Otter's Daily Life- Zebra's First Time

Story by Ragemend on SoFurry

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#68 of Otter's Daily Life

Kyle's project partner lets him in on a secret, and Kyle decides to help him out.


Kyle sat in the second floor of the library at his college, waiting on his own for his project partner to arrive. The otter quickly checked his email on his computer. He closed the browser and stared at the background on his laptop. A picture of him, Jean, and Austin was displayed. They were having a picnic in one of the city's small parks, smiling at the camera as Fawks took their picture. His phone buzzed and he checked it, Jean sent him a text reading: "Hurry up and finish your work. The bf and I are waiting~"

Kyle's ear twitched as he heard hooves clop down at the entrance to the second floor stairwell. A short and skinny zebra stepped out onto the stairs. He saw Kyle and waved, then walked over. He placed his bag on the table and the zebra sat down next to Kyle. He was cheery.

"Hey, Kyle. Sorry I'm late, got held up in class." Smiled the zebra.

"It's fine, Luke. Let's get started." Said Kyle, reaching over to his computer.

"Woah, who's the hot girl?" Asked Luke.

"She's my... girlfriend." Said Kyle, catching himself before calling Jean his sister.

"Woah. You're so lucky to be with a girl like her. And you just cost me $5. I bet my roommate you were gay." Laughed Luke.

"Well I'm pan so you both lose." Said Kyle, sticking his tongue out at the zebra.

"So you like guys too...?" Asked Luke.

"I like everyone... but yes guys too. The jackal in that picture is our boyfriend." Explained Kyle.

"You have a girlfriend... and a boyfriend...?" Asked Luke, just making sure he heard right.

"Yes." Answered Kyle.

"That's so unfair! You get two people and some of us have zero." Whined Luke.

"Not much luck with girls?" Asked Kyle.

"With anyone... I've never dated anyone." Blushed Luke.

"So, you're a-" Began Kyle.

"Ssh!" Shushed Luke. "Don't say it! Someone might hear!"

"It's nothing to be embarrassed about." Said Kyle, matter-of-factly.

"I'm graduating this semester. I'll have gone all throughout college a... a virgin." Whispered Luke.

Kyle held back a giggle and checked his phone again. It was a picture message from Austin. Thinking nothing of it he opened it in view of Luke, but it was Austin's first dick pic to Kyle, and Luke caught a full view. Kyle slammed his phone screen down on the table, but Luke was giving him a look.

"What was that?!" Balked Luke.

"That jackal's penis..." Blushed Kyle, pointing to his desktop photo.

"That's what dog's dicks look like?" Asked Luke, rhetorically. "It's so... hot..."

"You like guys too?" Asked Kyle.

"Maybe? I don't know if I even like girls." Said Luke, putting his face in his paws.

Kyle thought for a minute. He grabbed his phone and sent a quick reply to Austin: "You know how you can apologize for accidentally making me show my project partner your dick and for that we never did anything for my birthday? The two of you need to help me show my partner a good time. Anything he wants. Got it?"

He set his phone down and looked at Luke. The zebra wasn't making eye contact anymore, clearly embarrassed to have been so candid with someone he barely knew. Kyle tapped Luke on the shoulder.

"Wanna forget this and do something fun?" Asked Kyle. As he waited for an answer his phone buzzed twice. Both Jean and Austin gave him a thumbs up emoji.

"Like what?" Asked Luke, looking kind of melancholy.

"My girlfriend and boyfriend agreed to help you out tonight. They don't know why, but they've agreed to do anything you want. That would mean for me, too if the jackal's not your kind of guy." Explained Kyle. "Want to get out of here?"

Luke thought for a minute before nodding. Kyle put away his things and the two walked out of the building. They hopped on the subway and Kyle spelled out everything for Luke and his significant others. Luke was in control. As long as it wasn't too outlandish, he could ask for anything from any of them. Their job was to make sure his first time was as amazing as possible. Kyle lead Luke to Austin's apartment. When he opened the door he found Jean and Austin sitting at the table waiting for them. Jean was in a bra and panties, Austin was in his favorite blue briefs. Luke blushed when he saw them and immediately took off his backpack, holding it over his lap. Kyle closed the door and got undressed down to his red panties, joining his sister and boyfriend at the table. They all smiled at the zebra. Jean stood up and offered her paw to Luke.

