The Best Prize Ever

by StormLuna

Rating: mature
Tags: Twilight Sparkle, Anthro, My Little Pony: Friendship is Magic, Human, Romance, Porn, Self Insert, Sex
Length: 5515

After winning a trip to Equestria at a pony convention, I met Twilight as soon as I got there. We got to talking and after she got to know me and know what I like, things went in a direction I never imagined.

After winning a trip to Equestria at a pony convention, the first pony I met was Twilight Sparkle. Once she got to know me and what I like, things took a turn in a direction that I never expected. One thing was for sure, my trip to Equestria was going to be better than I ever imagined.

Humans and anthro ponies co-exist in this story.

Story includes: M/F, breastfeeding, bodily fluid consumption, oral, vaginal

Cover art source: https://derpibooru.org/images/2253735

Published 2022-01-14 00:00:02 UTC
Last updated 2022-01-14 00:00:02 UTC

Prelude: Winning the Trip to Equestria

Prelude: Winning the Trip to Equestria

It was Sunday afternoon and the pony convention I had went to was drawing to a close. This convention was something I had been looking forward to for a very long time. Some people thought I was crazy but I had been saving up for two years to attend it so I could stay in the hotel it was taking place, eat better food than fast food and hopefully get a couple of plushies, plushies that most people would not spend a ton of money on. The ones planned on getting were of Twilight Sparkle since she was by far my favorite pony. After realizing I wasn't hurting for money, I decided that I would get one of her both as a unicorn and as an Alicorn. That is how much I loved her, I wanted to get a plushie of her in both forms.

All seemed to be going according to plan when I arrived but then I learned about a grand prize that was a trip to Equestria, I was shocked. It was something that every single brony I ever knew would want so badly and here was a chance for me to maybe go. I then began to think otherwise because seriously, something like that has to be a scam. I thought that until I wound up meeting with some previous winners who had actually won trips to Equestria. I remember asking them why the hell they'd come back, I asked them why they didn't stay in Equestria.

Well their reasoning was rather ridiculous to me. They told me that it was an anthro version of Equestria and that it wasn't what they hoped for, it wasn't exactly like it was in the show. Me, that actually made me want to go even more. The fact that the ponies walked upright and had other human features caused me to start thinking about thoughts most people would ostracize me over, dreams of having something special with her.

I then learned another thing, I learned that there were a couple of winners who actually chose to stay in Equestria. What they did there after staying I wasn't sure but I did hope for one thing, I hoped that they didn't win Twilight's heart and hook up with her because a chance to win her heart was my dream come true! Now it was just a matter of buying enough raffle tickets to win the trip. Once I discovered that this was legit, I could win a trip to the one place I have fantasized about for so long and hopefully meet and maybe even hook up with the mare that had been my waifu since the very first episode, I scrapped all plans of buying plushies. I instead spend a great amount of money on raffle tickets, only leaving myself enough money for food and lodging, which were things that I would obviously need.

I met a fair amount of people at the convention, some of who had the same desires involving Twilight that I did. We ultimately couldn't stand to be around one another because we began to argue over who would get to go and who would wind up winning Twilight's heart and maybe share an eternity with her. Other people however, they thought people like me were nuts, wanting to get with Twilight like that. One guy really pissed me off though, he brought up Flash Sentry and I naturally put him in his place and brought up how they have never even interacted. Face it, that only happened in Equestria Girls so in all reality, she had never even met him.

Finally Sunday afternoon arrived and the convention was winding down. Some people had already left but those of us who had bought raffle tickets, well us along with the vendors, were staying until the very end. Some people only had one raffle ticket while some of us had well in excess of fifty. Me, I bought a hundred so discovering if one of my tickets was the winner would probably take a while.

At the very end they brought out a mirror and activated it. The head of the convention came out, activated it and began, "We'd all like to thank you for coming this year but we are sad to announce that with Friendship is Magic being over, this will be the final convention." He paused for a moment before adding, "Now I see that some of you have purchased a lot of tickets so we will give you time to go through them after we announce the winning number."

