Jimmy's Chaperone, a short story by Josh Terrence
Author's note: This short story depicts sexual acts between males of various ages. If you are offended by sex between men, teenage boys, boys or between males of any age, why are you here? If you are not a legal adult or if this content is illegal in your locale, leave now.
This story is a work of pure fiction. The taboo acts depicted in this story are not condoned by the author, this is fantasy only. All Characters in this story are portrayed by actors 18 years of age or older. This disclaimer applies to all installments of this story, past and present.
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I was fast asleep, still worn out from the previous night when I felt the warmth of a wet mouth encase the end of my dick. I started to blink, letting my eyes adjust to the light that was shining into the room from the bathroom by the door, then I let go of a yawn. As things started to come into focus for me, I saw the scant rays of daylight beaming in through the 4th story window of my hotel room, glancing off of the walls and the ceiling. I felt the wet sensation move down my shaft just as a tight, almost silky smooth tomb started to envelop its length, so I let my gaze travel down to my midsection.
A smile crept across my face when I spotted the cute 12 year old curled up to my side, bobbing his head up and down diligently while he moaned softly around my cock. He was fully naked, his clothes piled up in the chair right beside my bed, and from my vantage point, every disorganized cowlick on his head of sandy blonde hair was visible, each one pointing wildly in a different direction. I reached out with my right hand and ran my fingers through his short, messy head of hair, prompting him to smile up at me with a hungry look in his blue eyes.
It wasn't much of a surprise to see him in my bed again. When we parted ways the night before, he was still craving cock but his curfew was upon him. His young body was painted with cum trails that had splattered his fair skin and his rear end was sticking straight up in the air, anxious for the next hard dick to slide in and give him what he wanted. Unfortunately for the youngster, and for those of us who had gathered in the large suite to have fun with him, his mother had come to collect him for the evening. This put an abrupt end to the fun we were all having, though a few of the older bears at the party did wind up taking some of the twinks in attendance back to their rooms for a nightcap.
When I checked into the hotel early Friday evening, I thought I knew exactly what to expect. The establishment had long ago gained a reputation as an anything goes emporium for gay sex, and I was in the mood to score with a couple of 18 year olds all weekend long. The hotel bar was an easy place to meet a fresh faced youngster, looking for a safe place to get their cherry popped by an experienced man. The cover charge at the front desk is well worth the price, and while it's never spoken, the expectation is always clear.
When I checked in on Friday afternoon, I was a little stunned to find that a new manager had been hired to run the place over the winter. It turns out that the lady who'd been managing the hotel for years suffered a stroke and was no longer able to perform the day to day functions of the job. So she brought in her daughter, a pretty young lady in her mid thirties to assume the job. Even more astonishing was the presence of a cute blonde in his school uniform, sitting on a stool right beside the new front desk manager. His smile beamed through his pearly white teeth and his plump, moist lips, which were a perfect contrast to his baby soft skin. He looked no older than 10 years old, but I'd later learn that he had just celebrated his 12th birthday.
While his mom was collecting my money and my information, he was making direct eye contact with me. I smiled back at him when I thought his mom wasn't watching, then I turned my attention back to the transaction that I was completing. When the young lady handed me the swipe card for my room, I took it with a smile and a nod.
“Room 435, Mr. Love,” she said with a smile of her own. “If there's anything at all that we can do to make your stay more enjoyable, please let me know.”
“Thank you, madam,” I said politely. “I'm going to check out the suite first, then I'll be down to collect my luggage.”
With that, I got on the elevator and rode up to the fourth floor. When I walked into my suite, it was exactly what I expected. In previous years, my room was always plush, with a clean living area, a separate bedroom and a large bathroom with an oversized tub. As per my specifications when I made the reservation, the bathroom was stocked with plenty of towels and my bed had extra pillows.
Pleased with my amenities, I went downstairs so that I could retrieve my luggage from my car. When I got to the lobby, the little blonde was still seated behind the counter, smiling at me. I returned his smile, then I watched as his gaze traveled down to my crotch. I found myself studying his face closely, his cute features almost impossible to look away from.
“I take it that everything is to your liking, sir?”
Startled, I looked up to find the young mother watching me with a knowing look. I nodded silently, then I said, “The room is great. I'll be needing a bellman cart for my luggage.”
With that, I walked out to my car, not entirely sure if I was about to be thrown out of the hotel or not. Clearly, the manager saw me ogling her son, and she wasn't exactly smiling after the fact. I used the remote button on my key to pop the trunk and started to unload my bags when the sound of the bellman cart carried into my ears. I turned, expecting to find a young man dressed in hotel attire pushing the cart, but instead, it was the little blonde.
“I'll take your bags in, sir,” he said with a sweet smile, reaching down and hoisting my suitcase onto the cart with a boyish grunt.
“You don't have to do that, buddy,” I said jovially, earning me yet another smile from the cute boy.
“It's okay,” he countered, his smile beaming through his pearly whites while he squinted his eyes to protect from the glare of the sun. “It's my job here.”
“Oh yeah?” I said in an amused tone as he worked to put the rest of my luggage on the cart.
“Yeah, my mom said that if I want to earn money, I have to work here at the hotel for tips.”
