Spring Break 2020 (Extremeophile x AllThingsCuddly)

[Extremeophile]

Hey, look over there. Isn't that Zachary? I didn't realize he would be here." The voice of his best friend broke into Theodore's trance. He had been zoning out just watching the beach but at the name he perked up immediately.

"Where?" He asked, looking around. Chris might not have known that Zach would be here, but Theo had known. It's why he had picked this hotel in the first place. The three college students all lived in the same dorm but Theo had never spoken to Zach, only admired him from afar. For two years now he had been crushing on the other though he would never openly admit it. After all, no one knew that he was gay and he highly doubted that Zach was. So instead he continued to torment himself by watching him, imagining bringing the younger boy back to his own dorm and shoving him up against the wall, and fucking his brains out. How many times had he masterbated to the idea?

"Over there." Chris pointed and Theo followed the gesture. Sure enough, there he was. Pale green eyes took in the clothing the man wore and he could feel his cock growing hard. "What the fuck is he wearing?" Chris asked, chuckling. "Looks like some sort of 'come fuck me' outfit. Does he realize how gay he looks?"

Theo swallowed hard, his eyes traveling from the short shorts to the button down shirt and finally landing on the gay pride bracelet. Fuck. Was Zach really gay? He let out a heated breath but then took a deep breath and managed to compose himself. "I think that's the point, Christopher." He said, using his friend's full name for emphasis.

"Shit. You don't think, really?" He asked, raising his beer and taking a drink.

"Mmm." Theo made a noncommittal noise but inside he was rejoicing. He had come here because he had heard from Zach's roommate - whom he was good friends with - that the sophomore would be coming here for spring break. He had hoped to get the opportunity to see him in swim trunks, even if that meant having to see him with some chick. Now that he saw him wearing that, however... The possibilities were too good to be true. "I think I see my prize." He commented casually and when Chris looked at him he casually pointed to a younger girl standing near the exit. She looked like she was already drunk and like she was eager to leave with the next guy that walked up. "I'll catch you later." He told Chris then held out his hand for a fist-bump before walking over to the very intoxicated college girl.

It was easy to pick up college girls, especially drunk ones that were willing to jump into bed with the next guy to come around. It didn't take much to convince her to return to his room. Though after only twenty minutes she passed out on his bed. That was the best possible outcome to this. He didn't actually want her, he just needed an excuse to ditch Chris. Now if his friend came knocking in the morning he'd find the passed out girl and, hopefully, assume that Theo and she had a wild night then passed out and he had gone out prowling again in the morning before she woke. She was drunk enough that she wouldn't remember anything either way.

Now he had to go get ready to hit on Zach. What kind of guy would Zach like? After going through everything in his suitcase he decided nothing he owned would work. What if Chris saw him? He needed something else. With a quick glance at the woman passed out on his bed, he grabbed his wallet and left his room again. Thankfully the resort had a multitude of gift stores that catered to the party life of all sorts of college students. Deciding to go with the tall, dark and mysterious trope, Theo found a black tuxedo and then picked out a gold and black mask to go with it. Funny enough, with as outlandish as the outfit seemed - it certainly would have been out of place at the school for one - with the wide variety of tastes here on this island, he blended right in.

Feeling only a little nervous, he made his way back to the bar. As he searched he became increasingly more anxious. Where had Zach gone. Surely he hadn't left already, right? Just as he was starting to inwardly panic, he spotted the younger man at the bar. Damn, another man was already hitting on him. Though the overweight, drunk man did seem to be coming off far too pushy. In fact if Theo was reading the situation correctly, the college youth was trying to push the drunken man away.

Increasing his pace, he moved through the crowd and pulled the drunk man off Zach. "Can't you see he's not interested?" He asked in his deepest, most aggressive tone.

"Was it to you?" The man asked in a slur. "Clearly the little queer wants a man to come fuck him."

"I think what he wants is a real man. Not some drunken slob like you." Theo retorted quickly. The man didn't reply, just swung his fist at Theo.