"Hi Luke, I'm Jean." Smiled the almost naked otter.

"L-Luke." Stuttered Luke. He couldn't stop looking at Jean's chest. He'd never been so close to a woman in her underwear before.

Austin stood up too, offering his paw as well.

"And I'm Austin. Nice to meet you" Grinned Austin. Luke's gaze switched to the jackal's bulge.

"Well, now that everyone's introduced, Luke, why don't you join us in undressing, so while you get used to it we can discuss what exactly you'd like from us." Said Kyle.

Luke hesitated but eventually agreed. He slowly took off his shirt, revealing all of his stripes to the trio. Next, he carefully dropped his jeans, a modest bulge showed in his grey boxer briefs. No one said anything, but they expected something... bigger. He pulled off those boxer briefs and his half hard cock flopped out. It was equine, alright, but lengthwise somewhere in between Austin and Kaya. Luke sat down in the one free chair, then looked at Kyle.

"None of what we do here leaves the four of us unless I say so, okay?" Asked Luke. Austin, Kyle, and Jean nodded.

"O-okay. Jean, can you stand up and come over here? I've never seen a naked girl before." Requested Luke.

Jean got up and trotted over to Luke. She stood before him in all of her nearly naked glory. She reached behind her back and unclipped her bra, letting it fall to the floor. Luke's eyes widened and he finished getting hard rather quickly. He was throbbing so hard Jean worried he might spontaneously ejaculate. As she reached for her panties Luke hesitated.

"W-wait. P-please let me do it..." Blushed Luke.

Jean stopped reaching for her panties and stepped up to Luke, putting her paws behind her back for him. The zebra carefully reached for the Jean's panties, feeling where her pussy was covered first and then looping his fingers under the elastic and pulling them down. His eyes widened again as he the patch of pubic fur above her slit, and then her labia. The panties fell to the floor and Jean stepped out of them. Luke slid out of his chair to get a better look. Austin and Kyle watched the zebra inspect Jean, throbbing in their undies.

Luke caressed Jean's labia, she was very wet already. He had a basic idea of how things like this worked, but watching and doing are very different things. He felt for Jean's vagina, and when he found it he slid a finger inside slowly. Jean gasped as his invading finger slid in. Luke was almost in disbelief.

"If this is a wet dream I so don't mind the clean up it's gonna take." Thought Luke.

He pulled out his finger and held it to his nose. It smelled pleasant, and it tasted even nicer. He stood up, his erect cock now somewhere between Xeila and Kaya. Jean smiled when she saw it, it wasn't often she got a stretching like that. Luke turned to the boys.

"If you d-don't mind... I kinda want my first time to be with a girl... but I've always had a quick recharge so you both can have a turn if you want." Said Luke.

"This is your night, Luke." Said Austin.

"Yeah, take your time. We'll be fine out here." Smiled Kyle.

Jean took Luke's paw and lead him into Austin's bedroom. She closed it behind them and when Luke turned around to look at her she kissed him. He was so surprised he didn't even think to kiss her back.

"First kiss?" Asked Jean, sweetly.

"Y-yeah..." Mumbled Luke.

"How do you want to do it?" Asked Jean softly.

"Can I see something first?" Replied Luke, looking at his feet.

"What's that?" Wondered Jean out loud.

"Can I see your... tailhole?" Muttered Luke.

Jean heard him and giggled. He expected a slap but she merely turned around and raised her tail, using each paw to spread her butt cheeks. Luke kneeled down again, using a finger to probe the otter's pucker. She squealed when he did, but not in a bad way. Luke had always wanted to be able to rim a girl, so without warning he stuck his muzzle between her cheeks and lapped lavishly at her tailhole. Jean moaned loudly when she felt his soft tongue against her rump. Luke didn't know how much time had passed when he finally moved his mouth away from her pucker, but a small puddle of Jean's juices had dripped to the floor. Jean had to catch her breath when Luke stopped rimming her.

