Teach Me to Please | Please Me #1 - Chapter 35: Chapter 35

Book: Teach Me to Please | Please Me #1 Chapter 35 2025-09-07

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S I E N N A
"I'm ready." He said the words with complete conviction, so much so I thought I heard him wrong. I pulled my head away from his chest and looked back up at him. I could see it in his eyes, the complete conviction and trust staring back at me. I didn't know what to think of it.
Why was he suddenly ready now? He wasn't ready the night of the storm so what made him want to now? Did he feel bad for you? Did he think having sex with you would make you feel better?
"Right now?" I asked slightly taken aback.
"Yes – shit, this is probably really bad timing, isn't it?" that was an understatement. I didn't know how long I stayed in his arms until I stopped crying and even when I did, I remained there, in his warm comfort. I had never felt so close to him. He made me feel safe and gave me this sense of peace I had never experienced in my life.
"No, I just.... please don't do this because you pity me." I stepped away and spoke. Did he feel bad for me? Did he want to do this because I said I hated myself? Did he think sex would make this go away? However, something in me told me that this was different. He cupped my face between his large, warm hands and shook his head, his eyes never leaving mine.
"I'm not."
"Are you sure because I don't want you to feel you have to and –"
He cut me off by placing his lips on mine in a gentle kiss. It wasn't rushed or desperate. It was slow, telling me he wanted this. He wanted me.
He pulled away and rested his forehead against mine. "I want this."
My words had run out, all I could think to say was, "I just don't want you to feel like you have to make me feel better by fixing me with sex." Sex made people forget. I wasn't a stranger to that concept, that was why I slept with people whenever Adam and I broke up or had an argument. It made me forget all the horrible things said and done, but it never made anything better. It only made things worse.
"You're not broken, Sienna. There isn't anything to fix. But even if one day you shatter to pieces, I'm not going to be there with a bottle of beer and an offering of sex, I'll be there in whatever way you want. I'll be there to listen, to understand, to give you whatever you need. Trust me on that, okay?"
I swallowed my tears threatening to make a reappearance at his kind words and nodded.
"So, if you don't want to do this right now, you don't have to, I can wait. I'm just letting you know that I'll be ready whenever you are."
In that moment I realised that there was never going to be another Roman in my life. Whether in the future we part ways or remained our friendship, every piece of him would follow me. I couldn't help the thrumming of my pulse pounding against the blanket of my skin as I stared up at his eyes and saw the sky-blue storm that rain with silver flecks, telling me to trust him, to take that jump, to feel so much more closer to him. To all of him. And I wanted to take that jump. I wanted to fucking dive.
There were minimal minutes between us before I reached up and kissed him. Immediately, he kissed me back, pulling me closer to him making me get on my tiptoes and wrap arms around his neck. Every pulse in my body was pounding against my skin as he lifted me up and carried me over to my bed.
As soon as he placed me down, he crawled on top of me, his lips never leaving mine. I wrapped my legs around his waist and held my breath as his lips travelled down to my neck and circled that sweet spot with his tongue. I moaned, wrapping my legs around him tighter, pulling him closer to feel the swell in his jeans rub deliciously against my core.
I pushed my hand between us and palmed him through his jeans, feeling his groan vibrate against my skin. Fuck. His hands shakingly came to the hem of my shirt and gave me a look to check it was okay. I gave him a reassuring look back and he lifted it over my head. I wasn't even wearing a special kind of bra. It was plain grey with a little bow in the middle, it was old and worn out, my underwear was the same, black and old, still a thong but not even lacy.
I trailed my hands up his T-shirt to feel the hot, hard skin underneath, hearing his breath catch as I did so. Without hesitation, he took it off and threw it somewhere just like he did with my top. I moulded my hand up and down his torso, fixing them on his shoulder as his fingers traced around my back to the hooks of my bra. I slipped it off easily as he unhooked it and threw it somewhere behind him. Instantly, his hands cupped my breasts and kneaded them, taking his time to flick my nipples with his thumb as I continued palming him over his jeans. The swell of his erection grew, and I could tell it was paining him as he took my nipple into his mouth and groaned deeply around it. Jesus, those vibrations.
