Travelling Companion Part 1

***This story is completely fictitious*** ***None of these characters are real and none of the events ever happened*** ***Please read the Extended Disclaimer below*** ***I do accept commissions on stories if you wish to contact me directly, either by Kik Messenger at MissedFives, Email at MissedFives@Gmail.com, or on our Discord Server. Pledging on FanBox as a Best Boi gets you access to all 100+ completed stories as well as ONE FREE commission! ***You can join the FanBox with this link: MissedFives.FanBox.cc/plans ***Here is the link to our Discord Server: https://discord.gg/tYGCzq6edA ***These stories are 100% my works of art and intellectual property of Missed Fives. That being said, please enjoy what I have created so far and don't forget to leave some love (Likes) on this post. Let me know in quotes what part of the story made you cum (Comments) underneath this post. I'd really like that! ***Extended Disclaimer: All of the characters in this story are actors in a play that are consenting adults over the age of 21. None of the characters are related to each other in any way and anything contained in the performance depicted below fall under the Roleplay and Fantasy Kinks respectively. *~*~*~*~* Beginning of Story *~*~*~*~* I’ve been a traveling salesman all my life, ever since I learned that I could buy something from someone and then resell it to someone else for more money. Everyone in my family has already settled down and had children but not me. I consider myself the rolling stone of the family, always traveling to new places and meeting new people. Something about the victory of selling something to a person who wasn’t expecting to buy anything filled me with power and control. When I was young, I sold magazine subscriptions and now that it’s the new millennium and we all have all made it through a pandemic together, I sell little pocket vagina’s called fleshlights. This lockdown has left so many people feeling lonely and isolated… I of course find it very easy to sell these little toys now to alleviate such negative emotions and bring pleasure to people’s lives again. Of course the fact that now I am sexually arousing my clients to sell them something they weren’t expecting works in my favor as well. I always carried two suitcases with me. One had my demo units inside in order to allow my customers to see and feel the product. It was my experience that if I can get a potential buyer to hold the product, that they will most definitely purchase one from me. The other suitcase I had of course held all of the sealed and brand new units, which the customer would receive immediately upon sale. I was getting seated on a plane back to Alabama, so I placed my new unit suitcase in the overhead compartment. My demo suitcase of course I wanted to hold on my lap... My demo suitcase was special to me. It was given to me by my little sister a couple of years back. She was the only family member that ever truly accepted my way of life. I know we had some very interesting experiences together on some of our road trips selling things in the past. Hotels and motels… As my mind began to wander, my finger moved towards the back end of my suitcase. There I had a small worn in hole that I refused to fix. Circling the hole with my middle finger, my eyes glazed over as my mind went down countless memories of being alone with my little sister. Drawing circles, I finally slid my finger inside and felt the soft creases of the unit inside. Running my finger along the chubby bald lips I couldn’t help but slowly become aroused. It didn’t matter to me that there were people around me. It needed lubrication so I stealthily put my finger in my mouth and moved the glob of saliva back to the hole of my suitcase. Inside I went… found the hole… and pushed my finger inside of it. The feeling of power rushed through me. Not just of doing whatever I wanted whenever I wanted… but also in public with so many potential witnesses. To this day I am still amazed at how unbelievably tight it is. Sliding in and out with so much friction that I couldn’t go faster, I noticed myself licking my lips. I had to stop this… someone would figure out that I was being lewd. Sliding my finger gently out of the tight hole, I traveled lower and found those wonderfully small wrinkles I enjoy so much. Rubbing gently in a circle, I felt the hole slowly opening and accommodating my middle finger as well. I had less saliva for this one but I forced it in and out just as hard as the previous hole. The arousal was getting too much to handle as I started thinking about heading off to the bathroom to take care of my needs. This is when I remembered that I was on the redline back to Alabama, and that as soon as the plane was in the air, the lights would turn out and everyone would most likely try and sleep. I decided to wait for then to vent my sexual frustration. Just as I hoped, after a while the plane had taken off and the lights were turned out for the night. I just had to be patient. In the darkness of my seat next to the window… I quietly pulled out my cock and began to stroke it with about a dozen strangers around me. It was exhilarating as my cock filled to an impressive 8 inches. I lubed up my cock with my spit and rubbed it some more… I was excited to the point where I could have burst right then and there, but I decided to raise the stakes. I tilted my suitcase with the hole facing downwards and slid my thick cock inside. Resting my suitcase on my lap, my cock went right inside towards