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Let Me Help You

"Things get out of hand with my boss and his friend at a party."

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Author's Notes

"My boss and I hook up only for his friend to find us."

After I graduated high school, I got a summer job so I would have some extra spending money before I left for college in a couple of months. One of my work colleagues was throwing a surprise birthday party at her apartment for our coworker, Kristin. I was the youngest at the party, still only being seventeen, while most everyone else was in their mid-twenties to late twenties.

Since it was a casual party, I wore low-cut jeans and a brown shirt that was one size too small, so it showed off my ample breasts and cleavage along with some of my flat stomach. A few of us were playing single games of beer pong when my manager, Daniel, walked up next to me and asked if I wanted a teammate.

Daniel didn’t usually talk to me unless he had to and it was always work-related. If anything, he usually acted like I annoyed him and avoided me, so I was going to seize this opportunity for peace between us no matter if it was alcohol-induced. It also didn’t hurt that he was tall and handsome—tanned skin, green eyes, and short black hair that greyed on the sides, along with grey hairs scattered throughout his beard. He was also very fit and wore clothes that showed both his broad shoulders and well-muscled frame.

“Um, sure, Boss!” I responded, surprised he spoke to me, let alone asked to play with me.

Daniel leaned in close to me and said in a low voice, “I’m not your boss tonight. Call me Daniel.” And winked. I took in a sharp breath and felt myself getting wet instantly—my older boss was flirting with me, and I was feeling things for him that I shouldn’t. He was just being friendly, and I was reading into things way too much. I convinced myself it was the beer and tequila.

“Let’s play then, Daniel,” I replied, smirking at him. The alcohol made me braver than I usually would be and knowing that I could tease him without any repercussions spurred me on even more.

His nostrils flared as his eyes turned fiery. His gaze dropped to my lips. This was going to be fun tormenting him all night. As we played, we got more comfortable with each other and relaxed. I giggled at things he would say and would touch his arms when talking to him. He would nudge me and steal glances at my breasts when he didn’t think I was looking. When we would hand each other a ping pong ball, our fingers always lingered against the other person’s hand a little longer than needed. With each small graze of each other’s skin, I got wetter, and my nipples hardened. This man was turning me on so much, but he was my boss. I knew this couldn’t go anywhere, so I decided to do more and push my boundaries.

Daniel and I were winning our last game easily when I stepped between him and the table, which would look harmless to everyone else, but I was pressing my firm ass against him. I could feel his semi-hard cock between my ass cheeks when I turned to face him and asked coyly, "So, what are you going to get me for a prize when we win, Boss?” reminding him of his authority over me, but that same authority kept him from being able to touch me like I knew he wanted to do.

He locked eyes with me. His gaze was so intense I immediately soaked my panties before he had even spoken a word. He growled, lowering his lips to my ear so only I could hear him.

"Good thing I’m not your boss tonight, or you would be insubordinate. I said to call me Daniel. Now behave.” He quickly grabbed the back pockets in my jeans and pulled me into him hard, thrusting into me just once. I could feel his hardened cock pressed against my ass and gasped. No one around us seemed to notice our movements. I had to be soaking through my pants now I felt so wet.

“Am I doing something you don’t like, Daniel?” I asked slyly, grinding against him again.

I heard him sigh heavily, removing his hands from my pockets, and readjusted his dick in his pants so no one could see his excitement as he stepped away from me. My heart sank as I thought I pushed him too far, and he realized he shouldn’t be going along with my antics. The next play, Daniel and I won our game, and he asked me if I wanted to go outside and smoke with him. Although I didn’t smoke, I agreed so we could hang out alone and see where this was going. I partially expected him to lecture me about my behavior.

As soon as we walked outside through the sliding doors, we moved to the side of the apartment out of view of everyone inside and any neighbors. Almost immediately Daniel pushed me against the brick wall, my blonde hair tangling with the rough material behind me. His mouth was on mine, and his hands found my tits, squeezing them through my shirt. Our tongues slipped into each other’s mouths while my hands traveled up to his hair.

“God, I’ve wanted to feel and suck your tits since your interview.” He growled against my mouth. My mind raced back to my interview I had after school one day a few months back when I had worn a small, purple summer dress that my breasts spilled out of and it only reached halfway down my thighs. Knowing I had tempted this man at our first encounter made me feel feral.

I moaned into him as my hands searched for his cock through his pants. When I found his hardening length, I palmed and squeezed it, stroking it firmly but slowly. He groaned, squeezing my tits roughly again before letting them go and reaching down, grabbing the hem of my shirt. I leaned forward so he could pull it over my head, tossing it to the side he reached behind me, trying to undo my bra. He struggled with the clasp, so I reached back and undid it for him, dropping it into a pile with my shirt.

