Leo sat on the edge of his bed, his partially packed suitcase by his feet. He only had a few short hours, before he needed to head over to Andrea's place to bring her back to his. Tomorrow morning, they would take a shuttle to Georgia for a friend's wedding. But it wasn't the shuttle ride that was keeping him from packing. He was in a predicament, unsure of what to do or how to address it. He couldn't go to Admiral Pike, because the predicament as about his own daughter. Spock couldn't help him, because he simply wouldn't understand. It would be a cold day in hell, before he asked for any relationship advice from Pavel. And he simply could not ask Nyota, for she would kick his ass for even bringing up the topic he needed to address.
That only left one person. Jim. Captain Jim Kirk. Leo sighed, rubbing his hand across his face. They'd recently returned from a six-month mission, giving aid to those who survived the attack on Vulcan, and settling on a new planet. He and Andrea had just celebrated their eight-month anniversary, and things were getting serious. He'd planned on taking her to meet his daughter, Joanna as well as his mother and father.
The door to his apartment that he shared with Jim opened, and he was slightly grateful to hear his friend's voice.
"Bones? You in? " Jim yelled from the kitchen.
Leo got up and walked out of his room, entering the kitchen to find his friend opening a bottle of beer.
Jim looked over at him and grinned, "Hey, how's the packing going?" he asked, leaning against the counter.
"It's going," he mumbled.
"Andrea said she was already packed. Had her shit ready the day you told her about this trip. I never met a girl who could be packed and ready that quick," he smirked.
Leo smiled, "I got lucky with that. And she packs light too," he said, pulling himself up onto the counter top.
"So how long are you guys going for again?" Jim asked, pulling his leather jacket off.
"Two weeks. We're staying at my granddaddy's old beach house," he said.
Jim nodded, "And is Joanna staying with you guys?" he asked, pulling the chair out from the table.
Leo nodded, "Yeah for a couple days. Jocelyn is a little hesitant about her staying with us for a more than a few days," he said, rolling his eyes.
"She's a bitch. Does she think you can't handle your own kid? You should really considered filing some type of lawsuit or something. Fight for your parental rights," he said, pointing at his friend.
"I would but I don't want to cause any more shit between us. I'm lucky that I get to have her for a week. If I started a fight with Jocelyn, she'd probably turn around and tell me Joanna can't stay," he said, with a sigh of defeat.
Jim sighed, "I hope Andrea meets her, that way she can kick her ass," he said, taking a swig of his beer.
Leo looked at him for a moment, before clearing his throat. "I need some….advice," he said.
Jim looked at him, frowning. "Advice? From moi?" he asked, pointing to himself.
Rolling his eyes and pinching the bridge of his nose, Leo sighed. "Yes. I know, it's shocking,"
"I'm touched, Bones. That you actually want my advice about something," Jim said, wiping away a fake tear.
Leo growled, "Don't make me regret this, Jim," he warned.
Jim settled his beer down and held his hands up, "Sorry, sorry. Now, what do you need help with?" he asked.
"Well.." Leo started, trying to figure out how to put his question into easy terms.
Jim watched as he struggled to start off his question, frowning every time he opened his mouth to speak.
"Alright let's start with the obvious question; Does it have to do with Andrea?" he asked.
Leo nodded, "Yes , it does,"
"Okay good. Now, what's going on? Do you want to breakup?" he asked.
Leo quickly shook his head, "God no. I almost lost her once, Jim. I ain't stupid enough to let her go," he said.
Jim held up his hands, "I just wanted to make sure you weren't thinking of that. Calm down. Okay well, so no breakup. Hmmm., are you planning to ask her to move in?"
Leo pondered on the question, for it was something he thought about once or twice. But Andrea was finishing her first semester at San Francisco State University, and she planned on staying with her father as he continued to improve with his physical therapy. So moving in at that point didn't work.
"Not yet. She needs to be with Chris and with us coming and going, I don't want her here by herself," he said.
Jim nodded, "Ok so we can mark that off the list of questions. Are you.. planning on asking her to marry you?"
Leo shook his head, "Not yet. It's still early, Jim. I don't want to rush into marriage with Andrea. I did that already and look where it got me! Divorced and fighting for visitation!"
