The Girl is Trouble Pt. 19

It was Sunday and we were awaiting the arrival of Jess's brother and sister. Her mother came home around 10 am, freshly showered and in a different outfit than she wore before. She had plenty of her own things at Reggie's as it had been a second home to her for years.

As she came in she smiled sheepishly at Jess and me and went to give Ted a big kiss. He was beaming. It's probably a combination of absence making a heart grow fonder mixed with what Reggie sent him last night.

I realized at that moment that Jess had not gone into too much detail about what her mom and she discussed while I was talking with her dad Friday evening. How detailed do women get about their intimate lives, especially between mother and daughter?

Around 11:30, Jillian and Teddy arrived. Jillian was on the phone with Steve, her husband, talking about something Mia was looking for. Teddy came in after her and seemed annoyed.

"What's up?" Jess asked him.

"Oh, just Steve being oblivious and not being able to find Mia's favorite toy or something. I swear it's like she's talking to someone mentally challenged."

Jess laughed and hugged her brother. He realized he was being distracted and noticed me for the first time.

"So, you must be Darren, the fiancé then?"

"That I am. A pleasure to meet you, Teddy," I said shaking his offered hand.

"I'm sure I'm supposed to put you through the wringer or something as I'm her older brother, but you look fine enough. I'm good."

We laughed and Jillian finally finished her call.

"Oh for fuck's sake that man can be denser than a pile of bricks sometimes. Hi, I'm Jillian."

"Hi, Jillian. I'm Darren."

"Oh yes, I know. 'The Great Darren'. Mom has already given me quite the run down."

"Oh, really?" I said realizing that for whatever she'd been told, it's likely what's going to be discussed today would be bigger.

Hugs were given all around. Made me a bit sad to have been an only child in a pretty emotionless family.

Jess came over and wrapped her hand in mine, looking up at me with a smile. If things went as we hoped, I'd be spending a lot of time with these people.

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"Are you fucking kidding me?!" Teddy asked incredulously.

Conversely, Jillian didn't seem shocked, which was more surprising than Teddy's reaction.

Jess raised her eyebrow at this.

"I knew," Jillian explained. "Early on she wasn't as careful as she thought she was and I was a teenager who was sneaking out myself. So, on more than one occasion, we crossed paths coming home. She didn't see me but I saw her. Once I even saw that it was Reggie she was with. The only thing I didn't know is that you knew, Dad."

"I guess that explains your tense relationship with Mom all these years," Jess said to her older sister.

"Well, how was I to know that Dad knew and was ok with it? I thought she was betraying him. I got numb to it eventually, but yeah, it was hard to reconcile. Things changed a bit later..." she left that last line hanging and I caught a side-eye glance at Teddy. Not sure what that was about.

"Dad, how could you be ok with this? And why are you suddenly telling us now? What changed?" Teddy asked, clearly upset at the news.

"It's not something to easily explain, son. I know you're disappointed in me. But I swear to you, when you love someone more than yourself, it's really not hard to put their needs above your own and then to even come to appreciate their needs, the pleasure they get from having them fulfilled. Knowing that you are part of it by allowing it to happen. Supporting it," Ted told his only son, hoping to help him understand.

"We're telling you, Teddy, because... well, it's something that Jess needs to tell you herself," Betty added.

Jillian and Teddy's heads both turned towards their younger sister.

"I'm a... well... dammit... This is harder than I expected it to be," Jess stumbled in a way I hadn't expected her to.

"We have an open relationship. Similar to your parents," I added in.

"There was an incident on campus with one of my... lovers. He made a scene. A friend of mom's daughter goes to school with me and the gossip got back to mom," Jess finished the story.

"We're so sorry we kept this from you for so long, but I hope you'll understand why. Or at least come to appreciate why we made the choices we did," Betty told her eldest kids.

"Yeah, that's going to take some time, Mom. I'm not mad, just... processing. I mean, holy shit. My mom has a boyfriend. Someone we've known a long time. And I am soooo not in a place to process what that means... in a physical sense," Teddy said, trying to suppress an emotional gag reflex.

"Understood. And thank you for hearing us out. Let's not take away from our time of getting to know Darren and make this be the focus of the whole day, ok?" Betty said like the typical family peacemaker.

"Easy for you to say," Teddy mumbled close enough for me to hear, but the rest of his family missed it.

Betty and Jillian went into the other room to finish preparing lunch and Ted gave his son a look and then headed to his office.

"Soooo, not how I thought today would be going..." Teddy said to no one in particular.

"Dude, it was a shock to me too," Jess said to her brother.

"Yeah but like, you get it easier. You are doing something similar, I guess," he replied with a look that emphasized that he still didn't fully understand.

