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You are here: Home / Adult sex stories / Tiffany's First Time

Tiffany's First Time

Adult story Editor December 25, 2020 Leave a Comment

Tiffany nods, feeling a little embarrassed. “Um, can I see it now?” she says quietly.

John looks at her for a moment, then nods. “Sure,” he says, and starts to move his body slightly. Tiffany watches, fascinated, as he reaches down and starts to pull his boxers down.

When his cock is revealed, Tiffany’s eyes widen in surprise. She has never seen one before, and it looks much bigger than she expected. She can’t help but stare at it, feeling a mixture of curiosity and intimidation. It looks much bigger than she expected, and she can feel her heart racing with anticipation.

“Wow,” she whispers, her eyes still fixed on his length.

John chuckles, noticing her reaction. “Like what you see?” he asks, a hint of amusement in his voice.

Tiffany nods, feeling a little embarrassed. “I’ve never seen one before,” she admits.

John chuckles. “Don’t worry,” he says reassuringly. “I’ll be gentle.”

Tiffany nods, feeling a little more at ease. She looks at John’s cock for a few moments, then reaches out hesitantly and touches it with her fingertips. She feels it twitch at her touch, and she gasps softly.

John smiles, watching her reaction. “You can touch it if you want,” he says softly.

Tiffany nods, feeling a little more confident now. She wraps her fingers around his cock and starts to stroke it gently, feeling it grow harder and harder in her hand. Tiffany’s fingers trail down the length of his shaft, feeling the warmth and softness of his skin. She notices the veins pulsing under her touch and the texture of the skin, the way it feels smooth yet rigid. She can’t help but feel a sense of curiosity and wonder as she explores his manhood.

As she touches him, John reaches down and starts to touch her as well, running his fingers lightly over her breasts and down her stomach. Tiffany moans softly, feeling a wave of pleasure building inside her once again. John lay back on the bed and watched as Tiffany moved between his legs. She tentatively reached out a hand and brushed it over his length, tracing the veins that stood out against his skin. John felt himself grow even harder at her touch.

Tiffany looked up at John, her eyes meeting his. “Is this okay?” she asked, her voice barely above a whisper.

John nodded, his breath hitching as she continued to explore his length with her hands. He watched as she leaned in closer, studying him intently as she traced his balls with her fingertips. As Tiffany’s fingers touch John’s cock, she feels a jolt of electricity run through her body. She looks up at him, seeing the desire in his eyes, and it makes her feel bold. Slowly, she wraps her hand around his length and starts to stroke him, marveling at how it feels in her hand.

“How does it feel?” she asked, her eyes flickering up to meet his.

“It feels amazing,” John replied, his breath catching in his throat as Tiffany stroked him a little faster. “Just take your time.”

Tiffany smiled nervously but continued to explore him with her hands. She marveled at the way he responded to her touch, growing harder and more sensitive with each stroke. She spent several minutes just playing with him, feeling the weight of his sac and the soft skin of his length, getting more and more comfortable with him.

John’s breathing grew heavier, and he reached out to touch her hair, running his fingers through it as she worked. “That feels so good,” he said, his voice low and husky. “You have no idea.”

Tiffany blushed, but continued to explore him, her curiosity growing with each passing moment. She leaned in closer, studying him intently as she stroked him, and he moaned softly as she caressed his sac.

“Is this okay?” Tiffany asked again, looking up at him with wide eyes.

John nodded; his eyes closed in pleasure as she continued to work. Tiffany takes a deep breath and looks up at John, her nerves written all over her face. “I’ve never used my mouth before,” she admits, her voice barely above a whisper.

John looks down at her with a mixture of amusement and encouragement. “It’s okay, Tiff. Just do whatever you want to do,” he says, running his fingers through her hair.

Tiffany nods, taking a deep breath before leaning down and pressing her lips to the tip of his length. She’s surprised at how smooth and warm it feels against her lips, and she hesitates for a moment before opening her mouth and taking him in.

John gasps as he feels her mouth close around him, and Tiffany feels a sense of pride at the reaction she’s elicited. She starts by just taking him in as far as she can, her hands holding onto his hips for support. Tiffany pulled back slightly from John and looked up at him, unsure of what to do next. “You okay?” she asked nervously.

John let out a small laugh. “Yeah, I’m good. That felt amazing, Tiff.”

Tiffany smiled, feeling a sense of pride wash over her. “Good. I want to keep going.”

John nodded; his eyes fixed on her. “Whatever you want.”

Tiffany took a deep breath and took him back into her mouth, this time swirling her tongue around the head before taking him deeper. She felt him twitch in response and a small moan escaped his lips.

