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Ashley, The Younger Woman

"An unexpected meeting with a beautiful young woman leads to mutual pleasures."

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A few months ago, I took a three-week vacation and drove back to Illinois for family visits. Usually, my wife accompanies me on these road trips, but this one she encouraged me to go alone and enjoy myself. As I left and she kissed me, she also winked and told me to have fun. I took that to mean it’s ok if something extra happens and just to enjoy it.

During this trip, I was not looking for or expecting to have sex with anyone. I actually had two unexpected and incredible encounters. This story is a recount of my second encounter as I was driving back to San Diego.

For this trip, I decided to rent a car from the San Diego airport. The nice thing about being a Gold member is it allows you to pick almost any car when you arrive at the airport. As I scoured the rows and rows of cars I kept asking myself what kind of car do I want to live with for the next three weeks. The choices were endless, but then I saw a beautiful black Ford Mustang convertible. Perfect. This choice contributed to my two experiences.

When I drove East, I took the southern route across the country. I thus decided to take the northern route heading West which would take me through Denver and the Rocky Mountains. I’ve never driven this way, so I was excited for the new scenery. Plus, I had family in Denver that I stayed with one night. This worked out well and I had an enjoyable visit.

The next morning I headed out early. I wanted to make it to Nevada by nightfall, so I had lots of miles ahead of me. I left around 6:30 am. The sunrise with the mountains was beautiful. I had to stop and take pictures of the amazing views.

I was soon on I-70 heading West driving through the mountains. Everything was going smooth until I began to encounter snowflakes. Now, having grown up in the Midwest, I was very familiar with snow and driving in snow. But I left twenty years ago and haven’t driven in snow since. It was just flurries, so I didn’t expect it would be bad. Plus, it was early October. Even for the mountains, I didn’t expect huge snow for that time of year.

As I continued driving, I realized how wrong I was about the snow for that time of year. It kept getting heavier and heavier and roads were getting slicker and slicker. The digital road signs were displaying warnings for heavy snow and ice conditions. I still felt I could handle it with my experience. I just slowed down and kept on going. Eventually, it got a little scary as I going downhill, tapped the brakes, and the car began to slide. Luckily, I kept control. But I realized I needed to reassess how far I would be able to drive that day. I also knew a high-horsepower rear-wheel drive sports car was not the right type of vehicle for these conditions. I decided I’d take the next exit to stop and check the weather on my phone.

The next exit was only a few miles away. I pulled off and realized I was in Vail, Colorado. What a beautiful place to stop. I pulled into town and stopped in a parking lot to check my weather app. Sure enough, it was going to snow all day long along a good portion of my route. Since I was not on a specific time schedule, I decided I’d play it safe and stay where I was at. I logged into my Hilton app and found a DoubleTree hotel two miles away with rooms available. I booked a room and drove to the hotel.

It was only 10:00 am so I wasn’t sure if they would let me check in that early. I am a Diamond member with Hilton, so I knew they would get me in if rooms were available. They not only had rooms available and let me check in early, they also upgraded me to their best room. It was a loft suite with a king bed, fireplace, and kitchen. Not bad at all. After I got settled in my room, I called my wife to explain the situation so she wouldn’t worry. I then decided to check out the town. I love skiing, so being in Vail was exciting. It’s too bad there wasn’t enough snow yet to ski.

As I walked past the front desk to get to my car, I noticed a young woman checking in. I guessed she was about thirty years old. She was very pretty. Blonde hair and beautiful face. She was dressed for business with a nice skirt and business jacket over a blouse. I imagined she was in the same situation as me and decided to stop for safety too. I didn’t think any more about her as I headed to my car. I spent the next several hours in downtown Vail. Walking around, visiting shops and museums, taking pictures, and just enjoying the scenery as the snow continued to fall. It was very picturesque.

Around 3:00 pm I headed back to my hotel and went to my room to freshen up. Since I skipped lunch, I decided to have an early dinner and headed down to the hotel restaurant around 4:30 pm. Since the hotel was nearly empty, there were no servers and you ordered everything from the bartender. I placed my order and then settled in at a high-top table a few feet away from the bar. I started off with a nice beer and appetizers before ordering a nice salad, burger, and fries.

As I was waiting for my food to come, I noticed the beautiful young woman from earlier. She was ordering food from the same bartender. I overheard her asking if it could be delivered to her room. After she paid, she waited for the bartender to deliver her drink. As she was waiting and looking around, she glanced my way and made eye contact. I smiled at her and she smiled back. A very attractive and innocent smile.

