This story is a prequel to Best Friends Forever, and Best Friends Forever part 2.
Start at the beginning here.
He did not deserve Katie’s forgiveness, but he was committed to earning it for the rest of their relationship. He had been awake most of the night trying to structure his apology, and ultimately felt like it was a lost cause. When Katie had broached the subject, he was prepared to just step back- he knew that what he had done was unforgivable, and did not even want to ask for her to try. He thought that the best thing he could do for her is leave her alone. She was willing to give him so much of herself that night, and he had done nothing but take from her. To say that he was shocked that she wanted more was an understatement.
They spent the rest of the day ironing out their new dynamic. It was important to Katie that their relationship stay intact- she wanted to do movie night and dates and be able to have arguments and disagree. She didn’t want a full-time Master, and Jack understood that. They both agreed, though, that part of the thrill of the dynamic was for her to be subject to his use on a whim.
They agreed that Jack would still be able to shift their dynamic into the “Master” realm at will unless Katie used a safe word. They also decided that while they’d share their relationship with Julia, they would keep their dynamic a secret, so would only play when she was out of the apartment. They talked about limits, knowing that neither had a ton of experience so they would need to communicate often. They committed to trying new things and debriefing them after so that they could learn and craft their dynamic to suit both of them. Once all of their ideas and wants had been written down, they both signed their names- Jack tucked the contract in his bag with a smile.
They took the night to reconnect as friends, snuggling on the couch and watching a movie until the wee hours of the morning. Jack spent the night again, neither of them wanting to be apart.
The next morning Jack made Katie breakfast, kissing her goodbye as she headed off to placement. He tidied the place up a bit before he left, leaving her a note that he would bring dinner when she was done work. He spent the day running errands, picking up some last-minute Christmas gifts, including a few for Katie. He had a hard time thinking of anything other than her; his mind was rife with imagery at the possibilities that their new dynamic held. It wasn’t long before Katie had texted him a photo of his note, with the words “you are too good to me.” Jack smirked, typing back, “don’t worry- you’ll earn it,” before going to pick up their food.
Katie greeted him warmly when he made it back to the apartment, taking the food out of his hands so that he could remove his coat. She had changed out of her work clothes into her standard yoga pants and tank top, though Jack noticed immediately that her usual sports bra had been exchanged for something black and lacy. “Mmm, sushi- my favourite,” she said, as if he didn’t already know.
Before she could dig in, Jack took the food from her and put it in the fridge. He smiled at her pouty face, already eager to see more of what those lips could do. “If you’ll recall,” he said formally, “I did say you would have to earn it.” He grinned as Katie’s eyes widened, demonstrating her understanding.
“Yes Master,” she said obediently.
He walked over to face her, running his thumb along her bottom lip. “These lips are quickly becoming my favourite thing,” he said seductively, moving his hand down to gently grasp her neck, “and this throat- so welcoming.” Katie didn’t move, but held eye contact with him as he slid one of her straps down her shoulder, replacing it with a kiss. He kissed his way up her neck, lips landing to nibble her ear. “On your knees,” he whispered, causing goosebumps all over her milky skin.
Katie did as she was told, looking up at him through wide eyes. “Good girl, so obedient,” he praised as he undid his belt. “Now, Katie, I’ve been thinking. In this dynamic of ours, you have a way to delineate between our relationship and playtime with my name. I am Jack, your boyfriend, and Master, your owner. I think you need another name- something to signal that you are mine. Do you agree?”
He and Katie both knew that it didn’t matter whether she agreed, but she nodded anyway, “Yes, Master.”
“Good. I am sure that I will call you all sorts of things, but I think that a special name is also important. I have spent all day picking out just the right name but have found myself at a crossroads. I thought it might be nice to let you choose. Would you rather be addressed as cumslut or cockwhore?” Jack asked, his innocuous tone contrasting with the subject matter.
He could see Katie consider, her teeth biting her bottom lip in a way that made him want nothing more than to feel them wrapped around his throbbing cock. “Cockwhore,” she said definitively. “I want more than just your cum- I want your cock, always. I want to be your cockwhore, Master.” Jack smiled ear to ear, stroking his hand down her perfectly made up face.
“Good girl,” he said appreciatively, “you’ll be my little cockwhore. Now let’s teach you your name.”
