Jacinda crossed her legs and shook her head before sipping the coffee. When she was in her prime years, it was difficult for her to believe that she would find herself in the predicament she was in.
“Never thought dating would be this hard past forty,” she said. “Seriously, where have all the good men gone?” she added.
“I don’t know,” said Gwyneth. “They’re definitely in short supply. Just look at my situation. I honestly believe if Tommy’s father had stuck around I wouldn’t have a twenty-one-year-old who just dropped out of college and didn’t know what to do with his life living under my roof.”
In her defence, since Tommy returned home from college, he had spent most of his time playing video games in his room and napping. The only time he walked out of the house was to take a dip in the pool and stock up on alcohol and cigarettes.
Jacinda and Gwyneth were birds of a feather who flocked together, and they never considered the reason they were single is that something might be wrong with them. No, it was always a man’s fault they couldn’t hold on to him.
Fortunately for Jacinda, she was prepared to lower her standards for a quick boink. As a rich, divorced, educated woman, she would never be seen dead with a man she perceived to be of a lower status than her, but he was welcome for a night if he provided the goods in bed.
Tommy walked into the lounge and said, “Oh, hi, Jacinda. Didn’t know you were here.”
Her eyes sparkled and her lips curled. She hadn’t seen Tommy since he graduated high school, and he had put on significant muscle mass in the last two years while living at the hostel. She stood up and shook his hand, unable to prevent her eyes from lowering to his broad chest.
“My, look at you. You’ve grown up to be quite a man,” said Jacinda.
She kept holding his hand, and he locked eye contact with her and smiled. Tommy knew how to handle himself around women. He had slept with ten girls at college, even though he failed two semesters, gotten drunk almost every weekend and had no intentions of completing his degree.
But his muscular physique, wavy hair and alluring smile had many women weak at the knees.
“Lunch is in the fridge. We’re having lasagne today,” said Gwyneth to Tommy.
“Okay, mom,” he said before walking away from Jacinda.
Jacinda peeked at his ass and smiled while lowering her bum to the sofa with her hands on her thighs.
“Wish he would just sort his life out,” said Gwyneth. “The last thing I’d want is for him to become a loser like his father and embarrass me.”
Jacinda couldn’t stop thinking about how well Tommy had developed his body. She would’ve loved to run her hands over his chest and abs, then down to his…
The following night, while playing video games in his room, Tommy received a text. It was so nice to see you again after all these years.
Tommy smiled after reading Jacinda’s message. He knew what the deal was and opted not to respond right away.
Two days later, he sent Jacinda a text. What you up to now?
Just watching some TV. You?
Thought if you weren’t doing anything now, we could catch up.
Yeah, sounds great. What did you have in mind?
I can come over if you want.
Jacinda smiled. She didn’t have to spend two hours getting ready to doll herself up and then drive to a restaurant.
An hour later, Tommy rang the doorbell. Jacinda flipped her hair over her shoulder, exposing her neck, as she walked to the door.
She smiled at Tommy and welcomed him inside.
In the lounge, she asked, “Can I get you a beer, whisky or something else you like?”
“Beer sounds good.”
She returned, handed him the beer and then sat next to him, her knees facing him and only a few centimetres away from his legs.
Every few minutes, she placed her hand on his leg and leaned into him as she laughed. Tommy wasn’t particularly funny, but several women had used that strategy to touch him.
Her hand brushed his abs and slid up to his chest, which she rubbed. “You’ve gotten so strong. Last time I saw you, you were just so young. But now, I can see you’re developing into a man,” she said, ogling his chest. Her hand ran over his shoulder and then down his arm.
His eyes followed her hand, and they locked eye contact.
Their lips crashed into each other. Tommy immediately went for her tits, his hand fondling one as their tongues slithered against one another.
He scooped her into his arms and then carried her to the bedroom. She couldn’t remember the last time a man had carried her. Tommy flung her onto the bed, and she screeched.
He jumped onto her and ravaged her chest. She laughed while raking her fingers through the back of his hair. He tapped her leg to indicate that she should get on her hands and knees. Tommy was even better than Jacinda thought he would be. He banged her hard in doggystyle, pulling her hair and spanking her ass.
She loved every second of it and couldn’t get enough of his stamina. Her face glistened from the sweat covering it. Tommy continued the aggressive momentum, barely giving Jacinda time to breathe. She dunked her head and panted, but he pulled her hair and made her scream.
