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Wilbur had seen many things in his job as a fashion photographer.
He wasn't too well-known in the industry as a whole, not many mainstream magazines or sites had ever hired him to do a photoshoot, but that was exactly the reason why he'd seen so much weird shit in the eight years that he'd been doing this. You never knew what a customer wanted when they reached out; sometimes everything seemed completely normal at first but in the end he'd still find himself doing some weird pet-play photoshoot for some indie porno magazine. To be honest, that didn't actually happen that often, he mostly just did casual shoot of the latest fashion but hey, if someone offered a 20-year-old you money to sit in a room with a hot girl for an hour, could you really decline?
He'd actually done that so many times that Wilbur couldn't be bothered anymore to give to shits about the sexy outfits and poses that he encountered almost daily. While he didn't usually accept jobs from straight-up pornos, the casual fashion ones were usually suggestive in and of itself. He couldn't really avoid those if he wanted to get money.
That being said, he'd definitely seen a lot. A category of that "a lot" absolutely was cute femboys trying their best to seduce him into a hookup, but never had he thought that this kind of version of that group would get him so close to the edge.
When the boy had walked in, Wilbur didn't think too much about it. A tall, skinny blond, dressed in a white crop-top with an o-ring choker around his neck. The black fishnet stockings were up to his thighs and under a leather garter that Wilbur assumed went up to his waist, all covered by a dangerously short, pink skirt. The blond hair cornering his sky-blue eyes was fluffy and practically shining in the lighting of the room. Wilbur figured he took good care of his hair.
But his cute outfit was absolutely not the thing that threw Wilbur off. Because usually when a boy like him walked in, they'd immediately catch their eyes on Wilbur, wink and give him a dozen of suggestive touches throughout the whole thing. But Wilbur found out quite quickly as they shook hands and exchanged smiles that this kid was going to do none of that. Tommy, Wilbur learnt his name was, was completely oblivious to what he was doing.
Wilbur had gotten the instructions make the photoshoots sexy, so while he normally would have been glad to not have a pretty femboy all around him, for some reason seeing the oblivious blond get into all these kinds of extremely suggestive poses just made him so goddamn turned on.
Right now the boy was laying on the bed, his hands splattered next to his head. His legs weren't in the shot so Tommy was just keeping them crossed up with his feet against the mattress. His lips were slightly parted and his eyelids half-closed, and though it was all obviously just for the shoot, Wilbur couldn't help but think how pretty the blond would look like if he was splattered on his bed like this. Because of the position of his legs, Wilbur could see right under his skirt, and he felt his cock practically throb when he saw that he boy had black panties on. At lest he couldn't see his cock but he fucking bet that he he would have raised his skirt even an inch, it would have been right there in front of his eyes, pressed against the teen's stomach.
They changed the position, now Tommy was sitting on the armrest of a couch, leaning into his hands with his legs on both sides on the armrest. Instead of instructing him to bite his lip, like Wilbur usually did, he made the boy put on an oblivious, slightly surprised expression.
And god fucking damn it how good he looked.
Wilbur wanted to just drag the boy into a closet and fuck him into the wall with his stupid fucking skirt on. He wanted to hear all the pretty little whimpers that this blond would let out when he got stuffed with Wilbur's cock; maybe he'd even cry, beg for Wilbur to fill him with his cum. He was rock-hard and the only thing hiding that from the boy was the yellow sweater that Will had on that luckily was long enough to cover his crotch.
But of course he couldn't do any of that, though. At least Tommy wasn't underage, he was 19, so he wouldn't be committing a crime by just having sex with him, but there seemed to be no change that Tommy wanted him back and he obviously wouldn't do anything to him that he didn't want.
"I think we're done here", Wilbur muttered finally, after about two hours of endless teasing and struggle to hide his erection.
Something close to sadness seemed to flash through Tommy's expression. "Oh. Okay."
Wilbur gave a glance towards the teen, filled with frustration and mild annoyance. Was this kid seriously gonna be upset now, after two hours of showing Wilbur that he has not interested in the man? Wilbur knew he was being unreasonable, but the urge to pin the blond into the bed was still unbearably strong and the only thing stopping him was the assumption that Tommy didn't want that.
Their eyes locked for a second but Tommy looked away immediately after seeing Wilbur's frustrated frown. A shade of pink spread on his face.
