Rob and I met at work. He was in his twenties, and a few years younger than me when he started an entry-level job as one of my assistants. I trained him, giving him more attention than I did the others under my wing, as I genuinely liked the big guy. However, even though I was superior in age and employee status, I felt somewhat inferior to Rob. I found myself doing favors for Rob at work – I grabbed his lunch, picked up premium coffee for him every morning, drove him home, and even covered for him when he was late for work.
Office Cuckold Stories: My Girlfriend, My Boyish Assistant, and His Huge Cock
Rob’s looks got him a lot of attention – he had a smooth, boyish baby face. His arched eyebrows always made me feel like he was judging me. The kid loved to work out, too. He had the body of an athlete, with broad shoulders and a chest that puffed-out. He was taller than me at 6’2″ (I was 5’9″), and his muscles made my meek frame look puny when we stood beside each other.
I was so impressed with his physique that I began working out – Rob inspired me and even let me train with him. When we were at a gym together, I went out of my way to wipe up every bench before and after he used it. He didn’t ask me to, but it felt natural to do so, and it made me feel good doing it for him, especially when he’d return the favor with a thumbs-up or wink of approval.
I met Melissa a few months ago, and like Rob, she was way out my league, socially. Melissa was gorgeous, in her mid-twenties, and had brunette hair with a firm flawless body she kept fit. We met through a friend and went out on a few dates before she became my girlfriend. I knew she loved me, but I knew I didn’t satisfy her sexually. She was the hottest girl I had ever seen, let alone been with, and sometimes just body contact made me bust my nut too soon. Melissa and I shared a special connection, though. When Rob found out I was seeing someone, he seemed surprised.
“Wow,” he said to me in front of my subordinates. “I guess she likes the small cock.” This got a laugh from everyone except me, and when Rob could see my face turn red, he elbowed me and gave me a wink. Just like that, everything was okay again.
Rob insisted on meeting the girl who wanted to date me. I hesitated at first because the office gossip was that Rob had a huge cock. He used his gift with a lot of different women, all of which seemed to come to him It was formulaic whenever Rob would meet some new girl – he was easy to talk to and made girls feel like they wanted to see him again. The deal was sealed the second a girl saw his enormous cock. It was impressive to see all the women in our department, married or otherwise, fawn over him. With that in mind, you can imagine why I didn’t want Rob and my girlfriend to ever meet.
One day, while I was driving Rob home from work, I asked if it was okay if we made a pit-stop at my house first, which he said was fine. I expected him to wait in the car, but Rob got out when I did. I felt nervous with Rob behind me as I fidgeted to find the front door keys. I was worried that my place wouldn’t look good enough for him. When I got opened the door, I could see Melissa by the pool, which made me panic. Again, I was hesitant about my girlfriend and Rob being in the same place at the same time. You can imagine my confusion when I started to get an erection thinking about the two of them together.
When we got inside, Rob took a walk around my house while I fetched what I needed, completely oblivious to the tent I was trying tame in my pants. I used the bathroom, and by the time I came out, the inevitable happened: my big-dicked assistant was by the pool talking to my girlfriend.
“I heard a lot about you,” Melissa said to Rob with a flirtatious smile as I approached the two of them. Watching her talk to Rob was something else – the hottest girl in the world in her bathing suit face to face with the biggest alpha male I had ever met. Melissa was looking at Rob the way I did – in awe, and while he smiled down at her, she blushed. Rob smiled at me as Melissa swooned over him. His eyes had caught the movement in my crotch area. Though he only looked there for a second or two, there was no mistaking it – he saw my dick twitching in my pants as he talked to my girl.
I interrupted them so that I could drive Rob home, but my girlfriend insisted he stay for dinner, as she wanted to get to know him better. I began preparing a meal for the three of us, while Rob took off his shirt and got comfortable with my girlfriend by the pool. They must have hung out for just under an hour before I called out to them, announcing dinner was served.
