Christmas Entanglements Ch. 03

Anna thought for a moment, Aaron being a virgin did seem to fit. "I'm pretty sure he is, either that or he had a bad first experience."

Bridget was contemplative, "I'd believe he's a virgin. He always comes across as shy and introverted, I think it would be hard for him to make the first move if he's scared of getting it wrong."

George furrowed her brow as she thought, "If that's the case II think you're going to have to take the lead and be more forward."

Anna frowned, "I have been forward. I've let him know pretty clearly that I'm interested in having sex. So you think I should just outright tell Aaron that I want him to fuck me?"

George rolled her eyes, "I'm saying you'll have to take control and initiate sex. You can't just wait for Aaron to make a move, it will be up to you to get things started and guide him if you have to."

Anna looked at Bridget to get her opinion. Bridget nodded, "That sounds like the best option. He's probably feeling a little pressured by the hints you've made and is worried about messing things up and disappointing you."

That made some sense, that Aaron's aversion to sex could just be nervousness was comforting to Anna. While she hadn't believed that Aaron's reluctance was due to not finding her attractive she was still relieved to hear someone else say it wasn't some shortcoming on her part.

"I've never really made the first move with a guy. What do you think is the best way to ease him into having sex? I don't know if he'll freak out if I just jump on top of him."

Bridget laughed, "I reckon that a blowjob should do the trick. That should relax him enough that he'll go along with whatever you want."

George nodded, "Yeah. Start with making out and then get him so horny he won't have the chance for his nerves to take control." She grinned, "Or you could just get naked, if that isn't enough you might have to consider whether he's gay."

While her friends' suggestions were fairly simple Anna's mind had been too stuck on thinking about what the cause of the issue with Aaron was to think of how she could solve it. "Thanks, I'll see whether I can make some progress when I see Aaron tonight."

George grinned, "No problem. If you aren't able to get anywhere with Aaron you could always give Chris a call. I'm sure he could give you what you want."

Bridget's eyebrows rose, "You'd be okay with sharing a guy?"

Interestingly George didn't immediately make a flippant reply. The question had her thinking about her answer. "Since I'm not seeing Chris I wouldn't be 'sharing' him. If you're talking about being okay with someone I'm fucking having sex with my friends, I guess it would depend on the people involved. With Chris he's only going to be around for a short time so there's less chance for awkwardness and I wouldn't mind if Anna had sex with him because she knows him better."

Bridget turned to face Anna, looking for her thoughts on George's suggestion. "Would you have sex with Chris if you aren't able to get Aaron to loosen up?

Anna wasn't going to have casual sex with Chris but she didn't dismiss the idea outright. Last night's fantasy had already shown that in some way she was open to sleeping with Chris. She shook her head, "I'm not that frustrated that I'd take the step of going to Chris for sex."

A spark of eagerness appeared in Bridget's eye, "George, would you mind if I had sex with Chris? He's a decent looking guy and what you told us this morning was pretty interesting. If I get the chance, I'd like to see how good he is in bed myself."

At first George was taken aback but then her expression became neutral. "If you want to make a move on Chris, go for it. It wouldn't bother me if you have sex with him."

While George appeared nonchalant Anna wasn't convinced that she was completely okay with Bridget's interest in Chris.

Something caught Bridget's eye and she looked away, "Speak of the devil, isn't that Chris out there?"

Bridget pointed out the restaurant windows to two people standing outside. One of them was indeed Chris. To Anna's surprise the other person was her sister Danielle. As they watched Chris and Danielle hugged before Danielle walked off. Chris continued to stand there and then took out his phone to check it.

"Should we get Chris to join us and give a male opinion on what you should do?"

That seemed like it could be a good idea but Anna wasn't sure about letting Chris know about her lack of sex life with Aaron. "I don't know that Chris would add much to what you've already suggested, plus he probably has a busy afternoon planned."

The reluctance in Anna's voice made George smile. "I think he could be a great help, I bet he was a nervous virgin himself. As for him being busy, it doesn't look like he's in any hurry to go somewhere else."

They all looked outside to Chris and saw him put his phone away and begin to walk away.

