Picking up a Stray

A fantasy tale of traveling alone on a dark highway and wanting some company.

I had been driving long run truck routes for a few years now. Coast to coast, border to border on the back roads of the states.

We take the back roads because we encounter less humanity, less governmental restrictions. And being private contractors we haul let's say things government agencies might take issue with.

I was on a long haul through the great smokey mountains of Tennessee on a hot August night. I was driving a big van on this trip, that made it a little nicer, and cooler than a big rig. Kinda like a motor home with no windows, all black and kinda like somethingout of a movie. It was getting late and driving alone we know to stop and rest so we have no issues. I was on a pretty secluded road, and I saw a nice place to pull over and rest.

I climbed in back and settled in.

I had been sleeping comfortably for hours when there was a pounding on the door.

I grabbed my 9mm from the lock box, checked the cameras to see who was there.

He looked all of 17, 18...very skinny, 5' 6" maybe, shaggy shoulder length hair.

I opened the back door "can I help you boy"

I asked. "Sorry Sir, I didn't know if anyone was in there" he stammered..."what are you doing way out here, there's nothing around here for 100s of miles" I asked. "I was kicked out of the home because I just turned 18" he said.

"I've been walking for a few days, and I'm thirsty, and hungry" he continued.

"Well, sounds like you have a problem young man" I said smiling. In my mind I was salivating, he was 18, legal and all.

I wasn't into Minors, fuck that. But an 18 year old that looks like a young boy or girl....I can definitely do that.

"Look kid, I can help, but it ain't free" I said. "I'm broke mister" he said. "I'm sure we can figure something out, come to some agreement" I said.

I opened the back door and let the boy in.

He grabbed a seat on the bench. I pulled out a couple water bottles and a sandwich from the cooler and gave it to him. He downed a bottle of water and tore into the sandwich.

He finished his sandwich, and the second bottle of water and leaned back and was dozing off. I figured if I let him sleep and I could check things out. He fell asleep pretty quickly.

As he laid there sleeping I studied his body.

Small, petite almost. He has a sweet young female figure. I traced his thigh to his slender hips, flat stomach, I started sliding my hand down to his almost flat crotch...I could feel a small cock. I guess I rubbed a little too much as the boy jumped up. "No!" He said "I'm not gay" he continued.

"Relax boy" I said. "Look son, I said we would have to come to an agreement on that food, drinks and a safe bed." I continued

"Look mister, I can't, I've never done anything like this" he said shaking.. "the way I see it there are two ways that this is going to play out" I continued "either you're going to undo your pants and let me see that little cock of yours, or I will take your pants off myself and see that little cock of yours" I said firmly. Reaching for my wallet I could see the indecision in is eyes...

I took a $100.00 bill from my wallet, put it in the palm of my hand and placed it on his cock. He took the money from under my hand, leaving my hand on his crotch.

He started to stand and slowly unbutton his pants..."Nice and slow boy, I want to enjoy this" one by one he popped his 501 buttons.

I could see he wasn't wearing any underwear.

As he got to the last button his pants fell to the ground. He stood there for me to see...

He was almost hairless, his cock was thin and short. I reached out to fondle it and he jumped "relax boy" i said and continued to fondle his little cock. It was soft, and pink.

I slid my hand between his legs and pulled him forward swallowing his little cock in my mouth, again he jumped and tried to pull back, I just held him tight and continued sucking. His little cock was growing in my mouth. His moans intensified, I could tell he has never been sucked. His little cock was hard as steel and about 4 inches.

I slowed down and asked "you ok boy, you enjoying yourself" "yes sir" he said.

"Undo my pants" I said. He looked at me with an almost fearful look and started undoing my belt. I leaned back so he could undo them easily. He did my belt, slowly undid my button, lowered my zipper and stopped..."keep going, take it out" I demanded

He hesitated and grabbed my cock. I could see on his face he was in a daze of should I or shouldn't I...he pulled me out and softly rubbed it. His eyes opened wide as he got a look of my cock. I'm not huge, but I have a great cock. Strong 7 inches, thick shaft and a fat mushroom head. "Go ahead, put your mouth on it like I did to yours" I said "I can't sir, I just can't" he said. "Sure you can, just lick it softly, touch it" I said to him. I put my hand on the back of his neck and slowly pulled him forward to my cock. He licked the shaft softly. He put the head in his mouth and swirled his tongue around it.

I push his head down on my cock more and he gagged pulling up. I laughed, "easy boy, just relax" I said lifting my hips and pulling my pants off the rest of the way. I pulled him back down towards my hardening cock. He swallowed more this time. He really started getting into it. My hands were exploring his soft body, he was hairless from head to toe with just a little pubic hair. I fondled his ass cheeks, he really seemed to like that as he moaned while sucking my cock. I started to spread his cheeks so I could see his hole better, this made him stop sucking me and look up with total fear in his eyes. I think he realized that this wasn't stopping at a blow job. I pushed his head back down on my cock again, licked my finger and started massaging his tight pink virgin hole. He was moaning, squirming his ass, almost pushing back on my finger. My cock was rock hard at this point and he was struggling with it. I could tell he was starting to enjoy himself as he was trying to get more and more in his mouth...I pulled him up and positioned him on my lap. I kissed him forcefully and he didn't pull away, he kinda went limp letting me have my way with him. I kissed him, fondled his body. I know he was intrigued because he was starting to grind his hips in my cock that was standing hard between his ass cheeks.

We kissed for a bit longer and I decided it's time, I'm going to de-flower this young man.

I rolled him off of me and laid him on his back, ass on the edge of the bed and knelt down between his legs. His little cock still hard. I put my tongue to his asshole and started working it. I could tell he was really loving it. He was moaning, twisting and turning...I figured the time was right, I slid my pinky finger in breaking the seel on his virgin ass. He jerked back..."Sir, I can't, I've never done this, it's going to hurt" he said.

