I shined Jordan’s shoes as fast as I could, knowing I also had to pick up his dry cleaning. He was my wife’s date for a company function. We all agreed that I shouldn’t accompany them to the party, but Jordan threw me a bone and allowed me to drive him there.

High School Cuckold Stories: The Kid Who Tormented Me is Now My Employee…or Am I His?

You see, Jordan was my high school bully. He and his buddy Dominick weren’t tough guys by any means, they were more on the preppy side, but they certainly gave me my share of humiliation, which included multiple swirlies, wedgies, and locker stuffing incidents. They both liked to embarrass me in front of girls. It all ended after we graduated, but much to my surprise, 10 years later, Jordan applied for a job at the company my wife and I worked at. She was a Senior VP, and I was part of her team.

The plan was to hire someone as my assistant, as my administrative tasks weren’t being delegated properly. Everyone in our department had their hands full, so naturally, a new employee was necessary. When Jordan’s eyes met mine, he was shocked to see me. He hadn’t changed much since high school – he still had his preppy looks, and he was still an asshole. When I reached out my hand to shake his, he smacked my cheek a few times and ruffled my hair. The guys at work seemed to think that was funny, they liked Jordan already.

My wife brought him up in bed that night, referring to him as the “cute one”. I sighed and told her who Jordan was, and the things he and his friend did to me as a teenager. I told her every humiliating thing, inadvertently painting myself as a complete and total wimp while making Jordan and Dominick look like overpowering bullies. She couldn’t visualize a preppy guy like Jordan slapping me around, but I could see she was trying to, for some reason. I wanted her to know who Jordan was so that she wouldn’t consider him a candidate for the job anymore. Much to my shock, she told me Jordan was the number one contender, noting he was over-qualified.

I became nervous – Jordan was back in my head, 10 years later. I didn’t want Jordan at the same workplace as me. Even though we weren’t teenagers anymore, he was capable of making me look bad without laying a hand on me. I wondered why my wife considered him a job candidate if he was overqualified, but I didn’t question her decision-making process.

Just before lunch the next day, my heart stopped when I saw Jordan emerging from my wife’s office. I was the first thing he saw when he walked out, we made eye contact just as he zipped up his pants, giving me a thumbs-up and a smirk. My wife, smiling with glossy lips, introduced him as my new assistant. Jordan was smiling too, his firm handshake squeezing mine too tightly. I squirmed a bit and my wife noticed, squeezing her legs together while watching my discomfort. Before he left, she told Jordan, our newest employee, that he would be starting the next day at 9:00 am.

I asked her if she was out of her mind, and she said she was…but with the perfect plan. She was going to help me get back at Jordan for all the things he did to me! I told her I wasn’t angry with him anymore, but I could see what she was getting at. With him as my assistant, the idea was that I could get “revenge” for all the bullying Jordan put me through, in a ‘I get the last laugh‘ kind of way.

I walked into my wife’s office after lunch the next day intending to eat with her and to ask why Jordan never showed up for work, as I waited all morning for him to arrive in my office. He was in her office when I got there – they were having coffee on the couch, talking. Upon seeing me, my wife asked me if I congratulated Jordan on his new position. When I held out my arm for a fist-bump, Jordan hit my fist so hard, it almost smashed the bones in my fingers. I yelped a little, and once again, my wife noticed, biting her lip when he winked at her afterward.

I spent the afternoon with Jordan, showing him around the office, how things run, what his tasks would be, the full orientation. We didn’t talk to each other while together very much, it was strictly professional. Still, I was a little nervous around him, almost waiting for him to do something to embarrass me. He could tell I was timid around him, and it seemed to boost his ego. I felt like his sidekick while we walked around, even though I was his boss. I was talking nervously at times during awkward silences, eager to break it. He knew I wasn’t comfortable around him. When we made eye contact, I could see mischief in his eyes. He was trouble, and I suddenly wanted to stop this little plan of my wife’s, but it was too late – we already hired him, and I didn’t want to look scared of my former bully as a grown man.

I told Jordan he could go home early that day. My wife was leaving at the same time, asking if she could give him a ride. As they walked out, Jordan turned his head back gave me the thumbs up while walking away with my wife. She was looking at him like a celebrity, like someone she really wanted to get to know.

