Chubby Crush Dana - Pt. 03: Date

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Dana and I go on our first date. Other firsts occur...
2.8k words
4.75
3.2k
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Part 3 of the 6 part series

Updated 03/05/2024
Created 01/10/2024
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Today was the second day of my relationship with Dana Hartwell. Sure, we were only 18, we were both virgins, and neither of us knew what we were doing.

But that didn't stop us from getting off while we texted each other last night. I was loving every second of my life. At night she texted me. At school?

At school I got to be around her. Stare at her curves. Attempt to remember every inch of her generous chubbiness so I could think of her later.

We also talked, made jokes, and made each other feel good.

I was at school early. Dana's dad dropped her off. He waved at me, and smiled a friendly grin. I did the same. She sighed as she approached me.

"Don't mind him. I told him about you," she said as he drive off.

Dana wore jeans and a dress top. Her maroon top hung loosely over her ample curves. She gave me a big hug. Her chest and belly pushed up against me. She was warm, soft, and smelled amazing.

"Good things, I hope? And not all the things?" I said.

"Naw, I'm not a sadist. He thinks you're a sweet, nice guy."

"Aren't I?" I said, grabbing her hand.

"Of course." She smiled.

We walked to homeroom. I couldn't believe that a few days ago I was worried about telling my two best friends about crushing on Dana. Now the whole school knew.

I was worried people would judge me for dating one of the chubbiest girls at school.

What an idiot I was; It was thrilling to walk the halls holding her hand. I didn't care what anyone thought really. My friends supported me. Dana was beautiful to me. The rest was meaningless.

Any odd glances I got bounced off me. I hoped that she felt the same with me. With Dana, it felt like I was one of the few people who knew she was secretly the hottest girl at the school. Greg knew. I could tell how he looked at her.

We repeated the same routine as yesterday. We held hands in homeroom and on the way to first class. Weirdly we had no classes together this semester. Homeroom was it.

But there were moments in between classes, at lunch, after school...and after school today was our first date.

The day felt like a blur. Dana and I talked a bit, mostly about being excited for the mall. Not that it was special in itself. But being away from school and home, just dicking around together? Perfect.

Before I knew it I was saying goodbye to her in the parking lot again when her dad pulled up.

"Hey Dana," he said, "I got an earlier shift at the deli. You and your guy friend want a ride now? I can still pick you guys up after the movie."

"Colin? That works?" she asked.

"Yeah, I got my pack, though. Uh, maybe-"

"Hey," she said with a smile, "Just leave it in the car with mine. They'll be there after the movie."

Sweet. This meant we'd go to the mall earlier, and spend more time together. All these lucky breaks...what did I do to deserve this?

I climbed in the back seat of his car, and Dana followed me.

"It's like butler style, this way," she said. Her dad laughed at the joke. He seemed cool.

We left the school. Her dad had the music up a bit, but still chatted with Dana about classes. Then he addressed me.

"Colin, you treating her with respect? Just kidding, ha-ha. I know Dana wouldn't take any crap."

"Yes, sir. I'm...a good. Yeah."

"Dad, come on," she said, groaning. "Don't be hard on him." She put her hand on my leg. Pretty high up.

"Okay, okay. I'll shut up." He turned up the radio.

"Sorry, he means well," she said. She bit her lip and rolled her eyes.

"Hey, free ride. With you. No complaints!"

She rubbed my thigh. "Well," she said with a purr, "you got that right."

She kept her hand on my leg but didn't push it further. Good thing too. I didn't need a boner with her dad here.

We got to the mall shortly after. Our bags stayed with the car. We waited until he had gone, and she grabbed my hand.

"He knows we just started dating. I just, I dunno." She shrugged her shoulders. Her boobs jiggled a little.

"All good. Dads scare me, so...Less things for him to get mad at, ha-ha."

We walked hand and hand into the mall. It was a basic shopping center, with two floors and escalators.

We walked aimlessly for a bit.

"I hate that I couldn't change before, but a ride's a ride," she said. "I've just been sweating in these clothes all day. Can we sit? Maybe food court?"

"I'm pretty hungry," I said. "It's a plan."

We got some pizza and a Coke each.

"So," she said, "Like I was saying. Sorry if I'm all sweaty. I have a BO problem. Comes with the territory."

I leaned across the table, and performed a subtle sniff of her.

"Smell great to me."

She laughed. "Sure. You think my stink smells good though."

"That's inaccurate. I think you smell very pleasant normally."

"Ooh, pleasant!" She mocked me with a grin. "Okay. Thanks though."

"So only child?" I said.

"Yep. Just me and Dad. Mom remarried." She shrugged. She jiggled. Her maroon top and the V-shape dip into her cleavage was hard to ignore.

