Jordan had been my bully since my senior year of high school. Though both of us were late bloomers and behind a grade, we were both over eighteen when we first met. The fact that I was practically an adult made the bullying I endured all the more humiliating. I was cool before Jordan came to our school, but once he set his sights on me, I turned into a social pariah.
Going to the same school with Jordan was a nightmare. I’m not sure why Jordan picked on me. The other kids would get a good laugh watching him terrorizing me. I was meek and timid while he was stocky and aggressive. Jordan never did anything violent; he just loved watching me squirm. On one occasion I came into the washroom just as he had finished taking a leak, and I left that washroom with a mouthful of urinal cake. On another occasion, he grabbed me by my legs and used my body as a broom to wipe up all the sweat off the gym floor. To add insult to injury, during that incident, I saw the gym coach laughing from my peripheral vision before he broke up Jordan’s fun. From shooting spitballs at me, to shoving me in lockers, Jordan didn’t make my senior year a whole lot of fun.
When he visited the store I worked at; he would always do something to make my day miserable. Once, he intentionally kicked over two big piles of books on the floor that took me hours to organize. When I asked him why he did it, he used finger quotes to say it was an “accident,” but that it was my fault for leaving a safety hazard on the floor. The store manager made me apologize to Jordan in front of my peers, his friends, and other customers. He smirked at me when I did, patting my cheeks lightly a few times before leaving the store.
When Jordan would see me on the streets, it was no better. He did everything from throwing snowballs at my head, to taking a piss on my car (yes, I walked in on him doing it, and he didn’t stop when he saw me. He caught me looking at his flaccid dick, which was still bigger than my 6”).
Prom Night Cuckold Stories: Your High School Bully Meets Your Girlfriend
Things got worse when he found out I had a girlfriend, a beautiful girl younger than me, but older than him, named Kimberley. When he asked who the “piece of ass was” that I was talking to and learned that I was her boyfriend, he did a double-take, shocked that a guy like me could score a girl who looked like a hotter version of Jessica Alba. For the first time ever, Jordan was nice to me while asking all about her, and as he did, I felt like we were bonding. He was talking to me like he would talk to his other friends. After that day, Jordan ceased picking on me, and his newfound kindness towards me was something I immediately embraced. Jordan could tell I was eager to be his friend rather than his wimp.
One day after work, Jordan approached me on the way out, asking if I wanted to smoke a joint with him. I politely declined, saying I wanted to, but my girlfriend was on her way to meet me for dinner and a movie. Jordan walked with me, lighting up the joint while inviting himself on the date I had with my girlfriend. He wasn’t asking me to come, and I wasn’t opposed to him hanging out with us. On our way to meet Kimberley, I ended up taking several hauls of his spliff.
When we met with Kimberley, I was stoned out of my mind, as I had smoked way more than I should have, coughing like an amateur, louder than Jordan’s laughter at my inability to handle pot. My girlfriend was also laughing with him, introducing herself to my new friend. After learning I was with the man who I had told her was my bully, Kimberley’s eyes beamed, telling Jordan she heard so much about him. Jordan and I looked at each other, realizing that I had I had complained so much about him to my girlfriend, that I had made myself look puny in comparison to him. I inadvertently built up my bully as an alpha male to my girlfriend.
My bully and my girlfriend talked for a good 10 minutes while I tried to gather myself. Seeing as though I was in no way to go out, Kimberley suggested we cancel our plans, but Jordan suggested I cab it home and sleep off my high. He implied that it would be rude for my girlfriend to spend a beautiful night alone just because I couldn’t handle smoking weed. Jordan took the initiative and told me Kimberley would be safe with him all night long, whispering those last three words into my ear. My girlfriend loved the idea of getting to know my apparent bully-turned-friend, and within seconds, Jordan hailed a cab and physically tossed me in it. I looked out the window before the cab drove away to see my bully’s arm around my girlfriend, his other hand giving me a thumbs-up.
When my girlfriend called me later that night, it wasn’t so much to check on me as much as it was her gabbing away about her new friend, Jordan, and what a great guy he was like she was talking to one of her gal pals. I tried to explain that she was praising my bully, but Kimberley told me to grow a pair, seeing as though Jordan was younger than me. Instead of arguing with her, I was mindful that she perceived him as the alpha male, in comparison to me, no thanks to all that I told her about the things he put me through. She told me Jordan invited himself over to my place for dinner the next day, and that she would be coming over with him “as his date.”