“Well, that's not so bad, kiddo,” I told him, closing the trunk as he began to roll the cart toward the lobby doors. As he pushed the cart back toward the building, I couldn't help but notice his bubble butt, which was on full display in the seat of the navy blue dockers that contained them. He had both hands on the cart, pushing it almost as if he were struggling up a hill. I wanted to assist the boy, but the view from behind was so nice that I backed off and let him be.
When we were back in the lobby, he smiled at his mom and said, “He doesn't have that many bags, mom. I'm going to take his luggage to his room by myself.”
“You don't have to go to all that trouble, buddy,” I told him, reaching into my back pocket for my wallet so that I could tip the boy, but his mom waved me off.
“It's his job, sir,” she said courteously. “As long as you don't mind having him take your things into your room for you.”
“Not at all, ma'am,” I said, smiling at the little boy as I handed him his tip, five well deserved dollars. He smiled back at me and accepted the money, then his eyes moved back down to my crotch and he let go of a deep sigh and slid it into his front pocket.
“My name is Jimmy,” he said, looking up at me with an adorable smile. If I were shirtless, the top of his head would have barely cleared my belly button. His skinny frame was carrying no more than 70 pounds of weight, if that. His teeth were white, but they were spaced far enough apart that I could tell he needed braces. His lips were moist and shiny. They werent exactly plump, but they had a degree of fullness to them that complimented his boyish features.
“It's nice to meet you, young man,” I said, trying to contain my lecherous smile as I sized him up. “My name's Donald.”
His mom gave him a warm smile and an approving nod, then he pushed the cart onto the elevator. While we were waiting on the elevator, the youngster gave me a sweet smile, then the doors opened and he let me step inside before rolling the cart in and pushing the button for the fourth floor.
As soon as the elevator doors closed, he turned and gave me a smile, then, in an almost boastful tone, he said, “I know why guys come here. It's because they're gay.”
Not sure how I should react, I gave him a polite smile and nodded in acknowledgment, feeling a sudden awkwardness fill the air. Then, out of nowhere, he added, “I'm out of the closet to my mom and dad.”
I raised an eyebrow, the shock of what he said no doubt registering on my face. I cleared my throat and took a breath to compose myself, then I said, “Oh yeah?”
“Yeah, that's why I work here,” he told me with a grin. “After I came out to them, my mom told my grandma and asked if I could work here.”
“I see,” I said, feeling a strong stir in my loins. “It sounds like your parents are pretty supportive.”
“They said I can have a boyfriend if I want one,” he said with a smile that was suddenly mischievous. “Or more than one boyfriend, too.”
Just then, the elevator stopped and the doors opened. Once again, the cute blonde let me step out of the elevator, then he pushed the cart out and we made our way down the hall. I made it a point to let the gay youngster walk ahead of me, and he made it well worth my while. He gave me an innocent look over his shoulder, then he started letting his hips sway from side to side as he walked. My cock immediately filled with blood, knowing that this boy was up to something.
When we got to my room, he surprised me by pulling a key card out of his pocket that was marked “M” and used it to open my door. He politely held the door open for me, letting me go in ahead of him, then he rolled the cart inside. I watched with interest as he worked diligently to unload my luggage and stage it in the walk in closet. When he was finished with my suitcases, he closed the closet door and turned the lights on in my room, scoping it out while I contemplated continuing our conversation.
“So, do you have a boyfriend?” I asked, taking a seat on my bed. He shrugged noncommittally.
“Sometimes I do stuff with boys from my school,” he admitted. “My mom let's me get a room after school if I promise to do my homework.”
“Oh yeah?” I said casually, and he nodded, taking a step closer so that he was standing directly in front of me. “Do you enjoy that?”
“Yeah,” he said in a husky voice. “They let me play with their dicks and stuff.”
“I see,” I said with a slight catch in my tone, wondering how far this boy wanted to go. “What kinds of things do you like to do with their dicks?”
“I jack them off,” he revealed, then he licked his pouty lips and added, “I do other stuff with them, too.”
“That sounds like a lot of fun,” I commented, and he grinned at me. “What other stuff do you like to do?”
“Kissing,” he said with a naughty smile, placing a palm on each one of my kneecaps. “I really like kissing cute boys.”
“I imagine that you would,” I said, letting my gaze travel down to his crotch, where an obvious bulge had materialized. “Do you get to kiss boys as much as you'd like to?”
He shook his head no, his mischievous smile still fixed to his cute face.
“I've really been in the mood to make out with cute guys lately,” he sighed, licking his adorable lips again, then with a slight blush, he made his move. “I think you're really cute, Mr. Love.”
“I think you're very cute, too, Jimmy,” I told him. “But I imagine that your mom might not want you kissing a man my age.”
“She knows that I think you're cute,” he told me, running his palms all the way up to the tops of my thighs. “That's why she let me bring your luggage up here.”
With that, he leaned in and pressed his lips to mine. As soon as I puckered up, he brought both of his arms up to my shoulders and tilted his head to the right, then his moist tongue slipped into my mouth and he moaned. Right away, our kiss became passionate and it became obvious to me that this kid was a little pro. He was kissing me hungrily while his little fingers dug into my shoulders. I wrapped my arms around his skinny frame, running my hands up and down his back, then down to his plump bottom.