"Nnn-not a lot of... *pant* guys do that their first time!" Giggled Jean, out of breath.

"I t-think I'm ready to sleep with you now. C-can you g-get in bed on your back and spread your legs?" Asked Luke, his nervousness showing.

Jean grinned and nodded. She crawled into bed, making sure Luke got a good view of her pussy and tailhole as she did. When she reached the pillows she turned around and leaned back, grabbing each thigh in a paw to spread her legs for her first timer lover. Luke almost came on the spot when he saw Jean waiting for him. He almost jumped and bed, but slowed down before actually thrusting in... letting his zebrahood rest above her slit.

"What if I'm no good?" Asked Luke, blushing and looking away.

"No one is great their first time." Laughed Jean. "I once slept with a guy for his first time and he got one thrust in before filling me. Just make it two thrust in and you're already not the worst first timer I've had."

Luke nodded, a thought in the back of his mind that if he came right now he could take that guy's title. He pressed his cock against Jean's pussy, and with a little guidance from Jean found his way in. He slowly slid his whole length in, feeling how soft, warm, and wet Jean's folds felt. When his hips met hers he took a deep breath, he had been too afraid to even breath. It felt good, and he didn't feel like he was going to blow just yet. He pulled out and gave another slow thrust.

"S-see? You're already not the worst I've had, s-so just relax and have fun with this." Smiled Jean, leaning in to give the zebra another kiss.

"Is there anything I-I can do for you?" Gasped Luke, doing his best not to get overwhelmed by the pleasure he was feeling as he thrusted into Jean again.

"Lean in and s-suck on one of my nipples as you... you fuck me, and stop h-holding back and really go at a quick... quicker pace. I-I'm an experienced girl, you won't break me." Said Jean.

Luke obeyed quickly, shifting his paws closer to Jean's shoulders so he could suckle gently on one of Jean's nipples. He stopped making himself hold back and really started humping into her slit. Jean could feel his black member thrusting deep inside her and moaned at the sensation from Luke nursing her nipple. She felt an orgasm start to build within her when Luke moved one of his paws under them and rubbed against Jean's tailhole. After all the rimming he did it slid inside easily, and Jean didn't stand a chance at holding back. Her pussy clenched rhythmically around Luke's cock as she came, moaning loudly in the process. In the living room outside Austin got out of his chair and laughed.

"You were right, he actually made her cum. I guess you win." Grinned Austin as he walked over to Kyle and kneeled down in front of him to give the otter his prize. Kyle pushed down his panties and let his uncut erection flop out. Austin took it into his muzzle and bobbed on it slowly.

"I might have told him what Jean's eruption button was." Blushed Kyle.

"Cheater" Said Austin, lifting off Kyle's cock only to say the one word before hungrily taking the otter's length back into his mouth.

Back in the bedroom, Jean held tightly onto Luke, who was now hugged against her. Now that she had cum the zebra really wasn't holding back anything, and the bed shook as he thrusted heartily into Jean. He could feel Jean's ample breasts pressed against his chest and loved the slick feeling of Jean's cunt. He soon felt the beginning of the end as he felt his balls well up and slap loudly against the otter's rump. Jean could tell Luke wouldn't last much longer, in a few uneven thrusts Luke's equine cock erupted into Jean. She squealed again when she felt the force of his ejaculation within her. With each gooey squirt Luke thrusted into Jean, until cum would gush out every time he pulled back. He grunted as he came, until he ran dry and just leaned forward into Jean, his cock softened in Jean's pussy until it plopped out and the white content's of Jean's treasures poured onto the bed.

"Luke... that's a lot of cum..." Said Jean, examining herself.

"I may... I may have been taking a break from masturbation for about a month and a half..." Gasped Luke, rolling over and lying next to the flooded otter. "Should we go get Kyle and Austin?"

"You do it... if I get up it'll just create more of a mess." Responded Jean.

