Round two; this time it’s anal! Filling my co-workers ass like never before [MF]

Hello all; back at it with my follow up from my last post. Sorry it took so long, had to go back to work following quarantine.

If you haven’t read it here’s the link;

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] from gonewildstories

This was the Tuesday following the prior encounter, again before quarantine. Though I have a quarantine story for later too. Part 3 anyone?

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It had only been 2 days, but i woke up on Tuesday morning for work excited like a kid on Christmas. Alex and I had been texting a bit back and forth prior, teasing each other and sending nudes. She wasn’t holding back either; fingering videos, dildo play, and just the classic stripteases. I couldn’t stop watching her videos. I had to be sure to screen record them and save them for later. I probably beat off 3 or 4 times over the course of that day. Luckily my girl worked all night so she was asleep for most of the day. She almost got caught recording blokvr by her boyfriend, but she simply played it off as if it was for him. She was feeling empty and you definitely could tell her boyfriend just wasn’t enough for her. Alex felt desperate as she explained that her boyfriend simply didn’t cum as much as I did. She had me record a few videos of me masturbating, making sure I got all of my cum on my shower walls so she could watch it drip. “I cant wait to be covered like that wall ;)” she’d respond. It was a blissful 24 hours.

We didn’t discuss much of what we wanted to do on Tuesday, nor did we talk much at work aside from work conversation. We didn’t wanna raise any suspicion, not knowing if our coworkers who had been their Sunday evening were spreading any rumors. I guess in the end all she wanted was to be surprised and filled again. “Easy enough for me”, I thought. I’m pretty good with surprises. Alex got off work before I did, and so when she got back to her place, she texted me that we were to meet at her apartment. I wasn’t sure whether we would be there for the night, or go out again. I knew her boyfriends stayed over a lot at her place, so my guess was we would do the same thing as before, only maybe without the drinking and karaoke. I didn’t press her too much, so I said to leave the door unlocked before i get there.

I get off work and see she hasn’t missed a beat, leaving me a text message. “Bring lube.” it said. We had discussed lube usage a bit the day before. I mentioned i found this really awesome brand I like to use for anal; it is silicon based, not water. It makes everything so much more smooth, but it’s a little messy. She had responded “oh that sounds hot” and left it pretty much at that. My guess is that’s the stuff she wanted me to bring. I ran home really quick to get changed and grab the bottle, and got to her apartment as fast as I could.

I let her know I was close and she said that the door was unlocked. I went up to her door and did a kind knock before entering; I would’ve felt a little wrong if I had just barged in. I open the door and there she is, sitting on the couch. She’s wearing a tank top and, what I like to call, dick appointment shorts. (I think you all know which ones I mean.) She had tied her hair back in pigtails, which was different but definitely a turn on for me. She got up and walked over to me, and gave me a hug. “Hey you,” she said. “Hey,” I said as I wrapped my arms around the back of her head. She steps back and looks up at me with those cute plump cheeks of hers. “I wanted to tell you that I’m sorry for what we did on sunday evening. It was wrong of me to do that, wrong of us to do that,” she said sadly. I was kind of surprised; I didnt know what to say…

I just kinda stood there looking at her. I was sad, and I was slowly beginning to feel bad too now that she mentioned it. “You know, you’re probably right…I’m -” I stammered before she did something unexpected. She dropped to her knees in front of me, unzipped my jeans, and pulled them down together with my boxers. My dick flopped out, semi-erect from seeing her in such a cute, sexy outfit. She started stroking me with her hand and slowly teased me by sucking on my balls. “What the hell are you -,” I said before she looked up at me and put her finger over her lips. “Shhh,” she whispered. She eventually got me rock hard and stuck my dick in her mouth. She gave me the an almost identical sloppy wet blowjob from our prior encounter. She moved her tounge piercing all around, from the bottom of my shaft and up to the tip. “You better not cum yet mister,” she said, staring desperately up at me. I took one hand and grabbed her from underneath her chin and stared back into her eyes. “And why is that? I thought you regretted doing what we did?” I said, almost in a scolding tone. “Oh, I do. I regret doing it in the back of your car. We could’ve just came back to my place,” She said slyly as she winked at me.