Not only was Theo not drunk, but he was also a star athlete with quick reflects. He easily dodged the sloppy punch then used the man's own momentum to send him falling into the crowd nearby. It wasn't long before security came to escort the drunk man back to his room. Standing protectively behind Zach, he waited until the man was gone before turning his attention back onto the man whom he had been lusting after for far too long. "Are you alright, he didn't hurt you, did he?" He asked gently, setting a caressing hand on Zach's wrist and letting his thumb ever so lightly play with the bracelet there. Unlike the man he had just fended off, the only smell lingering to Theo was a warm, but not overpowering, cologne.

 

[Extremeophile]

It's had only taken 15 minutes before the fat horny male had come up to him to talk to Zachary. At first the younger male had been annoyed, the man had been acting rather kind and talking about his trip, but that's not what he had been here for. He was hoping that the rest of the night would not be a waste of him sitting at the bar, drinking alcohol free drinks, and having men not hit on him. What else could he possibly wear at this point? A singlet? Lipstick? He wished he had just had the courage to talk to someone his own age, seeing the groups of college men looking at eachother. What if they didn't like gay people? It was more likely they would beat him up than talk to him he thought.

Zach had toned out the stranger who had been talking to him, only to hear the words "come back to my room." Out of some hazy fog, like electricity zapping him right in his eardrum. He had been asked back to someone's room? He looked back at the older male who was grinning at him now. "Oh that perked up your ears did it?" He asks, Zach now blushing and squirming as he considered it. He wanted to have sex, he wanted to see a dick, but did he want it that badly? He takes a swing of his cranberry and soda, at least feeling out what this opportunity could be. "Go up to your room and do what?" Zach asks in his best femmy interested voice. "Suck my dick! Anyone at the bar can see you're a huge slut, I'm just the first one to come over here and ask." He says leaning in a little closer. "Come on, I'll be quick, you can always come right back down here and pick up someone else." Could he? Really? Maybe he could spend the weekend just like this. He wished he could have something different, not because of the age of the man, but just because he wished it could be one person. Could one person ever satisfy him? He hoped so. If not where would he end up? "Sounds like it could be fun..." Zach says tentatively.

That's when the college aged male stepped in between them. Dressed in a tuxedo and mask, the male looked out of place at this tropical resort bar, where most people we dressed in Hawaiian shirts and casual clothing. He seemed to Zachary like some kind of superhero out of a movie, wearing that mask and 'rescuing' him from the old man he had been planning on fucking just a moment ago. Yet it was clearly just an angle to get his attention, and Zach wouldn't mind either way. Zach was Theo's fantasy boy. A very cute twink that had sat in many of his classes and had a dorm in the same hall as him wearing tight clothing that showed off his small frame and tight looking ass. Theo wasn't Zach's fantasy, instead Zach's fantasy had been every boy on the floor of his dorm hall, Theo included, but also Theo's friends, maybe even some of his enemies, the boy fucked his toy thinking about each of them back where they were both from.

He doesn't recognize Theo just yet, but he's suspicious, swearing he's heard that voice SOMEWHERE although he can't place it. The male standing before him was much more of the build he had been hoping for, this one wouldn't get tired halfway at least, he was taller and more muscled clearly. Someone it would actually be nice to sleep with. He blushes and smiles, feeling some comfort in thinking he knew why the male had really rescued him. He wanted to throw himself into the males arms to be carried off somewhere, but he had struggled to keep his desires and his actions separate his whole life and he wasn't going to blow it by coming off as slutty as he actually was.

He lets Theo play with his wristband and caress his hand, laughing a bit at the cheesiness of Theo's line. Zach was sober too, and half that guy's age, he wasn't in danger of being beaten up, he was in danger of having a lousy fuck. "Ah, no, he didn't hurt me." He says with a huge grin. "He was almost going to have some fun until you came along." Clearly he was looking at Zach, but this wasn't the shy kept to himself boy he was used to. He was bubbly, putting on some kind of a show for Theo. "We could maybe do... What he was going to do?" Zach asks, shivering a bit as he pushed himself, infesting two fingers up Theo's sleeve to caress his arm teasingly. He felt like he had no idea what he was doing, but he wanted this. "In my room, if you want." He asks, secretly terrified he was going to fast. For Theo, it was as if his acquaintance was suddenly out of a porn movie. It almost seemed like a strange dream.