I prepared dinner the next day, slaving over it, and when my girlfriend arrived with Jordan, I could feel his cockiness piercing right through me without saying a word. But I remained a gracious host, even though he and my girlfriend were talking to each other like I wasn’t even there. When I asked how dinner was, my girlfriend loved it, but laughed and hit Jordan in the arm when he shrugged his shoulders and said: “meh, I had better.”
By the end of the night, I was watching dishes while my girlfriend and Jordan were sitting on the couch, talking. When I walked into the living room, my girlfriend was alone, telling me Jordan was in our bathroom. When he came out, he told me to get him a beer while sitting right back down with my girlfriend. I grabbed three, and when I gave Jordan his, he said to me, “that bottle cap ain’t going to twist itself off, buddy,” again making my girlfriend hit him, this time smacking his chest, caressing it for a few seconds. Jordan noticed my eyes on her hands touching his body, winked at me, and gave me another thumbs-up.
My Girlfriend Ditched Me and Left with My High School Bully
With my back to her, I could hear my girlfriend trying to conceal her laughter as Jordan lead her back to the living room. As I tried to compose myself, all I could hear behind me was whispering and heavy breathing. I gathered the courage to tell Jordan to get out of my house, angry at his betrayal and humiliated in my own home, in front of my girl, but when I went to the living room, I couldn’t find him or Kimberley. A text on my phone from her said she got a ride home with Jordan. I felt relieved knowing I wouldn’t have to confront my bully-turned-buddy-turned-bully.
When my girlfriend FaceTimed me a couple of hours later, she was giddy. Her blouse was buttoned incorrectly, and her hair was bunched up, like the back of it was gripped. Her lips were glossy, and some stain was on the right of her blouse. I told Kimberley I was fine with her having her own friends, but her hanging out with my bully – especially in spite of what happened that evening – was something that made me uncomfortable. My girlfriend wasn’t having any of it, telling me that the moment I start selecting her friends is the moment I become a possessive boyfriend. I bit my tongue, hoping she’d figure out on her own how much of an asshole he was.
A text from Jordan afterward surprised me, as he thanked me for dinner and told me to thank my girlfriend for “dessert,” which confused me because she didn’t mention serving him any upon driving him home. “No hard feelings, buddy” was the last thing he said to me. I realized that if he and my girlfriend were going to be friends, that it would be in my best interests to remain on his good side.
The next day I decided to surprise Kimberley at her place and stopped dead in my tracks when I saw her cuddled up with Jordan on her couch from outside. When she picked up her phone and dialed my number, she had no idea I answered from outside, standing right across from the two of them.
Once she started speaking, Jordan’s lips were in her other ear, and his big thick hand was on her stomach, sliding down very slowly. She made little small talk with me, flat-out telling me that Jordan was over and that he wanted me to know I was with her. My sweet, innocent girlfriend didn’t even try to sugarcoat the fact that she was with hanging out with a guy who loved to torment me. Part of me felt betrayed, but the fact was, she had her own life, her own friends, and it would be controlling of me to tell her who she could – and couldn’t – be friends with. I didn’t want to be that kind of boyfriend.
My Girlfriend Talked to Me Over the Phone While My High School Bully Fucked Her
Kimberley called my cell about twenty minutes later, while I was walking around the block, trying to get my bearings.
“OH GOD, I’M GOING TO CUM!”
“Honey” I asked confused. “Where are you coming?”
“RIGHT HERE, OH FUCK YEAH, JEEZ JORDAN, FUUUUUUUUCKKKKKKKK……”
“You’re not masturbating, are you honey?”
“Nooooo….no, I am not.”
“Where…is Jordan’s hand right now?”
“Do you really want to know?”
“Sweetie, his thumb is thicker and longer than your dick.”
(Obnoxious laughter from Jordan)
“Come here.” I could hear Jordan say to her.
“Whoooo!” She yelped. I looked back into the window and saw that he had gotten up and lifted her over his shoulder, carrying her upstairs.