He pulled some gloves out of his bag; they were black latex, long enough to go past Katie’s elbows- and cuffed at the wrists. He took great care in putting them on her, interlacing their fingers as he brought her hands behind her back and secured them. He stood back up, unbuttoning his pants and freeing his hard cock from the confines of his boxer briefs. Katie- his cockwhore- looked up at him, licking her lips in anticipation of her duties.
He rubbed his cock all over her face, saying “You have come a long way since we started, but you still have a lot to learn. Your cockwhore training starts today. You will learn to take my cock whenever I say, with skill and enthusiasm. Your throat is so perfect, your lips so lovely- I will need to use them often. You will learn your name, and you will train to take my cock to the very best of your ability. Do you understand, cockwhore?” His voice was gentle, but his grip in her hair was firming up.
“Yes, Master,” she said, looking up at him. She was the very picture of submission.
“Open your mouth, and stick out your tongue,” he said. He slid his cock into her wet mouth, loosely grasping her hair to hold her head steady. Her mouth was warm and inviting, and as he slid his cock back and forth along her tongue he found himself craving even more. “Suck,” he ordered, and moaned as she closed her lips around him. “That’s it,” he groaned, holding her head still. “What are you?” he asked, keeping his cock in her mouth as she worked her tongue around it to answer.
“Yr cockore, Masssssther,” she slurred.
“Very good,” he praised, shoving his cock further into her mouth. He felt her throat with the tip of his cock, and couldn’t resist pressing in. Her throat constricted around him immediately as she coughed, her body awkwardly leaning forward as she struggled to regain her balance with her arms bound behind her. She was truly at his mercy, and he took advantage.
He pulled out long enough for her to catch her breath, and then forced himself back down her throat. She was ready for him this time, her eyes watering as she struggled to keep him down her throat. She finally coughed, and he moaned at the sensation of her throat constricting around him. He pulled out again, a trail of spit connecting his cock to her mouth as she gasped for air. “What are you?” he asked, feeling himself getting lost in the moment.
“Your cockwhore,” she said confidently, opening her mouth to take him again. This time the thrust in and out of her throat a few times, holding tight to her hair so that she couldn’t resist. He felt spit dripping out of her mouth, onto his cock and down her chin.
He finally pulled out, delighting to see tears fall from the corners of her gorgeous eyes. She was off balance when he let her breathe, her body leaning into him such that he had to catch her before she toppled over. He could feel her composure weakening, and drug his cock through the spit on her chin, spreading it up her face. “Such a messy slut,” he purred before taking her throat once again.
He was relentless, allowing her one breath at a time as he continued to press through the resistance in her throat. Her body had surrendered to him; she was relying on him holding her up and she stopped fighting him as he pushed into her throat. She looked up at him, a willing vessel for his pleasure. She choked out answers to his questions as she struggled for air, her face as drenched in spit as his cock was.
“Who owns you?”
“You do, Master.”
Five slow, deliberate thrusts, deep into her throat.
“What are you?”
“Your cockwhore, Master.”
Holding his cock in her throat for a count of ten.
“What do you serve, cockwhore?”
“You…your cock, Master.”
Three slaps of his cock across her face, before allowing her to suck.
On and on they went, with Jack needling her with questions to reinforce her position, and Katie just barely holding on through his assault.
“Do you want my cum, cockwhore?” he asked as he fucked her face.
“Yes, Master,” she sputtered, desperately trying to keep her balance.
“Take it,” he said simply, and let her go.
She took a moment to regain her balance, sucking his cock into her mouth as an anchor. She bobbed her neck, setting a frenzied pace. Jack knew he wouldn’t be able to hold on for long. To his surprise and delight, she forced her head down on him until she pressed him through the back of her throat. She held him for as long as she could before taking a breath, and then thrusted him back. The surprise of her dedication- her offering up her throat like that- made him explode.
He filled her mouth with cum, holding her head steady as his body bucked and emptied into her. She held it in her mouth as he pulled out of her, bending to meet her at eye level. She opened her mouth for him to see his load, and he dipped a finger inside to paint her face with it. He closed her mouth with a finger under her chin, ordering her to swallow while he kissed her sweet, talented lips. “Such a good cockwhore,” he said affectionately, and helped her stand.
He unbound her hands and removed the gloves but did not allow her to wash her face until after they had dinner. Their conversation was casual, with their usual friendly banter, but each time Jack looked at her he could see the spit, cum, tears, and ruined makeup on her face, reminding him of her submission. She no doubt could feel it drying but didn’t fuss- no doubt his wildly adoring looks toward her made her forget about the mess.
