My Sex Life: Boss Pt. 02

My Sex Life: Boss pt. 2

Not much to say with this one. I am going to try to get back to more regular posting after far too long without. Story suggestions are welcome or if you just want to message your thoughts. I will respond to serious attempts to communicate. However I will not respond right away. This is the conclusion of this segment of the series, but I have a number of other ideas in the works for this series.

After my intense encounter with my boss, Makara, I arrived home tired and overwhelmed. Once in my room I quickly removed my clothes and with care pulled the underwear from my ass, moaning as I did so. I stood and hesitated a moment before dropping them in the trash. I considered further before pulling out my other pairs and piling them on the bed. I stared at the pile as I considered whether or not to comply with Makara's instructions to get rid of all of my underwear. Finally I put them away and took a quick shower before crawling into bed.

The next morning I woke late. I considered stroking myself, but noticed a text. Groaning I grabbed my phone and found it was from Makara. It was short and to the point.

- No Cumming

I stroked for a short time, but ultimately gave up without finishing. Foregoing the futility of swearing I got up and went to my dresser. I hesitated as I considered my underwear, but ultimately grabbed a pair of shorts and dressed. It was weird walking around my room without underwear. I was soon about half erect and wondered how I was going to get through a day, between being turned on and an erection would be hard to conceal. Fortunately I had no reason to leave home that day, but I knew that the next couple of days would be busy and that meant I would need to come up with something.

After a day of considering the issue I selected a pair of pants that were tight enough in the crotch that while uncomfortable would keep my erection in check. Fortunately I had another pair and I would be doing laundry on Tuesday. At last Wednesday evening arrived and I headed over to Makara's shop. I was amazed to find two rooms completely organized and ready for business. On Saturday night one had been almost ready, clearly Makara had been busy. When I reached the room he was working on he looked up smiling.

"Ah, good you're here." He immediately crossed the room and began rubbing my crotch with his right hand. I was soon straining against my pants. He grinned wider.

"Good, you're following part of my instructions. Have you cum since then?" I shook my head, unable to speak as I felt myself blushing.

"And my other instructions?" I avoided his gaze. However before I could respond he suddenly grabbed me and before I could react I found myself bent over a desk. As I attempted to gather myself for a response he pulled down my pants, allowing my hard dick to swing free. Again I was so shocked by this turn of events I hesitated and suddenly felt a sharp smack on my rear. I cried out, more in shock than anything else, but this was only the start. He continued to smack my ass, sometimes one cheek other times both, with a steady pace, slamming me into the desk.

In a short time my ass was stinging, while I'm sure both my ass and face were bright red. My dick was also painfully hard. It was only because he was holding me in place that I didn't drop to my knees. I had no idea how many times he smacked me and I was still swaying back and forth when I realized he had stopped.

"Now, get to work and next time I expect a report that you've completed all of my instructions." I nodded slowly. He looked sharply at me, but I spoke first.

"Yes, sir." He smiled and patted my ass almost affectionately.

"Good." He returned to organizing the room and I went to the other room that needed work and saw that he had made a decent start on it since Saturday. I worked steadily and by the time I was ready to leave the room was nearly finished. I headed to the other room to let him know I was done. He looked up when I entered.

"How we looking?" I swallowed as I tried to see him as my very personable boss and not the guy who had fucked me to an incredible orgasm.

"I think we might finish in time for your Saturday opening." He grinned.

"Wonderful. When can you join me next?" I thought carefully.

"I've actually finished most of my classwork, so Friday, yes, as for tomorrow, maybe about nine." He nodded.

"Excellent. Sleep well." He returned to finishing the room and I turned to leave.

Once home I got my underwear out on the bed and after staring for a bout twenty minutes or so I three them all into the trash.

The next day continued to be a struggle as I was certain that I was constantly erect and that it was obvious. However I got through the day and arrived just before nine. He was working steadily away when I arrived. When I entered he looked up, smiling when he saw it was me.

"Good." He quickly crossed the room and gently squeezed my hard dick. "A bit pent up. Well, did you follow my instructions?" I nodded as I failed to suppress a moan. He laughed softly.

