Flirting with the Devil – F/27 M/32

I have finally had it. Everything is unsatisfying. I have been the good girl my whole life and after spending the last five years at the bank working my way up, being polite, wearing my nice pencil skirts and blouses, I have officially had it. I had nearly straight A’s in college and barely knew what the definition of a frat party was. Then I got my job at the bank and being little Miss Perfect just continued. Everything about me and my life is typical, predictable, mundane, boring, and more than vanilla.

Get a tattoo? Nope, Cassandra would never do that.

Show up to work hungover after a Thursday night happy hour that lasted too long. Never.

Have sex on the first date. Not Cassandra.

I don’t know what happened, but I can’t live like this anymore. My life isn’t fulfilling, not even something I look forward to anymore. Granted, I can’t just quit my job at the bank, but outside of those 40 hours a week, I have to find something else to do with my time. Something exciting. Find a passion about something. Anything but continuing on the road I am on.

My genius idea? Head to a biker bar and start with a one night stand. I have rationalized this as my best shot for a complete 180 in my life. This could go one of so many ways. I am either the bravest or dumbest person in the world right now. It’s Tuesday, which leaves me enough time to order some leather pants, black lingerie, a low cut top and some sexy boots.

Thankfully everything arrived by Thursday and fit surprisingly well. I still had no idea how to do my hair or make up but I guess I would figure that out later.

I leave the bank by 5:15 Friday and head home to change. Time to get operation One Night Stand with a Biker underway. I need a serious makeover involving anything but a bun in my hair and probably some heavy black eyeliner around my eyes. I shower and shave eve..ry…thing. I slip into a black lacy thong and matching lace push up bra. I shimmy into the leather pants that are now hugging and showing every curve from my tiny waist down. I pull on the black spiked boots with a good 5 inch heel. My feet would probably kill by the end of the night. I stand in front of my vanity without my shirt, because I don’t want to get any makeup or hair product on it. I take my long auburn locks out of the towel and decide I am going to let my hair be wild and free like me tonight. Smoothed in a little serum and let my shiny waves tumble down my back. Time for makeup. I went with the black eyeliner, shimmering gray eyeshadow, and dark plum lip for a touch of color. I grabbed my shirt. A perfectly form fitting white t-shirt with the shadow of my black lace bra underneath, leaving just a tiny bit to the imagination but a little intrigue. I think I look good for 27.

This is it. Here I go, headed straight for Tommy’s Saloon. It’s the only biker bar in town and there is no way I will run into a soul I know. It’s a safe bet for a wild and fun one night stand. My way of jumping in feet first to jump start more new and exciting adventures in my life with this new leaf I am turning over. No more perfect Cassandra. I am going to be Cassie for the night.

I feel the nerves in the pit of my stomach and start thinking I can’t go through with this when I pull into the parking lot, full of all sorts of bikes and a few big trucks. I pull into one of the last parking spaces as the sound of the live band and running bikes fills my ear. Fake it until you make it, that’s my motto. I give myself one more over in the visor mirror, muster up all my fake confidence, and head into the packed bar.

Thankfully, the place didn’t go silent and stare at my entrance. In fact, I pretty much made it through the door and to the bar unnoticed. The bartender comes over after a few minutes.

“You aren’t a regular. Hope you know what you’re doing with this crowd. What can I get ya?”

“Is it that obvious? And a whiskey sour, no garish.”

He laughed, “Yeah you are that obvious to me and fuck, if you think there is garish behind this bar.

How do bartenders do that? They know everything about everyone. He sets my drink down and I slide him a $20 and tell him to keep it.

I finish my drink and contemplate a flaw in my plan. What if no one approaches me, how do I flirt and get myself a date for the night, without looking like a fool or pissing off one of these biker babes. I didn’t think I would have to do much besides order a drink at the bar. Single, no man with me, I thought this would be easy. Fuck, I am dumb or seriously unapproachable, which could be the case.

I am now completely beating myself up for being so stupid. I set my glass down and notice one of the guys at the other end of the bar looking my way. Another whiskey sour appears in front of me as the bartender tips his head to the guy at the end. I raise my glass in a toast to him and take a sip. Guess I could nurse this second drink. He starts to walk over to me.

