The Adventures of Lily Crossguard

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A Brief Glimpse into the Life of Lily Crossguard

(Sexually speaking, that is)


Caleb couldn’t help to keep the – he knew – stupid grin off his face. Here she was, beneath him. Him!

Well, when he thought about it, it probably did make sense. Hell, he was a good-looking boy, and he had just about nothing but girlfriends. Spending all that time with all those girls you were bound to learn a thing or two about what makes ’em tick. What they need from a man. And just the amount of time he’d put in, one of them was bound to get with him eventually.

But only in his wildest dreams could he have imagined it would be Lily.

Shit … she was getting bored. Get her going, man.

A smile. She was smiling. She’s into it. Those lips. So full and pink.

Her hand came around to the back of his head. A chill ran down his spine as her fingers twirled and then grabbed hold of a fistful of his hair. He let her have the control as his lips were moved towards hers. She opened those luscious crescents and exposed her perfect shade of pink tongue. The tongue flicked against his aching, wanting lips.

This was really happening. He was going to have sex. Finally! Here in the barn. He was actually gonna roll around in the hay. Fuck. Stop thinking about it so much and just do it — use your hands for Christ’s sake.

Her hands released his head.

Man, she used a lot of tongue. That was one of the problems he’d found with all those other girls he’d kissed — never enough tongue.

Your hands for fucks sake! You’re both still fully fucking dressed. Get busy.

He leaned back, staring into her huge brown eyes, her little nose – those totally cute freckles that spread from her nose and filled out over her cheeks. Her full, not too curly, deep red hair. Her … Enough!

He let his left hand drop to her right thigh, which along with her left was now clamped against his sides. He dug his fingers into the soft flesh.

She’s moaning. She likes it. Of course she likes it. Nobody likes sex as much as Lily.

She likes it because you — are — the — man. Let her have it.

He slid his hand down, letting his fingertips slip under the hem of that summer dress she’d worn in almost every one of the fantasies he’d indulged in while his left hand would hammer away. Which was weird because he was actually right handed.

Damn it, just go for it!

His fingertips moved under the edge of the white panties, which she had lifted her blue dress in order to show off to him only some twenty minutes earlier.

Oh God, why can’t I stop thinking? I’m here now — with her. This was no fantasy.

“Take them off.”

That rasp in her voice making him even harder. He wasn’t a smoker but he couldn’t say that the taste of the inside of her mouth displeased him. She moaned again and he felt the soft mound he’d first glimpsed only twenty-one minutes before, as it pressed into his rock-hard cock. He felt it give at his hardness and he shivered again at this preview of things to come. He smiled — ‘things to come’.


He went for it. Both hands taking them at the sides and pulling them towards him. She moved her thighs up, away from his sides and effortlessly brought them together against her stomach, grinding her firm ass up along his pole as she went. She held her legs down with her left arm crossing over them, pulling her bent knees down making those huge, round … what were they — Double D’s, E’s? … spread and bulge out over the lip of her massive bra.

This time he didn’t let himself drift too far. A girl like Lily demanded action from her men. He pulled her panties up making a rolling dent in the light creamy coloured flesh.

There it is. Oh God. She’s hairless. His mind briefly blanked – hypnotised by the tightly clamped bulge of her light, creamy coloured slit, exposing only a hint of the wet, pink lips tucked neatly away inside. But only briefly.

If I was any kind of man I’d bend down and kiss it.

He didn’t, deciding it was probably best to get those increasingly more and more tangled panties completely off, before they cut off her circulation or something.


Lily knew now that she was going to have to take the lead on this situation. Should have known that from minute one, really. That terrified look in his eyes back in the kitchen. It was sweet. She hadn’t come here to throw poor Caleb a mercy fuck. Twenty years old and still a senior in high school. Still a virgin and still gonna be one tomorrow unless she actually manually pulled his dick out quickly and put it in before he came over her hand, most probably.

Still, Caleb was a sweet heart and actually not entirely un-cute. If he had just a bit more confidence. Maybe a few male friends. Someone to give him some bad advice. Something, anything that might give him even the slightest of edges. Then pendik escort definitely – he could totally have fucked some ugly fatty by now.

But as it was he didn’t, at all, and he could be more than a little weird at times.

