A Big Wager


A Big Wager by Lou Bealy
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“That wasn’t too fast?” he asked, his face red with shame. He pulled his pants up and put the cash on the dresser.

“Thanks, baby,” Angelina purred once she was paid. “And no, that was perfect,” she soothed. If anything it was better that he came so fast. She wasn’t paid by the hour, after all.

“Okay, good. I uh,” he stammered, his face turning an even deeper shade of red. “With how loud you were and how quickly it happened, I uh...I thought you were…”

“Faking it?” She giggled. “Nah. Don’t worry about me, honey. I always get mine, just like a man would.”

He left quickly after. Her fake smile faded and she got up to count the money. It was all there. Good thing for the client, too. One word from her and Rooker the doorman would snap the guy in half. She had seen him do it and it was amusing but not pretty.

Angelina wasn’t lying to the stamina-lacking client either. She was fortunate that she basically had a hair-trigger and achieved orgasm very quickly and easily, which was definitely a benefit in her line of work. She was also a very attractive young woman, which also helped quite a bit in her job. She was a lithe and thin five foot two, with B-cups that looked large on her tiny frame, a nice round butt that had taken her many squats to attain, and long blonde hair. Her bright blue eyes were also a feature that men noticed. At least the ones that bothered to look her in the eyes.

Even with her ability to easily have an orgasm, she was still routinely disappointed by the men she serviced. She tried not to take their failings personally but it was hard not to think of them as pathetic, selfish losers.

She put on her black panties and matching little strapless black dress before she made her way back down to the bar area. She got herself a drink at the bar before taking a spot at her regular table to wait for another client.

“Hey, Ange,” Kyla, one of her fellow employees at the brothel said, taking a seat next to her. “How’s your night been?” Kyla cut a statuesque figure, being almost six feet tall with a slim but athletic build and dark swarthy features.

Angelina had always been jealous of her. She was so tall, athletic, and had huge boobs. Angelina knew she was probably “prettier” but somehow the amazon of a woman was able to exude sex so she got a lot more high priced clients than most, even more than Angelina. She was also very skilled at pleasing men and other women. Angelina had experienced that first hand a number of times. Clients sometimes wanted to watch two girls or engage in threesomes (if they paid enough) and Kyla was always Angelina’s first choice of female playmates when it struck her fancy. She didn’t know if Kyla felt the same about her but she hoped so.

“The usual.” Angelina sighed. ‘These guys would be just lost if they weren’t paying for sex.” She chuckled. “They’re totally lost when it comes to how to pleasure a woman.”

“Yeah, tell me about it.” Kyla sighed. “You’re lucky, though. They at least make you cum. I hear you in there and I can tell the difference between a fake orgasm and a real one.”

“Because you always fake it?” Angelina teased with a giggle. “Except with me, of course.”

Kyla laughed along with her. “Exactly. My clients aren’t any better at it than yours are, the losers. And I’m sure their dicks are just as small too. It makes me weep for their wives. Maybe we should offer to teach them the right way to use their mouths.” She flicked her tongue out and licked between her fingers in an obvious reference to cunnilingus. “Because they couldn’t do it right even if they didn't have tiny dicks.” They both laughed. “On the clock, of course,” she added.

They talked a little while longer before one of Kyla’s clients showed up and she left the table to go make some money. Angelina finished her drink and ordered another from the bar, surveying the room for any potential customers.

“I’ll get that, and a whiskey for me,” a deep baritone voice from behind her told the bartender who nodded.

She turned and saw a well-dressed man with long dark hair who appeared to be in his thirties. His business suit and expensive-looking haircut suggested he was a man of means. He had a full beard and plain features but appeared to be in good shape. She gave him the same smile that always made men melt.

“Hello, handsome.” She batted her eyes at him, but he didn’t seem affected by her flirting. He didn’t even return her smile. He just looked at her sternly and pointed to a nearby table. She followed him and sat down at the table, still smiling and attempting to charm him. She had seen plenty of times that it just took persistence to crack some men’s tough-guy front.

At first, she waited for him to make the first move and just sat, enjoying her drink in silence. He already bought her a drink so it was clear that he was interested. He kept staring at her with the same stern expression on his face. After a few minutes, it began to make her uneasy so she decided to break the silence.

“So, what do you do, mister serious?” She smiled again and then took a drink of her screwdriver.

He drained most of his whiskey glass and then answered, “I have a proposal for you.”

That relaxed her a little because he finally smiled back at her but also made her a little skeptical of the guy. “What sort of proposal? They told you the rules when you came in, right?” There was also something… predatory about his smile that unnerved her the longer he held it.

“It’s not your pussy that I want. Well, not like that.” He chuckled to himself.

“What are you talking about?” she demanded, dropping her sweet demure woman act.

“I would like to make a bet with you,” he said, finishing his drink.

She grabbed her drink and went to stand up. “A bet? This isn’t that kind of-”

“You’ll like this bet. So just listen.”

Something about him was very intimidating all of a sudden. The way he looked at her froze her to her chair. She looked around for the bouncers.

“You have a pretty low opinion of men that have small dicks or that lack certain sexual capabilities, am I right?”

“How did you…” Angelina looked to the spot she had been at when talking to Kyla, a secluded corner that she was sure no one was sitting close enough to hear their conversation. She looked back at the strange man.

“You fantasize about being able to prove just how much better at it you would be if you had a dick,” he whispered. “Don’t you?”

That struck her silent. How could he possibly know about her deepest fantasies? About her desire to actually fuck a woman with a real dick rather than with a strapon? She would always imagine a scenario of fucking for hours, giving her lovers so many orgasms they would beg for her to stop before she filled them with a torrent of cum. It was one of her many fantasies that she had throughout her life but it was one that she had never gotten the chance to indulge in, for obvious reasons.

But she had never told anyone about that particular fantasy. Ever. How could he possibly know about them?

He saw the creeped out look on her face and chuckled. “Anyway, as I was saying, I would like to make a bet,” he continued. “I want to see if you actually could do any better than these loser guys.”

If I could do any better?” she scoffed, trying not to show how nervous this all was making her. “Look, I don’t know what you think you know about me but I’ve had plenty of practice with other-”

“But that wasn’t really what you wanted, though. Right?” He leaned in and his grin was menacing to the point that she began to frantically look around for help until she spotted Rooker. “You weren’t using the same equipment as the men, with the same limitations, were you? But you were imagining that you did have that equipment.”