Hot damn, I thought to myself. This chick played me like a damn fiddle at first. I took my hand, still underneath her chin, & squeezed her face between my fingers. “Well we’re here now, let’s make the best of it,” and took my other hand and shoved her head back down onto my cock. I forced her head all the way down until I could here her gag, and held her there for a few seconds before letting her back up. She came up and looked at me like a lost puppy, those big brown eyes, a few tears running down her face. “I didn’t say I was going to cum yet,” I said as I forced her back down. She winced and gagged again; I was basically throat fucking her at this point. She came off for air a couple times, but I continued to jam my dick so far back down her throat. I eventually felt the wave that I was about to cum shudder through my dick, and proceeded to grab both her pigtails as I continued to slam my dick in her throat. Without saying anything, I held onto her hair, holding her in place, and shot my load down her throat, slowly pulling out after the first few pumps so that just the tip was sitting on her lips. I finished unloading into her and she looked up at me and showed me her throat and tongue, plastered in cum. She then grinned with her teeth and slowly let the cum ooze out of her mouth, onto her lips, and down onto her chest.

“Fuck i missed that feeling,” she said, slurping up the last few drops from the tip of my cock. Her mascara was running a bit. “I know,” I noted. “I hope you’re ready to get creamed in some more games!” She hopped up, went to her kitchen to grab a towel, threw it to me, and went back to the couch. “What!? I don’t think so,” I exclaimed. She didn’t clean herself off, she just plopped down on the couch and loaded up her PS4. “What? You think I was gonna let you off easy? No sir. C’mon,” she said hitting the seat next to her. I was baffled; she kept playing me again. I decided to play along and say next to her on the couch. She loads up Tekken again, and starts a head to head match. “What are the stakes, mr. Competitive?” she asked smugly. “I don’t know, let’s do strip tekken: you lose a round you take off an article of clothing. Winner is determined by whoever gets the other to their last bit of clothing first, and gets to decide our next move.” Admittedly that wasn’t my best idea, but she nodded and winked. “Sounds good. Prepare to be naked then!” she giggled. I reminded myself after the fact that I was indeed wearing my articles of clothing than her, and she was wearing probably 3 pieces at most, not including her glasses. She pummels me the first round and I take off my socks. “No fair that doesn’t count!” she yelled, slapping my arm. “Yes it does,” I proclaim. “My house, my console, my rules. Take off your pants!” she said trying to unzip them. “Woah woah no, you didn’t say that before we started. Stop being a sore loser,” I said jokingly. “Ugh you’re no fun!” she pouted and loaded up the next round.

She proceeds to beat me the next 2 rounds, so I admittedly took my pants and hoodie off. She looked so confident in herself, and it was mad sexy. Little did she know, I had hustled her into thinking I was gonna be the first one naked. But all I had to do was win the next two rounds, and she was mine. I bested her the next round and she frowned. She turns to look me dead in the eye, and without missing a beat, she slowly slips off her shorts. She revealed a lovely red pair of boy shorts, which were definitely a bit too tight. I could definitely see those beautiful plump pussy lips of hers through them. They were a bit wet, but I imagine they were soaked before. Again, I best her in the next round and secured my victory. She frowned again, and pulled off her tank top. Only to my surprise, she was wearing a strapless bra. Red, lacy, definitely unexpected. “Blasphemy! I didn’t know you were wearing that,” I said defeatedly. “I know, I guess in just full of surprises,” she winked again and readied up for the next match. She beats me again, and I’m left with just my boxers on. This was it, it was sudden death.

She locked eyes with me before the match and said “you know, I too am turned on by competition.” I wasn’t as surprised as I thought I’d be; I guess I should’ve gathered that when she had me play her in games again. “I mean, yeah I kinda figured that. Why else would you have wanted to play games again?” I asked. “Well, that and I knew you needed time to recoup all the cum I just drained from your balls,” she laughed. She definitely knew what she was doing, and she wanted to make sure I was completely loaded for our next go around. “Well then, you’re on missy,” I stated and readied for the next match. I had to win. It was our closest match yet, but I barely beat her. I was actually shaking, but I don’t know why. I was pretty good at hiding it as she looked over at me and and made this sexy pout face. “Well, which do you want off mister? Top or bottom?” I put my hand on her thighs and slowly slid it up to her boy shorts and stuck my finger in her pussy through them. She gasped, “While as sexy as these are, they gotta go.”

