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Introduction:

Jenny and Sarah befriend Amanda more. Sarah gets taught a difficult lesson by Mr. Michaels after receiving a significant reward and challenge. Meeting the challenge, the girls have a threesome, with Conner getting pegged by both of them in exchange for getting to have anal sex with them in return.
Author's Note: I appreciate the continued support and readership. Positive votes are of course appreciated, mainly to make sure that people see the story and try it out. But I would really appreciate more comments. Good, bad or indifferent. Tell me what you think, what you like, what you would change, or suggestions on where you want the story to go. I will keep putting out chapters every few days until the full story is told. That much I promise.

Jenny talked to Amanda at school on Friday and invited her to join her and Sarah on Saturday afternoon to go shopping at the mall. Mr. Michaels, up to his normal tricks, got Jenny first and then later Sarah with their vibrators while they were shopping. At one point, Jenny had to lean on Sarah when it went on high for three minutes straight. Amanda noticed and asked if everything was all right. Sarah brushed it off as Jenny still being a little hung over from the party the night before. Jenny had to run to the restroom afterward to try to dry her panties. Sarah barely held off cumming a short time later.

The girls had fun and Amanda got a cute outfit. Sarah made every effort to befriend Amanda, but she could clearly see Amanda had her eyes set on Jenny, watching as she used every opportunity for any kind of physical contact, even brushing Jenny’s hair off her face a couple of times. They invited her along to dinner with a couple other girlfriends and she accepted. At one point later in the day, they explained about having massages planned for the next day at the spa, but that the third of their group had to cancel at the last minute and with it already being paid for, they encouraged her to take the spot. She gladly agreed and they set a time to meet there.

In the morning, while Sarah waited for Jenny to pick her up to head to the spa, she got a text from him instructing her to come by later in the afternoon. Jenny confirmed she got the same message while they drove, before finding Amanda waiting for them at the spa. Once again, Sarah melted in the hands of the masseuse and knew that she could really get used to this type of treatment.

The three girls went to the sauna afterward. Sarah and Jenny both hung up their towels and sat naked in the heat. Amanda looked unsure but eventually hung her towel on a hook and sat down to join them. She looked self-conscious, but she had a great body. A few inches taller than Jenny and Sarah but thin with a curvy ass. Her breasts were smaller than Sarah’s, but were very firm with a perfect round shape and plump dark red nipples atop small areolas. She also had thick curly pubic hair to match her almost jet black regular hair that hung down straight, just above her shoulders.

Amanda’s eyes kind of popped when she saw both of her companions had completely hairless crotches. “When did you do that?” she asked Jenny and then immediately got embarrassed when she realized that her question made it obvious that she must have had seen Jenny’s pussy before.

Amanda blushed, but Jenny ignored the awkwardness and told her, “Last week. I decided I wanted to try something….new.” She and Sarah both chuckled a little.

“Do you like it?”

“I love it. I don’t know if I will ever go back.”

Sarah nodded and confirmed, “It feels great. Especially for sex. Maybe you can go with us next time.”

Amanda nodded but looked hesitant.

Jenny shifted and spread her legs several times and even blatantly bent over at one point to make sure Amanda got a complete view of her bald snatch, keeping Amanda’s eyes riveted to the sight.

Thoroughly relaxed, they left together with Amanda thanking them profusely. Sarah told her how much fun she had hanging out with her over the weekend and said she hoped they could hang out more in the future. Amanda gave her a huge hug and agreed. As Sarah watched her drive off, she thought to herself, “The net is cast.”

+++++++++

They got to Mr. Michaels around 4:00pm. Sarah noticed immediately that he didn’t seem overly jovial, especially given how well she thought the sex had gone on Friday. She still felt such gratitude toward him for helping with the job and hated to see him less than happy. In an effort to lighten his mood, she launched into a de***********ion of their weekend with Amanda and how well it had gone. But he seemed to dismiss it as incidental.

He took them in the den. “Go ahead and take off your clothes. The both of you.”

The command actually relieved Sarah. “So we are going to have sex today,” she thought as she and Jenny started taking off articles of clothing. All of the recent sex and teasing had left her horny all weekend making her crave it all the more. Even the thought of maybe being with Amanda someday seemed exciting in a way. When they were nude, he ordered them both to get in their slave poses. Immediately dropping to their knees, they complied with their legs about a foot apart and their arms crossed at the elbow behind them. He had taught them this pose the last time they were together as part of their submissive training, and both were getting used to it. They awaited instructions patiently.

He left the room and came back with a drink. In no particular hurry, he sat down in the big easy chair about six feet in front of them and took a long slow swallow. “I have a new challenge for the two of you this week. Sarah, I want you to approach Conner and tell him you would like to have anal sex with him. In fact, you want to have a threesome with him and Jenny and that the two of you will both let him fuck you two in the ass.”

Sarah and Jenny were both surprised by this and somewhat afraid at the prospect. But loooking at each other, in became clear neither had the courage to say anything. If that is what their Master wanted, then no amount of protesting would get them out if.

After letting that sink in, he continued, “However, you are going to have a condition. Before he gets to fuck either of your asses, he has to agree to be pegged by you both.”

Still stunned speechless, they continued to look at each other and each could see the same confusion on the other’s face. Finally, Sarah ventured to say, “Sir, I….I mean I think we…I don’t think we know what that means.”

