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Carrie Ann and the Wayward Sons

Category: Group Sex
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The stripper twisted her butt right Jake’s lap, as if she were waxing his crotch with her cheeks. His eyes were fixed on the tight rotation, while the rest of us watched her bare breasts swaying in time. Twenty minutes ago she had been dressed like a secretary, but now the G-string stretched between her cheeks (and her tip garter and high heels, of course) was all that remained, and pretty soon that would be gone, too.

She stood and returned to the middle of the floor between our circle of chairs, tossing her blonde hair (fake) and shimmying her hooters (also fake). The faint traces of stretch marks just above her crotch were real, but you can’t be too choosy, because there just aren’t that many strippers that make house calls.

The moment of truth was arriving. She started stretching the band of the G-string, pulling it out of position by her hip. She would undoubtedly play with it a few times before abruptly pulling it down to her ankles and kicking toward one of the four of us—and whomever she kicked it to would be the first one she would hit up for tips—or extra services. She had been kind of favoring Jake, but at the moment she was facing me. You never could tell for sure if the stripper did extras on the side or not, but something about this one made me pretty confident she did, so I had the Franklin pre-loaded in my palm. Another giveaway—her safety escort hadn’t started getting fidgety, meaning that he wasn’t expecting the show to be just about over.

As you might have guessed, this sort of thing is nothing new for me—or should I say for us. A dozen years ago, Jake found a stripper for Dustin DeWynn’s bachelor party, and it was the first time we’d ever heard of extra services. I had been married about two years at the time, and my wife was pregnant with our first child, so I hadn’t been getting any back home, and a blowjob on the side had been very welcome at the time. At a dinner party some weeks after the wedding, I kidded Dustin saying “Oh man, I can’t wait for the stripper to get here!”

Dustin laughed, but my friend Greg had overheard me, and agreed “Oh man, I hear ya. That was awesome!” Greg was in his first year of residency at that time, so although he had a fiancee he worked a lot and didn’t see her as regularly as he would have liked.

“All we need is a reason to hire one—hey Jake, when you gettin’ hitched?” Dustin called out as Jake walked by with a drink in his hand.

“Huh?” Jake asked.

“Dustin was wondering when you’d get hitched; we’re looking for an excuse to hire another stripper;” I smiled.

“That was pretty hot, hey?” Jake agreed, “but why do we need a special occasion? Let’s just make one up!”

And that’s how the “club” began. The four of us began getting together every other month or so for the express purpose of an evening of gentleman’s entertainment, and twelve years later we were still doing it. Sometimes we just went to a titty bar, a couple times we took road trips to Vegas, but most of the time it was just like this—drink, hire a stripper to come to the house, and if we were lucky, buy ourselves a blowjob after the music stopped. The next day we’d all stop by Greg’s office and pee in a cup, and he’d run our samples through the lab just to make sure we hadn’t picked up any unwanted visitors. Once I’d caught some unfriendly bugs from some chick, but Greg put me on penicillin and I was clean in a week, no one being the wiser. We’d even had a name for ourselves—The Wayward Sons, inspired by a sermon that Dustin’s pastor gave about carnal sins many years ago.

Flap. The G-string arched through the air and landed in my lap. She bend over and grabbed her ankles, one in each of our directions, so that we could peek at her snatch. She did a few of the obligatory rolls and open-leg, closed-leg teases, then crawled towards me to retrieve her panties. She stood in front of me, making the tip garter easy to reach. I tucked a five into it, then unrolled the Franklin and made sure she was what it was. Then I straightened my back in the chair and tucked the bill down into my drawers while watching her expectantly. I don’t know how this little ritual got started, but its been very effective. Even if the chick were an undercover cop—and she wasn’t, or she’d not have taken her G-string off—we never technically make the proposal to exchange cash for sex. It was just mutually understood—if the girl wants the Franklin, she’s gotta go into my shorts to get it. And if she’s gonna go into my shorts, she gonna have to be nice to the monster that lives there. If she’s the stuck-up type that doesn’t do extras on the side, she’ll turn up her nose at me and move on to the next guy—no harm no foul.

