Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 10 by Cyberweasel89 Cyberweasel89

What did you say to Eleanor?

You teased her.

You smirked at the buxom blonde. "Wow, you really are a cow," you said. The words cut deep and the girl whimpered, biting her lower lip. Yet, at the same time, her nipples leaked a bit more milk and her pale, freckled face flushed. Did she just get a little turned on from being called a cow?

You leaned forward over her breasts, a small hand cupping her cheek. "But cows are cute... And your milky tits are a beauty to be treasured."

A squeak came out of Eleanor's mouth. Her face was so red it was reaching the top of her giant tits. She looked surprisingly meek. "Y...Ya'll don't m-mean that..." she said, her voice cracking as her eyes teared up. "N-No one's... No one's ever seen my boobies or their milk and... and said that about them."

You were starting to think that, while she had lots of sexual confidence initiating and taking the lead, she had very little defense when it came to having the tables turned on her. Filing that nugget away for later investigation. You reached down and rubbed a hand over the top of one of her tits, causing a shuddering breath to escape her lips.

"I mean it, Ellie. By the way, I know this isn't exactly the right order of things while you're got my dick wedged between your cow tits," that term caused another sexual shudder to run through her. "But I'm John. John Doe"

"Eleanor Fairbreast, but..." She giggled, causing her tits to jiggle in your lap with your penis still between them. "Ya'll can call me Ellie like ya just did."

"Good." You raised your hand up high, and before Eleanor could tell what was going to happen, you brought it down, smacking the top of her left tit as hard as you could.

The audible slap of the contact echoed through the bathroom, sending ripples through the fat boob flesh that you'd just spanked, leaving a visible red handprint. Eleanor threw her head back, letting out an anguished gurgle. You couldn't help but raise an eyebrow.

"Did you just...?"

Eleanor lowered her head, her freckled face red as a tomato and biting her lip. She could only nod, ashamed that she'd had an orgasm from that.

You grinned. "Wow, that was downright masochistic of you. Now, finish the job on your cowboy's dick, cow."

She seemed to visibly get hornier at the way you put that. She redoubled her efforts on the titjob, but after foreplay like that, it really didn't take much longer before your hard cock shot its load out from between her massive melons. It shot upright like a fountain, landing atop Ellie's breasts with excess running off onto the counter. You spurted three times, the last much smaller than the other two, before your erection began to rapidly deflate within its marshmallow prison. Panting, Ellie pulled away, stumbling a bit from lightheadedness until she fell forward, her head in your lap. With her chin in the cleft between your thighs, your softening cock fell against her face, a little dollop of leftover semen touching her forehead. She looked up at it, then you.

"Hey, baby..."

"Yeah?" you panted.

"Did you uh..." her cheeks flushed and she directed a shy smile up at you from your lap. "Did ya'll wanna go on a date sometime?"

Uhhh... You reached over, gently ruffling Eleanor's blonde hair. She gave what sounded like a purr at the affectionate yet patronizing gesture. Shit... what were you gonna get into if you said yes?


After giving you her cami to wear, the still-topless Eleanor carried (yes, carried) you out into the school. With surprising luck thanks to the climax of the game outside, you didn't see anyone as you headed for the parking lot. There, Eleanor set you down by a bicycle with a rear basket, attached cargo trailer, flag, water bottle holder, headlights, rear lights, horn... Wow, this thing was really tricked it with tons of accessories. Was that little electronic thing on the handlebar a GPS, or something?

Eleanor climbed onto the bicycle after unlocking it from the bike rack, pulling it off the side walk and patting her lap. "Ya'll can direct me where to go from up here, baby," she said, a warm smile on her face despite being topless in the school parking lot.

To be honest, you were emotionally and physically drained after tonight, so you didn't object when she reached down. You raised your hand to accept, and she pulled you up into her lap. You managed to bury yourself into her warm, soft tits, noting the feel of your bare bum on her skirt.

Aside from directions to your house, you didn't really talk on the way there. You were pretty sure Eleanor wasn't sure what to talk about after the experience you just had. As she rode into the suburbs and pulled up in front of your house, you hopped off her lap, and Ellie put down her kickstand and walked you to the door. Rather than the front door though, you made your way to the side fence. It was your secret entrance, a gap below the gate that only you were small enough to fit through. Before you could climb in, Eleanor cleared her throat. You stopped, looking up at her.

With an uncharacteristically shy smile, she stepped forward and, with a quick motion, pulled her cami up and off you, leaving you naked. Before you could actually react and cover your dick, she picked you up and pulled you into a hug, squeezing you into her bare tits and leaving your legs to wrap around her waist for support.

"What the f-" you began.

"Um... So, did ya'll, uh... What was your answer to my... proposition?" she asked. Despite having just stripped you and pulled your naked body into a bare boobiehug, Eleanor's face was bright pink and she was looking away, clearly nervous and ****.

You sighed. With the time it took to get there, your dick had recovered, and it was now hard and pressing firmly into Eleanor's torso, making it harder to think. "Fine. One date. We'll see how it goes."

Her face lit up! "Yeeeee!" she squealed, spinning with your naked body still in her arms and bare tits.


That was how you and Eleanor met. It was the start of your long relationship with your girlfriend who hates when you wear clothes.

[End Story]

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)