They showered together after dinner, going to bed early. Jack was leaving for home in the morning, and Katie would go home a few days after. They snuggled up in bed together, spooning as Jack’s cock slipped easily inside Katie. He let her set the pace, reaching around to give her what she needed. He felt her pussy clench on his cock, her orgasm a whisper on her lips. He emptied into her soon after, the two of them falling asleep completely lost and wrapped in each other.
Christmas was a blur, and Katie was glad it was over. It turned out that balancing placement and the holidays was no joke, not to mention that missing Jack was a full-time job in itself. She was now back at school, the apartment still empty for another week as Julia delayed her return in favour of a trip south with her family. Katie missed her, but found herself distracted by her excitement around Jack’s return that afternoon.
He had sent her a Christmas gift, instructing her to open it in private- and she was glad that she heeded his warning. Not only had he given her more of her favourite (and expensive!) makeup, but the gift also contained several latex outfits, as well as a vibrating wand and…was that a butt plug? Katie had delicately replaced everything in the box and tucked it in her suitcase for fear that someone would see it.
She now put the box on her bed, picking through its contents to find something sexy to wear to surprise Jack. She landed on a two-piece set; a very short little skater skirt, and a short sleeved crop top, both made of smooth black latex. She completed the outfit with elbow length red latex gloves. She took her time getting ready, layering on some of her new makeup, and finishing with what was now her favourite dark red lip. Every time she wore the lipstick- even over the holidays- she thought about her lips wrapped around Master’s cock. She got butterflies as soon as she popped open the tube.
Once she was dressed, she went to the kitchen to wait, putting his Christmas present from her on the counter. He had texted her that he would be there soon, and that he was excited to see her. They messaged each other constantly over the break, Katie even sending some naughty photos to him a few times- my, how far they had come.
She heard him at the door, and stood up straight, her fingers laced behind her back, shoulders squared, and legs slightly spread. Jack came in the door and stopped short, surprise and awe written all over his face.
“My my, what do we have here?” he asked slowly, taking two long strides to close the gap between them. He kissed her deeply, pulling back and running his thumb along her bottom lip, smudging her lipstick slightly. They both smiled, a promise of more to come.
“I missed you,” she breathed, and he kissed her again to show his agreement.
“Open your present,” she breathed when they finally came up for air. He went back to the counter, toying with the ribbon on the box.
“For me? I’m touched,” he said with a smile. “I can’t imagine a better gift than what’s standing in front of me, but I’ll open it just the same,” he teased. Katie could feel herself blushing.
He opened a new belt- handmade, black leather, black stitching. He took it out of the box immediately, running his hands down the soft leather. “Katie, this is gorgeous,” he marvelled, and she was thrilled to see his pleasure.
“Look on the inside of the belt,” she prompted. He looked at her, puzzled, and flipped the belt over. Just above the stitching the leather had been stamped with an M. “M, for Master,” she said with a smile.
He came back toward her, forgetting the belt on the counter. “It’s perfect. You’re perfect,” he praised, kissing her again.
“I have one more gift to give you, actually,” he said as he went to his coat, pulling out a small square box. “I wanted to give this to you in person, so I hope you’ll excuse the delay,” he said, handing her the box.
Katie opened it quickly, revealing a delicate black leather collar. She turned it over in her hands, noting the dark red stitching. “It’s beautiful,” she marvelled.
“And so are you,” he said. “I wanted to give you a symbol- of our commitment, of my devotion to you,” he explained. “I want you to wear this when I am your Master, to demonstrate your service to me.”
She felt tears spring to her eyes. “Of course,” she said easily, and meant it. “Thank you, it’s perfect. Will you please put it on me…Master?” she said, a sparkle dancing in her eye.
“Of course, my little cockwhore. Come here,” he said, and deftly secured it to her neck. She felt the leather around her neck, just tight enough for her to notice, and she beamed.
“Thank you, Master,” she said demurely.
“I have been thinking about something you shared before Christmas,” Jack said, taking her latex-gloved hands in his, “about your needs not being met. You’re right, I was being completely selfish. I want to assure you that your needs- all of them- will absolutely be part of the equation as we go forward. I am going to prove that to you today,” he said with a grin.
“Where are the rest of your Christmas presents from me?” he asked.
“They’re in my bedroom,” Katie replied. Master took her hand and led her down the hall without another word.
