The Best Valentine's Day Ever

by StormLuna

Rating: mature
Tags: Alternate Universe, Human, Romance, Porn, Self Insert, Equestria Girls, Sex, Dean Cadance
Length: 3539

Valentine's Day has arrived again at Crystal Prep and like it was every other year, I was uninterested. While most of the students have a special someone, I don't. It was nothing special until I got called into Dean Cadence's office.

Valentine's Day has arrived again at Crystal Prep and like it was every other year, I was uninterested. While most of the students have a special someone, I don't. It was nothing special until I got called into Dean Cadence's office.

All characters are age 18+

Tagged AU since Cadence is single.

Published 2021-08-29 00:30:01 UTC
Last updated 2021-11-26 15:34:31 UTC

Our Intimate Moment

Valentine's Day had arrived and at Crystal Prep many of the students were in a very good mood. Despite Principal Cinch's constant bitchy behavior and rigid rules, this was the one day of the year that she relaxed things and allowed the students in relationships to kiss and hold hands. Unfortunately for me, I was not in that crowd. I was single and I'll admit, I was a bit envious of those in relationships. I suppose I shouldn't have been too envious though because a majority of the girls at Crystal Prep simply weren't my type.

It was not long after I got to school that morning when I was called into Dean Cadence's office. I was honestly wondering why I was being called in there. I hadn't got into any fights, I hadn't been truant or tardy, I hadn't cheated on any exams nor had I done anything else that would warrant me being called in. I simply kept to myself for the most part and counted down the days until I would be free from that cursed place.

When I got to her office I knocked on the door and she immediately ordered, "Luke, come in and lock the door."

I headed in but I had absolutely no idea where the lock was until I took a look at the door handle. I then locked the door and saw that she had a deadbolt further on up on the door so I locked it as well. She then continued, "Good, I was hoping you'd lock both of them."

It was dimly lit in there and as I began to look around, I saw absolutely no sign of her. I asked, "Dean Cadence, where are you?"

I stood there for a minute in a silent room until a figure came out of the shadows. It was Dean Cadence and my jaw dropped open in shock. She was not in her rather conservative, modest attire. She was instead in a very sexy red outfit, something that revealed what her normal attire did a good job of hiding, big tits. I stood there staring at them as she approached me and asked, "They're quite lovely, aren't they?"

As I continued to gaze at them, I got rock hard in a hurry and apparently she noticed this because she continued, "I'll take that as a yes!"

She grabbed me down south which broke me from my daze. I then asked, "Dean Cadence, why did you call me in here and why are you wearing night attire?"

Cadence gave me a smile and began, "Well first I would appreciate it if you called me Cadie. Formalities are the biggest turn off of them all and besides, Cadie is so much sexier!"

I gave her a smile and replied, "Alright Cadie, why did you call me in? Did I do something wrong?"

She reached around and squeezed my butt before continuing, "Oh no, not at all but I do need help with something." She again squeezed my butt and continued, "You see Luke, unlike so many others, I am single on this Valentine's Day and I really wish I had a special someone but no one seems to meet my standards."

I asked, "Cadie, are you...."

She cut me off, "None of the men in this town are friendly enough nor are they sexy enough but you, you are a different story."

I could hardly believe what I was hearing. Was Dean Cadence telling me that she thought I was sexy and more importantly, was she wanting something with me? "Cadie," I asked "are you saying you want something with me?"

Cadence licked her lips and replied, "Luke, I know this is probably wrong but I have been watching you very closely ever since you started school here and you are so hot!" I had a look of shock on my face as she giggled, "And I can tell you must think the same about me! After all, whenever you look at me I see your bulge, I know you probably fantasize about me, a lot!"

I blushed deeply because I had, a lot. I was always so scared that one day Cadence would approach me over my bulges and be angry over them. Yes she has approached me over it but she did not seem to be upset about it at all. I replied, "Cadie, I will admit that I have. I have fantasized about you, a lot." I blushed even deeper as I added, "I hope this won't make you think bad of me but every single night before I go to bed and I jerk off, I have images of you in my mind, you and only you!"

