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Introduction:

Summary: Alison has her night with Jimmie, but fails to follow instructions completely. The girls get freshly waxed to Ali’s chagrin. Sarah goes on a date with Jimmie, seducing him into getting pegged, before enlisting him to help set up the prom plans for the orgy. Ali goes to Mr. Michaels to pop her anal cherry and then gets introduced to the sex dungeon and the power of the Sybian. She also receives several daunting punishments for her failure to follow instructions with Jimmie.

This is a 28 chapter long form story. If you are finding this for the first time, I would encourage you to go back and read from Chapter 1 to get the most enjoyment from the overall story. Enjoy!



Feeling tired when she got to school the next day, after the long week with a lot of strenuous sex and more alcohol than her norm, Sarah found herself fighting droopy eyes during the first several classes. She ran into Ali after math class who looked anything put tired, acting and looking instead very nervous.

She pulled Sarah to the side and spoke quickly since they only had a few minutes. “You know I’m supposed to get together with Jimmie tonight, right?”

“Yeah. Is there a problem? Do you need help with a place?” Sarah asked soothingly, tried to calm her friend.

“No. No. He’s coming over to my place like Mr. Michaels wanted. My parents are going out with some friends and they aren’t supposed to be back until late. So that should be fine. But… but, look what I got when I woke up this morning.”

She handed Sarah her phone. Mr. Michaels had sent a text, “You are to fuck Jimmie in at least five different positions, but you are not allowed to have an orgasm. And make sure he wears a condom at all times while fucking you. When you get him off from fucking, get his condom off and let him cum on your tits and then use your fingers to lick it all up in clear view of Jimmie and the camera. When you blow him, let him cum in your mouth and this time SWALLOW IT ALL!. Jimmie is not allowed to eat your pussy or touch your ass.”

Sarah handed the phone back to her. “Just don’t forget to delete that text and I would do it soon.”

Ali stood shocked with her mouth dropped open. “That’s all you have to say?! Seriously? Did you see that? How am I going to do all that? How am I going to…” She stopped and looked around, lowering her voice after realizing she had raised it too loud. “How am I going to fuck him and NOT have an orgasm? I don’t think I can do that, Sarah?”

Sarah hugged her and tried to comfort her for a minute. “Relax! You can do this. Just stay in control. You fuck him more than letting him fuck you. And if it gets to be too much, stop for a minute.” Sarah took a second to look around and make sure nobody could hear them. “And if it really gets intense, pinch your nipples really hard. Or slap your pussy. And I mean hard, right on the clit. Pain will slow you down. Whenever you get too excited or really sensitive, feeling pain will stop it and let you reset.”

“What the fuck? Really?”

“Yeah, really. Believe me, I’ve done it plenty. Try it tonight before he comes over. Get yourself close and then pinch your nipple and see how it will get you back under control.”

Ali shook her head. “I still can’t believe I’m doing this. And then I still have to use that giant butt plug after he leaves. Then the waxing tomorrow.” Looking dejected and about ready to cry, her voice hitched as she continued, “And then he is going to fuck my ass…”

Sarah grabbed her shoulders and shook her. “Ali, calm the fuck down. It really isn’t that bad. You will have fun having sex with Jimmie. He is a nice guy. And you have to trust me that it won’t be that bad with Mr. Michaels. I was terrified, but I actually liked it. All the training this week will make it much easier and he knows what he is doing. Now stop worrying, take it one thing at a time.” Taking a deep breath, Ali tried to smile before Sarah continued, “First things first, delete that text. And go into the recently deleted folder and delete it there too like he showed you. Don’t get in trouble for that to make everything worse.” Sarah gave her another big hug. “We’re late. Get to class.” Still Sarah waited to make sure Ali had regained her composure before running to get to her class on time.

+++++++++

As expected, Ali called later that night. Sarah had gone out with Jenny and Amanda and they were back at Jenny’s place watching a movie. They were giving each other backrubs while watching and Sarah wondered if it would turn into something more before the end of the night. Excusing herself, she left them on the couch and walked into the other room.

“So how did it go?”

“Pretty good. Jimmie is a nice guy. We got pizza and came back here. I was so nervous. We kissed and he played with my tits. And then we got naked. He has a really nice body and a pretty big dick. I told him I wanted to fuck first and then I would give him a blow job. He was good with that obviously. He tried to go down on me, but I told him I didn’t want to do that. He thought he had done something wrong, but I grabbed his dick and jerked him for a few minutes and he stopped worrying!” She chuckled at her own joke, making Sarah join her with a giggle.

“Once his dick got really hard, I put a condom on him. I was terrible at it and we both laughed, but I finally got it on and I got up on top of him and started fucking him. It felt so good Sarah! But he started rubbing my clit at the same time and I almost forgot and had an orgasm. Then I remembered what you said and I pinched my nipples. At first, it just made it worse, but I pinched really hard and twisted them. I see what you mean now. As soon as it hurt, it stopped me.”

“See?! I told you. It can help you control yourself.”

“He asked what I was doing. I told him that I didn’t want to cum too fast and wanted to enjoy his wonderful cock more. He seemed really confused but didn’t argue. So we did that for a while and then I stopped and told him I wanted him to fuck me doggy style. That almost did me in as well, but I told him to spank me. He did it really light and I had to practically yell at him to hit me harder. I felt like a total slut but that worked as well. I think next was sideways. And then after that was the one where I was on top, but not facing him. What’s that called again?”

“Reverse cowgirl.”

“Yeah, reverse cowgirl. That is such a weird name. But Sarah, that is when I fucked up.”

“You had an orgasm, didn’t you.” Sarah unconsciously shook her head, but didn’t say anything more.

“Yeah. I tried to stop, but I just couldn’t. And I couldn’t hide it. I was facing right at the camera. And I didn’t just come once. Once it started, I came like three times. Even the nipple thing didn’t work.”

“Okay. So go on.”

“So we finished normal.”

“Missionary. Learn the right terms,” Sarah chided.