The stripper took the bait. She reached for my belt and undid it, unzipped me, and pulled my meat out from my jeans. Then she closed her mouth around my dick and began bobbing her head up and down while she felt for the bill with the other hand. Believe it or not, there is an honor among strippers—if she’s gonna take your cash, she’s gonna give you your blowjob. You might think that girls would just take the bill and play dumb about why you’d slip it in next to your junk, but I think it only ever happened once. Traveling strippers/hookers (if you insist on calling them that) get damn near all of their customers by word of mouth; play that trick once and you’ll find yourself all but out of business.

I cupped my hands and held the stripper’s tits while she sucked me off—technically an extra service in its own right, but pretty much a throw-in at the $100 level an up. She wasn’t too bad of a cocksucker. I gave her tits a little squeeze, sat back and enjoyed the ride.


“So what did you think of her?” Dustin asked after she and her escort had left.

“She was OK, but she was no Heather,” Greg replied, reflecting my sentiments exactly. Heather had been a favorite of ours—athletic, sexy, pretty, all natural, and disease-free. She’d probably done eight of our parties in the past few years, and we knew each other on a first-name basis (no lasts, of course). We felt safe enough with her that a few of us even paid the extra premium and fucked her pussy a couple times, something we otherwise viewed as too risky even with a condom. Unfortunately, when we tried to book her again we learned that she had gotten engaged and was out of the business. She was the third or fourth trusted regular over the years that had retired from the trade, and it was always a loss when it happened.

“So would you bring her back?” Dustin asked. He had found this us this one.

“I’m sure we can do better,” I replied, “I mean, it’s not like I wouldn’t do her again, but I’d take my chances that the next girl would be better first.”

“Well?” Dustin replied with some frustration—not because he didn’t agree, but because it was such a pain in the ass to find a good entertainer. “Do you have someone in mind.”

I started to say I didn’t when Jake stepped in and said “Don’t worry about next time guys—I think I’ve got something lined up, although it may be a little different?”

“Different? How?” I asked, “What ya got going on, Jake?” I said suggestively. Jake never had married, and most of the time didn’t even seem to have a girlfriend, yet he never talked like a man that wasn’t gettin’ any. Jake taught at the high school and coached the girls volleyball team; we had some suspicions.

“Well…” he began uncertainly, trying to decide how much of the story to tell. “There’s this girl at school, her name is Carrie Ann. A few weeks ago I found her smoking on school property, and I don’t mean cigarettes. Her friends had seen me coming and gotten the hell out of there before I could see who they were, but she’d been texting someone at the time and didn’t figure out what was happening until it was too late. Of course she freaks out when I catch her and gets all teary and begs me that she’ll do anything if I don’t turn her in. Normally I don’t listen to that crap…” I wondered how true that last statement was. “…but there was something about the way she said it that sounded…different from the way it usually does. And, I’m thinking, she’s a senior and I know she just had a birthday, so she must be 18. So I tell her that she should meet me later and explain to me exactly why I shouldn’t turn her in.”

“You dog!” Greg blurted.

“Goddamn cradle-robber,” Dustin chided, “I’m never sending my kids to YOUR school.”

“Yeah, yeah, yeah,” Jake returned, “the thing is, I think she’s a real, honest-to-god submissive.”

“No way!” I replied, by now absolutely not buying this story.

“I know, I know, it sounds like I’m making this up,” Jake answered. He was right. “But really…anyway, we’ll find out. I’m going to order her to come to our next party.”

“Order her?” Dustin asked with similar disbelief.

“Yes, order her,” Jake repeated. “I’m telling ya…I really think she’s a submissive.”