"I, uh- I-I guess I go now, then", Tommy said, standing in the middle of the room and swaying on his feet.
"Mhm", Wilbur said. "It was nice to meet you."
"..Yeah", Tommy said. His eyes me Wilbur's again and the man recognized shyness in them, covered with, as he had though, sadness. Wilbur nodded at him and Tommy slowly turned around and started walking towards the door through the big room, and that was when Wilbur finally snapped. He rushed to a cabinet and quickly tried to find a piece of paper, scribbling his address on it with hurried handwriting when he did find one. Tommy was standing right at the door and had turned around to look at him with a confused expression. Wilbur rushed to him and shoved the piece of paper into his hand.
"Only if you want to. 8pm. Today", he said with a voice deep from lust, opening the door and pushing Tommy out of it before the boy could give him a proper answer. He stood next to the closed door for a while before slowly walking back.
Wilbur had one photoshoot left to do but it was luckily finished quickly. He went home with a weird feeling lingering in his stomach; the world felt a little surreal at that moment. He was quite certain that Tommy wouldn't actually come but Wilbur let the hope rest inside him.
Time seemed to pass by slowly but still extremely quickly. He wasn't sure where it all went, in fact; at some point Will just noticed that the clock showed 19:43. It was nearly 8pm.
And 8pm came and went without any interruption in the suffocating silence of his apartment.
Wilbur sighed, rubbing his eye with a palm. He groaned in annoyance, frustrated at himself for ever thinking that the blond would actually come. Of course he didn't, of-fucking-course Wilbur had caught his eye on the one dude that hadn't shown any interest towards him.
His thoughts were cut off by the sound of his doorbell ringing, making Wilbur immediately drop all of his frustrated thoughts. Holy shit, he couldn't be this lucky.
Wilbur rushed to the door and opened it, locking eyes with the tall blond standing on his doorway. His hard-on had disappeared in the two hours that he'd had to wait for Tommy, but now that the sight of the boy was right there in front of his eyes again, he could feel his dick growing quickly hard again.
Little shit was wearing the exact same clothes.
"Fucking tease", Wilbur groaned, grabbing the boy by his forearm. He closed the door behind him and dragged Tommy inside the house, barely giving him enough time to quickly get his shoes off before he pushed the boy against the wall. He grabbed the sides of his face roughly, shoving his lips against Tommy's. The blond moaned into the kiss while his hands tried to sloppily find their way to Wilbur's shoulders, and attempt that was disregarded by the man who grabbed his wrists and pinned them to the wall. He grinded against Tommy, forcing his knee in between his legs and pressing it against his crotch. The light fabric of Tommy's skirt splayed across his thigh.
"W-Wilbur.." the boy panted out. Wilbur was slightly surprised by the fact that the boy still remembered his name, but the fact just made him groan pleasedly.
"Safeword?" Will asked, releasing his left hand from Tommy's wrist for a moment to rest it on his side.
"Uhh.. Maple", Tommy said after a quick frown.
"Alright." Wilbur swallowed. "How'd'you wanna do this?"
"Be dominant. Make me beg", Tommy's eyes flickered up to meet his own. Wilbur's eyebrows raised slightly at his boldness, and a grin spread on his face.
"As you wish", Wilbur chuckled darkly. His hand trailed back up to the boy's face. Wilbur's fingers brushed against his parted lips before he roughly pinned Tommy's wrist back against the wall.
"You wanted this all along, didn't you?" Wilbur growled into Tommy's eyes as he manhandled the boy and spun him around, pinning him against the wall with his chest pressing against the boy's back. Wilbur's dick twitched at the size difference of their torsos, and it grew even harder when his crotch pressed against the boy's plush ass. "You knew exactly what you were fucking doing."
"N-No, Wilby- I d-didn't.." Tommy tried to say but his words were cut off by a whimper when Wilbur's hand slid under his skirt and panties, caressing his hole teasingly. His other hand grabbed Tommy's side, his slim fingers cold against the boy's pale skin.
Tommy curved his back to lean into the wall by his forearms with his ass up right against Wilbur's clothed cock. He let out a shaky breath before sucking in air again, leaning his forehead against the wall as the man's fingers slid up and down against his rim.
