Tokay's Helping Hand

Story by DarkWolf79 on SoFurry

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#40 of Story Commissions

Tokay's roommate is a little nervous about his first time bottoming. Luckily, the gecko is more than happy to show Jackie some other ways to have some fun with his date.

Commission for FA: Jackiez

Tokay: https://cdn.discordapp.com/attachments/832592732425158666/832593298152488970/WhiteLeech_dehu9rd-ad4294b4-7097-4e87-a784-5df4fe7061d2.png

Jackie: https://cdn.discordapp.com/attachments/879705305947189249/879705376260497408/pchlnx_38848004_Mc5uyLJ66H5v1zX.png


"Hmmmm..."

Tokay turned up the volume, hoping to drown out the mumbling and whining coming from his roommates bedroom.

"Ummmm..."

Apparently there was going to be no drowning out Jackie's noise.

"Oh, what do I do... what should I wear...can I really..."

"Jackie!" Tokay called out through the slightly cracked door. "Would you just make a decision already? It's hardly your first time going on a date."

The door to Jackie's bedroom flew open, revealing the apartments other resident who looked far too stressed for his own good.

"That's not the point!" said Jackie. The other gecko's pants were sitting low on his hips, the loose black cotton threatening to slide right off him if he wasn't careful. "Tonight has to go right. I've got to find the right outfit!"

Tokay chuckled. "Why? Aren't you planning to spend most of the night out of it anyway? Why go through all the hassle of dressing up just to have it all crumpled up on his floor?"

"You just don't get it."

Tokay shook his head, "No I really don't. But I've never put much stock in that kind of thing anyway. Besides, he's not coming to get you for hours." The big gecko patted the empty chair beside the couch he was lunging on. "Come and take a load off for a bit and calm down before you pop a blood vessel."

Jackie moved into the living room, flopping down into the chair and leaning back, sighing heavily, while Tokay took the opportunity to look the other gecko over. Since he was dressed only in his loose pants, Jackie's brightly colored upped body was on display. The pale creamy white of his chest and belly gave way to a bamboo green at his shoulders and along the top of his head. Black spots dotted his shoulders and the snout, and Tokay could see more around his hips that disappeared under his pants. More black covered his hands like gloves, his white fingers standing out even more as Jackie rubbed at his temples.

"Seriously, why are you so worked up?" asked Tokay, lifting the bottle in his hand and taking a sip of beer.

"I'm nervous about my date, alright," said Jackie.

"I thought you liked this guy. Certainly didn't hear you complaining after he went down on you," Tokay added with a smirk.

"You heard that!?" exclaimed Jackie.

Tokay laughed. "Kind of hard not to. Who knew you got so noisy when you had a guy sucking your dick. I don't remember you getting that vocal with the last girl you brought home."

"Probably because she didn't like oral," said Jackie. "Or at least, she didn't unless she was the one getting it."

"At least that tiger of yours doesn't seem to have any objections," said Tokay. "And no wonder you were so loud; cat's like him have amazing tongues."

Jackie shivered as he remembered the feeling of that slightly sandpapery tongue lapping at his dick. "Yeah they do."

"So what's the problem then?"

Jackie shifted in his seat. "We've been talking about having sex tonight."

Tokay took another sip of beer. "Good! Maybe a nice hard fuck will help you relax."

"That's just it," said Jackie, blushing slightly. "I've never bottomed for another guy before."

"It's not like you've never had anything back there," said Tokay, I've seen some of your toys..."

"That's different," said Jackie. "My vibrators are pretty small. I've never tried taking anything as big as him before."

"How big is he?" asked Tokay. Jackie held up his hands to show him, and the gecko whistled. "Damn, not starting slow are you?"

"No kidding."

"Well, you could always use a dildo to stretch yourself out. Get some practice in before the main event."

"Great idea," said Jackie flatly. "Too bad I don't have enough time for that before tonight. And what if I can't do it? What if I don't like it? Or worse - what if he doesn't like it!?"

Tokay laughed. "If he's really that big, I don't see any way he wouldn't love getting your tight little ass around his cock."

Jackie's blush turned his cheeks pink. "Tokay!"