I slowly started sliding them off with both hands at this point. She kept her locked to me as she lifted her legs so I could completely slide them off. She pushed me back on to my back and began to climb onto me. “Nuh uh, not yet,” I said. I pulled off my boxers and grabbed her by a pigtail to pull her over. Her tits were looking extraordinary in that bra, and I was slowly stroking myself looking at them. I pulled her just enough on top of me to where her tits were sitting just above my dick, and then I slid it in between them while her bra was still on. “Spit,” I demanded, taking her face with my hand underneath her chin again. She looked down and spit on it, landing it near perfectly on top of my tip. She proceeded to look at what she was doing and maintained a solid tempo throughout. She spat again every once in a while to make sure it stayed nice and lubricated. She looked up at me again “can I have my pussy filled again, please?” she begged. I shook my head. “How about something different,” I slyly smirked.

“What is it?” she asked, still maintaining her tempo. “Turn around,” I said. She slipped her tits off my dick and turned around on all fours. I went over to my bag by the door and grabbed my bottle of lube. I walked back, grabbed her by the waist, and pulled her to the end of the couch; over the arm just enough where I could stand up and reach her ass. Without saying anything again, I opened the bottle and poured a bit down her ass crack. She squirmed, “Ohhhh fuck that’s cold,” she shivered. I took the lube and dumped some more, using my other hand to lather her asshole. “So this is what you wanna do,” she said, looking back at me over her backside. I just nodded at her and winked. Before I decided to enter her, I wanted to return the favor from the beginning of our encounter. I got down on both knees, spred her legs a bit, and began to eat her out. She moaned and gasped and started touching herself. I slapped her hand away and continued to press on her clit with my tongue. I ate her out vigorously, slipping my tongue in and out, up and down, nibbling on her clit ever so slightly. She squirmed and let out a big squeaking moan, I felt her juices rush down my lips. I slowed down and kissed her thighs, teasing her a bit. I slowly ran my tongue down her thigh, back up the other, and proceeded to eat her out again til orgasm. She squirmed harder the second time, making it know she came again. The juices tasted just as sweet as the time. I got back up on my feet and slapped her ass and made her yelp. “That was for earlier,” I said. I slapped her ass again. I slowly lowered myself into position and slid my cock down her ass crack, using some of the lube from the bottle on myself.

As soon as I knew I had enough, I guided myself to her asshole with one hand and grabbed her pigtail with the other. Slowly I pressed into her tight asshole, and she started to clench her ass and shake, gasping heavily. “Relax, you’re making it too tight,” I said yanking on her hair. She just nodded her head, still gasping. I felt her asshole relax and I pushed myself all the way in. She screamed “Oh fuck! Yes!” I stayed still for a moment before pulling back, watching her asshole grip my dick. She did not stop moaning as I stroked back and forth, slowly. I added a few more drops of lube and then set the bottle aside. I made sure not to slide out, as I reached my hand up and grabbed her other pigtail. I yanked them each time I went in, making sure I went as far in as I could. She constantly squirmed and yelled out in pleasure. I rammed her good, picking up the pace. “Stop! Stop! It hurts!” She yelled. I slapped her ass and kept going a few more strokes before pulling out. “I was just getting started,” I said, seemingly out of breath little. “Sorry it’s just…it’s just been a while. You’re also bigger than I’ve had down there,” she said. “Switch,” I said.

