Luna and the Guys, Part 1 [True Story]

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I'd just gotten out of a turbulent relationship with my high school girlfriend when Luna came into my life.

Text here. Visuals inside.
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I was still a virgin at the time. My ex girlfriend, Sophia, was emphatically not a virgin, and that was part of why she was my ex, but the less said about all that the better. 

Luna could not have been more different from my ex. She was kind, innocent, and romantic. It seemed like our dynamic would be completely free of the angst, jealousy, and betrayal that had characterized my previous relationship.

We lived in different towns, but despite the distance we were trading "I love you"s within a month of striking up our correspondence, and before long had promised to lose our virginities to one another. We even took each other into consideration when choosing which colleges to apply to, even though we both understood banking so heavily on a young relationship to be unwise. But the heart wants what it wants.

We ended up getting accepted to two schools quite close together. It meant we’d be much closer together and able to visit each other on a weekly basis. 

Senior year was a whirlwind romance. We talked every day, for hours into the night. We managed to meet up four or five times throughout the year and were each other's firsts as planned. 

Appearance wise, Luna checked all my boxes. Freckles, curly brown hair, pale blue eyes you could swim around in. Long legs that, as a dancer, she knew how to move around on. Full, teardrop breasts that didn't require support to maintain their shape, and rarely received any given Luna's earthchild sense of style. 

Luna's willingness to forego ever wearing a bra emphasized the cultural differences between the more hippie-like town where she grew up and my own. I had never observed any of my female classmates dressing like this, although I suppose some of the less-endowed girls might have been able to pull it off. 

But Luna was not small chested by any means. The first time I'd gotten to hang out with her in person, being treated to the thin fabric of her t-shirt adhering to her breasts like paint, it had struck me that everybody who was friends with Luna was regularly treated to a similarly intimate display.

It made me a bit jealous, and I pointed out to her how revealing her outfits were. Luna was so damn naive and innocent that she was actually totally blindsided by it! She looked down at herself and turned bright red like she was realizing for the first time how much she was showing.

"You don't think guys are actually staring, do you??" She was desperate for my reassurance.

Of course, I knew guys were definitely staring, but it also seemed like Luna had a good community of friends at her school and I didn't want to give her any reason to feel anxious about her place among them, especially because of my own jealousy or possessiveness. So I told her I was sure people treated her respectfully.

I kept thinking about it, though. Suddenly all the stories she told me about interacting with her classmates had a different context; whenever a male friend was mentioned, I had to wonder how this guy felt about my girlfriend’s braless tits.

I gradually put together that Luna had somewhat of a crew of male admirers at her high school. She spoke of them endearingly, like they were her little brothers (many of them were a grade below us) and she was their big sis. I was fairly certain they must have all been lusting after her, but there was no reason to burden Luna with my analysis.

Anyway, compared to Sophia straight up cheating on me, living with the fact that Luna's classmates all knew what her boobs looked like wasn't so hard to deal with.

There were things I missed about Sophia, though. Luna was generous in bed and willing to try things out with me, but it was obvious she was just trying to humor me. 

So Luna would tolerate me cumming on her full, gorgeous breast, whereas Sophia would have writhed about, rubbing my spunk into her flat chest while she moaned, bringing her fingers to her mouth to taste me. Luna would dutifully use her mouth to moisten my penis and get me hard for her, but Sophia couldn't get her face near a dick without her hand automatically slipping into her panties so she could pleasure herself to its sight, smell, and taste.

I pushed these comparisons from my mind. After all, I was in love with Luna, and I suppose I wanted to think of her as the antidote to the heartbreak I'd suffered with Sophia. So I wasn't really trying to dwell on the ways in which I preferred Sophia's bedroom talents.

—

Luna and I started our first year of college excited to fall even more deeply in love with each other. 

Just a few weeks later, she informed me that we Needed to Talk.

Her reasons made sense. Confronted with the reality of starting this new chapter in our lives, Luna was suddenly concerned that we were setting ourselves up for heartbreak. College was supposed to be about us discovering who we were. Assuming that she and I were destined to stay together forever would mean we already *knew* who we were, and if that was the case, what were we doing here in college?