Well…maybe Jake had found some kind of special escort service, and was giving her a larger-than-life backstory. I didn’t really believe that there would be an 18-year old submissive coming to service us at our next party, but Jake said he’d take care of the entertainment for next time, and that’s all that mattered really. If this pretext fell through, he’d have to be the one to find something else.

“Whatever,” I replied, “you volunteered, so bring whatever you want. Here again?” We usually met at Jake’s house because he was single.

“Actually, it would be bad if she was seen coming here,” he said. Um, yeah, if a known student was seen coming to a single male teacher’s house, that alone would pretty much be the end of his ever working as a teacher again. “Greg, is your summer place open yet?” Greg had a lake cottage that we sometimes used in cases such as this. The downside was that it was three hours drive away—we usually had to make it a two-day affair.

“It can be. That’ll be about the start of the season, let’s just make it a boy’s fishing weekend. No one will ever know if there’s an extra visitor.” Greg added slyly.


Six weeks later, we were convened at Greg’s cottage. We all drove up on Friday night—Greg couldn’t leave until he was finished with all his rounds at the hospital and didn’t get there until ten. We drank and played a little poker, slept, got up early, and fished all day, just like we’d told everyone we would. Carrie Ann was supposed to arrive around dinnertime.

We brought in the boat, made dinner, and ate it without any sign of Carrie Ann. It was almost 7:30 before a beat-up old sedan pulled up on the lawn. Out popped a cute, perky little girl with streaked blonde highlights. She was about five-foot-six, skinny, and dressed like an ordinary teenager. She had a short tank top over another that was longer but not long enough to actually meet the top of her shorts. She wore white shorts, very short and very tight, with a big belt, and of course the teen-girl essential, flip-flops. Her legs immediately drew my attention; her thighs were slender, a thinness only found in girls that had just grown into their bodies and hadn’t completely filled out and/or ever been pregnant. She opened the trunk and pulled out backpack that seemed to have a lot in it for an overnight stay.

Jake was out the door to greet and welcome her as soon as we heard the car pull up—I think he was starting to get nervous that the entertainment might not show up after all. It had happened before of course—in-home entertainers are notoriously unreliable—but he would have been hearing about it for quite a while.

“Hey Carrie,” he called out, “I see you found the place. I was starting to get worried you weren’t coming.”

“Sorry, Mr. Hofhartz,” she said, striding towards the cottage, “it’s my fault, I took a wrong turn and got lost for a while. I had to stop and google the map on my phone to find it.”

“Well, main thing is you made it,” he replied, as she breezed in past him. She stopped at the entryway, eyeing us just as we eyed her. I suddenly felt very old. What were we, four middle-aged men, doing in a cottage in the middle of nowhere hoping to obtain sexual favors from a barely legal high school girl?

Jake stopped to make introductions. “Carrie, these are my friends,” he said, telling her each of our first names while pointing to us in turn. We sort of mumbled hellos.

“Guys, this is Carrie Ann. Or perhaps, I should say this is Carrie Anna. Right now, she’s Carrie, like she is most of the time. But Carrie has an alter ego, Anna. No, she’s not a split personality or anything, but as you shall see, when she’s playing the part of Anna, she’s quite a different person than when she’s just Carrie. Right Carrie?” Jake explained. Carrie didn’t answer, but neither did her expression change.

“Did you eat? We saved you some dinner…” Jake asked. It was strange to see him taking on this paternal attitude towards her.

“No thanks, I ate on the way up. Besides, I can’t wait to get started. I’ve been looking forward to this all week.”

She’s looked forward to this all week? What did she think she was getting into? Somehow it seemed that being used as a sex slave by four middle-aged guys wasn’t it.

“And you’ve cleared it at home?” Jake continued.

Carrie smiled. “My mom thinks I’m at band camp, and Mr. Garner (the band teacher) thinks I’m at my grandmother’s funeral. Just don’t tell grandma, this is now the fifth time she’s died!”

