Excuse the slight title change. Everybody was 18+ mind you. Enjoy!
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—
It was the end of our first year of college. I had a plane ticket home and a few days to kill before my flight. Staying on campus wasn’t an option, but Luna invited me to shack up with her at her mom’s house and then give me a ride to the airport.
We weren’t sure what our status was, relationship-wise. Luna’s mom understood that we were broken up, but friends. A guest room was made ready for me, but Luna promised that if we were quiet, I could sneak into her room for sex.
I was super excited about three days of casual sex with my ex or current girlfriend, whichever it was. But the first night, I couldn’t get Luna’s young friend Sam out of my mind.
“So…” I said, “did you tell Sam you plan on making out with him?”
She blinked at me in confusion. “Why are you bringing up Sam right now??”
It was a fair point, since she was currently dragging her pussy up and down the length of my bare shaft. My mind raced for an answer.
“I mean… don’t I have a right to know? Since we’re, like, having sex and all?”
She sighed, dismounting me. Not at all pleased that I’d forced the topic.
“I did tell him, yes.”
My insides lurched. I was jealous, I knew, but I couldn’t quite put my finger on what made it so intense compared to the other guys Luna had hooked up with over the course of the year.
I just knew I really wanted details, so I asked how the conversation went.
“Things have kinda progressed a lot between us,” she told me.
“Oh okay..” I said, making a great show of how unaffected by it I was pretending to be. “Well, that’s exciting, right?”
Whatever irritation she’d had at our sex being interrupted vanished as she enthusiastically launched into her explanation.
“Well, I had this whole idea in my head that I was going to rock his world and, like, drop this bomb on him, you know? Like, ‘Hey Sam, guess what?’”
“But..”
“But I am, like, totally not as smooth as I think I am. It came out more like, ‘Ummm, Sam? How would you feel about, like, if you and I were to maybe… kiss?’”
“Wow.”
“And then I expected him to like, flip out about it or whatever? But he just got real quiet to the point that I started to worry I’d majorly embarrassed myself by suggesting it.”
“…”
“But then he said like, in this really quiet and almost dangerous voice.. He was all, ‘I would love that.’ And I was just a mess at that point, babe. Like, my heart was just pounding out of my chest.”
I could imagine it. Luna had been so electrifying during our New Relationship Energy phase; each declaration we’d made affirming our romantic interest in each other had practically sent audible crackles down her spine. You could just feel the intensity of her reaction.
“So,” she continued, “I had imagined it would just be me dropping this bomb on him and then like, ending the conversation shortly thereafter and walking away feeling all proud that I’d rocked his world. But that was totally out the window now, I needed to keep the conversation going.”
I murmured for her to continue, practically quaking with anticipation.
“So we started, I dunno, discussing how we were going to go about it?”
“Ah, jeeze, Luna…”
“I know, right? It was pretty hot…”
I’d been casually stroking her bare legs while we talked, and I leaned down to kiss her thighs. “Well? What did you say??”
“I dunno if I should..”“You have to tell me,” I pleaded.
“Well so, we don’t know for sure if we’re going to have sex.”
?!?!??!?!?!??!??! “You guys, like, straight up openly talked about the possibility of having sex?”
“I mean, yeah? Like, we both definitely want to. But like, he’s really shy about it, you know? So I like, tried to take some of the pressure off. I told him that the first time we make out, it will just be about us seeing what sort of chemistry we have. Absolutely no pressure to go any further than that.”
The first time…
“That’s… that’s very sweet of you,” I heard myself say.
“But, I did tell him that if he was comfortable, he should try feeling my boobs while we kiss. Now that one did blow his mind!”
Mine, too. I had tunnel vision and was watching events unfold from a distance. Without planning on it, I found myself scooting around behind her and reaching around to cradle a breast in each hand.
“Fuck. He’s probably fantasized about them for so long..” I said.
“Like, one thousand percent! He like, could barely speak after I suggested it. He got so excited babe..”
“He has to touch them,” I was saying. What the fuck?? “I mean, like, you love having them touched, so if you really want to evaluate your chemistry, that should definitely be part of the make out session.”
“Oooo, ‘session’… I really like that.”
Gulp.
“Well, anyway, I swear I was trying to not pressure him, but I kinda might have made him promise he’d let me take my shirt off for him.”
Of course, this meant she would be fully topless, since Luna had never been one for bras. But I would guess if she was at least a D cup, and her ample breast flesh spilled over my hands as I contemplated what was in store.
Obviously, I was in for it. I imagined spending the summer equally dreading and lusting for the next update on Luna’s conquest of this young man. Thank goodness I’d have Sophia around to vent my frustrations upon.
“So, when all is this going to happen?” I asked.
She took ahold of my hands and removed them from her tits, turning to facing me. All serious-like.
“Okay, so that’s the thing,” she said, avoiding eye contact. “Like… tomorrow?”
“I… what?!”
She was slightly frantic to explain herself. I was planning to head into town the following day and hang out with some classmates who resided in the area. Sam and his friends – all of whom, you’ll recall, I believed were equally smitten with Luna – were having a get together.
