The Liliad/Liliad Thread 1

Story time!

ITT: feels, hope you do not need to forever alone, anon loses his virginity.

This tale starts just over a decade ago. Today I am a 25-year-old semi-basement dweller, but once upon a time I was a 14-year-old total basement dweller. My human contact was limited to people I spoke to through AOL and those people I accidentally bumped into in school hallways. My father's business partner had a daughter who was my age, and in a desperate attempt to keep their son from going full-disappoint on them, my parents did everything to get us together.

This resulted in me helping her set up her family's computer and install an instant messaging program. We started talking every now and then, but still never acknowledged each other in person. She was my first real "friend" in my teenage years despite not being a friend at all. Predictably I fell in love with her, but she didn't notice/care. ;_;

So time passes, after about six months of online talking I got invited to her place for a movie. Exciting! This was almost definitely set up by our parents, but I still went along with it, as being a beta loser fag wasn't something I'd totally accepted yet.

At her home we settled on the couch while her parents fled to give us 'space'. She didn't pay much attention to me, just silently watched the movie. After some time her little sister joined us, and the two of them talked a bit. it was awkward. as. fuck. To the extent that I remember it today. I got the hell out of there as fast as I could.

Within a couple months they moved to another country. Oh well the end.

Just kidding, not the end. After they moved we continued to talk online, though looking back I guess I sort of noticed a personality shift. Maybe it was from being somewhere new, but she appeared to be more excited to talk to me and more interested in me. As my interests barely extended past pokemon and somethingawful I did my best to keep up with her cultural references. After a while she was really warming up to me and making me feel like I was worth something. Yes...all this happened in the warm glow of a computer screen, but it still felt very real to a skinny loser. I was happy.

It had been about a year and a half since we were 'set up', and I was still in love with her, though of course I said nothing about it. My father planned a trip to head out to their home to check on the company out there -- I hopped on that trip as fast as I could. We were going to meet face to face for the first time in nine months or so and I stupidly hoped that maybe...well, whatever.

When we arrived it was clear my social circle was going to be small. I don't speak Spanish (uh oh, now you can narrow down their location!) and was limited basically to expats. Which, in this area, was basically my 'friend', her sister, and her parents.

The plane ride was interminable, it felt like it took days. I was so nervous -- I'd even stupidly bought her a gift in the airport, some stupid Americana tchotchke that I thought would remind her of home.

Our first evening was going to be spent having dinner with the family. I was pumped, sort of, in the way that makes you feel like you're going to shit yourself. We'd been talking like old friends for months, about everything.

(It may seem like I'm leaving out something essential here. It'll be clearer soon.)


Her mother opened the door of their nice home in a gated community. As I stepped in, I looked all around, seeing only her sister and mother, not her, practically dripping sweat. The gift seemed incredibly stupid now as I held it in quavering hands.

She didn't show up until dinner. As we ate, she barely looked at me, didn't speak to me at all. I was horrified, what the fuck was going on? When we finished eating I managed to corner her in the kitchen.

"Hey." She just looked at me. I probably blathered for a bit, but then I said: "I've really liked talking to you."

She looked taken aback.

"I haven't been talking to you."

My heart sank approximately as low as the deep web.

That shut me up. The night ended extremely uncomfortably. I couldn't look at her, and ended p giving the gift to her mother, which came across as 'adorable', just the thing a 15-year-old wants to hear. My eyes didn't leave the floor. We've all had that feeling - shaky bowels, face red and pounding, palms sweaty as fuck. I felt tricked and stupid.

(Fortunately 4chan had just been launched, so I was able to go and hang out with my new best friends that night!)

The trip lasted a few more days. I found ways to not have to go to their home except for another uncomfortable meal.

I'd been really stupid. This girl didn't care about me, I was just a forever alone waiting to happen. When we got back home to the good old UNITED STATES OF AMERICA, seeing her username online made me well up with anger. What the fuck was her problem? My anger was palpable as I demanded that she explain herself. Why did she say she wasn't talking to me when we were talking at that moment??

"this is lily."

I probably stared at that sentence for five minutes before shutting the computer off.

Oh, right. An explanation.

Lily was my "friend"'s 11 year old sister.

The hell?

I swore to never use the internet again. I had been tricked by a little kid and it felt horrible, especially considering the sort of emotional things I had been talking to her about. Oh god, the way she had looked at me during our meals, the fact that she had met me at the door, it started to make sense, and it wasn't good.