"Yes...sir." He nodded and released me. I groaned in frustration.

"Let's see how far we get to tonight?" I nodded as I returned to the room that I had been working on. I frequently stopped to take a deep breath rather than rushing. However despite this I was still confident that we could finish in time for the opening. This time I didn't notice the time, but he came in.

"I think this is late enough. I shouldn't need long to finish the other room and together, two hours tops to finish this one. Let's go." As we walked to the parking lot I was just waving goodbye when he shook his head.

"Come on there's an all-night diner practically next door, on me." I smiled and followed him, we passed two store fronts before we reached the one that was lit. He led the way into a fairly traditional diner with no other customers, but one employee in sight. She was an older woman, close to fifty I would estimate, attractive, but probably a little old for me. She appeared bored, however she looked alert when we entered.

"Hi, sit where you like, I'll be right over." He lead the way to a booth second from the door, which I noted was closer to her, but I didn't give this any further thought. He smiled when I turned back to him.

"Her name is Veronica, no nickname and she owns the place. And I happen to know she likes younger guys." I'm certain that I was blushing and he laughed, but stopped when she got close.

"So what can I get you boys?" It was at that point that I suspected he had been telling the truth due to the honey she seemed to be oozing when she said "boys". Makara didn't even glance at the menus.

"Two large stacks of your famous pancakes with extra cinnamon and side of bacon to your exacting specifications. To drink, your fresh squeezed juice of the day." She smiled and I imagined that she was not easily embarrassed.

"Alright, should be about fifteen minutes for that many pancakes." She walked to the kitchen and he turned back to me.

"So, I'm curious have you ever been with a guy before?" I shook my head and he leaned back with a look of concentration. "Really I would never have guessed. Care to elaborate?" I sighed as I leaned into the table, elbows resting on it.

"I dated a girl who liked to use a strapon as much as she liked getting fucked." He nodded as he mimicked my position at the table.

"Does that embarrass you?" I exhaled hard.

"To discuss my sexual experiences? Yes. However I did enjoy it, as I'm obviously enjoying this latest experience." He nodded as he sat back again. He turned the conversation to mundane topics, sports, which he only had slightly more interest than I did, hobbies, he was too busy and I mainly read when I wasn't working on schoolwork. Finally he turned the topic to comic book adaptations, which resulted in a heated debate on my dislike of Iron Man 3, which he vehemently defended. This lasted about ten minutes before I realized that he had chosen that movie to intentionally get a rise out of me. I stopped and shook my head.

"Do you actually like it?" He laughed hard.

"No, it completely misses the mark, especially since it's the final solo movie for the character, even if it wasn't his final appearance. That being said the beginning that goes some to addressing his PTSD is good, but a good beginning does not make up for a poor ending." I exhaled slowly as I released the tension I hadn't known I was holding. It was at this point that Veronica returned with the drinks. I was blown away by the rich fruit flavor, although I wasn't sure what fruit as she had mixed at least three to make it. I sighed as I sat back slowly swallowing. My eyes were closed and they only opened when I heard him laughing.

"Wow, and I thought you moaned loudly before." My eyes shot open and I looked sharply at him.

"What?" He grinned wider.

"That must be a good drink. I thought it was amazing, but I didn't think it was orgasmic." I shook my head, blushing. We didn't speak for several moments until Veronica once more came over, this time carrying two plates stacked high with some of the most amazing pancakes I had ever seen. The first bite was as much a taste explosion as the juice had been. This time however he was initially focused on his own food and so didn't make any comments. This continued until I was about halfway through, when he spoke.

"So, good, huh?" I hesitated a moment before dropping my silverware loudly.

"Okay Makara, what is this? First you rather forcefully 'take me for a ride', now you invite me for pancakes, like friends." He sighed and deliberately lowered his own silverware.

"Don't be dramatic. I like to have fun, but that doesn't mean we can't just get some pancakes without it meaning something. Besides I thought we were friends. Otherwise why are you accepting the crazy hours without a huge compensation?" I sat back as I considered what he was saying. However before I could respond Makara stood and carefully laid some money on the table.

