Double Date

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Playboy arranges kinky manage a trois with two girlfriends
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Zeb
Zeb
17 Followers

by Zebulon

This is a work of fiction. No reference to real persons is intended. It contains strong, non-traditional sexual imagery and language. If you don't like this kind of thing, don't read it.

This story may be reposted anywhere as long as (1) proper credit is given, (2) I am informed of where it is being posted, and (3) I am allowed free access to the web site where it is being posted.

Feedback is welcome.

* * * * *

"Say again?" His voice was soft and teasing.

She was clearly embarrassed. She looked down at her dessert plate and said, almost in a whisper, "Please."

"Say it again." His voice a bit more commanding.

The small noises of the restaurant had faded completely behind the rushing sound in her ears.

She stared at her half empty plate and mumbled an unconvincing, "No."

"No?" he asked in a playful tone, knowing he'd tapped into a most secret place.

"Not really," she said with a trembling voice, "that is, not exactly."

"Explain." he said almost sweetly while increasing the tempo of his finger movements through her now squishy flesh.

* * * * *

They had met at a political fund-raiser. Sarah was a beauty from the local college. She was doing volunteer work for the campaign. Jason was a donor. He was tall, dark, and handsome. She was rather surprised to discover how wealthy he was. He seemed rather young to have so much money. She also thought he was a bit arrogant, if charming. He asked her out and she surprised herself by saying yes.

Sarah was even more surprised that their first date had gone so well. He had been a perfect gentleman and they'd had a great time. Within a month she had shared his bed and was again surprised to find he was an excellent lover. She'd somehow expected that with his good looks and money he'd be a dud at lovemaking.

Then the other shoe had dropped. On the third night, when making love, Jason pulled some soft ropes out of nowhere and asked if she'd like to 'play a little game.'

She was very nervous; almost scared. But she also found -- and this was the greatest surprise of all -- she was tremendously turned on by the idea. They played. It was great. She wanted more.

By the end of a few months their relationship had reached the point where they were taking their sex games out in public.

* * * * *

Dinner was at a very expensive and exclusive restaurant overlooking the bay. The lighting was subdued, the mood being set by moonlight reflected on the water and a small candle flickering on the table. There was soft romantic music playing in the background.

The food had been sensational. The other diners were absorbed with their own meals and conversations. Jason's fingers were gently sliding through the moist folds of Sarah's womanhood under cover of the long tablecloth. He had made her come to dinner in an expensive evening gown and no panties. Soon after ordering he had slid a hand under the table and hiked her skirt up into her lap. He had been toying with her privates and with her passions ever since.

Then there had been those questions. Idle conversation when anyone was within earshot punctuated with a whole series of personal, confidential, and often embarrassing questions when they were alone. That was the game. 'Had she ever faked an orgasm?' 'How often?' 'Why?' She was obligated to answer truthfully and had been doing so.

'Did she like giving head?' 'What did she like best about it?' 'What was she thinking that first time she asked him to do her from the rear?' That was a big one. She had always had a strange curiosity about anal sex, but she'd never worked up the nerve to ask any of her previous boyfriends to do it that way. With Jason it seemed an easy and almost natural request. And it turned out to be even better than she'd imagined.

'How long had she known she was a bottom?' 'Why did she like it so much?' 'What did she want to try that they hadn't already done?' She found, without much surprise, that having to answer these embarrassing questions in this public place was turning her on tremendously. Her pussy had been slightly moist when they'd started. It was quite damp now. She was afraid the back of her gown must be getting a wet spot and worried it would show when she got up to leave. She was very grateful for the dim lighting.

Then came the question she had been passionately dreading. It had really struck a nerve and she had done a miserable job of trying to hide the fact. 'Have you ever had sex with another woman?'

She had somehow known the question would be asked sooner or later. A part of her had actually been looking forward to it.

* * * * *

Jason knew early that he liked bondage and domination games. But finding playmates who shared his passion wasn't easy. When he first started dating he'd found only one. Then his father died and left him a large successful company and a fortune in cash and stocks. That made things considerably easier. And he'd developed an instinct. Over time he'd learned things to say and questions to ask when talking with new girls. More importantly, he'd learned how to interpret their answers. Now about one of every three girls he dated ended up being added to the growing list in his little black book.

