Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
"Unnn... yes ma'am," he whimpered, knowing she was toying with him. He felt he could cum at any moment.
Maggie recognized that. They hadn't been together long, but she'd been with enough men to read the signs. His were not all that dissimilar to the rest of them. She knew exactly when to back off of speed or pressure to keep him from popping off before she intended, and her goal was to draw it out. She wanted him to experience pleasure associated with anal play instead of thinking of it as humiliation.
She was toying with his nipples, tweaking them with her left hand while she played with his cock. Letting go she moved her hand between his legs, playing with his entrance with her fingertips. He bristled and stiffened up, which she expected, including his nervous protest.
"Mistress?" he called out quitely.
She smiled, even as he squeezed his eyes shut tighter. And his anal ring, trying to stop the impending invasion. "Yes, my love?"
"Pleeease... noooo."
"Ssshhhh. Trust me, Alex. Your Mistress knows what's best for you. You believe that, right?"
"Yes ma'am," he nodded.
"Then unpucker your asshole and let me make you cum like a rocket going off to space." Taking a deep breath he relaxed, nodding again to let her know he was ready. Taking up where she left off with her other hand, she lifted the weight of his shaft off his stomach, which was in danger of deflating at any time. Stroking the length again, she slipped the two digits back into his anal cavity, but with a much different purpose than to grease it up to be fucked with a strap-on on later.
She began moving them in and out, fucking him with them. She'd twist her wrist, spinning them around inside to vary the sensations, wanting him to feel the difference. In doing so, she would squeeze his cock tighter with her fist, making it feel like he was fucking an ass himself.
"Ooohhh gaaaawwd," he panted as she added a third finger.
"It's okay to admit it, sweetie. It feels good, doesn't it."
"Yeeeeeeeesssss," he mewled.
She felt his walls milking at her fingers, because while slowly fucking him with them, she had begun to massage his prostate.
"You're going to love me for doing this to you, sweetie."
"I already love you, Mistress," he replied dutifully.
"I know. But you're trusting me, and I'm going to reward you soon."
She drew it out another fifteen minutes. Twice he asked permission, which she denied, telling him she wasn't done with him and that he'd be thanking her later. He had to fight, and she helped by backing off, but he was able to control his urges.
"Please! Please can I cum, Mistress," he pleaded.
"No. You're saying it wrong. Use proper English."
He was confused, the need for release overwhelming him so that he couldn't think straight.
"Pleeeeese?"
"Whining isn't correct either. Ask me properly, sweetie."
He took a deep breath, trying to calm himself. His lower body was about to lurch upward, looking for stimulation it needed. She could anticipate that maneuvering and would let go of his cock, threatening the ruin his climax like she'd warned.
Finally a light bulb clicked on. "Please, MAY I cum, Mistress."
"That's better," she cooed. She started jacking him wildly while increasing the pressure on his prostate. He started to buck his hips and she cautioned him. "I'm doing the work. Lie still or I'll stop."
He froze, a long, low wail starting to emanate from his chest through his neck. It was pained, sounding a bit like a wounded animal. Yet the pleasure he was feeling was the most intense he could recall. His toes curled, and she knew he was ready. She stopped jacking him off, changing to more of a pump action like a shotgun. She'd start at the head, rammed her gripped fist down to the root as hard and tight as she could. Then she'd go back to the top and do it again. Timing the strokes, he began firing thick white arcs of hot white cum all over his chest. She was angling the shaft in order to get maximum distance. The first two shots landed on his chin and neck, before starting to shorten. But because of his incredible gift of being able to explode like a horse, it seemed more likely he wouldn't stop cumming.
She didn't stop, even when he seemingly emptied his balls. She doubled down on her finger work in his ass, while concentrating solely on the head of his cock. It quickly became oversensitive, feeling like little pins pricking at his skin as she tortured him sweetly.
"Again, Alex. You've got more cum for your Mistress. I want it now, please."
"No! I can't! Please stop!"
"No. I know best. You have more. Give it to me."
"Ooooohhh! Ooooohhhhhh! GOD FUCK IT!" he yelled as he started spewing again.