I pulled her off of the arm if the couch and laid her slightly angled sideways-esq on the main cushions. I had her on her back with one foot on the floor and one barely hanging off the edge of the cushions. Basically missionary anal position. I pressed hard and deep into her asshole as she moaned in pleasure again, making sure to slide all the way back inside her. “Are you gonna cum for me yet?” she begged. I shook my head and slapped her cheeks. She had a surprised look on her face. Luckily I didn’t leave a mark, but after she grinned at me. That was all the sign I needed. I grabbed on pigtail again with one hand, and proceeded to rub her pussy with the other. I was still stroking inside her and she just kept moaning in pleasure, squirming everytime she orgasmed. She was still rubbing her clit a little. “Please…don’t…stop…don’t…cum…yet…God…ohhh yes yess,” she begged, each time my balls slapped against her. Her noises were like that of porn, only I knew she knew wasn’t faking. This kept me going longer than I thought; I knew I was going to cum any second now. I slapped her tits with my hand, still rubbing her clit. She just lied there, and I became mesmerized by her tits just slowly moving up and down, like waves. I stopped rubbing her clit, moved one leg up onto my shoulder, and proceeded to stroke faster into her asshole. My balls were getting sore from then constantly hitting her ass. I wasn’t sure if I would cum as much or as hard. I was wrong, and suddenly I felt a wave rush through my body. I looked her and winked. I grabbed her pigtails and prepared to unleash inside her asshole.

I pushed as far in as I could, just like last time, and unleashed my first pump deep inside. I pulled out just a bit more, and let the second one go. She sighed in absolute relief and pleasure. She tried to look over to see my dick slowly sliding out of her ass. Third pump; I was about half way out this time, and I saw a bit of white seeping from the outer rim of her asshole. Fourth pump, and I was barely in at tips length. I saw more cum seep out of her, dripping onto the couch. I stayed there for the fifth pump and more cum leaked out. I let the rest of it go inside her ass and she pushed me off and instantly gazed upon the cream pied masterpiece that was coming out of her ass. She held her leg up and just watched it leak out of her, admiring the load. She let some of it drip onto her hand and proceeded to rub her sweet juicy pussy lips with it, giggling in pleasure. “Fuck that was amazing, I’m glad you didn’t finish on my chest this time,” she sighed, still touching herself. “Yeah me too,” I panted. Boy I was out of breath. She sat up, both feet firmly planted on the ground, legs spread wide open, continuing to rub her clit. “Well mister, how long do you need til our next round?” she smirked. She was serious about dehydrating me. “I’ve never been filled like that anally, do you think we can do that again?” this time she begged with her puppy dog eyes. I sat next to her on the couch and just took a deep breath. “Only if you can beat me in guitar hero.”

We proceeded to play guitar hero while we both recovered. She gave me a bottle of Gatorade from the fridge which helped me a bit. We followed the same pattern, only I beat her everytime. At one point, she paused the game and threw her hands up and shouted “i give up! Just fill me again!” She proceeded to suck my dick, give me a lusty tit job, and slip me inside her, riding me reverse cowgirl style on the couch. We fucked another 3 times, the last one being on her bed. She had me cover her face the last time; she was absolutely covered in white. She took a few selfies with my cum all over her face and one video of her letting it drip off and licking it back up. While she was taking the video she received a text that her boyfriend was off and headed back home. She quickly threw me a towel, jumped in the bathroom to wash her face off, and shoved me back into the living room to get dressed. She sent me the photos and video and hurried me out. Before I could grab the door handle, she pulled me back in and made out with me, slipping her tongue in my mouth. Turns out, she had a bit left over and let it drip into my throat. “Enjoy those pictures mister. Let’s do this again soon.” She winked at me, turned around, and I slapped her ass before leaving. “See you at work missy.”

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Hope you all enjoyed the second installment of my story. Don’t worry, there’s more to cum! She’s texted me asking her what I thought of the new girl we just hired, Theresa. She’s temporarily moved to our store just before we all got quarantined. I told her I think she’s hot and she just sent back a very suggestive text “I think she’s going to surprise you ;)” and left it at that. I think it’s time to put my threesome skills to the test. I know shitting where you work isn’t ideal, but hey she’s only there temporarily right?

Hope there aren’t any spelling errors. I’ll go back through it in a bit. Until next time.

Source: reddit.com/r/gonewildstories/comments/fulql5/round_two_this_time_its_anal_filling_my_coworkers