She got on her back and spread her legs. He grabbed her ankles and pushed her legs forward, with her feet to the side of her head. Tommy was surprised she was so flexible, but her pilates classes had paid off.
He stood on the bed and squatted so he could stick his dick into her pussy. He penetrated while holding her legs spread wide. Tommy clenched his teeth during the aggressive humping as he felt her pussy get wetter.
They also banged in the shower and the lounge.
After having sex for hours, Tommy got dressed. Jacinda walked him to the door and told him to call her. She intended to make their intimacy a weekly occurrence.
Always one to brag, Jacinda told all her friends about her sex romp. She withheld Tommy’s name initially, but eventually, her boastful personality revealed his identity. Her redeeming act was making the friends promise not to tell Gwyneth.
The friends kept their promise, but Jacinda said nothing about avoiding Tommy. Two of the friends contacted Tommy the following day. The third friend contacted him two days later.
Tommy wasn’t the sharpest tool in the shed, but he figured out when the friends called him that Jacinda had spilt the beans. He didn’t mind as long as his mom didn’t find out. There was no need for him to meet Jacinda’s friends at a restaurant. The first date was at their house, followed by a shag.
These middle-aged women had no reason to waste time. They wanted to get to the point immediately, and they knew Tommy was just the guy to give them what they wanted. He banged all three women the day after they contacted him.
Over the next few weeks, the word about Tommy’s extraordinary bed performance had spread. He gained a reputation for satisfying divorced and unhappily married women. His time had become a precious commodity, as women struggled to book a slot with him.
To compete for his time, some women gave him presents. He was spoiled with a watch, alligator penny loafers, silk shirts and golf clubs.
The gifts kept pouring in, becoming more extravagant. Tommy hid the gifts in his room as he didn’t want his mom to discover them. She was suspicious of him spending a lot of time outside the house, as she feared he was drinking himself to oblivion. But she respected his privacy by not going into his room.
Her anxiety dwindled after Tommy returned home sober numerous times. She figured that he was out looking for work.
Tommy had twelve women on rotation after several of them had given up on vying for his time. The women had noticed that the novelty of the gifts had worn out, and they needed to make their offers more alluring. They offered him money for servicing them.
Some of the additional services they requested were a massage before sex and cuddling after he banged their brains out. Tommy gladly catered to all their needs, as most of the women were attractive.
Two months later, his client base had drastically expanded, and he was on his way to making six figures for the year.
On his way out of the house, his phone rang. “Hi, am I speaking to Tommy?”
“Yes.”
“Hi, Tommy. My name’s Evaline. I heard you offer companionship.”
“I do, yes.”
“Was wondering if we could meet up on Friday.”
“Let me check my schedule, and I’ll text you back.”
“Okay, great. I look forward to hearing from you.”
After the call, Evaline sent him a photo of herself. “Oh, wow,” said Tommy as he admired the photo. She was definitely the most beautiful woman who had contacted him. Her auburn hair flowed below her shoulders, and her fit body was on par with 20-year-old women.
Tommy was definitely gonna make time for her.
He saw her on Friday at her house. She wore a black dress that reached her knees and had a slit, exposing her entire right leg when she sat on the couch and crossed her legs.
Instead of getting right to the intimacy, as he did with most clients, Tommy was surprised that Evaline wanted to get to know him. She smiled throughout most of his story, making him feel unjudged. Her energy made him feel like he could tell her anything and not be self-conscious.
He even told her how he became an escort, specialising in satisfying milfs. She chuckled, but it was the reason they met. Tommy was slightly embarrassed for admitting that to her, as he saw something in Evaline that he hadn’t seen in other women.
Evaline was different.
She even cooked dinner for him. After chatting for three hours, Evaline turned on romantic music. Tommy asked her to dance. She put his arms around his neck and his were on her lower back as they slowly waltzed in the middle of her lounge.
They stared into each other’s eyes and smiled. Tommy couldn’t get enough of her green, sparkly eyes. It’s like they magnetised him and put him in a trance. He was smitten.
She grabbed his hand and led him to the bedroom. In front of the bed, she looked at him over her shoulder and smiled. He stepped behind her, put his arms on her thighs and kissed her neck.
He unzipped her dress, and the straps slid off her shoulders, and the dress dropped to the floor. She stepped out of it and bent over the bed. The muscles in her quads and calves contracted, as her ass perked up. Tommy looked at her high heels, then raised his eyes up her leg.