“What’s happening?” I asked, nervously.
“He just lifted me over his shoulder. We’re going upstairs, honey.”
“Oh my god.”
“Honey…. oh god honey….” She whimpered.
“Are you okay?!” I asked, worried.
“I’m good…soooo goood….”
“What’s going on? “Suddenly, the phone rattled, and I could tell Jordan had taken the phone from my girlfriend.
“Beg me.” My bully said to me.
“Please put it back in!” Kimberley pleaded.
“Not you, him.”
“You can’t be serious,” I said, head in hand.
“Beg me, dummy. Beg me to finish off your girl.” He shouted.
“Fuck you, Jordan. “I said.
“That’s what she’s doing, buddy.” He chuckled, laughing at his own comment.
“Honey, please!” My girlfriend whimpered.
“BEG,” Jordan shouted.
“Do it! Please do it! I need to cum!” Kimberley cried out.
“Goddamn it, ask him! ASK HIM!!!” She demanded.
“Please fuck my girlfriend, Jordan.”
“I was. “He laughed.
“Please put it back in her.”
“Put what back in what?”
“Your cock. In her tight little pussy.”
“My what in her what?”
“Your big cock in her wet tight pussy.”
“Please put your big dick in my girl’s hole, man.”
“JORDAN, PLEASE PUT YOUR BIG FAT COCK IN MY BEAUTIFUL GIRLFRIEND’S SEXY TIGHT PUSSY. DO IT.”
“Well, since you asked so nicely…” he laughed.
“Ohhhhh…. god……fuck…. yeah….” Kimberley moaned.
“It’s nice, eh baby?”
“Yeah, it’s real nice…”
“Nicer than with him.”
“I’m a better lay than your boyfriend.”
“Who’s got the bigger dick?”
“You, by far!”
“Hear that, dummy?”
“Yeah, I heard it.”
“How much bigger is it, babe. Tell him.”
“Baby, it’s really thick. Now I know what a beer-can cock is.”
“Oh fuck,” I muttered, trying to tame my sudden growing erection.
“You hard dummy? You jerking off listening to your girl tell you how much better in bed I am than you?”
“I’m not jerking off.”
“But you’re hard.”
“Say it, or I’ll pull out again.”
“Do as he says, baby, I need this!” Kimberley shouted out.
“I’m pitching a tent.”
“Sissy cuckold,” Jordan said.
That was the last time I spoke to either one of them. I gave Kimberley the cold shoulder and cut her off completely. She tried to get back together with me, but I was way too hurt by how she cheated on me. I wanted to be with her again and didn’t think I could do better than her, but I would have been a total joke for taking back someone who cheated on me. She was my first girlfriend, but that chapter of my life had ended, thanks to my high school bully.
Things went great for weeks after that. I started dating a new girl from another school named Julia, who was the same age as me. Jordan was absent from school as a result of some suspension, so I didn’t have to see him. Prom was coming up, and I was so excited to ask Julia to go with me. I made a whole scene out of it, getting on one knee in a crowd to be my prom date. I was ecstatic when she said yes.
Julia and I met at a competitive rally, bumping into each other while getting refreshments. Something just clicked as soon as we saw each other, neither one of us could stop smiling around one another. Looking at her was like looking at a work of art. She was brunette, on the swim team, and on the honor roll, so she was beautiful and smart. The way she looked at me made feel made me forget about Kimberley. I chose not to mention anything about Jordan or my ex-girlfriend to her.
Jordan returned to school a week before prom. He went back to his old ways by picking on me in the hallways, shoving me against lockers, even tossing me into several dumpsters. This time there was no Kimberley to get me out – I had to rely on the kindness of the janitorial staff. I ignored the laughter thrown my way as they got me out each time.
Though we were both of legal age, Julia and I had not yet had sex. Although we didn’t talk about it, the unspoken idea was that we were going to do it for the first time at my school’s prom. I prepaid for a limousine for the night and spent the money I earned from part-time jobs on a five-star hotel room for us.
Things changed between us a couple of days before prom night, however. The sweet girl I fell in love with wasn’t acting so innocent. She was dressing provocatively, almost slutty. She seemed more confident and assertive, often texting, and giggling with someone else right in front of me. When I asked who she was talking to at dinner one night, she told me a friend of hers had introduced her to some guy she found fascinating. I didn’t pry, but it was clear that she was rather taken with whoever this new guy was that she had met.
