Whitney pulled, carefully, to a stop in front of the house. He was a very careful driver, unlike a lot of boys who delivered for Bob’s Pizza Place. The pizza was still steaming beside him, though, so the costumer shouldn’t complain. He opened the car door with an grinding shriek that sounded like it was in pain. He might be careful, but his car was still a piece of shit. It was old, rusted, and made funny noises at the oddest times. Kind of like his boss, Bob.
He bent over to retrieve the pizza from the passenger side seat, conscious of his ass the entire time. Bob’s Pizza Place was fairly lax on the dress code. As long as you wore a logo patch on your shirt and wore the Bob’s Pizza Place cap, anything went as far as Bob was concerned. Whitney liked to wear ass hugging shorts that left little to the imagination. He also wore a tight, white t-shirt, but his shorts were what made him blush now and then. They were great while he was standing up, but if he bent over they rode up and showed a bit more than was considered proper.
Not that Whitney was a naïve innocent, by any means. He’d done his share of sleeping around, but he wasn’t an exhibitionist either. Whitney wasn’t what you would call handsome. No, he was cute. Very cute. His features were soft and he had no beard at all. His hips had a slight curve to them, making him look a bit feminine. He was five foot six, slim without being bony, and he had absolutely no abs. His brunette hair tended to hang down into his hazel eyes. In high school he had had a pony tail but now he never let it get longer than neck length. He also had one of those smiles that made all the girls either want him as a best friend or a hot fuck.
Once he had the pizza out of the car he double checked the address and started up the walkway. As he made his way towards the door he caught a glimpse of someone peeking through the window blinds. Must be impatient for their pizza, he thought.
He walked right up to the door and pressed the door bell. A few moments went by. He had a tingly feeling like someone was watching him through the peephole. He shifted nervously and was just about to head back to his car when he heard the indoor lock click and the door pulled slowly open.
Oh…..my…he thought. The man in the doorway stood at about five foot ten, had sandy blond hair, dark brown eyes, and a strong jaw that looked like it needed a shave. He was in good shape, might even have a couple of abs. He looked thirty or fortyish, but that may have been the influence of the professor-like glasses.
“Um, pizza?” Whitney’s mind tied up his tongue and wouldn’t let him do anymore talking. God he’s hot.
The man looked back at him like he didn’t know what to do, “Uh, yeah, that is…um….bring it right in. I’ll, uh, I’ll get my wallet.”
Why’s he nervous, Whitney thought. It’s just pizza. He stepped inside and set the box on a small table next to the door.
The man walked out of the room, soon returning with his wallet in hand. He didn’t open it right away and stood awkwardly for a second, like he was trying to think of something to say.
Finally, “I’m Arthur, by the way. Um, you’re Whitney, aren’t you?”
Whitney raised an eyebrow, “How’d you know that?”
The man blushed, “I’d heard you do things for a….higher tip…”
Whitney raised an eyebrow, “What do you mean?”
“Shit,” the man scratched the back of his head, looking embarrassed, “I’m not good at this. Um, I’d heard that if a costumer pays you a big tip then you’ll give him a favor, in return…..a sexual favor.”
Realization dawned on Whitney, he threw his hands up in protest, “Hey buddy, I only did that once. The guy talked me into it and I really needed the money. College stuff, you know?”
Arthur nodded, “The ‘guy’ must have been my friend. He told me to ask for you when I ordered my next pizza…I’m sorry. I thought it was something you did on a more regular basis.”
“Well, it’s not,” Whitney shot back, trying to control the red he knew was flowing over his face, “I’m not like that! I only…”
“I know,” Arthur tried to placate him, “I’m sorry, I didn’t mean to offend you. Here, here’s the money for the pizza and a big tip anyway, I’m sorry, let’s forget about it.”
Arthur shoved some bills into Whitney’s hand and held the door open for him to leave. Whitney looked at the clearly mortified man and all the heat left him. He looked down at the bills in his hand and sighed, “Well, why would you want to pay for it anyway? I mean, you look like you could get anyone you wanted, for free.”
The man looked at him, a frustrated look stealing into his eyes, “Well…I just. I’m a really busy man. I don’t have time to socialize much. I just thought some quick fun with no strings would help me unwind a bit. And when my friend told me about you…..I thought it was the perfect solution. But instead I made an ass of myself, and I offended you. I‘m sorry. Could we just forget it happened?”