 

[AllThingsCuddly]

Theo listened as Zach spoke. At his words, however, his eyes went wide and he glanced back toward the door the man had just been dragged out of. What? Zach had been about to willingly leave with that? Why? The boy deserved something better. Glancing back at Zach he listened to the following words, felt his fingers slip up his sleeve and caress his arm. It was like electricity on his skin. It was a simple, small caress but for Theo, who had fantasized about Zach so many times, the touch was magical. And the other was being very open. Was he really that desperate to get fucked? Was this the whole reason why Zach had come to this island in the first place?

Whatever the case, this was too good to be true. He smiled, looking down at Zach and raised his other hand to caress his face. "And tell me, what exactly was he going to do?" He asked in a lusty voice. "Was he going to..." He leaned down and kissed Zach's neck, caressing the smooth skin there with his lips, trailing a line of kisses up to his ear where he nibbled gently, breathing in the scent of the smaller man. "Fuck you silly. All. Night. Long?" He finished his question at last, whispering it into the eager ear. Then his tongue slipped into that very same ear, teasing about for a moment before leaving just as quickly.

"Your room would be perfect." He backed up a little, just enough for the younger man to be able to stand up. Then he followed him through the crowd and back into the halls of the hotel. Walking behind Zach gave him a good view of that tight little ass walking away from him. He could feel his arousal mounting by the moment. Was this really going to happen? Was he really, finally, going to have the opportunity to be sexual with the man he had been thinking about for years? Fuck. If he had known how eager the other man was, he would have approached him that very first day!

 

[Extremeophile]

It was a mixed feeling seeing how Zach would have gone up with the man who was now being dragged out. On the one hand it probably meant that Zach was desperate and eager, probably willing to bend over for Theo at a moment's notice, but it also meant that it was likely Zach had no outlet, maybe never had an outlet, and to see that he had been that neglected for that long was painful to look at. His heart was racing now, especially as Theo leaned in and whispered into his ear, feeling that tongue along a sensitive part of his body made his guts twist into a knot. He had wanted the male just for how he had looked and acted, but now he was feeling even more lustful and safe to be himself, safe to be the person he really was instead of who he had pretended to be in front of his college peer for the longest time. "I don't think he was going to last very long, and if you could to that for me all night long I would be pretty thankful." He says, still trying on flirting for the first time.

Zach leads the male to the elevator up to the 6th floor. "My name is Zach by the way." He says giving the other male a warm hug as the floor numbers ticked up. "I kind of like the mask." He says flirtatiously, rubbing the tuxedo over. "I think the suit is a little much, but I don't think you'll be wearing it very long." Despite the confident words coming from Zach, his demeanor was still sheepish. He wouldn't look up into the man's eyes, just down at the floor of the elevator. The blush on his face betrayed his true feelings, he was nervous and excited, but he wanted to come off as being sexy, still worried he'd blow it somehow. "I can't wait to get up to my room." He adds awkwardly, his breathing sounding forced and uneven.

When he finally gets to the floor, he practically sprints to his bedroom door, wanting to get back inside quickly. He misses the locking mechanism the first few times, giving a soft nervous laugh, his hand shaking just a bit. "Haha, sorry." He tosses off casually, finally finding the slot and unlocking his bedroom door. "I've never actually done anything like this before." He says letting the masked stranger inside of his room, still having no idea who was underneath the mask. He closes and locks the door, walking further into his rather nice king sized bedroom and sitting on the foot of the bed. "So uh... What happens next?" He says, that mix of lust and inexperience coming off in waves

 

[AllThingsCuddly]

As Zach offered up his own name so freely, Theo wondered if he should give his own. Theodore wasn't that unusual of a name, would the other immediately know it was him if he gave it? Best not take that chance, he still had no idea how the other would react to knowing his mysterious date was one of his dorm mates. Instead he just kept his mouth closed. If the other directly asked him his name he would come up with something to tell him. All this was going through his head as he weaved through the crowd to follow the smaller form to the elevators.