Cadence shook her head and sighed, "My my, you are such a naughty boy!" She then grabbed my shirt by the collar and suggested, "How about we undress and you can do so much more than just jerk off to me, you can experience the real thing!"

I was not only shocked over her suggestion but I was excited, very excited. Here I was about to have sex with the absolute hottest woman in the world, in her office. As we were undressing, I just hoped that once she saw me fully nude that she wouldn't change her mind. When I saw her fully nude, I felt like I was in the presence of a goddess. Her tits were so sexy, her hips were nice and wide and those thighs of hers would make perfect pillows if we were to eat one another.

When she saw me fully nude, I could see a look of lust in her eyes. I could tell that she wanted me, bad. This would be further confirmed when she commented, "You know Luke, you are perfect. Your body will be perfect to hold up against mine and your cock, it is the only thing deserving of going up in me." She approached me and gently whispered, "I want it so bad. I want it to be my first, my only and my last!"

I could hardly believe what I was hearing. Was this Cadence's way of telling me that she was a virgin, that she had never been with anyone else. I knew it likely would hurt the mood but I had to know, "Cadie, are you telling me that you've never been with anyone else?"

She gave me a sultry look and replied, "Mhmm, I've never been with anyone else. This may sound bad but from the moment I saw you, I haven't sought anyone out because I knew at that moment that I wanted you and only you! I wanted you to be my first!"

I was in a state of shock but also a state of excitement when I heard this. Never once did I expect a woman, especially one as sexy as Cadence to save herself for me until I came of legal age. I returned the sultry look, "If you want that, then I shall be your first." I gave her a quick kiss before adding, "And you shall be my first too."

She then headed to her desk, threw everything off of it and laid down. She yelled, "Luke, come fuck me! Come take my virginity, come give me yours!"

Without hesitation I headed to the desk but in all my fantasies I had done so much more than merely fuck her, they always involved foreplay and I really hoped that she would want that. I headed to her feet, leaned down and immediately began to suck on her big toe. She giggled and gave a slight kick, "Oh my Luke, you must know what a girl wants! You must know I want so much more than just sex!"

I gave her a smile, "Oh Cadie baby, it wouldn't be any fun if all I did was fuck you!"

She gave me a smile and then began to giggle as I continued to suck on her toes before slowly moving my sucking up her leg. I wanted to make this as pleasurable as possible for her. After all, such a beautiful and sexy woman deserves nothing but the absolute best. As I continued to suck on her, she continued to giggle yet moan at the same time. I wanted so badly to move up faster and get to eating her prize but I held back, I wanted to make her happy.

After probably twenty minutes I got to her inner thigh and when the side of my face hit her lips, they were sopping wet. I stopped sucking and commented, "My my, someone must be very turned on!"

She turned beet red and giggled, "Mhmm!"

Oh how sexy I found that. I found her simple response so sexy as that was probably a sign that she was truly enjoying it. I got back to work on sucking on her. I wanted to be marked as hers so I began to rub the side of my face against her hot wet pussy and began to smear her juices on the side of my face. She giggled, "You want to be marked, don't you?"

I giggled in return, "Mhmm!"

She gave me a cute giggle before I moved in on her prize. The moment I began to suck on her she moaned loudly, "Oh oh oh, oh Luke!"

I then began to probe her with my tongue and damn she was sweet, incredibly sweet! I never knew that such sweetness existed. As I continued to suck and probe her, her moans continued to get louder and her breathing intensified. I could tell that I was about to get a very tasty treat when her moaning became nearly ear splitting. Finally she flooded my mouth full of her cum and that was even sweeter! I however was not about to just move on after that, I kept on sucking and probing.

When I kept it up after she climaxed she moaned, "Oh Luke baby, you really want to please me, don't you?"

I pulled my head up and snickered, "Hey, I want more than one mouthful of cum sexy girl!"