“This is too weird.” She shook her head, totally done with this strange conversation. It was freaky that he somehow knew what he knew. She began waving at Rooker, who saw and began to approach from the other side of the room. She still found herself unable to simply stand up and leave, most likely due to her fear of him retaliating in some way. “I don’t know what you are on but you’re about to be sorry you came in here all fucked up and talked to me that way.” She grinned at him smugly.

“I think a small demonstration will help to communicate what I want much more quickly than this useless banter.” He waved his hand with a flip of his wrist and the air seemed to shimmer for a moment.

“Oh…” Angelina swooned with a sudden swell of dizziness. She fell back in her chair and her head rolled back until she was staring at the ceiling.

Rooker arrived a moment later and looked to her to see what she wanted him to do. He stared daggers at the strange well-dressed man who just smiled at him.

“Can I get another whiskey? And what would the lady like?” He turned to her expectantly, still smiling his menacing smile.

“Angelina?” Rooker asked, clearly concerned but not willing to do anything without her direction. She knew that he had seen plenty of strange situations end up with money changing hands and everyone leaving happy.

It was that moment that her dizziness had passed and she finally was able to sit up but felt a strange tightness that she couldn’t explain. Confused, she felt herself all over as she looked to the burly bouncer. “Rooker, this guy…” She stopped when her hand reached her crotch, realizing where the bizarre sensation was coming from.

Rooker waited for her to finish her thought, but she momentarily forgot about him. She was far too absorbed in her discovery. Through her skirt, she felt a strange bulge in the front of her panties that matched the location of the strange pinching feeling.

No, she thought. That’s impossible...

“You want me to trash this asshole or what?” Rooker asked impatiently, interrupting her inner monologue. Rooker turned and loomed over the dapper man but he didn’t even seem to notice the presence of the huge bouncer. He just knowingly smiled at her even wider.

Her hand slipped under her panties both to relieve the pressure of being pinched by her panties and to verify the impossible situation occurring between her legs. She thought she might be crazy but she couldn’t deny what her hand was feeling nor the sensation from the other side.

Rooker gave up waiting and angrily strode around the table, reaching out to grab the strange man, who didn’t seem to react at all.

“Uh, sorry. I’m okay, Rooker,” she stammered, and he stopped and looked back to her skeptically. She felt awkward with the bouncer staring at her when only the table was preventing him from seeing the strange new lump in the front of her skirt.

“You sure?” the bouncer asked, still glaring at the strange man, his fists clenched.

“Y-yeah, I’ll be okay, really.” She forced a fake smile. “Thanks.” She turned back to the frightening man. Surprisingly, a good portion of her fear had been supplanted by what she could only describe as a thrilling excitement. “I’ll call you if I need you, though.”

Rooker shook his head and walked back to his post at the door.

“What do you think?” The man asked, laughing. He seemed almost giddy. “Is it everything you imagined that it would be?”

Angelina willed herself to release her grasp on the rapidly thickening shaft in her panties. As much as she would love to experience the new sensations she had never felt before in her life, she was still bewildered by this turn of events.

“I won’t know until I-” she stopped herself, the excitement of her new anatomical arrangement had distracted her from just how surreal the situation was. She took a deep breath and steadied herself. “Who- what are you?” she demanded in a whisper. Her cock continued to grow, despite her fear and the strangeness of the whole situation. It wasn’t even fully erect and it was huge. Her panties could barely contain it. Luckily they were made from very stretchy material.

“I’d prefer not to give my real name, but you can call me Hal.” His happy demeanor evaporated and he became very frightening in the blink of an eye. He glared at her. “And let’s not worry so much about what I am. Let’s just say I have the power to give you what you have always wanted.”

“Well, I definitely wished I could try it for my-” she started to say.

“But there’s a catch.” He cut her off.

“A c-catch?” Angelina asked, barely able to squeak out the words. Her sudden erection being constricted by her panties made it hard to concentrate on anything else. The urge to rip her panties off and free the monster was hard to resist.

“Yes.” His grin returned but she wasn’t able to relax at all. “I told you I wanted to make a bet, didn’t I?” He leaned back in his chair and snapped at one of the girls, “Can I get another drink already?” he asked, lighting up a cigarette.

“What sort of bet? And what if I am not interested?” She was able to summon a bit of confidence. Her cock throbbed as she crossed her arms in defiance. Was it somehow giving her more confidence she momentarily wondered?

“I could just take it away and leave.” He blew out a long breath of smoke and grabbed his drink from the server girl, taking a big gulp, draining most of it. “But I know you don’t want that. Not before you’ve had a chance to try it out. Why don’t you do that?”

“Do what? You mean... try it out?” she asked, her voice full of wonder.

“You’ve always wanted to, haven’t you?” He grinned. “You really should, you know. Before I change my mind and take it away just as easily as I gave it to you.” His grin faded to a stern expression. “I am losing patience.” He drained the rest of the glass. And took another drag from his cigarette. “There are plenty of other people with the sort of wishes and desires it would amuse me to grant,” he said as he exhaled the smoke.

Angelina didn’t need any more encouragement. She got up and walked bow-legged as quickly as she could to the bathroom, holding her hands in front of her crotch. She heard the man chuckle and order another drink.

She got to the bathroom and dashed past a few other girls who gave her a strange look as she passed by, still covering her crotch. She quickened her pace even more when she saw the confused looks that the johns were giving her.

She threw open the door to one of the stalls and locked the door behind her before hiking up her skirt. It was a bizarre sight, her erect penis sticking out of the waistband of her black panties. The swollen head was covered in foreskin that looked like it could barely contain all her man meat. The tip was leaking precum that had smeared against her belly as she walked. She pulled her panties down around her ankles and just admired her new anatomy.

Her new cock stood painfully erect, pointing up at an angle away from her body. It was at least a foot long and as big around as a beer can. She couldn’t even get her fingers all the way around it. She stared in awe at it for a moment, taking in every detail. The skin was smooth, all the way to the tip where it was stretched around the swollen and leaking tip. Her balls were huge, bigger than any man’s she had ever seen and the sack was too much for even both hands to hold all of. There were large black hairs covering her crotch that continued up her abdomen until almost reaching her belly button. Even erect, there was a certain heft to it when she held it in her hand. She felt powerful like she had a weapon that was the secret weakness of any woman that she used it on.

