Since my last post had me boasting a little bit about my success of whiskey dick, I might as well flip the coin to show one of many times I was not so suave. Thank you to the people who read my last endeavor, I figured it’s hotter than shit outside and I need to relax so here’s another. The story is “gonewild” but it’s more just a failure of my sexual prowess. As per normal feedback is welcomed and if it doesn’t get you going hopefully you can get at least get a laugh today.
This story is about the conquest it took to lose my virginity. It’s not the greatest story nor is it the sexiest, but I have no care to exaggerate or boast. Spoiler alert, I did well enough to have sex again and that was pretty rad.
So myself and Melanie were in our late teens, and had been dating a few months. Young love & all that shit. It was both of our first serious relationships. Myself because I was too focused on other stuff to try to commit to the energy it entailed, and for Melanie because she was incredibly quiet and didn’t get out much. It was a win-win for me, she asked me out and didn’t seem like a pain in the ass and 5 months flew by quicker than I thought.
She was starting to think of the L word, while I was just stoked I got to grab some consistent titty.
Description time
**Melanie**: Last stages of her late teen years. 5’9 with legs to her neck ala Stacy Keibler but with more of a Melanie Laurent from Inglorious Bastards (Ironically also named Melanie) face. 120 pounds and therefore really thin for her height. She was taller than me and while other people had all sorts of issues, I did not mind. We can’t all be giants. Bright blue eyes that many friend had told me could turn into a haunting stare. Luckily I never got to see it go that sinister. Natural blonde hair to her tits, which were small enough they didn’t require a bra and made it easier for me to not have to fuck with bras all the time. She still produced a good mouthful of tit, with light peach areolas and a shade darker nipple about the size of a pinky nail. Although a sheltered person , she was a sucker for Daisy Dukes and her ass held their own in them. Her pussy was exactly what you would imagine a camel toe without clothing. A palm sized handful, clit completely hidden and not a hint of lips showing. To be honest it set a standard that freaked me out the first time I saw labia protruding.
**Myself** As stated in the other post, 5’7 and at the time right at 117 pounds. The only reason I remember is because it took me years to get past that exact number and it pissed me off. Short but messy hair, hormones didn’t kick in for facial hair yet but sure did for pubic, so that was shaven clean. I helped Melanie shave her inner lips for the first time prior to this occurrence, so she was completely shaven as well. Luckily, she didn’t have hormones for facial hair either. I’ve got green eyes, and people say the first thing they notice is my smile so I’ll take that as a good sign. Genitalia-wise, my cock is built like a Wii remote, so if you were looking for a chest-buster story, you are in the wrong department.
Back to the fun stuff. She was getting ancy about committing our love for each other and I wasn’t helped with Christmas season just a few months away, love in the air, all that stuff. After weeks of her wondering and questioning, I decide to say Fuck It, she’s awesome it seems logical for me to love her. She cries, we ditch our classes that day and make out and I get to see her completely naked for the first time and get a finger past her lips. She was stoked, I was stoked, all was huky dory. After a few hours of practice I get fairly okay with my hand and after playing Bop It with her pussy, she has her first orgasm ever. We do this a few times and she starts feeling the Christian-Guilt from her upbringing and her parents who were very involved with the church.
The nakedness stops and you bet Jesus’ ass that I wasn’t get a damn finger south of her belly button. I respected her wishes and told her I was never going to make the first move towards the next steps in our sexual exploration. I saw her limit, and it gave me an excuse to miss any cues she wanted something since I was/am pretty oblivious. I still got to dry-hump her while sucking face and touch some titty. That was a better outcome than Palmela Handerson, and she was genuinely cool to hang out with.
Fast forward a couple weeks to right before Christmas. I had family that lived 9 hours away and for whatever reason they wanted to do Christmas early. In hindsight it really fucked with my school schedule as I was gone for 8 days, but I digress. Melanie couldn’t go with because she had to stay around for school and her parents still had her leash on a little tight.
I was trying to be a decent family member with a group of people that I don’t get the opportunity to see much, so Melanie and I both agree that communication would be few and far between while I was with my family. I text her that I made it okay and I that I would call her to wish her a goodnight later in the evening. I’m like, 2 blocks from my family’s house of which I haven’t seen in a couple years and she decides to text me:
>“Well when you get back, I’m ready.”
