs in his grasp.
He wasted little time, setting the toy next to her on the bed, and made his way towards her head, grasping her hands and quickly locked one in the cuffs, threaded the chain between the bed frame, and started to cuff the other. She made no effort to stop him, but had a questioning smile on her lips.
“Oh, since when did you have one of these?” she asked, nodding at the vibrator.
“I’ve had it for quite a while” he responded, feeling the cuff click into place. He tugged at them to make sure she was comfortably anchored, then circled back to the front of the bed.
“I thought of using it for punishment at some point, or perhaps just to have on hand should things have gotten serious between us, but now’s as good a time as any to put it to use. Spread your legs.”
With none of the usual embarrassment Ally displayed being naked in front of him, she eagerly splayed her legs, giving Chris quite the attractive sight of her bound to the bed and ready to be used. He briefly considered going back on his earlier statement and fucking her here and now, but though they weren’t all that drunk, he wanted such a thing to be a sober decision.
So he plugged in the Hitachi, sat down on the thick comforter next to Ally’s nude form, pushed the head of the vibrator against her wet pussy, and flicked the power on.
Ally instantly groaned and her eyes closed, seemingly awash with pleasure. Chris ran the head of the toy up and down her slit, pausing at the top every time for just a brief moment to push the head against her clit. Just because he planned on giving her orgasms, didn’t mean that he had to make it easy for her, and he teased the vibrating head up and down her pussy, never letting her get enough stimulation to tip over the edge.
For her part, she didn’t seem to much mind, grinding herself against it as best she could being bound at the wrists, her eyes closed as she was lost in the sensation. Even with his teasing, her lower body began to tense and she looked at him with hooded eyes.
“Please sir, can I cum? I’ve been a good girl…” she breathlessly asked.
Chris considered being cruel and denying her further, but relented, another idea in mind.
“You have permission” he affirmed, and to drive it home, he pushed the Hitachi against her clit fully.
Ally’s eyes rolled back and she let out a loud groan as her orgasm took hold. Her legs came together and squeezed, pinning the vibrator against her. She rode it out until it looked like the waves of bliss subsided. But he didn’t remove the vibrator. In fact, he pressed it down harder against her clit.
The effect was immediate. Rather than her orgasmic moans just a second ago, Ally started to groan in a mix of discomfort and masochistic pleasure.
“It hurts” she complained.
“Oh, does it?” he responded but only a slight hint of condescension. “You begged me to let you cum, and I agreed. I didn’t say how many times you would cum, or that I wouldn’t force a few out of you. So we’re gonna do this until I think you’re all orgasmed out.” He took her breast in his other hand and began to lightly rub her nipple with his thumb.
Ally breathed out heavily as the sensation started to take over again and within a few minutes a second orgasm quickly started to build. A scream of pleasure and pain ripped through her voice as it hit her washed over her again, her legs trembling as it shook her whole body. Chris continued to absentmindedly play with her breast until the orgasm died down again, before he stooped down to the floor and retrieved her panties.
“That was quite a loud one” he commented “and I don’t want the neighbors thinking I’m killing someone. So these are going in your mouth until we are done.”
He balled up the panties into a makeshift gag and pushed them against her lips.
“Are you still okay to continue?” he asked in a soft voice, reaffirming her consent. When she nodded, he resumed his role.
“Okay. Open up” he said in a tone that brooked no argument.
With a continued level of obedience that was slightly surprising to him, she took the garment into her mouth. It wasn’t the most effective gag, he did admit, but anything for her to bite down on and stifle the noise would help. With that out of the way, he pushed the vibrator against her sensitive hood again mercilessly.
The third orgasm was a powerful one, and Ally squirted all over herself and the Hitachi, soaking the comforter below. The fourth, and fifth were not much different, and though she was gagged, Ally still continued to cry out in tormented pleasure with each passing orgasm torturing her overstimulated clit. Still, after every orgasm Chris would check in with her, and every time she nodded her consent.
Even so, he could tell she was reaching her limit, and decided to make this one the last. He held the vibrator down heartlessly as the final orgasm tore through her body. Ally gave no struggle, and merely wordlessly moaned into the now soaked panties hanging out of her mouth. After the last tremors of pleasure ran their course, he turned off the vibrator and placed it to the side.
He looked down at Ally, tied up, absolutely drained of energy, with her panties in her mouth and covered in her own fluids, and felt a sense of satisfaction, and a second wind of desire building within him. Perhaps another time, he thought to himself, and clamped down on the thoughts.
He leaned over Ally, and uncuffed her hands from the bedframe. She looked up at him with half closed eyes, before petulantly spitting the saliva soaked wad of her panties out at him. He gave her a look of mock admonishment, and then with an exaggerated sigh, began the arduous task of cleaning up the mess of their night.
Quite a bit later into the night, Chris laid in bed next to Ally, under the spare comforter he exchanged with his normal one. He looked over, smiling at her sleeping form next to him. She had naturally fallen asleep while he had been picking up, and so she was still naked, her clothes folded neatly by him on the dresser. He studied her expression while his hand traced almost imperceptively along her arm. She looked so peaceful and serene in her sleep, hardly looking the part of the girl that put him through so much strife throughout the years.
He thought back through their conversation earlier in the night, trying to make sense of everything said, and the events that followed. After a few minutes of addled thinking, clouded by slight drunkeness and exhaustion, he gave up and rolled onto his back, staring up at the dark ceiling above him.
He truly did not know what the future held for them, if anything. He did not know whether this would all a mistake that he would regret with years of hindsight, or if this was exactly as things were meant to be. None of it mattered to him all that much in the moment. He closed his eyes, smiling at the warm presence next to him on the bed. All he knew was that through it all, he was happy to be her disciplinarian.