Shirley starred at the ceiling while the thirty-something-year-old banker from Finland thrust into her. She was on her back with one ankle on the man’s shoulder and the other splayed around his hip. It was a somewhat uncomfortable position to hold for a long time, especially while being penetrated. The entire evening had been a disappointment. He had promised to take her out to Candlenut but the reservation landed them at the communal table and the pictures she took always had other people sitting far too close. Her best photo had another woman in the frame giving an annoyed look. Every photo she took of the food had other diners hands and cutlery in the frame.
“None of these can be posted,” she muttered to herself. After dinner she was taken to Bitters and Love but it was only a ploy to be close to his condo at Sail, which she agreed to accompany him to after her second scotch.
Much like the rest of the evening, his condo at Sail was subpar. It wasn’t facing Marina Bay Sands but was on the backside of the glass skyscraper and more angled to Raffles Place. When they arrived in the lobby, Shirley was immediately disappointed when he ushered her to the elevator bank that didn’t go over the 20th floor. Had the condo been nearing the sixtieth floor with a well-angled balcony, she could have taken a dramatic photo for her social media with all of Marina Bay in the background, but the view of the MRT plaza across the street was hardly something that would impress her nearly two-hundred-thousand followers. Furthermore, Shirley felt the Sail was too played and didn’t offer the luxuries of some of th newer buildings. A lot of ang-mo’s and foreigners in the banking industry gravitated to the Sail due to it’s proximity to the DBS building and the financial center, but the real monied class of EP Pass stayed at other addresses.
Despite to all of these disappointments, Shirley allowed the man to undress her, place her on her back, and then penetrate her without a condom. She made no effort to give him oral sex, which was her benchmark for a well executed date.
The man had a very trim figure but a smaller penis than she had hoped; the final disappointment of the evening.
Shirley tried to make herself comfortable as the man spread her legs widely while thrusting in her, but she had been feeling bloated all week. The large windows offered enough light into the room where she could study his face and she could tell he was nearing his orgasm. A moment later he pulled out of Shirley and began spraying cum all over her.
“EEEEK!” she shrieked as she felt semen land in her expensive hair extensions.
The man quickly noticed her displeasure and, instead of angling his spurting cock elsewhere, he decided to stuff it back inside of the girl and inject the final burst of cum inside of the girl. As soon as he pulled out, Shirley felt the sperm rush out of her and trickle down the crack of her ass, but she didn’t care. She ran into the bathroom and frantically detached the real hair extensions and filled the sink with cold water to soak them while she cursed. Then she jumped onto the toiled in order to clean her sperm filled vagina. While on the toilet she rolled her eyes at how pudgy she had gotten. Her once perfectly flat tummy now protruded in an unsightly way. And this was especially annoying as she had gone out of her way to abstain from eating and remained exactly 44 kilos.
“I am becoming an auntie,” she sneered.
After she had finished cleaning herself, she walked naked back to the bed to find the man busy on his phone. She laid down next to him and began texting to her friends in Mandarin how awful her evening had been. A moment later, the man rolled over and immediately began snoring and Shirley rolled her eyes at him and texted for another hour before she couldn’t keep her eyes open then drifted off to sleep.
Abruptly, Shirley woke as she felt herself being rolled onto her stomach. Then a heavy body straddled her and spread her cheeks. A moment later she felt the rider penetrate her and begin to deeply thrust.
Shirley grunted while the man on her rolled his hips until he began grunting himself, expelling his sperm deep inside of the half-asleep girl. After he pulled out, he immediately sprung out of the bed and left. A moment later he yelled from the hallway about hair being in the sink. Not caring, Shirley wadded up the man’s bedsheet and used it to blot the semen spilling out of her while she attempted to sleep. Just as she was beginning to drift off, the man emerged, fully dressed in a moderately priced suit.
“You have to get dressed. I’m going to be late for work,” he complained.
“I will get up later!” Shirley complained.
