Pleasuring Henry, 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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It was a chilly, cloudy Saturday morning. My best friend Roger and I were in my backyard throwing the football when a familiar voice rang out.

Hey Jacob,” I heard Henry say from the other side of the chain link fence, where he was sitting on his bike and holding onto the gate for balance.

Hey Henry,” I said with a grin over my shoulder as I tossed the ball to Roger. “What are you up to?”

I just wanted to know if you and Roger wanted to do something,” he said suggestively, running his fingers through his short blonde hair. “I just left a friend and I don't feel like going home yet.”

With that, Roger and I shared a knowing look between us and silently communicated. Our knowing look soon turned to a naughty grin that we were sharing, and I invited him in.

What do you feel like doing today?” I asked, and he licked his lips hungrily as he looked me over.

I've been taking it up the butt all morning,” he said with a tinge of desire in his soft voice, batting his eyes as he approached the two of us. “I was kinda hoping to keep it going.”

With that, I hurriedly led him into my house through the back door and we made a beeline for my room. In no time flat, all three of us were out of our pants and Henry was on his hands and knees, sucking on my cock while Roger lined up to his easy access hole and pushed in. All three of us were moaning, but Henry was clearly the most enamored of us all. He was letting go of soft, almost girlish sounding moans while he sucked lustily on my prick. His supple bottom was sticking out so far that Roger only had to push his 12 year old rod through his entrance and rest his hands on his plump, round buns.

It doesn't feel like he's been fucked at all today,” Roger panted, his light brown curls bouncing with the momentum of the ride. “It's hot and tight.”

With a loud, wet slurp, Henry pulled off of my dick long enough to whimper, “I just got laid before I came over here.”

With that, he resumed his wet, pleasure filled sucking while he moaned softly around my aching cock. I responded to his confession by gently stroking his fine blonde hair and caressing his baby soft cheeks. While I was grinning down at the boy who Roger and I were double dicking, my buddy started to slam hard into his upturned bottom and I knew well what that meant. The look on Roger's face said it all; his brown eyes were filled with raw emotion as his boygasm neared and the sound of his bald pubic bone slapping against Henry's butt cheeks was gaining speed.

With a loud, sudden groan, he pushed in as deep as he could and froze, then his body shivered and a smile spread out across his face. Henry responded to this by pulling off of my dick again, then he smiled up at me and bit his lower lip while Roger pulled out of him and rested on the backs of his legs. In a flash, Henry spun around and got back into position, sticking his bottom out so far that all I had to do was stand on my knees and push in. As soon as I placed the head of my hairless rod up to Henry's quivering, winking hole, it bloomed for me and my entire 4 inches slid in with ease.

I looked at Roger, who was panting heavily, then down at Henry, who was moaning lustily. I took note of the fact that he was resting his forearms on the floor and using his hands to support his chin while he sucked dick. Roger had a look of amusement on his face as he watched the pussyboy who had come by for his fill of our cocks casually blowing him without a care in the world. While Henry was treating himself to a mouthful of Roger's 12 year old boyhood, I was running my own hardon back and forth in his familiar rear end, which as it turned out, was just as hot and tight as Roger said it was. I could feel it throbbing with every stroke that I fed it, constricting over and over again, just like it always does.

I reached down and ran my hand across Henry's fleshy butt cheeks and smiled happily, wondering how my best buddy and I got so lucky to have a cock hound like him in our circle.

Roger, Henry and I have lived in the same neighborhood our entire lives. Roger's my best friend, but we both grew up with Henry and have played with him off and on over the years. When we were in 5th grade he suddenly announced that he was gay on the playground. Along with a few other boys, we took it upon ourselves to protect him from bullies for the rest of the year. As the school year progressed, it became more and more obvious that Henry was telling the truth, especially when he started dating a boy in middle school named Tyler. It felt a little weird to see our 10 year old classmate holding an 8th grader's hand every day, but eventually we all got used to it.

When we went into middle school the next year, Henry seemed to be hanging all over a new boy every other day. By the time Christmas Break rolled around, he had developed a reputation as an easy lay but it didn't seem to faze him at all. In fact, he almost seemed to embrace his new found status and used it to get the attention of the boys in our school. At some point he started flirting with me, but at 11 years old I was too naive to understand what he wanted from me.