“Yeah, missionary. I really liked that. He put my legs on his shoulders and got sooo deep. I had another orgasm that way too. Then he started fucking faster and I had to remind him I wanted him to cum on my tits. He just kept saying, ‘Really? Are you sure?’. Then he grunted and I had to practically yank his dick out of me and the rubber came off with a snap. But I got under him and jerked as fast as I could and…Oh…My…God...did that boy CUM!”

They laughed for a minute and she continued. “So he blows his load all over me. And I mean it went everywhere. I got some on my face, some in my hair. I think one glob even went over my head. But then he also got a bunch on my tits and stomach. He came for like forever. And then when he finally finished, I pulled him up a little and kissed the head of his dick and then squeezed out one last drop and licked it off. His eyes got huge while he watched me. It was kind of erotic really.”

The big sigh that followed clearly indicated she was enjoying the memory. “So I still have his spunk all over. I told him to sit and watch me. And then I started to run my fingers through it and sucked it off of them. I don’t know if I will ever really get used to the taste. It took a couple of minutes and I felt kinda dirty doing it, but he really seemed entertained watching me. And I made sure to kinda looked toward the camera every once in a while. So I think I did it right.”

“Sounds like a good job to me.”

“So how do you get cum out of your hair anyway? It was like a total mess. I tried to wash it out after in the bathroom, but it was so sticky.” She didn’t really wait for a response and Sarah’s prompting to continue got her back to the story.

“So we took a break and got something to drink and then made out for a while. He got hard again pretty quickly. Then I told him I wanted to blow him. I kneeled down in front of him and did everything you showed me. I played with him and looked up and told him what a great cock he had. He got totally rock hard again. So it took like ten minutes and then he grabbed my head and blew his wad in my mouth. I had to push back on him so he didn’t jab the thing too far into my throat. And he just kept cumming, but I managed to keep gulping it down. I thought he might drown me, but he finally finished and I still had a mouthful, so I pulled off and showed him and then swallowed it.”

“Damn!! I’m impressed girl. You are a true cocksucking ho! So it went okay overall?”

She laughed. “Yeah. It actually was a lot of fun. I really like sex and I like the feel of dick inside of me. But am I going to be in trouble with Mr. Michaels? I mean, is he going to punish me for having orgasms? He told me not to, but I couldn’t help myself.”

Sarah sighed. She didn’t want to lie to the girl. “Look, you did most of it the way he wanted. There probably will be some sort of punishment for failing, but it probably won’t be that bad.” She waited knowing the thoughts running through Ali’s head and felt sympathetic. Having been in that same spot many times, she knew how demanding he could be and he expected perfect compliance. Breaking the silence, she asked, “How about the training. Have you used the big plug yet?”

“It’s in my ass right now. That hurt like a bitch going in. And it is harder to take out than I thought it would be. It feels like it is pulling my asshole out of my body. But it is getting easier with each try.”

“Good. It really will help. Just keep adding more lube and take your time.” She waited a second to see if there was anything else. “Listen, get some rest and we’ll pick you up for our appointment in the morning. Don’t worry about it. But call if you need anything. Jenny and I are here for you.”

“Thanks Sarah. See you tomorrow I guess,” she finished somewhat disheartened.

Jenny and Amanda were making out on the couch when she returned. Jenny stopped long enough to inquire about Ali and Sarah shrugged and told her she seemed fine and she would fill her in later before leaning in to kiss Amanda herself.

+++++++++

Ali looked white as a ghost when they picked her up. They reassured her that it would hurt, but not be as bad as she feared and they would be in it together. That helped Ali, but Sarah could see her shaking a little. Sarah went in first. It did get easier with each waxing and she soon looked down at her freshly bald genitals and admired how she looked.

Jenny went next. When she came out, Ali balked as the aesthetician called her name. Sarah asked if it would be okay if she and Jenny went with her and the technician nodded. Taking turns, Sarah and Jenny reassured her while Ali took off her shorts and underwear and got on the table. She had trimmed her hair short like Sarah had told her to do. Sarah took one hand and Jenny took the other. The aesthetician set her legs bent and apart in a butterfly position and rubbed oil into the area to be waxed.

“Just relax. Remember to breath,” Sarah advised.

After applying the wax, the technician pressed a cloth strip into it. Ali took several deep breaths and the cloth got ripped in a quick jerk, making her give a little yelp and causing a tear to roll down her face.

“See, not that bad. It will be over in no time. Just don’t tense and look at me,” Jenny consoled. “And remember, the first time is the worst. It gets easier each time.” When Ali’s eyes popped open staring wildly at her, Jenny realized that she probably shouldn’t have said the last.

The second rip still got a big grunt from Ali, but she seemed better knowing what to expect. A couple more finished the top. The aesthetician put her leg up on her shoulder and went in for the sides. The sides brought a few more tears and some whimpers. Then Ali grabbed both knees and pulled her legs up to her chest rolling her ass up off the table. The hot wax around her asshole made her jump. With the final rips finished, the aesthetician rubbed some lotion onto the tender skin and left the room.

“Fuck that hurt,” Ali said stretched back out on the table.

“Yeah, but now it’s over and it looks fantastic. You have a beautiful pussy, Ali. Come look in the mirror.” Helping Ali off the table, the other two took her over to the big full-length mirror on the side of the room. Ali looked at herself and then spread her legs.

Sarah dropped her shorts and Jenny followed suit. Neither had put underwear back on and had on loose fitting shorts. The three girls all stood in front the mirror and admired their freshly waxed private areas. Sarah took out her phone and got a picture and sent it to Mr. Michaels. She added, “Bald and ready for fucking! Three sluts, no waiting.” She showed the others and they all laughed.

Noticeably more cheered as they left the office, Ali commented. “It feels so weird. The air on my skin feels tingly.”

“I told you it isn’t all bad. It feels good and the skin will be so smooth for a while,” Sarah answered.

Jenny added, “Really, now that I’m used to it, I like it better.” She giggled and continued, “Which I’m sure means that if I like it this way, he’ll be telling us to grow out giant hairy bushes soon.” All three laughed hysterically on the way back to their car.

