Bobby's First Suit

"I thought it would be a good idea to buy Bobby a suit," Gladys Bradley told the little Italian tailor whose shop was down the road from their apartment. "Not only for the dance, but with Bobby going to college in a couple of months he'll probably need a suit for other things."

"A college boy now huh?" Tony Caruso asked as he rubbed the dense 5 o'clock shadow on his face, a hint of his accent still around despite living in the USA for nearly 50 of his 66 years.

"That's right Mr. Caruso. Anyway, Bobby's father - god rest his soul - always swore by you," Gladys explained as her son squirmed in place. "He said your work was wonderful and you were very meticulous. I recall you always had my husband come back many times for fittings to make sure it was perfect."

"Yes, your husband Richard. A good man. We became quite close," Tony said. "And you know I will take good care of his boy!"

"It's his prom and he has a date and everything," Gladys explained. "So I trust you to put him in something nice."

"Leave it to me Mrs. Bradley," the tailor said as he escorted her to the door. "You want Bobby to call you when we're done to pick him up?"

"No, Bobby can walk because it isn't far," she told the tailor before turning to her son and mentioning, "You can use the exercise."

"I know mother," the cherubic lad said as he watched his mother leave, and after the tailor latched the door behind her and flipped the OPEN sign to CLOSED he pulled the shade on the door down.

"I don't like to be disturbed," Tony explained as he led the lad around the corner of the room away from the front window. "I strongly believe you take care of one person at a time and do it right. So you have a date for the Prom huh?"

"Not really. It's my cousin," Bobby shrugged. "Mother insisted I go to the Prom and I couldn't find a date so she arranged it."

"Ah. Interesting. That tall blonde boy I see you walking with past the store a lot of times? Is he going to the Prom too?"

"Uh - Dylan?" Bobby mumbled as he tried to hide his shock of the tailor noticing him before. "No, he's not."

"Oh well. You never been fitted for a suit before Bobby, right?" Tony asked as he held onto the ends of the measuring tape draped around his neck, and when the teen shook his head the tailor nodded and said. "I'm gonna make you look like a movie star. Take off your shirt and slacks for me."

"Really?" Bobby asked.

"Of course. Gotta take measurements. A lot of measurements," Tony told him.

Bobby Bradley slowly unbuttoned his shirt, self conscious about his chubby frame, and after he took off his slacks he felt naked even though he still had on socks and baggy boxer shorts.

"You about 6'1"?" Tony asked as he looked over the lad's pudgy body, taking special note of the plump boy boobs on his smooth chest as he wrapped the measuring tape around his neck. "I figure by sight you might be a 46 regular - maybe a tall - but I'll need to do some altering. Lotta work but I love my job"

"Lift your arms for me Bobby," Tony instructed, and as Bobby reluctantly raised his arms so the tailor could measure his chest he saw the man look and smile at the sparse moist hairs pasted on the skin under his arms.

"Breathe normal," Tony said as he spun the tape around the lad's chest, the feel of the measuring tape against the boy's puffy crimson nipples making them swell even larger.

"Hot in here for you?" Tony asked as he reached for a towel, watching a drop of sweat roll down the lad's side from under his arm, and when he dabbed the perspiration Bobby giggled.

"Ticklish?" the tailor asked as he wiggled the towel under Bobby's arm, making his upper torso jiggle a little.

"Maybe a 48 regular," Tony reconsidered as he measure the lad's waist before kneeling down and explaining. "I like to measure the outseam and the inseam."

Bobby watched the tailor put the tape on his hip and pull it down to the top of his foot before bringing the measuring tape up between his legs, the back of his hand making contact with him and making the boy jump.

"That date of yours, she gonna have a treat coming after the dance," Tony opined as his hand nudged the meaty organ a few more times while looking up at his reaction. "You're a big boy alright. A lot like your father. Maybe even bigger."

"Something wrong son?" the tailor asked while looking up for Bobby's reaction before slipping his hand up under the leg of the loose boxer shorts, and it took no time to find what he wanted.

Bobby gasped and grabbed the arm of the tailor, the hairy forearm very muscular for a slim man, but the tailor's hand held onto the cock, rubbing the bulbous head and feeling the lad's manhood begin to get hard.

