Milking up a new Life

Before this story begins, I just wanted to note that this will be in a somewhat modern AU HTTYD world, it will be told in Hiccup's POV and Toothless will be shown as Anthro.

That's all, enjoy!

Before I tell you how I got to where I am today, I just wanted to state that I did not always live on a milk farm. I grew up in a fairly small town, went to public school like everyone else, and had what I considered to be a normal life.

That is, up until about a few months ago, when everything about my life changed, for the better I should say.

It all began soon after I had turned 18 and graduated high school. At that point, I didn't really know what I wanted to do with my life and my family didn't have the money to send me to college, but I had already decided that it was time for me to live on my own.

My Mom died when I was a baby, so my dad had to raise me all on his own with what little money he had, as a result, we didn't always have enough money for food which did leave me to develop my pencil-thin figure. I have no siblings, but that doesn't mean that it wasn't a challenge for him to raise me.

Despite that, my dad did the best job he could with what he did have and looking back now I do know how hard it was for him to have to go through all of that all on his own, but I survived 18 years and I intend to survive longer.

After graduating high school, I found myself a small studio apartment and moved out, something that my dad supported whole-heartedly as he knew I had to leave the nest at some point.

Anyway, I knew that once I had left Dad's place, I needed a way to get money, so I began job hunting. After two weeks of sending in dead end applications, I was starting to get worried as I knew some bills were going to be coming my way towards the end of the month and I needed a way to pay them while also having enough for food, clothes and whatnot.

That is until I saw an ad in the newspaper one day, yes I read the newspaper but as I couldn't afford a TV at the time and I had a phone, but it was just a basic flip phone. The ad was from a local milk farm with the initials T. N-F. who was looking for a few extra hands at his farm. I actually have always had a bit of a thing for animals, my Dad would take me to local farms and ranches all the time when I was a kid and the owners would show me how to do things like milking a cow or changing horseshoes.

I also was feeling somewhat desperate and was willing to accept about anything, so I call the number on the ad and a guy with a very deep voice, who I presumed to be T. N-F., answered and we talked a bit about the job and what things would look like.

I had to admit that he was somewhat vague with telling me the job details, he pretty much just told me that his farm was all about milk and that it would be a good work. Also, I asked him about how much the job pays and he basically told me that we'll talk after my first 'performance', he oddly seemed to emphasize that word. Honestly, that seemed fair, if I was someone's boss then I'd want to make sure I was giving them money for how well they did their work.

Desperation was bugging me, so I told him I was interested and he said I could come by tomorrow for my first day.

I had to admit, I was both excited and nervous about starting this job, my first job I may add, and I'm sure that whatever this was would at least mean money for me.

So the next day, I take the bus down to the address mentioned in the ad and find myself at the farm. I look up at the sign that said, 'T.H.W. Milk Farm' in black and white so I knew that this was the place. It seemed about what you'd expect, a small wooden farm house with a few sets of stables next to it. I didn't really see any milking equipment, but I figured they were all inside the stables or something like that.

I had dressed up in a pretty simple attire, just a light blue tank top and jeans, because I knew that it was a farm so it probably wouldn't be that formal.

T. N-F. mentioned that he'd be in the first set of stables to my right, so I walk past the house and enter the stables. As soon as I get in, my jaw nearly drops down to the dirt ground and hay below.

In front of me, sitting on top of a hay bale, was a hunk of a dragon who stared at me with a delightful grin. His whole body from head to toe was covered in jet-black scales that glistened against the sunlight as the sun was shining through a window directly to his right. He also had the most beautiful green eyes I've ever seen, eyes that shone brighter than emeralds!

For a second I wasn't even sure if he was real as I've never seen someone so…massive! First off, he wasn't even wearing a shirt, which I understood as it was an incredibly hot day that day and he was probably doing a bit of work before I showed up, and even with those scales I could clearly see his ripping, giant, presumably rock-hard muscles.

His biceps had to be at least the size of my head, his pecs were bulging out way past his chin, his deep-black nipples were bigger than my hand, his abs had a very clear 8-pack, I didn't even know an 8-pack was possible, his wings had to be twice the size of me and his tail, was equally long. Has he worked out every day since he was born or something? That's the only explanation I can think of.

