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A Sissy Tastes His First Cock
Jimmy was a shy individual. And while he would heatedly deny it, most people considered him to a be nothing but a big sissy. With his long brown hair, he was sometimes called 'miss' in stores and he tended to have a rather girlish figure as well. He was by nature, a weak-willed individual and was easily pushed around, even by both sexes.

Having been raised by his domineering aunt, he thought of himself as definitely heterosexual. And to be sure, he found the busty cheerleaders at his school to be very sexy and appealing, even if they didn't know he existed.
But deep down, deep down in his heart of hearts, Jimmy harbored a secret desire, one that he could barely admit even to himself.
Once in the locker room at his school, he'd caught sight of one of the jocks while he was changing out his sweats. Jimmy had marveled at the massive cock the guy had, so different from his own, tiny little pecker. It stirred something inside him and for the rest of the day, he found himself daydreaming of that cock, it's thick, manly width and the big bulbous head. He imagined what it would be like to have a pole of that size, like a baseball bat almost! He even wondered what it would be like to have it in his mouth.
Jimmy blushed as he thought about it and tried to change the color in his cheeks as his schoolmates looked at him in curiosity. But he was secretly fascinated to think of what it would be like to be on his knees, bowing before such a magnificent cock as that, and what it would be like to wrap his lips around it. Jimmy's own minuscule willie stiffened as he thought about it and he was glad he was sitting down so no one would be aware of his forbidden, dirty fantasy.
A year later, Jimmy's secret fantasy hadn't abated--if anything, it had only gotten stronger. But since he had no way of knowing how to go about meeting a man like the one he'd seen that day in the locker room, he picked up an adult newspaper that had personal advertisements for various things. In one ad, he read about a woman who was looking for someone (preferably a guy) to give her husband a blowjob. Evidently, she was concerned about having another woman do it and found a male to be less threatening. In any event, it was with trembling hands that Jimmy finally made the call and contacted the woman.
The woman identified herself as Brenda and Jimmy was immediately intimidated by her strong, forceful personality. She sounded older than him and it was all he could do to keep from wetting himself as she told him when and what he was to do. Instinctively, he felt a fear of this confident, superior-willed woman and he changed his mind a half dozen times before at last making his way to her house. On a whim, he'd worn his prettiest pair of pink panties but now as he stood in front of her house, he regretted taking the risk and being "found out" by her.
After hemming and hawing for ten minutes, he was about to turn around and leave when the front door opened and a striking brunette woman came out.
"Jimmy?" she called out, "Is that you?"
Jimmy's knees shook and he swallowed hard.
"Uh-huh," he replied weakly.
"Come along then," she practically ordered him, "My husband's waiting inside."
Jimmy gulped and stumbled his way up the steps of her entry and he stopped at the top where she looked him over appraisingly.
"How old are you, anyway?" she asked suspiciously.
"I-I'm eighteen," he croaked nervously.
He tried not to stare at her big breasts but she caught him in the act anyway.
"Stare all you want, little boy, but what you'll be getting is a nice big cock in your mouth to suck," she said with smug confidence.
Jimmy swallowed nervously and blushed a hot, beet red. He was not accustomed to be spoken to so bluntly, and especially not by such a pretty woman. It was all the more humiliating that she seemed to regard him as a limp-wrist sissy right off the bat and his presence here did nothing to dispel that image.
Not knowing what to say, he fidgeted anxiously until she opened the front door and led him inside.
It was a very nice house she lived in but it all passed Jimmy in a blur.
What was he doing here? Was he really going to go down on some strange man? He'd never even kissed a girl before and now he was strolling boldly into some woman's bedroom to slurp on her husband's cock. Jimmy's knees went weak and he suddenly didn't have the nerve to go any further.
"I-I-I can't d-do it," he abruptly blurted out.
"What?" Brenda said incredulously.
"This was all a-a big mistake," he bleated out, his face bright red again. His heart was thumping a million miles an hour!
"Oh no you don't," she said firmly, "You've come over to suck a cock and that's exactly what you're going to do," she told him in no uncertain terms.
Before he could stutter out another reply, Brenda snatched up a wooden Spencer paddle and stared at him with a look of steel.
"You're going to go back in that bedroom, or I'll pull you over my lap right now and blister your sissy bottom--Got it?" she said evenly.
Jimmy stared in shock at her before slowly nodding his head submissively.
"That's 'yes ma'am'," she insisted and before he knew what had happened, she'd grabbed his wrist, swung him around and swatted him fiercely on his bottom with the paddle.
"OWW!!" he cried, and to his shame, he felt his eyes welling with tears.
He had no idea she was going to be so strict!! His face burned at his open display of weakness and he sniffed to try and hide his tears.
"Y-yes Ma'am," he bleated like a wounded lamb.
"That's better."
Taking his hand, she pulled him into the bedroom where Jimmy got the first look at her husband. He stood over six feet with big broad shoulders and square, manly chin. Jimmy felt instantly intimidated (as if he wasn't already) and his mouth went dry.
"Here's the little pantywaist I told you about," she said in her imperious tone, "He's ready to service you like a good little boy."
