No Regrets
Your senior year of high school was going pretty well. You'd gotten into the college of your dreams, your grades had yet to falter, and you had no regrets. Well, except for one. You still had never had a girlfriend, but it's not like you didn't try. There were many an attractive lady at your school, but you never felt they were dating material. They were great to be friends with, but they just never seemed to click. That is, everyone but one. Rarity.
She was the purple haired goddess of your dreams given a physical form. Her hair was perfectly curled and long, reaching her back. Her face was near flawless, with puberty treating her quite nicely. Her eyes were the deepest blue, her lips irresistibly soft-looking. Her body was the definition of hourglass, always wearing stylish clothes that accentuated her assets. Her legs were long, slender, and quite honestly sexy. She was kind, knowledgeable, and always seemed to know exactly what to say to make bad days turn into heaven. You two had been friends for a few years now, but you always had a"thing" for her; whether or not she knew, that was a different story. You'd often thought of asking her out, but were afraid of the repercussions. What if she said no? What if this ruined your friendship? What if she said yes? What if it doesn't work out? These questions kept you from having a perfect senior year, you were convinced of it.
One day, you and Rarity were walking home from school excitedly talking about the future and what it may hold.
"I just can't wait to study at Manehatten! That's where all the action is, and I just love the hustle and bustle of city life!" Rarity said with stars in her eyes.
"I'm so happy you got into that fashion school Rarity." You respond. "I just wish we weren't going to two different places."
"Oh I know darling! But, you're the one that wanted to stay in-state. Besides, your college is pretty prestigious, you should be proud! I know I am."
"Thanks Rarity. You know, this is putting me in a celebratory mood, we should do something tonight!"
Rarity's eyes widen with excitement. "That's a splendid idea! Anything in particular?"
Little did she know that you had been planning this for a while now. You'd always wanted to take her to dinner and a movie, drive her back to your place, and seal the deal with a loving confession and romantic kiss combo. Cheesy: yes, but you were certain it would work, leading to a wonderful if short relationship.
You pretend to think the question over. "Hmmmm, how about a movie? There's a new scary one out right now. "Dead Meat 5: The Meatiest End', everyone says it's pretty good."
"Oh yes, that would be wonderful! Let's find a time right now." She pulls out her phone and eagerly searches the theater times. You knew it was going to be a good night.
The night went just as you planned, more or less. You decide to meet Rarity at a local sandwich place. Not the most romantic, but you thought it was better then waiting in line to then pay your entire savings on a date that might not even end well. She came dressed in a tight T-shirt and some skinny jeans, emphasizing those assets of hers. You both had great food and a great time. You talked about your futures and of the past, you even thought you saw some romantic hints. You couldn't quite explain it, but the way she said things and the way she looked at you when you talked seemed different.
Later, you both went to the movie, which was no where near as good as you'd been told. The plot and characters were shallow and the whole thing was designed to provide cheap scares, but you didn't care and neither did Rarity. You both laughed at the wrong parts and she jumped at the right parts, unintentionally clinging on to you, or maybe it was intentional. Every time she did this, her breasts would clamp around you as her arms did the same to your own, brushing against your shirt in a maddening manor. At first it was awkward, but it happened so often that the two of you got used to it. Either way, things were going well.
After the movie, you decided to initiate the next phase of your plan.
"So Rarity, do you maybe want to continue that fun back at my place?"
"Oh yes, that would be lovely! Are your parents home?"
"No, they left on a business trip, leaving me the man of the house!" You jokingly pose like you were a superhero of some kind.
She giggled. "Well big man, let me call my folks first and make sure its all right. This is a sleepover right?"
You hadn't even considered that. Ok, that was a lie, but you never thought she would be up for it. You assumed the night would end with you driving her home and giving that final kiss to seal the deal. Maybe you could give the kiss and revel in the new dating status. The night had gone well so far, and you were positive she was interested.
"Of course! That will be fun."
You drive Rarity back to your place after her parents had given their consent. You both change into some pajamas, you gave her some pants while she just leaves on the tank-top under her shirt. Her cleavage is even more prevalent, forming a perfect crack on her chest, one that is hard not to stare at from time to time. Your positive she caught you staring, but it seems like she doesn't mind. You offer to get her a drink, which she happily accepts as she sits down on your bed and looks around your room.
As you pour her some soda, you realize that this is the perfect chance to ask the question, to reveal your true feelings. It's now or never.
"Hey Rarity, I have something I want to say." You say this as you pass her the drink.
"Sure darling, what is it?"