He got on his knees, clutched her g-string and pulled it down. Her ass opened up, and he licked her pussy while running his left hand up and down her leg.
Tommy stood up and stuck his dick inside Evaline’s pussy. He grabbed her waist and thrust his hips. As she sputtered groans, he closed his eyes and raised his chin as his hands ran over her back. Her soft, smooth skin drove him insane.
The more he touched her, the more he wanted her. As he sped up, she put her left hand on his leg and smiled at him over her shoulder. She was the only woman he needed. Her femininity and smile made him so vulnerable to her.
She could control him any way she pleased, and he was fine with that. He trusted her and believed that she had good intentions.
His chest contracted and expanded rapidly as he breathed out of his mouth, with passion culminating in his chest. He wanted it to burst out of him, but he also enjoyed the intense feeling. He felt out of breath, with his throat seemingly tightening as lust burnt inside him.
Evaline was magical in every way. Tommy didn’t care that she was more than 15 years his senior. Her charisma elevated him to a king’s level, and he wanted more of that feeling. Much more.
His body suddenly convulsed slightly, and he had no control over it. The erratic feeling made him a bit anxious, but he realised that his body was reacting to Evaline’s touch. The image of them making passionate love flashed into his mind, unleashing all the lust out of him.
Tommy groaned as his load burst out.
Evaline turned around, put her arms around him and kissed him. They cuddled before she fell asleep.
In the morning, she handed him the money. Tommy refused it and said that the honour was his. There was no way he would make their intimacy a transaction. She was so much more than that to him, and he couldn’t wait to see her again.
Unlike most of Tommy’s clients, Evaline didn’t call him a few days after sex. That was strange to him, as the other women inundated him with calls. But she was different. Tommy realised he had to call her.
“Hi. It’s Tommy.”
“Oh, hi.” Evaline sounded nonchalant.
“I just thought I’d touch base and see how you are.”
“I’m fine. A bit busy at the moment.”
“Oh, okay. Um, you think we can hang out soon?”
“Thanks for the offer, but I’m not interested.”
That stunned him to the core. He couldn’t believe how brash she was about not wanting to see him again. It’s like she was a different person.
“All right,” he said softly. “Enjoy the rest of your day.”
All the energy was sucked out of his body. He felt depleted mentally and physically.
Lying on his bed, Tommy convinced himself that Evaline needed a few days to work out whatever she was going through. He was certain that she would respond differently when he called a week later.
“Hi, Tommy here.”
“Hi.”
“How are you?”
“Good.”
“Just wanted to see how you’ve been doing.”
“Everything’s fine.”
“I was hoping we could catch up during lunch. There’s a new restaurant that just recently opened up on Oxford. People can’t stop raving about it.”
“I’m fine, thanks,” said Evaline.
“Have I done something wrong?”
“No.”
“Okay, I don’t understand the change in your mood, all of a sudden.”
“There is no change in my mood. Look, Tommy. You provided me companionship when I was going through something. It was just sex. And to be honest, it wasn’t even that great. I’ve had better. I needed to get back at my husband for cheating on me, so I used you. But I’m over his infidelity, and we’re gonna make it work for sake of our kids.”
“You’re married?”
“Yes. I have to go. Bye.”
He was gobsmacked. It’s like he took a massive blow to the gut and was completely winded. He felt duped and stripped of the elevation that Evaline had provided. He couldn’t understand how someone who seemed fabulous could turn on him.
Tommy spent the next few days playing video games and neglecting his hygiene. His hair was dishevelled, and his breath reeked. Leaving his room felt strenuous. He barely had the energy to keep his eyes open.
Initially, his phone rang constantly. Women called for his services, but he had no desire to sleep with any of them. Not only could he not stop thinking about Evaline, but he feared a repeat of that experience with another woman. There was no way he could risk having his heart shattered again, so he switched off his phone.
In the lounge, Gwyneth was on the phone. “I can’t thank you enough, Evaline. He’s in his room, mopping around like a wounded puppy.”
“Shame,” said Evaline.
“A broken heart will do him wonders. I’m convinced that he’s never going to offer his services again. I can’t have a son who’s an escort. I mean, no offence to your profession.”
“None taken. I hope he’ll be all right.”
“He’ll be fine. I’ll give him a couple more days to lick his wounds and then motivate him to get a real job. Thanks again, Evaline. Have your agency send me the invoice.”
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