Fantasy Man Pt. 06

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Old friends help Jessica teach Corbin about anal.
11.9k words
4.83
16.7k
9

Part 6 of the 9 part series

Updated 06/10/2023
Created 01/02/2021
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Ian_Snow
Ian_Snow
1,627 Followers

Sasha sat atop a concrete table as Jessica hurried out from her last class. The beautiful brunette hopped off and snatched up a pair of paper coffee cups. She held one out as Jessica approached.

"Still hot," Sasha said.

"You're a saint," Jessica said, taking the cup and sipping. Coconut chai, one of her favorites. She closed her eyes and gave a deeply satisfied, "Mmm."

"Oh, to get you to make that sound a different way," Sasha said.

Jessica opened her eyes and grinned. "You have an open invite to my place any time."

"Might have to take you up on that. Ready to go? Billy and Josh are at the library working."

They headed in that direction. Sasha was enjoying being vague about why they needed to meet up with Billy and another one of the Representatives, the group of seniors on campus who ran the biggest parties of the year. All she did know is that it had something to do with a way for Jessica's boyfriend Corbin to sleep with Dr. Rosamund Madison. Sasha thought hooking up with her would be a gateway to Corbin hooking up with her own mother, Dr. Pamela Windsor.

"I have to ask, why are you doing this?"

Sasha grinned. "Mostly? I think Mom needs it. After the divorce, she's not really dated anyone. There have been a couple guys but no one who really wowed her. We both know Corbin can do that."

"There have to be plenty of other guys who would fit that bill, though. Why someone you've slept with?"

"I know Corbin's not going to stick around. He's not clingy and he's head over heels in love with you, so I don't think he's going to get weird."

"Come on," Jessica said, nudging her friend with her elbow. "That can't possibly be it."

Sasha looked behind them, then all around, and said quietly, "All right. The idea is hot. It always has been, since Brooke first told me about it. It's not... you know, an incestuous thing. It's this, hm, this idea that a guy who gave me the best orgasm of my life doing the same thing to my mom."

Jessica wondered how that wasn't incestuous, but it didn't pay to bring up the point. "That is kind of hot."

"Right? Speaking of, have you heard from Brooke?"

"Mm," Jessica said, finishing off a sip. "Yes. Remember Mike, my escort from the scavenger hunt?"

"Sure. Ohhh, did they hook up?"

"They did. I don't know if it's a long-term thing, but they seem happy enough."

"Aw. I think she had a tiny crush on Corbin."

"Me too," Jessica said. Truth was, she was still shocked Corbin wanted her instead of Brooke. Brooke was simply stunning. Then again, Sasha was too. He had his fun with both of them a couple times but it was Jessica he wanted and who he came home to every night. Why exactly, she would never know and never truly believe. There was just too much brokenness in her past to not wonder.

They sipped and talked, and all around them, the world was cast in autumn colors. The landscaping crews tried to keep up with the leaves on the ground but it was always a losing battle this close to Halloween. Not too many weeks until fall break, and then Jessica would drag Corbin four hours to her hometown, Norrell. The thought excited her, and not just because of getting to road trip with her boyfriend. Jessica missed her family dearly, and she desperately wanted her parents' opinion on Corbin. Her long and storied history of making bad choices with guys left her needing that approval, something that would have made her teenage self scoff.

That was why they were still playing this stupid game of "will he/won't he?" with Sasha's mother. Dr. Windsor. Once he'd slept with her, then Jessica felt like he'd finally understand he could sleep with anybody. That he didn't have to be saddled with Jessica if he didn't want to be. Though she grew more and more sure of the foundation of their relationship every day, that felt like the finish line for her. She could truly accept Corbin wanting her above anyone else at that point.

The library was just coming to life as students got out of classes for the day. Most flocked to the computers, but a few handfuls of students worked at the tables and armchairs too. Jessica saw some she recognized and waved, but the pair of friends were on a mission.

"Hey, Marlon, you seen Josh or Billy?" Sasha called to one of them. The guy didn't look up from his book as he pointed up. "Love you."

"Uh huh."

They headed up to the second floor. This was primarily the research section, bookended by a dozen small study rooms. Josh, Billy, Bethani, and a young woman Jessica didn't recognize sat around a table in one of them, a mountain of notes in front of them.

"Homework on a Friday," Jessica said to Billy as he glanced up and grinned. "Beth really has tamed you."

"Right?" he asked, rising. Josh stood up too, but he looked less than amused.

"Don't steal them away for long," Bethani said, faking a yawn. "Don't know how we'll survive accounting without them."

