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“Mr. Shelby and I made a bet… Unfortunately, I lost.”
“Oh… What was the bet?” You asked timidly.
“You.” Tommy said with the barest hint of a smirk on his lips. Your eyes widened in shock and you waited for them to explain. “But it seems your daddy is a little protective of you…”
“Cause I know you, Tommy. I’m not leaving her alone with you.” Jackson scoffed.
“Regardless…” He continued, not bothering with a reply. “That means I get to fuck you while dear ole dad watches.”
“What?” You choked out, looking at your stepdad and waiting for him to say this was all just an elaborate prank or something… But that’s not what he said at all.
“The only options are with or without me present. Either way, Tommy won the bet fair and square. At least if I’m here I can make sure he doesn’t go too rough on you.”
“But, I- I don’t…” You whimpered, eyes already tearing up.
“Are you a virgin, sweetheart?” Tommy asked gently, stepping forward and brushing the back of his finger over your cheek as he studied your face. You nodded and your bottom lip started trembling. “Aren’t you just the sweetest little thing…” He cooed, then glanced at Jackson. “I’m surprised you haven’t tried out her cunt yet.”
“She just turned 18 last month, Tommy.” He scoffed. “I’m a bad person, but I’m not that bad.” Tommy looked back at you with a small smirk.
“Shame… Because now I get to be the first one to use her little pussy.” He seemed absolutely delighted by the fact and your whole body started trembling in fear. “I can already tell you’re going to be such a good girl.” He said quietly, leaning closer to you. “Maybe even good enough to take us both, hm?”
You let out a choked sob and squeezed your eyes shut, feeling completely helpless. It’s not like you can ask Jackson to make this stop… He already made it very clear that this is happening whether you want it to or not.
“Tell you what, since I get to use her cunt first, why don’t you take her first kiss?” He grabbed your cheeks in one hand and turned you to face your stepdad. “I’m feeling rather generous tonight.” Jackson stepped closer and Tommy let go of your face as he backed away. Once he was in front of you, he gently cupped your cheek and brushed his thumb over your bottom lip. You stared up at him with glossy eyes, silently pleading for mercy.
“Fuck, don’t look at me like that.” He groaned, voice low and raspy, as his gaze dragged all over your face. “I’ll make sure he goes easy on you, don’t worry.” He promised, not calming you at all.
You stiffened when he leaned forward, unable to do anything but watch as he slowly approached. His lips brushed yours before finally taking you into a kiss. You let out a soft whimper and his hand snaked around to the back of your head, keeping you from pulling away. Letting out a soft gasp when his tongue brushed your lips, he used that opportunity to deepen the kiss, licking into your mouth, making it even sloppier. After another moment, he finally pulled back, but kept his face close to yours as both of you panted.
“You’re such a good girl.” He cooed and you blushed at the praise. “Fucking perfect… I hate that I have to share you tonight.” It was like a bucket of cold water was thrown on your head as you suddenly remembered what was about to happen.
“My turn.” Tommy said firmly, stepping closer again. Jackson reluctantly moved away, giving the other man enough room to grab your hair and roughly turn you to face him. You gasped at the pain on your scalp, and then again when his other hand settled on your lower back, pulling you into his body as he captured your lips in a kiss.
Snaking his hand down, he squeezed your ass over your dress, pulling you even closer until you could feel his bulge digging into your stomach. You whined in response, not used to being touched like this, or feeling something so crude, and he let out a low chuckle before moving back.
“Y’know… I bet your daddy’s been wanting to do this for a long time.” He said quietly, smirking a little. “Between you and me, I think he lost on purpose.” He mused, talking in a teasing stage whisper.
Your bottom lip continued trembling and you glanced at Jackson before looking back at Tommy, feeling tears brimming in your eyes.
“Oh, don’t cry, sweetheart. If you get me all worked up, I might not be able to be gentle.” He mused. You let out a choked sob, but quickly tried to stifle it because of his warning, which seemed to please him a lot. “So obedient…” He murmured, looking over you with a small smirk. “You’ve always been a good girl, haven’t you? Always so trusting and naive…” You swallowed nervously as you stared up at him, unconsciously trying to move away but being unable to because of his hand on your hair and your ass.
“Now,” His hand let go to start petting your hair as his gaze shifted between your eyes and lips, “I won the bet fair and square. So you’re going to be a good girl and let me claim my prize right?”
You bit your lip and looked over at your stepdad who nodded, telling you to agree. “Yes…” You whispered, looking back at Tommy.
“Good. I was hoping you’d say that.” He smiled, then took a step back, letting his hands drop to his sides. “Strip. Let your daddy and I get a good look at what we’re working with.” His smile turned into a smirk and you looked between them nervously, hesitating.
“Do as he says, sweetheart.” Jackson urged gently.
“Be a good girl and maybe I’ll even give you an orgasm or two. Would you like that?” Tommy asked, making your cheeks heat up. You’ve heard the word before, but you’ve never actually experienced it yourself.
“I- I don’t…” You swallowed thickly and averted your gaze, making Tommy chuckle quietly.
“Christ, Rippner, where'd you find such an innocent little thing?” He scoffed in amused disbelief and your blush darkened in response.
“Her mom had her in Catholic school.” He explained with a small shrug. You’ve always been a little embarrassed about your upbringing and the way it made you different from a lot of other girls your age.
Tommy hummed in acknowledgment, then reached out to grab your chin and turn you back to him. “You don’t want to disappoint your daddy, do you?” He cooed mockingly, brushing his thumb over your bottom lip. You glanced at Jackson again before shaking your head. “Then be a good girl and do as you're told.”