The room went dead silent when he pulled a ticket out of a basket and announced, "And the winning number is 7890513."

We all began to go through our tickets and as I continued to go through them, I seriously began to think that I had spent a massive amount of money on raffle tickets only to not win but when I hit my 100th and final ticket, the number on it read "7890513."

I dropped all my other tickets, held it up and immediately began to jump, scream and yell, "Yes, I did it, I did it, I won! I'm going to Equestria!"

Some people around me embraced me and congratulated me but another guy, not too far away from me, threw all his tickets down and stormed out of the hall as I excitedly headed up to the stage, ready to begin a new phase in my life, hopefully one with Twilight.

Once I got up to the stage the guy running it said, "Congratulations! You are the final one who will being going to Equestria and with that being the case, whether you like it there or not, you will not be able to come home."

I exclaimed, "That doesn't matter to me, I get to go and meet Twilight and her friends and hopefully win her heart!"

The guy laughed because apparently no one else had ever openly admitted they wanted to win Twilight's heart. He led me to the mirror and said, "Well hopefully you'll win Twilight's heart and just so you know, this is an anthro version of Equestria you're going to so it might happen."

I pumped my fist towards the ceiling, "Sweet, I bet she is going to be so beautiful and maybe even want me forever!"

The guy rolled his eyes before saying, "Well good luck on winning over Twilight!"

I gave the remaining crowd, which by this time was very small, one last smile and gave one final fist pump before heading into the mirror. I wasn't sure what exactly to expect upon arrival but I did hope that I would come out in Twilight's chambers with her there, ready to greet me and welcome me to Equestria and if I were lucky, we could get to know one another and take things from there.

Getting to Know Me

Once I had stepped into the mirror I was unsure of exactly what would happen but as I was going through it to Equestria, I was flying through a swirling portal of colors. It was one of those things that one would think of when one was on a psychedelic acid trip back in the late 60s. When I finally came through the other end, I crashed head first and I found myself laying on a stone floor.

I was wondering where exactly I was until I saw a lavender colored hand reach down, grab mine and pull me up. Once I was up I saw where I had came out and I was ecstatic. There standing right in front of me was none other than the Princess of Friendship herself, Twilight Sparkle. She gave me a smile and said, "Welcome to Equestria!"

Hearing her voice in person was a dream come true for me but that was nothing once I saw those gorgeous purple eyes, I immediately became lost in them. I continued to be in a daze until she continued, "Like what you see?"

I finally snapped out of it and replied, "I'm sorry your Majesty...."

She quickly cut me off, "Just call me Twilight for now, alright." She paused momentarily before adding, "And who knows, maybe I'll even let you call me Twily if things go right!"

Wow, just wow! Was this her way of saying I might have a chance with her? I certainly hoped so but I knew that I couldn't simply be lost in her the way I am if I was to actually win her over. The first thing I knew I had to introduce myself her, "Twilight, I'm sorry I've been in such a daze. My name is Luke."

She gave me a smile, "Oh it is nothing to worry about, every single winner has been lost in my eyes when they first see me but I must say, Luke is an incredibly sexy name." She then pointed to a chair at a desk and suggested, "How about we get to know one another some, well I guess it is more a matter of me getting to know you. Every single winner seems to know a fair amount about me."

This was my chance to maybe win her over. Now I was nothing special in my world but I knew how Twilight was, she wouldn't expect someone to be a millionaire or have a PhD or anything like that to win her over.

I began, "Well in my world I work as the manager at a convenience store. The pay is decent....."

She cut me off, "A manager? So you're fairly well accomplished then?"

I personally didn't think I was but one thing I knew that Twilight liked in folks was confidence but not cockiness. I replied, "Yeah, you could say that. I worked hard to get to my position."

Twilight smiled, "A hard worker, I like that!" She paused for a moment before continuing, "Enough about your job because that doesn't matter anymore. So what kind of things do you enjoy in life, what kinds of hobbies do you have and were you close to your family?"

