Unlucky in Love Ch. 01

"And then all three of them ended up fucking me up my ass against my will. They took video and everything." Jenny texted her coworker, Matt, whom she was trying to get to take her out to dinner and maybe more.

Matt had been playing coy... hard to get? Impossible for Jenny to crack. Jenny is a very average looking Chinese girl with two nice attributes—her "dick sucking lips" and round, peach shaped ass and thick legs. You might give her a 6 depending on your tastes... guys who like Asian girls could stretch to a 7, guys who didn't care for her, a 5 or 6. She was a bit overweight but not fat... just you know, like 132 pounds on a 5'3" frame but with no tits to speak of, sadly. Even when she gained weight it didn't go to her tits... they were just a bit more than A cups.

And Jenny had been very unlucky in love. Her first boyfriend was a complete tool who always made her feel substandard, and who only seemed attracted to her when she was sucking his cock. Her second boyfriend broke her for years. He fawned over her, was respectful to her, and was loving and kind. Most importantly, he seemed really into her; he made her feel beautiful, sexy, even desirable. Sometimes he even had her pose for intimate photographs, which scared her at first but over time came to make her feel cherished and wanted. When she was with him, she felt sexy.

They even experimented in the bedroom a bit with some exhibitionism, leading to several three-ways with one of her boyfriend's friends before they broke things off when he moved to France for work. She wanted to do the long-distance thing, but they both knew it would prove too hard. When he began dating a Parisian girl just a few months later, she was devastated.

She fell into a deep depression and she medicated by sucking and fucking their mutual friend who remained in New York with her but as he had a steady girlfriend, he was getting more serious about, he too became less available. Jenny didn't find many men in New York like her boyfriend—not ones that were into her, and needing affection, sex, and attention, she turned to dating apps... and she lowered her standards, considerably.

Most men took advantage of her, and as her self-esteem dropped, she opened herself to greater and greater abuse just to feel wanted by someone... anyone. In her desperation to get Matt interested in her after flirting with him at the office for months, she picked up on the fact that he lingered on a detail of a sex story she had told him while lamenting the trials and tribulations of hook up apps in New York.

They had already exchanged some nudes—as usual, his was just a dick pic, but Jenny in her quest to please and entice, had been sending full frontal nudes, pictures of her in bondage apparatus, even pics of a man's hand pushing a dildo into her ass while she grimaced. She had sent that one when Matt seemed to engage on the topic of forced and coerced sex.

"Oh god, any date that survives the restaurant I usually finish off with a blowjob just to get out of there safely and so that I don't have to call the guy back if there's no connection." She told him one night.

"Wait, you're telling me any guy that takes you out has a better than 50/50 chance of a BJ?" Matt asked incredulously.

"It's New York... I'm no ten... they expect you to put out. Believe me it's a lot better than the date rapes." She replied.

"Oh now you're just trying to titillate me." Matt replied.

Jenny knew the topic of forced sex could be highly erotic to some men—hell, even though she had been date-raped multiple times there were still certain scenarios even she felt were erotic, and Matt had just laid out the chance to explore it. Jenny took the bait.

"Oh you have no idea... I was on a date once with this guy from Flushing who picked a restaurant near my apartment in Brooklyn just for the chance to try to get back to my apartment. I don't know what I expected... I could see right through his attempts to go back to my place to 'check out my vinyl collection' and other things that could only be done in my apartment." Jenny said to Matt.

"Well what happened?" Matt asked, obviously wanting the story.

"Well... within minutes of getting into my apartment, he got touchy feely right away. It didn't feel right... he tried to make out with me—but his hand... it went to my throat right away. Like, that's not exactly first kiss material is it? I like to be choked as much as the next girl, but it freaked me out... then... you know..." Jenny said, leaving the details.

"Wh—what... what happened?" Matt asked, his voice the tiniest bit strained.

Jenny decided to get graphic and see how Matt would respond. She was 90% sure he wanted details...

"God, I hope you don't think less of me if I tell you." Jenny said, in a thinly veiled attempt to get him to goad her on.

Matt simply said, "Tell me."

"Well... I pushed him away from me and asked him what he was doing... he got mad... like, real hot, real fast. He slapped me twice and screamed at me to cut the bullshit. I just shook in fear... I didn't know what I did wrong. He told me I knew why we were up in my apartment... he said he knew what I wanted..." Jenny said in a meek voice.