Rob sat in my seat at the table, still shirtless, while my girlfriend covered herself up modestly, but enough to show her cleavage. They continued to make small talk with one another, despite being inches away from me. I might as well not have been in the room; they were so enamored with one another. Before I took Rob home, he invited Melissa over to a party he was having at his place on the weekend. She kissed him on the cheek and told him she would be there. At no point did Rob give me an invitation, but I had just assumed I was going Melissa’s date.
When we left, all Rob could talk about was how hot my girlfriend was. He was talking about Melissa rather inappropriately, forgetting that she had a boyfriend – me – his boss – who was sitting right beside him.
Likewise, Melissa spent a good half hour in bed talking about what a stud Rob was, how hot his body looked, and how cute she found him. I felt a little jealous, especially when she asked me for his number. I gave it to her before rolling over and falling asleep. I was awoken later that night to the sounds of incoming and outgoing texts from my girlfriend’s cell. Before some of her texts were sent, I heard her phone snap a pic more than a few times.
Later that night in bed, my eyes shut, trying to get some sleep with a blindfold on my eyes. Melissa was wide awake beside me doing her own thing, and I felt like she was waiting for me to nod off. I awoke later to the sound of her moaning and caught my girlfriend using her thick rubber sex-toy on herself under the covers. Her eyes were closed as she silently masturbated to full orgasm, something I had never given her. She drifted right to sleep while I beat off beside her, needing to tame my sudden erection. There was little doubt that we both fantasized about the same scenario.
The next day, Melissa and I went out to dinner, and I decided to get the inevitable out-of-the-way and invite Rob to join us. I was getting nervous watching my girlfriend talking to Rob. This was the second time they met, and their attraction to one another was palpable. I was hardly surprised at how well they got along but felt like an outcast when they talked to each other more than me.
My Assistant Has a Big Dick, and My Girlfriend Has a Crush on Him
I started inviting my girlfriend to hang out with us when the guys and I went out. Melissa got along fine with everyone, especially Rob. No matter where we went, either to a restaurant, a movie or out for drinks, they would always sit together. The more time passed, the better friends they became. She even started coming by the office to pick me up more often, but when she did, I would often find myself waiting for her and Rob to finish talking to one another.
One night I went out with some of my friends to a club. Laryssa had plans with her friends, so it wasn’t like I was ditching my girl to hang out with the guys. The last thing I expected to see Laryssa at the same club. Even more shocking – she was sitting beside Rob! I deduced that they met by chance, as the other people at the table were all of Melissa’s friends. When I approached their table, Melissa looked disappointed that I was there, while Rob gave me a look like I had just blocked him from something. Rob thumbed to a milk crate near the washroom and told me to pull it up to the table and sit on it if I wanted to join them. I looked around, and there were no chairs available, so I grabbed the milk crate and sat lower than everyone there. I looked up at Rob and Melissa, continuing to talk amongst each other despite my arrival. When Rob looked down at me, the expression on his face wasn’t the happy smiling one I was used to. He looked at me with superiority and authority. I felt very intimidated by him that night, so much to the point where I wanted to flee the scene.
I rejoined my friends after feeling like a third wheel between my assistant and my girlfriend, although neither one of them tried to stop me from leaving. Later, I saw the two of them on the upper level outside in the smoking area. I watched the two of them talk for a while before Rob put his arm around my girlfriend, who leaned in and rested her head on his shoulder. At one point, Rob nodded in my direction and made some sort of gesture squeezing his thumb and index finger towards each other, illustrating narrowness of some kind, which made Melissa laugh quite loudly. I stepped out to use the men’s room, and when I returned, my girlfriend was no longer in view on the rooftop. The only person out there was Rob, who had his back to me. His head was cocked back while his hand gripped something I couldn’t recognize like a basketball. He then began panting like he had just run a mile. Worried, I texted him, telling him I was downstairs and saw him convulsing, asking if he was okay. Rob looked over his shoulder, spotted me and began laughing. He turned his back to me again and texted back.