“Good girl,” Jake said, patting her on the shoulder. “You have everything you need?” Carrie nodded. “All right, let me show you to your room.” It was a three-bedroom cottage, so Dustin and I were sleeping on the floor so Carrie could have one of the bedrooms to herself. The three of us looked at each other while Jake showed her to the room. Just before the door closed, we heard Carrie say “I’ll be right back…or should I say, Anna will be here in a minute.”

Jake rejoined us. All three of us were looking at him with looks like “What the hell?” He laughed at our faces. “I told you, I’m pretty sure she’s a submissive. Just wait.” He crossed the room and relaxed in a wicker chair. I wondered just what Carrie, er, Anna would do, but more to the point, how much of it had one Jacob Hoffhartz already tried out for himself? I turned a little green inside imagining him rolling a hot little 18-year old.

After about five minutes, we heard the rustle of a door on the hallway carpet as it opened. We all looked expectantly down the hall. It took longer for her appear than expected, but when she emerged into view it was plain that this was because she was walking at a dirge pace, eyes downcast, completely solemn. It would not taken much to convince me that it was not, in fact, the same effervescent teeny-bopper that had entered the room five minutes before. The tank tops were gone; in its place she wore a white shirt, tied up in a knot just below her bust, none of the buttons buttoned. Her breasts were not particularly large, but they were definitely round breasts, not the pointy bumps that girls that skinny sometimes have. Given the cleavage I could see, there must have been nothing underneath. Her belly was flat as a washboard except for a silver navel ring, and her waist was subtly curved. Instead of the white shorts, she wore a black-and-white plaid pleated skirt, inspired by a private school uniform skirt. I say inspired by, because the skirt was at most twelve inches in length and would never have been allowed in any school. Her cheeks were peeking out the bottom even when she stood still, and there was no way she could sit down without showing the world her underwear. And instead of flip-flops, she wore black patent leather stilettos with pointy toes, straps around the ankles and, get this, small black iron slave rings sewn right onto the strap. They matched the other iron rings she wore; one on each wrist, attached to a black leather wristband, and another on the slave collar around her neck. My jaw literally dropped, while my dick went from zero to sixty faster than a goddamn Ferrari.

Jake’s demeanor suddenly switched as well. “Anna!” he said sternly, “It’s about time you got here. We do not like to be kept waiting!”

“Sorry, Master,” Anna said softly. She stood near the hallway, arms clasped behind her back.

“We shall deal with your tardiness momentarily. First, I have some friends that have been waiting to meet you. Show yourself to them!”

“Yes, Master,” Anna said softly. Still looking at the floor by Jake’s feet, she grabbed her shirt and pulled the two halves further apart. She adjusted it so that now rather than covering her breasts, her shirt acted like a hammock, holding her breasts up from underneath for maximum visibility.

“You know better than that! The rest, too!” Jake snapped.

Carrie/Anna widened her stance slightly, then did a deep knee bend. Although it wasn’t covering anything anymore, she nonetheless flipped up the front flap of the skirt to show us a tiny black G-string covering her crotch—and not, so far as I could see, a single hair.

Jake grunted unhappily. “Get over here!” he snapped. Anna stood up from her knee bend and walked across the floor at the same dirge-like pace until she stood in front of Jake. He turned her slightly and lifted up the back of her skirt. “What the hell is this?” he snapped, pulling the G-string far out and letting it snap back in place. Then he smacked her left ass cheek—perhaps not as hard as possible, but certainly no delicate love tap. “Get that damn thing off!” he commanded, smacking her right one, too.

She quickly reached for her G-string and pulled it down to her ankles—without bending her knees, mind you. “Stop!” Jake commanded, and she froze. He lifted the back of her skirt again. If ever an ass begged for a spanking this was it. He slapped her cheek, though not as hard as the first time. “This is for being late!” he growled. He kept smacking her ass, reddening it, but at the same time he snaked his other hand around her leg until it found her slit. “Ah, good…you have shaved completely, as instructed.”

“Yes, master,” she said softly.