She smiled and pulled back on the skin, exposing her flared tip to the cool air. She touched the glans with her finger and sucked air through her teeth when she felt her finger touch the smooth skin. It was much more sensitive than she had expected. She slowly stroked the foreskin back and forth, savoring the stimulation from her skin gliding over the smooth head of her cock. When she heard the last girl leave the bathroom, she couldn’t resist striding out of the stall to look at herself in the mirror. She stared at herself, taking in the big change. She didn’t take her eyes off of her reflection. Her plan had been to have a quick peek and then go back to ask that strange man what the deal was, but she was now mesmerized by her altered anatomy and appearance.

“I can’t believe this,” she whispered in disbelief to petite young hottie staring back at her, stroking a huge throbbing penis. “Well, look at you, gorgeous.” She said to her reflection and giggled. She reached up to her chest and cupped her boob through her dress. She squeezed and rubbed it, loving the feeling of her erect nipple rubbing against the soft, thin material. The stimulation and the hot scene in the mirror made her cock seem to grow even more erect if that were even possible. She stared at her reflection as the stroking motion of her hand increased in both speed and vigor.

Her hand glided up and down the long shaft, feeling her soft skin with hard flesh underneath. She removed her hand from her breast and then spat on it. She rubbed her slick palm across the sensitive head of her huge cock, which made her knees weak. She couldn’t decide what felt more amazing. In almost no time, her legs began to shake as she felt her orgasm building. She leaned against the counter and stroked with the other hand until she exploded, feeling her muscles squeeze and spasm inside of her, she closed her eyes and it felt like emptied her balls all over the counter.

She surveyed the scene as she caught her breath, wondering where all of the cum must have gone. She looked down and saw one little glob on the floor. She wondered where the rest went but gave up when she heard the door open and another girl, a voluptuous brunette named Crystal, came in. She was staring at her phone so it gave Angelina a chance to pull her skirt down and conceal her huge, still mostly erect dick.

She didn’t even bother grabbing her panties- they didn’t fit anyway- or cleaning up her mess before she returned to the bar, thankful that the dark lighting made it difficult to see the bulge in her black dress. She looked down at the bulge and smiled to herself. She knew that she would have to try that again. It had made her feel amazing. Potent. Powerful. She was instantly addicted, there was no denying it.

Hal grinned at her as she sat down, and scooted up to the table so her crotch was fully concealed.

“I won’t rub it in. But since you rubbed one out, I know you believe me now,” he said with a chuckle, then took one more puff and put out his cigarette. “I trust you had fun trying it out? You came back pretty quick, though. It didn’t take as long now that you’re the “man”, huh?” he teased.

She didn’t answer, trying not to give him the satisfaction. She was just getting used to her new anatomy, so she didn’t think cumming as quickly as she did was necessarily a problem. She was sure she would figure it out. Besides, she was trying to cum quickly.

“Alright, be that way.” He drained another glass and plopped it down on the table. “So what do you think, would you like to make a wager?” He lit up another cigarette.

“What kind of wager?” she asked warily.

“Well, since you had fun with it, I am guessing you want to keep your new toy?” He grinned, staring unblinking at her.

She didn’t answer, stubbornly refusing to give him what he seemed to want.

“You know,” he said, his grin draining from his face. “For fulfilling your deepest desire, you could show me a little gratitude.”

She sighed. “Yes,” she said quietly, looking away from him.

“Yes what?” he demanded in an even and stern tone like he was talking to a child. He fixed her with that unnerving stare again.

“Yes, I would like to keep it,” she said finally. “At least for a little while.”

“Well, you can keep it, if you win the bet. But you won’t be able to go back to being regular old you. You’ll be thinking with two heads from now on. Well, mostly just the little one like most people who have them.” He laughed at his own joke. He gestured toward her crotch, still hidden under the table. “You think you’ll be able to keep hiding it, in your line of work? Or are you just going to embrace it?”

“I can keep it if I win this bet?” She crossed her arms defiantly and leaned back, exposing the lump in her dress that he seemed to think embarrassed her. If she was going to keep it, she decided that she would flaunt it. So why not start immediately? “Would you just explain what the wager is, already?”

His smile returned. “Of course.” He looked very menacing as he breathed smoke out around his face. “Simple. Give a woman an orgasm.”

“That’s it?” she asked in disbelief and laughed.

“With that.” He pointed with the cigarette in hand to her crotch, then took another drag. “No using fingers or tongue,” he said, blowing out the smoke.

“So I get to keep it after that?” she asked, thinking about how easy she would win this bet.

“Exactly.” He took a long drink and a puff of his cigarette. He stared at her, seemingly just pausing to make her wait. Finally, he spoke again, “You get to keep that big chunk of man meat.”

“I know I’ll win but what happens if I lose?” she asked with a self-assured and cocky tone.

“You don’t get to keep that nice big gift.” Hal gestured to her crotch. “Simple, no? You will have until the end of tomorrow to give another woman an orgasm and win, keeping your new toy.” He offered his hand to shake and thus sealing the wager.

“Too easy,” she laughed and reached out to shake his hand. His hand enveloped hers and squeezed hard as they shook.

“See you here soon, Angelina.” He released her hand.

Then something even stranger happened. She looked away for just a moment when she saw someone enter the bar that she thought may have been a client of hers. When she looked back, Hal had disappeared. She thought for just a moment that she may have dreamed it all but his empty glass and a still-burning cigarette were still on the table. The exciting presence of the huge lump in her dress remained as well.

She couldn’t wait to share this with the other girls. It was too amazing not to share. She waited in the bar for one of her friends to enter and it wasn’t long before Kyla came back in, looking just as primped and pretty as she always did. Angelina knew how important clean up was after seeing a client. You had to always look your best and not like you just got done sucking a cock.

Kyla came over to the table with a drink in hand to say hello but she immediately noticed how Angelina was absolutely beaming.

“What’s going on?” she asked, laughing. “Did a guy finally find the man in the boat, or what?” Kyla plopped down in the seat next to her at the table.

