The Telemachus Story Archive

Breaking Dean
By Cracker
Email: gelded_alpha@outlook.com



Deconstructing Dean

By Cracker

Growing up in the South, where football was king, it was natural for Dean to gravitate towards that sport. In those school years, he was your typical All-American Southern jock. He grew up in a town that worshiped football and treated the young men that played that sport as local heroes. In the atmosphere, he soon developed a sense of entitlement and arrogance. It helped that Dean, soon just shy of 6 feet, was good looking with a well-proportioned muscled body. They were attributes which he exploited to the fullest in his interaction with others to assert his assumed superiority.

As Dean got older, discovering he was bisexual, didn’t cause him any problem. He treated his sexual conquests as something owed to him. Even realizing his preference was more decidedly towards men did not faze him. Confident in his masculinity, Dean’s self image of superiority remained intact. When it came to men, he had a “I only fuck not get fucked” attitude.

About midway through college, he also discovered that, some guys that he met online, would pay to be dominated by him. Happily utilizing that knowledge, Dean spent his college years and, later his 20s, practicing the art of cash mastering. During those sessions, he was his usual arrogant self in dealing with them. He would trash talk, feminize, and mock them online while exploiting them for financial gain. In his mind, those that he cash-mastered were losers and deserved everything that was happening. His favorite part was always draining them until it hurt and then demanding that they thank him for it. After every session, Dean would masturbate while reliving those chats. Throughout it all, he was unaware his overly stimulated brain was failing to focus on who was doing what to whom.

Yet, in the end, karma always has a way of winning.

What he did not realize was he had an untapped inner inclination to submit to authority. A predilection that had been reinforced by the years of obeying his parents and coaches, his military service as an MP, ending with his job in the police force. Without realizing it, Dean unconsciously craved the security that came from following orders. Further, his after-chat masturbations had programmed his subconscious to link humiliation with sexual stimulation. It was only a matter of time before someone else realized his true inner desires and reawakened his subconscious to turn them on him.

However, let him tell his story…

* * *

My name is Ward. I’m a gay African American in my 20s. I enjoy cyber role-plays. I particularly like flipping so-called Internet dominants especially the ones who cash master. I’m not saying that every guy who comes across as an alpha online is a fake. Still, I think a good percentage of them can be flipped. For me, I’m not fixated up on this whole top or bottom labeling. If the sex is hot, I can be versatile. However, like I just said, turning out a guy who boasts a long being an alpha can not only be sexually hot, but also financially satisfying. Especially when these guys are unconsciously, aching to be turned out into a bitch. I called the process: deconstructing their facade then reconstructing them into their true sexual nature

Since I brought up the subject of financial domination. I will admit that I’ve not only cash mastered, but also, I’ve gifted one or two times for fun. Still, I prefer being the one doing the financial tapping. Which brings me to this thirty-four-year-old guy named Dean. We were in the chat room, and the subject of financial domination came up. I started talking about how I did it and the techniques I used. Right away this guy was showing me a hell of a lot of interest in what I did. A bit too much eager interest. When they kept asking you to go into detail about what you do to subs…you know.

So, we began chatting privately. Both of us doing the old “just a bunch of Bros” boasting about how macho we are. Pretty soon I was pumping him for information about himself. I didn’t press too hard. I didn’t want him to think that I was getting information to use on him. Pretty soon I’d sized him up. One of those Southern jock boys who were full of themselves. He talked about how following his coach’s instructions had given him structure in his life. At some point he mentioned he had found the hierarchical structure of his job as a cop was just as satisfying. I listened, noting this was further proof that he might be mentally predisposed to follow orders. Having figured out where he was coming from, I moved to the next step. Discovering that my “good old boy,” as he described himself, was with the police only added to my interest in flipping.

I slowly moved the conversation into discussing sexual exploits. When I am going to flip a guy, I like to know what turns him on when he is hot to get off. Find out what arouses them so, when you flip them, you can keep him in heat. My Southern boy had a thing for trash talk and feminization. I made a note for future reference

Taking my time until we were both pretty comfortable in our sex chat, I got into asking about fantasies. I zeroed to ask what secret fantasy he might have that involved his occupation. After a bit of coaxing, he admitted that he sometimes fantasized about the guys he was arresting overpowering him.

Gotcha

That was the first word that came into my brain when I heard this one. My boy secretly fantasizes about being submissive. I had my key!

Pretending to be innocently curious, I pressed him for more details to flush out that fantasy and, honestly, get him aroused. It was soon obvious that, as he went on about it, he was getting into the fantasy and enjoying being able to tell me about it. At one point, I told him I was turned on and asked him if he was too. When he admitted he was, I knew I’d made the first thrust into his head. I suggested that it would be fun to do some role-play and offered to do his fantasy online. Of course, clearly insisting this was merely a fellow alpha, helping another get off.

He was at first reluctant but, with guys like that, the key is to not press too hard. He was already turned on. It was only a matter of getting his balls to take over from his brain. The trick was to back off and say things like, “it was just an offer” to imply his reaction had offended you. It put him on the defensive and he apologized. Score one. The next part was to subtly hint that you didn’t realize he would be nervous about playing the overpowered cop role. I didn’t use the word “scared” but implied it. With guys like Dean, their self image compels them to agree to playing rather than let another guy think they are a pussy. All about using their own arrogant self image to chip away at that very self image. When he agreed, it was score two for my side.

Next, I casually pushed a little further and suggested that, to help the fantasy and chill things, to take a shot or two of whatever liquor he had. I added that I thought it enhanced role-play and made it even hotter. Again, without saying, I implied that it would be fine if he were too afraid to do anything like that, knowing that again, his ego would override his common sense.