She heard Mark breathing a bit more heavily, before he said, "Go on..."

"Well... then... then he raped me." Jenny said, pausing... " I mean... I don't want to scare you off with too much detail... I like you, Matt."

"No... it's okay." Matt replied. She knew he wanted more detail. All of it.

"Okay... well... he reached for me and ripped my button-down blouse open... he spun me around as he tore it off my shoulders... somehow he tore my bra off of me as well. It all happened so fast... I just remember him pushing me over my dining room table right here in my apartment... he flipped my skirt up onto my back... he tore my thong partially off so that it didn't block him... I just remember him slamming my face down into the table two times and telling me not to scream... then he pushed into me from behind. I just remember his sounds... like an animal... growling at me as he pounded into me from behind... he had licked his fingers and rubbed my pussy some before pushing into me I guess... so it didn't really hurt much... I just remember thinking... fuck... this is going to happen to me again sometime." Jenny said.

"Oh... God..." Matt said, groaning.

"I thought he would just cum in me, pull up his pants, and leave... but he was in for the long game..." Jenny said trying to see if Matt was excited or sad or angry or what. She felt like she was hearing 'excited.'

"What else did he do to you?" Matt bluntly asked.

'Excited. Perfect!' Jenny thought as she continued, "Well then he flipped me onto my back on the table so he could fuck me and see my tits and my face... he covered my mouth and told me what a stupid whore I was... how I knew I was going to put out an how I was trying to dine and dash... he fucked me a little slower like this... like he was trying to slow down and savor it... I just laid there and let him do it... I didn't fight back at all... I didn't want to get slapped again."

"Fuck..." Matt said.

"Yeah, fuck... so then when he realizes I'm not fighting anymore, he tells me to come over to the couch and face him and ride him. Me. He wants me to just fuck him while he lays there and enjoys it... so of course, I had to. He would have beaten me senseless if I hadn't... it wasn't a suggestion or polite request. And I just remember looking up at him with my "am I a good girl" blowjob eyes when he stood and told me to kneel in front of him... both of his hands in my hair holding me down on him as he stabbed at my throat with his cock. I just wanted him to cum and think he had a good time and not hit me anymore. He asked me if I was loving his cock... I told him I was. I told him I wanted to make him cum. I did want him to cum... to get it over with."

"So he slapped you, stripped you, bent you over a table and fucked you... flipped you on your back to fuck you some more... then made you ride him on the couch... then he facefucked you?" Matt asked... Jenny thought she could maybe hear him pumping his cock in the background.

"Exactly... can you see that? Can you imagine that happening to me?" Jenny asked.

"I'm imagining it right now... I hope you're not upset... I mean... you know." Matt replied.

"No... no it's in the past... and I can see how maybe it's hot for you. I wish this was the only time that had happened... but it's more common than you think here." Jenny replied.

"Fuck... so... so how did he finish?" Matt asked.

"Like, did he cum on my tits or in my mouth?" Jenny asked with a laugh.

Matt laughed too, but clarified, "No... I mean... was that all... He came from your blowjob and left? He didn't... try to fuck you in the ass or anything else?"

"Oh no, thank God... I mean that's happened... just not with him. No, he just fucked my mouth and then pulled out and pumped his cum all over my face... the asshole even took a video of it and texted it to me to show me he had leverage on me and that he was going to get away with it. No girl would want that as a matter of public record..."

"Wait... wait... so... you're saying there's video of this guy's cumshot after date raping you... And... you're also saying... You've been raped in the ass?" Matt asked borderline wistfully.

"Two for two." Jenny said, hoping he'd ask for more... Matt was out of her league, looks wise... he seemed nice to everyone in the office, had a good upwardly mobile career... She didn't want Matt to rape her, but she did think getting him on the playing field for a little dinner and a BJ could give her a chance with him. Jenny had done some kinky things... that can be pretty enticing for a while to any guy.

There was a long pause in the conversation... Matt's breathing was heavy... he was obviously turned on and thinking about everything she had told him.

"Can I see?"

"Oh my god... Promise you won't show anyone at the office... I'd be dead." Jenny said.