"I'm serious," said the big blue gecko. "The feeling of a smaller guy squirming under you or bouncing in your lap, his tight, hot ass squeezing your cock..." He shamelessly adjusted himself through his shorts, his cock starting to poke out of his slit as those thoughts filled his head.

"But how am I supposed to be ready for that by tonight?" asked Jackie.

"Look on the bright side -- at least you don't have to worry about getting knotted your first time," said Tokay. "You'd be walking funny for days."

"You're not helping," said Jackie. "What am I going to do?"

Tokay took another swallow of beer, thinking. "Well, I guess the simplest thing to do would be to put him off until you get some more practice."

"Now, let's not be too hasty," said Jackie. "He's really hot--"

"And now that you've seen his cock you want the full experience," finished Tokay. Jackie nodded eagerly. "Well, if you need some help getting used to taking dick..."

Jackie held up his hand. "Forget it. My tail cherry is spoken for, thank you very much. I did not shamelessly flirt with a sexy tiger just to give it away to my roommate."

"Love you too, buddy."

"Eat me."

"Happily," said Tokay. "Take off your pants."

Jackie smacked the other gecko's arm playfully, the pair laughing as they slid into their usual banter. Knowing each other and living together for as long as they had, it was only natural the two would be so comfortable with each other. And after you'd traded blowjobs a few times or gone to a sex shop together, any sense of shyness or embarrassment about their bodies or sex lives was dead and buried.

"Well, if you're really that worried about taking it in the tail, there's always the other option," said Tokay.

Jackie looked confused. "I told you, I've already sucked him off--"

"No, not that," said Tokay. If you're worried about taking him under your tail, you could always start with your slit."

Jackie starred at the other gecko for a full ten seconds before finally saying, "What?"

"If you're really that worried about having your ass fucked, why not just offer up your slit instead?"

"My... you... y-you can't be serious!" exclaimed Jackie. "You want me to have him fuck my..." His hand drifted to the front of his pants.

"Why not?" said Tokay. "You know it's big enough to take a hard cock since it can already fit yours. Who knows, you might even realize your enjoy it."

"You really think I'd enjoy having another guy's dick in my slit? I don't see how anybody would like that," said Jackie.

"You only say that cause you've never tried," said Tokay, grinning slyly at the other gecko. "But trust me, you haven't lived until you've gotten to feel another guy squirming under you when you fuck his slit."

"That's all well and good for you," said Jackie, "but do I need to remind you that I'm the one with the slit, not him? I'll be the one getting fucked if I agree to that."

"So why are you complaining?" asked Tokay. "Just imagine how it'll feel, both of you stuffed in your slit. Your cocks rubbing together while he fucks you. And hey, if you let him cum inside you, you'll be all lubed up to get under his tail."

Jackie started to protest, but slowly closed his mouth as he thought about it. Seeing that the other gecko no longer seemed to be completely opposed to the idea, Tokay made his move.

"You know, if you're really that nervous about it, why not try it for yourself before your date?" suggested Tokay. "That way you'll know what to expect and if you even like it. No point in totally shooting down the idea before you know how it feels, right?"

"I suppose..." said Jackie slowly, considering the other gecko's words. "But how am I supposed to test that out? I don't have any toys that big."

Tokay grinned, cupping his crotch through his shorts. "Who needs a toy when you've got the real thing?"

"You must be kidding!"

"You really gonna try to tell me you're feeling bashful now? How many times have we sucked each other off? We spend more time here naked than we do dressed," said Tokay. "Besides, you need to try it out and all this talk has me horny as all hell. What's it gonna hurt if we have some fun?"

"Well... I guess it wouldn't hurt--HEY!" Jackie exclaimed as Tokay reached over and yanked him into the big gecko's lap.

"Let's see what we're working with," said Tokay, laughing at the way his friend yelped when he slipped his hand past the green gecko's waistband and started rubbing at his slit.

"What are you doing!?"

"I'd think that was obvious," said Tokay, slowly starting to work a couple fingers into the squirming gecko's slit, feeling his muscles clenching down on him at the alien feeling of another man's fingers in a place nobody else had ever touched. "Just getting a feel for how tight you are. And not gonna lie, if the rest of your ass is even half as tight as your slit is, your tiger's in for quite the treat."

