One summer during my high school years, my parents sent me off to spend a few months at my grandparent's farm. I tried to protest as I thought I'd be bored silly out in the boonies, but my parents insisted that they knew what was best for me. Little did I know or expect what was in store for me.
I had known at an early age that I was attracted to men, especially masculine, hairy, older men. I had not yet had the courage to get together with other guys yet, so I was still a virgin. But I knew I would like male-on-male sex and I masturbated, thinking about or looking at nude pictures of men, every chance I could.
On the second day I was at the farm, I noticed a tall, strapping guy in his 40's doing some chores around the property. When I asked my Grandfather about him, he said that Jake was a farmhand who he had hired to work weekdays to help with the animals, the crops, and any other chores around the farm. Grandad mentioned that he spent weeknights at the bunkhouse on the farm, but spent weekends in the city. "C'mon Sonny, let me introduce you to him."
The strength of Jake's handshake sent a tingle up my arm and down my spine. He had a handsome face which wore whiskers of one or two days. He was wearing a tee shirt with sweat stains in the middle of his chest and khaki shorts which came to about mid-thigh; cowboy boots completed his attire. From what I could tell from his bare arms and legs, he had a toned, very hairy body. His shorts clung to his thick, muscular, tree trunk thighs as if they were a second skin. I couldn't help but notice the outline of his flaccid dick pressed against his upper left thigh. I could feel my dick begin to react to what my eyes were reveling in.
That night as soon as I got in bed I began to masturbate as I envisioned Jake completely nude. I was so hot for this man that I must have brought myself off 2 or 3 times before I fell asleep. This became a nightly occurrence. Some nights I would dream of the two of us being naked together and fondling each other; most of those nights I would end up having a wet dream.
I began to spend most of each day watching Jake as he did his chores. As he went from area to area around the property, I'd find a reason to be near the area too. I tried to be discreet so that he couldn't see me, but sometimes he would catch me starring at him, and then he would just wink and smile at me. Most times when that happened, I'd be embarrassed because I had been caught, so I'd quickly run away. A few times I was even brazen enough to peak through the windows of the bunkhouse when I knew he was in there, hoping to see him naked. The same thing would happen at times when he was in the barn or any other buildings. In looking back now, I could have been considered a stalker. I was so completely mesmerized by this hot, sexy man.
At the end of my third week at the farm, my grandparents announced that they were going to attend the wedding of their friend's son that weekend: they would be gone 2 nights, so I could either go with them or stay at the farm. They said that Jake had agreed to stay at the farm that weekend to watch over me and keep me company if I decided not to attend the wedding. Though I hemmed and hawed a bit about making a decision, I knew exactly what I wanted and where I wanted to be that weekend; I just didn't want to appear obvious.
After my grandparents, Jake and I had breakfast the morning they were leaving for the wedding, Jake took off to attend to chores and I agreed to do the after meal cleanup so that my grandparents could leave earlier than they had planned.
As soon as I had finished in the kitchen, I rushed off to see where Jake was and what he was doing. I went from building to building, trying to be unobtrusive, but Jake was nowhere to be found. I was getting a little anxious and annoyed. The barn was the last of the buildings where he could be, except for the main house, but Jake only came to the house for meals.
I crept behind the back side of the barn to a section where the siding had some gaps between the planks. Oftentimes I'd come here when Jake was working in the barn so I could watch him. Sometimes he'd scratch his crotch, his ass, or one of his nipples and I'd get almost an instant erection seeing him touch himself.
That morning I tried to be as quiet as possible as I approached the space. But before I even got my eye to the peephole, I heard Jake's enticing voice addressing me.
"Why don't you come inside the barn, Sonny? I know you like watching me and you'll be able to see much better closer up. Maybe I'll let ya touch it, and maybe, if you're really good, I'll even let ya smell it. Would you like that, Sonny? Don't be shy, son, we both know that you wanna come in here by me. You're just wasting our time alone together, kid. Who knows if we'll ever have this much time together again?"
Sheepishly, I slowly walked to the entrance to the barn, but stopped in the doorway. Jake was leaning against some hay bales, completely naked except for an old black cowboy hat and a red bandana around his neck, and a pair of black, well worn, cowboy boots. His right hand was slowly stroking his hard, throbbing cock. He was looking straight at me with a smirking grin on his face.
"Don't be scared, son, I won't hurt ya," he said as he sat at the end of one of the bales of hay. "C'mere, kid, come sit next to me so you can see me better. And ya better take your clothes off too; yer little pecker is making a tent in the front of yer shorts. You must really like what ya see. Right, kid?"
Like a zombie, unable to take my eyes off Jake's big, hard dick, I undid the few clothes I had on and let them fall to the hay covered floor, then sat next to Jake. He took my left hand in his and placed it on his throbbing cock shaft. Unlike my smooth boy-cock, his was dominated by a series of thick veins. Shivers of pleasure ran up and down my spine. His shaft was hot and hard and was so thick that I couldn't close my fingers around it. I felt like I was hypnotized.