His fleshy mounds were incredibly soft, and I could feel their warmth through the navy blue dockers that contained them. Unable to control myself, I gave his supple rear end a series of firm squeezes with both hands, using my fingers to knead both cheeks like bread dough. He let go of a throaty moan when he felt my fingers manipulating his buns, then I felt his fingertips release their grip on my shoulders and run all the way down my torso to my crotch. His hands made contact with my raging boner from the outside of my trousers, and without disengaging our kiss, he smiled widely. I felt his little fingers working to unbuckle my belt, then he unbuttoned my fly and worked my zipper down.
In a flash, he had his left hand in my boxers, wrapping it around my shaft and letting go of another hot moan. At the same time, I felt a shiver run through me when I felt his hand wrap around my cock, letting off a moan of my own. I felt the cool breeze from the air conditioner vent flutter across the head of my dick, cooling the precum that was oozing from the end and letting me know that it was out of my boxers. I groaned in appreciation, then I felt his hand start to stroke it with slow, deliberate motions. I let out another moan that carried into my young partner's mouth, but he made no move to break our kiss. So instead of protesting, I increased the force of my squeezing on his plump rear end, causing him to sigh contentedly.
Out of nowhere, his dockers fell loose and I realized that he'd used his free hand to work them open. I pulled my hands away from his buns just long enough to let them fall around his knees, revealing a pair of white briefs that hugged his hips so perfectly. Practically breathless at the sight of the now semi pantless boy, I grabbed two handfuls of his underwear clad bottom. Once again, I could feel the warmth of his fleshy rear end, this time through the knitted fabric of his white, cotton briefs. At the same time, the heat that was pouring out of his crack wrapped itself around my fingertips, telling me that the boy was loving what we were doing. Another indicator of his enjoyment was the tent that had formed in the front of his briefs, caused by his three and a half inch boner that was sticking straight out into them. I pulled one hand away from his buns and ran it over his little hard on, and right away he shook his head no and broke our kiss.
“Squeeze my butt instead,” he practically commanded me, then he leaned in and planted a wet one on my lips while I heeded his call.
“You don't want any attention down there?” I asked curiously, letting my gaze drift down to his bulge. He bit his lower lip and shook his head no, his left hand still stroking my shaft quite expertly while precum poured from the piss slit.
With both hands back on his rear end, I resumed massaging his plump mounds while he looked deep into my eyes and sighed, then he told me, “I do other things with boys besides kissing and jacking them off.”
“What kinds of things?” I asked him tenderly, and in a husky voice, he revealed his naughty escapades to me.
“I give them head,” he said breathlessly, tightening his grip around my cock. “I really like sucking dicks.”
“I enjoy it too,” I told him with a warm smile. “Do you do anything else with boys?”
“Yeah,” he practically whispered, his eyes filled with lust. “I give butthole, too.”
“Butthole?” I asked, raising an eyebrow at his curious description of what I could only discern as anal sex.
“Yeah, I like it when boys put their dicks in my butthole,” he admitted.
“I see, Jimmy,” I said, watching his eyes drift down to my engorged member, which was still in his tight grip. “Have you had a dick in your butthole today?”
He nodded his confession, then he leaned in and kissed me again. His tongue slipped back into my mouth, and for a full minute, we shared a deep kiss. When we broke our kiss, he went on.
“I gave two cute boys some head after school,” he told me. “One of them let me ride their dick with my butthole.”
“Did you enjoy yourself?” I asked, and he nodded with a dreamy sigh.
“I always enjoy myself when I have dicks up my butt,” he said. “I like having dicks in my mouth, too.”
“Would you like to have another dick in your mouth?” I asked softly. He nodded in the affirmative, then he leaned in and rested his head on my shoulder so that he could speak softly into my ear.
“I want to have your dick in my mouth, Mr. Love,” he said seductively. “I want to give you some butthole, too.”
“What do you think your mom would say about that?”
“She already knows,” he said quietly. “As long as I do it at the hotel, it's okay.”
With that, he planted a kiss on my cheek, then he kissed me on the lips and dropped to his knees, his left hand still wrapped around my cock. His eyes lit up when he came face to face with the mushroom head, and with a determined look, the cute boy used his right hand to push my thigh over and give himself more room. With his skinny frame now comfortably between my legs, he leaned in and wrapped his lips around the head. I felt his tongue run all over my glans, lapping up as much precum as he could while he let his eyes drift up to my face, as if he were seeking my approval. I smiled down, meeting his expressive blue eyes, and with a grin, he immediately swallowed my entire length as if it were nothing at all.
I felt a powerful burn in my midsection as soon as my shaft moved into his throat, then his pert nose smashed into my pubic bush. With the expertise of a well practiced cock sucker, Jimmy proceeded to deep throat my dick with hot, horny moans of desire. From my vantage point, I couldn't see much of his face. He was hanging onto the tops of my thighs for support, bobbing his head up and down with passionate motions. His mop of hair was a perfect contrast to his cheeks, which were filling with air every time he bobbed up, then sinking into his face with every downward bob. I could feel the air that was blowing through his nose flutter through my pubes every time he swallowed my length, adding to the magnificent sensation that this boy was giving me. His pointy shoulder blades were poking up through the stitched white cotton of his shirt and his underwear clad bubble butt was sticking straight up in the air. His pants were still bunched around his knees, giving him a comfortable cushion to rest his knees on.
