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Chapter 7 by thehuntsman-king
What's next?
Practice
Because Eleanor didn't have infinite money, and because she wasn't trying to be overly ambitious for her first toy, she selected a basic 6-inch dildo of modest girth. She shyly approached the cashier to pay, and the woman there gave her a kind smile and did not ask any questions - it was a sex shop, after all. Their goal was to put customers at ease.
Purchase complete, Eleanor made her way home with her discreet bag. She let her parents know she was going to take a nap, and closed her bedroom door. Excitedly, she stripped off her clothes and unboxed her new toy. Her cock and nipples were hard just looking at it. She bit her lip and took a few deep breaths.
She knelt on the floor by her bed and rested her chest on the mattress, setting her bottle of lube down nearby after squeezing some onto her fingers. Arching her back to stick her ass into the air, Eleanor rubbed a slippery finger against her asshole. She started licking the dildo as she rubbed, then, ready for more, took it in her mouth.
She sucked and slurped on the dildo, then pushed it further in, toward her throat. The first attempt was not very successful, as she gagged almost immediately and had to pull it out.
She took a deep breath and resumed sucking the dildo, now pushing a finger into her tight ass. She moaned onto the cock, tried her best to relax her throat, and pushed again.
She had more luck this time, feeling her throat part just a little around the very tip of the dildo. She didn't gag, and she kept slowly thrusting the toy in and out, letting the tip just ease a tiny bit further into her throat each time.
Meanwhile, her other hand steadily fucked her ass with just one finger. Eleanor hadn't forgotten the eventual goal of her purchase, so, as she enjoyed the fruits of her labor with the dildo in her mouth, she added a second slick finger to her ass.
The feeling of being filled at both ends made her feel good, and slutty, and Eleanor found herself wondering why she hadn't done this before. She kept going, picking up the pace on both ends.
She pushed the dildo a bit too far and gagged again. She pulled it out and kept fucking her ass...and decided she was ready. She pulled out her fingers, lubed up the dildo, and took a deep breath.
Willing her ass to relax, she pressed the tip of the toy against her hole and pushed slowly. Patiently, she rocked back and forth as she pushed, and eventually she felt the head of the cock enter. She gasped. She pushed more, then thrust in and out, taking more of the dildo with each thrust.
She bit down on her sheets. The size of the toy made this a little painful, but she couldn't pretend that was necessarily a bad thing. The pain added a layer to the pleasure, and it was fading as she got used to the sensation. She pushed, more, and the dildo got deeper and deeper inside her.
And soon her hand pressed the base of the dildo against her ass. It was all the way inside. Eleanor grinned wide and pulled the dildo out halfway, before pushing it all the way back in. She groaned softly as she started to fuck her ass, picking up a bit of speed and grabbing a handful of bedsheet as the feeling ramped up toward overwhelming.
She felt wonderfully full, and started to fantasize about the cock filling her being Eddie's. His would fill her even more, she imagined, which turned her on. She imagined him fucking her from behind, pressing her into the mattress, pinning her down. She hoped she could take it - and in that moment, resolved to practice with the dildo every day until their date.
Her fantasy brought her to the edge of orgasm. She didn't want to move, but didn't want to cum on her mattress or the floor, so she brought her other hand down and cupped it in front of her cock. One last thrust all the way in made her cum with a shudder, and she filled her cupped hand with her cum.
Eleanor came up into a squat, and kept fucking herself as she brought her hand up to her mouth and slurped her cum out of it, licking her palm and fingers to get all of it, imagining that she was swallowing Eddie's cum.
What's next?
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A Virgin Trans Girl's Mission
Catching up before starting college
Eleanor had spent high school finding herself, and as a result was still a lonely virgin the summer before starting college. She has three months to fix that. Story is likely to feature: - domination - submission - ENF - dubcon - lesbian - threesome/foursome - humiliation - orgasm control/denial - bondage - and more
Updated on Feb 25, 2025
by thehuntsman-king
Created on Aug 24, 2020
by thehuntsman-king
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