Dorm room hi-jinks and apologies

(The following chapter contains my first attempt at M/f/m content. If that bothers you and would like to see an iteration of this chapter that is 100% straight. Leave your thoughts in the comments section. If it is good and you want to see more content of its kind, leave those comments as well. Honestly, I just like the comments. I am always willing to entertain requests.)

Jack had tried to convince Amanda to let him have one final conversation with Olivia for closure’s sake, but Jack was to discover that Olivia’s roommate would not see reason. If anyone had reason to feel grateful for the drastic transformation of The Kennels it was the overweight acne covered girl with whom Olivia had to share her dorm room. Amanda was barely recognizable. Jack was delighted to discover that the **** girl was exceedingly eager to show her owner how grateful she was for the transformation into a hottie. “You will have to wait your turn.” Jack told Amanda. “But help me move into my new place and I am sure that I can find some space for you in my harem.” This made Amanda squeal in delight.

Jack had walked in on Olivia and her man slut about to get it on. As much anger and jealousy as he felt towards the pair, the absolute power he had over the situation with the soul-trainer in hand gave the twenty year old a lofty confidence far beyond his years which bordered upon the arrogant. Jack thought he might have to banter with the pair, but the muscle-bound girlfriend-thief being eager for **** took the decision out of Jack’s hands. A second faster and the douchebag would have been punching Jack in the face, but Olivia’s boytoy was a second too slow; the man Jack hated more than anyone else was kneeling at his feet.

Jack admired the beautiful sight of Olivia bound for his pleasure. Toying with her and watching her squirm seemed all the more fun when he knew that in a few moments she would be completely under his thrall. These last moments of her defiance added a spice to what Jack knew was coming. Her indignant response to his honest inquiry about her status as a virgin made Jack almost feel grateful that she had broken up with him. Of course that did not mean that he was not going to enjoy what came next.

Like all the slaves who returned from The Kennels. Olivia looked like the most perfect version of herself. To Jack, her loveliness was almost painful to gaze upon. Jack gestured for the ****-boy to release her. Olivia fell to her knees. “Master. I am so. So. sorry. After how I treated you, I cannot imagine how you thought me worthy of the sacrament of bondage. But since you have chosen me. I promise to spend the rest of my life showing you how grateful I am for the opportunity to be owned by you. Master.” Olivia said.

Jack took a moment to admire his two new slaves. He was surprised. Jack had imagined that turning Olivia into a **** would feel good, but he had not counted on how much he enjoyed owning this guy as well. As someone who had always been on the smaller side, Jack had resented how people born lucky with big bodies and powerful muscles could intimidate him. But now one of those gym bros was under his command. It was like having most of the benefits of being big and strong without having to do any of the work. Plus…

“Tell me, boy. Do you like guys?” Jack asked the dude he now owned.

“No, Master. I am straight.” The guy responded. “But what I like does not matter. A **** serves his Master however his Master desires.”

“Good answer. Whatever your name is.” Jack said.

“My name is Theo, Master.”

“I did not ask.” Jack sat down and grabbed an empanada from the box. “Both of you, strip.” He commanded his slaves as he took a bite out of the savory pastry.

The two slaves did not hesitate to remove what little clothing they were both still wearing. The pair stood side by side, Jack could not help but notice the way that their fingers’ instinctively clung to one another as Jack scanned their nude forms. Jack scarfed two empanadas and bounced up to his feet. The slaves watched their owner stride towards them to get an upclose inspection of their exposed bodies. “Were you always hairless or is this something you work on?” Jack asked Theo as his fingers caressed the bare patch around Theo’s cock where a man would normally keep his pubes.

“I get waxed and shave regularly. Master.” Theo said, his tight body language illustrating clear discomfort.

“Did you shave for him?” Jack asked Olivia as he fondled her bare pussy.

“I. I was a fool, Master. But the lectators have remade my body. They restored my hymen and made everything REALLY tight down there. So I am even better than a virgin.” Olivia said proudly.

“Oh Liv. It does not work like that.” Jack said as he caressed her lips. “You broke a solemn vow. You said that we were boyfriend girlfriend. You said it would be so wonderful for two virgins to have their first time under a full moon. You went behind my back. You got wasted and acted like a slut for everyone to see and just let the first guy to smile at you at a party stick this…” Jack grabbed Theo’s cock and squeezed it violently enough that no amount of training could prevent Theo from wincing in pain. “In your holiest of holies. A place you promised me.” Jack moved his hand from Theo’s dick to Olivia’s face. “Tell me.” Jack stroked Olivia’s cheek and lips with his thumb. “Were you telling me the truth when you said that I was the first boy you ever kissed?” Jack asked.

Olivia nodded vigorously. “Yes Master. Before you the only people my lips had touched were family. You were the first boy I had ever kissed. The first person I ever called my boyfriend.” Olivia said with a slight sniffle. Jack could see her regret and shame and reached out to kiss her. For a brief moment the pair were transported back to a simpler time when they were two kids far from home who were trying their best at learning how to adult. She tasted sweet on Jack’s lips. Jack smiled as he gazed lovingly into her eyes. Without breaking his eye contact with his first love and first love lost Jack addressed his other ****. “Boy, get down on your knees and suck my cock. If I am not hard in two minutes. I will. I will…”Jack had to think of a good threat, he came up with. “I will send you back to The Kennels for a refresher course.” That got the ****’s attention. Despite his claims of being straight. Theo showed himself to be a skilled and enthusiastic cock-sucker and worked away at polishing his owner’s pole while Jack made up for lost time kissing Olivia. “Liv sweetie. That Halloween costume you posted on Instagram, do you still have it?” Jack asked.

