Unlucky In Love Ch 02

I usually give a brief catch up on multi-part stories, but honestly in this case, just read Ch. 1 first. Enjoy!

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Matt never returned Jenny's text messages... even when she apologized to Matt and told him he could "do anything he wanted to her" if he'd just come over.

Believing that Jenny had actually enticed Nick to come over that night, Matt told Jenny he didn't know what she was playing at but that he wasn't going to be a part of it. He avoided her at work, which was easy because they weren't in the same department, and they didn't run into each other coming and going from their apartment building except twice—and he just turned around and walked away both times.

After trying a range of overtures to Matt over several weeks, Jenny gave up. Her self-esteem was at a low, and she decided the only way to get over Matt was to get under someone else. Back to the dating apps she went. Jenny tried hinting a little more openly that she was easy to get to know (wink wink) and predictably she got way more swipes than before. Also predictably, she got some pretty lewd and direct messages from the guys who swiped right on her.

She went on a few dates and sucked a few dicks... and on one of those dates she felt a bit of a connection to a guy named Brent who seemed really charming and had a great job. Things naturally progressed from the restaurant back to her place where he didn't just want to get his cock sucked, he wanted to facefuck her. When he was about to cum for the first time of the night, he asked her if he could take video of her taking a money shot. He told her he loved her mouth... told her she had a beautiful face... and he wanted something to masturbate to on his business trip later that week.

Jenny happily let him pose her—he even tied her wrists together with strips of a torn up towel for the video. Jenny knew he was into the rough stuff... they had chatted about BDSM / role playing / etc. before their date. But now, on a first date, she was helping him put his phone in her personal tripod with phone mount so he could keep both of his hands free for the cumshot vid. The results were amazing, for him at least. The video was well lit, 4k, and 60fps... and in it, he held Jenny's arms over her head by the strap and fucked her face roughly. Every now and then he'd pull his cock out and slap her across her face with his free hand. Jenny tried not to recoil too much from the slapping but he seemed to be hitting her harder and more frequently as he got closer to cumming.

Finally he pulled out and began stroking his cock in front of her mouth, which Jenny Dutifully opened wide, with her tongue outstretched. "Take it, whore!" he groaned at her, "Take my fucking cum!"

Brent fired several thick globs of cum straight to the back of Jenny's throat before changing his aim to put a couple blasts across her face and then down to her flat chest. He slapped her tits and face when he was done, then went to turn off the camera. The moment he turned off the camera his entire demeanor changed. He asked Jenny if she was okay, if he slapped her too hard, if she thought it was hot or degrading... or both?

Jenny felt happy that he helped towel off her face and chest. After she washed up, he kissed her and effusively told her how hot the sex was and how hot it was that she let him take the video. As they made it his cock began getting hard again. Jenny thought about cooling things down, but for the first time in a series of bad dates she was feeling wanted and desired... Brent wanted more from her... and he wanted to make another video with her. When he explained the video he wanted to make with her if she'd do it with him, she said "yes" by just asking him not to post it on the internet.

While Brent was definitely going to show his close friends, posting a video like this on the internet would not have been good for his career... because what he asked was for Jenny to let him take a video of him breaking into her apartment, stripping her, tying her hands together, then fucking her against the wall. And for the rest of the night, they moved the tripod around, and shot the video a little bit at a time.

In the beginning he pushed Jenny back into her apartment and slapped her hard across her face. It was Jenny's idea to shoot it several times from different angles... it hurt her, but it made Brent's cock super hard and him super passionate... also, she wanted it to look good in the video. Anything worth doing is worth doing right, she thought. Then he tied Jenny's hands together and tethered them over her head to a standpipe that ran vertically floor to ceiling in the apartment. Immobilized, and practically hanging from her wrists, Brent tore her blouse open. He made sure to shoot it at 240fps so that he could slow it down if he wanted. Jenny didn't really have tits to speak of, but what she had shook beautifully in slow motion as he jerked the fabric open, exposing her chest.

Using a knife, he cut her skirt and panties from her, leaving her nude... her face, tits, and pussy in clear view in the video. He took his time on this part before moving the camera in closer to show her pussy as he fingered her and stepped between her legs. He dropped his pants, took out his hard cock and pushed it up into her pussy and began fucking her. They paused briefly so he could reposition the camera so that he could take closeups of Jenny's face as he choked her, slapped her, and pulled her hair while fucking her.