"You like what I'm doing, don't you Bobby?" the diminutive tailor asked as the lad squirmed, moving his weight from foot to foot as the tip of his dick drooled on the man's fingers.

"I don't understand, Mr. Caruso."

"I'm gonna take care of you like I used to take care of your Papa," the tailor promised as he pulled his hand out from the leg of the briefs and looked at the string of cream before licking his fingers.

"My father?" Bobby asked in a quivering voice.

"You didn't know? He told me he was going to tell his boy about his other life, but I guess he didn't get the chance," Mr. Caruso explained. "He wasn't ashamed and he loved his wife like I love mine, he just needed things that your Mama couldn't provide. Now let me get a look at you."

Tony Caruso slipped the boxer shorts down off Bobby's belly, dodging as the lad's erection sprang free, the thick stub pointing straight out as the older man took the boy's underwear from around his ankles.

"Chip off the old block," Mr. Caruso declared as he reached up and wrapped his fingers around the shaft of the fat organ, the taut skin of the plump glans beet red and oozing seed. "Nice thick piece of man meat you got there."

The tailor wasted no time in leaning forward to swab his tongue all around the head of the circumcised cock, circling the ridge before flicking around the generous opening that kept leaking sap.

"Tony's making you feel good, no?" he asked as he looked up at the still stunned lad, and without waiting for an answer opened his mouth wide and let his lips moved down the stiff organ, not stopping until they reached the stump and his face was buried in the bush.

"Holy crap!" Bobby cried out, his knees buckling as the old man suckled on his tool hard, and the teen had to grab onto the man's shoulders for support as those lips moved back up to the tip.

Up and down the tailor's mouth went, his stubbly chin hitting the lad's nuts each time he swooped down, and Mr. Caruso didn't stop until he sensed that Bobby was about to cum.

"Nobody ever suck your fat dick like me I bet," Mr. Caruso crowed as he stood back up, gently twisting the lad's nipples before stepping back and starting to unbutton his own shirt. "Let me get comfortable before we really have fun."

The tailor peeled his shirt off his skinny torso, the mat of hair that covered his chest mostly black with some silver mixed in, and the gold cross around his neck stood out against the dark carpet behind it.

"You aren't mad about me telling you about your father, are you?"

"No sir. Actually, it makes me feel better about myself because I was always afraid he would be ashamed of me because of the way I am. I love him."

"And so did I. He was like a younger brother to me," Tony said as he lowered his baggy pants and carefully folded them. "How many times he used came down here to get his suit altered? The fun we used to have."

"You like?" the old man asked the lad after he saw the way Bobby was staring at his privates after the boxers came off. "Your Papa, he used to call this my dipstick. He used to love me to - what did he call it? He used to love me to check his oil after I sucked him off."

Bobby stared open mouthed as the tailor wiggled the flaccid hose around, the brown uncut cock as absurdly long as it was incredibly thin with a thick vein that made its serpentine way down most of the shaft.

"You gonna let me check your oil Bobby?" Tony asked softly as he came up to hug the chubby teen, rubbing his hairy chest against the boy's soft baby fat before sliding down to his knees again. "Don't worry - it don't get much longer than it is now."

Mr. Caruso went right back to the lad's cock which was just as hard as it was when he left it, and as he deep-throated the pulsating organ both of his hands went around Bobby, squeezing his chubby bottom in time.

"Oh man Mr. Caruso! Can't hold it back! Gonna cum!" Bobby cried out as his hands went through the wavy hair of the tailor, feeling his orgasm begin to race through his loins, but the older man was relentless.

Bobby's knees buckled as his dick exploded, sending volley after volley of his seed down the throat of his father's friend, who swallowed it without blinking. Only after the lad's member shrank back into his pubic hair did he release the toadstool and rise back up.

"You like?" the little man asked as he took Bobby's flushed cheeks in his palms, and after the lad nodded he kissed him softly on the lips.

The older man's hands went down to Bobby's round shoulders, easing him down to his knees, and after he got there Bobby took the long slender shank in both hands and raised it to his lips.

