The Boss Ch. 02

Story Info
Frustration at work leads to a one night stand.
2.7k words
4.22
19.7k
2
0

Part 2 of the 3 part series

Updated 10/09/2022
Created 11/18/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is chapter two of an ongoing story. If you haven't read chapter 1 yet, I suggest you do so first. As I said before, I file this under BDSM because of the strong power exchange undertones... the full manifestation of the D/s relationship won't happen until the next chapter, but if you're willing to stick with me, I hope you'll find it worth the wait. This isn't a quick story. The plot builds slowly, and each successive chapter is longer than the one before it, so far. However, the rest of the chapters will have more sexual encounters than the first one. All comments welcomed and appreciated, but if you have criticism please keep it constructive.

Special thanks to Fetishep for editing.

*****

The next morning I took special care with my appearance. A slightly less conservative blouse than usual was paired with a slightly shorter skirt and taller heels. I left even earlier than usual too, and made sure I was already at my desk working when my boss walked through the door. It could have just been my imagination supplying what I wanted to see, but I'm pretty sure she almost smiled. I reported to her office after work, exactly as instructed. She had me give her a back massage, then a foot massage, and then she dismissed me, much to my disappointment. Once home, I cooked my dinner, and then treated myself to a night of porn and orgasms.

The weekend passed slowly, and Monday evening I was back in her office, hoping tonight would be the night she took advantage of my not-so subtle offer. Once more, she sent me home after just a massage. For the fifth night in a row, I tried to appease my body's cravings before falling into a restless sleep full of dreams of her. The rest of the week passed almost exactly the same. Friday afternoon, after Janet left, I reported to her office as usual. After I closed the door behind me, she instructed me to kneel on a pillow at her feet. She had provided me a pillow to kneel on earlier in the week, so I thought nothing of it as I began massaging her feet. This time, however, she told me to continue my work on her legs. I used the opportunity to admire the incredible muscle tone in her calves. I was almost in a trance when she gave me her next order. "Now lick my pussy."

I stared up at her for a few seconds, uncertain I'd heard her correctly.

"Is there a problem?" she asked, after the silence had stretched on just a little too long.

"No, ma'am, you just surprised me."

"I see. Well, either do what I told you and lick my pussy now, or go clean out your office. Which will it be?"

I didn't answer with words. This wasn't a situation that required much talking, after all. Either I obeyed, or I left. After the last week of sexual tension, I wasn't about to give up now that I'd finally gotten the invitation I was looking for. I began to kiss up her leg, using the tips of my fingers to slowly pull her skirt up her legs. As the skirt exposed more, I began to wonder what she would have on underneath. Would it be something sexy, the stereotypical sexy executive in the matching lingerie? Would she be as conservative underneath as she was on the surface? It never even crossed my mind to anticipate that underneath her skirt she would be wearing nothing, but that's exactly what I found. I gasped a little, surprised and even more turned on.

I slowly dragged my tongue up the soft skin of her bikini line, and then repeated the move on her other leg. I breathed in deep, luxuriating in her scent filling my awareness, trying to memorize every facet of this experience to savor in private later, and then flicked my tongue across her clit, quickly. I then ran my tongue up from her opening up to her clit, and moaned as her taste filled my mouth. The world narrowed to the pussy in front of me, and the need to draw even a single moan from her. I swirled my tongue across her clit in broad strokes, then returned to her opening, probing it, letting her fluid coat my tongue, before bringing it back up to her clit, mixing swirls and patterns with horizontal and vertical lines. I continued to alternate my attention between her increasingly swollen clit and long strokes down to her opening and back up. I used my tongue to probe her opening, which elicited a surprised moan.

Before long, her hand came to rest on the back of my head, her fingers twined in my hair, applying the subtlest of pressure to limit my focus to her clit. When her fingers tightened in my hair, pulling it just a bit, I could tell she was getting close. I redoubled my efforts, determined to bring her to orgasm and prove just how useful I could be to her. As she started to cum, she gripped my hair tight, shoving my face into her pussy as she writhed and bucked. I struggled to stay on the right spot, and breathing became quite difficult for a few long seconds. After her orgasm, I slid my tongue back down to her opening, and then licked up to her clit in one slow motion, flicking it lightly, causing her to shudder. I smiled up at her, suddenly shy and unsure. I got a hint of a smile in return before she dismissed for the evening.

