WATB Outtake: The Virginity Scene

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Status: Finished  |  Genre: Romance  |  House: Booksie Classic
(Hannah decides to cancel on her tinder date, and goes to Jake's apartment for a drink and to talk to him. little does he know, she has quite a huge favor to ask of him, and it may just be something he wants to do as well. all she has to do is find the courage to ask...)

*** This is an excerpt I cut from my novel that's currently in progress! Very sexually detailed content ahead. ***

Submitted: June 29, 2019

A A A | A A A

Submitted: June 29, 2019



Part 1: Hannah



As Jake got up to get another drink, my heart was pounding in my chest. I had no way of knowing what his reaction would be, or if he would even say yes. I stared longingly at him, taking in his strong, muscular body and perfect profile. I was already feeling a little hot. And it wasn't just from my nerves skyrocketing. 

Okay, Hannah, you canceled that date with Adam for a reason, I reminded myself. You would feel way more comfortable having sex for the first time with Jake than a total stranger. And I knew that was the truth. My conscience was definitely right; Jake and I have been close friends for five months now. And I really do think that he likes me. There've been so many signs that he's attracted to me in that way. Unless I was completely misreading the situation...

Nevertheless, I'm a hundred percent ready.

I've been ready for quite some time now.

The moment could finally be here. For once, it might actually happen.

"Jake?" My voice came out quiet and squeaky. He turned towards me and smiled, making his way back to the sofa. The moonlight shone on his face, making him look almost ethereal. "What's up, Han?" His green eyes were locked intently on mine. Focus, girl.
"Um, can I ask you something?" I tried to hold eye contact as best as I could. "Yeah, of course, anything," he replied. I took a deep breath to steady myself. "Okay so... I know that you know, that I'm still, um, a virgin," I began. Not sounding too confident so far. "Well, I'm pretty tired of that, and I'm just, I'm ready to experience sex. I've wanted to for so long, but I don't really see my next boyfriend coming around any time soon. And I've always wanted my first time to be with someone who at least truly cared about me, and wanted to be in my life for a long time." I paused to gauge his reaction. His eyes were still trained on me, and I couldn't read the expression on his face. He motioned for me to go on. "Jake, you're one of my closest friends. You're always there for me, and you're such a great guy. You're genuine, kind, actually a decent human being." He shyly smiled at that and brushed his hand through his hair. Flustered, maybe?

Okay, time to hit him with the big question. 

"So, I don't know if you can see where I'm going with this but... Will you sleep with me?" 

Jake raised his eyebrows at me but still said absolutely nothing. There was a beat of silence that seemed to stretch on forever. I shook my head, angry with myself for thinking this was a good idea. "Y-You don't have to say yes, I'm sorry-" "Hannah, wait," He cut me off, grabbing my hand. "Sorry, I just wasn't expecting that to be your question," he chuckled. I gave him an embarrassed smile. "Listen, I honestly feel so... So honored that you want me to be your first. Seriously, Han. I've always really respected you for waiting this long." He moved closer to me. My body started to tingle slightly. I could smell the musky scent of his cologne. It would be all too easy to grab his shirt and pull him in, finally feeling those lips on mine. Should I? The temptation was rising rapidly. I moved my leg closer and he started stroking it with his other hand. "So, is that a yes?" I teased him, trying to sound seductive. He nodded. "Of course. I would love to. Are you sure you're ready? Like, you want to do this tonight?" I bit my lip. Fuck, I want it now. Right now. More than ever.

"Yeah. Are you gonna kiss me or not?"

And we both went in. Jake started kissing me softly at first, but it started to get faster and more aggressive by the second. His hands were all over me; My thighs, waist, hair, but he carefully avoided the breasts and crotch. Which only fueled the fire of my lust. Ugh, he really is going to make me explode. He pulled away, his eyes mischevious as he unbuttoned his shirt. One by one, his toned chest and abs came into view. My underwear already felt a little bit wet. "Tell me what turns you on the most, Hannah." 

And with that statement, I knew I had made the right choice.




Soon after, we were in his bed. Both of us had stripped down to nothing. So far, he had been fucking perfect. He handled all my sensitive spots with great care, stroked and used his tongue in all the right places. It almost made me thankful for all of the guys I had fooled around with before that were atrocious at foreplay. Now, I know how real men treat the girls that are tangled up in their bedsheets. 

"Ohhhh," a low moan escaped my lips as Jake worked his magic on my clitoris. Whatever motion that his tongue was doing, the swirls and pressing, it was way too fucking good. The thirst for him, for his cock, has taken over my whole body. My mind. Every fiber of my being. Euphoric pleasure crashed over me like powerful ocean waves, sending me into a whole other dimension. I gripped his sheets tightly and arched my back as he shoved his tongue in deeper. Wow, okay. He needed to stop soon or else I'll come right now, and ruin what I wanted this evening to be. "Jake, stop," I breathed heavily. His handsome face emerged from between my thighs. He pulled me up to a sitting position and kissed me, letting me taste my own juices. His fingers lightly petted my pussy, which was more drenched than a river at this point.

