Humiliated by a Dominant Coworker

Hello,

Long time fan of the site. I wanted to describe my first cuckold experiences that started on halloween a few years ago.

My girlfriend's name was Amanda. We were in our late twenties and worked together at a crappy retail store. Can't go into too much detail but I worked primarily in the back of the store managing deliveries and inventory. The only time I went out on the floor was to merchandize something on the shelves. Amanda worked at the register in the front. And then there was this guy named Steve who was related to the owner. He didn't do much actual work but his technical job was 'security'.

We were all 'friends' and hung out a bit outside of work (getting lunch together, etc). I never really liked Steve though. He teased and bullied me, though never directly in front of Amanda. Almost every week, he'd come back to the warehouse area and make some comments about Amanda to me. He'd talk about what she was wearing, how hot she was, and how he didn't understand why she was with me.

He asked once if I had a huge dick and that's why Amanda would date me. I was frustrated and said no but soon realized that I should have lied and just said yes. I was trying to stand up for Amanda but ended up just humiliating myself. Anyways, he made fun of me quite often after that and talked a lot about how big his dick was and how much Amanda would appreciate it.

Amanda knew there was a bit of friction between Steve and I but she tossed it off as just normal guy stuff. She was very outgoing and friendly in general and tolerated Steve's jokes and casual flirting throughout the day. Amanda was very pretty and undoubtedly used to all her male friends flirting with her a bit.

Leading up to halloween one year, Steve invited us to a big party with some old frat friends of his. Amanda agreed for both of us. We didn't have anything else planned but I was still a bit hesitant to go. Frat parties were never really my scene in college.

Amanda and I went to a halloween store to pick up some costumes for the party. I found a harry potter costume that looked normal enough. And trying to match me a bit, Amanda found a witch costume. Her costume was more on the sexy side with a short black dress. It came with a big cape though so it wasn't too revealing overall. Adding a pointy hat, she looked like a sexy witch and she posed a bit for me outside the dressing room before deciding to buy it.

When we got to the party later that night, it was huge. It took us ten minutes just to find Steve inside. When we did find him, he was dressed up as an 80s police officer. He had an all black uniform, handcuffs, and a badge. He also had a fake mustache to apparently make it more '80s'. He was chatting with a bunch of his friends and he introduced Amanda to them when we walked up. They all complimented her on her costume and she thanked them. Standing slightly behind her and Steve, I received no introduction.

Amanda and I headed to the dance floor and danced together for a few songs before Steve buttted in. He jokingly said he was jealous seeing Amanda dance with me so much and asked if he could dance with her for a song or two. Amanda eventually said ok and Steve asked me to go get them drinks and come back. I headed off and waited in line for a bit before being able to pour three beers out of the keg. When I returned, I saw Steve and Amanda dancing together quite closely. She had her back to him and he held her hips while grinding his crotch into her ass. I carried the drinks over to them and danced awkwardly in front of Amanda while Steve continued to hump her from behind.

After that song, we all headed off the dance floor to drink our beers. When we were all finished, Steve left to get more beers for us leaving Amanda and I alone finally for a bit. While he was gone, the DJ announced that there would be a couple's costume contest shortly. Amanda wanted to do it and said we'd be a good fit since we were both wizard/witch related. I was hesitant and didn't want the eyes of everyone at the party focused directly on me. Amanda was disappointed but understanding.

When Steve came back with the beers, though, he was really excited. He told Amanda he had the best idea for a couple's costume between him and her. She was happy to find a pair for the costume and asked him what his idea was. Steve explained that he'd be a cop still and she would be a captured criminal. He told her to take off her hat and cape which she did, handing the clothes to me to hold. She was now just wearing a short black dress. He then told her to hold her hands behind her back and he handcuffed them together. And for the final touch, he took off his belt and looped it around Amanda's neck, effectively collar and leashing her. Amanda was a bit concerned but agreed to go through with it. One of Steve's other friends saw them and said they looked great which gave Amanda some confidence.

I remained in the corner while I watched Steve lead Amanda on a leash to the front of the dancefloor. There were only three couples who entered the contest and Steve and Amanda were last in line. As each couple presented themselves, the DJ played a song and they would walk around and dance with each other a bit. When it was their turn, Steve walked out in front and pulled Amanda behind him to the middle of the floor. He then turned around and pulled her body against his. He put his hand around her back and they danced together while all Steve's frat friends cheered. He was all over her and he had easy access while Amanda's hands were handcuffed behind her back. She seemed to be having fun though and fed off the positive feedback from the crowd.

