The bell signalling that the first class of the day was going to begin in ten minutes rang and students began to head for the front door of the school. Michael and Todd waited in the parking lot to catch their friend Lisa before she joined the sea of students flowing into the school. As Michael calmly scanned the paths leading to the school, Todd fidgeted nervously.

“You okay, man? You look like you’re going to pass out,” Michael asked.

”No, Mike, no. It’s just that, what we’re about to ask-” Todd looked around side to side like an addict nervously looking out for cops when he went to go see his buyer. “Lisa’s been our friend since we were in middle school. Do you really think she’s going to go for this?”

“Chill, Todd. You know Lisa wants to go to Columbia out in New York, and it’s one of the most expensive schools in the country. By agreeing to do this, she’ll collect a nice chunk of change to go towards that.”

“But she’s seventeen like us, so she’ll have this year, next year, and two summers to earn enough money to go there. Isn’t that enough?”

“Yeah, but going to school in New York is going to be REALLY expensive. Tuition, books, food, rent, transportation, and I’m sure she would like to enjoy the entertainment of New York as well, so she’s going to need all the money she can get. Besides, doing this with two friends has to be less weird than doing it with most of the people she normally does this for.”

Todd was on his way, but he still wasn’t fully convinced. “Yeah, but, why the both of us at the same time? I gotta admit, I really would like to do it with her, but I’m not too keen on looking at your dick while we’re doing it. Besides, I always figured that my first threesome would involve two girls and me, not a girl, myself and one of my male friends."

Michael was starting to irritate him; they had gone over most of this already. "Damnit, Todd, I told you like ten times already that Lisa’s schedule is booked up a month in advance, that’s how good she is. The only chance we have to get her to squeeze us in is to offer for her to take care of us at the same time, therefore making twice the money in just one appointment space.”

“But, do we really need to do this? I mean, we can hold out for a while, can’t we, or maybe find some girls on our own? We’re both relatively good-looking guys, right?”

Todd’s questioning was transitioning from irritating him, to pissing him off. “Again, it’s like I told you; my stepmom is away with dad for a month in Europe, and Jaclyn is studying for a semester in Europe. Everyone thinks that I’m a nice guy that wouldn’t cheat on his girlfriend, and I would like to at least keep the illusion of that intact by not having sex with a girl who will end up gossiping about it with her friends.”

“And you’re sure Lisa won’t?” Todd asked.

“No way.” Michael shook his head. “She’s got rules, and confidentiality is one of her biggest, she wouldn’t keep any of her clients if she didn’t.”

“I guess that makes sense, but unlike you, everyone knows that I’m a sleaze, so I don’t have any reputation to maintain. I’m a free agent, baby,” Todd said as he spread his jacket open to show himself off, as if he were hot shit. Michael laughed in response.

“And you think that makes you more desirable to women? You actually had an attractive girlfriend, and you fucked it all up, Todd.” Another laugh escaped his mouth. “Her best friend and her mom, really? You should have thought about the likelihood of getting caught, especially with a girl like Harper. Oh, and mentioning how you also had sex with Becky’s stepmother? You know how she hates her, and she would love to tell her dad about it, and as a result, you also lost her stepmother, and your last remaining source of reliable pussy.”

Todd’s smile vanished from his face and he stuffed his hands into his pockets as he was hit by a cold blast of reality.

“I mean, you might be an ok looking guy, but your personality is shit, Todd,” Michael added.

The reality of Michael’s observations really hit Todd in the gut. “I guess,” he admitted with a depressed sigh. He realized that while sex did come to him, it was often inadvertently, and the times he actually tried to land a girl usually didn’t go so well, in no small part due to his lack of tact, and reputation for being a horn dog. How Becky ever put up with him was a mystery to him, even with a dick his size.

“Besides all of that, I really doubt that you care about the circumstances of how you get into Lisa's pussy. I know that you think about her as more than a friend.”

Todd’s face crinkled questioningly. “How would you know that?”

“Because I think about her the same way."

"Yeah, you're right about that. Alright, I’m in, for sure," Todd said, with certainty this time.