I wasn’t a jealous type of guy, at least I hadn’t been up to that point. Either this new guy in her life was just a friend, or I had competition. I figured if I had to tell my girlfriend that she was mine, then she wasn’t really my girlfriend in the first place. I wasn’t concerned that she was going to start dating someone else because I felt that she would see me as her true love if she had someone to compare me with. But the change in her was congruent with this new guy she met. It didn’t take long before I began to feel out of her league, like she had evolved, and could do better than me.
On prom night, Julia dropped a bombshell on me in the limo. The new guy she was talking to went to my school, and he was going to be at the Prom! She kept that from me because she didn’t want to make things awkward between myself and this guy, who she named, “Jordan.”
That was the first time she said his name.
I never thought to ask what the guy’s name was. It had no relevance. The guy she was talking to had no identity to me, and now that I knew who she was talking to, my heart was beating rapidly. I was sweating; I didn’t look good at all. I was getting faint, panicking, trembling. The possibility that she could have been referring to some other Jordan was unlikely – he was the only one with that name in our grade. I was so lost in my love for Julia for the last several weeks that I hadn’t even entertained the thought of bumping into Jordan at the prom, or what he could do to me if I did. How humiliating would it be if he bullied me in front of my girlfriend?
I made a fool of myself at the prom within the first five minutes of arriving. I looked terrible, so meek and scared of my own shadow, knowing that at any minute, I was going to be face to face with my bully, in front of my girlfriend. Julia was embarrassed, but stuck by my side, coddling me as I tried to get a hold of myself. I asked her if Jordan had mentioned anything about me, and she looked at me confused. I had never mentioned anyone named Jordan to her, so she didn’t think we knew each other.
“The only person he ever talked about at your school was some wimp he liked to bully around.” She said to me, shrugging her shoulders.
“What did he tell you, exactly?” I trembled, barely getting the words out.
“About this so-called wimp?”
“I don’t know, some kid who goes here he liked to have fun with.”
“What kind of fun.”
“Just…what did he say?”
“Geez, I don’t know…he mentioned some stuff. Shoved the guy into a locker a few times, I think he got tossed into a garbage truck.”
“He got tossed into a dumpster.”
“Oh, you saw it?”
“It happened a lot.”
“Wow, how funny was that?”
“It wasn’t funny.”
“Oh, lighten up, the kid obviously liked the attention. Any sort of man would have stood up for himself.”
“So, that kid didn’t defend himself, and that makes him less of a man?”
“How could you say such a thing?”
“Honey, no girl is attracted to a spineless wimp. You chose who you want to be in life.”
“You’re saying this kid chose to be a sissy cuckold?”
“Well, yeah, duh.”
“Actually, from what Jordan mentioned, this kid was volunteering to do his homework, sharpening his hockey skates, hand-washing his jock strap…”
“Because Jordan told him to!”
“If Jordan told him to jump off a bridge, should he?”
“Whatever. Jordan told me this little twerp was going to be here tonight.”
“This little twerp…”
“Geez, lighten up, what’s with you all of a sudden?”
“You’re defending a bully.”
“You’re vouching for a bully!”
“I was thinking about that…is he really a bully, or is he just confident?”
“There’s a fine line between confidence and cockiness. Assertiveness and arrogance.”
“You’ve clearly got some issue with Jordan. Honestly, I didn’t even think you two would know one another. I know he goes to your school, but you two are polar opposites.”
“Everyone knows who Jordan is, Julia.”
“Yeah, he’s popular, confident, hot…”
“You think he’s hot.”
“Oh relax, just because I find someone attractive doesn’t mean I’m marrying them. You’re being awfully defensive. Wait a minute…”
I could see the wheels turning. Julia was putting things together, and she started smiling. I wasn’t sure if it was because she figured out I was the twerp she was referring to, or because Jordan was approaching us.
My High School Bully Fucked My Prom Date in the Limo I Paid For
My prom date sprung up and walked over to my bully, who looked rather buff in his black tuxedo. Julia and Jordan looked like a model couple standing together. After they greeted each other with a hug. Julia took his hand and walked over to me.
