Chapter 3: The Penthouse, Part 1

Over the next few weeks, Jonathan made all the arrangements with the lawyers, signing paper after paper for his inheritance. Once it was all official, and he had the keys to the various properties in hand, he decided to go to New York first to check out the penthouse on the Upper East Side.

It was being managed by a rental company that was letting it as a service apartment. They had canceled all the bookings though when they learned of the death of the owner.

When he arrived at the swanky apartment building, the doorman warmly welcomed Jonathan, offering his sympathies about the passing of Charles. He shared some basic info about the apartment building and explained that it wasn’t a true penthouse, as there were two apartments that shared the top floor. But they did have a private elevator and a small lobby area and both were being used for short-term rental. When he went up, he didn’t know what to expect but was wowed by the apartment. It was huge, with four bedrooms, multiple sitting areas, a kitchen that would make any gourmet chef jealous, including an espresso maker that looked like you needed a Ph.D. in astrophysics to operate it, and an amazing balcony with a great view overlooking Central Park. There was also a shared rooftop terrace for the two penthouses only. After settling in and checking out the place, he ventured up the private stairwell to the terrace.

There were noises coming from one corner, he could hear a bunch of women chatting loudly, giggling, and seemingly enjoying the evening.

“Hello,” Jonathan offered, unsure of who was up there.

“Who are you? What are you doing up here? This is supposed to be a private terrace. You aren’t supposed to be up here.”

One of the women started off, quite rudely.

“I believe this terrace is shared by the two penthouses,” Jonathan started to say, but the rude woman, would not let him finish.

“We were told no one was in the other apartment. What are you doing there? We had rented it months ago and the bastard who owns it canceled my reservation last minute. This is my bachelorette party, and the ass canceled on me, making us all squeeze into the one apartment. And now he rented it out to someone else! Fucking unbelievable, these New Yorkers!”

“Well, the owner that you had rented from was recently killed in a car accident. So, yeah, the booking company had to legally cancel all bookings.”

“Well, I don’t know about that, but who are you? Why are you up here then?”

“He was my uncle and I now own it and half of this terrace.”

She huffed and puffed a bit, “well, still, canceling last minute on my bachelorette party just isn’t right.”

“Well, I apologize on behalf of my uncle who could not time his death conveniently for you.”

That got a couple of the girls with her to snicker. She just huffed and puffed some more.

“Look, I’m sorry about what happened with the cancelation, but hope you are enjoying yourself. And congratulations on your upcoming marriage. May your fiancé be blessed with the patience to survive marriage.”

She glared at Jonathan.

“By the way, I’m Jonathan,” he said, extending his hand out. The woman speaking turned her back on him, but a few of the others reached out and he walked over and shook their hands, each introducing themselves.

“Knowing my uncle, I’m sure there is a bottle of fine French wine downstairs I’m willing to share if you like. In the meantime, I’ll let you all enjoy your party.

Jonathan slipped away and could hear the woman, whose name was Brie, say “the nerve...” He was in a generous mood so brought up a bottle of wine and a couple of the girls warmly thanked him and invited him to stay and enjoy it with them, which drew another glare from the queen bee Brie. Jonathan declined and went back to the apartment and continued exploring its nooks and corners, checking all the drawers to discover anything more of his uncle. It didn’t look like he had been there in a while, it was all just standard stuff for a short-term rental, including a very impressive-looking telescope, which he knew wasn’t for looking at the stars through the thick haze of the city.

After going out to eat and just wandering the streets of the city, he meandered back to the apartment building. He checked the terrace and it looked like Brie and friends had moved their party elsewhere, so he grabbed a pair of swimming trunks and headed back up to the hot tub, bringing a bottle of wine with him.

He was enjoying the evening when he heard the distinct voice of Brie. She popped around the corner of the partition wearing a very short and transparent robe, with nothing on underneath. A few of the other girls had towels wrapped around their waists but were completely topless.

“Looks like I overdressed for this party.”

Brie sure did like to huff and puff. “This is my bachelorette party,” she started to yell, “stop ruining it!”

Jonathan had had enough. He had tried to be civil, even offered her a bottle of wine, but she insisted on being a bitch.

He stood up and removed his bathing trunks and told the girls that they were welcome to join him. As he stood there with his cock half-hard facing them, a couple of the other girls gasped and all were staring. It is not like he was huge or anything, a little above average so he was told, but just the boldness of the move shocked them. Two of the girls dropped their towels and joined him in the hot tub, followed by the others, leaving Brie standing alone huffing and puffing.

Jonathan just started chatting with the other girls, ignoring Brie, and sipping from a bottle of tequila that was being passed around.

“This just isn’t right!” Brie said, though no one paid much attention to her. Jonathan scooted over and indicated that there was space for her to come sit next to him. She glared some more, threw off her robe, and pranced her way into the hot tub, making sure Jonathan got a good look at her body. Not too bad, Jonathan thought, at least her fiancé has taste when it comes to looks if not necessarily personality.