I mean, right now he seems more focused on turning my panties into a Chinese-finger-lock than he is on my pussy. And it’s a nice little pussy.

She could see that drift happening again in his eyes. That shift when he started to wander. She couldn’t even pretend to guess at what must be going on up there.


Maybe I shouldn’t take them off completely. Lily’s an experienced kinky girl, maybe I should use them as some kind of make shift bondage rope for her ankles and … Save that kind of shit for your second fuck! This time round just focus on sticking your dick inside her. Oh fuck, I don’t have a condom. That’s it. It’s over. It’s never gonna get better than Lily and now it’s not going to happen.

Finally. He chucked the freed panties an aimed two meters along her sight line so as not to potentially annoy her into distraction with thoughts of having to find them in a hay filled barn when it came time to leave. Which was probably not going to be too long from now. Like trying to find a pair of white cotton panties in a hay stack.

God, those legs can spread.

Her feet were again planted to either side of him, but now with the inside of those creamy thighs aiming up. Should you ask before diving in to eat pussy? No, great lovers don’t ask, they take. They … Oh shit. Is she shifting back so she can get up? Shit, she is. Shit. Fuck! Fuck! Fuck! I’m gonna cry. Not now, but definitely later. Later I am going to have a serious cry.


Lily pushed herself up into a sitting position, elbows resting across her hiked-up knees. She was conscious of not letting her dress slide back down to cover her up. She didn’t want him to think this wasn’t going to happen. She wanted to let him know that she wanted him to look — though she wasn’t exactly sure he’d actually noticed this – but she knew she was going to have to do more than subtly take the lead on this one.

Not wanting the harshness of him coming on her hand when she yanked it out meant she was going to have to talk him through it. It was going to embarrass him into some pathetic macho posturing, but this was tough love. It wasn’t about being horny and taking advantage of a friend anymore. This was about helping him become … well, less of a fuck-wit. Also, talking him through it would help him have something to focus his mind on.

“Okay, Caleb. Now I don’t want you to panic.” He’s like a dear in the fucking headlights. “You are definitely going to lose your virginity tonight.”

There it was. The inevitable shift to that cool-guy-above-it-all look in his eyes. But it was a specific choice of word. If he was going to get through this he was going to have to completely surrender himself over to her.

“I’m not -” His voice was quaky, but it had dropped at least a full octave.

“Caleb. Don’t fuck with me and I’ll let you fuck me.” She reached behind herself and began to undo her bra. “Consider your response — very carefully.”

She pulled her arms in through the straps of her bra, making sure to not let her boobs come out completely from behind the curtain of her blue dress. She was going to make sure their grand entrance was a good one. With her bra free, she flung it somewhere behind herself. She was thinking about actually leaving it with him as a kind of trophy/memento to remember her by, but then she figured that having it might fuck him up even more. And it was expensive.

“I don’t have a condom.” His eyes drifted down sheepishly and seemed to catch that her nice little pussy was still staring up at him.

Ooh … that tingle was back. The one she’d first felt while sitting sidelong at the kitchen table. Without a thought, she had just opened her legs and pulled up her dress. Only came round to say goodbye to one of her closest friends before she left on the bus for LA – but with that click of the front door as his parents left for their party, her oven had well and truly been turned on.

Felt like a life time ago. She’d said: “Show me the barn.” — and now here they were, and she was going to get to play teacher.

“That’s okay, gorgeous. I’m on the pill and you’re obviously clean. Unless you’re worried about my hygiene?” She was going to break this tension.

He almost tripped over his tongue trying to reassure her that he had nothing but the firmest of confidence that she was as pure as the driven snow.

“No, I don’t think you’re a slut or anything. I …” Realisation. “Oh, God. No, I mean — I don’t care. I — I — I …”

She let him play it out, giving him the arched forward neck and full pupil exposure accompanied by an interested nod. Cruel, but funny.

He continued. “I — I — I …” He settled back taking a breath. “I mean, I trust you.” maltepe escort He’d saved it. She knew he could.

Lily smiled him her sweetest but genuine smile and leaned forward to kiss him softly on the lips. “You’re sweet.” He instantly seemed more relaxed than she’d ever seen him. This was going to be fun. Onto her knees and a quick ‘two step’ over.