Matt was elated her response wasn't "NO!"

Matt watched his cell phone patiently, thinking a 10 second tiny cell phone video of a guy popping in Jenny's mouth was about to drop. Instead, there was a cloud drive link to a 484Mb MP4 video.

"What... the fuck..." Matt asked.

"Please don't show anyone." Jenny replied.

"Let me uh... let me watch this and call you back." Matt said as he hung up the phone.

Jenny waited almost 30 minutes to hear back from Matt, but when he called, he sounded rested... relaxed. She knew he had just jacked off watching a video exactly as she described to Matt, picking up with the guy fucking her on her back at the edge of the table for about 2 minutes before telling her to come ride him on the couch. The words he used were the words she described... the way he talked to her sounded like a rapist... in control... The camerawork wasn't great, especially when she mounted the man and rode him for about 5 minutes, but the blowjob... and massive cumshot... was excellent... even by PoV porn standards.

"That was... that was intense." Matt said to her.

"I'm glad it got you off." Jenny replied... before adding... "You know... I could get you off."

Matt told Jenny he was uncomplicating his life at the moment and that their date would have to wait... but that he was certainly eager to hear and if possible, see more.

Jenny knew she should hold some things in reserve, so she told him to call her when he was more able to act on his impulses, and that's where things landed for a while.

--

Weeks went by and it became clear to Jenny that Matt was avoiding her a bit at work. She began to feel resentful that she had opened up so much to him, but then one night she got a text, "You up?" from him about 1am.

"I am... you need to hear more date rape stories?" Jenny asked with a winking smiley face emoji.

"Just one." Matt replied.

Jenny called Matt and Jenny talked for about 20 minutes through a bunch of her "so I gave him a blowjob" stories before he wanted to stop beating around the bush and asked bluntly, "So have you actually been raped in the ass?"

"More than once." Jenny solemnly replied.

"Fuck, I love that." Matt said, leaving no question of his intentions.

Jenny began telling him the story of a guy she dated for almost a year that she met on the dating app... telling about how she sucked him off on their first three dates to keep him interested, to the part where she kept teasing him with thong covered pics of her ass in 'fuck me' and 'pound my ass' face down, ass up pics -someone- had taken of her, to the point that he began telling her he was looking forward to fucking her ass someday and could they please go out Friday night?

"So, I'm like, yes... this is going somewhere... we might have sex on Friday!" Jenny told Matt.

"So wait, are you saying you sucked his cock the first three dates you went on and on date number four he... somehow... raped you in the ass?" Matt asked with a hint of excitement in his voice.

"Well just wait and see! So anyway, anal... is not something I'm like, in love with, ok? I know guys love it... my ex bf loved it... but since he moved away I really didn't give my ass to anyone else... so I was like... out of practice, and fearful it would hurt again... and that guys wouldn't be as patient as my boyfriend... you know." Jenny said, painting a grim forecast for anal to Matt.

"So... he comes over... we do dinner at my apartment... and he starts telling me how nice my ass is... how much he loves the pictures I send him... how much he wants to fuck it... and he reaches into his jacket pocket and pulls out this tube of lube... and I look at him and I'm like... 'Oh.' And before you know it, he's on top of me and he's kissing me like crazy and telling me he's been waiting for it so long, and in my mind I'm like '3 dates is a long time before anal??' and I begin telling him he's rushing things... that I don't like anal—big mistake, by the way... he takes it as a challenge or insult, since I had been sending him one provocative pic and text after another. In hindsight, you know..." Jenny explained.

"Oh god, tell me he holds you down and fucks your ass." Matt said, obviously excited.

"I assume you want the deets?" Jenny asked.

"Duh!" Matt exclaimed with a laugh.

"Okay... well... we haven't even had vaginal intercourse to this point, and I pointed that out to him as he began tearing my skirt and panties off my legs. And he pushes me over the arm of the couch, like this..." Jenny said before taking a selfie of her bare ass as she bent over the back of her couch and sending it to him. The wide-angle lens on her phone put her body in view over the back of the couch perfectly and the slight fisheye effect made her peach shaped ass and perfect rosebud look almost cartoonishly nice.

"fuck!" Matt replied.