Jake fingered her clitoris the whole time. He fell into a rhythm; he would spank one of her cheeks, then rub it forcefully in time with the other hand, which was stroking the hell out of her snatch. Every few seconds her experience alternated between pleasure and pain. The rest of us couldn’t take our eyes off the show.

After doing this for several minutes, Jake let go. As he pulled his left hand away, I noticed the his middle finger was glistening from dampness. “Now finish what you started. Show yourself to your guests.”

She turned so the three of us could see, did the deep knee bend again, and lifted the front flap of her skirt. Now instead of a G-string, it was a hairless crotch that we saw. Her vulva were so pink they were almost glowing, and appeared damp—this chick was getting herself all wet from this. Goddamn, she WAS a submissive.

“Come on, don’t waste our time!” Jake snarled, “I said SHOW yourself to them.” Eyes still downcast, she brought her hands to her crotch and pulled her vulva wide apart. I could see the opening of her vagina as a small black empty space. Her clitoris was enlarged and engorged; her entire genitalia glowed pink and glistened with dampness. Not only did she spread her pussy wide open for us to stare at, but she stayed that way. Strippers, sometimes they’ll flash you a little crotch but then immediately close up again. Anna just stayed put, showing herself until given further orders. When her fingers lost their grip on her own slippery tissues and her lips started folding in again, she reestablished her grip and spread herself open as wide as possible again. This was unbelievable.

“All right, that will do,” Jake ordered. “Now as I said, I am not happy about being kept waiting.”

“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 really tried. 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.

“Lie down,” he said, and realizing what he was going for, lay on my back. He now pulled out of Anna and more told than commanded her “sit on his dick.”

Anna easily shifted over to the side to straddle me, then brought her hips down until she her pussy was gripping my dick. She started to ride me like a bull, but then Dustin stopped her, and holding her still, re-entered her ass. Now she was double-penetrated, skewered in both ends. I couldn’t move very far to get a very long stroke, but it was made up for by other stimulation. Anna was again going crazy. She arched her back and grunted, mouth half-open with a faraway look, as she received stimulation in both holes. Her pussy was practically flowing like a river, and each labored breath made her pussy squeeze my dick just a little. I kept making my little strokes, but I probably could have cum sitting still, just watching her—her lithe young body impaled on my dick, arching her back, face twisted in ecstasy, pushing her crotch back and forth what little she could, and being rewarded for each stroke by the feeling of two erections penetrating her orifices. I had the best seat in the house.

I noticed that her breasts were hanging down, pointed right at my face. I tried to reach up to kiss them, but they were too far for me to reach without pulling out, which I was NOT about to do. So instead I ran my hands along her slim waist and ribcage, working my way towards them until I reached the tits. I gently touched the erect nipples and squeezed them in my fingers. The third source of pleasure was too much. The sensations of her ass and pussy together were almost overwhelming; feeling her sensitive nipples being caressed as well put her over the top—again. Her eyes shot open, she got a faraway look, and I felt the ripples in her vagina as she came for the third time.

All of a sudden, Carrie/Anna was tired. I guess three orgasms will do that to a girl. She collapsed on top of me, head to the side next to mine. Yet she still lay there, keeping her legs wide, allowing Dustin and me to keep fucking her. What a woman—totally spent herself, yet she still opened wide and let her partners get what they came for. Shortly after she came, Dustin was done, too.

When he pulled out, Anna drew on energy reserves. She sat upright and began to fuck my dick with her pussy. But there was one more man yet to account for. Greg came over sheepishly, openly jerking himself as I had done earlier. He came over where she could see him, but didn’t actually force himself upon her; he could tell she was tired. No need; reminded of him, she bent forward to try to reach his dick with her open mouth. He quickly took two steps forward, and now again Anna had two dicks at once, just not in the same places. When Greg was good and hard we switched; she straddled him, and now I plugged her ass. It was really tight, and I heard her suck in a little when I penetrated. I suppose that three men was a little much for doing anal the first time. But I hadn’t ever had the chance to do it before, either, and was anxious for the chance to try it. I wondered if I should pull out, but Jake was watching her closely and nodded that it was OK. So I screwed her up the butt, watching the ripples on her tight-as-a drum cheeks. It didn’t take much of that before I was ejaculating into her murky depths.

