A Career Change? Ch. 02 - Preparing

"Being naked didn't seem to faze you at all."

"It did take a little getting used to. The hard part was having to come out with an erection each time. Luckily, I had some help with that."

"I am not sure that getting a hand job can be hard. Who helped you?"

"Both Kendra and Amy at one point in time."

"I think she likes you."

"Kendra or Amy?"

"Both. Which one do you have your eye on?"

"I asked Kendra out, we were supposed to talk about it after the party, but she was gone after I took a shower."

"I think she got called in for a sick bartender that night. You know she is gone all week and most of next on a distillery tour. Her new boss is spending all kinds of money getting them trained again."

"Oh, that explains why she has not been around this week."

"So, what do you think of Amy?"

"She seems like a lot of fun; she was the one that encouraged me to give such a long show. It doesn't hurt that she has a great ass."

"That she does."

"What's this about Wild Night?" Marshall tried to get the spotlight back off him.

"Well, give me a few minutes. I am working on something for the party." A wicked smile was on her face as she waggled her phone in his direction. "You do have next Saturday open, right?"

At the small industrial kitchen that Eric and Jillian worked out of with several other local delivery-only restaurants, each company was required to take two days off a week so that the kitchen was not impossibly crowded. They rotated on a schedule so that nobody had to forfeit the far more profitable Friday and Saturday multiple weeks in a row. Monday and today had been the days off for this week, while Wednesday and Saturday were next. Marshall served as the delivery driver three or four nights of the week whenever they had large deliveries planned. As they were not scheduled to work next Saturday, he had nothing on his schedule. "Yeah, I was hoping to ask Kendra out then, but it probably wouldn't work into her schedule anyway," Marshall responded.

"Would you be willing to work naked again? I can't promise as good of a payday as last time, but I can't imagine it being much worse with it being Wild Night."

Marshall thought of his bank account and smiled. "I think I could do that. They need me to host things?" After nearly a year and a half, Marshall had been able to pay down a few months of student loans. He had wanted to help his parents out a little too, but he had not yet been able to shake the feeling that there would be questions over where the cash came from. He did not feel remorse for his actions but thought this was probably one thing his parents were happier not knowing.

"I think they have something planned there, but they want you for that if that falls through. The club may have something else scheduled for you." Last time he had gone further than he had thought, but the rewards had been worth it.

"You tell him what we are doing yet?" Eric walked out of the pool and sat on the lounger on Jillian's opposite side.

"No, I am waiting to hear back from someone." Jillian sounded just a little irritated as she turned to her husband.

"Oh, okay, I'll start the grill and whip up some food. I don't think we all need to be drinking too much on an empty stomach."

"Probably a good idea; you need me to help you?"

"Yeah, that would be nice; I think we need to talk about some things."

"Get some sun. Just make sure you don't burn your junk." Jillian got up and followed her husband inside.

Marshall closed his eyes for a minute, soaking in the warm sunlight.

"Marsh, are you just going to sleep all afternoon?" Lincoln had appeared out of the pool and was sitting on the lounger two over from him.

It took a second for Marshall to get his bearings again. Looking at the now melted ice of his frozen margarita on the small side table beside him, he had apparently dozed off for more than a little bit. "How long was I out?"

"Half-hour or so," Lincoln replied, not looking at Marshall but staring into the cloud-dotted sky. "So, I haven't talked to you since... Since you caught me getting off."

"Don't worry about it." Marshall shrugged, it had been an awkward moment, but he would be happier never talking about it.

"No, I need to apologize. I should have waited until I got home or gone into one of the stalls. I wasn't thinking straight until after I came. All those sexy, naked women, I couldn't help myself."

"Believe me, I get it, but next time, be more discreet."

"You could not have stood and watched me," Lincoln replied stoically.

"And you could not have been watching my show. Sorry, it was like watching a train wreck; I couldn't move."

"What are you two discussing?" Jillian walked back with some cold bottles of water.

"Marshall caught me jacking off." Lincoln turned to his sister.

"Just now? Come on, Lincoln, I don't need to see that again." Jillian looked super annoyed.

"Not now; I am not a crazy person. After the party, I snuck off to the locker room. I thought I was alone, and somebody walked in on me."