+++++++++

While Sarah got ready for her date with Jimmie, she talked to the camera in her bathroom like she knew that Mr. Michaels was watching. In reality, she had no idea. She didn’t know how much he checked in on her. But she assumed that the cameras were motion sensitive and he could scan through quickly if he wanted to look for interesting action. Showing off her clean smooth pussy, she spread her labia wide in a close up and fingered her clit while thanking him for her hairless sexy pussy. The light touch as she circled her growing button made her pussy instantly wet.

“I wish it was going to be your dick enjoying this pussy tonight. You have turned me into such a wanton slut. I think about fucking you all the time. And taking that big cock of yours deep into my mouth. I can’t wait to gag myself on it again soon sir.” Sarah rubbed harder before stopping and feeling the edges of orgasm wanting to be let loose. She loved being right on the edge and feeling the energy course through her.

Feeling sexually charged, she finished getting ready. Luckily, her parents were going out and she planned on bringing Jimmie back right after they got a quick dinner. Her sister would be home, but they kept secrets for each other and got along well, so she felt sure it would work fine. They were going to Chico’s for tacos. Sarah loved Mexican food and she had picked it for their date.

While applying the final touches to her makeup, she heard the doorbell. Not wanting to subject Jimmie to too many questions from her father, she finished quickly and checked herself. Sexy, but nothing too risqué to get looks from her parents. She grabbed her purse and ran downstairs.

As expected, her father had been grilling Jimmie. Jimmie looked to Sarah as she came down the stairs for a lifeline.

“Okay, Daddy. That’s enough. Leave the poor boy alone. We are going to get dinner and go to a movie. I won’t be late.” She kissed her Dad on the cheek and gave her Mom a big hug then grabbed Jimmie’s hand and dragged him to the door.

Sarah decided on shrimp tacos and they had a big bowl of chips and guacamole. The waiter made it right at the table by hand and it tasted awesome. The conversation proved easy and lively about all of the normal things that teenagers talk about. And Sarah told him that she had something really special planned for prom, but didn’t go into specifics.

After the entrees had been served, she really shocked him. “So how did you like fucking Ali last night?” She asked it so matter-of-factly that Jimmie almost spit the soda he had been drinking across the table.

“What the hell Sarah? I mean, you helped set it up and all, but damn, to just ask like that?”

“Calm down. She and I are friends and we share and share alike. Just like Jenny and me. Play your cards right and I might share you with her as well. You’d like that wouldn’t you?” she asked with a wicked smile.

“Well yeah, of course. I just didn’t know….I guess I just forgot who I was talking to,” Jimmie said chuckling.

“So?? How was the sex? You know, you are only the second guy to fuck her, right?”

“What?! Seriously?”

“Yeah, up until about a week ago, she was a virgin.”

Jimmie almost spit his soda again. “You’ve gotta be fucking kidding me? She came at me like…well, like you. And she wanted to try all these different positions. I can’t believe she is…inexperienced.”

“But the sex was good? You enjoyed it?”

“Oh hell yeah. I mean it was fantastic.”

“And the blowjob?”

Jimmie just stared at her for a minute. “So no secrets at all, huh? You two talk about everything?”

Sarah laughed and grabbed his hand. “Yes, Jimmie. We talk about everything. We do everything together. What if you could have both of us and Jenny after prom. Does that sound like fun?”

“All three of you? You mean at the same time?” Jimmie leaned in, and continued, “Like when Conner and Terrance and I got together with you?”

“Exactly like that. The three of us want to have an orgy. I haven’t told the other boys yet. You are the first.”

“Holy shit! Like a real orgy?! With all of us together at the same time?” he asked incredulously. When Sarah only nodded with a smile and raised eyebrows, he responded, “Well, yeah, of course. That sounds unbelievable.”

“I even have a hotel lined up and a limo to drive us. Doesn’t that sound cool?”

“How the fuck did you do all of this? Why me? How did I get this lucky?”

Sarah patted his hand. “The evening has just started. Let’s finish up dinner and go back to my house and we can talk about it more.” She smiled and took another big bite of her taco. Jimmie ate up and they continued to laugh and have fun.

+++++++++

They got back to Sarah’s house around 8:30pm. Sarah figured she had at least a couple of hours before she needed to worry about her parents coming home. Saying a quick hello to her sister watching TV in the den, they didn’t stop while Sarah pulled Jimmie up the stairs.

Once in her room with the door shut, Sarah pulled Jimmie’s shirt off and sat him on the edge of the bed and kissed him while stroking his growing cock through his jeans. After a minute, she stood in front of him, pulled her shirt off, and undid the clasp of her sexy bra. She held her hands over her tits and let the bra fall to the ground and then looked at him with an alluring expression.

“Do you want me, Jimmie? Tell me how badly you want me.” Rubbing her tits up and down slowly, she kept them covered teasing him.

“Oh fuck baby. I want you so bad. My dick is getting so hard for you. I think about fucking you all the time.”

“Take your pants off for me.”

Jimmie undid his belt and slid his pants to the floor and kicked them out of the way. His cock head peeked out of the top of underwear, clearly fully engorged.

“Now the underwear and stroke your cock for me,” Sarah asked while showing more of her breasts, only covering her nipples with two fingers on each hand.

Jimmie dropped his underwear and kicked them over to his jeans. Spreading his legs, he confidently stroked his cock all the way up and down the shaft.

Sarah moaned and pinched her nipples, rolling them between her fingers. “I can’t wait to fuck you Jimmie. I love your cock. I love to feel it in me. Tell me how badly you want to fuck me.” Sarah turned while she said this and slowly peeled her skirt and underwear down to the floor while bending at the waist. She stepped out of them and spread her legs to give Jimmie a complete view of her pussy and ass.

“My dick already feels like it could explode. I want to fuck you deep and hard. Grab your hips and drive myself into you as far as I can.”

Sarah stood back up, turned back to him and took two tentative steps toward him. She took his cock in her hands replacing his and continued to stroke it. She looked up into his eyes. “But do you want to fuck my pussy or my ass? Or both big boy? Do you think you can get this giant dick into my tight little ass as well?”

“Oh fuck yeah! You have such a perfect ass. I want to fuck your pussy, mouth and your ass! You are so hot and you drive me crazy.”

“You can Jimmie. You can fuck me any way you want. I’ll do anything you tell me. Tonight and at prom. But I want something special from you too,” Sarah teased with a little pout while stroking him faster.

