Alex slipped into the crisp linen dress, twisted her long blonde hair up with a silver hair comb, and slipped into sky-high sandals. She was conflicted about last night and the upcoming dinner party this evening. She picked up her champagne flute for a long sip. It was time to go - the driver had been out front for more than ten minutes. She felt mildly guilty but since she almost told him to leave, it was better to be late than to no-show. Plus she wanted to return the ‘gift’ in person. This escapade had quickly gotten complicated.
It all started a few weeks earlier. Alex travels for work and lives in California. She’d closed a deal near home and needed a trip to her downtown NYC office to regroup with her larger team. Her firm had been the broker/dealer and she had played a big part in the hard due diligence. She has been completely heads-down during the process. She was ready for fun so she planned to see a new ‘friend’ in New York. She met Rick in Palm Beach and decided to see him again. They met at an old-money watering hole, Ta-boó, and had a totally hot dance. Alex would be staying at her grandparents’ apartment on Fifth Avenue on the Upper East Side. She would meet him at The Pierre.
Alex arranged to have coffee with his PA since he was traveling. She spotted him as he strolled into the lobby dressed casually as if he was in Palm Beach. She suspected that he was a trust fund baby. That was completely unappealing to her. She had a hard stop in an hour to be downtown to 383 Madison before her working lunch meeting.
“I barely recognize you with clothes on,” Rick said loudly as he approached the table.
This mildly amused Alex but also semi-irritated her. It is true she likely was barely recognizable from their last meeting. She most definitely was never in Vacay Mode in the City, and she was suited up and sporting glasses. Men like Rick have zero appreciation for the ‘uniform’ and attitude and approach she has to take to succeed in her business.
“Ha, I bet you say that to all the girls,” she tried to say evenly.
“I am beginning to realize you are much different than the other women I have...dated,” he chortled.
Alex already knew this or at least kind of suspected this. For one, she was one in a million. She had elected to leave her family stronghold of New York to move to northern California. Her family was shocked and disappointed at her decision but she wanted to go where truly no one would know her family name. She had eschewed being a debutante, had gotten kicked out of boarding school, and if it hadn’t been for her outstanding grades likely wouldn’t have even gone to a top university at all. But she had. It was a running joke among her friends that not only was she not trying to get married, but she was known for her very casual ‘dating’. She had zero interest in a boyfriend, a sugar daddy, a socialite, or a husband. That said, Rick was exceptionally well-endowed, so she could overlook his shortcomings. She was completely interested in a hung fuck buddy.
“Truer words have never been spoken. Now tell me, does Joy live with you in Florida or just a visitor to Palm Beach?” Alex asked politely. She wasn’t very skilled at small talk.
“Well, I will repeat what you told me when we met. I bet you have zero interest in my relationship with Joy, or where she lives, or even anything about either of us,” Rick said glibly. “I bet you are most interested in learning when we may fuck. Am I right?”
“Actually you are right. When are we going to fuck, and don’t say now? I have to be in midtown shortly. My schedule is packed up until my flight tomorrow,” she said.
“Ah, how disappointing. I thought for sure that you were staying here or would grab a room to accommodate us,” he said.
“Actually I live near here. It’s a convenient spot for me to meet before work,” Alex stated.
With this, Rick raised an eyebrow with a gleam in his eye.
“I am available after 9 PM this evening. But if you can meet then…” Alex had surprised herself by the offer. Rick was a little new and a little old to fit the Booty Call bill, but she was free later.
“Great, let’s meet at my place at 710 Park,” Rick said.
“Excellent, call me if something comes up.” Alex was getting up to leave. In her mind, there was nothing left to discuss.
That evening, Alex finished at the office by 7 PM, had dinner before 8 PM, and even fit in some yoga before Rick’s. She showered, threw on some jeans with the silk blouse she wore to work, took her hair down, and had the doorman call her a cab. She usually walked everywhere but she wanted to arrive calm and collected.
Rick met her at the door in a robe. Following his cue, as soon as the door shut, she started taking her clothes off. She noticed a coat rack in the foyer and hung them there. She followed Rick into the cavernous apartment to stairs that led up to a bedroom. By the time he turned around, she was standing only in a brief thong.
“Nice birthday suit,” he laughed.
Alex leaned into him and turned her face for him to kiss. He had kissed her neck and caressed her at the club, but they had not kissed. His lips and mouth were delicious, and they stood in an embrace for a long moment. The bedroom featured an antique sleigh bed. He broke the kiss and gave a gentle push to the bed.
“Face down, ass up. I want to eat your gorgeous pussy from behind and savor all of your treasures,” he commanded.