Greg decided to forgo the butthole. When I was done, though, he rolled Anna over onto her back and pounded her missionary style. That was a good thing, because she could satisfy him with little or not effort of her own—she just had nothing left to give. It may or may not have still felt good, but she obediently laid there let Greg fuck her still-soaking box until he got his second helping, too.

As soon as Greg finished, Jake was on his knees by her head, stroking her face, asking if she was all right. She nodded weakly. No one needed to be told that she was done and the night was over. Jake picked her up like a bride and carried her to her bedroom. Although he had his own room, I’m pretty sure he spent the night in hers. Dustin and I pulled out our sleeping bags, laid them on the floor, and fell asleep, the scent of sex still hanging heavily in the air.


I was awakened by the sound of sizzling and the smell of bacon and percolating coffee. I stumbled out of my sleeping bag to find Carrie/Anna up and cooking breakfast—naked, save the slave collar, wrist restraints, and stiletto heels. She didn’t look up from her work when I appeared in the kitchen. I saw the bacon grease splattering from the pan, and without thinking I blurted out “Put on an apron before you get burned!”

Anna looked over at me. The expression on her face seemed to say are you sure you want me to cover this up with an apron? “I can be careful, master,” she said, pleading; she would wear one if I ordered it, but she didn’t want to.

“OK, but be sure that you are,” I relented, “I don’t want to be driving you to the hospital and trying to explain third-degree grease burns on your tits!”

“Yes, master,” she replied, but I saw a hint of a smile on her face as she imagined the scenario.

Jake was now up, too. He said good morning to me briefly as he shuffled past. He stopped by Anna, saying “Ah, breakfast is started. Very good. I am pleased.”

“Thank you, master,” she beamed. Then Jake grabbed her hair and pulled it down. She had no choice but to bend her head back. When she did, he put his mouth over hers; I could tell they were busy intertwining tongues. He also slipped his finger between her thighs, stroking her slit. It was heaven for her—affection earned through submission was the only affection she would trust. It seemed like she was lost in the kiss, like all time and space had disappeared for her and that she would have happily stayed in Jake’s grasp forever. But then the bacon did splatter her, a tiny speck on her belly, and as much in surprise as anything she gave a start. Jake let her go, saying “You’d better get back to your cooking or else you’ll burn the bacon.”

“Yes master,” she replied, glowing with happiness.

The rest of us were up now. Jake told us to go sit at the kitchen table, breakfast would be served shortly. Sure enough, Carrie/Anna came out with a plate of eggs. It was not enough that she made breakfast, she also served it. She came up to Greg first, holding the plate so he could spoon in some eggs. I followed suit, but when she came to Jake, he said “three spoonfuls please,” then stuck his finger between her legs again while she served out the requested amount. She involuntarily shifted slightly and bit her lip in response. When she went over to Dustin, he did the same.

She returned with the bacon, and now all of us specified how much we wanted, then groped the chef while she served us. Finally she came back with coffee. When she was finished serving, Jake said, “Thank you. Now, masturbate for us while we eat!” She immediately did the deep knee bend, pulled her vulva apart, and began stroking her tender pink flesh.

“Isn’t she going to eat?” I whispered to Jake.

“No, she won’t eat while she’s being Anna,” Jake answered, “at least, not food. I’ll save her some for later.” That would explain why he had taken at least two people’s worth of food on his plate.

Anna closed her eyes and got into her task. I had to keep reminding myself to keep eating, I was transfixed by the show. I’ve never been able to look at a plate of eggs the same since.

