On The Road

Everyone in this story is over 18

Constructive criticism is welcome and may be used in future versions or chapters.

My wife and I have a great sex life together, one that has become kinkier and better the longer we are together. I am in my late fifties while my wife Tiffany is nine years younger than me. Tiffany has stayed very fit, while on the other hand, I have gotten a little soft in the middle over time. I still have a crazy sex drive and my wife's drive has gotten stronger the last few years.

I travel a lot for my work and get urges on the road that we often satisfy with phone sex. About four years ago, during one of those sessions, Tiffany told me that if I felt the urge and could not control it, she would not mind if I found some relief. She just told me to not come home and tell her about it. I thought that was amazing of her, and though intrigued, I have not taken her up on her hall pass yet.

Since as far back as I can remember, I have always had a thing for girls/women in sporty attire like workout gear. It started with the gym outfits in the eighties, all the way to the half-dressed women jogging down the side of the road today in their tight, shiny, booty shorts and bright sports bras. Tiffany knows how much those outfits turn me on, she stays fit and wears those kinds of outfits around to tease me and keep me primed.

I was out of town this week and feeling the need for some relief. I was hoping to have a nice long phone session with Tiffany, but the stars did not align where I could get to my hotel room and call her while she was free too. Frustrated that I could not get her on the phone, I left my room and went to the lobby to get a cup of coffee. On my way to the lobby I passed by the workout room, it had a glass wall so that you can see into the room from the hall. I looked in and almost stopped in my tracks. I see this woman that was probably in her late twenties or early thirties running on the treadmill. She is a brunette with amazing bronze colored skin. She is wearing some black spandex booty shorts with a neon green sports bra and some neon green Nike free or flex style sneakers. I swear my mouth was hanging open looking at her, I had this sudden deep lust for her. She looked over my way and caught me staring at her. She waved and smiled at me as I turned red and waved back.

I walked the rest of the way to the lobby and got my cup of coffee. On the way back I wanted to watch her again, but after getting caught the last time, I just walked past looking out the corner of my eye into the workout room. To my surprise she was gone, I felt robbed that she was not there for me to look at again, even though I was not really going to look this time. I went back to my room and was doing some work, but I couldn't take my mind off that woman. I was getting hornier as time passed. I tried several times to call Tiffany but was not able to reach her.

It was now around five pm and I worked my way to the lobby to get something to eat. I passed the workout room again, but there were just a few guys in there. I worked my way to the lobby bar area, and there she was standing near the bar. This time she was wearing one of those skintight spandex type dresses, that went just below her ass. It was black and she had on some all black high-top converse sneakers. That strong lust returned, and I was nervous as I walked closer. I started to walk up behind her to get in line, but she turned and walked away without noticing me. I ordered a drink and some food and found a table. I could see her sitting on the other side of the room from where I sat.

My food arrived and as I was eating, I noticed movement near me and looked up. She was standing in front of me and looking right at me. I froze as we made eye contact. She walked closer sticking out her hand and told me her name was Ashley. I was at a total loss for words as the lust is beginning to overwhelm me again. I finally spit out that my name is Bob and shook her hand. She smiles and asks me if I am leaving in the morning, I tell her that I will be there for a few more days. As she releases my hand, she tells me that she will probably see me around then, she turns and walks away. I can't help but to watch her until she walks out of site. She looked amazing in that outfit, what an ass and body.

The next morning came and I went to the lobby for breakfast. I found a table and waited for my food to be brought to me. As I was sitting there, she walked in the room and got in line to order her food. She then worked her way to a table that was directly in my view and not too far away. She sat down facing me and when she noticed me, she smiled. She was dressed almost the same as last night, only this time her tight dress was white, and she had on white high-top converse. I was going out of my mind after seeing her three times now and not being able to get my wife on the phone for some relief. I could see her from head to toe and she was sitting with her legs crossed, one foot bouncing up and down as she looked through her phone.

