Disclaimer- This is a work of fiction. It has no basis on real events or the actors themselves. I do not encourage underage sex. In no way shape or form do I own this fandom.
Summary
Jackson knew he had it easy. Rocki as his girlfriend, she put out unlike other girls but now she want him to do the same and he fears that if he says no she will break up with him. So he said yes and wilfully and admittedly slowly, made his way over to her room.
It was fear that made him agree to it, otherwise he would never be in this predicament. He looked it up the night before and what he found was reassuring, he was almost tempted to try it but he really, really didn't want to do it.
It, was fingering himself, well... not really. It was much bigger then a finger it was actually a dildo. He truly did consider fingering himself but chickened out. Rocki wanted to fuck him with a dildo and Jackson feared if he said no she leave him. So he laid on her bed, naked, face down, recalling everything he read and hoping it be over immediately.
"You have such a cute bottom" Rocki said, her fingers caress his buttocks. It actually felt nice.
"Thanks" moaned Jackson miserably.
"Come on babe, from what I've read it is an amazing experience, some guys cum without any stimulation on their dicks, others find it more thrilling then cumming even"
"I know" he replied sullenly.
"You know we don't have to do this" she replied. She wanted him to enjoy it, she believe it open up new doors and possibilities. She never ask Jackson to get fuck by a boy, oh no even if she imagine that be hot to watch but role plays, Christmas gifts of anal toys, vibrators she can turn off and on by an app. Her eyes shine as she imagined by most of all how thankful he would be learning the joy that his ass could provide.
Jackson however, saw this as a test. If he said no she be furious at him. He gets to fuck her but she never gets to do him. He never taken her from behind but he has taken her cherry and returned for more.
"No, I want to, really... I'm just nervous" he gave a small nervous laugh.
"Don't be, I be careful"
She laid on top of him, Jackson appreciated feeling her nude form pressing into him, her mouth seeking his and he leaned towards it.
It was a awkward kiss but nice. If he wasn't sick to his stomach he have been hard.
"so" he begun "have you got lube? I read spit isn't wise for anal"
"I got lube but I won't be using it just yet"
"Oh!" This cheered Jackson up. Perhaps she wanted a little fun first and he could distract her with his sexual prowess.
"Of course we aren't going to dive right in the deep end"
Jackson would have turned over if she wasn't sitting on his ass.
"What have you got in mind?" he asked, while thinking of getting blown, eating that fine pussy she has or even kissing her stupid. They all sounded wonderful at that moment.
"Rimming"
Rimming? She wanted him to rim her? She never asked or hinted to be rimmed before!
"I... guess I could give it a try. As you know I've never done that before"
They were both each others first.
"Not me you" Rocki laughed.
"Me? Oh!" His eyes widen in shock.
He was going to get rimmed. His heart started to beat faster. He wondered again how thorough he cleaned himself but knew he was clean. Her beautiful mouth was going to be intimate to his crack and hole.
He wasn't sick at the thought but turned on, her tongue was not as big as some of the dildos she owned. It couldn't hurt him, might discomfort him, it might feel sickening kissing her immediately after knowing where that tongue has been but at that very moment it was as if they were embarking on a quick journey into a land of taboo.
Her tongue was magnificent, the way it moved up and down his crack had him squirming, it was borderline between tickerlish and pleasure. Then when her attention was purely on his hole it changed, became more serious. He almost ran out of the room starkers but he somehow controlled himself, he was thankful he did.
The sickly feeling was replaced with one he couldn't explain. It felt like Rocki was orchestrating where his lower organs should be. What was freaky or freakier was while things twist and turned in his gut dancing to Rocki's tongue it didn't hurt. Yes he wasn't expecting it to hurt but things, organs, whatever shouldn't be moving and they were!
He moaned, he wouldn't mind if this continued. He wouldn't mind rimming Rocki as long as she compulsively checked to ensure that she was cleaned like he did before heading over to get this nightmare over with.