Jake ate about half his plate, then announced “Anna! I am finished for now, put this in the microwave for later.” Startled back to earth, she quickly jumped up and complied. When she returned, Jake was standing and had pulled out his chair. He said nothing, but pointed under the table. Obediently, Anna crawled under the table. He undid the belt on his robe and sat back down. I didn’t need to look under the table to know that his dick was buried in Anna’s throat.

The rest of us kept eating, not sure where to look. “C’mon guys,” Jake said quietly, “there’s a naked girl under the table. Grab her and stuff.” So we did. Dustin and I had easy access to her breasts, while Greg played footsie with his big toe and her clit. I wasn’t finished, but I no longer gave a damn about my food.

With a small grunt Jake popped off in her throat, then told her to swallow it right away. An instant later I felt fingers at my boxers; I lifted my butt so she could pull them down. I sighed as the warm ecstasy of gentle tongue engulfed my junk. She sucked with vigor—of course—and I found myself resting my hand on her head just so that she didn’t bang it on the bottom of the table in her single-minded drive to bring me off.

Jake did something I hadn’t expected; he got up and began to clear the table. I would have thought that would be something your servant would do…until I realized he perhaps wanted the table for something else. She was still sucking me when Jake finished clearing and threw what was left of our supply of condoms on the table. “Do you want her to stay down there, or?” he asked.

Actually, I was interested in diving into that hot young pussy one more time, so I ripped open a rubber. I stopped Anna for a second, showed it to her, and she immediately took it into her mouth and then rolled it onto me with her teeth like we had shown her the night before. I pulled back my chair and got up; Anna crawled out from under and without needing to be told lay down on the kitchen table. “Grab your ankles,” I grunted, and she did. Then I slipped my dick easily into her pussy, dripping wet from masturbating.

I aligned her hips with the edge of the table and gleefully pounded her young flesh. The table was a bit too short, though; her head hung over the other side. This gave Dustin an idea. He whipped his dick out, lay his hand on Anna’s throat, and gently pushed her head down below the level of the table. Then he shoved his cock between her lips and began to throat-fuck her. With her head tilted down, it straightened the throat and allowed him even deeper penetration than her usual efforts, to the point that his balls kept whacking her in the nose.

For my part, I kept fucking her, enjoying what might very well be the last time I would ever fuck a girl this young. I touched her firm breasts, and ran my fingers along her flat belly, pumping her vagina for all I was worth all the while. I couldn’t see her face because it was draped around Dustin’s dick, but it seemed like she preferred being fucked by more than one guy at a time. It was OK, I had plenty of stimulation from that young, firm body as I plowed her hairless snatch. Eventually I could hold it no longer and exploded within her.

I now backed away to give Greg his turn, but he seemed to want to wait until Dustin came, which wasn’t going to be much longer. He actually came down her throat—as in, she caught his load on her epiglottis and swallowed it, but it was so far down that she couldn’t retrieve it display it like she usually did without choking herself. Dustin didn’t seem to mind.

Greg now whipped on a rubber. He had Anna stand up and bent her over the table. I think he wanted to nail her up the ass, having missed the chance to do so last night. When she was spread out before him, though, he saw the inflammation of her anus and as a doctor knew that meant she was sore from the night before, so he settled for plugging the hole designed for the purpose. As he drove her, Jake came close and got down on one knee next to her right leg. He reached up and found her clitoris even as Greg was pounding her cunt. He began rubbing it wildly, and succeeded in bringing her to her own orgasm just before Greg blew his load.

Greg backed away, still in the post-orgasmic semi-stupor, when Jake stood up and took charge. “Guys, Carrie Ann needs to get back to town pretty soon. Is there anything else you required of Anna?”

We were caught by surprise by the suddenness of the request, but I suppose it had to end sometime. Sadly, we all shook our heads. “All right then, Anna…you are dismissed.”

