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I will Not Break

The true story of a two day test of who I could become

I am writing this to not forget the details- the sounds, the scents, the feelings- as they are sure in time to fade and blend into a concept of an event and not the intimate seconds and minutes that changed me.

Less than six months ago, being freshly divorced and newly confused with the decisions I made in my life, found myself at an educational conference for work. It was the first time since my ex, James, and I signed off on no longer being married, and I was still struggling with the fact that I had given up my mid-twenties to mid-thirties trying to make things work with him. And now here I was, forced out into a new life of solitude, staying at a hotel for three days and two nights to learn how to be a better employee.

I’m by no means a model, but do find myself to be a little above average in looks. Before meeting James toward the end of college, I was no prude nor too sexually adventurous. I had dated a few random guys and even had a couple one night stands. Now at thirty-three years old, I still stood at about 5’8”, could lose a few pounds, but still had an hour glass figure and my DD’s still seemed to gather attention, or at least I liked to think they did. My shoulder length brown hair that I usually kept up I decided to curl and keep down for no particular reason as I dressed for the conference.

On Monday morning I arrived at the conference to register. As I was leaning down to sign in, I noticed a tattooed arm, a very defined tattooed arm, signing in next to me. Intrigued I looked up at the same time he looked over at me and smiled.

“Hello,” he said confidently as I could only smile back while uttering no words.

Finished with registering, he wandered off, leaving me there to complete my registration.

About three hours into the conference, I decided to skip the next breakout session and look through the materials.

“Playing hookie?” I heard a voice say to me from behind?

I turned, and noticed the man talking to me was the guy with the tattooed arm from the registration table.

“Just taking a break,” I replied.

“Me too, but it’s close to lunch, so I figured I’d take a break at the bar. Interested?” he asked.

“You drink at lunch?” I asked, suddenly regretting it for sounding judgemental.

“I do when I’m not working, and this conference I don’t consider work. I’m Mike by the way.”

“I’m Monica,” I replied.

Long story short, I accepted his invite and had lunch with him at the bar. I’m not a big drinker but can hold my own. After a few hours of conversation and drinks which flew by, we noticed the conference participants leaving for the day.

Mike mentioned that he was staying at the hotel next to the conference center, which also happened to be the same place I was booked for the next two nights. We decided to walk back there, freshen up and then meet again for dinner in the lobby’s restaurant. I changed my clothes and put on a yellow summer dress that I brought. It was far from sexy but was the best item I had packed.

Just like lunch, the conversation, drinks, food and time flew by.

As we continued to drink, I continued to open up, explaining to Mike my divorce situation and my anger toward wasting so many years with James. Slipping up my words, I stated, “Who knows, maybe I could have run into someone like you in my twenties.”

Mike calmly replied, “You seem nice, which makes you not my type, or someone who could have handled me back then, or even now.”

A little taken aback, I questioned why he couldn’t be with someone like me.

"I'd break you,” he responded coldly while looking at me directly. “Look, you mentioned that you spent close to a decade with a guy and the sex was very vanilla. I was turned on to a different lifestyle pretty early, and people like you…you just couldn’t hang. Trust me, and don’t be offended. It’s a desired taste.”

My mind flashed back to my divorce and how often James told me what was good for me, what I couldn’t do, or what I wanted in life. Looking at Mike, I furiously vented.

“You don’t know me. And you sure as hell can’t break me, so get off your fucking high horse and quit thinking I’m some fragile being.”

Mike started to laugh, then asked if I was willing to prove it.

“Try me!” I panned.

“Fine,” Mike replied. “I’m in room 319. And there’s one very important thing you need to remember…”

“Yes?” I replied curtly.

“At any time you can say you’ve had enough and we’ll call it good.”

Mike slapped three $20 dollar bills on the bar, smiled at me and walked off.

"What the hell did I get myself into?" I started to think as I sipped the rest of my gin and tonic.

I slowy meandered to the elevator and pressed the number 3. Butterflies filled my stomach; I hadn’t had sex in close to a year and had no clue what I was in for. Could I really handle this?

As I walked up to his door I lightly knocked. He opened it quickly wearing a large smile. As he opened the door he motioned for me to come in, which I did, walking past him.

I turned toward him and he leaned in, pushing me against the wall in his room, his hands on my hips as he came in close to aggressively kiss me.

I melted in his arms, kissing him back passionately, embracing his desire with my own.

His hands dropped down to the sides of my dress, lifting it up so his hands could roam over my ass, gripping it with authority. I liked it.

Breaking from the kiss, Mike looked down at my cleavage and smiled. “I want to see these.”

I moved my hands up to my dress straps and pulled down my dress, leaving me in my white bra and boy shorts.

“Kick the dress off and spin for me,” he inquired.

I did as he asked, slithering the dress off me and slowly spinning, a little self-conscious as I stood there in my underwear while Mike was still fully dressed.

“And the bra?” he asked.

