Letting my [M]Virgin Coworker Test his V-card Chip on my [F]Holes

This is what happens when I try to write a “shorter” story lol, oh well.

This story happened when I was 18 (21 now) and working my first full time job at a sort of gas station/rest stop/food court place. Most of my coworkers were guys between the ages of 18 and 25 and the majority of them were obnoxious assholes who clearly didn’t want to be there and would do the bare minimum on a good day. I’m a whore, but I still have SOME standards, and I tend to avoid people who make my life difficult.

There were a few exceptions though, and one of them was such a sweetheart that he quickly became my favorite to work with. We’ll call him Mike, and I think he was about 23 at the time. Mike wasn’t all that good looking, intelligent, or even funny, but he was a hard ass worker and an incredibly kind and considerate person. He was the type of person that, when surrounded by mostly lazy assholes, was an obviously easy target to take advantage of and bully, and he definitely got his fair share.

I can’t say I felt exceptionally bad for him because he never seemed to bother to stand up for himself in the slightest, but it was also obvious that no one had ever taught him how. Since I’m a bit of a caretaker at times, I would occasionally find myself fighting some of his smaller battles for him. I didn’t really want to, but I just couldn’t help myself watching him get verbally pummeled and shamed by the other assholes we worked with.

At one point some of the other guys got it in their heads that he was either a virgin, asexual, or in the closet, because he would NEVER talk about anything sexual with anyone – never a mention of dating apps, hookups, sexual experiences of any kind, etc. I think the only other girl who worked in our store section of the rest stop had spread some shit about him too, but I never figured out if it was true or not.

I overheard him taking shit one day near the end of our shift and I don’t know if it was just a long day, or if I was in a fightin mood, but it was pissing me off more than usual and I decided to get involved. I came out from the back into the main room with the register and saw him organizing the coolers about 10 feet away from me with 2 of our other coworkers (Dave and Josh) standing next to him, not doing their jobs, and relentlessly mocking him about “not ever getting pussy”.

As usual, he was pretty much just sitting there and taking it, clearly extremely uncomfortable and wishing it would stop. Dave said something like, “No seriously, Mike, I’ve got three girls all competing for my dick tonight and I need to drop the ugliest one and make sure she never talks to me again, can you tell me your secret?”. Josh started laughing and chimed in with, “dude, just show her a picture of his micro penis and you’re good”. Dave responded with, “nah I’m good, I don’t wanna be the first person to see his dick”.

That was it, I hated these fucks and wanted them to eat their words, so I said, “I gotchu Dave, give me her number and I’ll send her a picture of Mike’s dick. You can’t see half of it cause it’s in my ass, but I think she’ll get the message and leave you alone”. Josh laughed, clearly not buying it, but Dave went quiet for a second and was likely trying to figure out if I was serious. Dave had tried to hit on me and fuck me when I first started working here, and even sent me a pathetic dick pic before I blocked him, so I shut that shit down real quick when I learned what a fucking douchebag he was. He was definitely still butthurt about it.

“You fucked Katie?” Dave asked with an incredulous look on his face. I could tell that, for at least a brief moment, he was wondering if Mike’s quiet and meek demeanor wasn’t actually a sign of weakness, but instead a kind of confidence-induced apathy that a man displays towards people he knows are beneath him, and has no need to bother with. Dave actually looked momentarily threatened by the idea that Mike may not at all be the person he had assumed him to be, and that he might make a fool of himself if he tried to argue my claim.

“Wow, you fucked a whore” He conceded. He paused briefly, as if wondering whether or not he should risk saying what he was about to. “Was she as cheap as she looks?”, he practically stuttered with an obvious lack of conviction and commitment to the insult.

I could tell that a breeze would knock him over at this point, but I wanted to embarrass and shame him into crying himself to sleep tonight as he tried to imagine he wasn’t a total waste of life. I put on a dead serious face with a healthy serving of genuine pity, looked him right in his insecure little eyes and said, “Hun, all it costs to fuck me is an adult-sized dick, which is why you’ll be working your Bathmate again tonight while Mike tries to work the rest of his dick in my ass”.

