Carrie Ann and the Wayward Sons

"Yes, master," she said softly. She rolled deftly from her heels to her knees. She knelt before Jake, reaching for his pants and freeing his erection. Then she bent over and damn near swallowed it whole. It was amazing; she was focused entirely on his dick and trying to get it off. With every stroke she tried to swallow it all, then pleasured it as she let it go. She wanted to suck that dick. When someone doesn't really want to suck your dick—which is most people, most of the time—they'll just suck the tip while doing a lot of stroking with their hands; a lot of blowjobs are really handjobs with a wet tip. Carrie Ann couldn't have fit two fingers around what little of his dick she didn't swallow. And most amazing—she held her hands behind her like she was wearing handcuffs the whole time, even though she wasn't. She was doing all the work with her mouth. Jake tried to keep up the stern demeanor, but he couldn't help but wince and squirm at the amazingly pleasurable sensations. Suddenly Jake grabbed Anna by the hair, pushed her face onto his knob, and stiffened. There was little question he was filling her mouth with semen.

Jake released her hair, and she knelt back on her haunches. Then, to my surprise, he said "Well?" She responded by opening her mouth. "Show your guests," he commanded. She went in a circle, showing her open mouth first to Dustin, then Greg and finally me. The load that she had just milked from Jake's dick was balanced carefully on her tongue. Apparently she was holding on to it until she was given orders as to what to do with it. "Swallow it, then get started on the next one," Jake commanded.

She swallowed the mouthful of cum and soberly began to work my penis free from my pants—not difficult, as my rod had damn near ripped itself out of my pants by this point. Without hesitation, she swallowed me almost whole. It's a good thing I wasn't standing, because my knees would have buckled as I felt her use her tongue down my entire length as she pulled her head back, and again as she swallowed as much of me as she could. She didn't look up once; she was focused on my dick and how much of it she could swallow at once.

I noticed that she was holding her hands behind her back again. As a result, her soft breasts made contact with my knees as she sucked me. What a waste, I thought—I'm one of those guys that likes to hold a chick's tits in my hands when she blows me. I grabbed the free mounds; they were soft but firm. She had large nipples, with I pinched gently between my fingers. Then realizing that she might like it, I pinched them harder. She looked up at me for a second when I did that, not in alarm, but as if to tell me that she did, indeed, like it. I grabbed them even harder and pulled, forcing her swallow my dick and hold her position. She looked up at me, not in fear or surprise, but with raised eyebrows that seemed to say "what would you like to do with me next?" I let her nipples go and she resumed sucking. Damn it was good—I couldn't remember the last blowjob I'd had where the girl was this focused just on getting me off. Maybe it was on the honeymoon, more likely it was before my wife and I were even engaged, back when we were both still trying to sell the other on the idea that we were worthy of them. I was so used to half-hearted blows and uninspired spooning I'd forgotten just how amazing it felt when someone reallytried. I watched my dick disappear into the pretty, blond-haired face, then closed my eyes in response to the incredible sensations running up my spine. I wasn't long before I felt my nuts tighten up. I grabbed her tits with both hands while I pumped spurt after spurt of hot sticky cum into her mouth. She obediently held her position, her mouth wrapped around my dick, until she didn't feel me spurt anymore. Then she let me go, kneeling on her haunches, mouth open to show me my own spunk yet eyes somehow downcast. "Swallow," I commanded, and she did. I wondered what other options there might be?

She moved towards Greg and started giving him the same kind of wonderful blowjob that she had given Jake and me. I moved to a chair closer to Jake and whispered "so what's her story?" while Carrie/Anna worked on swallowing Greg's dick.

"Sad," Jake replied, "her mom is a total wack job. Spent time in the nuthouse, the whole bit. Daddy was always the one she cried to when she scraped her knees, you know what I mean? Unfortunately as Carrie grew older, he was still the TLC but started to demand something in return, if you know what I mean. What was she supposed to do? It's not like she could turn to mom, so she gave daddy what he wanted so that he'd still be there for her, and in time she started to like it." Now that he wasn't acting as her master, I could tell he had really taken this girl's plight to heart. He continued "then all of a sudden Dad just disappeared. My suspicion is that he saw that Carrie was starting to really get into doing what he told her to, and it freaked him out. He probably decided to leave better leave before anyone found out what he had been doing to her and he ended up on the front page of the newspaper."

