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Straight Hitchhikers's First Ana

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 250 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." 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 I 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 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 now 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 since he was on the inside of my thighs. 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 and learn more about yourself. You have a chance right now to do exactly that you know. Have you ever been fucked like that guy?" "No" I replied softly. "Ever had anything in your butt?" "No". I said. "Now be honest, you're curious aren't you, how it feels to have a cock fucking you in your ass like that aren't you? "Yes" I said in a near whisper unable to hide the truth. "Do you want to do what they're doing? Do you want to feel my cock fucking you in your ass?" Barely audible and to my total dismay as if a third person was speaking through me, I said "Yeah". "Cool! Lay on your side and bend your legs as much you can for me. Oh, and put your dick on the backside of your legs, It's more comfortable that way." Bill instructed as he clambered onto the bed and grabbed a bottle of lube from the other side. I did as he said and got into position. Bill started rubbing my buns then fondled my penis and ball sac k. It felt nice. Next, he lubed up his finger and touched my anus with his cold slimy finger caressing it gently for a couple minutes. Then he pushed and I gasped as it suddenly slipped all the way into my rectum. I suddenly felt my penis go stiff as a board and since it was at the back of my drawn up legs I knew Bill saw it. Bill chuckled, "Well, judging from your hard on I can tell you like my finger in there, just wait. Let's see if you can handle two fingers now. If you can take them, you're probably ready for my cock. A bit more lube and the next thing I knew, I had two fingers in me exploring my inner passage. "This is your prostate." he said as he pressed his fingers against the front wall of my rectum and massaged it. A pleasurable spasm sent chills through my body and I let out a groan. "Nice huh?" he said as his big fingers fucked my hole. A few minutes more and I had really loosened up. "Well kid, you're ready for your fucking. Now you need to get me ready." he said grabbing a condom and the lube. I sat up to see Bill lying on his back with his huge penis hard as a steel pipe. "Have you ever handled another guy's cock? Go ahead, grab it and explore it but don't make me cum, I want to do that in you." he said. It had to have been well over eight inches long with bulging greenish veins and a tip the size a large plumb, it virtually reeked manhood and sexuality. I had only ever played around with my own cock, never another guy's. My hand squeezed the soft, rubbery tip, caressed the meaty shaft and hefted his weighty balls. It was terrifying and highly arousing to think it would soon be inside me. Bill handed me the condom and showed me how to pinch the end and roll it all the way down the shaft. He squirted copious amounts of lube on it and had me smear it all over his organ. "Ok kid we're both ready now. Time to lose your anal virginity. We're gonna do it the way they're doing it on the vid now. Having been so caught up with mine and Bill's activities I had almost forgotten the porn was still playing on the laptop. It was showing a side view of the guy on his back, his legs drawn way up and his ankles over the shoulders of the guy who was vigorously fucking his hole! This was going to be intense!
Bill put a pillow down and told me to lie on my back with it under my hips explaining it would be more comfortable for me. Trembling from fear, anticipation and lust I did as he said and brought my long smooth, athletic legs back till my knees rested on my chest. The farther I drew them back the more I felt my buttocks separate fully exposing Bill's target, my anus! Never had I felt more exposed and vulnerable.
