First time with Jon Ch. 01

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Jenna loses her virginity to an older man.
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jennahale
jennahale
98 Followers

The week I turned 18, I got a job at a local restaurant. Just your average burger joint. The waitress outfits were a bit too small, and the busts too revealing, but that was the way the patrons liked it. It was on my birthday that I was called into work by my boss, Jon.

Jon was the type of man that demanded respect. He was almost 43, tall, about 6'1, with brown hair and hazel eyes that could pierce straight through your heart. I was intimidated, almost frightened of him. That was why I cancelled my plans with my friends to go into work. I couldn't afford to lose this job, the economy was so bad, it was a struggle to even land this one.

I got to work in my uniform, just a few minutes late because of the last minute notice, but Jon was furious. The moment I arrived he called me into his office.

"Jenna, just because it's your birthday doesn't mean you can be late," said Jon in a hushed voice. There was something in the way he said my name that sent chills down my back. "Now get to work, and don't disappoint me." He winked at me.

I turned around, and I could swear he briefly touched my ass as I turned around. I looked at him startled as he feigned innocence. Annoyed, I brushed it off and walked away, determined to finish my job for the night and then leave to go have fun.

I finished off the rest of the night in haste, skimping on my duties and barely making conversation with the customers. After everyone had left, I was busy cleaning off the rest of the dishes when I felt someone looking at me. Slowly, I turned around and saw Jon standing roughly 4 feet behind me, staring at me working. I tried to shrug it off, a bit nervous as I quickly finished scrubbing the table. I turned around to go grab my coat and leave when his hand grabbed my arm.

Startled, I dropped the bucket of sanitizer I was carrying and it fell crashing to the floor. Jon caught his breath and I looked up just in time to see his eyes gleam with sinister malice.

"Better pick that up bitch. You have 60 seconds." I was caught off guard by his words. Jon was intimidating, yes, but never derogatory towards me or any of the other female workers. "55, 54, 53, 52, 51..."

I practically ran to the kitchen to get the mop, but tripped over my own feet. By the time I got back to the floor, Jon was already at 41.

"41, 40, 39, 38, 37..." I tried to clean up the mess, but in the time that I was gone, Jon had flipped over the remaining water to other spots of the floor. With tears forming on my eyes, I tried as best as I could to clean up the sanitizer. "29, 28, 27, 26, 25..."

"Please I'm tryin!" I screamed towards him. That made him angry.

"You're not trying hard enough, you slut!" Jon slapped me hard across the face. Pain sprung to my cheek and I brought my hand to my face. "10, 9, 8..." Panicking once more, I struggled to clean up as much as I could as he counted down "5, 4, 3, 2," Another slap. "1."

"Well well well, looks like little Jenna couldn't finish her task. Too bad it's your birthday and I'm going to have to keep you late."

Angry, I replied "Well I wouldn't have had to stay late if you hadn't made me spill it in the first place you prick!"

Jon looked down at me cooly, my shoes soaking wet and my cheek still burning red with pain from his slap. "Pack your things and leave. You'll never have a job here, and you'll never have a job in this town again."

I was caught off guard. I knew that Jon was powerful and had money, but I had no idea the amount of his significance and power within my small community. "Please sir.. I'm - I'm sorry."

"Prove it to me then."

"How?" I was becoming suspicious, it felt like a set up to me.

"What would you do to make it up to me?" He smiled. A charming smile that on any other day would have made me feel at ease.

"Any - Anything sir." This felt like I was in one of those bad blackmail porn movies, with an unsuspecting girl willing to do anything for a secure future.

"Good girl. I know that today is your 18th birthday. Now I can finally have fun with you girl." As he said this, he pulled me towards him and embraced me, managing to caress my breasts as he pulled me in. At first, I struggled, but I finally gave in as I felt his cool embrace. I knew that I would do anything to keep my job. I had become one of those slutty girls. But I didn't care. I needed this.

He let go of me and circled around me, admiring me. "Good, now take off your clothes." I did as I was told, not wanting to anger him anymore. I slipped off all of my clothes. "And your panties and bra, Jenna. Please, hurry. I don't have all night." Quickly I slipped off my bra and panties.

I wasn't hot, but I had a good body. My blonde hair fell to my mid-back, my green eyes ecuntated with light makeup, my 34C breasts, and my shaved pussy. I was proud of my body, and proud that I managed to keep my virginity intact throughout all of my high school years so far.

"Very nice, Jenna.." He trailed off as he took off his clothes slowly, almost menacingly. "I will not do anything without your consent, but just know that my recommendation can make or break you in this town."

I hesitated "But.. but I'm a virgin, Jon."

He threw his head back and laughed, "Even better!" With that he took my by my arms and shoved me to my knees. I wouldn't have protested but he didn't leave me enough time to say a word as he took my head in his hands and shoved his enormous dick into my mouth.

