The Old Repairman Pt. 02

"What are you doing?" She asked, a little worried as she was not sure if she was ready to lose her anal virginity.

"Do you trust me?" He asked.

"Yes, of course." She replied.

"Then trust me, you'll like this." He said.

"Ok." She responded.

Vernon inserted his right index finger into her butt, slowly to not hurt her too much. His finger slowly dove in and eventually got further than his tongue had ever been. The finger in her butt was slightly painful for Courtney, its thickness was stretching her ass out more than anything before. Courtney gritted her teeth through the pain as Vernon inserted his finger all the way in. He held it there while he banged her pussy.

The pain quickly subsided for Courtney, and suddenly, she only felt the pleasure of being double stuffed. She moaned loudly, which prompted Vernon to begin to move his finger in and out of Courtney's butt. With both her pussy and ass on fire, Courtney soon came, her whole body shook from pleasure.

She was now ready to lose her anal virginity. She knew and tonight she was going to ask Vernon to take it. But first they had to talk about their future.

Courtney prepared dinner tonight as Vernon changed the sheet on their bed. Courtney wore that red dress she had bought a week ago, she wanted to look good for Vernon tonight.

Vernon's jaw nearly dropped when he saw Courtney in that dress. She looked good in everything but when she dressed up, she went from good to goddess. Vernon walked up behind Courtney as she stirred the pasta. He grabbed her breasts and she turned her head to kiss him. He loved how easily he could control her, how she just gave in to him. He hoped it stayed like this forever.

"Alright, that's enough." She said, pulling away. "Now go set the table."

Vernon gave Courtney a hard slap on the butt, which caused her to audibly yelp a little, before Vernon walked away.

He set the small table Courtney had as usual, but turned the overhead light down and lit a couple candles. Soon Courtney was done with making dinner, she set the 2 plates of pasta down on the table. Vernon had opened a bottle of red wine for the 2 of them, poured each of them a glass. They sat down, began to eat and chat about their day.

As dinner winded down, Courtney got a more serious look on her face.

"Vernon, I really enjoy having you here." She told him, as she reached over and touched his hand. "But since you've come, I've had to buy more food and you're not paying rent or paying for anything really. I know it'll be hard, but maybe you can find a part-time job to help out with bills."

"You know I was thinking, I got some stocks I could cash in and retire off of." He told her.

"Do you know how much?" She asked.

"Couple million at least." He answered.

"Really?!? Why were you working then?" Courtney asked surprised.

Vernon shrugged. "I don't know. Didn't know what I'd do." He replied. He then grabbed her hand gently so they're holding hands. "But I think I found something." He said.

Courtney blushed. "Ok well, I'm leaving tomorrow afternoon to take the train home for the weekend. Figure out how much you have and we can discuss finances on Monday." She told him.

"Ok." Vernon replied. "Heading home for a reason?" He asked.

"Ya, it's my birthday Friday." Courtney responded.

"Oh I-uh, didn't know." Vernon stammered.

"It's ok, we've only known each other for just over 2 weeks." She told him. "But I do have a little idea of a birthday gift you could give me."

"Oh, and what's that?" He asked.

Courtney stood up, then bent over at the waist and gave Vernon a kiss while pulling her dress up over her butt.

"You fucking me in the ass." She whispered in his ear.

Vernon quickly slid out of his chair and got right behind Courtney. He grabbed her cheeks, spread them, and started to gently lick her ass, just getting it lubricated. He then licked his index finger and inserted it into her ass. Courtney groaned as she felt his pudgy finger enter her ass. He moved his finger slowly in and out as he went down and licked her pussy. Courtney was moaning like crazy as Vernon brought her to the precipice of an orgasm. He then suddenly stopped, pulled his finger out and made her suddenly feel empty.

Vernon stood up and pulled his already erect cock out. He slapped it against Courtney's pussy before he slid it between her butt cheeks, right over her ass.

"Wait! I got something." Courtney said, remembering the lube she had bought earlier. She ran to her purse and pulled it out. She came back and dribbled a bit on Vernon's cock, then jerked him off, covering his cock in lube.

'God, is that thing even going to fit in my ass.' Courtney thought, looking at his massive meat. She had forgotten how big it was, over 11 inches and thick, her hand barely able to wrap around it. She gulped, getting a little nervous about what it might do to her.

"Alright, we're ready." She said, trying to remain calm.

