Jessica was used to getting her way. Most college students from overly affluent backgrounds, still at one time or another meet a challenge and realize that they aren’t the smartest, most beautiful, most talented person their parents told them they are since birth. Not Jessica. She was a genius at everything. She was also tall, and had a body that might have been considered “lanky” on anyone else. This could have made her awkward and that awkwardness could have given her the self-awareness she needed to avoid her downfall, but that didn’t happen.
Jessica was selfish, unthinking, and arrogant. But she was also loving to those who broke through her facade and fiercely loyal to her family, especially her little brother. This is just to say that while some parts of her life might make her out to be a caricature or a cliche, taken on the whole she was not.
There was a boy, Paolo. He was a pledge in Phi Kappa Theta, a Catholic fraternity on campus. He was 19. Brown hair. Brown eyes. A chemistry major, like her, but he worked at it harder than she ever had. Jessica was a natural. Paolo squinted at his organic book and moved his lips when he read difficult passages. He had beautiful lips. Jessica was almost sure he was a virgin.
Jessica spent weeks seducing him. They went on dates. They studied together in empty corners of buildings at odd hours. She would walk him through the things he found hard, leaning far over the table in low cut tops. Finally the kiss happened. His lips were everything she thought they might be. Paolo kissed like a movie star.
But Jessica pressed her advantage too far. For the next study session she wore no bra. She considered a skirt and no underwear for supremely easy access, but in the end she wore jeans because she had a fantasy of Paolo thrusting his hand into them and finding her wet cunt with his fingers. She picked a place that she knew people never passed, downstairs in a study room in a blind corner. They met there. At first things went well. Cursory attention was paid to studying. Her nipples poked against her top and Paolo re-read the last paragraph every time he caught sight of them.
They kissed. Paolo grabbed her breast exactly how she hoped he would, kneading, twisting – he was rough, passionate, like his kisses. They made out for half an hour. Her breasts were sore from the attention, but he hadn’t ever made a move to the button on her jeans. Finally Jessica grabbed his hand and put it where she thought he’d get the idea. But he moved it again. She undid the button herself, took his hand, started to slide it down her pants, but he pulled back, and stopped kissing her. Confused, she thought maybe he was just being dense, so she said, “I want you to fuck me.”
“No.”
“What? No, it’s okay, I want you to. I’ve wanted you to fuck me for weeks.”
“Jessica, you’re beautiful, and I love kissing you and making out with you, but I can’t have sex with you. We’re not married. We’re not even dating! It’s just – this is just,”
“Just what, Paolo? You get what you want and leave me high and dry?”
“Oh, I doubt you’re dry,” It was a poor, misguided attempt at humor. It earned him a pile of papers in his face and a slap so hard Jessica’s hand was red when she stormed out.
“Fuck you!”
Something snapped. Jessica apologized a day or two later, but she didn’t mean it. She spent another two weeks rebuilding her friendship with Paolo. A plan formed in her mind. She went to one of the campus computer labs. She signed in anonymously, rather than use her student id. There she looked up how to order Viagra online, and how to disguise it.
She had second thoughts the minute she clicked “order” on a shady website that her research suggested sold actual viagra online without a prescription. Until it arrived, she was determined not to go through with it. She felt awful for even considering the idea. But the pills did arrive. Jessica stuffed them in a drawer, thinking to use them with a future boyfriend, or sell them to someone needy. But every time she looked at the drawer she thought about them.
There was a party after new pledges were sworn in to the fraternity. Paolo invited her. And as the day approached, certain thoughts kept intruding, “All you have to do is get him started. He wants you. Think of how he made out with you in the library. You know that the second he got his cock inside you he’d keep going of his own accord. You’re just helping him along. After all, he still has to decide to do it.” Night after night before the party the intrusive thoughts wore on her.
On the morning before the party, Jessica showered, then while she was drying off, she pulled her illicit stash out of the drawer and set it on the bed. Fuck me, this is stupid. I can’t do this. But the tingle between her legs suggested otherwise. She undid her towel, pinched one of her nipples between her fingers and palm and tried to convince herself not to masturbate. She finally laid back and spread her thighs to dry the rest of the way off, but the pressure building in her pussy was too much. She reached a finger down, traced the outlines of her labia, and imagined what Paolo’s cock might look like and his face when he finally gave in to his (she imagined) hunger for her. A clear drop like honey fell from her pussy when she stopped herself just short of coming. She would do it. Her orgasm would wait for tonight.
