The Wager
The Wager
My name is Nathan, and I made a very foolish bet a few weeks back. But before I get to that, let me tell you a little bit about myself. I recently turned eighteen years old. I live at home with both my folks, and I go to the high school just down the street from where I live. I'm just your average, small-ish coyote with light brown fur and a cream colored belly. I have a slightly athletic build because I like to run, and I'm on the track team, though I stick to myself most of the time. Despite being a pack animal, I always found it difficult to make friends. Up to my junior year in school, I spent my lunch and after school times alone. That is, until I met Owen. I don't really know how it happened. He had been in a couple of classes of mine, and I asked him one day in the library at school for help on a project. And the next thing I know, we were inseparable.
He was much like me, a pack wolf without a pack. He's a plain, grey wolf, with black tips on his ears and tail, and matching black 'socks' and 'gloves'. He's quiet and very unassuming looking. His best talent was blending into the crowd. I always told him he'd make a great spy. And he's amazing with anything related to computers. I always thought he was more machine than animal.
Well, one day after school there was a track meet. Owen showed up to watch me run as he always did. Only this time, he had a proposition. "I bet you guys are gonna lose. No one has ever beaten South Hill's running team," he said, pushing his glasses up his snout.
"What?! Are you mad? Of course we're gonna win. Have you seen our record this year?" I retorted. I lifted my legs to stretch them one at a time and I caught a glance from Owen. I had always expected that he liked me a little more than just a friend, but he never said anything about it, so I just ignored the occasional peeks. "Now, I don't normally bet on anything. I don't have enough money to waste on stuff like that. But I bet you we win this, hands down." I bent over and massaged my paws a little bit to loosen them up.
Owen reached into his back pocket and pulled out his wallet. "All right. One hundred dollars says you guys lose today." He pulled out a one hundred dollar bill and slapped it down on the aluminum table behind the bleachers where we were.
I scratched my head in confusion. "You're seriously going to put a hundred dollars down on us losing? What a friend you are." I picked up the bill and checked that it was real. "You know, I don't have this kind of money. And where did you get this anyways?" I asked him. High school students don't normally carry around large bills, much less large amounts of any bill.
"It's some of my graduation money that my aunt and uncle sent me," he replied plainly, like it was chump change for him. And it probably was. He did computer repairs for a bunch of the students and teachers on campus. "So, are you in or not?"
I looked at the hundred dollar bill again. It was definitely tempting. There was a lot I could do with that kind of money. "I would love to, but I don't have that kind of money to spare. I gotta make the car and insurance payments, and my lovely minimum wage job barely covers that alone."
"Well that's all right. You don't have to put up any money," he said in a comforting tone. I hated when he talked down to me like that. I know he doesn't mean anything by it, but it still makes me feel like he's trying to be superior. "How about this? If you win, you get the money. And if I win, I get you..."
"You get me? You get me, what?" I was genuinely confused. I cocked my head to the side, trying to understand what he was getting at. "Uh, Owen, I don't think that's how bets work. But I'm in. It sounds like I win either way."
"Oh, we'll see. We'll see. Now scoot! Your turn is coming up soon," he ushered me away. Owen is my friend, and I know him fairly well. But I was getting a knot in the pit of my stomach trying to wrap my head around what he was talking about.
The coach saw me come from around the bleachers and ran up to me. "Nathan! There you are. I was beginning to worry you skipped out," the burly bear of a coach said to me as we walked towards the side of the track.
"I never run out on an obligation, coach. You know that," I answered. I stretched my back and shoulders a little, trying to loosen up and forget about what Owen has said.
"Good. That's what I like to hear. Now, we're in a bit of trouble here. We need you to win this match. Otherwise, I don't think we can make enough points, and there goes our perfect record this year," he said. We reached a bench by the track, and I picked up my water bottle that I had left there and took a drink.
"What about the others?" I asked. It all couldn't possibly be left up to me now.
"We're neck and neck right now, which is why I need you to pull us through all this. It's up to you Nathan. Now go knock 'em dead!" The coach slapped my back and shoved me towards the starting line. I was really worried now. I never work well under this kind of pressure. I had to focus on the race, but I just couldn't clear my mind. The next thing I knew, the starting gun went off and I instinctively took off down the track. All was going well at first. I had taken the lead right off the bat, but the South Hills runner was catching up fast. We were running side by side through most of the track. As we rounded the last corner, I took a glance in the bleachers and saw Owen sitting there, cheering me on. And that's when it happened. With all the things running through my head, I lost track of what I was doing. My paws tripped over themselves, and I fell face first into the dirt track. Needless to say, I let the whole school down. The coach and Owen were down by my side instantly, picking me up and taking me off the track.
I was still worried about our bet while the school nurse was icing my scraped up chin, but he didn't say anything about it. I didn't bother showering up after the race because I still had to walk home, and I'd clean myself up in the privacy of my home. Owen met me out in front of the school, and we started walking home together like we had since we had met. He conveniently lived just a few houses down from my own. "So, am I still staying over?" he asked as we neared his house.