the unit. The tip of my cock felt the smooth lips spread apart… so far apart to make room for my cock head. It wasn’t going in very fast ad the unit was in the process of stretching… My cock was bent slightly as the rest of the weight of the suitcase pressed on my lap. Having no where else to go, my cock straightened out with a gradual motion and sank itself deep inside. The heavenly feeling of this hole… it was so tight and inviting. So forbidden. My brain tingled with the thrill of what I was doing as the contents of the suitcase shifted violently. I held onto it as the weight dropped just a little more and I felt that final inch make way. With a bump… I felt my cock enter completely and hit the back of the unit. It was all the way inside. Every slight motion… every vibration from the plane… sent shivers though my cock head. It was enough for me to sit back and relax and eventually cum. I didn’t even have to move my hips. The hole was perfect for me… so warm... “Is there anything I can get you Sir?” I heard as I turned to my side and noticed the stewardess in the dark. She had startled me! “OH! No, thank you…” I responded trying not to act suspicious. My eyes focused as I noticed a beautiful blonde doing a polite squat next to me with her knees together. For a split second, she looked just like my sister… but that couldn’t be. For a brief moment we looked at each other as I actually felt my cock grow larger… the fact that she was staring at me while I was inside the unit and about to cum… I was getting a little too large it felt as there suddenly was no stretch anymore. “Normally we don’t allow passengers to hold onto their luggage during flight.” she continued on with a slight look of worry on her face. “Oh yes, I understand,” I began while thinking up the rest of my excuse… “See, I’m afraid of flying and squeezing this suitcase makes me feel a little less anxious.” I concluded. I was very proud of my on the fly excuse and felt that it was going to be good enough to get me out of being found out. The vibrations were making it difficult to keep myself contained though… it was so unbelievably tight and my entire cock head was lit up with sensations ready to make me burst. “I think you might have to put it in the overhead compartment just to be safe.” she said while giving me a sympathetic look. “I can’t do that…” I started as the stewardess shifted her balance a little bit to listen. “See my little sister gave this to me…” I continued. “...She passed away last year.” “Oh, I’m sorry to hear that” the stewardess said in a consoling voice. I continued on with my story feeling this would work in my favor. “She and her husband died in a car accident last year leaving behind my niece.” “Oh no… poor child.” I could hear in her voice that she was invested so I continued on. “It’s ok though, I was the godfather so I took her in. She has been the reason why I work so hard. I want to give her a wonderful life you know?” “I understand that completely.” The stewardess agreed. “Well, just be sure that if the seat belt sign turns on that you buckle up and if you can, place the suitcase on the floor.” she compromised as she reached forward to place her hand gently on my shoulder. At that very moment the plane hit a large pocket of turbulence and the stewardess braced herself gently against me for support. It was only a couple of seconds, but it was enough for my cock to slide in and out of the unit just enough to trigger my climax. I leaned back with the touch of the stewardess and focused on my cock. I could feel the pulse from my sack pump up my cum through my shaft as my cock head lit up in ecstasy. Spurt after spurt, I silently came inside the unit and felt it ooze along my shaft lubing me up. My cum was being forced out of of the hole it being so tight and I felt myself free up from the friction now that everything was sloppy. I had shudders of mini climaxes while the stewardess got herself standing. I could feel more cum pushing out of me and filling up the unit. She looked at the seat belt sign just when it turned on and gave me a look of “I told you so.” “I totally understand, will do.” came out of my mouth in response. I was glad that the cabin was dark or else she would have noticed that I had the glow from freshly cumming. After she walked away, I let my cock get squeezed out of the tight hole as most of the cum was cleaned off. Putting my cock away, I couldn’t help but feel the orgasm wasn’t completely finished. I was going to have to stop by a bathroom and finish off the rest when we land. Sure enough, about thirty minutes later we landed. As I took both of my suitcases with me the stewardess said her farewell. “I’m sorry again for your sister,” she began. “How old is your niece if you don’t mind me asking?” I answered her question with a simple “two” as she cooed and said that it was a nice age and that she was going to be fine. At two, toddlers don’t remember much and she will only have memories of her wonderful godfather. I smiled and made my way down the walkway while looking for a bathroom of sorts to finish taking care of my business. The suitcases were heavy and my cock was beginning to grow again. It was so very early in the morning, which made this even more difficult for me. I found a room labeled, “changing room” as I went inside and closed the door. Luckily this room had a lock, so I barricaded myself and put my demo suitcase on the table with the hole facing the edge. I was slowly starting to lose my composure as I dropped my pants, kicked off one ankle, gripped