But don't forget who the main character here is - a hormonal baby /b/-tard. We see where this is going. Hang on. By some miracle I did manage to stay away from the computer for a solid day or two. A feat of mental strength I've yet to match. And when I did get back on it, I saw her username flash green and immediately signed off every time.

My masturbatory fantasies got confusing. I was attracted to the girl who was my age - she had boobs, good looks, and all that. Mostly the boobs. But then, her sister was the one...who... It was weird.

One time I wasn't fast enough, either I wasn't at the computer or she was invisible or something, who knows. But she got a message onto my screen - "I'm sorry."

Immediate sign off. But I didn't block her. Even if my one 'friend' wasn't who I thought she was, I didn't want to think about not having any friends at all. So we kept playing AOL hide-and-seek.


Over time I started to transfer some of my feelings. I did like the girl I had been talking to. She was fun, and even managed to talk about which water type pokemon was best. If I managed to scrub out her age from my mind, or all my memories of her as the annoying pest ruining all my fun, she was kind of an okay friend. This was all internal, mind you - I still refused to speak to her.

But the walls started to come down. She literally lived a continent away. It wasn't like she could come get me, or shame me to my school, where I continued to live my completely invisible, friend-less life.

Well...being friends with her wasn't SO BAD. Was it?

No need to play it cool for much longer. We started talking again. Mostly it was me berating her. Why the fuck did she do this? Why did she trick me? This was utterly uncool. Did she tell anyone about it? Did she talk to anyone about the anxiety issues I discussed with her? How the fuck was an eleven-year-old even handling me?

She told me her sister stopped using that account after they moved, it had been her since then. She said she liked talking to me. She said I was cool.

We all know I wasn't and am not currently cool. Doesn't change the fact that it feels nice to be told you are cool.

My romantic feelings had no idea where to go. I was not 'into' her like that, she was a kid as far as I was concerned.

Our friendship became my biggest secret. An online relationship with a little girl would likely be the final straw my reputation needed to be decimated forever.

We kept talking. It was probably another eight months of talking before the next major development happened. Almost daily chats with her, getting intimate about our personal lives (not like that you pervert), our emotions, everything. She knew more about me than anyone else. I guess it was because she was just a name on a screen, not really a real person. Lily was so far away, she could not hurt me. It was a perfect situation, sort of. Except the part where she was an 11yo girl. Other than that.

I remember posting about this exact thing briefly on /b/, in a topic that died rapidly. I asked if it was weird to have a best friend who was several years younger than you that you only talk to online. 99% of the replies reminded me that girls do not use the internet. A fair point.

Obviously, my dad had to go back down there eventually. When he told me I'd be accompanying him again, to 'broaden my horizons' and/or 'make him hope his son wasn't a broken human being', I fought it slightly before lying away in my bed every night, terrified of the meeting I knew was coming. When the plane touched down and I knew I was physically closer to Lily than I had been in a year, I put a smile on my face and tried to stop my nonstop nervous farting.

Seeing her this time was going to be completely different. Lily had been window dressing for the scenes of my life before this moment, now she was suddenly a main player.


Dinner at their home. An almost exact repeat of the situation a year previous. Her mother opened the door. Lily was standing a few paces behind her.

An important sidebar now:

Lily at 12.

Lily's mother is Asian, her father is 100% WASP. She picked up the best of all presented DNA and was wearing it proudly. She had almond-shaped eyes, full cheeks with deep dimples, and the most incredible skin I'd ever seen -- ivory white, smooth, blemish-free (unlike me at 16, let me tell you). She was short still, while I was horrifically tall, and comparing between the two of us was another reminder. It was winter and she was wearing a sweater, with obvious lumps of breasts underneath that my kinda adolescent mind was immediately trying to dissect - how much was real? how much was bra? was there a bra? etc. You know the drill, you did it too.

One thing I like in a girl is nice hair. Lily had luxurious, slightly curly black hair that she wore pulled back into a pony tail. It gleamed in the light.

She looked good, anon. A kid, mostly, but moving towards something more than a kid.

By the time we sat down for dinner I had the most confusing erection. (a fun reminder that my previous 'friend' was now basically invisible to me, I assume she was there too but for the life of me I can't place her in any of these memories)

I managed to talk through dry lips, probably lots of gross smacking as I tried to get my parched mouth to produce normal speech instead of just grunts and creaky sighs. I had been talking to Lily online for over a year - or just under a year since she told me who she was. She was probably my closest friend.