Jim sighed, "Well, what the hell do you need my help for? Just spit it out, Bones. I can't read your fucking mind!" he shouted.
"I need advice on how to.. approach the subject of.. you know.." Leo said, waving his hands at him.
Jim frowned, "If this is about how to interact with Joanna, I'm not sure I can help you with that. Andrea seems motherly enough, Bones. I mean, she takes care of her father and he's the biggest baby I know," he said.
Leo shook his head, "Jim, Andrea's thinking about having sex while we're in Georgia," he finally said.
Silence fell between them, as Jim was taken back. "Oh.. well.." he said, looking down at the floor. "I don't see why you need my help. You're a man and you've done it before, obviously. And I thought you two were already sexing it up," he asked.
"No, we haven't been "sexing it up". Jesus Jim, you act as if we're teenagers," he said, rolling his eyes.
"Um.. Andrea is a teenager. She's eighteen, remember?" he asked.
"Dammit Jim! Never mind, I'll just figure it out on my own," Leo snapped, as he hopped off the counter.
Jim sighed, "Alright, I'm sorry. Take a seat and let's see what I can do to help you with this.." he said, pointing to the chair across from him.
Leo walked towards the table and pulled the chair out, sitting down. He rested his hands on the tabletop and looked at his best friend across from him.
"So, Andrea wants to have sex and you two haven't done it before. I honestly don't see what you need help with, Bones. If you're in bed and she turns and asks for you to fuck her, just do it," he said, shrugging.
Leo glared at him, "I'm not going to just "fuck" her, Jim. She's not a goddamn hooker or one-night stand. She's my girlfriend!" he yelled.
"Okay so.. I don't know. In fact, how the hell do you know that she wants to do it? Did she tell you?" Jim asked, confused.
"No. She told Nyota and Spock picked up on what she was thinking- how, I have no clue- and he informed me that it would logical to bring contraceptives on our trip," he said, blushing in embarrassment.
Jim snorted, "Oh my god. I can only imagine what was said after that,"
Leo sighed, shaking his head. This was turning out to be more difficult than he thought, and it was staring to stress him out. Jim took notice of his friend's distress and stopped laughing. There was obviously something wrong, if he needed advice.
"Alright. Tell me what's wrong. Do you not want to do it?" he asked.
Leo shook his head, "No, I want to. I've wanted to do it for the longest time. God help me, I know that makes me sound like a perverted old man," he said, shaking his head.
Jim shook his head, "No it doesn't. You're a man, who's in a serious relationship with a woman he loves. And you want to express that love by being intimate," he said, with a shrug.
"She's a virgin, Jim," he finally said, feeling the weight being lifted off his shoulders.
"Oh. Well.. that's good! I mean, now you know that she's not carrying some foul disease or anything," he said, unsure of what do say.
Leo sighed, "Jim, this is difficult to even talk about," he said.
"Well, wasn't Jocelyn a virgin when you two did it?" he asked, frowning.
Leo shook his head, "Nope. Andrea's the first and only. So now you see why I'm freaking out here, " he said.
Jim nodded, "Have you two… done anything of sexual nature? Or is she like no hands or anything below the belt kinda girl?" he asked.
Leo blushed, "We've fooled around a few times," he said, rubbing the back of his neck.
"Define fooled around. If you want my advice, I need to know so I can give you the right information," he said.
There was silence from the older man. Jim rolled his eyes, "Whatever you tell me will not leave this room. I'm not a total asshole, Leo. I wouldn't talk about yours and Andrea's sex life. If it got back to Pike.. " he shuddered.
Leo sighed, "Alright fine," he said, letting out a deep sigh. "We've done oral and heavy petting," he said, closing his eyes.
Jim nodded, "So she's not totally unaware of what to do. And you've done this more than once?" he asked.
"First and only time was the night before we left for the mission. We've been busy- between her classes and Chris's physical therapy and us moving into here- to do anything else. I'm lucky if I can kiss her goodnight before she passes out," he said with a sigh.
"But she knows how to work.. things, right?" he asked.
Leo sighed, "Yes, for the most part. Jesus you're making this harder for me. I'm about to just cancel the trip and forget about it!" he cried.
"Don't! She's been talking about this for the last two weeks!" Jim said, shaking his head.