I reached down and placed my hand on the back of his head, earning me another long, depraved moan from the boy, then he doubled down on his efforts. For three straight minutes, the little cock hound stayed where he was, sucking diligently while his throat expanded and retracted with every up and down motion of his head. I knew I was getting close, so I used my fingers to caress his baby soft cheek, but he paid me no mind. I knew that the train was leaving the station shortly, and that unless this boy wanted a mouthful of hot cum, he was going to have to stop. Just as I was about to warn him, he pulled off with a slurp and gave me a passionate smile, then he told me, “I like to swallow.”
Before I could reply, he went back to work, taking my cock all the way to the back of his throat while he used his tongue to lap away at the underside. I felt his hands start to gently caress my ball sack, sending another powerful tingle through my loins, then I felt a familiar burn and knew what was coming. I put my hand on the back of his head again, earning me yet another horny moan, then I felt his left hand wrap around the base of my dick. At the same time, he pulled my cock out of his throat and wrapped his lips around the head, forming a seal just below my glans. With his sucking mouth now in place, he began to stroke my cock with his hand, hastening the approach of my climax.
With his hand stroking my cock at the base and his mouth sucking on the head, I felt the sperm start to travel up my shaft at an unstoppable pace. He must have felt it too, because he rolled his underwear clad rear end around with a long, needy moan and used his tongue to bathe the head of my cock. With his scratchy tongue and his talented hand working in tandem, a fire spread quickly through my groin and I let loose with a loud groan. At the exact moment that my groan carried into my ears, my cock began pulsating over and over and a fountain of hot sperm spewed forth, filling Jimmy's sucking mouth. His eyes were shut tight and he had a dreamy smile on his cute face. His Adam's apple was bobbing up and down as he swallowed the load that I presented him with. I was startled at how he was able to keep up and not lose a drop, knowing that the load I had stored up seemed to be shooting out with the force of a cannon.
When my sperm sack was empty, Jimmy used his tongue to bathe my entire shaft, then he took to my pubic bush, anxious to find and lap away any jizz he could find. While he was carrying on with his task of licking my crotch clean, I laid back and let my post orgasmic glow wash over me. I felt him press hard on the tops of my thighs, using them for leverage to stand up. I smiled when his cute face came into view from my prostrate position on the bed, then I patted the spot next to me and a smile spread across his lips.
When he cuddled up to my chest, I wrapped an arm around him and held him close, loving how warm his young body felt. He rested his head on my chest and sighed, so I ran my fingers through his blonde hair and spoke to him.
“You never made it out of your underwear, kiddo,” I said softly, prompting the little boy to turn his head so that he could smile at me.
“I was kinda thinking that I could pull them down while we're on the bed,” he said with a sweet inflection in his voice. “I still want to give you some butthole.”
With that, he leaned in and pressed his dick sucking lips to mine, letting his tongue slide into my mouth with a soft moan. As our kiss lingered, he used his hands to grab his underwear at the blue striped waistband, easing them off of his hips and freeing his hard pecker, which was still sticking straight out. I gave off a moan of my own when it came into view, feeling my cock jump as it filled with blood all over again. His dick was so adorable, just three and a half inches at full mast and completely hairless. It was pressed tight to his bald pubic bone, a tribute to the pleasure he received from the blow job he gave me and the resulting cum load that he swallowed.
As much of a shame as it was not to be able to wrap my lips around his precious boy rod, though, I didn't press the issue. Instead, I grabbed his left ankle and gave it a tug, prompting him to break our kiss and give me a curious look. Without a word, I tightened my grip around his ankle and pulled his body around so that we were in the 69 position with his ass directly in my face, then I parted his plump cheeks and opened up his deep crevice.
His boy pussy looked like a delectable slice of heaven. It was about an inch in diameter, slightly sunken, but its folds were uniform. His pucker was shaded dark pink, perfectly in tact with just a little evidence of its frequent use. The aroma that was pouring off of it was pure boy, a strong pheromone that was filling my nostrils and dancing all around my face.
Without having to be told what I wanted him to do, Jimmy took the initiative, parting his legs even further and splaying his hot hole for my dining pleasure. I grabbed his hips tightly and pulled him back far enough to bury my mug in his crack, then I dug in with my tongue. With my tongue buried in his pucker, little Jimmy started moaning wildly. At the same time, he wrapped both of his hands around my cock and wrapped his lips back around its head, nursing on the end like a baby with its bottle. His ass was delicious, a tasty treat that any boy lover would be grateful to dine on, and I knew that I needed to fuck this kid right away. His warm ball sack was resting on my chest while his hard little dick stayed pressed to his pubic bone, barely an inch away from making contact with my skin.
I stayed where I was and dined at Jimmy's back door for an extended period of time, feeling like I could taste the activities of his entire day back there. I was in a state of sheer bliss when I felt Jimmy pull his mouth off of my cock and plant a long kiss on the end, then he whimpered, “I'm ready for you to put your dick in my butt, Mr. Love.”