He frowned at each of them for a several long seconds making them both feel stupid. “You wear the strap-on dildo and fuck him in the ass first.”

Every time Sarah thought she had gotten a handle on her situation and had accepted it, he threw another curve ball and made it harder. But this seemed especially weird and difficult to achieve. She had never conceived of fucking a guy. Then she remembered she had just rimmed Mr. Michaels on Friday, so maybe ‘pegging’ a guy might not be the craziest thing in the world. The more she thought about it, the more intrigued she became. She liked the feeling of power that fucking Jenny with the strap-on gave her, so what would it be like to actually do that to a guy? Would that make him feel like a homosexual? Or a woman? Would it be enjoyable for him? Would it be better to fuck a guy than Jenny? All kinds of questions launched in her head as she processed this.

“What if he won’t let us do that though? What if he won’t agree?” Jenny asked.

“It’s up to Sarah to convince him. But if she can’t then he doesn’t get either of you and he doesn’t get to fuck you both in the ass.” He looked right at Sarah. “I will be very disappointed if Sarah can’t convince a horny teenage boy that he will get to have the wildest threesome probably of his whole life, and get to have anal sex with two gorgeous sluts, when all he has to do is take what he gives.” He paused for a pregnant moment and Sarah could feel his stare go right through her. “You won’t let me down, will you Sarah?”

She shook out of total fear. Entering the house so happy and horny changed so quickly to feeling only terror over the prospect of letting Mr. Michaels down, let alone what he had proposed. “No. Nooo sir. I promise. I won’t let you down. I’ll get him to do it sir. Master. Sir.” So flustered, she couldn’t think how to address him. Her cheeks flushed and she trembled a little.

He seemed pleased and nodded. He took another long slow drink before starting on a new topic. “I know the week after next is your spring break. I’ve arranged for a beach house down on Miami beach right in the heart of the spring break action. I want you to invite Amanda and five other friends to join you. Tell them that you got lucky with an Airbnb and you can all go for $300 apiece. You will collect it from them and give it to me. It will obviously cost a lot more than that, but I will cover the difference.” He let that sink in.

Both girls were astounded, and their mouths had dropped open. He continued, “There will be four bedrooms. You two will share the master bedroom. Let the other girls pair off as they would like. I will have extra clocks for you to set up around the house so I can watch the action. You will have to figure out how to do this discretely so nobody else knows. There will be other instructions once you get there. But for the most part, I expect you to have the senior blowout trip that everyone else will be envious of and to enjoy yourself. How does that sound?” He waited for their response.

Jenny and Sarah stared at each other and then back at him. Jenny recovered first, “Un-fucking-believable!” she almost screamed. And then nervously, “Unbelievable sir!” she corrected.

“Thank you sir!” Sarah exclaimed. She started to get up to thank him and kiss him, but he stopped her midway by holding up his hand. Quickly dropping back down into her pose, again shocked and unable to figure out how to respond, she felt lost and struggled to understand his demeanor. He always tempered good news with bad. Reward with challenge. Pain and pleasure. Everything with him remained a constant balancing act.

They both looked at him expectantly. His eyes just went back and forth between them. Eventually he said, “Come over here Jenny.”

She rose and went to him. He stood and she went back into pose standing with feet apart and arms crossed behind her. “Clothes,” he stated in a simple one word command. With only a slight hesitation and a half glance backward to Sarah, she moved to start taking off his clothes. Struggling to understand why she wasn’t helping, Sarah stayed quiet and in her kneeling position.

When Jenny had finished removing all his clothing, stacking it all neatly on the ottoman and returned to stand in front of him, he put a finger on her shoulder dropping her to her knees in front of him. She took his cock into her mouth and got him hard playing with it and licking it as she had been taught. He never took his eyes from Sarah. She kept waiting for him to call her over and join, but he didn’t.

As Jenny started working harder to try to make him cum, he stopped her, pulled her up, turned her around, bent her at the waist, spread her legs, and wiped a big amount of saliva on her pussy. He then, without any fanfare, pressed his dick into her waiting cunt. He penetrated slowly and deliberately, but never stopped or paused. He started fucking her harder and harder, grabbing her shoulder and pulling her too him. Jenny started moaning and clearly enjoyed it but did little other than try to keep her balance.

After a couple of minutes, he grabbed her by the waist enough to pull her off the ground without letting his dick leave her and sat back in the chair. He kept his legs between Jenny’s and spread her legs wide. Then he grabbed her waist and started thrusting up into her. She got into the rhythm and soon bounced up and down on his dick meeting his thrusts. She grabbed her tits and playing with her own nipples as she bounced and tossed her head from side to side getting into it.

Sarah still couldn’t figure out why he was only fucking Jenny and left her kneeling there. Her knees and back started to hurt from holding her position. She wanted to ask if she could join. She looked at him pleadingly and waited for any sort of signal from him.

Mr. Michaels bent Jenny forward a little and really got into screwing her. Jenny begged to cum, but got denied. He pulled her off of his dick, made her stand up on the chair and straddle his face. He proceeded to eat her out and tongue lash her clitoris. Grabbing his head, clearly in the throes of passion. Sarah could see him start to finger fuck her at the same time. Sarah’s pussy wept while she watched, and her envy grew with Jenny getting all the attention. She had never had to sit on the sidelines like this before.

