Chubby Crush Dana - Pt. 01: Sharing

Tyler, Jordan, and I were having our last real sleepover before graduation. We were all 18, and on the cusp of whatever manhood looked like. Ty and Jordan were my best friends.

Other guys in our class made fun of us still having sleepovers. But I thought they were idiots; What was more fun than staying up late, and having conversations only we could have?

We talked about death, the universe, girls, sex, porn, you name it. We were all virgins, but we had all had some kind of story to share.

Ty was more handsome than us, and had more "popular kid" friends than Jordan or I had. Jordan was heavier, but used his humor to bypass a lack of confidence. I was the average between them: I looked okay and I was sometimes funny.

We ate junk food, drank pop instead of booze, and finished a couple horror movies. It was about 12:30 at night, and now the game was to chit chat until everybody passed out.

I lay awake, staring at the ceiling of Jordan's basement. It was nice down here because there was a whole floor between us and his parents. We could afford to talk all night at an acceptable volume.

We were all in our own sleeping bags, and we just talked.

"Colin," Ty said, "Marry, fuck, kill: our year."

I thought for a moment. "Sarah B, Sonya, and Dean. How about you Jordan?"

"Ooh, yeah," Jordan said, "Swap those first two. Then Mr. Ross. Hate him."

Ty laughed. "I got a thing for Heather. She's got a nice ass."

Heather and the girls we named, they were pretty for sure. But I was kind of in the closet. I had learned pretty recently that I was either a chubby chaser or had a fat fetish. I didn't like the terms but that's what you got called if you liked girls who were even a little overweight.

"Heather," I said, "She's cute. Her bellybutton is pierced!"

Jordan laughed. "I heard her punani is too!"

I didn't even know that was a thing. It sounded intimidating to me.

We joked around for a bit, but then we fell into a common pattern: reviewing our past experiences with girls, limited though they may be.

Jordan was the least savvy with the ladies, but he still told the story about him kissing Megan Bauch at this year's dance.

He milked it for all its worth.

Ty brought up his impressive list of 7 girls he kissed this year. Each was at least a 7 or 8 on our rating system. We included personalities, imperfections, and whatever rumors we heard about.

Ty also told the story of fingering Gina Roek last month at a party Jordan and I were too scared to go to.

Like I said, I was pretty lame. But I had my moments.

For whatever reason, Pia Rutherford had a crush on me. She was short, athletic, and was very confident. We went on a date at the start of the year, and we made out in her parent's garage for a while.

I even got to feel her up, over a bra. It was pretty awesome. I used it as my number one source of jerking off.

Ty turned the subject somewhere I wasn't expecting. "You hear Greg is going out with Yvonne? Guess he likes 'em chunky."

"Oh, yeah?" I said. Yvonne was my first curvy crush. She had glasses and was a bible type. She was chubby, but a little bookwormy.

"Yup," Ty said. "Fat girls are like scooters: fun to ride but don't tell your friends." He laughed heartily.

I didn't get the joke, and objected to the mean aspect of it. Jordan was heavier, but we didn't make fun of him.

"I used to have a crush on her."

It sounded weird coming out. It was the truth, but I felt guilty. I wasn't sure why I said it. These hangouts tended to reveal some secrets from time to time.

Ty stopped laughing. "Colin, you're serious?"

I nodded.

"Well, you and Greg have a fat fetish I guess." He didn't say it in a cruel way, but I felt shame wash over me.

Jordan said, "Yvonne's nice. I don't think she's ugly at all."

Not exactly a confession on the level of mine, but Jordan sensed I put my heart on the line a little.

"Sure," Ty said. "But she's chubby. So if you like that, I mean, I don't get it. But no big deal."

I wanted to unload some stuff, but Ty made it seem risky. He was the most judgmental, the most superficial. I don't know if telling him how deep this went was a good plan.

I did it anyway. I needed to talk about it.

"I actually have a crush on Dana Hartwell right now."

The room went silent.

Dana Hartwell's nickname was Dana Hartwhale. Nobody ever said this within earshot of her. She was the academic type, and was involved in many school clubs and whatnot. She wasn't bullied, but she wasn't ever spoken of as hot or beautiful.

But she was, to me. She was the heaviest girl in our year, but she wasn't morbidly obese or anything. She just had a big butt, and big thighs. She wore jeans and khakis that did nothing to hide this fact.

Ty broke the silence first. "Hartwhale? Oh my god, dude."

Jordan didn't say shit.

"Okay," I said, "I know. She's big. But I think she's really pretty. She's in my homeroom. I talk to her sometimes."

"What do you say?" Jordan asked.

"Just about...whatever. I just say hey and we talk. Nothing much."

"So, dude," Ty said, "When did this start? When did you start liking fat girls?"

"Look, I don't want to get into this." This was half true.

"C'mon! Don't be mad. I'm sorry. I just don't see her, or girls like her that way. I'm curious. I won't be a dick."

"Yeah," Jordan said, "All good man."

"Alright, I'll start at the beginning. But don't be shitty. I feel crazy in my head about all this, but I'll feel better if I get it out. Don't judge me."

Ty shook his head. Jordan too.

"Okay. It started this year. I was at Dave's house doing a homework thing. I used his bathroom. His sister's laundry was in the corner. I grabbed a pair of underwear. They were huge.

"Dave's mom doesn't live there, so I know it's the sister's. They were granny panties, and so incredibly big. She's like twenty five. So I...sniffed them and jerked off in his bathroom."