The man would not allow it and pulled the covers off her. Begrudgingly, Shirley hunted on the floor for her clothes. She found a plastic bag on a table and used it to collect her soaking hair and walked out with the impatient man. In the elevator Shirley was embarrassed by the other men and women, pressed and fresh, on their way to an office, looking at her without makeup and wearing a cocktail dress that was obviously from the previous night.
They probably think I’m a prostitute, Shirley thought, annoyed.
One of the more convenient aspects of the Sail was its proximity to the mrt and Shirley jumped on the red line to get home. As she rode, she texted her helper to prepare eggs and toast with Kopi C when she arrived.
As soon as she reached home, Shirley was ravenous and ate all of her breakfast rather quickly, which was quite unusual as she typically skipped breakfast.
“Can you make another egg and toast?” she asked her helper.
“Yes, of course now that you eat for two,” the older Malay replied.
“Eat for two? Eeyer!”
“You are quite late. I go to Watsons for you last week but when I place the Kotex under sink, you not use what you already have!”
Shirley suddenly realized she was several weeks late. She had been partying more than usual and had completely forgotten about the miss. Panicked she opened her phone and began going through her text messages.
“Who is the man?” her helper asked.
Shirley said nothing, scrolling through her phone. There were so many men in the last few weeks.
“I do not know,” Shirley wailed.
“Jialat,” the helper whispered.
The main reason Shirley had been so reckless was the fact she had gotten a Progestin IUD over 6 years ago, just after she had aged out of competing in the pageants. She then trembled, wondering when her brand needed to be replaced. After digging up an old email from her gynaecologist, she discovered the IUD should have been replaced a year ago. She had switched gynaecologist’s a year or so after she got the implant and, upon further inspection, she had an email she had never opened from her old doctor reminding her of the expiration.
“Expired last year!” she groaned.
In Shirley’s phone she found fourteen text conversations with men since her last cycle. She wrote the names down and what she could remember about the sex. Several of them had worn condoms. Others had not worn condoms but pulled out. And a few of them had inseminated her. She narrowed down the list to five very possible men and two less likely potential fathers. Of the seven, three were Chinese Singaporean, three were westerners, and one was Indian. The most likely candidates were the Indian and one of the Chinese Singaporeans. Both of them had unapologetically inseminated her during the week she had estimated her ovulation.
“Go get me two different pregnancy tests,” she told her helper then went back to her list.
Twenty minutes later, the Malay woman returned and Shirley peed on one stick and then another. Both returned a positive result.
“Kan!” Shirley shouted then looked at the crotch of her thong rolled between her knees. It was encrusted with dried semen. “Kan!” she repeated.
Shirley removed the thong and jumped into the shower. When she finished, her helper was in the bathroom with her, handing her a towel. The woman looked at her and smiled. This annoyed Shirley immensely because she felt very judged and did not take the woman’s smile to be honest. Then Shirley had an idea and took a picture of the positive pregnancy test and sent them to every man she had fucked the previous month. They all read the messages and it was nearly twenty minutes before the first one messaged back.
“Cannot be mine!” A Singaporean man replied.
“Who is this? Wrong number!” a westerner texted.
“Are you keeping it?” Another westerner asked.
Of the other eleven, five responded later that night and six never replied at all. The ones that didn’t reply, Shirley forwarded them pictures she took during their date where they were both in it. The men panicked and asked what she wanted. This worked so well, she sent pictures to every man. Pretty soon they were all very communicative.
“What do you want from me?” One exasperated married Singaporean asked.
“The procedure is five-thousand. You should pay, lah!” Shirley demanded.
“How do I know you are telling me the truth?” he demanded.
“Will you take the risk?” she replied, coyly. An hour later the funds landed in her PayLah account.
Her plan worked smoothly until she got to the westerners.
“I’m not just giving you money. I think this is bullshit. Have the kid or not. I don’t care!” One replied. Shirley gave up on that one.
Another agreed to the money but demanded proof.
“I can google positive pregnancy test too!” he retorted.
