Travelling with Sheila

Finally I had done it; I had gotten my first real job out of college. I was 26 and had worked a few other jobs to get by, but now I was at a company where I would be working with clients that were having issues with our products. I would be answering any questions on how to use them and on occasion, go out to their business and help them. My mentor was Sheila; who had been doing this job for many years. We spent many days working close together as she taught me the ins and outs of our products and some of the more common areas for issues. I really enjoyed working with her and really was learning a lot. It also helped that she was very easy on the eyes. She was 56, but with her diet and exercise regimen she could have passed for 10-15 years younger than that. She kept her sandy blonde hair cut short and wore glasses over her blue eyes.

As part of the job we did go on the road to visit customers and help them. I went with Sheila and helped with what I could but mostly took everything in, learning from her. I really loved watching her at the customer's site. At the office it was casual dress, so we wore jeans and t-shirts mostly, but to visit customers we were expected to be dressed up more. As great as Sheila looked in jeans, when she wore the skirts and satin blouses when we travelled it made it impossible not to try and sneak glances at her. Also, since she was so small up top, she rarely, if ever, wore a bra. This would cause many times where her nipples would be trying to poke through her top, something I found incredibly sexy.

Over the first two trips Sheila and I got to know each other well and the trips became something I looked forward to. During the day we worked side by side and then we'd go out and have a drink and dinner and talk. Over these dinners, I found out Sheila was married for the second time. She and her first husband had only been married a few years, they had gotten married too young and things just didn't work out. Her current husband was 17 years older than her and was still selling houses, something he loved to do. I too was married, had been for 3 years, so each night after dinner we would go back to our rooms and call our spouses and turn in for the night.

We were two days into our third trip. Things were going well and we were scheduled to go back home after the following day. That night as we walked back to our hotel after dinner, Sheila told me that her husband was taking some clients out showing houses that night so she wouldn't get to talk to him. She said she was going to rent a movie off of the tv and that I was welcome to come over and watch it if I wanted. As we stepped in the elevator, my eyes looked down at the floor, then drifted over to her legs, then up her body and finally into her blue eyes.

I smiled and said, "As long as it isn't a chick flick, I'm in."

Sheila laughed, "I'd never make you sit through one of those."

The elevator door opened and we stepped out. We arrived at Sheila's room first and stood outside her door. I said that I had to call my wife first but that should be quick and I'd be right over. Sheila nodded and opened her door and stepped into her room.

After I had called my wife, I changed into the shorts and t-shirt I slept in. As I walked over to Sheila's room, I stopped by the vending machine and picked up a couple of bottles of soda for us. I then walked over to Sheila's room and knocked on the door. Sheila opened the door and I saw she was in the terrycloth robe that came with each room; I did a bit of a double take. It was open down a long ways down the front and with me being over 6 foot and her about 8 inches shorter than me I could look down and see she wasn't wearing anything on under it. I looked back up, as she invited me in, and held the soda bottles up. She pointed over to the nightstand and said to set them there.

I walked in and set the soda bottles down. As I turned, I saw Sheila walking over and getting into the bed. She sat with her back resting against the headboard. I asked her if she had found a movie. She smiled and let me know she had found a comedy that we both would like. I sat on the chair next to the bed and kicked my feet up. With the tv turned towards the bed, it made for an awkward angle from the chair, but if I leaned just right I could see it. Sheila started the movie and then looked over at me and must have seen the funny angle I was sitting at and started laughing.

"Are you comfortable?" She asked

"I'm good." I replied with a smile.

"You don't look so comfortable. There is plenty of room on the bed here." Sheila said as she patted the bed next to her.

"You don't mind?" I asked, looking over at her.

"Of course not, now get over here." Sheila said laughing.

I got up and walked over and sat next to her. As I slid back, our legs almost touching, she turned and asked, "There, isn't that better?"

I nodded, and told her that was much better. I could see her smiling out of the corner of my eye and then she turned and we started watching the movie. It turned out to be a movie neither of us was into that much and we ended up talking through most of it. We talked about a lot of different things and slowly slid close enough to each other so we were touching. Sheila rested her hand on my leg as we talked. I slid my hand over the back of her hand so our fingers were intertwined.

When the movie ended, I turned and faced Sheila and told her I really enjoyed watching the movie with her. She responded by clasping her hand around my leg, which tightened the lock of our fingers. She told me she had a good time too. I sat there, looking into her eyes, and started thinking about how great this felt, sitting in bed with her and my shorts began to rise. As I squirmed a bit to try and hide what was happening in my shorts, Sheila leaned over slightly and her robe parted just a bit. I looked down quickly and confirmed there was nothing on under it and thought I saw one of her nipples. When I looked back up she had a little smile on her lips.

