Bigger for Gwen

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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

This fictional story is the artistic expression of the author who wrote it. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this story, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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by smallercuck

“I noticed that Darren joined the gym.”

Gwen looked up from her papers at the young salesman as he walked into her office. As VP of Finance, Gwen Wilson hadn’t interacted with Steve Wills often, he was much lower on the pecking order than she was, but she liked the younger man. He was charismatic, good-looking, and confident, in short, an excellent salesman.

“Oh yeah, he sure did. You saw him there?”

“Yep, He was swimming, I think. I saw him in the locker room.”

“He didn’t mention it. I’ll tell him to keep an eye out for you. Maybe you can give the old man some pointers,” she smiled. Steve was twenty years her husband’s junior, but undoubtedly knew his way around a gym. He was a very fit guy.

“Well, your husband is brave, I’ll give him that.”

“What do you mean?”

“I just mean that in my experience, most guys with his physique wouldn’t be caught dead in the shower at the gym. Darren went right in there. Not a hint of self-consciousness.”

Was Steve making a dig at her husband? Gwen wasn’t sure, but there was something in his comment that was patronizing.

“Yeah, it takes guts to start working out. I’m proud of him. Maybe he’ll put you to shame one day, Steve.” Gwen was annoyed at the younger subordinate and had decided to put him back in his place.

“Well, maybe he can tighten up that flab if he sticks with it. He won’t be putting me to shame, though. Some muscles you need to be born with. Know what I mean? ” Steve held his thumb and forefinger up. The one-inch space between the two digits indicated exactly which muscle Steve thought Darren was lacking.

“I most certainly do not know what you mean!” Gwen couldn’t believe how impertinent the young man was being.

Steve just smiled at her, cockily. “You’re still great-looking for an older broad. Just give me the word and I can show you the difference between me and your hubby.”

Gwen’s face was red. “I think you should leave now, Steve.”

He was smiling now. Gwen was out of sorts and Steve was getting a perverse pleasure out of needling her. He reached down and adjusted the lump in the front of his slacks. Gwen couldn’t help but look at the substantial bulge. She blushed.

“Gwen, you are too good for that bum. You have great tits and you’re in amazing shape for your age. I could do things to you that you’ve never imagined. There’s nothing sexier than married women. I find that most of them haven’t been fucked properly in years. And judging from little Darren’s equipment, you’ve been missing out.”

Gwen recovered her wits. “Get out of my office, Mister Wills. You can expect to hear from HR about this.”

Steve just smiled. “You’re going to tell them that I was teasing you? Really, Gwen? I can see the report now: the complainant was upset at the mocking of her husband’s small penis. We both know you’ll never file that grievance.” The young man smiled confidently at the older woman. She was shaking with rage.

“Just think about it, Gwen. You’re still sexy. Don’t you deserve something more before you get too old? You’re what, 50? 55? You won’t have that body forever.” He spun on his heel and strode from the executive office.


That night Gwen had the dream again. She was back in her college dorm room kissing Dean Stevens. He was an amazing kisser and Gwen was wet and ready for him. Gwen was about to lose her virginity and she was falling in love, as well. She practically swooned as Dean moved her hand onto the hard lump beneath his slacks. He was so big and so hard. She wanted him.

In her dream, Gwen removed Dean Steven’s clothing to reveal an impossibly large cock. He was so strong and masculine. Gwen held Dean’s muscular torso as his hard rod took her virginity. She lost herself in waves of orgasmic pleasure as the college stud ravaged her body.

Gwen woke sweating and horny. It was only a dream, she realized. The same damn dream that had tormented her for thirty years.

Gwen had fallen for Dean Stevens and she had felt his hard cock under the fabric of his denim jeans. Dean urged Gwen to unzip him. She made him painfully aroused, he said. But as fate would have it, Gwen’s roommate retuned from the library at just that moment. She didn’t lose her virginity to Dean and she never saw the beautiful cock that was hidden in the college-stud’s pants. Two days later Gwen found out that Dean Stevens was fucking half a dozen different girls around campus. She was heartbroken.

Gwen was popular in college. She was the tallest girl in the accounting program and she knew that all she had to do to make most men drool was to give them a look at her long legs. When she wore a tight skirt, even her professors stumbled over their words. Gwen had a wide ass, which was accentuated by her narrow hips and large chest. Guys were always staring at her breasts when she tried to talk to them. Gwen was forced to become an expert at dressing conservatively , just to be taken seriously.

