Night in a Hotel with My Boss

This is a story about how a week away for a project led me to hook up with an mature woman who was also my boss. This story is a little long to build up the how we ended up hooking up in a hotel.

I couldn't have picked a better time to escape the winter storms of Philadelphia and spend a week in Florida. My company paying for the trip was just the cherry on the top. It was a warm Saturday morning in Orlando and I was looking forward to spend a nice weekend in the city before heading to our Orlando office for the week long project I was there for.

"Hey Om?" I heard a questioning call for my name as I was waiting at the carousel for my luggage.

I turned back to see Sonia.

"Oh hey Sonia, I see you decided to get in early as well," I said.

"Yeah, I needed to get out before the storm hits. Also, need to get some work done before the project begins on Monday," She replied.

"Not planning to get any sun?"

"No not really. I don't suppose I will get much time to do anything else," she said with an urgency on her face that was quite common, "Hey listen, I am glad you are here early as well. I am assuming you are staying at the Hilton near the airport as well?"

"No actually I am staying at the one near the downtown. I thought," I said before I got interrupted.

"Yeah yeah no issues. It's not too far. Let's plan to meet in a few hours. I have some documents I need to review and I could use your help to get it done. I think I see my baggage coming too, I will give you call later. See you in a bit!" she said and hurried to her bag before I could say a word.

I picked up my luggage and took an uber to the hotel.

I was furious. Not only did she never apologized for what she did previous week, she expects me to work with her on the weekend instead of enjoying the beautiful city. Sonia was a Director at the company and was the Program Manager for the project I was travelling to Orlando for. She had recently joined the company and held a very important portfolio of projects that I wanted to be part of. For all my efforts to impress her, she almost every time ignored me and my work like everything I did was just regulation work. Not to mention the reaming she gave me during a team meeting previous week for missing my deadline once by a single day.

She was an Indian, like me. She seemed like she was in her early 40s. Short, about 5'2", and a slim figure. She had straight short hair to a shoulder length. Her hair were straight and always perfect whenever she was seen by anyone. Not sure if it was the discontent towards me or if her eyes just had the cold dismissive look.

I got to the hotel, checked myself in and immediately took a shower to wash off the flight lethargy off me. As I was in shower, I heard my phone ring twice, I got out to see it was Sonia who had called. I saw her text, "Hey, Good Morning. Please meet me at my hotel after lunch around 1 pm."

I was irritated but I knew this was a major project for the company and I would learn a lot from this but project. Sonia was brought in the company for her expertise is Patent Technology. She had an extensive an reputed network and I definitely wanted to get on her good side. Everyone wanted to but at the same time very few could manage to get past her attitude. She wasn't the most easy person to work with.

I replied back with a simple "Okay." I got dressed, got some lunch and then headed to the hotel.

Then I started thinking, she asked me to come to her hotel, could that mean something more? My thoughts broke as I heard the concierge's word, "Ms. Verma said she will see you in conference room 2B. Once you get out at the elevator on the 2nd floor you will find it two doors down to your left." I thanked her and moved on.

Wow, conference room, she really is the ice queen. I met her in the conference room. She was dressed as usual in her business attire. She was wearing dark blue jacket and skirt with a pink shirt inside. Her stilettos made her looked taller which probably put her on the cloud from where she was judging me wearing my casual clothes. I was wearing light blue shirt and white trousers hoping to get out in the city.

"Okay, let's get started. I have reserved this conference room for all day, so we won't be disturbed.

"All day?" I thought as I nodded and got on with the work.

We spent the next 6 hours working in the conference room. I was hoping to get some time to unwind I thought, but this was turning out worse than regular work I thought.

At around 7 pm she asked me, "Hey I am sorry to keep you here all day, but we are almost there. Maybe 3 hours more at the worst, would you prefer us cranking it out tonight or want to get back at it tomorrow?"

"Oh, so you are familiar with the words, I am sorry," I said.

"What?" she replied in surprise.

"I apologize I didn't mean to. I was just a little exhausted and it slipped out of my tongue. I am okay with either," I replied in an apologetic tone

"You do realize the importance of the project, don't you?" she said in a sharp tone which triggered an unexpected reaction from me.

