This is the second series installment, post in Gay, Encounters. and maybe you can start a series for me as I will be submitting more soon. thx
I am a truck driver who drives all 48 states. I consider myself bisexual and am having the time of my life exploring my gay side here on the road. All my stories are true experiences that I encounter on the road. This is my second submission, but im backing up a bit from my first to get caught up. This encounter happened in early Feb, 2009. If you liked this story, please feel free to let me know. My email is truckerboy09@gmail.com
I grimace as I pull my big rig into the Pheonix, AZ terminal and approach the guard shack. My truck is due for a safety inspection and this particular terminal is one of the notorious prisons for us company drivers.. Its easy to get into, but hard to get out of. Sure enough as I sit in the safety lane, one of the mechanics puts a red tag on my truck. Im thinking to myself, there goes three days... "you tire tread depth isnt matching up on your drive axle, you have a leaky shock on the cab stabilizer, we'll fix those marker lights, and your block is developing an oil leak", he said as he looked up to me in the drivers seat. Now, once your truck is red tagged, you are not alowed drive the truck until its repaired.. so I knew with these particular repairs, the company would be providing me with a free hotel room for the next couple nights. "not so bad", I thought to myself. I tend to make the best of things.
I immediatly grabbed my duffle bag and filled it with everything I would need for the next couple days. Changes of underwear, sweats, shirts, socks, lube and a bottle of poppers... I smiled as I climbed out of my truck and walked to the shuttle, put my stuff in and asked the driver to take me to the hotel. The hotel provided is actually really nice, right off the interstate, and I got a bottom floor room... I managed to have a craigslist add up within 10 minutes, took a shower and checked for messages.
It was early evening, so I didnt get a lot of responses to my add yet. One older gentlemen did stick out. He was 55 and really wanting to play. He discribed himself as having an uncut 6.5" cock, very oral, likes to play with an ass, and available now. I do and always have gotten turned on by older gents. I find them to be more experienced, horny, and usually a bit on the kinky side.. which I like. I could see in his pic his cock wasn't really that big.. just an average cock, looked more like 6" and not that thick at all. Usually 7" would be my minimum for a thinner cock, I thought to myself that this could still be fun.. The whole idea turned me on so I gave him the hotel name, my room number and invited him over.
I put on some sweats with no underwear underneath and a simple white t-shirt, put the lube and poppers in the nightstand drawer next to the bed. Just then I heard a soft knock at the door. I opened it and saw him, he was a pretty good looking older daddy type, about 5'10, thin, mustache and about a days worth of stubble. I stepped away from the door, gave him a smile and he walked right in not saying a word. I sat on the edge of the bed and he stood in front of me looking down. Immediately, I rubbed his soft daddy cock through his jeans and unbuttoned his pants, pulled them down along with his underwear and took his now semi hard cock into my mouth.
His cock was pretty easy to suck because of its average size. I concentrated on the his uncut cockhead, swirling my tongue inside his foreskin around the edges of his bulb. I would then suck his skin up and over and nibble a bit, then slide my tounge back through the skin and prod at his piss slit. This was getting him rock hard, he was breathing heavy.. "oooh yea, baby" he said as he grabbed the back of my head and pushed his cock in my mouth. I grabbed the base of his cock and pulled the skin down and started sucking down the shaft. With its perfect size for my mouth, I could really work his cock and take it in all the way to his pubes without gagging as the tip of his rock hard cock pressed against the back of my throat. For the next couple minutes, I contunued sucking.. then he stopped me. He was good, hard, and horny and had something else in mind.
He took of his shirt and pushed me back on the bed as he said, "lemme see that nice boy ass of yours". He pulled down my sweatpants and my cock snapped straight up, he gave it a really quick suck and reached his hand down under my balls and started to rub his fingers around my asshole, massaging it in circles. He looked me straight in the eyes, smiled, and said, "thats a nice tight asshole you got there, and I bet its going to taste great!" With that he turned me over on my stomache and spread apart my ass cheeks. I buried my face in the pillow as I felt his tongue lapping at my hole. It felt great as he would lick all the way up and down my ass crack and then back to my rosebud, flicking his tongue barely inside. I was breathing very deeply now, I was in heaven. He sucked, tongued, and rimmed my ass for a good 15 minutes.. then I felt a finger penetrate my hole "aaaaaaah, yeaa!", I moaned.. I reached over, and opened the drawer handed him the lube and put the poppers on the nightstand. "Yea, I love playing with a nice tight hole.. You like that"?, he asked.. "Yea, I love having my hole played with, it feels so good", I replied. He opened the lube and applied it to my hot hole and penetrated me with now two very wet and slippery fingers.. all the way in, I could feel his nuckles pushing hard between my ass cheeks and against the rim of my hole, stretching it wider as he twisted his fingers inside my canal.. sliding in and out, loosening me up.. making me wet.. making my hole very hot inside... It felt great and I wanted more.