Brent couldn't hold back, though, and so he pulled out and came all over Jenny's stomach. They had already shot the cumshot he wanted during the BJ video of course, so they could cut it here and have the whole thing complete, but Brent wanted to fuck Jenny again so she sucked his limp cock for ten or fifteen minutes until he managed to get hard again. In moments, Jenny would regret it.

When they began shooting again, Brent began talking even more roughly to Jenny than before, turning her around to face the wall, sticking her perfect ass at the camera. Brent began spanking Jenny's ass—something she enjoyed most of the time, but when he pressed into her from behind to begin fucking her again, she noticed Brent was fingering her asshole while he fucked her pussy—as if he was trying to loosen her back door up for anal. They hadn't discussed anal sex... And getting fucked in the ass... on video no less, was a bridge too far in her mind.

"Oh GOD!" Jenny grunted as Brent began choking her with one hand while pulling her hair with his other. "Not there... No—please... I'm begging you!"

Jenny was completely resisting at this point... fighting back with all the strength she could muster while being tied at her wrists and ankles.

"I'm going to treat you like the whore you are." Brent said, echoing a line he had been using throughout the night.

"That's the wrong hole... you're putting it in the WRONG HOLE!" she exclaimed.

Finally, as Brent obviously began forcefully pushing his cock up her ass, Jenny screamed, "THAT'S MY ASS!"

Brent covered her mouth tightly as he began pumping Jenny's unwilling back door. Nothing was left to the imagination in the video... you can see her body shaking as she writhed in pain under his fierce anal assault. Occasionally Brent would growl "I'm raping your ass, whore..." or "take it up the ass you stupid bitch!"

Brent even stopped long enough to reposition the camera to shoot up from below and between their legs so you could see his cock ramming her asshole deeply from the tip to his balls. She begged and begged for him to stop / to cum / or to just quit... but Brent continued ramming her ass for over 20 minutes before cumming.

Brent began making out with Jenny when he was getting close to cumming for the third time of the night, and with most of the initial pain subsided, she began enjoying getting fucked so passionately by him even if it was rough anal. She wanted to egg on his passion so she began begging him to stop... "oh god, you're raping my ass... please... Please let me go... you're killing me!"

"Yeah, I'm raping your ass, bitch! Take my hard cock up your stupid little slut ass!" He growled as he pumped her back door harder still.

She knew he was getting close... she could tell based on his previous two orgasm, so she began whispering "Rape me! Rape my ass! I want you to rape my ass as hard as you can... Rape my slut chink ass!" to him as he rammed her as hard as he could.

"God I love it... I love raping your ass, Jenny... fuuuuuuuuck!" Brent groaned as he began filling Jenny's ass with his cum.

He pulled her hair and choked her a little more as he kissed her while his orgasm subsided, and he pulled out and collapsed to the floor by her, even as she remained weakly standing, tethered to the stand pipe with his cum running out of her ass. She stood shaking for several minutes until Brent was able to stand and unfasten her wrists from the standpipe, where he took Jenny in his arms and laid her on the floor, naked except for the high heels he made her wear for the shoot.

Brent asked Jenny if he could sleep with her that night as they were both exhausted and it was now around 2am. She thought better of it but agreed, enjoying the feeling of a man's arms around her as she fell asleep. As it was a weekend, Jenny didn't set her alarm. When she did wake up about 11am, Brent was still there, sitting at his laptop. He had been up since 8am editing video and had stitched together the finished product.

"I emailed you a link to my cloud drive... you should download a copy if you want one... I mean... you know... if you want to watch it or anything." Brent said, bringing his laptop over to the bed where Jenny was still naked.

Jenny wasn't sure she wanted to see herself in a sex video... until she saw the first few minutes of what Brent had put together... it was shockingly well done... erotic even... The way he edited; the way he used certain filters and slow motion... the way he repeated certain clips for emphasis, cut in the various extra angles they shot of her being stripped, her being slapped... of her being fucked in various positions... he had even layered in some footage she hadn't seen him take... closeups of him stroking his cock... it made her want it in her mouth as she watched. Her hands found her pussy... her clit.