Every now and then we caught one another's eye, during dinner and during washing up afterwards. It was always followed by a swift look away, sometimes a slight smile (though I convinced myself I imagined this).

It took one night for me to decide she was definitely cute. I considered the wait - what age was acceptable? 14? 16? A couple years... It seemed doable. Emotionally I was probably still an eight-year-old, so it wasn't that bad, right? The justifications were so easy and started to come fast and furious (just like me later as I thought about Lily taking off her sweater - the first time I'd actually masturbated to the thought of her, leaving me wondering if I was in fact a goddamn gross dirty pedo bastard). She knew my birthday was coming up. Our in-person talks were severely limited, as we were never alone and I was usually off getting into the "family business" (import/export is the dullest thing in the world, in case you were curious). But she managed to find a moment to slip me a small gift, telling me to open it on my actual birthday.

I had started noticing her outfits every day, started noticing her as a girl and not just a kid. But...it was confusing. I was on /b/ enough to know what pedos were like and what they were into, and while I was into her, sort of, it wasn't like that. Was it? The mental struggle was starting to consume me as I entered a cycle of jacking off/shaming myself/repeating for infinity.

On the day we left, I passed around handshakes and hugs. When it came to Lily, she put her arms all the way around me, pushing her head into my chest, bumps of breasts in my stomach. I wondered if I imagined she was shaking as she did so, but when she pulled away I saw her eyes shining. She was...sad. Despite our interaction being far more limited than usual, she didn't want me to go.

My own tears started to well up on the plane. When would I see her again? Another year? Longer?

I ached for her. It was weird.

Was I. Did I. I couldn't figure it out. It was a weird feeling. I was way too old to be into a girl of that age, halfway through my junior year in high school was not the ideal time to decide to be into a preteen. But I did sort of like her but also I didn't but also oh god what was I going to do.

The pedos of /b/ had basically normalized it in my mind, what with the constant rounds of loli and pizza being circulated in the early days of /b/. But just because it worked for them didn't mean it was going to for me.

Anyway let's get this plot to progress. Upon arrival home we went right back to how we had been, complete with daily chats and constant intrusive thoughts. She was becoming way too important to me, really my only friend outside the other total losers at school who I managed to eat with.

Moving Forward

My father wanted me to get into the family business. Applying for college was on the near horizon, and getting some good experience was smart. So I worked at his office some, it was boring as fuck though I managed to upgrade the IT system from butt to slightly-less-butt which made me feel useful.

When he suggested I go do an international internship with his partner down in the country they were working with, I leapt at the chance. Not only to get great experience and to be in a different culture, but also to, um, well. To see Lily. I wanted to see her and I knew that working with her Dad would mean a pretty constant access stream. The awkwardness of an online friendship taken real-life wouldn't last for long, would it? I was 17 and she was 12 and a half and seeing her was all that was in my mind as I prepared for the move, packing, talking with her, brushing up on my Spanish through her help, though she found my sad attempts hilarious. It had only been six months since I'd left her the last time and suddenly I was heading back. This was far sooner than I had anticipated, but hey, I wasn't going to explain.

Oh god, the sight I was in for. Summer time in south america means lots of immodest clothing and Lily was no exception when the family arrived to meet me at the airport. Her tank top, with spaghetti straps revealing her rounded, narrow shoulders, was burned into my head the moment I saw it. I probably stared at her throughout the airport greeting. We shared a brief, awkward hug - again with me trying not to be so aware of her size compared to mine and the way she felt in my arms. This was a cute girl - or a hot girl? - and she wasn't into me like that. She wasn't. Couldn't be.

Work started. It was boring but profitable. Look, none of us care about that shit. Sadly I was not staying in their home with them. The my-age girl seemed opposed to the idea, implying that they were just setting up some sort of rape fest by putting me in the same house as her. But I was nearby, with coworkers who had a son slightly older than me. It was cool, if difficult as I tried to habla some espanol (I still can't).

But I got to go over frequently, for meals, social events, etc. It was always Lily and her mother, sometimes her father and rarely her sister, that would take me out to do things (either through a sense of pity or my father paying them, who knows).

I still had access to a computer. So did Lily.