The week between Christmas and New Years he showed up at my door, knowing that Roger was at my house and that my dad was at work. We let him in and casually gamed online, then we put a Blue Ray in and watched a movie on my bed. Seizing the moment, he made a rather blatant pass at us while the movie played on my TV.

“I want to suck your dicks,” he announced as if it were nothing out of the ordinary, then he gave us a look of longing. “I was kinda hoping that you'd want to do me in the butt, too.”

“Fucking hot!” Roger exclaimed, then he covered his mouth with both hands with a naughty smile.

Realizing that Roger wanted to play, Henry made the next move by offering him a blow job. Then, with a hopeful smile, he assured me that he wanted to suck my dick too.

“How would you do it?” I asked curiously, and he gave me a sweet smile.

“You can let me do it here in the bed if you want to,” he offered, then he sighed dreamily. “Or we can go in the bathroom by ourselves so it's more private.”

I wasn't sure that I wanted to go through with it, but before I could answer for myself, Roger blurted out, “Let's do it in the bed!”

With that, Roger sat up with his back against my headrest while I sat next to him and watched Henry give him a blowjob. It looked like it felt so amazing and I slowly came around to the idea of getting my dick sucked by a boy. Henry had an animated smile on his face the entire time, his wet, plump lips seeming to double task as they ran along the length of Roger's boner and translated his pleasure all at once. I could hear Henry letting loose with soft moans that only added to the moment while he sucked diligently.

For his part, Roger was wearing an expression of sheer Nirvana while Henry blew him. His right hand seemed to gravitate to Henry's short head of blonde hair, where it came to rest while Henry smiled up at him with appreciation. My best friend was biting his lower lip and exhaling over and over while his midsection pushed up from the bed over and over.

“It tingles,” he whimpered out of the blue, then he started to pant and moan almost helplessly while Henry's lips looked like they were tightening around his boy cock. All of the sudden, Roger's eyes shot open and he let loose with a hard groan, then his expression melted into a blissful smile and his hand slid from the top of Henry's head.

“Dude, you have to try it!” he told me when Henry pulled off of his dick, still panting from the rush of the moment. “That was fucking amazing!”

While I was preoccupied with Roger's proclamation, Henry reached over and gave my inner left thigh a tender rub while he looked up at me with desire. Realizing that I might miss out, I lifted my butt up from the bed and eased my undies down, causing a grin to spread out across Henry's face. As soon as my cock sprang free, I looked over at Roger and blushed, but he didn't seem to care about my nakedness at the moment. He was still glowing with absolute contentment that I was studying when I felt the warm, wet sensation of Henry's mouth enveloping my stiffy with an effortless swallow.

To this day, I have no way to describe the feeling of carnal delight that was coursing through my system as I received my very first blowjob. I could hardly believe what a pro Henry was at sucking dick, and how much he seemed to enjoy it. It was almost as if he were in a state of sheer euphoria as he worked his head up and down and used his tongue to pleasure the head of my dick. Less than a minute into his act of oral goodness, I felt my legs start to tremble and the joints in my toes cracked loud, all at once.

Just like Roger, I lifted my midsection off of the bed as my very first orgasm built to a crescendo. When it hit me, I threw my head back so hard that I slammed it against the bed board, prompting Roger to exclaim, “Holy crap, dude, are you okay?”

I nodded my head to assure him that I was fine, then I heard my cocksucker moan with delight and looked down at him with a labored expression. His blonde hair looked like it was moving in a blindingly fast up and down motion while he savored the end of the blowjob he was giving me, then my prick got sensitive and I had to practically beg him to stop.

When he finally pulled off of my dick, he sat back on the bed and smiled at Roger and I. His khaki pants were tenting with his own erection and he had a look of arousal on his face that he couldn't have covered up with a ski mask.

“How was it, man?” Roger asked excitedly, and I turned to him with a smile while I panted and nodded again.

“It was... it was so...,” but I couldn't get all of the words out. I looked at Henry and we locked eyes for a moment, smiling dumbly while I struggled for words that I couldn't find.

Once again, Roger broke the silence by asking Henry, “Do you still want to take a dick up the butt?”

“Uh huh,” Henry practically stuttered. “I'll pull my pants down so we can do it.”

And just like that, he pulled his shirt off over his head and bunched it up. As if it were business as usual, Henry stood up on his knees and unbuttoned his khakis, then he slid them off of his waist, leaving him in a pair of white briefs that were tented in the front. In a matter of fact manner, he hooked the blue striped waistband and pulled them down, revealing his hairless, three inch boy boner. Then, without batting an eye, he turned to face away from us and got on his hands and knees, presenting his round, pale rear end to us.