Jenny wrapped her legs around his head and begged her Master for permission again, wailing as she pleaded. In one quick motion, Mr. Michaels stood up and Jenny’s body slide down his until she stood in front of him. Without a pause, her turned her, bent her at the waist sideways to him and spanked her a half dozen times with long roundhouse strokes. Both Jenny and Mr. Michaels were facing her, but Jenny’s eyes were closed while he looked straight at Sarah with an expression that made her want to shrink. He sat back down and put Jenny in the same position as before, reverse cowgirl with her legs straddling him and her pussy open. He started thrusting again and they went right back to hard core intercourse.

“Get over here and lick her pussy,” he ordered. Suddenly knocked out of her trance, Sarah jumped to obey. He pulled Jenny back some toward his chest, but never stopped thrusting up into her. Sarah reached forward and did her best to lick both his dick and her pussy. With their genitals bouncing up and down so quickly, it made it difficult to do. She eventually found it easier to just hold in one place while they banged into her tongue. Regardless of the effectiveness, the added touch had Jenny trembling again and she begged, “Please master, I can’t stop, this feels too good. Please may I cum?!” He finally consented and Jenny let out a yell and her body shook. Mr. Michaels never slowed down. Even after she had clearly past the intensity of the release, he continued to fuck her. Using her as a masturbation toy. It took several more minutes before he shoved Jenny off to the side, stood up and grabbed his cock in one hand.

Sarah moved to take him in her mouth, but he stopped her and continued to jerk his own cock. His groaning increased as did his tempo. As he prepared to cum, he grabbed Sarah’s head and jammed his dick into her mouth and released a torrent of jism. Now with both hands free, he grabbed her head with both hands and ground his cock back and forth while several more spurts filled her mouth. It happened so quickly, she didn’t have time to swallow and just held it all in her mouth. When he finished letting go of his semen, he pulled his dick from her mouth and turned to pick up Jenny.

Sarah swallowed the load in her mouth still completely confused by what had just happened. He used her mouth as a cum dump. He never touched her, didn’t include her in the sex, nor give her any enjoyment. She felt totally used in a way she had never felt before. Meanwhile, Mr. Michaels had picked Jenny up and gave her a big kiss and told her what a good job she had done.

Utter turmoil filled Sarah internally. Sick to her stomach, wanting to ask why he had treated her so badly, but kept quiet. He told the girls to get dressed and get going.

“So you have your instructions for this week. I want you both to try to get together with Conner on Wednesday. We will have our normal night on Thursday with the three of us.” He looked directly at Sarah. “Sarah, I am counting on you to get this done.”

“Yes sir,” she said meekly. When they were ready to head out, both girls moved forward to kiss him as their ritual went, but he kept it to just a quick peck instead of his usual deep tongue probing. Sarah could only shake her head as she walked out, ready to cry.

She and Jenny walked silently to the car. Jenny looked just as confused by the situation as Sarah felt. Sarah could tell Jenny wanted to comfort her, but had no idea what to say. When they got in the car, Sarah had tears in her eyes and slumped forward. Jenny patted her back trying to console her before finally turning to start the car. She got halfway down the driveway when Sarah insisted she stop. Before the car had fully stopped, she popped open the door and jumped out to run back to the house.

Mr. Michaels still sat in the den drinking his bourbon. He didn’t look surprised to see her, but he also didn’t yell.

“What did I do wrong? Why are you punishing me?”

“Why do you think I am punishing you?”

Sarah just stood there for a minute trying to figure out what to say. There were still tears rolling down her face. “You….you…ignored me. You….didn’t….didn’t….fuck me or touch me.” She tried to stifle a sob, unsuccessfully. “And then you just came in my mouth like that. Like…..like….like that was all I was good for.” Crying silently while waiting for some kind of explanation.

He remained very quiet for an agonizing period of time. Then he said in a very soft tone, “I’m not mad at you and I’m not punishing you.”

“But after Friday, I thought I had done such a good job. And I’ve followed all of my rules and did everything you said. So why would you only fuck her? Do you like her better or something?” Sarah’s insecurities had bubbled back to the top of mind. She loved Jenny but had always been jealous of her looks and her money and how easy everything came to her. And now it looked like Mr. Michaels wanted her more. She felt totally lost.

Mr. Michaels held out his hand and she went to him and took it. He pulled her to his lap and had her sit. “I’m not punishing you and nobody will ever replace you, Sarah. Tonight had nothing to do with that. Tonight was a reminder of what this is all about. This is not a love affair. You are my willing submissive. You do as I say, when I say, and I take care of you in return. There is so much you and I will do for one another, hopefully for a long time to come. But there are some things I can never be for you. I can’t be your boyfriend or your husband. We can’t have children together. And I would never rob you of those things. I don’t want you to fall in love with me. I told you when this started, you will have your own life. You and I will have many many private intimate moments, but I want you to flourish and find true love for yourself and that is not me. I will be your teacher and supporter and I will show you how to get the best out of life. That will include always being my submissive willing to do anything I tell you. You were getting confused, and I needed to make sure you understood this.”

He waited for a minute to let that her digest his explanation. She had stopped crying. “But what if I do want more with you?”