I stayed at work until about 7:00 pm that evening, and when I pulled up to the driveway, so had my wife – she had not been home yet since leaving the office. She looked disheveled, her hair was messy, and her blouse wasn’t even buttoned properly. She was eager to get home and shower. I just shrugged it off to feminine issues and made dinner. In bed that night, my wife asked me a series of questions about things Jordan did to me in high school. Apparently, Jordan brought her up to speed on the dynamic between the two of us a decade ago. My wife went to sleep with a smile on her face, while I lay beside her, wide awake, worried about the consequences of my former high school bully’s return.

By noon the next day at work, Jordan asked me to pick up lunch for him and his new friends in the accounting department. The girls at the office loved him, and the guys took to him naturally. He didn’t talk to me like his superior, he talked down to me like an underling. Jordan subtly took lead by directing me – his boss – and with that, my staff no longer looked at me like a person of authority, especially not after seeing me fetch him coffee earlier that morning. Even though I was delegating a lot of responsibility to him, he wasn’t good at following any of my orders, not like me, who was flawless at following his.

I asked my wife to fire him, but she immediately put the kibosh on that plan, telling me that Jordan had only been back in my life for a few days, to ride out whatever discomfort he was causing me. I hadn’t realized that by asking her to fire him for me, I had shown that my former high school bully had broken me as an adult. Jordan walked in at that moment asking what was going on. My wife, to my horror, told him I wanted him fired. Jordan shook his head and thumbed to the door, asking telling me to leave her office because he wanted to talk to my wife about me. I left the office with my head down, embarrassed, and intimidated.

Even Though My Bully from High School Was Now My Subordinate at Work, He Manipulated Me Into Working for Him

My wife left the office at 4:00 pm that day, and Jordan again left at the same time with her, but without my permission – he should have stayed as long at the office as me, being my assistant. When my wife came home at 8:00 pm that night, she told me she made a business decision, agreeing with me that Jordan is not cut out to be anyone’s assistant. She did say he excelled at delegation, noting how easily he could get me to do whatever he wanted, with precision. She told me at one point, she looked out her window and saw me on my knees tying up his shoelaces. She talked to several senior staff members privately and asked what they thought of Jordan and I switching places. With Jordan’s experience, she felt that he could help the company grow. She mentioned Jordan’s qualifications were stronger than mine, and that her staff unanimously agreed that I had taken the company as far as I could with it, but it was time for someone better to take it further. With that, Jordan was promoted to my position, while I was demoted to the job he was hired for.

I didn’t challenge the decision, it was made. It’s hard to make business decisions when you’re married to the boss. Besides, if Jordan taking my job away from me was best for business, it would have been selfish to stop it.

“Try not to think of this as a demotion.” My wife said, trying to make me feel better. “So what if your high school bully is now your boss.” I caught her squeezing her legs together upon saying that last part.

When I went to work that morning, Jordan had me move all my stuff out of my office, since he was moving into it. He assigned a small classroom desk to me beside the washroom, the only place available that was close enough for me to come running when he snapped his fingers, as he put it.

As humiliating as Jordan’s quick ascension at my expense was personally, whatever he told me to do, I did it quickly and efficiently, ready and waiting for my next instruction. The office watched with awe each time I scurried around for the new guy. I was making Jordan look powerful. To be honest, as the days passed, I felt more comfortable taking direction than giving it. Part of me didn’t want to admit that this was because of Jordan, but I wondered if I would have been so obedient if anyone else had replaced me.

By week’s end, my awkwardness turned into loyalty. Jordan was nice to me, not so much in a respectful, friendly way, but in a big-brother to kid-brother approach. If anything, the compliments he gave me, if any, were not that different than a dog owner commending his pet. “Good boy” and “attaboy” were words frequently coming out of his lips to my ears. I didn’t take this as an insult. I felt like we made a good team, and quite frankly, with my former bully as my boss, the company was running like a well-oiled machine.

At a staff meeting, Jordan arrived late, and not finding a seat, asked me to give up mine. I got up without missing a beat, which got a few chuckles from the guys at the table. When my wife walked in, Jordan thumbed to the door and told me to leave, telling me assistants don’t belong in executive meetings. The laughter continued as the door hit me on the ass on the way out.

I continued to work hard for Jordan with each passing day. I was losing a ton of weight, my body was really shaping up from all the running around I was doing for him, both for business and his personal errands (yes, Jordan had me pick up groceries, his dry cleaning, polish his shoes and other things “for the betterment of the company“). I was overworked, but Jordan needed the help, and who better to help him than the guy who used to have the same job, as my wife pointed out. I felt like we were a team, even though he was getting exclusive credit on just about anything I did with for him.

