[FM] How this painfully shy virgin finally got fucked.

I’m taking a break from my Sophie saga as things are still developing there (in a good way); I want to give it some time before posting another update. For now, here’s the story of how I lost my virginity…

I was invisible in high school, which suited me fine because my conversations with people usually ended with me anxiously bumbling random words as I desperately searched for the nearest exit. My motto for those awkward teenage years was simple: *it was better to be thought a weirdo, than to speak up (or stand out), and remove all doubt.*

So I did my best to blend in and go unnoticed, and I was pretty good at it too, probably because I was average in every way: short, but not too short, with boring brown hair and moderately fashionable clothing that wasn’t too colorful or flashy (for some reason I really liked Taupe tones back then). I was the living embodiment of teenage camouflage, perfect for a shy and awkward teen.

Then, sometime in my senior year, I started to question whether I was ugly. My curiosity increased as I overheard guys rating other girls from 1-10, which made me wonder where I ranked, so I decided to consult the fair, accurate, and impartial opinion of the internet. Yes, I posted faceless nudes online, obviously not a smart move, but I was eighteen, at that perfect intersection between raging hormones and stupidity.

The result was surprising – the internet consensus was that I was a solid seven, which was definitely higher than expected. And it helped my self-esteem when I got comments about how “fit” I was, with “banging legs”, and “nice tits” (not my words, believe me). It boosted my morale a bit, but part of me assumed they were just saying those things to get more nudes out of me. The praise made it tempting, but I deleted everything after about thirty responses.

At first, I was perfectly content to be a seven. It was comparable with the ratings of the average cheerleader, which made me feel pretty good about myself. But then it dawned on me: if I was a seven, then why didn’t anyone talk to me? Had the internet lied? Did my face bring down my overall score? Those thoughts started me on a downward spiral of low self-esteem and I knew I had to talk to someone about it.

There were only two people I could really go to: my best friend Lisa, and Josh. Lisa should’ve been the obvious choice, but for some reason it felt easier approaching Josh. (Looking back now, I realize that I had a crush on Lisa, so the thought of asking her if I was “pretty” probably triggered some subconscious insecurities). So I decided to talk to Josh.

The thing about Josh was that he was the most popular guy at school. Yes, believe it or not, a shy girl like me was good friends with the most popular guy in school. Well, *kind of* friends. See, Josh lived on my block and our parents had been best friends for years. That meant we’d spent most of our childhood on joint family camping trips, vacations to Disney World, and weekend barbecues during the summer.

He was practically family, and despite us being polar opposites, I felt completely at ease around him. But we never acknowledged each other at school, which wasn’t intentional or malicious – he was just super popular and busy with sports, girls, and doing whatever it is that cool kids do, like planking and cinnamon challenges.

Despite his popularity and busy social life, we’d still hang out once or twice a month, usually during the traditional joint family gatherings. He did most of the talking and would tell me all the latest school gossip, like who was hooking up or cheating, and what depraved sexual acts went down during parties. He smirked every time I sheepishly asked for explanations of things like tossed salads, pearl necklaces, and pegging. I think he reveled in making me squirm uncomfortably and blush radioactively as he describing each sexual act in graphic detail.

One Sunday afternoon, while hanging out in his room, I decided to ask him *the* question.

“Josh, am I ugly?”

He put down his phone, sat up from his bed, and raised an eyebrow. “Who called you ugly?” His tone was unexpectedly protective.

“Nobody,” I replied, avoiding eye contact. “Just wondering.” I tried to sound casual, like it wouldn’t be a big deal if his answer was yes.

“You’re not ugly,” he said confidently. “I know lots of guys who’d be into you.”

“Not true,” I said. “Not possible.” I stared out the window, feeling a little sorry for myself.

“Emi, where’s this coming from?”

Then I told him about my paranoia and depressive thoughts. About posting the nudes online, the comments I’d received and how it had made me feel even worse. He listened patiently with a mildly surprised look on his face, probably because it was the first time I’d ever unloaded so much raw emotion and talked for so long.

When I finished, he chuckled to himself.

“*What*?” I asked, half-worried that his laugh meant the worst.

“It’s not what you think,” he said quickly. Then he gave me this strange, intense look. “You were my first crush, you know.”

What? Why would he say *that*? He obviously wasn’t taking me seriously, and more than that, he was teasing me just when I had opened up to him about something important.

“Shut up,” I said, really layering on my annoyance.

