Back many a year ago, after I finished college, I decided that I was not ready to enter the job market right away. I had grown up on a farm in Virginia and attended a college near Richmond, but had never ventured far from my home. Someone suggested that I should get out and see the world, if not at least the U. S. This thought stuck with me until I decided that I would back-pack my way around the country. Since I was rather poor and in debt to my parents, for what I imagined to be the rest of my life, buying a car or even a bus ticket was not a realistic way to get around the country. I thought I my try to stop in all of the southern states. I had even thought I would go as far as Alaska. My only affordable means of travel were walk'en and thumb'en. After a few days of figuring out what I could at maximum carry on my back, and thinking about where I might want to go first, I headed out to start what would be a most memorable odyssey.
My dad drove me out to the nearest highway, which wasn't any where near our home. He was not pleased with my back-packing trip, which he saw as a dangerous waste of time. On the way, he unloaded all of the fatherly advise he could come up with. The only piece of advice I still remember is, 'Don't get into any car you feel uncomfortable about. Another car will be by sooner or later.' He dropped me off on the southbound ramp, wished me well, told me to keep in touch every week, gave me some cash and just left me standing at the side of the road. Without a serious plan, and only a cheap U. S. atlas to go by, I stuck out my thumb and hoped for a friendly face. "Maybe I will try to visit every state in the country...."
I really did not know how I would deal with eating on my meager budget. Soon the money I brought along ran out, and I found myself begging the managers of fast-food or truck-stop restaurants for any food that they couldn't sell. Somehow, I always found someplace to eat each day. I wasn't eating three squares, but enough. I developed a knack for finding a lone trucker at truck-stop lunch counter and would strike up a conversation with him. Sometimes after hearing a bit of my story, I would be offered a bite to eat, a ride to the next state, or even use of the truck-stop shower facilities.
Those words of my father kept coming back to me every time a car stopped to offer me a ride. It is true you sometimes meet some rather strange people on the highway. Often, though, it was a trucker looking for company for a while, sometimes it was people who just felt sorry for me. I kept myself clean, as best I could, shaved daily, and dressed comfortably. I did not want to fit the bill of your regular hitch-hiker. As the old joke goes, 'Why is it that hitch-hikers look like someone you would never want to let into your car?' The other side of the coin is that being a good-looking young hitchhiker (in my early 20's), I attracted people I did not count on. I had thought my biggest fear was meeting someone who would take me down an old dirt road and try to rob me. Since I carried little or no money, I didn't worry too much about it. Most of the people who picked me up were just friendly folks looking to help, but the number of men who stopped looking for _s_e_x_ was significant.
Now my _s_e_x_uality is something I was still working through. My memories of my high-school years are of me chasing the girls and finally laying one before I headed off to college. For me, college opened up many opportunities for _s_e_x_. I discovered in those days that I could be _s_e_x_ually stimulated by girls and boys (or should I say men). When I tied to understand this bit of _s_e_x_ual confusion, I seemed to reason that my childhood memories of love from men, always seemed to take to form of being spanked at home or paddled in school. Even my grandfather, whom I loved as a father, was not shy about warming my backside. I was not a bad kid, maybe a bit mischievous. Though I would have _s_e_x_ with boys my age, I would fantasize that they were older than myself and wanting to spank me.
Back on the road, these things would come to mind. How the issue of _s_e_x_ was broached was as diverse as the people who stopped to offer me a ride. Sometimes it would be as simple as being asked if I liked boys or girls. Sometimes, the hand would miss the shifter and land on my knee-cap. I passed on at least half, and would soon find myself let out of the car soon after. There is a way you know right away if you want to be touched by someone or not. From a few I was able to secure a bed to stay in for the night, and others were happy just to blow me. I discovered that truck stops were a great place to find a ride from someone who wanted _s_e_x_. After a while, I found myself hoping and even fantasizing about the next fellow who would pick me up.
