Traveling with Charlene Pt. 01

Friday:

I have been fortunate over the years to have traveled all around the Western United States. My job as an IT Specialist for a major grocery chain in Northern California sends me out to our retail stores to install or upgrade computer systems. With every trip I meet many wonderful people and experience new adventures along the way. The travel is never dull as we get to experience great restaurants and check out the local scene in every city.

My partner in crime for most of the travel is a beautiful lady named Charlene. She handles all of the telecom duties while I concentrate on the computer networks. We make a good team and have been traveling together for over a decade.

We are both happily married, in our 50s and look forward to retiring together in the not too distant future. Aside from our spouses, we probably spend more time together than with any other person on the planet. This suits me just fine since Charlene is my dream girl. She stands five foot four and might be considered to have a thick body type by some people. Personally, I don't see it. What I do see is a lady with sparkling blue eyes, wavy auburn hair cut to a stylish shoulder length and an electric smile that lights up a room. What I also see is a pair of incredibly large breasts, rounded and sitting high and proud. They are balanced by her well-formed and generous bubble butt on the lower end. Her overall appearance always keeps me in a state of semi arousal whenever we are together, which is most of time.

Our current assignment has us flying to Phoenix the second week of March to upgrade a grocery store in Scottsdale. It's a small store and only minor upgrades are required. We'll be working most of Friday and part of the morning on Saturday. We are required to be onsite the following Monday to make sure all of the upgrades are functioning properly. This schedule means we will have most of the day on Saturday and all day Sunday to play. This is a pretty typical schedule and one that Charlene and I have come to enjoy for many years.

Our travel always includes dining at nice restaurants and enjoying local events wherever we find ourselves. Spring Training will just be getting started, so we hope to catch a game while in Arizona. Our West Coast travels have allowed us to share many fun activities including the Oregon Shakespeare Festival and Seafair in Seattle; not to mention a weekend in Sun Valley, Idaho.

Where ever we find ourselves, you can bet Charlene does her best to fluster me one way or another. She knows I love big boobs, especially hers. When we are away from work, she rarely wears a bra and is always shaking or jiggling them trying to get a rise out of me. I've gotten into the habit of wearing loose fitting pants as my seven inch cock is always in a semi-erect state, if not totally rigid when we are together. She will discretely glance at my crotch looking for a distinctive bulge or trying to catch me adjusting myself.

When at work we are all business and conduct ourselves in the highest order. Secretly I fantasize about what she is wearing under her business attire. I have always wondered what her nipples are like; their color, texture, size. Does she have wide, pale areole, or maybe rose colored with stiff nipples as big as my thumb? My fantasizing about Charlene's tits has fueled many masturbation sessions on the road.

The two items I always take with me are my Tablet and my Fleshlight. I have an HDMI converter cable so I can plug my Tablet into the flat screen TV and stream porn to the big screen. I learned long ago not to waste money with the hotel's so called adult channels. Paying $15 a night to watch edited simulated sex on their cable channels just doesn't cut it. It's especially embarrassing trying to explain such charges to the accounting folks when I turn in my expenses. One thing I always pay for, or should I say the company always pays for, is the premium Wi-Fi service so that the porn streaming from my Tablet is fast and never buffers. I justify the charge to my boss by saying it allows me to VPN into the office network anytime from my hotel room. Yeah, right.

I've never shared this info with Charlene. Some things are sacred. Although, I've often wondered if she travels with a favorite vibrator or dildo to help her unwind at the end of the day. Ahhh, the fantasies I can conjure up.

Our trip to Phoenix begins with an early morning flight. I meet Charlene at the check in counter where we drop our bags and receive the boarding passes. The airport is usually very quiet on Friday mornings. The weekly commuters will fill this place later on in the afternoon. We sail through security and have plenty of time for breakfast before boarding the airplane.

"What do you feel like eating this morning?" I ask Charlene.

"Oh the usual, scrambled eggs and toast."

Charlene, like me, is wearing the standard business casual attire, tan khakis with dress shirt. Or in her case, a lovely satin green blouse that is straining to keep her huge melons contained. She has a matching jacket that covers her top from prying eyes. Not my prying eyes, of course.