I'd sucked cock before. Nothing too huge, my biggest was almost 8. But Jon was 9 inches of pure thick cock. I gagged every time he thrusted into my mouth. He was groaning, and I did my best to please him. Maybe I could make him cum quickly and I could go home. I worked my tongue quickly on his cock.

After a few minutes of me sucking and gagging, he pulled back. "My my my, wouldn't have pegged you for a cock sucker. I almost actually cummed. Let's see how you do with this next step."

I shivered, suddenly cold, as he pulled my hand and my body to the nearest table. "Get on and spread your legs." I obeyed him. What harm could a little pussy licking do?

I quickly spread my legs and he shoved a finger in hard. I gasped, taken off guard. He kept pushing until he found my hymen and pushed tentatively on it. "Ohhh please Jon no. I'm a virgin."

"Obviously, Jenna. You told me that before, and that's what this" - a quick push " - is." I arched my back, trying to distance my pussy from his finger. "But don't worry, I won't be taking your virginity quite yet." As he said that he brought his face down to my pussy and licked me up and down slowly. "This is quite the cunt you have."

I moaned loudly. This was the first time a man had ever licked my pussy before. Most guys were concerned about themselves and cumming, not caring whether I was pleasured or not. I groaned, gyrating my hips as he shoved his tongue inside of me. "Ohhh Jon. God that feels so good."

He paused for a second, grinning up at me and I could see something on his face. I realized that it was my pussy juices. I was so horny, and getting so turned on by this man. This man who had brought me into this situation, knowing that I would do this. He returned to my pussy, eating me out as he brought me closer and closer to orgasm. I could feel my pussy tightening, something rising up deep inside of me. He shoved in one last time, all the while looking up at me as I orgasmed hard.

"Oh God! Yes Jon yes!" My hips bucked and he stood up while I finished orgasming.

"I knew you'd like that. Virgins always do." He brought his cock to my pussy entrance and tapped on it, sliding his dick on my slit. I moaned, still turned on and in my post-cum stage. "Are you ready for me Jenna?"

I looked at him briefly, saw the greed in his eye as he watched me breathing heavily. I nodded my head slowly, frightened now.

"Don't worry, it will only hurt for a bit." With that, he lined up his cock with my pussy and shoved in gently, less than ½ an inch. Just enough to stretch me briefly. I gasped. "Too late to back out now," Jon said as he grabbed my arms and held them by my side. He looked down at me and saw me biting my lip in quivering fear as he slammed into me hard, rocking me back on the table. He tore my virginity in one thrust. My pussy was on fire. I started to scream as he took his cock completely out before shoving in again, harder. I struggled beneath him, craving something to hold onto in my pain, but he was stronger than he looked for being 43. He kept a hold on my arms pinned to the side as he rocked his hips.

"Jon please.. please it hurts!" I continued crying, the pain mounting in my pussy as he took his cock out again and again, slamming in harder and harder, stretching out my no-longer-virgin cunt.

"Just deal with it slut. You knew this would happen and you gave your consent." With every word he thrusted in again, adding to the moment as he smiled down at me. His grip tightened on my arms as he started to thrust faster, no longer going for depth. I could hear his grunting, felt his hips bucking and slamming into me.

My pussy was no longer on fire. In fact I started to enjoy it. The dull throbbing coming from my cunt almost masked the feeling of another orgasm rising within me. But nothing could stop it from arriving as I let out a shrill shriek of "Jon, I'm cumming!" as my hips bucked and rose to meet his thrusts.

He was fucking me like an animal now. Letting go of my arms as he switched to holding my waist, pounding in and out of me. My orgasm continued as he kept hitting my g-spot over and over.

"Jon yes!" I screamed and begged him, gyrating my hips as he kept fucking me.

"You're so tight Jenna!" After a few more seconds, he let out a bellow as I felt something warm gushing inside of my pussy.

Alarmed, I realized he hadn't used protection. "Jon.. Jon did you just..?" I asked him, while trying to catch my breath and trying to pull away with my hips.

"Of course I did, baby," Jon leaned down to kiss me on the lips, pulling my hips back towards him and his cock back into me, letting the rest of his cum fill my tight pussy up, "and I will continue to creampie your tight pussy as long as you are under my employment. Is that clear?"

"Very clear, Sir," I said up at him as he collapsed on top of me, pinning me to the restaurant table. There was nothing else I could have said, I would be under his command for a few more years. And I needed the money. We breathed heavily for a few minutes, not saying anything as he caressed my body.

After a few more minutes he extracted his penis from within me and put on his clothes.

He started to walk away before he turned around. "Clean that up..." he pointed at the mess we had made on the table as he he trailed off for a second before he added, "slut."

jennahale
jennahale
98 Followers
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