"Really, Linc? You couldn't wait until you got home?" Jillian looked at him rather cross.

"Says the woman that locked herself in the bathroom with her husband. Why do you think I had to go all the way to the locker room."

"Touche, Well, don't do it again. You told Marshall anything about Wild Night?"

"Nope, that's on you and Eric; I don't have a dance partner for that party."

"Okay, time to clue me in on this whole Wild Night thing." Marshall's gaze fixed on Jillian, whom he had been told had the answers.

"Yeah, yeah, it is. So, you know how you gave everyone a show on Friday?" Jillian sat on the lounger across from Marshall.

"I did what?" Marshall feigned shock.

"Your little masturbation performance impressed several of the women there." Jillian had a smirk on her face.

"Are you calling me small?" Marshall couldn't resist being a bit of a smart ass.

Jillian responded with an eye roll so enormous that he could see it through her mirrored sunglasses. "No, your penis is not small, and the show wasn't short. Your ego feel better now?" Marshall nodded exaggeratedly. "Good, moving on. Wild Night is a much bigger deal than any bachelorette party they host. It is large enough to warrant signing and notarizing an NDA. Apparently, it goes for both workers and club members."

"Wow, that sounds officious."

"It does indeed. They take this very seriously. We will be meeting with Chief Smith and a lawyer on Sunday before noon if you want to come along and get your paperwork buttoned up."

"I don't have plans, so I can make it if I agree to this."

"Good, good. Wild Night is a once-a-year free pass for the ladies at the club. Their men apparently do something similar in the winter months in Vegas. We won't be cooking more than appetizers and tapas. There will be dancing and drinking as well as a few games. The club has a DJ, some big local deal that has agreed to the club's rules."

"Okay, doesn't sound so wild yet, but I assume there's more."

"For starters, about half of the people at the party will start the fun nude. There won't be any pretense of having to slowly strip as the night goes on. There will be sex toys for the ladies to buy and bring. Women will be having sex with one another on several mattresses and other soft surfaces set up around the ballroom."

"Where do I come in?"

"While the ladies do not want to cheat on their men, with another man at least, they want the illusion of being picked up at the show."

"Uh-huh?" Marshall couldn't help a look of disbelief as he began to guess his role in this.

"Most of the servers will have their girlfriends or wives with them. Those individuals are going to give the club a show. For example, sometime during the evening, Eric will pull me up on stage. He is going to eat me out for the audience. Then I'm going to blow him in front of everyone." Jillian blushed a little as she admitted this. "We're scared, but it's also exhilarating. They want you to be the main event again."

"Can't help but notice, I don't have a significant other for this." Marshall had no idea what she had planned for him.

"I've made arrangements for you. As Linc puts it, Kendra has agreed to be your dance partner." Jillian smiled broadly.

"Kendra? Really?" Marshall could feel his sleeping anatomy stirring to life.

"Yup, I didn't tell you earlier because I was waiting on her to give me an answer. She won't be back until the party, so you two won't get to practice." She motioned with one finger going in and out of her opposite fist. "Are you in?"

"Well, it sounds like fun, and if the compensation is better than Friday was, it's hard to say no. I have already given a public show; this might be lower on the embarrassment chart." His body craved a chance with Kendra so much that he cared little for the downsides.

"Great!"

"I just have one problem. I have not had sex in over a year. I don't want to be a two-pump chump in front of an audience."

"You're going to need some practice?"

"Yeah," He nodded, feeling a little embarrassed by his inability to find a girl; he battled his feelings of inadequacy between living at home again and a global pandemic.

"Well, I tried to fill your dance card. Kendra said it sounded like a good time but won't be back until the party itself." Jillian gave a little shrug. "So, she's out. I made an inquiry to Amy on your behalf." Marshall felt both a flash of anger that she had needed to do that for him and a feeling of hopeful excitement. "She seems interested in you, but I think she wants more than just a hookup, for some reason. Eric and I may have talked you up too much. Stephy also thinks your cute but doesn't want to get in the way of Kendra." Stephy was Kendra's best friend, an avid cosplayer, and radiant beauty in her own right. "Most of my other friends are in relationships or far away; I can't even set you up on a date and hope for the best."

"That sucks," Marshall looked a little defeated. "I guess I'll have to practice on my own somehow."