"Yes, I know. And we have reviewed these documents twice now front and back. Last week you insulted me in front of the entire team and now you are asking me to get stuck here all day when I had plans to tour the city." I blasted off.

"Listen Om," she was about to say as I interrupted,

"No, you listen Sonia. You didn't even ask if I was okay with this. I had plans today to see the city today. I admire you a lot, but we are not working now any more this weekend."

"Okay I get it; you can go ahead. I will review these one last time," she said in a somewhat apologetic tone.

"Hmmm. Thank you," I said meekly and started wrapping up my stuff.

"What are your plans?" I asked.

"I am just going to wrap up and maybe get some wine. Why do you ask?" Sonia replied.

"You want to get dinner and a drink?" I asked very nervously.

"Uhmmmm." She said as she took a few seconds to reply. "Okay. Let me change into something comfortable and we can go," she said and went to her room.

She headed to her room and I to the lobby waiting for her. In about half an hour I saw her shop up in the lobby.

She was wearing a black sleeveless top and a matching colored skirt which just about revealed her smooth thighs. For the first time I was able to look at her and admire how smoking her body was. Her boobs were medium sized but upright and perky, something I thought was uncommon for a woman her early forties. She had her hair down which just about reached shoulders.

"So where do you want to go?" Sonia asked.

"How about, we head downtown and figure out then?"

"Yeah, that works as well. Just as long as we get back by" she was about to say as I interrupted her and said, "You look good."

"Thank you, you as well" she said nervously and let out the smallest of smiles.

That was a woman who has not been complimented for a while, I thought. We went to an Italian restaurant in the downtown. We order some appetizers and drinks. The place wasn't too loud, but the awkward silence sure made me wish there was loud deafening music playing.

She broke the silence finally, "Hey listen I am sorry about last week. I know it was the first time you missed a deadline I should have gone easier on you, and definitely not in front of others. And also, for today."

"That is fine, I appreciate you saying that" I replied.

"Thanks! And maybe I haven't said this before, but I really appreciate all the work you are doing on this. I am not good when it comes to complimenting people, but I am glad you are part of this project team. It's just that," she stopped for a second to take another sip of her wine, "I have been so involved with work that I forget people do things outside work as well."

I sensed that the alcohol was starting to open her up, "You don't mean to say that you are either working or thinking of work all day?"

"When I am not with the lawyer, that is pretty much what I do?" she replied.

"Lawyer?" I asked inquisitively.

"Yeah I am in middle of a messy divorce. Well, almost at the end of the line now," Sonia said with visible sadness on her face.

"I am sorry to hear that," I said.

"No that's fine. At least it is about to get over and I can put that behind me," she said while ordering another glass of wine.

"Should we get a bottle?" I asked with a kidding smile on my face.

She laughed and said, "yeah that would have made sense about 4 glasses back, wouldn't it? I don't know about a bottle, I think I will be done after this one last glass, it is quite late."

I reached out my hand to her with a gentle touch and said "It is just 10 pm relax. Tomorrow is a Sunday."

She noticed me touching her hand and looked at me but didn't move her hand. I held her hand just a little bit more gently and said, "There's more to this city than this restaurant, after this one drink let's look for some other place?" I spoke.

She pulled her hand back with the excuse of straightening her hand and said, "yeah you are right. Let's see what we could do. But I still need to do the final review of the documents tomorrow so I can't afford to get too drunk."

"Here's a deal, you relax tonight and don't talk about work and I will spend as long as it takes tomorrow to review the documents? We have a deal?" I spoke.

"You win," she replied, "so tell me about you. Do you have a girlfriend?"

I was surprised her asking this. Never thought I would have been having such a conversation with the ice queen herself. I chuckled and said, "Not right now. Not for a while actually. I have been single for a couple of years now."

"Two years? That's a long time for a guy like you to go without sex"

I almost spat my coke and rum hear her say "sex". I took a breath back and said, "I don't have a girlfriend but I see other girls. There are a couple of girls I have been, you know, going out for a few weeks now."