Overall getting rimmed was pleasant then he groaned.
She hit a nerve, the thing, nerve, whatever went off like fireworks, literally. It was a chain reaction that had him shaking and panting. If her tongue continued assaulting it he could, nay, would shoot his load all over her sheets.
And she did, Jackson, shook, moaned, groaned and sigh as his girlfriend relentlessly stimulated that area that caused him pleasure. It was better then his hand, equal to a blow job. He started humping the mattress, and wasn't aware he was doing so.
Rocki was pleased, she knew her guy would if he gave it a chance. Next up fingering. Rocki didn't want to spoil the mood by stopping, now that he was humping her bed, so she kept at it for awhile longer.
"Oh my gawd" moaned Jackson, he felt so close to cumming.
Then she stopped and started licking her fingers.
"Huh? What?" Jackson realised he almost cum, more importantly that he was fucking her bed.
"Shit" he said.
"Don't worry cutie, I don't mind you boning my bed"
"That was... Wow"
"This probably hurt at first, but by all accounts it should pass very quickly"
"What will... ouch, Rocki, love I... I-"
"Shh, push out babe, push out"
"Fuck, and this is with lube?"
"No spit, saving the lube for the dildo this is just my finger"
"Your finger? This is your finger! Take it out and use lube."
"Just relax, its almost all in and the dildo will be heavily coated in lube, I promise."
He did his best to relax and push out. Finally she was buried knuckle deep, her finger wiggled, he would have smiled if he wasn't weirded out by she was moving it in and out and he started feeling normal, as normal as he could be with his girl fingering his hole.
That amazing spot was not touched, she either avoided it, or lost where it was. Then he winces as she added a second, then more in and out, it was almost soothing, strangely enough. She started spreading his inner walls by moving her fingers apart. He didn't like that.
Then she added a third, she also brushed that magic spot. She didn't always touched it but she made sure to do so from time to time. It was the only thing that kept him on the bed.
Then she said it was time for toys and his heart sank.
"This is a prostate massager, it's also you birthday gift. I hope all the time you use it you think of me"
He was bracing himself for pain but none came.
"What are you doing"
"Putting lube on it, now push out babe"
It felt cold, the lube that is. He could feel it against his hole. He pushed, even though he wanted to clench his ass. Then it was slowly going in and Jackson was gasping in air like he just been in a run, it was like it was made just for him!
It hit that spot, that sweet, loveable spot, it spread him sure, that was discomforting but it wasn't terribly bad. He almost drooled so thrilled to have that spot touched. Then Rocki jiggle the toy and his cock was leaking precum and throbbing.
The Prostate massager was replaced with a butt plug, then a vibrator which had him drooling on her pillow then the moment he feared the dildo.
He would have ran if he didn't feel so weak from the anal stimulations.
She entered him slowly, Jackson didn't protest and after her tongue, finger, massager, few butt plugs, each bigger then the last, and two vibrators her dildo had no difficulties entering his hole, but he was still tight. It took effort for Rocki to thrust in and out. She soothed him as she worked, sure that he was still fighting it even if he was doing so unconsciously. She had planned to up the size like the other toys but was wavering if she should or not.
If she pushed him to much to soon he be dead set against doing it again, but he might already decide not to do it again in which case she passed on the opportunity to use larger sizes on him. He looked so cute naked on her bed with her favourite toys going in and out of his ass. That was what appealed to her. He shook and groaned as she buried all of it inside him, aiming for his prostate. She was almost convinced he be willing to do this again.
She got down low and made small thrusts as she nibbled on his earlobe. Jackson rose his ass off the bed, he was meeting her thrust. Her hand made its way around him and touched his dick. It was wet with precum and very hard.
She stroke him as she fucked his ass. He helped but still seemed tight.
He cum with a large cry, cum flying everywhere, both were surprised by the volume.
"Shit" Jackson gasp in shock.
"And I just washed these sheets too" Rocki said sorrowfully.
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