When they were alone in the elevators he wrapped his arms around the other, perfectly content with his closeness. "I'm glad you enjoy the mask, Zach." He said to fill the air and not come across like he was ignoring the other.

Finally they reached the sixth floor, their apparent destination. He glanced around and noted that the hallway was pretty quiet. Most everyone was still down on the main floor partying. Very few had retired to their rooms just yet. His ears perked up and he turned his attention back to his date. "Never done this before. Now Zach, you're not telling... You're a virgin, are you?" He asked if in a casual way with a light grin on his face. Being Zach's first, it was unexpected but somehow he found it all the more arousing. Stepping closer he let out a small moan of lust as he wrapped an arm around Chase and dipped his head, bringing his lips to meet the others.

"Next? Well there's one of two things that can happen... Either we can take the time to get to know one another better over drinks or perhaps a meal, my treat... Or we can skip straight to the main course..." His left hand gently roamed down the man's body until it found his crotch. There he began to caress the bulge already forming. "It feels to me like you are more eager for the main course but I'm open to either scenario, just tell me what you want."

 

[Extremeophile]

((I think maybe something might have been misinterpreted as a kiss? I'm rolling with it anyways))

"I'm not... exactly a virgin." Zach admits with a blush. "When I was a lot younger I sucked a dick once... It was nice, I've been thinking about it ever since." He says with a nervous laugh. "I guess I was either always focused on something else, or at least I never wanted anyone else to know. I'm always afraid that people aren't going to like me, or I'm going to get hurt, or that my identity will become 'the gay guy' instead of 'Zach'" He admits as he enters the room, finally getting his keycard right. "I've never really told anyone that, but I'm on vacation so who cares?" He says, trying his absolute best to be more comfortable even though he was on pins and needles.

Zach hadn't expected to be kissed as soon as he had entered, but he was definitely not opposed or resistant to it. He gets up on his toes, wrapping his arms back around Theo's neck and kissing him back. He had wanted it to be a tame kiss, but he couldn't help but feel his tongue slip free eagerly. Was it all about to happen? Was he going to be picked up and thrown on the bed suddenly. He braced himself for something long or sudden, but instead Theo pulled back, being the gentleman he was. Zach's heart was racing, and his modest bulge apparent between his legs. He shakily makes his way to the bed, still looking over at Theo and asking him his question. "So what happens next?" He says eagerly. It was plain to see how badly he wanted it, was Zach really this slutty underneath it all?

He gives no hesitation when he's groped, taking in a sharp breath through his teeth and gasping in pleasure at the touch. It was true, his modestly size cock was hard as a rock and throbbing, jumping in Theo's hand. He lets Theo continue talking, but as soon as he's done he grabs the male and pulls him into another kiss, this time being a bit more aggressive than he had been just a few moments ago now that Theo's hand was actively grabbing at his cock. The kiss was incredibly eager and needy, Zachs whole body shaking, his tongue pushing around inside of Theo's mouth. It wasn't the kiss of a timid bottom who wasn't sure what they wanted, it was the kiss of someone who was incredibly thirsty and needy, someone who wanted sex badly. His hand grabbed at Theo's ear, blowing steam on his cheek. He didn't pull back for some time, pushing the larger male onto his back and crawling on top of him, sitting against his bulge and whimpering into the intense and aggressive kiss.

He pulls back, panting, looking down into Theo's still masked face. It looked familliar somehow, but he still couldn't place it. It was afraid, afraid of taking it off and seeing who it was and changing his mind. He didn't want to know, not until Theo was somehow deep inside of him. This was the real him, feeling lustful from head to toe, grinding his ass down eagerly, shaking like a leaf from the emotion that felt like it was surging through him like lightning. "Sorry..." He says pushing his hair from his face, biting his lip. "I'm sorry... I'm just so... I didn't mean to..." He says with a small nervous laugh. He seems barely able to talk, and after only 30 seconds of awkwardly, impossibly, trying to talk he instead pushes his lips against Theo's again, needing to taste him, needing to feel his lips against Theo's again. He had been waiting for this moment for so long and now, finally, he was going to have all of the sex he had imagined himself having since he was in high school.