My fingers fiddled as I tried to rip away his belt, finding his zipper, pulling his jeans down. The ridge in his boxers was now far more prominent and I couldn't help myself as I slipped my hand under the band and grabbed a hold of him. Holy shit, he was so hard and throbbed under my single touch.
"Fuck." He groaned around my nipple, drawing it between his teeth, making me moan. I pumped him slowly, squeezing him gently before picking up the pace. His breath became heavier, kissing up from my breasts to my neck then finally to my lips.
I pumped him faster, swiping my thumb against the slit at the tip causing him to let out a slight moan in my mouth. Holy fucking shit. That was hot.
"Keep doing that." He praised, connecting his lips to mine. I felt the wetness grow in my underwear as I felt him grow from my touch. I remembered when I first jerked him off, how nervous he was but now... god, now he knew exactly what he wanted.
The feeling of his fingers pressing against my clit over the soft fabric of my underwear made my back arch and I let out a moan. They circled my clit, playing with the fabric to create more friction.
I pumped him, wanting him to c um so bad. Before that could happen, however, he pulled my hand out of his boxers and grabbed the band of my thong, slowly pulling it down my legs, his lips simultaneously kissing down my stomach. When he reached my core, his hands softly spread my legs and his tongue licked all the way up my slit.
"Ah." I moaned and gripped the sheets when he sucked my clit into his mouth and flicked his tongue around it, groaning to create vibrations. "That's so... That's so.... Fuck." I cried when his tongue delved inside me. Jesus Christ. He licked back up to my clit, pushing two of his fingers inside me.
I bucked my hips off the bed as he did so, curling his fingers to hit that oh-so amazing spot as his tongue flicked my clit faster and faster.
"Fuck, fuck, fuck." I groaned, pulling myself up on my elbows to watch him. Something about his head between my legs made me lose even more control.
"You're so tight." He groaned as he thrusted his fingers faster, his groans vibrating against my clit. "Fuck, I want to be inside of you so bad."
A wave of euphoria crashed over me mere seconds later as his tongue and fingers reached a speed, I didn't know was possible. My cheeks felt flushed, and I felt my juices drip down my legs.
Finding my recovery several seconds later, I pulled myself up on my knees to kiss all the way up his chest before reaching his lips. Simultaneously, I yanked down his boxers and grabbed his throbbing cock, pumping it faster than ever.
We fell back down on the bed, pure bliss circling us as I got lost in his limbs. His erection pressed against my stomach as I grinded my pussy up and down it. He let out a deep groan and as I closed my eyes as his head nudge my clit that was now so sensitive.
"Sienna..." he groaned in a whisper. I wrapped my legs around his hips and flipped us over, so I was on top. Roman looked up at me in utter awe.
"Are you sure?" I asked carefully. I wanted him to do this for him, not for me.
"I'm sure." He nodded certainly. This was happening. Fuck. This was really happening.
"D'you have a condom?" I asked and he cocked his head to the side in confusion.
"Sienna... I'm a virgin remember?" shit, oh yeah. Roman had gotten so skilled in... other areas I found myself forgetting about the fact he was still a virgin.
I used to be on the pill, but after Adam and I's breakup, I became lazy with it to the point of not taking it at all. I reminded myself to get back on it after this.
"Oh... yeah, hang on a second." I climbed off him and rushed over to my desk, rummaging through stacks of random papers and whatever to try and find a condom. Oh c'mon, Adam must've left something round here one time. Finally finding a blue, foil packet, I rushed back to Roman and opened it with my teeth, I would do it with my hands if they weren't so shaky.
Carefully, Roman watched me as I rolled it down him, breathing heavily. Once it was on, I gazed back at him, my heart beating intensely rapid.
"You're sure you're sure about this?" I asked once more. He chuckled and shook his head.
"Yes, Sienna. I'm sure."
"Because we don't have to if –"
"Sienna, if you don't want to do this, it's okay. I can wait too." My heart melted. Why did he always have to be so sweet?
"No, no. I just want to make sure because I don't want you to... regret it, you know?"
Roman sighed with a sympathetic smile and sat up to meet me. "I could never regret it. Not when it's with you." He muttered and pushed a lock of my hair behind me ear. A small smile took over my lips as I lightly nodded. Gently, I lifted myself up and grabbed his cock, placing it at my entrance, slickening it with my wetness. I glanced up at him to see him watching me do so, his eyebrow furrowed together and his breath shaky.
