The Shrinking Confidence

Jerry nervously stepped into Dr. Ava Collins’ office, his heart racing as he took in the familiar surroundings. The medical practice, with its warm lighting and cozy atmosphere, was a place he had visited many times before, but today was different. Today, he was about to reveal his deepest, most intimate secret to the woman sitting behind the large mahogany desk.

Ava, a seasoned psychologist in her early fifties, looked up from her notes, her hazel eyes meeting Jerry’s blue gaze. Her shoulder-length brown hair framed her face, and her glasses gave her an air of intelligence and authority. She was well-known for her direct approach, and Jerry had sought her professional opinion on a matter that had been weighing on his mind for years.

“Please, have a seat, Jerry,” Ava said, her voice calm and reassuring. Her C-cup breasts were subtly visible through her blouse, a hint of her femininity that Jerry couldn’t help but notice. He had always found her attractive, but today, he was more focused on the issue at hand.

The 18-year-old college student sat down, his hands fidgeting in his lap. He was of average height, with a lean, attractive build, but his confidence had taken a hit due to a certain physical attribute he believed was lacking.

“So, Jerry, you wanted to talk about something personal,” Ava prompted, leaning forward slightly, her eyes curious yet kind. “You mentioned it was regarding your… intimate life.”

Jerry took a deep breath, his face flushing with embarrassment. “Yes, Dr. Collins. I… I have a problem. A very personal one.” He paused, gathering his thoughts. “You see, I’ve always felt insecure about my… my penis size.”

Ava’s eyebrows rose slightly, a look of understanding crossing her face. “I see. And how has this been affecting you, Jerry?”

“Well, I’ve never been in a relationship, and I’m afraid no woman will ever want me because of it,” he confessed, his voice barely above a whisper. “I know it’s small, and I wanted to ask for your professional opinion. I mean, is it… is it really that bad?”

Ava’s expression softened, and she leaned back in her chair, considering her words carefully. “Jerry, I appreciate your honesty. Many men struggle with similar insecurities. Can I ask, how small are we talking about?”

Jerry’s face turned an even deeper shade of red, and he hesitated for a moment before answering. “It’s… it’s only about two inches when erect.”

Ava’s eyes widened slightly, and she took a moment to process the information. “I see. That is indeed on the smaller side, Jerry. I won’t lie to you.”

Hearing her words, Jerry’s heart sank, and he felt a lump forming in his throat. He had known this all along, but hearing it from a professional confirmed his worst fears.

Noticing his distress, Ava continued, “But, Jerry, size isn’t everything. Many women find satisfaction in various ways. It’s about the connection, the intimacy, and the skill of your partner. Some women may not even notice the difference if you know how to please them.”

Jerry shook his head, his eyes downcast. “But what if they do notice? What if they laugh at me or reject me because of it?”

Ava sighed, her expression turning more serious. “Jerry, I won’t sugarcoat it. Some women might not be satisfied with a smaller penis. It’s a reality you may have to face. But, there are also women who would be understanding and willing to explore other ways to find pleasure.”

“I-I just want to feel desired, Dr. Collins,” Jerry said, his voice cracking. “I want to know that I can satisfy a woman. That I’m enough.”

Ava’s heart went out to the young man before her. She could sense his vulnerability and the pain he carried within. “Jerry, I want you to know that you are enough. Your worth isn’t defined by the size of your penis. It’s about who you are as a person, your kindness, and your ability to connect with others.”

Her words were like a balm to his wounded soul, and Jerry felt a glimmer of hope. “Thank you, Dr. Collins. I appreciate your honesty. I guess I just needed to hear it from someone else.”

Ava smiled, her warm gaze holding his. “You’re welcome, Jerry. And remember, there are ways to compensate for size. It’s about the overall experience you provide. Foreplay, oral sex, and using your hands can all be incredibly satisfying for a woman.”

Jerry’s mind began to wander, imagining himself in intimate situations, his fingers tracing a woman’s body, his mouth exploring her sensitive spots. He felt a stirring in his groin, and his small penis began to harden, eager for attention.

“Dr. Collins, would it be… inappropriate if I showed you?” Jerry asked, his voice trembling. “I mean, I’d like to know if there’s any hope for me. Maybe I could… masturbate for you, and you could give me your honest opinion?”

