Sitting at the outdoor cafe, Derek took one more look at the waitress' shapely legs and was ready to make his move. He had been chatting her up for several weeks and decided she was the perfect candidate. A pretty "girl next door" type with a slightly raunchy sense of humor. Today would be the day he asked her to go to a hotel with him.
"And my wife will love her." He thought.
His wife Janet had issued this challenge over drinks a month or so ago. They could have another "anything goes" threesome but Derek had to find the person. And three rules: no professionals, no using apps, and Janet would not be his "wingman" for the pickup. He'd have to do it all by himself.
"You'll appreciate it more if you have to work for it" Janet had told him.
Threesomes were not new to them. In twelve years of marriage they'd had a variety of experiences and both liked their sex wild and filthy. But Janet had always been the one bringing home the woman, and on a few occasions the guy. She rarely got a "no" from women she approached, and never from the guys. But the dynamic would be much different with Derek making the proposition, especially without Janet there to show to the woman.
"I'm liable to get slapped." Derek laughed.
"You could always bring home a guy." Janet said with an evil wink.
Still looking at the waitress, Derek remembered the last time his wife found a male for their third. They were on a weekend trip to New York and had decided to spice things up on a whim. Janet put on her sexiest black dress and went down to the hotel bar, with Derek taking a seat at a small table across the room. Janet and Derek were both attractive, mid thirties with toned bodies. It didn't take long for her to be approached. She could afford to be picky and sent the first couple of guys away. Derek trusted her instincts as he watched from a distance, butterflies already in his stomach.
She settled on an average looking guy, trim, about their age. Glancing over at Derek, Janet raised an eyebrow. Derek responded with a nod and headed up to their room, leaving her to close the deal. The guy didn't need much persuading; Janet had him to the room only a few minutes behind Derek.
Slightly awkward pleasantries were exchanged; the guy gave his name as "John", which Derek doubted was real, but no matter. To break the ice, Janet poured drinks from the minibar and directed them to sit down. She and John sat on a small sofa, Derek in a chair opposite them with a low table in the middle. They chatted a bit, with the king bed looming just a few feet away.
Their unwritten rule was that Janet always took the lead in any threesome or group situations. It just worked out better that way and also allowed her to exercise her dominant streak. Janet decided they had talked enough, gave Derek a wink, then leaned over to John and planted a hand on his crotch.
"Are we ready to play?" Janet asked as she gave John's crotch a squeeze. She got her answer as his erection bulged against her hand.
Derek still remembered his hesitation the first time a man was brought into the mix. He didn't mess with guys, but he was extremely turned on at the sight of his wife taking total control of another man. John sat back motionless as Janet massaged his hard-on through his pants. Derek was fully erect just watching her go to work, her animal sexual desire on display.
After a final hard squeeze of John's cock, Janet moved to her side of the couch and sat back, her dress riding up on her thigh. "Now strip for me. Both of you."
The two men quickly complied, and sat back down. John stayed on the couch with Janet, and Derek still in his spot on the chair. Janet, now the only clothed person in the room, reached over and began to stroke John's rock hard dick. His breathing got heavy but he didn't move a muscle, allowing her to play with his cock. Derek gripped his own, very much enjoying Janet's show.
Janet stood up and moved to stand directly over John, facing him as he sat on the couch. She lifted her skirt up to her waist, showing off her tiny lace panties. Her crotch now inches from John's face; Janet slid a finger under the waistband and pulled her panties partway down, showing her neat triangle of hair to John. She then turned around to face Derek and bent at the waist, dropping the panties down around her ankles and stepping out of them. Her perfect nude backside was presented to John as she leaned forward resting her hands on the table facing Derek.
"Lick." Janet commanded, while staring into Derek's eyes. John was happy to comply. He started his tongue at the back of her thigh, ran it up between her parted legs, and ate her pussy from behind. Derek could soon see from Janet's face that this guy knew what he was doing. Derek, now wild with lust, stroked his cock as he watched the ecstasy on his wife's face.
Janet lifted her head a little and licked her lips, staring at Derek's cock. Derek didn't need an invitation. He stood and held himself in front of Janet's mouth. She sucked him in all the way, rocking forward a little from John still pressing his tongue in from behind. Now on the low table on all fours, Janet held the men there for a bit, John running his tongue around Janet's pussy as she swallowed her husband's cock. She then got up and moved to the bed, shedding her dress as she went.
Now it was John's turn to watch. Janet laid back, her pussy dripping wet from John's oral skills. Derek ran his hands over her body as he climbed on top of her. Already revved up, he thrust his cock into her as she threw her head back and wrapped her legs around him.
After a few minutes watching the couple fuck like wild animals, John moved closer, laying on his side. His dick was now right by Janet's face, and she leaned over to lick and suck him. The sight his wife sucking cock made Derek go faster, Janet's mouth now bobbing onto John's dick in time with each of Derek's thrusts.
Taking charge again, Janet got up from under Derek and moved John onto his back. John's cock was still soaked with her saliva as Janet straddled him and positioned him under her pussy. She slid halfway down his shaft then back up, teasing him a little first. Then Janet sat down fully onto John, taking his erection deep inside her.
As she rocked back and forth on top of John, Derek moved behind her on his knees. From there Derek had a perfect view of his wife sliding up and down on the cock of the man they just met. Hearing Janet's soft moans as he watched her fuck drove Derek even more insane with lust.
Derek moved closer and Janet leaned forward onto John, her breasts now close enough for him to suck. John fucked Janet from underneath while taking in mouthfuls of her tits. Derek, behind her on his knees, placed his cock against her ass and gently pushed forward. Janet took a sharp breath as the head of Derek's cock eased into her ass. She let out a loud moan as he continued, plunging all the way in.
With a cock now in each hole, Janet pushed back and forth into both of them. The feeling was overwhelming for Janet as John fucked her pussy with Derek filling her ass. Janet was moaning loudly now, and losing all control she bucked wildly as she came in several waves, causing both men to explode inside her.
The three of them unhooked and Janet lay there between them. So dominant a short while ago, she was now quivering and trying to catch her breath. She rolled toward Derek and laid her head on his chest. John got the hint, and started to get dressed. There were smiles and thank you's all around as he left. Derek had drifted off to sleep thinking about how lucky he was.
The waitress snapped Derek out of his daydream/memory.
"Hey there, can I get you something to drink?" She asked.
"Yes. And also, I have a question for you." Derek said with a smile.
The waitress' name was Mindy. Derek laid out his proposition; She got giggly and seemed nervous but said ok fairly quickly. Derek had figured it would go well; he had been laying the groundwork for a couple of weeks.
