Double Date

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A man, two women, and multiple fantasies.
9.4k words
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RedJohnny
RedJohnny
83 Followers

Lisa jumped as she felt his fingers under her dress. She couldn't decide whether to look and see if anyone could see or if she was more afraid of knowing the answer.

As his fingers danced on her clit, she became oblivious to the background noise of the restaurant. She could feel his eyes on her.

"What would you like for desert?" he said almost sweetly while increasing the tempo of his finger movements underneath the napkin in her lap.

* * * * * * *

They'd been introduced by a mutual friend. It was an introduction that could only take place in the age of the Internet. The friend lived in Connecticut. He lived outside of Washington, DC, and she lived in Chicago. In an earlier time, the introduction might have led to being distant pen pals, but nothing more.

In the age of email and IM and cell phones, however, their contact quickly blossomed. For whatever reason, they began sharing fantasies – telling each other intimate secrets.

This dinner was the result of their first bet. She was a die hard Cowboys fan, and, as a Washington native, he backed the Redskins. The teams played, the Cowboys lost, and he won. The bet was made before they'd started exploring and fantasizing together, but that just made the upcoming payoff even more exciting for both of them.

Dinner was at one of the best restaurants in Washington – a French restaurant outside the city in the wealthy suburb of Great Falls, Virginia. The lighting was subdued, the mood being set by moonlight a small candle flickering on the table.

The food had been sensational. The other diners were absorbed with their own meals and conversations. Nick's fingers were gently sliding through the moist folds of Laura's pussy under cover her napkin. He had made her come to dinner in a cocktail dress and no panties. Soon after ordering he had slid a hand under the table and hiked her skirt up into her lap. He'd been toying with her 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 felt obligated to answer truthfully.

'Did she like it when a guy came in her mouth?' 'What did she like best about it?' 'Had she ever had anal sex?' That was a big one. She had always had a strange curiosity about anal sex – a combination of fear and forbidden desire, but she'd never worked up the nerve to ask any of her previous boyfriends to do it that way.

'He knew she liked the idea of playing master and slave, but what turned her on about it?' (She knew he knew the answer, but having her say it out loud was part of the game.) 'What did she want to try that she 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 dress 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. "What's the most sexual thing you've done 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. Her curiosity had been hinted at in some of the fantasies she'd written. They'd never actually talked about anything she'd done, though.

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.

Laura was stuck and knew it. "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?"

Laura, still looking down, closed her eyes and said, "Yes, Master."

"So . . . you're curious about being with another woman," Nick mused, ". . . and you like the idea of being told what to do. Is it just the idea of being with another woman that turns you on, or the idea of my watching you with her?" His finger slid across her swolen, hypersensitive clit as he spoke.

* * * * *

Even before the dinner, the second bet was made – the Superbowl. Neither of them had a vested interest, but it was an excuse to play the game. They waffled over who would take which team, and then she asked what the terms of the bet would be. "Winner gets to pick one of the fantasies we've written," he said.

She was torn. She wasn't sure whether she wanted to win or lose. She'd spent so much time fantasizing and there were so many things she wanted to try that she almost said yes immediately. "But wait," she thought, "I might lose. Then he gets to be in charge," and that thought was almost even better for her. On game night, she lost, again.

He already knew that he wanted a fantasy that hadn't been written, yet.

* * * * *

She'd come to DC for the weekend on the condition that they act out one of her other fantasies along with her treating him to dinner.

She waited for him in her hotel room. She'd left a key in an envelope for him at the front desk. She was wearing the oriental-style silk dress she'd had made on a recent trip to Asia. She loved the way the silk brushed against her skin as she moved, like an invisible lover's hands over her body. She loved to look at the way the cut of the dress shaped her body – it was elegant and almost sleazy at the same time in the way that it emphasized her breasts and the high slits on each side of the skirt exposed her legs to the upper thigh - and teased the imagination with the possibility of more – with every step she took. She sat waiting on the edge of the bed. There was something erotic for her about the edge of the bed. She felt the corner of the mattress underneath her hips and thought about being bent over it – her skirt pushed up over her ass, him behind her driving into her. She ran her hands along it – feeling the stiffness of the edge with anticipation.

As he'd directed, she was blindfolded with a black silk scarf. She felt excitingly vulnerable sitting in the room knowing that she wasn't wearing underwear. She'd gotten a full Brazilian wax in anticipation of the weekend, and the feeling of her dress on her now bare pussy made her feel naked despite the dress. She thought about how she'd look to him sitting there – it made her feel sexy and very feminine.

She ran her hands up her ribs to her breasts. The anticipation was almost enough to send her over the edge.

Lost in the feeling of her hands on her breasts, she almost missed the gentle click of the door.

"Nick?"

She heard the door close with a more solid thunk.

"Nick?" she asked a little more hesitantly.