I have not been able to get Tiffany on the phone and have been texting her letting her know I was ok and what I was up to. I texted her as I came down for breakfast letting her know she could call me while I was eating. I texted her last night when I went down for dinner for the same reason.

I am sitting there eating my breakfast and kept looking up to watch her as she moved her Converse and repositioned herself throughout breakfast. She is fucking amazing looking, that coupled with the dress and sneakers is kicking my mind into a sexual frenzy. I took my time eating as I wanted to soak up as much of her as I could, before returning to my room. I noticed she was getting ready to leave, so I got up and headed to the elevator to return to my room so that I could answer a few emails before heading out for the day. As I was waiting for the elevator, she walked up next to me and said, "Hi."

I nodded and said, "Hi" back, then the elevator doors opened.

A few people stepped out and I let her get in first. She had already hit the button for her floor and when I went to press mine, I noticed she was on my floor.

"So, how long are you in town? "she asked.

"Just until Thursday," I said.

"Me too," She replied.

"So, what are you int town for?" I asked.

"Just a little get away, I live in Tampa and just felt like coming to Orlando for a few days," she smiled.

"Here to go to the parks?" I ask.

"No, not really. I just wanted to take a little drive and get away, "as she looks down at her feet and curls her toes flexing her sneakers.

I followed her eyes and looked down at her feet too, I watch her as she flexes her sneakers again, as I am looking at her sneakers I say, "I am actually from the Tampa area too. Crazy how that happens on the road sometimes."

She looks back up and says, "Really, that is crazy isn't it"

The elevator doors open, and we are on the tenth floor. I let her lead the way and she ended up walking the same way that I needed to, so I was more than happy to follow behind her and watch her walk. I was surprised to find she is in the room right next to mine. I walk past her as she opens her door and she watched me go to the next door and open it.

"Guess were neighbors here too," She says with her sexy smile.

I get in the room and check my phone. No texts and no calls from Tiffany. I start to wonder if she is ok and send her another text asking her if she is alright. I get a text back from her saying she is sorry, but she has really bad service at her sister's house. I know this to be true and understand why I have not been able to reach her.

I finish my workday and return to my room. As I walk past the workout room, she is inside running on the treadmill in the same outfit as last time. I don't want to be caught staring, but she sees me and waves me in. I reach for my key and open the door to see what she wants.

"Hey, since we are both from the same area, I was wondering if you wouldn't mind joining me for dinner tonight?" she says as she is running on the treadmill.

I am more than happy to go spend time with her and say, "Absolutely, I can do that. I get lonely on the road at times, so it is nice to have a conversation with someone."

"Great, so do you want to eat here or go out?" she says without missing a beat on the treadmill.

"I am ok with either, what do you prefer?" I ask.

"Here is fine, I hate the traffic, how does five thirty work for you?"

"Five thirty is great," I smile

"Ok, see you then," she smiles back

I return to my room and take a shower and get changed into my more comfortable loose-fitting shorts and Polo shirt. Five thirty rolled around and I heard a knock at my door. I answered the door and there she was. Her beautiful face, nice full lips, bronze skin, young toned body, this time wearing some short blue jeans shorts, a white crop top hanging off her breasts showing her bronze stomach and at the end of her long bronze legs was pair of black and white, checkered slip on vans.

"Hi," I stammered as I took her in.

She smiled, "You ok?"

"Yes, just surprised, I thought we would meet in the lobby, so seeing you surprised me."

"Ready?" She asked with a giddy smile.

"Yep," I said as I walked through the door and into the hall.

She led the way down the hall and I just took her in as she walked in front of me to the elevators. Once inside she moved between me and the door so she would be ready to get out on the ground floor. I looked her up and down and was out of my mind thinking of the things I wanted to do with her. The elevator stopped on the seventh floor and I moved into the back corner to allow her to move back to make room. She backed up so she was off to my right and just in front of me. A couple walked in and the doors closed. She is too close for me to get a good look at her now and I was kind of disappointed I could not keep fantasizing, when suddenly the back of her hand grazed my crotch. Then it grazed it a few more times. I am thinking what a happy accident and my mind drifts into fantasy land again. I can feel my cock start to grow as the back of her hand grazes it a few more times as she shifts her weight around waiting. The elevators in this hotel are very slow, but I am finding myself wishing they were even slower now as I watch the floors count down.