“I’m great, buddy. And so is ur GF.” Rob’s text read. He was laughing to himself as he was typing.
Suddenly, Melissa came into view, wiping her mouth. She was rising like she had been kneeling or crouching in front of Rob, who said something to her before thumbing over his shoulder towards me. Melissa went wide-eyed, but something Rob said to her made her breathe a sigh of relief before laughing with Rob in unison. Melissa made her way down the stairs while Rob, still grinning at me, gave me a thumbs-up. A security guard, who must have been a friend of Rob’s, fist-bumped him before they began talking to one another. Rob’s body language suggested he was bragging, but of what, I’m not sure.
Melissa came up to me with a smile before kissing me on the lips, which were glossier than usual. Her lips tasted funny, almost salty, and a cream of some sort was lingering on her tongue. I assumed whatever her drink of choice was that night; it was thick. What struck me as odd was the smile my girlfriend gave me after my lips tasted hers. It was almost like she was laughing at me. I looked up at Rob and saw him laughing as well.
Rob treated me completely different at work the next day. He seemed to be capitalizing on the unconditional favors I was doing for him, too. For instance, one afternoon, he handed me all his paperwork, rubbed my hair, and told me to make him look good, as our boss was paying attention as to who was dead weight at the office. Rob left early that afternoon while I stayed late finishing both our workloads.
On another occasion, Rob saw me in the bathroom, put me in a headlock, and nudged my head, right in front of my subordinates, who loved how he was making me look. On top of everything else, when I was picking up his lunch or coffee, he would tell me to “hurry up” before I left, sometimes even raising his eyebrow at me for not getting things for him sooner than I arrived. I began to worry that I fell out of my assistant’s good graces.
On the weekend, I tried to make plans with my girlfriend, but she told me she had other plans. When I asked what she was up to, Melissa saw my dick twitch upon telling me Rob had invited her over to his place – he was even coming by to pick her up on his way home from work. I never knew it was possible to feel jealousy and arousal at the same time. I texted Rob a few times to ask him why he didn’t tell me about taking my girlfriend out, but he didn’t return my messages. With that, I chose to drive my girlfriend to my assistant’s party with the intention of crashing it.
my girlfriend saw my dick twitch upon telling me my assistant had invited her over
My girlfriend had dolled herself up, dressed to the nines. Rob – along with every one of his friends – couldn’t take their eyes off Melissa. When we arrived, Rob’s bicep came between Melissa and me, and when he escorted her away with him, he looked over his shoulder and instructed me to “make myself useful now that you’re here.”
I did as he asked, grabbing a couple of beers, and walked towards him. Rob took his hand off the small of my girlfriend’s back and took both bottles out of my hand, handing one to Melissa, while taking a sip of the other one.
“Thanks, sport!” He said, winking at me. I instinctively went to get a beer for myself, and when Rob saw me lift one up, he ran up to me.
“Dude,” he said, putting his arm around my neck. “Those empty bottles ain’t gonna pick themselves up.
“Oh…” said, putting the bottle down, realizing I was looking like a slacker in front of him and his friends. “I’m really sorry, Rob. I don’t know what I was thinki–”
“That’s the problem. You weren’t thinking. Get to work, bro.”
The Kid with the Big Cock Gave Me a Swirley in Front of My Girlfriend
I felt like a third wheel at the party, as my assistant and my girlfriend spent most of the party together, moving from one place to another as if they wouldn’t be in my line of sight. I didn’t know anyone at the party, so made the best of my idle hands and continued to clean up as the party progressed picking up empty cups and beer bottles, and asking other guys if I could fetch them another. The smiles on their faces were borderline smirks, but I’m sure they appreciated my generosity.
At one point, I saw Rob going upstairs to a bedroom with Melissa, holding her hand. I followed them up there, and when Rob saw me, he told her he needed to take a piss first. Rob had a look of irritation on his face as he walked towards me, and on his way to the bathroom, he grabbed me by the shirt, dragged me to the toilet and flung me onto it. Trying to catch my barring, I got on all fours when suddenly I felt Rob’s knee on my back, which prevented me from moving. I heard a zipper, and suddenly, heard a stream of his piss over my head, followed by the sight of it landing into the bowl in front of me. This got a good laugh from most of the guys who followed us.
