Anon and Gilda strapon cuddle time

>You are anon
>Age: 17 or whatever the legal age of consent is in your backwater state
>You woke up blearily early on a saturday morning to your phone vibrating
>You check the ID
>Its your best friend Gilda
>You two have been pals since middle school
>Usually bullying everyone else into giving up their cookies or lunch money
>Although you've sort of drifted apart in high school you've still kept in touch and hung out frequently
>You stare at the message on your phone
>"Meet me by the old treehouse around noon today...dweeb"
>You rub your eyes, the old treehouse huh
>It was a major project for you two the first summer before highschool
>Your dad provided the money and you two went and bought boards, nails, hammers
>Built that sucker from the ground up no adults required
>Lately you've been using it as a hang out spot to drink stolen beer or light up a joint
>Its pretty isolated and its got a gorgeous view
>Yours and hers little secret
>Glancing at the clock you decide you're not going to get any more sleep anyways
>You pull yourself out of bed and zombie walk to the shower
>An hour or so later you're feeling more like a functioning human being
>Checking the clock you head outside and grab your bike
>The air feels nice flowing around body as you pedal lazily towards the woods
>Hell you could do this in your sleep
>Its a good 10 minute ride but you enjoy the exertion
>When you get to the tree house you notice a bike already leaning against it
>Its still a little before noon, but it seems shes beaten you there
"Hey, Gilda!" you call from the ground
>You see her peak her head out of the door and wave you up
>Once you get in you see her leaning against the far well
"So whats up Gilda, why the sudden need to meet up here, and this early too, couldn't it have waited?" you ask
>You think her cheeks redden a bit but you're quickly distracted as she walks over to you
>"No dweeb, it couldn't wait. Now turn around" she says
"W-what? Gilda what is this about?" you stammer, you've never seen her act like this
>"This is about you not picking up on anything for the past five years dweeb, so I'm going to make it just real clear what I'm after" she says grabbing one of your arms and spining you against the wall
>You're in too much shock to really register anything thats going on as your brain struggles to try and comprehend whats going on
>However your mind is dragged cruely back to reality by a clicking noise
>You look back in horror as you feel cold metal on wrists
>She handcuffed you! Oh god, its october, shes going to kill you and eat you or something crazy
"G-gilda, what the hell are you doing!? Let me go!" you exclaim starting to panic
>Much to your surprise Gilda pushes herself up against your back wrapping her arms around your stomach and kisses your neck softly
>"Shhhh dweeb, I'm not going to hurt you, well, maybe just a little but thats only if you don't play along." she whispers in your ear
>Suddenly what she said earlier hits you like a ton of bricks
>She likes you
>Like really likes you
>Suddenly this situation doesn't seem so bad
>You're trapped alone in a tree house with a very attractive girl and from all accounts she wants to have her way with you
>You're still lost in your fantasy when you hear her rummaging around in a backpack
>And when she pulls something out your fantasies come crashing down
>Suddenly you wish she WAS going to kill you and eat you because the alternative is looking a lot worse
"G-gilda...what exactly are you planning to do with that..." you say, glancing in terror at her
>She grins evily
>"Well dweeb, I meant what I said earlier. I gave you plenty of opportunities but since you squandered them, well, I guess I'll just have to take the opportunity won't I?" she says
>You've heard enough
>But with your hands shackled theres no way out and the tree house is a good ten feet off the ground
>Besides Gilda is the better sprinter between you two even if you did manage not to break anything landing she'd be on you in a second
>Your only option is diplomacy and 17 years of being a smart ass have taught you that you are the least diplomatic person alive
>Hell if you tried to negoiate with Canada you'd end up at war
>But its your only shot
"Look, Gilda, how about you unshackle me and we try this again later, maybe over dinner and a movie or something you know?" you say
>She grins
>"Trying to talk your way out huh dweeb? You know thats not gonna work, now maybe I'd be willing to uncuff you, but how do I know you're not gonna run off. I want this and I want it now dweeb, you've made me wait long enough" she says
>You're in full panic mode now, shes tying the strapon around her waist and she seems fully intent on using it on you and there is not a damn thing you can do