He’s tall, dark and handsome. Nothing extraordinary but will fit the bill for what I had in mind. I am not about to be picky trying something new.

“You aren’t from around here.”

I can’t help but chuckle. “Seems to be the observation of the night.”

“So where you from?”

“Here, just never been HERE.” I confess.

“Oh yeah, what brings a pretty little thing like you into a place like this.”

“Thank you. Honestly, I am looking for a change in my usual routine. And wanted to try out this new outfit.” Now I am flirting, fishing for more compliments.

“Your outfit does look hot. What’s your name?” He finishes his Bud Light and the bartender brings him another.

“Cassie. What’s yours?” He slides my whiskey closer to my hand, urging me to finish it. I can already feel a buzz working into me. I didn’t entirely want to be plastered for my little endeavor.

“Sam.”

“Sam, if you could excuse me a minute. I have to run to the restroom but I’ll be right back.” I decide to finish my drink with the intent on coming back but you know that whole don’t leave you drink unattended thing.

I push through the crowds of people. Starting to feel that second whiskey working through me now. I need to slow it down, maybe order a coke too. I check myself in the mirror, makeup still nearly perfect and I put on my brave, but slightly buzzed, face to go back out there. I came to screw a biker and that is what I am going to do.

I get back to the bar and Sam. There is a fresh whiskey in front of my seat. Thanks I say picking up the glass and setting it down, but I really need to drink a coke or something else first. He waves the bartender down and orders me a coke. He sets it down in front of me and I grab the glass and gulp it down. That should help me. I continue to chat with Sam casually as I grab the whiskey and contemplate continuing to drink. As soon as I raise the glass for a sip this huge arm comes out of nowhere and knocks the drink out of my hand.

“What in the actual fuck?” I scream.

“Yeah what the fuck motherfucker?” Sam shouts as he turns to the guy standing to my other side.

I am literally sloshing whiskey and ice off my lap as I turn to look at the asshole who dumped my drink. Wait, what?

“Anthony?” I swear to God I am staring straight at Anthony, our bank branch manager.

“You need to leave right now Cassandra!” He is stern, nearly angry with my presence in this bar and I have no idea who this Anthony is in front of me. He is in jeans, big black combat boots, a cut off t-shirt, and a leather vest with patches. He has tattoos up both arms and even up to his neck. If I didn’t know any better I would say this must be some twin brother because this can’t really be him.

He is toe to toe with Sam. I grab a few of those square napkins and attempt to pay myself dry. I think this is it. I am done with this little fiasco. I should really leave while I can, and hope this is not really my manager, about to get into a bar fight. I go to stand up and my legs buckle and I can barely hold myself up on the barstool.

“What the fuck?” I mumble. I look at Anthony fear in my eyes as I look back at Sam in front of him. I might be perfect little Cassandra but I am not a complete dumb ass, I watch those crime documentaries and Law and Order. I have been drugged, by Sam or the bartender or both, and I am truly fucked. FUCKED.

The last thing I see is Anthony throwing a violent punch to the side of Sam’s head, Sam falling straight to the floor, and then him pulling me into his arms as my vision goes black and I pray this really is the Anthony I know or I am screwed.

I wake with a pounding headache and sour stomach. I try to adjust my eyes to the light and scope my surroundings. I am on top of a bed, with a blanket. I push the blanket down. I am in a men’s oversized t-shirt. I still have my bra and thong on but just those and this t-shirt. I instinctively begin feeling my body trying to wrestle with the question of whether or not I was assaulted or if I had sex. My stomach flips, I am going to be sick. I bolt from the bed and run to one of the two doors across the room from me. Thank God it’s the bathroom as I throw my head into the toilet and empty whatever was left in me.

“I didn’t touch you. Well, not like that. I put you in one of my shirts to get your alcohol soaked clothes off of you.”

I stay holding the toilet as I register that is in fact Anthony’s voice. Oh God what kind of mess did I just make for myself at work? How could I be this dumb? I try to pull his shirt down my body knowing my ass is still in my thong for him to see as I am leaning into the toilet.

“Cassandra, say something.”