He shook his head. “No. It can’t be more than it is. That doesn’t mean it won’t be great. But it can’t be more. You will have to accept that.”

Sarah mulled his words around quietly. Eventually she started to nod. “I think I understand. But you aren’t angry with me? You’re not getting tired of me?”

Now he laughed, but in a light-hearted way. “No, definitely not tired of you. I don’t think I will ever tire of you!” He got more serious. “Nobody will ever replace you, Sarah. There will be others. You and I will have fun with all of them. And I will continue to punish you and scare you and challenge you. But hopefully make you cum the entire time.”

She ventured a small smile. “Promise?!” He laughed and hugged her and kissed her properly.

“Now get back to your friend. And don’t let me down this week! I’m counting on you!”

She got up and hugged him again. “I’ll come through for you. Promise. I’ll make you very proud of me.” She felt a world better. She thought she understood. She accepted it and ran out of the house without another word.

Jenny looked surprised at the turn around in Sarah as she bounced down the driveway to the car, with the hint of a small smile. “What did he say?” she asked.

“It’s good. I thought he was mad, but he wasn’t. I just have to accept that he is my Master and I am his submissive. I get it now.”

Jenny didn’t get it but didn’t question it anymore. Sarah saw the goofy look on Jenny’s face and knew the girl still suffered from being cum drunk. Sarah put the teaching moment with Mr. Michaels out of her mind and focused on the kick-ass spring break they were going to have. She and Jenny spent the rest of the drive trying to figure out who to invite.

+++++++++

After Mr. Michaels pep talk, Sarah felt more determined than ever to get Conner to agree. She found him early the next morning and told him she wanted to talk to him after school. Wanting someplace private, they agreed to talk in her car right after the last bell. Leaning in to tease him, she whispered, “I have an offer you are going to really love.”

They met at her car and waited until they were sure that no one else was around. He turned to her with clear lust in his eyes and asked, “What is this about? What offer?”

Sarah couldn’t quell her nervousness, but she had it planned out in her head. “Well, you know my friend Jenny, right?”

“Yeah of course.”

“Weeelllll… she and I were talking over the weekend. We were a little drunk and well, she and I want to have a threesome with you.”

His eyes bugged out. Sarah could see the wheels turning in his teenage brain. Every young man dreamed of a threesome with two hot girls. “Holy fuck, really?” Sarah just nodded with a coy look on her face. She could practically see the drool coming out of his mouth.

“There’s more.” Sarah tried to put on her best suggestive face. “She and I both want to try anal sex with you.” She tried to look embarrassed at even having said it and then realized that she didn’t need to act, feeling her cheeks blush.

Conner didn’t say anything for a minute, too stunned by her announcement to even breath. “Seriously? Both of you?” He considered. “Is this some sort of joke?”

“No joke. You get both of us. You can fuck us both. And we will both blow you. But then, you get to have anal sex with both of us. We’ve both wanted to try it and I told her how good you are in bed and how good you are at keeping secrets.” She emphasized the ‘secrets’.

Conner was blown away. He sat back shaking his head with a Cheshire cat grin. But Sarah watched the grin slowly turn to a frown as his skepticism seeped in. “What’s the catch? You always have a catch.”

Sarah nodded. He knew her too well. This was the make-or-break moment. “She and I have had sex before.” She looked at him to gauge his reaction. He seemed surprised. “We use a strap-on and fuck each other. You can watch us do that to. Would you like that?”

“Fuck yeah. Of course, why wouldn’t I?” The big grin returned.

“It is really hot. We like the feeling of fucking like we have a penis and it feels amazing. She and I cum like crazy.” She had Conner practically salivating while she described it. She had him right where she wanted him. “So you get to fuck us both in the ass.” She paused and got up her courage for the next statement. “But we get to fuck you in the ass first with the strap on.”

Conner’s face crashed. “What the fuck are you talking about? NO FUCKING WAY!” He shook his head, slowly at first and then with more determination. “I knew you were a crazy bitch. A fucking slut. But this is nuts! No fucking way!” He pursed his lips tightly and crossed his arms like a resolute statue. “Nuh uh. No fucking way. Fuck me in the ass? No. Not going to happen.” He even started to reach to open the door.

She grabbed his arm. “Hold on. Hear me out. I want you think about this.” He stopped trying to leave and looked at her with crazy mad eyes. Finally, he let out a huge sigh and relented enough to let her talk.

“I want you to imagine, Jenny and I both on our knees sucking your dick at the same time. She is fucking hot Conner. You know that. You can tell us to do anything you want. We will lick each other’s pussies right in front of you. You’d like that wouldn’t you?”

He considered and rocked his head from side to side. “Well yeah, of course.”

“Have you ever had two girls suck your cock at the same time? Taking turns going up and down on your fat dick?”

“No.”

“You know it would be insanely sexy. And you can put us side by side and take turns fucking her pussy and then mine. You’d like that wouldn’t you?

“Well yeah.”

“What else would you like? Have you ever had one girl fuck you while the other girl sat on your face. Or fucked a girl from behind while she was eating cunt right in front of you?” Sarah needed Conner to see it. To picture everything that could happen.

Staring off in front of him, he clearly started getting a full mental image. “Yeah, fucking you while you were eating her out would be hot…” he said dreamily.

“Have you ever fucked a girl in the ass Conner?”