It was senior year before she met Darren. All the guys were after one thing from her, it seemed, and their clumsy sexual advances just reminded her of Dean, who had broken her heart. Things were somehow different with Darren. She never lusted after him the way she had for Dean, but that was a good thing. Feelings of lust lead to feeling of pain and betrayal. Gwen lost her virginity to the safe guy and eventually married him. One thing haunted her dreams though: Gwen remembered the way the lump in Dean’s slacks filled her hand. It seemed much larger than Daren’s thin penis. The difference was stark. Gwen told herself that she was mistaken about Dean’s size. She had, after all, felt him only once and she had been so excited that perhaps her mind was playing tricks on her.


Steve Wills’ comment about Darren’s small penis rekindled the buxom brunette’s long hidden doubts. Steve was an asshole and she would never admit, to him or herself, that his horrible comments had gotten to her. The truth, though, was that the young salesman had managed to get under Gwen’s skin. That Friday night when Darren massaged her back, she closed her eyes and imagined it was a younger, more aggressive man in her bed. When Gwen’s husband penetrated her, she tried to gauge his girth and to imagine what a larger penis might feel like.

Gwen avoided Steve for several months. She sometimes watched him from afar and she realized that he had a handsome youthful face and an athlete’s body. Why is it that the jerks are always so good-looking, she wondered?

When Steve caught Gwen looking he smirked and even winked at her. Gwen blushed and looked away. She was a successful vice president, but this guy made her blush like a schoolgirl. He sometimes winked at Gwen when no one was looking or stared at her until she was forced to meet his gaze angrily. Gwen resolved to be more careful and to stay away from Steve, even as he began to replace Dean Stevens, her college crush, in her unwanted sexual dreams.


Gwen was sitting near a pair of young secretaries at lunch one day. She overheard the giggly conversation between the younger women when the attractive blonde secretary excitedly told her friend about her plans for the weekend. “He’s taking me to Vegas.”

The dumpier brunette friend’s eyes widened. “Oh my God. Really? You are so lucky. You bitch.”

“I can’t wait. He is so sexy. I don’t plan to leave the hotel room at all. I plan to keep Steve’s python busy from Friday to Monday.” The pair laughed.

“Can I see the picture again, Beth? I can’t believe the size of him. I need to find a cock like that. I’d leave Thomas in a heartbeat for that.”

Gwen almost choked when the blonde handed her phone to her friend. Gwen could see the backlit screen over the girl’s shoulder and she couldn’t fail to miss Steve Wills’ athletic naked body. He posed and displayed the mocking grin that had so infuriated Gwen. His penis was magnificent. It hung proudly between Steve’s thick thighs and Gwen was startled by both its length and girth. Although it was soft, the younger man’s cock was much larger than Darren’s aroused penis.

That afternoon Gwen did something she had never done before: she sat in her executive bathroom and pleasured herself. The brunette rubbed a hard nipple and bit her lip as she rubbed her hard clit. She imagined herself in her college dorm. In Gwen’s mind, Steve was kissing her as she rubbed his enormous penis beneath his slacks. He guided her to her knees and she began to unzip his pants.

The sound of Gwen’s finger in her soaking pussy could be heard throughout the bathroom, and Gwen was worried that her assistant on the other side of the bathroom wall would overhear her. She bit her lip to stifle a moan and curled her toes inside her expensive designer heels. Gwen clenched her eyes shut and enjoyed a powerful orgasm as she imagined worshiping Steve’s giant cock. The housewife briefly compared the fantasy penis to that of her husband’s and she wondered how it would feel to be penetrated by something so much larger. Gwen bit her lip to stifle a moan as she gripped the handle with white knuckles.

After the waves of pleasure subsided, Gwen found herself blushing and shaking as she lifted herself off of the toilet on shaky legs. Hers cheeks were flush and her body tingled. It was the best sexual release she’d had in years.

Gwen couldn’t get the image of Steve Wills out of her head. As months passed, Gwen lost interest in sex with her husband as the thought of giving herself to her co-worker began to dominate her thoughts. She often refused to have intercourse with Darren, claiming to have cramps or a headache.