Anna felt a surge of relief, "Well it's too late now, he's walking off. We won't be able to catch him."

George smirked, "That's not a problem, I can just call him and let him know we're here."

Anna sighed, "Fine." George picked up her phone and sent a message to Chris. Not long afterward Chris walked into the restaurant and found where they were sitting. He said hi to everyone and took a seat. To Anna's amusement, Bridget sat up straighter, pushing her chest out and then took her knit cap off.

The movement caught his attention and Chris' eyes settled on Bridget, "How has your day been?"

Bridget gave him a quick summary of what they had been up to and even went so far as to show him a few of her purchases. When she asked if he wanted to get something to eat or drink Chris told her that he had already had lunch. Chris chatted a bit with George and Bridget until he noticed Anna looking at him anxiously, he met her eyes and raised an eyebrow, "What's up Anna?"

Anna was embarrassed to be talking with Chris about the problems with her love life. She was at a loss as to what to say, she didn't want to sound like she was bad mouthing Aaron. After an elbow bump from George, Anna opted to try and word it like a hypothetical, "If a guy was reluctant to have sex, possibly due to being a virgin, what do you think would help him overcome his reluctance?"

Chris immediately knew that she was referring to Aaron and she could see discomfort in his expression. After some thought he answered carefully. "Well it will be up to the guy's partner to take the lead with sex. How she should treat him will depend on what the guy is like. If he's nervous then his partner could help him by being patient and encouraging.

If he's just unsure of what to do, his partner could tell him what she wants him to do and how she wants to be touched. As long as the guidance is natural and not just giving instructions and there's a lot of positive feedback, the guy would probably appreciate it.

It's also important to have a lot of time so the sex isn't rushed. If the guy is quick to come, he'd have plenty of time to relax and get ready to go again."

Anna nodded, "That makes sense, do you have any other suggestions?"

"The guy and his partner should go somewhere where they can relax without the worry of being interrupted."

Bridget smirked at Chris, "So not the backseat of a car?"

Chris paused for a moment and Anna thought his face coloured slightly. He then turned to look at George with a profoundly displeased expression. "Really? You told Anna and Bridget about us at the Christmas dinner?"

George frowned,"Yeah, so what? I haven't done anything wrong."

"You don't think there's anything wrong with telling people all about how you had sex with someone else?" Chris' tone was incredulous.

George's jaw clenched and it looked like she wanted to snap at Chris. She managed to suppress that urge and keep her voice level down, "It's not like I was complaining about your performance. If anything, I made you look good."

He made a dismissive gesture, "Okay, but the issue is you're telling people private things involving me without my consent. Look, I can accept that there's going to be some chatting but it isn't necessary to give other people in depth details."

George's eyes narrowed, "Whatever Church boy. You don't know what I said and it's not like I've spread the news around town. Since you're a guy I doubt anyone would even care."

Chris frowned, "I care though. I think it's a matter of respect to not share things that should be private without making sure that it's okay with the other person."

Anna felt her stomach twist, she could practically see the spite building in George and sure enough a brief ugly look crossed her face before she snapped at Chris. "Then it's fine, because I don't respect you at all."

Chris looked at George evenly for a moment before speaking. "Clearly." He shook his head then looked toward Anna. His expression lightened, "Anyway, if the guy's partner makes it clear to him that she wants to be with him that should help his confidence."

Unsure of what to say Anna nodded, "Thank you Chris."

He looked at his watch, "I'm going to have to go now, have a good afternoon ladies."

Bridget tried to lighten the tension, "We haven't scared you off have we? If you stick around you can come with us and help me pick out a bikini."

Chris seemed half puzzled, half intrigued by Bridget's offer and he paused for a moment before he smiled gently and shook his head. "It's tempting but unfortunately I've already got plans for the rest of the day."

He got up out of his seat, "I'll catch you all later." Chris waved, meeting the eyes of both Anna and Bridget before walking off.

When Chris was out of sight Bridget turned to George with an apologetic expression, "Sorry about letting it slip that you told us about having sex with Chris."

