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Part of a summer spent at a friend’s house proves to be very interesting for eighteen year old Andy Mason.
Chapter One: Night visitor.
I’m what you might call a light sleeper, so I was aware of the presence in the room from the moment the door opened. I was not familiar yet with my surroundings in the guest room I was going to be staying in for the next week, but the person who silently entered the room and closed the door before coming to the side of my bed was, as he moved like a cat in the dark.
My heart raced with anticipation as the bed sheet slowly came down off of me as I lay on my bed with my arms and legs akimbo. It was happening. What I had hoped for and dreamed about ever since that night last fall in this very same room was about to happen again, and as my eyes slowly adjusted to the very dim light I called out quietly to my very welcome visitor.
“Ssh!” came the response of the person who was kneeling on the bed beside me.
The voice – or at least the sound that came out of the person – was much deeper than my friend Jason, and as my eyesight improved a little, I could tell that the person kneeling at my side was much larger than my friend. Taller and heavier, and along with the manly aroma he carried with him was the faint scent of pipe tobacco.
“Mr. Caldwell?” I asked.
“Ssh!” came the reply, and as he spoke I felt the top snap of my pajamas get popped open, followed by the other snap and the feel of warm air on my very erect penis.
It was Jason Caldwell alright, but not my life-long friend Jason Caldwell. Not the one who I would be going off to school with in the fall. The Jason Caldwell who was taking down my pajamas and leaving me naked and shivering was his father, Jason Caldwell Sr. to be precise. As for me, I was shivering from fear, not from cold, as the room had been warm before and was getting hotter by the minute.
I gasped audibly as I felt Mr. Caldwell’s hand lift my dick from my belly and give it a slow and gentle stroke from the tip to the base. The hand went back up and down a couple of times as he let out a sigh of his own.
“Not very big down here, are you Andy?” I heard him murmur as he rubbed the tip of my dick, spreading the gooey drippings all over. “I like them small though.”
The shadowy figure bent over and I felt my dick slide into a very wet and warm place. Mr. Caldwell’s hand was working over my balls as his mouth slid down and enveloped me right to the base, and after only a few more such movements I felt my orgasm rise within in me.
“Gonna cum,” I managed to grunt out just before my dick spewed a series of volleys of cum into the throat of Jason’s father, and he didn’t miss a beat as he continued to go up and down on me until I went limp in his mouth.
The room was silent as Mr. Caldwell’s mouth came away from my dick, and when he got up from the bed I thought he was going to leave but he didn’t. Instead, I heard the rustling of fabric as the shadowy figure took off the boxer shorts he had been wearing and climbed back into bed beside me.
Mr. Caldwell was so close that I could feel the heat that glowed off of him, and the prickly hairs on his leg touched my smooth calf as he arranged himself to get comfortable. After a minute of us staring at the ceiling in the dark, I felt Mr. Caldwell take my hand and bring it down between his legs and onto his cock.
Chapter Two: Reciprocation.
Where he took my hand in no way resembled my buddy Jason, because while Jason’s cock was also bigger than mine, the tool that my hand was dropped onto was way bigger than anything I had ever imagined.
Mr. Caldwell’s cock was warm to the touch and felt like steel as I tried to get my hand around his throbbing organ. Jason’s father guided my hand along the length of his manhood, and just when it felt like there would be no end to the monstrous cock, I felt the taut skin of the fat bulb and the sticky tip against my palm.
“You know what I want,” Mr. Caldwell said gruffly as his hand let go of my wrist and reached up to grab me gently but firmly by the back of my head, pulling me over and down to his sex.
The musky scent of his genitals filled my nose as he bought my face to what I held gingerly in my hand. I opened my mouth after I felt the knob of his tool hit my lips, and I was forced to open my jaws as far as I could to take in the bulbous head of his cock.
This second cock to ever pass my lips stretched my mouth to what felt like impossible limits as I struggled to get my lips down the plump crown of it.
“Watch the teeth,” Mr. Caldwell cautioned.
Easier said than done, but when he pulled me around so that I was on my knees next to him, it got to be a little easier. Helping too was the lubrication that Jason’s father squirted onto the shaft of his cock, as it was obvious that there was no way my lips would ever get far enough down his cock to taste it.
It made the stroking much easier, and as I got my balance I found I was able to use bursa escort both hands on the shaft of his cock, milking him with the slow, spinning motion that I used on his son that time.
