My Daughter's Best Friend

"I, er, guess I'll," I started the sentence hesitatingly and once again Lily chose to jump in, essentially ignoring me.

"Oh, did you want to see those skirts?" My face probably just showed confusion, I only barely remembered what she was talking about, but Lily was unconcerned. She was already reaching for her phone. "I should be able to get them pretty quickly." I was happy for the excuse and stepped closer as she tapped away.

"Here they are."

She proffered her phone and I dutifully nodded my appreciation. I could barely tell the difference between each one as she flicked through and, sadly, they weren't modeled by anyone, let alone Lily, but they looked nice enough as far as skirts went.

"That's my favourite," she said as ended the show, putting her phone back on the table. She looked thoughtful, idly glancing from my face to my groin and then back again. "I'll probably wear it next week, so you'll get to see it then."

"Sounds good."

She smiled at me and I could feel my heart beating throughout my body. I was as nervous as I'd ever been but I still found it thrilling. As we'd talked Lily had pushed the stool away from the breakfast bar and was now slightly facing me as I stood to her right. The experience of chatting to her mostly naked and letting her look wherever she wanted was as exhilarating the second time as the first. There had been a slight pause in conversation, but this time it passed perfectly naturally waiting for Lily to speak.

"Is that the only kind of underwear you have?"

As ever she asked it perfectly innocuously and we both looked down.

"No, I've a drawer full of the stuff upstairs." It was true as far as it went, over the years I'd acquired them from various sources and rarely threw any away. Largely because I only ever actually wore this style and the rest just hung around.

"Oh, right." She sounded mildly surprised by the answer, enough to look back at my face. I was a little offended as, although she was essentially correct, she'd only seen me undressed a few times. I needn't have been that predictable yet.

"Yeah, if you came, say, tomorrow, then you'd probably see another style."

I'd started the comment imagining I was making some semi-vague hypothetical statement, but as I was about halfway through I realised it was partly a slightly pathetic brag, and partly an indication I was planning to do this as often as possible. I'd tailed off into semi-silence by the end, but no doubt Lily heard everything. She waited a slight moment before replying.

"I'm not sure if I'll be here tomorrow."

"Oh, yeah, of course. I didn't mean." I paused, wondering how to restate things even slightly better. "I might exercise in the morning anyway, it was just." I tailed off again as I'd not really been faring much better. This time Lily replied immediately.

"You've got a pair you'd like me to see?"

That had not been what I was trying to say. I was still totally unsure both how much we were supposed to be trying to make this happen, and also how much we were supposed to actually say out loud.

"No, er, not particularly." My total lack of certainly was evident in every syllable.

"I suppose you could show me one now, if you liked." She glanced at the clock as cool as ever. "We should have the time."

I was still lost but I felt I just couldn't agree to that. I felt sick and conflicted, though, so I mostly stammered for a second or so before replying properly.

"I, er, I don't really have anything I want you to see, I don't think." I could already feel the disappointment but I knew I wasn't capable of anything else. Yet.

She shrugged, "OK."

I stood there, still feeling as much embarrassment and excitement as ever. I didn't want to leave but she was again acting as if our conversation was over. Her eyes left my body and strayed to her phone. I knew I could either choose to leave or be dismissed very shortly.

"Well, I should head upstairs and." I hoped the sentence didn't need to be finished, but of course Lily thought otherwise.

"Put some clothes on?"

"Yeah." After that I just headed out, no doubt still under observation.

I didn't see or speak to Lily again that day, and, although I did spend more than a little time imagining how my fashion show might have gone, none of my fantasies seemed the least bit realistic, so I wasn't even able to feel that disappointed.

My failure, if you could call it that, put some things in perspective. As exciting as what was happening with Lily was, I clearly didn't dare let it go any farther and that was a good thing really, so it was somewhat counterproductive of me to do it every time she came round. That was the way to go if I wanted to escalate things, when what I really wanted was just a little treat every now and again. I wasn't quite sure what the frequency needed to be, but it at least meant that tomorrow I should be on the bike in the morning.

