The Ugly Duckling(19F) loses her virginity to the first guy that hits on her. [MF]

This story took place about 7 years ago when I was a freshman in University. And I’m going to try to explain how I lost my virginity in such a stupid (a bit slutty) way, so if you wanna skip the boring origin story of a pretty big slut, skip to ***

Let me start off by saying, I was a LATE bloomer. I was dorky throughout elementary and middle school, with big glasses, lob-sided smile and curly hair that I had no clue how to control (my single father raising me assured that it would be well into high school before I learned to manage my frizz. Side note to this side note: my hairdresser Vanessa was the first to really teach me a lot of techniques, which later evolved into make-up youtube tutorials. These days, I’d recommend Hair Romance and IndiaBatson if you need help with curls) I’m confident enough now to say I’m good-looking, I get a lot of looks and a lot of tinder matches. But let me stress that my life was a real Ugly Duckling story.

I had a few friends throughout school but no one really stuck around for very long, I was really awkward. Most friends I had throughout elementary ditched me as soon as looks started to become more important and I was clearly a lost cause. Most friends I had were from my religious programs on weekends and after school. Like, did you have a girl at your school that would talk about the fun they had at Shabbat improv on the weekend and never got the hint that no one was interested their weird congregation stories? Well that was me. So with all of this going for me, I was very inexperienced with boys. The majority of my male interaction in high school came from bullies. Girls and boys both teased me relentlessly and I hid away in my cocoon for most of high school.

I had started to get prettier near my high school graduation, my braces were off after 4 agonizing years, Vanessa taught me the fine art of curly hair, I started wearing contacts and my skin had gone from an acne minefield to the occasional landmine (mostly because I learned how to use concealer). I even started talking to the girl that is, to this day, my best friend (we met at anime club). I even started wearing SHIRTS instead of baggy sweaters. I was very ashamed of my body, although I shouldn’t have been. I’ve always been skinny and my breasts may not be the biggest on the planet but they’re perky and rounded, but alas, I was very self-conscious. Around this time I was asked out to our grad dance (Americans would call it a prom, I guess) by a boy loosely related to the anime club, but since he used to tease me, I assumed it was a “She’s All That” situation and promptly turned him down.

So I went into University with my best friend close at hand and managed to survive my first term without having any fun. When the second term started my friend suggested we join the LGBTQ Alliance club on campus (she’s Bi, and before you ask, no we haven’t). So I tagged along for support, and we ended up going to a party hosted by a member of the Alliance about 2 weeks later (my friend was crushing on the aforementioned member). I should have seen this coming, but I was promptly ditched at the party by my friend so she could make out with her crush. And I’m glad she did, because an hour later I’d be sucking my first dick.

I was wearing tight jeans and a baggy knit sweater over a long sleeve shirt and possibly my worst granny panties and bra (I still cringe thinking about how frayed and ugly they were), but I think what made me an easy mark was being 3 coolers drunk (lightweight). Jacob had just come in from the outdoor hot tub in -40 weather so he was only wearing a towel and he had styled his hair with water into a frozen pompadour, he literally had frosted tips. He was much taller than my 5’5 self, almost by a full foot. Pale skin that was turned red from the cold air between the hot tub and the door and had long dark hair that you could tell was curly as it slowly melted it’s way down. He wasn’t particularly muscular but he had broad shoulders and a clean sharp chin (I like chins, sue me). He was young like everyone at the party, but I guessed he was a little older than me.

God, I was dreading admitting this, but I think it’s important to paint a picture as to how drunk and awkward I was that I leapt on the first thing I saw I could make a conversation out of… He had a Straw Hat Pirates tattoo on his forearm and I pounced.

