I [26F] tortured my years-long childhood crush with his lipstick fetish years after graduation [MF]

*Note: If you’re familiar with my work, I love revisiting* [past encounters](https://www.reddit.com/user/xoleni/)*. Part of me can’t believe I haven’t written about this one yet. Maybe because it’s so laden with emotion, and set over a long and winding tale of my life—dating all the way back to childhood. I’ll try to skip the life part and head straight to the sex part as quickly as possible. But the life part is what makes the sex part so, well…triumphant. I’ll let you know when the sex starts, though.*

I still remember the day I decided I had a crush on Cole—let’s call him Cole. We were in fifth grade. Only 11, and we understood each other on a level that we didn’t with our classmates. It was like everyone else was doing addition and we’d skipped ahead to multiplication, speaking about the *world*, not just each other. Cole seemed to like the part of myself that I liked best. He seemed to see the me I hoped to be.

Which is why it hurt so much, I guess, when my raging crush went unrequited for years. Don’t get me wrong: He flirted with me. A lot. He sought me out at my locker every afternoon with a story, or the perpetuation of an inside joke. He gave me kind of attention that many a nerdy high school girl longs will blossom into a flower if she watches it long enough.

I watched it, all right. I watched him flirt with my former best friend, and unload his feelings for her onto me.

I watched him get girlfriend after girlfriend, and tell me that they didn’t understand him like I did.

I watched him, at the end of parties, find me to talk. To relax. To be himself.

And I answered him when, at 11pm at night, every night, he messaged me on AIM (I’m a millennial, OK?). That’s when the real talking began. Though by then we weren’t speaking much in school—I was a nerdy good girl, and he was a popular guy—we had an active social life online. Actually, make that *torrid*. To this day I think I’m a fast typer because of the skills I developed keeping up with Cole’s racing thoughts, and our winding conversations that felt like exhales.

Cole was willing to be honest and vulnerable during those conversations, more so than in school. He expressed my importance in his life. And so, I learned that I could have a power over him online that I didn’t have in the hallways. Soon, these conversations became my sex education. Cole, who was more sexually experienced than I was, would talk to me about his fantasies, and I’d share mine. We’d be blisteringly honest. He’d encourage my yearnings. I developed a craving for a secret life—one which I satisfy today on reddit.

And then some nights, he started asking for help in getting off. **Enter: The lipstick fetish.** Cole confessed he had a thing for women wearing striking lipstick. The image of the colored lips covering his cock, leaving traces of color all over his body—it did something for him. Our double life continued. In the hallways, we were polite. I was the SGA president, helping him cum at 1 in the morning.

Then the conversations dwindled. I don’t know why. We moved on. I got a boyfriend. We went to college. He got a girlfriend.

But after college graduation, our circles kept intersecting. He was a social butterfly. I clung to the sidelines, making wry jokes with my fellow outsiders. And keeping my eye on him, still. Wondering why, when I saw him, I wanted to see more of him.

Every time I saw Cole, even into our 20s, it hurt. The sting of rejection was still there, yes—why was I not enough? I’m pretty, and charming, and smart, and and and…But also, the pangs of curiosity. I still felt like we had unfinished business. And finally, the longing. After all this time, we still got along oddly, freakishly well.

The last two times I’d seen him, the unfinished business was in the air, swirling. I thought I was imagining things. Until we went to a mutual friend’s concert. I knew he’d be there. And though I wouldn’t formally admit it to anyone, I knew that night would be the night.

The night I finally, FINALLY, kissed Cole, and could banish him from my heart. This was the final exorcism, in a way, of a long, long crush.

As if I’d made it so just by thinking it, Cole gravitated toward me all night. The funny thing about life is that he peaked in high school, and I only got hotter. And more successful. And more magnetic. I could tell that he was now under my spell, in a way. My best friend and I ended up alone with him and his friend. And when they left, it was finally us. Talking and laughing, the way we always did. His eyes, I’m telling you, they sparkle—it’s one of the reasons I could never quit him. To this day I still haven’t met another person who always seemed, with every sentence, like they were letting you in on a joke, and you should be so lucky to be included.

