Riding the Boss Another Day

The second time that I met Nick was last Friday. The week at work following that weekend sucked. Seriously it was awful. True to himself he was the same incompetent manager as before. Same as the entire time I worked for him before the first time our paths crossed at the ABS. I couldn't stand him. There had been some euphoria that took over my consciousness Saturday and Sunday that made me forget who he was. I seemed to forget that he wasn't smart, wasn't competent, wasn't aware of the stupid things he said and did.

I came into work Monday and quickly had that euphoria smacked from me. It didn't help that I was unhappy dressing as a male at the office. My button down shirt now feels funky having the buttons on the male side. My male slacks were as feminine as I could find and the dress shoes as close to women's flats as I dared. All clothes I now only wear at work. The rest of the time I was a woman. It's been a week and a half since I made that change completely. Like many things in life, when things feel right the adjustment is negligible.

He was waiting in the conference room for a 'team' meeting. After the first minute I didn't listen to a word he said. It was all his typical BS. I sat wondering how he was employed. Perhaps his boss is just as incompetent, or maybe just unaware or isolated from him. My current conclusion was that he was just an ass trying to get away with everything he could. Fuck, I guess that means some people will think he was the smart one and I was dumb by working hard and being honest. Fuck it, I went to my cubicle.

Most days I could get straight to work but today I was distracted. I was thinking back to both times I had met Nick to try figuring out what I was thinking letting him fuck me. I should have turned and ran. I had met him on the last two Friday nights. I was out at the ABS dressed as Brianne. He had not recognized me either time even though we had been quite intimate. We had fucked. I rode his cock and we even kissed. It is hard for me to believe but I honestly don't think he had any suspicions whatsoever. Each time I had been sure that I kept my back to the movie screen keeping me backlit. I knew it would make my face difficult to see. But like I said, he had to be dumb, conceited or just self-involved. Plus, he constantly made rude and snide comments about anything and everything at work and it would have come up.

Still, fuck though. The sex we had was intense to say the least. It took over my body and my mind. How else can I explain that I fell in love with him each Friday night. Or maybe it was just falling in lust. I can't explain it even to myself. I spent the weekend completely satisfied yet wanting more. More from him. Blocking it all from my mind I finally was able to concentrate.

The rest of the week wasn't any better. I honestly couldn't stand him at all this week. By Tuesday he had been such an ass that I had already decided I wasn't going to meet him out again. Ever. Well fuck, at least not this Friday. I would see how next week goes but didn't expect any change.

Friday morning came and had me twisted, completely twisted. My feelings had started taking me over on Wednesday and strengthened further Thursday. Half of the time it didn't even register that he was talking. I had started overlooking some of his flaws. He was the same jerk but I found myself staring at his crotch whenever I could. I was admiring his strong shoulders and solid physique other times. I arrived early for both meetings he set up for Friday just to get a glimpse of his crotch as he walked in. I stared watching the outline of his cock hanging down while he walked. Fuck I wanted it again. I just had to tune out his voice. Tuning out his voice definitely made things better.

Each time I shifted in my chair I felt my slacks brush against my ass, my thong helping to keep my cock, well, my sissy clit really tucked. Normally this was a feeling I noticed but thought nothing of. All day long every time I moved I felt them. The soft fabric slid easily over my cheeks. Fuck I needed his big hands gripping my ass again, pulling me down balls deep on his cock.

Many times throughout the day I found myself thinking about him fucking me. I would zone out remembering him grabbing my ass, pulling me down to his hips. Pulling me down to take his cock deep. Feeling him cum deep in me while our tongues played together. Fuck, I had to stop this, stop thinking about it. Stop thinking about him railing me. Fuck I needed it though.

Unfortunately I hadn't had any release since I was with him last Friday so I was starting to really need it. This had combined with the deep craving for his cock becoming stronger by the minute. I fought the feeling until five o'clock arrived. Relieved to have made it, I headed home expecting to find Tracey getting ready to go out again. I had to come up with an alternative place for us to go.

I went upstairs removing my dull male clothing on the way. I detested every piece of it. None of it felt right. Every piece pulled off gave me a liberating feeling. I wanted to donate it all and live free but today wasn't the day.