Ava was taken aback by the bold request, but she admired Jerry’s determination to face his fears head-on. “Jerry, I’m not sure that’s necessary, but if it would help you, I’m willing to accommodate your request. However, I must ask that you respect my boundaries and understand that this is purely for professional purposes.”

“Oh, I would never cross any lines, Dr. Collins. I just… I need to know if there’s any chance for me with women,” he pleaded, his eyes pleading.

Ava nodded, understanding the importance of this moment for Jerry. “Very well, Jerry. Go ahead. Show me.”

Jerry’s hands moved to his belt, his fingers fumbling slightly as he undid the buckle and unzipped his pants. He slid them down, revealing plain black boxer briefs that tented outwards, showcasing his growing erection.

As he pulled down his underwear, Ava’s eyes widened slightly at the sight of his diminutive manhood. It was indeed small, barely two inches in length, but it stood proudly, the head glistening with pre-cum.

Jerry’s hand wrapped around his shaft, his fingers easily encircling it. He began to stroke himself, his eyes closing as he focused on the sensation. His strokes were slow and deliberate, and he bit his lip, trying to control his breathing.

Ava watched, her professional curiosity piqued. She couldn’t help but notice the way his hand moved, the way his slender fingers caressed his tiny cock. There was something incredibly intimate about the moment, and she found herself transfixed.

“How does it feel, Jerry?” she asked, her voice soft. “Tell me what you’re experiencing.”

“It feels good, Dr. Collins,” he whispered, his voice hoarse with desire. “I-I like the way you’re looking at me. It makes me feel… desired.”

Ava’s heart softened at his words, and she realized that Jerry’s insecurities ran deep. “Keep going, Jerry. Let me see you find release.”

He complied, his strokes becoming faster, his breathing more ragged. His other hand reached down to cup his balls, gently massaging them as he pleasured himself. His eyes remained closed, his face a mask of concentration and pleasure.

Ava’s gaze traveled up and down his body, taking in the sight of his slender form, the way his muscles tensed with each stroke. She felt a stirring within her, a mixture of arousal and compassion.

As Jerry’s pace quickened, his breath coming in short gasps, Ava leaned forward, her voice low. “Come for me, Jerry. Let it all out.”

Her words were like a trigger, and Jerry’s body tensed, his hand moving frantically up and down his shaft. With a low groan, he climaxed, his small cock pulsing as it released a few strands of warm cum onto his hand and stomach.

He slumped back in the chair, his eyes fluttering open, a look of relief and satisfaction on his face. Ava watched, transfixed, as he gently stroked his softening penis, his fingers smearing the sticky fluid across his skin.

“Thank you, Dr. Collins,” he said, his voice hoarse. “That felt amazing.”

Ava smiled, her expression softening. “You’re welcome, Jerry. And I must say, you have a beautiful technique. You know how to pleasure yourself, and I believe that skill can be transferred to a partner.”

Jerry’s eyes lit up at her words, a newfound confidence shining through. “Really? You think so?”

“Absolutely,” Ava assured him. “But remember, it’s not just about the physical act. It’s about the connection, the trust, and the desire you build with your partner. Size is just one aspect of a much larger, more complex experience.”

Jerry nodded, his mind racing with the possibilities. “I understand. And I appreciate your honesty. I guess I just needed to hear it from someone like you.”

“Anytime, Jerry,” Ava said, her voice warm. “And remember, if you ever need to talk about this or anything else, my door is always open.”

Jerry stood up, his confidence seemingly restored. He pulled up his underwear and zipped his pants, feeling a sense of empowerment he hadn’t known before.

“Thank you, Dr. Collins. I’ll see you next week for our regular session,” he said, a smile on his face.

Ava nodded, her eyes sparkling with a hint of mischief. “I look forward to it, Jerry. And remember, don’t be afraid to explore your desires, no matter how unconventional they may seem.”

As Jerry left her office, Ava couldn’t help but wonder about the impact of their session. She knew that Jerry had taken a significant step towards accepting himself, but she also understood that his journey was far from over. The world of intimacy and desire was complex, and she was eager to guide him through it, one step at a time.

Little did Jerry know, as he walked out with a newfound sense of self, that his story was just beginning, and the path ahead would be filled with unexpected twists and turns, each one leading him closer to discovering the true nature of his desires.