“What? What do you want?” Jimmie asked lost in ecstasy.

“I want to put on a strap-on and fuck you in the ass too.” Sarah braced for his reaction.

It took a second for Jimmie’s expression to change as he digested what Sarah had said. “What? What the fuck?! What are you talking about?” Jimmie looked confused.

Sarah dropped to her knees and took his big black cock in her mouth. She used both hands and stroked him quickly, plunging her mouth down his shaft, waiting for him to moan at the warm sensation. Without stopping stroking his cock with both hands, she pulled her mouth off of him and repeated, “I want to fuck you in the ass with my strap-on. While I am stroking this cock. You will cum harder than you ever have.”

Jimmie fought to focus through her steady manipulation of his male member. “You can’t be serious. Why?”

“Why do you want to fuck my ass, Jimmie? Fair is fair, if you want mine, I want yours.” Sarah took him back into her mouth and stroked even faster.

“Oh fuck. You are going to make me cum already.” He let out a deep growl.

Sarah stood and grabbed his balls and squeezed hard around the head. “Not yet Jimmie. Answer me first. Is this going to be an amazing night and an amazing prom, or do we stop right here and now?”

“That’s not fair. You can’t stop. Not now!” Sarah didn’t move and just held him. When she didn’t move and stared at him, he broke and continued, “You want to fuck my ass on prom night too?”

“Yes Jimmie. That is what I want. And I want you to help me with the other boys. Conner should be easy. But I want you to agree right now. Think about what I am offering. You can fuck all of three of us in the ass at prom too. You just have to agree to let us have our fun too. What do you think?”

Jimmie stared at her clearly confused and over stimulated. “And if I say no.”

“You don’t want to say no Jimmie. Tonight won’t be fun and prom won’t be fun. Try it tonight and see if I’m not right. It will feel good and like I said, you will cum like a firehose.”

Jimmie looked distraught. “Come on!! This isn’t fair. Why are you doing this?” Dropping back down to her knees, she stroked his cock and waited. Then she took a slow deliberate lick over the head. She could feel his legs quiver and knew his balls must be ready to explode.

“Say yes Jimmie or you leave her tonight and you’ll never touch me, Jenny or Ali again. And you leave with some pretty heavy blue balls from what I can tell.” She tilted her head and looked down at his balls while she lightly fondled them and then back into his face with a disappointed pout.

He closed his eyes and grimaced. When he opened his eyes back up, he stared at her and she could see his resolve melt. “Fuck it. Fine. Just please let me cum. My balls are starting to hurt.”

Sarah smiled, leaned over to kiss the head of his cock before looking up at him with another big smile, and then finished him off, swallowing every drop of his thick man butter. Kissing the cock head one last time before she laid down on the bed and told Jimmie to eat her out. He brought her to two big orgasms and Sarah had to clamp her hand over her mouth to stop herself from screaming out. Having grown accustomed to being unrestricted at Mr. Michaels house, it proved to be a challenge to stay as quiet as possible. And while she felt confident that her sister knew what they were up to in her room, she didn’t want to make it too obvious.

Jimmie recovered quickly and Sarah grabbed a condom and covered his hard member while asking, “How do you want me Jimmie? You can have me any way you want.”

Jimmie put her on her hands and knees and fucked her in doggy style. Grabbing her hips, he drove his rod deep into her. She encouraged him and told him to grab her shoulders and fuck her harder. Following her instructions, he pulled her back with each thrust, slapping against her ass. He thrust hard enough that he knocked her forward and she landed on her stomach. Without withdrawing, Jimmie positioned his legs on either side of her and pushed her legs together. He rolled his pelvis up on her ass and the deep penetration with his dick banging on her g-spot made her cum again. She buried her head into the mattress to cover her loud screams of pleasure and clutched the sheet with both hands as her body shook.

Pulling back too far during a thrust, his dick slid up between her ass cheeks. He reached down to reinsert himself, but aimed his cock head at her buckeye. Sarah stopped him, “Not yet Jimmie. You first and then you can have me.”

Jimmie reluctantly backed off. “Really? Are you sure? I don’t know about this.” He shook his head with a deep sigh.

Sarah rolled and sat up. She kissed him and stroked his cock, carefully sliding the condom off him. “Trust me Jimmie. You’ll like it and it will be worth it. You get my ass next, I promise. And you can spank me while you do it. It will be so hot and you will make me so happy. You want to make me happy, don’t you?”

Resigned to his fate, Jimmie just responded, “Fine.”

Sarah pushed him back onto the bed. Kissing down his neck, chest and stomach before she repositioned and licked the shaft of his dick and sucked each ball into her mouth. She got off the bed and reached underneath for her strap-on and the bottle of lube. Moving quickly so he wouldn’t have time to reconsider, she put on the strap-on with the thicker side in her. Still, her smaller fake dick sticking straight out in front of her made Jimmie’s eyes bulge at the size of what she intended to stick into him. “Lay back and relax. Let me take care of you,” she ordered.

Sarah got a generous amount of lube and coated the dildo with it. Getting on the bed, she got another handful and reached down between his legs. “Grab your knees and pull them up toward your chest. And get ready for one of the best orgasms of your life.”

Jimmie groaned but did as told with his knees pulled up exposing his own puckered asshole. “Just remember, if you want to fuck a girl in the ass, then isn’t it fair to try a little yourself? And I am going to be so gentle.” She rubbed the lube all around his clenching knot. With her other hand she stroked his cock and waited for him to moan in response. Sarah slipped a finger into his ass about an inch. He grunted and sucked in small breath between his teeth and held it.

“Relax Jimmie. The more you relax and breath, the better it will feel.” Sarah slowly finger fucked him with one finger. As he started to relax, she added a second finger. He grunted again and tensed for a second but tried to take several calming breaths. Sarah continued to work his cock and finger fuck him deeper with each thrust. When he fully relaxed, she let him enjoy the dual sensation for a few minutes.