"Does she have a boyfriend?" I asked.

"Are you kidding?" Jake replied, animated, "look at her. She's a teenage boy's dream come true—just tell her to suck and she'll give you the best blowjob of your life, no questions asked. By now a handful of guys at school have found out about her, and now they use her on a regular basis. Little pricks don't even bother taking her for dinner and a movie first, they just take her home and fuck the shit out of her. And they don't even appreciate it—I've seen her show up to school on Monday with bruises on her neck and back... let's just say I doubt this is the first time she's done four guys at once."

"You care about her," I observed.

"I just feel so sorry for her," he replied. Then earnestly, he added "Look...that first time I when caught her smoking, I admit I was kind of hoping for an exchange of favors, but I certainly had no idea what I was getting in to. Part of me feels awful every time I screw her, because I'm just feeding into the pathology, keeping the sick cycle going. But you know what—if I don't do her, one of those scumbags from school will. At this point, she literally can't say no, can't protect herself. She wants to get used like this, by now it's the only thing that makes her feel like anyone cares she's alive."

We both paused and watched her work. Greg had grabbed the back of her head and was forcing his cock into her throat. She was looking up at him with doe eyes while fighting the urge to gag. Everything took on a different light all of a sudden. Then Jake spoke again. "So I'm taking a different tack—I'm trying to help her capitalize on her strengths."

"What do you mean?" I said.

"She really needs to get out of that house and away from her wacko mom. But just look at her—she's dripping fucking wet just from being ordered around and manhandled. You can't fake that," he explained. "I know there's gotta be some rich guy out there looking for a submissive girl just like her, who'll be the dom she needs but who'll take care of her as well. There's a bondage webring I've been looking into, trying to find a match for her. Otherwise, she's just gonna get used by one loser after another until one day the find her dead in a ditch somewhere." His voice trembled as he said the latter—it seemed he was really afraid that one day she'd just turn up dead. It certainly explained his initial demeanor when she arrived.

Greg meanwhile was arching his back and closing his eyes—clearly he was now ejaculating into her mouth. With a slight satisfied grin, he let go of her head and pulled his dick out. As with us, she opened her mouth to show him his load resting on her tongue. He didn't tell her to swallow it right away though; he gently touched her chin and inspected her open mouth from several angles before giving the order. Without getting up from her knees, she moved over to Dustin.

"So, fucked up as it may be, we're actually doing her a favor," Jake said with some sadness. "She was gonna be fucking someone somewhere tonight; I know, because I tried getting her off the streets and not fucking her, and all she did was ditch me and find her way over to some guy's house to get laid. At least we'll sure she's fed, and keep her away from the goddamn drugs." "It's hard for me to play the master with her," he continued, which kind of surprised me because he'd done it so convincingly, "but that's the way she likes it. Not necessarily pain, she puts up with it but that's not what she likes. Giving her orders—she totally gets off on that. So by all means, command her to do whatever you like—the more demeaning the task, the hotter it will make her."

I don't know if Dustin was listening to our conversation, but it was clear right away he wanted something different. Anna was moving to free his dick when he barked "Show me yourself." She got back into the deep knee bend position and spread her pussy wide. "Now, masturbate!" he commanded. She let go with one hand and began rubbing her own clit. "Come on, MASTURBATE!" he urged. She slipped two fingers of her other hand into and out of herself while rubbing her clit with the other. Her fingers glistened from the dew inside when they emerged from her hole. She gulped and closed her eyes in response to her self-stimulation.

Dustin was enjoying this. He let her play with herself for a while, then stood up, dropped his pants and shoved his dick into Anna's face. Reopening her eyes, she offered her mouth to him as she returned to a kneeling position. Instead, Dustin grabbed her by the hair and nearly screamed "Bitch! Did I tell you you could stop masturbating?" She shook her head no quickly, then thrust her fingers between her thighs again. "That's better," he said, stuffing his dick back into her mouth. She did her best to blow him while jerking herself off.

Our conversation ended on account of my watching Dustin. Jake stood up and went to the back room. Dustin meanwhile said "Masturbate harder!" She dutifully rubbed herself at an even faster pace, still sucking his dick. She was getting really hot now.