Maggie giggled as she moved his shaft back and forth, covering as much of his sexy tan chest as she could. When his cock stopped twitching and it became apparent she'd milked him sufficiently, she stood triumphantly over him.
Snapping the gloves off, she walked toward the bathroom to discard them and wash the latex smell from her hands. But not before asking, "Do you have something to say to me, Alex?"
"Th... thank you Mistress," he panted.
Peeking her head out as she lathered her hands away from the sink, she wanted more. "And?"
He nodded. "You were right. That was amazing."
"Yes. And so am I, aren't I."
"Yes ma'am."
"There. Now you know that anal stimulation isn't always a bad thing. And since you just experienced it, I'm hoping it will make what might have to happen today a little easier to accept. If you release your tension and relax, you might even be able to enjoy it."
"I don't think that will happen."
"I promise it will if I get to do it."
"If you don't?"
"I just showed you what's possible. You need to trust me."
"We're talking about me being pegged again."
"I'm well aware. Why do you think I just did all that for you? It's because I love you, and I want to make it as easy for you as I possibly can."
"I know. Thank you."
"I don't want you to thank me. I want you to trust me. I know you don't want to do this. I know it's not what you envisioned. I don't want you to have to go through it either, but I'm going to be with you and we're going to get through it together. And if you'll trust and listen to me, I'm hopeful you might get pleasure out of it in the end."
"I'm going to get it in the end alright."
"Stop it."
"I was joking. I really do appreciate you helping me try to make the best of it."
"Remember, sweetie. Positive attitude, positive results."
Alex was showering when Maggie made her way down the spiral stairs to the kitchen. Kalinda and Billy were still at the table, their head buried in their laptops. Kalinda saw her approaching first.
"Is Alex okay?"
"No, but he will be. He's crying in the shower. He just doesn't think I know."
Billy shook his head. "Takes an evil cunt to do that to a man against his will."
"Don't blame Christina. At this point I think she's brainwashed. I just don't know whose doing it."
"We do," Kalinda replied.
"Well, we can't go that far yet. But we know a lot more than we did an hour ago. It's not pretty, but it does answer some questions," Billy corrected.
Maggie held her hand up. "Let's wait for Alex. I want him to hear this so we can all process it together."
~*~*~*~*~*~*~
Late Wednesday Morning, May 21st -- DAY 6
Christina was in the shower, trying to wash the events of the previous day off of her. Frankly she didn't think she had enough soap. At least the water was hot. Having rinsed the shampoo from her hair, she began shaving her legs and then her pussy, careful to navigate around the blonde 'V' that her pubic hair was styled in; yet another personal feature that highlighted the persona she was adopting. She was in Las Vegas, and she was Venus Butterfly.
Washing her hair and shaving her pubes brought to mind those new, daring styling choices and the stylist who gave them to her. The talented and irresistibly sexy Sasha. In any other circumstance she could have seen things turning out where they'd actually become friends. Very good ones, even considering they came from vastly different backgrounds. She was a good person, with an genuine heart, and Christina could feel that.
There was a part of her that wanted to see her professionally again in the future, knowing she was far better than anyone that had ever done her hair before. The way Sasha listened to her story of how she became a hotwife, and the relationship she was trying to forge pursuing that lifestyle with her husband, and turning that into the style she chose for her? It was, in a word, impressive. She'd even thought of an appropriate song, using it as a muse, describing line for line how the lyrics spoke to the journey that she and Alex were on. It was inspired, which was reflected in her new hairstyle.
Yet Sasha was a potential issue.
Christina didn't know who was really calling the shots. While she at first thought for certain it was Gerard, that changed the more she was around Brandi alone. There was something about her friend that troubled her, yet she didn't have enough information to go on. It was more of a gut feeling; one she wanted to trust, but couldn't for fear that if she were wrong and it was truly Gerard at the helm, it put Alex at greater risk. Particularly since he'd yet to show up in Vegas.
With him still in California until what she thought was later that night, she had to keep her thoughts close to the vest. Alex was going to be going to see Sasha later that afternoon, and the thought of what might happen while he was there made her nauseous.