“Yeah. I mean, yes Master.” Olivia said, Jack thought it was amusing how she seemed to be slipping between her personality as ****-Olivia, Veteran of The Kennels and Liv, Jack’s girlfriend. Something for Jack to work on.

“Go put it on, no underwear though.” Jack said. Placing his hand on the head of his cocksleeve, Jack watched as Olivia put on a reverse strip show. In a slow and sultry manner, the naked **** girl seductively robed herself into a red bedlah which matched the one Jasmine wore in Aladdin when she was enslaved by Jafar’s power, complete with snake armlet. Jack’s face sprouted a wide grin as his cock sprouted a long and thick erection. Jack pulled out his phone and started playing Missy’ Elliot’s ‘Get Ur Freak On.’ “Dance ****. Dance like you are at a party and want to show off.” In those few minutes, Jack saw a whole new side of Olivia, the nineteen year old girl moved with a sensual vitality that she had never shown Jack the boyfriend. Jack definitely preferred being Jack the Master.

Jack popped his cock out of Theo’s mouth and beckoned Olivia to his side. The sexy **** girl sauntered over to her owner her wasted no time cutting the inseam of her see through harem pants. Olivia was confused for a moment before she remembered what Jack had said before about anal. “Please. Master.”

“Please, what, ****?” Jack waited to hear what excuse she would come up with to dissuade him from claiming what she had promised, her virginity, in the one place she was yet inviolated. Olivia stood there in silence. “That is what I thought. Boy, fetch the lube. I know Liv has some vaseline around here somewhere. Thank you.” Jack said as Theo handed him the petroleum jelly container. Jack bent Olivia over her desk and slathered a generous dollop of the goo on his cock before smearing the substance over Liv’s ass. The nineteen year old squirmed in anxious anticipation. “FUUUCK you were not kidding, that is TIGHT!” Jack said as he **** his way inside her virgin asshole. Olivia cried out in agony.

Olivia wanted to run, but knew that she could not. She wanted to shut down, but the pain was too great. Olivia the **** girl did the only thing that her training would allow for her to do. Jack felt Olivia slam her ass back into his crotch. The man heard his girlfriend turned **** girl take in a long sharp breath and let out mewling pants. “Oh fuck yes, harder, fuck me master, fuck me master, fuck me master…” The **** went into an almost sex-bot like performance as she focused all of her attention on making her owner cum as fast as possible.

Theo watched as the love of his life was fucked in her ass by their mutual owner. With the taste of Jack’s cock still in his mouth, Theo worried that his owner would come up with some way to make Theo a part of his Angel’s violation. Theo knew better than to turn his gaze away. He watched dutifully, hoping that this particular duty would be over soon.

“Are you sorry bitch?” Jack asked Olivia as he pulled back on her hair taking another hard thrust.

“Aaahhhah. Yes, Master. I am sorry for hurting you. I am sorry for cheating on you.” Olivia struggled to say amidst the pain and tears.

“Are you sorry for becoming a slut?” Jack asked.

“YES! I am sorry for becoming a slut.” Olivia said.

“I bet you regret ever meeting Theo now, don’t you?” Jack said. Olivia was silent as she bit her lip.

“I…” Olivia’s breathing became even heavier. “I regret not sharing our first time together.” Is what the **** girl eventually said. These words were enough to make Jack cum. He grabbed the ****’s neck and hair as he pulled her back as his body spasmed and gobs of semen leaked into Olivia’s ass.

Jack stumbled backwards and wobbled around as the young man struggled to get his legs. When he realized that was a lost cause Jack collapsed onto Liv’s bed. Out of breath and in no mood to speak. Jack gestured to his slaves, assigning them to their tasks. For Liv that meant sitting on her bed with Jack for cuddles and kisses. For Theo, it meant cleaning the Master’s cock with his tongue.

Jack’s hands explored Olivia’s new body as the two would exchange smiles between exchanging saliva. “Now that that is over with. I hope that you and I can move on and have a normal relationship. Or as normal as any master/**** relationship gets.” Jack said. This seemed to make Olivia happy because she kissed him with the same sweetness he had tasted on her lips when they first met. “Tell me. Among your girlfriends. Which ones are still virgins?” Jack asked.

Olivia had to think about it for a moment before she said. “Well. Stephanie is engaged to her high school sweetheart and keeps talking about how much she is looking forward to a fairy tale wedding followed by a magical honeymoon once her fiance is back from his Missionary work. Marissa is in a similar boat, but her fiance is in the marines. Leah and her wife Kendra love to brag about being gold and platinum star lesbians respectively. And then there is Emily. If I had not seen her ID saying that she was 18, then I would not believe that purity ring wearing weirdo was old enough for college from the way she talks about her teddy bear collection. To say nothing about how her mom escorts her from class to class and lurks around.” As Olivia showed Jack pictures he smiled and nodded. He could imagine them all lined up, each of them doing their best to convince him that theirs should be the first pussy Master fucks.

There was a small voice that cried out that these girls were innocent and that if he enslaved another man’s virgin bride that would make him little better than the girlfriend-thief turned cock sleeve Theo. But then he remembered that no one was complaining about being his ****. Everyone who came back from The Kennels did so with enthusiasm and zeal. They all said that Jack had been doing them a favor and that a lifetime of submission and obedience was simply their way of saying thank you.

(This next sentence is only relevant to those who have not read the Ball Breaker arc yet)

Of course there was the matter of Claire and Ms. Jeaneen. He could not leave that issue unattended. What was it that they said in the comic books? With awesome power comes awesome problems.