The Old Repairman Pt. 04

When Skyler came up for air, Courtney took control and started sucking Vernon's cock again. Skyler took Courtney's position and licked Vernon's balls. She dragged her tongue along his balls from bottom to top, tasting the cum left in his pubes.

The girls continued to switch positions, one sucking his cock, the other licking his balls, until Skyler couldn't anymore. She pushed herself further down, only a little over an inch outside her mouth. But her throat was now raw from sucking and she needed a break.

"Good, it's time I got some attention." Courtney told them.

Vernon got up as Courtney went to her hands and knees. Vernon got behind her and pressed himself into her. Skyler, meanwhile, sat in front of Courtney, being face to face. The girls gave each other a few quick pecks as Vernon thrusted in and out of Courtney.

"Did you enjoy your date with Vernon?" Courtney asked, already knowing the answer, but wanting to hear it nonetheless.

"Ya, it was really nice. I see now why you fell for him." Skyler replied.

"And you enjoyed being in bed with him again?" Courtney continued.

"Ya, it was even better than the first time." Skyler answered.

"Good, because all of us are gonna be spending a lot of time in bed together." Courtney told her.

Vernon continued to fuck Courtney how he knew she liked it. Courtney and Skyler kissed and fondled each other, feeling each other's loving touch. Vernon's cock filled Courtney up like nothing she'd felt before. Like clockwork, she soon came on his cock hard. Vernon kept himself inserted as he rode her orgasm out, feeling her insides clamp around him.

"Huh!" Courtney gasped as Vernon had pulled out of her pussy and stuck it in her ass.

"What?" Skyler asked, seeing Courtney's reaction.

"Mmmm, Vernon just stuck it in my ass." Courtney replied as Vernon thrusted in and out of her ass.

Skyler's eyes went wide upon hearing that. "Wait, he stuck his dick in there?!?" Skyler asked surprised.

"Mmhmm." Courtney responded as she moaned from Vernon fucking her ass. "Oh, it's really good. You'll try it one day."

"I'm not ready for that." Skyler replied.

"Not yet, but flip over and I'll help you get ready." Courtney told her.

Skyler hesitated for a second, but then saw Courtney cum. Her eyes rolled back, and she panted as her body shook and stirred, while her ass spasmed on Vernon's cock. Skyler had to admit it looked good.

Skyler and her husband had experimented with anal one time before. He had licked her ass and Skyler didn't really like it, but as she would come to find out, it was more that he didn't know what he was doing than she didn't enjoy anal.

Skyler slowly flipped over, aligning her ass with Courtney's face. Courtney didn't waste any time stuffing her face between her cheeks. She started by gently licking her ass, giving it some lubrication before diving in further. Courtney then circled her tongue around the outside of Skyler's ass, teasing her just a bit.

"Huh, oh!" Skyler moaned as Courtney inserted her tongue.

The gently stretching of her ass from Courtney's tongue was rather enjoyable. Courtney was being very gentle with Skyler, not going too far to hurt her but slowly inserting her tongue. Courtney was exploring around, feeling how Skyler's body reacted.

Vernon had slowed down to watch. Skyler had a nice ass and he couldn't wait to fuck it. When she heard Skyler moan, he knew Courtney had found a sensitive spot. She would surely push down on the area and have Skyler cumming in no time. He thrusted in harder now, wanting to get Courtney off with Skyler. He hadn't used lube, which he knew she loved. The increased friction between them was quite enjoyable.

Courtney felt Vernon pick up the pace and knew she would not last much longer. She had found a sensitive spot, but knew Skyler needed more simulation. Courtney took her right index and middle finger and traced a line between her pussy lips, then stuffed them in knuckle deep.

Skyler now had Courtney's tongue in her ass and her fingers in her pussy. Over the past few days, Courtney had become very acquainted with her body and knew just how she liked to be fingered. Now being double stuffed by her was too much. She came hard, her ass clamping around her tongue as her pussy did the same around her fingers.

Courtney was glad to feel Skyler orgasm just in time, too. Courtney had felt her own orgasm building to a crescendo, and soon after Skyler's orgasm, she had her own. She pulled her tongue out to moan out as her ass once again began to cum on Vernon's beautiful cock.

Vernon held himself inside Courtney, allowing her to have the full magnitude of her orgasm. He was close and had an idea of how he wanted to finish. He got off the bed and stood up.