 

[AllThingsCuddly]

((no worries, a kiss was exactly what I intended))

Theo smiled. "Sucking a cock and being fucked by one are two entirely different things." He commented when the other defensively said he wasn't a virgin. True, Zach wasn't entirely innocent in sexual activity but if sucking a chick was the furthest he had taken it, Theo would consider him a virgin. He just wouldn't bother saying that out loud. Though when he mentioned that he didn't want to be known as the gay guy, he could only nod. "No one back home knows about me either. I play sports and I've always been afraid that if I come out my team mates won't want me in their team. They'll be nervous around me and not want to shower when I'm around for fear that I'm getting turned on by seeing their naked bodies. It won't matter how I explain it to them."

After Theo offered to buy dinner or just get straight to the fun, Zach practically threw himself at Theo, wrapping his arms around him and kissing him with a fierce resolve. There was so much force and desire to the kids that Theo soon found himself tumbling backwards into the bed with the smaller male on top of him. Strangely enough, his first concern was his mask, which he reached up and made sure was secure in his face. He didn't want Zach knowing his identity. Not now and maybe not ever. His tongue sparred with the invading tongue, pissing back and forth and around in circles.

The small frame was grinding against his own growing erection and all Theo wanted to do right now was fuck Zach for all he was worth. With a lusty groan he rolled them over so that he was on top. "There's no reason to be sorry. You are a passionate lover, I like that." That said, his hands undid the short shorts and pulled them off aggressively, making sure to get the underwear with them.

He didn't bother to undress himself, all he did was undo his pants and pull them down low enough to reveal his hard and aching cock. Bringing the hard phallus to the tight hole that had just been grinding against him, he paused. "Are you ready for me?" He asked.

 

[Extremeophile]

"Uh... Yeah I guess so..." Zach says in response. "At least I've seen one and touched one..." He adds defensively. "I've used a toy before... I mean I have one." Zach continues, trying to defend his limited experience to the masked stranger. "It would be hard for you but at least you're a top! Try being the guy who wants to get fucked like a girl and see how people feel about you then." He says with small blush and a nervous laugh.

Only moments after grinding on Theo and kissing him, he was suddenly grabbed and flipped. He let out a loud gasp of surprise when he's suddenly pinned by Theo who looks down at him, making him laugh again and push up to catch Theo's lips again from underneath him the second he was done talking. Wrapping his arms around the other males neck, his breath tickling over his cheek while he pushes his tongue back in again, his own bulge throbbing and poking against Theo's inner thigh.

As soon as Theo pulls away, he begins to yank at Zachs shorts and underwear, tugging them off roughly and exposing his lower half. Zach's length was small, somewhere between 3.5-4 inches of hard and drooling cock. When Zach was younger, he was so embarrassed and disappointed by the size of his cock, but as he got older his smaller length was one of the things that pushed him into being a bottom. He had started to think in high school that his relatively thin hairless body and smaller length made it so that he was built for bottoming, thinking that he looked like a hot twink and if he was bottoming his size wouldn't matter anyways.

When Theo poked at his backside, he gives another gasp, then a whine. He opens his mouth, then closes it, wondering if he should protest or not. In the end he feels he has to say something. He may not have been topped before, but he had used a toy in the past, and now that Theo's dry cock was poking at his dry entrance he could already feel his sensitive skin being pulled this way and that by the burning hard length grinding between his cheeks. "I uh... I think I might need some lube or..." He pushes his fingers through his hair. "Haha, I guess I didn't expect to get this lucky." He says rubbing one of his bare feet against Theo's cheek, the closest he could come to a caress. "Maybe we could get some or?" He says, not sure what to do.

 

[AllThingsCuddly]

Not wanting to push Zach past his limits, Theo hovered over him while he waited for a response and the one he got was unexpected. It was reasonable. With such a tight, virginal (mostly) hole, trying to shove his hard, 6.5" cock into it would be uncomfortable for him and most likely painful for his partner. He himself didn't have any lube in his pocket, he hadn't thought about that at all. Though he did have a couple condoms in his pocket. How could they handle this situation? He didn't want this moment to pass and leaving the room to go get a bottle of lube would definitely ruin the mood. He hesitated for a moment, looking down at the younger male. He had been waiting years for this moment! But, he also didn't want to ruin things by making it an unpleasant experience for either of them.