Not wanting to push my luck, I told Sheila I should probably be going, since we had another day to get through tomorrow. I saw her smile fade as I released my hand from hers. Seeing her smile fade and not wanting this night to end, I gently brushed my fingers over her cheek. Sheila leaned into it, bringing her face close to mine. I leaned forward and our lips touched. Her full lips on mine felt so soft, she was so gentle. My lips parted and I sucked softly on her bottom lip. I heard her moan as she ran her fingers through my short, brown hair. She then started sliding down, until she was lying on her back. I laid on my side next to her, holding my head up with one hand, my other hand running down her neck and to the opening of her robe. I leaned back in so I could feel her lips on mine again, our kiss so slow and light. My hand running down under her robe until my arm reached the tie in the robe. I untied the robe and began to open it. I watched her eyes close and heard her exhale slowly as my fingertip touched one of her very long nipples once the robe was opened. I then looked down and saw she only had on a pair of panties. Her body looked so sexy laying there as I touched her.

I slid down her body and took her other nipple between my lips, my tongue flickering over it in rhythm with my finger on her other nipple. Sheila reached her hand over to my shorts and started rubbing my hard cock which made my hips start pushing back and forth slowly. I slid my other arm under her body, pulling her on her side and in close to me. I began moaning softly, while sucking on her nipple, while my hand pressed between us started running down her body. I slipped my hand into her panties and ran my fingers through the soft hair covering her pussy. One of my fingers ran between her pussy lips, and began to rub. I rubbed softly up to her clit and circled it with my fingertip as my tongue circled her nipple. Sheila wrapped her arms around me, pulling me in so tight to her and moaned for me not to stop. I rubbed her clit, then slid my finger down and slipped it inside her wet pussy. I began to fuck her with my finger as I slid back up her body to kiss her lips.

I wanted Sheila so bad at this point. I rolled her onto her back, my finger never leaving her pussy. Sheila was moaning louder now and her hips were starting to buck as she tried to get my finger to go deeper inside her. Between kisses, I moaned to Sheila that I had to have her, wanted to feel inside her. She responded by pulling on my shorts, trying to tug them down. With my free hand I helped her slide them down and kicked them off. I then slid my finger out of her pussy and rolled so I was on top of her. I reached down and slid her panties down and off of her. I held myself up, looking down at her pussy, seeing grey patches mixed in her black bush. It looked so hot, at that moment I wanted to be even closer to her. I looked back up into her eyes wrapped my hand around my cock and rubbed her pussy with it, spreading the lips open with it. Sheila's hands were at the bottom of my shirt, pulling it up and off of me. So we were both laying there, our naked bodies pressed together.

I looked down into Sheila's eyes and leaned in for another kiss. As our lips touched, she spread her legs wider and I slowly started to push all 6" of my cock into her pussy. Our kiss broke, and she looked up and let out a long exhale, moaning softly as she did. I slowly pushed in further wanting to feel as much of her pussy as I could. My cock so hard and so thick, making her pussy feel tighter than I thought she would be, but as wet as she was I was able to slide in effortlessly. Once I was all the way in, I stopped, my fingers rubbing over Sheila's cheek and I told her how wonderful this felt. Sheila nodded and moaned softly and ran one of her hands through the hair on my chest. I wrapped my arms around her so our bodies were held together so tightly as we started to fuck.

I was slowly pumping in and out of Sheila's pussy, giving her lips a kiss each time I'd push in. I could feel her body getting warmer under me, and saw her body glistening in the low light from the lamp by the bed. Sheila was raising her hips, meeting each of my thrusts. As my pushes into her got harder and faster, I felt Sheila's body start to tense and she buried her face into my chest. I felt her warm breath on my chest as her moans grew louder. I pumped into her and then lost control. One thrust pushed in deep and I stopped, my cum shooting inside her. Quick little thrusts pumping more and more into her.

"Yesssssss" I moaned into the pillow as I felt my cream fill her tight little pussy.

"Mmmmm, don't stop, keep going, keep going." Sheila whispered into my chest.

Then I felt her whole body release as she pushed up hard forcing my cock deep into her and she cried out, "Oh.....My.....God......yes, yes, yes!"

I kept fucking her slowly as we both came down from our orgasms. I then pulled my cock out of her, seeing a string of cum follow and a moment of panic crossed my mind. "I'm so sorry, I lost control." I said to Sheila.

She responded with a little laugh, "Nothing to be sorry about, and there is absolutely nothing to worry about."

I relaxed a bit, and looked back down at her. Seeing her big smile, I leaned down and kissed her lips as I rolled over to her side. "Wow, that was so amazing." I said as I pulled her close to me.

"Yes, that was needed very much." Sheila replied between kisses.

We ended up lying there naked in each other's arms the rest of the night. We talked for awhile. Sheila told me that with her husband being 17 years older, things don't happen too often in the bedroom. We agreed to do this only on our trips together, trips that would happen often over the years. Each trip after that was something the both of us would really be looking forward to.