Meanwhile, at the sex shop!

The place that Lilly had casually referred to as the sex shop turned out to be more or less exactly what the title described. It was a smallish building, tucked away between two other shops at the side of the street. Alex had never been to that part of the city before, but Lilly led him unerringly to it, talking to him the whole way.

“It’s not the biggest shop like this around.” She said with a grin. “They do a lot of their sales online, actually. But it’s a small place with a good atmosphere. Probably exactly what you want, Alex.”

Alex mumbled, blushing slightly at the thought of where they were going. She chuckled at that, chided him for being too innocent, and continued forwards. As it turned out, Alex had been quite right that she was experienced in bed. With an athletic body, a confident personality, and the ability to know exactly what she wanted, Lilly had experimented with many different ways to enjoy herself, or so she told him as his face grew more and more red.

“Whips and chains are traditional.” She laughed. “But it really depends on what hits Clara’s buttons. How far she wants to go, how far you want to go, and so forth. I’d recommend small stuff at first. Handcuffs, maybe? Dunno. Something like that, and moving onto chains if you decide you like that approach. Otherwise, there’s always vibrators, dildos, collars are a classic, of course. Maybe tiny weights for her nipples? Some girls like that. Can’t say I was ever one of ‘em, but some do.”

“You sound like you’re already compiling a list.” Alex moaned. “I don’t know why you even bothered to bring me at all. I feel like I am just gonna get exactly what you tell me to anyway.”

“Well, of course you are, Alex.” Lilly grinned at him. “After all, between the two of us, you’re not the one who has actually felt most of those things being used on you. But it’s important for you to come as well. Otherwise, how are you gonna start to network or understand why I am recommanding what? You still have hella money, right?”

“Not you too.” Alex groaned. “I just finished telling Clara I wasn’t rich, and now you’re in on it too.” He paused, narrowed his eyes. “Are the one who keeps encouraging her to say that I’m rich?”

“Well...” Lilly said slowly. “I wouldn’t say that exactly, but…. Hey look, a convenient distraction!”

They turned to watch the old car. It looked like an antique that someone had spent a lot of time and money fixing up. It turned the street, then left. Silence.

“So...” Alex said. “Did you think that would distract me for so long I’d just forget or…?”

“Eh.” Lilly shrugged. “Worth a try. Anyway, if you have the money, I’ll help you pick out some stuff that I am sure you’ll both enjoy.”

“I have money.” Alex nodded. “So we don’t need to worry about that. So...um… you seem pretty experienced in this sort of thing...”

“Been doing it for a while.” Lilly nodded without shame. “Why, you curious what it’s like?”

“No! I mean… maybe...” Alex paused, **** himself to relax. He took a deep breath, fighting through the fact that he was talking to one of his oldest friends so casually about what she liked to do in bed. It didn’t help that Lilly had always been a fantasy of his. Not as deep as Clara, of course. With Clara, he might dare say that there was something more than just desire. But while he loved Lilly as a friend, he also had to admit that he was pretty sure anything more was just lust. When he dreamed of her, as he had done often during his puberty, it had always been concerned with what they could be doing to each other. He’d fantasised about touching her, stroking her, making her squeal with desire. Never had he put much thought to anything beyond it. Whereas, fantasies of Clara felt a little different, and he had sometimes imagined what it would be like just to be with her, to be close to her emotionally, not just what it would feel like to have sex with her.

Nonetheless, as any human would be able to tell you, lust was a strong ****, and the more Lilly spoke so casually about what she had done, the more and more he pictured it in his mind, in spite of his best attempts not to do so. She spoke of nipple clamps, and he imagined her naked; she spoke of collars, and he imagined her wearing only one of those and said clamps. She spoke of dildos or vibrators, and he couldn’t help but picture her pleasuring herself with them, or being pleasured by someone else. Alex had never seen her naked, of course, but he’d seen her stripped mostly bare before, when they had gone swimming, so he already knew the shape of her body, the lure of her long legs, and toned skin. He felt like a traitor for imagining it, but he couldn’t help himself, so casually and easily did she put the images into his mind.

