I [23M] got to casually compete and bet against a coworker [21F] who let me fuck her and fill her up to the brim, all because of a bet…[MF]

Skip to ***** for the good stuff. It’s pretty lengthy.

I had decided to go out with coworkers after a long day of work. Alex, we’ll call her, suggested a karaoke and video game lounge. We agreed and she said she knew the hostess and could get us in for free.

Eventually we make our way over and things got pretty intense fast. Shots were poured, drinks were freely tossed at us, and songs were blaring from the TV. Alex was having a grand time, meanwhile I sat in the corner and sipped my drink because I don’t usually like karaoke.

Alex was hot, but she definitely didn’t strut about like she was. She was so chill and calm and she definitely put time into her looks. She had plump cheeks; not like “fat” plump, that’s just that’s best way I can put it, they were just plump and adorable. She has an ample set of tists, a nice slender waist that accentuated out to her wide hips and nice thick, thighs and adorably stubby, but stocky legs. The perfect combination of busty petite.

Things get heated in the game room and our coworkers finally start to trickle out. Eventually it was just Alex and I, playing games. It was awkward at first, but eventually she perks up. “Let’s widen the stakes huh mr. Competitive?” She proceeded. “What do you mean?” I ask confused. “Who ever wins gets to truth or dare the other, no limits” she stated. I looked at her confused but agreed and nodded. First game was a fighting one. She won hands down. I suck at them. The dares and truths got pretty sexual pretty fast. Alex wasn’t holding back. Which was odd for someone who had a boyfriend…

Eventually it was just Alex and I agsin in the final match. I managed to win but barely. “Damn it, well about time you beat me” she smirked. “Dare me! I dare you” she said. I couldn’t help it. “Fine…name the category” I said, being nice. “Sexual favor” she said. I was confused and aroused all at the same time. “Like…ok…uhm…I dare you to touch my crotch” I said. Without much of a second thought, she proceeded to slowly run her hand from my knee to my crotch, slowly. She ran her fingers up and down, gently over my pulsating and erect dick. “My my, excited are we?” She said as she jerked her hand away. Such a tease. My coworkers didn’t seem to notice as they were nose first in their phones.

*****
Eventually my other coworkers said their goodbyes and left.I stood up and said goodbye. Alex stayed seated, and i could have sworn she was just burning a hole in my crotch with her adorably squinting eyes. She jerked away as I turned to sit down. She exclaims “just the two of us huh?” I nodded and decided to up the stakes, seeing as how we were down two players. “Winner of the next round gets two truth or dares” I said. “Deal, but you won’t win” she said proudly. She then proceeded to pulverize me the next match. I was not on it, I truly.suck at fighting games. “Ha! Not so tough now mr. Competitive huh?” She said giggling. She then proceeds to sit on my lap, facing me, and began to rock back and forth. “I dare you to not cum, and to be truthful if you want to” she said, in a very demanding tone. “O…ok, but what abo-” I stammered before she locked lips with mine. “Mmm mmm” she said pulling away after a few seconds. “The only thing you’re allowed to say is if you’re going to cum or not.” She locks lips with me again and pulls my hands to her waist.

Admittedly, I was going to bust any minute now. I was spiraling out of confusion mixed with booze mixed with the hot air in the room. “I want to cum” I murmured. “You what?” She said pulling away, pinning my hands on her thighs. “I want to cum but I dont know if I should. You have a boyfriend and I have a girlfriend, why are you doing this?” I said. “Now now, what did I say about saying anything else?” She asked. “This feels so wrong” I said. I wasn’t complaining on the inside. I was face first with one of the best chests I’d ever seen. “Uh huh…sure. Well we’ll see about that huh mr competition?” She said. She proceeded to continue to rock back and forth on my crotch, leaning back holding on to my shoulders and almost began to moan before I interrupted her. “I bet if I don’t cum soon I’ll make you cum first!” I yelled. She stopped and sat up, her tits at eye level again. “Oh?” She said slowly grinding again on my lap. “You’ve already lasted longer than expected. But I’m definitely not done” she said. She got up and turned around and proceeded to give me a lap dance, only this time she pulled my hands to her tits and made me feel her up. They were definitely not fake, but super firm and ample. I was getting close. The grinding pace didn’t stop. “Ready to let loose yet?” She said. “Not in the slightest” I smirked. I was really trying to hold it together but I didn’t think I’d last any longer. “Well I guess we’ll have to up the stakes” she said. “Make me cum or I won’t finish you off” she said, hopping off my lap. “But nothing comes off, not even unzipped” she smirked. “And if I win?” I asked. “You get to do whatever you want to me, clothes off” she smiled. “Deal” she said.