He tried to hide it, but I caught a little smile escape from Mike’s face. Dave started to say something, but I cut him off and almost yelled, “get your fucking broke, baby dick-having ass out of here before I show it to the cops and they have you arrested for child porn”. Josh broke out laughing, possibly just trying to make sure I didn’t come for him next, and Dave looked like he suddenly realized that all three of us were against him, and that he was going to dig himself deeper if he stuck around. I can get a little scary when I’m angry, and he definitely caught a glimpse of something in me that he knew better than to continue poking.

He made up some bullshit excuse about how him and Josh get to leave early while we’re stuck closing, no doubt trying to salvage his crumbling ego, and walked out of the store. Mike looked like he really wanted to say something, but just couldn’t work up the courage. “Spit it out, dude”, I told him. He sighed and reluctantly said, “thanks, but they’re right, I’m a fucking virgin”. Damn, I wasn’t expecting that, and I don’t think I’d ever heard Mike swear before lol. It wasn’t the kind of confidence that usually gets my juices flowing, but the way he said it demonstrated an ownership of his predicament that I couldn’t help but respect at least a little. But he wasn’t done, he turned his head to look me in the eyes and asked, “would you seriously fuck me?”.

What the hell was going on? The image I had made up of Mike’s dick in my ass was suddenly flashing through my mind as if it actually happened, and I had this sort of pained regret that it wasn’t a real memory, as well as a building curiosity of what it might look like if it were to happen for real. I had never really considered fucking Mike before because he seemed like the kind of guy who was incapable of fulfilling my rule of being the initiator and, frankly, I also thought there was a very good chance he was just gay, and in the closet still.

My caretaker side was at war with my whore rule, but my body was telling me I should figure out a way to take advantage of this opportunity and help him out. “Do you want to fuck me?” I asked, half expecting total silence in return. His face went pale, and I could only imagine he was thinking, “oh shit is this about to happen? What if I suck, what if I embarrass myself, what if I…” Whatever he was thinking, he was definitely frozen in his head, but I could also see his eyes look over me as if his body was desperately trying to pull him back into the moment, find his momentarily misplaced V-card, and hand it to me.

I reached under the counter where the register was and pulled out a half-empty bottle of Tito’s that one of our managers would break out and “sneak” sips out of when things were slow or stressful, placing it on the edge of the counter near Mike. I started walking toward the back room door, turned to him and said, “if you want to fuck me, you have to come take it. I’ll be in the back for 5 minutes”. I almost felt bad putting so much pressure on him lol, but I figured hey, all the guy has to do is slam a few gulps of liquid courage and manage to follow me into the back within 5 minutes, and my holes are all his. Can’t make it much easier than that.

I took a seat in an area of the back room, which is a sort of rinky-dink employee lounge area with a couple chairs, a mini fridge, and a countertop with a microwave on it, and suddenly I felt myself get nervous. It wasn’t that I was nervous to fuck, it was that I was nervous FOR Mike lol. I so badly wanted him to capitalize on this moment that I found myself emotionally invested in his choice. It seriously felt like I was watching Frodo decide whether or not to cast the ring into the fire lmao.

A minute or two went by and, despite the fact my heart was pounding through my pussy at this point, I had almost fully convinced myself that there was no way Mike was going to take me up on my offer. Even so, I was still going to sit here for at least another few minutes and imagine his dick inside of me.

Another 3 minutes or so went by and, just as I was about to give up and finish closing up, I heard the door creak open. Seriously, had he set a fucking timer on his phone or something lol? Cutting it close there, Mike! I supposed he needed the time to psyche himself up and maybe even catch a decent buzz with the Tito’s I left for him. Whatever the reason, he slowly entered the room, not making eye contact and said, “sorry, Katie, I’m extremely nervous”. Shit, was he telling me he was too nervous to fuck me? I was going to try and get clarification before he continued with, “can I play with your boobs?”. Good enough for me, I guess the liquid courage had done its job after all!

I stood up out of my chair and quickly pulled [my tits](https://imgur.com/a4XUOlJ) out for him, looking him in the eyes as I teasingly squeezed and fondled them. He wasn’t meeting my eyes though, as his gaze was fixated on my soft, perky tits and rapidly hardening nipples. I pinched one hard and pulled it in an outward motion toward him, almost as if I was trying to move my body closer to him without actually taking a step forward. His hesitance broke, and I could see that familiar male instinct flood his being – the one that never fails to kick in when a man’s body recognizes and embraces an opportunity to reproduce.

