NUMBER 1: A week with Olivia! (day 3)

DAY 3

I woke the next day with Olivia's warm hand in mine. I noticed she was still asleep, so I decided to repay the favor she'd done for me the previous day. I slipped my hand out of hers and moved down the bed before gently spreading her legs a little, presenting her slit to me.

I lightly ran my tongue all along her entrance, coming to the clitoris and sucking on it gently before letting it out of my mouth with a soft pop and switching instead to softly slurping at her folds, running my tongue gradually further and further into them. Olivia moaned groggily, still not quite awake but clearly already feeling the effects of my actions, because her body had begun to move in waves at my licking, as my tongue penetrated deeper into her love nest, swirling around her walls hungrily, taking in the sweet taste of her. After some time, I seemed to have reached an especially sensitive spot, because all of a sudden Olivia jolted wide awake, sitting up with a loud, gasping moan as her vagina seized up in her first – but undoubtedly not last – orgasm of the day. I looked up at her, smiling, my mouth wet from her juices, and said: “Thought I’d repay you for yesterday.”

“You cheeky boy” – she said once she’d gained her breath back, a grin painted across her pretty face.

We kissed, got up and went to breakfast. After that, we played video games for a little while, and Olivia beat me for the first time because she was distracting me the entire time by giving me a lap dance – and it was extremely difficult to focus on the screen and not the stunning singer massaging my crotch with her round backside. Once she’d won, she got up, and I said to her: “Come on Olivia, you’re not going to both beat me and leave me hanging, are you?” – gesturing to the tent in my pants. “What do you think I am, some kind of monster?” – she replied, smirking and rubbing my erection through the fabric before fishing it out and beginning to stroke my shaft up and down. I sat back and closed my eyes as she stroked, eventually involving her mouth too, licking all up and down my length before starting to suck on the tip, swirling her nimble tongue all around the most sensitive part of my penis. I had already been damn near ready to climax from the stimulation of her backside during the lap dance, so this did not last for all that long – soon enough, I thrust my hips forward and pushed more of my length into her mouth and down her throat as rope after rope of semen shot from it. She gagged a little, but managed to swallow it all greedily, lifting her head from my member and licking her lips sexily. “There, much better now” – I said, running my hand affectionately through her dark caramel hair. She giggled and wiped her mouth with her hand before replying: “I’d never turn down a good second breakfast.” I laughed, and we went for round two at the game we’d been playing.

We relaxed on the couch in the game room and played until lunch, then ate and went out to play some soccer outside – this time not involving stripping, unlike my basketball game with Sydney and Chloë. As we played, I could see Olivia was getting a little upset that she wasn’t winning at anything we played except for the one round of the video game, so I let her win this time. We started over, and I felt like she had started to catch on that I’d gotten worse, but didn’t seem to realize it was on purpose. “Come on Luke, you can do better than that!” – she teased playfully, before unexpectedly adding: “If you score this goal, I’ll give you my butt right here, right now. I’ve never done that for anyone before. How’s that for some motivation?” Wow, that was pretty forward of her. “Say less!” – I said, before burying my shot past her into the top right corner. “There you go, I knew you could do it!” – Olivia said, before hiking up her short skirt and sliding down her panties. “Well, a promise is a promise” – she said, approaching me and once again pulling my shaft from my shorts and stroking it until it was hard, after which she bent right over, putting her hands on her ankles and presenting her tight rear entrance to me. I wasn’t one to hesitate in this situation, and, having lined my tip up with her backdoor, pushed in cautiously, making her gasp and bite her lip as I put my hands on her hips to keep her from falling as more and more of my length slowly sunk into her virgin anus. She shrieked a little as I went deeper, penetrating unexplored parts of her rear passage and making her legs quiver violently from the wild sensations she was experiencing. “Does it hurt?” – I asked cautiously. She nodded. “Do you want me to stop?” – I asked. “Hell no. Take me. I’m all yours” – Olivia replied, her voice dripping arousal. The way the gorgeous singer said that drove me absolutely crazy with how sexy it was, and I began thrusting in and out of her rear with more purpose and ****, yet again rapidly scrambling her mind. This was amplified by me taking one hand off her hip and reaching over to finger her while I penetrated her from behind, the other hand on her lower back for balance. Eventually, Olivia lost all ability to stand upright, and we instead switched to the prone bone position, with her lying flat on the ground and playing with herself furiously and me thrusting down vertically into her now well-worked, but still supremely tight backdoor. It felt like she could orgasm just from me in her rear, but now with extra stimulation she went over the edge very easily, time and time again screaming out and pushing her face into the artificial pitch as I kept pushing myself up and down inside of her. Eventually, after a long time of keeping this up, I allowed myself to finish too, filling her rear passage this time. I lay down next to her, and we both panted intensely, tired but very pleased. “Best…promise…I ever…made” – Olivia breathed out, stroking my cheek. Her face had marks on one side from where she had been pressing it into the ground, and I ran my hand along them caringly: “Does that hurt?”