She giggled and began to moan again as I got back to work on her. I could tell that she was truly enjoying it and I definitely was enjoying it. I absolutely loved the taste of her and seriously hoped that this was something that her and I could do on a regular basis. After getting three more climaxes out of her I gave her a smile and exclaimed, "Oh my Cadi, you are so so tasty!"

She too exclaimed, "Oh Luke, you are so good! I never imagined such pleasure existed!"

I gave her a smile, "Well get ready, I'm moving up now!"

She gave me a smile and immediately began to giggle and squirm as I was sucking on her stomach. This was something that I not only found incredibly hot but I also found it cute. I began to suck on her harder and she giggled, "Luke, this isn't fair! I'm so ticklish there!"

I stopped and gave her a mischievous smile, "So now I know what to do when you're being a naughty girl!"

I then took right back to her stomach, causing her to giggle and squirm further. While I was enjoying making her squirm and giggle, I was so close to something I wanted so badly, those sexy big tits of hers. Very quickly I moved up to them and the moment I began to suck, her squirming and giggling changed to a moan, "Oh Luke, yes baby yes!"

Her breathing became harder as she continued to moan. Soon she began to run her fingers through my hair as her moaning became louder, "Oh Luke baby, oh, ooooh, oooooh baby, oh Luke baby, oooooooh!"

She let out a loud moan and I knew that she had came all over her desk. I stopped momentarily and reached down to her pussy and gathered what had yet to drip out and scooped it up with my fingers. I then brought my hand back up to myself and licked it off. I gave her a smile, "You know sexy girl, I'm not about to let all of that go to waste!"

She giggled, "Oh my Luke, you must really find me tasty!"

I too giggled, "Oh I do Cadie, I do!" I crawled on top of her entirely and asked, "Are you ready hot stuff?"

Cadence had a nervous look on her face as she replied, "I am but please be careful, this is my first time."

I gave her a smile and inserted my member into her tight little hole. She let out a gasp of delight when I began but I could tell that she was getting nervous the further my member went. It was not too long until I hit a barrier which gave way easily, causing Cadence to sink her fingernails into my back and let out a loud scream of pain.

I stopped moving forward and asked, "Cadi, are you ok? Are you sure you want to do this?"

Cadence wrapped herself around me and yelled, "Yes now don't move. I'll be ok."

I laid there for I'm not sure how long until she gave me the go ahead to begin to thrust her. As I was thrusting her, I never once imagined how good the warmth of being inside of her felt. Both of us soon began to moan loudly, very loudly. She must have realized that there was a chance we could get caught so she pulled me into a deep, passionate kiss which muffled our moans somewhat.

I soon began to thrust her harder and I could feel my member making contact with her cervix, the opening to the womb. I knew that if I was to unload into her right there, that I could very well get her pregnant but it simply felt too good to pull back any and each time I hit her cervix, she let out a moan of pure pleasure. Soon she broke the kiss and moaned, "Oh Luke baby, I'm so close, I'm so close!"

I too moaned, "Oh Cadie baby, its coming, its coming!"

"Oh Luke baby, oooooh Luke!"

"Oh Cadie, oh Cadie, oh Cadieeeeee!"

When we climaxed simultaneously, my member was shoved right up into her cervix, sending a flood of semen straight into her womb. Once our climaxes were complete, we collapsed into one another's arms and Cadence would be the first to speak, "Oh Luke, that was fantastic! I never knew such pleasure existed!"

I exclaimed, "I know Cadie, this was millions of times better than simply jerking off to you!"

Cadence calmed down and became more serious, "Luke, I absolutely loved our moment together but you were in my cervix when you climaxed and I'm worried that you might have got me pregnant."

I became nervous, "I'm so sorry Cadie, I didn't mean to shoot it straight into your womb."

Cadence seemed to have calmed down a bit, "Well if you did, no one here at the school needs to know it is yours and then right after graduation," She then began to smile, "we can get married." She saw a smile on my face and added, "I take it you like the sounds of that as much as I do?"