my cock and shoved it back inside the hole of the suitcase. This time there was no resistance… no friction… my cock head pushed it’s way inside the slimy hole all the way to the back. With a bump, I knew I was fully inside and began moving my hips forward and backward. I tilted my head back as I relished the feeling of being inside this soiled and tight hole. Leaning back and putting my weight into my thrusts, I fucked harder and harder until I felt the sweet feeling of relief coming closer and closer. This was it. This was going to be the entire load. Not just a couple of spurts… It hit me like a brick wall as I began to cum with such power that I had to pull the suitcase towards me while fucking forward. I was hitting the back wall of the unit so hard that part of me was worried I was going to damage it. Before I really began caring for that, my climax was finished. I had felt like gallons of semen had left my body and filled the unit my cock was destroying. Along my shaft, I could feel my cum oozing out. A slight feeling of annoyance crept into me as I realized that I was going to have to clean up the mess at some point, but then I remembered a game that I had started playing last year. Last year when I began sticking my cock into the suitcase and fucking the unit inside, I would open it up and see which hole I was inside! But first I had to guess and then reveal if I was right or not! Alright… I stood there for a while with my cock still buried inside completely. Not just the tip… my entire shaft was pushed all the way in, my cock head gently bending at the back of the unit. I looked up at the ceiling and went through the events of the plane flight. Let’s see… I fingered one hole, lubed my finger, fingered the same hole… hmmmm Then I fingered the other hole… which one was the one I slid into when I set it on my lap? I know from past experience that the second hole stretches faster and takes more of me inside… hmmm But I did finger the other hole twice and it could have been lined up with the hole of the suitcase when I flipped it onto my lap… this one was a bit tough. I decided to cheat a little bit and move my cock in and out of the hole I was inside… hmmm I don’t feel any wrinkles and I have a clear back that I am hitting… I moved my hips gently forward and tapped the back of the unit with the head of my cock. “Yes… this has to be your cervix!” I said out loud as I opened the suitcase and folded the top to the side. “I was right! I am inside your little cunny hole sweetie!” I cooed Under me laying on the table was my 2 year old niece. She was naked of course with her hands tied behind her head. I had a special custom size dildo gag made for her that was strapped to her face and in her mouth to keep her from making sounds while we traveled. I admired looking at her and how flexible she was as a toddler. I had stretched her legs up and over her so that I could tie her ankles behind her head as well. This of course gave me full access to both of her holes at the bottom of the suitcase where the hole of the suitcase was! It was ingenious I thought. Speaking of holes, I was right. My 8 inch cock was fully buried inside her tiny 2 year old cunny hole. It was bright red and pink but undamaged as this wasn’t the first time that she had taken care of my needs while we traveled. It was stretched so nicely… her bald puffy toddler lips looked so beautiful wrapped around my cock. The inside of the suitcase was messy though. I was right about that as well. My cum had gotten everywhere. On both of her sides were the actual demo units of the fleshlights that I sell and almost all of them had a little bit of me splashed on them. My niece of course needed a bath from what I saw. ALL of her nether region was covered in my thick white cum and most of it was sitting in a pool on her smooth belly, drowning her belly button. I pushed my cock in and out of her a little just to watch as the sight was one of the most thrilling I had ever seen. I don’t believe it was ever going to loose its appeal to me. Maybe tonight I would remove her from her bondage for a proper cleaning… then I could use her other hole to even things out a little bit. Pulling my cock out of her 2 year old cunny for a second time within the hour, the gaping hole remained a little, oozing out thick globs of my cum. I looked around for something to clean her with and frustrated, I just shoved one of the demo units inside of her to stop the leak. “I will clean you at home.” I said while twisting the unit deeper inside her toddler pussy. I looked one more time to check to see if she was leaking any more and after I was satisfied that all of my fluids were sealed within her, I closed the lid again. Making my way to the taxi out front with my two suitcases, I settled in the back while cradling the demo suitcase in my lap. The taxi driver turned back and asked me if I wanted to put that suitcase in the truck with the other one and I began my story over again about the death of my sister and how important this suitcase was to me. “It’s going to be a long drive, your choice” he said as he turned around again and started the drive. He was right. The drive to my hometown was going to be two and a half hours. My fluids would be plugged up inside of her for that entire time. I had a decision to make… Let it stay inside her… have her soak all of me up over the next two and a half hours? Or have a pit stop somewhere at a halfway point… maybe a truck stop bathroom… clean her up and abuse her other hole to even her out a bit?