Tim reached for the doorbell, but then his hand hesitated. He turned, ready to walk away, but then paused, pivoting back towards the door with a new determination. He placed his finger on the bell, allowed himself a brief moment of hesitation, and then finally rang it.
He pressed his ear to the door, but there was no sound. In fact, a wave of relief washed over him. Turning away, he made his way down the stairs leading to the low, single-storey red-brick house—well-kept, despite its modest size—when the door behind him creaked open.
Tom froze. For a fleeting moment, his strongest urge was to keep walking, to simply leave. But where would that lead? In a week, or maybe even sooner, he’d regret it and end up trying to set up another meeting. And if that happened, it would be even more awkward—if that was even possible.
Tim turned back.
In the doorway, a woman stood expectantly, dressed in a sheer, dark-blue gown that clung to her stunning figure. Her long blonde hair fell halfway down her back, her large, tired blue eyes highlighted with black liner, her enlarged lips bore traces of red lipstick. Her face, once undoubtedly beautiful, was now marked with the telltale signs of time—not the kind that comes with age, but the kind that comes with life’s cruel twists. It wasn’t hard to see that fate had not been kind to her.
She smiled.
“Phill?” she said. “I was expecting you twenty minutes ago. No matter, come on in.”
Tim took a deep breath, wiping his sweaty palms on the brand-new jeans he’d bought just for this occasion. With a slightly faster pace than necessary, he ascended the steps and entered the house, after the woman graciously stepped aside, her smile still in place.
If Tim had any doubts about where he was or who the woman was, they’d vanish the instant he stepped into the first room from the narrow hallway. What most would expect to be a living room or dining area was, instead, an enormous bedroom with a massive four-poster bed—the largest he’d ever seen.
The entire room, bathed in shades of red and black, had a strangely inviting feel. The bed and floor were scattered with cushions of all sizes and colours. Each wall sported a mirror, and each one was unique in its design. Hanging between them were large posters of a much younger version of the woman who’d just let him into the house. In every picture, she was naked, striking provocative—but not vulgar—poses.
He turned, only to find her standing right behind him. She flashed him a pleasant smile, but without hesitation, reached out her hand.
“Oh, of course,” he mumbled. He fumbled through the front pocket of his jeans, pulling out a roll of cash. He awkwardly unwrapped it and handed her ten fifty-dollar bills. She counted them quickly before slipping away for a moment. A minute later, she returned, her face wearing a tired smile.
“Call me Gina, darling,” she purred in a voice that was trying a little too hard to be sultry, oozing experience yet feeling ever so slightly fake. She sauntered over to a table in the corner, where an assortment of intriguing items awaited: a box of tissues, a variety of vibrators in all shapes and sizes, and two mysterious boxes. One was black and velvety, the other an innocent-looking tea box.
It was the tea box Gina reached for. With a practised flourish, she opened it and motioned for Tim to step closer. He did, only to discover that instead of teabags, the box was packed to the brim with condoms. Every brand, size, flavour, and colour imaginable spilled out like a cheeky rainbow of intentions.
Without another word, Gina let the dark-blue robe slide from her shoulders, pooling at her feet. Dressed in nothing but a devilishly sexy red lingerie set, she stretched out languidly on the bed. This time, the smile on her lips wasn’t just for show—it was enticing, genuine, and left no room for misinterpretation.
Tim’s chest tightened with panic. He swallowed hard, his eyes darting between the narrow plastic packets of condoms and the half-naked woman sprawled on the bed. Gina noticed his hesitation, and in the blink of an eye, her shameless smile melted into one of concern.
She sat up, grabbed one of the larger cream-coloured cushions, and held it against her chest, shielding her bare skin from Tim’s gaze. He was grateful for the gesture.
“What’s the matter, honey?” she asked in a kind voice. “Your first time?”
Tim lowered his eyes, shaking his head, but he still couldn’t bring himself to look at her. She studied him for a moment, then gently patted the spot on the bed beside her.
“Come, sit down. What’s your real name?”
“Tim,” he exhaled, barely above a whisper.
“Tim, if you just want to talk, that’s perfectly fine,” she said warmly. “A lot of men come to me just to chat—they want someone who’ll listen. So, take a seat here beside me, or over there in the chair if you’d feel more comfortable. And whenever you’re ready, you can start.”
Tim dragged the chair closer to the bed and sank into it. He avoided meeting her eyes, his gaze instead drawn to the elegant curve of her smooth, flawless legs.
“I don’t want to talk,” he said, his voice low. “I want to…” He trailed off, nodding toward her and the sprawling bed piled high with a riot of cushions.
Gina studied him, then slowly shook her head, a knowing smile playing on her lips.
“Tim, trust me, whatever you’re holding back—whatever you want to say or show me—I’ve heard it a hundred times and seen it a thousand. If you’re not a virgin, then there’s only two things that could be bothering you. One, you’re a closeted gay, and you think I might help you figure it out. But you’re not gay—if you were, you’d be forcing yourself to look at me, not away.” She paused, letting her words hang in the air like a teasing challenge. “So that leaves one thing: size. Too big? Or too small?”
