“Matteo”, Isabella yelped, and she clenched her hand into a strong fist as she felt his sheathed cockhead brush against her moist folds. She was shaking in panic. The first time hurt, so she was definitely sure it was going to hurt her again. She was so scared to feel his cock against her entrance again because it hurt the first time she tried to push him inside her.
“Shit!” Matteo cursed as he had no idea if she was a virgin or not, but if she isn’t, there are chances the cock she fucked was smaller compared to his, so he took it slow. “It would only hurt a little since you are wet”, Matteo convinced her, and Isabella nodded. He ran the head of his cock along her slit to spread her ample wetness all over his cock once again before pressing the tip of his erect cock against her entrance, getting ready to penetrate.
Isabella widened her legs for him and took a quick breath. She swallowed hard as she recalled the agonizing sensation she experienced when she attempted to shove his cock into her. The thought of his cock penetrating her cunt once more both terrifies and sends thrills down her spine.
Matteo pulls his hand out from between them and settles his chest against her boobs. He lowered his gaze to hers. “It’s okay, princess,” Matteo whispered, sensing her fear. “Don’t be scared princess. I promise I’ll take it slow and easy on you. Just relax for me, princess, and don’t try to pull me out.” He said in a calm tone that soothed her. He gripped her breast with his free hand, raking her nipples between his thumbs and forefingers.
The feel of his rough hand giving her a good squeeze felt so good, and Isabella moaned, feeling at ease and pleasure in having her breast pressed by him.
“Are you ready for me, princess, to feel my cock base deep inside you?” He asked, keeping his eyes on her as he teased her entrance with his cock. Isabella nodded, giving him approval, but he wanted to hear her say it. “Use your words, love; are you ready?” He asked in his deep voice, causing a vibrating feeling inside her.
Isabella hates it when men call her that sweet name, but with Matteo, it actually sounds different and hypnotizing. She looked up at him and said exactly what he wanted to hear. “Yes, I’m ready, Matteo; do it,” she said boldly as she felt a little comfortable with him.
After hearing her response, Matteo pushed his hip forward and gently started to enter her, watching her face for every reaction. He took it slow since his cock was too huge for her to take it all in at once.
Isabella closed her eyes, anxiety engulfing her once more, but she convinced herself that she was only repaying a favor and nothing more even though she knew it was for her own pleasure. She was only afraid of the pain. “Matteo!” she shouted in anguish as she felt his massive cock-head penetrating her pussy.
“Relax, princess”, Matteo says, his tone reassuring her that he would not harm her. “I want you to hold on to me if it hurts”, He added, and she gripped his bicep. He took his time, pushing his huge cock inside her just to ensure he didn’t hurt her or make her feel much pain.
“Are you okay? Are you comfortable with this?” Matteo asked, staring down at her tenderly and making sure she enjoyed every sensation.
“Matteo, I’m fine… Don’t stop”, Isabella gasped out, tears brimming in her eyes as his cock split her entrance open and the first inch of him began disappearing inside of her.
Matteo leaned down to the side of her face and whispered, “Is this what you want?” He asked, nibbling on her ear.
“Yes”, Isabella whimpered, her cunt quivering as she felt the head of his massive cockhead start to stretch her insides open. His cock is so huge that it made her feel like a virgin who was being deflowered for the first time. It hurts so badly.
“Fuck!” Matteo groaned; she was extremely wet, yet he kept struggling to get inside her without forcing it. “Are you sure you haven’t done this before?” He asks, not wanting to go hard on her.
Isabella closed her eyes and nodded her head in embarrassment.
“You’re just so tight inside, princess,” Matteo said as he observed her face, gauging her reaction to see if she was in pain or not in case it could prompt him to stop in any way.
“Matteo, please don’t stop”, Isabella implored, feeling her core stretch. “Please…” She whimpered in pain, clutching his bicep.
Matteo was concerned. It felt like she was feeling pain instead of pleasure. “Do you want me to go easy on you, Isabella?” He asked because he wanted to make sure she was feeling pleasure instead of pain. “Please be free with me, sweetheart”, he added, causing her to blush hard even though she was in pain. “Does it hurt?” Matteo asked, and his deep, soothing voice made her stomach churn.