"Does this mean you want to break up?" I asked. "Or, like, have an open relationship?"

"No, I still love you and I still want us to be together," Luna said. "I just want to acknowledge that you and I might change, like, a lot. We might meet new people we're excited to get to know, and I just think we should be honest with each other if that happens."

The astute reader will correctly have deduced that Luna had already met someone; this conversation was after-the-fact damage control. 

Luna trickled me the details of her new crush over the next month. His name was Peter. She was sure to let me know she thought I was better looking, more charming. But he was around her every day, and she had to admit that they had chemistry, and would it be the end of the world if she maybe spent some time with him and even flirted a little? Just to see if there was anything there?

I had a few reactions to this. The first was despair. How was it possible that Luna had turned out to just be another Sophie? After all, Sophie had loved describing to me her feelings towards other men, and constantly reminded me how much danger I was in of her cheating on me or leaving me for one of them. Which she eventually did, of course.

On the other hand, Sophia had just acted that way for her own apparent amusement. Luna wasn't trying to hurt me, she was just trying to have an honest and mature relationship, right?

And then there was the third thing. The one I wasn't ready to admit yet, even to myself in the privacy of my own mind: the fact that I found the whole thing darkly, sickeningly exciting.

The third thing may have been there, but it wasn't enough for me to take it in stride the way things developed between Luna and Peter. Every couple days I'd get an apologetic phone call from Luna about another "mistake" she'd made. First, they'd studied together and fallen asleep cuddling, her round behind thrust into his crotch and his fingers spread across her bare stomach beneath her shirt. Then, a few nights later he'd gone in for a kiss, and she'd made out with him for a bit before admonishing him that they weren't supposed to do this because she has a boyfriend. 

When she admitted it was only a matter of time before she fucked him, I broke up with her.

—

I got over the breakup and went about having my own college adventures. Luna was out of the picture for a while, until she decided to transfer to my school. The decision had nothing to do with me, but she let me know I might be seeing her around campus.

It was actually really great to see her from time to time and we discovered that neither of us had any bad feelings around our history. After all, it was probably silly of us to think a high school romance could have survived the transition into college, and we'd given it an honest shot.

Like friendly ex-lovers often do, we started sleeping with each other on occasion, out of familiarity and convenience. The sex was way better. Before, there'd been this pressure to live up to some imagined grand romance, and our slightly mismatched sexual interests had seemed like minefields to navigate around. Now, we were much more open and honest with each other about what we wanted and what we didn't. 

We became talkative lovers and chatted casually while we had sex. It became a regular thing for us to compare each other to different sexual partners we'd had. Favorably for the most part, but I also teased her for not being as nasty in bed as Sophia, and she teased me for not being able to eat her out as well as Peter could. It all seemed very low-stakes and neither of us felt competitive with each other's partners.

Nonetheless, by the end of the freshman year we'd somehow come full circle to where we were basically exclusive with each other. So we had a bit of a talk about how we wanted to leave things before we parted ways for the summer. 

"Are we, like, together together?" I asked.

"I don't know. I mean, we obviously kinda are, regardless of what label we put on it."

"Right."

"But on the other hand, I don't necessarily want to be in a long distance relationship for the whole summer."

"Yeah, I guess I don't either."

"Oh? Do you have something planned?"

Actually, I did. Back home, Sophia's latest relationship had gone up in flames, and she'd indicated to me that I might get to take her "sexually upgraded holes" (her words!) for a spin. I was quite keen to finally get a sample of what she'd given up to a couple of my close friends, but not me. Again, the less said… ah, who am I kidding, we'll have to make another post about that whole adventure later on…

Anyway, I said as much to Luna, and as soon as the words left my mouth I knew I'd made a mistake. 

"… I see," she said, staring at the floor between us.

I played defensive. "You're seriously going to get jealous?? You've slept with twice as many people as me since we broke up!"

"But this is your ex, who broke your heart!"