After bouncing through all of the southern states and then to the beaches of Florida, I decided to head to Texas. When I reached Texas, it seemed like a cool thing to hit all of the big cities starting with Dallas. Not much developed in Dallas, but outside of Dallas heading toward Houston, I was picked up by a short elderly man in a late model Jaguar. Mind you, this was my first time in a Jag, and my eyes were all over this car, and I hardly noticed the man driving. After introducing himself as Bob, he immediately jumps into small talk -- Where am I from?.... Where am I going?... How old am I? I was half paying attention and sputtering off answers while following the lines of the dashboard and gauges and the fanciest radio I had ever seen. I was snapped out of car-lust when he asked something that I didn't quite understand. I looked at him and said "Huh? What's that you asked?" He paused for a moment keeping his eyes on the road, took a deep breath and asked, "Would you let me _f_u_c_k_ you for $100." For the first time I sat up and took a good look at this man. Silver hair, strong jaw, and rather good looking. He was in a business suit, so anything else about him I could only guess. I didn't answer right away. I had never been _f_u_c_k_ed, and did not think I would like it. The money sure could be useful, and I wouldn't mind seeing this man in his birthday suit. Immediately my dick was twitching in my jeans, as I just stared at him. I wasn't sure what to say at first.
Without much thought, I decided to go for broke. I still hadn't answered, and he broke the silence with a rather strong and maybe even demanding, "WELL?" At this point I found his demanding manner annoying. I shot back, "I'm sorry, I don't think you can afford me". He sat up straight and looked at me and with an attitude and responded, "What $100 is not enough, what do you want? $500? A Grand? Well your not worth it." Half yelling as punctuated his final "it". I was half expecting him to stop the car and let me out, but he drove on. I waited for him to say something. After a few minutes, he calmly asks what he can't afford. I took a deep breath and began, "I'll let you _f_u_c_k_ me, if you can get past my tight virgin asshole, but only if I can have my way with you." He smiled and asked, "What do you have in mind." My heart was racing as I continued, "I would like to tie you down and spank you and even whip you with a rod of some sort until you cry like a baby."
He sat in stone silence for a long time. He would look at me now and then, but said nothing. Finally, he said, "That sounds like an interesting arrangement. You whip me and then I _f_u_c_k_ you. I think we have a deal. This is more than I was hoping for. You could even spend the night at my place." We shook on it and spoke little of it until we reached his house outside of Houston. It was smart ranch house with lots and lots of land. Far bigger than my daddy's farm. I couldn't see a neighbor in any direction. Quite private, and a swimming pool to boot. He showed me around his house and stables. He was divorced with no children and, according to him, now with a late blooming interest in having _s_e_x_ with men. It was late afternoon and he offered me food and a shower or even a dip in the pool if I preferred. He didn't offer to shower with me, but I didn't mind. I really needed a moment alone. I found a bathrobe waiting for me when I got out of the shower. It took great effort not to jack-off, just thinking about what might happen next. I found him in the kitchen, in his bathrobe making food for the two of us. I wanted to hug him, but he seemed not to want to get into it that moment. I did think that I saw his dick poking from inside his robe, but he never opened up. So I kept my bathrobe closed as well. We didn't talk about our agreement, just small talk about his farm.
After we ate, he suggested that we go out to the barn. We were still both in bathrobes at this point. Passing some trees on the way out to the barn, I stopped and searched the branches over our heads. "Whatcha looking for?", he snapped. "Something to whip you with," I responded, not looking in his direction. He headed off to the barn without me, and I found a long straight branch, but not too thick that made a great swishing noise when I swung it through the air.