"Oh, gotcha." I sipped my drink. "I'm an only child. Parents are together, but there's no romance anymore, ha-ha."

"Aw. Couples need romance."

She started playing footsies under the table. I daydreamed I was under there, staring at her thighs. Imagining the jeans coming off...

"So...remember last night?" She stared at the empty plate.

"Yeah, of course" I said, watching her. I stole a glance at her fair skinned breasts, again.

"I really did...come...to you," she whispered, "telling me why I turn you on."

I could already feel myself stiffening.

"I really did too," I said quietly. "It's so easy with you. Well, not easy like fast, I mean-"

"Don't." She looked up into my eyes suddenly. "Don't ever feel bad if you get horny because of me...Or if you don't last long, especially if I'm the reason."

"Okay," I said. I wasn't able to elaborate further, it seemed. She was so much more confident than I was at saying intimate things.

"Let's walk around a bit more?" She got up. "Movie's not on for an hour."

I got up hesitantly, mostly sure that I wasn't hard enough to be noticeable.

I watched as she cleared her tray at the trash. Her soft curves looked so squeezable. I did the same with my tray and we clasped hands again.

We didn't see many people our age. Didn't recognize anyone. I realized how anonymous we were here, instead of school, where everybody knew everybody.

I felt strangely empowered. I stopped Dana abruptly, and when we were standing in the alcove of an empty store, I kissed her.

She tensed for a second, then melted into me. Her lips encircled mine, and she let out a tiny moan. I broke off the kiss early to avoid losing my ability to appear respectable in public. Dana put me on edge, constantly.

"Wow," she whispered. I grabbed her hand and led us back into the mall traffic.

"Our first kiss," I said a little sheepishly.

"Aw," she said, "you're so sweet." She hugged my side and we walked hip to hip. Her wide hips bumped against me over and over.

She stopped at the entrance of a women's athletic store.

"I think I need a spare change of clothes. How about you?"

"I don't think they have anything in my...gender?"

She giggled. Her cleavage heaved. "Funny. No, I'm feeling gross in my all-day clothes. I'll feel...sexier...if I'm in something fresh. Guys wear the same clothes days in a row, right?"

"Yeah, I'll survive," I said, "but you can shop. I'll wait out here, or...?"

She looked at me funny. "Nope, you're going to come to the change room, I'll try on some stuff for you."

She led me by the hand through the store. She grabbed a few pairs of leggings, and a couple tops. I waited for her to come out of the mirrored doors while I sat nearby on a small couch.

She emerged wearing a dark blue tank top that hugged her curves, and black leggings that were skin tight.

I wasn't prepared, as it was one step closer to seeing Dana naked. Jeans hugged tight against her legs and ass. But these leggings exposed every subtle surface detail of her thighs, her calves, her crotch, and her large ass. It was a sensory overload.

"Well," she said, a little unsure of herself, "is this...okay? I feel a little naked. I don't usually wear things so-"

"Dana, you look really, fucking, good."

I could see the shape of her love handles, and her soft belly, which stuck out a little but was otherwise fairly smooth, just round.

"Aw, thanks. If you don't hate it...these are good for now. I won't try on the others."

I almost objected as I would have loved to stare at another variation of tight clothes. But I could tell she wanted to get going.

A chubby, middle aged woman rung her up at the till. She was nice enough to let Dana wear the clothes out, after de-tagging them. She put her old clothes in a shopping bag.

"You two are a cute couple," she said. "Nice to see a guy who appreciates us curvy ladies." She winked at Dana.

Dana surprised me by saying, "Oh yeah. He likes that my ass is big."

I blushed, and smiled.

"Aw, you made him go all red! Anyways, you guys have fun!"

We left hand in hand. I looked back and the woman winked at me. She looked...hungry.

"Sorry if I was weird," Dana said. "Just seemed like she would appreciate your preferences."

I laughed weakly. "All good. I felt bad, I sort of just...said nothing, ha-ha."

"I put you on the spot. I think she thought you were hot. She would be right." Dana hugged me again. I loved the constant PDA. I loved how her tight new clothes made her skin feel almost naked to my touch.

We made our way to the movie theatre. We got some popcorn, candy, and a large slush.

We found our seats. As the trailers played, we realized nobody was sitting ahead of us at all. It was the last week of the showing, and the theatre was mostly empty.

The movie was pretty scary from the start. We held hands tightly and she hugged into me during some tense scenes.

Halfway through the show, she moved my hand, placing it between her legs. These seats were older, still not yet replaced by the reclining versions. It meant we were pretty close to each other.

She moved my hand along the inside of her thighs. Her cushiony, amazing thighs. She let go once I was keeping up the movements solo. I was un heaven massaging her legs.

She reached over my arm and starting rubbing her hands on my junk, over my pants.

