Chapter 4
by
OnTheMind
Which bedroom do you use?
Master Bedroom
"My bedroom is fine," Jack tells her, pointing to the room at the end of the hall. Hannah shrugs and heads there. Inside, she takes a seat on the large king-sized bed and looks at Jack with an expectant expression, but her eyes had a hint of hesitation in them. He realizes quickly that she's waiting for him to explain what to do.
"You ever do anything like this?" He asked as he slowly began to undress, pulling his shirt over his head and undoing his belt. Hannah looked at his exposed chest with a slight blush before slowly following suit and pulling her tank top off, exposing her plain white bra.
"I gave my boyfriend a BJ a few times," she told him honestly, unclasping her bra and exposing her heavy tits. They were beautiful when fully exposed, perky but with a clear show of heft to them.
"I didn't know you had a boyfriend," Jack said as he finished getting off his belt and pulled his jeans down. His cock was straining against his boxers and it was clear Hannah noticed right away, her hands pausing as she got to her shorts. She swallowed nervously for a moment before slowly pulling her shorts off and adding them to the pile of her clothes next to the bed. Her panties were cute pink things with yellow dots.
"Umm, yeah," she finally answered his question. "We broke up after graduation. He's going to college out of state and we didn't want to make long distance try to work out. So I'm not like totally new at this."
"But you've never gone all the way?" As he asked, Jack pulled off his boxers and exposed his cock to the girl for the first time. She blinked a little at it before she looked back at him and shook her head. Finally, she pulled her panties down and exposed her pussy. It was barely a slit between her thighs and he could tell from here she either shaved regularly or she never grew much hair down there to begin with.
"Tell you what," Jack said as he walked over to where she was sitting. Putting one of his hands between her legs he rubbed her pussy lightly. She shivered at the contact. "As much fun as it will be to wear this little kitty out it's been a while since Katey put out and I don't want to bust too soon. So why not show me what you got up to with your boyfriend and then we can get to the main event."
Hannah screwed her face up at this, whether because he talked about wearing her out or because she didn't like hearing about her best friend's parents' sex life Jack didn't know. He also didn't care. With a gentle push on the back of her head he guided her face towards his erect cock. Obligingly Hannah opened her mouth and wrapped her lips around his manhood. Jack decided to let her set the pace at first, simply keeping his hand on the back of her head as a guide. She wasn't bad, sucking gently on him as she slid up and down. She brought one hand up to slide along his shaft as she went. It was clear she couldn't take down his whole length but he wasn't about to **** the issue. There would be time to try more daring stuff as her stay went on.
"Mmh," Jack groaned as he used his free hand to play with her tits. "Why don't you rub your pussy, Hannah? It will help get you ready for what's next."
Hannah tried to pull her head back all the way, likely to tell him something but Jack didn't want to hear it, keeping her mouth on his cock with his hand on her head. After a moment of struggle, she seemingly gave in and slid the hand not on his cock inbetween her legs. It was clear she wasn't exactly thriving on the moment but she did start to moan lightly around his cock as she rubbed, her body responding to the erotic situation even if her mind wasn't. Jack smiled as he switched between playing lightly with her heavy tits to tweaking her nipples. They were small pink things and with a few twists stiffened a lot. Each time he twisted Hannah let out a small whine in her throat. Clearly they were sensitive little nubs. That promised to be fun.
After a few minutes of Hannah's oral lavishing, Jack could feel his balls tighten. Pushing himself a little deeper into her mouth he tightened his **** on the back of the girl's head before he let loose a burst of cum. She squeaked in surprsed and tried to pull back, but realizing quickly that he wasn't letting her she was **** to swallow as much of his load as she could. Some slipped past her lips but Jack didn't mind. After the thrill of the climax passed he pulled back letting the girl up for air.
"Ugh," Hannah groaned as she struggled to get her breath back. She wiped at the cum dripping down her chin. Bending down Jack picked up her top and handed it to her. She looked confused for a moment before he mimed cleaning her face with it. She rolled her eyes but did as she was told, smeaning semen all over her own clothes. "That was a lot of cum."
"I did tell you it had been a while."
"Yeah...um do you still wanna?" She asked as Jack nodded with a smile and pointed to his half-deflated cock which started hardening again as he watched the girl's heaving chest and cum stained clothing. She nodded, at this point resigned to what was about to happen. Hannah didn't complain, after all it would be rude to make a fuss but she did look at him with a small hesitant glance. "How...how are you gonna? What do you want me...um..."
She trailed off, clearly realizing just how at his mercy she'd be as his guest. Jack looked down at her, this red-faced girl who he saw grow up, who was friends with his daughter since the days of kindergarten, who had never been fucked and had no idea what to expect. He considered his options carefully.
Take her hard fast and raw or tender slow and careful.
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Sexual Privilege
Freeuse for One
These branching stories are going to have 3 very simple premises: 1) You exist in a world where your character AND ONLY your character gets to have sex with whatever group or groups of people you choose wherever and whenever he or she desires. 2) The circumstances under which he or she can have sex with that group can be specified generally or specifically. 3) The response of the people you have sex with and/or the general public can be chosen.
Updated on Jun 8, 2026
by Cross C
Created on Aug 31, 2017
by SanctifiedVillified
You can customize this story. Simply enter the following details about the main characters.
With every decision at the end of a chapter your game state can change. Here are your current variables.
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