My Boss and I in Vegas

We had done it. Lori, my boss, and I made it through our first convention together. We normally do travel together one week each month, but that's for corporate meetings to discuss goals and how we're performing for the year. It was at one of these meetings earlier this year we found out we were selected to be the reps from our division to attend the conference in Las Vegas. Now as we worked on closing things up, we both finally started to let down a bit.

I looked over at her, as I put a packet of pamphlets in a box. I noticed she really did look good for her age. She was 53, but could easily pass for 5 years younger. In the heels she was wearing now, she was almost as tall as me at 6 foot, but normally was 5'6". She had a great fuller figure which I've always been attracted to. I had managed to keep that attraction hidden in the years we had worked together. She looked especially good this week in the dresses and skirts and blouses she wore for the convention. One of the dresses even showed off a little cleavage, which was always fun to see, as my eyes did tend to wander at times to her full breasts, probably 40D or so. My eyes would always make it back up to her green eyes and dark red shoulder length hair, yes, she did look good. But we were both married and she was my boss so she was off limits.

I'm 38 and as I said, 6' tall. Over the years I've added a little more as eating out on the road can do. I'm a little over 200 pounds but, I like to think, I carry it well. I have short light brown hair and hazel eyes. Normally it's business casual around the office, but this week it was all shirts and ties. I thought I noticed Lori looking a few times, but I just did my best to ignore it and concentrate on why we were there.

As we finished closing up we started talking about our dinner plans. It was Las Vegas and we had been to some nice places all week but it had been a long week. I asked her if she had any other ideas on places she wanted to go and she just answered, "James, it's been a long week, I'm actually really tired. I think I'm just going to head up to the room when we are done here and get room service. If I'm up to it, I may rent a movie. You go out and have fun, enjoy your last night in Vegas."

"That sounds wonderful, I think I may just do the same thing. We've been talking to people all week, a quiet night sounds perfect." I said as I thought about the week.

"Well, you are welcome to join me if you'd like, but it will be an early night for me." Lori said invitingly.

"I think I will take you up on it." I said smiling back at her and turned back to clearing the pamphlets from the table.

Once everything was put away the two of us walked toward the exit and then to the elevators to our rooms. As we approached the elevators I noticed Lori was moving a bit slower than she had the rest of the week. So I asked if everything was ok.

"Yes, it's just been a long week in these heels and my feet are killing me. I'm so ready to get them off and sit back and sip a bottle of wine." Lori stated as the elevator doors opened.

We stepped in and I looked down at her feet, then up her legs and finally up to her eyes where I thought I saw them looking down my body. "That will feel good tonight" I said "to, just let the week go. Plus our flight leaves later tomorrow so we can finally sleep in for once."

The elevator doors opened on my floor and I let Lori know I'd be up in a bit after I freshened up and changed out of my dress clothes.

When I got back to my room, I changed into a pair of jeans and a t-shirt and just sat back for a bit and took in the week. It had been a long week, but a very good week. Being with just Lori all week had seemed to bring us closer. We had been talking more now than we had in the last three years of us working together. I was really looking forward to spending some time with just the two of us tonight and nobody else around. I got up from my chair and headed out and went up to Lori's room.

As I approached her door, I started to feel a little nervous and a little excited. I wasn't sure why, we had gone out to dinner many times when we traveled and had even done room service a few times before. For some reason though, tonight just felt different. I knocked on her door and smiled when she answered. She had changed into a long t-shirt and pj pants. My eyes, did a quick glance down and I could see her nipples just barley trying to poke through the shirt. I looked back up as she invited me in.

We walked into her room, which was definitely bigger than mine. Nice to be the boss I thought. I looked over at the table with a couple chairs and saw the room service menu was open. She pointed to it and said I could take a look, she had decided what she wanted while she waited for me. I looked through and made my decision, then I asked her if she still wanted that bottle of wine. She just smiled and said, "Yes, I've been looking forward to that all day." So I picked one out and called in our order.

