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You are here: Home / Adult sex stories / Lily's Saga

Lily's Saga

Lady_PenumbraLady_Penumbra November 25, 2021 Leave a Comment

“Oh it-it’s ok sweetie I’m sure she’s just as excited.” He smiled a sweet, sheepish smile and took another drink.

“Hey, Jimmy. Didn’t she mention her parents were gonna go out of town sometime?” She looked panicked at Tyler.

“Oh fff-uck she did! I’ll text her and….oh uh mom would it be ok if she like…came over?” He asked plaintively.

“Oh Christ is he already drunk?!” She thought. The pleading way he was looking at her made her pause to try and think of an excuse. She stalled a moment by looking towards Tyler and making some non-committal noises, but Tyler nodded, clearly telling her to say….

“Y-yes sweetie sure but maybe this isn’t the week her parents are away.” She stressed and flitted a few glances at Tyler. “So don’t get your hopes up.”

She looked pleadingly at Tyler. “No I’m certain it was this weekend.” He said firmly.

Jimmy’s joyous shout was followed by her phone lightning up.

Snapchat- “Tyler”

“Hey baby Tyler told me you’re home alone this weekend. Why don’t you come over to my place? My dads not home but my moms gonna let me have a few friends over.”

Before she could even think of what to reply Tyler grabbed his phone.

“Here bro let me talk to her for you, you’re still learning.” He said, eyes on Lily.

“Oh thas a good ide-uh bro!” He laid back hands behind his head and laughed “Damn, whiskey feels fugin awesome!”

“Haha yes it does!” Tyler laughed.

He pretended to be typing as he looked practically through Lily.

“Oh shit bro she’s on her way. She’ll be here in 10! Guess you didn’t even need my help.” That last line really stung Lily for some reason.

“Letssss gooo!” Jimmy said as he punched the air excitedly. Tyler got up turned off the big lights and turned up the music. She sat frozen as the minutes ticked by.

“Oh Mrs. M, would you mind waiting for her? Let her in and all that?” Tyler ‘suggested’ with a sly, wicked smile. Lily looked daggers at him but she quietly said “Sure.” Before getting up to leave.

Jimmy rolled over and asked Tyler in a very audible whisper. “Hey bro, do you got a condom?”

Lily’s eyes couldn’t have gone any wider and she shook her head tensely and urgently mouthed. “Please.” At Tyler.

“Oh your first time should totally be without one.” He said in a fake whisper looking her dead in the eyes. “Besides I’ll bet she’s on the pill.”

“Oh yea! Good looking out, don’t don’t tell me mom though! shhhhhh.” He rolled over and off the bed. He stumbled over to her. “Oh man mom this so cool of you but like could you maybe go watch a movie or something so I could have a little alone time with my girl…..?”

She managed to get out an “Ok” As she left the room to stand against the wall and tried to think of a way out of what Tyler was setting her up for. She could hear Tyler clearly egging him on through the door.

Jimmy mumbled agreement to something she missed. “But shouldn’t we have some lights on?” Jimmy asked drunkenly. “Nah bro, chicks hate fucking with the lights on.” Tyler said smoothly.

Her phone vibrated again.

“You’d better go change into something else. Don’t wanna risk him noticing his gf is dressed just like his mom.” It read.

“Oh man thanks for looking out for me” Jimmy replied to Tyler. “Are you gonna go like hangout with my mom?”

“I was planning on it but Lily just texted. She says she likes the idea of being watched.”

“Hahaha I told you she was a freak bro”

Lily went and changed and put on some make up. Anything to try and keep Jimmy from noticing. Her heart thumping almost audibly in her chest. She chose a pleated skirt Tyler had made her get and a rock tee shirt she’d seen a teen girl wearing at the mall once. She realized for the first time she had put forth extra effort with those little Snapchats that she didn’t notice before. She checked her reflection in the mirror.

She hardly recognized herself, she could easily pass….

Yea… for some used up high school party slut on her way to flunking her second senior year…..

She beat herself up over the situation she’d landed herself in, but she had to admit. in the right light, dim, she looked younger and certainly not like herself.

She walked back down the hall to Jimmy’s door and stood just out of sight, texting.

“Tyler this has gone too far. We need to- ” She never got to send it though.

“Dude I think she’s here, come on in…Lily.” Tyler said flatly.

Time seemed to move like cold syrup.

She opened the door and stepped into the dim room, the sound of the music hit her like a gust of wind. She could just barely make out Tyler sitting in the computer chair by Jimmy’s desk, his face illuminated by his phone.

The shadowy lump that was Jimmy layed on the bed. He perked up and practically jumped off the bed and scrambled to stand up when his booze addled brain finally noticed her.

Tyler’s shadowy, phone-lit face looked sinister but his smile seemed genuine. She didn’t know what she was hoping would happen but whatever hopes she had were quickly disabused when Jimmy started talking.

