"I want to have a threesome with you and another guy."
Dylan wasn't sure when she decided to share this with Jason, but she knew that now was the time. A wave of relief washed through her, followed by the crashing of an even larger wave of anxiety.
She wanted to say a thousand things to dilute the moment, but she didn't dare say more without Jason's first reaction. Dylan had to wait for that since Jason was on the other end of the phone on the other side of the country. She couldn't see his face or his body.
Jason's initial reaction was a silence that felt ten times longer to Dylan than it really was. Dylan's first instinct was to apologize and dismiss her comment as a bad idea.
But her second instinct was to trust her relationship with Jason. It was strong. It was safe to share feelings, ideas, and desires – safe under all circumstances.
Dylan's trust in the relationship paid off. After what seemed like minutes, but was no more than 30-seconds, Jason responded with the simple statement, "Tell me more."
The anxiety waned and Dylan took a deep breath. She had mentally rehearsed many times what she was about to say next. She had even said it out loud a few times in the shower just to make sure the words were hers.
"I liked our threesome with Claire," Dylan said. "I liked it even more than I thought I would. I would like to spend time with her again. And it got me to thinking about whether I'd want to be with two guys."
Jason spoke up, "You had never fantasized about it before then? Or even thought about it?"
"Actually," Dylan replied. "I have not. At least not in the way you think. You see, years ago, just before I turned nineteen, I had a very brief experience with two boys at once and it didn't go well at all."
Jason let out a "whoa" that interrupted Dylan. A period of silence ensued before she spoke again.
"Do you still love me?"
"More than ever," Jason replied. "This can't be easy to talk about."
"Well, it's not and I'm not going into details," Dylan answered. "There was nothing bad or dangerous about it. It was more awkward and clumsy and stupid, to be honest with you. We were all too young. But I came away from it knowing that I'm not interested in playing the slutty whore."
Jason jumped in, "You want caring, sexual attention from two guys. The same way two girls are expected to please the man in a threesome?" It was more a statement than a question.
"Exactly," said Dylan. "I keep thinking about how much pleasure you had when Claire and I were both taking care of you. I know I enjoyed being part of giving you that. I'm asking you to return the favor."
This time there was no silence. Jason felt he owed Dylan and responded quickly, "I'm in."
All of this transpired over the phone because Dylan and Jason had mismanaged their client calendar and double booked their time this particular week. Jason was on the East Coast helping one client. Dylan was on the West Coast helping another with a 10-day project. Jason took the shorter gig and was heading west the next day to help Dylan finish her job.
Jason continued, "So when and how does this happen?"
Dylan explained that she met a guy at the hotel bar and had seen him there a few nights in a row. He was in town for a real estate convention. Clean cut guy. No wedding ring. He was friendly, not flirtatious, but clearly happy to spend time chatting with her each evening.
He didn't hit on her and seemed genuinely interested to hear how Dylan and Jason were both work and life partners.
Still, Dylan had the sense that he might welcome an advance from her. Maybe not for a guy-guy-girl threesome, but she told Jason that was a risk she was willing to take. He seemed like he could respect her wishes for the encounter.
Dylan finished and waited again for a response from Jason. She realized that she had given him a whole lot to process in a short period. But time was short. Dylan wanted the threesome the next night, when Jason arrived and before the real estate convention closed. It wasn't that she was in a hurry to fulfill this relatively new desire; it was that it all seemed so possible right now and an opportunity such as this one might not present itself again for some time.
"Well, you seem to have a pretty good overall plan baby," Jason said. "Now it's down to the details."
"I'll take care of those tonight," she said. "I'm sure I'll see him at the bar."
"What's his name?" Jason asked.
"Mike."
"Well, good luck with the planning and tell Mike I look forward to meeting him."
Jason sounded sincere and Dylan was relieved that he didn't ask if she had already had sex with the guy. She hadn't. She wouldn't. And it made her feel good that Jason didn't feel the need to ask.