I then said to her, “I’m sorry for eavesdropping, but I heard you ordered your meal to go. If you’re interested in some company, you’re welcome to join me.”

I could see her thinking and deciding what to do. After a few seconds, she said, “Thank you. I could use some company after my bad day today.”

I introduced myself as James and she introduced herself as well. As I expected, Ashley got stuck in the snowstorm too. She is in pharmaceutical sales and had flown into Denver that morning from Florida. She was driving to a client when she got caught in the storm and decided to stop for safety. She missed her meeting with her big client and was upset.

We had an enjoyable meal together. It was so nice to just spend time talking to someone new. Ashley has always lived in Florida, so she has very little experience with snow. I was impressed she was able to drive as far as she did with no winter driving experience. We both enjoyed getting to know each other better.

As we were finishing drinks, Ashley asked, “What are doing the rest of the night?”

I said, “I’m going to enjoy the pool and hot tub.”

She said, “But they’re outside. Isn’t that cold?”

I just laughed and told her how they are both heated and it’s an amazing experience to be in the water as snow is coming down.

“You should join me,” I said.

“I don’t have a swimsuit with me,” Ashley said.

I suggested we stop at the gift shop to see if they have any leftovers from the summer season. Or I suggested she just wear a T-shirt and shorts.

We walked over to the gift shop. As Ashley looked for swimsuits, I looked for some wine. I was looking forward to a nice glass of wine in front of the fire after a soak in the hot tub. I found some nice local wines and bought three bottles so I had two to bring home. As I was paying, Ashley came walking over with a swimsuit in hand.

“Found one,” she said as she smiled. “They only had bikinis though.”

“That’s fine, Ashley,” I said. “Just use the robe from your room when you come down.”

She looked at me and said, “What robe? I didn’t see any robes in my room.”

I realized that must be one of the perks for my room or my Diamond status. I offered her the use of one robe from my room so she would feel comfortable.

We finished paying and went to my room to get a robe for Ashley. I first went into the kitchen area to put a wine bottle in the refrigerator. Ashley looked around in amazement.

“Wow,” she said. “Your room is amazing. I can’t believe you have a fireplace. Where is the bedroom?” she asked.

I pointed to the stairs and she noticed the loft. Her amazement continued.

“This is so much nicer than my room,” she said. “Can I see the loft?”

I told her of course and we both walked up the stairs. I had to go up anyway to fetch the robe from the closet. Ashley stood at the top looking down at the fireplace, balcony, and snow falling outside. I could tell she really liked what she was seeing.

“Here’s your robe,” I said as I handed her a nice fluffy robe from the closet. “Why don’t you head back to your room to change, and I’ll meet you outside by the hot tub.”

She smiled and thanked me. “If you don’t mind, James, I could just change here and we can head down together.”

Hmmmm. Now this is getting interesting I thought. For the first time, I started thinking perhaps this beautiful young woman was interested in me.

“That would be fine,” I said. “Why don’t you use the bathroom up here to change and I’ll use the bathroom downstairs.” Conveniently my room two bathrooms. I grabbed the second robe and my swimsuit and went downstairs to change. As I came out of the bathroom, I saw Ashley coming down the stairs looking like an angel in a white robe.

We made small talk as we headed down to the outside hot tub. She was excited about the new experience of being in an outdoor hot tub during a snowstorm. When we reached the hot tub, I was happy to see there were no other people in the hot tub or the pool. Just me and Ashley. She took her robe off and I got my first real view of her body. Slim, long legs, perfect-sized tits. Just a beautiful woman. Having gotten to know her over the past couple of hours, I was even more attracted to her.

We both slipped into the hot tub and sat on opposite sides of each other. She loved just looking up and having the snow fall on her face and then started laughing. It was so nice to see her experience something so unique for the first time. We continued talking and just enjoying the tranquil situation.

Suddenly, three young guys came running out the doors screaming and wearing just swimsuits. Clearly, they were very cold. They all jumped in the hot tub with one on either side of Ashley and one next to me. After they settled down, one guy started to hit on Ashley. I could tell she was getting uncomfortable. I was about to say something when she stood up, moved right next to me, put my arm around her, and said, “I don’t think you should say stuff like that to a married woman.”

The guy acted surprised. “He’s your husband?”

I was a little offended by the way he said it. But I reacted calmly and said, “Yes, we’ve been married a few years. We’re here on a nice vacation and you interrupted us.” I then turned to Ashley and said, “Let’s go back to the room hun, and let the boys enjoy themselves.”