"Come here, on your knees." He ordered the girls.

Courtney and Skyler listened, slipping off the couch and onto their knees. Courtney took a few licks of his cock, tasting the many flavors on his dick.

"Put your chests together." He told them.

The girls understood what he wanted and stuffed their chest together, Vernon's cock between them. Their hands squeezed their boobs together, making it tight for Vernon's cock. Their tit flesh surrounded his cock as he began to thrust between them. Courtney and Skyler looked up at him as he fucked their tits, seeing the enjoyment on his face. Vernon looked down, first at their amazing tits perfectly wrapped around his manhood. Then he looked into their loving green and blue eyes. It was too much, and he felt his cock begin to pulse.

"Kiss each other." He moaned, holding off his completion for just another second.

Courtney and Skyler leaned in and kissed right as Vernon began to cum. His wads shot up and hit the girls' chins as they sucked on each other's tongues. They were soon covered in his cum from chest to chin. Courtney licked his cum off of Skyler's chest as Vernon sat down on the bed.

"I think Skyler and I should get cleaned off in the shower together as you prepare for the next round." Courtney said, getting up with Skyler then heading to the bathroom.

------

"It's gonna happen tonight, isn't it?" Skyler asked.

"As long as you think you're ready." Vernon replied.

It was Sunday night and Skyler found herself bent over Vernon's couch. Katy and Courtney had spent the day together, leaving Vernon alone most of the day while Skyler was with RJ, but luckily her ex-husband would take him for the night.

Skyler went over to the condo in a matching red top and small tight skirt. She left her underwear at home. No need for those tonight. She had dinner and danced with Vernon again, teaching him a bit more.

Just like the previous time, their dancing quickly turned into them making out. Vernon groped her body as Skyler sucked on his tongue. He was acting much faster this time and took her top off quickly.

Skyler loved his treatment of her breast. His coarse hands roughly massaging her breast, tugging on her nipples. It was like nothing she'd felt before. Her pussy was dripping just from that. Vernon went up and kissed her again. He slowly moved them towards the couch, her soft lips pressed into his.

Once at the couch, Vernon turned her around and bent her over the side, her ass in the air for him. He pulled her skirt up and over her waist, exposing her intimate lips. Vernon began by licking the juices on her thighs that had dropped down her thighs. He would lick the trail they left all the way up, stopping just before the source. He was teasing Skyler, which only made her wetter.

He eventually gave in and licked her pussy, his tongue entering her and finding a sensitive spot. Skyler became very aroused, but before she could get close to cumming, Vernon pulled his tongue out. Skyler was a little disappointed, but only for a moment as his tongue returned, but this time licked her ass.

Skyler and Courtney had worked on loosening her ass up the previous day, Courtney even stuck her finger in Skyler's ass. Afterwards, Skyler asked if she was ready for anal. Courtney told her it will be a while yet. But as Vernon's tongue pushed past her sphincter, she had a feeling Vernon had a different plan.

Vernon was swirling his tongue around in her ass. He could feel how tight she was that it would be a tight fit, but was doing his best to loosen it up. He knew he needed more girth and Skyler was now warmed up, her soft moans telling him that.

He pulled his tongue and returned with his right index finger. He slowly guided it in Skyler's ass, stretching much further than the previous day. Courtney's finger was much smaller and smoother. She was enjoying Vernon's finger. It was just a different experience.

Once Vernon had pushed his finger in knuckle deep, he began to pull it in and out of her. Skyler closed her eyes as he did this, imagining that this must be what his cock feels like. Her ass was stretched, but not to the point of major pain, although the friction between her ass and his finger gave her a warming sensation. She could feel her orgasm building in her stomach.

Vernon could sense how much she was enjoying it. Her body had begun to gently shake and her moans had become louder the longer he fingered her. He knew he needed to push her a little more, so he pulled his index finger almost all the way, just the tip still inside her. He then took his middle finger and spread her asshole just enough to get its tip in as well. Just as Skyler realized what he was doing, Vernon plunged his fingers in as deep as possible.

"Uhh!" She groaned out as her ass stretched far beyond what she thought was possible.

Vernon held his fingers there. "Just breathe and tell me when he no longer hurts." He told her.

"It's gonna happen tonight, isn't it?" Skyler asked.

"As long as you think you're ready." Vernon replied.