We take our seat in the modified diner and order breakfast. I use my napkin to cover my growing erection, hoping Charlene doesn't notice. We chat about the weather and upcoming duties once we get to the store. We also make tentative plans for Saturday and Sunday. We expect to see the Giants play in Scottsdale stadium on Saturday. Since it's still early in Spring Training, it will probably be a split squad game, or one that features mostly backup players or boys destined to begin the year at AAA. It doesn't matter to us, as we will be enjoying the warm sunny weather of the Southwest and drinking beers.

"You look lovely as ever, Charlene."

"Why thank you Rob, I am so looking forward to this trip. I am tired of the rain and tired of winter. I need sun. It's supposed to be in the high 80s and low 90s while we are there. Will you take me out to the ballgame on Saturday? I packed my favorite jersey and cap."

"That's the plan, my dear. It may be hot in the sun so you may not want to wear anything else under that jersey. I have lots of sun screen for us."

Charlene flashes that enticing smile my way as we are served our meal. While we eat, we discuss the game plan for upgrading the computer and telecom systems in the store. We will hit the ground running and put in a full day.

With breakfast finished, I pick up the tab. The company card gets its first use. We head over to the gate and wait for boarding. We compare our boarding numbers, whoever boards first always saves a seat for the other. This morning, Charlene has the magic number. Actually with all the flying we do, we are always in the A group, so finding a seat up front is never a problem.

Finally, the gate opens and boarding begins. Charlene is one of the first in line. She hands off her boarding pass and heads down the jet way. I soon follow and find her in row three, sitting in the middle seat. I plop down in the aisle seat and get situated. It doesn't take long for me to notice she has unbuttoned the three top buttons of her blouse. From my vantage point I have a clear view of her black lace brassiere and the mouthwatering cleavage formed by her luscious Double-D's.

"Starting early, are we?"

"I just thought I'd help you pass the time for the next ninety minutes. I know you get antsy when we fly."

Our luck was with us this morning. It was not a full flight and we managed to avoid having a seat mate next to the window. As far as anyone on the plane knew, we were a couple looking forward to a weekend getaway. Once we are up in the air, we settle back and relax. I try to relax, but the nearness of Charlene's tits has my cock twitching. She keeps smiling and adjusting herself which causes her blouse to flutter open. The more I look over, the more my cock hardens.

Halfway through the flight, after drinks and peanuts are served, Charlene does something completely out of character. She reaches over and places her hand on my thigh. I look at her with a quizzical expression. She winks and moves her palm ever so slowly up and over until she is resting her hand on my stiff shaft. I feel my cock pulse. She feels it too. She presses her hand down as if she is measuring my full seven inches.

Charlene leans over to me and whispers, "I think this weekend may be special."

At this point we hear the announcement to prepare the cabin for landing. Charlene removes her hand from me. We both look down and see the unmistakable outline of a bulge pressing up against my pants. Even the shape of my swollen glans is apparent under the fabric. Charlene looks me in the eye and smiles. As we make our decent into Phoenix, Charlene rearranges herself, buttons up her blouse and adjusts her seatbelt.

The plane arrives at the gate and we disembark. Charlene and I head to baggage claim. She has returned to her no nonsense approach to work. She acts as if nothing at all happened on the flight. Meanwhile my head is still turning and wondering what she means by a special weekend. I guess I'll have to wait and see. We grab our luggage and hop on the shuttle to the rental car garage.

The Scottsdale store is about a 20 minute drive from the airport and we arrive just before 10:00 AM. On the drive over we discussed our action plans for the data upgrades. Charlene rides shotgun while I maneuver through the city. I can't be sure, but I felt like she was staring at my crotch on the drive over, trying to catch a glimpse of my bulging cock. Or is it just my fertile imagination.

We enter the store and are greeted by the manager, Jim. We've been to this location on a few other occasions so we know our way around. On our way to the back office, Jim introduces us to some of the newer employees. We tell him about the upgrade plans and our agenda for the day. Once we are situated in the back office, the work begins.