And being rich he wasn't obligated to play by the same rules as, what his father had called, 'the little people.' He wasn't monogamous and didn't pretend to be. He was, in fact, very truthful to his playmates about his other partners. Those who could live with it did so. The others left. And still his list of names grew.

Sarah had been quite a find. She was a tall girl with a vaguely middle-eastern look. Something in her shape and bearing reminded one of a belly dancer. But her skin tones weren't dark. And her long wavy hair was such a light brown it almost looked blond. All in all, Jason thought she was quite a treat. And then to discover her deep capacity for submission.

* * * * *

He thought about her non-answer as he continued to stroke his finger over her clit. Even in the unclear light he could tell she was blushing furiously. "Go on, explain," he again prompted.

Sarah was stuck and knew it. "I . . . That is, I've never actually been with another woman."

"But you think about it?"

She flushed even deeper and nodded her head.

"You think about it a lot. Don't you?"

Bingo! He'd hit the mark. Sarah, still looking down, closed her eyes and said, "Yes, sir."

"My, my, my, . . . you like women," Jason mused, ". . . and you like to be dominated." His finger slid across her engorged clitoris as he spoke. Sarah unexpectedly tripped over the edge and orgasmed right at the table, just as the waiter was walking up with a carafe to freshen their coffee.

"Please pardon my friend," Jason explained, "she has asthma."

* * * * *

Their lovemaking that night was the best ever. There was an intensity Sarah had never before experienced.

Then she didn't hear from Jason for the next two weeks. She didn't know if she'd done something wrong. If the whole thing was over. Or if he'd just upped and died.

She was moping around her dorm room one night when the phone rang.

"Hello?"

"Are you free Saturday night?"

"Jason, where the hell have you been?"

"Busy," he said brushing aside her question as well as her implied question. "Are you free this Saturday?" he asked with a little more iron in his voice.

She was tempted to say 'No' just to get back at him for leaving her hanging. But instead answered meekly. "Yes, sir."

"Good. My place, 6:45 pm sharp, informal attire, but look nice. Eat a snack before you come, dinner will be late." He paused. She said nothing. "Oh yes," he continued, "and don't beat off between now and then." The phone went dead.

Part of her was furious at this cavalier treatment. But she was also quite turned on by it. Her panties were very damp indeed. She hadn't felt like having sex for over a week. Now she most certainly did. But she couldn't beat off for the next five days. Sarah felt like howling in frustration.

* * * * *

Jason lived alone in an impressive penthouse apartment in the business district. It wasn't even a penthouse in the regular sense. That is, it wasn't part of an apartment complex. It had started out as a temporary residence for his father, who quite literally 'lived the business.' He had it set up using the entire top floor of his corporate headquarters.

When his father died, Jason made sure the company continued to thrive. Knowing he had no head for business, he'd done a good job of hiring excellent managers to run things. Aside from the occasional public event he was obligated to attend, he stayed out of their way and let the cash roll in. The enterprise grew. Soon the corporate headquarters had moved to a larger and more impressive building in a neighboring city. Jason expanded and converted the top two floors of the building into a rather flamboyant bachelor's pad. The 28th floor he reserved as a buffer and a kind of storage facility against his future needs. The rest of the building had been converted to office space.

All of which made for good neighbors. The building was largely deserted nights and on weekends.

There were security guards to guard his security. There was a maintenance crew to deal with maintenance. And there was a discreet cleaning lady who came three times a week to straighten up, do laundry, and make sure the larder was well stocked.

All in all, it was an ideal life for a young, well-to-do, and rather kinky man-about-town.

* * * * *

Sarah arrived by taxi at the front door of the complex a bit early. The security guards knew her face and let her in. She took the executive elevator up to the 29th floor and waited in the anteroom, killing time and checking her wristwatch. She wasn't sure what this new game was, but Jason had said '6:45 sharp.' Punctuality had become an important part of their game. So she waited. Before leaving her dorm she had called and set her watch by the atomic clock in Washington.