He took a step back, admiring my tits as if they were a work of art. He grinned and leaned down, grabbing both my breasts, he teased my nipple by licking it first before he latched on sucking so hard it felt like he would leave a mark. My left hand reached up and stroked his hair while I held him firmly against me as if I were feeding him. He moved to my other side and bit my nipple. I yelped as he started sucking again the cool air hardening my abandoned nipple still coated in his spit. His hand traveled into my pants. Slipping his fingers beneath my lace panties, circling my clit, he elicited a choked cry from me. I was watching him feast on my breasts when we heard the door slide open. We both froze and looked, Daniel doing his best to shield my exposed body from whoever was standing there.

We had gotten caught. Here I was, seventeen, hooking up with my boss, who was much older than me, outside for the world to see. The person looked at us and stopped in their tracks. I couldn’t see who it was, but I could tell it was a very tall man as he reached and slowly shut the door behind himself, never looking away from us. That’s when Daniel squeezed my tits that he had been shielding, kneading them.

Purring, he whispered, "Are you okay if Stephen watches us, love? You can’t be shy with tits like these, baby. That would be a fuckin’ crime.” He leaned back, massaging them while showing them to Stephen.

Did I care if Stephen watched? I knew him pretty well because we worked together often. I knew he was longtime friends with Daniel, and he had started working there a couple of months before me. He was always nice and sometimes flirty, but he had a serious girlfriend, so I decided it would be fine if he watched. It’s not like he’d be joining us because he would be cheating on her. With Daniel still kneading my breasts, I bit my lower lip looking at Stephen and moaned, bringing Daniel’s mouth back onto my tit, showing my acceptance of having an audience. God, my pussy was dripping wet, and I felt like I could cum if someone barely touched me.

Stephen was standing there, not moving but watching us intently as Daniel slipped his right hand back down into the front of my pants, inside my panties making me gasp. He slid his fingers up and down my slit, spreading my arousal until he stopped at my clit. Circling and pressing his fingers against it, my breathing quickened as I bucked against him. Needing more of his touch.

“You’re so fucking wet for us,” he teased. Groaning against my breast, he added, “I was right- I imagined you’d have a shaved pussy too.”

Wait… He said, "Wet for us.” What did that mean? So many scenarios rushed through my mind when I felt Daniel latch onto me again, biting my nipple, making me cry out, and bringing me back to reality.

Daniel laughed, pulling off me briefly. "Seems like someone likes being watched, huh? Cum for us, baby. Cum.”

He sucked my nipple back into his mouth as he kept rubbing my clit with his thumb while his middle finger slid into my pussy. He added another finger, stretching me. It was all too much and I was about to come undone.

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“Ohmygod, yes! Faster!” I begged Daniel as I looked into Stephen’s eyes. “I’m going to come!” I panted.

Daniel increased the speed and pressure, and it sent me over the edge that I had barely been clinging to. I came, shuddering against his hand, and covered my mouth while trying to keep my screams down so no one from the party or her neighbors heard us. My orgasm was so intense I would’ve fallen had it not been for Daniel’s hand between my legs and his face pressing me into the wall as he sucked my tit almost painfully hard. When my orgasm finally subsided, I reached for Daniel’s belt, undoing his pants, not caring if someone else was there. I felt my pussy clench when I thought about Stephen watching me blow Daniel.

Kneeling in front of him, I pulled Daniel’s erect cock out of his pants. I had gotten lucky again with him as his cock was above average in thickness and his length was about five inches. I moaned and smiled up at him. Grabbing his cock, I spread his precum up and down his length while I twisted my wrist up and down his stiffened rod. I leaned forward, covering the head of his cock with my mouth, twirling my tongue around it, and licked his slit that oozed more precum. He moaned, and his brows pursed together as he put one hand on the wall behind me and his other behind my head.

I started to bob my head up and down his cock, while he thrust into my mouth, sucking in his length more and more, my tongue brushing against the vein underneath. I soon had my nose pressed to his body, his cock hitting the back of my throat. I swallowed a couple of times, squeezing his cock, then came back up gasping for air, thick spit covering him and running down my chin. I smiled up at Daniel and looked over at Stephen as he rubbed his bulge through his pants before I quickly placed my mouth back on Daniel, swallowing his entire length again. I bobbed my head up and down, slurping and moaning, savoring his cock and loving the mess I was making while pleasing my boss and getting his best friend off.

“Hey baby, what do you think about Stephen coming closer and getting a better view? You look so beautiful with my cock down your throat,” Daniel asked. I moaned on his cock, shaking my head up and down the best I could. I glanced at Stephen, and he had stopped stroking himself. Taking that as he wasn’t impressed enough with my performance to cheat on his girlfriend, I brought my hand up and gently squeezed Daniel’s left testicle, palming and massing it. It was much smaller and felt tighter than I had imagined as I swapped to the right. Just as I started massaging it Daniel placed his other hand on the back of my head, thrusting further and harder into my throat, making me gag and choke at the repeated, deep intrusion.