Gulping, I reached around my back to undo my bra. As I let it slide off me, I cupped my breasts to cover them.

Mike smiled and walked toward me, his hands removing mine from my breasts. Leaning in he cupped my breasts from underneath, pushing them together. Lowering his head to them, he slowly circled my left nipple with his tongue before moving to my right nipple, making them harden.

I gasped with pleasure as he continue to flick his tongue on my nipples, then started to suck one and then the other into his mouth, pulsing on them with increased suction.

Mike then straightened up and reached for his belt. Frantically he loosened his jeans and lowered them, then reached at his waist to remove his shirt over his head.

He was stunning, standing there in just his boxers. His frame easily told that he worked out regularly, as his chest, abs, shoulders and arms were perfectly defined.

“Ready?” he asked.

“I am,” I replied.

“On your knees,” he demanded as I was a little taken aback.

I must have taken too long to fulllil the request, as Mike shook his head disapprovingly.

As he was ready to speak, I dropped to my knees and looked up.

He smiled, then wiggled out a massive cock, easily eight inches, from his boxers. Easily the largest dick I have ever seen in person.

“Take it,” Mike stated. As I started to reach my hands to wrap around it, Mike slapped my hands away.

“Mouth only,” he clarified.

I have obviously given head many times in my life, but I was always in control. I tried to keep my breathing steady as I leaned in, opened my mouth and extended my tongue out to circle the tip of his cock.

Mike’s hand started to run through my hair, then started to push my head forward, pressing his cock quickly deep into my mouth. I struggled to keep my gag reflex in check as he started to move his hips toward me as his hand pushed my head toward his cock. Rhythmically he started to fuck my mouth. This was no longer a blow job. This was my first face fuck.

My hands reached to his legs, grabbing them for balance. I could feel my eyes watering and started to wonder if my mascara was running down my cheeks. I tried to keep my jaw open as much as possible as he moved my head back and forth, his cock sliding through my mouth and into my throat.

I suddenly gagged hard, trying not to vomit as I reflexively pulled away.

Mike stood there watching me as I sat on the floor breathing heavily.

“Had enough already? That was quick!” he stated.

My eyes shot back up at him as I responded surely, “Not even close.”

Mike laughed and walked past me, leaving me on the floor as he kicked off his boxers.

“Get on the bed. All fours,” he ordered.

I pulled myself up and walked past him to the king bed. As ordered, I got on my hands and knees.

I felt his hands grab at the sides of my undies and pulled them off me roughly. I then felt a wam wet object, his tongue, trace over my ass and down to the crack of my pussy. I then felt him place two fingers, facing down, into my soaked vagina. Mike started to rock his fingers deep in me, curving the down to stroke at my g-spot. The webbing of his hand rubbed back and forth against my clit as he did.

I was in heaven and felt an orgasm coming on strong. The harder and faster he moved his fingers the sooner I was going to explode. Unexpectedly, he then moved his mouth to my asshole, circling it with his tongue as his fingers fucked me. It was too much to control and I shook into an intense orgasm, cumming loudly. It was the first time I ever felt anything like it.

Mike removed his fingers and got behind me. Roughly he placed his cock between my pussy lips, grabbed my hips and shoved his eight inches straight into my tight wet pussy. I gasped as I lunged foward from the momentum. Mike then pulled me back as he started fucking me deep and fast. The sound of our bodies colliding filled the room and I could feel waves of flesh flash across my ass each time we collided, my breasts swaying beneath me wildly as I took it from behind on my hands and knees on the bed.

Mike removed one hand from my hip as he continued to fuck me. I heard a snap, and then a snap again. I then felt a slick thumb circling my asshole. Somewhere he had lube already sitting on the bed and coated his thumb with it. 

I reached back to move his thumb away from my asshole. I suprisingly liked the feeling of his tongue on my ass, but prior to that ass play was uncharted territory for me. As I reached for his hand, he swatted mine away, making his intentions clear.

"Enough?" he asked as he started to push his thumb in my asshole as he continued to fuck me.

"No," I said, trying to hide my hesitation.

His thumb started to work in, circling and pushing, until I felt it pop and slide in. I froze up from the feeling. Strange, but good... maybe even great.

His thumb pushed in and started fucking me sliding in and out at the same pace of his cock. I was speechlessly in ecstasy.

I felt my legs tremble... was I going to cum again? Twice in one evening was rare when I was married.

Closing my eyes I let loose, moaning and releasing from the sensations Mike was putting me though.

I collapsed to my chest, my ass still up in the air as he fucked me fast and relentlessly.

Mike stopped and got away from the bed. He directed me to get off the bed and lay face down on the floor. I obeyed.

As a lay flat on the short-woven hotel room carpet, Mike forced my legs apart and then his hands slid up and yanked my ass cheeks apart.

"You can say you had enough,” he stated as he lowered his mouth to my exposed asshole. Stiffening his tongue, he began circling my asshole and then stabbing into it, forcing his tongue into my puckered star.

