The last thing I wanted was for my husband to feel guilty that he isn’t comfortable getting railed in the ass by a man. I quickly reassured him. “Babe, you never need to feel bad that you aren’t immediately comfortable with a crazy fantasy like this. It’s my fault for bringing it up! We have plenty of wacky sex fun as it is, no need to push boundaries to a weird point.”
Clearly, he still wasn’t convinced. “You’re willing to have sex with other women, I shouldn’t have a problem doing the same with other men.” He shook his head. “I’m not ruling it out babe, I just need to find a way to feel more comfortable. As a straight guy you just see it more black and white – women are beautiful and sexy and alluring and men are…not that. Just other dudes.”
He sighed. “Like I said, give me some more time. Maybe we can come up with a way to tease me into it or something.”
I grinned at him. “Like a shemale? You know my dad has that one cousin.”
Chris laughed. “Not what I was thinking, but a good start to our brainstorming.” Then he paused.
“Actually, that gave me an idea. What if we role play this scenario our next time at Maggie’s? Except, we have Jac play the role of the other guy. Jac wears her strapon the entire time, we treat her as if she was a man, and you dom me into getting fucked up the ass ‘by a man’? That might help me at least feel more comfortable with the concept for the future.”
I gazed at my husband with a mix of gratitude, lust, and unfettered love. “You really are the best. Now come fuck me, stud.”
——————————————–
Unsurprisingly, Jac was locked in on the plan from the start. We worked together in the days leading up to our Maggie’s night to come up with a full character for Jac, complete with backstory and unique traits. She practiced several different voices on me, though in the end we both agreed to keep it simple. It was ok to be a little silly, but if Chris couldn’t take the scenario seriously then we had no shot to take the next big sexy step.
For his part, Chris showed nothing but positive energy for our upcoming session. Jac and I kept him out of our planning conversations, but he knew what was going on and was excited about the situation. Of course, the physical aspects would be nothing new for him; he had been pegged before, both by me and Jac. Only the psychological side was supposed to be different, as we wanted him to imagine as much as he could that Jac was actually a guy fucking him, a real man with hot, veiny cock.
It was easier said than done of course, and I had no idea if it would work. But with nervous excitement, we waited for Jac’s closing text before heading out to Maggie’s. Chris had fully shaved again, cleaning all hair off his body beginning below his armpits. He was wearing his ruby banana hammock under a pair of tight khaki shorts and a salmon polo, with tan Sperries to complete the look.
“Mmm babe, you look hot for a closeted frat boi,” I quipped as we pulled into the diner lot. He gave a nervous chuckle in response. “You sure you are ready for this?”
“It’s the same type of stuff we’ve done before.” Chris adjusted his shorts as we stepped out of the car before continuing. “It’s easy for me to enjoy the physical aspects. I just need to set my mind on it being a guy that’s fucking me. We’ll see how that goes.”
We walked in to find Jac already in character. “Welcome to Maggie’s! Table for 2?” She was wearing a flannel, tight jeans with a big belt buckle, boots and a trucker hat with her hair tied back and hidden, and her voice was passably deep. Most importantly, you could see the outline of her thick strapon hanging loosely down her leg.
I grinned and continued our planned dialogue. “Ooh! Hey there, hot stuff. My husband and I would love a table. Maybe one with a good view of that tree trunk you’ve got in your pants?”
“Special treatment table for two, got it!” She led us over to a booth before continuing. “And what would you like to order?”
“My husband here would love a big order of your meatiest sausage, isn’t that right babe?” I gazed with lust at Chris, who played along with fake trepidation.
“I don’t know babe, you know I’ve never swung that way before…”
“Why don’t you show him exactly what you’re packing, Mr. Hot Waiter. Let’s see that thick link.”
With my prompting, Jac began to unzip her jeans, slowly pulling them down to reveal tight white briefs with a distinct bulge from her cock. “One sausage special, coming right up!”
I grabbed Chris’s hand and guided it to Jac’s waistline. “Feel that thick cock babe. Imagine how sexy that is, how hot it will be to take it down your throat, to have him fill up your mouth with his gorgeous meat. Ooh babe, it’s gonna be so sexy to see that meat splitting you open, fucking you in the ass! Please babe, do it for me, take this hot cock for your wife.”
I could see my passionate speech turning Chris on, and I knew if Jac had actually been a guy with a real dick, he would be ready to cross that line for me and give me the show of a lifetime. He grinned and licked his lips.
“Anything for you babe. Now let’s see what you’re packing my man.” He began to pull down her briefs, preparing for her strapon to flop out, when the door to the diner slammed open.
“Holy Fuck! So this is the shit you do on Sunday nights when you close us down, Jac? Play weird sex games with strangers?”
We all froze, turning our heads toward the intruder. A tall, good-looking dark-skinned man about our age stood in the doorway of the diner, staring at the three of us incredulously. “So? You gonna clue me in on what the fuck is going on here?”
I looked to Jac, unsure whether to respond or let her handle it. She was frozen with embarrassment, flannel still on but pants off, the head of her strapon peeking out of her halfway-pulled down briefs. Chris had quickly pulled his hand away as well and sat back down in the booth, clearly wishing he were somewhere else.
I jumped in to try to cut the tension that was hanging over us all. “Hey, I’m sorry, you clearly know Jac but we haven’t met. I’m Laura, and this is my husband Chris.”
The newcomer looked us both up and down, focusing his gaze slightly longer on my husband. He looked a bit like Ricky Whittle, I mused. Tall, dark, muscular, and handsome without an obvious tell as to his ethnicity. Definitely wouldn’t have any issues with the ladies with those looks.
Another moment passed in awkward silence before he spoke, showcasing his slight but noticeable Hispanic accent. “I’m Danilo. Jac’s foster brother, night manager, and part-owner of Maggie’s. And right now she has about 30 seconds to start talking before I lose my cool over whatever the fuck is going on here.”
His frustrated tone finally broke through Jac’s mental block. “Dani, I’m so sorry, I should’ve been more honest with you about this. I’m not gonna say it’s not what it looks like, because basically it is. Laura, Chris and I are using the closed day each month to live out some of our sexual fantasies here. It’s just the three of us, no orgies or anything. If we make any sort of mess, the cleaning crew tomorrow has us covered.”