“Way better than that. Better than I ever expected.” Angelina replied, reaching over and grabbing Kyla’s free hand.

“What are you-” she stopped when her hand reached Angelina’s crotch. She looked at her friend in confusion and raised her eyebrows, asking a question nonverbally.

Angelina smiled back. “You want to see it?”

Moments later, the pair burst into one of the unused rooms giggling.

“If you wanted to get me alone with you for some play time, you could just ask,” Kyla said good-naturedly. “Alright, let’s see it,” she demanded, laying across the bed. She was clearly still skeptical.

Angelina gave a little strip tease, bending over to show her ass through the dress before slowly pulling it up from the front. She then spun around. “Tada!” she sang with a giggle as her long cock swung over and hit her leg with a loud SMACK. “You want to come say hi to my monster?” She teased, continuing to flap her dick back and forth.

Kyla opened her mouth to say something but was struck speechless and just stared for a moment before finally stammering, “What- how?”

“It’s complicated,” she said evasively. Angelina didn’t really care to explain the strange man and the bet she had entered into. Besides, she was already getting horny thinking about what she was going to do to Kyla.

“I bet,” Kyla replied, still staring at the huge cock that was rapidly growing even bigger. “I guess we can skip all of the boring explanation and go straight to the main event.”

“What do you think?” Angelina fixed Kyla with her best seductive look. “You want to play?”

Kyla slowly sat upright on the bed as she stared in awe at the biggest cock she had ever seen, and she had seen more than her share. “My god… it’s so… huge.” She reached out and grabbed it, barely able to get even her large (for a woman) hand around it. She pulled the foreskin back, causing Angelina to softly moan. She flicked her tongue out, sliding across the sensitive head.

“Mmm…” she moaned as her cock entered Kyla’s mouth for the first time. “It’s lovely, isn’t it? It’s a cock worthy of such a fine specimen as me, don’t you think?”

“I’d say so…” Kyla said, popping the swollen head of her dick out of her mouth for a moment. “And worthy of me as well,” she added before slurping the cock back in and bobbing her head.

“Oh yeah…” Angelina began to thrust her hips forward slightly and fuck her friend’s face without even meaning to. After a short time, she grabbed Kyla’s hair with each hand and began to pick up speed, shoving her cock deeper and deeper until Kyla was deepthroating. Kyla handled it with unsurprising skill and didn’t even gag as inches of cock meat disappeared into her mouth. She loved the view she had from that angle.

Kyla suddenly pushed Angelina’s hands away and pulled her mouth off of the cock. She threw herself back on the bed, reached down to slide her panties off of her legs and then tossed them aside. She spread her legs, revealing her hairless pussy which was already dripping wet and engorged with blood, showing just how eager she was. She gave Angelina a needy, impatient look.

And Angelina’s throbbing dick showed she was just as eager. “You have no idea how long I have been wanting to do this,” she whispered, climbing on top of Kyla. She lined the head of her cock up with Kyla’s juicy pussy and slid in the first few inches.

“Ah” Kyla cried out, trying to get used to the size of it.

A part of her wanted to ask if Kyla was okay, but she thought better of it. She was in charge, and Kyla would get whatever she would give her.

“You’d better be ready for more…” she whispered, pressing her hips harder. She had plenty of lubrication, she just needed to stretch.

“Fuck yeah,” she replied in a husky voice. Her eyes went wide and said with her voice full of awe, “Just slow down. You’re so big….”

Angelina waited for a moment then pushed a little more, and a couple more inches of her cock disappeared inside Kyla who was writhing on the bed, moaning.

“And you’re so beautiful…” Angelina told Kyla a moment later and slid her cock in just a little more. She looked down and saw that she wasn’t even halfway in yet. It almost made her want to laugh but she was able to control herself. She didn’t want to ruin the moment.

“Jesus Christ.” Kyla’s eyes rolled back into her head as her pussy accepted another couple of inches of Angelina’s cock.

Angelina concentrated on doing it the way she knew that she would want it. She was loving every second of Kyla being at her mercy. She knew to pull out and thrust back in slowly a few times before pushing even deeper. She slid in and out again a few more times until her cock was finally able to fit all of her cock inside…

And then she came. “Ahh…” Angelina softly cried, her body began to shake as she was hit by her first male orgasm. Her toes curled and she thrust in as hard as she could, her cock erupting inside of Kyla. Her body shook in time with a few more spurts of cum. She kept thrusting her hips back and forth, her now ultra-sensitive cock slid against the walls of Kyla’s pussy. She cried out again and was forced to stop. She was too sensitive.

“What- already?” Kyla said, sounding very disappointed and almost offended. “I guess I expected better from…” She saw the look of horror on Angelina’s face and stopped herself. She then smiled like she had probably smiled at many a man who had cum as quickly as she had. “I'm sorry. It was pretty great, babe. I had fun,” she said, sounding very sincere.

Angelina almost felt offended that her friend would placate her. She took a breath and tried to start fucking again, but by that point, her dick had started going soft but was still just as sensitive.

“Ah,” Angelina whimpered, her softening cock slipping out of Kyla’s pussy. She realized at that moment that she couldn't continue any longer and it made her even more embarrassed. She had actually met a few guys who would just keep fucking after having an orgasm but she evidently couldn’t pull it off. At least not so quickly. She could get better at it, she told herself.

“It’s okay. Really.” Kyla insisted but Angelina definitely wasn’t buying it. She knew better.

She had said the same thing in the same tone as that so many times, she knew it was just humoring her to prevent her ego from getting hurt. Not that it really mattered because she had just barely gotten her dick in before cumming. It was pretty undeniable how lousy that would be if a john had cum as quickly as she had. She couldn’t bring herself to call Kyla out, though. It would only make her shameful performance even more shameful.

“This was fun but…” Kyla pulled herself away and rolled off the bed. “I have to go.”

Angelina almost wanted to argue, to say that they could keep going, that she could eat her pussy or whatever, it seemed like the moment had passed. Kyla was already pulling her panties back on while Angelina continued to dither on how she was going to react. She watched in shameful silence as Kyla slipped out of the room.

She sat in the empty room for a while longer, looking down at her dick and wondering how something so big and powerful was still so disappointing. She held the still slimy male organ in her hand and stared at it, almost as if she was trying to glare at it in disappointment.