"Oh, I am so sorry to assume that. I am just, so out of touch with the rest of the world I didn't think, ummm, nevermind," she stopped in her tracks trying to sip her wine that already had reached the glass's bottom.

"Let me take care of that for you," I said as I requested the waiter to get another glass, "what were you saying?" I insisted her on continuing.

"No nothing," she said as she grasped the other glass and took another sip.

We were both tipsy. Each of us had about 5 drinks now.

"Sonia, you can say what were you saying," I said look straight into her hazel eyes.

"Well," she said as she sipped her wine, "My ex-husband is the only guy I have been with. And for second I forgot that people other than myself in this world do have sex without being married or even being in a relationship," she stopped looking at my shell-shocked expression, "I am sorry I didn't mean to appear judgmental. It's just I have not had a conversation like this for a while and I didn't know what I was saying."

"No, it's okay. You can talk," I insisted.

"No, it's not exactly okay," she said with a firm voice that indicated me she was about to let the dam break. She started telling me the story about her marriage. How she married her high school sweetheart. They went to same colleges and attended same universities. Got job in similar fields but in competing companies. How they thought that would be better cause now they won't be talking about work to each other cause of the existing legal restrictions, but all it did was they ended up not talking at all. At all times either they were working or getting back home tired. That they never took any vacations in the 8 years they were married. How the sex started to dwindle down within the 3 years of the marriage.

She continued, "It was good in the beginning. But after about 3 years of our marriage, it started to get monotonous. And the worst part was it most likely my fault. I was so consumed with work that I thought of sex and just an activity to do so you can get to sleep before the early morning meeting. It was the same thing, we would get in the bed, kiss a little then undress and then he would get on top for a few minutes, and we would be done. And after a few years even that stopped."

I realized this was a woman who wanted to talk and have someone listen to her. So, I did. But even listening to boring sex life was starting to excite me.

"I am sorry, I just dumped all that on you. You probably are thinking what I am doing sitting here with a boring old woman instead of hooking up with a girl her," she said with an embarrassment.

"Listen, I am glad you opened up about it. And you are by no means an old woman. You are as beautiful a woman as I would have expected to sit across on a Saturday night in a new city," I said.

"Really?" she said back with a surprised tone.

"Yes, I promise. And I don't mind if you want to talk about it anytime. But right now, we are getting out of here. I am sure even you can hear the loud club next door. Let's go check it out," I said as I foot the bill and returned it to the waiter.

"I have not been dancing for a long time. I don't even remember how to,"

I got up and grabbed her hand, "It's simple, you put your hand where you like them to be and move the rest of the body to the music," and guided her out of the door as I finished my sentence.

We got in the club next door. It was dark, loud and crowded like any of the other million clubs in this country. I went to the bar and got us 4 shots of tequila. Sonia initially seemed a little nervous, but the tequila seemed to relax her nerves. We got on the floor and started dancing.

I was swaying to the music and she seemed to still be a little nervous trying to remember what her moves were. She was looking at others feeling out of place. I took her by her hand and pulled her a little closer to me. I could sense her perfume now. My hands were on her waist and her on my shoulder as we started getting in the rhythm of the music. I grabbed her waist a little bit firmer now and pulled her a little closer. She didn't seem to mind. She was much more immersed in the music now as she closed her eyes and put her hands in my hair.

I turned her around to have her back face me. I was about 4 inches taller than her. I could smell her hair and I am sure she could my cologne. She continued to caress my hair as her body was moving to the same rhythm as mine. I was breathing close her ear and seemed to enjoy it. There was a bulk starting to form in my pants as her tight butt was rubbing against my crotch. My hands were still on her wait but starting to raise her top just a little to feel her smooth skin on the stomach underneath the top. I pulled her further towards me thrusting my bulge against her. She may have noticed that. She reached out one hand below trying very meekly to create some separation, but I didn't budge. I moved one hand from her waist upwards. My hand moved over her sumptuous breasts to her cheek. I turned her face sidewards through her weak resistance. My lips moved past her heavy breath and met hers. She hesitated a little. Almost like wanting a slight separation. My left hand which was initially just on her cheek moved ahead where now I was holding her firmly with my forearm. She melted in the moment and started kissing me back passionately. I moved my other hand to her breast and started caressing them syncing with the rhythm of our bodies moving. Her hand which was trying to push my waist behind was now instead grabbing my bulging cock.