I couldn’t believe this was happening. My assistant was making me look like a complete wimp, humiliating me in front of everyone, including my girlfriend, who was watching this in complete awe.
When the last of Rob’s piss came out, a few drops landed in my hair before he took his weight off my back. I immediately jumped up and pushed Rob’s big chest in anger, in a futile attempt to regain my dignity. Of course, my meek arms pushing Rob’s muscular pecs was like using a twig to move a boulder – he didn’t even budge. If anything, I looked even punier in front of the audience watching us. Rob laughed while looking over at his friends while thumbing in my direction, a “this guy?” expression on his face. Rob walked up to me, reached out his arm for a handshake, and told me he was just joking around, and hoped there would be no hard feelings, winking at Melissa with a smile. I instinctively reached my hand out to shake his, when suddenly, my assistant spun around and gave me my first wedgie since high school, to a round of laughter, this time from a bigger crowd. The entire party was watching Rob and I the bathroom as if we were putting on a comedy show for their benefit.
It got worse. Before I had a chance to regain my composure, Rob grabbed me by the hips, flipped me 180 degrees with easily with his big arms, and dunked my head into his un-flushed piss in the toilet bowl. When he pulled me up and dropped me to the floor, I saw him high-five several of his friends before walking away with my girlfriend. I ran out of the bathroom and out of the party in shame, making eye contact with no one, but did see the reflection of Melissa and Rob entering his bedroom as I left his place. At first, I was hurt that my girlfriend didn’t check on me, but then I realized that Rob saved me from further humiliation by not letting her get near her piss-soaked boyfriend. Not wanting to ruin her night, I texted Melissa and insisted she stay behind. She replied telling me not to wait up, that she might crash at Rob’s place. I wanted her to, not wanting to face my girlfriend after watching my subordinate wedgie and swirlie me.
They had assumed I left, but after pouting alone in the corner for a while and being scared to show my face in public after the embarrassment I had just endured, I decided to see what Rob and Melissa were up to. I didn’t want her to be around me at that moment, but the fact that she left with Rob without missing a beat was not lost on me. The more I thought about the two of them, the harder my erection became. Walking by his bedroom, I peeked in as the door was slightly ajar. There they were sitting together. Rob’s arm was around her shoulder, and she was hanging on his every word. I tried to decide if I should interrupt them or leave. I didn’t like the feelings that came with being a jealous boyfriend, but the sight of Rob and Melissa sitting so closely together made my dick almost burst through my pants. Hearing my girlfriend laugh and giggle, I decided to give her and my assistant some privacy, leaving the house. As I walked back to the car, I received a text from Rob.
“No hard feelings, buddy,” it read, “Hope I wasn’t too hard on ya. Speaking of hard, don’t worry, I won’t tell her you were spying on us.”
I felt humiliated beyond belief. Rob thought I was spying on them! And he just brushed off the piss swirly he gave me like it was something to brush off. My instinct was to get angry, but this was Rob. Boys will be boys, I figured. I didn’t want to fall out of his good graces. Besides, it’s not like he beat me up or anything.
Rob dropped Melissa off the next morning. With a big smile on his face, the alpha male fist-bumped me and apologized for what he did to me, and justified it by saying he just wanted to get a rise from the guys. Rob explained that it was nothing personal, if he hadn’t done that to me, he would have done that to some other wimp, but unfortunately, I was the only one around. I found an apology somewhere in that comment and told him it was water under the bridge. He called me a good sport, and when I saw him reach his big hand out, I did the same, but looked stupid in the process, as my young assistant was reaching out to slap my cheeks a few times. Before he left, Rob kissed my girlfriend on the lips goodbye and gave me a thumbs-up.