"Yes it will boy" I said. "But I will take my time and you will enjoy yourself" I continued.

He laid back again getting as comfortable as he could...I slid my pinky all the way in and he let out a muffled scream. I pulled it back out and slid it back in. I did this for a few times, then switched to my middle finger and he noticed...his moans were getting louder, his body was twisting and squirming. I reached in the bedside drawer and grabbed my lube.

I sprayed some on his hole and my finger, sliding it back in all the way. He enjoyed that.

I lowered my head taking his rock hard little cock in my mouth and he jumped. He arched his back as I worked a second finger in his asshole. I probed his insides with my fingers as I continued to suck his cock. I knew he wasn't going to last but I didn't care. I sucked and finger him till he screamed out shooting ropes of cum down my throat. His cum was sweet and hot. I kept sucking and fingering him till he was dry of his juice. I sat up, gently lifting both his legs to my shoulders, I leaned in and kissed him softly. "I'm going to fuck you now, I'm going to bury my cock in you and you are going to love it" I whispered.

"Please sir, I'm a virgin, it's going to hurt" he said "yes, yes it will, and my cum will flow through you making your asshole mine" I continued "please sir" he started as I placed my cock at the entrance to his tiny tight pink hole...once again he begged "please sir, I can't" and with that I popped his cherry, and stuffed my thick mushroom head in his asshole. He jerked up but I was holding him tight, he could move anywhere. "Relax, that's just the tip" I said. Tears were forming in is eyes, I slid more of my cock in. His tears started running down his cheeks...I grabbed the lube and sprayed more on my cock shaft and is asshole. I slid more and more in him.

I could see the pain level was intense for him. I let him adjust a bit to the size in him. As he closed his eyes and continued to cry I decided it was time...I slid out a bit, and slammed balls deep in his virgin ass. He screamed like a school girl, tears ran down his face. I held him steady and let his asshole feel my girth. I slid back out a little and back in. I was going slowly so he could adjust to the pain. I leaned in whispering "your ass is mine now boy, I am going to impregnate you and your going to love it" and started working my cock in and out. I hadn't had a virgin in a long time, he was so tight it was heaven.

He was crying like a child who had his favorite toy taken from him but I just kept fucking him. I could tell he was changing, his tears were drying up, and his moaning had intensified, he was starting to move his hips.

I kept my pace up pretty good pounding him.

I slowed and removed my cock, I started to roll him over on his stomach, placed a pillow under him so his ass was up ready for anything...I stood up behind him and lined up my cock to his hole and slammed it deep.

He lunged forward a bit then to my surprise he wiggled his ass backwards so his ass took all of me. I continued working is ass knowing I was going to cum soon. I pounded him hard so he knew I was in charge. I could hear his moans as I pummeled his young prostate.

I reached under and felt his little cock and it was hard again and leaking cum. I pumped his ass and his cock simultaneously.

He tensed up and came once again and I knew what to do. I sped up my pace and was fucking him like he was a whore. I felt my balls tingling, my rod pulsating and rammed one last deep thrust filling his ass with my seed. I kept pumping my cum in his ass.

Thrust after thrust I pounded him.

I slowed allowing my cock to pop out. I slid my fingers in his hole scooping my cum up and raised it to his mouth and made him clean my fingers. He did so to my delight.

I leaned back and took a deep breath and to my surprise my little friend rolled forward and started licking my cock and cleaning it up.

He was really working it, I started getting hard again and in no time I shot another load deep into his mouth. He continued eating it all down, continued to clean my cock and then slid up on my chest to rest.

We laid there and dozed off to sleep.

I wasn't sure how long we slept but I was waking up and he was still lying on me, head on my lap. His soft body was like nothing I've had. He was like a little girl I used to fuck when I was a teen. She was in her 20s and could pass for 13. He had much of the same attributes. Feminine curved hips, flat stomach, high tight butt cheeks. I was thinking as he laid there sleeping. If I put him in pigtails, and a little dress, maybe some light makeup he would be a perfect little sissy slut.

I started stroking my cock again as it started getting hard thinking about my new little toy all dressed up and worshipping my cock. I slid my hand down his back as he laid on me, finding his ass, I slip my finger in his crack and massaged his hole. He squirmed on me twitching slightly as to say yes sir, enter me. I found the lube, squirted some on my hand and worked my finger deep in his asshole again. He looked up at me and started sliding up my body so he was sitting on my lap. My cock was hard and sitting nicely between his ass cheeks...he lifted up some so I could position my cock at his hole, he leaned in and kissed me softly...and sat all the way down on my cock...he screamed and tears ran down his face but he smiled and stared lifting up and slamming back down, I knew I owned this boy know. He bounced like a slut up and down on my cock till I tightened up and filled his ass again with my seed.

He sat there for a moment with his head on my chest and my cock still in him. As my cock softened and poped out of his ass he rolled off. I stood up and went into the bathroom to clean up.

I came out and started getting dressed, and told him to as well.

"Where can I drop you boy" I said

"I have nowhere to go, I don't have anyone or anything" he said softly. "Can I ride with you for a while?" He asked with sad puppy dog eyes. "Look boy, you ride with me we will have to discuss your future and what you're willing to do for me" I said "anything sir" he replied smiling.

I thought to myself, he has no fucking idea what he just agreed to...

We got in the front of the truck and started heading out.

I looked over at him, he was staring out the window with a little smile on his face.

Yeah, I own him now.

I hope you enjoyed this tale. And you got just as hard as I did writing it. The open road is full of surprises, and I can't wait to see where this story goes.