Guiding Lily (Season 1 Episode 6)

A Youthful Mistake.

Previously in Guiding Lily (Season 1 Episode 5).

Lily discovers how her youthful decisions can haunt her.

This story and headline were written without the assistance of AI.

WARNING: This story contains sexually explicit content that some readers my find disturbing. Reader discretion is advised.

Bryan, my best friend Janet’s brother had died in a car crash and at his wake, I saw people I hadn’t thought about in years.

One of them, Janet’s cousin, Danny, smiled as he approached me and said jokingly under his breath, “I remember when Janet would secretly give her brother Mark hand jobs over at my house in the day.”

And just like that, I was eleven years old again.

I hadn’t thought about that version of myself in a long time.

I was the girl who had chosen exploration instead of morality.

I was the girl who had chosen to try it all before she was really ready to understand the consequences.

It wasn’t that anyone forced me to do anything at the time. Not in a way that’s easy for me to understand today anyway. At the time my older brother Randy projected a certainty about what he thought was right for me.

And at the time Janet and I hadn’t yet developed a voice to seriously question the right or wrong of what we would shamelessly convince my older brother to do with us.

Some times simply hearing a shower running will take me back to that point in my life.

On that day Randy was taking a shower after he got home from school when he heard the bathroom door open. Randy turned the water off and stepped out of the shower to retrieve his towel.

**“Your towel fell on the floor.”

What was Lily, his eleven-year-old younger sister doing in the bathroom while he showered?

“Ah Lily… I’m naked here.”

“Yeah, I can definitely see that,” Lily replied grinning.

“Is there something that I can do for you Lily?”

“You’re actually doing it.”

“What am I doing… what are you doing in here?

“I’ve never seen a naked guy before.”

“I think you might be too young Lily to be worried about looking at naked guys.”

“Most of my girlfriends have already seen naked guys… even seen their erections and touched their hard-on.”

“Do you really believe them?”**

**“Janet, said that I could go to her house if I wanted to see a naked guy. Her sixteen-year-old brother, Mark, parades around the house naked all the time. She says that he forces her and her friends to jack him off and makes them show him their tits or pussies while they do it.”

“Are you going to take her up on her invitation and go over there and be forced to jack her brother off?”

“I told Janet I’d much rather see you naked and she said she would to.”

“So you came in here just so you can see me naked?”

“I came in here to ask if you would let both of us see you naked.”

Randy felt a twinge in his dick. He was already horny and his little sister standing there staring at his nakedness just made him more so. He could feel his dick starting to grow and knew that he was getting a hard-on.**

**“Janet said she wants to see if she can make another guy cum the same way her older brother cums when he forces her to jack him off.”

“So it would be okay with you if Janet tried to make me cum?”

“Yeah, I guess.”**

**Lily pulled the bathroom door open and stuck her head out in the hallway.

“Janet,” Lily yelled down the hallway.

Janet appeared in the bathroom doorway.

“Randy wants to make sure that we really want to do this and that we won’t tell anybody.” Lily told Janet.

Janet quickly stepped past Lily and stopped in front of Randy and stared down at his hard-on.

“Yours is bigger than my brother’s.” Janet said.

Janet started breathing through her open mouth as she looked at Randy’s hard-on. She slowly reached out with both hands and started fondling Randy’s dick.

“So do you want to try and make me cum?”

“I think I can, but I’m not sure,” Janet confirmed.

“Well… let’s all just go to my bedroom and we’ll find out.”

Randy walked into his bedroom and walked over to his bed and sat down.

Janet followed him to his bed and when he sat down she dropped to her knees on the floor in front of him as she so often did with her brother. Lily stopped a couple of feet away from the bed and just watched.

“I’m sitting in front of you naked and I’m thinking it’s only fair if you two get naked to.”

In less than thirty seconds the two young girls had undressed and were standing completely naked in Randy’s bedroom.

Randy scooted backwards on his bed and lay in the middle. He patted the side of his bed indicating that he wanted Janet to come up on the bed and lay down next to him.

Janet climbed up on the bed and stretched her nude body out alongside of Randy and reached out and wrapped her fist around his hard-on. Randy motioned for Lily to come closer and stand next to the bed on the opposite side where Janet was laying.

Randy pulled Lily closer to the bed. Randy leaned over in Lily’s direction and kissed her little pussy mound. Randy slipped his tongue out and pushed the tip of it between Lily’s tight pussy lips and started searching for her virgin clitoris.

Lily was breathing rapidly through her open mouth as she watched what Janet’s hand was doing to her brother’s dick.**

Janet then leaned over and slipped her lips over the head of Randy’s dick and sucked mightily as she squeezed his dick shaft tightly in her fist.

**“Oh hell Janet… your mouth feels so good!”

Janet took her mouth off Randy’s dick and leaned back and started stroking his dick again.

Randy put his arm over Janet’s back and pulled her naked body closer to his. Janet snuggled closer and put one leg over Randy’s thighs and began humping her young pussy mound against Randy’s upper thigh.**

**Randy moaned aloud as Janet started stroking his dick at a faster pace to match her humping motion.

Randy threw his head back as he moaned and arched his back trying to push his dick higher in the air trying to give Janet easier access as her stroking hand got him closer and closer to blowing his load.

It took another ten strokes before he pulled Janet’s naked body tighter against his as his dick started erupting between them.