He moved toward me, his eyes never leaving my swollen teenaged tits, and almost tripped over the other chair as he reached out with both hands and squeezed them roughly like he was trying to pop them. I didn’t care, as I love being groped like some kind of toy, and I found myself watching his work – the firm, fatty tissue of my breasts bulging out between his spread fingers as he worked them in such a way that I could only imagine he was trying to cover a lifetime’s worth of tit-fondling in a single moment. He clearly wanted to remember and make the most out of this experience. I took a step toward him and gently pressed the palm of my hand on the bulge of his work slacks, thrilled to find what felt like a good-sized, and FULLY rigid cock straining to be set free.

He briefly pulled just his hips back from my hand as if forgetting for just an instant that, in this moment, this was no longer his “no no square” lol. As his hips came back to where they had just been, correcting his mistake, I met them with a firm squeeze and stroking motion of his shaft over his pants. “Oh my God” he exhaled in a breath that smelled of Tito’s and Funyuns. Yummy! I moved forward to give him what I assumed might have actually been his first kiss. I normally wouldn’t find it absolutely necessary to kiss someone who’s about to fuck me, but I really wanted to give him the most comprehensive experience possible.

His hands moved to my ass and pulled me in as our lips met, squeezing my butt cheeks in the same manner as my tits, and getting me genuinely worked up in the process. I took my hand away from his dick momentarily to pull my leggings down beneath my butt so he could grope my bare skin. Our kiss continued as I felt his fingers slowly inch their way toward my holes with each squeeze, no doubt testing to see what he could get away with, and I moaned a little to reassure him. You can get away with anything dude, just go for it lol.

He wasn’t a terrible kisser, actually, and I wondered if maybe he had at least kissed someone before this, but my thoughts were interrupted when he suddenly moved one of his fingers directly on my butthole and pressed hard – not hard enough to get inside, but enough to feel the muscle of my hole give way to his pressure. I love it when guys do this. I groaned, and my slutty little body was suddenly over the foreplay and needed to be filled. “Get your dick out and fuck me” was all I said as I broke our kiss, looked him in the eyes, and matter-of-factly bent over the counter to give him access.

“Can I see what your mouth feels like? I’ve never had it sucked before” he said, obviously referring to the dick he was now nervously taking out of his pants. I turned back around to face him and his eyes went down to my shaved, puffy little pussy, now clearly visible to him from this angle. His hands seemed to find themselves, the view of my young pussy no doubt reinvigorating his lust and purpose as he reached into his boxers and grabbed himself before pausing again to look up at me. “I hate my dick…” he admitted with a pained expression. I suddenly found myself wondering if something was wrong with it, was this his problem all along?

My own lust and curiosity propelled my body forward and onto my knees in front of him, it couldn’t be that bad right? I had to see it. “I’m sure it’s fine, let me see” I said. He hesitated for just a second before pulling the whole thing out in an instant as if he thought revealing it quickly would be like tearing off a bandage. I studied it with a determination to figure out what he was talking about, but there was absolutely nothing wrong… It was a solid 7 inches, uncut, straight, with better than average girth. What the fuck was this guy on about? I swear, guys these days apparently think that porn dicks are the standard, so sad.

I demonstrated my approval by taking about half of it into my mouth and gently sucking, licking, and moving it in and out of my mouth – trying again to give him the full experience. He moaned and said, “oh my god you’re amazing, Katie”. Thanks babe! I brought my hand up to stroke him while I sucked but I guess that was a little too much for him. I was hoping the Tito’s might prevent him from cumming fast, but it wasn’t meant to be. He pulled back from me saying, “shit hold on, sorry!”, and I watched a jet of cum shoot out and onto my tits before I quickly moved toward him, taking him back into my mouth and making the most out of his orgasm with firm tonguing on the underside of where his shaft meets his head. That cum was mine, and I wanted his first orgasm with a girl to be a good one.

He groaned and jolted as I milked the rest of his cum from his balls and swallowed. “Fuck!” he practically shouted as I pulled back and looked up at him expectantly. “Can we keep going?”. Well would you look at this little stud lol? I answered him by immediately resuming my blowjob, reveling in the taste of his cum as I focused on his shaft and tried to avoid overstimulating the sensitive head. He never even started to go soft, this guy was intent on seeing this through lol.