The DJ declared Steve and Amanda winners and they cheered together. Still with his belt around her neck, Steve led Amanda back to the corner where I was. I congratulated them and Amanda teased me for not wanting to participate in the first place. Steve finally unleashed Amanda but her hands were still handcuffed behind her back. He asked Amanda what his prize was for winning with her. Amanda laughed and asked what he wanted. He put his hands on her sides and tickled her while explaining that he might let her free if she gave him a kiss. She giggled and contorted her body before eventually saying yes. Steve stopped tickling her and she came to her senses. I gave her a look but she said that I could have received the kiss if I didn't chicken out in the first place.

Turning to Steve, Amanda told him to uncuff her and take off his fake mustache first if he really wanted a kiss. He unlocked the handcuffs and then peeled off his mustache with a giant grin on his face. She then stepped towards and stood up on her tiptoes to be able to reach his lips while he wrapped his arms around her back. She gave him a quick peck on the lips and then feeling like she might have short changed him, went back in for a second longer kiss. Both their mouths were slightly open and they kissed for a couple seconds before she broke it off and pushed him back. Steve looked pleased at his minor conquest. Slightly embarrassed, Amanda said she'd get drinks this time and left Steve and I alone together.

Once she was out of sight, Steve exclaimed that he knew Amanda wanted him. I told him he was wrong but he shot me down immediately. He teasingly asked how it felt to see my girlfriend kiss him like that. I was speechless and felt deflated. Steve continued to turn the knife and said that maybe Amanda felt his big dick earlier while they were dancing together.

And I had been dancing with her immediately beforehand so it must have been an easy comparison for her to make. I told Steve to shut up just as Amanda was returning with drinks. She had a girl named Claire with her that she had just met. Claire introduced herself and Steve and I and complimented Steve on the costume contest. We all chatted together as we drank our beers. Claire wasn't very pretty but she was super nice and engaging. Amanda liked her and I could tell they were quickly becoming friends.

It was getting late so I tried to make an excuse for Amanda and I to go before Steve could have another run at her on the dance floor. Amanda agreed despite Steve's protests for us to stay a bit longer. Before we could exit though, Claire stopped us and invited us to her apartment the following weekend. She said she was having a casual get together with a bunch of friends and we should stop by. We agreed to come and Amanda and Claire exchanged info.

The next week at work was hell. Steve found every opportunity to come to the warehouse and tease me more about Amanda and their kiss. I tried pushing back and then I tried ignoring him but nothing seemed to work. Amanda for her part played it cool and acted like nothing out of the ordinary had happened. On Friday, I was looking forward to the weekend and two days without Steve but I suddenly remembered Claire's party which Steve was also invited to.

Thanks partly to my stalling tactics, we arrived a bit late to Claire's party on Saturday. Steve was already there along with a handful of other people we didn't know. Claire introduced and showed us around. It was a nice time and we avoided Steve's attention mostly. About an hour after we arrived though, Claire's other friends said goodbye and left Amanda, me, and Steve and the only people remaining with Claire. Steve asked if we should do something together and Claire suggested we go down to the pool at her complex. She said it was late enough that no one else would be there so we'd have the pool all to ourselves. I mentioned that we didn't have any bathing suits but Claire said she had an extra that Amanda could wear and Steve and I could just go in our boxers. She said guys did it all the time and it wasn't a problem.

I hesitantly agreed and Amanda went off into Claire's bedroom to try on the bathing suit. Alone with me once again, Steve said he couldn't wait to see Amanda in a little bathing suit and he bet that Amanda would enjoy seeing him in his boxer briefs as well. Thankfully Amanda and Claire came back out relatively quickly. Claire was wearing a one piece bikini and Amanda had a two piece bathing suit that wasn't too revealing but had string ties on the sides and back to hold it together. Claire got some towels and we headed down to the pool together.

The girls jumped in first while Steve and I took our clothes off. I felt very self conscious being in my underwear next to Steve so jumped in the pool as soon as I could and Steve followed soon thereafter. We swam around for a bit before Steve suggested we play a game. He suggested marco polo but Claire countered and said we have two boys and two girls so we should play chicken fight. Steve agreed and Claire quickly got onto Steve's shoulders to battle us.

I knelt down and Amanda got on my shoulders as well and the fight was on. Unfortunately for us, both Steve and Claire were taller than us and towered over us when stacked on top of each other. In the first round, Claire pushed Amanda over quickly. In the second round, we held our ground a bit longer but Claire accidentally caught Amanda's top strap and momentarily revealed her left boob to both her and Steve. Steve looked straight at me and grinned. Claire immediately apologized but Amanda told her it wasn't a problem and went back to fighting after fixing her top. Steve then stepped on my foot underwater which made me lose balance and Amanda and I fell over again.