"Tomorrow?" I nodded slowly. "See you then." He walked off and I stared at my pancakes before starting to eat mechanically. As I was finishing Veronica approached.

"You guys have a fight?" I shook my head and looked up.

"No, not a fight, I was trying to figure out what was going on, where I stand I guess." She nodded as she cleared up the dishes.

"I'm closing up. Want to keep me company?" After a moment's hesitation I nodded. A glance told me he had paid for both of us and a tip, so I followed her into the kitchen. As she cleaned the dishes she spoke. "So, what are you thinking about my invitation?" I shrugged.

"I honestly don't know. My first thought is to simply take you at your word that you simply want someone to talk to, but that does sound a bit naïve to say it out loud." She laughed as she put a plate in the drying rack.

"You are cute, but I haven't slept with someone I just met since I got out of college. Maybe if you come back." I smiled and just suppressed a snicker. Relaxing against a counter I spoke.

"So, how long have you had this place?" She put the last of the dishes in the drying rack and dried her hands.

"Hmm, I guess it's just coming up on fourteen years. I bought it after I decided to quit my job at the law firm." I batted an eyebrow, but waited for her to continue. She smiled. "Yeah, you probably wouldn't expect a lawyer to quit to run a diner. I was successful, but I just got tired of it. I had the money so I bought it and only occasionally regret it." I laughed a bit at this.

"That is a bit unexpected, but I guess you got to find something you can be happy to do day after day." She nodded and I took the opportunity to more carefully appraise her. As I had noted before she was about fifty, with dark hair, green eyes and pale skin. She grinned as she finished prepping the place for the next day.

"Care to guess how old I am?" I inhaled slowly as I felt I usually guessed low and you never know how honest you should be.

"Forty-eight, forty-nine maybe, but you're probably going to tell me you're actually fifty." She laughed as she led the way to the door.

"Fifty-two actually. I was a lawyer for about ten years before I quit. Well, good night..." This time it was my turn to laugh.

"Lukas." She nodded.

"Nice. Good night, Lukas. No promises, no expectations. I'll see you again sometime."

The next day was pretty uneventful as we focused on finishing for his opening. We barely spoke and I soon realized it was because he was giving me space. I soon finished my part and went to find him. He was apparently finished and going over paperwork, but he looked up when I entered.

"Ah, Lukas good. See you tomorrow?" I hesitated briefly before speaking.

"Yeah, about eight?" He nodded.

"Sounds good. Night." I briefly considered stopping at the diner, but decided I just wanted to get to bed quickly to be ready for the next day. The night proved to be long and confused before I finally settled.

I arrived a couple minutes after eight and found Makara going over everything in the main room. He was tweaking the positions of things, straightening and re-straightening, in other words he was keeping busy. He continued for several moments before he saw me. He paused, looked down and looked back before laughing.

"Right. I should just stop." He led the way to the counter where he had set up a computer. "I'll deal with purchases. Why don't you circulate, see if you can help people. Until we get a feel for what kind of business we get. I'm going to be interviewing tonight and all day tomorrow, so I should have this place staffed next week." I nodded and went into the next room to familiarize myself with what was available. The morning proved fairly quiet, from opening, at nine, till about eleven only two customers made it beyond the main room. One of whom needed my help to carry a small cabinet up to Makara and then out to their car. Around a quarter till noon as it continued to be quiet I made my way to the main room and Makara smiled.

"Maybe not a very successful day, but it's fine." He paused as I stood around trying not to look bored. "Let's have some fun." He pointed to where he was behind the counter. I joined him.

"What do you mean?" He grinned as he double checked that we were alone. Before I could react he grabbed me between my legs and I just managed to suppress a moan. He nodded.

"Good still following instructions I see. On your knees." My eyes went wide and I hesitated before slowly dropping to my knees. He wasted no time in pulling out his cock, which was already hard. He patted my head and took me in both hands to begin slowly pushing forward. The head briefly touched my lips before I opened my mouth to let him inside. Makara slowly moved forward until he was about halfway inside when he waited holding me in place.