“How could you let me down like that? That was Kyla of all people!” she jokingly scolded her penis. “You’re so big and perfect! How could you…” she stopped when she noticed something strange. It seemed smaller than it was before her encounter with Kyla but she chalked it up to still recovering post orgasm and left it at that.

She decided that she could do better, she just had to get more experience with her new little- that is big buddy. Then she could win the bet. She had until the end of the following night and she was still confident that she had it in the bag.

She took a shower, relaxed for a bit and recuperated from the encounter. She knew enough about male anatomy to know that they would need some time to recover before being able to perform again and it seemed to hold true. She tried a few times to get hard again but only got to about half-mast. The last thing she wanted to do would be to incur further embarrassment to add not being able to get it up on her earlier premature ejaculation. That would be utterly humiliating. No way would she put herself in that kind of position.

Eventually, after putting her dress back on and grabbing a handbag to hold in front of her crotch, she made her way back down to the bar area. She needed a drink to soothe her bruised ego. She took a seat at her normal table and signaled for the server to bring her one of her usual.

She had already made her money for the night and so wasn’t expected to pick up any more work unless she wanted to, so she was able to relax and just watch the ebb and flow of men coming in for sex with one of the beautiful, high-class prostitutes working there. She didn’t normally watch the goings-on. She didn’t like to pussyfoot around and mostly did her business on an appointment-only basis, unlike the other girls who didn’t have a series of regular clients and referrals. She was always too into her own business of making money and then leaving to go shopping when she had enough cash.

But now she was intrigued by both the mostly well-dressed men and the exquisite female bodies on display. A few men came by her table and asked to buy her a drink and she was tempted at first. She could maybe make some extra money while working on this bet but she reminded herself that they probably wouldn't be as thrilled when they discovered her male organ, so she politely turned them down. Despite her distracting predicament, she had the wherewithal to give the particularly well-dressed ones her card for later on. She giggled to herself, thinking that they would probably be jealous that she was so much bigger than them.

She paid a lot more attention to the girls than she usually did. She was a switch hitter when she needed to be but that was usually for business and only occasionally for pleasure when she was feeling adventurous and not because she was particularly attracted to women. But since the change, she found herself drawn to the scantily clad bodies of her coworkers. Even with the wealthy, affluent men that normally she mostly found quite attractive walking around, she was still more interested in the sexy curves, asses, and tits that were barely covered and on display.

She just watched the proceedings for a short while, until she became more and more randy. Her cock was straining in her dress, just waiting to be put to use. She could even feel it leaking into the fabric of her dress.

She was about to lose it and go back to the room to take care of it herself, when the cute brunette waitress, a girl named Charmaine came by to offer her another drink. Angelina made eye contact with her and then slid back in her chair. The huge lump in her dress sprang into view from under the table in a way that was impossible to miss. Charmaine’s eyes went wide when she saw it.

“What time do you get off?” Angelina asked, grinning. She thrust her hips forward, emphasizing the bulge even more. She had never realized how cute Charmaine was. She knew that her slim body and girl-next-door face were appreciated by the guys, but she had never noticed just how hot she was. Despite being so slim, she had b-cup tits that looked huge on her and a nice round ass.

Charmaine just smiled back, unable to break her gaze from the obvious shape of Angelina’s clothed cock. “I, uh.” She blushed and reached out towards Angelina’s crotch before stopping herself and jerking her hand back. “I could take my break here in a few minutes…”

Convinced she had one on the hook, Angelina stood up to leave. She turned back to add, “I’ll be in room eight. I won’t wait long.” She gripped her handbag in front of her erection and left without looking back.

When she got there, she quickly stripped off her clothes and climbed onto the bed. She looked down at her rigid cock and again for just a moment, she thought it might look a little smaller than when she first got it but quickly pushed those thoughts aside. She couldn’t help herself and began to slowly stroke her leaking cock, trying her best to keep the pace slow so she would have plenty of stamina left.

Just as Angelina expected, less than five minutes later there was a knock at the door. Angelina called out, “Come in, Charmaine.”

In walked the cute brunette, blushing and looking timid. She was staring at the floor so it took her just a moment to notice that Angelina was sitting on the bed naked, jerking her twelve-inch leaking uncut dick.

Charmaine’s eyes went wide. “Holy shit. It is real.” She walked over towards the bed and kicked her shoes off. She climbed on to the bed into a sixty-nine position.

Angelina’s face was inches away from Charmaine’s clothed crotch and thought she could smell her aroused pussy through her thin pants. She found it intoxicating in a way that she never had before.

Charmaine grabbed ahold of Angelina’s cock near the head and gently stroked it, her hands enveloping the swollen purple head. Her precum served as lubrication for her hands rubbing over the entire surface. She leaned in and began to lick the head with the tip of her tongue.

Angelina’s hissed, breathing through her teeth. The head of her cock was so sensitive, similar to her clit. Not quite as sensitive, but it was so much bigger with so much more to stimulate. Charmaine was rubbing her slimy head with both hands and it was so intense that her legs started to twitch and she couldn’t hold back a moan. She knew that if this went on she would blow her load before she had a chance to win the bet, so she stood up on her knees, and began to undress Charmaine, unfastening her pants and yanking them off, which took a moment because of how tight they were.

Charmaine didn’t even react, seemingly transfixed by the slab of man meat in her hands. She slipped the tip into her mouth and slid her tongue all around the head. Which caused Angelina’s whole body to stiffen as she was wracked with pleasure so intense it made her twitch.

“Oh fuck…” Angelina moaned. Her hips seemingly started jerking on their own, shoving her cock deeper into Charmaine’s mouth. She felt an orgasm coming but was powerless to stop herself.

“Mmmf!” Charmaine struggled to fit the cock and its sheer girth into her mouth, she wrapped her hands firmly around the base and began to stroke in time with Angelina’s thrusts.

“Gah!” Angelina cried out, feeling her cock swell even more and then explode inside Charmaine’s mouth, spraying a load of cum that hit the back of her throat.

Charmaine swallowed it all and then continued to slide her tongue around the head, which drove Angelina nuts. Her cock was so sensitive after the orgasm that she could hardly stand it.