Whitney looked down at the bills in his hand and then back up ant Arthur. The man looked so sad and embarrassed. And he was hot, besides, “Well….I am going to college and I could always use more money….and it’s not like I haven’t done it before…”
Arthur looked a bit relieved, “You sure? I wouldn’t want you to do anything you don’t want to.”
Whitney gave him his best grin, “Sure, why not? I feel kinda bad for making you frown like that anyway. I hate to see a nice man like you so sad…”
Whitney leaned in, his body close to Arthur’s as he gave him a kiss on the cheek. The man looked startled at first, but he soon relaxed and slid his arms around the younger man.
“What do you want me to do?” Whitney murmured as he melted into Arthur’s strong arms.
Arthur’s body language changed as he stepped into an area he had more experience with. Firmly but not roughly he pushed Whitney away from him and towards a doorway leading to a hall, “First, I want you to change. There’s already an outfit waiting for you in the last room on the right. Be thorough. I want to be impressed when you come back.”
Whitney felt a rush deep inside himself as Arthur took control. He had always been a sub. He started for the hall with a grin, “Dress up, huh? Sounds fun.”
Arthur watched hungrily as the boy disappeared down the hallway, his ass swaying from side to side.
Once Whitney had reached the room and closed the door behind him, he gazed around, a look of delighted awe stealing onto his face. Reaching into his pocket, he snaked out his phone and quickly dialed a number.
“Hey, Boss? I’m taking the rest of the day off. I’ll bring by the cash for that last pizza tomorrow. Nope, something‘s come up. Something personal I really can‘t get away from.”
Thirty minutes after the phone call, Whitney looked at himself in the mirror of a vanity set against one of the bedroom walls. He couldn’t help but giggle a little. The dress was simple. Short. Very, Very short. But simple. It was predominately light blue with white trim. Thin straps held up the torso hugging bodice while the skirt flared out, barely covering the top of his hips. Thigh high stockings and simple black heels along with a white rose in his lightly styled hair finished off the outfit. He had to admit his girlish hips and petite form made it hard to distinguish the person in the mirror as male. The transformation made him tingle all over. The short hem of his dress would be tenting if it weren’t for the snug and incredibly soft turquoise panties keeping him secure.
He nervously nipped at his lower lip and headed out the door. The heels changed his entire walk as he carefully made his way down the hall towards the living room. Arthur was sitting on the couch, his brow furrowed in concentration as he studied a mess of papers spread over the coffee table in front of him. He looked up as Whitney entered the room. He looked stunned for a half moment, but quickly recovered himself and grinned. He set the document he was currently studying down and patted his knee. Motioning for boy who looked like a girl to sit.
“You look amazing,” he praised as Whitney obediently slid into his lap.
“T-thank you…” a girlish whimper escaped Whitney’s lips as Arthur’s hands slid around his waist and over his thigh, “Y-you have good taste.”
“I’m glad you approve of my selection,” Arthur murmured, his lips millimeters from the Whitney’s ear, “Having never seen you, I wasn’t sure if it would suit you, but I knew it was perfect the moment you stepped out of your car and showed me this fine rear.”
Whitney yelp as he felt a hand slide under him to cup his ass cheek, the fingers playing with the hem of his panties. He turned his head bashfully away as the man handled him like he owned him.
“Please…” he breathed, “You’re making me blush…”
Arthur chuckled, “Why would you blush? You’re so beautiful.”
Whitney bit his lip ineffectively trying to hold back a squeal as the hand slipped around his leg and cupped his nylon covered bulge, “God! You have to stop! If you keep this up I’ll go crazy!”
Arthur laughed and stood them both up, turning Whitney around he brought him close, “That’s the idea…” he murmured as he brought the boy’s lips to his own.
Whitney melted as Arthur kissed him. He felt the man’s hands grip his ass and pull him close. He found himself pushed against a wall, one leg hiked up to allow Arthur’s jean clad thigh to scrape against the straining erection between his legs. His mouth surrendered under the possessive onslaught of the other man’s tongue. At that moment, Arthur owned him in every sense of the word.
He almost cried when the embrace suddenly ended.
Arthur pushed away with a smart slap to Whitney’s thigh. The boy watched, yearningly, as the older man walked to the opposite side of the room and took a seat in a comfortable looking chair. Arthur picked up a remote and punched a button. Dance music filled the room.