Only needed one hand with Jason, I thought to myself as Mr. Caldwell held onto the back of my head by the hair ad he guided it up and down, and while my mouth barely got past the ridge of his glans, I must have been doing something right because Mr. Caldwell was breathing harder and heavier.
I felt Mr. Caldwell’s hand let go of my hair and slide down my sweaty back and into the crack of my ass, and I jumped when I felt his finger slide into my anus.
“Oh, that’s tight,” he grunted.
I squirmed and tried not to choke on his cock as his finger impaled me deep and hard, and when he pulled out his digit and let his hand go down to my nuts, my cock sprang a little back to life.
Mr. Caldwell grabbed my semi-turgid dick and began pulling on it with a savageness that was both painful and pleasant, stretching my modest stem to what felt like outrageous proportions. Even though I wasn’t even hard, I felt my dick tingle and start spitting out cum onto the bedding and Mr. Caldwell’s hip despite everything.
“Damn! That’s it,” Jason’s father hissed. “Suck that cock, Andy. Oh! Here it comes boy.”
I felt his cock throb in my hands a second before he spoke, and I barely got my tongue to the tip of it before he started cumming. I gagged a little as he kept cumming and cumming and the sheer volume of cum start to overwhelm me, but I managed to let it slide down the shaft as I milked him until his body relaxed and his dick went soft.
I straightened up and knelt in the quiet darkness as Mr. Caldwell’s breathing returned to normal. His cum was all over the back of my hand and I felt it drool down my fingers as he sat up.
“Not bad,” Mr. Caldwell said softly. “You’ll get better.”
With that he stood up and left the room as quietly as he had entered, and after a while I eased back onto the bed, landing in the now-cool puddle of semen I had left there minutes earlier.
What if Jason came in now? That was the thought that kept me awake for the longest time, until sleep finally came.
Chapter Three: The morning after.
Jason’s bedroom door was still closed when I got up the next morning. I heard his Mom saying goodbye and the sound of the door closing, followed by the purr of a car engine outside, and while I knew both of Jason’s parents worked there was no way that I could tell which one had left first.
My kidneys didn’t care, as I had to take a leak in the worst way, so I tiptoed out of the room and into the bathroom which was mercifully unoccupied.
Barely making it to the toilet, I sighed as I let the torrent of piss drill into the waiting bowl. I was just getting started when the door opened.
“Uh, I’ll be done in a minute,” I said, shielding myself and turning away as I saw the hulking form of Mr. Caldwell, dressed in a camel colored suit, filled the doorway.
“I’ll wait,” he said, coming into the room and closing the door behind himself. “Don’t turn away from me. I want to watch.”
He was standing right next to me, at least a head taller than my meek 5’7″, as I kept peeing very self-consciously under his watchful eye. His musky and manly scent was now replaced by the woodsy musk of cologne, and as my stream turned into a dribble, I shook my dick and tried to pull my pajamas back up again.
“What?” I asked, not sure what he meant and feeling very uncomfortable.
“I said drop them pajamas,” he snapped, yanking them down for me, and I stood there trembling as they landed around my ankles.
“Now get yourself off,” he said, glancing at his watch. “You’ve got three minutes.”
“Come on,” Mr. Caldwell said. “You’re gonna pop your wad before I leave here. That’s it. Stroke it like you mean it.”
I felt so pathetic as I pulled in my flaccid dick while standing next to the toilet under the very watchful eye of Jason’s father, whose physical presence was just as imposing as his attitude was.
“Get it up. I’m not going to leave here so you can run into Jason’s room with a boner an stick it up his ass.”
“What? I asked, continuing to pull on the limpest dick imaginable. “I – we don’t.”
“You don’t fuck him in the ass?” he asked incredulously. “Does he do you?”
“No, it’s not like that at all,” I insisted.
“Well, you two are doing something to each other,” he said. “I had you pegged for a cocksucker the minute I laid eyes on you. Now get busy with that thing. Think of what you did to me last night.”
Amazingly, I started to get erect, and as I did Mr. Caldwell grunted his approval.
“That’s better,” he said with grudging acknowledgement. “Figured you for a bigger dick, that’s for sure. You can’t have more than 5″ there.”
To my dismay, he was an excellent judge in that regard, but his degrading my equipment was not helping me do what he wanted me to do. In fact, just the opposite was going on.
“I bursa escort bayan can’t,” I whined as my hand moved rapidly up and down my dick without accomplishing anything. “I can’t cum.”