You hesitate, but then let the words fall out. "I have to admit that I think you are absolutely beautiful, and I've thought this ever sine I first saw you all those years ago. Your personality is stunning, your face is an image of perfection, and your generous nature is just icing on the cake. I've always wanted to take our relationship to the next level, but I've always been afraid. I invited you out tonight with the intention of taking this to the next level, and I feel like I've made the right choice. What I'm saying is, do you want to start going out with me?"
You start to catch your breath as the words linger in the air. Rarity is stunned, looking like a train has hit her head-on. She seems deep in thought, and you start to regret your decision. Maybe you said the wrong things, maybe you came on too strong, maybe yo-
"Yes."
Time stops. You look to the girl of you dreams, unable to fathom what she just said.
"I'm sorry, what was that?"
She laughs. "I said yes, of course, I would love to date you. I've honestly been waiting for you to ask me."
"Really?!"
"Yeah, I thought I was being pretty obvious with my advancements, but I guess not!"
"Oh, that is such a relief, you have no idea!"
...
You look to her in guidance. "What now?"
"I have an Idea." Rarity seductively says, lowering her eyelids to cover half of her shimmer blue orbs.
You're slightly confused when she suddenly moves in, planting a long kiss on your lips. You both hold this position for what felt like an eternity, then another, and then another. Each kiss becomes more passionate then the last, both of you wanting to express your love in the best way you know how. Her lips are soft, her breath is hot and husky, and it's all melting your brain. She holds onto your neck as you grab her waist, not wanting to ever let go, which you only do to gain a few fleeting breaths before you're at it again.
The make-out session continues as your tongues are added, only heightening the experience, among other things. You would feel embarrassed for pitching a tent, but you're too encompassed by lust to even care. Rarity removes her lips suddenly, quickly looking down at your crotch then back at you, a sexy smile etched across her face.
"Well, it would appear someone wants to take the next step." She licks her lips, which causes your member to pulse in anticipation.
"Are you sure? I don't want to take things to-"
You're cut off by Rarity's tank-top hitting the floor, causing you to realize she isn't wearing a bra. Her breasts are a solid D cup, both perfectly round and supple with erect nipples. She looks at you, beckoning with her half-lidded eyes, which you comply with a passionate kiss. You place your hand on her tits, at first not sure what to do but quickly forming your own method of play. You squeeze, fondle, and generally feel her boobs, occasionally pinching her nipples. This causes her to moan into you mouth as you continue to make-out, her sexiness increasing.
During the process, she has taken off your shirt, now feeling your chest and back as you continue your fondle session. Rarity forces your mouths apart, instead placing your hand near her pajama pants. Taking the hint, you quickly remove them along with her panties, throwing them near the other discarded clothes. She now stands there completely naked, her heavenly features there for you to see. You can't help yourself and pounce on her, forcing you on top of her. You decide to spice things up a bit and kiss her neck, slowly moving down her body. You cover her chest in your kisses, along with her abdomen. The whole time Rarity is moaning with increasing pleasure, urging you on as she becomes excited.
You finally reach her pussy and gaze at its magnificence. You'd never seen one up close, and quite frankly you weren't sure how to proceed. You heavily breath into it, staring at the fluids releasing from its entrance. This pause is too much for the girl and she responds in the sexiest way she can, in between breaths.
"Darling, I need you to lick me dry, before I go crazy."
Not wanting to disappoint, you stick your tongue out and proceed to lick up her juices of pleasure. Her moans tell you your doing something right, so you continue your vaginal assault, tasting her every drop. The taste is sweet, not at all what you thought it would be. It's a good surprise. The scent is simply intoxicating as you keep licking, wanting to keep Rarity in bliss. Her moans start to become screams, her breathing turns husky, it only turns you on more.
"Put you tongue in me already!"
Wow, never thought of that. You comply with her command and slip inside her, she responds with a long moan, one that drives you wild. You can feel her vaginal muscles convulse around your tongue, contracting and releasing in response to your erratic movements. You continue your single man dance as Rarity simply eats the pleasure up, yelling for you to never stop. Her moans keep at a steady pace of increasing tones, moving faster then when you just licked her outsides. After several minutes of this pattern, Rarity screams into the night.
"I-I-I'm cumming!"
Before you can even respond, you feel her walls clamp around your muscle as her climax fills your mouth. Like the gentleman/animal you are, you eat it all up, not letting anything escape your hungry mouth. Once she finishes riding her high, you both look at each in tired but satisfied bliss, at least she's satisfied. Almost as if she can read your thoughts, she pulls you up towards her mouth to taste herself, all the while moving her hands towards your crotch.
The bulge in your pants had not let up this whole time, and honestly it was starting to hurt. As she removed your lower clothing, she also removed her lips to look at her prize. Once your underwear finally passed by your cock, it stood in attention, ready to please.