"Nervous?" I whispered to him.
He gulped, "Yeah, a bit." He shyly admitted. I hadn't seen shy Roman in a while, but it was cute.
"I am too." I confessed and he looked back with a small, appreciative smile. "Relax a little for me, okay?"
He nodded and took a deep breath. I then, as slowly as I could, sank down, letting the head of his cock slip between my folds and inside me. Holy fuck did I miss the feeling of this. I let out a pleasurable sigh of relief as I let him slip inside me further.
A groan mixed with a sigh rumbled at the back of Roman's throat as he watched me do so. This was really happening. Roman was losing his virginity in my bed in probably the most unromantic setting ever but there wasn't a thing I didn't love about it. He accepted me. Fully expected me for all the good and the bad and, as cheesy as it sounded, I was honoured to be his first.
"How does that feel?" I asked breathlessly, bracing one of my hands on his shoulder, trying to stop myself from moaning.
"Holy... fuck." He groaned as his chest rose up and down rapidly.
"Can I move?"
He nodded hastily. "Please — fuck."
Carefully, I began to move up and down, bracing both my hands on his shoulders this time. He was so big. Jesus, I've never had sex with a cock this big.
I put pressure on his shoulders to aid myself in going up and down faster, taking him in fully, feeling a tug in my stomach. Holy fuck.
"Oh my god." I moaned and tipped my head back. I could hear Roman groan loudly as I closed my eyes and just felt the sensation of his size fill up to my walls.
I tilted my head forward, my hair falling over my face. Roman ran a hand through my hair to push it back and the expression on his face had me melting in seconds. His eyes were beaming in a storm of lust and pleasure and his jaw was tensing so hard as he let out a grunt through gritted teeth.
"You feel so – fuck – you feel so good." He praised bringing his hands to my hips to help me move faster.
My breath became pants as his fingers dug hard into my hips. I leaned forward to kiss him and moaned in his mouth accidentally causing my face to go bright red. He didn't seem to care and instead hungrily captured my lips; his tongue delving into my mouth to explore and caress. I tangled one of my hands into his hair and pulled earning another groan from him.
"Roman..." I moaned. I started grinding on him to stimulate my clit. He caught on to what I was doing and mirrored my movements.
"So, this was what those dry-humping lessons were for, huh?" he chuckled between groans. I did the same, arching my back as he hit a spot only his fingers had so far. I didn't even know if he realised he did it as I grinded faster.
"Holy shit, Sienna. That feels so.... god." He groaned, burning his face into my shoulder. "You're so fucking tight."
I kissed him again, not being able to contain anymore moans as I pushed him back down to lay on the bed and placed both my hands on his abdomen to ride him faster.
"Ah!" I moaned and tipped my head back to cry. His hands came up to my breasts to massage them as they bounced up and down with my pace. I felt him grow harder inside me, throbbing against my walls and I knew he wasn't going to last long.
"Sienna..." he grunted, throwing his head back against the pillow. "It's so... I-I can't..."
"It's okay." I consoled, riding him faster and faster. Up and down. Back and forth. Faster. So much faster.
"I – fuck – I want you to but – shit – I don't know if I can..." he grunted again. He was so worried about me, even when this moment was supposed to be about him.
"It's okay, Roman." I assured, holding back a moan. "C um, okay. C um for me." It felt so fucking good. He felt amazing inside of me. But this was his first time, and it wasn't going to be some porn star, erotic sex tape. However, I didn't mind it. This moment was enough. This moment was so much more intimate and erotic than most of my experiences because it was him. It was him and me and I couldn't feel any better.
I watched in awe as the euphoria washed over him, "Fuuuck!" his guttural grunt cried in echoes around the room as he threw his head back and climaxed. I felt the warmth of his seed fill up the condom and I helped by riding him throughout his climax before he turned limped inside of me.
As I glanced down at him, the beauty of his face glowed, his eyes were closed, his body gleaming with sweat, his chest heaving up and down, his oh-so kissable lips slightly parted.