I reluctantly pulled my tongue from his boy pussy, hating to abandon such a heavenly feast. At the same time, though, I was eager to feel the tight confines of his rear end around my shaft, then plant my seed there. As soon as I pulled my face out of his ass crack, Jimmy took the initiative again, this time by putting himself into position and straddling my midsection. I was concerned that he might not be accustomed to accepting a cock the size of mine, but once again, the little cock hound proved me wrong. With a glazed over look in his eyes, he lowered himself down so that the head of my cock was nestled in his ass crack, pressing snugly against his entrance. Then, with the ease of an experienced pussy boy, his rear end opened up and my entire length was swallowed in one impressive motion.
The feeling of his tight bottom wrapping itself around the length of my shaft was incredible. Given the difference in our size, I was amazed at how easily he accepted my shaft. My cock is certainly no trophy, but at 7 hard inches, it's still man sized. The fact that he took it all at once was stunning. The fact that he did so with a dreamy smile on his face told me that he'd taken his fair share of cocks up the ass, and that he clearly loved it. When I felt his soft buns come to rest against the tops of my thighs, I gazed up at his face. He was grinning hard, the look on his face one of total decadents as the muscles in his ass flexed around my shaft.
Through pursed lips, Jimmy started a sensual up and down motion with his thighs. The hot, tight, silky ribbons of his boy pussy felt like heaven as they pulled and pushed along my length. The moist membranes that lined his ass were wrapped tight around the head of my dick, giving me a luscious feeling as he settled into a steady ride. His ass felt like an oven set to broil, and its heat was pouring out of his hole, pushing down my shaft, running through my wiry pubic bush and wrapping around my ball sack. At the same time, the head of his little dick was starting to moisten with a single droplet of precum that shined like a pearl. It was bedded in his piss slit, serving as a reminder that he was enjoying our union as much as I was.
Of course, his moans and the growing smile on his cherubic face had already given that pleasure away. So did his hard on, sticking straight up and pressed so hard against his bald pubic bone that his nuts were protruding through his ball sack like two little almonds. I felt his palms come to rest on my torso, then I felt him use them for leverage as he picked up the pace of his ride. Almost as soon as his tempo increased, I felt the heat in his boy pussy intensify, adding to the building pleasure that I felt in my body. I felt the familiar burn of an orgasm starting to creep up on me, then I felt the muscles in his ass get tighter around my cock. Before I could compute what was happening, I felt a frantic tremble roll through my entire groin region, then the cum started to rise up my shaft.
Almost as if he knew what was about to happen, Jimmy quickened his ride again. This sent a wave of orgasmic signals through me and I lost control, firing my load straight up the 12 year old's ass with a loud groan of pleasure. Jimmy was such a little pro that he somehow managed to time his ride so that he was catching the spurts of cum on his downward thrusts, causing each shot to squirt deep inside of him while he continued to enjoy the ride. When the final string of cum shot from the end of my cock, the horny little boy continued to ride my dick, eager to keep his fuck going as long as he could.
Finally, the stimulation was too much on my sensitive cock and I had to reach out with both hands, taking him by the hips and slowing him until he stopped. When he climbed off of me, he quickly wrapped his lips back around my spent shaft and gently sucked it clean. Once again, his experience showed, as he used his tongue to bathe the underside of my cock while taking care to treat my sensitive dick with tenderness. When there was no more cum to lap up, the little sperm lover moved down to my nuts, where he sought out and found the remainder of his prize.
From my prone position, I watched the boy work with what I'm sure was an expression of shock. He was so efficient in his cock cleaning process, licking up the maximum amount of cum with the minimum amount of stimulation on my cock. When he was satisfied that there was no more cum to swallow, he crawled up to my chest and collapsed in my arms, letting me hold him close while he purred like a kitten.
“My mom and dad said I can have some fun tonight,” he said quietly. “We're staying at the hotel tonight because she has to work early in the morning.”
“Are you planning to have some friends from school sleep over?” I asked curiously, wrapping my right arm around his slight frame and rubbing his back under his shirt.
“No, I wanted to have some fun with the hotel guests tonight,” he told me. “Sometimes when we spend the night at the hotel, my mom and dad let me have some fun with the guests until its my curfew.”
“All of the guests?” I asked, and he nodded with a hopeful look in his eyes. “That sounds like a lot of fun.”
“It is,” he said with a husky voice. “I wanted to invite you, too.”
“Oh yeah?” I said in a jovial tone.
“Yeah, I wanted to have a glory hole in my room tonight,” he admitted.
“Have you done that before, Jimmy?” I asked, and he nodded.
“If you come, I'll be really happy,” he said with a sweet smile. “My curfew lasts until it's midnight, so you can use me a lot of times.”
“You must be really horny, buddy,” I observed, letting my forefinger trace along his body until it reached his hard little pecker. I ran the tip of my finger along its length, and with a naughty smile, he swatted my hand away.
Upon leaving my room, Jimmy went straight down to the registration desk to report to his mother. He let her know that he enjoyed our visit, and she seemed quite pleased with this. While Jimmy was dishing to his mom about our encounter in my room, a hunky 28 year old walked up to the desk with his reservation itinerary in hand. Jimmy took notice of the brunet hunk and felt a shiver run through his horny young body. The man made eye contact with the boy and felt his cock fill with blood, then Jimmy spoke up.
“He's cute, mom,” the youngster said, and the man felt an instant thrill run through him. Right away, a large bulge appeared in his pants. Both mother and son trained their eyes on the man's package, then the hotel manager nodded her approval.
