Okay, so I am a long-time viewer of this subreddit, but this is my first ever post, the most recent quarantine having pushed me over the edge as my boredom and horniness increase exponentially. This is not your normal perfect scenario r/gonewild post with multiple orgasms from both parties, but I think that the story is interesting and unique enough to be given a platform to be shared on.
## Before all of you start screenshotting this post and plastering my account all over r/thatHappened, please stop to consider that the reaction that this story provokes is the whole reason I want to share this with all of you.
I’m going to be providing quite a lot of context, so I will place an asterisk line (***) where the juicy part of the story actually begins. The reason I have added so much context is to give you a better idea of what it felt like for me and how the night I lost my virginity was a culmination of events spanning nearly 2 years.
I was the skinny nerdy kid growing up and was unbelievably shy throughout my secondary and high school years, barely taking to anyone, let alone the opposite gender. I was deprived of female contact for the first 18 years of my life, (this happened not long after my 18th birthday) and I had only kissed one girl about 4 months previous.
I was tall, with dark curly hair, tanned skin and glasses – which makes me sound much more attractive then I was, (picture a young Stephen Hawking if he lived a little further east). I was active but extremely skinny until I was about 17, when I started going to the gym, which was honestly a god send, as without the working out I would put money on my virginity being intact even now.
Going to the gym improved my confidence 10-fold as well as making me look better as I started to take more pride in my appearance, so the attention from girls finally started coming my way, which I was wholly unprepared for, as you will hear about later on.
My first meeting with the girl in this story was at my first house party. As I have loosely described myself, I will now describe her, (let’s call her Immy). Immy was the polar opposite of me, where I was shy and nerdy, she was outgoing and popular. Immy was about 5 inches shorter than me, with long brown hair, big brown eyes and a gorgeous slender figure and tiny, cute tits. She was good-looking and she knew it.
Right from when Immy got to the party, she made every effort to get as close to me as possible, which was weird to me at the time, as we had never spoken before (although we shared a few classes). Every time I would go to get a drink or speak to one of my few friends at the party, she would ease her way through the crowd, right to my shoulder, to the point where I began to take notice.
We made eye-contact several times and after 3 or 4 times she beckoned for me to come and speak to her in the garden, away from everyone else.
At this point my heart was in my chest as I had never kissed a girl before as I took what felt like forever to walk to where she was standing.
The conversation, to the best of my knowledge, was as awkward for her as it was for me, as we very quickly realised that we had nothing in common whatsoever and I lacked the conversational skills to spark anything and the resulting conversation ended up something like this:
“Hey”
“Hey”
“How are you?”
“Good, you?”
“So how many times a week do you go to the gym?”
“6”
“Wow, that’s a lot”
I could probably try and write down more of the exchange we had but I would just involve lots of silences and the same question repeated about 4 times.
After about 5 minutes of the single most painful conversation I have ever had in my life, Immy got as bored as I did and pulled me towards her by my shirt for a kiss.
This is where I panicked, the significance of this situation became overwhelming and my body and brain simultaneously turned to mush. As she pulled me in, I pulled away, so when she leant in, hands clawing and my t-shirt and the intoxicating smell of her perfume became even stronger, I just sat there frozen, which stands uncontested for the most pathetic moment of my life.
Safe to say after that interaction, Immy got up and left me, whilst I sat in the garden of my first house party feeling like the world’s biggest idiot.
The day after, back at school, Immy pulled me aside after one of our lessons together and apologised for making advances on me the day before, blaming intoxication, which did nothing to heal my pride.
The reason I have elaborated so much on the moment me and Immy met is not without reason. The way my hormonal body worked back then and the way I work even now, is that when someone displays affection or any interest in me, my feelings for them increase by 1000%.
So you can imagine, the fact that first girl to ever try and kiss me was someone so popular and good-looking I had dismissed them as being out of my league long ago left me with the biggest crush I had ever had on a girl to date, which is important for the build-up in the next part of the story.
After that, communication ceased between us for a couple of months, until the summer, where she messaged me on Instagram one day out of the blue. It was only a simple hey but from there the conversation moved over to snapchat, where we would start messaging and lightly flirting for a couple of months (another first for me) which only strengthened my feelings towards her.