Her leggings were so fucking smooth, and I rubbed closer and closer towards the entrance of her thighs. We kept our eyes on the movie, no longer following the story.

Dana opened her legs. I felt my way down, and found where her leggings dug into her camel toe. I stroked along the soft slit, totally unsure of my actions.

She undid my jeans with shocking ease. Good day to forget my belt. Her hand slipped under my boxers. She grabbed hold of my hardening member. Holy fuck.

I'd never had a girl touch me, Let alone Dana Hartwell.

"Go under," she whispered into my ear. Her breath was very hot. She widened her legs further.

I lifted my hand towards her tummy, and slid it down inside her tight leggings. I was touching her bare skin. It was pillowy soft, and crazy warm.

My hand grazed down, over her chubby mound. She was totally smooth-- she definitely shaved this morning.

She made a breathy moan in my ear.

I probed further south, as she started stroking my junk. I was as hard as I've ever been. My heart felt all fluttery.

My fingers found the familiar shape of her slit, only this time it was skin on skin. No underwear. She was very wet. Her creamy smooth thighs brushed against my hands, gripping them gently. I pressed in a little and her lips guided me inside. She gripped my dick harder. I pressed on.

I was in totally new territory. I didn't know my way around. I only knew the clit was there, somewhere.

I pressed inside her lips. I found a slick, wet entrance. I pushed a finger inside.

The sound she made in my ear...It was the hottest sound I'd ever heard. A whimper that was all pleasure.

I was fingering Dana in a theatre. No one could tell.

I pushed as far as I could, and my finger slid in deep. She was so fucking wet. Suddenly her free hand found mine, and at first I thought she was pulling me away. She directed my hand slightly higher. I felt a bump, a nub. Oh. What a dumbass.

Dana helped me find her clit. I started to massage it quickly with my finger. She tensed a little, and whispered, "Slow, baby."

That was now the second hottest thing I'd heard. I reduced my pace. "Mmm-hmm," she quietly moaned.

I was facing a dilemma. My first handjob was about to end very abruptly. I wanted to keep touching her, and I didn't want to ruin my only pants. Her dad was picking us up in an hour.

But, fuck, she was talented with her hands.

Finally, I whispered, "Dana, I'll come if you don't stop. Let me take care of you right now."

It was a whisper, but it was a demand. She slowed, then stopped her hand. She moved it to my thigh. She gripped my leg a little hard.

I never stopped my diddling, and I was only now realizing I was about to make Dana come already.

The musical score started to swell, as if the horror movie itself was intentionally assisting to mute her upcoming orgasm.

She seized her legs together tightly, burying my hand tightly between her marshmallowy thighs.

She gasped into my ear, a feminine yet guttural noise, that topped all sounds prior. She quivered against me.

The music died down.

I made Dana come, I heard her come, I felt her come.

She pulled my hand up and out of her pants. "Holy. Fucking. Fuck," she panted in my ear, with a breath between each word.

"That was...incredible," I said.

"Thank you, sexy," she whispered back. "So, so, much. Poor you though, you got nothing in return..."

"Naw," I said. "Not true. I got to do...that."

"Well, I owe you big time." She sighed deeply and rested against me. The smell of her arousal was new to me. I loved it so much.

The movie sucked. But it wasn't a total waste of time.

We got up and left when the credits rolled. We walked hand in hand to the parking lot.

When her dad pulled up, she didn't let go.

"Hey, happy couple," he said, as we climbed into the backseat.

"Hey, Dad."

"Thanks for the ride," I said politely.

"No sweat. Guys had fun?"

Dana gave me a secret look.

"Pretty fun," she said, downplaying it for the sheer irony.

"Good stuff."

He didn't say anything further. Dana held my hand the whole drive home.

They dropped me off at my house, and I resisted kissing her goodbye. It just seemed tacky with her dad there.

"See you tomorrow," I said, and turned to her dad. "Thanks again for the ride."

He said, "No sweat." She just smiled, and said, "Bye."

Then they were gone.

Surprisingly, Dana wouldn't wind up texting me tonight. My best guess was that she was tired from our day.

I took off my grimy clothes and crawled into bed, naked. I rubbed my face, and realized Dana's scent was imbued into my fingers.

I grabbed a clean sock, and inhaled every last aroma from my finger as I came quickly, right after I put my finger in my mouth.

Dana's secret taste. The flavor of her pussy. I tried to imagine tasting the source, but my imagination couldn't get there.

I'd just have to experience it for myself.

With my progress so far, it couldn't be long from now...

...And Prom was on the not so distant horizon...

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AnonymousAnonymousabout 1 month ago

Love the stories of teenage first time lust!!

Reminds me of my own. Nice pacing

And descriptions of the action. Hope to read

More from you. 5 stars.

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