Both him and Michael had had a crush on Lisa for a while now, but especially since she turned sixteen and began to dress and act sexier. When they discovered her new side business to save for college, they only lusted after her more, but up until there new time of sexual desperation, neither of them wanted to risk their friendship with her by either asking her out, or by asking to pay her for her services.

”Okay then, let’s do this. Look, here she comes, man. Just act normal, ok?” Michael directed Todd.

The guys saw Lisa approaching them from the same route that she always took to school in the morning, and looking as sexy as usual. She was wearing a short, lacey black dress that showed off her cleavage, and black combat boots with black thigh-high socks. The ensemble was completed black nail polish, black eye shadow and black, naturally, eyeliner. Despite this, Lisa didn’t have any tattoos or piercings, other than her ears, and her black hair flowed down to her shoulders, rather than being cut in some kind of extreme do, such as a mohawk, or a buzzcut.

While Lisa’s look incorporated many gothic elements into it, it was not as extreme as most of the goth crowd at school, nor was it because she actually liked goth culture. In reality, the reason she dressed like she did was a business decision. Lisa was a working girl, trying to save up money for college, and the dark and moody look really reeled a lot of guys in. There were already a ton of valley girl type, cheerleaders and nerds working as professionals at the school, and seeing as how no girls in the authentic goth circles were interested in doing her kind of work, Lisa had managed to corner a very exclusive market.

The two guys looked at each other and nodded, as if to say, let’s do this. They walked towards Lisa and stopped her before she made it into the school.

"Hey, Lisa. How’s it going?" Michael asked, confident as usual.

"Hey, Lisa." Todd added nervously.

“Hey, guys. I’m good, what about you?” Lisa replied as her mouth sprouted a big smile. She ran her left hand through her hair and let it fall over her shoulders, inadvertently causing the boys to look as it fell next to her impressive breasts.

“We’re good, we’re good.” Michael replied as he took the lead, knowing Todd would be useless in convincing Lisa to go through with this. “Listen, you know how we know about your side job, right?”

Confusion crept into the smile on Lisa’s face, while her eyebrows crinkled questioningly. “Yeah, I know. I told you guys about it after my first client and you both said you were cool with it as long as I stayed safe. Why are you bringing it up?”

“Well-” Despite taking the lead and being confident up until that point, Michael still couldn’t help but feel awkward asking one of his friends of several years to have sex with him, and another male friend at the same time, for money. “Todd and I are going through a bit of a dry spell lately in terms of female, companionship. We know you’re pretty busy with other clients, but we were hoping if we could have a session with you, all three of us that is, and we each paid you your usual fee you might be able to squeeze us in.”

Finally, the smile on Lisa’s face had melted away completely, leaving a look of confusion, and even a little hurt, on her face. “Are you really asking me to have sex with the both of you at the same time? We’ve been friends for years.”

To show he was serious, Michael removed a wad of twenty-dollar bills, totalling one hundred, and Todd followed suit, leaving Lisa with a total of two hundred-dollars staring her in the face. She couldn’t believe that two of her longest friends actually wanted to pay her for sex. They had never shown an interest in her like this before; sure they commented on how good she looked and how her clients weren’t paying her enough, but this was the first time they done something so much as hint that they were interested in her for her services.

At first, Lisa was kind of weirded out, even hurt and offended, by the prospect of having two of her best friends pay her to have sex, but the idea actually grew on her after thinking about it. She would have been lying if she denied being curious about what Michael and Todd could bring to the table sexually. Rumors about the two of them and their sexual prowess, and the hardware they used for it, had swirled around the school for a while now, but she never gave any serious thought to having sex with either of them, until now at least.

Eventually, Lisa smiled again, but not in the way a friend would towards another friend. This time her smile was mischievous and tantalizing, the kind of thing she usually did when convincing shy and nervous guys that they should utilize her services. The dirty thought of having sex with TWO good friends was actually pretty appetizing to her, but there was also a business angle to it.

“Well, boys.” Lisa reached out and started stroking one arm of each of the guys as she spoke in a seductive tone. “I’m sure that I could do something for two very good friends of mine, but I am a business woman after all. What say you raise my fee to, oh say, one hundred and fifty, a piece, and then we have a deal.”

The guys’ mouths literally fell open.

“One-fifty each? You’d already be making twice what you make for the same amount of time you spend with one client,” Todd countered.