I hurried home, desperate to satisfy the ache that had been building between my legs since she first told me to eat her out. My skirt was around my waist and my panties were on the floor within seconds of my door closing behind me. I flopped down on my couch and began furiously rubbing my clit with my right hand while my left undid the buttons on my shirt and freed my breasts from my bra. While I worked my clit, I began to knead my breasts, stopping frequently to pinch and twist my nipples. I replayed the scene in her office over and over while I brought myself closer to the brink, and then backed myself off, and then brought myself there again. I drove myself into a frenzy picturing the way she'd smelled, the way she'd tasted, the look on her face as she came. Within a few minutes I was at the edge, and then falling over it into bliss, holding a pillow hard over my mouth to muffle my screams as I roughly massaged my clit with my fingers.

I lay on the couch after I was done, panting, but not even really close to sated. Then it occurred to me that today was Friday, which meant I had 2 more nights to get through before I could service her again. I pulled myself off the couch, showered, dressed, and headed out to find someone who could take the edge off the ache that threatened to drive me insane if I left it untended for an entire weekend.

I walked into the bar down the road, dressed in a short skirt, low cut shirt and high heels, and headed straight for the bar. It was a typical Friday night, which meant it was packed, but that suited my needs just fine. I ordered a drink, and then leaned against the bar while I scoped out a likely prospect among the crowds of girls trying too hard to pretend they were only interested in having a girl's night out, and guys trying too hard to score their next lay. From across the room, a guy caught my eye. He was blatantly checking me out, and just grinned when he saw me catch him. I smiled at him in invitation, and as he crossed the room to me, I took the opportunity to size him up. He was about 6 feet tall and well-muscled with dark hair and a 5o'clock shadow that actually worked, wearing dark jeans, and a casual button down shirt. Let's just say he was hot, and leave it at that. He nodded at my nearly empty drink when he reached me, "May I buy you another?"

I nodded, as I downed the rest of the drink I'd been nursing. He told me his name, I told him mine, and with the pleasantries out of the way, we got down to the flirting. The tension mounted between us as the time passed and the drinks flowed, and finally he said the words I'd been waiting to hear.

"I'm going to kiss you now," he whispered in my ear. I responded by angling my face toward him to give him better access. The kiss started sweet, but given my hyper-aroused state, it quickly became aggressive. Our tongues danced together in a fight for control of the kiss as his hand stole around my neck to embrace the back of my head. I stepped further into him, pressing myself against his body, waiting for the telling press of a bulge into my stomach that told me he was as turned on by the kiss as I was. I finally broke off the kiss.

"Let's get out of here," I said as I grabbed his hand. I led him out the back door into the alley that joined the bar with my apartment building a block away. He shoved me up against the building and reinitiated the kiss. He began to knead my breasts through my shirt, but the bra blocked too much sensation.

"Not here," I managed to get out, "my apartment is just over there. Follow me." As soon as the door of my apartment shut behind us, he pushed me up against it, kissing me passionately. His hands trailed across my stomach and up under my shirt. He broke the kiss long enough to pull it over my head, then unhooked my bra. His hands came up to massage my breasts, and I moaned as his fingers found my sensitive nipples. Meanwhile, I had been working on the buttons on his shirt, and as he leaned down to take my nipple into his mouth, I got the last one free and pushed the shirt off his arms. His tongue swirled over my nipple as he drew it into his mouth and I arched my back into him, gripping his forearms with my nails.

"Sensitive, are they?"

"Very."

He smiled up at me as he shifted his attention to my other breast. I ran my hands down his arms and across his back before pushing lightly on his chest to direct him towards the couch. He sank onto it first and I straddled him, positioning myself right over the bulge in his jeans that had been growing since we first kissed in the bar. He moaned a bit as I settled myself on him, and I leaned in to kiss him as my fingertips traced swirls across his abs. He began to kiss down my neck as his hands found my breasts again, gently rolling my erect nipples between his fingers.

