Riding the Boss

Tonight wasn't a spontaneous, spur of the moment act. Tracey, a close 'girlfriend' had really wanted to go out dressed. The more she talked about it the more I was in. We often dress together but it has always been at her place or mine. We have never gone out dressed. Our neighbors haven't seen us either as far as we know. We decided to go to the C & C ABS. We had been to this adult store many times before alone and together and often seen and talked with other CDs.

We both had a difficult week at work with overbearing and sometimes unreasonable bosses. I needed something to help me completely forget about it until I was back on Monday. Tracey had suggested we start with a little chardonnay.

We were getting dressed at my home to spend a Friday night at the C & C. I had been practicing on weekends and occasionally on weeknights. I felt I was getting reasonably good at applying makeup but I needed a test albeit an easy one. I finished and was happy with how I did. The red lipstick was bright and I knew it would play off my lingerie. Tracey needed no help. Her makeup was always stunning.

I am 5'11" and love wearing high heels. I usually wear stilletos around but I also have a pair of red five inch heels that I decided to wear tonight. They would compliment the red lingerie I also planned. I used the adhesive to attach my breast forms then clasped the lace bra in front. I carefully pulled on red lace stockings and matching garter belt. I put on my shiny metal cock cage to keep myself under control. The only interest I had in coming that night was if I was fucked right. Skipping any panties I pulled on a conservative grey pencil skirt that had enough stretch to pull up over my ass. A black sheer blouse was next, buttoned to the top. My wavy brunette wig was next followed by a pair of nonprescription glasses to disguise my face the last amount.

I came out of the closet to check out my work in the full length mirror. After a couple of adjustments here and there I looked perfect. Well not perfect but as good as I have been able to get. Tracey had a similar outfit on matching my red lace and black sheer blouse. We had both been wearing plugs to keep us ready to be fucked. We took them out and lubed up a bit. It's nice to be ready. I tucked a small tube in my bra.

We had already made it through most of the second bottle of wine as we were getting ready. We walked out to the cab arm in arm. The wine was part of the reason. We were really leaning on each other for emotional support tonight. The drive went by quickly. The driver dropped us at a trans friendly bar close to the bookstore. We needed our liquid courage topped off.

After a glass or two we walked the three blocks over to the store. I noticed the parking lot was half full as we walked in. Tracey commented that she hoped there would be some decent guys tonight. I hoped so too.

We paid and headed to the straight theater. We sat together for a bit. Soon we each had a guy standing next to us with their cock out. I quickly had my guy in my mouth. He didn't last long. He shot a small load and bailed. Tracey's guy had finished also so we got up to move to the gay theater.

We split up to sit next to a couple of guys already there. I sat next to a guy sitting bare in the seat. His pants were off to the side. I replaced his hand on his cock with mine and started stroking him. After a few minutes I leaned to him and asked in my sexiest voice to suck him. He moaned and stretched his legs. I took it as a yes and started sucking his cock. It was a nice cock too. It was a perfect 7 inches or so and thick. Definitely it was above average. The biggest size that I can usually handle comfortably.

I soon had him deep throated but he asked if he could fuck me. Normally my first thought would be a resounding Yes. The problem was that I recognized his voice. I panicked with the knowledge that I had my boss, Nick's cock in my mouth. In my mouth and down my throat as far as it would go. He wasn't my favorite guy in the world. Quite the opposite. He was difficult and liked to bark orders without ever doing any work. And he was usually clueless about things.

I had to think what to do. He obviously hadn't recognized me. He was naked in a gay theater. And he wants to fuck me. Before I could process the situation and decide on a course he asked again.

"Cocksucker, can I fuck you?" He repeated. "Aren't you a slut? That's why you're here. Isn't it? I bet you don't have any panties to take off either."

I let his cock fall from my mouth and moved close to his ear.

"Hmmm, I don't have panties on." I whispered. Then I moaned and breathed lightly in his ear.

I pressed my breasts on his chest and took his cock in hand again.

"So yes big boy, you are going to fuck this slut tonight." I responded in a sexy whisper.

"Ride my cock. Facing me so I can watch you take my big cock." he ordered.

"Sure thing stud. Your the boss tonight." I couldn't help it.

If I was honest and said anything, even just 'No' in my normal voice he probably would recognize me. I chose to keep my voice soft so he wouldn't recognize it. He probably won't see my face well enough in this light. Even so my makeup and glasses would throw off any last chance of recognition. I still felt trapped somehow so I went with it and took the risk.

And somehow it felt right being the good slut. He was right this time. I am a slut.

I kept my face turned away while I moved to straddle Nick. I pulled my skirt up over my hips. He had already lifted the arms of the seats back out of the way. I felt his legs slide along my thighs as I lowered onto his lap. My stockings rubbed his legs. I heard a quiet sigh over the film playing when the head of his cock touched my ass. I kept my head next to his with my mouth close to his ear. It would keep him from getting a good look at me and I could whisper anything I needed him to hear.

I used one hand to balance myself while my other directed his cock to my entrance. I nibbled on his earlobe as I slid down his cock.