Eventually, Charmaine removed the already softening cock from her mouth. She gave the same fake smile that Kyla had already given her, the one she knew so well and that was making her more embarrassed and angry.

“Wow, that was… something.” Charmaine stood up and wiped her mouth. “Nice cock. I’ll, uh...” She pulled her pants back on quickly and moved towards the door.

“Don’t go-” Angelina started to say but she couldn’t find her voice.

It seemed Charmaine didn’t even hear her and said, “I’ll see you later, I guess.” And slipped out.

Angelina sat there feeling humiliated. Again.

It took her a good long while to collect herself. She tried not to think about what had just happened because it only made her want to scream. Or cry. Or both. And again, whenever she looked down at her now flaccid cock, she thought that it definitely looked smaller.

She cleaned up and got dressed before grabbing her things to leave for the night. On her way out she passed through the bar and saw Hal sitting at her table, smiling at her. She almost missed him and had to do a double-take. He wasn’t sitting there a moment before, she was sure of it.

“Having fun yet?” he asked with his now trademark grin. He was dressed in the same suit and had a drink and lit a cigarette in front of him.

“You-” she pointed at him angrily. “You did this to me.”

He laughed. “Well… yes.” He pointed to the chair next to him and she angrily sat down. “I gave you what you have always wanted, right?”

“No!” she practically yelled then realized people were staring, including Rooker from his spot at the door, and lowered her voice. “I mean, yes… but-”

“But what?” He chuckled and took a drag from his cigarette. “It’s not how you imagined it?” he teased.

“I- no,” she stammered. “I thought it would- you know- be easy to win this wager.” Her eyes narrowed at him. “You gave me a cock that isn’t up to the task!” she yell-whispered.

He laughed and swallowed the rest of his drink. “Well, if it were a forgone conclusion,” He chuckled and took a drag. “It wouldn’t be much of a bet, would it?”

“So you did sabotage me!” she yelled, getting mad again.

“No,” he said, between laughing in his deep baritone. “I think you simply underestimated how difficult it would be to do it with your new anatomy.” He straightened up and said in a mock paternal tone, “But you don’t have time to worry about that too much. You only have until tomorrow night.”

“I’m not even sure I want to keep it anymore…” she muttered despondently.

“Well, you wouldn’t want to admit that most guys are way better at it than you are, would you?” He laughed a cruel, mocking laugh.
“Fuck you!” she shouted, then realized how much of a scene she was making. She again felt embarrassment for raising her voice and turned to look around and make sure that no one was staring. Rooker looked at her with a confused expression but she just shook her head no. There was nothing he could do for her.

When she looked back, Hal was gone. His empty glass and what was left of his burning cigarette were all that remained. Her confidence was shaken and she didn’t think she would have any success that night. She was already exhausted physically and mentally.

* * *

The next day she decided to get up early. She was tired from her poor night’s sleep, strange dreams of her coming to work naked with a tiny penis plagued her throughout the night. She got herself a cup of coffee and sat at her computer desk to look up some porn. She knew a bit about male anatomy, and she had an idea. Her plan was to shoot a load before going into work, so she would take longer to cum when she did eventually hook up with someone. She figured there would be enough time to recover from the orgasm so she could get it up but it would still help her stamina. Besides, she was already hard as a rock and it would not go down. She couldn’t help herself; it was just begging to be used.

She pulled on her cock and quickly got it hard. Once hard, she inspected it closely for a bit and eventually decided that it didn’t look any smaller. She was still worried, though.

Getting back to business, she found some lesbian videos with some hot women fucking each other with a strapon and a few minutes later she was shooting a wad into a paper towel. Curious, she looked at the size of her load and saw how unimpressive the first load of the day was. Just a few little unimpressive globs.

A moment later, she actually could see it shrink. Her eyes went wide as she watched the head of her dick seemingly slide closer to her balls. She reached out to grab it but it slipped right through her fingers.

"Oh no…" she muttered to herself, staring in horror. She had seen her fair share of dicks in her life, or even more than that due to her line of work, and hers no longer looked as large and impressive as it had before. It was still big, but definitely not even close to as large as it had been. She was running out of time and she knew it. She choked back tears, realizing that she had really missed the opportunity to utterly dominate a woman with a huge cock.

It seemed as if she was only getting smaller every time she had an orgasm. She was sure of it because she was the same size as the end of the night before and then suddenly shrank after masturbating. She tried not to dwell on it, though. She had a bet to win.

When she had waited what seemed to be a good length of time, she showered and got dressed in a bright red sundress and matching panties. She was able to find a bit of her confidence from before, but it had definitely suffered pretty badly.

She went in to work early and cleared her appointments for the day. The girls there largely handled their own business and just had to pay a flat fee for the week, so there were thankfully no questions about what she was still doing there after she canceled her work for the day. She texted a few lady friends and told them she had something they had to see, got herself some coffee to help wake her up and then took a seat at her usual table and waited for one of her friends to show up.

She watched and waited, trying not to let her anxiety build. Her confidence had been eroded by the events of the previous night but she was still hopeful that she could learn how to perform the way she originally thought she would have performed. And besides that, she didn’t seem to have much choice now. She didn’t want to lose this bet. The conversation with Hal had led her to believe that she would be left with a small, shrunken penis if she lost. That would be even worse than not having one at all, which she was becoming more unsure she should have accepted in the first place.

Besides that urgency, she was still feeling urgency in a more biological sense as well. She was constantly rock hard.

Eventually, she spotted her friend Jackie walk in. Jackie worked there only a couple of days a week and had a regular job in the city most of the time. She was a ginger so she got all of the guys who were into that. She had long straight red hair and was covered head to toe in freckles. She was medium height, with nice C-cups and an athletic build. But better than that, she was a total sexpot, always flirting with everyone and just oozing sex wherever she went. She was perfect.

Angelina waved for her to come over.

"Hey, Ange." Jackie smiled warmly as she got to the table. "What is it that you absolutely needed to show me?" She sat down next to Angelina and was about to order a drink but stopped when she looked back at Angelina.

More specifically she was looking under the table. Angelina was stretching her red sundress tight across her lap. Through the tight, thin material she could see the outline of a good-sized penis. Her mouth went wide in shock but then curled into a smile.