Of course my gay eyes were soon drawn to the massive, head sized bulge that seemed to be barely contained by the red shorts he was wearing. I could only imagine what wonders rested within those shorts.

I must've been staring at that bulge longer than I realized, because I then heard the owner of said bulge clear his throat and make me turn my attention back to his stunning green eyes. "My eyes are up here, you know." He says to me with that same grin in the exact same deep voice that I heard on the phone.

I stammered a bit. "OH, uh, sorry I-"

He then starts laughing while slapping his firm-muscled knee. "I'm just yanking yer chain. Hiccup, right?"

He holds out his giant hand for a shake. "Uh…yeah, I'm Hiccup…sir." I shake it, only to realize that his hand was also twice as big as mine, though he seemed conscious enough to not squish my hand.

He then shakes his head. "Ah, there's no need for the formalities. Call me Toothless. Might I say, yer mighty cute."

I blush so hard that I could actually see my nose turn red. "Uh, thanks…Toothless. So, uh, you gonna..show me around, show me what I'll be doing."

Toothless then stands up and towers over me, being at least 4 feet taller than me. "Hiccup, there's only one thing I need you to do for this job." Before I could even react, he puts his fingers around his red shorts, which were hardly leaving anything to the imagination, and lowers them to the ground, and seconds later, something equally massive springs to life.

Staring in front of me was a 2 foot, bumpy, black cock that extended up to just below his massive pecs. My word, what a beauty it was. I've seen a few cocks in my time, but never one quite as big or impressive. That cock pulsed and throbbed from being exposed to the open air and was already leaking, or should I say, drizzling pre-cum from the watermelon sized balls that hung right below the cock, just inches above the hay covered ground. No wonder he has such muscular legs, those balls must weigh at least 30 pounds each!

Did someone in his family become mates with a horse? There's no possible way anyone can have a cock like that without passing out from blood loss when they get an erection.

Again, catching myself in my gaze, I look back up to Toothless and comment, "…Oh, so it's THAT kind of milking."

Toothless nods. "Indeed. To explain further, you milk me until I'm satisfied, then I'll pay you based on performance. Now, before we go any further, I should tell you this. You do not have to do this job, I know it's a little much to ask since it's your first day, so if you want I can 'take care' of it myself and I can find you some other jo-ohhhhhhhhh!"

He stopped speaking as I began to wrap my arms around his incredibly girthy member, finding that I really did need both arms to wrap around it. Not both hands, arms. I begin to stroke the cock up and down, making Toothless groan loudly as I comment, "Can't really let you walk around with an erection like this, can I?"

It seemed that Toothless couldn't agree more as he bare-ass sits back down on that hay bale, lowering the cock a bit so I could bring it down and begin suckling on the fat tip, drinking up his pre which had a very pleasant sweet and salty taste.

Glancing down, I saw Toothless's presumably hefty balls resting on the ground below and I had to imagine that they must have a ton of sperm stored up so I quickly remove my shirt and toss it to the side as I imagined things were about to get messy.

I squeeze my arms around the cock and tug at it as I suckle on the sensitive head until, only moments later, the cock head expands and I make sure to slip the urethral opening into my mouth as his cock erupts with cum which I try my best to swallow.

It was no easy feat, as there really was a lot of cum that he was releasing, it was like he hasn't had any kind of release for a month and, well, it seemed that my mouth was bigger than my stomach as I soon become so full of cum that the rest just spurted out of my mouth and splattered on me, Toothless's cock, Toothless's legs and the ground. I didn't gag, necessarily, I just couldn't take another drop.

Once he seemed to be empty, which seemed like it took 5 minutes, Toothless lifts his head and looks at my cum-covered self and comments, "Well, I suppose I should've warned you that I do release a LOT of cum, and I even jerked off this morning so it wouldn't be as much." That was only a few hours of storing? Geez, he's got some real cum factories hanging below his cock. "Anyway, really great job, I do feel very much satisfied."

I nod to that. "Thanks. Hey, uh, you got a towel or something?" He picks up the red shorts that he was wearing earlier with his tail and dangles them in front of my face.

