Lilly d'Flower

Author's Note: I don't write this fandom and I'm not sure what came over me that I wrote this out. I haven't written a full on HET story in years either. Anyway, I thought someone might enjoy this and who am I to deprive?

This is a rough draft un-beta'd one shot.


After high school Miley and Lilly had gone their separate ways. At least during the school year. Lilly had gone off to college and Miley had resumed being Hannah Montana on a more than full time basis. She did plan on going to college someday, but wanted to wait until her career died down a bit on it’s own.

But during the summer the two friends planned to go home and see each other again. Miley’s plane had been running late, and Lilly arrived at the house on time to wait for her.

She carried her sleeping bag with her along with a bag full of reinforcements for the night. Miley and her had managed to remain virgins to this day, neither finding a boy they trusted enough to experience sex with for the first time.

Lilly’s bag consisted of, among other things, a few porn magazines and a movie. Both girls decided to do a little investigated prior to making any leaps n that direction.

When Lilly knocked on the door it was Miley’s dad, Robby who answered.

“Well hey, Lilly,” Robby said. “It’s good to see you.”

Lilly gave him a big hug.

”Miley won’t be home for another couple hours though. Her plane’s late.”

“Oh,” Lilly frowned.

“But you can come in and wait for her if you want,” Robby offered standing aside to let her in.

“Well,” Lilly seemed to think of it. “If you don’t mind, then don’t mind it If I do.”

She smiled and made her way inside. Robby closed the door before heading back in.

“I was just watching the NASCAR races,” he said.

Lilly looked at the TV and saw the cars seeming to fly by.

“I can watch with you then,” she said.

“Sure,” he replied. “You want a drink or something? I got some water, and OJ, and soda…”

“OJ sounds good,” she said. She took off the bags on her shoulder and dropped them to the floor by the sofa. To her horror the contents started flying out of the messenger bag.

“Oh, I’ll get that,” Robby started to reach down to get the things from the floor.

Lilly tried to fling herself to stop him or to at least pick up the dirty magazines herself, but it was too late. Robby had already picked up and turned over the magazine “Stud Muffin” with the half-naked guy on the cover with a cowboy hat.

Lilly wished the floor would swallow her up. Robby just looked at the magazine and then grabbed the other one titled “Rodeo Riders.”

“Um,” Lilly didn’t know what to say.

“I’m sorry Lilly,” Robby said handing them over to her. “I didn’t mean to intrude.”

“God, this is so embarrassing.” She grabbed the magazines and stuffed them back into her book bag.

“Hey, it’s all right,” Robby said. “You’re 18, you can… well you know.”

“Yeah, but it’s different when they fly out of your book bag in front of your best friend’s dad.”

Lilly made an exaggerated gesture while putting the magazines in the bag and the porno “Leather Cowboys” fell out of the bag.

Lilly went to grab it but Robby was faster. He looked at the cover and laughed.

“Okay, just kill me now,” Lilly sighed.

“I’m sorry Lilly,” Robby said and put the movie back in her bag. “Don’t be embarrassed.”

Lilly frowned.

“It’s not like I’ve never read a nudie mag or two.”

“Two?” Lilly asked a little disbelieving and then gasped before covering her mouth.

Robby laughed. “Okay, a lot more than two. But that’s not the point.”

“Are you mad?”

“well,” Robby thought for a second. “No. I mean Miley’s got to be curious about sex right? I understand, I was 18 once. Adult magazines and film can be healthy way to satisfy curiosity, but…”

“But?” Lilly asked.

“Well, I’m not sure it’s the best way. You got to know that this stuff is just posed to sell. It doesn’t really reflect reality.”

“Should I get amateur porn then?” Lilly asked before she could stop herself. “Oh, god I did not just say that.”

Lilly got up and started gathering her bags.

“Lilly,” Robby said calmly. “I just want to say one more thing. If you or Miley have any questions or concerns I want you to know that if you’re comfortable enough to talk to me about it that I’m open for discussion. Okay?”