"yeah... he didn't even take my top off... I just got a thumb full of lube up my back door as I begged him to stop. I literally begged him. And at this point he began to get confused and annoyed... like, he legit thought I was trying to tempt him into a 4th date butt banging and all I was trying to do was keep him interested enough that he might go deeper with me than just the superficial BJs... and he gets angry. His thumb begins ramming into my ass as he pours lube down my crack and as I practically yelled for him to stop he screamed at me to shut the fuck up... that's when he covered my mouth with his right hand and he just kinda put all his weight on top of me over the back of the couch right? And I'm screaming muffled screams into his powerful hands... this guy worked out... a lot... he could do anything he wanted to me... and he did. When his thumb stopped stabbing my back door, his cock was next in line... I felt him pushing against my back door... I tried to keep him out... he growled at me and pushed harder still... finally, it's like a damn broke... He pushed inside me and didn't stop until his hips rammed my ass. If I could have leapt from the couch up to the chandelier like a cat, I would have, but he was so strong... he was just on top of me... I just took it and cried."

"Fuck!" was all the response Matt could manage... she could hear him masturbating on the other end of the line.

"Yeah fuck is what he did... he fucked my ass... long and hard... he told me later that he had jacked off before coming over so that he could last... I wish he hadn't... it was like... an hour of agony." Jenny admitted.

"Oh... Fuuuuuck... he... he raped your ass... for an hour?" Matt asked incredulously but while panting.

"No, I'm sure it was much less time than that, but honestly I have no idea how long it took... I just know he fucked me long and hard... he changed pace... took it slow... did it rough... did it smooth... he absolutely destroyed my ass... but that's the other thing about it taking so long... after the initial shock wore off, like, most of the pain subsided." Jenny recounted.

"Are you saying you were loving it at the end?" Matt asked.

"Oh god no... nothing like that... just that... it wasn't like the beginning. I just kept begging him to please cum... please cum... when he did, like the little blowjob whore I am, I fell to my knees in front of him and let him jack off over me." Jenny said.

"FUUUUUUUCK... I'm cumming!" Matt exclaimed.

The phone was silent for several minutes and then Matt asked in a raspy voice, "So... that was it? You guys broke up? Why no cops?"

"Oh no... it wasn't even over for the night... my crying was over... the rough part was over... I practically smiled through his cumshot. I can't help it... it was inappropriate then for sure, but like... there was this guy I liked cumming because of me and I just took it. I wiped my face off as he went to use my shower... When he came out, he was hard... said he was thinking about my BJs in the shower... said he loved my pictures... asked me if he could take some of me sucking his dick."

"The same night he raped you?" Matt asked.

"Literally right then. So stupid me... or smart me... I don't know... I just didn't want him upset like before... and I was already making excuses for his behavior in my head... he said I was beautiful while shooting pics and vids as I sucked his dick. I tried my best to make these fat bitches look plump and amazing as I sucked him... I let him take a complete cumshot video as he erupted in my mouth and on my face a second time. I wanted to tell him he raped me and I was done, but he just texted me a restaurant URL from Yelp he wanted to take me to the next night and then kissed me after I'd wiped up. We dated for almost a year after that." Jenny admitted.

"Fuck, you are perfect." Matt said to her.

"Hey, no anal rape on our first date, ok?" Jenny said to him.

"I'm not making any promises!" Matt joked before they ended the call.

--

More weeks would go by though, and that date never happened between Jenny and Matt. She had sent him the video of her ex, Kevin, from the BJ and cumshot of her first anal rape and even followed it up with a brief video of her sucking off three different guys—but Matt still stayed on the fences about actually taking her out.

Jenny didn't want to use her best ammo on him yet, but she was running out of options, so one night she texted Matt with an edited 10 second video clip of a guy pushing his cock into her ass while she cried.

"what the fuck is this and why don't I have all of it?" Matt asked, taking the bait hook, line, and sinker.

"So I told you how Kevin and I started experimenting in... other things... after the anal rape, you know... after we were really dating... silly, simple things like giving BJs to his friends while he watched or took pics or whatever... I had had threesomes with The Perfect BF, you know... I was no prude, really... so it was easy... I enjoyed the attention... the sex was good... I felt wanted and desired, all the things I had been struggling for." Jenny told him as she heard him unzipping his pants.