“Jordan, this is my boyfriend,” Julia started to say, “But you already know that, don’t you?”
“Hey, shitstain,” Jordan said to me with a smirk. “I gotta hand it to ya, you have GREAT taste in women.” I closed my eyes and swallowed hard.
“Oh my God.” She said very incredulously. “This is amazing. This is just…wow.”
Jordan smacked my cheeks a few times and told me to get some punch for him and his Julia.
“You here with anyone?” Julia asked Jordan as I walked away.
“Nope,” Jordan smiled. “Came here stag with the boys. It’s not who you come with and all that…”
“Good, you’re with us tonight.”
“You’re with me tonight,”
“What about the shitstain?”
Julia just smiled at him mischievously, and as I returned with 2 cups of punch, I worked up the courage to confront my bully and let him know how things stood that night.
“Julia is my date tonight, Jordan,” I said, defiantly. Jordan took his hand and placed it on my face, pushing me away.
“Not anymore, she’s not.” He said putting his arm around my girl.
“Tell. Me. EVERYTHING.” She said to Jordan, her hand stroking his arm. “I wanna know more about the relationship between you two.”
“There is no relationship,” I said to Julia.
“He’s right,” Jordan laughed. “I wouldn’t be friends with a douche like this.”
“What happened to the girl you two had in common? Laura, was it?”
“Kimberley,” I spoke up.
“Yeah, is she here? I’d love to talk to her.”
“Haven’t seen her,” Jordan replied. “But if I do, maybe you, me and her can have some fun tonight.”
“You’re so bad,” Julia said stroking his chest. Jordan looked over at me and winked.
I will never forget my prom night. With his arm around both of us, Jordan made me give Julia a tour of the school, specifically showing her all the places he tormented me. My girlfriend asked me details about the things Jordan put me though, and when I wouldn’t speak up, Jordan’s hard slaps to the back of my head got me talking. I showed Julia every dumpster and locker I was ever inside of, the urinals my head was placed in while he pissed, and the locker room I received wedgies in.
I watched my bully and my girlfriend dance to our song at the end of the actual prom, and at one point, with her back to me, Jordan grabbed her ass while looking at me over her shoulder. I saw everyone look at me and snicker at that moment, including Jordan, who was giving me the finger while grinning ear-to-ear. I went to the bathroom to get a hold of myself, and when I came out, Jordan and Julia were sitting at the table…making out.
When Julia and Jordan returned the table, she looked over at me with pity.
“It’s not who you come with, it’s who you leave with.” My date said to me before kissing Jordan on the cheek. That was her way of saying her and I were done.
Jordan did it again. He stole my girl again, and this time, he did it at my prom.
I grabbed my jacket and began to walk away, but surprisingly, Jordan yanked my shirt and pulled me back.
“Julia tells me you rented a limo and a hotel room?”
“Yeah, what about it”? I asked while pulling himself away from his grip.
“Well, since you’re not going to be using those things anymore, why put them to waste?”
“I’ll get a refund,” I said.
“You said you pre-paid for those things, sweetie,” Julia said, blowing my cover. “Don’t be selfish. Besides, don’t you want me to have a good time tonight?”
“Yeah, buddy,” Jordan said while slapping my cheeks. “Don’t you want me to show your girl a good time? Again, I mean?”
Julia laughed at his joke.
Twenty minutes later, I was sitting in front of my bully and my now ex-girlfriend in the limo I paid for, watching Julia kiss his lips, taste his neck, whisper things in his year. Jordan kept looking at me, knowing how much this was tormenting me. He was bullying me all night without even trying. At his instruction, I took a picture of Jordan giving me the thumbs-up with my girlfriend’s lips in his ear, and posted it to Instagram, hashtagging the photo with #promnightcuckold. Later, I stood outside the limo having a smoke with the driver as the car shook back and forth.
“Fuck, that kid’s the man.” The limo driver said. “Isn’t that the girl you came with that he’s banging in there?”
“Yeah,” I replied, watching the car increase its rocking pace. The car was almost bouncing, that’s how hard my bully must have been fucking my ex-girlfriend 5′ away from me.
