Traveling with Laen

The flight was on time, we were sipping coffee waiting to board and laughing about how early it was; what was ahead of us was a long flight and even longer meetings. Laken loved her coffee paired with heavy cream, it was the only thing she needed to be cheery this early.

Laken asked, "Want a sip?" As she handed me her coffee before I could reply.

I took a pleasurable sip, realizing we were close enough that sharing a drink was completely normal. She was so great to be around, conversely, I needed a little more time to be fully awake. Still, Laken always made me smile with her infectious energy, even before I was fully awake.

Watching her ready herself for the flight, I observed her casually flip her thick, dark shoulder length hair and even though happily married, I could not help noticing her attractive baby blue dress and smooth legs; the lotion, she must have put on earlier today, made them glisten. Also all too noticeable, in her form-fitting dress, was her chest which stood out against her yoga formed waist. I casually averted my eyes, hoping she didn't notice me checking her out at this early hour - or any hour, for that matter.

Being good friends, my checking her out was mostly innocent, I actually had no intention of ever cheating on my wife and also knew she was faithful to her husband, Manny. In fact, being comfortable travel partners was an important part of our jobs - sexual tension might not be the best scenario in the long-term. Still, I'll admit from time to time she did come up in an evening fantasy session. Those ended with me masturbating, thinking of her naked on top of me with my hands on her attractive chest, resulting in a slightly guilty, yet satisfying orgasm.

Those fantasy sessions might have been heightened by the fact that I had seen her naked a couple of times. And as such could fully imagine what it might be like to have her on top of me.

We often spent time at a mutual friend's lake place and as a group of friends, late night skinny dipping on warm summer nights happened. Laken was very bold and often one of the first ones naked diving in the lake. Her confidence probably elevated by her very nice body. Plus her fun personality made others play along. Though it is worth noting that in all our skinny dipping sessions, there was no touching, just admiring. Still, those nights seeing her naked were hard to forget.

The overhead call to board broke my momentary trance of remembering Laken fully naked in the water, my wife and I diving in to join her, her husband and about three other couples all splashing about.

On the plane, we had chosen to sit next to each other as we usually did when we traveled. As she sat down, she crossed her glimmering legs and immediately opened up one of the magazines she had purchased right before boarding. We were comfortable enough with each other that we didn't need to fill time chatting and could just hang out together. Gradually it was easy for us to both settle into the flight, me with my laptop and her with her magazines.

About an hour into the flight, I took my attention away from the laptop and noticed she had relaxed her posture and in doing so her dress had moved up further on her beautiful legs. I wasn't always this horny but for some reason today I was wound up. To make matters a tad more intense, one of her legs was lightly touching mine, in noticing this, I felt a little like a teenage boy at a movie with a new girl, not a 40-year-old adult traveling with a friend and coworker.

We were both so comfortable with each other, I had no idea at what point she had moved closer but she had. Now that I was aware of her closeness, I also took notice of her smell, which included a lite-citrusy perfume. She smelled fresh and sexy.

Deep into her magazine, she seemingly unconsciously shifted in even closer towards me, my male mind drifted and I started to wonder not only if it was on purpose but deeper still to the point of wondering what color and type of underwear were hidden beneath her dress. I tried to quickly divert these thoughts. I was suddenly thankful for the tray that held my computer, as there was a subtle tent growing in my jeans.

And just as I started to wonder if she could notice my predicament, she broke my fantasy and turned to me with her sparkling blue eyes said, "Hey let's take this quiz!"

I leaned over and saw it was one of those typical magazine quizzes, but this one was about sexual compatibility and nodded in appreciation.

She asked, "Do you want to do it together or answer it separately and compare answers?"

Jokingly I added that we needed to do it separately if it was to be real. Given the content of the quiz, I consciously wondered if she had any thoughts about me beyond our friendship. I was pretty certain she didn't - we never truly flirted with each other - it was always just friendly and fun. In fact as far back as I could remember knowing her our only physical touching was in hugs of greeting or departure. Still, between my thoughts, and this quiz - that tent in my jeans was not going down.