Lisa’s smile just broadened in response. “Yeah but, I’m saving up for university, a very expensive university, and a girl needs to spend money on fun stuff as well. Besides, I’ll be doing twice the work, and I don’t usually do threesomes. Don’t worry, I can assure you boys, I’m worth it.” Her hands made their way from the guys’ arms over to their crotches and she started rubbing their cocks through their pants.

The seductive tone, the wicked smile, and finally Lisa rubbing their dicks in public with other students around convinced Michael and Todd that Lisa was worth the ridiculous price. They each took out their wallets and scraped together enough cash to pay Lisa, although Todd needed to borrow thirty bucks from Michael to pay off his share, although he assured him, like he always did, that he would pay him back. Not likely, Michael thought.

The fact that she was able to make the guys scramble to pull out more money to pay to have sex with her made Lisa feel both powerful, and horny. She bit her lip and gave her most seductive smile. "Well, boys. My mom and dad are at work right now, and if you want this to happen, we’re going to need to do it during class, otherwise I’m all booked up after school, and during lunch break. So, you boys coming?” She began to walk away slowly, putting one foot in front of the other and turning to look back at them with a pouty face.

They knew that they could get into serious trouble for missing first period, but they didn’t care; Todd and Michael were hornier than the Devil himself. They walked with Lisa to her house. After she let them in, she took each of them by the hand and led them to her bedroom.

As they all filed into her bedroom, Lisa grabbed Michael’s head with both of her hands and pushed her lips against his and started kissing him passionately. She shoved her tongue into his mouth so far that it actually tickled his tonsils. The teens’ bodies pressed against one another as they made out, Lisa grinding her crotch into Michael's already stiff cock. While she didn’t normally kiss clients, things were different today, considering she was friends with the two clients in question.

While Michael and Lisa kissed, Todd entertained himself by bending down and lifting the hem of Lisa's short black dress to find a pair of sexy black lace boyshorts that didn’t manage to completely cover her ass cheeks. He grabbed two juicy handfuls of her butt cheeks and squeezed them like oversized stress balls. Since Michael and Lisa were still fighting their duel of the tongues, Todd got up and started to kiss the back of her neck, while his hands remained affixed to her luscious ass.

Sensing that Todd needed some attention, Lisa broke her kiss with Michael and snaked an arm behind her head to grab Todd’s as she turned her own head and started to kiss him. She kissed him just like she kissed Michael: with a whole lot of tongue. As she made out with guy number two, she kept grinding herself against Michael’s crotch while he started kissing her neck and breasts. He lifted her dress and proceeded to pull it over her head, causing Todd to usher a ‘Hey, man,’ while Lisa simply giggled at the two boys before resuming her kiss with Todd.

Upon removing the dress, Michael smiled as he feasted his eyes upon Lisa’s ample C sized breasts, held within a black lace bra that matched her boyshorts. He reached around her and unhooked the bra, letting it fall to the floor, revealing her puffy, pink nipples surrounded by light brown areolas. The sight caused Michael to groan in delight and he started sucking on her left nipple as he squeezed her right breasts.

Lisa removed her crotch from Michael’s and started grinding her ass against Todd's granite-hard cock as he slid a hand into her boyshorts and began rubbing her wet pussy lips. Lisa’s grinding was slow and sensual, like an experienced stripper, while Todd’s performance was a little less skillful, quickly abandoning the lips of her pussy, and unfortunately for Lisa her clit. Instead, he plunged two fingers into her pussy and began to fingerfuck her, driven by such horniness that he practically forgot any skill that he had previously accrued from his experience with other women; that was how much Lisa excited him.

As Todd continued his fingering, Michael, no longer preoccupied with Lisa’s mouth, or crotch, lowered her underwear and slid them down her long, milky white legs, leaving her in just her black thigh high socks and combat boots. A medium sized landing strip of pubic hair trailed from Lisa’s lower abdomen to just above her clit, as to provide a map for anyone to follow to her sweet spot. This aroused him, as it was easy to just shave everything off, or just let it grow it, so this kind of care was really impressive.