I stare at him, wondering if it was ok and he shrugs. "I can just wash it."

With that confirmation, I begin to rub the soft shorts on my face and chest, quickly getting the musky scent of Toothless's balls from inside the shorts, and once I felt like I had gotten enough off of me, I fetch my shirt, pat away the dust, put it back on and thank Toothless before heading out, feeling about as satisfied as he was.

Over the course of the next few days, I pretty much followed the same routine. Every day I would head out to Toothless's farm and give him a 'special service' and then leave. I still had some training to do as I still couldn't swallow an entire load from Toothless, but it is a lot of cum so who can blame me?

However, as I went along, I noticed something…different. Following the first visit, I noticed that my appetite had increased by a ton and I recall that night I ate two cheeseburgers, an extra-large fries and an extra-large chocolate shake.

And that was just the start, after each time I visited Toothless's place and did my job, I noticed my appetite increasing more and more and as a result I had begun to put on a bit of weight. And by a bit of weight, I mean a lot as my stomach went from my usual flat to as round as my head.

It was unusual because all my life I thought I could never put on…anything, be it fat or muscle, though I had to admit it was kind of nice to see some junk in my front trunk for once, if that makes sense.

I also had to admit that it kind of felt good to be bigger for once in my life, so I just went with it.

Each day that passed, I would continue to visit Toothless whenever he requested me, which would often happen multiple times a day, and swallow as much of his creamy load as he had to give, and each time I did my service, I noticed my appetite increasing and increasing and with that I just became bigger and bigger.

It was mostly noticeable in my stomach as 2 weeks after first visit to Toothless's farm, I looked in the mirror and saw that my stomach had expanded to where I looked like I was 6 months pregnant. I also noticed my ass cheeks were getting bigger as well, again going from being pancakes to as big as my hand.

The other big thing to note is my chest was getting just as big if not bigger than my ass, almost starting to look like boobs.

What did Toothless think of all of this added weight, well he actually seems to love me more than my former slim self. Lately he would stand behind me and firmly grasp my newly formed love handles and comment on how it's great that there's now more of me to love.

I had suspected for some time that Toothless knew as well as I did that he's responsible for making me gain this weight, but with how well he's treating me and with how good it feels, I really have no room to complain, in fact I kind of wanted to see how much bigger I can get!

As an added note, I was able to swallow a whole load from Toothless as my stomach had expanded and made much more room for all the dragon baby batter that his cum tanks had to offer, something that Toothless had to admit he was impressed with as well.

It was a month after the first visit that I really started to take notice of my new form. My stomach had expanded so much that I could no longer see my feet when I looked down, my ass had filled out with enough squishy meat that Toothless would often fondle and squish them, and my chest was also bigger, but somehow it felt…different. I couldn't put my finger on it, but somehow it felt like my chest was actually full of something other than fat, though I didn't know what it was.

Then came the other day that truly changed my life.

On that day, I had my back turned to Toothless, inflated ass was pointed directly at him as he grabs my ass with his firm, black hands. Toothless then asks me, "You sure you're ready for this?"

I just nod.

That seemed to be all the confirmation Toothless needed as he lines up the fat tip of his massive cock with my puckering anus and pushes himself inside. I immediately squeal, yes squeal, out from both the pain of having such a large object in my ass, but also excitement as this is the moment I had been waiting for since my first visit.

I'm certain that Toothless made some comment about how tight my ass is, I wasn't really focusing in that moment as I was getting ready to have 2 feet of thick, black dragon cock shoved up my ass.

I was groaning deeply to that cock spreading out my ass and causing my already thick thighs to look even thicker. The old thin me would probably have split into two by this point, so I really was appreciating my new size that much more.

As Toothless was going along, he had reached up from under my armpits and began squeezing and groping my man-boobs and commenting, "Sheesh, these milk bags are full. Must be begging to release something."

What did he say? Milk bags? I mean, my chest certainly wasn't flat, but I highly doubted they actually had milk in them as well. Course I still wasn't thinking that much as Toothless's cock spreading out my ass just felt that good.

As Toothless went along, I could look down and see the tip of his cock bulging through just below my sensitive chest and at the top of my beanbag chair of a stomach. I probably would've fallen right onto the ground if it weren't for Toothless's beefed up arms holding onto me.