“Wow. Sucks to be you, dude. You don’t even get to watch your girl get fucked good and hard on prom night.”
I shot the limo driver daggers as I stomped my cigarette butt out. Jordan suddenly rolled the window down and, looking sweaty, told me to go get him some water. Steam was coming out of the limo, which said a lot about how hard my bully was fucking my prom date.
“Hey, I’m billing your ass for any cumshots on the upholstery, dude.” The limo driver said to Jordan.
“Just bill the sissy cuckold,” Jordan said with a smirk, reaching his arm out for a fist bump to the driver, who reciprocated. A pair of hands pulled Jordan’s head back to the action. Julia wasn’t finished worshiping my bully.
Thankfully, Jordan didn’t fuck Julia in the limo. He made it clear to me that the hotel room I rented was going to be the place he nailed my girl. When we got there, a whisper in Jordan’s ear from my girlfriend caused Jordan to hand Julia his phone, walk over to me with mischief written all over his face, and before I knew what hit me, I was getting a wedgie. I saw Julia take a picture with Jordan’s phone, and just like that, Jordan opened the door with one hand and shoved me out the door with the other. I landed on my ass, and when looked back at my bully, he smiled at me, gave me the finger, and slammed the door. I could hear my girlfriend and my bully laugh at me from behind the door as I walked away.
Jordan sent me a text about 20 minutes later of my girlfriend’s mouth wrapped around my bully’s big cock. “She says it’s her first time sucking big dick, dude.” His message said under the photo.
That made it official. My bully had corrupted my girlfriend with his big dick.
24 hours later, the hotel management called to inform me that I would not be getting my deposit back, as there were damages to the bedsprings, headboards, and walls behind it. I knew that was Jordan’s last fuck-you to me, and I knew how hard he must have fucked my girlfriend to inflict that kind of damage to the bed.
Julia severed ties with me, telling me that, although she did feel bad about the way she was dumping me, she couldn’t help her feelings for Jordan. She told me she wasn’t in love with him, but her infatuation with such an alpha male overpowered any romantic feelings she had for me. And with that, I was an afterthought to the girl of my dreams.
“I know what happened to you was wrong,” Julia’s message to me said. “And I know what a bitch I must have looked like the way I went along with what Jordan did to you at Prom…but I can’t help it. Your bully is fucking amazing to me. Fucking amazing.”
I eventually had to block Jordan’s number from my cell, because he would send me pictures of my girlfriend doing things to him, specifically his big dick, things I had only seen in porn. I was so far beyond heartbreak, to the point where I had no choice to block Jordan because my dick was starting to twitch looking at how my girlfriend worshiped my bully.
THREE MONTHS LATER
I was happy high school was coming to an end, eager to start college in a different city. The few days that remained at school were difficult, as I had become a laughing-stock, thanks to my bully stealing my girlfriend on prom night.
I spent the summer preparing to relocate, getting an apartment to be shared with a fellow freshman, to be selected by the college. I also got a part-time job close to my college dorm room. I moved in a few days early, tidying up the space, and took dibs on the bigger bed. I met a girl in the cafeteria named Stephanie, who gave me her number the second time I saw her. I couldn’t wait to start college!
One day I walked into my dorm room and saw all my stuff tossed on the other smaller bed parallel to the one I had claimed. I could see luggage on the floor and heard movement from the closet.
“Hello?” I shouted. “You must be my new roommate. My name is—”
I froze and went wide-eyed as my new roommate turned around, raised his eyebrows, and smiled, which led to him bursting out in laughter.
“No fucking way,” Jordan said to me. “You’re my new roommate?!”
Just then, there was a knock at my door. Jordan’s eyes and mine turned to the door at the same time as the door opened. I swallowed hard as Kimberley walked in, popping in for a friendly visit. She was about to say something to me but was immediately distracted by the alpha male in my presence.
“Hello,” she said to Jordan while shaking his hand. “Nice to meet you. I’m Stephanie.” The girl I had just gotten to know could not take her eyes off my high school bully.
“You didn’t tell me your roommate was so cute!” Stephanie said to me, elbowing me in the ribs. My eyes went to Jordan, who looked back at me and winked.
“Oh, I’m sure he didn’t tell you a lot of things,” Jordan replied with a smirk.