Steve then said that we should switch partners to make it more fair height wise. Everyone agreed and Claire climbed onto my shoulders while Amanda got on top of Steve. I couldn't help but think of anything other than her pussy pressing against the back of Steve's head and how he'd tease me about that for another week. As we battled again, I apparently proved to be the weak link as Steve and Amanda managed to push Claire and I over three times in a row. We were exhausted and decided to stop playing. Calling back to the halloween party, Steve asked Amanda if he got any reward for winning again. She teasingly said you wish and turned away from him. Steve then grabbed the straps on the back of her top and pulled it off. Amanda shrieked and chased after Steve to the other side of the pool with one arm covering her boobs and the other arm trying to swim.

Eventually she caught up to him but Steve held her top high above his head. Both Amanda and I were yelling at Steve to give her top back but he held firm. He told Amanda she could have her top once he got his kiss. Eventually Amanda said fine and kissed him quickly while holding her boobs in both hands. Steve then said that wasn't good enough and said she had to really kiss him. At that point, I was surprised to see Amanda drop her hands off her boobs, wrap them around Steve's shoulders, and give him a prolonged kiss with her boobs pressed against his chest. She finally broke off her kiss and snatched her top back while playfully punching him in the chest. Claire and I watched the entire thing from twenty feet away. Claire thought it was funny and assumed this was a normal thing that Steve and Amanda might do. In fact, she mentioned that they should probably start dating, apparently not catching that Amanda and I were already dating after all our time together.

I was humiliated as we all got out of the pool, dried off, and headed back to Claire's apartment. Claire told us guys to use the bathroom to change while she and Amanda went back into her bedroom. In the bathroom, Steve started laughing just looking at me. He said Amanda's boobs were top class. He even mentioned that she kissed him with a bit of tongue and he was grabbing her butt underneath the water, in case I hadn't been able to see those details. Steve then dropped his wet boxers and exposed his flaccid yet giant cock in front of me. He caught me staring and said that Amanda would be enjoying it soon enough. I tried to slip off my boxers under a towel but Steve pulled it away and told me to show him my dick. I covered myself at first but eventually accepted my fate and stood up straight. My dick wasn't even half the size of Steve's.

He pointed at my dick and laughed saying that he felt so sorry for Amanda. I was about to put my pants back on when Steve said he'd stop pursuing Amanda if I got on my knees and kissed his butt. I said no way but he promised he was being honest and he'd completely stop if I did this one thing. He said that I didn't even have to kiss his butt, just the side of his butt cheek. I asked why and he said he was just doing it all to fuck with me so if I did this one thing and showed submission to him, he'd stop. Stupidly, I agreed and we even shook hands completely naked before I got on my knees.

I sat down and Steve told me to close my eyes. I refused initially but he insisted saying that he just wanted me to kiss his butt but not check it out up close like a fag. I reluctantly closed my eyes and heard him walk up to me. He then told me to kiss and I pushed my lips forward. I didn't feel anything at first and Steve told me to go further. I kept leaning further but never touched anything. I finally opened my eyes and looked up to discover Steve recording me on his phone with his dick inches in front of my face. I fell back as he laughed.

I told him to delete the video but he said he'd keep it just in case he ever needed it in the future. He said it's only natural that guys with small dicks worship guys with big dicks and maybe Amanda would be interested in seeing an example of that sometime. I pleaded that he could never do that but Steve just said he'd see what happens. Angry and humiliated, I put on my clothes quickly and walked out to the living room. The girls were already there and asked us what was taking so long. Steve came out a minute later and we all said goodbye to Claire and then left.

The next week at work was torture again. Not only did Steve go to great lengths to describe Amanda's boobs and their kiss to me, he also made me admit that his dick was much bigger than mine. Knowing the blackmail evidence that Steve had, I had no choice but to be more accepting of his bullying. I readily agreed with most of his points which made him laugh endlessly and only furthered my humiliation. He flirted more openly with Amanda as well and asked her out to go dancing again. Amanda was nice and laughed at his jokes but turned down his proposals to my relief.

A week later, we were heading into black friday which is a big day for our store. Amanda and I got placed on an overnight shift to get the store ready the night before we let customers in at 7am. Unfortunately for myself, Steve worked his way onto that shift as well. We arrived at the store on thanksgiving day at 10pm and started to get everything sorted. Amanda put up signs in the front windows while I got extra merchandise out on the shelves. Steve didn't do much besides flirt more with Amanda and pester me whenever she was away.