"This is so awkward to say."

"what?"

"Its dumb, really."

"Lol just say it?"

"I think I kind of like you."

When I typed it, and I am sure I said it far less eloquently like that, it felt like I was just whipping my dick out there for a car to run over. But I had to say it, the summer was a third over and soon I'd be gone and it'd never be the same. Never. Thank goodness that I was still that dumb the summer before senior year.

"Ok." "....sorry..." "we should talk in person."

I popped as many boners as loli-chan inspired with her swimsuit series. Soon we moved on to talk about other things. But there it was - we were going to talk about it.

Trying to find alone time with Lily was a near-impossible feat. But we did find it eventually, with her sister away and parents watching a movie while the two of us carefully orchestrated some time where she was supposed to be on the phone while I was leaving. Instead, we sat in their kitchen. Lily was up on the counter, legs dangling, her short-shorts showing off elongating legs with that same incredible ivory skin, smooth and seemingly endless. I tried not to stare for too long at one part of her, but staring was becoming impossible. I was into this girl, no way around it. Fuck. I had become a pedo.

"Anon. It isn't a big deal." She said it lightly while I heard my heart pounding.

"It kind of is."

"Why do you think I talk to you? We've been talking for more than a year."

"You're being nice. You're my friend."

"Oh my god. Obviously I like you."

Fortunately she had a social IQ of >5, managing to beat me by a minimum of 4. I couldn't believe it. My heart went from sinking to leaping, and my dick did much the same. Holy shit she liked me oh my god this was real a girl liked me /b/ was wrong.

We agreed we could mutually like each other before a creak from upstairs sent me scurrying back from whence I came. Finding another slot of alone time with her suddenly became top priority, as did finding out what things girls like and researching how to not be a complete beta.

Of course all this frantic excitement was tempered by her age. And the fact that if anyone ever found out any of this, it'd be the end of me. Fortunately I was thinking not with my brain, so this hardly stopped me.

She asked me if I'd ever kissed a girl. I said no. I asked her if she'd ever had a boyfriend. She said yes, but then qualified that it was in fourth grade. She asked me what made me like her. I answered honestly, describing her personality and what drew me to it, leaving bits about her body -- her skin and hair -- for the end, trying not to appear too shallow. She asked me if I would kiss her.

This was two days after the mutual confession of attraction. Saying you like someone is a long way from kissing them. But I said yeah - I wanted to kiss her, and I would given the chance.

She said she was way too short for me to kiss. I said we'd find a way.

The next arrangement of private time took a couple weeks, but it was finally upon us. I all but had an aneurysm when we finally worked it out - her parents were away, and I could go to her room if we stayed quiet and avoided her sister. A stupid plan, but I was willing to do anything.

Oh god. Her room was a reminder of how fucked up I was being -- it had stuffed animals in it and even a poster of some Latin heartthrob. But Lily was there too, and she made everything else pale.

We talked for maybe ten seconds, me in her desk chair, her on her bed. Then she pounced at me.

I'll always remember her outfit - a pair of black exercise shorts with a horse t-shirt. Her hair was in a ponytail. Her feet were bare. The straps of her bra were slightly visible protruding under the thin shirt, and soon easily felt as my hands went around her back.

captcha: age

Her arms rested on my shoulders, legs splayed to either side of mine as I scrambled to adjust the sudden olympic-size boner that had reacted to this - likely the first amorous touch I'd ever received from a girl.

"Hey."

Her voice was husky, sexy even, way more than it should have been for a girl her age. I wondered how many TV shows she had watched to create this moment. Actually - that's a lie - I only thought about how light she was in my lap, how close our faces were, how her shy smile made those magnificent dimples appear.

"Hey."

I responded in kind. My voice was probably shaking, and I definitely whispered it as I was terrified of being walked in on. The thought of her age, of this being wrong - it was all gone.

This was my big chance to not be a beta faggot and I took it.

I leaned my head in and kissed her.

Her lips met mine as she moved forward as well. This was my first kiss, hers too, and my god I immediately knew why people liked to kiss. Her lips were so incredibly soft and warm, more than I had imagined. Her hands came around my neck, clasping together, holding me there, our lips moving slightly, mostly mine as I tried to...feel her mouth with my own, the idea of tongue seeming miles away at that moment.