She settled on Bombay Sapphire to disguise the taste. She couldn’t figure out how to get the viagra into his drinks alone, so she crushed some pills and dissolved them in the bottle itself. She would go, stay for the party, and sneak upstairs with Paolo and the spiked booze.
She had to touch herself several more times before the party. Every time she stopped herself short of release. Every time she got wetter. She didn’t go out. She couldn’t think of anything but to be nervous and excited and ashamed all at once.
The party went on for hours, like good college parties always do. Music played, people made out in corners. At one point she heard a couple fucking so loudly someone had to turn up the music. The energy of the night was charged. Jessica was on edge. Paolo looked fantastic in an untucked button down oxford shirt and chinos – the uniform of every frat guy the world over. And so she didn’t notice at first when someone pulled the bottle of gin out of her bag and start using it to make drinks at the bar.
It was only afterwards, as the party started winding down and people started to pair off. Some of the women went home. The music got slower. Paolo grabbed her arm, “Hey, want to go upstairs and shoot pool?” He was looking very flushed.
“Sure!”
She picked up her bag and realized it was too light. There were two half empty bottles of Sapphire on the counter. Shit. Everyone had their dose of viagra tonight. But Paolo had too, so she only worried a little.
The stairs did Paolo in. He leaned on her as they ascended. They opened the door into the game room and found it empty. Paolo grabbed a pool cue sat down in a battered leather chair while Jessica closed the door behind them, aware of the moment of private time and suddenly anxious. When she turned around, Paolo was asleep, passed out from alcohol. Fuck me.
Jessica grabbed the pool cue from his hand and it didn’t disturb him at all. She shook him, but he barely stirred. He seemed to be sleeping soundly, and his breathing was regular, so it was probably just “regular old” black-out drunk. She made a face, chalked the cue, re-racked it, and slumped down in a chair next to him to clear her head.
She waited for him to wake up, to no avail. After what felt like an hour but had really been no more than ten minutes, a thought occurred to her. No. But five more minutes passed and it came back again. No, she thought again, but this time she unzipped her pants. She got up to check the door and make sure it was really shut. Then she sat back down across from Paolo and slid her hand down her jeans. It felt good. But Paolo would feel better.
She stopped herself once more and buttoned her pants, but didn’t zip them. She leaned over to Paolo’s chair and shook him once more. He mumbled something in his sleep and she whispered, “Paolo!” in his ear. Nothing. Then Jessica bit her lip and popped the button back open on her jeans. She pulled them down and stepped out of them, then tossed her panties on the floor beside them. She bent down on her knees between the sleeping Paolo’s legs. Her hands shook. She stared at his face for any sign of movement while she popped his button, then drew the zipper down tooth by tooth. He was soft. I wonder… She rubbed his cock through his boxer briefs. It felt so good she put her other hand between her legs. There was no real movement inside his pants, though. She dared to pull his boxers down, tucking them between his jeans and balls so that she could access his whole package.
It was not huge, but he a beautiful cock. It was shaped perfectly, cut and she could tell that when he was hard he’d be nice and thick. Now that she had his cock out, she felt more confident. Hunger woke within her. He’d had enough viagra, she was sure of it: she just needed to make him hard. She just had to do it without waking him up. She took it in her hand and pumped it experimentally. Then she leaned in and ran her tongue from the base, where his balls met the shaft, all the way to the tip. He was salty and sweet at the same time, and she allowed herself another go. On the second go, she felt things begin to change, firm up. He wasn’t hard yet, but he could be. She took his cock her her mouth and took as much as she could, letting the tip rest against her throat before sucking and pulling back. With every stroke, Paolo got harder and Jessica more determined. Her arousal fell to the floor from deep inside her pussy in clear, sticky drops. She sucked until he was rock hard. He was thick as she’d hoped for. He was still asleep, but his cock throbbed its willingness. She reached into her bag and pulled out a condom.
“What the fuck are you doing? Is Paolo passed out!?” At some point she must have stopped listening to the door. She’d gotten too engrossed in what she was doing. “Get the fuck off him, he’s not like that!”