"Do you want me to put it in now?" He asked, his voice quiet.

"Yeah, I do. You have condoms, right?"

"Of course. Hold on," he got up and went over to his dresser and opened the top drawer. His cock was still incredibly hard from me servicing him, making me feel a little more relaxed and reassured. The fact that he liked to moan and make a lot of noise as well really diffused any awkward tension. So far, we're a pretty good match sexually. I played with myself while he got the condom on. "I'm just gonna put some lube on, okay? This will just make it so that I can get inside of you easier," he stated. He took out a small purple tube and squeezed a little bit out. I watched him rub the clear liquid over his wrapped-up dick. Finally, he came back and crawled on top of me. My legs instinctively spread out, falling open as we passionately kissed. His dick was lightly rubbing my clit now, and I could feel him poking at my pussy. "Fuck, you're so wet, babe," he moaned. I smirked and gave him the cue to put it in. His eyes, glazed over with intense want, lit up. I held onto him as he continued to rub me up and down, up and down. He grabbed his cock and started to slowly, ever so gently, slide it inside of me. I felt the tip moving around, sending shivers over my whole body.

"Hold on, you're a bit tight," he told me. I tried to relax my body even more, taking full deep breaths as quietly as possible. Reaching down with one hand, I worked with him to make it go all the way in. I cried out in shock as we succeeded.

Oh. My. God. The pain was almost unbearable. It was a sharp, intense kind of pinching sensation. Like a needle at the doctor's office, but ten times worse. Tears sprang to my eyes automatically. I was clawing Jake's back so hard at this point, that I'm pretty sure I could be drawing blood. He gave me a worried look.

"Are you okay? Does it hurt that bad?"
"Uh, um, yeah. It kind of really hurts. But don't stop. Please, keep going. Just, be really slow..."

He looked concerned, but did as I said. He went achingly slow as he thrusted in and out of my soaking wet pussy. I gripped his arms, overcome with this new feeling, this odd sensation of having something in me. The pain was subsiding with each thrust he made. It started to feel better, the pleasure was coming over me again and it felt so fucking incredible to have Jake like this. To have him be mine, even if it was just for tonight. I started to softly moan, letting him know that he was doing great and sending me over the edge.

"God, Jake, that feels amazing," I gasped he started to change the motion up. His cock hit up against the walls of my vagina, almost in a circular motion. "Yeah, you like that, eh? Is it nice finally having a dick inside this perfect pussy of yours?" I wanted to answer him but I was too busy moaning and whimpering. He started to suck on my chest, marking me with hickeys that were sure to show up in the morning. Should I do something other than just lay here like I'm paralyzed? I wondered. I started to slightly buck my hips, matching Jake's rhythm. "Oh man, fuckkkk," he panted heavily. The sound of our moaning and my wetness filled the air, coming together in perfect harmony. Suddenly, he stopped. I opened my eyes, confused.

"Do you want me to give you your first orgasm? Or would that be a little too much for you?" Jake asked, his dick still inside of me but not moving. I opened my mouth in surprise, wondering what his own personal strategy for that was.

"Y-yes, I wanna come for you so badly," I managed to speak. Desire was pulsing through my veins like electricity, aching to finally break free. He looked satisfied with that response and sat up. He started to thrust again. And by the way he sucked his pointer finger, I knew he was about to put that in there and find my g-spot. Holy fuck, how is this going to feel? I braced myself.

They weren't kidding when they said an orgasm is unlike any other feeling you've felt before.

Jake was making me go insane. I was screaming in pleasure, unable to contain all of this sexual energy anymore. He watched me in amusement as I grabbed at my breasts, the pillow above me, anything to stabilize my shaking body. His cock pumped slowly as his finger stroked at my g-spot. The pressure he used wasn't painful at all, it was just the right amount. I shut my eyes tightly, desperate to climax. The electric feeling had intensified, almost as if I was a bolt of lightning just waiting to strike.  Building up, up, up.

"Let it go, baby. Come for me," Jake commanded.

That was all it took for me. My toes and fingers curled as I let out a series of loud moans, my body vibrating and pulsing from the things Jake was doing to me. I felt a burst of liquid come out of my vagina, making me feel an extreme release. As Jake plopped down beside me, I started to feel a foreign, relaxed feeling. Kind of like my body was satisfied with finally getting to know what it was like to be that intimate with someone.

And I was. 

I turned to Jake, who was disposing of the condom in a tissue. "Th-thank you, Jake," I stammered. He tossed the tissue in the nearby trashcan and rolled over on his side, facing me. "You don't have to thank me, Hannah. Did you enjoy that?" I smiled shyly. "It was really amazing. I'm glad you said yes. This really meant a lot to me, more than you'll ever know," I confessed.