“Ohmygod, I love your tattoo! I’ve had the biggest crush on Zoro since forever.” (I still cringe thinking about this, but I mean, HE’S the one with the tattoo, and screw you, it’s a good show/manga)

“Oh thanks! Yeah I love it too, although I think Sanji is hotter and Robin is a knockout.” (Jacob is Bi)

What followed was a nerdy/dirty debate comparing Sanji and Zoro, all the while his curly dark hair slowly thawed and fell onto his face. He was peppering me with the odd compliment throughout our talk, about our matching curly hair, and that I was cute. I was really happy but I didn’t know how to flirt so I just kept bringing the conversation back to One Piece and other anime. I could tell he was fairly drunk, he was pretty confident at this point and you could smell it on him.

I should mention that I’ve been perpetually horny since I was a young teen and had already developed a few kinky fetishes. So when I admitted that the only reason I preferred Zoro was that I was sure he would be far more willing to choke me than Sanji. I think I gave Jacob all the courage he needed to make his next move.

“Hey, I’m getting thirsty and cold, wanna come with me to get a drink and get changed?”

“Sure!”

So sure enough I followed him to the kitchen, talking about pirates. And then I followed him some more.

It wasn’t until the door to the bedroom closed behind me that I realized, what I had just followed him into.

Dirty stuff starts here ***

So there I was, in a room with a boy in a towel, and as he started to move stuff off the bed and into drawers, I realized it was HIS room. He lived here. Turns out he’s the alliance member’s brother. When he finally turned back to me, I must have looked like a deer in the headlights and judging by the bulge of his towel, a semi was coming right for me.

I started to stammer apologies for not realizing I just followed a guy who told me he was going to get changed and I apologized for being a virgin and I apologized for dumping that on him and then I apologized AGAIN for being a virgin. After about my 6th apology in 5 seconds he calmed me down and told me it’s okay, we’ll just continue talking outside and he’ll get changed once I’m out the door… but the entire time I had been apologizing, I was just staring at that bulge of his towel. I had NEVER seen a penis in person before…I started to take deep breathes with my mouth hanging just a little bit open, my tongue badly wanting to wet my lips but staying at the edge of my perfectly straight teeth. And then I said it and my head exploded.

“Can I see it?”

I wanted to smack the smug, self-assured grin, right off his face but the only thing I could do to stop my hands from shaking was holding my unopened cooler tightly.

“Sure you can” Jacob said, as he uncurled the towel from his waist.

I’d like to say the first penis I saw was gloriously big with a perfect bulging vein running up the length of it, but it was amongst the smallest I’ve had. Around 5 inches (which is normally plenty to work with) but it was on the thin side. And yet he may as well have pulled out a gun, I froze up so badly. I had been fantasizing about dicks with every phallic thing I could find in my home while watching pornhub on my phone under the sheets, for what felt like decades at this point. So this penis was hardly the cock of my dreams, yet I was already getting wet and I could feel my face go flush.

Jacob was the first to speak, bless his heart. “Do you want to touch it?”

“Can I?!” I felt like he was doing me a grand favour and I leapt at the opportunity.

So Jacob sat down at the edge of his bed and told me to go ahead. I think all of the late nights watching Digital Playground while teasing myself with a hairbrush handle, taught me that when a guy sits at the edge of a bed, you kneel in front of him, so that’s what I did.

By this point, Jacob was perfectly erect and I was poking and gently stroking up the length of his cock with only the tips of my fingers, slowly working my way to gripping it with my entire hand. And as soon as I gave it one good stroke, a bit of pre cum trickled out of the end. Maybe it was instinct or maybe it was shock, but for whatever reason when I saw that bit come out, I pressed my lips to the end of his dick to lick it up. Like when you open a shaken bottle of coke the foam just rises to the top, you gotta do something to stop it.

Jacob let out a loud gasp of pleasure as it dawned on me that my first kiss was with a penis. He ran his fingers through my hair which was currently tied up into a bun, almost petting me. “You are so fucking sexy.”

Another compliment. That just revved my engine and I took his dick into my mouth. It was salty and tasted like chlorine but fuck did it taste good. It was everything I wanted so badly for so long. It would be a while before I could deep throat, but I took in most of it and got it as wet as I possibly could. Between his little moans, Jacob breathily said,

“Damn, you’re good at this, are you sure you’re a virgin?”