Luna and Sam had already made arrangements to sneak off with one another so they could … evaluate their chemistry.
“Are you mad?” she asked.
I was a fucking wreck. But, for whatever reason, it was of the utmost importance to me to downplay it and act like I was less affected than I was.
“Not mad. It’s just … sooner than I expected.”
“Well…”
“…?”
“At least now I’ll get to tell you all about it when you sneak into my room tomorrow night?”
It was the most directly we’d acknowledged this weird dynamic that was arranging itself into being between us.
If I had known then what I now know, I would have been able to lean into it more. I would have told her, “Yes, that’s what I want. Badly.” I would have fucked her, and uttered filth in her ear, nudging us down the rabbit hole over our mutual lust for her burgeoning romance with Sam while we fucked.
But alas, I was nineteen, and a coward. The best I could manage was to grunt my assent, and pray my that my desire for her to have this experience wasn’t too obvious or embarrassing.
—
I texted Luna the next night from my guest room at her mom’s.
S: Hey, is it okay to come over?
I stared at our chat, trying to hold panic at bay as I watched the “…” appear and disappear over the course of the next few minutes, as she apparently agonized over her reply.
Finally:
L: Come
All that deliberation for just four letters. I became filled with sense of dread; this was not going to plan.
The previous night, Luna had been naked when I arrived. Never one to be shy about her body, one of Luna’s favorite stunts was to flash her pussy at me unexpectedly. Like she’d say “Hey babe…” and I’d glance across the room to see she’d hiked up her skirt, pushed her underwear to the side, and splayed her labia apart lewdly with her fingers. She’d then cackle with glee while I turned bright red with embarrassment.
That’s how it had been last night. She’d whipped the sheets off when I entered to reveal legs spread obscenely. A gloating expression on her face as my eyes bulged at her open vagina.
But tonight, she was clad from head to toe in pajamas. It was one of the least revealing outfits I’d ever seen Luna wear.
“I don’t think we can have sex tonight,” she said as soon as I’d clicked the door shut behind me.
“Is everything okay?”
“Yeah! I mean, I think so. I just…”
“??”
“I just don’t know if I’m the sort of girl who can have sex with, like, two different guys in the same day.”
Gulp. “… I see. So, you and Sam..”
She looked down, abashed. “Yes.”
She walked me through the evening’s events.
—
Totally independent of her anticipation of making out with Sam and showing him her tits, Luna was thrilled to spend time with her high school crew. The Luna Fan Club, as I thought of them.
To set the tone: Freshman year was wildly transformational for myself and my classmates. Many of us felt that we’d discovered and harnessed a secret universe; our minds had been awakened, and we now saw the world in a Deeper way than the normies back home who’d missed out on the voyage.
To various degrees, that was the underlying tone of the social interactions we’d have as we returned to our families and high school friend groups for the summer. For Luna, the way it manifested was: she couldn’t wait to get her hometown friends on board with the fact that every conversation held such magical possibility for what ideas could be communicated and explored.
Luna’s debut of the new, college-enlightened Luna was a hit. It was one of the best parties she’d ever been to and she felt like she had her whole friend group eating out of her palm, considering the charm and witticism and philosophy she was dropping on their freshly-high-school-graduated asses.
This was apparently not what Sam had had in mind, and she began to detect about him an aura of frustration. As far as Luna was concerned, the world was wide open for the taking, just waiting for her and whoever would join her to shape in the fashion they desired. She couldn’t imagine stressing out about whether or not they would get to kiss right this second.
Nonetheless, a frustrated Sam led to a determined Sam, and eventually Luna found herself being led upstairs by the hand. Floating on her feet now that the moment was upon her, she told me; in an optimal state of mind to be receptive to his advance.
“Did people notice you?” I asked.
“Honestly, I have absolutely no clue.”
It was kinda-sorta a point of concern. Luna and I had enough friend group overlap that any actions which might shed light on our status as a couple (or not-a-couple) would produce speculation and gossip.
“So basically all of our friends watched him lead you upstairs to fuck you,” I said, all accusatory. Giving in to my jealousy. But also setting her up to deny it and chastise me for saying something so out of pocket.
“Pretty much,” she concurred. “But, like, I didn’t care at all at the time.”
She didn’t say it to be hurtful. Just honest.
It started awkwardly. Luna had allowed him to pull her into a bedroom and shut the door, which in her opinion basically meant that she’d strongly signalled her willingness to fool around with him, as the two had schemed.
But as she’d insisted to me many times, Sam truly was a shy virgin, and had no idea what to do with the full-chested beauty eager to offer him her body.
So at first, they’d danced around it. This not being Sam’s house nor room, they were surrounded by artifacts and decorations mysterious to both Sam and Luna. They made some attempt to banter about these, avoiding the issue at hand.
Luna got impatient first. “So, like, can we fucking kiss?”
She embarrassed both herself and Sam with this utterance. His immediate reaction was to consider himself a failure. He should have already made a move, and Luna was ridiculing him for not doing so.
Luna had to perform emotional damage control on her young prospective sex partner. She apologized. She fucking apologized for being to eager to kiss him.