Then I realized my fists were clenched. I was Angry. Enraged, even. Those emotions seemed so foreign to me, but there they were, dissipating the haze of anxiety that seemed to follow me around wherever I went. I suddenly felt brave and in control, like I’d found a key that unlocked an unknown part of me. And it felt *good*. I narrowed my eyes at him and for the first time in my life I didn’t hesitate to speak forcefully.

“You’re such an asshole,” I said. It wasn’t the most original of insults, but I delivered it like a whipped piece of barbed wire, hoping it would cut him deep. Then I waited for him to respond, but he just stared at me, trying to look all surprised and hurt.

“I’m being serious,” he insisted.

I crossed my arms. Was he doubling down on an obvious lie?

“Emi, I’m not joking. I first noticed it at that beach house on Emerald Isle. Remember that summer? You hated wearing swimming suits and never came out to play in the water, so you just sat in your room and read books all day. That’s the year you discovered The Hunger Games. You used to practice shooting an imaginary bow and arrow in front of a mirror whenever you thought no one was around. I’d never seen you look so intense and confident.”

I was totally confused. Was he really being serious?

“I’m over it now,” he added. “But it’s true, I promise. Pinky swear. And I didn’t mean to make you angry, I just wanted you to know that you’re not ugly.”

Did the most popular guy in school just admit to once having a crush on me? Not a chance. Not possible. But his expression said otherwise; he looked sincere and a bit embarrassed, and *that* was a feeling I was intimately familiar with. This was real.

“Oh,” was all I could think to say.

He sighed deeply, as if the confession had released some deeply-held internal pressure. A moment of awkwardness hung between us.

“I feel like you at least owe me some nudes after that confession,” he said half-jokingly.

I think he was trying to lighten the mood but I didn’t respond right away. To my own surprise, I was actually mulling the idea of showing him one of my nudes, not because I felt sorry for him or because I felt bad that I had basically called him a liar, it was because a warm, electric feeling was spreading from somewhere deep inside and it excited me.

“You promise to never tell anyone?” I said seriously. His eyes flashed with surprise, but he quickly nodded.

“Promise,” he said, and we interlocked pinkies like we used to do as kids. Then I pulled out my phone, found the best picture – a neck-down naked shot of me in front of a full-length mirror, then handed it to him. He zoomed in and out a few times, examining different parts of the image. I watched his expression carefully as he took his time (it felt like hours), then he gave it back.

“Well?” I asked after he was silent for a while.

“The internet was right,” he said. “Your legs are banging.”

I bit my lower lip. “And… the rest?”

“Nice tits, too,” he said.

I punched him in the shoulder. “That’s all?”

An almost imperceptible smirk curled up at one corner of his mouth. “Yeah. It was one photo, Emi, the angle was terrible and your face wasn’t even in it. If you want more commentary, I’ll need a different angle and the whole package.”

I bit my lower lip again as I contemplated his request; that excited energy began to thrum inside me. I glanced at the door, paranoid that someone might walk in, so I walked over and quietly locked it as Josh eyed me with curious and excited eyes. I looked at the windows. He must have read my intentions because he shut the blinds, darkening the room.

Then he sat perfectly still on his bed as I stood in the middle of the room. I reached down, curled my fingers under my tan hoodie and t-shirt, and slowly began to lift them.

“Emi…” he said, interrupting me just as my belly button came into view. “…you sure?”

I nodded once and continued lifting my tops until they were up and over my head, leaving me in a skin colored bra and brown cargo pants. I wasn’t sure what to do with the tops, so I neatly hung them over the back of his chair.

He waited silently for me to make the next move. I had assumed that removing each additional piece of clothing would get progressively harder, but I felt like a boulder in motion, rolling downhill and gaining momentum, unable to stop until it reached some unknown final destination.

I unbuttoned my pants and pushed them down, stepping out and placing them on top of the t-shirt and hoodie.

“*Damn*,” he whispered to himself. He looked genuinely surprised, which didn’t make sense because he was constantly around the prettiest girls in school. That gave me the confidence to remove the last two pieces of clothing, leaving me naked. Well, naked except for my socks, which I left on for some reason.

“Damn, Emi,” he said a little louder this time. “You’re definitely more than a seven.”

I expected to lose my nerve at any point, to quickly rush to put my clothes back on, but his transfixed gaze emboldened me, and curiosity and desire urged me forward. It helped that I trusted Josh; I knew that he’d stop if I asked him to, but that was the opposite of what I wanted at that moment.

“Is this a good angle?” I asked, taking a step forward and turning slightly so he could see me in a partial profile.”

Josh visibly swallowed. “You have no bad angles.”

I stood there for a while as he admired me. I knew he’d seen many other naked girls before, so I felt a sense of satisfaction and he stared, dumbfounded. Did he do this with all of them? Or was it just me?