Five, then four, then three, then the elevator stops on three. Two more people get in and she is forced over in front of me now. I can smell her hair it is so close to my face now and she smells good. The doors close and the elevator starts to move. She shifts her weight and her ass rubs up against my crotch now. She is shifting her weight from foot to foot and her ass is grazing my crotch each time causing my erection to firm up even more. I am getting worried because in these shorts It will be obvious that I have a boner when I get out. In my mind I am wishing I could just slip the crotch of her jean shorts over an inch and slip my cock inside her right now in the elevator. Then I shake it off and deal with the emerging issue of my erection.

We get to the first floor and I follow her again watching her ass, her legs, even how her feet look flexing those vans. We find a table and wait for the waiter / bartender to take our order. We start to discuss the area we are from and it turns out she lives closer to me than I thought. She lives within five miles of my house. She told me she has only been in the area for about five years and has made many friends already. With how she looks I would think she would have hundreds; I think to myself. We continue our small talk over our meal, then we get into what I do and what she does for work. I am in a technology field, while she has a few part-time gigs she does. It seems she is a model as well as a masseuse and a fitness instructor at a gym near me. The last one was a bit of a shock, since that's the gym my wife uses.

We finish our dinner and decide to have a few drinks out by the pool and talk for a while. I should have probably drunk a few less than I did because I found myself getting buzzed and losing some control. It was hard to keep my thoughts off of fucking Ashley's brains out right there by the pool for all to see. I think she sensed I was a little buzzed and decided it was time to call it a night. I followed her to the elevator and got in the back corner again. I was just looking her up and down as we rode the elevator up to our floor. Ashley took her phone out and was texting someone as she slowly moved backward in the elevator. She had backed up to being almost next to me again. As she put her phone away her hand dropped to her side. Right away the back of her hand started to innocently graze my crotch. Being a little buzzed I moved my hips into it so that it was happening more and more as the elevator climbed. I had pushed forward enough, where my cock was in constant contact with the back of her hand as it moved around.

Two more floors and this would end, the doors would open, and her hand would no longer be touching my cock. In my buzzed state I forgot I was wearing the loose shorts and my erection was very noticeable by now. I was dreading that the doors were going to open, but just before we got to our floor, her hand spun around and she grabbed hold of my cock through my shorts. Ashley turned her head, looked at me over her shoulder with a smile and said, "Hey buddy, what's this?"

"I'm sorry, I didn't realize I was touching you," I lied.

"It's ok, but why are you so hard right now?" she asked with that sexy smile still on her face.

I looked into her beautiful light brown eyes and just as I was going to speak the doors opened. She pulled her hand from my cock.

"I sense you want to talk about it, do you?" she asked.

"Kind of, but we just met," I reply

"No worries, I will go down and grab us two coffees and meet you in your room with them," She said.

She spun around and hopped back into the elevator before the doors shut and she was gone. I had a very noticeable bulge in my shorts as I quickly returned to my room hoping that no one would pop out and see me on my way. I entered my room and dropped into the desk chair while waiting for my erection to go away. It was only minutes before I heard the knock on the door. I was still semi hard as I opened the door. She handed me my coffee and sat down on the end of the bed as I returned to the desk chair. This put her slightly higher than me with her legs hanging off the end of the bed.

"So, what is it?" she asks with a worried look.

"It's nothing, I just get horny at times when I'm away from my wife, we have a very active sex life and it is difficult at times when I see a good-looking woman," I say with a shy smile.

"So, based on that erection you have, you find me good looking?" she smiles like a bird that ate the canary.

"I think you are fucking hotter than hot," I say.

She smiles and says, "Is that it, your horny?"

"Horny, tired, stressed, and have a little back pain," I smile.