After a solid thirty seconds, maybe less, maybe an infinity more, we pulled away and I smiled at her. Her cheeks were flaming red, I assume mine were as well.

"Wow."

That was me.

She didn't bother talking. She leaned in for more. I think my hand was probably shaking when I moved it up to her head as our lips pressed against one another. Her hair was so soft, so smooth, and her head felt so small beneath my massive apeman palm. I stroked her head kind of awkwardly as we kissed before deciding that was weird and moving my hands around her back, hugging her into me as I pulled away again for a breath. Her face hovered an inch from mine as she grinned, this time a full toothy grin, seemingly very pleased with herself and the moment. Or something like that. I tried not to read into it very far. Her breasts pressing against my chest were almost the last straw, and when she rocked her hips to bring them almost against mine, I am sure she must have felt the trident I was wielding between my legs.

I decided - fuck it - might as well try. When I leaned in for the next kiss, still no words spoken, I pressed my tongue gently against her lips. As this had JUST been my first kiss I obviously had no clue what I was doing, but her mouth tentatively opened, and I felt her own tongue meet mine, and suddenly they were swirling together, our mouths moving against one another's in an incredibly more intimate way, my hand now back in her hair, holding the back of her head as we moved against one another.

Holy fuck. I am seriously about to ejaculate just at this memory. It was fucking incredible - whatever you are imagining, multiply it by two.

We continued kissing like this for ten, maybe fifteen minutes. No words, just smiles, breaths, gasps, and two insistent, horny kids trying to get as much out of the other as possible.

The idea of going further was out of the question. That would have been crossing a line. And I at least knew I could make some sort of stand there.

We kissed and kissed.

Look, it is great. I realize being 17 and having a "never been kissed" moment is the ultimate in faggotry, but it was worth waiting all that time for this. It really was. We knew I'd be missed soon. We knew we were tempting fate with her sister in the house.

We pulled away from one another regretfully. When she got off my laugh I almost felt like I could cry. I wanted her there, permanently. Any moral qualms were gone, now it was all about Lily, this girl, whom I suddenly saw as so much more than I ever had before.

"I like you." I think I probably said it first, pathetically. She smiled, lips slightly swollen from all of our fun, glistening with our combined saliva. "I like you too."

I snuck back out and likely masturbated twelve times, once for each year of her life, within the following hour.

Going into work the next day, it took everything I had not to scream in my boss' face that I had made out with his daughter the previous night. I felt like I was on top of the world and nothing bad could happen. Planning our next meet-up was on the top of my to-do list.

We talked that night. She said she had really liked our time together. I said I had too. I said I hoped it'd happen again soon and she agreed. Oh my goddamn - this girl wanted me too. This had to be a bizarro fantasy dream world, not real life. But the memory of holding Lily was all-too-real.

She was soon my sole masturbatory fantasy. I only wanted her, all the time and everywhere. Only Lily. I definitely reached some level of obsession, and it probably showed when I had dinner with them, desperately trying not to leer at her (she played it incredibly cool every single time, obviously far more mature than I). I just wanted to run into a closet with her briefly, meet her in the bathroom, do anything. I mostly managed to keep this to myself - but in our chats she revealed much the same desire.

It took a couple weeks, but we made it happen again. Back in her room, her in the exact same outfit though this time with her hair down. Me in her chair. Her on my lap. Our faces pressed together, kissing like we needed it to live. Later in a conversation she decided this meant she was my girlfriend. I was fine with this, totally abandoning whatever worries I had had about this situation before. Fuck it, if I got to keep kissing her I was willing to do and say just about anything.

I had a month and a half left before I had to go, and I planned on making the most of it. The desire to take her on a date was strong but ridiculous, there was no way I could get away with that. The desire to go public was barely-kinda there, mostly to shove it in my friend's faces but as I had no friends and they would just call me a pedo I mostly ignored it.

But the desire to go further. Well, everyone who was ever male knows what that desire is like. How far was Lily willing to go with me? How far was I willing to go with her? Kissing was great - that must mean the 'rest' was even better.

I bought condoms, sort of on a whim. After all...I had a girlfriend now. We managed to meet up and kiss one more time before reaching the end of my tenure in south america. It was a sad time, mostly punctuated with me realizing I would do anything to have her around me and her trying to act as if she didn't care while doing everything she could to empty out her house for me to come over. Despite being a 'kid', Lily had some brains and I respected that about her.