I rubbed my hands up and down his abdomen, trying not to move to make myself moan. I didn't want him to feel bad about this. I expected it to happen. First times weren't perfect, if they were, mine wouldn't have hurt like a bitch and resembled a crime scene on the sheets afterwards.
"How was that?" I chuckled lightly.
"Fucking incredible." He sighed breathlessly. I laughed and brushed my hair out of my face before climbing off him. I carefully took off his condom, tied in and threw it in the trash.
My horniness was still extremely prominent as I looked back at him lying butt naked on the bed, and I rubbed my thighs together attempting to get rid of the ache.
"You didn't finish." Roman then spoke, a hint of disappointment lacing through his tone.
I smiled back sympathetically. "I know, it's okay though. This time was about you." He noticed my wince as I climbed back onto the bed, biting my lip as the longing ache between my thighs grew stronger. "You already made me c um beforehand though, so it doesn't matter."
He shook his head and gripped my hips hard, pulling me up his body so my clit rubbed against his hard skin. I straddled his chest.
"Come up to me." He ordered, exhaustion leaking through his tone but desire streaming out.
"W... What?"
"Come up to me." He ordered again.
"Roman, I don't think it's a good idea to – ah!" I squealed as he pulled me up so each of my thighs rested either side of his head and before I knew it, his mouth latched onto my core.
"Oh my..." his tongue flicked my clit, sucking it in his mouth just as he did before as he hands dug into my thighs.
"I love the way you taste." He murmured against me.
"Ah! Roman..." I moaned. "Please don't stop." Holy shit. First you ride his dick, now you ride his face. Damn, this boy was sent straight from Heaven.
I rocked my hips, trying to savour the sensation of his tongue. I kept flicking and sucking, his fingers digging into my skin to leave bruises.
"Fuck, I'm gonna... I'm gonna – ah, Roman!" I cried as I climaxed, I gripped my headboard with both hands until my knuckles turned white.
I was a withering mess as he planted a kiss at my centre and slid me back down his body, so my head rested on his chest.
"I can't believe you just did that." I muttered in awe against his skin.
"I think we've established that you make me do things I don't even know I can." He chuckled softly and brought his hand to my hair, stroking all the way down to my back, rubbing small circles into the small of it.
A loud yawn escaped my mouth as I wrapped my arms around him subconsciously. "Thank you." I whispered against his skin.
"For what?" he asked in confusion.
I fluttered my eyes closed as exhaustion took over my body. "For accepting me."
❦❤︎❦
I didn't remember falling asleep afterwards, but the soft, morning light peaked through the window as I opened my eyes to hear the birds chirping outside. What time was it? All I could feel was the warmth of my duvet and the hard arm resting under my head. Roman.
Memories of last night came flooding through.
"Fuck, I want to be inside of you so bad."
"You feel so – fuck – you feel so good."
"Come up to me."
"I love the way you taste."
Jesus. I needed Jesus.
I already felt the soreness of my pussy as I shifted under the sheets and mentally cursed. It didn't help that I hadn't had sex in a while and Roman was so... well, huge. I stared over at the sleeping boy next to me, his dirty blonde hair tousled, his lips slightly parted letting out soft breaths, the whole of his chest on display, streaks of the morning light painting glowing gold on his muscular body.
We had sex last night.
Holy shit, Roman and I had sex last night.
Gone was the innocent, anxious boy who had never as so much kiss someone. Here was the sexiest man I'd ever seen.
I smiled softly, admiring his features in the light, hesitantly taking one of my fingers to lightly brush over his face, trailing around his jawline, up to the bridge of his nose which looked a little crooked due to boxing, then through one of his eyebrows before trailing back down the side of his face to his lips.
He subtly scrunched his nose before fluttering open his eyes. He didn't say a word and stared back at me, adjusting his vision to the morning light.
"Morning." I whispered.
He let out a deep sigh and rubbed his eyes. "What time is it?" he asked groggily. His morning voice was so deep and rough I felt the noise of it rumble inside me. Damn.
I looked over at my clock. "9:30. We're late for school." I didn't care about being late for school, in fact, I didn't care about going to school today.
"Oh well." He rubbed his eyes again and chuckled lowly. He then gazed back at me, a different feeling lingering in the air.