"Oh, you naughty boy.." Wilbur hissed through his teeth, cupping Tommy's cheek with his hand before he stretched his arm back and laid a swift slap on his bare ass. The sound rang through the room alongside the shaken moan that the blond let out, making Wilbur groan and his erection grow even harder.
"I'm gonna fuck you real hard and good, kitten, don't you worry", Wilbur mumbled before he roughly grabbed Tommy, dragging him to the living room and bending him over the table in front of the TV.
"F-Fuck.." Tommy breathed out as Wilbur slid his hands under the blonde's top and swiftly took it off, leaving the black choker on to contrast with his pale skin. Wilbur loved the sight, knowing that in not too long that pale, unmarked skin would be filled with hickeys. Wilbur slid his hand across the boy's chest.
"Such a pretty boy", he admired the teen. "And all for me." The last part was a mumble, breathed out as Wilbur reached to lay his hand across the garter he had on his waist.
"Stay right here" Wilbur said, sliding his hand across the thigh-high stockings. "I'll be right back."
Tommy nodded and the man smiled at the deep-red blush that was covering his face before leaving the room. He went to his bedroom and quickly grabbed a bottle of lube from the drawer. When Wilbur came back, he was pleased to notice that Tommy was still in the same exactly position as Wilbur had left him in- His ass was up in the air, the thin fabric of his skirt barely covering it.
"Jesus." Wilbur let out a breath. "You're gonna kill me." He poured some lube on his fingers before moving closer to the boy, his hand making it's way under Tommy's skirt to remove his panties. He slid the black fabric off around the boy's legs, letting it fall on the floor.
Wilbur pressed his crotch against Tommy's ass, bending slightly as well to wrap his free arm around the younger's torso. Will's lubed fingers pressed against his hole. Tommy gulped under him pressed himself tighter against them man in anticipation.
"Come on, Tommy", Wilbur grinned. He wasn't going to let this boy get what he wanted this easily; he had to tease him a little bit. "What do you want?"
"I want you to, fuckin'-", Tommy's sentence got cut off by a frustrated breath. "To get your fingers in me already, dipshit."
"Mhm", Wilbur tilted his head. His fingers moved slightly away from the entrance. "That's no way to talk to me, is it now, Tommy? Y'know, I could just walk away if you don't want me to-"
"No!" Tommy didn't let him finish his sentence. "I want it."
"What do you want?"
He could see Tommy biting his lip. His face was flushed red and he was breathing faster than normal. "I want you to fuck me, Wilbur."
"That's what I'm talking about", Wilbur smiled. He slowly pushed the tips of his two fingers in. Tommy's body winced back against his fingers, clearly wanting the man to go faster. Wilbur stopped. "Slow down, kitten."
"Fuck you-"
"I thought we went over this."
"Yes, yes, sorry", he boy mumbled. His voice sounded a bit like he was about to cry. "Sorry. Please. Wilbur, please, I want you. Don't stop."
Will hummed as a response, pushing his fingers deeper inside the skinny boy. Tommy let out a whine, clearly having trouble to remain still and not force the older's fingers deeper in him. Wilbur chuckled. "If you want more, you're gonna have to beg for it, Tommy", Wilbur said, grinning. He wanted to know how far he could go. He was painfully hard and didn't want anything more in the world than to just get inside of the teen already, but he was really enjoying the boy's frustratement. Also, this seemed to be exactly what Tommy had requested.
"Fuck", Tommy mumbled. "Please, I need you, Wilbur", he whined. "I want you inside me. Deeper than this. Will, please", his head dropped against the table when the pleas didn't work. "I want you to fuck me so hard, Wilbur, I want you to take me and fuckin'- SHIT-" Tommy's head snapped back up when the man pushed the two fingers deep inside of him, his knuckles pressing against the boy's rim. He moved the digits around a bit to find his prostate, but the angle seemed to be a bit off. Wilbur let out a shaky breath the feeling of the younger's body pressing hard against his fingers. His hand gripped Tommy's torso.
"Holy- holy fuck, okay, I- I want you to pin me against the wall so I can't move, I can't leave even if I wanted to, I want you to fuck me against the wall so hard that I can't even get a fuckin' word out of my mouth", Tommy babbled the words out quickly. It didn't seem like the boy could really thin straight.