Jotting down our answers to the first question in the quiz - favorite position - the choices were - missionary, doggy style, sitting, cowgirl, standing. I choose doggy style. She flipped her answer over - doggy style as well. A max of 10 points for compatibility. We both laughed.

I said, "There sure weren't many chooses to choose from."

Without pause or change in tone, and somewhat surprisingly, she whispered, "It is easiest for me to orgasm from doggy, especially when Manny stimulates me with his fingers. Plus she added, "I like the man doing the work sometimes." She giggled at this revelation.

This conversation was more open than the conversations we usually had and I wasn't quite sure why.

The next question was - a favorite place to have sex. These choices weren't crazy either - bedroom, kitchen, outdoors, shower, car. I wanted to answer - any and all of the above - but it wasn't a choice, so I choose outdoors - the thrill of being exposed and finding a little bit different place made that a bit more exciting. Plus something about remembering the skinny dipping experience might have swayed me.

She flipped her paper over and had actually chosen the same - adding that she loved having sex with her husband at the lake in a chair outside wrapped in a blanket. Back to the lake!

I was seriously surprised by her openness today. I also added, "Wait is that the same chair I sit in when I'm at the lake with you two?"

Laken smiled teasingly and nodded.

Laken shared an additional little secret, "I often sit naked in that same chair, wrapped in a blanket sipping a glass of wine and just enjoying the lake view. I even sometimes do this when friends are around, just for the subtle challenge of not getting caught."

I shook my head, now wondering if she had ever been naked in that chair when I was around her.

Another 10 for our score. We had a max of 20.

Laken the added, "I don't know if our spouses would appreciate us being so compatible."

Instead of finishing the quiz though - which still had four more questions, she folded her magazine and asked - very bluntly, "Do you shave your privates?"

I was very surprised by her boldness today. She was an open person but this was a little out of character.

I answered, "I usually trim up the area but haven't gone bald."

She said, "Most of the time I do the same, but a warning here as this is maybe TMI, I wanted to surprise Manny last week so I shaved completely. He loved it so much I'm going to keep it that way for a while. Only thing is I have to use this special lotion to keep it smooth and itch-free and it is kind of expensive but works wonders. I even used it on my legs this morning."

Now knowing the secret to her glistening legs, I looked down and added, "It looks like it is worth it." I knew this was subtle flirting but given our conversation to this point I allowed it to come out.

She smiled and said, "Thank you for very much for saying that."

She then asked, "What's my best feature?"

I pondered, the innocent side of me wanted to say her eyes - which were deep blue and were, in fact, beautiful - but honestly, even though I'm not necessarily a boob man, I had to say she had awesome boobs. She playfully hit me at my response.

"You asked!," I replied.

She smiled and nodded. Just then the flight attendant announced we were landing so the two of us started gathering our things for readiness to get off the plane and to the meeting. That long flight was made much shorter by our intriguing conversation. I thought of other things so the tent in my pants would be less noticeable when I had to actually raise my tray. Lucky Laken had shifted to put her stuff away so didn't continue with the line of questioning she started.

After landing we completed traveled to our client and completed our long day of meetings. We then had an early dinner and a couple glasses of wine. We were both emotionally exhausted from the day so we decided to head back to the hotel and get ready for bed, knowing we had another long day ahead of us tomorrow.

After we checked in and headed to the elevator, Laken suggested we grab a nightcap before heading up.

I agreed thinking a nice glass of wine would taste great before bed. She led the way to the small bar. A few others are mingling about but for the most part, it is casual and on the quieter side. We each started with a few small sips.

Laken who was a huge sports fan, suddenly realized the Monday Night game was about to start - with that she said, "We need to go upstairs and watch!"

I suggested we could watch in the lobby but she thought it would be better upstairs. Explaining that we can get ready for bed, have the volume where we want, and still enjoy wine up there.