She turned around with a flush. Everyone had gone home but her. The music had stopped. It was her, Paolo, and five of his fraternity brothers crowding the door. The one in front who yelled at her, Graydon, was red with fury. She could think of nothing else to do. She stuffed his cock back in his pants and zipped him up, then stood to face them. Now the thought of what she had done hit her full force, and she started to cry. Graydon shouted, “If you want to fuck someone so bad, why don’t you fuck someone who’s awake for it? Bitch!”
Jessica cowered. She started to reach for her panties and jeans, meaning to grab them and bolt out the door, but what she’d done and what she was about to do overwhelmed her, and she looked at Graydon. He had been nice to her earlier that evening. Now he looked like a monster between her and the door. *I’ve fucked up*. Jessica paused. Looked him in the eye. She looked at all of them. Then she sobbed and said, “Yes. Alright.”
“What!?”
She walked up to Graydon. Tears clouded her eyes, but she held his gaze. “I said, ‘yes.’” She pulled her shirt up over her head and threw it on the floor. She unclasped her bra and dropped it. “Alright,” She bit her lip, turned her head down, blinked tears away. Then she said “I’m sorry,” and she turned her back to him and got down on her hands and knees. She spread her thighs apart and waited.
She felt Graydon’s cock enter her moments later. He was the steely kind of hard that comes with viagra, rage, and hormones. Even as wet as she was, his cock felt rough. She welcomed every pounding thrust. Fuck me! I deserve it! Make it hurt! At first the thoughts were only in her head, but as he came closer, she started saying them aloud, “Hurt me!” Graydon’s hands left bruises in her hip where he gripped her. He kept going faster and harder. He let loose a primal sound and then long, slow, deep thrusts came one after another and she knew he was filling her body with his cum.
She panted. Before she could catch her breath, she felt the second one’s cock inside her. He started slow, and when she could finally manage a word, she said “What’s your name? Which guy are you?”
“Jason.”
“Jason, I’m sorry for what I was going to do to your friend. Fuck me hard. Make it hurt.” He did, and as his cock slammed into her she reached between her legs and began masturbating, fingering herself with the same fury that the men took her. She came on Jason’s cock hard. He bucked as her vagina clenched down around his cock. Another primal groan and he emptied himself into Jessica’s waiting body. He walked around front as another guy entered her, and she began sucking his limp penis until it was hard again. Graydon was masturbating, leaning against the pool table.
The next cock went in her ass and she screamed, but yelled for him not to hold back. She pounded back against him as he thrust into her. She fingered herself, and came once more as he emptied into her.
Five. Six. Seven men entered her, spilled their seed inside her. She felt weak in the knees. At some point they picked her up and put her on the couch while someone’s cock as still in her, and she lay face into the cushions and accepted each of them in turn, some more than once. Her pussy throbbed. Her breasts ached from being mashed and pulled and kneaded by men. Her ass was red, turning to purple in places from the rough ones who spanked her while they forced their cocks deep inside and spurted their cum into her.
Jessica felt another set of hands on her hips. She wondered how much any of them could have left in them. Then she realized this pair of hands was new. “Paolo?”
“Yes.”
“I’m sorry,”
“I know. I had been planning to have sex with you tonight anyway. I knew you wanted to, still. I was just waiting for the right time, then I fell asleep. Now’s not – uh – the right time, I think. But I’d still like to anyway.” He paused, “If it’s okay…”
Jessica choked up. “God, yes,” She spread her thighs a little further and rocked back to encourage him. Paolo unzipped. She heard his pants hit the floor. Paolo was so hard… He slid into her through all the other men’s come and fucked her gently. After all the others pounded and punished her, she still managed to feel every stroke from Paolo. When he finished – inside of her, like all the others – everyone else was gone. He stroked Jessica’s hair once, and then sat down beside her. Her face and hair and body were a wreck of tears and sweat and come, “Sleep here. I’ll stay with you. Tomorrow, I’ll take you home. After tomorrow, I don’t know… I need to think about it. But tonight we are okay.” He put a pillow on his naked lap, and she lay her head down on it. He stroked her hair, kissed her forehead, “Sleep. By the way, you felt really good.”
Source: reddit.com/r/sexystories/comments/7gzekp/jessica_was_used_to_getting_her_way