Apparently, when I was in the shower, he was setting the scene for me in the barn. In the middle of the floor, was a modified saw horse. The lights seemed to be especially bright in the center of the floor. He had wrapped some carpets around the horizontal part of the sawhorse, probably to make his position there more comfortable. I was surprised that so much effort had gone into setting up the sawhorse, as I had not even thought about this part. I asked, "Where are the ropes? We agreed that you would be tied down." He left and came right back with some long thin leather straps. He walked over to a hook on the wall to hang up his bathrobe. So I took mine off as well, keeping my eyes on him the whole time. For the first time I was looking at the man in all his glory. He must have been about 65 years and was he beautiful from head to toe. White air, strong arms, no gut, broad smooth chest with almost no hair, and one huge erect penis (must have been 10" or 12" and much thicker than mine) with a proportional set of balls to go with it. His dick was so un-proportional to his height, as he wasn't more than 5'5" tall. I was a bit embarrassed, as my 6" cut-penis paled in comparison. I felt kind of weak all of the sudden. I didn't want that tree in my ass. "Let's get the show on the road", he shouted.
He started to try to un-nerve me by shouting off orders. "I'm giving you my ass, but don't break skin or cause bleeding, or hit me anywhere but my ass. I don't want any permanent scars, and ...." I cut him off and shouted back, "Bend over the horse already, and stop your whining -- you big baby." He straightened up with a huff of disgust and walked over to the sawhorse. I shouted, "Spread your legs wide and bend over." He bent over, and I secured his hands and his feet to the four legs of the sawhorse. "Now listen", I said matching his tone and volume, "We never agreed that only your ass would be whipped or that you would not bleed. We only agreed that I would be free to whip you until such time as I think I have had enough." Every time you open your mouth, except to plead for mercy, I will strike you somewhere outside of the area of your ass. The first time you threaten me, I will play billiards with your balls." I took my time and walked around him, checking out the view of Bob from every angle. Seeing his balls and his penis dangling down from between his legs as well as his asshole, wide open for me, I could have eaten him. Until this point, I did not occur to me that I would have a change to _f_u_c_k_ him, but I had never been so turned on by the site of an asshole before this.
I slid my hands around his body for the first time. Feeling the firmness of his chest and the contours of his legs. The grand prize was his mighty penis.... his magnificent penis. I got down underneath him and slid my tongue around the head. I had to get completely underneath in order to take his whole dick in my mouth and into my throat. I could not take it all without choking, I had never sucked anything this big before. While I was mouthing his dick, he was squirming with what I understood to be enjoyment. Finally, he whispered to me, "Please don't blow me, I want to save it for your ass." I moved behind him, and knelt down to face his ass and tongued his ass-hole and the outline of his scrotum. He squirmed with delight at my tongue in his ass. "That is incredible, please don't stop," he said sounding like he was on the verge of an orgasm. His balls were massive and I felt empowered holding them in my hands. I had only dreamed of balls as perfect as these.
I stood up and asked, "Are you ready?" He responded with a half-hearted, "Have a ball". I started spanking him with a bit of rhythm, as though they were a pair of drums. Harder and harder I spanked him. I changed my strategy when I felt I was not getting through to him. I tried winding up and slapping his ass with great force, left cheek, and then right cheek, and on.... He squirmed a bit and his penis was hard and long, pressing into the bar of the sawhorse. I would take a break from spanking him to see how his dick was reacting. It seemed as though his balls had tightened up some. His ass was quite red at this point. When the numbness left my hands, I continued to slap his cheeks as hard as I could, except this time concentrating on slapping his asshole.
Eventually, I took a break and sat down on a bail of hay behind him, so that I could study this man from his best side, and examine my progress. Up to this point he had hardly said anything. I think that he was determined not to give me the satisfaction of breaking down. "How's it going?" I asked. "If you are finished, I am ready to get off this thing," he replied. "Oh, we have yet to get started," I said as I picked up the tree-branch I had carried in with me. Cleaning off the extra bits and leaves, I wondered how long was too long. This branch was about 6 feet long, and tapered down to a thin point, and as flexible as a rubber hose. I swished it through the air over his body, just to give him chance to hear the sound of inevitability. He body immediately tensed up and I could see him trying to get his hands free. I yelled, "The moment one of your hands gets free I will cut your balls off with my whip." He stopped fighting his wrist-ties. I could hear him cursing me under his breath.