Gasping, I lay there motionless, flat on my belly, my breasts pressed against the floor.

Mike removed his tongue from my asshole, then I could hear the sound of the lube cap snapping open before feeling a slick finger steadily enter my asshole.

Gasping I tightened up and flinched. Mike placed a hand on my lower back hand, forcing me to lay still.

“Reach back and spread your ass apart now!” he commanded.

I did want he said, half afraid to say no and half not wanting to prove him right, prove that I was too soft for him.

I spread my ass apart and tried to breathe steadily as I felt him twist his middle finger in and out of my asshole before adding another one. My breathing increased as my heartbeat pounded through my chest and into the hotel room floor.

With both fingers deep in my ass, I could feel Mike trying to spread his fingers apart while in me, then he slowly inched them out.

“Good girl,” he proclaimed.

Mike suddenly placed more force with his hand on my lower back, holding me down on the floor. I could hear him sliding up as I kept my ass spread and closed my eyes.

Instant cold hit my asshole as more lube was applied, then the feeling of his cock’s head twirling in the lube.

“Keep breathing,” Mike directed as I felt the pressure of his cock pressing into my ass.

I closed my eyes tight and tried to breathe, reminding myself that I can do this-I must do this.

Inch by inch his bare cock split my ass apart and it was unbearable, or so I thought for a second. The sensation was numbing, painful at times, but also paralyzing and massaging.

“You like it in your ass?” Mike questioned as I felt a fullness I never dreamed possible.

My response was wordless, just heavy breathing as I tried to adjust to being pinned to the floor with close to 8 inches of cock in my ass.

“Answer me or say you’ve had enough!” He demanded.

“No,” a single word squeeked from my mouth.

“Enough?” He questioned again.

“No,” I replied a little less tentatively.

“Enough?” Mike barked again, this time starting to move his hips, sliding his lubed cock back and forth through my tight sphincter.

“No,” I uttered, trying to just breathe and not pass out from the overwhelming situation.

“Enough!?” Mike said again, speeding up his thrusts, forcing me into the carpet as he fucked my ass into the floor. We were in a nice hotel, but based on his fury as he took my ass we might as well have been in a jail cell.

No words were able to come out of my mouth, just the guttural sounds one might while going through an out of body experience. Each time his hips rose, withdrawing all but his cock’s head from my ass before slamming all the way back in, I could only grunt as I felt him race through my ass and sphincter, my breasts, belly and left facial cheek moving back and forth against the ground.

Time seemed to stop. I could have been there for seconds, minutes, or hours. Six months ago I felt lost, now I felt a cock in my ass.

I suddenly felt vacant as a suction sound filled the room and Mike quickly withdrew his cock from my opened asshole.

“Good girl. That felt so fucking tight!” he replied.

I rolled to my side, part of me wanting to roll into a ball and cry, part of me excited to see what else I could take from him.

Smiling, Mike, squatted over me, on his knees, stroking his hard, shiny cock.

“Press those breasts together,” he commanded.

Shifting onto my back, I obeyed, cupping my breasts from the sides and pushing them together. Mike straddled my chest, running his hard cock between my tits as he fucked them.

“You look so hot,” he stated.

I smiled.

Leaning in a bit, he started to knead my nipples as he fucked my breasts with his shiny, lubed cock.

“Open your mouth,” he commanded.

I shook my head to say no, not wanting to taste a cock that was in my ass, unsure of what his intentions were.

“Enough?” Mike asked for the millionth time.

“I want you to cum in me,” I stated quickly, trying to come up with an excuse that didn’t make me sound like I was tapping out.

“On the pill?” he inquired.

“Oh, shit,” I thought to myself, as the pill was something I hadn’t been on in quite a while.

“My ass, please,” I mumbled as my mind tried to verify why in the world I would say that.

“You want me to cum in your ass?” he asked.

I nodded yes.

Mike slid back as I lay on my back, and with his arms lifted my legs up over his shoulders.

Reaching down he moved his cock back to my ass, sliding it in.

“Play with your clit as I fuck your ass again,” he commanded.

I did as asked, taken aback by how quickly and easily his cock was buried in me again. I stared at his hot body hovering over me, taking me, taking the new me. Our eyes didn’t lose contact as I rubbed my clit while getting assfucked by a gorgeous animal.

A wave started to overcome me. Was I about to cum from anal? Building slowing, then overwhelmingly I started to moan, having one of the hardest orgasms in my life.

“Do it, do it!” Mike repeated as he fucked me while I came, loving every minute, every inch, every feeling that was occurring. My pussy soaking my hand as Mike continuous to ravage my asshole.

“I'm cumming!” Mike uttered shortly after I came. He started jabbing into my ass deep with shorter strokes as he tightened up, filling my ass with cum for the first time.

The feeling was overwhelming, one I knew could never have happened in my previous life.

Mike rolled off me and started to laugh. “You proved me wrong. But we still have tomorrow.”

I looked over at him and smiled, accepting his challenge.

 

 

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