“Dance for me, Boy. Give me you’re best lap dance.” Arthur settled back into the cushions looking expectant.
Whitney bit his lip, looking a bit shy. He started to move back and forth, finding his rhythm in the song as his hips swayed. He looked into Arthur’s eyes and grew more confident, somehow finding strength in the man’s gaze. His entire body began to move, his dress accentuating his form as he moved closer to the easy chair. A flash of more hip here, fabric stretching tight over a curved stomach there. When he had crossed the room, he bent at the waist, his face an inch from Arthur’s knee, he moved forward, gliding up the man’s relaxed body until they were face to face with Whitney’s crotch sliding sensuously across Arthur’s knee. With soft kiss to the tip of his audience’s nose, the dancer twisted around and ground his ass over a clearly aroused crotch. God he’s big! Whitney thought as his thinly clad ass cheeks felt the man’s length.
He leaned back, his head next to Arthur’s, stretching his arm back to hook behind the man’s neck. His lips brushed along a rough jaw line as the rest of him undulated against his Arthur’s body.
Arthur reached around the boy’s legs, gripping and spreading both of his thighs. He pulled and Whitney levered, rubbing ass to crotch for a moment before the younger man gripped the arms of the chair and brought his knees up. His feet planted on either chair arm allowing him to stand and turn. He dropped back down, his knees to either side of Arthur. He gyrated, grinding his crotch against the man’s face, making him grin. Whitney grinned back and reached his hands down to grip the chair arms again. He lowered himself back and down till his knees were on the floor instead of on the chair. He dipped his head and placed his mouth over the bulge in Arthur’s jeans, giving in a wet suck as his teeth clamped around the denim edges.
Arthur’s head bent backwards as he groaned. Looking down again, he moaned, “Take it out.”
Obediently, and not a little eagerly, Whitney reached up and unbuckled Arthur’s belt. He slowly pulled down the zipper and reached inside. Pulling aside some constraining underwear, he found what he was looking for. The shaft was hot to the touch and thick. Whitney’s small feminine hand barely reached around it. Carefully he pulled it free and let loose a hungry whimper. It looked to be about eight inches or so(Whitney prided himself on the accuracy of his sight measurements) and he was pleasantly surprised to find it smoothly shaven. His hand was still wrapped around the shaft so he gave it a couple of strokes, biting his lower lip at how soft and malleable the skin was over the steel hard poll.
Arthur looked a bit flushed, though his voice didn’t betray anything but authority as he said, “Taste it, Boy. Let’s see how good you are with a man’s tool.”
A shark-like smile spread over Whitney’s face as he determined to show Arthur just how talented he was. His tongue snaked out and swirled over the shaft, sliding up around the glans. He love the clean, meaty taste of it. He lowered his mouth down to the base of the shaft and began to kiss and nip his way back to the tip. He took the head into his mouth, giving it an experimental lollipop suck. He looked up into Arthur’s flushed face, smacking his lips before diving back down to deep throat the entire length. Arthur gave a surprise and satisfying groan as his entire manhood was swallowed by the pizza delivery boy. Whitney bobbed his head a couple times, feeling the stretched sensation of having a thick cock shoved half way down his throat, before pulling back to a more manageable position. He worked his lips and tongue over the top half of the phallus, using techniques he’d been honing since junior high. He’d never had a boy or man last more than a few minutes under his tongue.
The minutes ticked by, and though Arthur let loose with a lot of grunts, moans, “Oh God”s, and a large and varied selection of swear words, he didn’t seem any closer to popping off into the hungry boy’s mouth. Ten minutes went by, and then twenty. Finally, after a half hour of furious sucking and slurping Whitney felt back, gasping from exertion.
“How are you doing that!?” he gasped, looking up at Arthur, “Nobody’s ever been able to last for so long when I blow them!”
Breathing hard himself, Arthur reached down and stroked Whitney’s cheek, “I’m very good at holding back until I’m ready to cum. I have to say, though, you make it harder than anybody I’ve ever been blown by,” he chuckled, “I think I‘m ready for the main course, now.”
Whitney gasped as Arthur stood and pulled him up. He found himself bent over, hands firmly planted on a window seat, legs spread, presenting his ass conveniently for the older man‘s use. He realized he was extremely grateful that the blinds were lowered as Arthur lifted up his skirt and pulled his soft nylon panties down, letting them drop to the floor around his ankles.
