As Vinyl lay on her bed, music softly thumping its way into her brain, she focused less on the lyrics and more on her life. Staring up at the ceiling, she could almost see scenes from her romantic endeavors play out: from her first date with Octavia at that stuffy concert hall (which Vinyl had actually invited her to as a gift) to her previous girlfriends from high school.
"How am I going to do this?" Vinyl thought. "How's this gonna go down?"
Vinyl was still a virgin, though she didn't want anypony to know it. That didn't mean she was a prude, far from it, in fact. Vinyl knew exactly what she liked, and had gotten quite adept at relieving bouts of heat with a dark room, her hoof, and a good playlist. And she knew what types of activities she and Octavia would likely get up to in a week's time: several issues of Moist Mares Monthly were tucked beneath her mattress, and they'd taught her a thing or two about how two members of the fairer sex could clop hooves.
What she liked had been influenced a bit by her history with her own sexuality. Vinyl had first discovered she was gay at age 13, when estrus first hit her. She'd always enjoyed playing the same games that boys did, but that summer at the pool, instead of ogling the colts in their swimwear like so many young fillies did, Vinyl just preferred hanging out with her friends to see what they were wearing. In the locker room, she'd completely zone out while everypony was changing and try to hide her fiery face whilst surrounded by butts that, though she'd seen them before, suddenly took on a whole new meaning for her. Around that time, she also had an all-female health class to learn about this sort of thing; Vinyl was secretly glad it was the last class of the day, which allowed her time to sneak off after the bell and study what she'd just learned.
Vinyl's mother had caught her kissing one of her best friends in her room when she'd come to hang out after school, but didn't mind; in fact, she said it was one of the cutest things she'd ever seen. Vinyl had come of age in a home that accepted her preferences... unlike Octavia.
Vinyl came close to having her first sexual encounter at age 15, at a high school party, with a mare two years older than her. Though there had been alcohol present, both of them were sober, and had secluded themselves on a stone bench in a little backyard garden. Vinyl couldn't remember her name, but that she was a dark-furred unicorn, an exchange student from Marebourne.
The older, larger mare was practically laying on top of Vinyl, though Vinyl liked her body heat. Locked in each other's embrace, they'd been exchanging powerful kisses across muzzles, necks and collarbones for several minutes; Vinyl's legs twitched as her forehooves gripped the dark mare's jacket, pulling her closer as they kissed.
The older mare popped her lips off of Vinyl's neck with a heavy breath as she looked her in the eyes.
"Huff... I want you, Scratchy..." she said lustfully. Vinyl bit her lip upon hearing this, her ears twitching. The other mare slid a forehoof from Vinyl's shoulder down to her knee, playfully rubbing it.
"You've got just rippah thighs, y'know that, Scratchy?" She said with a smile and a chuckle. Vinyl tried to reciprocate and thank her, but she couldn't form the words. The accented unicorn pushed herself further onto Vinyl, bringing their faces closer together and slipping her free hoof up the inside of Vinyl's thigh.
"Why don't you spread 'em for me?"
Vinyl felt an immense shock of pleasure, as well as surprise, as a hoof was suddenly pressed against her marehood. Her eyes grew massive, and she uttered a quick "WHOA!" before scooching backwards out of the mare's grasp.
"Wazz wrong?" The other mare enquired.
"Sorry about that..." Vinyl said, folding her forelegs nervously and crossing her rear ones at the knee. "I just---"
"Well you liked all o' that other, didn't ya?" The mare seemed slightly offended.
"Well yeah!" Vinyl quickly tried to correct course. "I just... don't want to go there yet."
"Scratchy, you can trust me, I know what I'm doing."
"I just don't want to go there yet."
"...Alroight…" The dark mare's eyes narrowed and she assumed a position similar to Vinyl's.
"But that was still a lot of fun!" Vinyl tried to encourage her. "If you want, I know someplace we can get food and---"
"Maybe you should go."
"...Oh...o-okay..."
Vinyl hopped down from the bench and headed back towards the party. The other mare continued to sit with her forelegs crossed and a scowl upon her face.
