The s*x Journey of A Virgin

I sat at my desk in a small booth staring at the computer screen divided into 4 equal parts. I worked the night shift in the security room and my job was quite simple– Monitoring each session and intervening only if necessary. In this position, I was tasked with reviewing each applicant's paperwork, ensuring that whatever went down was in accordance with the participant's wishes and desires. My eyes briefly flicked up to the upper right corner of the screen, the camera picking up voices from outside the closed door. Judging by the time, this was most likely going to be tonight's last session and it was happening in the room dubbed 'Newbie Center'. Another deflowering. I had seen this kind of thing before. A girl, tired of being a virgin or clueless during s*x talks with her friends, would come in, wanting to lose her virginity and get it over with. Most could hardly wait until the dawn of their eighteenth birthday to come to our club. Some even had friends who paid for our services as a birthday gift. In such cases, the friends would pick a fantasy from our multiple selections, pay to make it happen, and leave the birthday girl here to receive her treat. Then they'd come back for her in an hour or two, bombarding her with questions as she profusely blushed at the memories of her experience. I was well acquainted with the scene, it had happened so often, and I was certain this would be no different. I enlarged the panel to full screen before settling in and reading through the girl’s specification sheet. This one was a self-entry. She chose to go by “Leah” and according to the file, she had just turned eighteen last week. Her only requirement was to get someone to pop her cherry. Fu*k, this girl had to be naïve—or incredibly stupid. She hadn’t even listed any hard limits or boundaries. I knew the admin staff would have red-flagged her very blank request form and only screened it as available to a few selected clients. Definitely nothing hard-core, no rough play, no one that would take a perverse pleasure in f*****g a virgin and wrecking this girl's pus*sy in the process. In the unlikely case that happened, that's what I was here for. If a scene got out of hand, or if a girl was in over her damn head and wanted out, I would first flick the lights on and off as a non-confrontational warning that the scene was finished. If the guy didn’t stop, I would send the guard on floor to the room to stop him. I hoped like hell it wouldn’t come to that for this girl.... Though I hoped it wouldn't end like the last one that I had to watch through my fingers. It was cringy and the most awkward scene I’d ever had the displeasure of watching. Just then the door opened and in walked Leah, her long thick curls tied up into a loose messy bun. She wore a black tank top and ripped black jeans that hugged her curves enough to show what she hid beneath the fabric. Yet as intriguing as she appeared, her lack of confidence screamed 'first time.' She walked towards the corner of the room, her brown eyes nervously taking in her surroundings as she sucked her bottom lip into her mouth. I felt my di*k stir ever so slightly, but being in the business for just over 3 years, I was pretty damn good at controlling myself. The room carried the feel of a hotel, no “playroom equipment”, just a king-sized bed and some expensive soft furnishings positioned off to the side. Leah sat on one of the chairs in the corner, nervously wiping her sweaty palms on her jeans just as the door opened again. I smiled when I saw who walked in and instantly felt relieved. I’d seen him do scenes here before. He was a decent man. Probably not what the girl was expecting to see, given he was well into his late twenties, probably early thirties, and his physique wasn't the ideal for most girls. But his gentleness? He was a true gentleman. Leah seriously couldn’t have been luckier to have him walk through that door, rather than some of the other guys I’d watched. Leah stood up, her eyes subtly raking up and down his body. “Oh.” The guy walked over to her, his strides purposeful and confident, his lips curved in a calm reassuring smile as he held out his hand to her. “I’m Troy.” Okay, so he was playing Troy tonight. “You’re nervous,” Troy stated. “You don’t need to be. We’ve got as long or as little time as you need.” Leah looked back at the door she'd come through, now her exit. “I um, I wasn’t expecting….” Troy smiled. “Someone my age, my size?” Leah swallowed hard and cringed. “I um, I don’t know what I was expecting….” “You thought you’d get some jock-looking guy or some Calvin Klein model,” Troy joked, his tone light and even a little amused. He put his finger to Leah’s chin and swiped his thumb across her bottom lip. “You know what? You could have some guy who’s only interested in f*****g a virgin and getting himself off, or you can have me.” Troy slipped the tip of his thumb into Leah’s mouth. “I will make every inch of your body sing, and as many times as it’s able. Because I will make this all about you.” Leah swallowed hard. I couldn’t tell if she was breathing. Troy moved in a little closer. “Do you want me to go find you someone else?” Leah shook her head, exhaling a shaky "No" that was barely audible. Troy smiled and stepped back. “Good.” He shucked off his coat and pulled his shirt over his head. “I think we should get started." Leah nodded, quickly beginning to undress herself as though it had been demanded of her. But Troy swiftly placed his hand on her arm. “Slow down. There's no need to rush– unless you are in a hurry