"Fuck, your cock is testing me. It feels so thick." I said. Little more than the head was in.

"Are you going to be able to take it all slut?" he asked. I bit his ear again.

"Fuck, yeah I can take it all. What's your name big boy? Just in case I need to scream it out." I worked his cock in a bit more. It was stretching me good. If I accidentally moaned or screamed his name I had to be sure there was a reason I knew it.

"Nick."

"Nick, I think I have you in the rest of the way." I was sitting on his lap with his cock impaled in my ass.

"Fuck your cock's big stud." I started to ride him. The pain was constant but I could tolerate it. I knew it would change to pleasure in a moment. "You like that?"

"Yeah, that's good." he said. "You're tight." Fuck, I was only tight because his cock was so thick. His cock was feeling good already. I was sitting so it would press on my prostate.

As I rode him my caged cock bumped his stomach. He teased me about it, lifting it up and trying to twist it.

"Fuck, Nick, your cock feels so good. Oh. I..." I said trailing off before moaning repeatedly in his ear. My breath was heavier as I started riding his cock faster. My ass had accommodated him completely and it was feeling even better. I gradually increased my pace as he started grinding back in time.

"Fuck, yes Nick fuck me good. Ohh fuuck Nick." I moaned. I could tell this would eventually make me cum. I'd cum only if he could hold off himself for long enough.

"Yeah, ride my cock you slut. Take it deep in your ass slut." he said. I slammed harder on his cock. He was getting me close to the trigger.

"Yeah Nick, I'm your dirty slut. Fuck me good. Fuck me hard. Fuck your dirty cocksucking slut like a real man with that thick fucking cock." Fuck I was on the edge. I was riding him furiously. His cock was about to be sending me over the edge.

"Yeah slut, you have me close. You're going to make me nut."

That did it. It made me start cumming the next time I dropped on his thick cock. My legs were shaking and unsteady but I pressed on.

"Oh, Nick your cock feels so good. Nut in me Nick. Nut in me please." I begged. "I need your cum blasted deep in me."

My cum started running out of my cock. It didn't shoot or squirt but ran down my balls to my ass.

"Look at me slut." he said.

I was hardly comprehending him. I was in ecstasy as I sat again on his cock. My cum continued draining from my cock and through the cage. It ran down to my asshole and was adding to the slippery feeling each time I landed.

"Look at me slut. I want to see your face when I nut bareback in your ass." he said.

What he had said had registered this time. So fuck it. The lighting sucks. I'm back lit by the movie playing behind me. I'm wearing heavy makeup and glasses. He won't recognize my face, my eyes. I complied. I looked at him, directly into his eyes.

I whispered "Fuck me with that huge cock big boy".

His fingers dug in trying to hold me still. I dropped down on his cock one last time squeezing as much as I could. I felt him grinding his hips against me as he shot his cum deep in me.

"Oh yes, do it Nick. Shoot that load right in me. I need your cum. Fuck that's so good." I lifted up and sat on him again. His cock throbbed depositing more of his cum in me.

"Fuck Nick that's a lot of cum." I said just before he pulled me to his face. Before I knew what was happening let alone could react he had his lips on mine and his tongue was fighting to part my lips. Fuck, I was kissing him now.

I let his tongue in teasing it with mine. We wrestled tongues for the space in my mouth. Nick won and pressed even harder on my lips. His arms now wrapped around my waist holding me tight to his body, keeping his cock deep in me.

I relaxed on him, kissing his neck as my body went limp. He started to move so I felt he was ready to go. I panicked not having an exit plan. I lifted off him and moved to a seat away from the aisle.

He picked up his pants from the seat and put them on. Before leaving he turned to me and leaned down close to my face.

"Be here next Friday at the same time if you want to fuck again."

"Sure thing Nick, already looking forward to it."

With that he left. Tracey came back to me.

"That was hot Brie. I watched the whole thing. You looked so good. How was it?"

"It was hot for me too. That was my boss, Nick. He didn't know it was me."

"Oh fuck, that asshole? Did he know it was you?"

"No." I responded.

"Fuck, that's crazy. He came in you, too. And you kissed him. Sorry, how did you even handle that?" Tracey asked.

"I don't know. It just happened."

"What's going to happen Monday? Will you tell him?"

"I don't think I should. I mean, he might get upset since I knew before he fucked me. I think I'll have to keep it a secret. Everyone knows he's gay but I haven't come out there. No one knows I dress. I have more to lose.

"And he wants me here next Friday for him to fuck again." I added. "And I want to. I want his cock again. It's amazing."

"Ok, if you're sure." Tracey said.

"I think I am. Will you come with me then?"

"Fuck Brie, that was so hot I wouldn't miss an encore for the world. We are going back to the bar so you can tell me what you were going through. I had no idea."

I pulled my skirt back down and we headed out to get a few drinks at the bar. It was the same bar as before, friendly to our persuasion so we weren't too worried about being out.

The following week was thrilling. I was very nervous Monday but I should have known better. Nick was clueless about it being me that he fucked and kissed Friday.