While we waited for the food to arrive Lori went and sat on the bed and I sat in one of the chairs by the table. We browsed through the list and found something both of us could agree on, but neither of us seemed too excited to watch. Then I turned to her and started talking to her about the week and asked her how she thought it went.

Lori smiled and said "I think it went really well. I know I got some very strong leads and was able to talk to a few of our existing customers. When we get back to the office I'll be setting up some training sessions with a couple of them. I think they'll be very happy at the corporate office and will probably send us back again, possibly as soon as next year. We really make a good team James. But that's enough about work. The week is done."

I asked her if she had any plans for the weekend once we got back. She laughed and said, "After leaving David" her husband "alone all week I'll probably be cleaning the house and doing laundry the whole weekend. Sounds exciting doesn't it. So I guess tonight is the night I have to get my fun in for the weekend!" She laughed as she said it.

We would pause momentarily at times to see what was going on in the movie, though clearly neither of us were too interested in it so we continued to talk. Then the knock at the door as our food arrived. Lori got up to open the door and I saw her ass sway back and forth in her pj pants. I just smiled and tried to get those thoughts of my married boss out of my head. I stopped the movie as she opened the door and pointed to the table as the waiter wheeled the food in. He set everything up and then put a little electric candle in the middle of the table, then poured wine in each of our glasses. We both smiled and laughed a little at the thought that he was trying to make it seem romantic. Lori signed the slip and he left.

Once she came back to the table and sat down we started to eat our meals and talk and laugh. We sipped our wine and both started to relax more. As I finished my meal I asked her if everything was ok, I noticed it looked like she might have been limping a bit. She just laughed and said, "Yes, I'm fine it's just standing in those damn things all week." Pointing to her heels.

I smiled and said, "Well you looked great in them and if you'd like I can give you a foot rub and see if that helps at all."

"Oh that would feel so good, but you really don't have to. I'll be ok after a couple days in decent shoes".

"Really, it's fine Lori." I replied as I slid my chair from the table and positioned it in front of her. I patted between my legs for her to put a foot up as I looked into those gorgeous green eyes.

She set her foot between my legs and it brushed ever so slightly against the crotch of my jeans. A little tingle of electricity jolted through me and then I reached down and started to slip her sock off. She had clearly just had a pedicure before we left and her toenails were all painted. I slipped one hand up her calf and pushed her pj pants up slightly, then started to use my thumbs and rub under her foot. I looked up and saw her lean back and take a sip of wine as her eyes closed. I heard a soft moan and she said, "Ooooh that really does feel good, I guess I did need that."

I worked her foot and lower calf for a while until she seemed much more relaxed. I then whispered and asked if that foot felt better.

"Mmmmm much" she said in a soft, low voice.

"Great, now time for the other one" I said quietly.

She set her foot down and lifted the other. I helped her set it between my legs and worked her sock off and then started to work it. She sat there sipping her wine, looking totally relaxed as my fingers rubbed and pressed into her foot.

I let one hand slide a little further up her calf and she didn't try and stop me at all. She actually slid down in her chair, pushing her foot forward and now it was resting against my jeans. I looked down and was glad her eyes were closed because the bulge was growing in them.

My hands left her foot and leg and I looked up at her as her eyes opened and she told me, "That felt great James, thank you so much."

I just smiled and said, "If you'd like I could give you a shoulder rub too."

"That would be amazing, if you're sure you're ok with it I'm not going to turn that down." Lori said

I got up and walked over to the bed and sat against the headboard. "Come over here." I said as my legs spread for a place for her to sit.

As Lori sat, I could still smell a hint of her perfume and I leaned in a little closer. Then my hands started to work her shoulders. Lori just leaned back into me and moaned how good that felt. I felt so close to her, and wanted to make her happy. Now not caring that she was my boss, just a close friend that was relaxed and feeling good because of me. I started to work my hands down her back, my thumbs pressing small circles into her shoulders. While I did this, I leaned in and gently pressed my lips to her neck and kissed softly. Lori's reaction was just a long low moan and she leaned back into me, pressing my hands between us. I stopped rubbing her back and held still and just let my lips plant small kisses over her neck. Lori just leaned back and moaned with each kiss. Her hands resting on my thighs as she tried to slide back against me, rubbing against the bulge in my jeans. She leaned forward, freeing my hands from between us and I wrapped my arms around her body, holding her. As I kissed her neck, my hands worked up over her shirt and cupped her breasts. I could feel her nipples really pressing against her shirt now and I circled around them slowly causing Lori to buck softly and cry out, "Yesssss."