He looked at her with bravado that soon evaporated, and finally admitted, “I tried once with Sloan, but she said it hurt and made me stop right away.”

Sarah had hoped it would be something like that. “She and I won’t make you stop. We will take it all the way. And it is going to feel amazing. Very different from a pussy.” She really had no idea of course, but she needed him to want it more than anything. Forbidden fruit.

“Yeah, but I’m not gay. I don’t want anything up my ass.”

“Wait, so you think it is okay for a girl to have to take it up the ass, but your ass is off limits? Having something in your ass doesn’t make you gay. It makes you cum extra hard. Have you ever cum with something in your ass?”

“No,” he said defensively.

“Don’t be stupid Conner. Something in your ass doesn’t make you gay. If girls can like a little anal play, then why can’t it also feel good for a guy? I’m not asking you to fuck a ‘guy’! This is a threesome with TWO GIRLS! How is that gay?”

He started getting defensive. “Well it’s not I guess, but it just sounds weird. Why do you want to fuck me in the ass?”

“Why do YOU want to fuck ME in the ass?!” she accused. “How is it okay for you to ask it of me and not be willing to try it yourself. What kind of hypocritical bullshit is that?” She shook her head trying to look amazed at his stupidity. “I mean, think about what I am offering. A threesome. Two girls willing to do anything. Willing to let you stick your prick ANYWHERE you want. Do you honestly think something like this will ever come along again? You just hit the fucking lottery and you are arguing with me on a little dildo in your ass. Maybe you are too fucking stupid for this. There are a hundred guys in the school that would jump at this chance. Maybe I’ll just get one of them.” Now Sarah had her arms crossed and shook her head with a sour puss on her face.

Conner rolled his eyes. He sat back and sighed again. “What if someone found out?” as his only retort.

Sarah kept the frown on her face, but she smiled inside. She had him. He would go for it. “Find out? Who the fuck is going to find out? Has anyone ‘found out’ about the gang bang? Remember that? Did I not come through for you taking on THREE guys? How many times did you fuck me that night? How many different ways? Who would have been hurt if that got out?! You? NO! Me. That’s who. But I still did that for you, didn’t I. You think Jenny or I are going to spread it around that we had a threesome with you AND let you fuck both of our asses?” She shook her head again. “Fucking think.”

He got quiet having no idea what to say. She could tell he wanted it and was internally trying to rationalize it. But she needed him to commit before he had too much time to think about it.

“Offer is on the table for exactly ten more seconds. If not, then fuck you and you and I are through. You’ll never fuck me again.” There it was. She had played all of her cards. Actually, she felt very proud of herself. Controlled the situation perfectly she thought. Now she just had to wait for the fish to really take the bait.

“When?”

Sarah softened. She looked excited and smiled at him, knowing she had him. He had agreed. “How about Wednesday at my house?”

“What if I agreed not to fuck you in the ass? What if we just did, you know, normal sex with the three of us?” he bargained.

She shook her head slowly. “It’s all or nothing Conner. One time deal. Take it or leave it.”

He struggled with himself and shook his head. “Fine. But you better use lots of lube. And nothing too crazy.”

“We will be very gentle and go slow. Just like you will be for us, right? Just think about Jenny sucking your dick while I fuck your ass. I can promise you, you will cum harder than you ever have.” Quickly slipping back into a seductive tone, she needed to rev him up again now that he had climbed on board.

She continued laying it on thick, “And Conner. I want you to be thinking about how you want Jenny and I. Like I said, we will do anything you want and fuck you anyway you want. No complaint. That’s pretty amazing, isn’t it? Your every fantasy?”

He continued to shake his head. “You are such a slut Sarah. I’m not sure if I am happy I met you or if I regret it. But you are really fucking sexy.”

She reached over and kissed him hard. “I’m your slut Conner. And Jenny will be your slut. You’ll see. It will be the most amazing time you have ever had.”

“Okay. Wednesday. Your place. Right after school.” He got out of the car and left without looking back. Sarah sat back and let out a huge breath. Mr. Michaels would be pleased with her.

+++++++++

Sarah of course informed Mr. Michaels that she had succeeded. His confirmation at being pleased with her efforts made her feel good. Jenny had focused on the spring break trip. She got Amanda and Samantha to agree first. Then found four other girls that were more than happy to join them. Two of them even had to cancel other plans, but the thought of having a beach house right on Miami beach was just too good to pass up. All of the girls were amazed at the deal and readily gave Jenny the money. By Wednesday, they let their Master know they had completed their other task as well.

Sarah picked up two sets of strap-on dildos from Mr. Michaels for the event. As the time approached, both Sarah and Jenny were excited and anxious to carry out the plan. Sarah got more and more turned on at the thought of fucking Conner. The sense of power she knew she would feel became her masturbatorial focus for the days leading up to the event.

Conner showed up at her house. He seemed reserved and nervous, but perked up when he saw Jenny waiting inside. Both girls had on sexy outfits. Sarah grabbed Jenny and kissed her hard and grabbed her ass and then looked at Conner and said, “We are going to rock your world Conner.” His reservations dropped and were replaced with lust.

With little other preamble, they headed straight upstairs. Sarah had even moved the clock-camera from the bathroom into her room to make sure all of the action would be covered. They sat Conner on the edge of the bed and stood in front of him in each other’s arms. “What do you want first Conner?”

