A Little Fun Outside Of Work

"Wow, this week has dragged on," I said to my coworker as we walked out the door to the parking lot.

"It certainly has, Amanda. Anything going on this weekend to help you forget about it?" Brian asked me, much like he did every Friday afternoon.

"I'm not sure what's going on just yet. I might go out for a few drinks with some friends later tonight. That should help me relax," I responded with a smile, before adding, "Got any hot dates tonight Brian?"

"You know I'm not one for Friday night dates, Amanda. I've got a few buddies that want to go pick up chicks, but that's not my scene, so I might just hang at my place tonight. Where are you headed, maybe I'll send my friends down after you," he chuckled.

"Funny you should ask, Brian. We're going to that new lounge that opened over on Weston Street. If you decide to go out you should stop by and say hello," I said, as casually as I could.

Brian simply nodded before giving me a quick hug goodbye and heading to his car. I waved after him as he looked over his shoulder, then got into my car and drove home. The traffic was terrible, so after an hour behind the wheel, I was more than ready to go relax and get ready for a much needed night out. I walked through the door only to catch the end of a voicemail on my answering machine. It was Lily, letting me know she wouldn't be able to go out because her daughter was sick and the sitter wasn't quite competent enough to handle a spoonful of cold medicine before tucking Julie in to bed. I sighed loudly before picking up my cell phone. I knew this was unlike me, but I just could not stay in after the week I had. I dialed a number and made the arrangements to meet at the lounge shortly after 10.

After returning a call to Lily, I made myself a light dinner and headed to the shower. My mind raced as I tried to decide what to wear out tonight. I was much more nervous than usual, but I couldn't figure out why. Brian and I had worked together for years. This wouldn't be the first time we hung out outside of work either, yet there was a ball in the pit of my stomach. I knew Brian found me attractive, we had always had a flirtatious relationship once he ended his engagement, but nothing had ever come of it. I had thought about coming on to him in the past, but never could find the confidence, so I was more than happy with our flirtatious and friendly relationship. I shrugged off these thoughts and continued to get ready. I found myself planning my outfit again, deciding that I would wear a sexy navy blue dress that showed the perfect amount of cleavage. With that dilemma out of the way, I showered mindlessly.

Within an hour of getting out of the shower I was ready to head out. My dark hair was mostly straight, with a loose curl at the bottom, falling just past my shoulder. My make up was simple, just a light eye shadow, some eye liner and a subtle pink lip gloss. I decided on small black heels to show off my legs. I grabbed my small black handbag and headed for the door. As I opened the door, I imagine my face showed quite a bit of confusion. At the door, muttering to himself, was Brian. He looked at me with a shy smile before backing up and letting me step outside.

"Is something wrong, Brian?" I asked, truly concerned.

"Oh no, Amanda, there's no problem. I just stopped by to see if you'd like to drive with me. I know I told you a few of my buddies wanted to go out, but they bailed at the last minute, so looks like it's just you and me. If that makes you uncomfortable then we can cancel, but I know how much you were looking forward to a fun night out. When you called me the plan was still to go out with Tom and Justin, but apparently they decided to relive their high school days and head to a house party. Please don't be upset that I didn't call or anything, I just thought that if you didn't have to worry about driving, you might enjoy yourself more," Brian babbled, his face blushing a slight pink color.

"Don't worry Brian. Your offer was very nice, and I will gladly accompany you. I'm sorry that your friends ditched you, but I guess it makes me feel a little better," I said with a laugh. "Do you still want to check out Weston Street?"

"I've only heard good things," he responded with a grin. I locked the door and we walked to his car. He looked like he was contemplating something as we approached the car, but as I smiled and reached for the handle, his look changed and he walked to the driver's side and got in. I hadn't noticed his appearance until we were in the car under the light. His brown hair fell naturally over his forehead. His green dress shirt drew extra attention to his already bright green eyes and his smile was crooked. He wore a pair of dark jeans and black dress shoes, and carried a black jacket, which he gently tossed into the backseat. He looked over at me, smiling, as he started the car. We made small talk while we drove, discussing his sister's marriage as well as my lack of control when shopping.

The drive seemed very quick as we pulled into a parking lot on Weston Street. Again I opened my door, while Brian waited to take my hand and help me out. I looked into his eyes and felt my face flush red, whispering a quick thank you to him before walking towards the entrance. Once inside, we found a small table in a quiet area, away from the bar. The two person booth was cozy, and we sat a foot from each other. After ordering out drinks, we began another simple conversation. The waitress returned with our drinks and after taking in Brian's looks, she nodded at me and walked away. I found myself smiling, when my thoughts were interrupted.