"I am." She responded.

Both knew what that meant; Vernon was going to fuck her ass. While Courtney might disapprove, Vernon knew there was no point in waiting. Waiting only allowed doubt to creep in, and he didn't want that to happen. If Skyler thought she was ready, she was ready.

A little doubt did creep in as she felt his second large fingers stretching her ass out. The pain radiated out from her ass and almost made her legs buckle. But she held firm and soon the pain dissipated.

"The pain has gone away." Skyler said nervously.

"Good." Vernon replied, then began to finger Skyler's butt. He pulled slowly out, then would quickly shove them back in.

"Uh!" She moaned as he shoved his fingers back in.

As Vernon fingered her butt, he went down and stuck his tongue in Skyler's pussy, causing her to gasp. She was being double stuffed. Courtney had done the same to her yesterday, but Vernon's fingers and tongue were much larger and more aggressive. She couldn't hold back any longer. The orgasm that had been building in her stomach finally popped and she exploded, squirting all over Vernon's face.

Vernon got a good taste of her sweet nectar, then stood up and removed his clothes. Skyler remained in position, letting her body come down and catching her breath. Vernon was already at full length and he put some lube on.

Vernon saddled up behind her, slapping his cock between her cheeks. He hot dogged her ass cheeks, dragging his cock between them, letting her feel his length along her ass. It made her a little nervous. She had forgotten just how big he was.

Vernon then pulled back and aligned himself, pushing his tip into her ass.

"Huh!" She gasped as her anal virginity was now gone. "Mmmm..." She moaned as he pushed his entire head in.

Skyler wasn't sure what all the fuss was about. Sure, his cock was a little thicker than his 2 fingers, but not insanely. The pain from stretching was there, but it wasn't overwhelming. Vernon was moving in slowly, not going too far as to hurt Skyler too much. He then got in as deep as his fingers had and knew things would be kicked up a notch from here on out.

"Oh shit!" Skyler screamed as he pushed in deeper to parts unexplored.

Skyler felt an intense pain in her ass as Vernon pushed his cock in deeper. Now she realized why Courtney didn't think she was ready. While fingers could substitute Vernon's thickness, they couldn't match his length. She felt her mistake as her legs turned to jelly and she was hanging on the arm of the couch.

Vernon pulled back, sensing her pain. He knew how painful anal can be, especially the first time. He also knew that he had to completely get it in her or she may never want to try again. So Vernon pushed back in.

Skyler was relieved when he pulled back, allowing her to regain her legs and release the breath she'd been unconsciously holding. Her relief was short-lived as he pushed back in. This time, it wasn't as painful until he pushed further in. He pushed in another inch and then stopped and pulled back. Vernon continued to push in further, then pull out slightly, until somehow stuffed his entire cock inside Skyler's ass.

Vernon loved virgin asses. The tightness was incomparable. While he loved doing anal with Katy and Courtney, there was nothing like breaking in a new ass. He could never last as long because of the grip, but he would enjoy every moment with Skyler.

For Skyler, it was a much different experience. The stretching in her ass was more than a little painful. It was radiating throughout her body, and she wondered how she would get through it. Vernon held himself all the way in, stretching her ass to the fullest extent. Skyler tried to breathe, but it did little to alleviate the pain. Skyler would soon get relief, but not how she thought.

The nerves in her ass had begun to fire the moment Vernon inserted himself, although Skyler hadn't noticed at first. Then, like a switch went off in her brain, she felt the overwhelming pleasure start to take over. The pleasure swallowed the pain and mixed with it. Skyler's body was overwhelmed by sensation and it broke her mind.

Vernon felt Skyler relax and started to slowly pull out. As he pulled out, Skyler suddenly felt empty, and the sensation started to leave. But before it could go away completely, he shoved his cock back in, bringing the sensation right back.

Vernon continued to do long, slow strokes. Every time he plunged back into her, it only increased the sensation in Skyler. She soon found it overwhelming and began to cum. She screamed out as her body violently shook as an unbelievable amount of pleasure ripped through her body. Vernon was forced to stop, as Skyler's already tight ass gripped him even harder.

"Go harder this time." Skyler said once her orgasm had finished.

"Very well." Vernon replied.

He began to thrust in and out of her at a steady pace. Not too fast, as he was still worried about hurting her.

"Harder." Skyler said.