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She smiled and kissed me on the cheek. Their mouths dropped as she stood up and saw her body in the bikini. They looked at her and me as we exited the hot tub and I’m sure were trying to figure out how this old guy got this young beauty to marry him. I handed Ashley a towel and then her robe. We both quickly dried as much as we could with the towels and then put on our warm fluffy robes. She then put her arm in mine as we walked back to the hotel.

“Bye boys,” she said. She then looked back and blew them a kiss.

We both were laughing as we got back inside the hotel and went to the elevator. Surprisingly, she didn’t drop the act and kept her arm inside mine. I think it was comforting for her, and I enjoyed it as well. We continued talking and laughing about the situation as we headed back to my room.

As we entered my room, I suggested that Ashley could use the shower first. I hoped she would ask me to join her, but alas she did not. As she showered, I started the gas fireplace and opened the bottle of wine. I kept the lights off downstairs and just let the fireplace and outside snow light the room. It was so peaceful as I sat down enjoying the wine.

Soon I heard Ashley at the top of the loft. “Wow!” I heard her say. “That is so beautiful and romantic.”

“Isn’t it amazing?” I asked her.

“It is beautiful,” she said as she came down the stairs.

I fully expected her to be dressed, but she was still wearing the fluffy robe. I wasn’t sure what she was wearing underneath since she had it pulled closed. I was happy she felt so comfortable. I handed her a glass of wine and then told her to enjoy while I took a shower. I went upstairs to shower. My cock was so hard as I thought about this gorgeous woman in my room. I resisted masturbating and cumming in the shower.

I finished my shower and got dressed. As I exited the bathroom, I saw Ashley on the bed with her robe opened. Her beautiful breasts were displayed and she was slowly playing with herself. Wow!

“Come take care of me, my husband,” she said smiling at me.

I moved to the bed. As I got in, she rolled on top of me and we began to kiss. Deep, passionate, erotic kisses. Our tongues entwined as we both tried to get deeper and deeper with our kisses. As we were kissing I reached up and felt her beautiful tits. She moaned as I massaged her right tit and began pinching her nipple.

“Let’s get naked,” she said.

She took her robe off as I got off the bed and began undressing. My cock was so hard as I looked at this beautiful woman in my bed. I crawled back in bed and we kissed again. Ashley pushed me to move on my back and then she started to suck on my nipples. I moaned in pleasure. Ashley then moved down to my cock and slowly began to give me a blowjob. I loved seeing her suck my cock. She would make eye contact with me and smile with my cock inside her mouth. It was heaven.

Then Ashley did something that no woman has ever done to me. She began nibbling the head of my cock. More and more she nibbled. Her lips were around my cock head, her tongue flicking all over the tip of my cock, and her teeth grinding on my cock head. Fuck it was amazing. Somewhat painful but in a good way. I was squirming and moaning. I didn’t know if I wanted her to keep going or to stop. She kept going more and more and before I knew it I was cumming in her mouth. God, what an amazing cum. After Ashely had swallowed, she moved up to me smiling.

“Did you like that?” she asked.

“It was amazing,” I said. “I’ve never had a blowjob like that. Come here and kiss me.”

Ashley looked at me strange and said, “I just swallowed though.”

“That’s ok. I like to share,” I said as I laughed and pulled her to me for a kiss. She had swallowed all my cum, but I could still taste it on her tongue.

As we continued to kiss it was now my turn to worship this amazing woman. With Ashley on her back, I started with her tits. Squeezing, licking, nibbling, and playing with her tits and nipples. As I played with her tits, I also started to finger her pussy. She was so wet as I pushed two fingers inside her. I focused on sucking just one nipple as I began to finger fuck my lover. Ashley was clearly enjoying as I heard her moaning and moaning. Soon she was pushing me down indicating she wanted me to eat her pussy.

I happily obliged as I moved down to her pussy. I stared at this gorgeous shaved pussy and then dived in. I loved sucking her clit as I continued to finger her. I used my tongue all over her pussy, inside and outside her pussy. I took my time enjoying her taste and listening to her moan. I then started nibbling her clit like she did to my cock. I kept finger fucking her and licking and nibbling her clit. I knew she was close and soon she orgasmed.

“Oh gawd I’m cumming. Ohhhhhhh James,” she moaned as she orgasmed.

I took my fingers out of her pussy and moved up her body, licking as I went. When I got to her face, we kissed and this time she got to taste her cum.

“That was amazing, James,” Ashley said.

I just smiled, kissed her again, and then wrapped her in my arms. We held each other for a long time and gently kissed each other.

After a while, Ashley looked at me and smiled.