"Oh my god!" Ty laughed. "Jesus!"

"You said you wouldn't be a dick," I said, dejected.

"No, I'm not. It's just crazy, keep going."

"Fine. So I put them back and leave when I'm done. I never went back to his house since. We don't normally hang out.

"So maybe that started it. But next time I'm at school I start noticing the bigger girls. And I almost get a fucking boner talking to Yvonne."

"Damn," Jordan whispered.

"Yeah," I said. "So for a bit I think I have a crush on her. But she's not my type, personality-wise.

"I even look at mom's differently too. You guy's are safe, your mom's are scrawny. But like, Mike Terrence? His mom is huge. I saw her at the corner store and I thought about it next time I...yeah. Anyways...

"Then I start talking to Dana Hartwell. I like her, but also I'm like crazy turned on by her. I guess I was before but I didn't admit it to myself. So when I'm around her I'm constantly worried about getting hard.

"And I started jerking off, to thoughts of her, or like scenarios I make up. When I'm in bed."

The three of us don't usually get that deep into talks of self-servicing. But I knew if I was going to unload, I had to say it all.

"So after I've jerked off to her, seeing her at school is weird. I worry she could know, somehow."

"I get that." Ty nods solemnly. Sometimes, I swear they can tell. Sorry! Keep going."

"Mm-hmm," Jordan adds.

"So now I like her, and I know people say whale and fat and everything else, but...I wish she was my girlfriend.

"I used to enjoy thinking about Pia, and what we did. But picturing doing that with Dana? Or having actual sex? It does something to me on a whole other level.

"I can't even imagine it. It seems like my brain would overload with pleasure. Fuck, I know how weird that sounds.

"So the last thing is...we were in the band room last week, Dana and I.

"We were just hanging around chatting at lunch. We sat in the instrument room, in those little cubbies?"

"Oh, yeah." Jordan nodded.

"So she sat in one, with her feet up. I sat next to her. I shared my Coke with her. I was close enough to like, smell her? It was a warm day, so we might have been sweaty. But like her sweat smelled good to me. Wasn't too strong.

"But now I'm getting a fucking boner. Cause she smells good and I can feel her heat. Maybe it was just the way I was sitting."

"Okay." Ty scratches his head. "So Dana sees your boner?"

"No. But the bell rings."

Ty and Jordan say "fuck" at the same time, and groan at the predicament.

"Exactly. So Dana says, 'You getting up?' and I just laugh like a fucking dummy.

"It isn't about to go away, not with her there, in this little room that smells like her, with her so close.

"But I still scoot out of the way and stay sitting on the floor. She comes out and sits next to me but I still can't stand up.

"I wanted to kiss her. I think she would have let me. But I feel like a freak so I just sit there in silence, just waiting for her to realize what's going on.

"She says, 'Can you help me up?' and I just hope to god she doesn't notice as I finally stand up. And offer her my hand."

"Why didn't you just tuck it up into your pants?" Ty asks.

"No way to do it without being seen. So she grabs my clammy hand, and I help her up. She pops up right against me. She bumps it with her stomach. She looks down."

"Fuck!" says Ty. Jordan looks on with intense focus.

"So she just looks at me, and smiles. And just right away, says, 'I'll take that as a compliment,' and leaves. Haven't talked to her since."

Both of my friends express their exuberance at my tale. They laugh a little but I can tell it's not at my expense.

I felt lighter, but still didn't like how that was the last time I talked to Dana.

"I just don't know if I should say something, or act like it never happened?"

"It happened, so forget that. But she seemed cool, mostly," Ty said thoughtfully, "So just talk to her. It'll work out."

"If I were you," Jordan said, "I'd use it as your next icebreaker."

It was good advice, from both of them.

"I want to ask her to prom."

Nobody responded.

"But I'm not confident. I hate that it would bug me, and I feel shallow. But I am worried what people might say. The looks I'd get."

"Well..." Jordan said, "You can only worry about yourself. If you like her, and want to go with her to prom, then ask her. She might even say no. Someone might have asked her already. Fuck anyone else. You like what you like. That's everyone on Earth."

"Wow," I said. "Thanks, Jordan."

"Dude, sorry if I was a dick. I think she's nice." Ty laughed. "Just cause I don't like something doesn't mean it's not hot to you. Thanks for telling us what you're going through."

"I do feel better."

"Just don't jack off to my mom's underwear!"

We all laughed. We talked for another hour before we ran out of steam.

The following week I walked up to Dana in homeroom.

"Hey, Dana." I smiled. My plan was to ignore the fiasco.

"Hey!" She looked around, then leaned in close. "You gonna get a boner again if I talk to you?"

She was smiling weird, and I could tell she was a little nervous talking to me too. Not enough to resist teasing me, though. I was impressed by her boldness.

"Well, we'll see." I tried to be cool. " I wanted to ask you...Are you...I mean, do you have plans for prom?"

She smiled sweetly. She had green eyes. I was smitten.

"No," she said. "Totally free."

I was lost in that moment for a while. I eventually asked her. She said yes.

I said prom, but I really wanted to date her. Like boyfriend/girlfriend. But I had an in.

Prom was a month away. There was plenty of time to start something new and exciting.

We exchanged cell phone numbers, and said bye for now.

I thought about her all day.

Just before bed, I got a text. It was from Dana.

"You up? :)"

...