"Well I can help with a few of those, I am a masseuse, "She smiles.

I found myself looking at her legs and sneakers getting horny again.

"Yeah, but your helping me with some, might make another one worse, "I smile back.

"Well, nothing to lose then based on that tent in your shorts," she smiles.

"Guess not," I reply.

She stands up and taps the bed, "Climb up here, head on this end, face down, with your head hanging over the end a little."

I get on the bed as instructed. I am lying face down and I see her sneakers come into view, then I feel her hands on my shoulders. She starts by rubbing my neck and shoulders and it feels great. I close my eyes as she keeps working my upper back and shoulders. I start to feel really relaxed and open my eyes. I see as she is rubbing my upper back she is rocking in her sneakers and the way they look flexing on the end of her bronze legs is making my erection return. She keeps up the massage and I am feeling more and more relaxed but getting more and more horny again.

"Ok, let's have you flip around now so I can do your legs, "she instructs me.

I roll over to sit up and she giggles. I see her looking at my crotch and I look down to see the tent in my shorts with my cock as the tent pole. I finish turning around and lay face down again.

"I told you it would get worse," I said, as I felt her start to massage my legs.

She giggles again, "It's ok, I think it is all going to work out, you will see."

After about ten minutes of her massaging my legs she stops, and I hear her walk into the bathroom. She returns and throws two towels on the bed next to me. "I need you to take your clothes off and lay face down on one towel and I will cover your lower half with the other when I come out."

I am more than happy to get naked with her in the room. I am hoping it will be more than me being naked eventually.

Ashley walks back in the bathroom and as she closes the door says, "Let me know when you are ready, and I will come out."

I call out to her to let her know I am ready, and she returns to the room. She grabs the other towel and drapes it across my ass. I feel her climb up on the bed and straddle my legs. She goes back to work massaging my legs higher now and working her way up. She gets to just below my ass and moves to my lower back. She is doing a wonderful job and I am so relaxed at this point. After several more minutes of this she pulls the towel out of the way and starts to work on each butt cheek, giving them a deep muscle massage. I can feel the last bit of tension drift away. I am completely covered in massage oil at this point from head to toe on the back of my body.

I feel her shuffling around some and then work her way back up my back to my upper back and neck. Then as she moves, I suddenly feel her breast hitting my lower back, only it feels like naked breasts touching me. She moves up more and I feel them press into me more as her head becomes even with mine.

She whispers in my ear, "Did I mention that I do Nuru massages too?"

She giggles and starts to rub her body up and down mine. Her hands working themselves along my side and her upper body slipping up and down mine. I feel her shorts hitting my legs as she keeps rubbing my back with her tits. I want to spin around and look at them but am enjoying it too much right now. I don't think my cock can get any harder than it is at this point.

"Ok, time to do the front", as she grabs the towel and holds it over my ass and tells me to turn over. She drops the towel over my crotch, but my cock is holding it up in the air. She looks amazing as she looks at it and giggles again. Her tits are perfect in every way. If you were going to design a girl, her tits are what you would order. She pours oil on her hands and starts to rub my feet and work her way up my legs, eventually my cock softens enough for the towel to drop. She avoids getting too close as she works her way back up my legs. She is trying to avoid causing another pitched tent. She moves around on the bed and is above me looking down now. She massages my chest and arm. I am looking up at her tits from underneath as she does, of course my cock goes to full mast again while she is massaging me from this angle.

She giggles, "Damn it, I thought we got rid of that damn thing, maybe if I take my sneaker off and whack it, that will help."

I giggle now and say, "No, that would probably make it harder."

"So, you like to have your cock smacked then?" She asks.

"Not really, I just have a thing for women's sneakers is all," I say in a shy voice.

She smiles and keeps massaging me. Then she has me flip over again and repositions herself at my feet. She takes the towel off again and goes back to massaging my ass. I suddenly feel her hand reach under me and pull my cock down between my legs. I grunt, and she says," I want to keep it from getting crushed under you."