He licked his lips. “Take each other’s clothes off.”

The girls started taking off each other’s tops. Taking turns and playing it up. Each girl covered their breasts as best they could until they both turned to him and made the big reveal. They stood in front of him and played with their tits and took turns sucking and licking each other’s nipples. Sarah bit Jenny’s nipple between her teeth so Conner could see it and pulled back until it hurt. They slid down each other’s shorts and thongs, bending over like strippers and kissing and licking each other’s asses. Conner’s eyes were saucers at the sexy display. And they showed off their completely bare pussies.

“Sarah, lick her pussy,” he commanded. Sarah dropped to her knees and drew Jenny’s pussy lips wide apart and slowly licked her whole slit. Jenny cooed and moaned loudly. He had them come over and he touched and played with them both and fingered each one. Together they took off his clothes. His member stood at full attention sticking straight up in the air as only a teenage boy could achieve. Unsurprising to Sarah, he demanded a dual blow job. She knew he probably wanted that the most of all while describing what they would do in the car.

Sarah made sure that he faced right toward a camera. Using the same technique they used for Mr. Michaels, with no hands and just mouths at first with his shaft held between their lips on each side. Followed by taking turns popping his dick into one mouth while the other girl licked all over including his balls. Within minutes, the dual action had him shaking and moaning to the point that Sarah feared he might pop already. She clutched his dick hard until he slowed down telling him they still had too much playing to do to blow his load early.

Getting on the bed in a 69, he watched their tongues work up and down and into each other. But he soon got restless and pulled Jenny around on her hands and knees, put a condom on and sunk his throbbing prick into some strange pussy. Jenny kept her face in Sarah’s crotch and Sarah moaned loudly. She knew that a good show would get Conner to lose it and he soon grunted and ground his erupted cock into Jenny’s pussy.

While he ran to get rid of the condom, Sarah put on a strap-on with Jenny’s help. He had returned quickly before they had finished and paled at the site of it knowing what Sarah would want next. But she made sure Conner saw the bigger dildo go into her pussy with the thinner longer side sticking out through the harness whole. Conner looked unsure but warmed right back up when Sarah started fucking Jenny. She slammed into her forcefully in missionary and they rubbed their tits together while they kissed.

Conner’s raging boner returned quickly when Sarah flipped Jenny over and split her ass cheeks wide open and tongued her asshole. Jenny squealed and her body shook at the welcome intrusion. Sarah made a show of running lube down her ass crack and sliding her fingers in and out of Jenny’s ass. Jenny moaned loudly telling Sarah how good it felt and how wet it made her. Then she applied a ton of lube to the phallus and got into position behind Jenny. Sarah went very slow and gently worked the cock head into her ass.

The girls had choreographed this part to show Conner both how gentle it would be and how much Jenny loved it. When the cock made it past her anal ring with a small pop, she made an appreciative groan and told Sarah how good it felt. She eased it in over several minutes. Jenny totally got into it and soon moaned loudly encouraging Sarah to fuck her ‘sweet ass’. Jenny practically ordered Conner over to her and made him lay in front of her and then took his swollen pecker deep into her mouth and stroked it hard. Within a minute, his balls were already starting to churn. Sarah pulled Jenny up on her knees and spread her legs wide while she kept fucking her ass. She handed the vibrator to Conner and told him to help get Jenny off. He moved to get access under her and rubbed the vibrator all over her pussy and clit and before long Jenny had a huge orgasm, shaking and gasping for breath begging Sarah to keep fucking her ass. Conner watched from his vantage point mesmerized.

When Jenny finally calmed down, Sarah pulled out of her. She told Conner to take her place. He took a deep breath. “Come on big boy, time to pay the piper” she said in a sexy drawl. His reservations were obvious. Once on his hands and knees, Sarah got a pillow to get to the right height. Jenny kissed him and reached under him to stroke his cock. Sarah got a generous amount of lube on her hand and warmed it for a minute. Then she reached between his butt cheeks and ran her fingers over his butt hole. Conner immediately clenched.

“I promise you are going to enjoy this more than you can know,” Sarah said trying to sooth him.

Jenny offered, “You just saw me. It was amazing. I came twice as hard. And I’m going to suck on your cock while she is fucking you and you are going to cum twice as hard in my mouth.” That relaxed him a lot, but he clearly still felt nervous.

“I’ll go even slower than I did with Jenny. The key is to breath out and not clench. Try to push out like you are trying to have to go. Feel yourself open up and accept it instead of fight it,” Sarah instructed. With that, she slid a finger into his puckered hole. He clenched immediately at first, but started to relax. Jenny working his cock, distracting him to help him relax. Sliding a second finger in, it went in a little easier. She applied more lube and started to pull her fingers apart to open him up further. He groaned but tried to stay loose.

“Of fuck, your cock is like granite Conner. It feels so good. I can’t wait to take this in my mouth. Just don’t cum too fast. I want to make this last,” Jenny encouraged.