George shrugged, "Don't worry about it. I didn't think it was that big of a deal. It's not your fault he's so sensitive."

Anna was feeling guilty, Chris had been unhappy about her and Bridget knowing about his tryst with George during Christmas dinner and he clearly wasn't aware that she had watched him and George having sex. She had also been the one to ask George to share the details of her encounter with Chris. "I do feel bad though. I don't think I'd be all that happy if a guy I had slept with talked about it with his friends."

George wasn't all that happy to hear Anna taking Chris' side but she didn't get offended so it seemed like she was expecting it. "There's nothing for you to feel bad about. I was the one who told you and Bridget."

"There's also the fact that it seems like he had no clue that I watched him and you in the car for a bit." Anna looked to Bridget, "We can't tell him that we know he went over to George's place last night."

Bridget nodded, "Yeah, I hear you. Do you reckon he thinks George told us about it?"

Anna shrugged, "He probably suspects it but he won't bring it up in case we don't know." She then turned to George, "I'm sorry that I asked you to tell us all about last night with Chris."

George was a little subdued, she had a stubborn set to her jaw but she also looked like she regretted what happened with Chris. "That's alright, you two aren't going to go around telling everyone else. He might have a point but he didn't have to treat me the way he did."

As they finished up lunch, Anna saw that George was frowning slightly and staring blankly while lost in thought. Her disagreement with Chris was apparently still weighing on her mind. It was interesting to see that George hadn't been able to just brush off Chris' displeasure.

After lunch the three of them visited a few more stores. Bridget managed to locate some bikinis and convinced Anna and George to come with her as she tried them on and give their opinion on how the bikinis looked. To the surprise of Anna and George, Bridget didn't call out to them to come to the dressing room. Instead Bridget came out of the dressing room into the waiting area where Anna and George were sitting.

The bikini that Bridget was trying on was a metallic dark blue triangle bikini. The triangles in the top were able to be adjusted so if the wearer wanted to show more flesh they could. The bikini bottoms had string ties at the sides and a minimal amount of material covering the crotch. Besides the bikini Bridget was also wearing her knit cap, her coat and her boots. It was an interesting look that in this situation was comical. Out on the ski slopes it would be a lot more impressive. Underneath the bikini bottoms Bridget had kept her hipster panties on so the look of the bikini bottoms didn't have their usual impact but in a way it also highlighted just how little the bikini covered.

Bridget's modelling show was very entertaining and it helped lift Anna and George's mood. She tried on a couple other bikinis but in the end they weren't as good as the metallic blue one so Bridget ended up buying that one.

When Anna took George and Bridget back home, as they said bye they each wished her good luck with her date tonight.

****

As Anna was getting ready to go out with Aaron she agonised over her appearance. She wanted to present herself attractively but was unsure of what would be most appealing to Aaron. At first she thought she should try to look as seductive as possible but then considered that might be coming on too strong. Anna didn't want to make it obvious to Aaron that she was looking to seduce him and potentially make him nervous. She wanted him relaxed and then she would slowly raise the heat until he couldn't help but go along with what she wanted.

In the end Anna went with some tights and a knee length skirt with a blouse and sweater up top. Underneath she chose to wear her sexiest underwear as it helped to put her in a seductive mind frame and if by chance she was able to convince Aaron to go all the way she wouldn't be caught unprepared.

When Aaron arrived to pick her up Anna put her coat on but left it undone. As she approached his car she could see he was checking out her outfit with a smile on his face. "You look great Anna."

"Thanks." Anna smiled and leaned toward him to give him a quick kiss.

In the car Aaron and Anna talked about where they wanted to go to eat and ended up deciding to go to have some mexican food. As they ate, they told each other about their days. Of course Anna left out the details of all the salacious conversations. Aaron had spent the day with his parents, visiting family that they hadn't had the chance to see on Christmas day.

Anna then asked Aaron if he had anything planned for tomorrow. Aaron told her that he was free but was hoping to have a quiet day at home, his parents would be out all day so he would have the house all to himself. That seemed perfect for Anna, it would be a great opportunity for her to seduce Aaron. She told him that she was looking to have a quiet day as well and asked if she could join him, to which Aaron happily agreed to.