"Nah," Jillian smiled and handed Marshall a bottle of water. A wicked smile overtook her face. "I do know where to find one other, very nice pussy. You are going to fuck me, probably a few times to get you back in shape and rhythm."

"What!?" Marshall and Lincoln both exclaimed, shocked by the revelation. Marshall had a severe aversion to being near a hint of infidelity, owing to family beliefs and an awkward incident when he was a freshman in college. His beefy cock had no such issues, now fully erect as he was reclined in the lounger. He did nothing to hide it.

"Yeah, I need you to fuck me, Marshall." Jillian glanced over her shoulder, likely to check where her brother was. Evidently satisfied that he could not see, she spread her legs further. Her pussy gleamed with a liberal coating of moisture.

"But, you're married." Marshall had an automatic response of refusing.

"I sure am, don't worry about Eric; he will have his own fun lined up. What do you think we have been discussing all afternoon?" Jillian traced her fingers over her sex.

"Can I talk to him first?"

"I would insist you do, although playing a little clandestine hookup could be fun." She smiled again, plunging a pair of fingers into herself.

"When?"

"I'd like to blow you now, then we can eat, and you can go get some condoms. We can spend the evening practicing." She used quote fingers, her sheer wetness shiny on the one hand.

"C'mon, sis, I don't need to see this," Lincoln exclaimed behind her.

"You sure don't; you and Eric will go play some video games or something," Jillian exclaimed over her shoulder.

"You going to fuck my wife or not?" Eric walked out of the house with a tray of uncooked burgers. "Trust me, it's a good time." He had a confident smile.

Almost a year and a half without sex had Marshall's libido screaming above the din of his brain, arguing about infidelity. Does it really count as cheating with both of their blessings? "Are you sure this is good with both of you?"

Jillian nodded aggressively.

"Just make sure you wrap your tool. I don't need to explain why our baby came out white to my parents." Eric looked back and threw several thick patties on the lit and warmed grill.

"Oh... okay then." Marshall's voice wavered slightly.

"You might want to leave, Linc." Jillian reached back and put her vibrant mane in a ponytail while standing to her feet.

"Yeah, I am going to go play something." Linc retreated into the house.

"Find something multi-player. I'm not going to stand around and watch. You two have fun." Eric closed the grill and headed back into the house.

"Why don't you come over and join me in the pool. It's a little hot out here." Jillian swaggered her hips as she walked toward the pool. Marshall sat forward but was in no hurry to get up as each step gave him a peek at her juicy pussy. A fat drop of clear precum surged out and deposited itself on the straining red head of his cock. "You coming?"

"Yeah," Marshall stood, gravity pulling the precum to the sweltering grey concrete at his feet.

"You will be at least." Jillian fired a satisfied smirk at him as she stepped into the water. Marshall followed, hypnotized by her confident sensuality. When she got a couple of feet out into the pool's shallow end, she dove beneath the smooth surface and jetted through the clear water. Her colorful hair rippled as she swam.

Even though it was still early in the season, the water was almost warm as he stepped into it. Not too hot to feel like bathwater, but not too cool to cause shrinkage. Marshall walked a few feet into the water and then dunked himself beneath the surface, carefully hanging on to his sunglasses, so they didn't float away. Jillian had traversed the length of the pool underwater and returned before she popped up beside him.

"Why don't you come sit on the stairs?" Jillian reached out and grabbed his cock as he stood back up. He imagined the lass would pull him over to the entry by his penis, but the combination of pool water and sunscreen caused him to slip from her grasp. She tried to play it off as intentional, but the little giggle she uttered gave her away.

After a couple of tests, he found the correct level. First, trying to sit on the third stair. The water level came up to his belly button, too high for Jillian to breathe as she went to work. Next, he overcompensated; the first step was a no-go. Jillian shook her head no. Sitting on the second step, the water came up to the middle of his thighs, his cock and balls just out of the water.

Jillian wasted no time grasping his shaft and then running her tongue up and down. Her opposite grabbed his testicles, giving the smoothly shorn balls a little squeeze. Wanking him slowly, she looked up at him with a smile. "I have wanted to get another close look at this guy."