I followed through, though by the time the next day came round I felt it was as much because it seemed extremely unlikely she would be there later, as because of my new tactic of moderation. Of course Lily confounded me again and the sound of the door opening filtered up to my office just after four o'clock. I was slightly pleased to realise that I still supported my decision, even despite the stirring in my groin as I wondered what she might be wearing. I resisted even the urge to find that out and continued working. I felt almost virtuous.

Lily came up after about an hour, I turned to greet her and resolved to act slightly reserved and not mention anything we'd done in the last few weeks. At first it seemed as if she had possibly decided something similar and it was a fairly quick and superficial chat, we'd even mentioned the weather.

"Well, I'll head back down."

"OK, Lily, see you again." It was a pretty standard goodbye for me.

"See you tomorrow, actually. I think I'll be coming round."

It was pretty unusual of her to tell me her plans out of the blue, but you'd never have guessed that from the way she said it. I somehow remembered my resolution and didn't react.

"Bye, then."

"Bye, Lily."

Of course, the mere possibility that she had been effectively asking me to shower for her the next day was more than enough to undermine all my thoughts from the previous twenty four hours. Even as I heard her leave a short while later I was already deciding exactly what different kind of underwear to have on.

It was tricky because, although I had been telling the truth and I did indeed have a drawer full of different styles, they weren't really all that different. They were just underwear I'd bought myself here and there or got as a present from an uninspired relative. There certainly wasn't much that would particularly impress an eighteen year old girl, nor, crucially, would be particularly more exciting for me to wear than the tight trunks she'd already seen me in.

In fact, the only pairs that had sprung to mind were some brightly coloured briefs I'd had to buy when I'd mispacked for a work conference several years back. They were all I could find in the hotel shop on short notice and I remembered them as pretty small and tight, though there was every chance they'd been abandoned at the room. As it was I found them after a bit of a rummage. They looked even smaller than I remembered. I had worn them at least once so maybe they'd been shrunk in the wash, or maybe I had just bought the wrong size. They looked like a boy's pair of speedos made out of thin bright orange fabric, and I quickly realised I didn't have the nerve to wear them for her.

In the end I decided on a pair of novelty Christmas underwear I must have got as a present at some point, with dancing Father Christmases all over. They were fabric and of the much looser style of boxer shorts, with a button fly. I didn't think they would be as revealing to wear but they were still underwear and should at least provide a talking point to keep me in the room. I made sure my work for the day was largely done and headed to the basement that afternoon with my now customary air of anticipation. Lily was as good as her word and arrived not long after four.

I decided to not bother with any preliminaries, just shouting a hello to Lily from the corridor as I passed, and telling her I'd see her in a minute. "OK, Mr Hill," was the reply and I was quickly upstairs. I'd already got out the novelty underwear and was soon pulling them on my otherwise naked body. They felt loose and I realised that my penis would be moving around beneath them, perhaps Lily would be getting a real show nonetheless. A jolt of excitement ran through me and I almost bounded down the stairs. As I headed into the kitchen I couldn't believe how almost normal this felt.

"Hi, Lily."

"Hi, Mr Hill."

This time I went with purpose and was soon standing where she could see all of me. As expected she looked down and I stood still for her, there was essentially no pretence any more.

She laughed, "it's only September."

"It gets earlier every year!" That got another chuckle out of her. She was wearing more or less the same she'd had on the other day and again looked great in a tight skirt, black stockings and an off white blouse. Her hair was down and it looked like she was wearing makeup.

"So, will I get to see a different pair every time now?" She was sounding almost teasing and it was the most blatant way yet that she'd acknowledged we were establishing a routine.

I shrugged, "maybe not every time."

"I guess I'll need to wait a while till I see the Easter Bunny ones."

"Yeah, of course."

We smiled at each other a little bit more but I was sad to realise the conversation was already petering out, perhaps novelty boxer shorts weren't quite the conversation piece I'd hoped for. As ever nothing too inspiring came to my head, and I was soon nodding towards the bathroom and Lily was switching focus elsewhere. Despite having just been again practically naked for her I couldn't help but feel mildly disappointed.