Whitney sighed with relief as his cock was allowed into the open air. A small squeal erupted from his lips, though, as he felt fingers walking over his balls and down his length.
“Five inches, huh?” Arthur breathed, “Perfect sucking size…”
Whitney squealed long and loud as soft experienced lips slid over his length, taking him inside a warm mouth. He moaned as Arthur’s tongue slid over and around his shaft. He shuddered, barely holding it together as the tongue and teeth played with his glans.
Suddenly, he felt a hand on his ass. Then fingers spreading his crack open. When the first finger wriggled its way down into his tight boi cunt he couldn’t hold on any longer. He cried out, squealing as he came, feeding Arthur ropes of creamy white cum. His knees were shaking so much he nearly collapsed, but Arthur braced him, never stopping his onslaught of Whitney’s ass, he stroked and pulled till the opening was wide enough to slide in another digit. He drained Whitney’s dick of juice and then let it slide wetly from his lips.
“You’re so tasty, Boy,” Arthur quipped as he rose to his feet, his finger still buried inside Whitney’s quivering ass. He gave a round cheek a light slap, extracting a whimpering moan.
Whitney squirmed as a third finger was put inside him, all three pumping his boi cunt as Arthur added spit for lube. He gulped when the fingers were removed, knowing what was coming next. He felt the soft tip of Arthur’s cock press against his open hole, stretching him just a bit further as it popped inside.
Arthur grinned as the boy moaned with his entry. He pushed a little more, feeling the slick, wet tube that was Whitney’s rectum wrap itself around him. Soon he was half way in. He pulled back and then pushed again, his tool making a soft squelching sound as it worked further inside. Whitney bit his lower lip as the cock worked its way inside him, pumping slowly back and forth until…
“Oh god, I can fell your hips on my ass!” Whitney whimper. “You’re all the way inside me. Fuck you feel so good!”
Arthur chuckled, reaching forward, “You’re so hot and wet around my cock, Whitney. But now the real show starts.”
Whitney’s eyes flew wide open in shock as Arthur raised the blinds all the way, exposing them to the traffic in front of the house.
“No!” he shouted, “I don’t do this! I’m not an exhibitionist! Stop! OH GOD!”
Whitney’s protests died as the man behind him began to stroke him hard and fast. He looked out at the cars and people passing by. None had notice them yet, but he blushed anyway, feeling on display as Arthur fucked him from behind.
Suddenly some skate boarders sped by, one looked to the side just in time to see the pair in the window going at it. A look of shock passed over his face before he lost focus and tumbled off his board. As he got back to his feet the others returned to see what had happened. Whitney groaned, Oh fuck! as they all turned to watch him. He could just make out some of what they were saying through the thin glass that was his only protection from the rest of the world.
“Fuck, man! He’s really pounding her!”
“Look she’s watching us too!”
“What a slut!”
Whitney’s jaw dropped as he realized they couldn’t see his dick bouncing away behind his upper body. They think I’m a girl!! The thought somehow made him harder, sending tingles down his spine.
Above him, Arthur was bearing down, ramming into him harder and harder. Whitney’s cock was completely hard once again and he didn’t know if he would last under the onslaught. He yelped as the first sharp slap bounced off his ass. He could hear the boys outside cheer as Arthur gave him repeated spankings, reaming him all the while. He looked outside again, blushing a deep crimson as he saw a passing middle aged man with an open, disbelieving mouth, stop and gape for a second before hurriedly moving on. Cars began to slow as they passed by, one even parked on the side of the street as a man and a woman watched the show.
“You see,” Arthur grunted as he thrust away, “They love you. They want to watch you get fucked. If it were just me the cops would have been called by now.” He reached down and began jerking Whitney off as they fucked.
People outside kept walking and driving by. A few stopped for a moment before getting embarrassed and continuing on. Only the boys and the couple in the car stayed to watch. Whitney whimpered and blushed harder than he had ever blushed under their intent stares.
“Are you about ready to cum?” Arthur asked as he stroked Whitney’s tool.
Whitney nodded, “I-I can take much more of this!”
“Good.” Arthur smiled weakly as his own control wavered, “Time for the finale.”