This was something that I wasn't overly worried about how Twilight would react so I wasn't nervous as I replied, "Well I like sports, sports like football and hockey. I also like to play cards" I saw her begin to frown and added, "just for fun. I don't gamble if that is what you're thinking." The smile returned as I continued, "My family, well we were fairly close until they discovered I like My Little Pony. After that, they thought I was weird and began to distance themselves from me."

Twilight shook her head and sighed, "You know, I have heard that a lot and I don't get how a family could react that way over someone liking a wholesome TV show, it isn't like you got addicted to shows about hunting or anything like that!"

"Hunting shows? That definitely isn't my thing, just a bunch of guys out killing things for ratings."

"Mhmm!" Twilight continued with the smile, "What about relationships? Have you had any of those?"

This is one thing that caused me to freeze. I knew that Twilight was rather extroverted while I was very introverted. Then it hit me, at one time she was very introverted so she'd hopefully understand how I was. I replied, "Well I've never had a relationship before because I'm kind of nervous interacting like that and I really fear rejection."

Twilight gave me a bigger smile, "I know what it is like to be introverted so I know where you're coming from." She then scooted down to the foot of her bed and asked, "What do you like in a woman? What kind of a personality do you like and what type of a woman do you find attractive?"

I froze when she asked me this. Here she was asking me what I liked in a woman and brought up what I find attractive. I knew that this was perhaps my chance to either win over her heart or maybe wind up losing that chance. If I lost it, what would I do here in Equestria? Given the line of work I'm experienced in I'd likely have to move to a big city but what if I impressed her? Would I get to stay with her forever and become hers?"

After a brief moment of hesitation I replied, "Well I like women who are kind, sweet, understanding, caring, have a great amount of empathy and I will admit, I find intelligence very attractive."

"Mhmm!" she giggled, "And what about physical appearance? Certainly there must be certain body types you find hotter than others!"

This was something that kind of unnerved me. The thing is, Twilight was a bit chubby, she had curves and big hips. She was basically everything I looked for in a woman, she had goddess level beauty and was the exact definition of sexy in my eyes but I was afraid that she'd think I was simply saying it, although maybe if I gazed directly into her eyes she'd know I was telling the truth.

I leaned forward and began, "Twilight, what I find attractive in a woman is what you have. I find women who are a bit chubby, women with curves and big hips so incredibly beautiful, so incredibly sexy!"

She gave me a smile and pointed towards her average sized breasts, "So you don't demand that a girl have F cup tits?"

I replied, "Not at all. Twilight, like what I said, you have everything I find attractive in a woman....well a mare in your case."

She got up and headed towards what was most likely a walk in closet and giggled, "Well then, how about you get to see my incredibly sexy body in much more detail! You're the only one who I've ever even thought about showing my body to." She winked at me and said, "I'll be back shortly!"

Wow, just wow! I could feel it, I had a feeling that I was well on my way to winning over Twilight. What would I have to do to fully win her over? She said that she had never even thought about showing her body to anyone else. Does that mean that if she was to want sex that I would be the one to take her virginity? If that was the case, my ultimate dream would come true. My dream of taking the virginity of the sexiest pony of all would come true!

Fulfilling Our Fantasies

Five minutes later Twilight came out of her closet dressed in nothing more than a light pink bra and a matching pair of panties, panties that were clearly too small for her. My jaw dropped open, "Twi-Twi-Twilight!"

Twilight gave me a smile and suggested, "How about you strip down to just your underwear, I really want to see your body in much more detail."

This unnerved me a bit because I was no body builder, I didn't have ripped abs, huge biceps and to make matters worse, I had a bit of a spare tire but Twilight wanted me to expose myself so that is exactly what I did. Once I had stripped down to my boxers she licked her lips and commented, "I like what I see, I really like what I see!"

I was in a state of shock. Here I was, an average human male with a bit of a spare tire yet she really liked what she saw. "You do?" I questioned, "You really like what you see?"

Twilight approached me and stroked my stomach as she giggled, "Of course I do, you look natural." She paused before adding, "Past winners, the ones who I never let things go this far with, normally went over to visit Rarity after I threw them out. She told me about how their bodies were built and the truth is, such builds just aren't that attractive to me. The thing is, those guys seemed to have rather big egos but you my sweet Luke, you are perfect!"