Luke nodded and rolled out of bed, his hooves clopped on the floor as he walked. Jean looked down at her leaking slit and swiped a finger in the sticky mess, taking her first taste of equine semen. She giggled to herself as she saw that Luke had seen her sample his cum and it pumped a little life into his limp zebrahood, making it throb gently. Luke opened the door in time to see Austin take all of Kyle into his throat.

"See! It just takes practice... oh hi, Luke. We just got a little distracted... is it our turn?" Said Kyle, noticing the zebra watching Austin blow him.

Austin lifted his muzzle off of Kyle's cock, coughing. Kyle patted his boyfriend on the shoulder and both stood up. Luke stared down at their cocks. Austin's canine cock was partially sticking out of the flap in his undies, and Kyle's hood was up. It was Luke's first time seeing either a canine or an uncut cock, so he wanted to take the opportunity to experience everything he could.

"Actually, why don't you guys just sit down and let me take care of you... Austin why don't you take that chair and pull off your briefs, Kyle just pull up a chair next to his." Instructed Luke.

The otter and jackal did as he said and arranged themselves. Luke kneeled in front of Austin and gripped his cock gently with one paw, his other gently gripping Kyle's. Luke tried to maneuver Kyle's foreskin but couldn't quite get it.

"Like this." Said Austin, showing him how to work the otter's cock.

"It's so... weird..." Laughed Luke.

"Yeah, cause yours is so normal." Huffed Kyle, jokingly.

Next, Luke leaned in to Austin. He remembered back to those blowjob instructions he had read online a year ago. He covered his teeth with his lips and lowered his muzzle, letting his tongue caress the underside of the canine member. His other paw worked Kyle's foreskin over his sensitive glans. Austin rested his paw on the back of Luke's head, letting him do short bobs on his cock. Luke's cock slowly throbbed back into life. They sat in silence as Luke sucked off Austin and jerked off Kyle, but Jean broke the silence by calling from the other room.

"Hey, don't forget about me in here. Just because you cream-filled me with a delicious load doesn't mean I won't get bored in here." Called Jean.

Luke quickly jerked up from Austin's lap. The jackal grunted a bit, disappointed, but they all got up and walked naked into Austin's bedroom. They all saw Jean leaning back into the bed, footpaws on the bed but legs spread with a puddle of zebra cum forming at the base of her tail as it dripped in thick glops out of her slit, down her rump, over her tailhole, and down the sides of her rudder. Austin, Kyle, and Luke were speechless, but each shot a small rope of pre onto the floor when they saw her.

"Well boys, we've got plenty of lube." Giggle Jean, playing with some of the creamy white spoo between her fingers.

"Well Luke? What's next?" Asked Kyle.

"Kyle... since you know how to do it could you prep Austin to take me?" Requested Luke, feeling a little more confident.

Austin knew what to do and crawled into bed, raising his tail to let Luke and Kyle get a look at his furry tailhole. Kyle followed him and grabbed Austin's tail in one paw, holding it up while he buried his muzzle between Austin's cheeks, slobbering on and in his pucker. Luke hadn't expected this tactic, not that he minded. After a few minutes of rimming the otter leaned back and got a sticky pawful of zebra cum in his webbed paw and applied it to Austin's tailhole. Austin groaned as Kyle used his fingers to force the thick jizz into the jackal's rump, his canine cock throbbing and dripping pre on the bed. After he was satisfied with the job he had done he moved to the side and made room for Luke.

The zebra grabbed a swipe of his cum from the pool at Jean's rudderbase and slathered his cock with it, then took his position behind Austin. Kyle sat next to them on the bed, watching as Luke pushed his cock slowly against Austin's pucker. Austin bit one of his pillows, it was quite a tight fit for him. When Luke's hips met Austin's rump the zebra only pulled out a little before slowly humping back in.

"Tight..." Groaned Luke as he slid back into Austin.