I stood up and bent back over the counter, never leaving eye contact, and said, “Mike, get over here and fuck my brains out”. He practically lunged over to take his place behind me, moving the tip of his dick to my taint (where was he aiming?) and firmly pressing in as if playing a game of “which hole will it land in?”. For a second, I was expecting it to just force its way into my ass, but my pussy beat it to the punch and opened up for him as his cock found its way inside of me. Congrats, Mike, you’re officially not a virgin anymore!

He started fucking me in slow, long strokes, almost removing his cock completely between each thrust. Again, I assumed he wanted to really feel everything and cement it in his mind in case this never happened again lol. He wasn’t touching me with his hands though, and he had me wondering if maybe he was afraid to touch me too much, poor guy. I reached my hands back, found his, and placed them on my butt cheeks. He spread my butt open just a little bit, and in a manner that indicated he wasn’t sure if this would be okay to do, likely trying to get a better view of my holes and check off more boxes for his entry into the world of sex.

He picked up the pace a little, and I really wanted to try and squirt for him, but it just wasn’t going to happen, so I decided to make it more fun for him in another way. The next time he spread my butt open a little, I collected a good amount of spit on my fingers, reached back, and started fingering my asshole for him. That did it, and he finally spread me open with confidence to watch what I was doing, repeatedly taking his cock all the way out, watching my pussy snap shut, then forcing it back in. He was definitely having a lot of fun now.

“Omg that’s seriously so hot, can I try?” he asked as he removed his cock from me again. “You better!” I gleefully replied. I reached back and spread my holes myself this time, assuming he meant he wanted to try watching himself finger my now puckered little butthole as he stretched my pussy with his cock. Instead, I felt the tip of his dick find my asshole and push, causing it to almost instinctually swallow what he was offering – my ring giving way to accommodate him into the softer, but tight and pink flesh behind it.

He stopped at about the half way point, possibly concerned with hurting me, and asked, “can I keep going?”. UGH! JUST FUCK MY ASSHOLE INTO AN EARLY GRAVE, FOR THE LOVE OF GOD, is what I wanted to say lol, but I took a more helpful and encouraging approach by saying, “Mike, I want you to use my tight little butthole to make yourself cum, okay?”. He definitely interpreted that as a kind of dirty talk he was supposed to respond to in kind, but didn’t seem to know what to say, so he paused before saying with a little laughter in his words, “you are like, my dream girl”. Very sweet, but shut up and fuck your cum into my slutty asshole.

He took my words to heart though, and slowly forced the rest of his cock in me before bottoming out, holding it there for a moment, then pulling it all the way back out of my hole. He must have really enjoyed the sight of my butthole repeatedly closing as he pulled out, then swallowing him as he pushed back in, because he continued to do this for another 30 seconds or so before I realized that maybe I could actually squirt from this. It was the perfect mix of pressure then release, which is the kind of thing that is most likely to make me squirt. I started rubbing my clit as my orgasm reached the point of no return, hoping he would continue exactly what he was doing so I could gush for him as I came. As soon as he felt my cumming asshole clench around his cock though, he grabbed my hips and practically started jerking himself off with my body, keeping his cock buried in me and groaning as he blasted my insides with his cum in unison with my own surprisingly massive orgasm. I really love being used.

The pressure that had built up was intense, and the moment he let his cock slip out of me I pushed hard and felt both his cum and my own gush out of my body in a sublime sensation of release. This virgin just creampied my ass and made me squirt! What a perfect end to this experience. “Woah!”, was all he could manage as he watched his cum and my own leave my body and spill onto the floor. I don’t think he was at all ready for that lol!

“Omg, nice fucking work dude”, I breathlessly said as I pulled my clothes back on and started cleaning up the mess with a nearby paper towel. He just sorta stood there, clearly not knowing what to do next, his sexual energy released and his balls drained. “Maybe we can do this again sometime”, I said as I gave him a little kiss and motioned for us to get back to work and finish closing. “Fuck I should have taken a pic or a video or something” he said as we made our way back into the front of the store. “Next time, babe”.

Source: reddit.com/r/gonewildstories/comments/uxn9v7/letting_my_mvirgin_coworker_test_his_vcard_chip