Without a word he rolled me over on my back and lifted my legs, applied more lube on my asshole and on his fingers.. I closed my eyes as I felt another penetration that stretched my hole even more.. Three fingers now were sliding in and out of my now juicy asshole.. same as before twisting back and forth inside my canal. "ooooh, yeaa.. that feels so good" I told him. I thought to myself how nice it was to have this dirty older man playing with my ass.. Just then I felt the entrance of my ass being stretched even more as he inserted a forth finger.. sliding in and out he looked me in the eyes and could tell I was really enjoying the intense feelings in my hungry ass.. he then applied more lube, cupped all his fingers and his thumb together and pushed inside gently, being careful not to hurt me as he worked up to his second nuckles. He said "push down on it"... I reached over and grabbed the poppers because all this felt so great, my hole was now stretched to its limit, but I still wanted more... It felt soo good and I've never experienced anything like this. I took a large hit of poppers and pushed down on his hand.. his fingers and thumb were still cupped as I worked my way all the way down to his knuckles. "your a reall man for taking that", he said as he applied lube all over the rest of his hand.. He was going to try and fist me and just the thought of it made me quiver and push against his hand even more. He was now applying steady firm pressure, pressing into my asshole.. I have never experienced the euphoria of being stretched so much, took another hit of poppers and I could feel him twisting and pushing, trying to get his big nuckles inside past my first ring...All of a sudden it went from euphoria to intense pain as I felt as I was going to be ripped and had to stop him. My entire body was flushed, heart beating, breathing heavy, and I could feel beads of sweat running down my face.. He withdrew and said, "you almost had it all the way in man, almost." I replied, " it was awesome, but I dont think Im ready yet to take a fist.. im really glad we tried".
I sat up and took his cock back into my mouth. It was still hard, playing with my hot hungry ass really had him going. I could feel my hole was very wet, stretched, sloppy, and had a very empty feeling now.. but it was satisfied. To my suprise he said, im gonna fuck that ass now. I thought to myself who would want to fuck a sloppy stretched out asshole, but OK. He laid me on my stomache on the edge of the bed and quickly rammed his entire cock inside to the balls. He stood there and gyrated inside me swirling his hard cock in circles inside my hole. I could feel the walls of my inner ass actually and naturally squeezing around his cock without my effort and I could feel the head of his uncut cock deep inside me being squeezed by my swollen prostate. It felt so good, but how could my ass be so tight after such a workout I though to myself as he started ramming me hard. "ohhh baby, thats a nice tight ass", he said as he grabbed my shoulders and pushed his cock in as far as it would go. I am breathing heavy now, this was actually a very nice fucking.. better than I expected. I could feel his cock making short powerful thrusts inside my well lubed ass and hitting my prostate perfectly with every jab. His breathing got heavier and his thrusts got harder and even more forceful as he plunged in and out of me.. I could feel his cock swelling inside me and knew he was about to explode inside me. I closed my eyes and concentrated on what I was feeling going on inside my asshole waiting to feel the warm flood of cum. "ahh yea baby, im going to cum in your ass, Im gonna cumm.. ahhh ahhhh" He pushed in as far as he could and just held it in there as his whole body shook with his orgasm. i could feel the warmth of his cum spilling against my sensitive prostate deep inside my ass. It felt like my entire asshole was on fire, like someone had inserted a dildo soaked in steaming hot water deep in my ass. This older gent has satisfied me like nobody has done before. As he pulled out, I fell on my back and he sat on the edge of the bed and caught his breath.
"man, that was amazing", I said. He replied "this was so much more than I expected, you are by far the hottest and horniest boy I have ever fucked.. Thank you". We sat there and chatted naked for a few minutes then he started putting on his socks and getting dressed. I just lay naked savoring the after effects of what I just received. I smiled and looked at him with my boyish face, he smiled back and said he wanted to get together next time I was in town. "absolutely!!" I told him that I would keep his email and look him up next time I was in Phoenix. We exchanged goodbyes and he headed out the door.
For the next couple weeks I would just think back about how close I came to getting fisted and how good it felt having all five fingers inside me. Many many times, I would be rollin' in my rig down the highway and think about actually getting an entire fist in me, and that day with that older man. My cock would get hard just thinkin about it, making me squeeze it and play with it through my jeans as I look down at passing motorists with a grin on my face.
This is a true experience I had on the road. Please let me know if you liked it, I plan to write more as I have to get caught up to date. Email me truckerboy09@gmail.com The next story I will post happened in Fontana, CA when I actually did get fisted. Who knows, I might even be in your town soon!