"I think we could arrange that", Wilbur breathed out heavily. He slid a third finger inside as well and pumped them in and out while stretching the boy's hole. Tommy let out a long, shaky moan in between his heavy breaths.
Tommy was a bit loose, so either he'd stretched himself before this, or he just fucked a lot; either way, Wilbur was sure that this, plus lube, was enough so that his dick wouldn't hurt the boy. He was quite big, after all, especially when this hard.
He just couldn't wait any longer. Wilbur unzipped his pants and pulled his jeans down to his knees. He was sweaty all over, so hard that it physically hurt- Wilbur pulled his cock out of his boxers and shakily grabbed the lube from the table. He poured it over his member and quickly spread it around. Wilbur was shaking from the anticipation of finally getting to fuck this gorgeous boy, and it seemed like Tommy had the exact same thought in mind.
"Holy fuck, you're so beautiful", he said, having to break character for a moment. Something in Tommy's expression seemed to change when he heard Wilbur's words. The man pressed his tip against Tommy's hole, and heard the boy suck in a breath.
"Will, maple", Tommy suddenly said, making the brunette stop on his tracks immediately. "I don't wanna stop, can you just be like, more gentle, now? And loving? I liked the previous too, though, I just.."
"Of course, gorgeous", Wilbur felt a soft smile spread on his lips. His grip around Tommy softened and Wilbur took a moment to just slow down his breathing a bit. "D'you wanna go to the bedroom?"
"Maybe later", Tommy said. "Wasn't lying about the wall thing", he grinned, making Wilbur chuckle. "I do wanna see you, though."
"Okay", Will said. He helped the boy turn around on the table and wrap his legs around Wilbur's waist. Tommy shuffled around to get comfortable before licking his lips and meeting Will's eyes. His face was still red, and the blond's bright blue eyes shone through pure want for the man above him. It made Wilbur feel a weird, bubbling feeling in his stomach.
Wilbur went into this thinking it'd be just a sexy one night thing. But the way Tommy was looking at him right now made him feel that maybe.. maybe it was more than that.
Will shook the thought out of his head. His biggest concern right now was to get himself and the stunning boy on his living room table off.
"Jesus Christ, you're pretty", Wilbur muttered. He quickly took his sweater off, leaving both of them now shirtless. He'd kept the shirt as a sign of dominance, but it didn't really matter anymore. He was feeling hot, anyway. He also took off Tommy's stockings, the leather garter and the choker, leaving on only the pink skirt. His hands grabbed Tommy's waist from both sides after he lined himself up with his entrance again. Tommy placed his own hands on the forearms of the taller. Wilbur's arms felt bigger compared to his own. Stronger. "Gonna go in now, yeah?"
Tommy nodded, his body tensing up.
"Relax, love", Wilbur said. "It'll feel better that way." After saying this, he gently pushed himself in. Tommy sucked in a quick breath through his teeth and let his head fall back on the table. He could see from Tommy's face how good he felt, but the boy forced his body to relax. Wilbur grabbed his torso tighter as he slowly pushed his whole length in. Tommy's breathing, as well as Will's, sounded heavy and quick by the time their naked pelvises were pressed together. The soft fabric of Tommy's skirt pressed against Wilbur's skin.
"Oh my god", Tommy whimpered. "feels good." His voice sounded small and fragile. It was similar to the tone he'd used previously, but there was still something more genuine in it.
Wilbur groaned at the feeling of his cock filling the boy up completely. As his eyes flickered over the teen's face, he realized how bad he wanted for Tommy's expression to turn into one of pure bliss and pleasure in the hands of the taller.
He wanted this boy to, tonight, feel better than he'd ever felt before.
Wilbur started to slowly move, first out, and then back in with such delicate care that it almost felt like he was making love to the boy. He was big enough that he was hitting Tommy's prostate with every thrust, so Tommy's nails dug into the brunette's arms as waves of pleasure rushed through his body, making soundless gasps escape his mouth and his body to slightly tremble around the older man.
"Fuck", Tommy said with a quiet, high pitched voice. Wilbur's pace quickened, but the loving feeling of the way he pushed back into the boy just grew. He released his grip on Tommy's right side to wrap his hand around the younger's leaking member, but felt slim fingers grab his wrist before he could do so.