“Do you like what you see, sweetie?” she asked in a soft voice, and the cute boy nodded without taking his eyes off of his crotch. With a knowing smile, his mom told him, “Well, you'll have to invite him to your party.”
“I'd really like that, mom,” he told her, then he bit his lower lip and gave the guest a hopeful smile. The entire time that the hotel manager was assisting the guest, the horny boy was licking his lips and smiling seductively. Once the man was checked in, the youngster hopped off of his stool and followed him to a nearby men's room. With a knowing grin, the hotel manager continued to work, sure that her son was getting lucky with the man.
Indeed, Jimmy had managed to lure the man into a handicapped stall and was now bending over with his pants and underwear bunched around his knees. His bubble butt was sticking straight up into the air and the 28 year old stud was holding onto his hips, fucking a hot, satisfying load into it while both man and boy shivered with pleasure and lust. When the horny boy was seeded, he quickly made plans to have the man visit his glory hole later on. After a deep kiss, they both pulled their pants up and the boy returned to the lobby.
Still feeling incredibly horny, the youngster immediately started to flirt with men in the lobby near the cocktail lounge. In short order, he was ushered back into the bathroom by a tall, husky man in his 50's. The boy was treated to a mouthful of hard cock that he didn't even have to drop to his knees to enjoy. The man pulled his horse cock out of his trousers, and with the height difference between them, Jimmy only had to wrap his lips around it and suck. Soon, he was rewarded with a large load of cum that he swallowed with urgent gulps, then he spent a glorious afterglow licking and sucking the man's balls.
Now on a certifiable tear, he meandered back out to the lobby, where he started to flirt openly with all of the men. He soon found himself back in the stall, bending over for a quick ride that brought him nothing but pleasure. When his butt fuck was finished, he went back out and found another man to give him some cock in the men's room. After having his bottom serviced with another big dick, the boy hiked his school pants and made his way back out to the lobby. As he walked out of the men's room, he felt a torrent of cum run from his ass, soaking through the seat of his pants.
No longer concerned with being discreet, the gay youngster made it clear to every man within earshot that he was horny to service cocks, and that he would be hosting a glory hole in his room as soon as his mother's shift was finished. He also made it clear that he was interested in getting as much action as he could until he made it to his room for the night. His mother watched from the desk as her son led a trio of men to the restroom, eager to take their loads. The stall was too cramped for three men and one boy, so they simply got busy by the sinks. The boy quickly dropped his drawers and bent over, wrapping his lips around the cock of one of the men while another got behind him and buried his dick up his ass, treating him to a pleasure filled lay. His top pulled out without shooting, and the third man quickly mounted the boy and fucked him fast and dirty until he was ready to blow. Jimmy's fun with the men finished when he dropped to his knees and let all three of them blow their pent up loads all over his smiling face and in his hair, then he sucked them all dry.
After his romp in the men's room, he rejoined his mom at the front desk. Seeing the state of wreck that her son was in, she instructed him to go upstairs to their room and wait for her there. When she joined her son, she made sure that he was ready for his evening. At his mother's insistence, Jimmy laid across her lap and took two enema's, then he pulled his knees to his chest so that she could lube his rear end up. He dressed in a pair of blue jeans and a plain white tee shirt, giving him the appearance of a rugged boy, then she kissed him on the cheek and promised to come collect him at midnight.
Jimmy rode the elevator to the sixth floor, then he made his way down the quiet hallway to the last room on the right. Much to his delight, the door to the room was already propped open, just as he hoped, and there were three men waiting inside. With a naughty smile, he quickly undressed and walked up to a man in his 40's who was sitting on the bed, naked and stroking his cock. Jimmy immediately wrapped his arms around the man's neck and engaged him a long, tongue filled kiss while the others watched knowingly. When they broke their kiss, Jimmy was lifted into the man's naked lap.
“Did you have a good time in the lobby, son?” the man asked, prompting the boy to nod his head with a hard grin on his face.
“I took a lot of cocks in the bathroom, dad,” he sighed contentedly. “I was so horny that I couldn't wait.”
“That's what mom told me,” the man said, running his fingertips through the boy's sandy blonde hair. “Did you get a good warm up down there?”
“Yeah,” the youngster said, feeling his father's cock nestle between his buns. “But I'm ready to get started.”
“Whose cock would you like to ride first, Jimmy?” the man asked, and the boy gave his father a love struck smile.
“Yours, daddy,” the youngster practically sang. “I've been horny for it all day.”
“Give daddy another kiss,” the man commanded, and the cute boy quickly complied.
With his father's tongue now dominating his own, Jimmy felt light headed with lust and started to moan. The loving father, whose cock was pressing against the lubed up entrance of his son's boy pussy, decided to move things along for the horny boy. He effortlessly picked his boy up by cradling him in his arms, then he gently laid him on the bed so that his head was right at the edge. Then, without ever breaking their kiss, the man used his hands to lift his boy's legs and line up to his hole. When he pushed in, Jimmy gave off a series of frantic moans, then he felt his little body shiver with pleasure as he accepted a deep butt fucking from the man in his life.
In the midst of taking his first cock at the gathering, Jimmy heard more men file into the room. Eager to be a true glory hole, he broke his kiss with his dad so that he could have a cock eased into his mouth. With a cock once again filling both ends, the boy felt overjoyed and soon took a cock in each hand. When his dad seeded his boy cunt, Jimmy sighed with a dreamy smile, then he felt his dad pull out. Seconds later, another man cock slid deep inside of him, giving him more chills of delight.