“Oh hell… that was awesome… thank you Janet… nobody has ever done that for me before,” Randy admitted as he lay on his bed panting for air as cum still oozed out of his dick.

“Did I do it right? I only want to do it right just for only you Randy. That was a lot of fun. I have to go home shortly and I don’t want my brother to force me to do this in the same way with him when I get there. But I also don’t want him to beat me if I refuse to do everything the same way with him as I did with you.”

“I know your brother Janet,” Randy panted out between breaths, “but if he already forces you to jack him off now, then I think he’s going to force you to do this to him the same way you did it with me.**

**Randy turned towards Janet and slipped his right hand between her thighs, “let me return the favor.”

Janet’s arousal level hit a new high as soon as Randy’s fingers started to penetrate her vagina. Janet’s legs thrashed and jerked a couple of times and then she shot cum all over Randy’s fingers.

“Hey sis, now it’s your turn. Climb up here on the bed and straddle my chest. Reach out and hold on to the headboard and lean forward. Keep your knees by my shoulders and lower your beautiful pussy to my mouth.”

Randy moved his tongue in and out of Lily’s vagina a couple of times before sliding it upwards as he attacked her clit.

Lily started making a low moaning sound and moaned louder and louder.

The sheer eroticism of his little sister allowing him to eat her pussy made Randy’s hard-on return with a vengeance.

Janet wrapped her fingers around the base of Randy’s hard-on and leaned over and slipped her mouth over the head of his dick and closed her mouth and started sucking on his dick for all she was worth.

At the same time Janet fingered herself to another orgasm while she sucked on the head of Randy’s dick.**

**Janet felt the head of Randy’s dick swell larger in her mouth just before his balls twitched and his dick started shooting cum into her mouth. Janet swallowed in self-defense.

Randy moaned into his sister’s pussy as Janet sucked the cum out of his dick.

Randy’s moans against her pussy made Lily cum all over Randy’s face. She’d never felt anything like that in her entire life.

Randy laid back and wiped his face of Lily’s cum. He’d just eaten Lily’s virgin pussy. He’d eaten his sister to her first ever cunnilingus orgasm.**

**Randy reached over and gently put his hand on the side of Janet’s face and turned her face in his direction. He leaned in closer and gently but deeply kissed her on the mouth in a long French kiss. Janet opened wide as she sucked Randy’s tongue deep into her mouth. Janet quickly returned multiple French kisses and fought to overcome the need to tell Randy about the deep warm feelings that were suddenly flooding her heart.

“Those are kisses of one lover to another lover Janet. Thank you for giving me my first ever blow job. I love that you did that for me. You do know that a guy always eventually falls in love with and marries the girl that gave him his first blow job, don’t you?”

“I didn’t know that but I will forever hope that what you just said comes true.” Janet blushed.

“I know that you need to get home soon. But I want to tell you something. You have the right to refuse to let your brother force you to do anything to him you do not want to do. If he doesn’t stop beating you when you refuse him, then you come to me and I’ll put a stop to it however I have to in order to keep you safe.”**

“I think I am falling in love with you Janet and it would be my pleasure to kick your brothers ass if he beats you or forces you to do something you don’t want to do from now on.”

“Thanks Randy. My big brother has been making me do things to him since I was five years old. He didn’t always beat me when I refused him. It’s just been since I got my period that he started beating me when I refused. It’s just been easier to give into him rather than always lying to everyone around me about how I got all my bruises.”

As Randy and I left Bryan’s wake to head back to his apartment I couldn’t help thinking that as fate would have it my older brother Randy would in fact fall in love with and marry Janet and unfortunately one day make good on his threats against Janet’s older brother Mark. I needed to know more about just how Bryan’s death had left Randy so messed up.

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Relive Lily’s life journey from the start here:

MEDIUM PUBLICATION

The Medium link for Season 1 Episode 1 https://medium.com/@p_f_cogan/guiding-lily-season-1-episode-1-921fc600f727

The Medium link for Season 1 Episode 2 **https://medium.com/@p_f_cogan/guiding-lily-367af0e538f3**

The Medium link for Season 1 Episode 3 **https://medium.com/@p_f_cogan/guiding-lily-season-1-episode-3-08318229c9e9**

The Medium link for Season 1 Episode 4 **https://medium.com/@p_f_cogan/guiding-lily-season-1-episode-4-fbc7b4a37a3a**

The Medium link for Season 1 Episode 5 https://medium.com/@p_f_cogan/guiding-lily-season-1-episode-5-79d29f1930d3

INFINITE WITHIN PUBLICATION

The Infinite Within link for Season 1 Episode 1 https://medium.com/the-infinite-within/guiding-lily-season-1-episode-1-b84e9498c3a5

The Infinite Within link for Season 1 Episode 2 https://medium.com/the-infinite-within/guiding-lily-2df22e09a823

The Infinite Within link for Season 1 Episode 3 https://medium.com/the-infinite-within/guiding-lily-season-1-episode-3-8d68c84a43f2

The Infinite Within link for Season 1 Episode 4 https://medium.com/the-infinite-within/guiding-lily-season-1-episode-4-f9b8b0296153

The Infinite Within link for Season 1 Episode 5 https://medium.com/the-infinite-within/guiding-lily-season-1-episode-5-1527d6ba2255