“Burns a little, yeah, but I’ll be okay. Thanks for asking, Luke, you’re the sweetest” – she replied, kissing me before lifting herself off the ground and going to get her panties from where she’d left them. I soon got up too, and we headed inside. We had quite a quiet rest of the afternoon and the evening, recovering from our intense time on the soccer field by taking a shower and cuddling on the couch, chatting about nothing for hours, interrupted only by dinner. As the night set in, I had an amazing idea. “We’ve had quite the day today, wouldn’t you say, Olivia?” – I asked her. “Uh-huh,” – she answered, curiously, - “Where are you taking this, Luke?”

“I think we should round it off in style,” – I responded cryptically.

“By which you mean?” – she asked.

“Let’s have sex on the roof and spend the night there under the stars” – I said bluntly. Her chocolate eyes lit up upon hearing this. She nodded enthusiastically, before saying: “Oh my God that’s amazing! I’m so down.”

I went to ask for our sleeping place on the roof of the mansion to be arranged, then, once it had been organized, took Olivia’s hand and led her upstairs all the way out to the top, where a bed had been prepared for us. The night was a little chilly, so we threw off our clothes and quickly got under the covers. We embraced each other and began to kiss affectionately, my hands eventually making it down to her sexy rear and squeezing as we made out, while hers found my penis and stroked it to erection before slowly guiding it into her slit. I picked up on what she was doing just in time and pushed her backside softly from behind to get further into her, continuing to kiss her soft, beautiful lips, my tongue dominating hers with ease. It was a magical feeling – me and Olivia Rodrigo, lying on our sides facing each other under a star-filled night sky as I gently slid in and out of her moist sex, making out passionately. Her heaving chest pressed up against mine as we got closer and closer together with my shaft sinking deeper into her, and I could feel the goose bumps all over her heavenly body from the cold night wind blowing through her dark caramel hair and making its way under the covers. I was trying my very best to keep her warm though, hugging her as tight as I could as we made passionate love under the moonlight.

After a while, I could feel her begin to tremble lightly, but it wasn’t from the cold, as she soon began to shake harder – she was climaxing again. I kissed her even more passionately as she reached the ultimate high yet again, thrusting harder, making the utmost effort to give her the most pleasure possible. She turned around, and her warm back pressed up against me instead, as I began spooning her gently, kissing all over her neck and putting my hands on her bust, squeezing her breasts as I slowly ran my length deeper into her folds from behind. She moaned softly at the sensation, rhythmically rocking backwards to match my movements inside of her. It was truly heavenly – it felt like the entire world had disappeared, and all that was left was us, joined together in a rush of passion, and the night sky.

Olivia gently rolled herself, and me, over so she was on top of me, turned herself over and put my shaft back in, then slowly, tenderly began to rock her hips back and forth, her arms around me, her lips once again on mine. Her walls soon clenched again as she reached another climax, rocking a little more wildly for a little while before slowing down and steadying out once again. We could both feel our energy waning after such a rollercoaster day, but kept going nonetheless, searching for that final peak, hoping to reach it together, bodies moving in perfect harmony with one another. We eventually did just that – I heard her breath getting heavier and heavier again and let go just as she orgasmed once again, her vagina clutching my shaft as I once again filled it with my seed. And that was the last thing I remembered that night, as we both almost immediately fell asleep, exhausted from all the sex we had had that day. To think, this was still not even the halfway point…