Courtney bent over the table again. She reached both hands behind her to spread her cheeks. Vernon slapped his cock against her asshole, then started to put pressure on it. Slowly, he increased the pressure until her sphincter gave in and the tip of his cock slid in.

"Aahhh!" Courtney gasped as Vernon took her anal virginity.

She released her grasp on her cheeks to hold herself off the table as Vernon held his cock there, trying to let Courtney get used to his cock in her ass before going any deeper. As he felt her calm down, he started doing mini thrusts, pushing his cock in a little deeper.

"Deep breaths." He told her as he slid in a bit further.

Vernon's finger had loosened Courtney's ass up a bit, but the pain she felt as her ass stretched far beyond that by his cock was making it hard for her to enjoy this. Courtney took deep breaths and Vernon was being as gentle as possible, making the experience tolerable. It took several minutes of Vernon stretching her ass until she derived any pleasure. It was very slowly that the nerve ending in her ass began to fire, making the experience pleasurable.

Vernon had barely stuffed 1/3 of his dick in when he heard Courtney whimper.

"Are you ok?" He asked.

"Ya keep going. It feels kinda good." She replied. Vernon slid about half his cock in now.

"Huh!" Courtney groaned as Vernon pulled back slightly. "No, don't stop, keep going." She told him. Vernon slid another inch and a half into her, Courtney groaned. "Give it all to me!" She demanded.

Courtney's ass was the tightest hole Vernon had ever fucked. His cock felt clamped in, as her muscles squeezed around him. Somehow he could push further, forcing inch after inch inside her, until somehow he was able to force every inch inside her butt. The warm tightness of her ass was incredible, and he just hoped it was good for her, too.

Courtney couldn't believe she was able to take all of Vernon's cock in her ass. It was both incredibly painful and incredibly pleasurable. The mix of the 2 broke Courtney, causing her to babble incoherently as Vernon held his cock deep inside her ass.

Vernon eventually grabbed Courtney's hips and gently started to thrust in and out. Every nerve in her ass stood on edge as he slowly moved in and out of her ass. The warmth and tightness of her ass brings Vernon very close to a climax.

"Harder." Courtney was able to blurt out.

Vernon didn't waste any time, quickly picking up the pace of his thrust. A loud slapping sound reverberated through the condo as his fat thigh slapped against Courtney's muscular glutes. Courtney began to scream in pleasure as her ass was on fire from Vernon's cock. It wasn't much longer until she orgasms, her whole body spasmed, causing Vernon to release his seed in her ass. Courtney enjoyed the warm sensation of Vernon filling her ass with cum.

Vernon pulled out once he was done, staggering back into a chair. Courtney dropped her body onto the table, both of them out of breath.

"Wow." Was all Courtney could say.

------

"Oh fuck yes!" Courtney screamed as she slid Vernon's big dick up her ass again.

She had just returned from her trip home and had been craving that feeling for a while. The day after her first time, her ass was pretty sensitive, there was a slight pain when she would go to sit down. By Friday night, the pain was gone and she craved being ass fucked again. She went out with friends Friday night and thought about letting someone else try to scratch her itch. But she knew no one could satisfy her like Vernon.

She was surprised how fast she accepted a fat old man as her lover. She was petrified after their first session together. That feeling would slowly go away as she slept with him more until it was gone and she was his.

"So, any cute guys in Chicago?" Courtney's childhood best friend Patricia asked on the car ride home from the club on Friday night.

"Plenty, but I'm focused on my modeling career right now." Courtney replied.

"Nobody said you can't do both." Patricia said.

"Maybe I'm just over boys." Courtney responded.

"If you're getting into women, you know I get first dibs." Patricia replied, and the 2 girls laughed.

When they got back to Patricia's place, she told Courtney she had one more surprise and handed her a small, wrapped box. Courtney opened the box to a pink 8-inch dildo.

"If you don't want a boyfriend, I figured you'd need another way to get off. And trust me, that thing will get you off." Patricia told her.

"Thanks, P." Courtney said through a fake smile. She knew this dildo could not scratch the surface of the pleasure Vernon could give her. He was longer, thicker and knew just the right places inside her, places she didn't even know about. It was a thoughtful gift, but one that was about 2 weeks too late.

Saturday morning was hell for Courtney. She had a need for Vernon's dick, but obviously he wasn't around. She tried using her fingers, but it just wasn't the same. She then pulled out Patricia's gift.