"What's got you in such a good mood?" he asked me, clearly catching me with a smile on my face.

"Nothing, I'm just glad to be out of my house tonight," I said quickly. My eyes on Brian as I crossed my legs, letting my foot rest against his shin. He smiled at me with a nod, accepting my vague answer. We quickly fell into another conversation. There was no trouble holding a conversation with Brian, and his quick wit made any conversation fun. As the waitress fed us more drinks, myself especially, I became more blatant in my flirting. While not drunk, I was allowing myself to break out of my usually reserved shell. I found myself touching Brian's arm from time to time, and letting my foot graze his leg every time I moved it. I even found myself sliding closer to him, allowing my shoulder to press against his arm. Brian didn't take long to wrap his arm around my shoulder, and I rested my hand on his thigh. We continued making idle conversation, but I couldn't take much more. I excused myself and went to the bathroom.

On my way back from the bathroom I noticed our waitress. I approached her quickly, asking her to bring us one more round of drinks, but told her that she could bring the check then because we wouldn't have any more after that. She smiled a knowing smile and walked off. I returned to the table and took my place cuddling up with Brian once more. His arm returned to my shoulder, stroking my skin softly as the waitress returned. She left the drinks and the check and winked at me before wandering off. Brian looked at me with a confused look. Before responding, I slid my hand up his thigh, letting my nails draw circles on his inner thigh. The confusion was still evident in Brian's face, so I leaned in close to him.

"I hope you don't mind but I told the waitress we wouldn't need her services anymore," I whispered into his ear, letting my warm breath tickle his skin.

"Are you ready to go then, Amanda?" He asked. I simply shook my head and lifted my hand to his cheek, pulling his face closer to mine and kissing his lips softly. He kissed me back and I parted my lips for him. His tongue entered my mouth as I began to moan softly. My hand was still on his thigh, so I slowly slid my hand up over the growing bulge in his jeans. I could tell he was moaning as his hand slid down my back, gently squeezing my ass. I broke the kiss at the same time I squeezed his cock teasingly, holding my grip while we spoke. He looked at me, confused by my forwardness.

"Amanda, are you sure we should do this?"

"I want you, Brian. Don't you want me?" I asked back.

"Of course I do. But we're not alone, people can see us," he pointed out, as if I hadn't noticed.

"So then do you want me to stop?" I asked very teasingly, while stroking him through his pants.

"No. Please don't stop," he managed to say before kissing me again.

We kissed deeply as my hand slide up to the button of his jeans. I carefully and slowly unbuttoned his pants then slid the zipper down, letting my hand slip inside his boxers and continue stroking his cock. His moan grew louder as we kissed. He squeezed my ass again then slid his hand down, under my skirt, finding my panties already wet. His fingers slide along my slit outside of my panties. I moaned into his mouth as we kissed, then felt my hips grinding slightly against his fingers. My fist wrapped around his cock tighter as I began to stroke him faster. I pulled my lips away from his and pressed them to his neck, sucking and kissing his neck. Slowly his fingers slipped inside my panties, making me bite down suddenly on his neck. My hips began rocking back and forth, matching the rhythm of my hand stroking his cock.

"Oh god, Amanda," he half moaned, half grunted, as his fingers slid in and out of my wet pussy. I continued sucking along his neck, eagerly leaving my mark on his skin. I could feel him starting to tense up, and when I pulled my lips from his neck, I noticed a small amount of sweat forming on his forehead. His breathing was labored and I knew he needed to cum. I brought my lips to his ear, nibbling his ear lobe gently.

"Do you want me to make you cum now, baby?" I whispered in a raspy voice.

He couldn't speak, he just nodded. I grinned to myself and continued stroking his cock while rocking back and forth against his hand. I knew I would cum soon, and I wanted to make sure Brian did as well, so I moved my hand faster on his cock and returned my lips to his. We kissed passionately, devouring each other, while stroking the other intimately. I felt my pussy tighten around his fingers as my orgasm approached. I closed my eyes tightly, but continued stroking his cock. As the realization hit him that I was cumming, Brian let out a loud groan into my mouth. I stroked his cock several more times before feeling his balls tighten. I stopped rocking my hips once my orgasm subsided, but I continued stroking Brian's cock. Within seconds, he was cumming all over my hand and his clothes. I pulled away from the kiss and moved my hand to my lips, tasting his cum on my fingers as I sucked them into my mouth. I grinned at Brian, who then did the same with his fingers. After cleaning off our fingers, I kissed him again while buttoning his pants back up. Without a word, Brian paid the bill and we stood up. After fixing my dress, we walked to his car hand in hand, kissing once more before driving back to my place.