Dustin grabbed her by the collar and pulled her toward him, forcing his dick deep into her throat. She had to bend her neck to accommodate him, and was fighting to keep from gagging. "Keep masturbating!" Dustin ordered. She dutifully rubbed her clit while his dick was in up her mouth up to the balls. "That's it. You're a dirty slut," he leered. "Aren't you? Aren't you?" He let go of the collar, allowing her to release his dick and breathe. Then he pulled her hair and so that she was looking up at him and challenged "What are you?"

"I'm a dirty slut," she repeated.

"Louder," he commanded, "and keep masturbating!"

"I'm a dirty slut," she repeated louder.

"Harder!" he urged, "rub yourself harder!" He reached for one of her nipples as well.

Carrie/Anna rubbed herself as fast and hard as she could. "I'm a dirty slut!" she repeated.

"What?" Dustin urged.

"I'm a dirty..." she began loudly, but then lost her steam, suddenly slouching over. Instead of the word slut, all that came out was "oh..." I saw her trembling briefly, and knew she had just had an orgasm. How the fuck did Dustin know so much about domination that he knew that would get her off?

"What are you?" Dustin asked in a normal tone of voice.

"I'm a dirty slut," she repeated in the same voice.

"Yes you are," he commanded, "and you're welcome. Now show me your appreciation!" With that he stuffed his cock into her mouth once more, and she did her best to oblige him.

Jake now returned from the back room with two boxes of condoms and a huge tube of KY jelly.

"Perfect," Dustin said when he was them, "toss me one of those, will ya?"

Greg opened the first box and pulled off one of the dozen condoms inside, tossing it to Dustin. He ripped open the package, then pulled Anna's hair again so that she had to look up at him. "Put this on me!" he ordered.

She started to reach for the condom, but Dustin slapped her hand. "Not like that, you whore!" he commanded. She looked at him with a mixture of surprise and bewilderment...how else should she put on the condom? "What...don't tell me you've never done a no-hands condom???" She shook her head. Dustin sighed with exaggerated weariness. "Fine," he said, holding the tip of the rubber in front of her mouth, "make a little 'O' with your mouth...good, now suck in slightly, just enough so the rubber won't fall when I let go...OK. Now, position it...there. Now, GENTLY scrape your teeth along the top and bottom of my dick, and you'll unroll the condom in front of you as you go. Get it as far back as you can." It took her a while to get the pressure right, she got it started fine but slipped off a few times, having to start over again, until she succeeded in helmeting him.

"It's about time," Dustin growled, "now GRAB YOUR ANKLES!" She rolled over onto her back, grabbing her ankles, and before she could collect her wits Dustin was on top of her, penetrated her, and was hammering her for all he was worth. She swallowed hard; she had just come a short time ago, and with his relentless hammering of her pussy she was approaching another rather quickly. I was suddenly feeling very inferior to Dustin. I felt better when he went nut inside her before he could bring her off again.

Dustin, breathing hard, fumbled back to his chair, but there was no rest of Anna. "Come here, Anna," Jake said in a normal tone of voice, sitting now on the sofa. She came over to him on her knees. "I see you've learned one new thing today already—did you still want to do the other thing we talked about?" For just an instant, a little of Carrie shone through, as she nodded her assent. "Very well, Anna, come here." When she was right in front of him, he gently reached for her arms, drew them forward, and brought them up towards her face. With a strange mixture of kindness and cruelty, he locked Anna's wrist restraints to her slave collar. "It will be easier if these are not in the way," he said softly. Anna said nothing.

Jake now stood and went to the side of the coffee table. "Here," he commanded. Still on her knees, she moved to the spot. He pushed her until she was bent over the coffee table, resting on her chained arms, ass up in the air. Jake took up a position kneeling at her side. Jake now took the KY, squeezed out a generous amount and began to work around and, one finger at a time, into her ass. Jake was being very gentle now, not being the stern taskmaster as earlier, as he worked on prepping her virgin asshole. Of course, it was pretty clear he was about to buttfuck her, so maybe he was still being the demanding master after all.

Neither of them remained entirely in their prescribed roles as Jake prepared her for her first anal penetration. "Is it OK?" he asked when he expanded the hole to three fingers.