'Might as well give it a shot.' She thought.

Laying on her back, she sucked on the dildo to give her some lubrication. After a while, she spread her legs and slowly pushed the dildo into her ass. She had to admit it was far less painful than Vernon's cock, but something was off. It didn't feel right, and no matter the angle she took or how furiously she pumped, the dildo just didn't do it for her. After 15 minutes of trying, she threw the dildo into her bag and accepted that she wouldn't be getting off this weekend.

Most of the weekend was fine as she had friends and family to distract her, but the train ride back felt like it took an eternity. Courtney had nothing to do but imagine what she was going to do to Vernon when she got home. Her pussy got increasingly wet and fluid started dripping down her leg. She was kinda mad she had worn white shorts but felt lucky the train was mostly empty. It had been almost 4 days since Vernon fucked her in the ass and she needed it badly.

When she entered her condo, Vernon was making dinner.

"Hey, Courtney, I was just..." He began to say.

Courtney ran at him and kissed him passionately. Vernon was surprised at first, but who was he to reject a sloppy make out session with Courtney.

"Get on the floor, pants off." She whispered in his ear.

Vernon realized she'd been craving his dick and quickly got his pants off and lay down on the cool kitchen floor. Meanwhile, Courtney ran and grabbed the lube while undoing her shorts. She was a woman possessed by horniness. Once back in the kitchen, she pulled her shorts off, revealing she wasn't wearing any panties. She got down and dribbled a few drops of lube on Vernon's cock, jerking it off to cover it. Then she moved her right leg overtop of him, so her back was to Vernon. On her feet, she slid his cock back into her ass.

Vernon had forgotten how tight Courtney's ass was, as they struggled to stuff his cock up there. He had been masterbating to the thought of fucking her ass again since she left. He didn't dare touch her ass when they fucked the morning after, knowing it would be sore. He had hoped a few days away would cause her to crave it. And as he could clearly see, his wish had been granted.

For Courtney, this time was much less painful. The first time and the dildo had muted the pain, so now she just felt the pleasure of having a big dick in her ass. She rode Vernon's cock up and down, her ass was already convulsing as she'd been missing this feeling. She went to her knees and leaned forward and gave Vernon a nice view of her ass as she thrusted her hips up and down his length.

"God, this feels fucking great!" She moaned out.

"You missed me, didn't you?" Vernon replied, giving her ass a slap.

"Ya, I was so fucking horny all weekend and I knew only you could satisfy me!" She responded.

"You really are my little slut now, aren't you?" He told her.

At hearing those dirty words from this ugly old man, Courtney couldn't help but orgasm, her tight ass squeezed around Vernon's big dick.

Once finished, she got off him and turned around, putting his cock in her soaking wet pussy as she looked him in the eyes. She moved her pussy slowly up and down his rod, feeling the familiar brush against her cervix. She then leaned forward and kissed Vernon's lips as he raised his knees and began to fuck her back. He reached behind Courtney and grabbed her butt cheeks, Courtney loved it when he touched her body. They soon came together, Vernon filled Courtney's pussy up with his seed once again. They continued to kiss for several moments after completion, as Courtney couldn't get enough of her fat old lover.

"Dinner's gonna be overcooked." Vernon joked as Courtney got off him.

"I can live with that." Courtney said as she grabbed her shorts and headed to the bedroom to change. She came out a few minutes later in a skintight white dress that showed off her every curve.

"How do I look?" She asked.

"Incredible as per usual." Vernon answered.

Vernon had set the table. He prepared Courtney's favorite, honey glazed Salmon with scalloped potatoes and asparagus. This was Vernon's belated birthday dinner for her. He still wasn't sure what their relationship was, but he felt like he should do something nice for her. He had another surprise for her later, but right now they enjoyed their meal together, talking about their weekend apart.

"Thank you for dinner, babe." Courtney said, as Vernon cleared the table.

"I know it's a little late, but happy birthday." Vernon replied, giving her a kiss on the lips.

"Mmm... shall we take this to the bedroom?" Courtney asked.

"I have one more surprise for you." He answered. "Here." He said, handing her a blindfold.

"Ooouuuhhh, naughty!" Courtney replied, taking the blindfold and putting it on.

Courtney stood up, and Vernon took her hand, leading her to the front door. Courtney heard Vernon opening the door and got a little concerned.