"Don't", Tommy said simply. "I wanna see if I can.. This is good", he couldn't finish his sentence, but Wilbur understood and brought his hand back on Tommy's torso. Tommy's body rocked back and forth at the same pace as Wilbur kept thrusting into him with loving passion. Their bodies kept moving closer together as Tommy's legs around the older's waist forced him closer, and Wilbur wrapped his arms tighter around the teen.
Wilbur's arms made their way up Tommy's body until they were under his back. The pace was now fast enough that he was thrusting mercilessly into the small boy, and it almost seemed like his body couldn't keep up with all the pleasure he was feeling. Wilbur was panting more than Tommy, but there were endless moans and whimpers escaping from the poor boy's lips. Wilbur pulled the blond closer and raised him up from the table.
"Wall", Tommy managed to get out, as Wilbur had to slow down. He carried the teen to the nearest empty wall and forced him against it. Tommy was pressed against the white wall with his legs wrapped around Wilbur so that he couldn't fall down, with the taller's arms around his waist, locking their bodies close together.
Wilbur could feel Tommy's body trembling and shaking as he began to fuck him against the wall. Tommy let out a loud moan, his arms shooting up to wrap them around Wilbur's neck. Will used the opportunity to press his lips against the boy's throat. He sucked on the skin and kissed him everywhere, leaving red marks behind as Tommy squirmed against him.
"Holy shit", the boy cried out. Tommy's hand trembled down to wrap around his cock; he'd seemingly changed his mind since his previous statement. Tommy was so out of it that he couldn't even properly jerk himself off, instead moving his hand mindlessly around his tip to match up with the pleasure he was feeling.
To be honest, Wilbur was quite out of it as well. He could feel the bubbling feeling of an orgasm growing in his stomach.
"Wilbur", Tommy said as his expression turned into something that Wilbur could only describe as ecstasy. He was looking Wilbur straight in the eye with the man's name on his lips as his body trembled violently and he reached his climax. Wilbur slowed his pace a bit, gently fucking into the boy through his orgasm. Tommy's eyes rolled up as his eyelids closed.
Tommy's expression was enough for Wilbur to finish as well. He let out a shaky laugh and sucked in a breath before burying himself deep inside the boy, spilling in him. Wilbur rested his forehead on Tommy's shoulder as they both just stood still for a moment, panting and gripping on the other.
Wilbur swallowed before finally looking at Tommy. The boy looked just as fucked-out as you'd expect, but his expression was also filled with joy. Wilbur smiled softly.
"Amazing", Tommy said. "You're amazing."
"Round two?" Wilbur grinned.
"Holy fuck", the boy responded with an eye roll. His head fell down in exhaustment. "Fine", he said after a moment. Wilbur's grin widened. He let the boy stand for a second as he finally took his pants off completely.
"You wont regret it", he said, picking the boy up in his arms. Tommy squirmed against his chest as the man carried him into the bedroom. "I'll make you feel even better than before."
"I don't know if that's possible", Tommy muttered as he was laid down on the sheets. Wilbur's fingers pressed softly against his waistband before taking off the boy's skirt. They were now both naked.
"You'll see", Wilbur smiled at him. The boy, for some reason, looked confused by this, and a faint blush spread on his face.
Wilbur pushed back into him. Tommy seemed to relax way more easily now than the first time. He immediately relaxed around the man as he bottomed out inside of him. Tommy shifted a bit to find a more comfortable position and laid his head on a pillow, and Wilbur placed some more pillows around them.
He started the familiar pace, his fingers lingering on Tommy's skin and placing loving touches around his body.
"You're incredible, Tommy", Wilbur mumbled. "So pretty." Tommy whined under him, his fingers searching for Wilbur's before wrapping around his wrists. Will placed his hands on the bed to lean into them as he gently fucked into the pretty boy under him.
Before, he'd fucked Tommy hard and had concentrated on making him feel physically as good as possible, but now.. Something felt different. The way their naked bodies moved against each other, they way Tommy's fingers gripped the older male's wrist, the way they mumbled each other's names under their breath and whispered sacred words to each other... the way Tommy looked at him through his lashes and the cloud of pleasure that blinded his sight. It was something different.