Agreeing with her logic was easy, I thought I would probably fall asleep before the end as I cozied up in my bed.

We took a ride up the elevator and she jumped off on the second floor, then added, "see you in a bit. I'm room 217, give me 15 minutes so I can take a quick shower and get ready for bed before coming back down."

I did not expect the invite for me to watch in her room. I figured we were going up to our separate rooms.

Before I could agree she was out of the elevator and gone. I actually wanted a shower myself so that after the game I could get back up to my room for a good night's sleep. After dashing through my shower and throwing on a t-shirt and a clean pair of comfy jeans, I headed back to Laken's room.

She texted that she would leave the door open at about the exact same time I was about to knock on her door. I walked in, announcing my presence.

She harkened back from the bathroom saying she was just about ready and asked me to find the game - controller was on the bed.

I walked deeper into the room, taking off my flip-flops and sat down on the bed, grabbed the controller and started searching for the game. I noticed Laken's blue dress, matching bra and panties were thrown casually on the floor next to her suitcase.

Laken came out of the bathroom a few seconds after I found the game, which showed the first drive. She then went to pour two glasses of wine. As she was walking over I could smell her freshly showered self, she handed me a glass of wine and sat down on the other side of the bed. It was then that I also noticed she was wearing a white cotton tee with no bra - her nipples were slightly poking against her shirt, paired with short white shorts. She looked amazing.

And in what seemed like the fifth time today, my penis started to grow in my pants. And for at least the fifth time, I tried to contain the thoughts that came with that experience, I also grabbed a pillow and put it in my lap and shook my head slightly. I knew I was having thoughts I shouldn't be having.

Again, I had never cheated on my wife and had absolutely no intention to tonight. Laken and I were friends and really to this point, while things were somewhat flirtatious they were generally innocent. In fact, had my wife been in the room with us, we would have all been piled on the bed and watched the game together. It just so happened Laken and I was alone in another town in a hotel on a bed.

Laken slid in under the covers and propped up pillows, I followed her lead and did the same. We watched about a quarter of the game, cheering and finishing our glasses of wine. We didn't flirt over the course of the quarter and it felt like we were back into our normal way of being.

Just as I thought that she jumped up and poured us two more glasses of wine and I again could not stop looking at her breasts, they were so big compared to her waist - and now her nipples were more pronounced. Her shirt had ridden up and her waist was exposed in a sexy manner, plus her ass was now partially visible at the bottom of her white shorts. This was especially true as she bent to get the wine bottle, I could not help but think thoughts of bending her further over and removing those shorts. I was pretty sure she did not have underwear on, given what I was seeing. What I was sure of, I needed to concentrate on the game and not Laken's body.

I got up to use the restroom and distract myself.

As we both came back to bed, her with the wine and me from the restroom, her leg again touched mine as we found our way under the covers. Then she said something very unexpected, "I'm about to bring something up that is really inappropriate - and I need to know if I should continue?"

I hesitated but answered, "Of course, we're friends."

She continued, "I am super horny but don't ever want to cheat on my husband or my friend." I was taken aback by this boldness as in all these years she had never flirted or been this overt sexually.

I nodded, "Same actually." I thought that would be the end of it and then immediately offered to go back to my room, "I can watch the game upstairs and we can still text the highlights of the game and have a conversation."

She immediately said, "No that is not why I mentioned it, I completely trust you and know we can control ourselves if we want." Then added, "I do have an idea to alleviate the tension though. Wanna hear it?"

I was confused by the whole dialogue because I was completely turned on but agreed with her completely and did not want to cheat. And still with that said, I did not dissuade the conversation at this point.

Her suggestion ended up being bolder than I suspected - to mutually masturbate - with a set of very specific rules. The rules included no touching the others privates and no kissing. Her idea was to masturbate together to orgasm and not cheat. She even suggested we could then continue watching the game more relaxed.