"Stroke it slowly, boy, nice and easy. Oh yeah, son, that's just how I like it. You're doing me good boy. See how the cock honey is seeping from my piss slit? That's how you can tell if a cock is happy. And mine is so happy now that it's leaking all over your hand. Now, taste my honey, son; just lick it off your fingers. Good boy, kid, you follow directions well. Do ya like that? Well, lick the rest from your hand. Now taste it right from my cock tip. Just put your tongue on the head and lap up my sweet juices. Nice, son, real nice. Now put the whole head in your mouth and caress it with your tongue. Oh, baby, that feels so very fuckin' great. That's heaven, Sonny boy. So, so good. But, why don't we go over to my room where we can both lie down and get comfortable on the bed?"
Jake pulled my head off his prick, picked up my clothes, took my hand in his, and led me to the bunkhouse. I complied with his every wish, a bit apprehensive as to what would happen next, yet so very eager to get closer to this hot, naked man that I've desired for so long.
As soon as we entered his quarters, he directed me straight to his bedroom. He slipped off his boots, undid his bandana and threw his hat to a nearby chair. I just stood there watching him as he settled himself on his back on the bed. He then smiled at me and patted his chest a few times. "Come to Daddy, Sonny boy. Come get what you've been waiting for."
I quickly joined him on the bed and he positioned me so that my face was near his crotch, and my crotch near his face, with my body atop his hairy, muscular torso. "Ok, Sonny, get your hot little mouth back working on my rod." I quickly obliged, tasting, licking and sucking his pulsating man meat. And, as I did so, Jake began to rub my ass crack with his thumb, occasionally wetting his thumb with his spit until it was smoothly gliding up and around the opening to my virgin love tunnel.
The musky aroma of his crotch, the throbbing heat of his cock in my mouth, the feel of his hairy man flesh rubbing against the fat underbelly of my cock, and the attention he was giving to my eager pink pucker made me completely oblivious to everything else in the world. Then Jake stretched my ass cheeks so very far apart that it almost hurt and I felt something warm, wet, and slippery flicking at my pucker. That felt so fuckin' great that I pushed my hips back toward it as I wanted more. At that point, Jake's tongue completely penetrated my pussy lips and my entire body convulsed. My sensuary system overloaded and my boy dick soon spasmed as I shot a hot, creamy load of jism on Jake's hairy chest. The orgasm seemed to last forever and tears of joy filled my eyes as I moaned and whimpered, Jake's prick still buried in my mouth.
"You're really enjoying this, son, aren't you? Daddy's gonna turn you into his private little slut. And you'll love that, won't you?
"Well, son, I've just helped you shoot a hot load and now it's time for you to help Daddy shoot one too."
Still in a 69 position, Jake told me to stay where I was but to raise the back end of my body so that I was on my knees. After I did so, Jake spread my cheeks with the fingers of one hand, and with the fingers of his other hand he began to scrape up the juices of my orgasm from his chest and transfer them into my fuck hole. As this progressed, the process became more and more pleasurable to me, especially once the walls of my boy-pussy were well coated with my own cum. I knew what was coming next, and though I was apprehensive, I was eagerly awaiting it.
"Now Sonny boy, take the rest of your cum load and lube up my fat dick. Daddy's ready to bust that hot little cherry of yours."
I did as he asked and soon his cock was very slippery, and also super hard and throbbing; his piss slit was opening and closing like the mouth of a guppy as it oozed his cock honey and the color of the entire organ was almost a deep purple.
"Come here and straddle my hips, boy. That's it, kid. Now just kneel there, spread your ass cheeks, and then lower your butt down until you can feel my cockhead against your pink pucker.
"Oh yeah, Sonny, that's the spot I want. Just take it easy and slowly lower yourself onto my cockhead. It's gonna hurt for a little while as you press down and my prick stretches your pussy opening, but I promise you, after a few minutes, you're gonna love having Daddy's prick deep inside you.
"That's good, son. You're doing really great. Now if the pain gets to be too much, just stop and take a breather. We've got pleanty of time, baby. That's it kid. From the looks of that smile on your face, I think you're enjoying this; not even complaining about any pain.
"OK boy, you've almost got it all, just an inch or so more to go. Here let me help you." As he said this, Jake put a hand on each of my shoulders and pulled me down quickly on his dick until I could feel his hairy balls pressing against my butt cheeks. An uncontrollable cry of pain shot out of me and tears welled up in my eyes.