Slowly, he had started to realise that Lilly was a lot more open about sex than he was. It wasn’t that she was trying to tease him for once. It was just that, what to her was casual, to him was enough to stir the mind, and inflame his desires. She could speak of how some dildo had made her squeal, and he would picture it. His traitorous hormones already rushing to flame the fires of his lust.

Clearly, this would take some getting used to.

“So, Lilly...”

“Yeah? What’s up.”

“You’ve been into this sort of thing for a while, yeah?”

“Sort of thing? You mean BDSM?”

“Y-yeah.” Alex said. “BDSM. You talk like someone who has done it all, and you definitely seem to know your way around a sex toy. Just how long have you been doing this anyway?”

“Hmm.” The blond woman considered for a moment as she led him towards the shop. Her green eyes half closed in calculation. “I’m actually not too sure.” She admitted after a moment. “It’s been

a while… do you remember one of my boyfriends? Jonny?”

“I think so…?” Alex said. “It’s been a while. Is he that one who drank that whole bottle of hair spray on a dare?”

“No.” Lilly said. “That was his friend, but right era. He was the one with the bleached hair, you remember?”

“Oh right! Yeah, I know that guy! What, did he get you started?”

“Sort of.” Lilly admitted. “It was with him that I first decided to do something more than the usual touching and groping, you know? At one point, I had to go to his house, and I ended up wearing my tennis uniform. Not because I had any kinky ideas though. I honestly had just finished playing tennis. You remember that thing has the small skirt?”

“I noticed.” Alex replied wryly. “I think most of us did. The boys, anyway.”

Lilly giggled, and Alex breathed a sigh of relief. It wasn’t really like him to talk so candidly, but Lilly seemed to appreciate that, and he’d taken a risk in order to try and reach out to her. He was happy it seemed to have been well received.

“It was really that bad huh?”

“The age we were at, Lilly?” Alex shot her a look. “Don’t tell me you didn’t suspect.”

“Weeell.” She drew out the word. “Maybe a little?” She laughed. “I have to admit, I did wonder what you all thought of me It made for some nice fantasies. But anyway, we’re getting off track. You remember the uniform? He had me kick off my panties for him, and spend most of the day naked under the skirt. Let me tell you, to the innocent girl I was then, that was a real shocker. By the end of the day, I was just living on adrenaline, convinced that someone would see me. He stayed with me the whole time, steering me around outside in the town. I remember how exciting it was, as well as how scary. I kept wondering ‘’Who will see me like this? Why am I doing this?’’ but I couldn’t deny that I was enjoying it. That was the start. Since then, I just sort of escalated notch by notch. Maybe even the same thing that Clara is trying to do. It’s why I feel for her so much, honestly. When you tell me about what she has done, it reminds me of my own first step, that mix of fear and excitement, and I wanna help her a little bit is all.”

“And since then, you’ve done other things as well? You said about dildos and vibrators, and you said that you had tried nipple weights? What else have you done?”

“Plenty of other things.” She said. “Rope bondage is fun. I’ve done edging, candles and wax, chains, and handcuffs. Games of all sorts, exhibitionism, and plenty of others as well. Why, are you thinking of trying to get me involved in your little game?”

“What? No, no!” Alex spluttered, holding his hands out as though to ward away her words. “Nothing like that! I just… I wanted to know what you had done so I could maybe figure out what I want Clara to do...”

Lilly shrugged.

“Honestly, I’d just go with your gut there. Your gut, and her own inclination, obviously. Keep an ear out to see if she doesn’t want to do something, but it sounds to me like she wants you to take control. Just remember that a fantasy is one thing, but reality is another. Make sure your game doesn’t become too real is all I can say. That’s when things go bad. Remember that she is trusting you, but also remember that you can’t make it all about her. If you want to actually have something other than mindless sex, you need to think about you as well. She wants to be your ****? Okay then, have her do what you want her to do too. Do you have any fantasies about her?”

