Riding the Boss Again

The week at work went surprisingly smoothly overall. It had started with the boss, Nick acting differently. Suddenly he was a quiet and reasonable person, well at least compared to before. Eventually though, throughout the week he started getting worked up over stupid problems he had caused.

The Friday before had led to an interesting encounter with Nick. I had dressed as Brianne, visited my favorite ABS and been fucked by him. Fucked very well by him actually. And he didn't recognize me. I still couldn't believe it but there were no signs during the week that he figured it out either. That Friday I had done my best to transition to Brianne wearing makeup, glasses and a wig. Of course I had a tight skirt, sheer top and heels on as well. The theater wasn't well lit and I kept what light there was behind me shadowing my face. I was well disguised from my usual dull, boring, unfortunate male self, but in such an intimate act I was certain something would spark some recognition. After thinking about it for a few days I also realized that he probably wouldn't have expected anyone he knew to be there.

Friday night came. I had spent most of the day trying to steal glances of him. There were a couple occasions where he was talking to someone and I could have sworn I heard him say 'slut'. It had to have been my imagination though. I think I was just hearing what I wanted to hear.

I realized I was craving the attention, craving his attention and I hated it. I hated it and struggled to understand why I needed more of him.

I couldn't believe that I was getting excited about meeting him tonight. I suppose a big part was being Brianne. I always look forward to that change. What was wrong with me though? I still didn't like him any more than last week but was excited to have him fuck me? I was truly obsessing on it. Realizing that I had spent most of the day thinking or fantasizing about it brought me to the conclusion that I had to just stop thinking about it. It just didn't make sense.

I arrived home from work finding Tracey was just starting to get ready. I had given her the code for the door quite a bit ago. Something about arriving home having her already here was reassuring. I headed upstairs to the master bath where she was showering.

She had laid out the outfits for us on my bed. She had a black lace bra, black skirt and red sheer blouse for me tonight. She wore black and red with red stockings.

Two glasses of riesling were on the nightstand. I took a few sips from the full one making it even with hers before walking into the bathroom.

Tracey was showering so I stripped and joined her. With the steam from the shower warming the room we started helping each other. I picked up where she had gotten to, shaving the rest of her body. After, she took the turn to shave me completely. The hot water always feels so sensual running down my hairless skin. When we finished we used body lotion on each other. Her hands felt so sexy on my skin. The warmth of her fingers started me fantasizing about tonight already. Her soft skin was equally erotic under my hands as I massaged the lotion in.

Tracey helped me occasionally with my makeup while she did her own. It looked stunning thanks mostly to her work. I wore the same glasses as the last week but selected a blonde wig with black tips styled into a bob. I always love the feeling of it brushing my cheeks when I move my head.

We dressed and headed out. We took a cab to the bar again arriving earlier than we had last week. At least I hadn't had as much wine as before. Still I felt quite anxious. It was different from the worries I had before of being completely cross dressed and in public. Tonight I was really craving attention. I fretted over whether he would show. What if he didn't. What would it mean? I had to stop thinking about it.

We had a couple glasses of wine at the bar before walking to the ABS. The tension built as we walked. I reminded myself that it was just sex. Someone else would be there if he wasn't. It wouldn't mean anything if he wasn't there. I couldn't figure out why I cared.

Once inside we paid and I walked straight to the theater. I fretted over whether I would see Nick sitting in the same area. Feeling like I almost passed out working myself up whether he would be there I had to stop and catch myself against the wall. What is wrong with me? Before last Friday I wanted nothing to do with this man. This was supposed to be my escape from the reality of my male world. Work shouldn't be intruding. No one from work should be intruding. Yet I am worrying about him not showing up? Before I could contemplate my own question my feet walked me into the theater. I heard my stilletos click on the floor until I reached the carpet.

There he was. I walked to him and sat to his left.

"Hey there stud. Nice to see you again." I said moving close enough to whisper it.

Nothing. No response. No acknowledgement. I could feel my heart beat. Finally I noticed it, the smirk on his face. He leaned back in the chair stretching his legs forward and a little apart.

I took his subtle invitation. I denied that he thought he owned me. That he thinks I was becoming his personal cockslut. Denied I was there at his whim instead deciding that I wanted to use his cock for my own personal enjoyment. He would be my toy to use.

I reached over to unfasten his belt and open his fly noticing he was still wearing his business casual clothes from work. I wondered if he came straight here. Releasing his cock came easily making me notice he was not wearing underwear. I was surprised that I was getting excited about it. I felt my cock start to strain against its constraint. I wondered if he had been commando all day at work too. Was he anticipating having me again while meandering around the office? Did he fantasize about me when he shifted in his office chair?

His wiry hair was untrimmed and his cock limp. I put my lips on the head, kissing it before wrapping my lips around it. I found a hint of the taste of cum on his cock. I wasn't sure if it was my imagination.

"Mmmmm" I moaned keeping his cock in my mouth. I teased the head and massaged just below it with my tongue.

"Fuck, your good at that slut." he said. "A lot better than the CD here earlier. She helped me out a bit before my slut got here."

"Mmmmm." I acknowledged what he said. I sucked him in the rest of the way. I felt his cock stiffening as I used my tongue to play with it. His hair rubbed my cheek when I had my lips around the base of his cock. I already knew I was better than whatever tramp he had earlier. I lifted up to just the tip of the head. I slowly lowered my head back to envelop his cock again. I heard him groan. And groan again louder. I glanced around as much as I could while staying on his cock. There were at least a couple of guys now watching. I pulled off again letting our audience see the seven inch length of his thick cock. Then I buried it in my mouth showing off my ability to easily swallow his cock a couple inches down my throat.