I replied, "I do." I paused for a moment before continuing, "Cadie, whether that happens or not, I want you to know that I love you with all my heart. I want you to know that I feel like my life would be incomplete without you so I have a question for you."

She gave me a huge smile and exclaimed, "Yes Luke yes, yes I'll be your girlfriend!"

The two of us wrapped our bodies together, rolled on our sides and began to kiss passionately. As we were kissing, so many thoughts began to run through my mind. I was ecstatic that I had Dean Cadence as my girlfriend and that she was my first but I did have my concerns about whether or not I got her pregnant. One thing that did surprise me though was that she didn't seem upset over the chances of it and as far as marrying her if I did, I'd be all for it. An eternity with Cadence would truly be wonderful after all.

The Big Test

A bit over two weeks had passed and things seemed to be going fairly well. Cadence and I did manage to talk to one another on a daily basis and the past two weekends were filled with us making sweet, passionate love. I could tell that Cadence truly did love me, I could tell she loved me just as much as I did her.

It was an early Saturday morning in March when I got a phone call. When the screen read "CadieMyLove" I immediately answered it.

"Hi Cadie sweetie, how's it going?"

"Luke honey, I just thought I'd let you know that I'm late."
"You're late?"

"Yes I'm late. I have a pregnancy test right now and I was thinking that you could come over while I take it. I think it would be more romantic if we got a positive result together."

"I agree with you there so I will be over there ASAP."

"Alright Luke sweetie, I love you."

"I love you too Cadie, see you soon!"

*CLICK*

Once I got off the phone with her, I couldn't help but be nervous. I knew that a positive result would change both our lives in a significant way but I knew that if it was a positive result, I could get a job somewhere so that I could contribute to what would eventually become a three member household. One thing that did excite me though was that if she were pregnant, that we would be getting married right after I graduated.

After ten minutes I arrived at her house. I knocked on the door and I heard her yell, "Come in Luke but lock the door behind you."

I did as requested and once I got inside, there she was standing fully nude in her living room. She gave me a smile and said, "You know the drill sweetie, no clothes on in my house!"

I gave her a smile and proceeded to undress. Once I was fully nude, she motioned for me to come to her and ordered,

"Come with me Luke and we'll see what our futures have in store."

I gave her a smile and followed her to the bathroom. She got sat down and gave me a smile as she opened the test, sat on the toilet and peed on the strip. The test said that it would take one minute and I swear, that one minute felt like it took forever. I could tell by the look on Cadence's face that she was as nervous as I was. After one minute the result came up, "+."

Cadence leapt up into my arms and exclaimed, "It's positive Luke, it's positive." Her happiness turned more into a squeal,

"We're going to be parents Luke, we're going to be parents!"

Both of us broke down in tears of joy as I exclaimed, "I know Cadie sweetie and you're going to be the best mother ever."

Cadence exclaimed, "And you'll be the best father ever!"

We began to jump up and down in a loving embrace for several more minutes before finally calming down. Once we had calmed down, Cadence grabbed me by the hand and suggested, "How about we go and lay down for a while, just like we will every single day forever before too long."

I gave her a smile and she pulled the covers back so we could crawl under them. Once we got covered up, we wrapped our bodies together and began to kiss passionately. As we were kissing, I felt so much love for her and I felt so much love coming from her. I knew that chances were we would encounter struggles ahead but I knew that in the end everything would turn out just fine. I knew that in the end we would be a happy, loving family.

After we broke the kiss I said, "Cadie, I love you so much. You are my everything and I can't wait until we can spend all eternity together."

Cadence blissfully sighed, "I love you too Luke. I know we may have rough times but in the end I know everything will be fine and we'll have a lovely family."

The two of us then decided to try and get some rest. Cadence fell asleep rather quickly, quicker than I did. As I listened to her rhythmic breathing, I couldn't help but realize how truly lucky I was. I realized that I was going to wind up marrying the most beautiful, most caring, most loving and most sexy woman in the world. I realized that life truly was great and that a truly wonderful future awaited both of us.