I told her to sit next to me. Before she got to it I pulled her down and threw myself on her lap, quickly asserting the position. I put my hands on both her thighs and begin to rub the inside through the slight tears in her jeans, running my hands ever so slowly towards her pussy and backing away at the last second. It was getting good before her friend came back and interrupted. “oh my!” She exclaimed. I hopped off and Alex looked embarrassingly at her, I just looked out the window. “Well I’ll leave you two alone. Here’s the last round of drinks” she said and shimmied out the door, almost slamming it. Alex slid over and grabbed and downed the drink rather quickly. “Let’s go. I wanna go home” she said demanding me. I was confused to say the least. My balls hurt and I was disappointed that neither of us finished.

We get the drinks finished off, tip her friend, and left. Since I had driven her it made for an awkward few minutes before she perked up. “You still hard? Or did I blue ball you?” She giggled smugly. “Definitely blue balled” I sighed. “Well that sucks, looks like I won” she smirked. “Wait how did you win? Neither of us came” I remarked. We pull into where he car was parked and she grabs my crotch and says “well you’re about to” and begins to unzip my pants. “Get in the back” she halts and climbs over my back seat. I obliged and crawled back with her. What are we doing? I thought.

I lay down the bench seating to give us more room, and she proceeds to pull out my fully erect dick. Without any hesitation she proceeds to give me head, being super sloppy with it. Every now and again looking up at me with her white, wide eyes. She puffs out her cheeks and sucks them in, letting my dick poke out on the side. Her tongue was pierced, and I had never experienced anything like that before. She pulls my dick out of her mouth and jerks it up and down just face sitting in her hand looking at me, looking at it, and then back at me. “You will cum soon. I know it. I’ve felt it” she said. “I wo-” I stuttered before I felt a geyser erupting sensation fill my dick and before I knew it, let loose the first line of cum. She smiled and immediately put my dick back inside her mouth and sucked me dry, licking up every drop. I tend to cum a lot, and I can see her not ready to handle it all. She starts to gag and wince a bit, as i feel some cum drip down my shaft. Eventually i let two or three small pumps out before she finishes up the last drop and shows me her completely white tongue, letting me see it fall back into her throat, which is also covered in white. She swallows for a few seconds before gasping for air. “That was a lot, my goodness” she said, seemingly struggling for air.

“I’m sorry…it’s been a while. And you had me pretty well worked up” I sighed. Sweat was dripping down her chin and cheeks, but after closer observation it was actually some my cum had slipped off her lips that she missed. “No it’s ok…I just wasn’t expecting that at all” she said, seemingly caught up on lack of air now. “Well…anyways…you lost. But really we both won, dont you think?” she proclaimed, finally wiping the dripping cum from chin and licking it off her finger. “Yeah you beat me. I just couldn’t resist” I said putting my hands behind my head. “Damn…” she said. “Bet you can’t cum like that again now seeing as how I just drained your poor balls” she smirked. “You underestimate me. I could do that again no problem” I said smugly. “Then it’s my turn” she said.

She grabs my dick and begins to stroke it up and down, going from flaccid to erect by the time she gets it in her mouth again. “Uh uh, top off this time” I said. I was in control now. “Ugh fine, but yours are coming off too” as she ripped pants off. I lay there as she took off her top and revealed a partially lace, very lavish black bra. I gazed and made sure to snapshot in my memory for later. It didnt last long as she threw off her bra rather quickly revealing her ample firm tits. “I bet my dick would look better in between those” I snickered. “Not until I get off first” she said. At this point i wasn’t going to say no. I rolled over on top of her and pulled down her pants just enough to reveal her cute, luscious pussy. Just as plump as her cheeks, I slowly licked her thighs up and down and blew gently onto her sweet lips. I could feel her squirm. I gently lowered my tongue onto her sweet pussy and began to lick her up and down, up and down. She moaned and quivered, shaking her thick thighs against my head. She stopped abruptly and reached into her purse. “That’s enough. I can’t hold on anymore” she panted.