“Um hi…. Uhh thanks, I guess.”

“What were you thinking?”

Two can play that game, although I am in no condition to match him at the moment. So I responded with my own question, “Who the heck are you, Anthony?” I try to stand myself up. It wasn’t graceful, I held on to the counter for dear life to avoid falling to the floor. He just stares back at me. Fine. “Who the hell are you Anthony? Tattoos, every inch of you is covered but your neck, face and wrists.”

“So?”

“And a biker? And you’re in that gang there too?”

“Maybe?”

“Maybe?!”

“Cassandra who the hell are you? Why were you in Tommy’s bar? Dressed like your were? I barely recognized you, except for your auburn hair.”

“Anthony, what happened?” I sounded desperate to know.

“Sam and Tommy, the bartender and owner, took you for an easy target. They have a bad habit of drugging the newest girl in the establishment. I thought I recognized you and had been watching you all night. I didn’t think the coke was laced, I thought the whiskey was. I was wrong and didn’t get to you in time. I am really sorry about that.”

“Sorry?” I screamed at him. “You associate with people like Sam and Tommy who drug the unsuspecting new girl because they can! You know it happens and allow it! What the fuck?”

“Cassandra, it’s not that simple in this life.”

“Simple enough for you to lead a double life, look at you!”

The room started to spin, my screaming made a ringing in my ears, and I started to drop to the floor. Anthony barely caught me as my body slumped forward.

“Come on, you need some water, Tums, toast and ibuprofen.”

He held me up and walked me over to the bed and laid me back down. Lifting my back up for an extra pillow. He handed me the water on the bedside table with a couple ibuprofen. I took a sip and the pills. Then he handed me a Tums and a plate with some cinnamon toast. I continued to sip the water and take small bites of the toast as I start to feel guilty for yelling at him in the bathroom.

“Better?” Anthony asks.

“A little,” I whisper. “What time is it?”

“Around lunch on Saturday.”

I sigh in relief. I still have the weekend to recover from this incident and hope Anthony forgets all about this.

“Cassandra, answer me, what were you doing at Tommy’s?”

“I don’t really want to explain that to my boss. Can’t I just thank you, forget this whole thing happened and I promise I will never walk into that bar ever again. I think it’s safe to say I learned my lesson.”

“And what lesson is that?”

“You will think it’s so stupid and it’s way too personal to share with you.”

“Cassandra, I got you out of that dangerous situation, carried you to bed, undressed you, I could practically see what was under your ‘fuck me’ lingerie, put a t-shirt on you, and tucked you into bed and telling me why your were in that bar is too personal. I think we are past some of these ‘personal’ formalities. If it helps you are the only one at the bank who knows about my tattoos and potential biker gang ties.” He shrugs his shoulders at the last part.

“Fine, if you laugh at me or make this awkward, then I am shutting up and asking to go home immediately.”

“I won’t laugh, promise.”

“Ok, I was sick of being a goody two shoes. I have been perfect all my life and I am tired of being boring and predictable, so…”

“So you walked into a biker bar? I would think there is something else you could do instead of that, like go to a rock concert, dye your hair, something!”

I tried to push back away from him and put some space between us. He noticed and moved away, dragging his hands through his hair, clearly frustrated with me. “Ok, I agree it wasn’t my best idea, but at 27, I just feel like I wasn’t living. I have never gone to work hungover, had a one night stand, or anything remotely off the straight and narrow. I am really unhappy. I figured I would jump in feet first and go have a one night stand with a biker to turn over this new leaf.”

Anthony dropped his head into his hands and a weird choking sound came out of him. Oh no he didn’t, “See you’re fucking laughing at me and you said you wouldn’t. Can you please give me my clothes back and take me to my car? I don’t want to be here anymore.”

“I’m sorry, but Cassandra you do realize how crazy that sounds, right? Like dangerous. Which is clearly how this would have turned out if I didn’t intervene for you.”

He was right and now my head dropped. I am so ashamed. I couldn’t help it, I started to cry.

“It’s ok, Cassandra, it really is alright. Nothing bad happened and you are here now. I am sorry I laughed at you.”

“You just don’t get it Anthony, probably never will, since you lead a double life anyway. Maybe that’s all I was trying to do?”