"Oh, Ted. Come on. You know I was with most of your friends in high school. You're only two years older. You had to know your guys were all banging your slutty little sister."

"Yeah, guess I did. They were smart enough not to brag, but yeah I knew."

"I'm sorry, bro. I like the D. I like the D a whole lot," Jess said, obviously enjoying teasing her brother.

"Ew. Yes, I get it. Just, ugh, I don't need to think about it."

"Ummm, what's up with you and Jill?" Jess asked him.

"What do you mean?"

"There's something... off about you two."

"Nah... you're imagining things. What's off is our mom just told us she's had a long-term side guy and Dad is cool with it."

"He just loves her. Wants her to be happy and to keep coming home to him. I think it's sweet."

"Sure, sure. Is that how it is with you two, then?" Teddy asked, by his look including me in the question.

"Yeah. I'm crazy about your sister and, well, she's just crazy. Completely unexpectedly I've discovered her... adventurousness is exciting to me," I replied.

"Well, I guess there's someone for everyone," he said, glancing towards the kitchen. "I mean, I suppose there are stranger tales."

I guessed he was pretty weirded out about his mom, so learning his sister was into kinky stuff was less of a shock.

We talked a bit more, just getting to know each other. He was a really nice guy that obviously cared about his family. I could easily hang out with him around family events.

The later discussion with Jillian was more tense. Teddy and Ted did the cleanup and Betty made herself scarce so that we could chat with Jillian, or Jill as Jess called her.

"I had a long talk with mom while preparing dinner. I mean, I understand her perspective. I'm glad she's not hurting Dad. That makes it feel better to me."

"Sure," Jess acknowledged.

"What about you two though? For Mom and Dad, it feels like something they got into to break the rut. This going to be your thing the whole time?"

"Maybe," Jess said, looking at me. "Probably. I mean, something could change, but we're both going into this with opened eyes."

I nodded in agreement. "It works for both of us. It's not commonplace, but we like it. I don't feel a need or expect there to be a point to change it."

"What about when you're ready to start a family?" Jillian asked without putting to much judgement into the question.

I found myself blushing unexpectedly. Jess's dirty talk about pregnancy risk with Jacen creeped into my mind. It wasn't a big part of my fetish of watching her with these other men, but I was strangely aroused thinking about it. Would I want her to actually have another man's child? I mean, people adopt kids all the time and men raise stepchildren all the time. It's not like I have some strong need to procreate or pass on my heredity.

And of course when my mind tends to wander into my deeper thoughts I get distracted. Both of the women were staring at me, noticing my blush. Jess saved me though.

"Well, we'll be smart. We'll figure out how to adjust for events in our lives."

Jillian gave us both a look, especially me. I could tell she was skeptical. "I hope so. Oh god, I just thought about what if Mom had gotten pregnant by Reggie."

Jess just gave me a side glance but answered her sister quickly. "Well I guess we'd just have had a half-sibling with an interesting story."

"God, this family is so weird," was all Jillian could come up with. "The bottom line, Darren, is do you love my sister? Will you stick by her no matter what?"

"I'd really like to think so. I can't predict the future, but I know when I think of one without her I don't like it."

"Best answer you could give," Jillian replied with some relief in her voice. "Have you considered what you want to do for your wedding?"

"To be honest, not really," Jess answered her and then looked to me.

"I was thinking something small, close friends and immediate family only. Maybe a destination one."

"Oh, really?" Jess said, amused by my answer. "How close of friends?"

I knew what she was suggesting and, unfortunately, so did her sister.

"Ew. Gross. Like even on your wedding night?"

"I don't know. We'll see," Jess answered defiantly.

"Ugh- why did I ask?"Jillian grimaced.

"Envy. I mean, Steve's a great guy and all but don't tell me you haven't ever had any urge to step out on him."

Now it was Jillian's turn to blush. Seems like she might have some secret of her own.

She quickly recovered though. "Screw you, Jess. Don't play mind games on me. I'm not like you and Mom."

"Jill, you are forgetting just how much I know about your past. You were no innocent. And that wasn't a denial."

Jillian just rolled her eyes and changed the subject. We got talking about destinations for a wedding. I was interested in Jess's thoughts. They were mostly tropical which I was pretty aligned with.

Jillian asked at one point if money was an issue and Jess beamed while looking at me.

"No, not an issue," I said, without going into specifics.

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The rest of the day went well. Jillian warmed up and Teddy was a lot of fun to hang with. It seemed like the whole family got along well and overall handled the news fairly well considering.

It might be weird to say, but in a way I think I fell deeper in love with Jess after meeting her family. It was such a relief to have our relationship, the truth of the relationship, out in the open to both her family and my father. It gave me such hope for the success of our relationship.