Deciding that they had all had enough foreplay, Lisa fell to her knees and unzipped Todd and Michael. Upon pulling down their pants and underwear, she was rewarded with two eight-inch cocks to pleasure, although she swore that Michael’s was just a little bit bigger. She immediately began to stroke each of them, while deciding to suck Michael’s first, managing to swallow almost all of his shaft in a single gulp. With a little bit of pushing, she was able to fit in the last half an inch of him and press her nose against his lower abdomen.

Both Michael and Todd were amazed at what they were witnessing; a good friend of theirs for years, dressed like a sexy goth, was going to town on their cocks with her mouth and both hands while she gazed up at them longingly, as if she desperately needed to please their cocks for some reason, as opposed to simply being paid to. While Lisa was apt at making herself look interested while she was having sex, there was no need to pretend this time; the whole situation was just as hot for her as it was for the guys.

At that point, Lisa had switched between the two cocks several times, but the fourth time she switched back to Todd, he grabbed Lisa’s head and forced her to deepthroat him roughly, eliciting a loud gasp from both of them. After squeezing his whole cock into his mouth, he let her take him out of her mouth, but he kept his hand on the back of her head and forced her to suck him faster. After almost a full minute, even though Lisa had kept stroking him off while she blew Todd, Michael thought that Todd was getting greedy.

“Hey, don’t be a hog, asshole,” Michael said as he shoved Todd’s shoulder.

“Come on, man. I’m just having a little fun. I’ll-“

Michael cut him off. “I’ll tell you what you’re gonna do-“

Lisa then pulled herself away from Todd and took his cock out of her mouth. She continued to stroke the two of them, but at a much slower pace.

“I’ll tell you two what you’re going to do. I have to be back to school in time for Mrs. Klein’s economics class, because I can’t afford to miss that one, but grades are only in the high eighties. So, what you’re both going to do is stop arguing over my mouth, shove each of your cocks into one of my holes, and fuck me senseless, got it?”

The goth-looking teen’s declaration got their attention and they both nodded.

Lisa smiled. “Good. Now, since I know you two will probably fight over who gets what hole first, Michael, lie down on the bed, and you’ll get my pussy. Todd, come up behind me, and you can have my ass.”

Normally this as where she would ask her clients to put on a condom, but she trusted Michael and Todd. The two may have been using a friend of theirs for her body, but they were still friends. In addition, Lisa really wanted to feel two unwrapped cock in her body, as it had been too long since she had been fucked bareback.

All the teens took their positions: Michael lay down on the bed, Lisa lay on top of him, and Todd came up behind her and stroked his cock as he aimed it at her ass. Lisa took hold of Michael’s cock and started to lower herself onto him, letting every inch of him penetrate her. Her eyes were squeezed shut as the large shaft made its way to the back of her vaginal canal. After getting used to the feeling for a second, she began to slide his dick in and out of her pussy.

It was a surprise to Todd to find the image of two of his friends fucking to be a real turn on. Even though he was straight, and he thought that seeing a male friend having sex might have made the situation weird for him, he was so aroused by the thought of double teaming a hot friend like Lisa. As good as the view was though, it wasn’t nearly enough for him, so he moved closer to Lisa and shoved his cock forcefully into her asshole, causing her to let out an ‘Ahhhhh,’ but after that she didn’t do or say anything other than moan in pleasure as she was fucked by her two friends.

Looking up at her bouncing breasts as she rode him, Michael couldn’t resist lifting his head up and sucking one of her nipples into his mouth, swirling his tongue around the stiff little mound. While Todd licked lovingly at Lisa’s nipples, Todd was a little less gentle, slapping her ass cheeks and turning them red whenever he wasn’t squishing them in his hands like silly putty. All of the action made Lisa moan and scream like a complete slut as she had both of her sexy holes stuffed.

"Fuck, fuck, FUCK,” Lisa screamed. “Oh my God, this is so fucking amazing.” She giggled. “Ohhh, you have no idea how much I love cock. Come on, boys, drill me fast and deep with your big cocks."

The dirty talk from the girl who, until this morning, was just one of their friends caused Todd and Michael to pick up the intensity of their thrusts. Her words did the trick, and after several seconds of the guys intensified thrusting, Lisa’s muscles in and around her pussy and ass tightened around the cocks inside of her. The sensation of her muscles squeezing his dick sent Michael over the edge and he blew a massive load into Lisa’s cunt.