-----
Dylan and Jason had dinner together before meeting Mike at the hotel bar. Jason had arrived early enough to work out and shower at the hotel gym. He was dressed pretty casually in jeans and a button down shirt with an open collar.
Dylan was dressed as though she was coming from work, but she looked crisp and smelled fresh. Jason could tell she had spent time nicing herself up. She was wearing her favorite black dress for presenting to groups. The dress fit snuggly up top but had some nice flow below her waist. The neckline was low but not racy. It was cut wide on the shoulders with shortish sleeves. She was wearing Jason's favorite red bra underneath with the straps showing on her shoulders. It was professional but sexy.
The initial dinner conversation focused on work items as the couple tried but failed to act as though this was just another night. Dylan was radiating so much nervous energy that Jason finally asked her about the plan.
She started by describing Mike. He was six-two, fit but not buff, and had sandy brown hair. She walked Jason through her meeting with Mike the night before. She and Mike had covered all the difficult topics and both of them were comfortable the sex would be safe. Mike agreed to respect her wishes throughout the night. And he kept hinting that he was big.
Jason laughed at that last part.
"For your sake," he told Dylan. "I hope he is under promising and over delivers."
Dylan's eyes got real big.
"What?" Jason asked.
Then he heard a voice from behind him.
"I will over deliver."
That was Jason's introduction to Mike. Dylan cracked up laughing. Jason flushed red. Mike stuck out his hand, introduced himself and called the bartender over to all three of them a round of drinks.
They had a fun night with both Jason and Mike giving Dylan more and more physical attention as it got later. A hand on her shoulder here. A squeeze of her calf there. The touching and rubbing had its desired effect, causing Dylan to get hornier and her imagination to go into overdrive.
The bartender was great mixologist. Instead of taking drink orders, he would ask each member of the group about their favorite spirits and flavors and then invent something on the spot. Most of the drinks were original creations and many drinks were consumed.
Dylan wanted to make sure the boys weren't too drunk, or in Jason's case, too tired, to please her so she called for the tab a little before 11pm. She signed it off to the room with a generous tip and herded Jason and Mike out of the bar towards the elevator.
Once inside the elevator, Dylan positioned herself between the two guys. She first wrapped her left arm around Jason's waist, pulled him close, and gave him a deep, passionate kiss. As the kiss broke off, Dylan pivoted to her right, slipped her right arm around Mike's waist, and pulled him next to her. She had a big smile in her eyes.
"It's your turn," Dylan said as she released her hold on Jason.
Mike stepped a little closer and closed his eyes as his lips met Dylan's. Just before they touched, Dylan felt the warmth of Mike's breath. It sent a wave of lust through her body and she could feel the dampness begin to build between her legs. She pulled Mike closer, parted her lips slightly, and received the kiss.
Mike was feeling the lust too and forcefully pressed his lips against Dylan's. She backed away ever so slightly, just enough to separate for a moment and speak. Her left hand came up to brush Mike's cheek.
"Not so hard, not so fast," Dylan whispered.
"Romance me with your kisses first."
"I'm sorry," Mike replied in a startled voice. "I was taking my cues from how you kissed Jason."
Dylan laughed and said, "He's earned it. But don't worry, you treat me like a queen tonight and you'll get plenty of rewards."
She put her hand around his neck and brought her face closer. Mike gave her a gentle kiss and then another. Dylan pressed up against his body and Mike slid his right hand along her waist line and down to her ass.
Jason watched all of this with mixed feelings. Jealousy and regret were not among them. He was getting horny but he was also somewhat bemused. As always, Dylan knew exactly what she wanted and how to get it. She didn't want to be the slutty whore but she did want to be sexually doted on by two guys in ways that turned her on. She just established that with Mike. And it made Jason feel pretty good that she gave him that deep passionate kiss first. It was her way of reassuring him about their relationship as they entered this uncharted territory.
The elevator doors opened and Jason started to step out. Dylan and Mike were unaware they were at their floor. Jason spoke up.
"Hey folks. Let's head to the room."