By 2am which was our 'lunch' break, the store was in pretty good shape and we didn't have much else to do. There was only one other worker on the night shift with us who was an older janitor. Everything was clean though so he took off for the night while Amanda, Steve, and I took our break together in the warehouse. We had a pizza we ordered earlier as well as a six pack of beer. As we ate, Steve complained that we had to wait another several hours with nothing to do until the morning shift workers came in. He said we play a game to pass the time.

Amanda smirked and said that Steve was just trying to steal another kiss from her somehow (which was indeed true). Steve didn't admit his intentions but just said whatever happens happens. Pretending to be frustrated, Amanda said she was done with games so Steve and I should just play each other and then tell her who wins afterwards. Steve asked if the winner gets an award from her and she said yes with a bit of a grin. She then left the warehouse and went back on the floor to finish the remainder of her work.

Steve looked at me and said I should just admit defeat. I meekly asked what he wanted from me. He said that we would both jerk off and whoever cums first loses. I was startled and told Steve no way. He said if I did it, he'd give me his phone and let me delete the previous pictures he had of me (if I won or not). And if I was able to last longer than him, then he'd go out to Amanda and personally tell her that I won our contest. I desperately wanted to have those pics deleted. Getting the award from Amanda was a bit of an afterthought to be honest.

I rebutted Steve and said it was just some sort of trick again but he promised that it wasn't. Steve kept telling me that he knew I was gonna do it and I was just wasting time by stalling the decision. I eventually caved and told Steve I'd do it. He erupted with a big laugh and we headed to a bathroom in the back of the warehouse.

Once inside, Steve started stripping off his clothes and told me to do so as well. I hesitated at first but he said he already saw me fully naked so I should just get on with it. I took off my clothes and folded them up on the toilet. Steve said he wouldn't touch me and I couldn't touch him. I readily agreed. He then added though that I had to get on my knees again. I asked why and he said that was the last and final rule.

Eventually I folded, got on my knees, and started jerking off. Steve then positioned himself a foot in front of me and started jerking off as well. I was turned on by the sight of his hard cock in front of my face but also worried as I came to terms with the two potential scenarios that were gonna happen. And Steve made sure I understood the predicament.

As he jerked off, he said that if I came first, he would win and get a nice long kiss from Amanda. However, if he came first, I was gonna end up with a face full of cum. Steve asked me which one I preferred while grinning down at me. To be honest, I didn't know which was worse than the other. I then realized that if I did win, I wouldn't want to get a kiss from Amanda with a face that smelled like Steve's cum. I started jerking faster and Steve noticed. He teased me and said I must really want him to hook up with Amanda afterall.

I didn't reply but kept jerking. Steve then said I was a bitch and should beg him to hook up with my girlfriend. I resisted but he kept pressing the point and I was a bit surprised that the thought turned me on a bit as well. I softly said Steve should fuck Amanda. Steve told me to say it again louder. I said again that he should fuck Amanda. Steve then told me to beg for it. I finally broke down and said please Steve take my girlfriend and fuck her with your giant dick. As I said it, I started to cum and Steve backed away while laughing at me.

I was completely humiliated as we put our clothes back on and walked out to Amanda. When we got to her, she asked what had happened. Steve looked at me grinning again. I paused for a moment and then told Amanda and Steve won fair and square and deserves a reward. Amanda was surprised I said it instead of Steve boasting about it but agreed to honor the result.

She walked over to Steve and playfully asked him what he wanted this time. He didn't even say anything but just pulled her towards him and they started making out. I stood awkwardly as they groped each other and kissed for over a minute. Steve eventually broke off this kiss and told me that he thought I had something to clean up in the warehouse. I took the hint and left and they resumed their kissing.

Twenty minutes later, Steve and Amanda came back to the warehouse. Amanda said they were gonna go back to our apartment and asked if I was ok to watch the store until the morning. I said yes and they dashed off together out the back door. I waited alone in the store for a couple hours before the first morning shift workers arrived.

I then left and headed home in complete defeat. When I arrived at our apartment, Amanda and Steve's clothes were on the ground and they were in the bedroom together. I laid down on the couch exhausted and fell asleep. Several hours later, Amanda woke me up. She apologized a bit for how crazy things got but said she appreciated what I said to Steve. I asked her what she meant and she explained that Steve told her that I had asked him to hook up with her. Embarrassed, I admitted it was true. Amanda said it was good though and gave me a kiss. And as she walked into the bathroom to go into shower, she said it wouldn't be the last time.

Since then, Steve and Amanda hook up regularly. I'm often sleeping on the couch a couple days a week. A few times even, Steve has taken Amanda into the bathroom in the warehouse where we had our jerk off contest and fucked her there too. Amanda doesn't hook up anymore but I often masturbate while listening to her and Steve in the other room. And I still always cum before Steve while doing that.

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