Whitney squealed as Arthur pulled him back and up. The viewers outside all gasped as they saw his cock being stroked and realized he was a boy. Two of the skater boys quickly turned and skated away but one boy and the couple remained, watching, fascinated as the two continued to fuck. Whitney lay his head back against Arthur’s shoulder, his eyes locked with the boy’s as strong hands gripped his hips and a thick cock thrust hard and fast inside him. He milked the rod with his ass cheeks, feeling it close to finally cumming as he gasped, ready to spew, himself.
Arthur growled out his climax, filling Whitney’s bowels with shot after thick shot of cum. The feeling of having his ass filled with hot jizz combined with the sensation of being watched by complete strangers was too much. Whitney orgasmed a second time, his cum shooting out of his bobbing cock to hit the window seat and the window behind it. The couple in the car grinned their approval. The skater boy gulped at the sight. Suddenly, he seemed to remember himself and he took off like he was being chased.
Arthur pulled out and slid a supporting arm around a weary Whitney. He folded the boy into a loving embrace and kissed him. The couple watched them, smiling. The woman even giggled and blushed at the display of affection. After the kiss ended, Arthur turned and waved a smile at them before reaching out and lowing the blinds. The car sped off as Arthur pulled an exhausted Whitney to the nearby couch to rest.
“You ok?” Arthur asked, concerned as he held the unsteady boy in his arms.
Whitney nuzzled his nose against Arthur’s chest and sighed, “Mmhmm…just spent. You really wore me out! I’m glad I took the rest of the day off.”
“You going to be able to drive yourself home?”
Whitney froze, suddenly remembering that this was a business transaction, not a romp with a boyfriend. “Yeah, I, uh, I think I’ll be good in a moment.”
“Good…” Arthur was suddenly awkward again, “Take all the time you…need. I, uh, I need to get back to work…”
Whitney knew he shouldn’t feel hurt as Arthur gently but firmly moved him away to lean against the back of the couch before returning to the paperwork he had been working on. He knew he was just a pizza boy who had made a rather unethical deal with a costumer. He knew he should just get up and go home, happy to have more cash in his pocket.
But, then, why did he have this sinking sensation in his stomach.
With a sigh, he got up and started for the bedroom, “I’ll just…change…and go…then.”
Arthur stopped working and looked up at him, “Uh wait a sec, would you?”
Whitney paused next to the entry to the hall.
Arthur coughed nervously, “Eh…you’re money’s on the table..”
Whitney noticed a big wad of cash sitting next to the papers on the table. “But you already paid me…”
Arthur scratched the back of his neck, “Well, since you decided to stay and you were wonderful. Really…I just thought I’d throw in a bit more…”
“You didn’t have to do that…”
“I know…but I insist…you really did earn it…”
You really did earn it…Whitney couldn’t help but feel a bit dirty as he walked over to the table and picked up the bills. He was about to turn and head to the bedroom to change when Arthur stopped him again.
“Um, could I ask you for one more thing?”
“What…” Whitney snapped a bit harshly before he could stop himself.
Arthur winced, “Uh, never mind. I’m sorry, I was just going to ask for your number. It was bad idea.”
Whitney froze, “Why would you want my number?”
Arthur blinked, “So I could call you to schedule next time, of course. Instead of the awkwardness of going through the pizza service…That is, if you want there to be a…next time.”
Whitney had so many conflicting emotions that he barely got out, “You want to do this again?”
Arthur looked really cute when he blushed, “Well, yes…”
Whitney fairly scrambled around the table, making the older man yelp in surprise as he grabbed his hand and a pen before scribbling down his cell number.
“There! Call me anytime! But next time, lets do this in the evening after I get off shift, k?”
Arthur nodded, a bit dazed by the sudden burst of enthusiasm, “Okay…Oh and by the way, you can keep the outfit. On one condition, that is.”
Whitney brightened at the prospect, “Condition?”
Arthur grinned, “That you wear it the next time we meet.”
Whitney laughed, “Okay! Deal! I’ll go grab my stuff now.”
He scampered back to the bedroom and grabbed his things, deciding to leave the dress on. Everyone at the dorm knew he was gay so it didn’t matter on that account. He walked back into the living room and headed for the door. “Till next time,” he called.
Arthur nodded, his head bent intently over his papers again. Whitney shook his head as he turned the knob to the front door. This man was going to take some figuring out.
But at least he’d have another chance.
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