Yes (Shopping and Dinner)

After mulling it over, you decide the best way for you to quell your own suspicions about Jennifer's new friend is to just meet her. "Sure thing, honey." She smiled with your response and told you to get ready for a day of shopping and dinner after. You went upstairs and picked out a semi-casual outfit from the walk in closet. You put on a pair of boxers, white undershirt, striped polo, best pair of blue jeans, and a pair of loafers. Jennifer followed shortly behind you, slipping into a white lace thong, a matching bra, leggings, and a comfortable blouse. After she applied her light makeup, you both went down to the car and drove to the mall to meet up with Rachael.

Your back hurt, but it was almost a relief to find out that Rachael really was just a friend, but it was clear that you were the pack mule for the bags from the store. Shoes, perfume, lingerie, and such were in all the bags you held, after a while you stopped going into the stores with them and just sat on the bench outside. You got some looks from the other people in the mall as they chuckled, even some concern that perhaps you were carrying a bit too much. A blonde haired guy walked up to you and smiled, "Hey, you want a hand with that? Sorry I'm late, Rachael didn't exactly give me good notice." He started grabbing some bags and you were a bit confused.

"Sorry, I just met Rachael. I guess she's been palling around with Jennifer for a while. What's your name?" You asked, trying to be polite.

"Reginald, but you can call me Reggie." He was a bit taller than you, definitely seemed like he's seen his fair share of days at the gym. Reggie was dressed in a tight fitting t-shirt and some khakis. He was also wearing sunglasses. You two didn't have to wait long when the women came out of the store.

"Reggie!" Rachael exclaimed, "I'm so happy you're here. This is Jennifer and her husband." She smiled. "So boys, what's for dinner?" She asked.

"I mean, I'm up for anything." You said.

Reggie looked around, "Well, nothing beats the steakhouse at the hotel on 8th." He rubbed his chin a little in thought, "Hey, my treat, especially after you two made this guy carry around all your stuff." Everyone got a laugh and even you were excited at the idea of a free meal at a fancy steakhouse.

You all decided to pack up into your and Jennifer's SUV, plenty of space for the shopping bags and everyone in it. You'd just drop off Reggie and Rachael after dinner at their car. The place seemed a little busy, but you didn't have to wait long. They set you out on the balcony on the second floor. You had a nice view of the river and the city lights reflecting off of it. A really nice benefit was that you weren't close to other tables like you would have been inside, so you didn't have to talk over anyone or worry about anyone overhearing your conversations. Everyone ordered their food: Steak for you and Reggie, Jennifer ordered chicken parmesan, and Rachael ordered filet mignon. Reggie looks at you and Jennifer as everyone waited for their food, "So, how long have you two been together?"

Your wife answered before you could, "Well, we met in college and started dating then. Feels like forever." She chuckles, "When did you and Rachael start dating?"

Reggie scratches his head, "Well, I wouldn't exactly say we're dating." Rachael blushes, "But a few weeks, I'd say." Jennifer's curiosity was piqued.

"What do you mean?" Your wife asked.

"Friends with benefits would be more accurate." Reggie said.

"Oh, I get it, so you two just hang out every now and then and hookup. Why thought? You make such a cute couple." There was a bit of an awkward silence as Reggie looked at Rachael with a smirk. Just as Reggie was about to speak, the food arrived and everyone started chowing down on their food.

After Reggie swallowed his first bite, he looked at Jennifer, "Okay, so I have more friends with benefits than Rachael. I'm a single guy, not tied down to anyone, just living my best life. Works out for both of us because she scratches my itch and I scratch her itch that most guys can't."

"Hey, why are you being so upfront?" Rachael protested.

"There's nothing to be embarrassed about, Rach. Some guys just aren't good at sex. I'm not a medical professional, but you don't see me getting broken up about not being able to do open heart surgery. I'm also not bothered that I'm not really tall enough to play on a successful pro basketball team either. We have our strengths, and one of mine just happens to be that I'm good at sex." Rachael blushed, but didn't really say much. Jennifer was fascinated.

"Good at sex?" You wife asked. "I guess I just don't understand."

"Well," Reggie started, "does your husband make you cum every time you have sex? Have you ever came more than once during sex?"

"Hey wait a minute," You piped up, "This is pretty personal, we just met you. And why does that matter anyway?"

Reggie held up his hands, "Hey, sorry. I guess I got carried away, I'm not trying to overstep a boundary. I guess I'm just use to being candid."

Jennifer put her hand on yours, "It's no biggie. I was just curious, maybe we can talk about it later." You all continued to eat dinner and engage in small talk. Reggie isn't from the area and apparently used to do various construction jobs while he was working on his degree. Now he manages construction. You and Jennifer shared the details of your professions. Rachael was in-between jobs, but she had plenty of savings in the meantime. She came from a wealthy family and used to work in banking, but she's trying to open a business.

As Reggie put his wallet away after paying the server for the meal plus a generous tip, he looked back at you and your wife, "Well, I think you two are a nice couple. I'm glad we met." He looked over at Rachael, "We're doing something this weekend, wanna go with us?" He asked.