The feeling mostly dissipated, though, and I began to feel largely content. I had intended for things to stay at this level and become perhaps even more casual, and had really just got carried away by her comment. I began to enjoy the shower and the thought of Lily waiting for me on the other side of the door, and I lingered under the water quite a bit longer than I had in previous days. As I got out I was once again sporting what was close to a full erection. I idly dried myself, still thinking pleasant thoughts about Lily and her legs, and then picked up my novelty underwear.

I soon started to get a little less relaxed, however. While earlier these shorts had seemed more conservative, now my semi erection was tenting the front of them quite significantly they were anything but. My penis was using the extra room it had to lift them away from my body, meaning anyone looking could very well get an eyeful either up one of the legs or past the waistband, and my dick was even mildly threatening to slip out of the fly. Of course, given my previous daydreams about her, the idea that Lily could soon see me like this was at the forefront of my mind, which made it close to impossible to somehow think myself flaccid. If anything the situation was getting worse, and it was only the pressure exerted on my dick that prevented it from getting completely hard. It likely wouldn't stay that way for long, though.

Again I considered masturbating, but I still had the issue I'd thought of last time. What's more, I'd already been in there for a while and the shower had obviously stopped minutes ago. I didn't really know if it would occur to her or not, but the idea that Lily might figure out what I'd been up to didn't feel good at all. It felt seedy and against the fun spirit of how we'd interacted up to this point. It seemed like I needed to get out there and quickly, and of course a significant part of me was more than OK with Lily seeing my erection so blatantly. In the end I decided I would need to at least try to cover up with my towel, so taking a deep breath and keeping it close by I opened the door.

"That was a long one, Mr Hill."

Lily smiled at me as I nodded my agreement, by now feeling quite nervous. I found myself holding the towel hopefully casually at waist level not quite right in front of my still hard cock, but just to the side of me that Lily was sitting on. For now, at least, I think it blocked the worst of it, and, as I started to walk I found myself hunching forwards to lessen the uncomfortable pressure that the shorts were placing on my straining penis.

Although she hadn't yet figured out why, Lily clearly saw something was up.

"Are you OK?" It sounded like there was genuine mild concern in her voice as I passed her by. She turned her head to keep watching me.

"All fine." I shuffled on, I was now past her so if she stayed sat down then there was every chance I could get out without my predicament becoming obvious.

"Have you pulled a muscle or something, you're walking a bit funny."

"Yeah, that must be it." Feeling more comfortable now I was likely obscured by the breakfast bar I felt able to reply.

"Oh, you should let me give you a massage." I heard the sound of a stool moving, so I felt the need to speak again.

"No, no, that's fine, it's nothing really."

"Seriously, Mr Hill, it's no trouble. I'm trained, remember, my Mum's been teaching me for years. I've helped out friends lots of times."

From the sound of her voice she was now past the breakfast bar and was likely staring at my back. I'd paused just outside the kitchen door and was unsure how to handle things from here. What she'd said was true, I knew her mother was a massage therapist, my wife had even used her services a few times, and, although we'd never discussed it, it made sense that her daughter had picked up a thing or two. I turned my head back to her and made sure the towel was again near my groin on the side that she could perhaps see slightly.

"Oh, I know, but, it's alright." I was rambling partly because, of course, in reality I wanted nothing more than to be able to say yes please. "Besides, you don't have a massage table or anything, so, you know." I ended vaguely, waving my free hand and hoping it was enough to allow me to walk back upstairs.

She laughed as if I were being ridiculous. "That's no trouble, the bed or even the floor is just as good as a table." She started to walk towards me, "come on, I'll follow you up." She sounded so matter of fact I found myself turning and setting off ahead of her just to keep her from seeing my still throbbing erection.

I was now completely confused as to how I could get out of this situation, but also entirely uncertain that I wanted to. If I could somehow get the massage without her having to see how ridiculous I currently looked, that was surely the best outcome. Once again at the merest hint of something more my resolve to keep things from escalating had gone out of the window. As I approached my bedroom with Lily still following behind I, hopefully casually, wrapped the towel around me.