Tokay pulled his fingers out of Jackie and made a show of popping them into his mouth, sampling the other male's taste.

"Delicious."

Tokay thrust up against Jackie's ass, letting the other male feel the way his cock had slid free of his own slit, his erection straining to be free of his shorts. Pushing Jackie to his feet, Tokay grabbed Jackie's pants and yanked them down to pool around his feet. The green gecko had just enough time to register that he was naked before Tokay stood and picked him up, leaving Jackie's pants on the floor as he threw the other man over his shoulder and walked towards Jackie's bedroom. Tossing the smaller gecko onto his bed, Tokay laughed at the way he bounced before coming to a rest, nervously looking up at the big gecko, his legs unconsciously spread almost in invitation, exposing himself to Tokay.

Tokay slowly unbuttoned his shirt, shrugging it off and undoing his shorts. "You just wait right there while I get ready."

Tokay let his shorts fall to the floor, kicking them away and leaving him just as naked as Jackie. He couldn't hold back a smirk at the way Jackie's eyes widened when he saw that Tokay was already fully hard and out of his slit, the deep purple-red length of his cock a stark contrast from his blue belly. He could practically feel the other gecko's eyes of his ass when he strolled over to the bedside table to grab the lube Jackie kept there, smearing a generous amount along his cock, making a show of jerking himself for his friend, Jackie's white cheeks a bright pink from blushing while he watched his roommate put on a show. It wasn't until Tokay moved onto the bed that Jackie really registered what was about to happen, the size difference between himself and Tokay very obvious once the blue gecko's penis was pressed against his slit.

"Tokay," said Jackie nervously, "You're, uh... you look really big right now. I mean, I knew you were big but... I-I don't think I really thought about how big your dick is compared to mine."

"Flattery won't get you anywhere, bud."

"That's... you know that's not what I meant!" exclaimed Jackie. "There's no way you'll fit!"

"Oh, I'll fit alright," said Tokay, lining up the pointed tip of his dick with Jackie's slit. "You aren't the first guy I've done this with." He took hold of Jackie's hips, holding the smaller gecko still. "Trust me, you're gonna love it."

Jackie gulped heavily, his eyes locked onto the point where his body met Tokay's as the other gecko started to push against him. At first his slit didn't give way; Jackie was too tensed. But when he took a breath to steady himself, his body relaxed for a moment, just enough for the tip of Tokay's cock to push through his resistance and start to enter his slit. It was a very strange feeling having another guy inside him like that, and Jackie couldn't help but whimper a little at the stretched, full feeling of Tokay spreading him open.

"Tokay, I don't know..."

"Just relax, Jackie," said Tokay gently easing his hips forward inch by careful inch. "You won't be disappointed, I promise."

"B-but, Tokay--Eeep!"

Jackie yelped when he felt the other male's penis touch his own, gasping when Tokay's crotch pressed flush with his own, realizing that he'd actually managed to take the other gecko's entire dick. It felt so full, but what really got his attention was the feeling of his friend's cock pressed so tightly against his own. Jackie had never known it was possible to feel something like this.

And that feeling only got more intense when Tokay started moving.

It was the strangest feeling he'd ever had, feeling Tokay's cock sliding in and out of him. When the other gecko pulled back, Jackie felt strangely empty, only to gasp when his friend thrust back into him, their bodies slapping together as Tokay set a steady pace, properly fucking the smaller male's slit.

"Oh, Tokay!" grunted, Jackie. "I-I... I t-think this might be too muuuuuhhh!"

Jackie couldn't hold in a moan as another thrust from Tokay made him realize something he hadn't noticed before. Despite his nervousness and the unusual feeling of Tokay inside him, it seemed he might be enjoying himself more than he thought. He was hard. But with the other man inside him, no matter how hard he got, he couldn't leave his slit. Inside he might be big enough to hold them both, but there was no way his opening was letting them both out at the same time. And since Tokay made sure not to pull all the way out of him, Jackie's penis was trapped, being pressed firmly against the other gecko's cock, the delicious friction of their dicks rubbing together making his toes curl.