Throughout the day Charlene and I work on our various projects and touch base with each other every so often. The day proceeds like any other. We don't break for a formal lunch as Jim has provided sandwiches and snacks. The hours pass by quickly and before we know it the clock on the wall strikes 6:00 PM. We have a couple of more hours of work ahead of us, but decide we both need a dinner break. Charlene wants to go to one of her favorite restaurants that is close by. She called over earlier and made a reservation. As we walk over to the restaurant, Charlene grabs my hand in hers. At this point I just go with the flow.

We enter and give our names at the front. Immediately we are shown to the table. It's one of those high backed semi-circular booths that provides a bit of privacy and also dampens the overall noise in the restaurant. I excuse myself and head to the men's room as Charlene gets situated and studies the menu. When I return, I see Charlene has moved to the center of the booth and placed my menu and silverware right next to hers.

I slide in the booth and Charlene beckons me to sit close to her. As I study the menu, I look over and see that Charlene has once again unbuttoned the top three buttons on her blouse. Just like on the airplane, I can see a fair amount of cleavage and her black lace bra. She looks at her menu as if nothing is unusual. We both make our dinner and drink choices.

Our server arrives to take our orders and is very attentive. Charlene suggested a pepper flake ahi appetizer which is delivered promptly.

Charlene whispers, "I love working with you and being here for dinner. I can't believe how quickly the day flew by."

I agree with her assessment. We enjoy lite conversation and look around the room. We both love to people watch. A moment or two passes and then I feel her hand rest upon my knee. She looks at me, grabs one of the ahi pieces and presses it to my lips. I instinctively open my mouth and take the food. Charlene's finger follows the ahi and I find myself sucking on her digit.

After I swallow the piece of tuna, I ask, "What are you doing, you little minx?"

"Just playing and enjoying the company."

I respond, "You know we have more work to do after dinner?"

"I know, but it will be just be you and me in the back office tonight. I hope we don't get into any trouble." With that said, Charlene moves her hand up my leg and starts massaging my inner thigh. I feel my cock start to respond to her wandering fingers.

Soon the main course arrives and Charlene requires both hands to eat. Reluctantly, she removes her hand, but not before dragging her palm across my semi-hard shaft. We talk about work and family and weekend plans as we eat. I steal glances down her blouse every so often. I know she sees me, but doesn't say a word. Her breasts move and sway as she eats. I find it hard to concentrate on our topics.

As we finish dinner, Charlene tells me to order ice cream for dessert as she excuses herself to the ladies room. Our server clears the plates and I place our dessert order. Charlene returns in five minutes and scoots in right next to me. She pushes her hip up against mine.

"Hello handsome. Do you have some dessert for me?"

Just as she says that, our ice cream arrives. As I dig into mine, I glance over and sneak another peek at my sexy work partner. I do a double take as I look and don't see her black lace bra.

Charlene looks at me with those big doe eyes and asks, "Is everything OK? How's the ice cream?"

I choke out a response as she sways in her seat. Her mammoth boobs shake from side to side under the green satin material. Another button was undone as well. I look and I swear I can see a bit of her nipple poking out. I try focusing on my ice cream but I'm thinking I'd love to suck on those tits for dessert.

We finish dessert and decide to head back to work. We work our way out of the booth. Charlene's tits shake and shimmy as she slides along the seat.

"Oops, I better button up before going back."

"Ya think?"

Charlene smiles at me as she buttons her blouse and then wraps and buttons her jacket. She grabs my hand again as we exit the restaurant. On our walk back to the store Charlene holds on tight.

"I like when you look at me and I hope you like the view. I don't mean to tease you, I hope you are OK?"

"I'm very OK." I say as I squeeze her hand.

We enter the store which is bustling with evening shoppers starting their weekend. We walk to the back office and pick up where we were before dinner. It's back to business for another few hours. By nine o'clock Charlene and I are both quite tired, but happy we completed our upgrades. It means we won't need to come back until Monday morning. We have the whole weekend to ourselves.

Charlene says as we are packing up, "Whew, I'm exhausted. I think I'll sleep well tonight. How about you, Rob?"

I agree, "Yes a good night sleep will do us both good."

I say one thing but think another. I should just take her back to my room and ravish her for all the teasing. I would love to get her out of that green blouse, pay homage to those tits and spend the rest of the weekend in bed.

We arrive at the hotel with our luggage and check in. Once we secure our room keys, I suggest a nightcap. Unfortunately I am rebuffed.