We were still for a few minutes. Jake eventually began to caress my face with his hands, wiping away the tears. "Well baby, Daddy Jake finally did bust yer cherry. Now I'm gonna christen its walls with a few loads of my baby batter that will signify that I own yer boy cunt forever. I'm gonna shower every fucking cell in your tight little pussy. "
Jake then put his hands on each side of my hips and began to move my body up and down. He'd move my body up and pull his cock almost out of me until just the head was in me, and then he'd pull me down on it as he'd quickly thrust back into me. After 5 or 6 strokes, my body began to move the way he wanted, and he removed his hands from my hips. There were big smiles on both our faces; our bodies were meshing like a well-oiled fuck machine. My pleasure filled body tingled and trembled and began to move faster and faster; I wanted more and more of his cock in me; I loved the feel of being fucked hard by Jake.
"Sonny you're a natural cock-loving cunt; a very quick learner. Now get on your hands and knees so Daddy can give your pussy a good reaming. That's it hon, now raise that sweet little ass of yours a bit.
"There that's great. Now let me slip this fat hog back in ya and I'll take us both for a super ride."
Jake re-entered me and began thrusting, varying the speed at times, holding onto my shoulders as if he were using my body as a masturbation device. I was delirious with pleasure and unconsciously moaned and groaned and begged to be fucked deeper and deeper.
Jake removed his right hand from my shoulder and clasped my cock shaft with it. "I want you to cum off with me, baby. I wanna feel your pussy lips spasming on my shaft as I shoot in you."
His stroking of my dick was doing what he intended, and within minutes, I cried out, "Oh fuck, here I cum, Jake, here I cum." As I orgasmed, I could feel my pussy lips doing rapid clasps against Daddy's hard shaft. I had never cum off before with anything in my ass, so I was never aware that this was a normal part of the male orgasm process.
"I felt that, Sonny, oh sweet fuckin' jesus how I felt that. Your tight pussy was clenching my cock like it never wanted it to leave your fuck hole. I'm ready now, baby...... I'm ready to breed your virgin hole. Take it you horny little bitch cunt!"
As Jake neared orgasm, his cock grew larger and thicker within me, so I knew before he told me, that he was ready to mark my cunt with his seed. As the girth of his prick increased, some pain returned to my stretched sphincter muscle. But the pleasure he was bringing me outweighed the pain, and I continued to revel in his thrusts.
And then Daddy cried out as he began to unload his balls in me. I was amazed that I was able to feel his cock shaft throb and spasm with each spurt of jism that he shot deep inside me. As he kept thrusting in me, I could feel the wetness of his fluids oozing from my ravaged, but happy, love tunnel, and later the slow trickle of his semen down my inner thighs.
Jake soon stopped thrusting and we were still for a few seconds. Then he gave me a massive hug which almost took my breath away. My legs collapsed, and I fell flat on the bed on my stomach, with Daddy's stiff cock still imbedded in me.
Jake began kissing my neck, my shoulders and my ear, and then he began to softly whisper to me. "I own your ass now, kid. No other man can ever do to you, what I just did. No other man can ever bust your cherry. No other cock can ever be the first to enter your fuckhole."
He then rolled off me and turned my body on its side so that I was facing him. "I know you enjoyed that, Sonny. You were so enthusiastic through it all. And I loved it too. I'm gonna want a lot more of that mouth and pussy of yours. And over time, I'm also gonna teach you how to deep-throat me so you can swallow my entire fat hog. Now why don't we nap for a while so we can get a few more fuck sessions in today? And then we have some nights and days to play some more, don't we, babes?"
"Thank you so much, Jake. I love having you as my Daddy. I love what we did today. And I wanna do it more, a lot more. You can be my Daddy any time you want. May I get a kiss from you before we nap?"
Jake pushed me over on my back and got on top of me. He began kissing my eyes, my cheeks, my ears, and finally my lips. He hadn't shaved that morning so he had a coarse stubble on his chin, cheeks and around his lips, and I loved the feel of that against my smooth flesh. As he was kissing me, Jake manuvered himself so the lower part of his body was between my legs. His tongue started exploring my mouth and instinctively I started sucking on his tongue as if it were a cock. As our kissing became frantic, I drew my knees up and wrapped, my long, lean legs against Jake's strong back. Soon I felt something hard and warm against the flesh of my ass crack. A few seconds later, his slippery cockhead was pressed against my sopping wet, and wide open pink pucker. I trembled in delight as it entered me. "Oh Daddddddddy.......," I purred.
Jake & MeOne summer during my high school years, my parents sent me off to spend a few months at my grandparent's farm. I tried to protest as I thought I'd be bored silly out in the boonies, but my parents insisted that they knew what was best for me. Little did I know or expect what was in store for me. I had known at an early age that I was attracted to men, especially masculine,
Losing My Cherry To DadMy parents divorced when I was about 5 years old. Dad evidently had had a long time sexual affair and when Mom found out about it, she couldn’t accept that. I rarely saw my father once they separated as he moved to California shortly thereafter. During the summer months, I would almost always visit Dad for 3 or 4 weeks and I really enjoyed those visits. I loved him so
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