"I wish I could find a way to text him and warn him," she said to herself as she started crying. She knew the waxing was going to be traumatic, but not nearly as much as what she knew would follow. Brandi had convinced her before she'd come to her senses that she needed to keep pushing the cuckold button with Alex like she did with her husband Scott. And the next step was for Christina to up his torment by having him pegged not only away from the comfort of his own home, but have someone else do it. Someone besides the person she'd left in charge of his sexuality, which was Maggie.
Christina tried to control her emotions, not wanting Brandi to discover the internal turmoil she was struggling with. She had to maintain like she was on board with the direction she was allowing her husband to be dragged. She'd gotten ahead of herself, drunk with the power of a Femdom led relationship. That she'd gotten to test pile-drive a huge, grotesque looking bad dragon dildo into Scott's well trained ass, a man already used to such treatment at the hands of his Mistress wife, made her amenable to Brandi's subtle urging for her to do similar things to Alex.
Unfortunately she'd set that ball in motion, again following Brandi's suggestion to recruit Maggie in her scheme to control Alex from afar, using her hatred of Ashley as the catalyst. Alex had fucked the buxom blonde a second time, as a way of providing closure for the two of them; a gift to the two of them by Jack Austin, who was Alex's friend and Ashley's new Dom. It was twisted logic, but it made sense to all of them. All except Christina. She began seething when she discovered the indiscretion, tasting Ashley's cunt on Alex's cock, of all ways.
Her distrust and anger caused an argument. The idea that Alex had just salvaged Ashley's law career by winning a lawsuit against her former firm for firing her, in part because she outed them for shady practices, but also because she'd fucked Jack at Alex's urging... well, it was an ugly, messy shitshow of Alex's own doing. But with it fixed, and Ashley hired by his firm, the two of them seemingly doubled down and fucked up again by fucking again.
Post argument, she called Brandi for advice on whether or not she was overreacting. Brandi listened, and took advantage by telling her she was. But she also used the opportunity as the catalyst to shift the focus away from Ashley, saying she needed find a way to encourage Alex to fuck Maggie. Christina was on board. She trusted Maggie, even though they'd never met in person. And she found Maggie as a willing ally, because Brandi was expertly manipulating the narrative behind the scenes.
It worked so well that Christina had actually talked Maggie into not only being in charge of what she considered her cuckold, she talked her into disciplining him, and then pegging him. With that precedent set, it was seemingly inevitable that he'd be pegged again that afternoon. She'd held out hope of finding a way to stop it, but she had her own problems. Namely, the reaction she was having to the crazy amount of drugs she'd taken in the past twenty-four hours. Not only had she smoked five hits of THC, including two already since she'd finally woken up, she'd had so much cocaine that she could feel herself crashing from what she could only presume was withdrawal of some sort. She'd woken up shaking, craving more. At least that's what it felt like. She wondered if the reaction she was having might have been paranoia, or perhaps psychosomatic.
The THC calmed those cravings, but she knew it was an uphill battle to stave off doing more coke. She'd be back at the club later that afternoon, ready to start another eight hour shift of drugs and sex, to be followed by the next gangbang. She actually couldn't wait for that part, wanting to experience it again with more men like Brandi promised. Seven verile cocks wasn't nearly enough to satiate the both of them.
She still regretted fucking up her first opportunity for a group encounter like that with Brandi at Gerard's house, the willing participants all being men that worked for him. She'd ruined that night by refusing to suck the cock of the pizza delivery driver. She'd done far more degrading things since that time that it embarrassed her how she'd acted toward what turned out to be a sweet man that had lost his wife to a car accident and was working several jobs to support his kids. A man that Gerard gave another chance to have sex with her the following day, where Christina learned not to judge a sexual book by it's cover. That is until she fucked up the very next time she'd been given the opportunity. It was why she was dealing with the current plight she was in.
With no recourse to save Alex that she could think of, she tried to put him out of her mind. Calming herself, she turned off the water and stepped out into the steamy bathroom. She couldn't see her reflection in the mirror, the glass surface fogged up. She didn't really want to see the monster that would be looking back at her.
Brandi had already showered, much to Christina's chagrin. It seemed like the woman never slept. Or if she did, it wasn't for very long. She kept looking for the opportunity to be alone in the room, thinking she'd be able to find her phone and fire off a quick text. To that point she hadn't been able to make it happen, and it was frustrating.