Sam wanted to kiss, he told her. He just wasn’t sure how to initiate it.
Luna gave him some options, all pertaining to physical arrangement. Sam’s preference ended up being for Luna to sit beside him on the bed, but with her body angled towards him at 90 degrees. So instead of sitting on his lap, she was sitting beside him, but turned to him and with her long legs arched over his.
Sam wanted to know where he should put his hands. There were a lot of exciting possibilities; her legs were mostly bare, since she’d worn very short shorts, the fabric thin and loose where it wasn’t stretched across her butt cheeks. She was, of course, not wearing a bra, and her nipples were visible through her thin shirt, making her anticipation obvious. And then there was her tummy, her hair, her face…
“Was it, like, a turn-off that he didn’t know what he was doing?” I asked.
“Oh, not at all,” she said. “Like, totally the opposite. And actually I don’t even think he really was as unsure and hesitant as he was pretending.”
“Oh?”
“Yeah.. I think we both were just really into the whole teacher slash student dynamic we had going, and trying to play it up?”
“Oh my god.”
“Like, maybe this is just how foreplay is with me and Sam? Like how our particularly chemistry expresses itself?”
She delved into the comparison.
Foreplay with me was like trying to constrain an angry animal, she said. Physical and forceful. Not bad, right? I was proud to be a passionate lover and didn’t take it amiss.
Foreplay with Sam, she said, was like two puppeteers working in tandem to guide and tug at the same concept. Within minutes, the two had figured out that just jumping right into the physical stuff wasn’t gonna cut it. The psychological context was of utmost importance to them both.
That’s when I really started to panic. I felt so close to this woman; we’d lost our virginity to one another! And here we were, talking in graphic detail about her sex experience with another man. Which should have been hot as fuck for a burgeoning kinkster like me, but it was starting to seem like the two of them had a very advanced level of sexual compatibility I could only begin to comprehend.
So they hatched a plan for how to kiss one another, arranged their bodies accordingly, and put it into motion.
How did it go for them? She told me things that continue to fuck with me to this day.
Luna and I had considered each other to be our first loves. We’d had a storybook romance and travelled across the country to steal what time we could with one another. We’d discussed the possibility of us having sex extensively before the opportunity eventually arose.
But when those headline moments eventually came to pass? It almost felt perfunctory. “Oh, so this is what sex feels like.” It hadn’t been the transcendent event we’d built up in our minds and our mutual mythology.
And here she was, explaining in vivid detail to me how that promise had finally been fulfilled through her makeout session with Sam.
Much emphasis was placed on taking things gradually, she told me. Lip to lip kissing is wildly intimate and intense, so they agreed to start with “butterfly” and “eskimo” kisses. This meant fluttering their eyelashes against one another’s, and teasing one another with the tips of their noses.
Soon, they’d obliterated the awkwardness that had shepherded them into this scenario together. The touch of nosetip and eyelash was mutually ecstatic, and they moaned their pleasure for each other as they interfaced in this manner.
“Can I please kiss you on the lips?” Sam had finally begged.
But Luna had a better idea. “Let’s play a game,” she suggested.
The game was basically this: go in for a kiss, but resist making contact. If your resolve crumbled and you pushed your face forward that tiny distance for lip on lip contact, it meant you lost.
Luna told me this was the most intense sexual encounter she’d had in her life so far. Her and Sam’s lips hovered within millimeters of each other, but they pulled back time and time again, denying themselves. Moaning harder each time they did it.
Here, I made a bold play during Luna’s recapitulation of events, and asked her to demonstrate for me.
“That sounds mind-meltingly hot, babe,” I said, trying to hide my angst and jealousy. “Can you, like, kiss me the same way so I can see what you mean?”
She actually didn’t hesitate, at all. She was excited to show me.
And it was like lightning in my veins. I was suddenly aware of every contour of her face and mouth. I was certain that whatever sexual discoveries she’d made with other men, I’d be able to adapt to and revisit upon her may times over.
Except…
“See, you’re fucking it up,” she said a minute later. “You keep like, actually kissing me and putting your tongue in my mouth and stuff.”
“It’s cuz you’re so fucking sexy, Luna..”
“Well, the point is the more I tried to like, torture Sam with the denial, the more he went with it? Like we hovered our lips for way longer before they actually made contact.”
I was literally being told that not being kissed by Sam was far more exciting than actually being kissed by me.
I didn’t even bother suggesting we try again and try to duplicate Sam’s greater capacity for restraint. And plus, Luna was clearly more interested in getting back to her story than engaging in more physical contact with me.
“Babe, I can’t explain it but it was crazy. When we finally did, like, actually kiss? We spent so long building up to it and then we were like, literally moaning at each other while kissing as if we were pornstars? But like, this must have been so much hotter and more authentically, like, sexual than anything in a porn…”
“You moan when we have sex,” I pointed out. “Was this different?”
“Yes! VERY different. I…. babe, are you sure you’re okay with this?”
I was no longer sure that 1+1 equaled 2, even, but I told her to continue.