“A good cockwhore earns her orgasms, and never cums without permission,” he explained to her as he bent her over her bed. She was face-down on her mattress as he lifted up her latex skirt and started exploring her pussy. His hands weren’t gentle, but they weren’t overly rough- deliberate, focused. He rubbed her clit, thrusting a couple of fingers inside her.
Before she knew it, she was already ready to explode. “Please, Master, can I cum?” she asked, hoping that she was saying the right things. He stopped abruptly, causing Katie to gasp in frustration.
“Oh, I almost forgot- because I owe you a few, I am going to make sure that today’s orgasms are extra special. Where is the plug I bought you?”
Katie was still reeling from her missed orgasm, but managed to say through gritted teeth, “on the dresser.” The next thing she knew she felt cold metal against her ass as Master warmed the plug on her skin. Her body tensed, and he obviously picked up on her nerves.
“It’s okay, I am not going to hurt you. This will make your orgasm so much more intense, you need to trust your Master, okay?” Katie nodded, too nervous to speak. She felt him spread lube between her cheeks, his finger gently penetrating her for the first time. He let her get used to his finger, tentatively inserting it in and out until she was more relaxed. She then felt the more substantial tip of the plug, and focused on Master’s voice telling her to relax as he gently applied pressure and then relaxed, letting her work up to taking it.
“Okay, Katie, it’s time. Take a deep breath, and relax around the plug,” Master said gently. He pressed the plug into her, eliciting a moan as Katie swallowed it. It hurt, but not excessively. Once it settled into place, she felt full in a way that she never had. It was a very interesting feeling.
“Good girl, I’m so proud of you,” Master purred, and Katie smiled. She felt his hands on her pussy again, and moaned as he stroked her clit. “How does it feel?” he asked her, to which she replied “Full, Master.” He made some sort of comment about filling her up more before putting his fingers back into her pussy, curling them around as he stroked her g spot.
Katie could feel her orgasm building, and with her ass plugged the sensation was doubly intense. She felt like her focus was being pulled in different directions; part of her was focused on the sensation in her ass, another part on the relentless pleasure provided by Master’s fingers. Katie felt her knees weaken, and heard herself scream as she started to cum. She tried to ask permission, but she was already falling.
Katie’s legs gave out as her body convulsed. Master let her finish, but she knew that he had picked up on her failure to ask permission. “I know,” she said, the high of her orgasm quickly being replaced with the dread of disappointing him.
“I was very clear in my instructions, cockwhore,” he said, his voice a sharp edge through the clouds of her cum-addled mind.
“I know, I’m sorry Master, I didn’t have time…” she trailed off, knowing that her excuses weren’t going to matter.
“Stand up,” he said firmly. She did, unable to meet his eyes. “Go get my Christmas present; I think we have found a use for it.” It took Katie a moment to realize he was referring to the belt that she had bought him. Fuck.
She walked slowly to the kitchen, keenly aware of the plug in her ass. She took the belt off the counter, chiding herself for not realizing its potential dual purpose. She reluctantly handed it back to him when she returned, refusing to meet his gaze and see his smug smile.
“Such beautiful leather, so soft…” he mused, “I bet it bites hard. Bend over,” he ordered, and she did.
Twenty slaps with a leather belt made her cry. In truth, ten slaps made her cry. The soft leather bit into her flesh like a hand couldn’t, leaving striking marks across her ass and thighs. She refused to give in, taking his advice and relaxing through it as best as she could. He was silent as he gave out each blow, requiring her to count and thank him. When she was delayed on her count, and he growled to propel her to act. A couple of times he intentionally hit the plug, sending a shock reverberating through her. She felt small when he was finished, her crying dying to a whimper so as to take up less space.
“Next time, you will ask permission to cum,” he said as he retired his belt. He ran his fingers over the marks on her ass and thighs, trailing featherlight kisses over the worst of it. He helped her to stand, embracing her with a gentle kiss as she tried to regain composure. “Good girl, it’s okay, you’re okay, it’s over,” he cooed, stroking her hair as she cried into him. “Lay back, and I’ll make you feel better,” he said, gently pushing her onto the bed.
Katie followed his lead, allowing him to easily part her legs. The plug was starting to feel even more tight, but it was easy to ignore with the sting in her ass. She felt his tongue on her clit, sending a bolt of electricity through her body. He sucked gently, draining all of the hurt and tension from her. His fingers penetrated her, rubbing up against the plug delightfully. He coaxed her easily to the edge, and this time she remembered her lesson. “Please, Master, may I cum?” she asked, her body squirming under his lips. “Good girl,” he said, the vibration of his voice tearing through her, “cum for me.”