As soon as he got in the doggystyle position, he parted his legs so that his butt was hanging out, making his pale, plump buns part on their own. Right away, I took notice of the way his slender midsection gave way to a pair of buxom hips that were curved in a way that made his bubble butt even more alluring. His rear end was comprised of two perfectly formed half moons, giving it the shape of a beach ball. Between his buns was a deep, warm looking valley with a dark red, nickel sized pucker that looked slightly sunken. I couldn't help but notice that it was moist and seemed to be throbbing, maybe even winking at us.

To my right, Roger looked like he was in a trance. He had his brown eyes trained on the same thing I was looking at, but his mouth was watering. I followed his gaze into Henry's crevice, then let my eyes wander down to his seam, which was bright red and surrounded by goosebumps. Just below that, his boyish package was on full display, almost teasing us with his shameless exhibitionism. His hairless ball sack was pulled tight to his body and his miniature sized boner was pointing at the bed while the vertebrae of his spinal column bulged through the smooth skin along his back.

Henry's bottom looked so irresistible as he hung it out for Roger and I. It was beckoning us to pay it more attention, practically screaming for us to forget about his cock and balls, even though they were right there. As if he were reading my mind, Henry lowered his torso so that his rear end was sticking straight up and the side of his head was resting on the bedspread, then he gave his hips a slow, sensual stir and I felt my cock jump.

“Fuck, he wants us to do him in the ass,” Roger spat, and Henry nodded almost absentmindedly in agreement while he continued to churn his bottom.

Just like before, Roger was the first to saddle up to Henry's rear end and slip his 11 year old prick inside. Henry was gazing back at him with a set of bedroom eyes that I'll never forget. The instant that Roger placed the rigid head of his boyhood up to Henry's hole, a strong, hot scent reminiscent of poop filled the air. Roger didn't seemed to be fazed by it at all, and in a strange way, I found it intoxicating. When Roger pushed through his opening, Henry let loose with a long, horny moan of desire and the aroma in the room grew even more powerful for a moment.

The entire time that Roger was humping in and out of his hole, the blonde bottom was moaning with contentment and switching his gaze between us. While he was gazing at Roger, he had a look of sheer devotion on his face. When he would fix his gaze on my face, the look on his face was one of pure arousal, as if he were pleading with me to take a turn in his love tunnel.

So when Roger's bald pubic bone started to slap so hard against Henry's bottom that his fleshy cheeks jiggled, I knew that I would be taking my turn. When Roger let go of a long, boyish moan that sounded like a wolf cub howling, I stood up on my knees and prepared to move in. When Roger shut his eyes tight and exhaled with a satisfied smile, I prepared for his eventual withdrawal while Henry watched with hopeful eyes.

Happily for Henry, I didn't make him wait long. As soon as Roger's still twitching boy cock emerged from the depths of Henry's bottom, I eagerly slipped my rod into what I can only describe as paradise. It was the most amazing feeling that I'd ever experienced. There was so much heat and moisture, but at the same time it was incredibly snug, silky and fulfilling. Henry was grinning back at me while I rested and got used to the binding environment that my dick was now occupying. There was a distinctive poop smell dancing around my head but I didn't let it bother me because the pleasure that I was feeling far outweighed the stinky aroma.

“It stinks a little, but it feels so fucking good,” Roger said, and I nodded in agreement. “Start moving your hips back and forth and it'll feel even better.”

Of course, Roger was right. The sensations that I felt as I started to hump Henry's rear end were incredible. Indescribable, even. All I can say is that I could feel a constant tremble rolling through my 4'5” frame while I lost my virginity with my best buddy in the whole wide world. When I felt my boygasm erupt all over again, it was a different feeling than before. It wasn't a wet mouth that I was shivering inside of, it was a smelly butthole. And somehow, that made it even more pleasurable for me. By the time the explosion rocked my body, the tremble I'd been experiencing had turned into a full scale rumbling that I was helpless to control.

When it was over, I pulled out of his bottom and collapsed on the bed while Henry crawled up to Roger and I, sucking our cocks clean with satisfied moans while his sleepy eyes stayed trained on our faces.