Vernon picked the pace up, banging her ass hard, his thighs slapping against her ass.

"Harder!" Skyler demanded through gritted teeth.

Vernon again picked up the pace, his balls wildly swinging as he slammed himself into her.

"HARDER!" Skyler screamed as she approached another orgasm.

Vernon put it all on the table as he wildly rammed into Skyler. He released all his tension of holding his own orgasm back, meaning he wouldn't last much longer. His cock was a blur as it went in and out of her ass. Skyler was screaming as her mind was once again overloaded with sensations.

Neither of them lasted more than a few minutes. Vernon was the first to release, dropping his load in her ass. The warmth of his seed caused Skyler to cum with him. Her ass tightened up around him, milking his cock for all the cum he had.

After about a minute, Skyler's ass finally loosened its hold and allowed Vernon to pull out. He took a step back and admired Skyler's round ass as his cum leaked out.

"Again." Is all she said. It's all she had to say as Vernon felt the blood quickly rush back to his cock.

It was early the next morning when Courtney arrived home. She was tired and sore, as Katy had shown her just how much she missed her. They had spent the night in a hotel room for some privacy. Overall, it had been a great day with Katy, but now she could use a little sleep. She opened the door to a big surprise.

"Skyler!" Courtney said as she saw Skyler riding Vernon reverse cowgirl, his cock clearly in her ass. "I thought I told you that you weren't ready."

"We had different conclusion." Skyler snarkily replied.

------

It was Wednesday night and a big one. Skyler and Katy were to have their first meet up. Courtney was worried. She cared about them both and desperately wanted them to get along, but knew there was a history. They had not gotten along in the past and had avoided each other for years now.

Courtney wanted Katy and Skyler to meet with all of them together, but Katy had been adamant that Skyler and her met alone. Outside of a text from Skyler saying she'd arrived, Courtney was left in the dark.

The nice thing about Katy and Skyler connecting for the night was it left Vernon and her alone. They had made time for each other over the past while, but hadn't had a night alone in a while. But tonight, they had rented a hotel room and were having dinner at a nice restaurant. Vernon wore a nice dark blue suit, while Courtney had worn a dark blue dress with a floral pattern and a deep V-neck.

"Everything alright?" Vernon asked as they were escorted to their table.

Courtney had been looking at her phone, hoping for an update. "Ya, just worried." She told him. "I'm going to put this away." She said, putting her phone in her purse.

"Don't worry, I know Katy's a little rough on the outside but she's a big, softy underneath it all." He told her as they took their seats.

"I know." She replied. "But I can't help it."

"I know." He responded. "Let's get your mind off it and get a bottle of wine."

After a few glasses of Chardonnay, Courtney's nerves had calmed down, and she could focus on what was at hand. She remembered she had an important thing to discuss with Vernon.

"I need to ask you something." She said as Vernon filled her wineglass again.

"And what's that?" Vernon replied.

"Do you feel like bringing Katy and Skyler into our relationship, makes what we have less special?" Courtney asked.

Vernon gave it a second of thought. "No, you're my number 1 priority. I love Katy and Skyler, but you'll always be the most important person to me." He answered. "How do you feel?"

"I feel like it has." Courtney responded. "This is our first night alone in a while. I feel like we don't have time for just us."

"You know if you wanted to end..." Vernon began to say.

"No, don't even finish that sentence." Courtney interrupted. "I love Katy and Skyler. I don't want to end anything. I just want us to feel special somehow."

Vernon got a serious look in his eye, like he was contemplating saying something. "What is it?" Courtney asked.

"What if we... got married?" Vernon said to Courtney's surprise.

"Are you asking?" Courtney replied.

"I'm... offering." He responded. "I love you, and I know I want to spend whatever time I have left with you. We could still be with Katy and Skyler, but you'd be my wife. A symbol that you'd forever be my number 1." He told her.

The idea had never occurred to Courtney. Their relationship was already so weird, she kind of blocked out the thought of getting married. Courtney was staring blankly at Vernon as she contemplated his offer.

"What are you thinking?" He asked.

"I... I think you should ask me." She answered.

Even in the packed restaurant, the place felt silent to them. Their sole focus was on each other as they blocked out the rest of the world. Vernon pulled his wallet out, Courtney was initially confused. It soon became clear why, when he pulled out a diamond ring. The band was gold while the diamond had a light red color.