Coffee Shop Connection


Madeline strolled into The Latte Bean, her favorite coffee shop, feeling a little more adventurous than usual. It was a cozy place, nestled in the heart of the city, with its quaint, kitschy decor and the aroma of freshly brewed coffee filling the air. The warm atmosphere always made her feel at home. She loved the buzz of the place, the sound of the espresso machine hissing, and the sight of the baristas skillfully crafting each drink.

She took a seat at her usual spot near the window, where she could people-watch while enjoying her coffee. Her green eyes scanned the room, taking in the familiar faces of the regulars and the occasional new visitor. That’s when she noticed him.

William, a young man in his late twenties, sat a few tables away, his nose buried in a book. He had a gentle, boyish face with brown hair that fell over his forehead, framing his brown eyes. He wore a pair of glasses that gave him an air of intelligence, and his average build and height made him seem approachable. There was something about his shy demeanor that caught Madeline’s attention.

She couldn’t help but admire his subtle charm. He seemed lost in his book, occasionally taking a sip from his coffee mug, his fingers gently turning the pages. Madeline found herself wondering what he was reading, and her curiosity grew. She had always been drawn to intelligent men, and there was something intriguing about this quiet, unassuming guy.

As she sipped her latte, Madeline felt a sudden urge to strike up a conversation. She was usually extroverted and confident, especially when it came to men, but there was something about William that made her hesitate. She wasn’t sure if he was the type to engage in small talk, but she decided to take a chance.

“Excuse me,” she said, her voice soft and friendly. William looked up, startled, his eyes widening behind his glasses. “I couldn’t help but notice your book. What are you reading?”

He smiled, a shy grin that lit up his face. “Oh, it’s just an old novel I’ve been meaning to finish. ‘The Great Gatsby,’ actually. Have you read it?”

Madeline’s eyes lit up with recognition. “Of course! It’s a classic. I read it years ago, but I remember loving it. It’s such a tragic story.”

William nodded, his eyes sparkling with enthusiasm. “Yeah, it’s fascinating how Fitzgerald captures the decadence of the Jazz Age. I’m almost done, and I can’t wait to see how it ends.”

As they chatted about the book, Madeline felt a connection forming. William’s shyness seemed to melt away as they discussed literature, and she found herself drawn to his intellect and passion. His voice was gentle, and his words flowed smoothly, revealing a depth of knowledge that surprised her.

“So, you’re a reader, huh?” Madeline asked, leaning forward, her green eyes sparkling with interest.

“Yeah, I guess you could say that,” William replied, a hint of embarrassment in his voice. “I’m an online stockbroker, so I spend a lot of time in front of a screen. Reading is my escape.”

Madeline smiled, her lips curving seductively. “Well, I think it’s a wonderful escape. And you seem to have excellent taste.”

As their conversation flowed, they discovered more common interests. William’s shyness gradually faded, and he began to open up, sharing stories about his work and his passion for investing. Madeline, with her love for wealthy and handsome men, found herself captivated by his intelligence and modest confidence.

The coffee shop buzzed around them, but they were lost in their own little world. Madeline’s heart raced as she felt a growing attraction to this charming, unassuming man. She loved how his eyes lit up when he talked about something he was passionate about, and his smile was infectious.

“You know, I’ve always believed that a good book can transport you to another world,” Madeline said, her voice low and sultry. “But I think this coffee shop might just be my new favorite escape.”

William’s cheeks flushed slightly, and he laughed softly. “I’m glad I could provide some entertainment. I usually keep to myself, but talking to you has been… nice.”

Madeline leaned closer, her eyes locking with his. “More than nice, I’d say. I feel like I’ve known you for ages.”

As their gazes held, the air between them crackled with unspoken desire. Madeline’s heart pounded in her chest, and she could see the same longing in William’s eyes. Without a word, they both knew what was about to happen.

Madeline stood up, her shapely figure moving gracefully, and extended her hand. “Why don’t we continue this conversation somewhere more… private?”

William’s eyes widened, and he hesitated for a moment, as if unsure if he had heard her correctly. Then, with a nod, he took her hand, his fingers intertwining with hers. “I’d like that,” he said, his voice steady but slightly trembling.