At this point, Immy was my full-blown crush and I could not get her out of my head, the constant mixed signals that she sent my way just adding fuel to the fire.
Then, after a few more months of talking and late night conversations, (staying up on FaceTime to celebrate her birthday), disaster struck when in conversation with a group of people the topic of Immy’s boyfriend came up, which shattered my perceived chance of anything happening with her.
For almost a year, we stopped speaking, as she continued to date her boyfriend, our conversation limited to catching each other’s eye in lessons or in passing. Just enough time had passed so that I had started to lose interest in her and by this point I had kissed my first girl and had gained much more confidence.
Then, 6 days before my 18th birthday, I was with a group of friends on the way to football training when the topic of girls came up, as they normally do. I was half paying attention to the conversation, as they were talking about girls who I had no real interest in, so I wasn’t really zoned in.
That was until Immy’s name was mentioned. My interest was immediately piqued and I listened, with butterflies growing in my stomach, awakened after all this time as they talked about how Immy’s boyfriend had cheated on her and they were no longer together, (as bad as that sounds). I could barely contain my nervous excitement and although I had not spoken to her in a little over a year the possibility of being able to talk to her more excited me beyond comprehension.
As if by magic, the day after this conversation, Immy’s name once again appeared on my phone screen, the same message she sent to me the first time we started talking and we started talking again as if we ever stopped.
This time however, for whatever reason, we started to grow much closer, in a weirdly flirty best friends’ kind of way. We would FaceTime every night, which was slightly awkward at first but relaxed into a normal part of our daily routines which we grew more comfortable with each other.
Every chance she got, she would facetime me and tell me about something, which made fallback into the same intense feelings I had for her well over a year ago.
The one thing Immy would do that would drive me crazy however, would be the number of mixed signals she would send me.
One day it would be her sending photos of her in her underwear hinting that I should come over and the next day she would be round another boys house.
It had got to the point where she was all I would think about and looking back on it now, I am genuinely scared for my younger self and how much I thought about her, we often joked about how being her friend was like a full-time job as I had to commit so much time to talk to her.
Whilst I was still battling these feelings, she was still teasing me and it got to the point where we exchanged nudes one night and I felt on top of the world and I finally felt like I could make a move on her and get the kiss that she had offered me so long ago.
That was until the day after, where yet again she was in the back of another boy’s car and it was the final straw. I stopped talking to her for a little bit and I decided that enough was enough.
We didn’t speak for a few weeks and I started to talk to other girls and I think Immy sensed this, as after a few weeks and the realisation that I was genuinely moving on, she started to flirt with me, more heavily and without the part where she would meet other boys in the back of their car the day after.
We started to flirt more heavily and she started to invite me to whatever she was doing that night, where she would always ask for the jumper that I was wearing, ‘because she was cold’ until she amassed a collection of my hoodies that was bigger than my own, all the while becoming more and more suggestive, day after day.
At this point, we were going to the same gym, so she would start asking if she could come back to mine with me as she wouldn’t be able to be picked up for a while.
This happened several times, with it being nothing more than us sat at the opposite ends of my bed talking, each time leaving me wanting her more, until she started asking to come to mine during the weekend, just so we could spend time together. Nothing ever happened during these, but it didn’t stop her from flirting with me every chance she got.
It got to the point where I wondered if this was our ceiling, relationship-wise until one night, when she messaged me out of the blue asking if she could come round, to which I obviously said yes.
When she finally came, rather than just being on her phone, she made a show of leaving her phone in her bag as she hopped onto my bed and ever so slightly, cuddled up to me as a put on a random show I had no real interest in, (coincidentally it was the same one I was watching when we sent nudes to each other). Rather than talk like we normally did or make jokes, we just sat watching in silence, as Immy started to cuddle up to me more, putting a hand around my waist and resting her head on my shoulders, so that I could feel each breath that she took.
I can honestly say that at that point, I had never been more excited and nervous at the same time – bear in mind that in my head it was like nearly 2 years of me knowing Immy had led all up to this moment.