By the end of the month, Jordan had hobnobbed with senior executives, including my wife, on a daily basis. Actually, my former high-school bully and my wife spent a lot of time together, going to corporate get-togethers, business dinners, trade shows, etc. At times, he invited me, but only if he needed me. For example, Jordan was invited to a golf course for a business meeting, and I scurried behind him all day in the heat as his caddie.

One day, while I was buffing his shoes, Jordan mentioned to me that he knew my wife and I hadn’t been having sex. When I asked how he knew that, he patted my cheeks and told that my wife doesn’t keep any secrets from him. I felt weird about my wife telling our private matters to my former high school bully. My dick started to get hard when he told me he guaranteed he could get he and my wife naked in the same room. When I asked how, he told me to suggest to my wife we have a threesome. I knew right away he meant a threesome with him. He told me not to worry, nothing gay would happen between us and promised me the threesome would end with her cumming. He told me to trust him because I was his buddy, and he had a plan. I gave in and accepted his offer.

It didn’t take much convincing for my wife to agree to Jordan’s threesome idea. I don’t think I sold it as a way for her and me to be intimate, as much as I did that Jordan would be naked with us her. I was surprised she wasn’t offended – she was squeezing her legs together the more I talked about Jordan. We talked about the threesome with my former bully in bed. I marveled at how much things have changed – a month ago, I wouldn’t have entertained another man naked around my wife, and now all I wanted was for Jordan, my wife and I to be naked in the same room together. I think we were both horny enough to want to have sex right then and there, but without mentioning it, both of us preferred to hold out for Jordan to be in bed with us.

On the night of the threesome, Jordan came over that night with me, and when we walked in, my wife was wearing the sexiest Victoria Secret lingerie I’d ever seen. We had a few drinks – they sat on the couch and I sat on the floor. The more my bully and my wife talked, the closer their lips got – if you didn’t know us, it would look like a young good-looking couple were on a date, and I was looking up at them like some creepy voyeur.

My heart stopped when I saw Jordan’s hand on her cheek, his lips on hers, her hand gripping his head and pulling him close. When the kiss ended, Jordan told me to get naked and without missing a beat, I did. When they both looked at my dick at the same time, he whispered in her ear, and she tried not to laugh, looking away from me.

Jordan had me take off his shirt, t-shirt, belt, and pants before walking to my bedroom. My wife made a beeline for the bed as I undressed my boss.

“Lemme go first, buddy,” Jordan said with his arm around me, before pushing me it a chair in the corner. They fell on the bed together in a lip-lock, and the kissing didn’t stop for a few minutes. Jordan’s index finger and thumb were rubbing my wife’s pussy and I had never seen her more wet. My wife began kissing his chest, licking his stomach. His thick dick burst out of his shorts the second she pulled them down. I was sitting there in complete and utter shock, but I had no intention of stopping what I was watching. My high school bully was about to stick his big fat cock into my wife, in my bed, in my house, right in front of me.

I watched Jordan’s right hand gripping the back of my wife’s head, guiding it back and forth on his monstrous tool. He was directing her verbally as she tried to worship all of his meat at once. My wife was so eager to please my bully, sexually. I noticed that there was a familiarity between the two. He knew where she liked to be touched, and she seemed to know exactly where liked to be licked and stroked.

That Awkward Moment When You Get Caught Jerking Off Watching Your High School Bully Fuck Your Girl

Jordan grabbed my wife’s ass and impaled her on top of his big dick. He used his finger to tell me to come towards the bed. I was reluctant, but Jordan sternly told me not to make him ask me twice, and within seconds, I was bedside. They both were laughing at the trail of pre-cum I had made on the floor on the way. There were so many emotions that were going through me at this point.

I wasn’t delusional – I knew on some level, I wanted this to happen. I was cognizant of my obedience to my high school bully, no matter how humiliating the task was. On nights when my wife came home late, I choose not to question her whereabouts, not because I didn’t want to be a possessive husband, but because I didn’t want whatever was happening between the three of us to end. I had managed to purge myself of Jordan’s nightmares as a kid, and sure enough, 10 years later, I was at the foot of my own marital bed watching my wife struggle to accommodate the thickness of his big cock.