Oh my goodness, she referred to me as her sweet Luke. Now I knew that chances were my dreams of becoming hers were much higher but still, I'm sure there was a chance I could still blow things. Twilight then stroked my fully erect member and giggled, "I must really turn you on!"

I took in her whole sexy body and replied, "You do Twilight....."

"Just Twily please and now, the time has come for us to get to know one another on a whole new level, a level I never imagined I would with anyone."

I gave her a smile as I replied, "Twilight....."

She then cut me off, "That is Twily to you now, there is no need to be so formal!"

Yes, I could simply call her Twily now. That moment of becoming hers was so close, I could feel it. I still however knew that it wasn't guaranteed so I had to keep on staying in her good graces and hopefully wow her when the time came. With the sexiest mare in existence standing in front of me, I began to fantasize about things, things that she may not like or things she may love.

I approached her and asked, "Twily, can I do something? Do you think I could do something I have only ever imagined of?"

Twilight giggled, "Are you talking about a fetish? If so, do it!"

I gave her a smile and then I got down on my hands and knees before grabbing her underwear with my teeth and beginning to pull them down. Twilight began to giggle as I was doing this, "An underwear fetish? I like that, no, I love it!"

I stopped and gasped, "You do?"

Twilight replied, "I do." Her voice became more demanding as she added, "Now get back to it stud! My underwear won't remove themselves!"

I got back to work and once I had got them down to her ankles, she stepped out of them and then I did another thing I wanted to do. I put the part that was right under her marehood in my mouth and began to suck on it and oh my goodness, it tasted so good!

Twilight saw that and giggled, "Wow, I'm loving this underwear fetish of yours more and more!"

I gave her a smile and then took her underwear and forced my head through one of the leg holes. She gave me a smile, reached down and grabbed me as she was giving me a very seductive smile, "You must love my underwear, huh?" I nodded and she added, "Well my underwear are one thing, I am another and trust me, you'll love me a whole lot more!"

I blushed at the prospects of what she meant by that and then she removed her bra, fully exposing her body. Her breasts weren't huge, C or maybe D cups, but they looked so natural. They didn't look like beach balls strapped to her body. She saw me eyeballing them and suggested, "How about we go over to my bed and you can taste them?" She then reached down and removed by boxers before adding, "After you shed these things, we can't lay together if all of you isn't fully available for me!"

Once she removed my boxers she looked down at my fully erect penis with a look I couldn't quite read. I knew that stallions had larger penises than humans do and wondered if she knew well enough that it would not provide her with the pleasure that she would desire, that maybe it wouldn't be long enough to penetrate her. I couldn't worry about that at that moment though because she was wanting us to lay together and for me to taste her breasts.

She was sitting up against her pillows and she pulled me down to where my head was level with her tits, at a level so I could suck on them and feed off of them if I were a newborn and she was a nursing mother. I moved in and began to suck on them, causing her to start moaning. She began to rub her hand through my hair as she was moaning, "Oh Luke baby, that feels so good!"

I wanted to give her even more pleasure so I intensified my sucking and while my eyes were closed, I could sense a light coming from above, a dark pink light. It wasn't long after that until I knew what had happened, she cast a lactation spell because suddenly milk was flowing straight into my mouth, very tasty milk. I wrapped my arms around her and forced my face deep into her larger tit.

As I continued to drink she continued to moan out my name and as I was drinking her milk, I began to feel my member not only growing in length but I began to feel it getting bigger around. I wasn't going to show it but that was making me very happy because I knew that I would be able to provide her with the pleasure that she was so deserving of.

Once I finished drinking that one, I gave her a huge smile, "Oh Twily, I have never tasted anything so good before in my life and damn, I felt myself growing as I drank it!"

She giggled, "Oh just wait until my girl gets him, it will be like a slice of heave for you." She pointed towards her other breast and ordered, "For now though, you have one more. After all, it isn't very nice to leave one all full and bloated!"