Tim shot her a surprised glance but kept his lips firmly sealed.
“Ah, so it is too small,” Gina said with a sly nod, her voice dripping with mischief. “Why don’t you show me, and I’ll tell you exactly what I think?”
Tim didn’t move a muscle, and his body stiffened with hesitation.
Gina’s lips curled into a wicked smile. Slowly, she let the cushion she’d been holding slip down, giving Tim an unobstructed view of her sheer lace bra and the tantalising curve of her perfectly sculpted breasts.
“Let me be perfectly honest,” Gina said. The tone of her voice changed. It was deeper now, more teasing. Amusement played in her eyes. “So you have a dicklet in your pants, is that it?”
He looked at her in shock. That was exactly what the last woman he’d tried to have sex with had said to him. He’d put it off for almost two months before she’d threatened to break up and he’d committed to sleeping with her. But the bitch barely saw his little penis and started laughing. Gina was different. Same word, yet – she wasn’t mocking him. She was teasing him. She provoked him.
And it worked.
Tim could feel the arousal slowly overwhelm him.
She continued.
“You’d like a proper cucumber, but what you can offer me is barely a baby carrot, am I right?”
She put down the pillow, licked her lips sensuously, then freed her large silicone breasts from her red bra and began to tease her nipples with her thumbs. And she kept talking.
“Don’t be shy, Tim. Show me your little dick. I want to see it. I love small cocks, they’re the best. Oh, as much as men with needle dick try, I’m almost always embarrassed to take money for such great sex. Come on, don’t make me beg.”
Tim watched in fascination as Gina lay on her back and turned her amazing body towards him so he could see clearly. She played with her nipples and slowly put her knees apart so he could watch her naked pussy as she was wearing tiny panties with her crotch cut out.
His little cock hardened. Without thinking too much about it, Tim unbuttoned his new jeans, stood up and let them fall to his ankles. He did the same with his white briefs.
“Oh,” a hoarse sigh escaped Gina’s throat. “I can see it now. It’s so tiny, so puny. One amazing petite package about the size of your palm. Come on, you know you want to grab your dicklet and rub it. Do it. Jerk it off for me. Right now. I can’t wait to see it all disappear into your palm.”
Tim did as she said. He cupped his little cock in his palm and even though he held it all the way down at the root, the pink head was barely poking out of his clenched fist, there was a milky droplet at the hole.
Gina grunted with satisfaction when she saw that.
“Now pump it hard. Show me how you like it best. I want to see your best wank job. Yes, that’s right. A little faster.”
Tim, his hand gripping his tiny member tightly, flicked his hand quickly at his crotch. Lips parted, eyes almost unblinking, he stares at Gina lying sensuously on the bed, pulling down her panties. Slowly, very slowly. All the faster he kept wanking.
“Slow down, Tim,” she growled sweetly. She ran her tongue over her red lips, her hand came close to her fully shaved pussy, but didn’t touch it, staying just a little closer. Waitfully. Ready. “Slow down; let me savour you a little. Show me. I want to see your stubby pink stump.”
Tim removed his hand and watched the woman’s face. He was pleased to see the lust, the desire, on her face. The woman wanted him. Gina craved his small cock, and his already firm erection grew even harder.
“Now just grab the head of it,” she said. “Squeeze the top with one hand and place the other hand on your balls. Yes, just like that. Very good, Tim.”
He did as she instructed. He watched as the beautiful blonde in front of him pushed two fingers into her stretched, wet vagina, and while he grabbed his throbbing cock by the top, he rubbed his balls with his other hand. A moan escaped his throat.
She smiled contentedly.
“Go ahead and squeeze your balls with the force that suits you,” Gina said. “Now slowly, very slowly, run your hand down the entire length of your tiny cock. Slowly I said! Yes, that’s right.”
Just as slowly, the professional played with her fingers inside her pussy.
“Now back up again, and back down now,” she tells him, her eyes fascinatedly fixed on Tim’s hand jerking his cock. “Now grab it at the root and squeeze. Squeeze as hard as you can stand. Then release. Squeeze again, loosen just a little, and run your hand up to the head. That’s it. Exactly like that. Now grip the head and with your other hand, grab the root of the prick. You’ve got an amazing dick, really. I’ve seen my share of cocks, but yours is extra. It’s so small, it’s cute. I want to take it all in my mouth and eat it. It’s so cute.”
As she said this, her breathing quickened, her fingers sinking deeper and faster into her wet pussy. Her eyes closed but didn’t stay closed, still her gaze was fixed on his hand in his lap as he jerked his hard little cock.
He grunted with excitement again and then, without warning, lava, milky and thick, gushed out of the little head peeking out of his clenched fist and overflowed his fingers. And then another, and then some more.
Tim sat back in his chair, exhaled deeply, and looked at Gina. She was sitting up again, her legs neatly together and a slight smile playing on her face.
“There you go,” she said as he reached for the box of tissues. “When you learn to love your little friend, you’ll find you wouldn’t change. A small penis is more aesthetically pleasing than a big one. A lot of women love small cocks. I promise.”
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