I found Tracey had again laid out clothes for us and placed two filled wine glasses on the nightstand. She was truly amazing to be friends with.

I removed the last of my male clothing and took a few sips of wine. A minute later I realized that I finished the glass, developing a strong buzz from doing it on an empty stomach. I got in the shower with her. We easily fell into our familiar routine of shaving each other.

Tracey again helped me with my makeup while she was doing her own. I was improving with each attempt but she was still able to perfect it for me. She gave me dramatic eyes and enough contouring to transform my look. It fulfilled desires I've had my entire life making my existence earlier today seem a million miles and a millennium away. I sat on the edge of the bed for a moment contemplating those thoughts. I wanted this to be my reality rather than the temporary fix. The male version of me needs to become and stay a distant memory.

Tracey snapped me out of my thoughts as I sat there. She handed me my little cock cage. I let out a slight chuckle and took it. It reinforced what I was just thinking. It was in the smallest cage I could find. And it barely worked on me. At times my cock shrinks enough to slip out as if it didn't exist. I put it on and the garter belt and stockings next. I followed with my bra and the sheer blouse Tracey had laid out.

Tracey sat next to me. I brought up the suggestion that I wanted to find something else to do.

"Tracey, we should do something else tonight. Something new."

"Okay, what do you want to do?" she responded.

"Umm, I don't know. Maybe just the bar. What do you think? Do you know of something?"

"I want to go to the bar, but the ABS is fun. We should go there too. It's been fun when we're there. I need something again this weekend Brie."

"I just don't know about the ABS tonight."

"Really? Don't you want to see Nick? I bet he'll be there again."

"Yeah, he'll probably be there." I said.

"Brianne, it's so hot seeing you two go at it. It's raw passion. It makes me jealous even. Did something happen at work?"

"No, nothing happened. I just thought maybe you wanted to do something else. To mix it up and have some fun too."

"Oh don't you worry I have plenty of fun there too." she said.

"Well let's get going to the bar." I conceded without really agreeing to go to the ABS. I would wait for her to have a couple drinks and maybe we could find a someone or two to bring home.

I took off the stockings and garter belt that I had just put on. Tracey gave me a questioning look and I shrugged. I pulled on my skirt and slipped my feet into my black stilleto heels. Standing in them again brought a temporary smile to my lips. Tracey finished getting dressed and we took a cab to the bar.

After our third round of drinks, the wine definitely helping me relax, I was no closer to finding anything that would change Tracey's mind or offer an alternative. I tried to make the fourth glass last the rest of the night but halfway through it Tracey was ready to go. She stood and took my hand. Her soft skin made me melt, knowing I would go with her. I finished the wine in one motion as soon as she turned away then stood to follow her.

I rushed to catch up with her taking her hand again. The walk to the bookstore was quiet. I spent the time listening to our shoes clicking on the sidewalk. Sometimes our steps were in sync but they kept changing to alternate. The sound subtly changed from the surface of the sidewalk to the asphalt parking lot as we turned toward the front door. We walked into the glaring florescent light showering the parking lot and entrance of the bookstore. We went in, I paid for us this time and we headed to the theaters.

As much as I felt like I disliked Nick I was looking forward to seeing him. To be accurate I was looking forward to fucking. I craved his cock slipping in me. I needed to feel it on my lips and tongue. Our past encounters ran through my head as we walked. I started to worry that we missed him. I can't explain why but my feelings for him had flipped.

Suddenly we were there. My eyes were slow to adjust to the light shining from the screen.

He sat in the same spot as last time. A memory of him being an ass to the administrative assistant at work today flashed through my mind but was quickly replaced with the memory of his lips pressed on mine. Fuck. I was here. I fought the last of my resistance. I needed dick, his dick. Fuck it, time to be selfish.

I made my way to his row and sat next to him. I sat properly with my legs crossed and my back straight. My skirt rode up to mid thigh as I sat. I leaned back slightly in the seat. My skirt slid another inch or two up my leg revealing more bare skin.