"These first couple swings will help me determine if I need to shorten my stick any." I wound my arm back and nailed him across the center of his buttocks. His whole body shuddered and he let go with a mighty, "AH _f_u_c_k_!" A welt rose up in a straight red line across both cheeks. I ran my fingers along the welt and smiled. My next swing was much harder, and the SMACK upon impact was loud. He swore again, of course. The welt this time was even larger, and I started to wonder if my whip was too long, as I had hardly started and already I was afraid of tearing the skin off his ass. I cut a foot off of my switch and tried again. The result this time was closer to a bruise, and more of what I was looking for. After about five stripes, he was begging me to stop, if not, just for a break of a few minutes. "Please let me go, I have had enough," he said with a slight quiver in his voice. "I'm just getting started. I think I have found the right form of swing, and the length of the switch feels great," I responded After about five minutes, I picked up the switch and started swinging again, without any warning to him. CRACK --- I caught him unprepared. "YOU SON OF A BITCH", he yelled, followed by a sustained scream of pain. "For THAT, you get one across the thigh," I yelled. CRACK -- I swung faster than before and I tried to cover every part of his ass, even in the crack of the ass-hole. On occasion I would venture further down his legs, but not too far from his ass. I did not want to destroy him, but I wanted him to beg me to stop. I suppose his pride, which I had early on suspected was very strong, would not give in too easily. His ass was an interesting shade of red and purple. His breathing became more rapid as the whipping continued, I could hear him saying under his breath, "Please stop" but he never addressed those pleas to me, until finally. "Stop....Stop....Please Stop. I can't take anymore. I'll give you anything if you stop hitting me." CRACK --- CRACK --- CRACK. "I'll give you a $1000 if you would stop hitting me" His voice was almost childlike with a quiver that made his words difficult to understand. I put the stick down and walked over to the bath-robe that I wore into the barn and found a tube of salve that I pulled out of my bag after my shower. I rubbed some of the salve in my hands and began to gently smooth the salve over his ass. I offered terms for stopping, "There is something else I want to do." "Anything, just please don't hit me", he groaned. Without saying anything I forced some of the salve into his ass-hole and smeared a bit over my prick. Carefully, I lined my prick up to his asshole and slowly pressed it in. His ass was really tight, and I did not go in easily. He yelled out in pain, "Please don't do that, I have never let anyone do that before." Not replying, I paused a bit to give his hole a chance to adjust, and then I pushed my dick in a little more. Slowly, I inched my way in until I was completely in. Then slowly I slid my dick back out and then pushed it in again. At this point he wasn't complaining anymore and seemed to be enjoying it. I found I enjoyed the experience better when I pulled my dick out completely an then re-inserted a fresh. I had penetrated a kid at college once, but I had never gone all the way before. Finally, I started to feel an orgasm coming on. I pumped faster and faster until, "Ahhhhhhhhhh, I'm coming, Ahhhhhhh....." I pushed my dick in all the way, and bent over his body and reached around to grab his dick as I released my load. That was the most incredible thing I had ever done.
I pulled my dick out of Bob and bent down to untie his hands and feet. He did not get up very fast. He took his time. When I finally saw his face, it was red and a bit puffy. I had broken him. He put both hands on his ass and then tried looking at the damage. He shook his head and headed back to the house without his bath-robe. He kept saying under his breath, "you son of a bitch".
I carried both bathrobes, and followed him back to the house. Bob went to his room and closed the door. I went to the guest room and headed for the shower. I wondered about what I had done to this man. I kind of felt guilty. I took a piss and then climbed into the shower. I soaped and cleaned my dick very well even with an antibacterial lotion I carried in my back-pack.
After I had dried myself, I came out of my room to see if Bob was around. His bed-room door was open and he wasn't around. I wasn't sure I wanted to go back to the barn just yet, but curiosity got the best of me.
PART II
Going back out to the barn, it was already dark out. The air was still warm, and so I didn't bother with the bathrobe. At first I didn't see him, but hearing something in the loft, I yelled "Hey Bob!" "I'll be down in a moment" he replied. Going out into the middle of the barn, I could see him coming down the ladder backwards and the fruit of my handy work in plain view. My semi-hard dick became rock solid.