“Make love with me.”

She reached down and slowly began stroking my cock which had now recovered and was hard again. She pushed me on my back.

“Do you have a condom?”

“I had a vasectomy years ago,” I told her. “So I can cum inside you if you would like that.”

She smiled and nodded, Ashley then mounted me on top. My cock easily entered her wet pussy. She began riding my cock faster and faster as I played with her tits. I then wrapped my arms around her and pulled her to my chest to slow her down. I put my hands on her beautiful ass and started rubbing them all over. As I did this, I took a finger and started rubbing her asshole. I fully expected her to tell me to stop. Instead, she pulled my hand to her mouth and sucked my finger getting it all wet.

“Now try it,” she said.

I used my wet finger and slowly pushed it into her ass while my cock stayed inside her pussy. I got my finger in up to the knuckle and then I started pounding my cock into her. I tried moving my finger in and out of her ass at the same time, but soon I just settled in with my finger in her ass and my cock moving in and out of her pussy. Ashley was moaning and asking for more. She isn’t a vocal lover with words, but she is vocal with her moans. All of a sudden as Ashley moved up, my finger went all the way into her ass. At that point, I could feel her orgasm on my cock. I couldn’t hold back anymore and I started shooting stream after stream of cum into her amazing pussy.

I pulled my finger out of her ass and wrapped my arms around her tight. My cock stayed inside her as I rolled us onto our side. I pulled the covers on top of us as I could now feel the cold. I held this angel in my arms kissing and cuddling her.

“Wow. I have never let anyone do that to me, James. Wow.”

I started laughing and said, “I’ve never done that to anyone myself. You were wonderful, Ashley.”

After about twenty minutes of cuddling, Ashley wanted to sit by the fire.

She went to the bathroom to let my cum out of her. I put on a robe and headed downstairs. I refreshed our wine glasses and set them on the table by the fire. Then I saw Ashley coming down the stairs. She was still naked and carrying some blankets from the bed. I immediately knew her intentions so I moved the table out of the way. Before she put the blankets down, I stopped her and went to the closet to pull out the bedding for the sofa sleeper. We opened up the sofa sleeper and together made the bed.

Ashley crawled onto the sofa sleeper mattress and sat with her back on the sofa back. I handed her a wine glass, took my robe off, and crawled in with her. We did cheers with our glasses and drank our wine as we watched the fireplace inside and the snow outside. We didn’t talk at all. We just sat close to each other enjoying the warmth of our bodies and the warmth of the fire.

“James, I want to make love again. Are you up for it?”

She smiled and wrapped her hand around my flaccid cock. I wasn’t sure I could get hard again. Ashley took our empty wine glasses and put them on the floor. She then started licking and sucking my nipples again. Clearly she knew how much I enjoyed it. My cock was starting to get hard again in her hand. She moved down and wrapped her lips around my cock. This time, she didn’t nibble my cock. She slowly moved her mouth up and down my cock until I was fully hard for her.

Ashley then got on her back and spread her legs. I gladly moved on top of her. She guided my cock into her waiting pussy. I put my hands on both sides of her face and held her tight as I kissed her. Looking into her eyes, I just smiled at her letting her know how much I enjoyed being with her. I began moving faster and faster. Ashley was holding my ass with her hands and pushing my ass to make me go faster and faster. I then felt her finger probing my asshole. I pulled her hand away and sucked her finger making it all wet.

“Now try it,” I said in a role reversal from earlier.

No one has ever done this to me. Ashley got her finger partly in me. The sensation took me over the top and I was soon cumming inside her as I screamed in pleasure. Amazing. I can’t remember the last time I came three times in one night. It was probably back when I was younger than Ashley. But this young woman brought so much out of me.

We were both spent after that. The fireplace was on a timer and soon shut off. That was our queue to move back to the bedroom loft. We went upstairs and fell asleep holding each other.

In the morning, the sun was shining as the storm had ended. We made love one more time and then showered together. We then enjoyed breakfast in the restaurant and went back to our rooms to pack up. Ashley still had to get to her client and I had to continue my trip home. It was a situation where neither one of us wanted the experience to end, but we both knew it had to end. It was bittersweet.

We both checked out and packed our cars which were parked right next to each other. We embraced and kissed again. We exchanged phone numbers and promised to stay in touch. Although we both knew this was a one-time experience. We drove off together in the same direction and drove for miles following each other. As Ashley took her exit for her client, we both waved and blew kisses to each other. And with that, I continued my journey back home with amazing memories of a beautiful young woman.

Written by Big12shoe
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