Just to be sure, Bill put even more lube on my hole then instructed me to relax my butt and take deep breaths as he entered me. Peeking around my raised legs I watched as his massive hairy body approached me. He arced above my scant five foot eight one hundred thirty seven pound frame in a kind of push up position straddling me with his muscular arms. Taking aim he lowered his hips and a shiver jolted through my body as the bulbous tip of his cock nestled against my reluctant orifice. "If you need me to slow down or stop let me know. I'll go slow." he said in comforting tones. He stared pushing and retreating over and over each push a bit harder and deeper than the last. "Remember to breath deep and exhale slowly, it really helps." he reminded me. I did exactly that and tried to relax as much as possible. My sphincter was slowly surrendering to the intruder and I felt myself stretching wider and wider, and wider still. The discomfort was starting to morph into pain just as my anus suddenly gave up its resistance and the rubbery, bulbous tip popped through my sphincter and I gasped. With the hard part over, the shaft followed easing with exquisite slowness into the hot, slick, velvet soft chambers of my rectum. Deeper and deeper and deeper it sank and with every inch the pleasure increased. Finally I felt his hairy groin press against my own then pause. Nothing had ever been in me this deep! "DAMN! THAT FEELS GOOD! YOU'RE SO TIGHT IN THERE! Doin ok there?" he asked. Answering I said" Yeah! It feels great!" I wasn't lying, between the sensations around my hole and the hard to describe feeling of fullness it was far better than I had imagined. After letting his penis get used to being in me by staying still for a minute or so, Bill started humping me and it felt even better. He dwarfed my slender body. With my legs still on my chest, his big penis pounded into my smooth virtually hairless bottom and his heavy balls slapped rhythmically against my buttocks. I WAS GETTING FUCKED! And fucked hard by a huge middle-aged trucker in the sleeper of his semi! What did this mean? How was it that till this night I had had no clue how much pleasure my lowly butt could offer. After fucking me on my back for several minutes Bill said "Let's try it another way. I want to see my cock going in and out of your butthole."
He had me Kneel on the edge of the bed while resting my head on the sheets with my behind and feet hanging over. He stood on the floor behind me and plunged his eager cock far into my youthful bottom. The porn flick was now showing close-ups as a guy was getting fucked doggystyle. It was amazing to realize that was probably what it would look like if I could see Bill's cock sliding in and out of my butt. The pleasure just kept coming. "You like having my big cock fucking you in you in your cute little potty hole don't you?" Bill said as his mighty organ pounded away in me. "Yes!" I managed to gasp as his cock slowed way down, nearly withdrew all the way then slid back into the deepest recesses of my rectum in long, slow strokes.
Next he put me on my belly, slid his dick between my buttocks and back into my bowels. He wasn't as deep this way but the sensations were intense, maybe he was rubbing my prostate better this way. Bill's groin made a loud, slapping sound and I could feel my butt cheeks ripple as he fucked. It was also very exciting as his big dick rubbed against baby smooth cheeks of my butt crack. It was great but I wanted something different. "Can we do it the first way again?" I asked. "Sure, that's my favorite position anyway and I bet we can get even deeper now." He said as he pulled out of me.
Once again I placed the pillow under my hips, lay on my back and pulled my knees back to my chest. Bill mounted me again, positioned his cock, and then with little effort slowly slid it deeper into my rectum than it had ever been. "Oh Yeah!" I gasped as it literally bottomed out and I felt his groin pressing against my wide open bottom. He started thrusting in and out of me like a piston. It felt heavenly. "Squeeze me boy. Squeeze me with your ass!" he grunted. I tried and clamped down hard on his pounding dick with my sphincter muscles. "OH YEAH! THAT'S IT, I'M CUMMING! "He exclaimed throwing his head back. Deep in my bowels I felt his penis throb as he let out a loud grunt. As the last pulsations ebbed he pulled out of my well used hole and removed the condom sagging under the weight of his ejaculate. Holding it up like a trophy he said, "Look what you made me do! You ok ?" Suddenly I felt vacant and incomplete without a cock in me. I replied, "Yeah that was amazing!" Discarding the condom bill said, "OK, your turn to cum, just stay like that. He lubed up two fingers and slipped them back inside me and began to seriously massage my prostate while his other hand started working hard on my balls and penis. The combined pleasure was so great my penis soon erupted spewing semen all over but mostly on my own body. "Damn you're a great fuck! One of the best I've ever had!" he said as we cleaned up. I glanced over at the laptop to see extreme close-ups of a big, long cock pumping in and out of a guy's hole when suddenly it pulled out and squirted everywhere, very appropriate I thought. Soon we turned out the light, got in bed still naked, and drifted off to sleep.
Bill fucked me again in the morning before we took off but not for as long and later in the day we stopped in a beautiful wooded area where he fucked me hard from behind as I braced myself against a tree. An hour later we arrived at a town where we had to go our separate ways. Bill had been right; it certainly had fit with the purpose behind my trip, that of new experiences. It sure had been that.
Bill had opened my eyes to a world of pleasure I had never considered. I have since fucked and been fucked many times but that first time will always be special.