"Tokay..." Jackie gasped, pushing half-heartedly against the big guy's belly.

Even if he'd really been trying, he would have had a hell of a time physically stopping the bigger male, and with the feelings spreading out from his slit he just couldn't muster the strength to really try to stop him. Especially when Tokay grabbed his wrists and gently pinned them to the bed, laying himself over the green gecko, his hips slapping against Jackie's thighs and making him bounce a bit under him.

"Feel that?" asked Tokay, pressing himself forward until he was hilted inside Jackie, flexing his cock a couple of times. "That's my dick in your slit. Admit it - you're starting to like this. Just image, your tiger getting you naked, pinning your sexy self down and fucking you like this."

He started working his hips again, angling himself to really press against Jackie's trapped penis, making the smaller gecko moan.

"His fur rubbing against you. His big dick pressed against yours. And think about this..." he leaned over to whisper huskily into Jackie's ear. "His barbs. Just think about how it's going to feel to have those rubbery feline barbs pricking at your slit, making you feel things no other guy can feel. I may be big, but add barbs to the mix." He chuckled. "You'll be squealing for more before he's even really gotten started."

Jackie's white cheeks where an almost luminous shade of pink. Tokay's words were so embarrassing! Though not nearly as embarrassing as the way Jackie's body was reacting to them. Because he was thinking about it. That muscular body. That luxurious fur. And the idea of the big, barbed dick pounding his slit and rubbing against his cock the whole time until Jackie was reduced to a cumming squealing mess.

That mental image was the last straw. Jackie's back arched, his head falling back as he came, his whole body seizing up as his orgasm hit. But because he was still stuck inside his own slit, his orgasm was made even stronger by the feeling of his own body clenching down around him, pressing his and Tokay's cocks together and milking both lengths at the same time.

A wet warmth filled him as Jackie realized his was cumming inside himself, the added lubrication letting Tokay thrust into him that much harder. Tokay slammed forward one more time, bottoming out with his penis squeezed firmly against Jackie's as he started to cum as well, adding to the mess leaking out from between Jackie's thighs.

The pair kept grinding against each other, riding the waves of their orgasms until they finally started to fade. When Tokay pulled out, Jackie's penis was finally able to slide free, their cum-covered lengths standing proudly between them. Jackie was far too spent to move, but Tokay spun himself around so they were facing opposite directions, pushing his dick past Jackie's lips and sucking the green gecko's cock into his mouth, the two men cleaning each other up with a leisurely sixty-nine. When they were finally as clean as they were going to get without a shower, Tokay pulled away, letting Jackie's cock retreat into his slit, grinning as some of his cum continued to ooze out of the other gecko.

"So," said Tokay, panting, "Feeling a little better about it now?"

Jackie was barely able to lift his head right now, but he managed to nod.

"Holy... shit..." he said, his chest rising and falling heavily. "That was... I just...wow."

Tokay laughed warmly pulling his shirt back on but leaving it unbuttoned, not bothering to put on his pants.

"Glad I could help. And hey, let me know when you schedule your next date for so we have time to get you ready."

Jackie raised an eyebrow as he slowly sat up. "Get me ready for what?"

By way of an answer, Tokay reached between the other male's legs and pressed a couple of fingers against Jackie's tailhole, teasing him open ever so slightly and making the other gecko squeak in surprise.

"Why, to take it under the tail, of course. I've been eying that cute ass of yours for a while, and I'd be happy to help you test some things out." Tokay eyed the other male eagerly. "And this time, I'll make sure we have plenty of toys ready to show you just how much fun getting fucked can be. And if you're a good boy," he added rubbing his own rump playfully, "maybe I'll even let you take on turn with me."

Jackie could only stare, mouth agape as Tokay walked out of the room, strolling back to the couch and lounging back like nothing had happened. The green gecko would have to take a shower to make sure he was fully cleaned up and ready for tonight, but he knew that now that sexy tiger wasn't going to be the only male on his mind. And while he was in the shower, maybe he'd have to try using a finger or two back there, just to see how it felt.

And if he had any questions, he knew just where he could find some help.