Lori rose up and started to turn. She reached down and pressed my legs together and she straddled them as she knelt in front of me. She reached up and cupped my face as she leaned in and pressed her lips to mine. My hands rubbing up and down her back, pulling her in close, I kissed back. Our tongues gliding over each other's in a long passionate kiss.

Our kiss broke and she looked into my eyes as she reached down and pulled her shirt up and off her. I finally got to see those big, gorgeous breasts. My hands instantly went for them and I cupped and held them as I breathlessly mouthed the word "wow." I then reached back and slipped my own shirt off before returning my hands to her breasts. I cupped them and held them as I leaned down and took one of her nipples in my mouth. I heard her whisper, "Yes James, that's it."

Her fingers running through my hair, to the back of my head as she pulled me into her breast. I opened my mouth wide and took in as much as I could. As I sucked her nipple, I felt her hands running down my back and her fingers slipped just barely in the waistband of my jeans.

While I continue to suck on her nipple, I reached down between us and unbuttoned my jeans. As they opened I felt her hands slide over my ass. I let out a moan on her nipple which caused her to buck against me. I looked up at her as I slid my jeans and boxers down. She rose up to allow me to slide them all the way down and off. Once they were off, she leaned in and kissed me hard. One of her hands running over my chest, the other reaching down and gripping me. My cock was at its full 6.5", and Lori moaned that she liked how thick and hard I was.

We continued to kiss while she squeezed my cock. Lori up on her knees, her lips pressing down on mine as we kissed. I untied her pj pants and stared to push them down. She didn't have any panties on under so my hands could feel the smooth skin of her hips, her thighs as I pushed her pants down. Lori reached down to help me get them all the way off. There we were, both naked, our bodies pressed together as we kissed. It felt so good.

As she lowered herself back down, she pushed my cock up and pressed it between us and she let go. Her hands cupping my face. My hands running up and down her back, pulling her in tight to me. Her breasts pressed against my chest. Soft smacking sounds of our lips filling the room. As our bodies moved together. I could feel her bush scratching wonderfully against the underside of my cock as we bucked up and down together.

I broke our kiss and looked up at Lori, then down her sexy full body as she leaned back. I saw her trimmed red bush covering her mound which caused me to almost explode when I saw it. I looked back up and told her I wanted her. Her response was a nod and she whispered, "Yes James, take me."

Lori started to rise up, as she did, I reached down and held my cock. I then watched as she lowered her pussy down onto it. I felt her wet warmth as she slowly slid down until I was all the way inside her. We sat there, our bodies as one as I reached up and brushed the hair from her face and kissed her softly. Lori's arms wrapped around my neck and she slowly started to rise up. We moved slowly together, taking in how amazing this felt until our kiss ended. I then leaned down and buried my face between her breasts. Lori pressed them against my face and she started to ride harder and faster.

Lori pressed her breasts harder against my face as I kissed between them. I heard her breathing start to get faster and she started dropping hard on my cock as I thrust up into her. Then she started crying out, "Don't stop, don't stop, don't you stop James." She dropped down on my cock hard and stopped. I felt her hands on the back of my head pressing me against her chest as she let out a loud moan of "Yesssss!" I just held still as I felt her pussy tighten around my cock.

As I felt her pussy start to relax, I looked up with a big smile on my face. I just said, "Wow."

"James, you have no idea how long it's been and how bad I needed that." Lori replied with a look of relief on her face. "Now, how are you doing?"

"I haven't gone yet, but damn does this feel good." I said as I looked into those sexy green eyes. I then pulled her tight to me and kissed her as we started to move together.

