My Ex Is Blacmailing Me

The following is a work of erotic fiction and is in no way meant to represent real people or events. It is completely written and owned by me, OfStarsAndDreams.

Contents: F, M/m, fetish, BDSM, blackmail, nonconsensual, degradation, verbal/situational humiliation, insults, raw/emotional, name calling, forced bi, bisexual, infidelity, clothed female nude male, ex-girlfriend, submission, psuedo-cuckold, light masochism, light sadism, oral (M/m, nonconsensual), anal (M/m, nonconsensual), anal creampie (M/m), ass to mouth, documentation without consent, threats, emotional abuse, emotional manipulation, psychological abuse, emotional sadism, gloves, lube, heels, forced crossdressing

Let's begin!

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The cold ground beneath my bare knees was familiar in an entirely unpleasant, trauma inducing way. The hard concrete scraping up the soft skin of my legs and hands, the top sides of my feet. Just walking into this room had made me feel ill, and this was unfathomably worse. It had been a couple weeks ago, but the experience had been thoroughly seared into my consciousness.

It had also been kept fresh by her frequent communications, her tormenting and teasing. I had bought a burner phone, but she refused to send the messages there and seemed to delight in my having wasted my money on it. She would send inappropriate texts and pictures - never of herself, of course - and I had to stay constantly vigilant so that I could respond and delete them immediately so my girlfriend wouldn't find them. I couldn't block her number, either, because I had to respond , as per her demands. It was horrible and humiliating.

"Look at you, so eager to please today. I barely had to order you to take your clothes off at all. Such a slut," her voice drilled into me. More like you have enough on me to ruin me if I don't, you mean. I felt a sharp pain in my side as she dug one of her heels in a little. "Look at me when I talk to you, you dumb bitch!"

I obligingly looked up, though it hurt my stiff neck to do so. She was slowly sliding on a pair of long black latex gloves. Like opera gloves, but in glossy black rubber. I hated her and I wanted her and I hated that I wanted her. I also felt so incredibly guilty. Surprising how something so simple could make me feel like such human trash.

"Would you believe that I got these just for you? I can't believe I wasted so much effort on you back in the day, you're such a pathetic piece of shit. Well now I certainly have you, don't I? Who knew it was actually so easy," she laughed, derisively.

She walked around my prone figure, occasionally kicking me for good measure. I could hear her heels clicking on the concrete. I knew better than to move. Then I felt those damn gloved hands on my ass, parting the cheeks. I had feared something like this, considering how she ended our previous encounter, but the cold and wet sensation of the lube still came as a shock, pouring out over my asshole and dripping down my taint to the floor.

"Be thankful I used lube," she said, mockingly. I wasn't sure whether I should try to look at her as she spoke or not, and decided against it. Then I felt a sudden shock as she veritably impaled me with her latex covered finger. "I SAID BE THANKFUL, YOU DICKLESS WONDER, as in, you know, SAY THANKS TO ME."

"Thank you!" I gasped, reeling from the pain.

"Thank you what?" she jeered, ramming her finger in repeatedly.

I had no clue what she was looking for. My mind was having trouble keeping pace with events, and I randomly babbled the first thing that came to mind. "Thank you, sir!" I immediately regretted it as soon as it was out of my mouth. Gee thanks, Full Metal Jacket. Such an idiot.

Her laughter was immediate and loud. "Holy shit, what a clueless pile of shit you are. But I guess that does show your true colors, doesn't it?" As she spoke she slowly started forcing a second finger into my already aching asshole, wriggling and stretching it. "You don't want a ma'am, do you? You want a sir! You pathetic whore, you want to be a little girly boy, don't you? A cute little sissy whore! My god you are disgusting. You make me want to puke."

She returned to where I could see her. "But, hey, don't you know whores need whore makeup?" she said, kneeling down in front of me and promptly slathering her dirty lubed fingers over my face, including my lips. I pulled away reflexively and she just grabbed my hair and pulled me back, shoving her fingers into my mouth in recompense. "None of that now, you bitch. I own your ass. I'll do whatever I fucking want." I could feel her fingers gliding along my gum line. "Who owns your ass?"

"You do," I struggled to say around her hand.

"Fuck you sound like a god damn retard. You know, this gives me an idea though. Since you want to be such a little sissy whore, maybe we can give you a little makeover! Cause you know girls love getting all dolled up. You're a shit ugly girl though. Well, a shit ugly anything."

She started rummaging around in her purse. I'm honestly surprised she brought it, but I guess she had to carry the gloves and lube in something . She pulled out a tube of lipstick, mascara, and some sort of powder along with a small hand mirror and brought them over, placing them on the floor in front of me. "Put them on! Let's make you look like the whore you are."