I broke the kiss and whispered in her ears, "I told you dancing was simple. You put your hand where you want it to be," and then turned her around again facing me.

We continued kissing grabbing each other's butts and we tried to still move to the music.

"How far is your hotel?" she said trying to catch her breathe.

"It's right across the street" I replied with a grin.

She didn't say a word, grabbed my hand and guided me out of the night club.

We hurried past the lobby and in the elevator. Before the door shut an old man also got in the elevator. We were feeling the tension between us that was stopped from breaking but the presence of the other man. As soon as he got off and the door shut, she leaped at me and started kissing me wildly. I wanted to fuck her right there and then in elevator, but I head the bell ding and we reached my floor. We got out a rushed in the room. As soon as we got it, she again pinned me back to wall and started kissing me as I barely was able to push the door shut.

She was unbuckling my belt clumsily while kissing my unbuttoned, partially exposed chest. I helped her unbuckle my pants and she pulled my trousers and pants down with one swift push. She wasted no time to get on her knees put my erect cock in her mouth. She held the base of my cock tightly with her tiny hands and wasted no time sucking on my cock. I could feel my cock growing in her mouth until she was struggling to take all of it in. She started stroking my cock as she licked my balls. Her sloppy blowjob and slurping sounds off my cock were raising all the hair on my body. She moved her hands to hold my butt as she started to pleasure my dick with nothing but her soft lips. I pushed her head all the way in, or at least as much as I could until I felt I was going to choke her to pass out.

The thought of pushing my dick down the throat of one most powerful woman in my company while she was on her knees in my hotel room was getting me harder than I ever had been. I could hear her gag as I continued to mouth fuck her. I released her. She coughed a little as she was gasping for air. The tears running down her eyes had spoiled her mascara making her look like the most expensive whore I could never afford.

She got up and slapped me hard. I thought I had gone too far and spoilt what would have been one amazing night. She slapped me again, put her left hand on my face like she was going to claw it off. She squeezed my dick hard with the other hand, came close to my face and said,

"Who the fuck you think you are?"

I was stunned and speechless.

"I asked," she said with a pause as she bit me on my chest, "Who the fuck you think you are to push your big cock down my throat? And who do you think I am?"

I grabbed hold of her hair and pulled it back to expose her sleek neck to me. I swiftly turned her around and pinned her against the wall. I put my hand on her throat squeezing just a little as I moved my face close to her looking straight into her eyes.

"You are my queen."

I moved my hand down over her wet panties.

"You are my dirty little slut."

I whispered into her ear as I slide her panty to the side exposing her wet pussy to my exploring fingers.

"You are everything I ever wanted."

I slowly pushed my finger up her wet pussy.

"And I am the guy who is going to fuck you like you deserve to," I said as I bent down on her like the queen she was. I lifted her leg up to expose her pussy to be and started kissing her pussy. I could taste the juices of her pussy.

"Fucckkkkk" she said as she started to moan.

I continued licking her pussy as I slowly increased the pressure and speed of my tongue. I was circling on the top of her pussy as a I nibbled on her clit. I pulled her panties down swiftly as I started eating her pussy aggressively.

Her moans kept increasing as she wrapped her leg around my shoulder and pushed grabbed my hair.

"That's so good Om. Fuck you are amazing. Fuck I am going to cum. Fucckkk."

I continued licking her pussy pushing her towards an orgasm.

I felt her body shrivel as she grabbed my hand and left out a loud moan, "fucckkkkk Om...aaaah...that was so good. You're tongue is unbelievable."

"Just until you see the rest of me babe."

I picked her up and she wrapped her legs around me. I carried her to bed kissing each other passionately. I softly dropped her on the bed as we our tongues continued to tangle with each other's. We continued kissing as I moved my hand all over her body. I couldn't get enough of her amazing curves. I started massaging her boobs as I unbuttoned her skirt. I got up and gently pulled her skirt down kissing her soft inners of her thighs.