I hovered over my high school bully, who lay on his back in my bed, while the woman I married – my bride – grinded and straddled him, clutching his chest, tasting his lips…. the second her tight little pussy swallowed Jordan’s entire girth, I shot my load over their heads without touching myself.

Jordan told me to make myself useful and support him on “like a bro“.

“If you wanna watch your girl get fucked, you gotta contribute.” Jordan said to me as if I wasn’t entitled to be in the room with him and my wife.

I felt awkward at first, watching my wife on all fours with a look of pure lust on her face, her hair tangled in Jordan’s hand behind her, his other hand on her ass. I watched him thrust in and out of her, calling her degrading names, awakening her animal urges, making her totally give into him. He looked me again and raised his eyebrow, a look that intimidated me right into cheerleader mode.

“Yeah dude, fuck her!” I shouted while she rode him faster. “Fuck her hard! Look how bad she wants you, man!” I felt ridiculous, and Jordan must have thought so too, as he laughed his ass off and asked my wife, “you hear that baby, your husband says you want me badly!”

“I do!” she squealed between breaths, her hot juicy pussy the wettest I’ve ever seen it.

Thumbing to me, my high school bully asked my wife, “has needle-dick over here ever fucked you this good?” I felt angry that he insulted me, and was about to tell him off when my wife shouted “NO!” I was mad that she didn’t defend me, and my 6″ penis was hardly a needle dick. Quite frankly, before I saw what Jordan was packing, I had assumed I had a big dick.

Jordan told me to get them some water, as both were sweaty profusely, our bed was practically doused. When I returned, she was on top of him, her head reeled back. Jordan was making her do all the work in bed, like a stud. My former high school bully kept looking at me with that smirk, and I was starting to realize this threesome wasn’t going to include me at all. Jordan had goaded me into fucking my wife in front of me, embarrassing me yet again, in front of the most important person in my life, in my own home. But he didn’t really goad me at all, did he?

“Yeah bro, look how hard we’re giving it to her!”, Jordan taunted after I was caught masturbating. “Jerk your little dick off buddy, tug on that piece of taffy, come on, you can do it!” My wife giggled and kissed him, asking if she was making him happy.

“You’ll do” he replied, making her work even harder to please him. Jordan gave me another wink and a thumbs-up as she hustled it up, riding him faster, moaning more sexually.

I knew they were both about to cum because the headboards were smashing the walls, and the bedsprings were creaking so loudly, I was sure the box-spring was ready to break. My wife was on her back, her legs on his shoulders, and Jordan was giving it to her hard. I could see the contrast between Jordan and I in bed – I always made love to her gently, while Jordan was using her wet hot pussy as a battering ram. She started screaming all kinds of things she never did to me, things about his cock, his looks, his body, his attitude, his confidence, his perfection…she was boosting his ego and he was loving it. Jordan looked at me every time she screamed his name the harder he pounded her – he could see I was loving and hating this at the same time.

“Come on, man, we all gotta cum at the same time if this is gonna be a threesome, right?” he said. “Don’t be discouraged about being caught jerking off in front of us! Come on!”

He was putting too much pressure on me and I knew I wasn’t going to cum with them. I started pumping my meat faster and faster at the side of the bed, watching them fuck like animals below me. They were both getting very aggressive. He was meeting her every aggressive thrust and vice versa, and when he came, a fountain of cum erupted out of her wet tight pussy and his big dick. Jordan knelt over her my wife’s face and shot 4 streams of cum all over her lips and huge tits. I could see cum splatter all over to the sides – on my pillow case, the duvet covers, the bed sheets, the nightstand, and the picture frame sitting on it. As perfect as Jordan may be, he had no control over how much cum he spewed out, nor the direction it landed in.

I found Jordan’s rope of cum on my wedding photo somewhat poetic. His thick load was dripping down a picture of my wife and me, a stream of my bully’s semen dividing us, covering my tuxedo and her wedding dress. I noticed something small in front of the picture frame, something shiny that caught my eye, but I was distracted by Jordan, who jumped out of bed. He slapped my cheeks and ruffled my hair, thanking me for the “threesome”, smiling at my wife before abruptly leaving – no romantic cuddling for him.

My wife and I looked at each other almost like strangers, no idea what to do or say next. The cum on our wedding photo finally finished dripping down and landed on the nightstand, directly onto the shiny object I identified as my wife’s wedding ring.

END