Sarah thought they had gotten him as ready as he would ever be and got into position. Running the head of the toy up and down his crack before pressing it lightly on his asshole. She rubbed more lube all over it and then pressed it right against his brownie, getting the head to just crest and making him let out a bigger moan. Going very slowly pressing steadily, she could tell his anal ring had stretched to the point where it would either clench and squeeze it out or let the intruder in. She pressed a little more using her hand to guide the floppy faux pecker into his virgin asshole. It took a lot more effort than getting into Jenny for sure. But it finally popped in and he let out a deep yowl.

She glided it in slowly making his ass surrender to her. Loving the feel of it. Of controlling this arrogant man child. She got halfway in and then pulled back before pressing in again going a little deeper. He moaned at her trusting but went with it and even pushed back. Jenny got under him and started taking him into her mouth. Sarah could tell the awkward position made it difficult for her to do, but she took long stokes with her mouth and hand.

Conner started to shake and groaned loudly. Afraid he would cum too quickly and spoil their fun, she slapped his ass hard. “Don’t cum yet you little bitch.” She slapped his ass again and kept fucking him. He continued to groan. “Do you like being my little cock slut? Tell me you are my cock slut!” Sarah didn’t even know where the words came from. Just getting lost in the moment and the control, the words formed on their own.

She slapped his ass again hard. “Tell me or you don’t get to cum. Tell me you are my cock slut or you don’t get my ass!” She slammed into him harder and as deep as she could go. His body shook more violently and he strained. Jenny fondled his balls and still bobbing her head as much as she could right over his cock head.

“I’m you cock slut!” he screamed and then released everything in his balls. Sarah could see Jenny slurping up his cum. She grabbed his waist and pushed as deep as she could and held it there, grinding from side to side. Conner’s hips continued to clench and unclench and his body trembled. He grunted and let go with a few expletives barely keeping his balance. With a loud release of air he had been holding, his body relaxed and Sarah knew he had finished cumming, hearing Jenny slurp up the last of his spent member. Bending to the side, she watched Jenny lap the few remnants from the shaft of his dick. The two girls shared a moment smiling with raised their eyebrows at each other.

“Oh shit did that boy cum. That was like a gallon of spunk. I thought I was going to drown,” Jenny stated in celebration.

Conner fell forward on to the bed. His gapped asshole tried to pucker to close. He never stopped groaning. Sarah went into the bathroom and started to remove the strap-on. She hadn’t cum, but her pussy had gotten so soaked that the larger dildo pulled out easily. Working quickly, she cleaned both sides of the toy.

When she got back to the bedroom, Jenny had laid down against Conner and he had a big smile to Sarah’s surprise. “Holy shit, that was the biggest orgasm of my life!” he exclaimed. “I mean it hurt like hell, but Jesus did I cum forever.”

Sarah told them she would be right back and ran downstairs to grab some beers. Jenny and Conner were kissing and he was fondling her tits when Sarah got back. They all had a drink and a moment of quiet reflection. Then Jenny announced that Sarah needed a turn since she hadn’t cum yet. Conner got between her legs and started to lick her pussy and Jenny sat on her face. After a few minutes, Jenny got off Sarah and put on her strap on. She took Conner’s place and turned Sarah to the side and fucked her from the side while holding the vibrator on her clit. Sarah rested her head on the inside of Conner’s thigh and played with his still soft dick.

By the time Conner started to get hard again, Sarah had reached the brink of orgasm. Out of pure habit and now deep training, she popped his dick out of her mouth and begged Jenny for permission to cum. She avoided saying “Master”, but barely. Jenny told her to cum and Sarah moaned and jammed Conner’s cock as deep into her mouth as she could take it. Feeling that cock start to gag her made her orgasm shake her body. Watching all of this and hearing Sarah beg like that had made him fully hard again.

Conner wanted to fuck Sarah in the ass, but she told him that Jenny still had to fuck him first. He didn’t look happy but didn’t object as much as the first time. When he started to get on all fours again, Jenny stopped him, making him lay on his back instead. He seemed even more unsure about this as she grabbed his legs and pushed them back, but he surrendered with all fight over the situation lost. While Jenny held his legs back, Sarah applied more lube to both Conner and the dildo.

Jenny pressed the dildo up against him and his ass opened for her. She slowly stuck it in and rolled his hips back farther, lifting his ass and making the entry angle easier. Making him groan again loudly at the insertion. When she had fully entered him, Sarah played with his balls and stroked up and down his shaft with her hand. He stayed only semi hard as his ass took the beating, but he clearly loved the feel of Sarah’s hands on him. Jenny picked up the tempo and soon had the fake penis drilling him. Both girls commented on how good he looked with a dick in him. Pre-cum leaked everywhere. Sarah would occasionally reach down with her mouth and suck on him or lick him. The treatment continued for a while until Conner got back up to full a full erection.

Sarah then instructed Jenny to lay down on the bed. She had Conner straddle her in a reverse position and guided the dildo into his ass. Once it had seated fully in place, she slid a condom on Conner’s erection and straddled him, lowering her pussy onto him. Soon all three bodies were connected in a weird chain and they bounced up and down, each feeling deep penetration. Sarah had to be careful not to crush poor Jenny on the bottom.

They switched again and Sarah proclaimed Conner should get his reward. Laying down on her stomach, she gave Conner permission to fuck her ass. She held her ass cheeks open while he soaked her back side with lube. Jenny applied it to his condom covered cock and then helped him by holding it to her friend’s asshole. Sarah reminded Conner that she had gone slow with him. He pushed forward timidly and backed off a couple of times trying to use what he had learned. Eventually popping past her ring and groaned as much as Sarah. The tight grip of her ass felt wonderful and he told her so repeatedly.