She felt more than heard him in front of her, and then she realized there was a rose under her nose. She breathed deeply, letting the smell roll through her.

She felt the gentle touch of the rose stroking her cheek.

"You look beautiful," he said.

He stroked her cheek, the warmth of his hand following the silken tingle of the rose.

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.

* * * * * *

Through desert, the questioning continued. "What attracted her to another woman?" "Did a particular woman turn her on?"

She looked at every woman he pointed out while his fingers danced over her clit. Occasionally he'd bring his fingers up to her lips for her to taste. She sucked his fingers greedily, enjoying her taste on them and knowing he was imagining her lips on his cock – she was, too.

* * * * * *

When they got to the car, he pulled out the blindfold, again, and asked "Are you ready for an adventure."

Laura 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.

Nick studied her for a moment. "I'll take that as a 'yes.'"

He tied the blindfold over her eyes and helped her into the car.

"We're going to play a game. Will you do whatever I say?"

"Yes, Master."

"Promise?"

"Yes, Master, I promise."

Once he was in the driver's seat, he told her, "Pull up your skirt and play with yourself. I want you to tell me, on a scale from one to ten, how close you are to having an orgasm. If you cum before I say you can I'll have to think of some way to punish you."

"But what if someone sees?" she asked, nervous about the fact that she was blindfolded in the car without any idea what was around them.

"Well, in the first place, you just promised to do whatever I said, but, second, I'll tell you that we're driving on dark, country roads and then we'll be on highway where no one will be able to tell. Now tell me, what level are you at right now?"

"Mmmm....Five."

"Start playing with yourself," he said.

She started hesitantly, still worried behind the blindfold. She made her movements small and furtive, focusing on her clit, trying to be subtle so that no one outside the car could suspect what she was doing.

Given how turned on she already was, she felt her nipples harden and tingle as they rubbed inside her bra. She shifted her hips forward on her seat, spreading her legs more, dropping her chest out view from the side of the car and started rubbing her breasts with one hand and fingering herself with the other. As her excitement grew, she said, "Six," almost immediately and, "Seven," seconds later.

She could feel the car moving, as she pinched and pulled her right nipple as her right hand flicked her clit with a flurry. She needed to cum so badly that her body was flying towards an orgasm.

"Eight," she panted.

"Nine," and he reached over and took her hand away from her clit. "Stop now."

Gasping as her body dealt with the sudden shock of the loss of her fingers, she squeezed his hand and grabbed the armrest.

After a minute, as her breathing began to settle, he said "Ok, start, again."

Her hands flew to play with her nipples and clit again. "Seven." She tried to rub slower this time, to somehow control her excitement and not lose control, but her body was not listening. "Eight" She grunted "Nine...can I cum, please?"

He watched her body tremble and turn beet red as she struggled to keep from cumming. Pulling her hand away, again, he said, "Not yet, Laura, stop now."

"Argh. Oh, Nick, please let me cum. Can I please play with myself, again?"

"Not yet. Put your hands on the dashboard." With a groan she did what she was told. "Tell me about Asia."

Struggling to put her thoughts together and ignore the raging desire in her stomach, she told him about the different countries, the people she'd met, the places she'd seen. As she focused on the memories, she felt the fire not really fading but a least getting under control.

As he saw her breathing gradually slow, he told her to start, again.

As soon as her fingers touched her pussy, she realized how little the fire had actually gone down. It raged back through her body. "Eight" she stammered as one hand stroked her clit and the fingers of the other worked in and out of her pussy. Her fingers were listening only to her body now, driving her hard towards the only thing that mattered – a huge orgasm. "NINE" she screamed as she tried to fight the gigantic orgasm that was building in her.

She didn't even realize that the car had stopped moving. Just as she was about to reach the point of no return, Nick said, "We're here. Stop now," and grabbed her hands and pulled them away from her pussy. "No! Oh my god, no! Don't stop me now. Please!" Laura sat there panting in frustration. Her body quivering with urgent need as it screamed at her to cum.

"We're at the hotel. It's time to go inside."

Suddenly aware that she was sitting in a car blindfolded with her pussy exposed, Laura wondered if anyone was around the car. Her fear of embarrassment fought with the burning need inside her and temporarily won out.

As he helped her pull her dress back down, he slid a finger along her soaking wet pussy, feeling her shiver as he touched her hypersensitive clit.

"I'll be around to help you out. Hold on." He got out and walked around to her side, helping her unfold out of the car. They drew some stares as they walked through the lobby because of her blindfold, but everyone assumed that it was simply some kind of special celebration. They had no idea what had been going on in the car only minutes before, and they would have been stunned to know what would be happening next.

In the elevator, he stood behind her and ran his hands up her stomach to her breasts. She jumped, hoping that there was no one else in the elevator. He gently pinched her rock hard nipples through the silk, sending bolts of lust straight to her pussy. She pressed her ass back against him, feeling how hard he was.