to be done with me." He chuckled. Leah froze, sheepishly grinning at him, her blushing not that hard to recognize despite her ebony complexion. "We can take it slowly. I want you to be comfortable with me.” Troy was so relaxed, so calm. He slowly undid his belt, then his jeans. “s*x shouldn’t be rushed into, or just be a fumble in the dark. It should be about exploring each other and enjoying the journey, not just the destination. Know what I’m saying?” Leah nodded, even though I doubt she knew what he was saying, but she took a deep breath and started to strip off her clothes, slower this time. There wasn't a bra beneath her tank top, immediately exposing her full breasts, but she kept her panties on– Maybe too nervous to be fully naked. Troy didn’t seem to mind, because he never questioned it. He did, however, strip completely naked. He had an average body, slight muscles– but nothing to go crazy over, with chest hair that led to a happy trail. Troy stood there completely naked, his steel c**k hanging heavy and thick between his legs. Leah stared at him, her mouth agape, as she unconsciously squeezed her thighs together. She was clearly aroused. Her nip*ples perked like pebbles drawing Troy's eyes to them, but then her nerves kicked in and her hands instinctively flew up to cover herself. Troy gave her a knowing smile as he casually tugged on his d*ck. “Relax, there's no need to be ashamed of your beautiful body. How about we lie down and talk, hopefully put some of those nerves to rest?” Troy offered, pulling back the covers as he climbed onto the bed. Leah reluctantly dropped her hands before scurrying onto the bed beside him. She then pulled the sheet over herself all too soon forgetting Troy's words to her. But even then he remained patient as he propped his head up on his hand. “I can’t see how beautiful you are and truly admire your beauty if you continue to cover up.” “Oh,” Leah sheepishly grinned, pulling the sheet back down to her waist. "That's right, a little lower." Troy coached with a smile. "I want a better view of that pretty pink panty" She complied, pushing the sheet down until the valley to her covered virginity was on display. I fidgeted in my seat, adjusting my posture slightly as my eyes remained riveted on the scene before me. Troy smiled fondly at her as his eyes flicked from her covered pus*sy back to her face. “So, tell me, what brought you here? Couldn’t a sweet girl like you find a nice guy to have your first time with?” Leah blushed. “Well, um, I was going to do it with my boyfriend but each time I'd chicken out, and well, even though he said he'd wait until I was ready, I could tell he wasn't too happy about waiting." Her eyes closed briefly, her voice slightly shaken as though she was recalling a painful memory. "Then one day, I stopped by his dorm to surprise him and I found him... well you know, doing it with his female best friend." Troy listened intently, his frown line prominent as she spoke of the douchebag. "I had made a promise to him before that no matter what, I was going to do it on graduation night, maybe he didn't believe me." She sighed. "So here I am doing just that, keeping my promise." "So you guys have broken up?" Troy asked, just as invested in the story as I was. She nodded, bringing a pleased smile to Troy's face. “Good. That a*shole doesn't deserve you, neither did you deserve what he did to you. But I'm glad that it led you here." Leah smiled. "So is there anything in particular that you want to try tonight?” Leah blinked. “Oh, umm, I don't know….” Troy ran his hand over his chest, over his n*****s, and down his stomach. Leah’s eyes trailed his movements as her eyes widened. “Have you ever been eaten out before?” Leah shyly shook her head. “OK, how about fingered?” Troy probed. Again, Leah shook her head with an embarrassed whisper. "Never." "Alright. How about you, have you ever played with yourself?" There was a long pause, a build of suspense but then her words were spoken soft– timidly. “I uh, I um… I haven’t really touched down there before.” Damn it, she seemed almost afraid to call her pus*sy by name. She almost seemed so pure, so innocent. “It's OK, that's nothing to be embarrassed about." Troy reassured her. "How about we start with the basic, some touching here and there before we work our way up to the s*x, huh?” “Okay,” "Have you ever watched p*rn?" She averted her gaze. "Yeah, I was a little curious so I watched a few videos." "And you liked what you saw?" Still refusing to meet his gaze she nodded, making him smile as he wrapped his hands around his c**k, the size growing in his grip. “So then tell me what positions would you like us to try first?” She seemed taken completely off guard by the question as her eyes widened in shock. “Oh, um….” Leah blushed but couldn’t seem to answer. “Never be embarrassed,” Troy said gently. “If you want to ride me or have me pound into you, just say it. There’s nothing wrong with knowing what you want and asking for it. Actually, some guys even find it sexy when a girl knows what she wants and isn't afraid to ask for it. It's your body, you call the shots, okay?” Leah nodded and Troy gave her a warm smile. “Alright, so right now, I just want you to relax; surrender your body to your needs. Don't think about anything else except you, me, and the pleasure you're about to have tonight. Close your eyes and slowly.... breathe in and breathe out for me... relax." Leah eyes fluttered close, her chest rising and falling at an even rhythmic pace. “Now touch yourself,” Troy whispered. “Show me how you like it.”