The video was raw in one sense, highly staged and refined in another... it really looked like she was being raped—especially the anal rape... but then you can see the passion between them towards the end... you could hear the words she used—at the end... he had layered those with an echo audio filter over video of Jenny's face as she's being stripped in slow motion... as if it's her thoughts... that she's dreaming of anal rape... he then layered a clip from the anal rape with a fog filter over it in slow motion...

"Rape me..." She said slowly... dreamily... slowed down... "I want you to Rape my ass..."

He layers the "rape me" quote in and out of the video several times along with a heavily filtered "rape me hard..." it's like she fantasized about it... and she's getting what she wants... it was pure editing genius.

"cum for me." Brent said as he inserted two fingers into Jenny's pussy while she continued watching the video and working her clit.

She was cumming... hard... in no time. He slowly worked his way to her g-spot... curling his fingers up and into her pubic bone as she thrashed and contorted her body as he slowly worked his fingers in and out of her pussy until by the time she was ready to cum again he was thrashing her pussy at a fevered pace.

"Fuck... who are you, Brent?" Jenny asked as he kept her close and made her cum a third time.

"I'm the guy who's going to rape your ass again." Brent said to her as he pulled her up onto her knees as he climbed behind her.

"Oh God, Brent... no... please don't!" Jenny begged in earnest. The truth is, she hadn't really recovered from the night before and would have happily given him a blowjob or vaginal sex.

Brent wrapped his right hand in Jenny's hair and held her down on the bed with her ass up in the air as he lubed her back door with his left.

"Please, Brent... I'm serious... my ass—OWWWWW!" Jenny exclaimed as Brent pushed himself into her unwilling back door. He took things in a new direction, though, wrapping his belt around her throat twice and keeping it tightly clinched in his right fist as he began pounding her slightly lubed back door.

Jenny had a hard time focusing on the passion in his voice... in his hands... in his breath. She began crying as she struggled to hold it together... Brent either thought she was acting, or didn't care that she was really in considerable pain, because she felt his cock get even harder and his breathing pick up even more intensity. "Tell me... tell me!" he grunted into her ear as he kissed her tear-stained cheeks.

Jenny's voice quivered as she held back full on wailing as she tried to say, "R—rape... My... Ass..."

Again and again she tried... but she couldn't muster more than a few syllables between sobbing and grunting. It didn't matter to Brent... he was in a world of pure, taboo pleasure. He absolutely had never felt something so rough and so pure as jerking his cock into an Asian girl's tightly clinched ass by a belt around her neck. It was fantasy sex... exotic... wild... he didn't care. It felt too good.

He knew he was raping her. He told her as much as he pounded her harder.

He flipped her over onto her back and pushed himself back into her asshole as he began slapping her in the face with his right hand while holding her belt around her neck with his left. Jenny tried to stop crying but couldn't... her new boyfriend was hurting her. Badly.

Brent really smacked Jenny around while raping her asshole as roughly as he had done in the last 48 hours. In the rough sex she had engaged in with others, she had never been hit so many times, or as hard. Brent was rough... rougher than even Nick when he followed her home and raped her after dinner that night months before. And then when he locked his lips onto hers... and made it seem like he couldn't breathe without breathing through her, Jenny's tears stopped. Her fingers were going crazy on her clit and she was begging him to "rape her harder."

Jenny would need to examine her choices once Brent left for the day, but for now she was desperate to be fucked harder, slapped more, choked more... as Jenny flipped into a screaming orgasm, Brent also began to lose control. While Jenny's mouth was wide open from crying out in ecstasy, Brent pulled out and bounded up to her face and began shooting his cum into her mouth.

Brent then shoved his cock in her mouth to make sure she didn't miss a drop, forcing another uncomfortable first on her. She had no choice, though, and moments later she had swallowed the batch he had built for 3 hours while editing and watching the rape video he made, which is to say, sizable.

When they were both finished and off their orgasms, Jenny just laid in bed thinking about all she had been through over the last two days. She asked Brent if he wanted to see her again or if he had gotten everything he wanted from her.

"I've just had two days of the hottest sex of my entire life. The only way you won't see me again is if you decide not to." Brent replied as he leaned in for a kiss. Then he added, "I'll call you when I'm back in town in 5 days."