"Yeah. Bring some stuff for a few days," I replied. My folks were both out of town on business trips for a week. So I had the whole house to myself. We waved goodbye to each other and I made my way down the street to my house. I opened the door and stepped inside, throwing my backpack on the couch. As I made my way to the bathroom, I slowly stripped off my clothes and left them where ever they landed. The warm water felt good against my fur, and helped calm me down. After my shower, I stood in front of the mirror, staring at my face. I still couldn't believe I fell like I had. I had never let anyone down so bad before.
I heard the doorbell ring and wrapped the towel around my waist. I figured it was just Owen, so I didn't bother throwing any pants on. We showered together during gym class, so I didn't have anything he hadn't already seen. "Hey, Owen. Did you bring everything you need?"
"Oh, I sure did," he replied. He had a couple of small bags. It was typical for a week long sleepover. "Oh! I also have this for you," he added, pulling out a small, black plastic bag from his own bag. "Don't think I forgot about our little bet."
My stomach turned in knots. I didn't know what he had in store for me. I thought it was going to be something silly. "What did you get me?"
"Just go put it on. You owe me now, don't forget," he answered. He picked up his bags and started down towards my room. I stood there, struck dumb, not knowing what to do. I figured it wouldn't be too terrible, knowing him like I did. I stepped back into the bathroom and opened the bag. To my horror, I discovered something I never would have thought. I stuck my head out the bathroom door and yelled, "You have got to be kidding me!"
"A bet is a bet, Nate," was all I got from down the hallway. I grimaced at the thought of wearing this stuff, but a bet is a bet, and a debt must be paid. It took me a little while to get dressed, and even longer to get the courage to leave the safety of the bathroom. Finally I just burst out and hurried down the hallway to my room, where Owen was lying down on my bed reading a book. I stood in the doorway, trying not to make a sound. I was wearing a small, white, sleeveless t-shirt that was way too short and exposed my creamy belly, and a pink miniskirt. Underneath that was a pink pair of panties with white hearts on them that barely contained anything.
"Well you sure took your sweet... time," Owen paused after speaking, just staring at me. I saw his eyes roam all over my body and the clothes that he was forcing me to wear for him. I couldn't help but blush and fidget under my friend's eyes. I crossed my legs, hid my tail between them, and tried as hard as I could to pull that tiny skirt down over myself to no avail. Owen stood and walked over towards me. "You look amazing."
"What? What are you talking ab..." but I was cut short as he pressed his lips against mine. It wasn't a long or rough kiss, but it was enough to make me wonder.
"I knew you'd have the perfect legs for this," he chuckled as he gently led my way into the room. I didn't know what he wanted me to do. I thought he just wanted me to dress up, and that was it. But that kiss told me something completely different. And it definitely unveiled some of Owen's secrets he held about me. He led me to my bed and sat me down. I had to cross my legs to keep everything hidden. It was an unusual act that I was not used to. "Now I get you," Owen said, then without me even noticing, he wrapped a collar around my neck and clicked it shut.
"What!? What are you talking about?" I said, tugging on the tight, red collar now around my neck.
Owen pulled a leash out of one of his bags and attached one end to my collar, and tied the other end around some of the bars on the headrest of my bed. "It was all a part of our little bet. If you win, you get the money. And if I win, I get you," he said, now pulling off his shirt and throwing it to the floor. Looking at him now, I never realized how big he actually looked. I knew he went to the gym, but I never saw the muscle tone he had. It wasn't massive, but it was noticeable. Somehow, that quiet, nerdy computer whiz I once knew had turned into a toned, dominant male.
"What... what are you going to do to me?" I whimpered. It was now painfully obvious what he intended, but I wanted to hear it from his mouth before I made any assumptions.
"It's all right, Nate. Trust me, ok?" he said, a hint of compassion in his voice. And for some reason, I seemed more relaxed after he spoke to me. I was still worried about everything, but I wasn't tensed up anymore. He reached out and touched my fur, gently rubbing up and down as he scooted closer to me. His hand ran up and down my belly and chest, slipping up underneath my shirt. His other hand rested on my exposed thigh.
Gently, both his hands crept up my body, sending shivers down my spine. He raised my arms in the air, and together, we rose higher on the bed. He grasped my wrists, and we hung there, centimeters apart from each other. I had no idea what had come over me. I was just letting him touch me like that. I didn't think I had any sort of feelings toward Owen like this, but my actions spoke otherwise.
I could feel my member slipping from its sheath, poking upward over the panties and pushing the miniskirt out of the way. Looking down in between us, I could see the pink tip of my penis peeking out from under the skirt. And Owen definitely had a noticeable bulge in his own pants. With a firm hand, he turned me around so I was facing the headrest. Still holding on to my wrists, he produced a pair of handcuffs, and cuffed me to the bar where my leash was tied. Now I was bent over on my bed, my arms out in front of me.
I could feel Owen's hot breath all over my back as he leaned in close, taking in my scent and giving the odd kiss or two all the way down my back. I shivered, and my tail instinctively lifted, giving better access. I was overcome with this feeling; this desire. It was like something feral that had been locked up inside me was finally released. I could feel my heartbeat quicken, and I began panting for breath. I wanted it; needed it.