This motherfucker just decided to play Lets Give DrummBumm Blue Balls, for 8 Goddamn days. I had the full Kevin Myers & Tara Reid reaction from American Pie, and I.Was.Pissed. Shall I mention my family are all strict huggers? It made for a real fucking fun time to try to not stab a hard-on up against Mee-Maw. Do I remember a single damn thing from that trip? Absolutely not. What were my Christmas Presents? The fuck if I know. All I knew was I had to get through 192 hours of obstacles to have sex.
Family time came and family time went over the next 192 hours. My direct family and I are driving back home at 4 p.m. therefore arrival is around 1 a.m. I make sure that she is 100% not fucking with me and is okay to stay up and wait for me otherwise I was going to have an aneurism if my cock did not penetrate something that night.
We get about 6 hours in, and a tree falls over on the freeway. That slows traffic down another two hours and I am sitting in the back seat mking a big deal about the difference of getting home at 1 or 3 a.m. and my Dad is thoroughly confused. I text Melanie letting her know the issue at hand, so she starts playing with me.
>“I am going to fuck out your 8 days worth of cum and ride you until we pass out from exhaustion”
Just the full gauntlet of dirty shit she must have Googled while I was gone, since she wasn’t one to say a cuss word let alone send a dirty text. Now I am trying not to choke on my drink and hide my cock that is burning through my jeans in the backseat of our Dodge Intrepid as she is having a blast sitting at home. She’s sending pictures of her shaving, warming up (since experiencing an orgasm jump-starts the masturbation train). The tension is built, Hanz Zimmer is at full Triple Forte with the Goddamn orchestra in the background. And how the hell am I supposed to live up to this climax?
We get home at ~ 3:30 in the morning. I’m sure we had lives to attend to the next day, but I sure didn’t care. My parents were of course not cool with me banging my girlfriend in their house, so I was going to have to sneak her in. Also, Melanie’s parents were a still a little wackadoodle and only let her drive to the grocery store & class, even though she could have signed up for the Military by this point, so I was going to have to pick her up. 4 a.m. comes and I still have not entered the sacred passageway. 4:15 I finally get her back to my house. Boy she could talk a big game, but once the situation was in front of her she sure crumbled. I was going to have to be the one to take control, and us two silly virgins were going to figure this shit out.
I started with what had to have been the world’s worst back massage. There was no passion in it, I didn’t give a damn about the tension in her neck, I just figured “This otta work right?”. Slap, rub, scratch throw some oil on it and every woman should be swooning right? Then we make out, and she is shaking like a leaf, and while a vibrating mouth works on certain areas of the body, it was strange as hell up top and was about as passionate as CPR to a Hypothermia victim. She finally calms down, gets a little flush in the face, I think I am solid. I slide a finger past her lips, just one, to make sure the baby factory is well oiled. Mind you this is also the first girl I had ever fingered, so while I kinda knew what I was doing, I had no idea what the hell I was actually doing. Sure I figured out how to get her to cum a few times, but I couldn’t tell you the directions. By this point I’ve got so much precum running down my leg I might as well have pissed myself. She seemed wet, I was leaking wet, finally down to business.
She wants to get on top and set herself down, perfect. I want to see her tiny tits bounce anyways, plus me having to do less work = good stuff. I roll the condom on in the most unsexy way possible just gawking lazy eyed and mouth agape at this magnificent being who wants my penis in her. After my sensual unraveling of the balloon (which of course the first time was inside out) she slowly lowers herself down in a squat position. Her heat was inches away from my cock, we both had no idea what it would feel like, but we would find out together.
Her lips open for my cock. I try leveraging myself up just an inch or so to help guide it in, and she stabs my cock square into her clit. 120 pounds of inexperience slamming onto my cock, with a lot more force than recommended for a first time penetration. Apparently she believed her hymen was more like He-Man in protection from penetration. Silly me has never stuck more than my middle finger into her pussy, and she only knew what I had shown her. A quick attempt at try number two, which we think maybe the condom had dried out, so a quick rip and switch was in order. As she lines me up right on the hole, she starts to squat at the tip, gasps and falls. She could have fallen to the left, and hit a wall. She could have fallen forward onto me. She could have fallen backwards onto the bed. Instead, She falls right, straight off the bed.
Of course, it all happens so fast that she hardly breaks her fall, and a tremendous thump rings through my dead-silent house. Me being to absolute gentleman I am, I bust up laughing as I help her up after making sure she didn’t seriously hurt herself.