They left the coffee shop, hand in hand, and stepped out into the bustling city streets. Madeline led him to her car, a sleek black sedan, and they drove to her apartment, a short distance away. The ride was filled with nervous excitement, and neither of them spoke much, both lost in their thoughts.

As they arrived at her place, Madeline felt a surge of anticipation. She unlocked the door, and they stepped into her cozy apartment, decorated with warm tones and soft lighting. The living room was inviting, with a plush couch and a fireplace, creating a romantic ambiance.

“Make yourself comfortable,” Madeline said, her voice husky. “Can I get you a drink?”

William nodded, his eyes taking in the intimate setting. “Sure, that’d be great.”

Madeline walked to the kitchen, her hips swaying seductively, and poured two glasses of wine. She returned to find William standing by the fireplace, his eyes fixated on the dancing flames.

She handed him a glass, their fingers brushing, and he took a sip, his eyes closing briefly as he savored the taste. “This is nice,” he said, his voice low.

Madeline moved closer, her body brushing against his. “I’m glad you think so,” she whispered, her breath warm on his neck.

William turned, his eyes locking with hers, and without a word, they kissed. It was a gentle exploration at first, their lips meeting softly, but soon the passion ignited. Madeline’s hands cupped his face, her fingers tangling in his hair, as she deepened the kiss.

William responded with eagerness, his hands roaming over her curves, tracing the outline of her shapely body. He pulled her closer, his hands sliding down to cup her firm ass, squeezing gently. Madeline moaned into his mouth, her body pressing against his, her C-cup breasts crushed against his chest.

“You’re so beautiful,” William whispered between kisses, his hands moving to unbutton her blouse.

Madeline giggled softly, a mix of excitement and anticipation. “I think you’re pretty damn gorgeous yourself,” she replied, her hands working on his shirt buttons.

As their clothes came off, piece by piece, they reveled in the sight of each other’s naked bodies. Madeline’s skin was smooth and tanned, her breasts full and inviting, with dark nipples that hardened under William’s touch. His hands explored her curves, his fingers tracing the lines of her waist and hips, making her shiver with pleasure.

William’s body was lean and toned, his skin pale in contrast to hers. His cock, already hard and throbbing, stood proudly, and Madeline couldn’t resist running her fingers along its length, making him gasp.

“I want you,” she whispered, her voice hoarse with desire. “Right here, right now.”

William needed no further encouragement. He lifted her, his strong arms wrapping around her waist, and carried her to the couch. He laid her down gently, his eyes never leaving hers, and positioned himself between her thighs.

Madeline spread her legs, inviting him in, her pussy already wet and ready. William’s cock hovered at her entrance, teasing her, and she arched her back, pushing her breasts towards him.

“Please,” she begged, her voice breathless. “Fuck me, William.”

With a growl of desire, he thrust forward, filling her in one smooth motion. Madeline cried out, her body welcoming him, her pussy gripping his cock tightly. He set a relentless pace, his hips slamming against hers, driving deep into her wet heat.

“Oh, fuck!” William groaned, his voice raw. “You feel so good, Madeline.”

She wrapped her legs around his waist, her hands gripping his shoulders, urging him on. “Harder, baby,” she panted. “Fuck me harder.”

William obliged, his thrusts becoming more powerful, his cock pounding into her over and over. Madeline’s breasts bounced with each impact, her nipples rubbing against his chest, sending waves of pleasure through her body.

The couch creaked with the force of their passion, and their moans filled the room. Madeline’s pussy clenched around William’s cock, milking him, as her orgasm built. She scratched his back, leaving marks of passion, as she rode the wave of pleasure.

“I’m gonna cum!” she cried out, her body tensing.

William’s thrusts became erratic as he felt her pussy pulsate around him. “Cum for me, Madeline,” he grunted. “Let me feel it.”

With a final, powerful thrust, Madeline’s orgasm exploded, her pussy contracting around his cock, milking him as he filled her with his hot seed. They cried out in unison, their bodies trembling, as they rode the crest of pleasure together.

As their hearts slowed and their breathing returned to normal, they lay entangled on the couch, their bodies still joined. Madeline ran her fingers through William’s hair, her eyes sparkling with satisfaction.

“That was incredible,” she whispered, her voice soft and content.