I then took to her other breast and began to drink from it too. The milk in that one seemed even sweeter than the other one. It was kind of odd, as I drank from it I began to feel shivers going up and down my spine while my desire to be with her became stronger and stronger. By the time I had drank it dry, I had gotten to the point where I would do anything to be with her, and I mean anything!

After drinking it dry I gave her a smile and said, "Oh Twily, that was the sweetest thing I have ever tasted!"

Twilight giggled, "Oh just wait, you're about to get something even sweeter but for now, how about we bond in a way I have always dreamed of?"

Before I could respond, she pulled us onto our sides and we began to kiss one another passionately. It was a very wet, open mouthed kiss. I was feeling ecstatic as I could feel her saliva flowing freely into my mouth, saliva that I greedily swallowed. It wasn't long after that until we began to massage one another and grind our bodies, producing plenty of body heat and getting ourselves all sweaty and sticky. That is another thing I had always fantasized about, having a hot, sweaty sticky body wrapped around mine. As we laid there bonding, I was so excited wondering what was yet to come. I did know one thing though, I was pretty sure that both of us would no longer be pure by the time the day was over.

After an hour of cuddling and kissing, Twilight broke us apart and suggested, "What do you say we share ourselves? I'm sure both of us have been pure for far too long, it is time to change that!"

I agreed with her and then she laid out on the bed and lifting one of her legs up, pointing to her inner thigh and then my head. I knew exactly what it was and I was more than excited for us to engage in what it was she wanted. I knew that she was going to wind up tasting so good and the very thoughts of her sucking on my member and the feeling of her tongue caressing me was making me so hot that I could already feel myself wanting to cum. She saw this and sighed, "Not yet Luke, not yet! You're not even in my mouth yet!"

I blushed, "I'm sorry Twily, the thoughts of us doing this has me so excited!"

She again pointed towards her inner thigh so I got into the right position and laid my head down right onto her. Her inner thigh was softer than any pillow I had ever laid on. I too raised one of my legs and she laid her head on mine. She immediately shoved my whole member into my mouth and began to suck on it gently. I then took to her marehood and began to suck on it.

As her sucking intensified and I felt her tongue massaging my member, I began to feel shockwaves going throughout my body. Never before had I felt anything so wonderful in my life. I began to let out muffled moans as she started thrusting it and her saliva was providing extra lubricant, making it feel all the better.

As I was sucking her and probing her, I was taking in how truly sweet she tasted. I felt warmth flowing through my body as small amounts of her cum had begun to flow into my mouth, warmth that provided me with a tingling sensation. As we continued to suck on one another, our breathing intensified and the muffled moans we were giving got louder and louder. Soon both of us could feel it coming.

I began to feel a bit light headed as I felt myself ready to unload into her mouth and right before the two of us climaxed together, I felt what was likely magic. When we finally climaxed, my body shook as I began to unload into her mouth and as she started to unload into my mouth, the warmth I felt throughout my body became greater and greater. It was odd though, her cum was flowing into my mouth like a fountain rather than exploding into it. I began to feel light headed as she continued to provide me with more and more nectar. I wasn't sure how long she continued to release but when she finally exhausted her supply, I was in a daze....such a daze that I barely knew what was going on.

When I was finally coherent, we were laying in bed gazing lovingly into one another's eyes. I gave her a loving smile, "Twily, that was amazing! I never knew such pleasure existed!"

Twilight giggled, "Once you've built your supply back up, you'll feel the ultimate amount of pleasure!"

We pulled one another into a passionate kiss and I realized that our special moment was almost here! Twilight and I had done so much so far but that final test, the moment I have to wow her was almost here. Very soon we were going to share our virginity with one another and hopefully forge something special that would last for all eternity.

After another hour of kissing, she broke the kiss, got on her back and spread her legs wide. The time has come my sweet Luke, the time has come for us to forge something special, the time has come for us to become one.

There she went with it again, calling me "my sweet Luke." I could tell by this point that she had developed feelings for me far beyond that of simply being a contest winner that she wanted to get it on with, perhaps she even saw me as her special somepony by this point. I did know though that it would not be long before I would find out.