I asked her about more in one conversation late at night. She said she wasn't sure, but since I was her boyfriend maybe we could try 'lying down and kissing'. This seemed like basically permission to go ahead with anything, so I agreed that some lie-down kissing would be next on the 'agenda' when I got to her home. The thought of lying on her bed, stuffed animals looking at us while I defiled their owner... Well, let's just say that it was no longer morally gross but rather incredibly hot. She wasn't a kid - she was my girlfriend, albeit a slightly young one. And one that would destroy my life were our relationship to become public. Still, though, my girlfriend.

It was getting down to the wire. Her parents were staying home almost every evening and I was actually doing some things at work. We were down to just over a week together and had only met up and kissed three times, zero times since we had decided to try it out lying down. I knew I was not going home without that attempt 'in the bag', no matter what it took.

Finally, Lily realized her parents were definitely going nowhere before I left. We had to come up with an alternate.

She was a good girl, not one for lying, so I knew her parents would believe anything she said. I told her to tell them she was going to a sleepover with school friends - her father was busy enough to not check and her mother's spanish was shit, so it might just be enough.

They went for it.

Meeting at mine was a no, so we decided to meet at the park just outside their community. It was decent, no homeless people and barely any AIDS. She came in a skirt, and my near-constant erection grew three times its normal size when I saw her. Lily looked incredible, like the first time I saw her in 'that way'. She was wearing a bra, as usual, I figured in order to make her breasts look slightly larger. Her skirt was dangerously short, so that with each step I wondered if there was a chance of seeing her panties. All in all, she was everything I desired. Everything.

We walked hand in hand for the first time, her small digits clasped tightly around mine, actually parading around like a couple, ignoring the danger of someone who knew either of us seeing us, wandering deeper into a more secluded area of the park. I don't know exactly what she was planning, but I knew what I was planning. And after all - we hadn't ever been able to keep our hands off each other before, so I was sure this would be no different.

There was no one on the path. There were ample bushes and the like to prevent an easy vantage point - we ducked off the path and found a clearing that seemed shaped just for us, Lily trailing slightly behind, my hand unable to let hers go. We lay down simultaneously, me pulling her next to me, lying on our hips and facing one another as I began to press my face insistently into hers, tongue tasting that mild sweetness, her own smaller mouth twisting around mine, kissing me hard, deep, almost frantically. This position was uncomfortable, of course, and after a few moments I rolled onto my back, with Lily coming atop me, one leg over my torso, entire body pressed onto mine as we continued to kiss, my hands up and down her back, on her head, brushing her cheek, touching her everywhere. Or at least everywhere 'safe'.

After a few more moments I rolled over onto her, supporting myself above her, not quite fully atop her, legs still to the side. We kissed like that now - her hands on my cheeks, daintier kissing, more loving, less animalistic. Then I shifted so I was fully on top of her, her legs spreading as my hips went on top of hers in line, my erection pressing into her abdomen without me even bothering to try and hide it. I pressed myself into her, feeling another human against my dick for the first time, her kisses faltering, stopping, and both of us freezing in the moment. The rushing sound in my ears was strange, perhaps just wind, perhaps something past excitement. I looked down at me pushing against her, pressing her skirt further between her legs.

"Um. I have a condom."

It was approximately that smooth, i.e. not smooth at all. She looked at me strangely for a moment.

"I haven't had my period yet."

Oh jesus christ. How old was this girl again? And was that permission? What now, did I just grab her breasts and go to town, or something else or, or, or... My mind was having a hard time getting around it.

But my cock had a mind of its own. I reached down to her sides, beneath her skirt, feeling her thighs for the first time as I reached to her panties and tugged at them, Lily lifting her hips slightly to let them slide down before she sat up a little to pull them down while I sat up and looked down at her.

Now, that was permission, right? It had to be. She lay back down and flipped up her skirt. I immediately spaghetti everywere. It was my first in-person pussy and it did not let me down. I am unsure what else to say about it, except that just as every other part of Lily was perfect, she was perfect there as well.

And no, there was not any hair.

If I had been better at the sex maybe I would have done more, but as it was I just let out a shuddering gasp and told her she was beautiful. Being a gentleman I asked if she was sure as I scrabbled at my belt, trying to get every stitch off as quickly as possible.