Wilbur wasn't just fucking Tommy. Maybe they weren't even just having sex. Maybe they were making love. Whatever it was, Wilbur realized that he didn't want for this to be a one time thing.
He didn't want for Tommy to be a one time thing.
Wilbur realized he was practically laying on top of Tommy, with the boy's hands grabbing his back. He pressed his lips against the younger's neck and placed kisses in a line-like format around his shoulders. The motion of both their bodies were perfectly in unison, almost like the two had some sort of unconscious connection between them. It felt like a dance, and Wilbur got lost in the feeling immediately.
He lost track of time completely. Will couldn't concentrate on anything else but this boy and their beautiful dance, and based on the look in Tommy's eyes as their gazes met, the younger felt the exact same way.
Wilbur wasn't sure how long it took until they reached their climaxes; it could've been hours, it could been five minutes. Wilbur didn't say a word, instead he gripped on to Tommy like his life depended on it and finished deep inside the boy, the warmth rushing through both of their bodies. All he heard from Tommy was a shaky gasp as his body trembled fiercely. Wilbur could feel the wet tears on his skin when their cheeks touched.
Wilbur rolled slightly to the side, so that he wasn't completely on top of Tommy, only mostly. He pressed their chests together and Tommy was immediately eager to return the action. The boy squirmed against Wilbur and seemed annoyed that he couldn't get closer. Then, they just laid there, for god knows how long, trying to calm their breathing. Wilbur realized they were under a blanket from the waist down. He must've put that over them at some point.
"What the fuck, Wilbur", Tommy broke the silence after an undefinable amount of time had passed. Despite his words, his voice didn't seem mad at all. He sounded in awe and loving, and top of all, exhausted.
"Did I accomplish the impossible?" Wilbur asked, referencing Tommy's previous words. He smiled against the younger's neck and rolled more to the side, giving Tommy the possibility of looking at his face.
It seemed to take a moment before the blond understood what he was talking about. "..Yeah", he sighed before closing his eyes for a moment.
"I'm glad."
"..Seriously though, what the fuck?" Tommy repeated after a moment of silence. The laughter in his voice caused Wilbur to burst out in giggles. "Stop laughing, dickhead!"
His demand didn't work; it only made Wilbur laugh even more, despite being at least as tired as Tommy was.
"You just- casually give me the best night of my life and now you're fuckin' laughing?" Tommy said, starting to chuckle as well.
"Really? Best night?" Wilbur asked.
"I mean.." the boy fell silent. "..Yeah. I mean I came in here thinking we're gonna have, like, a kinky fucking session and you just- you just look straight in my soul's deepest corner and make love to me or somethin'?" he laughed. "I mean, what the fuck, man?"
Wilbur's body shook as he laughed with the boy. "Well I'm glad it wasn't just me who thought that, then." Tommy chuckled for a while more before silence fell in between them again. "I'm down for a redo anytime, though. In case you wanna make this the second-best night of your life", he smirked.
"Oh my god", Tommy mumbled, making Wilbur burst out laughing. "You speak in big promises, Wilbur Gold", he joked.
"Wait, how do you know my surname?"
"It said it on the door."
"Oh", Wilbur said. "Right."
"..Anyway in case you were serious, I'm down for a.. Maybe not a redo, but- I wanna see you again."
"I wanna see you again, too", Wilbur said, his voice more serious now. "D'you.. Are you seeing anyone?"
"No. Are you?"
"I'm not. Do you.. Do you wanna just, see each other to have sex again or would you be down to.. Go out sometime?"
Tommy turned his head to look at Wilbur properly. The older couldn't really place what the expression on his face meant as he nervously waited for an answer.
"..Yeah", Tommy said slowly. "Yeah, I think I'd like that."
"Awesome", Wilbur said, maybe more excitedly than he'd meant. "I'll give you my number and all, we'll talk later."
"..Right", Tommy let out a hysteric laugh. "..I don't even have your number..."
"..Yeah.. don't worry about that, alright?" Wilbur laughed. "Anyway, we should probably clean up now. You can spend the night here, unless you've got somewhere to be. It's almost eleven", Wilbur said after checking the time from the clock on the nightstand.
"Okay", Tommy said and sat up. He looked a Wilbur and paused before smiling sheepishly. "Thanks."
Will had a feeling that the thanks meant more than just a response to his offer.