“God, Tiffany,” he groaned. “That’s good.”

Tiffany felt a surge of confidence and began to move her head up and down, taking him in deeper with each stroke. John’s hands found their way to her hair, holding it out of her face as she worked.

Tiffany was determined to give John the best blowjob of his life, so she carefully listened to his reactions as she tried different techniques. She started by bobbing her head up and down, taking him in as deep as she could. She felt his hands on the back of her head, guiding her movements and urging her to take him deeper.

Encouraged by his response, she took a deep breath and tried something new. She swirled her tongue around the head of his length, eliciting a groan from John. “Oh, fuck,” he moaned. “That feels amazing, Tiff.”

Tiffany smiled, pleased with herself, and continued to experiment. She tried using more pressure with her tongue, running it up and down the underside of his length. She could feel him twitching in response and she knew she was doing something right. She varied her speed and angle, trying to find the perfect combination to drive him wild.

She paused for a moment and looked up at him, her lips still wrapped around him. “Do you like that?” she asked, her voice slightly muffled.

John’s response was a guttural groan, and he pulled her back down onto him. Tiffany took it as a yes and continued her exploration, determined to make him come undone.

She reached up with one hand to fondle his balls, gently massaging them as she continued to move her mouth up and down his length. “Oh, fuck,” John moaned. “You’re so good at this, Tiff.”

The more she tries, the more into it she gets. She feels a sense of empowerment, knowing that she’s making John feel this good. She’s not sure how long she goes on for, but eventually, she feels him gently pulling her off him, his breathing heavy.

Tiffany looks up at him, a mixture of pride and disappointment written all over her face. “Did I do okay?” she asks.

John pulls her up to him, planting a soft kiss on her lips. “You did more than okay,” he says, smiling. “That was incredible.” John shifted his weight and propped himself up on his elbow, looking at Tiffany. “So, what position do you want to do it in?” he asked, his voice soft and patient.

Tiffany hesitated, unsure of how to answer. She had never really thought about it before. “I don’t know,” she finally replied, her voice small.

John smiled kindly at her. “It’s okay, take your time. Think about it and let me know when you’re ready.”

Tiffany nodded, grateful for his understanding. She closed her eyes and took a deep breath, trying to picture herself in different positions. Doggy style seemed too aggressive, missionary too vanilla. She opened her eyes and looked up at John. “Can we do it…with me on top?” she asked, her voice barely above a whisper.

John nodded. “Sure, that’s a great position for your first time. We can go at your pace.”

Tiffany felt a wave of relief wash over her. “Okay,” she said softly. “Let’s do it.” John and Tiffany moved into a comfortable position on the bed, with Tiffany straddling John’s hips. She was nervous but excited to finally have sex. John could see the mix of emotions on her face and reached up to gently stroke her cheek.

“You ready for this?” John asked, his voice low and reassuring.

Tiffany nodded, taking a deep breath. “Yes, I’m ready.”

John smiled and guided her hand to the bedside table, where a box of condoms was sitting. “Can you grab one for me?” he asked.

Tiffany hesitated before speaking up. “Actually, I have an IUD,” she said softly.

John’s eyebrows raised in surprise. “Oh, okay. That’s great then,” he replied, a small grin on his face.

Tiffany straddled John’s lap, feeling the heat between her legs and the weight of his arousal pressing against her. She took a deep breath, trying to steady her nerves as she positioned herself above him. John’s large hands rested on her hips, guiding her movements as she tried to find the right angle.

“Good girl,” John said, his voice low and reassuring. “You’re doing great. Just take it slow.”

Tiffany nodded, feeling a mixture of excitement and apprehension. As she lowered herself down onto him, she felt a sharp pang of pain, but it quickly gave way to a wave of pleasure. She moaned softly, feeling his length stretching and filling her in a way she had never experienced before.

“It’s okay, Tiff,” John whispered, noticing the slight grimace on her face. “Just relax and take it easy.”

Tiffany nodded, biting her lip as she adjusted to his size. She slowly began to move, rising and falling on his shaft, each movement sending sparks of pleasure through her body.

As the minutes ticked by, Tiffany grew more and more comfortable with the rhythm of their movements. She leaned forward, pressing her chest against his, her fingers trailing over his skin.

“Oh, god,” she moaned, feeling her body responding to him in ways she had never imagined. “This feels so good.”

“Jesus, you’re tight,” John groaned, and Tiffany couldn’t help but smile, feeling a surge of confidence. John’s hands tightened on her hips, guiding her movements as he began to thrust up into her. The sensation was overwhelming, and Tiffany felt a familiar tightening in her stomach.

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