I saw her point. 

"Okay. I mean, I guess, I don't have to do anything with Sophia if it bothers you so much," I said, seething inwardly.

She sighed. "No, it's fine, I don't really have a right to tell you not to. And, I didn't know if I should bring this up, but I've sort of been talking to Sam recently?"

"Okay, and?" 

Sam was one of the high school juniors who'd been a member of the Luna Fan Club while she and I dated our senior year. I'd actually met a few of these guys when I'd travelled to visit her, and there was no question in my mind that Sam worshipped the ground Luna walked on. 

When I had eventually pointed this out to Luna, she denied it vehemently. Plus, Sam was "basically a kid" as well as someone she thought of as a younger brother, and it was gross for me to suggest anything along those lines, she said.

"Well, it's gotten a little, I dunno. Flirtatious?"

I felt the heat of jealousy rush to my face. "I thought he was just a kid. Your little bro."

She shrugged. "I mean, he's not a kid anymore."

"Sam? Round little Sam?? Come on, Luna!" 

She actually punched me in the arm. "Don't talk about Sam that way! He's very sweet! He actually… well."

"Well what??"

"He sort of confessed to me," she said. "I guess he's had a crush on me, like, throughout high school."

"Of course he has, Luna. Your whole 'fan club' was totally in love with you!"

"That's so ridiculous! They were not!"

"They totally were and still are."

"Well, not like this, I don't think. I think with Sam it's something actually pretty deep."

"… I see."

"I swear I never thought about him that way before. But when he told me his feelings I guess…"

"You guess what?"

"It was just the way he said it? Like I realized he's not some kid, he's a man with real complex emotions? And the way he told me.."

"What did he say?"

"He made it clear that he wasn't trying to place any expectations on me. He just… he just wanted me to know how happy I'd always made him just to be his friend and like, exist in his world. And that he felt like I'd done him such a favor just by being me, that he felt like he had to at least compliment me in return and tell me how pretty he thought I was."

"… Wow." "So the little twerp was laying it on thick. "Um, and how did you respond?"

"I… got how I get, you know?"

I did know. Luna can't resist romantic lovey dovey talk like this, and was probably cooing her pleasure at his words and saying things like "tell me again you how you think I'm pretty" and then gasping even though it was the 11th time he was repeating it at her request.

A little flirtatious, my ass.

"So…. have you two, like, already made arrangements to fuck, or-"

"Oh my god of course not!"

"Okay.."

"He's still just, like, a k-… I mean, he's never done that before, you know?"

"Right."

"He's never even kissed a girl."

I stared at her for a few moments, trying to wrap my head around this. 

"D-do you want to kiss him?"

She blinked at me, eyes blazing. "I've been having butterflies thinking about it, yeah."

"Oh my god, Luna."

"I'm sorry. I knew it would make you jealous."

It did. But I'd also spent the school year trading stories with Luna about her college sex life, and by now I was no stranger to the fact that the jealousy and arousal were so closely entwined in my brain.

Nonetheless, this was different. She'd approached me with this in the context of figuring out whether we were an Item. She was clearing it with me.

I knew what I wanted to happen but it was hard to get the words out.

"Y-you.." I tried.

"??"

"You should kiss him."

If she thought I was a freak, she didn't let it show. She was too busy being overjoyed she'd been granted permission to kiss Sam. 

"Ohmygod, thank you," she said. "I'm so glad you understand. I can't wait to tell him!"

"You're gonna tell him?!? Like, in advance?!"

She nodded, unable to suppress her elation at the events that were unfolding in her mind. "Yeah! Can you imagine how happy he's going to be to hear I want to like, teach him how to kiss?"

"T-teach … him…."

"I really like that I get to do something so nice for someone," she continued. "And like, how we'll, you know, anticipate it??"

My vision was swimming, but my desires had come into focus beneath the surface where they'd always lurked.

"Will you… will you…." I tried to say. It was still hard to process that this was who I was and what I wanted.

"???"

"Will you tell me all about it? When you kiss him? Will you please tell me how it goes?"