Trying to gain her confidence, the prospect of a repeat performance of the previous twenty-four hours looming over her like a dark, drug induced cloud, she brushed her wet hair and shook her extremities to loosen herself up, thankful that she was in such great shape. Her stringent workout routine had enabled her to endure the stress she was putting on her system. She was sore, but the good kind. The kind that burned like she'd spent three hours in the gym. Working the pole was a good substitute for her daily regimen, at least when coupled with the marathon sex session she'd been on since arriving in Sin City. On that front she felt right at home. The only thing that was really different was the drugs. Actually, the cocaine she'd taken two days straight, staring down the barrel of her third. The THC seemed normal because she done it at home, albeit only with Brandi to that point. She could actually envision doing it herself on her own though. She loved it. But coke scared her, concerned she become addicted. Knowing she needed to do it again that night, she was already thinking about the preventive steps she needed to take.
Walking around the corner into the bedroom area of the room, she said, "B, can you throw me the asp... irin! What the fuck ARE YOU DOING!?"
Brandi was crying, tears streaming down her cheeks. On the table beside where she was sitting was a lighter and a spoon. Next to that her phone and a small plastic container, like something camera film would come in, the lid off of it. She had an orange rubber tourniquet tied off on her upper left arm; the needle of a loaded syringe poised to pierce a bulging vein on the inside of her elbow.
"I... I lost. I didn't know he... oh God."
"Is... is that heroin?!"
"Ye....essssss," she sobbed, nodding her head.
"Stop! Don't do it!"
"I... I don't have a ch... choice. I lost. He knooooows!"
The tears rolled, her body shaking. Christina could see the fear on her face. She raced over and gently put her hand on Brandi's right forearm, pulling the needle away before untying the rubber tourniquet. "Calm down B. What's going on? Tell me what's going on."
It took her a couple of minutes to get her friend to stop bawling; to get her to calm down long enough to think more rationally. Brandi's breath was ragged, catching in her throat as she tried to get control of her emotions.
"Are you okay?" Christina asked, kneeling in front of the naked beauty.
"Y... yes," she nodded. Then she shook her head. "No. I... I lost."
"You lost what? What's going on?"
Taking a deep breath, she sighed. "I lost to you, Chris. Last night. I, I just didn't think he was serious. But he was."
"Gerard."
"Who else," she shrugged and nodded.
"Talk to me. I want to know everything B. Right now. Spit it out."
"Sluts don't spit," she tried to joke.
"Enough. I can't help you if I don't know what's going on."
"You can't help me. Don't you understand?"
"Of course not. You haven't told me anything yet. Stop stalling."
"Last night, you and I were part of a contest."
"Wait, do you mean that 'Stripper of the Shift' bullshit? You know that was rigged, right? It was just an imaginary popularity contest."
"No it wasn't. The winner was the girl that pushed the most cocaine. That was definitely you. It was supposed to be me."
"What?"
"Gerard pitted us against each other. He set us up in that club. He knows Vinnie and Frank. He knows what they do there, and about the contest. I told you before that one of us had to win it. Thankfully you did, or we'd probably both be doing this."
"Doing what... herion?"
"Yes. But I thought as long as one of us won, we were in the clear. That's not what he meant."
"I don't get it. Do you mean the loser between us has to...."
"No. Just me."
"I still don't get it."
"I'm your mentor, Chris. I'm supposed to be teaching you how to be a slut, and a whore. The first time you've done something like you did last night, and you were better at it than me. I'm being punished for being surpassed by my protege."
"B, seriously... you can't do this."
"I don't have a choice. I've tried to warn you... you don't know what he's capable of. And if I don't do it, I'll end up having to do it to you. I..."
She started to tear up again, and Christina hugged her. "How? How did he even find out?"
"I told you, he sent us there. He knows the Mangini brothers. They sent him the video. By the way, you have to video me shooting up. I have to send it to him."
"Okay, first, you're NOT shooting up with heroin. We're going to wait, and we'll talk to him tonight. This is crazy."
"He's not coming tonight. He cancelled the flight. He's coming Friday night."
"What?"
"He said I failed him, and I have to make things right. Since we aren't on the next rung of that ladder, he's delaying his arrival."