Kyle crawled around the two and examined Jean's pussy, sliding a few fingers in to her to scoop out some of the cum still left in her depths. He got a pawful of it and then leaned over Luke and Austin. The next time Luke pulled out fully Kyle dripped the hot cum onto the zebra's cock. He groaned when he felt its warmth on his length, and Austin groaned when he felt it get pushed inside him. Luke grunted and started humping into Austin faster. Kyle wondered if this would make Austin splurt, but he knew if it didn't the jackal would be so worked up that he take out his frustrations on him without restraint. He got his answer when Luke let out a loud whinny and bucked into Austin, grunting each time his black cock spurted a powerful stream of cum into the jackal's depths.

"Ah! I can feel it squirting in me!" Yelped Austin, shuddering at the feeling.

Luke held tight on Austin's hips until his length had finished firing its load into the jackal, then fell back. Cum poured from Austin's tailhole, however he didn't care. After a few moments to catch his breath he got up. The look in his eye said everything. Kyle assumed the same position Jean had gotten into for Luke, holding his legs in the air. Just as Austin got ready to penetrate Kyle they heard Luke say: "Wait!"

"What's up, Luke?" Asked Kyle.

"Can you... can you do it to me instead?" Blushed Luke.

Austin and Kyle looked at each other, but knew their response.

"Sorry, but Austin this pent up would be a bit much for a first timer. Let him work off this frustration, then you can try taking me." Replied Kyle.

"That's okay, it looks like Austin's ready to burst and I'd need a lot of prepping for his cock." Smiled Luke, happy to take in a show instead.

With that go ahead Austin grabbed a pawful of zebra cum and slathered his cock with the sticky lube, then placed his cock at Kyle's tailhole and thrusted in, grunting and dripping more zebra cum from his tailhole while he fucked into the otter. Luke could see Kyle's uncut cock throb as he took his boyfriend's member into his tailhole. When Austin's knot rubbed against Kyle's pucker he pulled back out and shoved if in quickly, causing an audible slap when the jackal's knot met resistance against Kyle's rump.

"CareFUL" Squeaked Kyle as Austin brutally fucked into him. "I still need to top Luke, you can't knot me!"

"Gehhh... fuck!" Cried Austin, having to pull back on his almost mechanical thrusts to avoid knotting the otter.

Luke was so enamored by the boys that he didn't notice Jean crawl around them until her muzzle was nuzzling his soft length. Before he could ask her what she was doing she took his flaccid cock into her muzzle, letting it go in as deep as it could. Jean's webbed paws cradled the zebra's balls and soon he was hard again. Austin let out a loud groan and Luke looked up in time to see him go rigid and give one last thrust into Kyle as he spilled his load inside of his boyfriend. Jean looked up and watched her brother cling against their boyfriend as he shot his load inside of him.

Austin slowly pulled out of Kyle and flopped to the side, drained. Kyle sat up and patted the only clean and open spot on the bed. Luke crawled over and assumed the position that Kyle and Jean had. Kyle wiped up some of the zebra cum that had drained out of Austin as the jackal had fucked him and carefully prepped Luke. The zebra breathed in deep as each finger slipped inside of him, and before he knew it Kyle was placing his uncut length at his tailhole.

"Will this make me cum?" Asked Luke, a little nervous.

"It might, it might not. Cumming from just anal stimulation isn't the easiest thing to do. Though I'm sure Jean wouldn't mind helping you out, right Jean?" Replied Kyle, smiling.

"Not at all." Grinned Jean.

"O-okay. I'm ready." Blushed Luke.

Kyle slowly pressed into Luke. Austin sat up and watched as the zebra took his first cock. Kyle gently thrusted in until their hips met, then held it there for a minute before pulling out and repeating the motion. When he felt comfortable thrusting in at a faster tempo Jean got out of bed and walked around until she was able to climb back in over Luke. She leaned down and took the zebra's entire length into her mouth, and left her pussy in his face. She deepthroated Luke as Kyle thrusted into his tailhole. It was such an overwhelming sensation that Luke knew he wouldn't last long. He looked up at Jean's cunt. Not one to spoil an opportunity, Luke lifted his head until he was able to give Jean's slit a slow lick, then another, and soon he was eating her out messily. She giggled around his cock as she bobbed on it.