It had been months since Gwen had last spoken to Steve. Her heart skipped a beat when he walked into her office. He smiled at her coyly, and she wondered if Steve somehow suspected that she had fantasized about having sex with him. It was the same smile that had so infuriated her some months ago, but now Gwen couldn’t help but find it sexy. Why did that jerk have to be so confident and attractive?

“I thought I told you to leave me alone, Mr. W ills,” Gwen said. He continued to smile and hold her gaze. Her panties moistened.

“I’m just thought you might want to know what your husband has been up to behind your back, Mrs. Wilson.”

“What are you talking about?”

“I’m talking about Darren, your husband. He likes to hang out in the change-room and ogle the men. Maybe he has penis envy, I don’t know. There have been complaints, and I thought you ought to know.”

Gwen could feel the blood rush to her face. She wasn’t sure why she even believed the younger man, but something told her he wasn’t lying. She sat behind her desk and tried to regain her composure. “It’s not true,” she said.

“It is true, Gwen. You should have a talk with him. Put a stop to it before someone kicks his ass. I’ve seen him do it. He likes to watch the guys shower, and he gets aroused, Gwen. I think he has a little crush on me, to be honest. Your husband loves to stare at my cock.”

Gwen couldn’t look at the young salesman. “I’d like you to leave, please.” She looked down at the pad on her desk as her eyes filled with tears. She was shaking and trying to catch her breath. When Gwen looked up, Steve was gone.

That Friday night Darren reached for Gwen as they lay in bed. He rubbed her leg and slid his hand up to towards her mid-section. She removed his hand and rolled onto her side. Their sex life had dwindled the last few months and Gwen could tell Darren was frustrated and annoyed. She had been making excuses more often when he wanted sex.

Darren moved towards Gwen to kiss her, but she pulled away. She looked at her husband. “Tell me about the gym.”

“Umm, what do you mean?”

“Do you shower at the gym, Darren?”

“Yeah, sometimes. I guess I do.”

“You guess you do, hmmm? Do you shower with other men, Sweetie? Are there naked men in there with you?”

“Geeze, Gwen. What kind of question is that?”

“Maybe it makes me hot -the idea of all those hot naked guys. Maybe it turns me on to imagine all those studly bodies.” She reached under the elastic waistband of her husband’s pajamas and ran the tip of her fingers over the head of his soft penis. He began to stiffen.

“You know that Steve Wills goes to your gym. Have you noticed him there?”

Darren stuttered as he tried to answer the question. The combination of his wife’s questions and the feathery touch of her fingers on his hardening penis had him flustered. “I think so. Yes, he goes there. The gym, I mean.”

“The girls at work say he has a big dick. They say he is hung. He’s slept with several girls from the office. They all say he is great in bed, and that he has a sexy body.”

“Gwen, what kind of talk is that? What a thing to say.”

“It’s just bedroom talk, baby. You seem to like it. Doesn’t it turn you on?” There was no denying Darren’s now rigid cock. Just a few seconds of the lewd talk had produced the desired effect on his modest equipment. “I can stop now if you want, Sweetheart.” Gwen slowed the motion of her hand inside his pajama bottoms.

“No, Baby. Don’t do it. Please don’t stop.”

“Have you seen Steve in the showers, Sweetie? Did you ever notice his body? His cock? Is he as big as they say, Babe?”

“Ummm. Gwen. I don’t know. Uh. Don’t stop.”

“You don’t know if he’s as big as they say they say, or you don’t know if you’ve seen him in the showers?”

Gwen wasn’t sure why she had decided to question her husband in this way, but something in her wanted to hear it from his own lips. Was he getting a perverse thrill ogling the men at his gym? She wondered if he did have a crush on Steve Wills. Gwen’s emotions were confused and jumbled. Was she trying to shame Darren or was she titillated by the thought of Steve’s naked body?

Gwen continued to rub her fingertips on the underside of her husband’s penis. “Do the men tease you, my hubby? Do they make fun of this little thing?” Darren moaned as his orgasm approached. “Steve’s cock is so much bigger than this little dick, isn’t it? I’ve noticed the bulge in his pants too, Honey. I guess it turns both of us on.”

Gwen leaned towards her husband and whispered in his ear, “Oh, you like that? Do you like it when I talk about your little dick, or are you imagining Steve’s cock? Is that why you are so hard? You’re such a kinky little boy, aren’t you Darren? I wonder what those big sexy men would think if they could see you now.” Darren moaned as he ejaculated on Gwen’s hand and coated the inside of his pajama bottoms. His eyes were screwed shut, and he missed the look of distain on his wife’s face as she stood and walked to the bathroom.