"Well well" Rarity said as she looked into your eyes, "It seems I made the right choice when dating you!"
Pulling you in for another kiss, Rarity proceeded to jerk you off. It was your turn to moan into her mouth, as her soft hands took firm control of your dick, slowly and effectively fulfilling your desires. She twisted her hand around your cock, getting all she could out of you. Her other hand was firmly around your neck, making sure you would never escape her kiss, which you were happy with.
You start to feel that familiar pressure in your groin, knowing all too well that the fun was going to end soon. Desperate to keep it going, you grab her jerking hand to give yourself a moments rest. Rarity was not having this, as she flings herself on you, pushing you onto the bed cowgirl style. She leans down, her locks falling onto your face in the sexiest of ways, her beasts rubbing against your chest. She looks you right in the eyes, her own shimmering bright blue.
"I love you." She silently breathes.
"I love you too." You equally reply.
After some passionate kissing, and a long enough wait, she sits up and gently guides your dick to its final destination. You never imagined you be in this position, with this girl, but you know it's all for the best.
Your concentration is broken by a new sensation on your crotch as it enters inside your lover. Rarity takes her time easing your member inside her, moaning all the while. It takes all your restraint to not thrust the rest of the way, but you know this is the best way to make her feel good. Once her thighs finally touch yours, she proceeds to slowly gyrate, reveling in the pleasure you're bringing to her. Little does she know that she's easily returning the favor, driving you crazy with every turn of your stomach. You grab her plump and firm ass, eager to do what you've always wanted to for years, hoping it will distract your mind from releasing too early. Yet, Rarity is determined to make your struggle even worse. She quickens her motions, laying down so she locks lips, moaning into your mouth once again. It's like she knows exactly how to turn you on.
You know you're about to blow, so you place a greater grasp on her ass and stand-up. Rarity yelps in shock, but quickly adjusts by holding onto your neck and back, wrapping her legs around your lower half to keep you close, kissing you again as if nothing happened. You now have control and start to thrust, slowly pulling out and quickly pushing back in. This must drive Rarity insane, because she cuts off your kiss to scream in utter delight with every thrust. She digs her nails into your back just to hold on, but you don't mind. She then pulls back, extending so only her hand is around you neck, using it for support. She looks you in the eyes as you enter and re-enter her pussy, her breasts jumping with every thrust and an audible smack emanating from both your thighs. Rarity's hair is frazzled and covers her face, giving her a mysterious but irresistible look. You pull her back in for some more passionate kisses. After a while, you remember why you stood up in the first place. While still inside her, you place Rarity on the bed, taking the dominant position. You quicken your pace, causing her to shout her pleasure.
"I'm gonna cum again, please don't stop no-OHHHHHHH!"
"Me too!" It was all you could say during this time of passion.
Your thrusting reaches it's peak as you get closer and closer to the end. You feel that Rarity is reaching the same conclusion. You both decide to finish how you started, making-out while you moan in each others mouths. Her lips making contact with yours, their softness sends you close to the edge. Rarity then breaks the kiss to release a long and sexy scream/moan. You feel her vaginal walls close around your dick, her cum falling around your nether region. It feels like her pussy is trying to suck you dry, and it's working. When you think you've had enough you pull-out, remembering that you forgot to bring a condom. Rarity quickly realizes the situation and places her hand on your cock.
Expecting a satisfying hand-job finish, you're shocked when she puts her mouth around your lower head. She proceeds to take most of your length in her mouth, sucking with a tenacity that drives you absolutely insane. Just to put the cherry on top, Rarity removes her mouth and replaces it with her magnificent tits. She jerks you off with her breasts, sucking your head in between movements. The sight of your cock in-between her pillows would have been enough, but the sensation was even better. Her sweat and saliva mixed with your cum covered dick makes for a slippery but hot ride. You can't take anymore of this, and prepare to warn her.
"Rarity, I'm about t-"
Too late.
You release your seed all over Rarity's beautiful face. The first stream hits her lips and chin, dripping down to her breasts. After the initial release, she quickly places her mouth around your shaft, eager to eat whatever you give her. After you release your final string of semen, she sits up, looks you in the eyes, and swallows. Goddamn that hot.
You both lay under the covers, still recovering from your steamy night. Rarity decides to use you as a spoon, which you are eager to oblige. She places her arm under your back, intertwining your legs so you'll be ultimately close. You kiss her on the head.
"I love you, Rarity"
"..."
"Rarity?"
You look down to see that she's asleep, a blissful smile across her face. You smile and lay your head back, letting your suddenly heavy eyes fall as you realize that you are the luckiest man on Earth.