Carrie Ann and the Wayward Sons

"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.

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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 sayare 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 camedown 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.

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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.