“Give me your left hand. Seems like the one you favour.” He gave it to her. “Good boy.”

With her free hand, she then gathered her dress and pulled it up past what some dick head had once referred to as, her ‘child-baring hips’. Idiot. He hadn’t gotten laid that night. Truth was she loved her body. All of it. It was a nineteen-year-old hard body. Wide hips they were, but they curved into a tiny waist. Her black girl’s ass was as firm as a rock. Her legs were long, pushing her to an even 5.9, and her thighs were round and smooth.

And then of course, her tits. They got ninety percent of all attention thrown at her. They were big. Very big, but they were full and her tight nineteen-year-old skin pulled at them, making them dispute the very nature of gravity.

“Do you like my body, Caleb?”

His eyes and the slight spittle answered before he did. “I love your body. Your body is like something out of a thirteen-year-old boy’s fantasy.”

That was Caleb. Could always be relied on to say something really clever, if not always appropriate. But Lily quickly decided it was the best compliment she’d ever gotten.

“You want to be inside this body, don’t you?” She was pressing his palm against her inner thigh teasingly edging it upwards. He was nodding. His eyes now locked on her nice little pussy.

“I want you inside me. I want to feel you inside me.”

Lily leaned forward and licked him across his lips, pressing her tongue flat against them. His lips parted, his tongue drawn out towards hers. Hmm. She favoured him with a groan and then locked lips with his. Despite all his inadequacies, Caleb was actually a good little kisser. Their tongues dancing in time. Most guys were too weary of using their full tongues, but old Caleb here was giving it his all. With her guidance, she might even get some decent head.

As their dancing intensified she took hold of his hand and quickly guided it the rest of the way, making him palm her nice little pussy. His kissing became more forceful, but less good. More of a white guy dance now. He was losing his concentration. Good. She slid her fingers down between his knuckles, and then using her middle two she pressed and guided his middle and forefinger into her. That squelching sound.

“Wow.” He said mid-tongue dance.

Lily let out a gently laugh. “How does that feel?” With her fingers still in place she moved his in deeper.


A belly laugh exploded past her lips as she let her head rest on his shoulder — her own shuddering up and down as she tried to compose herself.

“Wow.” He said again. “You’re so tight.”

She got the shuddering under control. “You really know what to say to a girl.” She raised her eyes to meet his. “Go on Caleb.” She touched her wet lips to his. “Make me feel you.”

Guided for the first two strokes she then moved her fingers away from his. Lily almost always ran hot so gratification came quick for her. The flush of heat welled out from around his working fingers and spread down her thighs before blossoming up to fill her breasts. Closing her eyes, she felt her tongue independently glaze across her upper lip. Her hand, now free, quickly found her burning breasts, coming up under the left and letting it fill up her palm. The fire increased as her fingers dug into the pliable flesh through the clinging fabric of her favourite blue dress. She pushed up against its fair weight making it curve over the sides of her palm.

“Faster.” It came out as a hiss through her clenched teeth. He complied, picking up the pace. Her grip involuntarily loosened letting her breast slip down over her palm, her ever hardening nipple tracing a line down her inner wrist. It demanded more — both the girls did. Her eyes still closed, she grasped blindly for his right arm. Finding it she let her hand slide down to his.


My fingers are inside Lily Crossguard. I’m making Lily Crossguard wet. Dripping wet. It’s actually running down my hand. Oh, yes. She wants me to grab her tits. I think I’ve dreamed of this more than I have actually fucking her.

Her firm grip guided his eagerly twitching hand over to her two giant heaving tear drops. Then with more force than he would ever have dared, she pushed his spread hand deep into the flesh of one of her firm, round ‘mega melons’. Man, this is what heaven must feel like. He grabbed a respectable handful. He was gonna need bigger hands. Despite himself he shook it from side to side.


Cool. He increased the side to side jiggle. The force of the left sending a rippling wave through the right. Oh, wow.

“Your kartal escort other hand.” Her teeth more tightly clenched.