Sarah commanded him to lay forward on her and then told Jenny to fuck his ass at the same time. Again, the awkward position only allowed them to work at the triple fucking for a short time, but for several minutes, all three bodies were being penetrated. They all moaned with a combined pleasure. When they had had enough, Jenny pulled out of Conner and Conner pulled Sarah up on her knees before proceeding to fuck her with more intensity. Jenny pulled off her strap on and got under Sarah allowing Sarah to concentrate on eating her pussy. She tickled Jenny’s g-spot as Conner continually shoved her face into Jenny’s pussy while he fucked her harder. Jenny came again from Sarah’s expert service and before long, Conner came in Sarah’s ass.

They were all getting tired and sore, but the girls had promised Conner a chance at both their asses so he was due a turn with Jenny. Taking a short rest, Conner lay down and the girls nestled up to him on either side. Conner looked like the cat that ate the canary.

“So how was it getting pegged for the first time?” Sarah asked, actually very interested in his answer.

“Is that what it is called?”

“Yeah, I think when a guy gets fucked by a girl with a strap on, it is called getting pegged.”

“Well,” he considered, “I can’t say I’d want to do it all the time, but it was a lot better than I expected. And that first nut was amazing. I’ve never cum that hard.”

“How about fucking a girl in the ass for the first time?” Sarah continued and then giggled, “I mean the first time successfully.”

“Your ass is so tight. I thought I was going to bust right away. It felt unbelievable.”

Jenny chimed in, “So was it worth it? Would you do it again?”

“Fuck, to get you two angels again, fuck yeah I would.” He kissed one and then the other. They relaxed and the girls ran their fingers over his mostly bare chest. After five or ten minutes, their hands met down at this cock and Conner got treated to both girls slowly fondling and stroking him. Thanks to the miracle of teenage vigor, his body responded, and his pecker started to get hard again.

The girls kissed and played with each other’s tits right over his face, taking turns suckling on each other’s nipples. They next took turns dangling a breast down to his face. Sarah held Jenny’s mammary and traced his lips with the erect nipple. Then Sarah cupped her own breast and fed it to him.

Jenny asked how he wanted her. He had her lay down. Sarah put another condom on his well worn wood and rubbed the tip over Jenny’s pussy. Jenny remained plenty wet and Conner sunk into her easily. Sarah rubbed her friend’s clit and kissed her while Conner built up some steam. He pulled Jenny’s legs up to his shoulders and started fucking her harder and deeper. Sarah reached around Conner and fondled his balls while he fucked her friend. Fully excited, Conner pulled back and Sarah worked quickly to lube both of the other participants. Then she guided the dick back to the puckered hole and he thrust into Jenny. Jenny had to tell him to go slow for a minute and then he got deep enough to start fucking in earnest. Jenny groaned and rolled her head from side to side lost in the moment.

Sarah got the vibrator and worked it over Jenny’s pussy and clit while also pinching Jenny’s nipple. It only took three minutes or so before both Jenny and Conner were succumbing to their respective orgasms. Conner just grunted, but Jenny let out a pretty good scream and she shook again. The vibrator made her clit over-stimulated and she squirmed to get away. Conner’s dick popped out of her ass and dangled down, the condom threatening to fall off. Sarah grabbed it for him and went to the bathroom to dispose of it. When she got back, the two were kissing again.

For the second time in a week, Sarah felt a little like the second fiddle. But she didn’t mind nearly as much this time. She liked the group play and enjoyed watching the other two get off as much as she liked getting off herself. She glanced at the clock and winked, but also noticed they had been at it for almost an hour and half. The three fell back on the bed, this time with Jenny in the middle.

“Four orgasms for you Conner. Not a bad deal, huh?” teased Sarah.

“You drive me crazy, but I have to admit you are one insane slut. Between this and the gang bang, my mind is just blown. I never would have thought any of this of you,” he mussed.

Jenny perked up immediately to this, “Gang bang?! What the fuck are you talking about?”

Sarah rolled her eyes. “So much for keeping a secret, Conner, you asshole. Jenny, I’ll tell you the whole story later. Promise babe.” And Sarah kissed her quiet.

“Sorry Sarah. My bad. I just figured she knew,” Conner said defensively.

“Okay peeps. We gotta end this party and get cleaned up. Rents get home soon.” They started to pick up all the evidence and got dressed. Conner gave them both a kiss and told them he would see them at school. Sarah reminded him that this was a secret that he for sure did not want to get out. He promised he didn’t need reminding.

Once he had gone, Jenny turned to Sarah and said, “Well that was interesting!” They both broke out in laughter. “Now tell me about the gang bang.” Sarah went on to explain everything that had happened.
2 comments

FantasticgirlLReport 

2023-05-21 08:59:48
Wow some times you wish you are the upperhand and have once the control as submissive. I liked that part to peg Conner was fun and read that he enjoyed it the little bitch

boober70Report 

2022-10-17 14:14:26
Exploring Sarah's dominant side again.
Hey if you expect to fuck someone in the ass then you gonna have to be expect for it to be reciprocated.
Quid Pro Quo etc.
Thanks

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