****

We were talking, and then came the fateful pause. You know the pause I’m talking about—the one where both people are aware of what’s next, and what’s next is not a sentence. Cole kissed me. At last.

His lips were narrower than I expected, and his tongue clumsier. It felt like a 10th grade kiss, not a 24 year old kiss. But we were *kissing*, and I was screaming.

Before he needed to ask, I said he could come back to my place in Brooklyn, so he wouldn’t have to Uber home and cross many bridges. In the back of the cab we played my favorite game, which is the *i can’t wait to fuck you* game of ratcheting up tension.

And I had something planned. Because from our conversations long ago, I knew exactly what Cole liked, what he wanted: To be dominated by a woman wearing lipstick. And I fully intended to blow his mind, so that he knew, once and for all, what he missed out on.

Y’all, it was awesome.

When we got back to my room, I pushed Cole onto the bed. He wasn’t expecting it, I don’t think, and he sunk into the sheets.

“Don’t move,” I said, pulling open my makeup drawer. “What’s your favorite color?” I started grabbing a few lipsticks. Luckily, I have way too many. I spread them out on the bedspread, pinks and reds and oranges.

He said my name. “You remembered.”

I straddled him. “Of course I remembered. Now pick.” Cole chose a red, and looked almost pained in the intersection of fantasy and reality. I stood up in the mirror, slowly, and put it on. When I leaned over him slowly, he arched his back in anticipation of our lips making contact. I pushed him down, not in a rush. We made out and I made sure to leave traces of me on his lips.

Cole, it turned out, whimpered when he was turned on. He was whimpering a lot *before* I put my red lips over his cock. After, it was—well, it was a symphony. In addition to moaning, he was saying things like: This is the most turned on I’ve ever been. He felt seen, I guess.

But it wasn’t enough. I was ravenous. I wanted him to pour forward, melt. I put on different lipsticks, left traces of kisses all over his thighs.

He was naked, and my clothes were still on.

When he begged for me to take them off, I said i’d take my time. And when I straddled his cock and rode him, I took my time then, too. His face contorted as he asked for more. Why should I give him more, when he never gave it to me? I went up and down painfully slow. Just because the pleasure of him wanting more was greater than the pleasure of his cock.

Cole seemed ready to come at any moment, just from the environment I’d created of total domination. Normally I’m more submissive but here, I was able to lean into the power dynamics, felt it coursing through me. Eventually, I pinned his arms back and moved my hips back and forth, up and down until he came.

Cole didn’t reciprocate. As I realized that night, it was always all about him. He did turn over and tell me what I wanted to hear: Of everyone we went to school with, he said it was always me who understood him the most. He cloaked me in compliments. For a few minutes, we met in a place of shared honesty. I think I asked him why, then—why didn’t we get together? But I might not have been brave enough.

What I do remember is the surreal image of it; waking up next to a sleeping Cole. Now that what I’d longed for had happened, Cole’s allure had lessened. But my own self confidence had grown. It was cathartic. Cole wasn’t better than me, just because he didn’t want to date me. I don’t want to date anyone who doesn’t want to date me.

But he *wanted* me. I’d reduced him into creature moaning in a high-pitched voice about how that was the best fuck he’d ever had. To be honest, I hope that never changes. I’d lived with the shadow of him for so long. He might as well live with the shadow of me. Cole will never want me “like that,” but he liked me “like this.” It makes for a minor victory, and a helluva story.

**Note: If the real Cole is lurking on reddit, as part of me feels like he MUST be, then you should have texted me back after our night together. I hope you read every word.**

Source: reddit.com/r/gonewildstories/comments/k195oo/i_26f_tortured_my_yearslong_childhood_crush_with