Then Sarah withdrew her fingers and positioned herself between his legs. She rubbed the head of the dildo back and forth over his vulnerable anus before pushing it in. She went very slow and felt the head of the dildo push past his sphincter. Jimmie grunted while Sarah encouraged, “That’s it baby. Take that for me. Let that cock slide into you. God that is so sexy. I can’t wait for you to fuck my ass.” Sarah never stopped stoking his dick at the same time, but picked up the tempo as the dildo went deeper. “Now don’t cum too fast. Hold onto it. I want to give you a good fucking before you get to cum for me. Understand? Your cock is so hard in my hand right now.” Sarah pushed deeper until she had the faux penis four or five inches into his virgin ass.

Jimmie started to get into it, rocking his hips back in time with her thrusts. He clamped his eyes closed, and rolled his head to the side. “Oh fuck! Oh my god. Stroke my dick faster. Oh that feels so good.”

Sarah had kept her phone within reach. With Jimmie distracted, she silently picked it up with her free hand and started a selfie video. She held her arm out enough to capture the action. Jimmie kept up a steady stream of comments, “Oh yeah. Fuck my ass. That feels so deep. Uh, I feel so full.” She picked up the pace and got deeper still, pulling back an inch and then going forward two. Sarah looked at the camera and made an o-face for effect. She spit in her hand and stoked his cock with long strokes up over the head. His moans got louder.

“That’s my good boy Jimmie. Tell me that is my ass. Tell me it is my ass and I’ll let you cum.” Sarah said enticingly.

Jimmie’s voice stuttered and she could see him struggle to focus. “It’s your ass. I’m gonna explode. Oh fuck! I can’t hold back anymore. Fuck me!” Huge spurts of thick cum erupted from his dick, spraying forward all over his chest. Some landed on his chin and on the bed beside his head. With each spurt, his pelvis pushed forward and Jimmie let out a loud groan. Worried he might be loud enough for her sister to hear, she still didn’t attempt to quiet him, wanting to capture his whole reaction on the video. She lost count of how many times he spurted forth his man juice, but it covered his chest and stomach. When he seemed to stop, she made sure to squeeze out the last drop as he started to recover, panting to catch his breath.

He opened his eyes and saw the phone in her hand and looked panicked. “You recorded that? What the fuck?!”

She put the phone down and looked at him, running her finger over his cockhead and scooping up the last drop to bring to her mouth. “You know I like to make sure you boys keep your mouths shut. And I expect you to help me with prom.” He looked a little pissed, so Sarah softened. “Come on big boy. You keep my secrets and I’ll always keep yours. Now, tell me if that wasn’t the best orgasm of your life. Right?”

She could see Jimmie surrender his anger and a broad smile broke out on his face. “Holy fuck! That was unbelievable.” He brought his hand up to his forehead and tried to clear his head. “You weren’t lying. That was the biggest orgasm I’ve ever had.” Sarah carefully pulled the dildo out of his ass and let him put his legs down.

She backed off and took off the strap-on and wrapped it in a towel by the bed, strategically placed for just that purpose. Then she jumped on the bed next to him like an excited little girl. She laid beside him and started with the glob of cum on his chin. Leaning over him, she opened her mouth wide and sucked it all off. Moving down, she licked up every drop off his smooth hairless chest before moving even lower and slurping up larger pools on his stomach. She finished by sucking on his deflating penis. And then returned up to his face and kissed him.

“You are the wildest slut I’ve ever met. Are you a nympho or something?” he asked

Sarah laughed and bit his nipple. “Maybe,” she giggled. “And your gonna help get the other boys to go along, right?”

Jimmie shook his head. “Yeah, yeah. Fine, I will try, but no promises. Most guys would think doing that is…weird.”

Sarah crawled on top of him, smiling down into his face. “You’re turn next stud. How are you going to take my tight little ass? On my stomach? On my back?” Reaching forward, she started kissing his neck waiting for his answer.

“Jesus! Give me a second. I’m still recovering.” He flipped her over onto her back and kissed her neck and moved down to her breasts. Sucking her nipples into his mouth and biting down hard on the rigid flesh between his teeth. Sarah moaned without protest. They continued to play with one another and laugh. Sarah rolled him over onto his stomach and rubbed his back. After asking if he was thirsty, she threw on a robe to run downstairs and get drinks.

After twenty minutes, little Jimmie rejoined the party. He put her back into the same position as before on her stomach. After slipping on a condom, he entered her pussy and fucked her for a few minutes to get back into the rhythm. With Sarah egging him on, he dropped lube down the crack of her ass and ran his penis head through it. Pressing up against her butthole, she didn’t object this time and instead pushed her ass up back against him. His dick slid into her in one steady motion. Sarah moaned out loud as he drilled into her.

“Oh fuck that’s tight!” he exclaimed as he continued to work into her. Sarah pushed backward meeting his every thrust, begging for more and asking for him to fuck her little ass harder. She reached under her stomach and rubbed her clit in small circles.

“Harder Jimmie! I need you to fuck my ass harder and make me cum. Spank my ass! “ she gasped. His hand swung sideways catching her ass flat with a loud smack. Her groans of approval encouraged him to keep smacking her with steady repetition. When her orgasm made her whole body jerk and her legs shake, her gyrations only made it hotter for Jimmie who soon let go with a loud groan of his own, collapsing onto her back once his orgasm ended. They laid together, both panting from the exertion.

When they sat up, Sarah asked, “Have you ever had three girls suck your dick at the same time, Jimmie?”

He chuckled and answered, “No. Of course not.”

“Well you can. I want prom night to be a night nobody ever forgets. You have to help me make that happen. I want more of what you and I just did. We are going to fuck all night. But that includes all the boys doing what we did tonight. Getting pegged by the girls. Are you going to help me? Are you going to help make it the best night ever?”

Jimmie looked to the ceiling and closed his eyes and let out a big sigh. “Look, I’ll…ask the other guys. And I’ll do it if they will do it. I just don’t think they will. And I don’t want to be the only one. It would be….embarrassing.”

“Just tell them how great it was. I bet Conner is more open minded that you think. You two just need to convince Terrance.”

He sat still for a long moment and then nodded. “I told you that you are a crazy bitch. But what the fuck. The sex is also amazing and I’ll probably never get a chance at a girl like you again. Ever.”