Lilly looked at him for a moment. “Okay.”

“Good,” Robby nodded. “And between you and me I don’t think amateur porn is any better. It usually involves two not very attractive people.”

Lilly laughed.

“Do you still want that OJ?”

Lilly nodded and Robby went to the kitchen. Lilly relaxed a little and put her bags on the floor again more carefully this time. The two settled in to watch the NASCAR race together.

After about 10 minutes Lilly kept thinking back on their conversation. There was a question itching on the back of her mind that was burning a hole in her head. She kept looking back and forth between the TV and Robby. Form the corner of his eye he noticed but decided to let her build up her own courage. It paid off.

“Um, can I ask you something?” Lilly asked attentively.

“Sure,” Robby said.

“It’s about the sex thing again.”

“Okay.”

“Um, what did you mean by the magazines and movies not being the best way to learn?”

“Oh,” Robby said. He took a moment to think back. “The way the actors move. It’s just a show for the camera. For most women, it requires different attention to reach orgasm.”

“Oh,” Lilly said. “Is it like way different.”

“Depends on the woman,” he said. “All women are different in what they need.”

“So how will I know…” she trailed off.

“How will you know what?” Robby leaned back on the couch to look at her.

“How will I know what I like,” she asked shyly. “I mean the first time.”

Robby felt his cock twitch at the question. The current situation had all the making of a porn movie itself.

“You’ll know a little from when you’ve masturbated,” He said softly. “But other than that you’ll just need to be with someone who’s attentive. Otherwise you won’t enjoy it much, but it will get better.”

“Oh,” Lilly said. She was hyper aware of the man sitting next to her. Old enough to be her dad, but he wasn’t. He probably had a lot of experience. He could probably make her feel good the first time.

And that’s what she and Miley had been afraid of. The girls in their school who had all these horror stories about how much it hurt or how bad it was. But Lilly and Miley knew enough to know that most of that was because of fumbling teenage boys who had little to no experience.

“I’ve been afraid,” Lilly added. “The girls at school say it hurts a lot.”

Robby knew that he had offered himself up for advice. But he didn’t think as far ahead as having an 18-year-old virgin alone on his sofa looking at him as the knowledgeable older man. He was beginning to sweat.

“Does it?” she asked.

“Well, I’m not a girl,” Robby said. “I’ve heard it hurts.”

“Have you ever... you know. had... a virgin?” she asked. She didn’t mean for it to sound like an invitation. But she was feeling sorely tempted to invite.

“Uh,” Robby stalled. The air around him was getting really tense. He could see the slightly dilated look in Lilly’s eyes. He wondered if she knew where this conversation was headed if they kept on. “Yeah, yeah I have.”

“And what happened,” she said.

“It was fine. Yeah, she said it hurt a bit, but she said her friend’s had scared her into thinking it was much worse.”

Oh,” Lilly said again. She looked over Robby’s body. In her mind she could picture herself there on the sofa, beneath him like an R rated movie. It wouldn’t be a bad idea for a first time. And older experienced man she trusted completely. But she didn’t know the words to make it happen.

“I hope my first time’s like that too,” she said.

“You just need someone you trust and love,” Robby said.

“I…” Lilly looked at him lost hoping he could read her thoughts.

Robby grabbed her hand and gave it a squeeze in a reassuring gesture. Lilly inched closer to him and looked up at his face. He looked down at her. It was an invitation he imagined he should turn down morally. But really, there wasn’t any argument he could think against it. She was willing and legal.

So Robby leaned down slowly and kissed her softly. He was nervous until the moment he felt her respond. She was young, she may have been teasing unintentionally. But her tongue slipping into his mouth told him she wasn’t.

He moved his hand slowly up her arm and to her neck. They kissed for a while like that and then he moved his hand down to her waist for a while before he spread his fingers out more so his index finger grazed the underside of her breast.

The mewl she gave brought him to full hardness in the mere anticipation of what was to come.