She heard the ding and felt the rush of air as the door opened. He led her down the hall, opened the door to the room and took her in.

She felt him unbutton the top of her dress and then unzip it. She helped him slide it off, enjoying the brush of the silk on her skin. Her bra was next.

When Laura 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.

He stepped up against her and reached around her taut body to massage a breast with one hand and her pussy 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. Instead, he pulled away, again.

He sat her on the edge of the bed and laid her back. He took her left hand, tied a cloth around it, and she realized that her hand was now tied to something on the bed. He did the same thing to her right hand. Nick tied her ankles next. He cinched them tightly. Not so tightly that it was painful, but tight enough that Laura knew she wasn't going anywhere until he let her. She was spread eagle on the bed.

Nick stepped back again to admire the view. "Magnificent," he said again. "Simply marvelous." Laura 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?"

And then nothing much happened at all. Nick sat on the bed next to her and continued to kiss, lick, rub, and fondle her body around the restraints. But Laura 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 up the inside of her thigh, coming tantalizingly close to her crotch, there was a knock on the door. Glancing at the clock on the nightstand, "Right on time," he said, almost to himself.

"Nick," said Laura, very aware of her nudity and vulnerability. Surely he wasn't going to let some stranger see her this way. "What's that? What's going on?" Her voice had a slightly frantic edge to it as she pulled against the restraints. She felt his hand on her chest. It was comforting, and his breath warmed her ear while sending shivers down her body. "Trust me," was all he said, "This is part of the adventure." "I do." Laura quieted but didn't lose any of her agitation.

Nick kissed her ear and whispered, "Now don't go anywhere." And he was gone. Laura was left to writhe in her bondage. Then, realizing how hopeless that was, she got as quiet as possible and listened intently.

A few seconds later she heard the door open. There was a quiet muffled conversation. Try as she might, she couldn't make out the words, but she could tell one of the voices was female. She heard the door shut and realized the female voice was inside the room, and she began to struggle silently against the restraints, again. She was torn – she didn't want anyone to see her like this, but she also didn't want anyone to see her struggling against it. She felt absolutely helpless and she realized that it was turning her on. Her mind began to play out scenarios, wondering what Nick had in mind.

She strained to hear the conversation, but the only words she could make out were Nick saying, "Are you ready for an adventure?" Then the voices faded, again, and try as she might, Laura could hear no more. She was left trembling in her restraints, naked on the bed.

* * * * *

Nick met Taylor a few years before. They'd shared a close bond as they supported each other through difficult times – his separation, her separation. They advised each other, amused each other, and became very special friends.

Taylor had a fantastic body. Petite, bordering on tiny, she'd been a cheerleader and continued coaching cheer teams. She had a very athletic build and, long, flowing dark hair. She also had a set of rather impressive and very firm breasts. Nick also discovered she had a wonderful capacity for and interest in sex. And she loved to try new things. They'd half-joked, half-talked seriously about their mutual interest in the idea of a threesome and how much she'd enjoy being with another woman – not really out of desire for another woman, but out of her knowledge of how much it would turn him on.

Their relationship settled into a close friendship as they both moved on after their marriages. She met someone else, and he supported her and advised her regarding that relationship.

Things might have stayed this way forever. But then came that fateful bet with Laura. He was IMing with Taylor and asked if she'd be interested in living out the threesome fantasy they'd discussed. Just the thought got her juices flowing.

* * * * * *

Laura felt like she'd been lying there for hours, even though it had been a matter of minutes.

"And how have we been?" Nick asked as he entered the room. "Still horny, I hope."

Laura didn't answer. The truth was that she was well beyond simply horny. Her mind had been running circles trying to guess what Nick was up to. She hadn't been able to understand anything the Nick and the guest had said. But unmistakably the voice was soft and sexy and very feminine.

Laura thought about the stories she'd written and how they talked about the involvement of other women. And now he had brought her here along with another woman. She spent the whole time she was alone working herself into a state of erotic tension pouring over the myriad possibilities of what the evening held in store. "Yes," she wanted to tell him. "Yes, I have these secret fantasies all the time. But I'm not sure I really want to do anything about them. At least not yet. I don't think I'm ready for it." But she knew the other woman was there in the room, looking at her – tied up and naked on the bed. And she couldn't bring herself to say any of those things in front of the other woman.

Laura felt Nick reach in between her bound legs. She could actually hear the moist squish that accompanied the feel of slick fingers easily worming their way through her engorged flesh.

"I'm not sure I'm actually ready," she thought furiously as he removed his fingers and gave her butt a firm squeeze. But she still couldn't bring herself to say anything.

She wiggled her body impatiently. She wanted him to untie her and send the other woman away so they could talk about this. She wanted him to take off the blindfold so she could at least see the other woman.

RedJohnny
RedJohnny
83 Followers