Good tip of advice, don’t laugh when a petrified naked woman is in front of you and actively trying to sit down on your penis. It killed the mood. All my half-assed work and what I concluded was foreplay had come to this and the mood was gone. After consoling her and trying to makeup as best I can for laughing at her misfortune, she actually wants to try again, but gives me the reigns of control. Apparently whatever porn I was watching before did not help, since I was too stupid to use my hand to guide my cock into her womb. So I am just aimlessly jabbing at her entrance with her legs wrapped around my waist in my pitch black bedroom. She’s frustrated, I’m frustrated, we are just having a real blast with popping our cherries here. I feel like I find the magic spot, and upon pressure….holy shit this really hurts. I understand sometimes the first time can be uncomfortable the girl, but my cockhead was about to pop off. If this is sex, I’ll go back to abstinence fuck that jazz. She had dried up and indifferent to our opinions, her gate was closed.
We are both exhausted from a long day, it’s well past 5 a.m. and I see her point. She is on the verge of tears from disappointing me, I am pissed off and her pussy is dried up. I could have fucked a box of rocks with less pain than her womb. We decide to give it one more shot, and I decide that at minimum even if I fail tonight, the woman deserved some mouth love (which in a rush I had skipped over the first time).
Finally, I am a little more relaxed with her thighs between my head, and even if after 8 days all I get is to eat some delicious young, pure from any outside source pussy, it was worth the wait. I briefly mentioned in my last story my great enjoyment of eating pussy, and I believe it all started right here. I am having a blast down south, she is finally moaning for the first time the whole night and I pull myself and position my cock for the final stretch. This time I figure out my thumb can be used to guide my cock in, and after putting on condom #3 that night I get myself in. It wasn’t smooth, it wasn’t super slow, and it was still tight, but holy hell was it warm, it was wet, and her eyes exploded with fireworks and passion when I bottomed out into her. This may not have been the perfect time, but at the millisecond I bottomed out and we locked eyes, I knew I really did love her. She professes her love for me, I tell her I love her back, a handful of pumps pass, she moans my name loudly a few times and 8 days of teasing, a lifetime of buildup, and boom goes the dynamite. The whole time inside her marvelous pussy was less than the time putting on 3 different condoms, but by dammit I had sex and I didn’t feel bad about it. We got a taste that night and every microsecond was worth it. I pull out and we snuggle in the bed saying all sorts of cutesy shit and are happy it was finally over. We beat virginhood and won.
What happened afterword killed the endorphin’s. We are cleaning up a little and prepping to go to sleep since we were both exhausted mentally from the sex and physically – not from the sex- . We set the sheets, and somewhere around the room logically should be a condom filled with some DrummBumm Cumm. We tear apart the entire room, killing any hopes I had for round two as all the giddiness is gone and Melanie is freaking the hell out. It takes us much longer than it should to realize the obvious, the condom was still up there. When I had cum, I stayed inside for a half minute or so giving me enough time to soften up, thus letting me slip out from the condom.
No porn I ever watched showed this side before. What the hell do we do? I told her to try to pee real hard in the bathroom, jump up and down, wiggle, the works. You can picture two terrified freshly unviriginized folk trying to figure this out as the sun is rising in the background without trying to make too much noise to wake my family. She couldn’t reach up and grab it for whatever reason, therefore I was recruited to be the final savior in retrieving my lost soldiers from within the battle field. This was also the first time I had ever stuck more than 1 finger into a vagina, let alone trying to pinch a rubber together with the technique of a lobster claw.
How I ever was granted the opportunity to have sex with her again was a true miracle, but I am forever grateful. I had to buy my first Plan B pill the next morning, but I also received my first blowjob, which I will count as a win.
Our lack of technique was beaten out of us by humping like Guinea Pigs for the next few months afterwards, in which there might be a good story or two out of it. Like most first loves things fizzle out while people are young and stupid. Last I saw of her she made me a sandwich at a Port of Subs years later, which I will count as a final win to that relationship.
Thanks folks!
**Tl;Dr : Girlfriend told me she was finally ready for sex when I was away from her for 8 days. Upon arrival virgin sloppiness ensued and I lost the condom inside of her. Doesn’t matter had sex.**
Source: reddit.com/r/gonewildstories/comments/6ijrmf/after_192_hours_an_11_hour_car_drive_i_loose_my
It took me so long to read this. I couldn’t stop laughing. Great tale.
Agreed ^ I enjoy a good laugh to a sexual story more than a hot and heavy and this definitely delivered. Your use of comparisons were absolutely hilarious. The fishing out of the condom like a lobster claw had me rolling.