Shirley sent another image of her holding the stick with her face in the frame.
“I still don’t believe you… come over and pee for me!” the man demanded.
“If I come over, you will PayLah me?” Shirley pushed back.
“If you test in front of me, yeah!”
The next day she returned to a condo at Wallich she had been at three weeks prior where an English banker had came inside of her doggy-style.
“Alright then, here you go,” the man smiled, handing the girl the test and then followed her into the bathroom.
“Are you going to watch me pee?”
“Oh, I’ll have a butchers at this!” the Brit grinned.
“Fine!” Shirley replied and hiked up her dress, slid down her thong and plopped herself on the toilet.
She unwrapped the test and began peeing then exposed the correct end of the test to her stream of urine. After which she handed the pee covered stick to the man hovering over her.
Without flinching, the man placed it on the sink while Shirley finished peeing then pulled some toilet paper off the spool.
To the dismay of the man, the test registered positive.
“You lied to me and said you were on birth control!” the man sneered.
“The IUD failed… and I don’t want this baby. I will get rid of if you pay. Otherwise I cannot afford and will register you as the father,” Shirley flatly stated.
“And this is my baby?”
“Of course!”
“Well… since you’re already knocked up, I think I’ll have another go at ya before I give you get my bread and honey… I mean why not!”
“I do not want to have sex again. I just want the cost of the procedure,” Shirley bristled.
“Oh please, We’ve had sex twice and each time our date, if you can call it a date, cost me around a thousand quid… this time is just costing me a bit more!”
Shirley looked at the floor, calculating the transaction. She had never had sex purely for money before. She had an entire closet of bags and clothes that were gifts from the men she slept with, and a lot of her bills were paid by selling the luxury items after she had taken them out a few times. Still, she had never gotten a wire transfer.
“Can you be quick?” Shirley posed.
“For five thousand? You had better fuck me like you’re gagging for it!” the man replied, narrowing his eyes.
After thinking about it, Shirley decided she may not get the money without having sex with the man, so she shrugged then dropped to her knees and began working on his belt. He assisted her with the effort and a moment later his erect prick sprung free. It took Shirley by surprise because it was, indeed, larger and more girthy than she had remembered. It had a thickness, with ample loose skin that the girl found to be both unsightly and yet very appealing. The head was also very wide but rather lacking in depth, barely poking out of the bunching skin despite being fully erect.
It must have been dark when I had him, Shirley surmised.
Not wasting time, she put the wide tip in her mouth and pulled the loose skin of the meaty cock back and forth. The man groaned in pleasure and Shirley found herself becoming aroused at the thought of soon having this unusual looking penis inside of her. Then she became even more enthralled at the idea of being inseminated. She chocked it up to being unsatisfied from the last man and his thinner penis. She also figured her excitement stemmed from being coerced into having sex for money. She had always enjoyed the sex more when she was given a nice gift as a means to entice her into bed. Looking back on those transactional lovers, she always had to estimate the aftermarket value of a watch or a designer bag. Receiving the cash instead seemed quite optimal, she thought while slurping on the wilting cock.
Shirley reached under the cock she was sucking and cupped the balls. They were massive, misshapen orbs, floating inside of a wrinkled, drooping skinbag that seemed larger than some of her clutches. The springy hair around the sides curled in a way she found impossible as Shirley’s hair, whether on her head, or on her mons, when she used to have hair, was always perfectly straight.
How did I not remember this? Was I that drunk? Shirley puzzled.
The man pulled Shirley up to her feet by gripping her elbows. Instinctively, Shirley unzipped her dress from behind and stepped out completely naked except for her bra. After unhooking her bra the man made a wry smile.
“Too bad you’re not keeping the baby. It would probably do wonders for your tiny tits. But you may develop that big blue vein in them like some women,” he taunted.
Shirley had often considered implants but hated the idea of any scarring on her porcelain skin. She had taken great care to never allow a single mark on her body while other girls her age were rushing out to tattoo and pierce their bodies. The idea of stretch marks or verrucose veins horrified her.