Rick parted her ass and dove headfirst, licking from the tip of her clit to her slit to her sweetheart starfish of an asshole, which he licked and fingered. Her face pressed down into the duvet, Alex could hear him slurping, shuddered to meet his touch, and spaced out in the pleasure. He flipped her on her back.
“I am going to make you cum until you beg me for this cock. You won’t be able to stand or walk straight when I am through with you,” he gruffly told her.
“Promises, promises,” she laughed. Flipped on her back, Rick continued to tease her with his tongue. Suddenly she was ticklish. He was teasing her hip bone and inner thigh, which resulted in very loud giggling. He stifled it by focusing on her large hard clit, which he sucked and sucked until she came. But unlike so many other lovers who as usual were only able to give a one-and-done orgasm, he did not stop. And neither did she; she came over and over and over again. By the time she had lost counting, she looked at him and demanded his cock.
“I need to suck you now. Then I need to fuck you and I want you to cum in my ass.”
Rick ignored her.
“Stand up and bend over the footboard. I am going to fuck you how I please.”
She bent over the large bed, glad that she kept her heels on, and as soon as he tried to enter her, she realized he was bigger than she remembered. In fact, he was so big, she was now hoping he didn’t try to fuck her ass. Rick had other plans. As soon as she presented her backside to him, he plunged his cock into her pussy and his finger deep into her ass.
He barked at her now, “Make yourself cum on my cock.”
Alex was beginning to feel exhausted. She had a hair trigger from cumming so many times. She began to wither a bit.
“Stand up and satisfy me. I didn’t tell you that we’re done. Fuck me hard.”
She decided to clench down on his cock with her pussy to see if she could squeeze an orgasm out of him and spare her ass. It didn’t work.
“Out of kindness, I am getting some lube for your tight ass. If you move while I get it, I will fuck you even longer. I suggest you wait for me as you are.”
He was back in an instant and used his long fingers to spread her ass to pour some lube before coating his cock. Nothing prepared her for the searing, burning pain as he assaulted her ass. It gave way in a moment to the most exquisite sensation she had ever felt. And as he pounded her silly, she thought she could overlook how dominant he was, for now. Her mind was shocked back to reality, and she realized he was rubbing her clit as he fucked her, and soon she was cumming and screaming with his cock in her ass. They continued for a very long time until he came with a thunderous scream. They collapsed on the bed.
“Stay with me tonight. What time is your flight?” he said as she returned from the bathroom. She literally looked like she had been through a war.
“That’s not possible. I really do need a brush, some toothpaste. I’ve got to put myself back together.”
“I have some things for you in the bathroom I had delivered earlier today. Let me know if that works,” Rick offered. And when Alex went back to the bathroom, there was indeed a hairbrush, an elastic for her hair, a toothbrush, some deodorant body spray, and a robe. She wondered if it was actually Joy’s, but she didn’t analyze it. She took a quick shower, cleaned up herself, and emerged ready to dress.
“When are you back in New York or Palm Beach?” he asked.
“I am back in the city every three to five weeks depending on our schedule. I don’t have plans to be back in Palm Beach any time soon,” she replied.
“Well, coincidentally, I will be in San Francisco in two weeks, actually Palo Alto. We fly to Palm Beach from there. Would you like to join me/us?” Rick asked.
Alex thought about this for a minute. When she met Rick, he was with a date who he said was his fiancee, Joy. She was an attractive blonde and Alex wasn’t opposed to a threesome. She actually was selective about indulging in threesomes because it is really not fun to encounter couple drama brought on by insecurity.
“That’s a generous offer, Rick. I would be open to seeing you guys when you’re visiting but I live closer to San Jose than San Francisco. My schedule is really busy..”
“I understand. I’ll call you since we’re supposed to be in Palo Alto and we could always meet in Los Gatos or San Jose.”
Alex had been quietly picking up her stuff and shuffling towards the front door. And without any commitment to see Rick again, she headed out. Once back in California, Alex thought about Rick. On one hand, he was an exceptional lover. But she was wary about him in light of his engagement and since he seemed so nonchalant about meeting with her without his partner. She decided if he did invite her to meet again, she wanted to meet his fiancee. The last thing she needed was some jealous woman stalking her.
When Rick called Alex directly the next week, they arranged to meet with his fiancee, Joy, in Los Gatos. Alex was at the table already when they arrived. Joy was a statuesque blonde who was elegantly dressed. Although she was confident, Alex quickly surmised that she was European, did not work, and seemed to be totally attached to Rick. Lunch was fine but Alex got zero vibes that Joy was personally interested in her. She did read loud and clear that Joy wasn’t aware that Rick had met Alex alone in New York or that Rick had suggested a threesome. So Alex remained very reserved and did not engage in any playful banter. Soon lunch was over and Rick called for the check.