Mr. Caldwell sighed, looked at his watch and shook his head before pulling down his zipper and fishing his cock out.
“Look at this for inspiration,” Mr. Caldwell said, his hands on his hips as he faced me with his flaccid member hanging out of the fly of his trousers.
I looked at the preposterous sight of that long thick cock sticking out of his pants. The beige circumcised penis looked even bigger than it had felt, and he was easily bigger soft than I was hard. When he gave it a slow and lazy pull it seemed to get even longer and thicker, and that’s when I felt my body tingle from the tip of my toes on up.
“Awww!” I groaned, doubling over a bit as jets of my cum squirted all over the toilet, some finding the mark but most of it landing elsewhere, and when I was done cumming Mr. Caldwell calmly put his dick back in his pants and went to the door.
“Be sure and clean up the mess,” he said before turning back to me. “I’ll be dropping by your room again tonight. That will give you something to look forward too.”
Chapter Four: Jason Senior returns.
When the door opened late that night I was hoping it was my friend Jason, or at least that was what I was telling myself. It was his Dad, and I was shocked when after he locker the door behind him he turned on the light.
“No sense fumbling around in the dark,” Mr. Caldwell said as he let his pajama bottoms fall down and stepped out of them, his cock swinging back and forth with his movements.
“Not bad for a guy pushing 50,” he opined, looking at himself in the mirror while posing for me. “Of course, Andy seems to have a one-track mind.”
I forced myself to look away from his elephant trunk and glanced at his body, which was certainly in good shape. His chest was broad and his stomach was flat, and he had a thick mat of dark brown hair on his chest that I would have loved to have owned.
“Sorry,” I said. “You look fine.”
“Better than fine, I’d say,” Mr Caldwell said, pulling on his cock as he motioned for me to get up out of bed.
I hadn’t bothered with pajama bottoms, and this drew a chuckle from Mr. Caldwell as he watched me hop out of bed with my erect dick waving at him.
“You’re always ready, I’ll give you that. Now tell me about what you did after I left this morning. Did you and Jason suck each other’s dicks all day?”
“No,” I answered with frustration. “We only did that once.”
“Really?” he said. “So last night was only the second time you ever sucked cock? Well, in that case you weren’t that bad, and like I said, with practice you’ll get better. Here, rub your dick against mine.”
He held his rubbery cock out toward me, and when I pressed the tip of mine against his I felt a tingle run through my body. The feel of our sensitive tips scraping together was erotic enough, but when I saw the way my pale acorn-shaped glans looked against the dusky plum of his member, it was all I could do to keep from cumming.
“Feels nice, doesn’t it?” he asked. “You ever do this to Jason?”
I shook my head no, unable to look away from the sight of our dicks rubbing together.
“Tell me about it,” Mr. Caldwell said. “The time you two gave each other head.”
“I can’t,” I protested, and when he heard that he suddenly pulled his cock away.
“Too bad. I was just starting to get into that,” he lamented while waving his cock around, a weapon which had lengthened and thickened considerably during our contact. “And you! You’re drooling cum like sap from a tree.”
It was true, and when it was clear that he was done unless I talked, I relented.
“What do you want to know?” I asked, exhaling loudly when he lowered his cock to meet mine again.
“Who instigated it?” he asked.
“We both did. We were watching a movie in here and all of a sudden we started playing with each other.”
“Did Jason like it as much as you did?”
“I think so,” I said.
“How come you two haven’t done it again?”
“I don’t know. I think we are afraid to admit we liked it.”
Actually, it was because we haven’t have an excuse to blame it on like we did that night. We had gotten a joint and smoked it, and afterward we pretended that it happened because we were wasted. We weren’t, or at least I wasn’t.
“Tell me about Jason’s cock.”
“Mr. Caldwell,” I whined, and after he pulled his cock away again and chastised me for sounding like a sissy, I asked him what he wanted to know.
“Jason’s cock,” he repeated. “Is it as big as mine?”
“Oh. Well, he’s bigger than you, I hope.”
“How much bigger?”
“I dunno. Couple of inches maybe.”
“That’s good,” Mr Caldwell said, grinding the rubbery head of his cock into mine hard as my dripping dick oiled us both. “That would give him about 7 inches or so I figure. escort bursa That’s a decent sized cock for a man. I would hate it if he ended up with a little one like yours.”
“Why do you treat me so mean?” I asked, my face flushing with embarrassment.