Afraid of falling behind, Todd grabbed Lisa’s ass and really went to town on the sexy goth’s rear, his balls slapping against her cheeks as her tight asshole continued to clamp down on his cock even after her orgasm. Luckily it didn’t take long for him to cum as well, and he delivered a load of his own deep into her ass, a new sensation for her, as no one had ever come in her ass before. Todd collapsed on top of her momentarily, having exhausted all of his energy pounding her ass, squishing her between himself and Michael.

Up until then, Lisa had only ever let clients fuck her asshole if they were wearing a condom, and even when she had had sex simply for pleasure outside of work, no one ever blew a load into her ass until then. The feeling of the warm, creamy liquid being injected into her asshole was so pleasurable that she thought she was going to have a second orgasm immediately. Unfortunately, the second orgasm didn’t come, but she wasn’t disappointed; she knew at least one more was coming soon.

Both of the guys were pretty spent, awkwardly climbing off of each other and standing next to the bed as they stretched. They figured that after all of that, Lisa would say that it was time to wrap things up. Instead, she rolled onto her side, ran a hand back and forth over her sides seductively, and surprised each of them with a question that neither were expecting.

"Mmmm. Michael, I think you should have a turn with my ass now, don’t you think?” She turned to Todd. “And Todd, would you like to try out my pussy?"

The guys just stared at her in disbelief and then looked down at their soft dicks. Lisa knew what they needed and smiled sweetly at them.

”Don’t worry, boys. I got you covered.” She got off of the bed, kneeled down in front of them, and proceeded to stroke their cocks while taking turns sucking them off again.

It took less than a minute before both Todd and Michael were groaning in pleasure and their cocks were hard as rock again. This time Lisa climbed on top of Todd and guided his dick into her pussy. Meanwhile, Michael came up behind her, spread her ass cheeks, and shoved his cock into her ass. She screamed even louder than when Todd was in her ass, as Michael’s larger shaft pounded her asshole.

The insatiable teen jumped up and down Todd’s smooth, wet shaft, as Michael slammed her ass as hard as he could. There was still a part of Lisa that questioned whether or not it was a good idea to make clients out of two of her longest friends, but that part found itself quickly diminishing. While most of the sex she had was forgettable, the guys usually being those that had almost no experience, Todd and Michael definitely knew how to please a lady. The added bonus of them being two of her best friends only added to the sexiness of the situation and it drove her wild, and of course the money she was squeezing out of them helped excite her as well.

Said sexiness caused Lisa to have another orgasm, with each of the guys having an orgasm of their own a short time later. This time however, the guys wanted to see their cum all over Lisa’s face.

“Ugh, Lisa,” Michael grunted. “Would it be ok if Todd and I came all over your face this time?”

“Yeah, can we?” Todd added excitedly.

Seeing as how all of her clients had to wear condoms when they came, this wasn’t something that Lisa normally allowed, or had experience with. Still, she had watched enough porn to know what guys wanted when they came all over a woman, and the prospect of doing something new excited her.

“Mmmm, I’d like that boys. Go on then, cum all over my face,” Lisa said in agreement.

The guys pulled out of Lisa and she quickly got down to her knees on the floor. She massaged her breasts, stuck out her tongue, and urged them on as Michael and Todd stroked themselves off.

”Oooh, yeah. Come on, boys, I need your cum. I need it on my tongue and all over my face. Come on, cum all over your friend’s pretty little face.”

The dirty urgings of Lisa sent the two guys over the edge, and within the span of two seconds, both blew their loads onto Lisa. Mike came first, the first blast hitting her left cheek, with a second landing just below her left eye. Before he was able to unleash his third load, Todd released his first one and managed to get both it, and his second one directly onto Lisa’s tongue. Finally, both of them released a third stream, both of which landed on her chest, one stream landing in the middle of her breasts, the other one landing just above her right nipple.