I crawled up on top of her, aligned my member with her marehood and asked, "Are you ready for this Twily?"

Twilight replied, "I am but please be gentle, I'm still a virgin."

I gave her a smile before I began to give her what both of us clearly wanted so badly. We both gasped in delight as I entered her. I could see the nervousness in her eyes as I continued to push further back. I too was nervous because I didn't want to hurt her any. Finally I felt myself hit a barrier, a barrier that gave way rather easily. She wrapped herself tightly around me and let out a painful scream as she sank her fingernails into my back. Now that was very painful but it was likely nothing compared to what she was feeling.

Once she had stopped screaming I asked, "Twily, are you ok? Do you want me to stop?"

Twilight yelled, "No, just lay still for a minute! I'll let you know when you can continue but take it slow alright, I want our moment to last for more than just a brief moment!"

I laid there for a moment until she nodded and gave me the go ahead. I was thrusting her gently and oh my goodness it felt so good. She was so hot, wet and tight and she only became tighter when she wrapped her legs around me, tightening her hold on me further. It felt like my member was in the loving embrace of her marehood, an embrace that felt like a slice of heaven.

As I continued to thrust her gently, we were both moaning gently, gazing lovingly into one another's eyes before we closed them and engaged in a deep, passionate kiss. We then wrapped our bodies more tightly together and began to grind again, working up a good sweat. We continued to lay there making gentle love and soon I could tell it was coming, for both of us.

She broke the kiss and moaned, "Oh Luke baby, I'm gonna, I'm gonna!"

I was moaning louder too as I knew the time was coming. I then felt her grasp me in her magic and she cast a spell of some sort. Suddenly I didn't feel like I was going to climax yet she very quickly did climax. As I continued to gently rock inside of her, our moans became muffled as we once again engaged in another deep, passionate kiss.

She had to have climaxed a good dozen times before I finally felt it coming. I broke our kiss and moaned loudly, "Oh Twily baby, Oh Twily baby, I'm gonna, I'm gonna!"

She two was moaning loudly but just as I was about to unload into her, I felt her cast not one but two spells on me. The moment I began to unload into her, shockwaves of pure pleasure and warmth were surging through my body as I continued to unload and unload into her. Something didn't seem right though, there was no way I should have been able to continue to unload and unload.

When I finally exhausted my supply she exclaimed, "Oh Luke, I never knew such amounts of pleasure existed! It was more than I could have ever imagined!"

I too exclaimed, "Oh I know Twily, you are perfect, absolutely perfect! I could do this with you forever!"

She gave me a sultry smile and replied, "You'll be able to sweetie. I cast a longevity spell on you, you're immortal like me now!"

I was in a state of shock. I could hardly believe that she would cast such a spell on me and I knew that it meant one thing, it meant that we were going to be forever but I still wanted to make sure.

"Twilight," I questioned "does this mean?"

Twilight gave me a kiss and replied, "Yes Luke, it means that we can do this forever and ever!"

I returned the kiss and exclaimed, "Oh I love you so much Twily, I love you more than anything!" Then without thinking I added, "Twily, would you be my marefriend?"

Twilight jumped up, pulled me up with her and exclaimed, "Yes Luke yes, yes I'll be your marefriend!"

She then shoved me back down on the bed and pounced on me before pulling me into another deep passionate kiss. As we laid there kissing I felt a true sense of happiness. When I first bought all those raffle tickets, I hoped so much to win and when I did win, I looked forward to meeting Twilight, I never expected this to happen before.

I never expected that things would build up the way they did, I never expected us to make sweet passionate love and I certainly never expected us to become a couple. This was everything I had ever dreamed of, becoming the boyfriend of my all time favorite pony, Princess Twilight Sparkle.

After laying there kissing for a couple of hours, Twilight could tell that I was more than ready again. She asked, "Ready for another round my sweet Luke."

"You bet I am my sweet Twily!" I gave her a kiss before adding, "And here is to an eternity of sweet lovemaking."