A short time later he pulled back and pushed forward with care. However he soon picked up speed and I concentrated on not gagging. Suddenly I froze as I heard the bell ring signaling a customer. He tapped me and I slowly continued as he spoke to the customer. On an inward thrust he went too deep and I gagged. He pulled back and I heard the customer.

"Excuse me?" Makara made a sound like he was pounding his chest rhythmically.

"I apologize, it's about time for lunch." The customer made some noncommittal noise and a short time later I heard the door again. Makara chuckled softly.

"Sorry about that, try to keep quiet." Once again I focused on taking his cock in my mouth feeling some of his precum drip down my throat. When I heard the bell again it was everything I could do to stay still. It soon became clear that the person who had come in was delivering lunch. Once they left Makara tapped me and pulled out. He quickly crossed the room to turn the sign to "closed". When he returned he smacked the counter.

"Bend over." I nodded and followed instructions. A hand moved gently over ass and I moaned softly. However he did not linger, but swiftly pulled down my pants. He made a few swift smacks, eliciting further moans from me, and a quick stroke showed I was completely hard. In moments I felt a liquid being squirted into my ass. This was followed by a finger that soon pushed inside. I moaned louder as he thrust his finger in and out.

After he had been doing this for a bit I felt that if anything my cock swelled a bit and I felt that if he had continued I would cum. However he soon stopped to add a second finger, but he only made a couple of thrusts before I felt a third. This was not quite so easy and I felt more liquid being added. All three fingers returned and pushed as I moaned while still my ass resisted, however he kept pushing. It hurt mildly, but suddenly the fingers popped inside and I cried out. He hesitated before beginning to thrust. I moaned and the sound was almost continuous, once again suggesting that I might cum.

I groaned as he stopped and pulled out. I practically collapsed against the counter. Makara briefly stroked my ass before smacking it. I moaned softly but didn't move. He laughed and put a condom on my hard cock. I hoped he would start soon. I didn't have long to wait before I felt him lining up his cock.

After a few moments I groaned as I realized he was only rubbing the head of his cock between my cheeks. He pressed the head against my balls, but continued to rub up and down. However before I could voice my objections I felt the head pressed against my anus. I felt it press in, my ass resisted briefly, but he added lube and forced my ass as wide as possible. There was a brief burning pain, but all too quickly the head penetrated. I moaned loudly as he briefly stroked my hard cock. This caused me to relax allowing him to push further in. My moaning became louder as I pushed forward.

It seemed to take even longer than before for him to get all the way inside, during which I felt myself swell until it seemed as if once again I would cum. At one point he stopped, but only to reposition himself to start thrusting even harder. My moaning increased with the force of his thrusts. Feeling my ass spread under his assault I gripped the counter hard as I felt my cock swell almost painfully. He continued to thrust, seemingly untiring until I cried out, barely noticing the tingling in the head of my cock.

I came hard and was shaking in his grip, vaguely wondering when I would stop orgasming. I collapsed onto the counter, but his thrusts continued unabated. My focus was now entirely on my ass and I was feeling a bit sore from the position. After a while, full of more thrusts from him, he released my ass to smack both cheeks, I moaned softly as I was feeling subdued due to fatigue. After several more smacks he gripped my ass to make one more hard thrust, followed by several softer ones before he moaned one last thrust and I felt him cumming.

He moaned and his cock twitched inside me before he pulled out. He helped me into a chair and let me rest a moment. He pulled off my condom and squeezed the contents into my mouth as he held my head back. When he was satisfied he pulled off his own condom and repeated the process. Once more he set aside the condom, this time he thrust into my mouth.

"You know the drill. Clean me up." I still struggled to let him in as I used my tongue. At last he pulled out, although he was now hard and I realized I was as well. He handed me my clothes. "As much as it would amuse me to have you eat lunch naked, we don't have time." As I was dressing he crossed to the door, dressed enough to pass muster, and unlocked it. We ate in silence, although I was giving more thought to this being my first experience with public sex, rather than where this was going. When we finished he looked around to ensure there was no sign of our activities and soon customers began coming again. However it proved to be a slow day. Finally the day ended and he turned the sign to "closed".