She didn't wait for a reaction, sucking an impressively large portion of cock into her mouth in a single go. Marshall unconsciously leaned back and let out a groan of pleasure. This was already the most contact he had in a year and a half, outside a couple of unfinished handjobs. Sure, Jillian had blown him momentarily a week ago, but this had an intent and ferocity that brief moment had lacked. Her tongue swirled around the swollen red head of his giant cock as she sucked another gob of precum out of him.

"Don't tell Eric, but I think you're bigger," Jillian said with a conspiratorial smile. Her hands did not stop moving up and down his shaft as she spoke. "Can't wait to take him for a ride." Her firm breasts jiggled as she wanked him slowly, erect nipples begging to be sucked on and teased.

Jillian's blowjob skills were outstanding, walking his body to the edge of ejaculation before backing off. She played him perfectly. His testicles were aching to relieve their pressure all over her. Jillian toyed with him, not letting him cross into bliss. How she managed to take his entire length in her mouth was astounding, though he supposed she had plenty of practice with her husband. The way Jillian used her tongue to peak his excitement would be burned into his sexual memory. Marshall had thought she was trying to make him cum quick when they started, but she kept backing him off the cliff of orgasm.

"Pretend I'm not here, just flipping the burgers." Eric moving through Marshall's peripheral vision caused him to startle just a little.

Jillian leaned back with a cruel expression on her face. This was what the prolonging had been for; she would make him cum in front of an audience. Marshall was deadset against giving in to her; he didn't want to ejaculate while being watched by her husband. "How many times have we fucked in this pool, babe?" Jillian asked her husband as she increased pressure and speed on Marshall's straining cock.

"I lost count," Eric responded and turned toward them in the pool. He still had his burger turner in hand. Eric had only put on a pair of white athletic shoes to guard against the hot concrete. His enormous cock hung limply over his testicles.

Marshall tensed his core, hoping to stave off the inevitable momentarily. He really did not want to explode in front of his best friend. Jillian must have sensed his weakness as she encircled the most sensitive part of his cock in a solid yet silky hand. Her fevered wanking was concentrated on making him go off. The opposite appendage was fondling his scrotum, urging him to cum. "Nooo..." Marshall bellowed hoarsely, a last gambit to hold out a little longer.

"You wanna fool around again? How much longer do the burgers have?" Jillian's vision did not shift from her husband as Marshall cascaded into a rather shameful feeling of bliss. Her eyes snapped to him as the first warm expulsion fired through her clenched fingers. "Cum for me," Jillian ordered as she switched her grip to mid-shaft while her opposite squeezed his testicles almost painfully.

Although he didn't want to ejaculate with an audience, once his orgasm started, Marshall could do nothing but enjoy it. After nearly a year and a half of all his orgasms at his own hands, this climax was nothing short of epic. He gritted his teeth as a second, enormous spurt ripped out of his cock, and a line of sperm hit Jillian right across her cheek. Most of it ricocheted off her face and splashed into the pool water. "Gnrnk!" Marshall moaned as a third blast decorated Jillian's perky tits. Each subsequent jet of semen seemed to grow exponentially in strength.

Jillian's continued wanking, and insistent pressure on his balls coaxed out a monumental ejaculation. The fifth eruption was the single giant rope that seemed to bisect Jillian from her hair clear down between her breasts. A sixth connected from one tit to the opposite. While the fifth was the largest, the seventh was easily the most voluminous. The mega eruption spackled Jillian like grapeshot from a cannon. The eighth fired over Jillian's shoulder, landing in the pool beyond. Marshall shook as the orgasm seemed like it would never abate. Thick white ropes, one after another weaker than the previous ones, escalating pleasure soaked every neuron. Finally, after a fourteenth dribbled out his cock in a thick white bulbous drop of semen, Marshall groaned as his senses returned.

When the post-orgasmic kick of enhanced clarity surged through his mind, with shocking swiftness for the intensity of the climax, Marshall wanted to beat a hasty retreat. Jillian's continued firm grip on his shaft and testicles made running away impossible. She seemed entirely nonplussed by the torrent of sperm that now streaked and dappled her skin.

"Holy shit, dude! Do you ever masturbate?" Eric broke the awkward silence.

"Often," Marshall affirmed.

"That was a lot of cum." Jillian finally released him and then stared down at her naked torso. "Is that just normal for you?"