Sarah smiled and kissed him. “Don’t you forget it!” They got dressed and she saw him to the door.

+++++++++

The girls met in the morning for their brunch and massages. Ali looked apprehensive the whole time and Sarah and Jenny knew she worried about going over to Mr. Michaels that afternoon to have anal sex for the first time. Trying to stay encouraging, they gave her a big hug when they finished with the fun morning.

Ali called around 5:00pm and asked if she could come over. Sarah guessed from the tone of her voice that things hadn’t gone well.

When Ali arrived, Sarah started to take her to her bedroom, but Ali stopped her. Leaning close to Sarah, she whispered ‘camera’. Sarah nodded and suggested they go for a drive for privacy. They got into Ali’s car, but she didn’t start it.

Looking distraught, Ali couldn’t speak. Quietly, Sarah finally asked, “So what happened Ali? I take it that things didn’t go well. Start at the beginning and just tell me what happened.”

Ali looked at her with moist eyes, before she started with a shuddering breath, “Well, I got there and he took me into the den and looked angry right from the start. He pulled my shirt off and then grabbed my bra and asked why the fuck I was wearing a bra. That by this time I should know better than to show up wearing clothes that aren’t sexy and that I was never to walk into his house with a bra on again that he didn’t buy for me. He took it off and went into the kitchen and got scissors and cut it to pieces in front of me. He said that I was his slut and when I show up at his house to fuck him, that I better wear something sexy and slutty.”

She gulped and stared at her hands before continuing. “Then he said to learn my lesson, I am not allowed to wear underwear at all for a week. I have to wear a skirt and a tight blouse at all times. Even school. How am I going to do that? People will see?”

“Don’t worry about that now. Go on.”

“Well he took my shorts off and cut my underwear to pieces as well and then grabbed my arm and dragged me upstairs. He picked up the paddle and told me to lay on his lap and then he spanked me twenty times. I had to say ‘I will only wear sexy slut clothes for my Master’ each time he spanked me. It hurt like hell. I’ve never been spanked that hard. Then he made me bow and thank him for my punishment and kiss his feet and promise to do better. And I also had to tell him that he owned my pussy or something like that. I guess I didn’t do it enthusiastically enough, because he grabbed me by the hair right by the scalp and pulled me up to my feet until I was on my tiptoes and he got right in my face and told me that if I wasn’t serious that we could just stop everything right then. That I didn’t have to do anything for him anymore and I would just deal with cops all by myself.”

She looked at Sarah and grabbed her hand, “I was so scared Sarah. He can be so frightening. He let go and just stood there. So I dropped back down to my knees and begged him not to. And promised that I was his willing slave and I would do what I was told and he didn’t have to worry.”

Sarah nodded. “I understand. I’ve done the same thing. Go on.”

“Then things got a little better. He put me on the bed and went down on me. He told me that I wasn’t allowed to cum and ate my pussy and used his fingers. It felt so good. I tried so hard and I begged him to stop. But his fingers just kept hitting the right spots and I came. A couple of times. I think I even squirted a little. I’m not sure. I thought he was going to spank me again, but he didn’t. He stood me up and put cuffs on my wrists and ankles and a collar around my neck. He put nipple clamps on me and one of the butt plugs in my ass. The smaller one with the handle. And then stood me in front of the big mirror. He ran his finger tips all over me and circled my breasts while he kissed my neck and shoulder.”

She paused and looked at Sarah again. “He bit down on my shoulder. It wasn’t super hard, but hard enough. It sent tingles all through me. And then he spread my legs and started playing with my pussy again. I thought I was going to melt Sarah. It felt so good. I forgot all about the clamps and my pussy just kept getting wetter. He would alternate between kissing on my neck and shoulder and biting on both of them.”

“Every time I would beg to cum, he would stop and pull the chain of the clamps straight out. It felt like it he might pull my nipples off! He stretched them so far. The first time I said ‘Ow’ and he told me to take the pain and not make a sound and to keep my eyes open and look straight ahead. He had the camera set to record everything in the mirror. By the last time, I thought my head would explode.”

She sighed at the thought of it and took a deep breath while Sarah waited patiently. “So then he put me on the bed on my hands and knees and put the camera right in my face. He told me I had to look forward the whole time. Then he tied a string to the chain of the clamps and strung it through the collar and tied it to the butt plug. He told me I wasn’t allowed to cum or let the butt plug come out. Then he got up behind me and started fucking me. He’d pull on the string every time I started getting into it. I had to clench so hard to keep the butt plug in and then my nipples would kill. And then he was really unfair. He handed me the vibrator and told me to keep it on my clit.”

She shook her head and sighed. “I mean, that was it. I wanted to cum immediately. I begged and he either slapped my ass or pulled on the string or both, but I didn’t care. I tried to cheat and hold the vibrator above my clit, but he knew immediately and pulled so hard on the string that the plug came out. That pissed him off more and he got the bigger plug with a handle and put that one in me. And he wasn’t as gentle. He told me to keep the vibrator on my clit and to keep the plug in and focus.” She took a cleansing breath.

“He went back to fucking me. This time, he grabbed the vibrator and he pushed it onto my clit hard. And he grabbed my shoulder with the other hand and pressed his dick so hard into me that it kept hitting the top of my pussy or something. It sent crazy trembles all through me. He got me to the edge so many times. I don’t know how I stopped myself I wanted to cum so bad.”

She paused and looked right at Sarah again, “Then he pulled the plug out himself and told me to look straight ahead and keep my eyes open right at the camera. And he did it. He fucked my ass! It felt HUGE going in. And it went so deep. I think I screamed. As soon as he was all the way in, he took the clamps off my nipples and rubbed them. They hurt horribly. But he kept fucking me and started going faster. It felt so different, but it still made my pussy tingle. He reached under and put the vibrator back on my pussy, but this time down low by the entrance. And he started fucking me so deep and fast. He held my shoulder again and slammed me back into him. He moved the vibrator up to my clit and told me to cum without my having to ask.”