I was pretty sure her suggestion was on some level cheating. Even if we were just masturbating and not touching. No intercourse was a step in the right direction from a cheating standpoint, but still. My rationalization ended up being that I'd be masturbating one way or another tonight so I replied that I was up for it.

She smiled.

After a bit, she took a sip of wine and dimmed the lights without another word, at the same time I turned down the volume of the game.

Her next question, "Shirts on or off?" We figured one was way more innocent but maybe less fun.

Immediately my mind spun - I really wanted to see her boobs again - but clearly this was crossing another line. Again I rationalized, was it any different than skinny dipping as friends?

My horniness took over, "Off - let's be fully naked."

My question was next, "Where should I cum?" At home, if I masturbated with my wife, I'd cum on her breasts or ass or even once or twice - when my wife was really turned on, on her face.

Laken thought for about two seconds and said, "I'll grab something for you." She walked over to the pile of clothes she had been wearing earlier today, "How about in here?" And in the next moment, she tossed me her blue cotton panties, which had a super petite yellow lace bow as decoration. I was instantly rock solid.

I laughed and mocked, "They will do." I set her underwear on my stomach, seeing them there only made me hornier.

Smiling, clearly satisfied with her actions, she returned to the bed and got under the covers, then immediately slid off her shorts. I noticed that no underwear came off with them so I was guessing she did not have any on in the first place. Very gracefully her tight white top came off next. She was still under the covers so I could not see much of her body.

She added, "Okay your turn."

I first took my shirt off as she watched from under the covers, she had seen me without a shirt many at the lake but this seemed completely different somehow. I then slowly slid off my jeans and underwear. For this I had to stand up and was thus totally exposed. She watched the whole time and was paying a lot of attention to my now exposed 9-inch rock hard penis.

Looking directly at my penis she said, I might regret making the rules I did."

I shook my head and climbed back under the covers.

Her hand then started to go below the covers to what I imagined and hoped was landing between her legs.

I said, "Wait!"

She paused a little surprised, maybe thinking I wanted to stop the process, which I did not. There was a little disappointment in her expression. That changed when I asked her to hand me her hand and without hesitation, I proceeded to suck slowly on her fingers - the ones I imagined she was going to use to masturbate, she moaned in appreciation.

I added, "That should help you get started."

She smiled and said, "Okay now give me your hand."

I wasn't sure exactly what she was going to do when she opened my palm. She sat up, thankfully with her breasts now fully exposed, then very seductively spit a large amount of her wet saliva in my hand. It was incredibly sexy.

And added, "There, that should help you too."

I felt like I could cum just from watching her form the lips of her mouth to spit. I could not help but think about that mouth giving me a blow job if we broke the rules. With her propped up and the blankets up some, I could not only see her beautiful boobs more closely but also now see her hand working her clit and it was glistening. She was using the fingers I had lubricated to massage her clit. Her nipples looked rock hard and I was seriously considering breaking the rules and moving to kiss and suck them.

Instead, I worked her spit onto the tip and then the shaft of my penis and for whatever reason, the thought of that spit in my hand, made the experience different, better than using my own. I was so horny, so worked up but I purposely went very slowly. Not wanting to cum too fast or even first. Hoping this experience would last a while.

Laken though started breathing heavily and I wondered if she was already coming. She herself must have had similar thoughts as she slowed down her motion. She then moved her legs and put one over mine as she spread her legs further apart. This was a very sexy and intimate act. At the same time, she closed her free hand around mine.

She was now mostly exposed, as was I. The blankets pushed to the bottom of the bed. We were hot enough without them.

As she had mentioned she was completely shaved smooth. And I watched her as she played with her vulva for a while and then stuck her two middle fingers deep into her pussy. She gripped my hand tightly now and her smooth leg pressed more strongly into mine. Her chest moved up and down faster as she guided her fingers in and out.

Then she slowed down again and pulled her fingers out of her pussy and away from her glistening vulva and guided them to my mouth. It was awesome to taste her in this excited state. I moaned in pleasure.