“I gotta ask, Cansandra, you’ve been with a guy right?”

“No shit Anthony, I am not a fucking virgin for Christ’s sake! I just want something different, not boring, new, maybe a little wild and crazy.”

His face looked relieved and then something else settled in his eyes and he looked me over.

“What? Why are you looking at me like that?”

“Well um… I have a crazier idea than yours.”

“What?”

“I could be your one night stand with a biker, Cassandra.”

“You’re my boss, that’s a crazy idea. What would that do to us at work?”

“It’s a one night stand and you didn’t actually just say no. You’re considering it, aren’t you?”

I feel my face blush. Anthony steps back toward me on the bed and brushes some of my hair back behind my ear. I shiver at his touch and my breathing hitches. He notices. So, he takes it further, lightly brushing his fingertips down my arm. My eyes fluttered closed as I take a deep breath, the scent of him all around me.

He speaks again, “You’re a gorgeous woman, Cassie, with soft subtle curves, and based on what you shared, no doubt the body of women that hasn’t been treated like the Princess she is.”

My eyes shot open towards him once he said Cassie. He sucked me into his stare. His fingertips trailing up and down my arm until goose bumps appear. “What do you say Cassie, a one night stand with me? We will get this out of your system.”

I nod.

“No Cassie, words, consent, communication, are key here. I don’t do vanilla. I do BDSM and I am confident I can blow your mind and body in ways you never dreamed but you will have to tell me this is what you want and use your words. And submit to me.”

I let my mind stir over what he just said. And then I blurted out, “Can I just give you blind consent for the rest of the weekend? And then we forget this ever happened come Monday?”

“If that’s what you want, I am ok with it. You just need a safe word because saying no doesn’t mean much when people participate in this kind of sex. Just give me the first word that comes to mind.”

“Banana.”

“Banana it is. For the submission, I need you to clear your mind princess, do as I tell you to, accept what is happening unless of course you must your use safe word and then it will stop. But if you trust me for a day and give yourself to me completely, I think we can help you get over the this trapped in a boring life thing you got going on.”

“Ok, I think I can do that.” The dynamic is already changing, he is calling me Cassie and Princess and his eyes are dark as he looks at me like I am snack instead of his lead account specialist.

“Now let’s get you cleaned up.”

Anthony steps back and pulls off his own t-shirt revealing more tattoos. All different, all intricate and intriguing.

“Is there a part of you not covered in ink, Anthony?”

“Guess you will see in a minute, princess.” He scoops me off the bed and carries me back into the bathroom.

“Wait what? We are showering together?”

“You’re mine for the rest of the weekend. I do know what I am doing and I would prefer it if you stop questioning every move.”

He placed me on my feet as he went and started the water in the big walk in shower. The tile was cold on my feet. He turned back to me.

“Lift your arms Princess.”

I did slowly as he pulled his t-shirt from my body. I started to observe every inch of him to help calm my nerves. I am not sure it was working. His upper body bulged in ways I never noticed before. He chest and arms looked solid and there was that V dip into the top of his lounge shorts. He immediately went to my back and unhooked my bra. He grabbed at the center between my breasts and slowly pulled it from me, and they fell out, hanging firm and plump in front of him. He reaches for a nipple twisting it as I shiver head to toe.

He slides down the front of my body as the steam from the shower settles into the room. He hooks his thumbs into my thong and starts tugging down. I start to shake.

“Get out of your head Princess. I can almost hear your wheels turning over the shower. Relax for me, give yourself to me.”

I exhale and try as I step out of my panties. He stands and pulls his shorts down. And I watch his dick bob up, I gasp. I can’t take my eyes away, he is huge, more than two handfuls. This was crazy, he will hurt me with that thing.

“Stop Princess. Take my hand.”

I wobble and step forward placing my hand in his and he walks us into the shower. He pushed me past the rainfall shower head and pins my front against the far wall.

“Ahhh…” I jerk back. The tile is cold on my chest but my hands are pinned by him above my head so I can only get my hips and stomach away from the cold wall.