He complied, picking up the pace with his whacking off hand. Do I let it go? Her hand gripped hold of his ‘mega melon’ manipulator — (Not to pull it away, thank God) guiding it down. Finding the mark, she squeezed his thumb to the side of his hand, clamping her firm, hot nipple. Clamping it hard. She flinched, her spine involuntarily jerking her hips back — (Too hard). — Harder. Another shudder. Keeping his stride, he slipped his finger back in place. Faster. Her squeeze — Harder.


God, look at that. Caleb was licking his lips in time to Lily, lost in her expressions as her face fluidly shifted from slack to taught. From her licking her red top lip to bighting the plump bottom one.

She was like a Disney heroine. A Dirty one.


Forcing her spine to comply she angled her hips forward, deepening his thrust. The heat that now filled her whole body was seemingly trying to pin prick its way out of every inch of her skin.

“Oh, God. That’s good, Caleb.” She dropped her hand back down to the one in between her legs. Clumsily fumbling his fingers out, she then guided them to her little sailor. “Rub my clit. Fast and hard.”

He didn’t need to be told twice. That slick, smacking sound. She hadn’t been this wet in a good long time. A small ‘yelp’ came out instead of the exhalation planned. She let go of her gathered up dress and brought both her hands up to each breast. Ignoring that his right was covering the left she squeezed repeatedly at both — gripping her left through his hand. Another ‘yelp’. Her breath was being cut away, replaced by the short high sounds.

She could feel the toe nails of her bare feet digging into and pulling at the wooden hay covered floor.

His stoke was faltering. His overworked wrist clearly locking. She was so close. His left had had plenty of training for this moment — she knew he could take it. She was so close. He couldn’t be allowed to lose the rhythm now.

“Faster.” She based her voice to ensure the message got across. He powered through, giving her what she needed.

“Good — Caleb.”

Up — up — up — up … THEN.


Who the fuck? The third voice intrusion was instantly followed by the creak of the barn’s side door opening. Seconds short of the explosion, Caleb’s stroke stopped. Snapping her eyes open and slapping them onto the source, Lily was just in time to see Mr. Dudland stick his head past the obscuring open door to lay eyes on what she figured must have been quite the pride inducing spectacle.

“Oh, um, God. I’m sorry. I — I …”

Although frustrated at the stalled wave, pre-breaking, Lily still found pleasure in giving Dad a Devilish smile. His embarrassment, which should have been backing him out the door, was halted by the sight of her. Now particularly, her ass, which due to its firm, protruding roundness, was still mostly exposed — keeping the bunched-up dress at bay as it did.

“Dad!” Caleb’s octave range jumping in the other direction.

“Sorry. Sorry kids.” He backed out pulling the door with him. “We just came back because your mothers feeling … Uh — goodnight son.” The door clicked closed.

From the corner of her eye, Lily saw Caleb falling away from her and rolling onto his back.

“No — no — no — no …”

She turned back to him seeing his hands smothering his continued denial. This could potentially be a problem.

Yup. The unsubtle bulge at the front of his over worn blue jeans was sinking back into obscurity.

Here we go. Lily glided forward onto all fours and crawled over Caleb’s tense demeanour and eased herself down onto him. Face to face. The press of her breasts against his chest unfortunately failing to make the blood come rushing back, but she was undeterred. If there was one thing Lily loved, it was a challenge — and for her they were few and far between. It all just came too easy.

“Caleb.” The last syllable lilting up into a faux-musical query. His muffle diatribe continued. The new list of words lost to her.

“Caleb.” The teacher in her now back.

She eased his hands away from his face. His lines of despair had stopped but his eyes were trying to find something to lock on off to the side.

“This isn’t over. You and I are not finished yet.”

His eyes were still searching for answers over by the pitch forks and hoes. “I’m sorry Lily. I don’t see him coming back in action tonight.”

“Hey.” She took hold of his chin and made him look her in the eye. “I told you that you were going to lose your cherry tonight and by God I intend to be the one to take it away from you.”

“My Dad -“

“So your Dad saw us. What’s he gonna do? Other than give you an embarrassing wink in the morning.” His tension seemed to wane.

Then he went searching again. “Ah! It’s just too weird. I can’t shake his face from my head.”

She brought her knees up to her side and planted both hands onto his chest to push herself up into that all too familiar position. She played a brief drum beat on his chest. He actually had a nice chest. Farm boy body.

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