Then, just as I was mustering the bravery to reach over and ask to kiss her, her phone vibrated, and her friend called her about an emergency she was having. Much to my dismay, she very apologetically left, leaving me feeling teased in a way that I don’t think I will ever experience again.
After that night however, on a positive note, the mood between us shifted and the flirting increased even more, (yes, I’m aware that I sound like a broken record at this point).
At this point, as was confident enough in our friend/relationship that I was going to take the first chance that I got, because all of the months of build-up of flirting and my feelings was practically choking me.
As if by magic, as if it was meant to be, one day my mum casually mentioned to me that she was going away for a day and that I would have a rare free house for a night.
As soon as she said this and despite her explicit instructions to do otherwise, I dangled that piece of information in front of Immy, hoping for a bite, which I got.
Much to my despair however, she suggested inviting over a group of our mutual friends, which I reluctantly agreed to as I did not want to come across too strong.
With the date set, the build-up to the day felt like a lifetime, with my mind conjuring up scenarios at every spare second. Our messages became flirtier and less subtle, with photos of each of us in various states of undress being exchanged on a daily basis.
Finally, the day came, and I woke up in an intoxicating feeling that I can only describe as a cocktail of excitement, nervousness and anticipation.
I was out with my family for most of the day but me and Immy were messaging back and forth the entire time, with her sending me various photos of her only wearing one of my hoodies, which could’ve honestly made me cum there and then.
Those photos, combined with the suggestive messages only increased the build-up of those emotions that I could fill in the pit of my stomach – hell, even typing this is bringing back that same feeling.
Once we had got back home and everyone else in my house had left, I went into overdrive, making sure the house looked good for when people came, buying condoms and using the internet for sex tips – honestly not the best idea. I was just doing anything I could do to distract myself.
After what seemed like hours, just as I was finishing setting everything up, the doorbell rang. All those feelings that I had suppressed for a couple of hours all suddenly resurfaced, and I had to fight their appearance from my face as I opened the door.
There were 5-6 people at the oor, but there could’ve been 20 as I was only focused on one of them. Immy looked amazing, with a tiny white tank top and tight grey joggers as she beamed at me whilst entering the front door.
After composing myself, iI set about being a gracious host and showed everyone to the living room, where someone took control of the music and another set about pouring some drinks.
As the night progressed, the drinks started to flow at a quicker rate and Immy took every opportunity she could to drop little hints, brushing past me every time I walked past her, touching my arm or my chest whenever we were having a conversation and then making every excuse she could to lie on me, or place a hand on my thigh or whisper in my ear.
It was at the point, one of my friends[Ryan], who was very close to one of the friends Immy brought, must’ve had an idea about what was about to happen and tried to subtly hand me a condom under the premise of us just shaking hands and acknowledging each other.
Unfortunately, or fortunately if you look at the outcome, Immy saw that Ryan had passed me something and tried to get to the bottom of what it was.
“Ummmm, what was that”
“What was what”, I shot back, exchanging an embarrassed look with Ryan, who looked a little sheepish.
“I saw Ryan hand you something” she said in a tone that made my veins turn to ice.
“It was nothing”
“No, don’t lie, I saw something”, she said.
“What was it?”
“Was it a pill?”
“No, trust me”, I said, trying to assure her and get out of the situation.
At this point, Immy got fed up of asking me questions and started trying to pry the condom out of my hands.
Reluctantly, I gave in and let her take the condom out of my hand.
At this point, time stood still as we stared at each other, trying to gauge one another’s reaction.
Then, just as I was about to open my mouth and apologised, Immy pulled me in and we collided, grabbing at each other as we started messily kissing each other, sliding one tongue across the other as Immy started to bite my lip and moan slightly, which nearly made me implode on the spot.
As aforementioned, I had only kissed one person before, so I let Immy initiate the rhythm, trying to kiss and bite and use my tongue in time with hers. After about 10 seconds, I got more confident and held her face in one hand and pulled her in to me by her waist with the other, initiating another moan and bite of the lip and causing the pace of the kisses to increase, as I struggled to keep up.