“Just like that Princess.” His free hand palms and rubs my ass. “I have been dreaming of punishing you for last night’s activity since I carried you out of the bar. Have you ever been spanked Princess?”

He asked I question I didn’t hear. I was slightly shocked over the position I was in, the loss of control and with Anthony.

He slapped my ass hard.

“Owww!!!” I screamed!

“Get out of your head now and answer me.”

“No I have never been spanked until now.”

“Until now Sir.”

“Until now Sir.” I felt shame and embarrassment but also something else. I felt my arousal rising between my legs. I shook my head confused by what what happening.

“You were a very bad little Princess going into that bar, alone, with the intent of going home with some guy. You should be punished thoroughly for that risky behavior. I should make your remember not to do that again. I am going to spank you 10 times. You will count each one aloud and thank me for your punishment when I am through. Do you understand?”

I nodded. He squeezed my ass hard. “Yes, Sir, I understand.”

He smacked my ass.

“One, Sir.”

Again, the other cheek.

“Two, Sir.” Again and again. By the fifth blow I was sobbing. It didn’t affect him.

He paused and dipped his hand between my legs. He found me dripping wet. He dragged his two fingers through my wet folds, playing with my pussy lips and I sobbed harder.

“Why are you crying Princess? What is so wrong when you so clearly like what I am doing?” He pushed his fingers in me and a moan slipped from my lips. “Answer me when I ask you questions or your punishment will only get longer.”

“I am crying because I am ashamed Sir. And scared of what will come next. I am afraid of what else I might like.”

“There it is. You have a word Cassie, use it if you must. But do not be ashamed of your body and what it likes, let go and experience all of this for the first time. Let’s finish your punishment.”

He smacked my ass five more times.

He then stroked my wet pussy again. “Thank you Sir, for my punishment, I won’t go to that bar again.”

“Such a good Princess.”

He pulled his fingers from my core as I moaned. He moved me under the water and began washing my hair and body. I watched him through hooded eyes as he took care of me and treated my body like a temple. It was becoming easier to let go, my body becoming more fluid in his hands.

He finished washing both of us and walked me out of the shower. Anthony wrapped me in an oversized towel.

“Truth is Princess as much as I want to continue this right now. I need to feed and hydrate you. Let’s go make lunch and then we can get back to this shortly.”

My stomach growled in response as I couldn’t remember the last time I even ate. He passed me a robe to wear.

Anthony made us soup, salad and sandwiches. Far better than I thought they would be. I tried to stay out of my head like he has asked repeatedly. But I couldn’t help pondering him, his tattoos, his dark, mysterious eyes, all of this double life stuff he has been leading far longer than me. We ate and finished quietly. He stood holding out his hand for me. I took it and followed him back to the bedroom.

He stood in front of me still holding my hand as his other hand undid the robe’s belt. It fell open as he reached in for a handful of breast. I leaned into his touch. I let something between a sigh and a moan slip from my lips. He let my hand go so he could drop the robe completely. I watched his eyes graze over my body. I found myself looking him over down to noticing the tent in his lounge shorts. I was eager and scared to feel that in me.

He cupped my cheek. “Princess, I want to get started on doing so many things to you but you have got to stay in the moment with me, trust me and your body. Your body is more reactive than you know and I promise I will follow your body cues.”

I closed my eyes, “Yes, sir.”

“Good, now kneel before me.”

I did. “You look so good on your knees Princess. I want to play with you all night and in order to do that, you are going to have to suck me off. Keep your hands on top of your thighs. And open.”

I did. He fisted his length, tapping his dick on my bottom lip and then pushed into my mouth. I sucked him slowly first, covering him in my saliva. And then he fisted my my head and hair into his hand and he fucked my mouth. He was using me. Instantly choking and gagging. He pulled out and shook his head. I opened my mouth silently telling him to resume his assault. And he did.

“Fuck, your inexperience is turning me on. Fuck Princess, I am not going to last.”

He pushed in and held himself at the back of my throat as I gagged. He looked down at me, “Eyes on me and you take every last drop right down your throat. Suck and lick me clean.” He fucked my mouth again and again and again. I tried to breathe between thrusts, still choking and gagging as he slammed my head down on him one last time. Hot cum shot to the back of my throat I choked at first and then managed to swallow, and swallow again. He held himself in me until I noticed him go soft.