She looked at her friend with big eyes. “Sarah, I’ll be honest, it was the biggest orgasm of my life! I felt my whole body jerk and I think I tried to get off of him, but he kept holding me and fucking me. I don’t know how long I came or how many times, but it had to be at least two or maybe three. And then he dropped the vibrator and used both hands on my shoulders to fuck me harder. When he came, he ground right into my ass and held me tight. I could feel it! It was hot inside of me. I just stayed still and kept my eyes on the camera the whole time while he held me. I could feel his cock throb inside of me. It was….crazy.”

“So it wasn’t as bad as you thought, right? You actually kind of liked it?”

Ali rocked her head. “Well, yeah. I mean it hurt like hell too, but I also came like crazy. It was both. But no, I didn’t hate it. I wouldn’t want it every time, but I would do it again I guess.” She looked guilty at the admission.

“I felt the same way. And it gets better as you do it more,” said Sarah thoughtfully.

“But that wasn’t the end of it.” Ali took a deep breath and let out a sigh. “He told me to get cleaned up and we rested for a bit. Then he got a dog leash and attached it to my collar and pulled on it and said, ‘Follow me pet’. It was so degrading. I mean I think it was degrading. I don’t know anymore. He led me downstairs to the basement and into the wine cellar. And then he did something on his phone and the WALL OPENED!”

When Sarah didn’t look surprised, she concluded, “I thought so. You’ve seen it. You’ve been in there too.”

“Of course,” Sarah admitted.

“It’s a sex dungeon, Sarah!” Ali exclaimed angrily. “How could you not tell me about it?!”

Sarah felt taken aback. “Not tell you about it?! What the hell are you talking about? What do think all of this is? He makes us bow at his feet. We are his WILLING sex slaves. He has made you recite that like a thousand times even though he has given you an out over and over again. You are actually surprised he has a sex dungeon?! You can’t be that stupid!”

Ali just looked stupefied and couldn’t say anything.

Sarah continued, now getting more accusatory herself, “And why the fuck would you think there is anything I can do about it? Do you think I am ALLOWED to discuss it? I am in exactly the same position you are. I don’t do anything without his permission. I wouldn’t even think about it at this point. He didn’t tell me I could discuss the sex dungeon with you. So how am I supposed to do that?!” Sarah sat back in a little huff and crossed her arms looking forward, refusing to look at Ali.

Ali considered and sat back looking forward as well. The words hung in the air. “You’re right. I’m sorry. I didn’t think about it that way. I guess….I guess I was just so surprised by it.”

“How do you think I felt the first time he took me in there? All of those giant contraptions and whips and floggers everywhere. Knowing what he was going to do to me. I didn’t know what most of it was even for.”

Ali ventured, “How many times have you been in there?”

Sarah softened and looked back at Ali. “Enough. More than a few times.”

“And is it bad?” she asked tentatively.

Sarah shrugged. “It’s like everything with him. It is scary as hell and intimidating, but then he does something you’ve never even conceived of and makes your head spin with pleasure. It’s all pain and pleasure Ali. Punishment and reward. Sure, one thing on its own seems inconceivable. But he does it with other things and it becomes incredible.” She reached out and took Ali’s hand. “You just had anal sex for the first time. If I had asked you a month ago, you would have been adamantly opposed to even considering it. What are your thoughts now?”

Ali nodded. “I get it. You’re right. I never would have considered something like that before. Now that I’ve done it and if I’m honest, it was the best sex I’ve ever had. Not that I’ve had a lot.” Shaking her head, she finished, “I don’t know how I got here.”

“I’ve had lots of punishments. Mostly because I would object at first to a new demand or instruction. But then I did it and it’s like each punishment opens a door of sorts. I think it is freeing in a way, to just give in and do what I’m told without thinking about it.” Sarah said thoughtfully. “And it’s not like I don’t know he will continue to punish me. Give me crazy assignments. Make me do things I don’t think I can do. But it has also given me more confidence than I have ever had. Especially with boys.”

Ali sighed again, “Okay, I will try to be more open and not fight it as much.”

“Tell me the rest. What else happened?”

“Well, he took me inside and let me look at some of the equipment. He still had the leash on me and he led me but he let me look and didn’t say anything. There was so much to take in. Then he stopped me in front of that big chair. He took my leash off, picked me up off the ground and set me in the chair. The one with the two outstretched arms and the bent leg supports.” Sarah just nodded knowing exactly what she referred to.

“He strapped my arms down with several wide Velcro straps. And then he strapped my legs down. Around the thigh a couple of times, under the knee and around the ankle. He even put one around my chest just under my breasts. I couldn’t move more than an inch anywhere. He surprised me when he pulled the two leg supports wide apart. I felt totally exposed. He brought over that big hitachi vibrator and told me that I needed to work on my orgasm control. He was disappointed that I couldn’t control myself with Jimmie or with him upstairs. He didn’t seem too angry but I told him I was really sorry and I would try to do better.”

She paused and took a deep breath. “He put the hitachi on my pussy and told me that I needed to work on ‘edging’ myself. He said that is when you bring yourself right to the edge of orgasm, and then stop yourself from having one. He rubbed all over my pussy until I begged and then he pulled it off and waited. He told me to breath and control it. He did it like ten times. Maybe more. Each time I begged and calmed myself down when he would stop. My hips started humping and I couldn’t stop. It felt like I was leaking everywhere. Then I thought he had taken me too far when he grabbed my nipple and twisted it so hard. I screamed. He told me to stop screaming and control myself with my breathing. The next time he slapped my tits hard. I don’t know how long it went on. He slapped my pussy, my thigh, twisted my nipples, even used a long stick to hit the bottom of my foot. That one probably hurt the worst.”

She sighed before continuing, “But he never let me cum. I begged so much. I promised him anything to let me. He finally stopped and got up close and said he had a new punishment for me. He said he was going to make me cum. And cum a lot, but then after today, I am not allowed to cum again for a week. I have to edge myself five times a day, twice each time, get myself right to the edge, but then stop. Once has to be with a vibrator and once has to be with a dildo. I have to make videos while I do it and send them to him and tell him that ‘I have been a good slut for my Master and did not cum without permission. Thank you sir.’”