"Ready for act two?" :he asked.
"I'm really sorry for the damage I caused you. I got a little carried away."
"That's nice, now get over to the saw-horse and bend over. NOW!" He demanded.
"What do you have in mind?" :I wondered.
"Don't you worry your pretty little head about details," he shot back.
His magnificent penis was soft and hanging low. I was now really nervous about what he would do next. I walked over to the saw-horse and bent over, spreading my legs and preparing my ass to meet his dick. He immediately started to try to tie my hands. I protested, "What's up, this was not part of the agreement."
"Stop your whining. If the ties worked so good when you were in charge, I really think you need to know them first hand now that I am calling the shots. I followed your orders, now you will follow mine. Now bend over and hold still while I tie you down." He moved quickly, and tied my hands really tight, I think tighter than I tied him. He was a bit rougher on me than I was on him. It occurred to me that I have created a monster, an now he is out for blood. I wanted to go home.
He decided he needed to give me a little speech. "Never have I been beaten so badly. I submitted as we had agreed, but you abused your power when you _f_u_c_k_ed me without provocation. So now I claim full authority over your ass and the rest of your body, and you will remember this day for the rest of your life." He slid his hands around my body, and examined my ass-hole. "Your ass-hole sure looks small, I suppose I will have to widen it or rip you a new one" and then he laughed to himself. Suddenly I heard a loud swooshing sound, and before it registered, I heard and felt a loud CRACK across my ass. I screamed in pain. He's going to whip me! Oh God! My right leg spasmed for a moment, and my whole body became rigid and tense. It was now clear to me that I would now be getting the whipping of my life. I begged him not to do it, but he laughed. CRACK-- the next one landed halfway down my thigh, and again I yelled out with a "AAAAhhh.....Please Stop..".
"Now we will be doing this just a little differently", he explained. From now on, instead of you yelling 'Stop', you will be yelling 'Please hit me harder this time'. If you fail to beg, "Please hit me harder this time" , I will slap your balls, with ever increasing force until you beg. You will continue to beg, until I tire of this game. Then, I will _f_u_c_k_ your brains out. Do you have any questions?"
I paused for a moment, to collect my thoughts and wonder what I do next, when suddenly, WHAP, he slaps my balls. "Aahhhh!" I cried. "Please whip me again, harder than before" CRACK my ass is in flames at this point. "Whip me again, harder than before", I begged.
"What's the magic word", he enquired.
"PLEASE whip me", I cried. CRACK- my whole body was shaking. Compared to myself, he took it all very well; after a few strokes I feel like a weak little boy. He had only started and I was ready to cry. "Please whip me, harder this time." CRACK – he finds my ass on target. After about fifteen times, I could barely speak. I was having difficulty getting the words out. SWAP- my balls are in pain again and feeling like they have swelled up. "Please....please....please stop, I ....I ....can't take anymore...." SWAP-- My balls are in distress again. "AAAhhhh." He whipped my back, my legs and of course my ass. I tried not crying, but holding back only made the pain worse. "Please whip me harder this time" – CRACK -- "Please whip me harder this time" – CRACK -- "Please whip me harder this time" – CRACK....
Finally he paused for a moment. "Beg me one more time", he demanded.
"Please.... please.... whip me once more,.... but even harder", I said slowly with my eyes filled with tears and my throat going horse.
CRACK – The pain radiated through my whole body and I thought I would pass out.
Right in front of me he throws the branch (the same I had used on him) to the ground. It was over. I was relieved. But when I looked around for him, I saw him standing to the side with horse-whip, like those used for breaking new horses into submission. Suddenly he started attacking my ass with this whip. I screamed as it felt like he was tearing the flesh off of my ass. "Please stop....please stop...." I cried like a baby. But he continued to whip my legs and my back . "After what seemed like an eternity of crying "Stop", I began to beg for anything that would get him to stop. Then I cried, "Please _f_u_c_k_ ME!"