As we kissed, Lori rose up and had me slide out of her. She broke our kiss and said that she wanted me on top. She then laid back on the bed, her head at the foot of the bed. Her legs spread, her arms open inviting me to her.

I slid onto her, and guided my cock back into her inviting pussy. I buried my face into her neck and could smell her perfume. She wrapped her arms around me, then her legs wrapped around mine as she pulled me in deeper to her pussy. Hearing her moaning, and feeling her warm wet pussy around my cock was bringing me closer and closer.

I slammed into her hard and then held still as I felt my whole body release. I held her tight, and felt her hold me close as wave after wave of cum released inside her. I felt my cock throb as the last spurts shot into her. Then I felt my body start to relax and release my tight hold on her.

I pulled back from her neck and looked at her, seeing her in a whole new light. I gently ran my hands over her cheek and kissed her lips in a short but passionate kiss. As our kiss ended, and my cock starting to slowly soften inside her, I whispered to her, "You are amazing."

Lori laughed and said, "You're not too bad yourself."

I laughed with her as I slipped out of her and rolled onto my side. Propping my head up with my hand as I looked over at her. Lori slid a hand down her body and rubbed over her pussy and I could hear her finger running through the mix of our juices. "You really did need that, I'm very full." Lori said as she brought her finger up, rubbing it on her hip. With that she got up and walked over to her suitcase and pulled out a pair of bikini style panties and put them on.

As she slowly walked back to the bed, I watched her big tits bounce slightly with each step. She climbed into bed next to me and told me she had to put those on so she wouldn't leak all night in the bed. I then pulled her close and pressed my lips softly to hers and she pulled back. I looked her in the eyes and told her, "I'm not sorry this happened. I know we shouldn't have but it was an incredible experience. However, I understand if this can never happen again."

"James," Lori said as she snuggled in closer to me, "It was wonderful and I do hope this does happen again. We need to be so careful though. I don't do things like this. You are the first one I've been with since I met David. This wasn't planned at all but I think as we both know it was something we both wanted and needed. From now on though, we need to be smart about this. If anyone were ever to find out about this, it would be devastating both personally and professionally. I think of you as a very close friend and someone I can trust. This never would have happened if I didn't feel that way. When we are in the office we can't talk about this, can't let on about this, or even joke about things that would give people the idea. If this is going to happen again, it will only be when we are on the road. We are lucky enough that we do travel each month so we'll have our chances and this will give us something to look forward to. From what I see and felt, we both will be ready for our trips. Are you ok with all this?"

"Oh my god Lori, yes!" I replied "I think of you as a close friend, and more than a boss. I agree we can't let this get out. I know I will be looking very forward to our trips."

Lori then leaned in and kissed my cheek. "That's good, I will be too." Then she turned her back to me and snuggled in close to me. We talked for a good hour about almost nothing, but both of us feeling so good. Eventually the week caught up to us and we both started dozing and drifted off to sleep.

The next morning I woke up to a phone beeping loudly. I tried to figure out where I was, and then saw Lori laying in front of me and the thoughts of the previous night came flooding back. It hadn't been just a dream, we really had done that. Lori leaned over and grabbed her phone and turned the alarm off and flipped the lamp by the bed on. She then turned over and looked at me and smiled. "Good morning James."

I reached for her as I smiled back and pulled her in close for a hug. Feeling her breasts pressing against my chest made my cock start to rise and rub between us. As we hugged, I told her good morning and let her know how wonderful the previous night had been.

Lori looked over at the clock and said, "Well, we have 3 hours until checkout. We could make this a wonderful morning too."

She then turned back and wrapped her hand around my hardening cock as she looked into my eyes and told me, "Go pack up and get your stuff and bring it over here. I'll be waiting for you, so don't be long."

I got up and quick slipped my shirt and jeans on and bolted for the door. Once I got to my room, I was grabbing everything I could as quick as I could and stuffing it in my suitcase. As I stopped in the bathroom, I quick brushed my teeth and then packed all of the bathroom stuff up. I did one last pass around the room and then started back to Lori's room.