He knew the compliments were helping him and I didn’t care. It was around this time that I realized Jacob probably wasn’t a virgin and thus the perfect person to lose my virginity to. I think I startled him a little bit because in my mind I had already skipped a few steps, so my next question caught him off guard.

“My underwear is really embarrassing, can we turn off the light?” I started to jerk him off because that’s how the porn stars would have handled it.

Now it was Jacob’s turn to look like the deer, I mean, I was fully clothed but suddenly I wanted to get naked. He quickly recovered and had a devious smile on his face.

“No way, I want to see every last bit of your sexy body.” he pulled me up by the wrist and kissed me before I could protest. It was forceful, with lots of tongue and I absolutely loved it. I was terrified of him seeing my underwear but he kept pulling off my clothes. And kissing me hard whenever I tried to say something, but in his defense, I never told him to stop because I didn’t want him to. And to give him credit, he unhooked my bra before taking off my shirt so he could take off both without him getting a good look at them, and pulled my panties down with my jeans. Honestly, a classy move.

Once I was fully naked and only illuminated by his bedside lamp, I tried to cover up, it was the first time anyone had seen me laid bare. Jacob grabbed my wrists, locked them together with one big hand and held them over my head. I was completely defenseless. He peppered me with more compliments and kissed my neck and my ear (I learned that night it was a weak point of mine, and he made sure to take advantage of it) before gently running a finger up the lips of my pussy, his finger glistening after it’s first pass. I was drenched.

Before I knew what was happening, Jacob grabbed his towel and laid it under my hips and grabbed a condom from his side table. I covered my face and Jacob asked if this was okay. I only nodded. I’ll admit, this part hurt. I had damaged my hymen before but I guess it was still mostly intact because there was a lot of blood and a fair bit of pain. Thankfully, Jacob went slowly. This wasn’t his first deflowering. He talked me through a few moments of panic and eventually things started to feel good again. Just as I started to get into it and told him to fuck me a little harder, Jacob came into his condom. I guess the whole experience felt good to his dick, despite my tears.

We laid down next to each other for a while, making out, I cuddled up to him and we talked about random things in his room. Then I noticed something that made my heart drop, he had several text books on his desk, but 2 of them I also had, IN HIGH SCHOOL.

“Are you in High School?” I already knew the answer.

“For a few more months.” Chris Hansen alarm bells started going off in my head. But as if he could read my mind he said “I’m 18, I have been since October.”

My relief was palpable. Then I felt a little bad for my reaction, after all I had only been 19 for a couple of days. But I wasn’t going to start dating a high school boy when I was in University, much less a fellow Alliance member’s brother, rumours would spread like wildfire.

It wouldn’t be the last time I had sex with Jacob, but not until he joined us in University in the fall.

When I realized my phone was buzzing with about 20 messages from my best friend, who thought I left her there, I quickly got dressed and exchanged numbers with Jacob. I wasn’t going to complain if he sent me more compliments. My friend could figure out what happened once she saw me come out of the basement (where she already looked for me) and we talked about it once we got back to my house.

Although it was unsatisfying in the end, I think my first experience just left me hungry for more. I just didn’t realize how big my appetite would become. I became a real SLUT throughout University and even to this day to some extent. I think I’ll share some more stories if people like this one (I promise it’ll be shorter and dirtier). Like the time I tried to get revenge on a guy who bullied me mercilessly in High School, only to end up as his pet. Or the time I matched with the creepy old guy on tinder. Or having sex with my boss and ended up pimped out to his friend. It’s amazing how much trouble you can get into with low confidence.

Let me know what you think and feel free to DM me. I won’t say no to a dick pic or two (hell, I’ll probably masturbate to them).

EDIT: I just want to correct a misconception, the ugly duckling story is about a duckling that becomes a beautiful swan. By the time I lost my virginity, I looked much better than I did in adolescence. I’m very confident in my looks nowadays, but my low confidence got me into a lot of trouble once men started to look at me.

Source: reddit.com/r/gonewildstories/comments/re3cjs/the_ugly_duckling19f_loses_her_virginity_to_the