Lily followed me into the room, and if she felt at all uncomfortable at being in my and my wife's bedroom she didn't show it in the least. I stood to one side as she bustled past me and went over to the bed.

"Yeah, this looks fine." She pulled the duvet off quickly and straightened the sheet beneath. "I'll maybe put a few towels down." She smiled at me as she headed back to the door. "I bet Alice or Chloe will have something I can use for oil in the bathroom as well."

I smiled at her pointlessly as she went out, she didn't seem to look down so with the towel in place I think I was doing OK. I continued to just stand there, mind curiously blank. A large part of me wondered what on earth I was doing but I was clearly just going to do what Lily told me and hope for the best.

She came back a minute or two later carrying some towels and a couple of bottles of cosmetic products. She again smiled at me and walked past to the bed, where she put most of our pillows onto the floor, left one in place and then spread out two bath towels down the bed below it. Then she turned to me, still holding a third towel.

"OK, well then. I think we're ready." Her eyes flicked down seemingly noticing I was wearing my bath towel now for the first time. She frowned slightly.

"Are you, er, still wearing your shorts?"

"Yeah." I didn't know what exactly was supposed to happen next.

"Great, just take that towel off and come over here." It sounded like the simplest thing in the world. I felt my hand stray slowly to the towel knot, but I couldn't help but hesitate. Lily looked at me wondering what the issue was but I still hadn't figured out how to address my erection.

"Oh, right. Do you *want* to take your underwear off first?" She sounded surprised but also as if it might be an option. I was finding it very hard to get my brain in gear enough to usefully reply to anything she was saying.

"No, it's just."

She didn't wait for my spluttering to finish. "I guess it's fine if you do, I was going to use the towel to cover you anyway." She left almost no gap and then carried on. "I'll head out for a moment and you can get ready. Use this towel to cover up, that one you have on is all wet." She waved the third towel at me briefly then put it on the bed and quickly left the room.

At first I thought I was even deeper in trouble and wondered if I had the wherewithal to be able to speak up, but I then realised that at least her leaving the room gave me the opportunity to get into place unobserved. At that point I'd be lying on my front on top of my penis, so it should then be fairly safe and give me more opportunity to get things under control. I took off the towel and the shorts quickly, worrying that Lily might come back in when she thought I was ready rather than waiting for a signal.

My dick was at full strength as I climbed onto the bed and picked up the towel, which seemed to be a worryingly small one. I lay down trying to get it in place across my bum and I quickly remembered that lying on top of an erection is very uncomfortable, in fact it was actually painful if I wasn't careful. I reached down and tried to arrange myself as best as I could, and it seemed that pointing it down between my legs was the only position I could stand which let me lie flat. I worried it would be visible but I resolved to keep my legs together and thought that the towel should keep me just about covered. I waited a few moments, wiggling about slightly trying to get more comfortable, then, after another look back and a slight towel rearrangement I called out that I was ready. I heard the door open almost immediately.

"OK, Mr Hill, you just relax." I decided to not try and look up for fear of disturbing my careful arrangement, and I heard a pop of a bottle and then a cool feeling as liquid was poured onto my back. "It seemed like it was maybe your leg that was bothering you, but I'll give you the works."

"Thanks."

"Don't mention it."

She soon started and the sensations as she pretty expertly got to work were great. Although I couldn't see her, the idea of Lily in her sexy skirt caressing my now absolutely naked body was more than enough to keep my dick at least semi hard, despite it's still uncomfortable position. I gave myself over to the moment and tried not to worry too much.

After a little while her hands lifted off and I soon felt the liquid hitting my calves.

"I'll do your legs now."

Her hands soon started again, and although it wasn't quite as exciting as she worked my lower legs it was still a relaxing massage. When she moved up to my thighs, though, things got a lot more interesting. For a start after her first few strokes, which seemed to get higher and higher, I felt her hands lift off and my towel suddenly move.