"Well, then fucking help me! I don't want her first time to be a disaster!" he snapped, running a hand through is hair.
Jim sighed, "Fine. Okay, so you're going to be on the beach. You get Joanna the second week you're there, so you have the entire first week to do it. Plan something nice for her. Dinner and maybe a walk down by the water, something nice," he said.
Leo nodded and Jim continued. "I would say to use candles in the room, but knowing you two- that would be a disaster, he said.
Leo sighed, "How does this help me for when we actually do this?" he asked.
"You need to take it slow with her. It's her first time, so it's going to hurt. Listen to every single word she says. If she tells you to stop, you stop. If she tells you to slow down you do it. Hell, if she tells you to fuck her harder.. you fuckin' do it man! Let her tell you what she wants. And don't make her feel awkward! Tell her that you love her and that she's the most beautiful woman you've ever laid eyes on. Be gentle with her," said Jim, as he sat back in his seat.
"It frightens me that you've become a master at this," he said, looking at his friend in shock.
Jim smirked, "Hey, there's gotta be at least one of us in a social group. I don't mind giving out advice to my friends,' he said with a shrug.
Leo sighed, "God, I think I'm going to have a heart-attack," he said.
Jim snorted, "Better have it now then. It would suck if you had one right in the middle of doing it. Can you imagine the calls we'd get from Andrea? Oh god, can you imagine Pike getting a call from her? "Daddy, Leo had a heart-attack while we were having sex!" I think he would be in a bio-bed next to you!" Jim laughed.
"Shut up, Jim. That isn't funny!" Leo growled, as Jim laughed.
"Dude, relax! I'm trying to lighten the mood here, since you're so serious about everything. Just do what I told you. Bring condoms- I would probably raid the medical closet for more. Once she starts, she probably wont stop. You know how Andrea is about trying things for the first time. Girl nearly drowned the other day while surfing," he snorted.
"That's because you made her take the big waves, when I told her to take the less intense ones!" Leo snapped.
"At least she managed to stay on the board after her first wipe-out, unlike you!"
Leo shook his head, "Alright so I'll stop to get more, before I head over to her place,' he said, covering his face with his hands.
Jim sighed, "Look whatever you do, don't freak out on her. If she really wants to do this, then do it. It would suck if you rejected her because you were too chicken shit," he said.
That was the last thing Leo wanted for Andrea; rejection. He loved her with all his heart, and if she was finally ready to take it to the next step, then he would have to put his worries aside and do what she wanted.
"Thanks for.. you know- this," Leo said, pointing between them.
Jim nodded, "You're welcome. And if you need a pep-talk you can Comm me. But I don't think you'll need to. You're ready and she's ready, so that's all you need to know. Just make it special for her, Bones. You can't get your first time back if it sucks to begin with," he said.
Leo nodded, "I know. I'll keep that in mind when I'm having my heart-attack in the bathroom," he said, standing up.
Jim laugh, "Please don't die while doing it. I need my CMO in perfect health and I really don't want to explain to everyone how you died while getting some-" he said, shaking his head.
Leo chuckled, "Yeah well. I'll try, but I ain't promisin' you anything," he said.
"Go finish packing so you can get your extra rubbers before you pick Andrea up. I'll order some take out after I take a shower. But hurry because it's almost six and you two need to be up early for your flight," said Jim, as he got up from the table.
"Just don't tell her we had this conversation. If she knew that I knew about it.. she'll probably change her mind," Leo said.
Jim nodded, "I wont say a word. Bro-code or whatever the hell they call it," he said, shaking his head.
"Thanks," Leo said, before leaving the kitchen and returning to his room.
Setting the beer bottle into the sink, Jim made his way down the other end of the hall to his room. While he was touched that Leo came to him for advice, he still couldn't figure out why. It was obvious that he was crazy for the girl, and wanted to spend the rest of his life with her. Jim chuckled to himself, as he searched for clothes to change into. It was quite amazing how a 32-year-old man was simply afraid to take it to the next step with his girlfriend. With a sigh, Jim grabbed his clothes and headed across the hall to the bathroom. He would keep his Comm close by for the next two weeks, knowing the Leo would call in a panic. He just hoped it wouldn't be a daily occurrence; being a captain was enough for him. He didn't have plans to being a shrink as well.