Before she could put on the condom she just pulled out of her purse, I slid my dick in between her tits and moved back and forth. “Not yet, ” I said. “To be fair, it might be a complete waste” she smirked. “I’d rather not let your next load go into such a thing” I began to rub my dick across her chest, between her tits and eventually into her mouth again as for more lubrication. Eventually I was ready to let loose again and went back down on her, this time for longer. She moaned and squirmed and quivered all over. Eventually I knew I had made her cum as my chin was drenched in it. She then pushed me over and rolled on top of me and in one swift motion, forced my dick inside of her. It was gloriously tight, I’m surprised I didn’t two pump chump it. But she rode me, up and down, rocking back and forth. I put my hands on her tits and just controlled her back and forth. Eventually she squirmed again and told me to get on top. “I can’t believe you haven’t cum yet” she said heavily. “It must be a lot again. I want you to fill me up all the way again” she said putting herself in the missionary position. “Don’t worry, all in good time” I said.

I pull one of her legs on to my shoulder and slip myself in her tight pussy, once again trying not bust in two pumps. I kept going slowly then quickly, slowly then quickly. Eventually I felt myself on the edge of busting again and slowed down to long, deep strokes. She moaned and quivered, her sweet cum relubricating my dick. “Come on already! Enough of the games!” She demanded. I just smiled and looked at her and said “or what?” She wasn’t having it as I pulled out to go back down on her. She wanted me to cum more than I think I wanted to cum. “No! Get back and finish what you started” she said daringly. I just sat there and slowly slipped in between her lips again and went as far as i could inside. She let out the cutest, sexiest yelp. “Faster!” She said. I just sat there inside, pushing further in. She yelped. I pulled out and slowly stroked it again. This is it. I was gonna fill her to the brim. I edged on a little bit more, hitting the furthest I could go inside and pulling almost all the way out. “Here you go” I said as I pushed in the furthest I had yet. She squealed as I let go inside her. First pump; I then pulled back a bit slowly sliding out. Second pump; I was about 3/4 of the way out and still not done. Third pump; halfway this time. I could tell she was enjoying herself as she smiled and groaned in pleasure. Fourth pump; I could feel some cum start to seep out. Fifth pump; I was in just the tip this time, and it had become apparent she was trying to get a view of what was going on. Sixth pump and i was all over her chest and some on her face. Seventh pump and I was out for the count, finishing on her chest and face with a few drips.

“Jesus that’s all?!” She exclaimed. “Oh c’mon, more than you’ve ever had” I huffed. “Well yeah, you even had some left for my face. I’ve never experienced this much before” she said, wiping her face off and licking it again. “Round three?” She perked up. “Ahhhaha” I said. “It’s late, how about we rain check?” I said. “Deal. And you won’t even have to compete with me sometime” she laughed. “I bet you couldn’t even last three rounds, that’s why you’re chickening out right now” she boasted. “Actually the most I’ve done is five rounds in one day. Bet you can’t top that huh?” I smirked. “If they’re all that much, I seriously think I could dehydrate you after three rounds” she kept laughing. “You’re on then” I smirked.

We finished cleaning ourselves up, the windows were foggy as hell and it was pretty late. I had begun to think some of the workers from the bowling alley might have seen our cars thinking the hell was going on. We step out and I feel woozy and lightheaded. Probably just all the hot air I thought to myself. She seemed to stumble out too. I looked down and saw a big wet stain on her legs, glistening through her teared jeans. “You missed a spot it seems” I smirked. “No i didn’t, I like letting it run down my legs. I think I have enough to last me the ride home” she smiled. She gave me a hug and peck on the cheek and as I turned around to get in my car she smacked my ass and smiled. “See you on Tuesday mister” she said and winked at me. “See you Tuesday.” I said and got in my car.

I arrived home to a text from her saying “made it home and still dripping ;)” It was early AM on Monday but she’s already sent me a few teaser pics and needless to say, I responded a bit after “Tuesday can’t come soon enough ;)” and she simply responded. “Bet.”
*****

Part two soon, depending how you guys like this telling. Admittedly I’m ashamed we both cheated, but it was impossible to resist. I think we’re gonna keep it going for a while and see what happens. She’s been telling me how much of a little cumslut she’s been feeling because of me. She wishes she could be filled dripping like that all the time.

On mobile and apologize for any grammatical or spelling errors.

Source: reddit.com/r/gonewildstories/comments/fnfmso/i_23m_got_to_casually_compete_and_bet_against_a