He stopped whipping me. I laid there sobbing and my whole body racked in pain. He said nothing and I did not know what he was up to, all I could think about was how bad my ass and my whole body hurt. Then I felt a hand smoothing over my ass and down my legs and back up to my balls and my penis. He stuck his finger in my ass and pushed it in all the way, but my ass-hole was not cooperating. It took him a while to get two fingers in. He was stretching my asshole in ways it wasn't designed to be stretched. The pain was incredible, and I was sure that I was bleeding out the ass, as the pain was so great. I could fell him pressing some grease into my asshole.
He was now trying to get his dick in my ass. He pushed, and I yelled in pain. "It is too big for my ass", I cried. But he ignored me and just kept trying to get it in. He kept pushing and the pain was unbearable. He did not take his time either and wrestled and pushed his fat dick into my asshole. Finally, after what seemed like an eternity, he states with an air of triumph, "I am completely in".
"Please stop, I can't take it", I cried again, but he ignored me. He started pumping in and out and in and out and so forth. Several times he pulled it out completely and started again. After a while, it did not hurt so bad, but I was sure that my asshole would never be the same again. I felt like I would start coming again, as my dick pressed into the sawhorse. Faster and faster he pumped, harder and harder he pushed. He must have great control for it was a long time before I heard a mighty, "AAAAAAAHHHHHHHHH,.....I'm coming.....AAAAHHHHHHHHHHHHH." Like I did with him, he bend over my body and grabbed my dick and held on tight, and immediately I came as well. I matched his "AAAHHH" with one of my own. For the first time we were sharing a moment together. He held on to me for a long time with his dick in my ass. When he got off, he immediately untied me, and helped me up. He embraced me and kissed me around my face and finishing with a great big kiss to my lips. I embraced him in return, and just stood there holding him, shaking from all of the pain in my body.
He helped me walk back to the house and we showered together, and later fell asleep in each others arms.
Epilogue:
Neither of us could sit down without pain for over a week. Bob and I made love everyday for two weeks. My desire to continue my journey around the country was challenged by the desire to stay with Bob for a while. I think that I was in love for the first time in my life. The emotional attachment was great. One day while Bob was out buying supplies, I examined his video-cassette collection in a back storage room. Bob was apparently an amateur video buff. He had films of all of his vacations. Three cassettes marked XXX looked interesting, as they had no titles. I popped one in and found Bob _f_u_c_k_ing some kid (younger that myself) in the barn. Fast forwarding through the cassettes I found scenes of all kinds of men - young, old, white, black, Hispanic, all in the barn having various forms of _s_e_x_ with Bob. The last scene of the last tape was of my first night in the barn with Bob. I was apparently the only one who got a chance to whip or _f_u_c_k_ Bob. I was stunned. I replaced the cassettes and went out to the barn and into the loft. It took me a while, but I found Bob's hidden camera.
When Bob came home, I still did not know what to say, but immediately Bob sensed that something was up.
"What's up with you?", he asked.
"Nothing", I replied.
"Come on, no secrets between us, " he insisted.
"How many boys have you _f_u_c_k_ed in the barn?"
There was a moment of silence before he inquired, "Why do you ask?"
"I found your videos this morning," I responded.
"Oh!" after a pause, he said "I wanted to tell you about them. But I was afraid you would be mad about it."
I said nothing, I just stared at the floor.
"Listen, I have no one here. It is lonely as hell and when I need _s_e_x_ I have to go looking for it. The videos are my company after everyone goes home. I didn't know I would fall in love with you, or that you would stay. No one ever stayed before. I am too demanding for most people to live with. That is why my wife left me. Forget about it. I don't want to lose you and I will do anything to convince you to stay."
After a moment of silence, I asked "Would you be willing to march back into the barn and have your ass tanned again?"
Bob smiled and said, "Anytime my friend, Anytime." We embraced and kissed, and then headed for the barn.