While tomorrow would be when Anna would fully seduce Aaron, she wanted to start priming his lust tonight. If she filled his head with thoughts of her, he was bound to be easier to convince to succumb to her advances. Her idea was that she would get him heated up but not push so far that Aaron would get uncomfortable.

Anna thought about where they could go after dinner that would allow her to make a move on Aaron. Thinking back to lunch her initial idea was that they could drive someplace secluded and make out but Anna dismissed it as being too obvious. Both of their homes were out of the question as their parents were home and that would definitely play on Aaron's mind.

Looking outside for some inspiration she saw an advertisement on a passing bus for an action film that was currently playing in the cinemas. It occurred to her that while it wouldn't be private, a dark cinema should be secluded enough to let her make out with Aaron without drawing much attention. Even if someone did see them, they would just be another young couple making out in the cinema, nothing out of the ordinary.

Anna looked back to Aaron and caught him looking at her. They smiled at each other and Aaron flushed in a way that Anna found appealing. "Aaron?"

He cleared his throat, "What would you like to do now?"

Keeping herself from breaking out in a grin, Anna pretended to think for a moment, "How about we go see a movie?"

"That sounds good to me. Is there anything you wanted to see?"

"Not really, weren't you telling me about some action movie you were thinking of seeing?

Aaron smiled, "If you're happy to watch it with me, that would be great."

There was a session for the movie starting soon so they bought their tickets and went into the cinema. There were quite a few other people seeing the same movie but there was still a lot of empty space. Anna took the lead and went up to the back corner. Fortunately no one ended up sitting near Anna and Aaron. She was pleased to see that the arm rests for the seats in the cinema were able to be raised, allowing her to sit right up against Aaron. He put his arm around her shoulder and she rested her head on him.

When the lights fully went down and the movie began to play Anna's heart began to race. She barely paid attention to what was happening on the screen, her focus was instead on when she should make her move.

Once the introduction was over, Anna started with a few soft kisses to Aaron's neck, when he turned to face her she didn't give him a chance to question what she was doing. She took hold of his head and kept it still as she kissed him on the mouth. Caught by surprise Aaron was unresponsive at first but soon was pressing his lips back against Anne's. When it was clear that he wasn't going to move his head away she took her hands away and placed one on his chest. When the kiss broke Aaron looked at Anna with a curious expression but didn't stop her when she moved in to kiss him again.

As they kissed Anna gradually moved her hand down his chest and stomach. When she had just about reached the top of his trousers she paused and distracted Aaron's by kissing him even deeper with her tongue pushing into his mouth and pressing against his tongue.

When Aaron groaned into her mouth she slipped her hand further down so that she was touching his cock. Through the material of his trousers Anna could feel that his cock was starting to thicken. She pressed down and cupped her around the bulge and began to massage Aaron's cock through his trousers. Aaron jolted in his seat, broke the kiss and spoke in a loud whisper, "Anna. What are you doing?"

She didn't bother answering his question, "Does it feel good?

"It does, but this isn't the best place for this." Aaron's voice sounded a bit strained.

"Don't worry, it's dark and no one is close enough to see what we're doing." Anna wondered if she was pushing Aaron a little too far but she needed him to feel a build up of sexual tension so that he wouldn't think of stopping when she wanted to go all the way. He hadn't said no and he wasn't making any attempt to stop her so Anna continued to rub his cock through his trousers. Wanting to be sure that he was okay with what she was doing Anna lightened her touch, "Do you want me to keep going?"

Aaron breathed out heavily, "It feels great, but if you keep going I'll come in my pants."

"Then how about I suck your dick." Anna knew she should stop teasing Aaron now, that she was going too far but she just couldn't help herself. While her intent was to get Aaron hot and bothered, she had also managed to stoke her own desire and now she wanted more from Aaron.

"Right here? I don't think that's a good idea."

Anna's hand pressed more firmly around Aaron's cock. "So is that a no?"

He groaned and Anna felt his cock move. "No. I... if you think we're fine go ahead."