I heard the familiar sound of a zipper behind me, then the soft sound of cloth hitting a carpeted floor. Owen's hands rested on my hips, and I could feel his tight grip. He reached under the skirt and hooked his fingers under my panties and began to slowly pull them down. The feeling of the soft fabric rubbing against me felt amazing, and I let out a little whimper, wanting more. When my, now erect, member was freed from its silky prison, both it and my balls bounced out.
The panties were now only hooked around one ankle, while my skirt was still in place. Owen lifted the back end of the skirt, and rubbed my attention needing ass. I wiggled underneath his teasing touch, letting out a moan of pleasure. I had never had anyone touch me like this before, and I was enjoying my first experience of it all. And, for some reason, I was glad that it was my best friend with me here.
Owen then reached underneath me and began to fondle my balls. I let out a little gasp at his touch, but it was not want I needed. To emphasize what I wanted, I placed my head on my pillow and raised my ass as far into the air as I could manage. He got the message as I heard him chuckle and back away. Suddenly I felt alone and exposed on my bed. But that was soon replaced by a cold, slimy feeling against my virgin hole. That I had not been expecting, and I reactively recoiled from it. But Owen had gotten a firm grip on my cock at the same time, and kept me in place.
He was distracting me by giving little, playful squeezes to my cock while he lubed up my hole. But all the distraction in the world couldn't pry my attention from there when I felt him slip a digit inside me. I had secretly done this once or twice on my own before, but it was a whole different sensation when someone else was doing it. I practically started panting as I felt him probe deeper into me, then pull out. I felt him lean all the way over me until his mouth was right next to my ear. I could also feel his own member now pressing up against my hole. It was all almost too much to handle. "Are you ready? I'll start out slow," he whispered into my ear. I gave a little nod and prepared myself for what I had been yearning for since this all started.
"Please be careful. It's... it's my first time," I squeaked out sheepishly.
Owen leaned back again, and I heard him say, "Me too." Then I felt it. He started pressing against my hole, and I could feel the slickened tip of his wolf cock penetrate me.
"Ah!" I gasped out as his member invaded me. He stopped for a moment before continuing forward. He had used enough lube so that it wasn't too painful to enter. He slid in rather smoothly for it being my first time. But it felt like my rear was on fire. I almost told him to get out, but I didn't. I wanted to feel him inside me, even if it hurt. And it didn't for very long. It quickly went away, and was replaced with a pleasurable sensation.
It felt just like how I imagined it would. I had fantasized about being taken like a bitch before; though I had always thought of myself as straight. Owen continued pushing deeper into me, and that banished any thought of females. I only wanted him inside me. His length was thicker than I had imagined, and it took some getting used to. But he was slow and gentle enough that it took almost no time at all before I was begging for him to go faster.
And faster was what I got. He started thrusting himself into me faster and harder with every passing moment. I swear I could feel every throb of every vein on his cock inside me. Pre dripped freely from my cock and dribbled onto the front half of the skirt I was still wearing. My tongue hung loosely from my mouth as I panted for every breath. His thrusts were getting stronger, and I could feel his growing knot smack against my hole with every one. The bed beneath us creaked and rocked with our movements.
Owen had begun fucking me wildly now. He leaned over my body and bit lightly into my shoulder. I gasped and moaned as he placed both his arms on either side of me. I didn't think I could take his knot; it was larger than I thought possible. But he was determined to tie with me. I could feel him push harder and harder with every thrust, grunting with the exertion. Then it finally happened. My anus spread wide open for him, and he tied with me. The feeling of being so full sent me over the edge. I came, spilling my seed all over the inside of my skirt, dripping onto the bed beneath me.
I felt my muscles spasm and tighten all over with each heartbeat. It was most intense orgasm I had ever had. I don't know how many jets of my cum shot out of me, but that skirt is ruined now. Owen could feel it too, as I heard him moan into my shoulder as I came. He furiously fucked my hole as my muscles tightened around his member. It wasn't long before I felt him give one last, final push as deep into me as he could go. His cock, buried deep inside me throbbed and pulsed as he shot load after load of his seed into me. The jets of creamy liquid warmed my insides, and filled me more than I thought I could be.
We sat there motionless for a while, catching our breaths. Owen released my shoulder and licked the spot tenderly. One arm lifted from the bed and ran up and down my full belly. After a few more moments of cooling down, he reached up and unlocked the handcuffs, but left the leash tied to the headrest. My hands, now free, fell down to rest on the bed and give me a little extra support. "Thank you," I said to him. And I really meant it. My first time had been amazing, and with someone I cared about, though I hardly knew I did in that way.
"No, thank you, Nathan," he said back. He wrapped his arms around my waist and we both gently fell over onto our sides. His knot was still buried inside me, but I didn't mind at all. I could wait in his arms for as long as it took. He nuzzled into the back of my neck as we lay there together.
I closed my eyes and breathed deeply, taking in the musk and the scent of sex and sweat. When I opened my eyes again, I noticed something odd, hidden underneath a shirt on my dresser. "Has that little red light been on the whole time?"