Unlucky in Love Ch. 01

"Jenny, we live in the same building... you know you could tell me this story and suck me off right now!" Matt said in mock anger.

"And I told you all my dates at least end in a BJ... take me out, you idiot!" Jenny replied.

Matt hung up on Jenny, leaving her dazed and confused. She started and stopped about 20 different text messages—some angry—others with more of the purported anal rape video... she sent none of them. Right before she was about to turn her phone off and go to bed, there came a knock at her door.

"OHMYGOD OHMYGOD OHMYGOD!" Jenny exclaimed as she ran around buttoning her blouse and fixing her skirt before trying to calm herself to open her door.

"BK Brews is a block from here... their burgers are good... it's a start." Matt said, reaching for Jenny's hand.

They had a pleasant, flirty, actually, very flirty, dinner, where Jenny explained over a 45 minute period about how one night her ex, Kevin, held her down as she sucked his cock so that three of his friends who were watching and participating could pull down her panties and fuck her for the first time. She had tons of pics and video from the night, and she'd pull something out when it came to that point of the story to show him. Even though they sat in a corner booth, their server, Nick, managed to walk up on them when pictures of Jenny naked or getting fucked were clear. At one point, Matt handed the phone to Nick right in front of Jenny who was 50/50 dying from embarrassment, but thrilled and emboldened that Matt wanted to show her off. In the video, Jenny was getting fucked in her mouth and pussy, and the guy in her mouth pulled out and came directly into her throat, with the camera angle moving to show the whole cumshot.

When Jenny told Matt about how they wanted to "keep going" and fuck her in the ass, she explained how she told them in no uncertain terms was she not getting anally gang banged that night, and that they should feel lucky they had all gotten to get fucked and sucked by her. She was riding her boyfriend Kevin at the time and Kevin and one of the guys exchanged a glance that set off a chain of events where Kevin pulled her down to his chest and held her tightly as one of the three other friends crawled behind her, straddling their legs. She showed him the first video of the first guy pushing his cock up her ass while her ex, Kevin, held her and fucked her pussy. He had to keep the sound off, because Jenny was screaming at them to stop—that she wasn't doing anal... Nick came back with another round of beers as Jenny showed the second video to Matt—who immediately handed the phone to Nick, who watched with a mix of emotions on his face as Jenny's tear and mascara streaked face stared into the camera as the two men fucked her pussy and ass in unison.

"Would you do that to a girl?" Jenny asked Nick.

"I'd do it to you tonight, with him." Nick replied, surprising her.

"You're so bad!" Jenny said with a slap on his arm as they all laughed.

"You've got a nice ass... what can I say?!" Nick said with a laugh as he swiped forward a few videos to see Jenny taking cumshots from all four guys standing in a circle around her.

When dinner was over and the check was paid, Matt looked directly into Jenny's eyes and stared down at what he admitted was a perfect and beautiful mouth, and said, "So how about that BJ?"

"NO ANAL RAPE!" Jenny joked.

When they arrived back at their apartment building, the front desk guard smiled at them with a smile indicating he had seen inside hookups before. They disappeared into the elevator and began making out on the ride to the 6th floor before fumbling with the keys to get into her apartment.

"Okay... no anal rape... but... can I at least tear your blouse open and push you to your knees?" Matt asked politely.

"Buy me a new one?" Jenny replied.

Matt took that for a green light and sent the buttons on Jenny's white blouse showering to the ground as he tore the fabric wide open, then down and off of her body. Her bra quickly followed and he was soon holding Jenny's hair in both fists and fucking her mouth with abandon. He came in less than ten minutes, but told Jenny that was enough for a first date as she struggled to clean all of his cum from her chin, neck, mouth, and tits.

Jenny excused herself to go wash up as she realized she had cum in her hair as well, and when she came out, she found a note.

"You were worth the wait. I can't wait to fuck your ass, but I will at least give it until date three. Sleep well. Let's act normal at work tomorrow. XXXOOO -Matt"

She stood there, twirling her wet hair wearing only a thong, thinking about what to do next with him and contemplating the possibilities of it being more than just a fling. When she placed the note back on the counter with a smile, she was surprised by a ring of her doorbell. Had Matt forgotten something?

She opened the door and said, "Forget something?" without realizing it wasn't Matt at her door, but tonight's server, Nick, who entered and shut and locked the door behind him as she turned to look at the table and see if Matt's keys or wallet was there.

"Oh God! It's you! How did you get in?!" She asked in shock, before moving to cover her tits, which she knew, he had seen plenty of already.

"A lot of people in this building leave credit cards etc. at work... the super knows me as do all the front desk people." Nick said as he walked closer to her.

"I... what are you..." Jenny asked meekly as she backed away from Nick, who was now on top of her and pinning her back against her kitchen counter.