"Ange… I never…” she stammered and then looked up at her eyes and giggled. “Is that-" she began to ask but stopped when Angelina put her finger to Jackie's lips and gently shushed her.

"I'll give you a better look at it in room eight," she whispered seductively.

She was naked before Jackie had even closed the door behind them. Her dress came over her head in a flash and she was left wearing only heels. She turned around and her rapidly thickening cock swung into view a moment later, causing Jackie to gasp.

“You’ve been hiding that beautiful thing the whole time?” Jackie teased, reaching for it.

Angelina turned away. “Ah, ah!” she teased. She walked over to the bed and sat, her cock sticking up from her lap, throbbing and twitching. “Strip,” she demanded, not having any patience this time. She needed to get this done.

Jackie’s smile disappeared and was replaced by an expression of lust while she stared at Angelina’s leaking cock.

They got down to business immediately. Angelina pulled Jackie on the bed and rolled her over onto her back, then climbed on top of her, forcibly parting her legs with her knee. She slid her cock around Jackie’s entrance, wetting the tip before finding her center. She slid in the first few inches before hitting resistance, then pulled back and thrust in again, sliding in a lot more. She noticed how much easier it was to fit her dick than the last time but remembered why.

She had definitely lost some girth along with the inches of length, which was made even more clear when she bottomed out inside Jackie a moment later. She barely got her huge dick in the last time and this time it only took a few seconds.

“Mm…” Jackie cooed. “Fuck me…” she pleaded, squirming around enough to get some stimulation while Angelina shoved her cock in as far as she could, pressing with all of her might, flexing every muscle. Jackie just clung to her, wrapping her arms and legs around her petite frame and pulling with all of her strength at the same time.

“F-fuck!” Angelina sputtered.

Angelina finally began to slowly slide her dick in and out, making Jackie moan and squirm even more. She tried to start out slow. It felt amazing, the throbbing sensitive head of her dick sliding over the soft fleshy walls of Jackie’s pussy. Jackie began to roll her hips, creating a nice rhythm of Angelina’s cock sliding in and out.

She probably didn’t even last a minute before she felt another orgasm coming on. By the time she tried to stop, it was too late. Jackie’s writhing beneath her was just enough stimulation to send her over the edge.

“N-no!” she groaned then bit her lip. There was nothing she could do to stop herself. She began thrusting rapidly in very short strokes and then exploded a moment later with a muffled cry.

She opened her eyes and saw the surprised and then disappointed look on Jackie’s face.

“Really?” she said sarcastically. “That’s it? It took me longer to convince them to give me an early break!”

Angelina tried to apologize. “I’m sorry Jackie… I-”

“Just get off me.” She pushed Angelina off of her, got up and grabbed her clothes. She dressed in front of the door and then quickly exited, ignoring Angelina’s pleas to stay.

“Fuck!” Angelina cried, as soon as the door slammed shut. She looked down at her now limp dick and whimpered, watching it shrink again. In only a moment she lost a little more length. She was now just over average sized, maybe seven or eight inches but still decently thick. If she ended up keeping it at this size it would still be okay. Especially since her still large dick looked huge on her petite frame.

But she had missed out on her opportunity to truly dominate a woman with a huge cock. That was the worst part. It wasn’t even really what you would call big anymore. Just average or slightly above average. This whole thing was not going at all like she imagined. She fought back tears, wondering if she was even capable of winning this bet anymore. Her pride in being very proficient in bed was being seriously threatened.

One after the other that day, she tried to give another one of her lady friends an orgasm. It was the same each time. Over and over again she failed. She had the stamina (and the size) of like a fourteen-year-old boy or something. She was always erect, throbbing, and ready to go but it never lasted long. She kept losing inch after inch as she disappointed each of her friends in turn. She had a hard time holding back tears each time she failed.

She was doubly disappointed with herself since she was lasting longer and longer because of the repeated orgasms but she was also getting smaller and smaller. Her cock had also shrunk to less than three inches while rock hard. The last of her lady friends she tried to fuck rejected her. She simply laughed when she saw Angelina’s tiny dick, stifled further laughter, then apologized for laughing. Then she quickly turned and left.

She reentered the bar at around nine o’clock, feeling defeated. She took her spot at her usual table but she wasn’t even sure why she was there. She had run out of pre-arranged meetings and she didn’t know if she had it in her to pick up someone in the club. She barely even responded to anyone in the club. One of the servers brought her one of the usuals without her even having to ask and she stared at the floor sipping on it.

“I give up…” she muttered to herself, shaking her head.

“You give up?” She heard a familiar deep voice say. She looked up. And saw Hal sitting at her table, smoking a cigarette. “Well, that’s no fun.” He said, sounding disappointed.

“I guess I won’t get to keep that nice big cock,” she said sadly. “I’m already too small as it is so I may as well just give up and get my vagina back.”

He laughed a deep belly laugh. “What do you mean, get your vagina back?”

“What do you think I mean?” she asked, confused. “I don’t want a cock anymore. I give up so I don’t get to keep it. I don’t even want to keep it at this point.”

He smiled wide. “No I understand what you mean, that just wasn’t part of the deal.”

“What?” she shrieked. You said if I won I would get to keep it and-”

“And if you lost you wouldn’t keep that nice big cock. You have already lost, obviously.” He cackled.

“That’s not fair!” She hissed, trying her best not to raise her voice. “You said that I had until the end of tonight!”

“You’re already giving up, so what does it matter?” He taunted. “Yes, I did say you would have until the end of tonight. To win,” He laughed. “Or to lose as well.”

“Okay fine, I lose,” she said, exasperated. “Just make me normal again!” She commanded.

“I’m afraid that’s not going to happen. I said if you lose, you don’t get to keep the nice big dick.” He took a deep drag and blew the smoke out continuing, “Since you’re losing, you get to keep a tiny one instead.” He saw the shocked look on her face and added, “That is,” he chuckled and took another drag. “Unless you would rather not admit defeat and would rather keep what you currently have.” He blew smoke out through his smile. “You still have time.”

“Why don’t I just stop now before it shrinks any more and just keep what I have now anyway?” She crossed her arms defiantly.

“Because then you’ll lose and be stuck with the tiniest little shriveled dick that I can imagine for the rest of your life. One that makes the one you currently have look huge.” He laughed, holding his hand up with his finger and thumb close together in the universal signal for small. “Probably even smaller than him.” He laughed and pointed at Rooker at the door. When she looked back, he was gone again.