Her eyes may have widened when my boenr sprang into view, who knows. I was overwhelmed, too overwhelmed to pay much attention past this moment. I moved downwards again, on top of her, pressing myself between her legs.

I could feel the head of my penis press into something warm and soft. That was good enough for me, and I let out another groan as I pushed ever so gently against her. Surprise! Sex doesn't quite work like that, especially when you're dealing with some unripe goods. I slipped up and out of her on that first push - I could feel my cock pushing before popping upwards, smearing sticky liquid on her as I pulled back for another go. I reached my hand down to hold myself against her before looking at Lily - my darling, my everything, all I wanted in that moment. "Are you okay?"

"Yeah." She breathed. Her chest was rising and falling. Perhaps losing her virginity in a park to a guy five years older than her hadn't been her plan. But... Here we were.

I positioned, this time felt her labia spread around me, tightly squeezing the tip of my cock. This had to be right. I went even slower, pushing so gently, feeling a slight give, that incredibly tight, hot grip fighting against my entry into her.

It felt like my cock was going to break in half before it finally popped out again, this time bending downwards to press lengthwise almost into the ground. This was not right and I couldn't really handle much more. Lily was taking deeper breaths, her face red. "I can't really..." I muttered, looking downwards, our bodies blocking us and finding myself unwilling to pull back for a better luck, just wanting to feel her against me.

I pulled back and pressed against her, not bothering to position, feeling the underside of my penis slide wetly up her pussy. I pressed against her, a slight give in the puffy flesh down there providing me with even more stimulation. I rocked against her several more times - who am I kidding, probably once more, before I groaned, this time much more urgently. Leaning my body upwards and away from her I came, shooting white streaks up onto her shirt, leaving dark stains that in the moment didn't seem to matter. The sheer amount - and distance - was nothing like my solo experiences, and I was shocked at first before seeing her mild revulsion at the one shot that landed on her collarbone. "Sorry...sorry sorry!" I tried to wipe it up, using my own shirt, spreading it around, getting jizz essentially everywhere. I backed off of her, knees shaking.

"Oh my god, Lily."

Then I came back to her, on top of her, not caring about spreading stains on both of our clothing now as I kissed her, pulling back to say it -- "I love you." Getting back to her house was tricky but we managed it without making it too obvious to anyone that I had just ejaculated all over her outfit.

We had kissed more, lain together, whispered that we loved one another and would do anything for each other before finally deciding it had been long enough. She had always planned on telling her parents the sleepover was cancelled, I guess staying over at mine was never an option (ha).

I sat in my room after all was said and done.

I had just gone from debating whether or not like a 12 year old made me a pedo to cumming on one within the span of eight months. Holy hell.

And I knew one thing - that time didn't count, and it definitely wasn't very fun for her. There would be a second time - way better for her, and this time neither of us leaving as virgins.

But plans are all well and good until time comes to an end.

Soon it was time for me to go. We weren't talking online nearly as much, which I obsessed over, but when we did she seemed to mostly wonder if I had actually enjoyed my time with her as 'it wasn't real sex'. Apparently without full-on penetration she didn't think the guy could like it -- I guess her online education included plenty of porn or she was just smart. I assured her I loved it, and her, and nothing would change that. She asked if we could do it again, but this time somewhere nicer. I promised her we would, and this time wherever she wanted.

Other than that we talked about normal things. Missing one another. How we'd stay in touch. Whether or not Zelda has a goddamn victim complex. Just everyday stuff.

When I knew I was getting on a plane the next day, the regrets kicked in. I could've snuck into her house, could have done any number of things. This was it! It was over! Fuck! She was feeling it too, as evidenced in our anguished IMs. Lily was afraid about me forgetting her, not caring about her, going back to my nice life and leaving her behind -- the 'little kid' as she actually referred to herself.

I told her there was no way. I said she was mine, my everything, my first for all we had done together. I could never move past her. I'd wait for as long as it took us to see each other again.

On the way to the airport Lily cried broken-heartedly, not bothering to hide it. Her parents commented that we were good pals. I said yes, telling Lily to cheer up, we'd see each other again.

(the sheer craziness of looking a parent in the eye when you know they washed your semen off their daughter's clothing is...hard to explain)

I got on the plane.

I cried too. Tears that were very different from the last time. Now I was in love, and aching for Lily. My Lily.

(The fact that what happened made me a quasi-pedophile was...conveniently left out by my subconscious, which was kind of it)

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