With his cock sticky and dripping with cum and ass juice, Jimmy's dad sat on the edge of the bed and let a horny, 18 year old twink suck it clean. When the smooth teenager was through sucking the remnants of the sex that the alpha male had with Jimmy, he took his own turn in the boy's ass. With his 18 year old cock buried in a hot, tight boy pussy for the first time, the twink had no trouble seeding it in under a minute while someone blew their load all over Jimmy's chest. When he pulled out, he was quickly mounted by a 45 year old bear while Jimmy's moans carried into his ears.
By the end of the first hour, the room had filled up with men. Some of the visitor's to Jimmy's glory hole had left for the evening, but many decided to stick around and take another spin in the boy's talented ass or mouth. When I arrived, Jimmy was laying on the bedspread, flat on his back with his legs spread wide. A bearded man who had posted up between his thighs was feeding him firm strokes of cock up the ass while a cute 22 year old stood at Jimmy's bedside, feeding his dick to the little cock hound from the left. To the right of the boy, two men were resting on their knees, jerking their cocks over the boy's heaving chest while he used his hand to fondle their balls.
Once again, I spotted a look of sheer indulgence on his face. He had a sexual glow about him that told me how much he was enjoying his role as the glory hole. Around the room, there were men and young twinks sitting together, fondling each other and getting ready for their turn with the cock hungry 12 year old. While I was watching the boy service cocks, I caught the eye of an adorable boy who I later learned was just 15 years old. Knowing that I would have to wait for my turn, I gravitated toward the cutie and struck up a conversation with him. In record time, I had the youngster on his knees, fishing my dick out of my pants while he licked his lips in anticipation. After giving him the mouthful of sperm he was so hot for, I dropped to my knees and parted his cheeks, revealing his winking brown eye. Unable to resist, I dove in head first, eager to dine at his back door. After a heavenly feast that rejuvenated my cock, my young lover and I took our turns with the boy of the hour. The 15 year old got his jollies right away, blowing a fast load down Jimmy's throat while I pumped a hot load up his ass. Before I gave up my load, two more dicks were sucked by the boy, giving him two more hot loads to swallow while he used his hands to fondle any set of balls he could.
When my first turn in Jimmy's glory hole was over, I got intimate with a smooth 19 year old and his equally twinkish 20 year old lover. They both knew how to service a man, just like Jimmy, and were doing their best to work another load out of me. While the 19 year old ate my ass, the 20 year old treated me to a first rate blow job. While the two lovers were having their way with me, I watched Jimmy take a series of hard, fast fucks in the ass while he moaned around his father's hard cock. The boy was gazing up at his dad with a look of sheer devotion and pleasure on his face, running his little fingers through the man's dark, thick pubic bush. Which is why it was no surprise to me when he lovingly pulled his dad's cock from his mouth and said, “I want you to do my butthole next, daddy.”
Giving into his little boy's needs, the man petted his son's cum matted head of hair and watched as someone finished inside of him. When he assumed the position between his boy's legs, it was like the room stopped for a moment. Jimmy's loving smile was fixed on his dad's face, watching with tenderness as the man inserted his penis, then buried his entire length up the boy's rear end. It was strangely intimate, almost as if we were all intruding on a special moment. When he began to thrust, the sexual glow on the youngster's face seemed to intensify and he immediately started to climax. His little cock was jumping around almost aimlessly, erratically twitching and pointing in all different directions as his dry orgasm consumed him.
While he was in the midst of his boygasm, someone placed the head of their cock at his lips. With the instinct of a true pussy boy, little Jimmy let them part and the cock slipped into his mouth. This gave the climaxing 12 year old even more pleasure, extending his sexual peak while he sucked diligently. Moments later, the gay youngster was swallowing a thick load of cum at the exact moment that his dad was pulling out, having blown his own load deep inside of the boy. With his ass now absent a cock, the little boy kept his legs spread wide, inviting the next cock to enter him. Seeing his window of opportunity, a 60 year old bear crawled between the boy's opened legs and slid his eight inch monster up the boy's ass.
With my cock rock hard from the rim job and expert blow job I was receiving, I quickly took my next turn in Jimmy's glory hole. I watched him swallow a thick load, prompting me to gently pull the 20 year old cutie off of my cock. With a smile, Jimmy opened wide and wrapped his lips around my dick, sucking it with satisfied mews while the old man between his legs serviced his rear end. Much to the horny boy's delight, the two twinks that had been pleasuring me posted up on either side of him, providing the cock hungry 12 year old with a cock for each hand. While he was pleasuring their dicks, the two twinks took turns kissing me and the older bear hungrily. I was treated to a long, tongue filled kiss by the 20 year old while his 19 year old lover engaged the bear. When they were through with us, they fell into a deep kiss with each other while Jimmy watched with a naughty smile from the bed.