I watched the movie on the screen while I waited for him to acknowledge me. I waited for only a few seconds before he did his stretch. It was the same stretch as last week. He put his arms back with his hands behind his head. I saw him smirk. It was the same arrogant expression. I wanted to stand up for myself. I wanted to be the one to tell him off. I wanted to slap his arrogant face. I wanted to feel his hard cock push past my lips before going deep my throat.

Fuck. I kept ending up at the same answer.

I accepted my fate and submitted.

I reached out to his belt, my hands trembling the whole way. Suddenly afraid he'd push me away, I needed him. I needed his dick. I needed his dick balls deep in my mouth. I needed his balls pushed to my chin while the head of his dick was stuffed in my throat blocking my lungs.

I fumbled to unbuckle it. I saw that someone had sat down one seat over from him. I didn't look at them. There were two guys up front naked and fucking so I wasn't worried about him. It was most likely someone that wanted to get off watching.

Again Nick was commando. When I unzipped his pants his cock popped out like in a porn video. It was hard quickly tonight before I had barely touched it. I licked it from the base until I reached the head. I dropped my head on his cock taking it in fully. His hair tickled my face when my lips landed around the base.

I lifted up to just the tip of the head. I slowly lowered my head back to take his cock in again. I heard him groan. I pulled off and sucked him in again hearing him groan louder. I started getting into a relaxed rhythm on his cock. I had made it about to the point where he usually pulled me off so I could ride him.

Nick pulled my head up so we were face to face. We kissed briefly before Nick interrupted. He roughly pushed my head back to his cock. I barely got my mouth open enough to keep my teeth off his cock. I started fighting with myself over leaving. I shouldn't let him be so dominant. I lifted my head up and off his cock. I felt him push again so my lips just touched the head of his cock. Fuck I wanted it again but I wanted to leave.

Nick and his cock won out. I opened my mouth to rub my tongue across the head. The precum that had built up made me forget any feelings of leaving. Instead I opened my mouth further just in time for Nick to push my head down on his cock. He pushed me to his balls. His hair pressed on my cheek as he held me down and pushed his cock further into my mouth.

He let go of my head letting me take a breath. I pulled off completely. Before he could push me down again I sucked his cock back into my mouth. I sunk down on him until my face was buried in his hair again. I pushed myself down to match the pressure he had used pushing me. I put my hand between his legs to massage his balls. I felt their sweaty warmth as I started slipping a finger back to his ass cheeks. I pulled my head up letting his cock come out completely before taking it back in. I started sucking him with the same rhythm as before he had pulled me off.

Each time I sucked his cock back into my throat I pushed my finger closer to his asshole. The sweat was helping me slide back until I felt it. I took a deep breath and lowered my head again. I kept his cock buried as deep in my throat as I could while I wiggled my finger into his ass. I heard him moan louder and curse when it slipped inside. He lifted his ass so I could push my hand back letting my finger enter him completely. The sweat made it easy. I started massaging his prostate and returned to giving him a slow and relaxed blow job.

I knew that it would push him over the edge soon. His moaning was louder still and had attracted a few men's attention as they turned to watch us. I kept going, enjoying feeling the head of his cock sliding over my tongue. It pressed into my throat again. I massaged his cock with my tongue pushing him over edge. He moaned another curse and flexed his legs. He lifted his ass off the seat and pushed his cock deep into my mouth again.

I lifted up so just the head of his cock was in my mouth. I closed my lips tight around his cock to suck all of his cum up. I moved my free hand over to pump his cock so I could keep his cock in my mouth. I felt the head swell and throb. The first squirt of his cum shot out hitting the back of my mouth. Then the flood came. I had to swallow a couple of times to keep from leaking cum while he shot stream after stream. There were at least ten strong pulses of cum that he shot out before it slowed. It was the first time he had finished with me anywhere outside my ass. I knew that he had strong orgasms but still I was shocked at how much he came.

His body relaxed as I milked the last of the cum from his cock. When I was sure I had it all I let go of his cock and pulled my finger from his ass. I sat back in my seat to catch my breath. I watched his cock finish going limp.

One of the guys that had watched us walked up to me. He had been jerking his cock and still had his cock sticking out of his pants. My skirt was too tight for me to spread my legs when he stood in front of me so I moved them to the side. I sat forward and kissed the head of his cock. I licked the head letting my tongue explore a bit. The head tasted of his precum from him rubbing it around when watching us.