“Good Princess, such a very good Princess. Lay on the bed for me.” He lifted me to my feet and turned me towards the bed.

I did as I was told. Unsure of what to do or how to lay, and the nervousness seeped into me. He watched me closely and my face flushed. I didn’t know what I was doing. He approached me. He reached for my left leg. He caressed my ankle and calf before reaching down the foot board and producing an ankle cuff. He fastened me to the bed frame. He moved to my right, yanking my legs apart, and repeated the same steps.

He climbed between my spread legs and ran his thumb through my pussy. “Already wet and glistening for me.” He bent down and placed a soft and gentle kiss on my clit. Quickly he leaned over me, I pushed myself down into the bed to get space between us as he hand grabbed my neck with a squeeze. “That kiss is the most delicate and gentle I will be with you during the rest of our time together.” He let me go as I panted for breath.

He climbed up me further. His dick hard again and resting on my chin as he yanked my arms up and away from me to fasten my wrists to cuff on the head board. He kneeled over my immobile body. “Open up again.”

He shifted and shoved his hard, solid dick into my mouth again until I choked and gagged. He pulled out, grabbing my chin for me to look at him. “You can do better than that, relax and know whatever pleasure you give me, I will return 10 fold.” He let my chin go and my mouth fell open for him again and he pushed inside. I tried to relax my jaw for him and keep my tongue flat against his length. He fucked my mouth thoroughly again. I couldn’t help but gag. Tears pricked at the corners of my eyes this time and he pulled out. He wipes the tears away with a smirk on his face.

“So good to me.” He worked down my body, kissing and caressing along the way. He was between my legs again as I struggled to get lean up to see him.

“Such as gorgeous pussy. Can you tell how wet you are for me?”

I flushed and lean back into the bed not wanting to look into his eyes. He pushed two fingers into me and I moaned. He dragged them in and out of me slowly before putting his fingers in his mouth. “You have the sweetest honey I have ever tasted. Do you want a taste?” I shook my head no. “Have you ever tasted yourself Princess?” I shook my head no again. He pushed his fingers back into me stroking my walls perfectly. My hips instinctively bucked up at him. He other hand moving to hold my hip down. He pulled his finger away and I exhaled in frustration, trying to lift my hips to follow his touch or bring it back. Instead he pushed his fingers passed my lips, swiping at my teeth as I opened for him. “See Princess, honey, sweet honey. Lick them clean.”

Satisfied he dipped back down between my legs and brought his mouth to my pussy. He bit my clit and I yelped. He pushed his fingers in as his tongue made circles around my clit and dipping into my folds. I was getting close, so close to orgasm. He pulled his mouth away. “Your close Princess I can feel it, has anyone every found your g-spot?”

“No.” It came out as a breathy whisper.

“I am going to enjoy this.” He started to move his two fingers in me but as he sat between my legs, his other hand pressed hard into my lower abdomen. I was held firmly in place by him but it changed the angle his fingers rubbed my walls.

“It’s right here Princess, show me what this does to you.” He stoked the special little spot he found and my eyes rolled back and my breathing picked up. “It’s good, isn’t it Princess.” My body rippled and pushed against his hold on me. “Let go, Cassandra, show me what you really look like.” His words broke me. I started to scream Anthony’s name while my body rocked in waves against the pressure he held down on me. It was a ride I ever experienced before. I abandoned my body to him. I started to slowly come down already feeling a soreness in my restrained body.

“You creamed for me.” He swiped a finger through my folds and put it in my mouth. I sucked my cream from his finger without being told. “Can’t let that go to waste Princess.” And just like that he was between my legs again lapping me up. My body threw aftershocks with each swipe of his tongue. When he had his fill he sat up.

“You doing ok Princess?”

“I think so.” I whispered. “I feel kind of high or buzzed.”

“Oh Princess it only gets better.” He started to undo the cuffs and massage my arms into my body. He did the same with my legs before turning me over. My face down into the mattress. He pulled my arms behind me slowly and began to fasten then together behind my back. He positioned himself behind me, raising my hips off the bed. I tried to turn back to see him, but he pushed my head back down.