Gwen spent the night in the guest room and left the house early in the morning, before Darren woke. She was certain, now, that her husband was getting some sort of thrill checking out men in the locker room. Gwen had to admit that humiliating Darren and making him cum in her hand had been exciting, but she doubted that her marriage could survive in its present form. The business woman couldn’t imagine ever going back to the boring marital relations that she had lived with through the last twenty years. It was clear to Gwen; she wanted to be fucked by Steve Mills.

Gwen was unable to reach Steve all weekend because he wouldn’t pick up his cell phone. The leggy brunette avoided her husband and busied herself at the mall. Gwen bought some lingerie that she was sure would turn Steve on. Her legs would look great in the black stockings and the idea of Steve removing the snaps on the garters made her wet. The 52 year-old had never been so horny over the course of two days.

Gwen was anxious and nervous. She wondered if she might lose her nerve and call the whole thing off. Could she go back to Darren and act like nothing had happened? Gwen doubted it.

On Monday morning Gwen waited for an opportunity to discretely visit Steve’s office. She had made up her mind to go ahead with contacting Steve and she would deal with Darren later. The sexy brunette had just sat at her desk when Beth, the young blonde secretary, briskly entered the office and closed her door.

Beth was red faced. “What do you think you are doing?”

Gwen looked at the blonde, incredulous. “Pardon me?”

“I know you spent half the weekend calling Steve’s cell. He was with me. Why would he want an old hag like you when he can have this whenever he wants?” Beth spread her arms and posed as if to say, “I’m hot, and I damn-well know it.”

Gwen compared herself to the younger girl. She may have been old enough to be the twenty year-Old’s mother, but Gwen remembered that Steve had mentioned preferring married women. Beth’s tits were perky, but much smaller than Gwen’s. And while Gwen’s legs were the longer and sleeker of the two, Beth had a tight athletic ass that stopped men in their tracks. Beth was perky and cute and had a youthful smile and cute disposition that Gwen envied. Beth was athletic-looking and Gwen wondered wonder what sort of things she might do to please Steve in bed. Something primal awoke in the older woman and she knew she had to squash this rival for Steve’s attention.

“I’ll have you know, Beth, that I had to talk to Steve about the Wilford account. Now, what were you saying?”

Beth was stunned.

Gwen looked at the young woman and smiled inwardly. “I’ll tell you what. Why don’t you pack your things? You’re done here. Maybe you won’t be so quick to call a manager at your next job an old hag. I’ll notify your supervisor that you are being terminated.”

Beth left Gwen’s office in tears. The older woman felt little remorse for the young blonde. She sat back in her chair and thought about this turn of events. She was sure to have Steve’s attention now.

Gwen’s heart skipped a beat when Steve entered her office after lunch. “So now you’re fucking with my love life?”

“I’m sure I have no idea what you’re talking about.” It was Gwen’s turn to be coy.

“You didn’t have to fire the poor girl.”

“Yes I did. She was in my way. She had something I want.”

“No Gwen, I have something you want.”

Gwen blushed and stared at the salesman. She licked her lips as he rearranged the bulge in his slacks.

Steve walked around the hardwood desk until he reached Gwen seated in her leather chair. He took her hand in his firm grip and placed it on his cock bulge. Gwen blushed but found herself massaging Steve’s impressive cock in awe of his size. She remembered that moment in her dorm room with Dean Stevens.

“It’s a lot bigger, isn’t it?” Gwen looked up at her smirking coworker. “I’ll have to be careful. You aren’t ready for me. Darren is half my size.”

“He’s smaller than that.” Her voice squeaked as she traced the outline of his shaft with her index finger.

“Be at my place at eight, boss lady. You’re taking me out tonight.”

Gwen looked up at the younger man and nodded. Steve’s half-hard penis tented the front of his slacks obscenely and she wanted to unzip him right there in her office, but Steve backed away from her.

“I could tell you needed a real cock,” he said with a smug smile. “A sexy bitch like you deserves to be fucked properly.”

Steve turned and left Gwen at her desk. Her panties were soaked and she blushed as she imagined someone noticing Steve and his obvious erection exciting her private office.

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