She curtsied politely, saying “yes, master.” Then she went back into her room for a second, then hit the shower. When Carrie emerged fifteen minutes later, it almost as if she was another person that had been in the bathroom all morning and just now was coming out. She was drying her hair with a towel, wearing a bikini top with a tank top over that by design allowed her belly button ring to show. The white shorts and the flip-flops were back, as was the chatty, 18-year old personality.

Seeing her, Jake hit the “minute” button on the microwave. “We saved you some breakfast, Carrie,” he announced, returning to that paternalistic tone.

“Thanks, I’m starving!” Carrie declared. She bounced across to the kitchen table, where Jake brought her the re-warmed plate of breakfast. The transformation was downright bizarre; now she was the bubbly teen again, not the submissive servant, while Jake was the father figure watching out for her, not the demanding master. I couldn’t just flip a switch and relate to her in a completely different fashion the way that Jake did. I think the other guys felt the same, because none of us had a damn thing to say.

Carrie Ann and Jake chatted idly about school gossip and what her plans were for the rest of the day while she ate her breakfast. I felt like I was eavesdropping—I could scarcely believe that a half-hour ago I had been fucking this very same girl. Although, in some respects, Jake had been right, it wasn’t the same girl. This was Carrie; the girl we had just fucked had been Anna.


That weekend turned out to be the last regular meeting of the Wayward Sons. Jake succeeded in his quest—he hooked Carrie Ann up some billionaire businessman in New York through the web. This guy flew her out to New York for a test run, and on the spot asked her to be his mistress—for $5,000 a month plus all expenses paid in a swanky Fifth Avenue condominium. She was excited as a little girl when she came back to tell Jake about it—but under orders from her new master, she was no longer permitted to have sex with anyone else. The girl who could never say no had no trouble saying no now that she was under orders to do so. She stuck out the last few weeks of school, graduated, and within a week had moved permanently to Manhattan.

As for the Wayward Sons, after Carrie Ann, the thought of renting another stripper lost its appeal. A skanky slut distastefully licking the top three inches of your dick while thinking about the smoke or crack or whatever she was planning to buy with your money as soon as she was done? Or a hot little barely-legal submissive who sucks you dry with no hands, focused only on getting you off, and then lets you fuck her up the ass afterwards? There was no contest. It was hard enough to find a stripper that sucked dick on the side; finding a submissive schoolgirl was, well, it was never going to happen again. Dustin did some legwork looking into possibly going to Vegas to do something similar to that weekend, but the cathouse bill alone would have run like $1500 a head—and even then, it would still have just been a girl doing her job, not a girl that was really digging it. There would never be another Carrie Ann, and that fact pretty much meant the end of the Wayward Sons.

After she moved, Jake has stayed in email contact with Carrie Ann. He’s really become her surrogate father; the fact that he also fucked her who know how many times presented no incongruities for her, since her real dad had done the same. He would sometime pass on stories she would tell him—things like how many games she was getting to see at the Garden, and how there was this luxury box shared by all these rich guys who bring their mistresses to games there and can’t afford to be seen with someone not their wives, and even though there was a private bathroom you always had to go outside to pee because there was always someone fucking in the john. Last week, though, he told us Carrie Ann is coming back for a visit because her little brother is graduating from this year. Apparently she told her new master about Jake and what he’d all done for her, including getting her hooked up with him in the first place. He gave her permission to see Jake again, provided that he wore a condom. Jake was nice enough to ask how she felt about an evening with the gang and she was all for it—she even specifically said “make sure those guys do that double penetration thing again.” Besides, she said, her new master was going to punish her for every naughty thing she did while she was away, so she’d better come back with some good stories on just how naughty she had been so he’d have plenty of reasons to punish her.

So it looks like in a couple of months the Wayward Sons will have a reunion of sorts. We’ll ask Carrie about how she is and how she likes living in Manhattan. Then she’ll change into Anna, and we’ll abuse her like the submissive sex slave she is, taking her any way we want her until we can’t get it up anymore—and she’ll love every minute of it.

I’m already fucking hard just thinking about it.

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