William smiled, his eyes half-closed in bliss. “You have no idea how long I’ve wanted to do that.”

Madeline giggled, a mischievous glint in her eye. “Well, I’m glad I could help you cross that off your list.”

They shared a tender kiss, their lips lingering, and Madeline felt a connection forming that went beyond the physical. As they lay there, exhausted and satisfied, she wondered what the night would bring and whether this encounter would be the start of something more.

Little did they know, this was just the beginning of a night filled with passion and exploration, where they would discover new heights of pleasure and a connection that would leave them both craving more.

The Cougar’s Prey


I’ll never forget the day I met Kate. It was just a regular shift at the gas station, pumping gas and wiping down windshields for a few extra bucks. I was a typical college kid, working part-time to make ends meet. With my blonde hair, blue eyes, and slim, athletic build, I guess I didn’t look too bad, but I was shy and never really had much luck with women.

As I was finishing up with an SUV, I noticed a sleek black sports car pulling in. The driver, a woman, stepped out, and my jaw almost hit the floor. She was stunning. Short blonde hair framed her face, and her bright green eyes sparkled with a playful glint. She wore a tight black dress that hugged her curves, showcasing her lean figure. I couldn’t help but notice her small, perky breasts straining against the fabric. She looked to be in her late forties, but damn, she was hot.

“Fill ‘er up, please,” she said, flashing me a smile that sent a jolt straight to my groin. I managed a nod, trying to act cool, but my heart was racing. I couldn’t believe a woman like her was talking to me. I grabbed the gas pump and got to work, stealing glances at her whenever I could.

“You’re new here, aren’t you?” she asked, leaning against her car, one long, toned leg crossed over the other.

“Yeah, just started a few weeks ago. I’m Billy,” I replied, feeling my face heat up.

“Kate,” she introduced herself, extending her hand. I shook it gently, her skin soft and warm. “So, Billy, you go to college here in Salem?”

I nodded, feeling a bit more relaxed. “Yeah, I’m studying business. Just doing this job to pay the bills.”

“Ah, a man with ambition. I like that,” she said, her eyes twinkling. “You know, I might have a few odd jobs for you. I live nearby, and there’s always something that needs fixing around the house. You interested?”

My mind raced at the prospect of spending more time with this gorgeous woman. “Uh, sure. I mean, yeah, I’d be happy to help.”

Kate smiled, and it felt like she saw right through my nervousness. “Great! Give me your number, and I’ll text you the address. How’s tomorrow afternoon sound?”

I quickly recited my number, my voice cracking slightly. She saved it and sent me a message right away, letting me know she was looking forward to it. As she drove off, I stood there, dazed, the scent of her perfume lingering in the air.

The next day, I found myself standing outside a beautiful colonial-style house, wondering if this was all a dream. Kate answered the door, dressed casually in tight jeans and a low-cut tank top that showcased her cleavage. Her hair was loose, and she looked even more stunning in the natural light.

“Billy, right on time,” she purred, stepping aside to let me in. “Come in, make yourself comfortable. Can I get you a drink?”

I stepped into a spacious living room, my heart pounding. “Sure, water would be great.”

She disappeared into the kitchen, her hips swaying seductively. I took a seat on the couch, my eyes scanning the room. The place was tastefully decorated, with soft lighting and a cozy atmosphere.

Kate returned with two glasses of water, handing me one. “So, Billy, tell me more about yourself. What do you do for fun?”

I took a sip, trying to gather my thoughts. “Well, I like to work out, play some basketball… Oh, and I deliver groceries on the weekends to earn some extra cash.”

“Groceries, huh? That sounds… interesting,” she said, her voice low and sultry. “I bet you see all sorts of things delivering groceries to people’s homes.”

I felt my face flush, not sure where this conversation was going. “Yeah, I guess so. It’s just a job, really.”

Kate moved closer, perching on the edge of the coffee table, her knees almost touching mine. “You know, Billy, I’ve always had a thing for younger men. There’s something so… energetic and passionate about them.”

My breath caught in my throat. Was she flirting with me? I couldn’t believe it. “Really? I… I mean, I’ve always liked older women. They’re, um, more experienced.”

She let out a soft, throaty laugh, leaning even closer. “Oh, you sweet boy. I can show you a thing or two about experience.”