I felt him drag the smooth tip of his dick through my pussy lips, before slowly pushing himself inside me. “Oh fuck Cassandra, you are so tight.” I wish I could fist the bed sheets or hold on to something but I couldn’t. I tried to put some distance between us, his width was more than I could handle and I felt the stretch in my whole body. He grabbed my hips pulling me back and laid a smack in my ass. “Get back here Princess, do not pull away from me.” I stopped fighting him. And he pushed in another few inches. He was forced to stop when he hit my cervix, there was no more room for him. He adjusted the angle of my hips and then he pushed in more. He was fully seated in me and I was moaning beneath him. I could feel his breath on my back, panting against me.

“Fuck you feel good.”

“Please Anthony,” I begged aloud for something from him but not knowing what. He withdrew and then pushed in slowly again, he did that a few more times before he really commenced to fucking me. He found a pace he liked and then his hand was in my bound wrists pulling me on to him harder. His other hand moved down until I felt his thumb on my tight puckered hole.

“No!”

“Yes, Princess and remember ‘no’ doesn’t work here. Do you need to use a different word?”

I held my breath debating. Anthony leaned over me, cupping my neck in his hand, and he whispered in my ear, “You have no idea what you like if you haven’t tried. Let me do this to you. Let me finger fuck your ass while I pound your sweet pussy.”

He let me go.

“Ok I will try.”

He grabbed my bound arms and pulled me back down on him. Then he spit on my asshole. He started rubbing hard circles on my hole while fucking my pussy deep and slow. He started to push his thumb in and I began to whine and squirm.

He grabbed my arms to steady us. “Squirm like that again with your hips and this will be over too soon.” I briefly pondered the effect I was having on him and decided to stop fighting. I pushed back towards him trying to open myself up. He pushed his thick, wet thumb into me slowly. It burned like fire, fire I couldn’t get away from. Slowly he pulled out and pushed back in. He was methodical in each of his thrusts.

“Fuck…” I moaned.

“See you like it and fuck Princess you are tighter now with me in both holes. I may not last.”

Again with his words. My body writhed. I became a woman possessed by a man. A man named Anthony. I was moaning and screaming his name as my body bucked beneath him. I started to cry in pleasure. I couldn’t open my eyes. Only ride this wave with him. He held me in place with him thumb in my ass and his fingers stretched across my back and the other hand pressing hard circles into my clit. My vision was gone as the orgasm tore through me.

“Fuck Princess, fuck me, oh fuck. Your gripping my dick and thumb so hard I can’t pull out of you. That’s it Cassie, fuck I have all of you.”

His body jerked and stiffened behind me. I could feel his hot load filling all of me. I fell weak under him. He held me tight. I felt sated, blissful even, worn out, but also terrified. Silent tears spilled from my eyes. I felt like I was crashing. Anthony slipped from me but held me close as he undid my restraints. He pulled me into his arms.

“Sshhh. It’s ok, you did amazing Princess. Fucking amazing. Let’s clean you up and get some water.”

He stepped away just for a minute but I was still crashing. Vulnerable. And what now? My job?

Anthony came back, reading the panic and tears across my face.

“Oh no you don’t. Everything is ok. This drop is normal. I am right here. Talk to me Cassie.”

“We work together. My career is over. We shouldn’t of done this. I am so dumb. I am so sorry.”

“Nope, we are not doing this Cassie. Yeah we work together, no your career is not over. But I just had the best time and so did you. You’re not dumb and there is nothing to be sorry for. You are inside your head again and you still need to be here with me.” He grabbed one of my hands placing it on his chest as I tried to settle my tears and breathing.

“Besides Princess, we might be done this time, but this isn’t over, not even close.”

I was so shocked, I kissed him. “But what about work?”

“That’s easy Cassie, we can transfer you under Robert and then you won’t answer to me.”

“When did you think of all this?”

“When your pussy had a death grip on my cock and the orgasm made you cry. I am so not done with you Princess.”(Hopefully working on a Part 2 to this one.)

Source: reddit.com/r/Erotica/comments/x5kyyg/flirting_with_the_devil_f27_m32