"Umm, Vern, where are we going?" She asked.

"Just trust me." He replied.

"Ok." Courtney responded, not 100% sure what was going on.

Vernon brought her down to the parking lot, as the sun went down below the horizon and the street lamps turned on.

"Alright take the blindfold off." Vernon told her.

Courtney took it off and right in front of her was a new white Mercedes-Benz A-class!

"Oh my god, you didn't." Courtney said shocked.

Vernon held the keys up, which Courtney quickly snatched.

"Thank you, thank you, thank you!" An excited Courtney squealed, giving Vernon a big hug. "Come on, let's take it for a spin."

They hopped in the car and soon were speeding down the I-57 south. The radio was on as Courtney put the pedal to the metal and zoomed down the highway. The sun was down as the only light came from the street lamps above. Courtney looked over at Vernon as he sang along to 'California Girls'. She laughed as she watched the old man sing his heart out. She then got off the highway in an exit in the middle of nowhere.

"Were we going?" Vernon asked.

"I have a surprise for you." Courtney replied, which caused Vernon to get hard.

Courtney pulled into an empty lot and turned the car's lights off. She turned the radio down and unbuckled herself.

"Pull it out." She demanded, but Vernon was already out, his cock standing upright.

Courtney put her knees on her seat and leaned over into Vernon's lap. Courtney had only ever blown 2 of her previous boyfriends, neither had washed their dicks right and it ended up tasting like piss and sweaty. It's why she had always resisted blowing anyone, it was not an experience she wanted again. But when she jumped in her new car, she knew she had to do it for him.

Vernon wasn't expecting a blowjob from Courtney, he figured they'd fuck in the car at least once to break it in. He much preferred anal to a blowjob but as Courtney planted a kiss on his cock, who was he to complain.

Courtney kissed down Vernon's shaft, then licked back up, leaving a trail of saliva across his cock. Vernon hadn't had time to clean his cock, so it tasted like a mix of Courtney's and his cum. This gave it a salty flavor that Courtney rather enjoyed. Courtney licked his cock head, teasing Vernon as her hand jerked his throbbing dick off. Vernon groaned as Courtney's teasing hit a crescendo and she finally relented, opening her mouth and sucked him in. He leaned back and closed his eyes, enjoying the feel of Courtney's warm mouth around his cock head.

Courtney held his massive cock head in her mouth, jerking him off as she licked his head some more. She then sucked down a little more and already she felt a gag coming. She bobbed back up before going back down, determined to get further. And she was able to get further, although not far, but had to gag and pulled his cock back out.

That was why Vernon was never pushy about Courtney giving him head. No woman had ever been able to deep throat him completely and while still enjoyable, he much preferred stuffing it all in a woman's ass.

Courtney coughed a bit before returning her lips to Vernon's cock. She licked it up and down before going to his balls and gave them a licking. While not as tasty as his cock, she heard Vernon groan, letting her know he enjoyed that. So she popped one into her mouth and started sucking on it, then switched to the other. Vernon now moaned as Courtney went back and forth between his 2 balls, slobbering all over them.

Courtney pulled away, a glob of saliva trailed from her mouth to Vernon's balls. She sucked it in and used it to spit on Vernon's cock. Her lips then quickly returned to his dick, as she bobbed her head up and down his cock but never getting further than a third in her mouth before gagging.

Vernon opened his eyes and looked down at her wavy blonde hair, putting his hand on the back of her head. He didn't push her head, but guided it up and down, her beautiful lips looked even better around his cock.

Courtney used her hand to jerk the rest of Vernon's cock off. She got into a steady rhythm, her hand and lips worked in unison to get Vernon off. She began to feel Vernon's cock throbbing and figured he must be close. Her intuition was correct as she heard Vernon groan and suddenly rope after rope of cum started flooding into her mouth. It was extremely salty yet had an oddly familiar taste. Courtney held his cum in her mouth until she was sure he was done. She then moved back up and showed Vernon his cum before swallowing his entire load.

"Holy crap!" A turned on Vernon said.

Without saying another word, Courtney pulled her dress up and got on top of Vernon, lining his cock up with her insides.

------

Katy should be relaxing in her bath, but she couldn't. It was Sunday night, and she had run herself a bath, adding a calming lavender bath oil. She had just gotten in and decided to check out Instagram. She came across her and Courtney's photoshoot post that the modeling agency had made. She checked the comments, which was a mistake.