Before she could catch her breath, a vibrator touched her clit. It felt like fire, her taxed nerves not ready for another assault. “Please, Master, it’s too much!” she cried, but he didn’t react. He held the vibrator to her clit, moving it ever so slightly until she was screaming. She asked to cum, at least she was pretty sure she did, and barely heard his yes before she was flung off the edge again.
She lost count of the orgasms he forced from her; between the vibrator and his skilled hands and mouth, she was putty in his hands. At some point she tried to crawl away from him, and he bound her legs and wrists to the bed, rendering her completely helpless. He forced orgasm after orgasm from her, more than making out for the times he failed to let her finish. She was begging him to stop, sure that the next orgasm would cause her to black out.
He finally relented when he saw a tear fall from the corner of her eye. She was resigned to her fate, and completely defeated- completely his. She was beautiful in puddle form, and as he removed the plug and restraints, she barely even reacted. She was completely used, completely finished, and completely sated. He got in bed beside her, holding her tightly while she took the long journey back to earth. He fingered her collar, thinking that she really was his most prized possession- and his very best friend.
Two years later…
Julia (Best Friends Forever, Chapter 1)
It took Julia’s mind a few moments to process what she was seeing. The first thing that registered? Katie’s latex-clad ass.
Julia held her breath as she took in the scene in front of her. Katie was on all fours, ass pointed toward the door. She was fully dressed in latex- she had a painted on catsuit, showing only her hands and feet. Her small, fit frame was fully on display, only accentuated by the tight fabric. Beyond the flash of fire red hair, Julia could see a leather strap connecting Katie’s neck to…Jack’s hand.
Jack was standing in front of her, fully nude. He pulled on Katie’s leash, forcing her to sit upright on her knees. He kept the leash tight, so that her face was inches from his stiff cock. It was then that Julia noticed Katie’s ample cleavage popping out of the catsuit.
Neither of them had realized that Julia was there; when she finally regained her senses she darted back behind the corner. She leaned against the wall, catching her breath and trying to process what she had just seen. As she was trying to get a hold of herself, she hears Jack’s voice: “Are you going to be my good little whore today?”
Julia covered her gasp, shocked that Katie would ever let Jack speak to her that way. When she heard Katie’s meek “Yes Master,” in reply, Julia was sure that she was hallucinating. She dared a peek around the corner.
Katie stood on her knees, looking up at Jack. “Tongue,” Jack ordered simply, still holding the leash tight. Katie obediently stuck her tongue out, keeping her mouth open. Jack rubbed his cock on her tongue, and then all around her face, trailing spit everywhere. He forced it into her mouth a few times, and in her throat until she coughed, and then wiped it on her face again. The whole time, Katie stayed still- just letting him soak her face in spit with his cock.
Julia was shocked by what she was seeing but couldn’t look away. She knew she was intruding, but there was something happening deep in her gut that planted her feet and prevented her from looking away. Jack continued his measured assault of Katie’s mouth, using her to harden his cock.
He pulled the leash in and out, guiding Katie’s pace as his cock hit the back of her throat. Sometimes he kept the leash tight, forcing her to hold his cock in her throat until she gagged. The longer they continued, the more spit ended up on Katie’s face, chin, and now breasts. She was regularly gagging, allowing Jack to guide her and doing nothing to fight back.
As alarmed as Julia was, something prevented her from intervening. Katie looked…calm. Julia kept watching, listening to the gurgling sounds and watching the scene unfold. As she watched, she could feel her heart rate increasing, the nervousness and shock in her belly giving way to arousal.
Jack was holding Katie’s head on his cock, and she began to push back on him to be able to breathe. He jerked her back by the leash, Katie coughing and sputtering to catch her breath. He took her chin in his hands, and spit on her face before saying “Don’t you dare push away from me you filthy whore…you take my cock until I tell you to stop.”
When he then slapped Katie across the face, Julia reacted as if she herself had been slapped. Instead of a cry of shock or fear, she let out a moan. She had been so lost in the moment that she didn’t realize her hand had drifted up her skirt between her legs, her moan giving up her intrusion.
Both Katie and Jack looked down the hall, seeing Julia leaning against the wall pleasuring herself while watching them. Julia’s face flushed crimson, and without a word she turned and bolted out the door.
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