Jonathan got to enjoy the view of several pairs of amazing tits floating at water level and as the tequila bottle kept making the rounds, everyone, Brie included, seemed to relax a bit more. Within half an hour though the liquor and the heat from the tub had their effects on Brie. She sat up on the ledge, started to slur her words, then passed out, slumping over Jonathan who caught her before she hit her head. Of course, he caught her with one hand on one of her breasts, accidentally. But he kept it there as he pulled her out of the tub and laid her down on the wooden terrace.

Without putting his trunks back on, he carried her down to their apartment with a couple of the other girls, who had wrapped towels around themselves, though two just around their hips so their breasts were fully on display. Not that it mattered much as he had been appreciating all of their naked tits the entire evening.

Once they got Brie settled onto her bed the three girls turned their attention to Jonathan. There was Lynn who was Chinese American, statuesque, and quite thin, though with very ample tits and a killer ass, Isabelle, a brunette with shortish, very curly hair, who probably had the biggest tits of the group, and Kelly who was dirty blonde and on the thick side, but very sumptuous looking. As Jonathan learned, they had all been sorority sisters in college and were between 26 to 28 years old, ten years his junior. The three girls that had remained in the hot tub were already married, Brie was to be the fourth of the seven to get hitched.

Half-tempted to just grab one of them and start making out with her, which, from the way they had been behaving he assumed they would probably welcome, he realized it was probably best to retreat and head back to his own apartment. He did make an offer though, given that they were all squished into one apartment, that if any of them needed their own bed to sleep in, they could use one of his spare rooms.

It wasn’t even an hour later when all three of them showed up at his door, each in various nighties. Lynn was in a long, loose tee shirt that did not completely cover her bare ass, Isabelle in a crop top that did not hide her amble tits, and very tight short shorts, and Kelly was also wearing a loose tee shirt, her tits just swaying under the material. Jonathan smiled to himself at how the evening was turning out.

He invited them all in and he started to walk them towards the bedrooms down a hallway. As he was pointing out the rooms, Lynn leaned into him and started to kiss him, passionately. Jonathan welcome her tongue and immediately wrapped his hands around her, placing them on her amazing little round ass. After kissing and grinding their bodies into one another for what seemed like minutes, they heard an “ahem” from one of the other women. Jonathan broke his kiss with Lynn and welcomed Kelly into his arms and then Isabelle whose crop-top slid up over her tits, as she jumped into his arms, his hands on her ass. Carrying her, he guided them to the master bedroom and tossed Isabelle onto the bed. Within an instant they were all naked and he found himself diving between Kelly’s outstretched legs.

She grabbed his head and pushed him into her pussy as he licked her and rubbed her clit. At some point, he was able to free himself from her grip and looked over to see Lynn and Isabelle in a 69. Once he got Kelly off, he moved over to the two others and slid his dick into Lynn’s mouth. Isabelle turned around and the two of them licked and sucked him while Kelly returned to the action, kissing him and letting him suck on her tits. Enjoying too much the girls sucking him off, he pulled his cock away and then grabbed Isabelle, spinning her around, and taking her doggy style. The two other girls knelt down beside her, allowing him to alternate fucking all three of them.

He then decided it was time to finish them off, starting with Isabelle. He flipped her over onto her back, scooted her to the edge of the bed, and while standing just fucked her wildly, her legs swinging around in the air until she came. He then pulled out and grabbed Kelly, and then fucked her in the same way. Finally, was the beautiful Lynn. He knew he wasn’t going to last, but did his best to hold his own climax until she came, and came she did. He started to explode himself, pulling out of her pussy and shooting load after load of cum onto her stomach. Kelly and Isabelle moved in and gleefully licked his cum off of Lynn and then Kelly cleaned his cock. He collapsed onto the bed with the three women.

As they started to recover, Jonathan excused himself to clean up in the bathroom. When he returned, he found Lynn alone in his bed, the sheets pulled down, and her laying naked beckoning him.

“I won the lottery tonight, though I’m sure those two will have plenty of fun together too,” Lynn said waiting for him to join her back in bed.

“I am the one who won the lottery with all three of you!” Jonathan exclaimed.”

He climbed on top of Lynn, kissing her, then kissing his way down to her tits. After sucking on them for a while she rolled him over. Kneeling over him she slowly lowered herself onto his hard cock. It took a while before they both came, though Jonathan certainly wasn’t complaining, sucking on Lynn’s tits as she rode him. They both collapsed and fell asleep, their bodies entangled. When Jonathan finally woke, Lynn was still sound asleep. Staying naked, he walked out in search of the other women and found an equally naked Kelly making coffee. He went up to her and kissed her passionately, enjoying the feel of her tits pressed against him. Isabelle was in the shower, where he and Kelly decided to join her. As he fondled Isabelle’s massive tits and fingered her pussy, Kelly got down on her knees and gave him a blowjob until he exploded in her mouth. She opened it showing him his cum, then kissed Isabelle, sharing his cum with her.