Kyle was on the edge and as soon as he felt Luke cum it was all over. Luke dropped his head back on the bed and bucked into Jean's muzzle. He fired a barrage of cumshots down Jean's throat. Kyle felt Luke's tailhole clench as he spurted down his sister's throat and couldn't hold back anymore, humping into the zebra's rump, filling his insides with thick otter semen. Jean stayed on his cock until it finished unloading into her, then climbed off Luke and sat on the floor. Kyle slowly pulled out and Luke watched as otter spoo leaked from his stretched tailhole. The zebra relaxed on the bed. No one said anything, just enjoying post orgasmic bliss. Eventually Luke's stomach rumbled and they knew what to do.

"Jean, why don't you help Luke clean up while Austin and I handle the mess in here?" Suggested Kyle.

"Yeah, sure. Come with me striped conquest." Joked Jean, giving Luke her paw. He took it and got up, but as soon as he felt Kyle's load drip from his tailhole he blushed.

"I-is there a good way to get Kyle's spunk out of me?" Asked Luke.

"There's a few, but the best is to just let it happen naturally. Just clench until we get to the shower." Giggled Jean.

Luke and Jean left the room while Austin and Kyle found old underwear they didn't mind ruining to put on. Kyle went to the living area to get dressed while Austin grabbed some clothes from a dresser, then gathered they both up the messy sheets and took them downstairs to the laundry room. Jean let Luke explore her body all he wanted while they showered, but got out after she felt clean enough to let the zebra reflect on this experience and "clean out" in privacy. She got dressed and ordered a pizza, with the boys returning in time for her to hang up the phone. Luke emerged from the bathroom 10 minutes later and they made small talk until their pizza arrived.

"So... most lost virginity... ever!" Laughed Luke.

"Not many guys get to lose theirs like that." Grinned Jean.

"Heh, I wish I'd lost mine like that." Laughed Austin.

"What do you say we work on that project tomorrow night, Luke?" Asked Kyle.

"Yeah, of course." Smiled Luke.

They finished their meal and Jean finished washing their sheets while Kyle and Austin showered. Luke took a much needed rest on the couch. When everything and everyone was clean Luke got dressed and Luke and Kyle returned to their dorms. The next day Kyle found himself in the same exact spot that last night had started: the library's second floor. He checked Twitter and Facebook while he waited for his project partner to show up. The otter heard the telltale clops of zebra hooves and looked up to see Luke walking over to him, with more confidence than Kyle had ever seen him with before.

"Hey, Luke. You look happy." Commented Kyle.

"I just asked out that horse woman from our class." Grinned Luke, proudly.

"What changed? You always were too nervous to talk to her." Replied Kyle.

"After being with you guys last night I'm not afraid to ask people out anymore." Beamed Luke.

"That's amazing! Why don't you sit down and we can get started?" Said Kyle, pulling out a seat.

"Oh, I actually just came to tell you that I was so wired when I got back to my dorm last night that I couldn't sleep, so I just did the project and paper on my own. I emailed it to you before I left to come here. I want you to take a look and get familiar with it for our presentation." Smiled Luke.

"You didn't have to do it all by yourself." Responded Kyle, a bit surprised at the zebra's generosity.

"Just consider it a thanks for last night." Grinned Luke.

"Well, okay. Why not take a seat and walk me through what you've done." Said Kyle, returning Luke's grin.

Luke sat down and pulled out his computer. He pulled up their paper and moved the laptop over so Kyle could read. They spent the next hour in the library, reviewing and editing their project together. Luke found himself much more confident, since the first time he slept with anyone turned into the third time he slept with anyone. He no longer felt so self conscious when talking to people he found attractive, or talking about sex in general. When he graduated he did so without being in a relationship, but he didn't feel bad about it. Austin, Jean, and Kyle had given him the gift of self-assurance. He wouldn't trade that night for anything in the world, and the trio would remember it as the night they helped a guy get on his feet to better enjoy life.