Warm sperm bathed Lisa’s face and pooled on her tongue. She swallowed what was on her tongue and then stuck her tongue back out to show that she had consumed all of it. Next, she wiped the cum from her face and licked and swallowed it as well. The cum on her chest had run into the middle of her cleavage, while the final stream had dripped onto her nipple. Using a single finger, she swirled the cum around her nipple, causing it to harden once again before she licked her fingers. Finally, she scooped up the last bit of cum on her and swallowed it like the rest.

Lisa had somehow managed to feel both exhausted, and energized at the same time after what just happened.

“Well, well, well. That was quite some session, boys. I don’t think I’ve ever been fucked as good as I just was. It’s a shame you didn’t come to me sooner, before I started charging for it.” Lisa gave the guys a devious little smile. “We could have had a lot of fun… for free too,” she added with a giggle as she got up to get cleaned up. The guys moaned and released a series of ‘Damns’ as they realized how stupid they were for not trying to get with Lisa sooner, and without offering her money first.

All three of the teens were getting dressed, when Lisa had an interesting idea come to her. Just as she was reapplying her eye shadow as she looked at herself in the mirror, she made the guys a proposition of her own.

“So, boys, I have an offer for you two.” The guys stopped dressing and looked at her. “You know how busy I am with clients for the next little while, but I might be willing to bump some of them off of my schedule for such good-“ Lisa licked her lips and smiled a not so innocent smile before finishing. “Friends, if we can come to an understanding.”

The guys were intrigued. “What kind of an understanding,” Mike asked in a voice that he tried to pass off as sly.

“First, I’ll fuck the both of you again, but it has to be together. I need it to be financially beneficial to drop a client and risk my reputation, so with the both of you I will make enough money to make up for the loss of another client. I can’t keep skipping classes to fuck you guys just so I can avoid cancelling clients. Besides, I don’t think it would be anywhere near as pleasurable if I had sex with just one of you at a time.”

Both Michael and Todd nodded, not at all bothered with the prospect of double-teaming their smokin’ hot goth, best friend.

So far, so good, she thought to herself. “And two, it’s gonna cost you $200 a session, each.”

Once again, the guys’ mouths fell open in shock.

“Two hundred now?” Michal responded. “That’s insane. We just paid you extra on top of what you usually charge for a single session.”

“And, we’ve been friends for years, and I can tell you enjoyed yourself too,” Todd added. But Lisa only smiled more.

“Yes, but in addition to the effort I would need to put in to take care of two guys at once, I recently discovered just how talented I am at taking on two guys at once, so I think it’s only fair that I increase my rate for group jobs.” Her smile broadened even more, making her look even more devious. “The both of you have rich mommies and daddies, so I know that you can easily get the money for this.”

“Besides-“ To push the two over the edge for sure, she walked over to the two and started to gently stroke their cocks through their pants, just like when she first convinced them to pay her more than her usual fee. “You won’t turn me down, no matter how much I charge. You know I’m really good at this, so do yourselves a favor: give yourselves the pleasure you deserve, and stick with someone who knows how to give you that pleasure.”

To end her speech, Lisa kissed Michael on the lips, and then leaned over and kissed Todd just below his ear, and with that, the deal was done.

“Okay!” Todd blurted out. “We have a deal.”

Michael let out a sigh. He would have liked to at least try to squeeze out a slightly better deal, but Todd’s dick just ruined that possibility.

“Great.” Lisa beamed. “How about we get together next Friday at six? My parents will be out of the house to go see a play. Mr. Caan was supposed to be my client that night, but he has three appointments booked with me this month, so he can afford to lose one. I’ll see you guys downstairs when you finish getting dressed.” Without waiting for a reply, she left her room and headed downstairs.

The guys looked at each other. “Mr. Caan, huh?” Michael said.

“Well, it’s never gonna be the same again sitting in one of his classes,” Todd replied with a stunned look on his face.

“Hopefully Lisa won’t tell us anymore about her clients, or else school’s going to become too awkward to attend. Let’s hurry and get out of here. Neither of us can afford to miss second period,” Michael said.

The two quickly finished dressing and walked with Lisa back to school, each of them eagerly anticipating the coming Friday. All three of them thought that what they had just done was going to be weird, but they were pleasantly surprised that it turned out to be incredibly erotic, and they were sure that it would happen again, many times. As long as the boys can afford it, Lisa half-joked, half-promised herself.