“Oh man Lily you look soooo hot!” He was very drunk and could barely keep both his eyes open at the same time or stand steadily.

“Jesus Christ! He’s so drunk I could have worn exactly what i was wearing before with a name tag that reads. “Hi I’m Jimmy’s mom.” And he still might not notice!” She thought irritatedly to herself. She tried to sound like the stereotypical high school girls she’d seen on Netflix or TV in case his hearing was still sober enough to notice though.

“Oh ya, you like Jimmy? This party is lit A F” She cringed at how unconvincing she was but Jimmy laughed it off and leaned in to kiss her.

She tensed up, nose crinkling, fists clenching, but let him kiss her. His lips mashed against hers sloppily; it was apparent Jimmy hadn’t done this much, if at all before.

“Fuck, Jimmy! Am I Really THAT convincing or are you THIS stupid??” Her irritation rising.

She endured his terribly amateur kissing but she was growing less mad at Tyler and less embarrassed overall. She was starting to resent Jimmy a little. Her thoughts were almost instantaneous. He trusted his bully and went along with everything he said unquestioningly. He was catfished by his own mom with pictures and didn’t notice. Now she had his tongue in her mouth and had a dreadful certainty she was moments away from having to fuck him and he was still so infuriatingly naïve!

They made out for some time, making their way to the bed. She tried to mouth words at Tyler to get him to help or stop it or anything when Jimmy stopped kissing her to start sucking on her neck.

“Ouch!” She accidentally said out loud when Jimmy’s sucking started to sting.

“Oh sorry babe, here. Let me make it up to you”

He started to slide down towards her crotch, but she stopped him at her stomach. Tyler stepped in to thwart her though.

“Oh do you want me to watch as he sucks your nips, Lily?” He nodded as he spoke. His tone was more excited than she expected.

A single tear welled up in her eye from sheer humiliation, but she quickly wiped it away. She mumbled.

“Mmhm.” Indistinctly but Tyler’s look needled at her. “Ya.” Her strained tone should have tipped Jimmy off but he was busy lifting up her shirt and kissing her stomach and moving back up, her breathing getting heavier.

She gasped when she felt his mouth close around her nipple. He ran his tongue hard over the tender skin and his hands started massaging her thighs.

Despite all her mental protests her body betrayed her. Her nipple stiffened inside her son’s eager mouth, her pussy began to feel wet and she let out a small shameful moan.

Tyler taunted her from his chair, feet away, egging Jimmy on. She was trapped and had to play along.

“You really like being watched huh, Lily?”

“Not too hard Jimmy, ladies like it a little softer at first, right Lily?”

Tyler’s advice was infuriatingly spot on, and his taunts had her face so hot she wondered if he could see it even in the dim light.

He held the phone so she could see what he’d just typed.

“Tell him you want him to finger you.”

She shook her head stiffly but Tyler’s expression made it clear he wasn’t going to ask again.

“J-Jimmy I…. would you…finger me.” She sounded so nervous and hesitant she couldn’t blame Jimmy for believing she was a nervous teenager this time…

His inexperienced hands fumbled around her thighs and poked at her panty covered lips trying to lift the crotch of her panties. He started rubbing too low making her flinch and tense up. He tried to pinch the material to lift it up but pinched her by mistake, making her wince and pull back slightly.

She was embarrassed and not just for herself, his awkwardness made this all feel like so much worse of a violation. She wryly thought. “Well I’ve spared some poor girl having to endure this unskilled groping.”

He tried to slip a finger under the seam but lost it and it snapped her sensitive skin drawing another yelp of pain from her. She shot a glare at Tyler who was looking much too satisfied with himself.

“Sorry.” He said, his breath warm on her exposed tit. “This is my… first time” he said anxiously.

She was done being poked and prodded and reasoned helping this go smoother would spare them both a little extra humiliation.

“T-thats ok, h…here” She whispered, she hooked a finger under the waistband, steeled herself and just pulled them off. She laid there stiffly as his hands groped her bare pussy now.

“Mmm yea you like that don’t you?” Jimmy mumbled drunkenly into her neck, his booze-filled breath wafting at her between kisses that were sloppily wet.

A single “Mhm.” Was all she could muster, because miraculously between his awful kisses and sad pillow talk he’d actually managed to find her clitoris and was genuinely starting to make her wet. Much like most guys he thought a few twirls was all she needed and plunged his finger into her roughly and started to pull it out clearly determined to finger fuck her.

OOWWWWW! She winced and tensed up so hard Jimmy actually noticed.

“Oh sorry baby, Tyler said you’d be good to go… wha-wha should I..do?” He said laying half on his side, the whole awkward thing was ominously starting to feel like her own first time…..

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