He was really getting into it. He was grinding his hips every time I took him in. His cock felt perfect again, sliding on my tongue and pushing on the back of my throat. I had developed a rhythm and worked him for a while before he interrupted.

He pulled my face to his kissing me right away. The kiss was brief. He looked in my eyes and my heart skipped. Fuck, did he recognize me? I hoped that I was disguised enough.

It seemed like forever before feeling relief when he started pulling me over to him.

"I want your ass now slut." he said.

I followed his command quickly. I stood and bent down to pull his pants off. I pulled my skirt up over my waist. I straddled his legs enjoying the feel of his hairy thighs on my bare shaved legs and ass. It sparked my slutty feminine feelings immensely reinforcing my need to be his slut. I pulled the small bottle of lube from my bra squirting some on my hand. I reached back and massaged it on his cock. He moaned.

"You're really are a slut." He said matter of factly. I had a short lived desire to tell him to fuck off. It was pushed out of my thoughts quickly by the desire for his cock. I hated it but it was true.

"Hurry up slut. Get on it."

I moved to align his cock with my entrance. I felt the head just start to stretch my ring. The ecstacy was traveling through my body as the head slid completely inside. Then I dropped on him landing on his thighs, pushing my ass down to him to get his cock as deep as possible.

"Ohhhh fuck!" he said nearly yelling. He rested his head back on the chair and groaned again as I ground my ass on him. The electricity shot through me feeling his cock pushed completely in. I leaned forward kissing him on the lips. He returned my kiss as I started riding him. Our lips were barely touching as our tongues played together.

I started unbuttoning his shirt. When I had it open I pushed it to each side and off his arms. His undershirt was next. I pulled it up and over his head gaining full access to his chest. His hairy chest. His sexy, hot chest. I leaned in smelling his scent, savoring it while taking it in. It was a combination of a cheap cologne, deodorant and sweat. Fuck why was I hot for him.

I ran my hands over his pecs feeling the hair under my touch. His hard nipples announcing their location when I passed them. Our lips met again while I started teasing his nipples. I pinched them gently while continuing to ride his cock. That thick cock. It was stretching my asshole to its limit again. My own cock still restrained, pushing against the shiny cage with all its might.

I shifted a bit so he would rub on my prostate better. It was really getting me closer to cumming with each stroke. Somehow his cock did it right. It stands out as the best cock to have made me cum without having any attention directly on my cock. There has only been one or two before.

"Fuck, Nick."

"What is it slut?"

"Your cock feels so good fucking me."

He just put his head back. I don't think he cares if I enjoyed it. It turned me on more to know.

I felt an orgasm coming over me. My legs were shaking as I rode him harder. His cock was rubbing me perfectly. I moaned as my cum started to drain slowly from my cock. Some dripped on his stomach and pubes while a bit ran down past my balls to my ass. It kept going as I rode him. I could tell a little difference when it got to my hole. He started thrusting back as I slowed down a bit. It had taken over me and I couldn't concentrate. As my orgasm trailed off he told me to stand.

I pulled off of his cock and stood up. Not sure what he wanted I looked around to see four or five guys watching us. Most of them had someone kneeling, sucking their cocks. Tracey had her mouth on one's cock.

Nick stood and turned me away from him. Standing naked he kicked my feet apart and pushed me forward forcing me to bend over the row of seats in front of me. I felt his cock searching for my entrance and I bent over as far as I could. My vulnerable ass waited for only a few seconds before he filled me again. Once his head was in he pushed forward as hard as he could.

"Oh fuck Nick!" I started moaning as his cock stretched me again. It mirrored slamming into me like when I first got his cock in many minutes ago.

Nick started fucking my ass hard and fast. With each thrust I was pushed hard into the seat back. My cage bumped the seat and my hair swung back and forth. I had to struggle not to be pushed over the seat. The force behind his thrusts caused his hips to slap on my ass and his balls to swing hitting my legs. It felt so amazing I had a hard time believing it was really happening.

His stamina was impressive. Probably because he had came before I arrived. It didn't matter to me though. His cock continued to rub me right. Each time his cock filled me I was pushed forward. It was becoming hypnotic as my blonde hair swung forward, the black tips brushing on my cheeks. The weight of my breasts felt so feminine. My stilletos lifted my ass high enough to align perfectly with Nick's cock. At work he stood was many inches taller.

Nick's moans turned to grunts. Each thrust brought him closer until I felt one last push. His cock unloaded deep with his hips pressed tight to me. With each pulse of his cock he squeezed my hips pulling me tighter to him.

He pulled out leaving me feeling empty. He wiped his cock on my ass before stepping back and grabbing his clothes. He pulled them on.

"See you next Friday slut." Nick's parting words.

I stood recovering, catching my breath. I smiled feeling Nick's cum running down my legs. My cum had been spread around my thighs from our fucking. I was a mess. I left my skirt pushed up around my waist and sat on the seat. Tracey sat with me. I relaxed letting everything leak out on the seat. She held my hand as I finally caught my breath. We sat together in silence for several minutes before we stood to leave.

I walked to the restroom like that. My skirt was wrinkled around my waist. Cum, his and mine was glistening on my thighs and ass. My little cock in its cage jiggled and my ass was fully exposed. I cleaned up as much as possible with the paper towels before straightening out my skirt.

Tracey and I walked back to the bar hand in hand. Her soft, warm skin reminded me of how she cared about me. I wasn't sure what I was getting myself into but I was grateful she was there. I nursed one final glass of wine before we headed back to my house. We both felt tired and I'm sure Tracey knew I needed company. I managed to take off my skirt and blouse before falling into bed. She also made it to her lingerie before we drifted off to sleep together.