Each time Toothless thrusted forward, I could feel the weight of his heavy, black balls smack against the back of my thick legs and I could spot my stomach jiggling each time Toothless pushed his cock back into its spot below my chest.

Then, minutes later, Toothless thrusts one last time and I squealed even louder as I could feel a rush of hot dragon seed being dumped into my ass, inflating my stomach twice as much as it had already been. I also noticed that my chest somehow got this tingling sensation, but thought nothing of it.

That was until, once the heat of Toothless's spunk delivery had died down, he points out, "Well-well, I was right, these things really were full." He comments as he gives my man-tits another firm squeeze.

That was when I glanced down and noticed something that made my eyes widen as much as when I first saw Toothless's fuck pole. It seemed that my nipples had secreted some kind of white fluid that was running down my chest and onto my stomach.

D-did I just LACTATE? Can boys lactate? I was very certain that my chest was not supposed to be leaking milk, but then again I'm also certain that I'm not supposed to have a gallon of dragon batter dumped into my ass.

Toothless runs his sausage-like finger along the trail of man-boob juice coming off of my left tit and extended his tongue to lick his finger. He comments, "Hmm…sweet, sour, salty and just a little bit of spice. Dang, you've got some tasty milk."

I couldn't even respond as my mind was still trying to comprehend the fact that I, a male human, just made and released milk! Not only that, but releasing said milk felt…good. Great, in fact. I felt a good amount of pressure being released from my chest.

Also, since I was so full of cum, I now felt incredibly heavy, like I had a second me inside of me, so I had to lie down on the ground as I could barely even stand let alone walk, something that Toothless helped me out with by laying a very large blanket over me while I relax and let the pleasure in my mind wash over me.

As I lied down, I could actually hear all of the cum in my giant belly slosh and gurgle, which led to a surprisingly pleasant sensation. Toothless then rubs my bloated belly, presumably feeling quite proud of how much he had filled me up both today and this past month, and I felt quite happy to have all of what he had to give in me as I shut my eyes and let my mind rest.

The following days led to other events that further changed my life. I had to sell my apartment as I had just gotten so big and heavy that I could barely move and could no longer fit in a standard apartment doorway. I can actually say that I've gotten bigger than my Dad who was always on the larger side as well.

I also couldn't fit into Toothless's front or back doorway without him having to make new doorways, so he set up a sleeping area in one of the stables, something which I soon found to be quite cozy, even if it isn't technically inside a house.

Toothless soon found a milking machine that he would hook me up to and help drain my leaking man-boobs, the 'product' of which he would bottle and sell at local markets as 'Hiccup's special milk.' There was no real reason for him to keep any of it as he can just take it from the tap whenever he wishes.

Also, I noticed that, for whatever reason, I just couldn't stop lactating. Even minutes after just being milked, I would find myself still constantly dripping tit juice. Neither Toothless nor myself could figure out what was going on as males don't ever lactate, so we kind of just let it slide and see if it gets any worse.

I actually soon got the idea that I might actually be pregnant, especially with how often Toothless fucks me since that first experience.

Speaking of, I do still perform special services to Toothless's cock on a daily basis, something that was even easier and more frequent now that I was living with him, and while I would always be down for sucking Toothless's monster cock or letting the buff dragon fuck me, we do find ways to spice things up, but that's for another day.

Toothless also continues to be my milker as he is very much responsible for the way I look now, not that I was complaining about my figure for a second.

Oh, and for food? Toothless has that all taken care of. Since we now live together, he shares whatever money he makes from my milk with me and buys all the food that I need, which is mostly junk food since that's about all that I crave lately. Many times I will even let him shove food down my throat so I can further practice deepthroating him.

Looking back, I do somewhat miss my former self. I miss being able to walk normally, I miss having clothes (since I've gotten so heavy and massive, no amount of clothing fits me anymore so I'm pretty much always naked these days.), and I miss not having milk constantly dripping from my chest.

But then again, with how well Toothless treats me both with feeding me, milking me and giving me his monster cock, I think I can safely say that I can get used to this new life.