“Are you offering what I think you are Lilly,” Robby had to break away and ask.

“I think,” she looked a little scared.

“I just don’t want to push you if that’s not what you meant.”

“I just don’t want to promise I’m not going to freak out at the last second.”

Robby smiled. “You have my full permission to freak out. Like I said, I don’t want to push you.”

“I want to try,” she said. ‘I think this is a really good idea.”

Robby laughed softly and started kissing her again. This time he decided to try and be a bit bold and slip his hand underneath her shirt. Lilly was getting excited and she wasn’t completely sure what she should be doing with her hands. She continued to caress his back and moved a leg over his.

Robby took her then and made her straddle him. He leaned back on the sofa and caressed her skin under her shirt.

“Can I take this off,” he asked lifting the shirt slightly. She nodded and he removed it quickly.

Her bra was a pale blue. She looked down at him a little lost. He pulled her back down into him and ran his hands all over her back and chest and bra. He started to undo it and she froze momentarily before settling herself back into the kiss.

When he got her bra off he moved his mouth to her neck while he tweaked her nipples lightly. He paid extra attention to the sounds she was making and if he was honest with himself, he knew he hadn’t paid this much attention to a woman’s pleasure in many years. Most women his age already knew how they liked it.

Lilly broke off for a moment. “Can I?” she fingered the buttons on his shirt.

“Yes,” he answered and settled back on the couch. Lilly took her time more due to nerves than anything. Her tiny hands exploring his chest as it was revealed to her was making Robby’s hands flex on her hips trying to control himself from thrusting. It was so exciting for so many reasons.

Lilly leaned in and started giving his chest small kisses. It was slowly driving him insane and he grabbed her a bit roughly before kissing her again.

“Was that bad?” Lilly said when he pulled away.

“No, Lilly. It’s wonderful.” He said. He took a nipple into his mouth and sucked briefly before letting go. “ You’re perfect.”

Lilly ran his hands in his hair lightly. She looked down at him sucking on her. He seemed to be enjoying it so much she couldn’t help but get more excited.

“Do you want to go to my room?” He looked up at her, tried to convey a reassuring look in his eyes.

“Um,” Lilly said. “Yeah. That makes sense.”

“Lilly, I don’t want to pressure you,” he ran his hands down her back.

“No, I want to do this. But you’re just going to have to lead the way you know. I don’t really know what I’m doing.”

“I can lead,” he smiled and took his shirt off the remaining way. He picked her up and she wrapped her legs around his waist. With little effort he made his way towards his bedroom and closed the door behind him.

He laid her gently on the bed and started kissing his way down her stomach and undoing the buttons on her jeans. Lilly lifted up slightly, helping him take off her jeans. She kicked off her shoes and he removes her socks.

He looked down on her. She was only wearing panties that had matched her long lost bra. He could see they were a little wet for him already and his cock started to get uncomfortable in its confines. Still, he held off from taking his pants off for a while. He wanted her to be relaxed.

He leaned down slowly and started kissing her mouth again. Their tongues intertwined and he made a slight move to part her legs. Lilly took the hint and wrapped her legs around his waist again. Robby moved his hands up and down her body, calming her nerves.

“I’m going to take my pants off now, okay?” he warned.

“Okay,” she whispered.

Robby managed to get them off while still kissing her mouth and her neck alternatively. He kept his boxers on in any case.

He made a move then to take her panties off, her breath hitched, but since there was no protest he continued. She moved her legs from his waist to make it easier for him.

The first things he did then was begin to touch in between her legs while not reaching her cunt yet. Her breath sped up and he was encouraged to move closer to her center. He started by running a single finger up and down her folds. She was already wet enough o feel there.

“You’re so beautiful, Lilly,” he whispered in her ear. She shuttered beneath him.