Rob and my girlfriend started to become inseparable after the night of his party. If she wasn’t my girl, one might assume that she was his, based on the body contact and looks they gave one another.
One night, Rob invited Melissa to a movie with him and the guys. I tagged along with her, and while Rob was happy to see my girl, he didn’t even say hello to me, he just walked right by me. They all had sat in the licensed section of the theater before the movie started. Rob had his arm around my girl while the group chatted and drank. About 20 minutes into the movie, Rob and Melissa got up and changed seats, sitting all the way in the back. Rob saw me looking up at him and my girl and sent me a text – apparently the view was better up there. I agreed, getting up to join them, but was told to stay put via another one of his texts. Not wanting to disobey his order, I remained in my seat and watched the rest of the film.
After the movie, I asked Melissa if the ending shocked her, as I heard her gag loudly a few times during the last 20 minutes. Chuckling to himself, as if proud of something, Rob asked me if I wanted any of his popcorn, which I took. I don’t know why he was laughing, it was perfectly good popcorn, although I couldn’t recognize the thick white and wet linear topping he put on some of the kernels.
We went out for a bite to eat afterward. Rob and Melissa were sitting across from me. They didn’t take their eyes off me while I blabbed on about the movie. Rob seemed to be smirking at me, while my girlfriend was making weird facial expressions. I think she was exhausted, because she was shutting her eyes sporadically, quietly exhaling at times. I noticed only one of Rob’s hands on the table as I spoke. The other arm was under the table. What was odd was that the flinching of his arm was in sync with the weird facial expressions Melissa was making.
At one point, while referencing the movie, I talked about a list of things “as long as my dick.” Rob immediately joked, “so in other words, it’s a short list,” making everyone at the table snicker.
I took my girlfriend home shortly afterward, as Melissa started experiencing symptoms of lockjaw. Rob told her not to worry about it, and that it would go away on its own in no time.
“At least, that’s what my girls tell me.” Rob laughed.
My subordination to Rob started in the office, carried into my personal life, and came full-circle at work. I had become something of a laughing-stock with my staff, as Rob pretty much slacked off while I did his duties. Rob did keep me on my toes by suggesting that I would get another toilet-face-dunk if I didn’t do as he asked. My staff would snicker behind my back, or when walking past me, almost as if they knew something I didn’t. Management became aware of my reputation, with one of my superiors referring to me as Rob’s lap-dog. That same manager became friends with Rob, and it wasn’t long before Rob and I switched places – he got promoted to my job, while I got demoted to his assistant. The rationale was that, based on my reputation as Rob’s beta-male, I wasn’t a good representative of the company. Further, Rob’s dominance over me proved how natural he was at giving orders. He learned from the best – me, so he did well instructing my former employees and me. I, of course, executed all the work he was expected to do. Rob as my supervisor was a natural fit.
My relationship with him went from friendship to subordinate. I felt inferior to him, as 99% of his dialogue with me consisted of giving orders. He explained to me that I was the only one who could take care of his needs the way he liked it, and that he and I had a special kind of friendship. I appreciated his honesty and told him I would help him any way I could. Melissa told me she liked seeing this side of me, which only made me want to pamper Rob more.
Rob was harder on me than he was the other guys, but I understood that, because of our friendship, he couldn’t afford to let me slack, as it would look bad for both of us. He was right, of course, and had no trouble being the hardest working guy in the office.
Work eventually became unpleasant after my demotion. Employees formally under my management treated me like shit, dumping work on my desk, snickering at me, no one treating me with any respect. Some of the guys tried to pass off their laundry to me and delegate their paperwork to me the way Rob did. Thankfully, Rob having none of that. He protected me from would-be office bullies, telling everyone he needed me focused on his own needs, that he couldn’t afford to spread me too thin. Doing his work at the office was for the betterment of the company. Running his errands was for the betterment of the boss, aka himself. The message was clear – hands off – I was under Rob’s thumb, and Rob’s alone. Apparently getting my head dunked in his piss earned me his protection.