She fidgeted with her purse and waited some more. At precisely 6:44 and 50 seconds she walked to the apartment door. It opened even as she was raising her hand to knock.

Jason was dressed only in his black smoking jacket. His hair was slightly disheveled and to Sarah he looked positively delicious. Without saying a word he took her in his arms, pulled her close, and favored her with a long, luxurious kiss. She was almost breathless with lust when he broke off and pulled back to look at her.

"You look fabulous," he said, and then added with a sly grin. "Are you ready for an adventure."

Sarah didn't know quite how to respond. Her legs were weak. What did he have planned? She felt powerful jolts of lust, fear, and curiosity. She suddenly found she couldn't muster the will to speak. Instead she just looked at him with all the emotions she was feeling playing clearly over her face.

Jason studied her for a moment. "I'll take that as a 'yes.'" Taking her hand, he walked her through the penthouse to a far corner of the building.

Sarah found herself entering a large unlit room. She'd never seen it before. It was a den or office of some kind. There was a massive desk lost in the gloom in one corner. Wood paneling covered the walls. And there was plenty of fine conservative furniture scattered about. Jason led her to a massive leather sofa facing a great glass window overlooking the city. The sun had just set. The view was magnificent. The city was starting to light up. The bay was still visible in the distance. A large yellow moon was hanging overhead.

Jason didn't stop to admire the view. He turned and gave Sarah another long kiss. Then he reached down, grabbed the bottom of her fuzzy turtleneck sweater and, as she raised her arms, gently lifted it over her head. He kissed her again, reached around, and unsnapped her bra. Removing the garment, he leaned down and nuzzled and kissed her lovely breasts. Sarah's nipples were rigid and hypersensitive. She trembled as he kissed her. Then she noticed a small pile of bondage paraphernalia on the coffee table. She trembled even more.

Sarah wanted to ask questions, but that wasn't the game. And she had to admit that the uncertainty was adding a tremendous dash of excitement to the evening's mix. What did he have planned? She was already moist when he'd started undressing her. By the time she'd noticed the bondage materials, she was positively wet. Her panties were going to begin sticking to her crotch if this went on for long.

But Jason just kept kissing and licking and nibbling and undressing her as he went. He got down on one knee and carefully removed her sneakers and socks. He undid her jeans and slid them down as well. The panties were the last to go. He carelessly tossed her clothes onto the large leather chair.

When Sarah was finally nude, he stood up and stepped back to admire her. "Superb," he said. She suddenly felt extremely self-conscious and stifled an urge to cover her breasts and crotch with her hands.

Jason reached over to the table and removed a leather collar from the pile. He brought it up and held it before her face so that she could look at it. There was a brass plate with an inscription she could just make out in the dim light. It was her name. She didn't know what to say. So 'this' was what the evening was about.

Jason opened the collar and moved to put it around Sarah's neck. She helped him by pulling her long hair up out of his way.

Once the collar was in place he kissed her again. Then he turned her around, facing away from him. She heard him reach down and pick up something else off the table. She felt her hands being cuffed together behind her back. He stepped up against her and reached around her taut body to massage a breast with one hand and her twat with the other. She could feel the stiffness of his prick against her hands as he nuzzled her ear. If he kept that up for any length of time she would come for sure.

But he didn't keep it up. Just as she was about to grab his member with her cuffed hands, he pulled away again and moved her over to the sofa. With a little help (it was awkward laying down with her hands cuffed behind her), he positioned her so that she was lying on her belly on the sofa.

Jason cuffed her ankles next. He used a short strap to tie her wrist restraints to the ankle restraints. He cinched them tightly. Not so tightly that it was painful, but tight enough that Sarah knew she wasn't going anywhere until he let her.

Jason stepped back again to admire the view. "Magnificent," he said again. "Simply marvelous." Sarah felt very proud to hear him say that. But she felt more lustful than anything else. 'OK,' she thought, 'he has me tied up. Now what?'