"Mmm-hmmm," Carrie Ann replied, affected. She was concentrating so hard she forgot to say "Yes, master."

"Try to relax," Jake said soothingly, gently rubbing her back like a lover, "and maybe spread your knees a little wider, but keep your ankles together."

She adjusted her knees, and the fingers slipped in more easily.

"Oh...I forgot... there's a safe word," Jake said out loud. "I'm sorry, I should have done this right away. If Anna ever says the word 'ganja,' it means she's had enough. The game ends, and everyone stops what they're doing. Got it?"

We all nodded. I'd hear of safe words, just never had need for one. "Are you ready, Carrie Ann?" Jake said in a gentle, patronly tone completely incongruous with what he was about to do. "Yes," she replied bravely.

Jake wasn't even hard, he was so focused on prepping her. I'm sure she could have gotten him up in a second with that talented tongue, he didn't seem to want to burden her. He reached for a condom while jerking himself. When he was mostly hard, he stuffed it into her pussy; it was still so wet he had no trouble getting it in even though it wasn't completely stiff. A few strokes inside of her boiling slit, however, and stiffness was no longer an issue. He could have re-roofed a house with that hammer. Pulling out, he now helmeted himself and positioned himself above the tight hole.

"Now remember, just relax," he coached as he pushed against it. The tight muscle fought to keep him out, but he was so slippery from all the lube he pressed in despite the resistance. He pushed in just a little ways at first, asking "how is it?"

"It feels good!" she replied with some surprise.

He worked his dick in deeper and deeper until his hips hit her cheeks on the way in. "Still OK?" he asked.

"Mmmmm," she mumbled. It sounded better than OK.

Jake smile now. He started fucking her at a normal pace, although somewhat gently. At the same time, reached under and stroke her clit. She couldn't help herself but make noise now; between the dick in her ass and the finger on her clit, he was driving her wild. She was pinned down; his dick in her ass, her arms chained to her neck, and his fingers on her clit, she couldn't move—she was completely at his mercy, and combined with all of the genital stimulation she was being driven insane with pleasure. Jake seemed to be taking pride in just how excited he was getting her, as well he should. Suddenly she arched her back, she rose up as best she could with her arms chained, and practically screamed "nnnggghhhaaaa." She came so hard the ripples shook the whole fucking coffee table.

She collapsed onto the table, breathing hard. Jake pulled out and gently stroked her hair. He even kissed her gently on the cheek. I thought that maybe he'd decided she'd had enough and just ended the lesson after that massive orgasm, but when he took off his condom I saw that there was spunk in it. Apparently her orgasm in itself had triggered his. Given how it had shaken the coffee table on the outside, I couldn't imagine how intense it must have been to be plugging her ass during that climax.

The very strangeness of the scene struck me for a minute. Here was this young girl, naked, bent over a coffee table, ass lubed up, with her middle-aged teacher gently stroking her hair like a lover after having just finished reaming her. Jake definitely had way too many feelings for her, but then again, how could he not?

My thoughts were interrupted when I heard Dustin ask "Can I try?" Gone was the commandeering general from before; in its place was the meek, asking permission.

"What do you think?" Jake asked her, "are you up for some more?"

"It's fine...I mean...yes master," she replied, remembering her role. Jake and his student smiled at each other. It suddenly dawned on me that he had probably helped her out of more jams than just the smoking incident.

"OK, but let's get these off first," Jake said, letting her kneel upright and unchaining her arms. Then he pushed the coffee table aside and helped her get situated on all fours. Dustin knelt before her, and she began to harden him with her mouth, but this time he wasn't forcing himself into her—at least, not on this end. He was rigid quickly, put his own condom on, and then went around to her backside and slowly pressed himself against her sphincter. Once past the initial resistance, he could bury his rod up her ass. With her hands free, Anna now reached for herself and masturbated while Dustin filled her butt. It seemed that she did really like the anal sex, or at least the feeling of having an orgasm while anally penetrated.

I couldn't hold it anymore; I stood up, dropped my pants, and started jerking off just watching. Dustin saw me and suddenly felt bad—he had gone out of turn, skipping ahead of me in line just like he had always done back in grammar school. But he wasn't about to stop plowing her ass, either, so he decided he could share. He motioned me that I should come next to them, which I did.