I hadn’t moved for what felt like several minutes (it was probably just a few seconds). “What do we do now?” I asked.

“What do you want to do?” he replied.

“I’ve never…” I trailed off, not knowing how to finish that sentence. I’d never done anything and Josh knew that, but I knew that whatever I said would probably come across as a suggestion.

“I’ve never kissed anyone,” I finally said.

He stood up and walked towards me, our gazes locked as the distance between our bodies narrowed. Then we were only inches apart.

“We can stop at any time, okay?” He reassured me.

I nodded. Then his hand gently caressed my cheek and I closed my eyes. I didn’t have to wait long before I felt his lips press softly into mine. I worried that he’d try to move too fast – be too aggressive – but his kiss was tender and unrushed. Then he pulled back and I opened my eyes again.

“How was that for a first?” He asked.

“Really nice,” I said.

He brushed my hair back so that it was out of my face. I could see lust in his eyes; it matched the emotions charging through my body – like I’d been dipped in a vat of static electricity. Then he took my hand and slowly guided me over to his bed. I sat down, leaned back, and watched him pull off his shirt and slowly prowl towards me until he hovered just inches over my body. It was exhilarating.

I inched back so I lay fully on his bed and he followed on hands and knees.

“I want you, Emi.” He placed one hand on my stomach and drew circles before exploring upwards. Then he kissed me again, this time our lips parting and tongues dancing around each other, alternating between playful and passionate. Another first.

Our hands explored each other’s bodies as we kissed, his playing with my breasts, massaging them and teasing my nipples, while my hands reached out towards his stomach and followed the contours of his body until they reached his back, then explored downwards until I felt the fabric of his jeans. He broke the kiss for a minute to pull off his pants and boxers, then returned to kissing and touching me.

He started a trail of kisses down my neck, stopping at my breasts to suck and massaged them while he simultaneously rubbed my already-wet pussy. I felt heat and pressure, and electricity. I was starting to lose track of what specific part of me was feeling good. Everything nerve ending was on overload.

Then his lips moved even lower. I felt his tongue on my skin as it approached the folds of my pussy. I instinctively spread my legs as he positioned himself between them. Whatever coordinated effort was happening down there between his flickering tongue and his fingers was causing me to lose control. All I could do was lie there, stuff a pillow over my face, and hope that I could keep my moans quiet.

Just when I thought I couldn’t take any more, he brought his kisses and caresses back up to my lips.

“Do you want to keep going?”

“Yes,” was all I managed to gasp out. He pulled out a condom from his bedside drawer, put it on, then aligned the tip of his hard dick to my pussy. I was a little worried about how much it would hurt, but also excited and determined. He slid the tip in just a little and held it there for a while. But I was ready for more.

“It’s okay, keep going,” I said. More of him entered and I felt myself stretching to accommodate his size. It didn’t really hurt, probably because I was dripping wet and he took his time. It wasn’t long before he bottomed out.

“Stay there for a minute,” I said. “Let me get used to it.”

He nodded and started tracing his fingers along my sides sending jolts of electricity up my spine. I nodded and he slowly started pulling out then pushing back in, making each motion faster than the last until we were in a steady rhythm. Heat transferred between us and the friction created shockwaves that shot from my clit to my belly button.

“Wrap your legs around me,” he said, and I did. Then he increased his pace pushing me to a point where I couldn’t even verbalize pleasure. He thrust one final time and I felt him pulse over and over, each surge sending a jet of hot liquid into a condom that was deep in me and hopefully still intact.

After finishing, he relaxed and pulled out. We were a blissful heap of bodies, laying side-by-side, waiting for our heartbeats to slow down.

Afterwards, Josh wanted to make it official and asked me out on a date, but I turned him down. He was special to me, but something deep down told me it could never be romantic. I think he was disappointed, but us becoming friends with benefits for the rest of the school year was a good consolation (more stories there too, maybe for another day).

I also thought the experience would build my confidence and bring me out of my shell, but I was pretty much still the shiest senior at school. Turns out that losing your virginity doesn’t magically cure your social anxiety, which worried me a little. In the fall, I’d be at university, hundreds of miles from anyone I knew, so I really needed to learn to make new friends.

Fortunately, I did meet someone during freshman orientation. Her name was Sophie and she liked reading young adult fantasy books just like me. She was beautiful, charismatic, and by the end of the fall semester we were good friends, but you might already know that ;)

Source: reddit.com/r/gonewildstories/comments/ryn317/fm_how_this_painfully_shy_virgin_finally_got