His fingers continued their explorations across my stomach, and he bent down to take my nipple into his mouth again. I writhed a little on top of him, eliciting a low moan, and his fingers continued to move, now on my legs tucked up under me. His hands slid across the tops of my thighs until they encountered my skirt, which he began to gently push up. I reached between us and undid his jeans and then stood up to pull them off of him, before sliding my skirt down my legs and leaving it pooled in a heap on the floor. He took the opportunity to adjust himself so that when I sat back down his cock was perfectly wedged between my lips and pressed against my clit with just 2 thin pieces of fabric between us.

I kissed his neck and shoulder as I began to slowly roll my hips up and down, massaging my clit against his penis, and reveling in the pressure against my most sensitive areas. His whispered "fuuuuuck" made me moan in response. Being with such a vocal guy after the near-silence of my boss was a totally welcome change, and the sounds of our pleasure filled the apartment. Riding a guy has always been one of my favorite sexual activities, particularly because it gives me a fantastic opportunity to judge the size of his dick before I'm trying to deep throat him. While his wasn't what I would call massive, he was probably around 7 inches, and thicker than I was used to. I shuddered a little with the anticipation of having it filling me. He wrapped his hands around my ass, and then surprised me by standing up with me still clinging to him.

"Here or your bed?"

"My bed. It's right through there." I motioned with my chin in the correct direction, and he carried me into the bedroom, and then deposited me on my bed, lying on my back. My legs were hanging off the end of the bed just slightly, and I started to wiggle up further on the bed, but his hand on my stomach stopped me.

He knelt on the floor between my legs, and began kissing my stomach, working his way towards my panties. He gently dragged his nails across the skin right above them, before sliding his fingers under the waist-band and slowly sliding them over my hips and down my legs. I moaned in anticipation. If his kissing skills were any indication, this was going to be excellent. I wasn't wrong. He was definitely better than most men I'd been with, and it wasn't long before all I could do was grip the sheets, moaning loudly. I came hard and loudly, and I was relieved to see he was already wearing protection when he stood up, so there was no need to pause.

I scooted up the bed to make room for him, and moaned again as I felt him slide inside me. He entered me in one smooth motion and then paused to let me adjust to his size. I wrapped my heels around his hips as he lowered his mouth to mine, and he kissed me with all of the desperation I shared as I pulled his weight onto me. He began to thrust into me, slowly at first, but gradually increasing the tempo until I was clinging to him as the bed creaked underneath us. His grunts, my moans, and the creaking of the bed combined together, echoing in my ears. As my orgasm neared, I dug my nails into his back, holding him tightly. He didn't let up as I started to orgasm, and I rode wave after wave of pleasure. It briefly occurred to me that my screams might wake the neighbors, but I was beyond caring. I was dimly aware of him coming too, as I rode the last wave back down.

We lay together, panting and sweat soaked, for a few minutes. We finally disentangled ourselves, and he flopped on to the bed next to me. "That was nice," he said.

"Mmhmm. Just what I needed after the week I've had." I replied. We lay in silence for a while, lost in our thoughts, before I finally went to get cleaned up. He followed suit, neither of us really talking.

"I should go," he finally said after he'd gotten dressed.

"Yeah, I should get to sleep."

"Should I call you?" he asked, and I couldn't tell what he wanted the answer to be. There was an awkward moment of silence while I considered my response.

"I don't think that would be a good idea. I'm not in a good place to start anything right now," I replied.

He nodded. "Okay. Me either. This was perfect."

I nodded in agreement, and then he left. Finally sated for the first time in almost 2 weeks, I fell asleep quickly, and didn't dream.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

The Boss Ch. 01 Previous Part
The Boss Series Info

Similar Stories

Soccer Girls Ch. 01 The beginning of Katie and Melanie's story.in Lesbian Sex
Twin Troubles Pt. 03 - The Yacht Ashley treats Trin, Jessie and me to a weekend on a yacht.in Lesbian Sex
Women's Bondage Prison A bondage theme prison tests Lucy and her fellow prisoners.in BDSM
Women's Bondage Reformatory School Pt. 01 A reformatory school where bondage is the main lesson.in BDSM
Twin Troubles Pt. 02 - The Next Date I face the wrath of my sister when I get home.in Lesbian Sex
More Stories