“He said if I don’t get it just right, that I have to start all over. And if I ever have an orgasm, then my week starts over.” Her eyes were huge at this revelation and she looked terrified. “And the worst part is, it’s once in the morning, once during the day, even if I am at school, once at night, then at 1:00am and at 4:00am. He wants me to wake up twice during the night to do it.” She held her breath and stared at Sarah. “I don’t think I can do it Sarah. That sounds crazy! And that is on top of having to go without underwear all week. I’ll be leaking pussy juice everywhere!”

Sarah nodded. “You can do it Ali.” She decided to let her in on a secret. “Jenny and I have both had to do orgasm training. I’ve done it twice. You have to keep that to yourself. Don’t let on to Mr. Michaels that I told you. But I am telling you, you can do it.”

“You’ve done it TWICE? Seriously? I mean…how? How bad is it?” she asked.

“I’m not going to lie, it’s not my favorite. It’s hard. Especially getting up during the night. Luckily, you are pretty quick so it shouldn’t take too long. But it is exhausting. And frustrating. And you want to kill him by the end. But you will learn how to control yourself better. That much I promise. And it makes it easier when you are with him. But whatever you do, don’t cheat. Don’t think you can pretend to get close. You have to really edge yourself or he will know. He caught me cheating. I don’t know about Jenny. We aren’t generally allowed to talk about it.”

Ali dropped her head back against the seat and said, “Oh fuck! This is going to be so difficult.”

“Jenny and I can help you when you are at school. We used that downstairs bathroom. The small one. And Jenny had one of those signs they use when it is being cleaned. Plus, she and I can take turns to watch the door for you. I had to do it on my own the first time so I also had to worry about getting caught all the time. You can also run out to your car if you have a study period. That worked for me as well.”

“Okay. Thanks. That helps. I was worried about getting caught.” She looked pensive.

“Was that it? Did he stop there?”

She shook her head. “No. He let me out of the chair and took me over to this half barrel thing on the floor. It had this purple rubber piece on top with two bumps at either end and a four inch dildo in the center. He called it a ‘Sybian’. He made me, you know, sit on it with the dildo in my pussy. Then my clit pressed up against the one bump and the other kinda pressed right against my asshole. He told me to enjoy these orgasms as a reward and that I was allowed to cum without having to ask until he was done. And of course, he had another camera right in my face.”

“He put the controller on a stool next to me and stood behind me. He turned it on slow and reached down and played with my tits. That Sybian thing is so strong! Between his massaging my tits and gently pinching my nipples and the vibrations all through me, not to mention being edged for so long, it took like a minute and I had my first orgasm. He reminded me that I still had to announce each one.”

“And then he turned the dial up and the vibration got stronger. He turned the other dial and I felt the dildo start rotating inside of me. It rubbed right against my g-spot. He kept pinching my nipples and I had another orgasm, making sure to tell him. He turned up the dials more and I was so sensitive that I tried to sit up. He held my shoulders and wouldn’t let me get up and told me I had to stay on it just like I was until he told me I could get up!” She shook her head and a deep breath at the memory.

“The vibration got so intense and the machine got kinda loud. I moaned like crazy and had two more orgasms back to back. He pinched my nipples harder and turned the machine up more. It kinda hurt at first and then felt so good. The rotating dildo beat against my g-spot and I could feel my pussy leaking fluid everywhere. Then I lost track of the orgasms. They just kept coming. I could feel my hips grinding my pussy onto the clit bump and couldn’t stop.”

“If I tried to rock back to get it off my clit, it vibrated my asshole more and jiggled my butt. Then he moved around in front of me and guided his dick against my lips. After moving the camera right to the side of us up close. I tried to take him in my mouth but he stopped me. He told me to stick out my tongue and he rolled his cock head around my tongue and then put the shaft right over my face and pulled it down my tongue. He had just started sticking it in my mouth when I had to pull back to tell him I was cumming again.”

She looked over at Sarah. “My body started to shake but he didn’t care. He jammed his cock into my mouth and told me to suck him. I tried to reach up with my hands but he told me mouth only. Then he turned the dials up more while he fucked my mouth.”

“I had more orgasms while I was blowing him. but he told me that if I stopped or paused he would punish me. ’Focus on my dick slut. Don’t think about your pussy right now. Only my cock. Use your hands and make me cum. Hold it all in your mouth until I’m done. I want to see it before you swallow it,’ he told me.” She shook her head some more and picked at her finger.

“It was so hard to focus. I couldn’t stop the orgasms. They just kept rolling through me. It started to be like one long orgasm with peaks and valleys. He finally came in my mouth. It felt like a gallon, and I had to resist gulping. I came really hard while he finished and my brain felt totally scrambled. He pulled himself out and told me to show him. My mouth was full and a little dribbled down my chin while I tried to hold my mouth open for him. And then I came again and more spilled out. Each new orgasm started to really hurt. He told me to swallow and I got it all down and showed him before he would turn the machine off.”

She let out a deep sigh and looked at Sarah, “I was numb from the waist down. The Sybian was a wet mess and he made me clean it up with some towels. I tried to touch myself, but I was sore and even a little touch hurt.”

“Then he took me upstairs and had me sit on his lap for a while and took his time kissing me and fondling me. He asked if I understood both of my instructions for the week. And I promised to do my best. He asked about the Brazilian and if I liked how it felt. I told him that it hurt, but probably less than I expected and that I really liked how it felt when the air blew over me. He laughed and said I would get plenty of that this week. Then he let me get dressed and leave. I drove around for a little bit trying to take everything in and then called you.” She looked back at Sarah with a look of despair and a tear welling up in her eye.

Sarah nodded. “You did well Ali. I know this week has been a lot and next week will be challenging as well. But my guess is it will all get easier after that. We have prom to look forward to. And then graduation. Just don’t let it overwhelm you. And stop thinking that you should be fighting this. When you just accept it, it takes a weight off your shoulders. You don’t have a choice.. But remember, Jenny and I are both here for you. Anytime you need. Okay?”

Ali leaned over and hugged Sarah. She clung to her. “Thanks Sarah. I don’t know what I would do without you. Sorry I got upset earlier. I do understand that you don’t control this any more than I do.”

Sarah didn’t say anything but still felt guilty for setting Ali up in the first place. She let it go and gave Ali a more than friendly kiss before going back into the house.

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