"I really am exhausted. I'm going straight to bed. I'll see you in the morning; we have the entire weekend for us."

Charlene kisses me on the lips and heads upstairs to her room. I am weary, but still wide awake. Charlene's teasing and innuendos have had my cock at half mast all day. I need to take care of the strain straight away and know what to do. I head up to my room. It's time to get out the Tablet and Fleshlight.

I take the elevator to the top floor and walk the few yards to my room. I open the door and throw my suitcase and laptop bag on the couch. There will be plenty of time to unpack later. Right now I just need three items. I open the suitcase and pull out my toiletries bag and my trusty sex toy. I kick off my shoes and head to the bathroom.

First things first, I turn on the hot water at the sink and let it run until steam rises. I fill the sink with hot water. I grab my Fleshlight, unscrew the top and pull out the inner silicon sheath, dropping it into the sink. Next I open my toiletries bag and pull out the warming lube. It's cherry flavored, but that won't matter tonight.

I take a towel out to the bed and rummage around my laptop bag for my Tablet and HDMI cable. It only takes a few minutes to connect my Tablet to the TV, turn on the flat screen and test the connection. I connect to the hotel's premium wifi. Once the connection is made, I climb onto the bed and dial up one of my tube sites that streams unlimited porn videos. Soon images of huge tits and eight inch cocks fill the TV screen. I lean back on the bed pillows, begin to unwind and enjoy the movies.

I search for my favorite category of sex videos, big tit amateurs. I fantasize that one day I'll come across a video that features Charlene. I know it will never happen, but it's fun to think about. As I watch a few short videos, I loosen my belt, unzip my khakis and run my palm over my cock. It feels good to finally release my hard shaft from within the confines of my pants. I only wish it was Charlene's hand stroking me.

I dip my left hand beneath my boxers and grab hold of my seven inches. Finally skin on skin and it feels good. I wrap my hand around my cock and slowly move it up and down. My cock gets harder with each stroke. I lift my hips and push down my boxers and pants at the same time. I remove the garments and settle back onto the mattress, watching the action on the TV. A well-endowed young lady is being fucked doggy style. Her tits hang down and sway with each thrust by her lover.

My cock is rock hard and I'm ready to get acquainted with my Fleshlight once again. I get off the bed and remove the rest of my clothes. Off comes my shirt and socks. My cock points straight ahead as I walk back into the bathroom. According to the Fleshlight's manufacturer, soaking the inner sleeve in hot water warms the silicon and provides a more realistic experience. I drain the sink and insert the inner sleeve back into the plastic casing. I grab my lube and walk back to the bed.

My favorite position is to stand at the side of the bed, hold the Fleshlight down on the side of the mattress while I pump my cock in and out of the make-believe pussy. I spread the towel over the bed and grab my lube. I pour a generous amount on my turgid shaft and the Fleshlight's opening. I hold my sex toy in place on the bed and line up the tip of my cock with the silicon opening.

The opening is shaped like a vagina with small labia on either side. There is even a small nub at the top of the opening to simulate a clit. The whole idea is amusing, but the sensation is stimulating to say the least. I never fail to have an intense orgasm with this aide.

My glans is swollen and easily slides into the opening. The tight silicon structure grips my cock as I slide back and forth. I hold the plastic case in place and begin pumping in earnest. The lube provides for a smooth stroke in and out. I focus on the action on the TV while I thrust my hips back and forth. A new video begins showing two Double-D starlets servicing one guy. He is on his back with one lady moving up and down on his cock while the other sits on his face. They face each other, kiss and play with their huge boobs, pinching each other's nipples in the process. The lucky guy is licking a very wet pussy while his cock is buried deep into the other.

I watch the action on the screen as I pump faster and faster into my own love toy. I imagine I am pumping into Charlene's very wet cunt as my orgasm builds. The action on the screen heats up as does my fertile imagination. My balls press against my sex toy as I bury my shaft as deep as I can within the silicone sheath. My cock is on fire. I feel my climax coming on. That familiar sensation at the root of my cock spirals up through my shaft to my over sensitive glans. My cock throbs with every movement. I piston in and out and in and out. I maintain my grip on the Fleshlight as my knees shake and thighs quiver. I am ever so close.