"I say keep them," the other woman said.

"Oh, the jokes," Josh said. Whereas Billy was a hulking goliath of a wrestler, Josh was tall and slim, almost beautiful in his good looks. He used to play basketball for the university before another player slammed him into the bleachers and ended his sporting career with a devastating broken leg. In a way, that injury and the outpouring of support made him his class's version of Corbin, though he was far darker in disposition than Jessica's boyfriend.

Josh nodded towards the door and they headed out. They didn't go far, just to another study room, and he closed the door after everyone.

"No," Josh said flatly, staring at Sasha.

"Josh," she said with a sigh.

"Absolutely not. No. Hell no."

"No to what?" Jessica asked.

"The Phantom Masquerade," Billy said, grabbing a chair and sitting down. Jessica thought for a moment about sitting too, but her plans for that evening with Corbin included a hidden surprise she'd been wearing all afternoon and it made sitting uncomfortable.

Jessica blinked. "It's real?"

"Yeah," Sasha said quietly. "It is."

The Phantom Masquerade was one of the great myths of Agramonte University, a party so secretive and debaucherous no one really believed it existed. That was mostly because it wasn't just for students. It was rumored that the school's hottest professors and adjuncts invited a group of equally attractive students to a party once a year around Halloween. No one Jessica knew ever actually went to one. It was always "a friend of a friend," and so she dismissed it.

"This cannot leave this room," Billy said. He had never looked more grim. "If this got out, we can kiss whatever future we have in our majors goodbye."

"They have a lot of power," Josh agreed. "And they have the ears of everyone they need to."

"I'm not going to talk," Jessica said, taking a chair too. "It really is a sex party, isn't it?"

"It is," Josh said. "The Representatives pick a number of seniors every year to attend. No one's forced into anything, but there are expectations that there will be hookups. In return, the professors push the careers of everyone involved."

"Jessica's a senior," Sasha said.

"And Jessica's invited," Josh said. "But not her boyfriend, and definitely not you."

"There have been exceptions to the senior rule," Sasha snapped.

"Sure, if a professor specifically requests them. But it doesn't happen. Underclassmen always lead to problems," Josh said, folding his arms. "They get complacent, think they can coast. Or worse, they talk and damn near ruin the thing for everyone."

"Corbin wouldn't," Jessica said.

"I only have your word for that," Josh said.

"And mine," Billy said. Josh glared at him and he shrugged. "Corbin is a good dude. I'll vouch for him and Jessica both."

A tic in Josh's face made his lip quirk, and he finally turned back to Jessica and Sasha. "Why are you so desperate for this?"

"Dr. Rosamund Madison," Jessica said immediately. There was no sense in lying about that. She had no intention of mentioning Sasha's mother, though. "I want to see Corbin and her together."

"The biggest game at the party and you think you can break all the rules just for a quick peep show?"

"Nothing about fucking Corbin is 'quick,'" Sasha said. Every eye in the room fell on her and she smiled faintly. "It's the truth. He's the best I've had. He's big, he can go for a long time, and he knows how to treat a woman."

"She's right," Jessica said.

"There is precedent. It's been a while, but it's been done," Billy said. "It can't hurt to ask Dr. Madison."

Josh didn't look happy about that, but nodded. "I can tell her you two are interested. There's almost no chance she'll say yes, but send me on some pictures of him and maybe you can convince her."

Sasha grinned. "I think we can give you those right now."

She and Jessica both dug out their phones. Over the course of a frenetic night with Brooke and Corbin, Sasha had taken a number of faceless pictures of the freshman in various stages of undress and in the process of fucking Brooke silly. Jessica contributed a few of her own, blushing hard as she realized none of them were faceless.

"Josh, if I send you these..."

Josh's hard looks softened. "It stays between me and Dr. Madison. I swear. If they get out, I'll resign as a Representative. That would kill any chance at a good future I have. Okay?"

"It's for Corbin, so..." Jessica nodded and sent him a few choice ones of Corbin fucking her from behind in the bathroom, both of them staring at the mirror, Jessica in the middle of a laughing orgasm, Corbin on the verge of his own. She also sent some close-ups of his big cock stuffing her pussy.

Josh looked at them and shivered. "I'll get Dr. Madison aside and talk to her about this. You'll know one way or another by the end of the weekend."

"And me?" Sasha asked.

"Don't make me say it," Josh said. "You know why you can't come."

Sasha gave him a hard smile. "I suppose I do."

"Pamela? Really?" Jessica asked, shocked. She would have never thought Dr. Windsor would have gone to that sort of a party.