“No, it doesn’t, Matteo”, Isabella lied because she knew if she said yes, he would stop. “Matt…” She whined in pain when another inch of his cock slid inside her, and it made Matteo stop as he was completely alarmed by her whimper. Isabella’s eyes opened, and she wondered why he had stopped. “Could it be that he overheard the painful sound she made?” She thought.
“Does it hurt, princess?” Matteo asked with concern, his gaze fixed on her.
“No, it doesn’t,” Isabella answered, forcing a phony grin as she glanced up at him. “Just be gentle,” she said.
“All right, princess”, Matteo said, kissing her cheek as he continued but this time he was very careful with his penetration and never rushed, no matter how fervently his cock throbbed with the need to be inside her cunt.
Isabella started to grimace as his massive cock started to penetrate and stretch her inner-walls open. She flattened her forehead against his chest, biting her lips as she peeked down to see whether he was fully within her, but he was only halfway in. She grumbled softly in anger, realizing he wasn’t fully inside her yet and she was already in so much pain. “Tisssss,” she hissed as the pains intensified.
When Matteo discovers she was hiding her face from him, he grabs hold of her chin and forces her head up to him. “Look at me!” he ordered, staring deeply into her eyes. “Keep your eyes on Mine, princess,” He said, pushing another inch of his cock inside of her, stretching her cunt even further.
“Ouch”, Isabella hissed, closing her eyes. She wanted to cry, but she didn’t want him to stop.
“I can stop if you want”, Matteo offered again, this time soothing and coaxing her, but Isabella just shook her head.
“No, I’m fine. Keep going”, Isabella responded, as she didn’t want him to stop. She craved for the warm, loving sensation of his cock, even though she was afraid he would rip her apart.
Matteo suddenly stopped with his cock almost half-way in. “Are you okay?” he said, his voice filled with concern.
“Yes”, Isabella stuttered.
Matteo grunted as he pushed in further, until he was halted by her agonizing cry.
“Matteo,” Isabella yelled, her eyes widening. She tried to be strong, but the pain was getting unbearable.
“Fuck princess, are you a virgin?” Matteo asked. She was just too tight for him to go in, or could it be that the previous man she fucked didn’t stretch her enough?
“No, Matteo, please don’t stop,” Isabella cried as she lifted her legs, wrapped them around him, and trapped him in her embrace.
“Shit,” Matteo muttered once more. Despite his clear desire to fuck her, he didn’t want to force it because he cared about her too much to hurt her. He was definitely anxious and disturbed. “Then why are you so fuckin tight Isabella?” He grumbled about how difficult it was for him to penetrate his entire length inside her.
Isabella wanted to scream at his face that he was too big for her, but she held still. “Fuck me, Matteo; this is what I want “, she said, holding him tight with her legs wrapped around him. “Please don’t stop; don’t ever stop. Matteo, I want you to fuck me”. She moaned, despite her mind reminding her that fucking a guy she’d just met, especially without protection, was completely wrong, but nonetheless she didn’t care since she believed she could trust him after all he had said.
“Fuck”, Matteo groaned, struggling to push in slowly and steadily.
Isabella whimpered a little, hoping he wouldn’t notice.
“Does it hurt?” Matteo inquired once again, but Isabella persisted in pleading with him to continue. He knew she was yearning for it. They both wanted it! But he was afraid he was hurting her.
Matteo abruptly retreated his hip, drawing only half of his cock back and leaving only the tip of his cock inside her, as he peered deeply into your eyes with a concerned expression on his face. “Are you really sure about this Isabella?”
With the look on Matteo’s face, her brain was telling her to reconsider this once again and use this as an opportunity to make him stop and leave immediately. But screw that! This is what she wants-what her body desires, what her heart desires-and even if this was the last time she’d ever do this with her boss, she’d rather spend this whole night having this passionate intimacy with him. “Yes, Matteo, I’m 100% sure. Please fuck me”, she eventually responded, but Matteo wasn’t convinced.
Matteo wanted to stop since he knew this was going to hurt her, but something prevented him from doing so, and he was forced to give her what she wanted. He lowered his face down to her ear, and he whispered, “Hold on tight, Isabella, because I won’t let him have you first before I do” as he was finally ready to claim her as his.
Isabella wondered what he meant by that, but before her brain could absorb and comprehend the point of his statement, Matteo thrust his hip forward and shoved his cock sharply inside her with force.
Her thoughts went blank!