Olivia's Sex Checklist

"Well I was thinking that if we did everything all at once then you might get a bit overwhelmed. And also if you say didn't like giving Oral and then we tried to continue you might end up focusing on the bad bit rather than the bits you enjoyed if that makes sense?" Trevor nodded. "Yeah i get that. One bad thing might mean i end up focusing on that rather than the good bits. Im with you."

Olivia smiled. "Yeah so i thought maybe if sort of each week we try just one new thing and make a note of whether you like it or not. So I know you like routine so if we say every Friday we have a Battlebots marathon. We can watch it at other times im just setting out a Friday routine." She smiled kindly at Trevor who nods. "Yeah i get that. Routine is good. Please continue." Trevor said warmly. Olivia smiled more. "So every Friday we watch Battlebots then we'll do something. So lets say next week we just see each other naked. Maybe some light touching but nothing too serious. Then week after we do hand stuff. Handjobs, fingering maybe some spanking if you are up for that?" Trevor nods. "Of course you can spank me." He winks and blushes. Olivia raises an eyebrow. "Oh look at you. Aren't you just full of surprises. Ok i'll make a note of that. Im sure you'll want to see my ass jiggle too?" She winks and Trevor nods excitedly.

"Haha love that. Then week after that we'll move on to oral. Blowjobs, you licking my pussy and maybe you'd be open to eating my ass... and getting yours ate?" Olivia said nervously. Trevor went wide eyed again. "Wouldn't have had you for a girl who likes rimming... but if we're helping me with sex i best try everything." Trevor grinned as Olivia blushed. "Sounds great. Thank you for being open. And i'm fully aware if there's anything you won't like it is probably you giving oral so if you end up loving receiving oral but hate giving it i won't be upset. Your sensory feelings are valid too. It's not all about me." Trevor smiles. "Thank you. It means so much you are willing to do all this for me." He says with a tear in his eyes that Olivia wipes away.

"Ok so week 5... how would you feel about Anal?" Olivia asks much more confident. Trevor blushes. "Well i'll definetly give it a go but..." he blushes bright red. He picks up his phone unlocks it and hands it to Olivia. "Check the internet history." Olivia looks at him confuses but she does. She's shocked at the video she's seeing. "Are you... do you... Trevor... Do you want to get pegged?" She asks giggling but it's a kind giggle. Its not one where Trevor feels like she's making fun of him. "I'd umm i don't know if i'd enjoy it but... it does look fun to try." He says blushing again. "Thank you for being so open and trusting with me. I will happily try it with you. And i'd get a small strap to start and we can work our way up." Trevor nods. "Sounds good." He says relieved.

Then the penultimate week we'll do the big one." Olivia smiled. Trevor nodded. "The baby making one?" He said with a smirk as Olivia laughed. "Yes that one. What we'll do is i'll go on the pill for that. Because i want to be safe with you. We'll mostly use a condom but i'd like you to do a couple of thrusts without to get the full sensation." Trevor nods. "Ok. I'll trust you. I don't want to be a dad yet." He chuckled as Olivia let out a belly laugh. "Oh don't worry im not wanting one yet. Way to young to be a MILF." She laughs as Trevor drops to the floor laughing. "Oh you'd defo be the hot mom on the school run." He wheezed as Olivia cackled. "Dude thats hysterical. Fuck you are funny." She says tears rolling down her cheek. She finally recovers. "Then the final week we'd put it all together. Does that sound ok?" Olivia says with the kindest smile Trevor had ever seen.

Trevor looked at her. "I'm in awe. That's amazing. I love it. Just the fact you thought of all that for me. You're already the best girlfriend ever." He holds out his arms for a hug. Olivia runs in and hugs him. "Of course i'd do that. Anything to help you. Gosh you're awesome. And if there's anything you don't like be honest. I want this to be fun for both of us." She pulled away and put her hand to her mouth. "Oh shit sorry i just ruined your top with my makeup." Trevor looks down and sees a dark black cheek mark on his white top.

"I think this makes it look better you know. Feels like you've claimed me." Trevor chuckles. Olivia smirks. "You want me to claim you?" She said in a sultry voice. Trevor nodded. "All you have to do is say it." Olivia whispered in Trevor's ear. "Please claim me Olivia." He said slightly moaning. Olivia got out her red lipstick. But on a fresh coat of it. Then firstly kissed Trevor's white shirt before kissing his cheek. Leaving lipstick marks on both. "You're mine now you got that. Property of mommy." Trevor melted at these words. "Yes mommy." He responded as Olivia took a step back.

"Wait you actually like Mommy stuff? Awesome." Olivia grinned as Trevor wiped his brow relieved. "Phew i thought i'd weirded you out there." Olivia laughs. "There's very few things that coulf weird me out. Don't worry. I figured you might like the mommy stuff when you said you liked pegging."

Olivia looks at the clock. "Its getting late. I should probably head back. Thanks for such a great evening. I look forward to more." Olivia grinned kissing Trevor on the lips. Trevor watches her pick up her bag and go for the door. "Time to be brave" he mutters to himself. "WAIT" he says in a slightly loud voice. Olivia spins around. "Whats up?" She asked