“You love it. Look how stiff your dick is. Me saying that didn’t hurt your feelings. In fact, it turns you on doesn’t it? You love me telling you how little your dick is, just like you love looking at that tiny thing of yours rubbing into my cock. In fact, you’re going to cum soon too, aren’t you? Just like this morning.”
He was right, of course, and as if on cue my dick started spurting cum all over his cock and pubes, draining my balls while covering his pubic hair with so much semen it looked like tinsel on a tree.
“Now you have another mess to clean,” Mr. Caldwell said, as when his hands went on my shoulders and brought me to my knees, it was clear how he wanted me to clean the mess.
It took me a long time to suck my cum off of his crotch, but after I got him all clean, he was as hard as could be. The veins throbbed on his shaft as I milked and sucked him rabidly. I did better this time, finding myself able to go further down the shaft while avoiding the tooth contact he despised, and after Mr. Caldwell coated my throat with his cum, he told me that.
“You’re a natural born cocksucker,” he said after pulling his flaccid hose out of my mouth. “You know where this is going by the end of the week, of course?”
I didn’t, but he was happy to tell me.
“Your ass,” he said coldly, and laughed when I shook my head no. “I’m going to fuck you in the ass with my cock, and when I get done, you might not be able to walk, but you’ll be begging for more.”
“No,” I said, and I was certain of that. Not only wasn’t it possible, I didn’t want that gigantic thing in there. I would be long gone if he tried that.
“Yes. End of discussion on that. If I want to fuck your ass, that’s what’s going to happen. If I tell you to lick my asshole, your tongue had better be headed in that direction. First though, you’re going to do something for me tomorrow night,” he informed me in a matter-of-fact manner before leaving the room. “Something you will love to do.”
Chapter Five: Luring Jason.
“They’re asleep,” I told Jason as I brought him down to the basement and moved him against the wall, just as I had been instructed to do.
“We shouldn’t do this,” Jason said, but made no effort to stop me from taking down his pajamas and kneeling in front of him.
Jason’s dick was long and thin – much more slender than the one I had been sucking the last couple nights, and after my lips slid all the way down to his pubes, I felt him start to get hard right away as he ran his hands through my hair.
“Oh man, that feels so good,” Jason moaned as he got rock hard in seconds.
“I forgot how beautiful your cock is,” I said loudly as I leaned back and stroked his long boner, while I glanced over at the laundry room where Jason’s father was watching from. “Your cock is so long – way bigger than mine is.”
Back I went, my mouth devouring Jason’s cock that I found it so much easier to handle than his Dad’s. I brought him to the brink of orgasm several times, only to stop and prolong it, but when he finally came, he came so hard his knees gave out as I leaned against him to keep him upright.
I almost gagged on the copious load of semen that he had deposited in my mouth, but when he finally stopped cumming I jumped up to my feet and ran upstairs, locking my bedroom door behind me.
“Andy. Please let me in,” Jason said in a whisper through the key hole. “That was so good. I want to do it to you too.”
“Tomorrow maybe,” I mumbled, and after a minute or two I heard him go to his room. I unlocked the door and sat on the bed and waited.
I heard Mr. Caldwell’s footsteps coming down the hall rapidly, and when he came in the room this time he looked disheveled. His face was red, and when he opened his robe his swollen cock was even redder as he came over to me.
“Good boy Andy,” he said, cock in hand. “Do you still have it?”
I opened my mouth, showing him the load of cum that I had managed to keep, even if some was trickling down the sides of my mouth.
“Ah!” Mr. Caldwell groaned as he slipped his cock in my mouth, coating his tool with Jason’s seed as he held my head in his hands and fucked my face with short hard thrusts, reaching orgasm in less than a minute himself.
“You did good, Andy,” Mr. Caldwell said, moving me down onto the bed and taking my cock in hand before slipping it into his mouth. “You deserve a reward.”
Chapter Six: Tonight.
The next day Mr. Caldwell caught me on the way to wash my hands before dinner and eased me down the hall.
“Here, you’ll need this,” I said, handing me a tube of some kind of lubricant. “Tonight’s the night. I want your ass primed and ready for me.”
“I can’t,” I protested, and hearing that made Mr. Caldwell mad, and he shot me a cold glare while leaning me against the wall. “It will never fit.”
“Of course he does,” he hissed. “Look at my wife, for crying out loud. If she can take it – and love it I might add, you can. Stop being a pussy.”
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