When Jimmy was seeded by the bear between his legs, he was quickly mounted and fucked by the 19 year old. After three luscious minutes, he took the teenager's load across his stomach, then he was mounted by the 20 year old. After having his boy cunt seeded again, Jimmy was mounted and fucked by two men who each lasted less than a minute in his rear end. One of them was still wearing his jacket and only opened his fly enough to let his dick spring loose. When the two men walked out of the room, the 15 year old cutie who I had been with earlier crawled between Jimmy's legs and took a spin in the youngster's ass. When he pulled out, he was cuddled by an older man in his 40's. Eventually, the man managed to ease the youngster into a deep kiss and ultimately, he was mounted and fucked on the bed beside Jimmy. Watching the cute teen take a hard dick in the ass was enough to make me blow my load down Jimmy's throat, then I pulled my dick out and the bottoming 15 year old begged me to let him suck on it.
When the man pulled out of the teenager, I dined at the boy's back door for an extended amount of time, then I took a spin in his ass while he gazed up at me with an adorable smile. While I was still hard, two men finished inside of Jimmy at the same time. Seeing this, I pulled out of the grinning 15 year old and urged him to let Jimmy blow him again. While Jimmy was sucking his teenaged partner off, I crawled between his legs and got my rocks off up his ass one more time. When I pulled out, Jimmy rolled over onto his stomach, then he used his knees to raise his ass up into the air. With his enticing new position, Jimmy found himself accepting another series of hard cocks while his proud daddy watched from the other side of the bed.
When midnight rolled around, Jimmy was still in the doggy style position, taking a long, thick cock in his ass while he shivered hard. True to her word, his mom arrived to collect him, knowing that her husband would lose track of time. When the man spotted his wife, he smiled and greeted her with a tender kiss, then they watched with pride while their little boy had his horny rear end serviced one last time. When the boy was seeded, he stayed in position, eager for the next cock to enter him, but we all knew that the end of our orgy had arrived and no one moved to answer his mating call. Seeing that her baby boy was still in want of some dick, the sympathetic mother held firm, collecting her son's clothing and dressing him while we all cleared out.
When the room was empty, the hotel manager instructed her husband to take the boy back to their room and get him ready for bed. Following his wife's instructions, the man hoisted his sleepy son up into his arms and carried the youngster out of the room while she opened the patio door to clear out the smell of ass and cum that was permeating the air.
As they made their way toward the elevator, the 12 year old felt a torrent of cum and ass juice escape from his boy pussy, soaking the seat of his pants and underwear. His dad noticed it too, and as father and son contemplated the sticky contents of Jimmy's underwear, the boy whispered into his father's ear.
“I'm still horny, daddy,” the naughty boy admitted, simultaneously blowing into his dad's ear. “I want you to pinch my butt until we get to our room.”
The loving father quickly acquiesced, giving into his son's needs by treating him to sweet pinches on the ass while the youngster talked dirty to him.
“You were a busy little glory hole tonight, weren't you buddy?” his dad observed, and the cute little cum slut responded with a soft moan. “You didn't get enough cock yet, Jimmy?”
“Not yet, daddy,” the boy said, nuzzling his head into his father's shoulder. “I need my butthole serviced some more.”
“Daddy's little gay boy can't get enough, can he?” the man said, planting a kiss on his son's head.
Jimmy shook his head no and whimpered, “I need it from you, daddy.”
“I know you do, son,” the man said, rubbing his little boy's back tenderly as he stepped into the elevator. “When we get to our room, daddy's going to show you just how much he loves his little gay boy.”
“Thank you, daddy,” Jimmy sighed, a sense of pending relief washing over him as his father's promise carried into his young ears. “Your little gay boy loves you, too.”
When they got to their room, the man carried his son to the bathroom and the two of them got undressed. Knowing that the boy's ass was still filled with cum, the man instructed him to sit on the toilet while he prepared two enemas for him. With a naughty smile, the boy laid across his father's lap and accepted both enemas. When his boy pussy was flushed out, they both got in the shower and once again, Jimmy begged for some cock at his back door. Unable to deny his son, the loving father mounted his little boy and fucked him to a furious climax, then he pulled out and shot all over his smiling face.
When they got out of the shower, the youngster got dressed in his pajamas and crawled into the bed with his naked father. Needing something to soothe him into his slumber, the little boy crawled between his father's legs and wrapped his tender lips around his man cock. When his mom got back to the hotel room, she smiled at the sight of her horny boy, settling in for the night with a mouthful of hard cock. Both man and wife snuggled close on the bed and surfed channels, talking about their day while Jimmy sucked with a sweet smile on his sleepy face. When Jimmy received his daddy's load, he stayed where he was and nuzzled his head on the man's thigh, using it as a pillow and falling fast asleep.
Keith's Guilty Pleasure
Other Work by Josh Terrence:
Stuart's Insatiable Itch (Gay/Incest)
Corey in the Morning (Gay/Adult-Youth)
Adam Needs a Ride (Gay/Adult/Youth)
Sean's Day Out (Gay/Adult-Youth)
A Curious Tug of War (Gay/Adult-Youth)
A Stir in Ian's Bottom (Gay/Adult-Youth)
Jason in the Men's Room (Gay/Adult-Youth)
An After School Quickie (Gay/Adult-Youth)
The Boy at my Door (Gay/Adult-Youth)
The Coupling (Gay/Adult–Youth)
Taylor Made (Gay/Incest)
Phillip's Spending Habits (Gay/Urination)
James' Secret (Gay/Urination)
Kyle's Afterschool Snack (Gay/Urination)