“Well...” Alex stuttered for a moment. “Maybe a few? But nothing like this. This is totally new for me. I need to think of some way that I can carry it forwards.”

“Which is exactly why we’re going here.” Lilly said happily. “I’m sure when you see some of these toys, you’ll get a kick out of imagining her using them.”

Alex nodded.

“I suppose that’s true enough.” He managed to admit.

By then, they were at the door. Lilly pushed it open, and then gestured for him to follow her. For only a moment, he stood on the precipice, feeling as though he were teetering on the edge of something. Then, he gathered himself, and entered the building.

As soon as the two had entered, Alex heard someone call out. He spun around to see a woman at the counter; she looked around forty or so, with dark black hair flowing down to her shoulders. Her frame was full, and her eyes glittered with interest as they pinned down the two of them.

“Lilly!” The woman called. “It’s been so long since I saw you in person!”

“Oh, hey Jen.” Lilly said with a grin at the older woman. “Been too long, how have you been?”

“Oh you know.” The black-haired woman said. “Same old same old. Selling stuff Buying stuff. Making enough to live. What about you? Still trying to be the best at literally everything?”

“You know it.” Lilly smiled. “I’m probably not going to succeed, but I can try.”

“Who is this?” Jen asked, gesturing to Alex. “Another boyfriend?”

“Hardly.” Lilly replied. “He’s taken. Got a girlfriend and all. Just recently, in fact. That’s one of the reasons why we’re here, actually.”

“Ah.” Jen said with a sage nod of her head. “What’s your name, lad?”

“Alex.” Said Alex, stepping forwards. “I am called Alex. You’re Jen? It’s nice to meet you.”

“Jennifer to most.” The woman said. “Lilly here just likes to shorten it because she enjoys my pain and knows it annoys me.”

“Yeah, she does that.” Alex nodded, before being swatted gently in the head by said Lilly.

“Alex and his girlfriend are just starting to move into more kinky things.” Lilly said bluntly, making Alex flush a little. “And I thought that you might be able to help...”

“Really now? A newbie?” Jennifer’s eyes focused on Alex again, “Well, we can’t have that. Why don’t you tell me a bit about the girl and what she likes, and I’ll help you pick out some toys? I am sure Lilly has already given you her opinion on them.”

And so it was that Lilly and Jennifer spent the rest of the morning helping Alex to pick out toys and tools for the next week. By the time he was done, he had a bag full of various items, and a vague feeling that someone was going to see all he had bought and get the total wrong idea. He had more than enough money, and after a while, he started to feel that he was maybe going a bit overboard, but he didn’t stop, images if Clara in various predicaments rising in his mind. So many things that he had never even considered before now, and yet that he was now wanting to try.

By the time he left, he felt a lot heavier in goods, and a lot lighter in money. Lilly escorted him most of the way back home before peeling off to head to her own house. Before she did though, she reminded him that he had her number.

“Any problems, or if you need help of any sort, just go ahead and give me a call.” She said to him. “I’ll be happy to offer you some advice, or experience, or even a helping hand if you want it.”

She smirked at him as she said the last line, Alex felt his face heating up at the implications.

“Lilly!”

“Hah!” She laughed. “You’re just too easy! You’ll need to toughen up a bit if you wanna be more than a little baby master.” She grew serious for a moment as her laughter receded. “Seriously, though, if you need any help, Alex. Any advice or just someone to talk to, feel free to give me a call. I’ll be there for you. I know getting into this sort of thing can be a bit tough, so don’t hesitate if you feel the need.”

Alex nodded.

“I will. And Lilly? Thanks for the help.”

“No worries.” She said. “Clara was always like a little sister to me, so I am helping as much for her sake as for yours. Not that I don’t like you as well. It’s just that she has clearly spent some time planning this, and I don’t want it to be ruined.”

With that, she moved away, leaving Alex to make the short walk back to his home, all the while, his mind spinning with what he would do in the day ahead. Yesterday had been fun, experimental, but this was more. He needed to take control now, to be what Clara wanted him to be.

The question was, how would he do it….?