We were laying in a heap on my bed, still basking in the afterglow of our latest romp. Roger was sprawled out near the foot of the bed with his feet hanging off the side and his hard pecker sticking straight out from his body. Henry was snuggled into my side, toying with my nipple while I held him close. I looked at the clock and realized that it was getting close to lunch time, wondering if Henry was going to have to go home or not when Roger piped up.

“I'm hungry,” he announced, then he rolled over onto his side and grinned at me and Henry. “If you two love birds are finished over there, let's get up and find some grub.”

Taking his cue, we got up and walked naked into the kitchen in search of something to eat. While Roger and I were standing at the counter, Henry came up from behind and pinched our bare bottoms playfully. Roger moved to retaliate by groping Henry's bubble butt and giving it a smack, and eventually they wound up wrestling on the floor. It was no surprise to me when their playful wrestling match devolved into a tongue heavy kiss that I couldn't help but peek at while I worked at the counter. Eventually, Henry wound up on his hands and knees again, grinning over his shoulder while he took an impromptu butt plugging on the kitchen floor from Roger.

When it was over, we sat at the table and ate our sandwiches while Henry and Roger played footsie under the table. After lunch, Henry made a pass at me so I took a turn hammering his tight bubble butt in the living room while Roger surfed channels on the TV. After a satisfying lay, Henry and I shared a long kiss, then he got on his knees and sucked cock for the rest of the afternoon. Roger and I took turns getting off in his bottom while he sucked continuous dick for each of us, and it was clear that he was loving the action as much as we were.

At 3:30pm, he had his lips wrapped tight around my prick and Roger's dick was sliding back and forth in his rear end when his cell phone rang.

“Hi dad,” he said nonchalantly, then he wrapped his lips back around my cock with a soft moan while he listened. When he needed to speak, he pulled off of my cock with a slurp that I was sure his dad could hear and said, “I've been spending the day with Jacob and Roger.”

With that, he slipped his mouth over my dick head and resumed the blow job he was giving me, his hard pecker standing straight up the entire time. When his dad was finished again, he pulled off with another loud slurp and in an agitated tone said, “I'm sucking dick right now. I'll come home when I finish.”

I almost choked when he said that, but once again he casually wrapped his lips back around the tip of my dick and moaned softly while his dad talked. Pulling off one more time, he said, “I love you too, dad. I'll be home in a little bit.”

And just like that, he hung up the phone and got back to it, sucking cock with an animated smile on his face while Roger pleasured his bottom. When we were finished with our threesome, he thanked Roger and I for a good time and got dressed. Holding hands with Roger and I, we walked him to the patio door and kissed him goodbye, then we watched him ride his bike out of my yard, his well serviced bottom swaying from side to side as he pedaled off.

Coming Soon...

Henry Strolls through the Alley


♥Jacob's Valentine♥


Other Work by Josh Terrence:

Gay/Adult-Youth Fiction

Gay/Incest Fiction

Gay/Urination Fiction

Gay/Young Friends Fiction


All You Can Eat

The Persistent Trespasser

The Boy at My Door

The Coupling


Bobby's Thanksgiving Feast

The Birthday Boy

The Trouble With Austin

Saturday Morning Splendor

Taylor Made


Alan's Brown Experience

James' Secret

Kyle's Afterschool Snack


Simon Spreads His Legs

Short Stories:

Oliver's Eatery

Friday Night Delight

Spencer on the Prowl

The Rear Entrance

Justin's Peculiar Tail

Sticky Sweet Relief

At The Park

Ethan's Shameless Turn

Mason Gets Laid

A Package for Simon

A Ride Through the City

Andrew's Pajama Party

Keith's Guilty Pleasure

Corey in the Morning

Adam Needs a Ride

Sean's Day Out

A Curious Tug of War

A Stir in Ian's Bottom

Jason in the Men's Room

An After School Quickie

Short Stories:

Bobby Starts Christmas Break

The King and the Prince

Rite of Passage

The Family Seed

Daddy's Boy

Rearing Derick

Home for Lunch

Spare the Rod

Daddy Takes Control

Daddy's Little Prancer

Jimmy's Chaperone

Stuart's Insatiable Itch

Short Stories:

Tanner Orders a # 2

Kenny Reports for Doodie

Breakfast in Bed

Cooper's Naughty Craving

Hunter's Fetish

The Party Pooper

The Park Toilet

Phillip's Spending Habits

Short Stories:

Mating Sason for Caleb

Saturday Morning Cruise

A Quickie for Bobby