"We had sex yesterday." I blurted stupidly without having anything else to say.
Thankfully, Roman smiled and nodded, chuckling to himself. "Yeah, we did."
The same amused smile overcame my lips as I turned into him and rested my head on his chest. "Hmm, so how does it feel to be devirginized?" I playfully ran my fingers in circles over his chest.
"Amazing." He jokingly laughed. "I don't actually feel too different, just..."
"Giddy?"
"Yeah." He smiled. "Something like that." We shared a look for a moment then laughed. "Thank you though." He then said. I looked up at him and cocked my head to the side whilst furrowing my eyebrows. "For a good first-time experience. I know it probably wasn't ideal and I was that good at it but –"
"You made me o rgasm twice. I'd say it was good." I chuckled. Roman looked down and smiled slightly before frowning.
"Yeah but... the actual sex part wasn't really that... well, long and I feel bad that you didn't –"
"Shh!" I placed my finger on his lips. "It was your first time, I'm not gonna judge you for that. Besides, things can only get better from here." I took my finger off and felt his hands play with the ends of my hair.
"You think so?"
"I know so. D'you think I suddenly became good at sex over night? It happens with time and practice and we can definitely do lots and lots of practicing." I smirked with a smile and trailed my finger from his chest to his collarbone.
I expected a flirty retort back but found nothing but a look on his face I couldn't read.
"What was your first time like?" believe it or not, I didn't get asked that question often. The only time I had ever talked about my first time was with Rya after it happened the next day.
I took a deep breath, slowly letting it out, "It was good to be honest." I answered truthfully.
"Was it with....?"
"Yeah." I nodded and he gave an expression of discontent before I jumped in with, "He was actually really sweet. It was a good few months into when we first starting dating-dating in the spring break of Sophomore Year. We didn't really plan it. Adam lost his virginity to some Senior girl on the cheer team at a party a few months prior before we became official, so it was nice to do it with someone who knew what they were doing."
"And he wasn't a jerk or anything when it happened?"
I shook my head, "No, he made sure I was comfortable the whole time, even when I asked if we could take a break 'cause it hurt too much, he was completely understanding. When I got blood on his sheets, he never complained and took care of me. We even ordered pizza after." I laughed at the last bit.
Sometimes, I think that Adam is a good guy – deep down, of course. He has the potential to be a nice person, to do the right things, I just think he needs to step up and change. And not change because some girl is trying to 'fix' him but change for himself. I don't think you can ever really fix someone without their own input.
"Oh." Roman looked away, gazing out the window. I couldn't completely read the expression on his face, but it seemed to hint towards jealousy. Maybe it wasn't the best to talk about how good my first time was with Adam when he's only just had his first time with me.
"But this tops my first time with Adam." I quickly say and Roman looks down with a faint smile lingering on his lips. A worry couldn't help but cross my mind. "Does it bother? That I've slept with lots of people?" I always wondered if he thought any different about me for it.
The words 'slut' and 'whore' were always thrown around to girls who lived their life the same way a lot of other boys did, yet the boys got praised and the girls got shamed. It was mainly the boys who shamed funnily enough, and most girls just followed along because they didn't want to be a 'problem'.
In cases like these, ironic enough, Adam and Taylor would stand up for me whenever I got labelled as a 'slut' or 'whore'. It primarily came from the classic 'locker-room-talk' in which some boy on the basketball team obviously hadn't gotten the memo – or contained an ounce of respect to understand – that women could have sex as much as they want and still be more than their body count. It ended for me after that and no one questioned my sex life so much again but there was always a new girl, a different girl, and sometimes she'd be alright at the end, other times she wouldn't.
"No." Roman shook his head. "I mean, who am I to judge when my sex life is almost non-existent? Besides, you're still Sienna no matter how many people who have or haven't slept with. In reality, it's not any of my business unless you want to tell me any concerns about it, and even then, I wouldn't judge." I came to the conclusion that there needed to be more people like Roman in the word. Despite that, I could see the mention of Adam bothering him.
"You don't like that my first time was with Adam." I stated, not questioned.
I felt his sigh as his chest heaved up and then down, his exhale prolonged. "I don't like that you dated him. I'm happy you had a good first time, really, I am because the last thing I'd want you to be is upset about it. I just don't like the way Adam treated you when you dated or even after you broke up with Leah."