The 'now what' turned out to be a gag. It was made of black leather that almost seemed to match the sofa. There was a soft blunt penis prod on the inside that effectively filled her mouth to capacity. And once strapped in place, it kept her from saying anything or even from making very loud noises.

And then nothing much happened at all. Jason sat on the floor next to her and continued to kiss, lick, rub, and fondle her body around the restraints. But Sarah sensed that he wasn't going anywhere with it. He was just biding his time. It was highly erotic, but her curiosity was starting to drive her crazy.

Then, as he was teasingly running one fingernail over her butt coming tantalizingly close to her crotch, a little chime went off that she never heard before. She turned her head and looked at him. He was glancing up at the wall clock. "Right on time," he said, almost to himself.

Sarah grunted questioningly. He only smiled and continued with his gentle fondling. But noticing her uneasiness he said, "The guards ring me to announce guests." At this, Sarah became quite distressed indeed. Somebody was coming up? Surely he wasn't going to let some stranger see her this way. She thrashed about and grunted objections into the gag.

Jason just smiled again and gave her butt cheek a serious slap. It stung. "Quiet," he said. "This is part of the adventure."

Sarah quieted but didn't lose any of her agitation. She could hear the elevator mechanism gently whirring in the background.

Jason again glanced at the clock and then stood up. Leaning over, he kissed her ear and whispered, "Now don't go anywhere." And he was gone. Sarah was left to writhe in her bondage. This she did for just a half minute. Then, realizing how hopeless that was, she got as quiet as possible and listened intently.

At first nothing. The elevator had stopped. She looked up at the clock. 7:14 pm. The second hand was coming up to 7:15. With 20 seconds to go there came a distant knock. 'Hmmph' Sarah thought with a vague sense of superiority 'whoever it is didn't set his watch as accurately as she had.'

A few seconds later she heard the front door open. There was a quiet muffled conversation. Try as she might, she couldn't make out the words. The voices came closer, and Sarah thought she would void her bladder on the nice leather sofa. But the voices turned aside and began ascending the stairs before reaching her.

She was breathing a sigh of relief when she heard the only words she could make out. It was Jason saying, "Are you ready for an adventure?" Then the voices were out of range and try as she might, Sarah could hear no more. She was left trembling in her constraints.

* * * * *

Jason met Daria in college. He was a junior and she was a freshman. She was the most heartbreakingly beautiful girl he had ever seen. But when he studied her face closely, he could never understand why. Nothing seemed to match. Her face was almost square. Her eyes seemed too big and her eyebrows too pronounced. Her nose was slightly upturned and seemed the wrong shape for her face. Her lower lip was too thick and her upper lip too thin. Her mouth was crooked and ears were too big. There was no reason to believe that all these mismatched features put together would spell beauty. But they did. She was absolutely gorgeous and, not only Jason, but everyone who saw her thought so.

Daria had an equally lovely body. Just about average height, she had a very athletic build and deep brown hair. She also had a set of rather impressive and very firm breasts. Jason also discovered she had a wonderful capacity for and interest in sex. And she loved to try new things.

Together they discovered bondage. This lasted until Jason's graduation a year and a half later. Then Daria suddenly and rather unexpectedly had gotten cold feet. Jason was getting a little too serious for her. She was afraid he might start talking marriage. And their sex play was becoming more intense all the time. More intense than she seemed ready for. One day, a few weeks before graduation, he'd asked if she wanted him to take her to a sex club and put her on stage. That threw her for a bit of a loop. She said she'd think about it.

While she was thinking, Jason's father died very unexpectedly. First he was gone and when he returned he was busy. They hardly had time to speak during his final two weeks of classes and examinations. When he graduated he left for good. And that seemed to be that. Daria did get one phone message from him a few weeks later. It was on her answering machine with his new number, but she never called back.

In a fit of what was almost remorse, Daria went back to vanilla sex. For awhile she didn't miss her wilder side. She told herself it was just a phase she had gone through. She joined the cheerleading team. By the time her own graduation came up she'd met and gotten engaged to the star defensive end. Her life was starting to develop in a very traditional way. And that might have been the end of that . . . .

Zeb
Zeb
17 Followers