Before I could respond, she placed her hand on my thigh, sending a jolt of electricity through my body. “I’m so glad you came today, Billy. I have a feeling we’re going to have a lot of fun together.”

I swallowed hard, my dick already straining against my jeans. Kate’s touch was electric, and I could feel my shyness melting away under her confident gaze.

“Why don’t I give you a tour of the house?” she suggested, standing up and taking my hand. “That way, you’ll know where everything is.”

I followed her, our fingers intertwined, as she led me through the house. The kitchen was spacious, with a large island in the center. Kate ran her free hand along the countertop, her touch lingering. “I spend a lot of time in here, cooking and baking. Maybe you can help me with that sometime.”

I nodded, my eyes fixated on her graceful movements. “I’d love to.”

As we continued the tour, Kate’s hand found its way back to my thigh, this time higher up, dangerously close to my crotch. I could feel her fingers brushing against the bulge in my jeans, and I had to bite my lip to stifle a moan.

“Here’s the guest room,” she said, opening a door and stepping aside to let me enter. It was a cozy room with a large bed, covered in soft blankets. “This is where you’ll be staying when you work late or… when we get carried away.”

I turned to face her, my breath coming in short gasps. “Kate, I… I don’t know what to say.”

She moved closer, her body pressing against mine, and I could feel her breasts against my chest. “You don’t have to say anything, Billy. Just let yourself enjoy this.”

Her lips found mine, soft and warm, and I kissed her back, my hands instinctively reaching for her hips, pulling her closer. Kate’s tongue danced with mine, and I could taste her sweetness. My hands explored her body, tracing the curves of her waist, then moving upwards to cup her breasts. She moaned softly into my mouth, her hands now tugging at my shirt, eager to feel my skin.

Breaking the kiss, Kate whispered, “Let’s get more comfortable, shall we?”

I nodded, my body on fire with desire. She led me to the bed, her movements graceful and purposeful. I sat on the edge, watching as she slowly undressed, revealing her flawless body. Her breasts were firm, with pink nipples that stood erect, begging for attention. Her flat stomach led down to a patch of neatly trimmed blonde hair, hiding her glistening pussy.

“Your turn,” she whispered, her eyes burning with desire.

I quickly shed my clothes, my hard cock springing free. Kate’s eyes locked onto it, and she licked her lips hungrily. I joined her on the bed, and she immediately took my cock in her hand, stroking it gently.

“You’re so big, Billy,” she purred, leaning down to take the tip into her warm mouth. I groaned, running my fingers through her hair as she began to suck and lick my length. Her mouth felt incredible, and I could feel my orgasm building quickly.

“Not yet, baby,” she said, sensing my impending release. “I want you to fuck me. I want to feel you inside me.”

She climbed on top of me, positioning herself above my throbbing cock. With one hand, she guided me to her entrance, and with a slow, deliberate motion, she impaled herself on my shaft. We both moaned as she sank down, taking all of me inside her.

Kate began to ride me, her hips moving in a slow, sensual rhythm. Her breasts bounced gently with each thrust, and I reached up to caress them, pinching her nipples, which made her gasp.

“You feel so good, Billy,” she whispered, her eyes closed in pleasure. “I’ve wanted this since the moment I saw you.”

Her words drove me wild, and I thrust my hips upwards, meeting her movements. Our bodies slapped together, creating a wet, rhythmic sound that filled the room. Kate’s pussy was hot and tight around my cock, and I could feel my balls tightening as my orgasm approached.

“Fuck, Kate, I’m close,” I grunted, my hands gripping her hips.

“Me too, baby,” she panted, her breath coming in short gasps. “Fill me up, Billy. Give it to me.”

Her words sent me over the edge, and I exploded inside her, my cock pulsating as I filled her with my hot cum. Kate cried out, her orgasm hitting her at the same time. She collapsed onto my chest, our hearts racing in unison.

As our breathing slowed, Kate looked up at me with a satisfied smile. “Welcome to the team, Billy. I have a feeling you’re going to be a very valuable asset.”

I couldn’t help but laugh, still reeling from the intense pleasure. “I think I just found the best job ever.”

Little did I know, this was just the beginning of my steamy adventure with Kate, the cougar who knew exactly what she wanted and how to get it.