After about a minute, we both stopped and momentarily pulled apart and for the first time what we had just done properly hit me.
With a coy smile, to mask me nervousness I asked Immy if she wanted to come upstairs with me. Without missing a beat, she said yes and we both clambered up the stairs into my bedroom, barely letting the door close before we were on top of each other once again.
Trying to take a bit more control, I pushed Immy onto the bed and straddled her legs, using one of my hands to pin her arms above her head [thank you sex advice from the internet] as my other hand carried on exploring her body.
Over the next hour, we spent the entire time making out, moans becoming more frequent as we slowly started to undress, taking of each other’s clothes agonisingly slowly.
We rolled around my bed, using the other persons moans to gauge each other’s sweet spots, on the neck, by the ear and on the cheek as we carried on whispering filthy things in each other’s ear, which would only fuel the intensity of the kissing as we released months of built up tension and let our fantasies play out.
Immy straddled my waist and took of her bra and I started to kiss and suck her tiny tits, leaving tens of love bits all around her nipples, eliciting short, sharp moans from her as I manipulated my approach based on her moans.
All of the kisses and the moans had built up and I had never been more turned on in my life, so I pushed Immy off and took off her joggers. Lying next to her, I carried on the barrage of kisses, all over her face, neck as my hands slowly creeped closer to her panty line, drawing a sharp intake of breath from Immy.
At this point I was absolutely terrified because I had no idea what to do with the complex system that was the vagina. Whist still maintaining the intensity of the kisses, I started to slowly rub around the area where the clit was supposed to be, causing Immy to seize up and start to moan faster.
These moans gave me more confidence and I slowly inserted a finger inside of her and then another one before starting to move them in and out slowly, in the way I though was best [in hindsight, it was a mess] which caused Immy to start moaning faster and fumble for my joggers and boxers, ripping them off in one.
Now it is at this point that things started to go sour. If you’ve read up to this point you may have been thinking that it was so far, so good. I would attribute this to dumb luck as looking back on it I was all over the place. Immy was much more experienced than I was, so I let her take control as much as possible as I had no real clue what I was doing.
It would now also be worth mentioning that it was at this point, things start to sound made up, so bear with me. I am very lucky in the dick size department; I am about 8-9 inches when fully erect and I can barely get my full hand around the bottom of my shaft. I knew that my dick was big but because all my experience of sex was from porn, (again a bad idea), I thought that there were no negatives to having a big dick and that it just increased the pleasure for the lucky recipient.
I was very wrong.
We had already sent nudes, so the size of my dick was of no surprise to Immy, who took of her panties straight after she took of my boxers and spread her legs to adopt the missionary position.
I rolled a condom onto my dick [something I had practised before everyone came round] and slowly tried to slide myself into Immy.
It took 2-3 minutes of gasps of pain and me being as gentle as I possible could to be fully in Immy, at which point she looked to be in extreme discomfort. Scared of hurting her, I asked if she wanted to stop, to which she dismissed, before asking me to be very careful.
I started off as slow as I could, with absolutely no rhythm as Immy kept gasping and gripping my arms and back, not looking to be enjoying it whatsoever.
It was at this point I asked if she wanted to stop again, to which she again dismissed and told me to go faster, which I did.
Immy released a cry of pain and mortified, I took my dick out of her and watched in dismay as she started crying.
At this point I was convinced that it couldn’t get any worse, as I went about trying to console her and comfort her to which she willingly accepted.
I kept saying how sorry I was, to which she would murmur something about it not being my fault.
After what felt like an eternity, Immy had stopped crying and suggested that we go again, this time with the condom off, (easily the worst idea of the night). Again, I tried to slide my dick into Immy, but with the same result, to which I removed myself from her and began my apologising routine, which I knew was futile, but I didn’t know what else to say.
Immy then put her clothes back on to go to the toilet before she then came back into my room and cuddled up to me, smiled and just said that practise made perfect and we would just have to try again another time.
We stayed friends but 2 months after this, Immy got back with her boyfriend and we haven’t fucked since.
Source: reddit.com/r/gonewildstories/comments/kqjmdd/i_couldnt_lose_my_virginity_because_my_dick_was