Brenda's husband was wearing only a towel and as he let it fall, Jimmy gaped in amazement and wonder at his massive erection. It was a picture of manly pride, thick and long, curving slightly upwards like a samurai sword.
"Have you ever sucked a cock?" he said huskily.
Jimmy was too frightened to speak and he could only shake his head nervously.
"Well then, this will be extra special for you," he said with a hearty chuckle.
Brenda put her hands on Jimmy's shoulders and pushed him down onto his knees.
"Time to find out what a cock tastes like, Jimmy," she said in her smug tone.
Jimmy licked his lips as he wondered what he'd gotten himself into.
Seeing the hesitancy on his face, Brenda's husband took the initiative and without warning, shoved his mammoth pole into Jimmy's mouth.
"MMRFFGGHHH!!" Jimmy squealed, and both Brenda and her husband laughed boisterously.
Her hunky husband thrust his big cock deep into Jimmy's mouth, gagging the poor sissy until Jimmy placed his hand up to try and steady himself.
Although he knew he liked girls, he couldn't deny the hard-on he was getting as he started to slurp on this man's magnificent member. It filled every inch of his mouth and tasted wonderful to him. He tried his best to use his tongue and the man's moaning soon told him he was doing a good job.
Suddenly, Jimmy heard a click, and as he looked out of the corner of his eye, he saw Brenda snapping pictures of him with a digital camera. With a smirk on her pretty face, she took shot after shot of Jimmy with his mouth full of cock, slobbering and slurping like a cheap whore.
He heard her giggling and he regretted his inability to stand up for himself but it was too late now.
A moment later, the man grabbed Jimmy's head and plunged his mighty cock deep into his mouth. Holding it there, he blew his first load of cum down Jimmy's throat as he roared in ecstasy. The latter squealed like a girl as he was forced to swallow the warm sticky load that was threatening to drown him. After discharging his first ejaculation, the man pulled his cock out slightly and filled Jimmy's mouth with a second helping of warm, creamy semen.
Waving his hands in the air in protest, Jimmy squealed again, his eyes as big as saucers.
The man was still moaning but he wouldn't let go of Jimmy's head. The hapless sissy was forced to swallow a second, then a third load before the man at last withdrew his giant battering ram.
Jimmy was gasping and trying to get his breath as he sat back on his heels, still in shock. Sticky white cum was dribbling down his chin and without thinking, he ran his tongue across his lower lip, unintentionally getting one last taste of the salty fluid.
Without a word, Brenda pushed him down on his back and began undoing his pants, as if she were going to return the favor to him. Misunderstanding her motives, Jimmy sat back and did nothing to stop her, until he realized she was about to discover his pink panties.
"No!" he shouted suddenly but she merely ignored him and yanked his pants down.
Jimmy blushed hot red as his prissy lace panties came into view but Brenda just shook her head as if she'd suspected as much all along.
With a harsh yank, the panties also came down and Jimmy's tiny little wiener was exposed before both of them.
"No! Stop!" he pleaded, but before he could put too much fight into it, Brenda began rubbing some lubricant onto his genitals, although her manner was none too gentle. Jimmy relaxed a bit, thinking for sure she'd finally give him some relief after all he'd been through. However, to his surprise, she began working a strange metal device over his sack.
"Wha-what's that?" he asked curiously.
"You'll see," was all she would tell him.
In a second, she fed his half hardening penis into the stubby cage end of the strange contraption and she joined a metal loop around the back of his entire package. All too soon, Jimmy realized belatedly that his wiener was being trapped in some sort of device and he began fidgeting again.
"He-hey--wait! Stop that!" he protested but she ignored him as if he didn't even exist. With one hand grasping his tiny, child-sized genitalia, she took a long, narrow key and slipped it into a slot at the front of the chastity device. With a quick twist, the device was securely locked and she sat back, a look of immense satisfaction on her pretty face.
"There, that's where your little sissy penis belongs--locked away where you can't play with it," she told him in her no-nonsense tone of voice.
Jimmy quaked in fear as he stared down at his captive willie, the head securely contained in a restrictive steel cage.
"You--you can't do that!" he stammered frighteningly.
"I just did," she said with a smug look of victory, "And you'll be over, every other day from now on, to suck my husband's cock and swallow his cum. If you don't, you'll never see the key to that lock ever again."
Jimmy swallowed hard, the slick taste of semen still coating the inside of his mouth.
Like it or not, he was going to become an expert cocksucker for this strict woman.
Another well written story, Bobby. Poor Jimmy, at least he found a strong Woman like Brenda to help him.
(01-22-2021, 04:15 PM)afp Wrote: Another well written story, Bobby.  Poor Jimmy, at least he found a strong Woman like Brenda to help him.

All weak-kneed sissies need a strong woman like Brenda to keep them in line. Wink
Brenda clearly knows what is best for Jimmy. Quite understandably he was very nervous about a moment that he had waited so long to experience but that pales into insignificance next to the regret he would have felt had he been allowed to back out, and of course the joy he will now feel as a result of it having become a regular arrangement.  Big Grin
Another terrific read, Bobby.
Am sure our little sissy will soon grow to love serving Cock for his Mistress. A small price to pay for Her happiness, surely Wink
Know thy self, sissy.  Don't whine, don't pine, learn to expand your mind.   

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