Jake seemed to consider his next words carefully. "You know, with all of the stuff that happened in your past with guys, everything you've told me about... I'm really glad I was able to at least give you a good first time. You, of all people, deserved that. I've always believed you deserve so much more than what you've been through."

My heart felt fluttery. Is this the right moment to tell him? To give my secret away, and just let it out at last?

I was so close to opening my mouth, giving in to the temptation, but then I stopped. All those old thoughts, the worries and fears I have always been plagued with started to seep into my mind. The memories. It was like a movie playing in my head now, and there was no way of turning it off. Don't do this, Hannah. Not now. Not after this.

But it was too late.

The rejection, the paranoia, the constant anxiety that everyone who said they cared about me would up and leave at any second. No way of knowing when, or sometimes why. Breaking down my walls, letting in these men with the most beautiful, alluring facades. Only to be left in shattered pieces, struggling by myself to build my walls back up even higher. The never-ending cycle, the endless deep pain and misery. Thousands of nights being alone and wondering what it was like to feel wanted, to be at peace with everything. To not dream about the ones who hurt me so badly, and wish they were different people.

I see all of their faces now. Clear as day.  They leered at me, mocking me for my naivety and foolishness. Even with Jake right beside me, I couldn't just ignore it. The tears rolled down my flushed face, blurring all of the faces together. Morphing them into a hideous monster.

And in this moment, they all became Jake.

"I'm so sorry, I shouldn't stay. I have to go," I choked out between sobs. Bolting up from the bed, I got dressed haphazardly and ran to the front door. I was struggling with my heels when Jake came running into the hallway, clad in blue boxers. 

"No, Hannah, don't leave," he pleaded. His eyes were sympathetic. "Please, tell me what's wrong? Did I say or do something? Was it when-" I shut him up with a passionate, sloppy kiss. He didn't deserve to be walked out on. Maybe I should listen to him, and sleep here for the night. But at the same time, I couldn't shake the feeling that he could easily hurt me as well. Maybe even more so than the others, considering he did just take my virginity. 
I needed to go home.

I couldn't bear the thought of Jake also wearing a mask to hide his true feelings and intentions towards me.

"I'm just really tired, I guess. Don't worry about it, okay? I'll see you at work on Monday. Have a good night, Jake." I hugged him goodbye and left the apartment before he could get another word out.









Part 2: Jake



I can't stop thinking about last night.

It was Saturday morning, and I felt like I'd gotten no sleep at all after Hannah fled my place like a bat coming out of hell.  It still puzzled me. What was it that made her start crying? Had I hurt her feelings somehow during the night? 

Something was telling me that she was afraid of me now. Like she expected me to abandon her or emotionally abuse her like all those other assholes did when she got close to them. Fuck. That might be the reason for the outburst.

Sighing, I dumped the rest of my coffee into the sink, washing it down the drain. I had 20 minutes to be at the gym and start prepping my new client for his marathon. There was no time to be so stressed about Hannah today.



During the drive, I failed to not think or worry about her. I realized that if I wasn't such a coward, this wouldn't have happened. It wouldn't have been the worst idea to pour my heart out and share all of the bottled-up feelings that I have for her. She fucking needed that. Hell, in this damaged world, we all did. Talking is hard enough, but opening up is even more of a terrifying act. She opened up to me about so many dark and horrible secrets from her past, when she lived in Harrow. Hannah is so much stronger than she gives herself credit for. So why couldn't I be the same? Why couldn't I be honest and just say that I fucking love her?

Just like that, everything from last night was replaying in my head for the millionth time.

How gorgeous she had looked in that green t-shirt dress when she first came in. Her curled red hair falling over her slender shoulders. And most notably, how incredible the foreplay and sex was. Even with her being a virgin, she still topped every girl I've been with before her.  It drove me crazy in the best way possible to finally be intimate with her, and let some of the sexual tension free. 

Her body was so soft and smooth to the touch. Her moans were like music to my ears. How easy it was to make her pussy wet and her legs shake with just some flicks from my tongue. And being inside of her... It had seemed like a hollow dream for so long, that I'm still a little bit skeptical that it actually happened. But it was so goddamn perfect. Touching her, tasting her, feeling her. If anything, I had fallen for her even harder during our tryst. 

And I didn't even try hard enough to convince her to stay the night. I absolutely hated the thought of her falling asleep alone on the same night she had sex for the first time. 

I didn't even fucking say goodnight.

I pounded the wheel with my hands, frustrated at myself for being such an idiot. I was so flattered and surprised when she asked me to sleep with her, yet I couldn't even tell her to get home safe before she walked out the door. If only Hannah could read my mind. She would know everything.


She would know that I think she's my soulmate. 

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