I sucked his cock in tasting precum all down it. It wasn't a big cock but tasted wonderful. Taking the whole thing in was easy. It just made it to the back of my mouth. I grabbed his hips feeling his rough jeans. His cock was just sticking out through the fly. There was something impersonal about just his cock being exposed that turned me on more.

I kept a slow pace guessing that he was probably close to coming after rubbing himself while watching us. I rubbed my tongue back and forth on his cock. I was able to suck his cock in a few more times before triggering his orgasm. The last time I took his cock in I felt him swell. I held him tight letting his cum squirt on the back of my tongue. I pulled his cock out and savored his cum for a moment. I swallowed it and then licked the last drop from his cock.

He turned and pushed his cock back into his jeans while he quickly walked out. I sat back to relax for a while. There was one guy that was still watching. He walked over with his hard on sticking out and bouncing with each step. He stood in front of me presenting his gorgeous erect cock. I wasted no time pulling him closer and taking his cock in my mouth.

His cock was long but thinner than Nick's. I sucked it in letting him push it into my throat. I reached further around him grabbing onto his ass. His hairy ass was so masculine. Feeling it flex in my hands as he pumped my mouth was so hot and sexy. I love feeling in my place sucking a man's cock. I took my time, sucking it slowly. I explored it with my tongue. The occasional drop of precum reminded me each time of how lucky I was to be sucking a cock.

He interrupted by moving over to sit in the seat next to me. I followed him, taking his cock back in again. His cock felt perfect in my mouth but I was still craving something else. I was debating whether I should have him fuck me or finish the blow job.

Fate took over when I felt Nick's hands on my hips, at least I guessed it was him. He lifted my ass up making me break contact with this guy's cock. Nick put me on my knees on my seat. When I pushed my ass back toward him Nick pulled my skirt up. He pulled it roughly over my hips exposing my ass.

I reveled in the vulnerability while I was kneeling. My head automatically bobbing up and down on this cock as I felt Nick holding my hips. His hands moved to pull my cheeks apart. I felt him pause at my entrance. He reached around to my chest and slipped his hand inside my blouse. Before I could figure out what he was doing he had pulled out the little bottle lube I had stashed in my bra.

I felt him pull his cock away from me for a moment. When I felt it back it was again aligned with my asshole. He pushed slightly. I felt my ass opening to accept him. When he pushed again I felt the shockwave of ecstacy from him pushing his cock in balls deep. I wanted to scream out but I had the guy's cock filling my mouth and a little down my throat. The combination of sudden stretching and the extreme pleasure from Nick's thick cock rubbing on my prostate was intense. He pulled out completely and slammed back in.

I was lost as Nick was really getting into it. I tried to concentrate on sucking the other guy's cock. Most of the moving I did though was from Nick fucking me. He was gripping my hips tightly. He pulled me to him for every thrust, then pushing me forward forcing my mouth onto the cock in my mouth. Fuck it felt good.

I was going to cum. I was getting closer each time Nick's hips pressed against me. The hard cock from the random guy was being pushed deep in my mouth. Now each thrust forced it back into my throat. When I was able to concentrate again I slipped my hand back between random guy's legs. I gathered some spit on my fingers and slipped them back to his hole. He jumped a little when I pushed one finger in. His ass tightened around my finger and I heard him start moaning. I really wanted him to cum. I needed to taste it and take it. He cursed a few times before I felt the head of his cock start to swell.

"Oh, fuck, fuuuck" is the last thing I heard before his cum shot into my mouth. I massaged his hole while I sucked on his erupting cock. I had just the head in my mouth and collected all his cum. The first squirts hit my throat before it slowed. I swallowed it as he slowed down. I heard him gasp for air once after he finished. I swallowed the last of his cum and let his cock fall from my mouth. I licked the front avoiding the head, just collecting a last drop of cum. Once his cock had softened he stood up.

Nick continued to thrust into my ass until the last anonymous guy dressed and left. But then he pulled out and sat down. The orgasm I was approaching left. Fuck I needed it though.