"Not a word," Josh growled, going for the door.

While the guys returned to their studies, Sasha and Jessica headed back outside. They had to walk a bit before they broke free of an intermittent stream of students, and Jessica looked sideways at Sasha.

"Don't judge. Please don't judge."

"I wouldn't," Jessica said. "How long have you known?"

"I've suspected for a while. My mom and dad always disappeared for a night around Halloween. They wouldn't come back home until the next morning. I didn't think much about it until I started college here. One night, this was after the divorce, I was home. I was going to stay with a friend but she got sick. Mom didn't know I was home. She came back around midnight, and I was still up, watching a movie. She came in and nearly ran for the bedroom when she saw me. But not before I saw her. She was... I've never seen her that way before. Her dress was torn and held together with bobby pins. Her hair was all undone and kinda clumped and I think guys had..." Sasha blushed, and Jessica nodded. "Anyways. I thought she'd been raped, the way she looked. She laughed at that and told me no, she was fine, she just had a really wild time."

"And you figured it out."

"Yes. Well, not really until last year. I followed her to a mansion out near Lakecrest. They unloaded the students from a bus. All of them had hoods on so they couldn't see where they were at."

"Weird."

"Really weird. But they have to be careful like that." Sasha took Jessica's hand and squeezed. "I did what I can. I'm sorry again my mom came after Corbin like that."

Jessica stopped and turned to look at Sasha. "You don't owe use any apology. It's not your fault."

Sasha stepped in, and without any hesitation, reached around to cup the back of Jessica's head. They kissed, their first, and it was good and slow, warming Jessica to her toes. "Good," Sasha breathed against her lips. "Then I'll know it's for real when I do stop by and have some fun with you."

"It'll definitely be that," Jessica murmured. Her phone rang, and Sasha broke away, grinning. "The worst timing." She answered the call as Sasha began to walk away, blowing her a kiss as she went. "Hey, baby. I just met with Josh and Billy. I don't think it's going to happen but it's not a total no yet."

"That's, uh, that's great," Corbin said, sounding weak. "Hey, um, I've been back at your place for a bit, and, uh, you have a bunch of visitors. One of them is, um... kinda holding me hostage."

"What?" Jessica asked sharply.

"Yeah. Yeah. She... kinda has a knife and she's pointing it at me telling me I need to call you."

"A knife?" Jessica yelled. Then it hit her. The one and only lunatic who would pull a stunt like this.

"Hang on, she wants to talk."

A soft, pleased voice said, "Hey, Jessie. I like the new boyfriend. He's adorable."

Jessica gritted her teeth. "Hello, Sarah."

* * *

No work that evening, and Jessica hinted all week she had a surprise for Corbin. That left him in a good mood when he arrived at her place. She was supposed to be meeting with Billy and another friend about some chance they had at Dr. Rosamund Madison, but he wasn't holding his breath. All he needed was Jessica.

He grabbed a quick shower and laid out the homework for the weekend on the kitchen table. Not much, really, just a short essay and a take-home quiz. He could knock that out probably before Jessica got home, so he started in on it, trying to ignore the growling in his stomach. A couple hours and Jessica was going to guide him through grilling burgers, their first lesson in cooking together.

The doorbell rang, and whoever was on the other side giggled and hammered on the door too. "Jessica, you slut! Open up!"

"Be nice!" Corbin heard someone else say.

He rose to his feet, curious, and went to answer the door. The one doing the doorbell ringing and knocking was a short woman whose hourglass figure was so grossly exaggerated Corbin had a hard time not staring. Her bust and hips were huge, her waist and the rest of her petite. And holy hell, she was gorgeous, with long, playful pigtails and a delicate face with big, dark eyes glimmering with good humor.

A handful more women stood behind her, on the porch and the sidewalk. Two he recognized - Dakota and London, the twins Jessica was friends with. They were petite blondes, classically beautiful. Another was drop dead sexy, with long black curly hair, big pouty lips and doe eyes, and curvy proportions that would have been big if it weren't for the obvious comparison of the woman in the lead. She held the hand of a blonde with shorter, curlier hair and elegant looks somewhere between playful and gorgeous. The last of the bunch was a delicately featured Latina with some of the most beautiful eyes and lashes Corbin had ever seen. She flashed him a sympathetic smile just a split second before the one in the lead pushed Corbin aside.

"You're not Jessica," she said, storming in. "Jessie! Where are you?"

"Sarah!" one of the twins said, following her.

The other one came in too. "Sorry about this, she's... well, hormonal."