"Keep in touch?" Vinyl asked in her scratchy young voice.
"Oh yeah, sure, sure."
The two never spoke again.
Laying on the bed, Vinyl reached up and felt her neck; five years ago, there'd been a hickey there so huge she thought it might scar. She'd had a hard time explaining that one to her mom. After that, she followed her mother's advice and tried to find mares that actually appreciated her; there were a few, though she wasn't with any of them very long, and when the opportunity for sex arose, she backed out. Something about it just never felt right.
At 16, Vinyl had her first drink, again, at a party, though this time on Nightmare Night. Again, she wound up in close quarters with another, equally drunken mare. Though she'd gone farther with this peach Pegasus than with that stormy unicorn, both of them wound up passing out before they could get each other out of their panties. They dated awkwardly for a while after that, but never let things get intimate--or inebriated--ever again. Personally, though, Vinyl had discovered that alcohol was very useful for forgetting about how awkward she was around mares; she would eventually come to depend upon it.
At the age of 17, Vinyl entered into a long-term relationship... with a mare four years older than her. Vinyl could never fully explain why she had a thing for older mares, but she just did; ironically, Octavia was still older than her, but only by about four months. Again, the relationship was sexless, though it did involve some very charged situations for teasing's sake; though she didn't know what to call them at the time, Vinyl later learned they were referred to as scenes.
Vinyl discovered a lot about herself during that time: that she likes being submissive, but can take charge, that being called names or belittled was an occasional turn-on, and especially that sometimes--not every time, but sometimes--she enjoyed having pressure on her throat or being lightly choked, though only with a collar. Though their two years together helped Vinyl further shape her sexuality, things got bad when the dominant, controlling persona her partner adopted in the bedroom began to leak over into everyday life. Vinyl started to drink more, and think less of herself as a pony. Eventually, though, she found the guts to break it off when her partner hit her across the face during an argument... after that, her older brother and his friends had threatened the abusive mare so strongly that she left town. Vinyl had always loved her brother, but she loved him a lot more after that.
Despite her brother's attempts to sober her up, Vinyl still drank on a regular basis after she started college. She had begun to experiment with marijuana when a new mare showed up among the student body: Octavia.
Vinyl was instantly smitten with her, and tried to spend every waking moment near hear: from the music classrooms, to the cafeteria, to the student lounges. As the two started to become good friends and Vinyl's feelings for her started to deepen, Vinyl knew what she had to do.
"Vinyl, this is your one chance." She remembered telling herself. "This mare is the one for you. She is perfect. She's smart, she's beautiful, she likes music, but most importantly, she's responsible. And if you want her for your own, you've gotta shape up and be responsible too. Be worthy of her. If you frick this up, Vinyl, you'll die sad and alone, drunk in a ditch somewhere."
So, Vinyl Scratch quit everything cold turkey. She dumped her stash of alcohol down the drain and smashed the bottles against a dumpster. She took what weed she had and flushed it down the toilet. She started taking care of herself again, and dressing better whenever clothes were required. She kept a picture of the two in the corner of her mirror, something she still had, to remind her that her life was awesome. Before long, she and Octavia were dating, and she couldn't have been happier with herself.
That was her experience. She had no clue what Octavia had been through, if she'd taken time to discover herself like Vinyl had; all she knew for sure was that this was her first relationship. Vinyl wanted to make their first night together a loving, memorable, and fun experience for both of them. Vinyl knew how to get herself off, and probably how she could get Octavia off, but what she didn't know was how much the mare could handle or would want to attempt in her first rodeo.
The last thing Vinyl wanted, after all, was to pressure Octavia into something she wasn't comfortable with, just as Vinyl herself had been many times before--fortunately to little effect. However, no matter what experience the unicorn had, it was likely to be more experience than her partner; she would have to take the lead, something she preferred her partner to do. Vinyl told herself that she could probably rise to the occasion if Octavia wanted to submit, but... could she? And how much control was too much? With a great sigh, Vinyl rolled over and levitated a pillow to her face. This was going to take a lot of thought.