After making his finger wet with her own juices, he started fingering her clit lightly. She almost bucked him off her body. He thought about tasting her, but was worried that perhaps she’d never had that done to her either. A woman could be very self-conscious about that sort of thing. However, Robby thought, perhaps it was better to get her completely comfortable about sex the first time out. And with that Robby started to move lower and lower on her body.

Lilly watched him go and froze.

“Relax, Lilly,” Robby soothed. “I just want to make you feel good.”

Lilly nodded mutely. Obviously she knew what Robby might just be about to do. She was worried though. While she’d read most woman found it incredibly pleasurable, she’d also read a lot of men didn’t like doing it for many reason.

“You don’t have to,” she whispered.

“I know,” Robby said. He was already there, and she’d felt those words air in her core.

Robby didn’t waste anytime in devouring her, not wanting to give her time to protest. He managed to wrench a guttural moan from Lilly before she covered her mouth in embarrassment.

“You can be loud, Lilly,” Robby said. “I want to know you’re enjoying this.”

“Yes,” she breathed. ‘Yes a whole lot.”

Robby smiled before continuing his ministrations. She jerked when she orgasmic and he held her hips still, riding it out with her.

“Oh, god,” she breathed.

He wiped his mouth before leaning over her face again. “Good?”

“Yeah,” she said. “Incredible.”

“You still sure you want to lose your virginity?” He asked sincerely.

“Yes,” she said certainly. “This is exactly what I wanted.”

“What?”

“Someone who knows what they’re doing.”

Robby laughed softly. He reached into the nightstand and took out a condom. Lilly watched him, growing a bit nervous despite the post-orgasmic state. Robby could read the nerves coming in, but ignored it. He’d asked, numerous times, first-time nerves couldn’t be helped.

He lowered his boxers and kicked them off the bed. The he opened the condom packet and rolled it on himself.

He positioned her legs a bit wider, getting her ready for what he was about to do.

“It will hurt, Lilly. I can’t help that. But I’ll be as gentle as I can.

Lilly nodded. She could feel his cock at her entrance slowly making it’s way inside. She couldn’t help but tense up a bit, and then before she could even tense up any further he had broken through in a swift movement. She held on to him in a death grip and crunched up her eyes. It hurt, but she didn’t cry.

“That’s the worst of it,” he said. He kissed her lips trying to get her mind off the pain.

Slowly, very slowly, he started to move inside her. Slowly she started to relax and after awhile it didn’t hurt at all. She loosed her grip on him a bit and started to caress his back. Robby took the encouragement and started to move faster within her.

He was in bloody heaven. He took a look down at her, this flushed girl sweaty and spread beneath him. He was lucky man and he knew it. Her eyes were hald-lidded in lust and she kept whispering his name like a mantra. He bent down and licked at her neck, tasting her, before kissing her mouth.

His thrusts sped up, and his hand snaked down to torture her clit and try to get one more orgasm out f her before he couldn’t continue anymore. She arched off the bed and tightened around him. The heat of her body, the slickness of her cunt, and he couldn’t hold off anymore, thrusting a few more times into her young willing body before coming.

He didn’t pull out right away. He moved the hair off her face and looked into her eyes.

“Thank you,” she said.

“No, Lilly, thank you. “

She hugged him fiercely to her. She held like that for a minute and Robby hugged her back.

Then he moved off her and she was suddenly shy at her naked body.

“You’re beautiful, Lilly.” Robby said. He moved his hand over her body in a non-intent kind of way. “Make sure you don’t let any guys walk all over you. You deserved to be worshipped.

Lilly blushed bright red.

“Do you need anything? Does it hurt,” he moved his hand lower on her body.

“I’m a bit sore,” she confessed.

“You should take a warm bath,” he suggested. “I can get one ready for you.”

“Okay,” Lilly nodded.

Robby got up and put his pants back on.

He left to the guest bathroom and started to fill it up for Lilly.

A whiles later when Miley came home, her dad was watching TV in the living room. When Miley went upstairs she found Lilly laying on her bed sleeping peacefully, hair wet with a bathrobe on.