Hitchhiker’s First Time (Part 1)


It was a warm sunny day as I stood on the side of the road. The semi-arid landscape seemed to go on forever and heat waves rippled near the surface of the ribbon of pavement that stretched to infinity in both directions. Wearing nothing but well-worn hiking boots, a pair of running shorts that seemed almost too short, and an old backpack, my lean slender body glistened with sweat under the desert sun. It was not my intention to show off my body, in fact I was quite self- conscious about it, I was just trying to be comfortable. Though I was in my late teens I was still about as smooth as a girl and wondered if I would ever develop some manly looking body hair. Passing cars were few and I had now walked about three miles from the small town where I had stayed the night. With each passing vehicle my hopes for getting a ride diminished a bit more. Then I spotted something large approaching but it was still just a speck on the horizon.
Soon I could tell it was another semi, since lots of these had already passed me I didn’t get my hopes up. Though I was sure it was in vain, I stuck my thumb out anyway. As the massive truck came closer it slowed and pulled onto the shoulder, much to my astonishment.  The massive vehicle pulled up right in front of me and stopped; against the loud drone of the hot engine I heard the driver’s door open and close. Then the driver walked around the front of the truck and came over to me. His size got my attention immediately. He was about six foot three, middle-aged, had a goatee, and must have been pushing three hundred pounds, with a husky but not fat build. He was overall a stereotypical trucker.
“Hi, need a ride?” he said sounding much less intimidating than his physical appearance would suggest.
“Sure.” I said with a mix of excitement and apprehension.
“Cool, it’ll be nice to have some company on the long stretches coming up. We’ll get going in just a minute, just need to take a leak.”
He glanced around to make sure the coast was clear, unzipped his fly, pulled out a very sizable penis and proceeded to pee next to me. I couldn’t help but cop a look as the clear yellow fluid squirted from his glans onto the gravel.
“If you need to go I suggest you do it now, it’s gonna be a long haul till the next rest area.” He counseled.  I declined because I didn’t need to and was too shy anyway. He finished, zipped up, and said “Well, let’s hit the road.”
Clambering aboard the huge truck I was impressed by its size and power. The seats of the cab were so far off the ground it gave a nearly god-like perspective of one’s surroundings. Then off we went. We got acquainted and he said his name was Bill. He said the trailer was empty and he was headed home having made his last delivery so he had some leeway in his schedule. As the miles rolled by we talked. When we were having lunch at a roadside diner he asked the purpose of my trip. Basically I told him I was doing it for the adventure, to try new things, and learn more about myself.  He said he certainly understood and respected that.
The drive continued uneventfully and I think we were both surprised at our compatibility despite our obvious differences. Day had given way to night and Bill said he needed some rest. We parked at the next rest area, used the restroom and we went to his truck’s sleeper.  It wasn’t large or fancy, just a comfortable bed in an alcove that took up most of the space, some drawers and a couple hooks to hang clothes on.
While removing his shirt he said,”I sleep in the buff, hope you don’t mind.”
I wasn’t exactly but I said it was ok with me.  He wasted no time and stripped completely naked in front of me. His body was even more imposing now with abundant body hair, a bit of a belly, and powerful, muscular limbs. His penis was far larger than mine and hung several inches from his trunk.  He was the first fully adult man I had ever seen nude.  My feelings about it were very confused but I found it hard to not stare at his penis as I sat on the bed removing my boots.
“I noticed earlier that your muscles are all knotted up, I can loosen them for you. I was a masseuse a long time ago.” he said.  “We can do it just like at the resort I worked at. Sound good?”
My muscles did seem sore so I reluctantly said, “Sure, I guess so.”
“Great, undress the rest of the way and lay down on your belly.  I need to get a few things,” he said, as he pulled some items out of a drawer.
Now I was really uneasy about this but did as he asked anyway dropping my shorts and undies to floor and stepping out of them.   Ashamed of my little penis I quickly laid my very naked body on the bed and nervously waited.
“Comfortable?” he inquired as he placed the stuff in his hands on the other side of the bed.  “Yeah.”  I replied, my head flat on the sheets.  He went back and got a small laptop, put in a disc and forwarded it. “Would you like to watch some porn while I work on you?”
Being from an actively religious family I’d had very limited exposure to porn and thought it would be cool watching girls getting fucked so with some excitement I said, “Sure.”
He set the laptop down in front of me then I felt his strong hands moistened by massage oil kneading the sore muscles of my shoulders and upper back. “It might be a bit different than what you’re used to,” he said.
That was an understatement.  On the screen of the laptop was a close-up of a person’s bottom and a male hand, pointer finger extended approached the clearly shown anus and gently started to press against it. Then it pushed gradually deeper until it sank all the way into the rectum and started fucking it. I wondered if they were really going to show the girl getting butt fucked.
More immediate however were Bill’s strong hands lubed with oil deeply massaging my back and working ever lower down my body. It felt really nice and between his touch and watching the activity on the screen I started to wonder if my butt would be involved in his massage or how he would handle it. His hands were now at the small of my back working lower and lower.
The laptop now showed two fingers sliding in and out of the hole. Bills hands slipped over the sides of my hips and on to the outer regions of my thighs. When he finally reached my feet and massaged them he started on the inside of my legs working back up. I wondered how far up he would come. As I watched the screen, the fingers were removed and the camera zoomed out to show that the butt belonged to a GUY on all fours! Kneeling upright behind him was another guy with a big erect cock slowly sliding it into his ass. I couldn’t help myself and suddenly got a big erection, but I was straight! Or at least I’d always thought I was.
The two guys on the screen were  fucking earnestly when a shiver shot though me.  Bill’s hands were on my buns massaging them and getting close to my butt crack. His hands pressed firmly on my cheeks and pulled them apart to reveal my puckered little anus.  He was likely the first to lay eyes on it since my infancy.
“Beautiful little hole you have here!” he said as his pointer finger slowly slid down the length of my butt crack and brushed the pink flesh of my opening causing a powerful shiver to shoot through me.   “Do you like what you see there?” he asked, his finger caressing it. “Kind of.”  I replied, not wanting to let him know how intrigued and curious I really was. “You said earlier that the purpose of your trip was to explore and try new things…”

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