“So how does this work, the three of us?” asked Joy.
“I am sorry I don’t know what you mean,” answered Alex. It felt like it came out of nowhere and she realized Joy did know but had acted primly for some reason and territorial about Rick.
“I mean, do we go with you to a hotel room or to someplace you have?” she continued.
Alex laughed. “I don’t think you have anything to worry about, Joy! I don’t have a hotel room or a place where I 'entertain' couples or partners. I will help you out here - you two continue to enjoy your trip. It’s not a fit for me and I definitely am not interested.” Alex was flustered. She felt the older woman had tried to insult her or intimate that she was like an escort. It was definitely weird. She made a beeline for the entrance. Rick quickly followed.
“Wait, Alex, please don’t go. Listen, Joy is not very experienced and also not from the US and English is not her first language. Please let me explain,” he intoned.
“Rick, you’re an interesting guy. But I am not a playtoy for you and your fiancee. I’m not attracted to her and I am definitely not in the mood for amateur hour.” And as she delivered that message, her car had arrived from the valet and she left without another word.
The next morning she drove into her office only to discover two dozen roses from Rick. Nice gesture, but nothing had changed in her assessment. Rick began calling her assistant after she arrived and after the fifth call, they spoke.
“Just listen to what I have to say, please. Joy is staying the weekend and going to the wine country. I’d love to see you alone again. As I said, I have an obligation in Palo Alto near your office, any chance you’re available?” Alex wondered how he knew where she worked.
“Rick, listen, you’re exceptionally well endowed and a very good lover, but I am totally turned off by drama. I don’t think we should meet again,” Alex said.
“Well, I know you are free for lunch, can we meet one more time for coffee? I am just down the road.”
Alex found herself giving in. She agreed to meet down the road at a coffee shop. When Rick arrived, he came over and kissed her.
“I need to finish what I started in New York. A strong woman like you needs a strong man like me to have a great sex life. You know we have unfinished business.” She had to agree. She wanted to fuck him again, badly. Soon they were back at the entrance and Rick’s driver pulled up in a large Bentley.
Alex joined Rick in the backseat. He began whispering very suggestive, very naughty, and very explicit things in her ear. “Spread your legs, even more, how disappointing you have panties on, let me just pull them aside.”
In another motion, Rick flipped a switch on the door as a concealed privacy screen emerged to separate the front and back seats. He pushed Alex towards lying down on the broad seat while lifting her skirt and pulling her legs apart before going down on her. Try as she might, Alex found herself quickly giving in and being overwhelmed with pleasure. As she continued to cum on his lips, she heard the sound of his belt buckle and zipper. Rick kneeled on the floor now.
“Sit back and let me fuck you, or let me sit down and have you mount me.” Feverishly they started fucking in the car, obscured by the tinted windows and privacy screen. “You’re going to be mine, Alex. Oh, I probably will marry Joy, but I want to collar you. I don’t want to marry you. I want to imprison you with a hunger for me that will consume you.” Alex laughed. We’ll see about that, she thought.
“Come with me to Palm Beach. Meet me at the private hangar on the north end of the San Jose International Airport,” he said. “We fly the day after tomorrow. I will take care of Joy. I want you to go to a special dinner party in Palm Beach with me. It is strictly for those in the lifestyle. Do you know what that means?”
Alex did not know what Rick meant. She decided to check in with her friends if she was going. Rick could very well fly her to Palm Beach but she wanted a backup plan.
Alex did not know about ‘the lifestyle’. She had a sneaking suspicion that it was exclusive, naughty, and definitely not something to discuss with her friends, family, and work. But she was intrigued. She did know a little bit about being collared. A school friend opened up a BDSM sex club like one in Kabukicho, a famous red light district in Tokyo. To be collared is to signify a Dom-Sub relationship. She laughed to herself, he had a snowball’s chance in Hell to collar her.
Still, she found herself giving in to him one tiny inch at a time, including packing a bag to go to Palm Beach, setting up some time to be with her friends there, and actually even taking a vacation day on Monday. She’d flown out of SJC and General Aviation before, but she didn’t know what to expect. Once she got to Atlantic Aviation’s fixed operator terminal and hangar, she wandered around before finding an employee who directed her to a hangar. There was a Gulfstream 550 late model with the stairs down and a limo parked next to it. Alex stood by the car for a moment before Rick emerged.