"You're not the only girl to see my muscles and my tats and know I can fuck her like she needs, babygirl. You didn't show me those videos on accident." Nick said as he grabbed her by her throat and held her in forcefully and unwaveringly in place.

Jenny choked and her vision blurred as Nick ripped her thong from her body. He was so strong and so fast, that Jenny barely had time to gasp for air as he penetrated her pussy from behind, turning her over the counter and pressing her chest into its cold surface. Nick's cock was huge, hard, and ready... he had taken a Viagra at work before walking over... Jenny cried silently into his powerful hand as he held her there and fucked her.

"This is just the warm up, bitch! You're gonna get it all tonight!" Nick growled into her ear before picking her up and walking her with his cock still buried up to her stomach in her pussy into her bedroom where he collapsed on top of her and continued pounding her. He let go of her and took his cell phone and propped in up in a little portable tripod, pointing it at the bed, recording video of everything he would do to her the rest of the night. He grabbed her cell phone, held it in front of her face to unlock it, then placed it in another part of the room to record everything from a second angle.

Jenny was in tears but cried silently as Nick returned to the bed with her. She took his cock in her mouth when he knelt in front of her and choked her over and over with it, demanding she say things like "I love your cock" and "I need to be raped, daddy" to him which she had no choice but do or risk his wrath. When he pulled out to cum in her for the first time, without prompting she begged him to cum in her mouth. He made sure to capture this first oral cumshot, as it was guaranteed to be voluminous and powerful—and he wasn't disappointed.

This guy had porn cock and delivered a porn cumshot to go with it, absolutely flooding Jenny's mouth and fat, beautiful lips with his cum before forcing her to swallow what she could and suck him to keep him hard. Jenny couldn't believe his cock maintained its intensity after cumming so hard... she was scared when he pushed her over the edge of the bed with two pillows under her hips to prop up her ass even higher.

Lube and then one finger roughly entered her tightly clinched back door... then a second finger... then a third... She screamed as he positioned himself above and behind her, checking his phone to make sure it could clearly see his cock penetrating her ass. Her own phone would capture her face and his... his phone, the porn angles of the anal penetration that began seconds later.

Jenny's eyes shot wide in horror and her mouth gaped open though no sound came from it as Nick buried his entire cock up her ass in a single, powerful stroke. He covered her mouth and began roughly banging Jenny's poorly prepared asshole with his long, hard fuckpole... his hips smashing into her ass and sending shockwaves through her body over and over in long, powerful strokes. He buttfucked her ass harder than she had ever been fucked in her pussy... pain overwhelming her to the point of numbness... she lost track of time... she lost track of everything.

Nick then pulled her up onto her hands and knees and knelt behind her before penetrating her ass again, while holding her hips for stability.

Nick yanked on her hair and demanded she tell him to fuck her ass. He slapped her to get her attention and she cried out, "Pleeeeease... fuck... My asssss!"

He made her say lots of things like that... "rape my ass, fuck my ass, buttfuck me" etc. as he railed her tight back door.

"Honestly, you're not much to look at, but you have the nicest ass I've ever fucked!" Nick said to her as he pulled her onto her side and opened her pussy while pounding her back door for his camera.

Jenny continued crying silently as she got forcefully taken in her rear by her restaurant server from her date with Matt and she drifted into a dream, imagining that it was Matt, in fact, pounding her back door after the date.

"Fuck me, baby." She said to Nick before repeating the following phrase the entire time he pounded her, "Fuck my ass hard!"

When he was ready to cum again, poor Jenny was forced to do her first ass to mouth blowjob. There was no time for fighting or for words... he pulled her by her hair and just shoved his cock down her throat, which he fucked vigorously for a minute of her in a constant, retching gag, before pulling out and dropping another monster load into her gullet, shooting rope after thick rope of cum straight to the back of her throat.

He adjusted his phones and made her put on high heels where he forced his cock into her pussy with both of them standing and facing the wall. He pulled out of her pussy and fucked her ass in the same standing position, before lifting her in his powerful arms and literally raising and lowering her up and down on his cock in her ass while facing both cell phones as she begged to be fucked hard.

He fucked her that way and in various versions of that position for another 15 minutes before dropping her to her knees for another oral cumshot.

When he was done, he had been pounding Jenny for an hour without interruption. He left her a crumpled, exhausted mess on her bed as he uploaded all the video from her phone to his own cloud drive, before getting dressed.

"You know where to find me when you want me again," Nick said to Jenny as he turned to leave her bedroom before letting himself out of her apartment.

She lay there motionless for about 10 minutes before rolling over to check her cell phone. There was a single text message to Matt that Nick sent before leaving—it was the URL to the shared cloud drive. It was marked "read." There was no response.

Jenny was unlucky in love. Her luck, as ever, continued.