She was severely rattled at this point. She decided she was out of options here but she knew where she should go. It was a pretty short walk to the local lesbian bar.

When she got there she went to the bar for a drink. When she got to the bar she just started flirting with any woman that came by, and despite being as pretty as she was, her desperation was showing, which hurt her chances with each girl. She didn’t even have her large dick to show off through her dress to try and impress one of them. It was rock hard but now she was hiding it behind her handbag, which was pretty easy at that point. Even her shame wasn’t enough to stop her constantly being horny.

After failing repeatedly, she lost it and started crying. She quickly rushed to the lady’s room to minimize the scene she would make. She ran to a stall and sat down, closing the door and locking it before sobbing into her hands.

“What’s wrong?” she heard a sweet voice say from the other side of the door.

“Oh, it’s just-” she thought quickly and had an idea. “My girlfriend dumped me. She found out that…” she took a deep breath. “I have a dick.” She never pictured herself saying something like that ever, much less doing it to get pity sex.

“She left you because you are trans?” The sweet voice asked, clearly shocked.

She sobbed, “It’s so hard, you know?” She stepped out of the stall and saw a voluptuous brunette lady in her late thirties.

She was a little on the chubby side but she was thick with big round D-cups with wide hips and ass. She smiled, showing cute dimples. “I’m Bonnie.” She reached out and stroked Angelina’s cheek. “And I think you’re beautiful. It’s definitely her loss.”

“Thank you.” She sniffed and then smiled back. “I’m Angelina.” They stared into the other’s eyes for a moment.

“Can I, uh…” Angelina stammered and looked away.

“I would love a drink, thanks.”

After having a few drinks together and each sharing some aspects of their lives for a while, Angelina was sure that Bonnie was flirting with her and would be receptive. So she made her move and kissed her new friend right on the lips. Luckily, she reciprocated, shoving her tongue into Angelina’s mouth.

They found themselves at Bonnie’s apartment making out on the bed. Bonnie reached for Angelina’s crotch without breaking the kiss, but Angelina stopped her.

“I uh…” she swallowed. “It’s not as impressive as-”

Bonnie ignored her and reached under Angelina’s dress. And felt her crotch. Her hand encircled the shaft of the turgid little dick making Angelina gasp.

“More than enough to work with here,” she whispered, giggling. “I’m used to a lot less anyway.” She leaned in and kissed Angelina again before slipping out of her pants and climbing back on top of her.

Confused, Angelina asked, “What are you-”

“Shh…” Bonnie kissed her again, ending any further questioning. She entwined their legs so when she scooted up so their crotches would be mashing up against each other.

Angelina realized what she was doing just as it started. “Oh… fuck…” she sighed. The feeling of Bonnie’s wet pussy grinding against the head of her dick was amazing beyond description. She had only done this once or twice as a woman and it felt almost as good as it had then, and this time she was way hornier too.

Bonnie’s swollen clit rubbed across the sensitive head of Angelina’s dick making both of them squirm and moan. Bonnie seemed to know exactly how to do it, how hard to press and the exact angle so Angelina just let her take control. The grinding picked up speed until they were at a frantic pace. Angelina could hardly think or move, she was so stimulated.

“I’m gonna-” Bonnie said and then cried out. “I’m gonna-!” and she shrieked. Her whole body began to shake.

“Ooo… yeah, baby. Cum for me…” Angelina moaned before going over the edge herself. Bonnie’s smooth wetness slid back and forth on her cock as she felt her own orgasm hit. They continued to rub against each other a few more moments before collapsing in a heap on top of one another.

Angelina realized she was about to fall asleep when she remembered the bet. She pulled herself free of Bonnie, who was already snoring and stood up. She looked down at herself, smiling because she had won the bet. Her smile turned to a frown when she saw that her dick was way smaller than it had been when they started.

“Fuck, no way-!” She ran to the bathroom and looked at herself in the mirror. Even though she was soft it was easy enough to tell that she now had a micropenis, seemingly what Hal had described.

“It’s not fair!” she whined. “I won the bet.”

“Did you?” Hal’s voice asked, but she spun around and saw no one.

“I made her cum!” Angelina hissed, spinning around to try and find the source of the voice but came up with nothing. “I did it, even with the little dick!”

“But she did all of the work. Did you really make her cum?”

“You can’t be serious!” Angelina protested. “What kind of bullshit is that? I was sweating and grinding too!”

“Oh, alright.” The disembodied voice relented.

A moment later she felt something strange. She looked down and saw her penis grew, but only back to the size she was before she and Bonnie had started.

“Hey!” she protested again, gaining some confidence. “You said I would get to keep my big dick, didn’t you?”

“I said you could keep “it”, which could be a lot of things.” The deep voice teased. “I was deliberately vague.”

“Again, that is such bullshit! We both were referring to my dick right then! As it was then! Besides, how can you say I could keep it if it has been altered?”

“Alright, alright.” Hal gave in.

Her cock grew again, this time it was back to its original size. She swung her hips and watched her long dick waggle back and forth.

“Good, pleasure doing business with you,” she said smugly.

There was silence but a few moments later the voice returned. “There is one more thing, though,” it said.

“What?” she asked, annoyed.

“Look at what time it is.”

She glanced over at the clock and saw it was about one thirty.

“No! No!” she cried, grabbing her dick with both hands as it began to shrink again. “You said I had until the end of tonight! It’s still night!”

Cruel laughter seemed to come from all around her. “No, my exact words were ‘you have until the end of tomorrow.’ And since it is past midnight…” The voice began cackling again. “I already knew that you lost and it was too late. It was just fun to get your hopes up.”

She fell to the floor whimpering. “No…” she sobbed, watching her dick shrink back to its tiniest size. It was about as small as it possibly could be and still be called a penis.

End

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Comments

  1. Another good story. Quite different. I like a lot of the aspects. I appreciate it is a commission, so probably limited by outline/remit. Spoilers follow. I am not a huge fan on the micropenis stuff but I do enjoy a bit of shrinkage humiliation. Especially sexy when it is a woman. I knew she'd be stuck with a penis of some description but was kept guessing right up until the end.

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