Now that Shirley was completely naked, the man led her from the bathroom into his bedroom as if she were a show pony and walked her to the bed. Happy to get off her knees, Shirley flopped her naked body on the mattress and waited while the man undressed.
He was rather muscular while maintaining a round potbelly, most likely from consuming pints of beer every tight at boat quay with his peers from work. Still, Shirley’s eyes were locked on the large cock with the hanging loose skin. Then her mind recalled the list of men she had listed as the possible father and, by her calculations, this large, wrinkled dick was inside of her only a handful of days before she speculated that she was fertile.
Maybe it really was him? Shirley pondered.
The man grabbed both of Shirley’s ankles and rose them until the flat bottoms of her feet were just under his ears.
“Put it inside of you,” the man commanded.
In bed, Shirley absolutely hated to participate. She absolutely loved the feeling of a nice cock inside of her but the manner in which she was penetrated mattered far less than her concentration. She felt that if she were to be moving around or holding herself up, her efforts would be a distraction to the enjoyment she could possibly be receiving from that divine stretch.
“Just let him do what he wants and if you don’t like it then find someone who does it better,” she had once advised a friend who had been complaining about not being able to ride a cock to an orgasm.
Slightly annoyed, Shirley grabbed the giant wrinkled cock and pulled the tip to her slick opening then spread her labia with her other hand. The man leaned his hips forward, penetrating her. The cock worked itself into her pussy and then Shirley finally remembered having sex with the man. She had been quite drunk for the occasion, but she had made a mental note to enjoy his cock again as it was a particularly good stretch inside of her small body, which she did. However, when the man refused to take her to a third Michelin Star restaurant, or buy her the Dior purse she wanted, and simply wanted to have a casual evening with the girl, Shirley immediately ended the tryst.
“Is it really my baby inside of you or some other blokes?” the man sneered as he increased the pace of his thrusting.
Shirley remained silent, trying to focus on the pleasure she was beginning to feel in her stretching pussy.
“Well? How many other wankers had their bellend up ya cunt?”
“You are the only one who went without a condom,” Shirley finally lied.
“A scrubber like you? You’re taking the piss out of me,” he laughed.
Then he pulled out of Shirley and grabbed her hips, flipping her into doggy. A second later he penetrated her from behind.
“I must have been pissed to not ‘ave worn a rubber with you, ya slag!”
Shirley wasn’t even listening and was deeply enjoying being fucked by the nice thick cock owned by the foulmouthed Brit she was scamming.
“Hello… let’s see if we can’t make it twins!” The man groaned and then began grunting while pumping his load deep into Shirley from behind.
Feeling him pulse set the girl over the edge and she quietly orgasmed, doing her best to not make too big of a show for the man who had called her a whore.
“Now, clean this spunk off me meat dagger with that gob of yours,” he mumbled as he withdrew from Shirley’s pussy and took a step to his left to angle his cock at the girl’s face.
Obediently, Shirley opened her mouth and the man thrust into her face. With the cock in her mouth, Shirley noticed that she tasted slightly different than she usually did. After a few jabs from the man’s hips he withdrew and began putting his clothes back on. Since her task was over, Shirley went into the bathroom to sit on the toilet to let the sperm slowly dribble out of her.
“Paylah! Five-thousand,” Shirley reminded.
“Of course, of course, my fine slag,” the partially dressed man sang to her and picked up his phone and used the account number Shirley had provided in her text.
A moment later, Shirley got the notification in her DBS app that the money had arrived.
“Now… piss off you utter twat!” the man grumbled.
Without at word, Shirley stepped into her thong, then into her dress, stuffed her bra into her bag, and carried her shoes out the door and into the elevator. So far she had gotten nearly half the men to pay. Two had flat out refused and the rest had promised but not followed through.
“I may need to sleep with all of the holdouts,” Shirley wondered as she put her shoes on in the elevator while her thong collected the remainder of the Brit’s sperm.
Jack Lariat Stories 