It was very hard to position myself in a way that was still on my elbows and knees while holding the small hand mirror and any of the makeup. I started with the lipstick. A small part of me had the weird thought that it wasn't really my shade. The absurdity of it almost made me want to laugh, but it also made me want to throw up.

I was just starting to apply it when I felt someone feeling up my ass again. I was at first confused. I could still see her, watching my face with growing amusement and contempt, the vicious hatred oozing from her face, eyes like daggers. Then who...?

And then I felt something forcing itself inside me. A sharp initial pain followed by an unpleasant ache that seemed to fill me. There was something inside me, something warm and hard and smoothAnd now it was sliding in and out, there were hands on my hips, jerking me backwards. Someone was... oh my god someone was fucking my ass. I panicked, almost scattering the makeup across the concrete flooring. No, no, this can't be happening. Of course that's what she meant, I was such an idiot.

"What, tired of your little makeover already? Well I'm not tired of watching. Get to it, slut!" I could have punched her in the face, but instead, to my horror, I obediently picked up the lipstick again and tried my best to apply it, fumbling to maintain my position and hold the tube with any sort of dexterity. The thrusting kept jolting my body though, and I inevitably smeared makeup out from my mouth, like some sort of bad clown reject.

"I knew you'd be shit at this, but my god, did you not like, learn how to paint within the lines in fucking pre-school? You're so pathetic. Just as bad as you fucking. Arch your back more, you stupid bimbo! Don't make him do all the work!"

I could feel the hard cock pounding inside of me, hear the light groans escaping the man's lips. Was it the same one? A different one? I had no idea who it was that was fucking me, and the thought filled me revulsion. I could also feel the length of it running against my prostate, and I couldn't deny a certain amount of enjoyment from the sensation, buried under the pain. It made me feel sick to notice it.

I found that one of the powders was a blush, the other an eyeshadow (in sultry blue) and rapidly smothered it on my cheeks and eyelids. No use in trying. I knew it was going to look horrible. Her face only grew more excited, like some predatory animal circling a kill. I grabbed the mascara, and hesitated briefly. There was no way I could do this without jamming it in my eyes, the way he was having his way with my ass. Just thinking about it made me want to crawl in a hole and die.

"Get to it, cocksucker! Doll yourself up for your john!" She slapped me across the face suddenly, and I could feel the sting sharply across my skin and through my jaw.

I begrudgingly pulled it up to my lashes. I'd been right - there was no way I could. Whoever was fucking me seemed to take sadistic joy in using particularly harsh thrusts whenever I was holding the damn stick up to my lashes, causing my hand to slip and jam it into my eyes multiple times. The pain of the mascara brush and his cock both jamming into me caused my eyes to well up, and the emotional trauma started pooling up inside me, gushing out in big wet tears.

Her eyes lit up in delight. "This is so. Fucking. Great. Look at yourself." She forced the mirror up to my face, even though I'd already been holding it, so I could see the trail of mascara running down my face from my tears. In the mirror I could also see the form of the man fucking me, still shoving himself inside me, but I tried to ignore it. "You look like a girl who got pumped and dumped at prom. Such a stupid, naive, little slut, giving it up to any boy who shoves a dick in her face and calls her pretty. But you're not even pretty. You look like stupid trash - because you are stupid trash. Shake that ass, stupid trash!"

She grabbed my head by the hair and forced it down. "Lick my heels, you stupid pathetic slut. It's the closest you'll ever get to actually doing anything with me ever again. Oh, you'll get plenty of use, just not from me. I hope you like big, fat, cocks. Actually, I hope you don't. I hope you hate it. Every. Fucking. Time." She used her other heel to sandwich my face against the ground. I was barely able to maneuver myself in a way that I could use my tongue to lap at her heel. It tasted unpleasant, and I could feel the grit of dirt in my mouth.

She pulled out her cellphone. "Photo time!" she crowed, laughing and giggling.

As the light and the snap went off, I felt the hot cum pouring into my ass as the man behind me groaned and grabbed my hips, pulling me against him hard. He pulled out, spraying cum across my back, and jerked me suddenly upright and shoved his still dripping wet cock into my mouth. I could feel the cum dribbling out of me onto my legs and the floor. He held me like that, fucking my mouth as the last trickles of cum escaped him and until he finally went soft. He pulled it out and, laughing, slapped it lightly against my face like some fucked up gesture of endearment

And the whole time I could hear her laughing and the clicking sound of her cellphone as she took picture after picture.

"I'll keep in touch, okay, my little slut? Maybe I should put these up on the internet, what do you think? Also, I'm really hungry, I'm going to take the money in your wallet for dinner. If you don't have enough I'll have to punish you. Who owns your ass?"

"You do," I whimpered, cum still oozing down my throat.