"And also she's just Sarah," the supermodel-looking woman with the black curly hair said.

"That too," the twin said.

The women all pushed in past Corbin. Flabbergasted, he didn't utter a word in protest, though he had a feeling in his gut this wasn't going to end well. Sarah walked - or bounced, really - towards the stairs, and hollered up them, "Jess!"

"She's not here," Corbin said. He cleared his throat as the six women turned to look at him. "She's, ah, finishing up at the college for the day. Can I help you with something?"

Sarah stomped towards him. She wore a dress that didn't constitute much more than a skirt and a pair of crisscrossing wisps of material that fought valiantly to cover at least a small portion of her breasts. "Who are you again?"

"Cor-"

"Are you the new boyfriend?"

"Yes?" He cleared his throat and tried again. "Yes. I've met Dakota and London before. Um. Hello."

She studied him a minute longer, then stormed towards the kitchen. The Latina settled on the edge of the couch and said, "I'm sorry. We're going out dancing tonight and wanted to invite Jessica-"

"Oh my God, Sarah!" the playfully cute blonde said, looking towards the kitchen.

Sarah came out holding a long kitchen knife, her eyes gleaming. "One more time, what's your name?"

"Cor-"

"Can you satisfy her?"

Corbin blinked at Sarah. "Uh. What/"

She waved the knife at his dick. It was uncomfortably close. "Do you make her come? Are you a man?"

"I... yes?"

"Hm," Sarah said. The other women circled her but kept their distance. "I don't believe you. Strip."

"Sarah," the Latina said, rubbing her face.

"Don't listen to her," one of the twins said. "She's not going to stab you."

Sarah glanced over her shoulder, amused. "You really think I wouldn't?"

The twin blanched. "On, uh, second thought, better not move fast."

Sarah returned her attention to Corbin and rocked back and forth on her feet. "Okay. You can keep your clothes on, so long as you call her. Call her call her call her."

The supermodel-esque one said, "Put that down. You're being crazy."

"It's my pre-pre-pre-birthday celebration and I want to shove Jessica's face into my pussy," Sarah snapped. She jabbed the knife at Corbin. "Call. Her."

Corbin dug out his phone and called.

* * *

Jessica raced back home as fast as she dared. At one point, she thought for sure a cop was going to pull her over for going five miles an hour above the speed limit, but he didn't whip around.

"Goddamn it, Sarah," she muttered.

She didn't believe for a second her ex-girlfriend would do anything to Corbin. But Jessica hadn't really told him the extent of the debauchery she'd gotten into with Lionel's girlfriends and wife, and the thought of anyone telling him before she could made her sick. Would he run when he knew the truth? Would he look at her with shame and disgust? She'd done so many weird things for Lionel. For... well, all of them, really.

She had something of a goodbye with London and Dakota. Corbin had been there for that, and he knew she'd been with the twins sexually. That was about the extent of it. He probably suspected some of it - as he said, he was naïve but not stupid. But how could Jessica break it to him how quickly she spread her legs for all of Lionel's lovers just to please him? How she'd begged for it at more than a handful of their orgies?

Oh God, what if he fell for one of them?

How easy that would be. Sarah and Jenna were honest-to-God models, Jenna currently, Sarah before she took on an executive job with a clothing brand. Yvonne certainly turned heads when people saw her face on real estate signs. Victoria was the definition of Corbin's fantasies when it came to his fetish for teachers, not to mention she was an incredibly stunning Latina who radiated grace and kindness when she wasn't dominating one of the other women in bed. Then there were the twins. They were, at least, a known quantity to him, but there again was the taboo appeal of twinship. Jessica herself had found that pretty hot. Still did.

She shifted in her seat, the plug still inside her. She needed to pull it soon. The anticipation she felt about that night, the excitement of giving Corbin his first lesson in anal, melted away into tears that threatened to spill over every time she hit a red light.

"Goddamn it, Sarah," she croaked again, balling up her fists.

Jenna and Sarah's vehicles sat out front of her house. Jessica pulled in behind them and swallowed. Buried under her fear of losing Corbin was a residual fear of this very confrontation, with or without him. She said goodbye to London and Dakota, but the rest of her ex-girlfriends only really got a few texts from her before she cut off communications with them. It hurt too much to talk to them, much like it did Lionel and Morgan, though Jessica's ex-girlfriends hadn't really done anything to her. She had been embarrassed about trying to take Lionel from them, and assumed they would all be pissed at her for it. It had been easier to walk away with a quick "I'm sorry" and not listen to their responses.

Ian_Snow
Ian_Snow
1,627 Followers