The tailor's cock was no thicker than Bobby's thumb but he only got about half of the tube in his mouth before the tip hit his throat so he gripped the shaft with both fists and sucked on the rest.

"Ooh Bobby," Mr. Caruso sighed as he looked down at the boy eagerly sucking his uncut tool, and the way his fists were spinning and pumping showed he might be young but knew what he was doing.

Bobby peeled back the long foreskin and licked the olive-sized glans hidden beneath the shroud before going back to sucking, and in no time the tailor's cock was stiff and throbbing. It wasn't much longer than it had been, but was still outrageous looking to the lad on his knees.

"That's so good," Tony Caruso was saying as he reached down under Bobby's arms to help him get to his feet, and as he led him over to a big corner chair in the back of the room he said, "Now I'm gonna make it good for both of us."

On the way the tailor stopped at a cabinet and pulled out a jar of lubricant before taking Bobby to the corner, and after taking the lid off the jar told Bobby to do the honors.

"Make it nice and greased for us," Mr. Caruso instructed as the lad scooped out some and began to rub it up and down the entire 11" of the old man's organ, the brown skin glistening after he finished.

"Now let's get you ready," the tailor said as he began to move the boy onto his knees in the chair, but when Bobby was hesitant he asked, "What's wrong? You said you done this before, right?"

"Yeah but..." the lad replied, staring at the weapon waving in front of the hirsute man.

"It's gonna be good. Better than good," Mr. Caruso assured him as he moved the chubby lad onto his knees on the cushion and manipulated Bobby so that he was presenting himself to him, spreading the chunky pale buttocks so he could see the prize at the end of the crevice.

"Oh, that's a pretty one," Tony sighed as he looked at the pink puckered ring exposed when he spread the lad's ass, and he poked a slick finger into the tight knot before moving up against the doughy bottom. "Gonna make you a man now."

"Oh geez!" Bobby howled when he felt the tip of the old man's tool enter his anus as the tailor spread the fat bottom with his hands, and then the older man leaned into him until he had fully impaled him.

"Oh, you're so tight," Mr. Caruso moaned. "You okay right?"

"Yes sir," Bobby choked out as his hands gripped the chair while keeping his ass up as high as he could, and in fact in didn't hurt nearly as much as when Dylan took him, although the cock that was in him was going far deep than his friend's could go.

"Good," Tony groaned as he slowly extracted himself until only the tip was still in the lad, and then he plunged back in all the way once more.

In and out the tailor's prong went, sometimes coming completely out before drilling back in, the slender cock sliding in effortlessly, and soon Bobby was pushing himself back into the old man's thrusts which became harder and faster.

"Knew you'd like it," the old man snapped as he leaned over Bobby, reaching around to find his cock was nearly stiff again. You like it a lot."

The back of the chair bumping against the wall was in sync with the two men's grunting as the tailor milked the plump cock hard, and before long Bobby was moaning as his orgasm spattered all over the chair.

"Yeah!" Mr. Caruso snarled as he let go of the gooey dick and grabbed Bobby's hips, driving into his late friend's boy so hard the ass jiggled before his cock finally spurted his load deep into his bowels.

The older man collapsed onto Bobby's broad moist back until his manhood slithered out of him, and then he straightened up, his aching back not bothering him as much as it would tomorrow, but it was worth it.

"Don't worry about that," Mr. Caruso said as he grabbed a cloth and cleaned off the chair. "Not the first time that happened for sure. How do you feel?"

"Great," Bobby said as he got dressed.

"Now when in a couple days when I finish altering the suit I want you to come down and try it on," Tony told him. "Okay?"

"Yeah!" the portly teen replied. "Closing time again?"

"Of course," the tailor said as he slapped the big boy on his back on the way out.

***

"You're going back down to Mr. Caruso's again?" Mrs. Bradley said when Bobby told her where he was headed after dinner. "You gonna wear the suit again soon?"

"I might," Bobby told her. "He said he was going to get it dry cleaned for me. Plus, the stitching under my arm ripped a little so he said he would fix it."

"Well don't be a bother to the nice man," he was told. "He is still thorough though, isn't he? Don't know how he does it at his age."

"I don't know either," Bobby agreed as he made another trip down the street, smiling all the way.

***

Thank you for reading.