"Why?" I couldn't help but ask. Why did he care so much about mine and Adam's past and present relationship?
He chuckled slightly but not in humour, "Because he treated you like shit. I may not be in the 'popular' group of school but I sure as hell noticed when he'd get into multiple fights and you'd have to clean him up, or when he'd blow you off for some random party, or how he'd get extremely possessive or jealous when a guy flirted with you, causing some sort of argument." The fact that he wasn't wrong made me realise something. Adam's toxic. Not a dick, not an asshole, but toxic. He made my life hell, but I kept coming back because he'd say he loved me or didn't know what he'd do without me. Even though he helped me through my darkest of times, that didn't deny the fact that his behaviours beamed with toxicity.
I somewhat felt bad for Leah. Shocking, I know, but did Adam put that same toxicity into their relationship as he did with ours? Did she feel as if she had to threaten me to keep me away from Adam because of how insecure he made her from his actions? I didn't condone Leah's behaviours or past actions, but it definitely got me thinking. People do crazy things in times of desperation.
"I'm glad I'm not with him anymore." I rested my cheek against his chest. "I'm glad you're here instead of him."
Roman stroked my naked back and continued playing with the end of my hair, it felt so soothing I thought I was going to fall back to sleep.
"Can I ask you something?" he then spoke. I lifted my head to rest my chin on his chest. "How... How did you know that story about your biological mom?" I could tell he was hesitant to ask it.
"The lady at the orphanage was a friend of hers and told my mom the story the day they found me." I explained, my mom didn't tell me all the information at once, she fed it to me with little questions I asked throughout the years and as I got older, I was able to paint the bigger picture.
He stayed silent for a few. "And are we going to ignore the fact you're a massive book nerd?" my cheeks reddened, and I began to pull the covers over my head.
"Yep." I clicked my tongue, but Roman had other ideas and flipped us over so he was on top and I was pinned underneath him. I shrieked and his lips attacked my neck with small but harsh kisses.
"Roman!" I hissed trying to withhold my laugher but ultimately failing. "My parents are home!" he stopped and buried his head in the crook of my neck.
"You're the one being loud, not me." He slyly quipped. I rolled my eyes as he brought his head up to face me. "Are you going to elaborate or not?"
I bit in my smile and shook my head, "So what? I like reading."
"You have tons of books in here."
"I like the escapism." I confessed. "In books you can be anything you want to be, travel to amazing worlds, live hundreds of different lives. I like that."
He hummed in satisfaction. "I'm going to keep calling you a nerd now though."
"Oh, I dare you." I threatened.
"Dare accepted, nerd-girl."
I gasped and wrapped my legs around his hips and flipped us back over, pinning his arms up. "You bastard!" I playfully faked an offended look.
"Is the nerd-girl upset?" he teased.
"She's about to rip your head off." I shot back.
"So, you admit that you are a nerd-girl then?" fuck, he got me.
"You mention this to no one." I wave my hand in the air. He laughed and sat up, my hands still gripping to his wrists as he lifted them up.
"It'll be our little secret." He whispered and kissed my neck. God, that felt so good. My hands let go of his wrists and fell by my side before entangling them into his hair.
"Roman." I moaned as his hands came up to massage my breasts, pinching and playing with my nipples, his hardness growing against my stomach. "Roman." I moaned again. "My parents... are home..." I said between sighs. He pulled away and groaned into my neck.
"God, I want you so bad." His hot breath hit my skin and my want for him escalated higher but I knew it wasn't a smart decision with my parents sleeping a few doors away.
"Me too." I whispered. "But not right now."
He brought his head up and brushed the hair fallen in front of my face back. "Okay."
Just as he said that, my stomach grumbled causing me to let out an embarrassed laugh. I didn't have dinner last night due to Roman and I's.... fun, so the consequence was rattling inside my stomach.
"D'you want some soup?" I eventually offered. He gave me a charming smile and nodded.
"Soup sounds great."

End of Teach Me to Please | Please Me #1 Chapter 35. Continue reading Chapter 36 or return to Teach Me to Please | Please Me #1 book page.