"You don't have any?" He asked, swallowing hard. Okay, he could deal with this. Think, think. A thought occurred to him and he pulled back, standing up. Walking over to the phone, he picked it up and dialed a single number. As the front desk answered he turned his back to Zach so the other wouldn't see the blush that was sure to form with what he was about to say, even if it would mostly be hidden by his mask.

"Hello." He said to the front desk then took a deep breath. "Are you able to send up an item from one of the gift stores? You can? Great. I need you to send up a bottle of lubricant from the Romantix gift store. Thank you." He then hung up the phone and took a deep breath. Well, that had been embarrassing. The lady on the phone hadn't laughed at him but he was sure she probably had once the line went dead. When he had been looking for something to wear he had noticed the gift shop that dealt in sex toys, lingerie and other bedroom gear - it's where he had picked up his condoms.

Not wanting to spoil the mood by them just sitting here awkwardly waiting for room service, he made his way to the end of the bed and grabbed Zach's legs, bringing him closer to the end of the bed so that his rear end was right at the edge of the bed. Kneeling down in front of the bed, he set Zach's legs over his shoulders and leaned in, beginning his face closer to Zach's quivering entrance. His tongue began to tentatively prod at the hole and one of his hands came up to begin slowly stroking his partner's small cock.

 

[Extremeophile]

Zach watched as Theo picked up the phone, his eyes open wide at the things he was saying on the phone. A dark blush slowly crept over his face with each new word, now the whole hotel staff would know he was having sex in here, and maybe hearing the voice of a different male they would know it was gay sex! It was a silly thing for Zach to care about, but for him it felt like a big deal. Two things seemed to hit him at that moment: one was that he was laying on the bed leaving Theo's half naked body alone, the other was that it was kind of hot how casually the male seemed to be exposing him.

Theo was only away for a few moments, but by the time he was halfway through his phonecall, Zach couldn't take it anymore. He was horny, and this whole business wasn't helping. He crawls across the bed, and before he can finish chatting with the people downstairs, Zach grabbed his still hard cock and pushed it into his warm wet maw. He whimpers, caressing the males inner thigh, holding onto his left leg and hip for support while his head bobbed up and down on his tip. Even when Theo hung up, the taste and excitement of it was too much to pull away from. His breathing ragged, he did his best short of swallowing it reaching down and playing with the other males balls, suckling and whimpering.

After a few more moments, he pulls back with a soft pop, his own cock still rock hard and drooling from it before he was pushed back, the other male getting down on his knees. Zach knew what was coming, but he had never experienced it before. Was he actually going to have another male licking his ass? And then it happened, the wet tongue poking at his entrance. "Oh fuck!" He says with a gasp, twisting and whining as his head turns left and right. "Oh my god, oh no." He continues, breathing sharply through his teeth, his tight virginal hole squeezing at the invading tongue. He hoped they would take their time getting up here, not wanting this to end, never having felt so sexy before. "Please don't stop." He begs, putting his palms over his face and whining.

Then Zach does another unexpected thing, carefully putting his hand on the back of his partners and peeling his fingers off of his cock one by one. He didn't want to blow before it was time, and he was nervous that the rimjob and handjob might be too much for him. Once his fingers were laced through Theo's, he rubs his thumb on the back of his hand and bucked his burning hot length up against his palm, smearing some precum on it. "I... Ah... Uhm..." He starts, trying to find the words to explain himself while he was being pleasured, the combination of stimulation and embarrassment making it difficult. There was a long pause of gasping and shivering before he could finally speak. "I want to wait." He says, almost sounding like he was about to say something disappointing before he dropped the next part. "I want to wait until you're done... To cum." He admits, his blush still plastered on his face, revealing some of his kinky nature for the first time. "I want to wait until you're all done fucking me, and then I want to cum... Maybe..." He says, nervous, hoping that the mysterious stranger would be into it as much as he was.