“FUCKKKK!” He bellowed, holding me in place, shaking while spurting cum deep in my throat. I could feel his testicle twitching in my hand and his dick pulsing in my throat with each spurt of cum. I glanced over at Stephen who started walking toward us. I was still swallowing Daniel’s cum when I heard the door slide open again.

“Are y'all okay? Oh my god! What the fuck?!” I heard Kristen yell. I tried to pull myself off Daniel’s cock, but he was still coming and holding my mouth on his dick. I wasn’t able to see Kristen because Daniel had my face pressed firmly against him, taking all of his length and swallowing every drop of cum I could. The furthest I could look over was at Stephen as he and I locked eyes; he was only an arm’s length away. I could see the massive tent in his pants, and I still wanted him. Even with Kristen there, I wanted to reach out and stroke him as I was still sucking Daniel off.

“Shit!” Daniel hissed, still holding me firmly against him, bucking into my mouth. I heard Kristen turn and run back inside. When he finally let me off, I gasped for breath, spit, and cum webbing from my mouth to his cock and dripping down my chin to my breasts. I finally looked up at Daniel and then Stephen and smiled. I wanted Stephen’s cum now.

“God damn, that was amazing. I couldn’t stop coming,” Daniel sighed. “I’m in so much shit. We should go back in.” Daniel moaned, zipping his pants up.

He helped me clean up and get dressed. When we all went back inside, Daniel went to talk to Kristen. It mostly consisted of her and some of our coworkers yelling at him about how young I was and how he was not only older but also my boss. I felt bad that he was getting berated by so many people while I stood awkwardly with Stephen in the other room in silence. I glanced down at his pants, the voices drowning out in the background. He still had a boner and, my god, he looked massively thick. I was still new to sex, so I probably didn’t really know what I was looking at. My breath hitched and I looked up at him. His blue eyes were locked on mine as I blushed at being caught blatantly looking at his hard-on. Suddenly, everyone flooded through the room to the front door, informing us that they were all going out to a bar.

Seeing as I was only seventeen years old, I couldn’t get into a bar and Daniel wasn’t invited after our stunt. My pussy clenched when I realized it was just me and two men in an empty apartment. I grabbed another beer and went and sat in the middle of the couch, making sure there was space for them on both my sides. I still wanted them both and hoped our getting caught didn’t kill the mood. Daniel and Stephen started to walk over to the couch when Stephen’s phone went off. When he answered, we could hear his girlfriend yelling at him on the other end. He walked quickly back outside, trying to calm her down.

Daniel and I sat awkwardly on the couch. I still wanted to fuck, but I waited for him to make the next move. With him being my boss, I knew even the blow job crossed the line.

“I shouldn’t have done that with you. I’m your boss, and I can get fired if anyone talks about this.” He finally said, breaking the silence.

Let down by his realization, I told him I understood and took a gulp from my drink as I tried to hide my disappointment. I looked over at him and smiled, trying to reassure him, and myself, that I was fine with stopping there. The air was thick and tense with indecision. God, I wanted this man and his friend to take turns with me. To ruin me.

“Fuck it,” I said as I grabbed his face and kissed him. Our mouths collided and our tongues intertwined. I put my beer on the floor as he pushed me back on the couch and laid on top of me, in between my legs. He moved his lips down to my ear, then neck, and when I rolled my head to the side, Stephen was standing there again. I smiled at him and moaned as Daniel squeezed my tits. Daniel quickly unbuttoned my pants and pulled them off. He undid his pants in a fury and pulled them down to his knees. His cock was rock hard again.

I slid my left hand to my pussy collecting some of my slickness, and then grasped his cock, twisting my hand up and down his length a couple of times before guiding him to my entrance. I could feel Stephen still watching us from a few feet away, but I looked up at Daniel, ready for him to fill me with his cock. I slowly rubbed his cock up and down my pussy, teasing my swollen clit with his engorged tip. I couldn’t believe how great it felt. I only had to do it a couple more times, and I came again, somehow gushing more juice. We were both panting as I placed his cock at my entrance, waiting for him to impale me.

When he didn’t move, I reached down and grabbed him again, pushing my hips toward him trying to get him inside me. I felt the tip of his cock enter me when all of a sudden he grunted, closed his eyes, and shook, his cum shooting both in and all over my pussy as I moved away. I gasped, but I continued stroking him through his orgasm. I felt his dick lose its rigidity, and his boner was gone.

“That’s never happened to me before,” Daniel gasped.

“It’s okay. It happens...” I tried to sound reassuring, but I don’t think I sold him on it. When he got up to get me some napkins to clean off, he jumped back when he saw Stephen there.

“God dammit. Of course, you saw that.” He sounded pissed now. Daniel came back, handed me the napkins, and said he had to go, leaving without another word, thwarting my hopes of Stephen joining us. I realized I was still lying there on the couch, with my legs spread open, and I was covered in cum. I moved to wipe the cum off myself when Stephen spoke up for the first time that night.

“Wait. Let me help you...” he said as he approached me, kneeling on the couch between my legs.

Published 
Written by stormdoor32
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