"Um...if you don't stop, I'll yell rape!" you say desperately
>Oh, that got her attention
>She walks over to you all traces of amusement gone
>"I don't think I heard you right dweeb, you'll do WHAT exactly?" she demands standing right behind you
"I'll...um...yell..rape" you whisper
>You feel an arm around your neck while the other one aids her hand in unbuckling your belt
>"Listen dweeb, I'm trying to be nice about this alright, you're cute, I like you, a lot, I wanted you to fuck me but since you're as dumb as a brick it looks like I have to wear the pants around here" as she finishes this statement she yanks your jeans and boxers down
>"You wanna yell rape? Go ahead, theres no one around for miles and you know it, but I'l tell you this, you start yelling then I WILL make this a rape, by god I will make it so you never sit straight ever again. She snarls as you quiver in total fear
>Suddenly she grabs your sack and squeezes, hard
>"So whats it gonna be dweeb, you gonna let me consumate our relationship or am I just going to have a new fuck toy?" she demands
"okay, okay, just...promise you'll be gentle?" you say quietly
>She kisses your ear and rubs your dick gently
>"Anon, by the time I'm done you will be begging for more" she whispers
>You shudder as she reaches down and squeezes your butt
>"God dweeb, you're adorable has anyone ever told you?" she teases
>You hear her walk to her bag and back and then you feel something cold and slimy touch your butt
>You tense up on instinct and she slaps your ass
>"Come on dweeb if you don't let me lube you up its gonna hurt like hell, not that I mind" she says
>You relent and relax your ass
>She rubs two fingers around your tight sphincter and then very slowly pushes her index finger in to the knuckle
>You groan at the unfamiliar sensation
>You groan even more as she wiggles her finger around inside
"G-gilda stop that it, it feels so weird" you says
>She laughs
>"Don't worry dweeb, I bet it doesn't feel as weird as this" with that she inserts a second finger and you grunt
>It does indeed feel quite a bit weirder
>You try to relax as she moves her fingers around loosening you up
>After a few minutes she withdraws them and you let out a breath you didn't even know you were holding
>Although its quickly sucked back in when you feel the soft rubber tip of the strapon knocking at your back door
>True to her word Gilda is very gentle, almost loving, with you
>She pushes the tip in extremely slowly waiting for your ass to adjust before pushing in a little more
>All the while shes kissing the back of your neck and running her tongue around your ears
>Finally after a few minutes the entire dildo had bottomed out and her hips were pressed firmly against your ass
>"Not bad for your first time dweeb" she said running her hands up your chest
>"Now the real fun starts" she purred
>She pulls back excruciatingly slowly almost all the way out, the tip only just remaining
>You moan at the feeling and quickly blush
>She smiles, and forces it back in all the way just as slowly causing you to moan again
>"So dweeb, do you want me to go faster" she inquires and you can hear the smile on her face
"Yes" you say softly
>She grinds into you
>"Sorry, I couldn't make that out" she says
"Yes!" you say a little louder
>"Yes what dweeb?" you can hear the smirk
"Yes, fuck me faster Gilda" you say wiggling your ass
>She grins
>"Happy to oblidge my loving partner" she says as she begins to move back and forth at a faster pace
>Unexpectedly she pulls you away from the wall
>Without your support you fall over forward
>And the dildo in your ass suddenly hits a whole new place
>Before you know it the sluttiest moan you've ever heard is coming from your mouth and you're spraying your cum all over the floor
>"God damn dweeb, I knew I was good, but I didn't know I was THAT good" Gilda laughs from behind you
>You're too busy moaning like a slut to think of a come back and your head is starting to go blank
>Before long you feel Gilda slam herself as deep into you as she can a couple of times
>Then she drags you over to the mattress you two kept in the corner for camping
>She pulls out of you slowly and removes the hand cuffs
>She kisses your neck and then turns you around to kiss you gently on the lips
>"So, how about it dweeb, you wanna be my girlfriend" she asks smiling at you
>You glare back but its just for show, you're well and truly hers and you both know it
>She smiles and holds you close
>"So dweeb, how long untill you're ready for round 2?" she asks
"How about we just cuddle for a bit" you say
>She smiles even wider
>"Fine with me" she says pulling you close to her chest

~Fin