tagGroup SexCarrie Ann and the Wayward Sons

Carrie Ann and the Wayward Sons

byDrSqueaky©

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."

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