I knew I had reached the critical point. If I could get him over this one hurdle, and get his brain slightly buzzed, his balls would have a free of reign to take over. I really suspected that he just wanted an excuse to play a submissive role. The liquor was a fig leaf for him to hide behind when he fagged. I simply told him I would be the evil criminal who forced the innocent cop to drink vodka. When he didn’t fight me on this point, I knew he was ready to be fagged.

So, it began. Getting him lit, turned out not to be a problem. During our fantasy role-play, he was getting into it so much he easily complied when I suggested more shots. As the conversation went on, I could see his typing was getting worse. He was also increasingly compliant and showing signs of being happily buzzed. I decided to add a little trash, talk into the routine. He responded, as expected, by letting me know he had a raging erection. Soon, I was guiding his vodka use with more shots. Going further, I had him turn on his microphone and his cam “just to make things easier for him.” He was slightly resistant, admitting to me that he never shown himself. I can before because of his profession, but he didn’t take much to get him to do it.

I will say I was really satisfied when he did it. He was sitting there in front of his screen stroking an impressive erection with his right hand while taking hits from the vodka bottle in his left hand. He had that beefy jock body with a nice thatch of dark chest hair flowing into thin honey trail leading down to an impressive set of cock and balls.

I will admit the idea that someone, my age taking down someone his age who was also a cop, had me with a raging hard-on too. My hot looking ‘good old boy” was prime beef on the hook, and I had my hook in him. Did I mention his sexy thick Southern drawl made him even sexier? I secretly hit the video recorder on my computer. Turning out this piece of ass was worth preserving for posterity.

After a while he was lost in the fantasy of submission. Feeling himself up by twisting his nipples until they were clearly swollen, all while taking the occasional bottle sucks of vodka. There comes a point in cyber sex when the guy is in that “fag head” mode. When it arrives, you know it’s time to bring in home. It came.

(See below for the dialogue. I was so intent on bagging my prize. I didn’t care about grammar or typos. Trust me, he was so lit and horny, he didn’t care either. He just kept sniffing and edging as I turned him out. I left the lines as is so, you could get a feel for what was going down.)

Ward: I think you need another shot

Dean: I’m so fucking high now.

 Ward: come on boy …do one more for coach and I’ll let you get off. You’re using the microphone instead of typing on the keyboard, so you don’t have to type with your hand...play with yourself but take that shot.

(Since I was trying to get into his head, I figured using the term “coach” would be something his brain would be familiar with and geared to obey. I watched as he took a long drink, his lips wrapped around the neck of that bottle, sucking from it like it was a cock.)

 Dean: Fuck my head. Done… Shit I’m really fucked up

(Yep, it showed in his face…my alpha poser was flying. Edging and laughing. I went for it.)

Ward: what a good boy. Just for fun, go my throne page.

Dean: huh, why

Ward: i’m just doing part of the fantasy. The way you’re stroking for coach, you’re enjoying it so come on go there …. You’re there for coach?

 Dean: yes, coach.

(Love how that term works on my jock boy.)

 Ward: keep edging and imagining that I’m watching as you fill in an amount

 Dean: fuck I’m so hard

 Ward: don’t shoot yet… hold off? Did you fill it in?

Dean: yes, but I’m leaking like a mutha fucker

Ward: yeah, I want you to imagine me watching. It’s so hot. Isn’t it… watching you looking at that page? Look at that send button too.

Dean: fuck man I don’t know if I can hold off

(Yep, he was ready. I could see him sitting there with a goofy smile on his face really stroking himself. He was close enough to his cam that I could see that his shaft was really leaking. He was so hard and horny. By now, you could cut his Southern Mississippi accent with a knife, which only got me harder to do him. My horny submissive little cop was going to give it up. I began my move to drive it home)

Ward: just edge and concentrate on what you want. Look at it then tell me what you need to get off. It would be so hot if you asked me to fuck you. Go on tell me you need to get off.

Dean: I need you to fuck me. Oh, fuck I’m getting close

Ward: good boy…. I’m there looking at that throne page. You got a nice cash pussy too.

(I noticed when I used the term ‘pussy’ he squirmed in his chair and leaked even more. I decided to go for the feminization though lightly.)

Dean: fuck I think I’m gonna blow

(Last hurdle)

Ward: first, tell coach you want me to fuck your cash pussy.

Dean: Aw fuck…my pussy.

(All those times he played the man with all those other guys. He needed the right guy to tap his cash pussy.)

Ward: admit you want me to tap your cash pussy and hit send on throne.

Dean: oh, shit I can’t hold back.

Ward: hit send, fuckboy.

Dean: fuckboy…shit

(FUCK YES, I saw his left hand reaching for his keypad)

Ward: Then cum bitch...shoot. Go on give it up. You know you want it. Just relax into it. You’re so hard you need to shoot, boy. Send and shoot.

 Dean: I want you to fuck my cash pussy.

(His finger hit the keyboard)

Dean: Oh, fuck oh fuck, I hit send… it’s coming. fuck my cash pussy got fucked… my cash pussy fucked… fuck it fuck it fuck it.

Ward: YEAH. You popped that load bitch… what a good faggot.

Dean: Fuck. I cash fagged.

Ward: you did…faggot…Thank me nicely.

(I wanted that final nail to driven home.)

Dean: thank you (he softly groaned)

* * *

I had cash fagged him. Importantly, I’d shown him that not only could he be me submissive, but he would also pop his load being submissive. I let the next few days pass, knowing that what he had done would eat into him. I also knew that he would reliving the chat. No doubt getting a hard-on doing it, which would only further dissolve his alpha image. I waited, figuring he would reach out to justify what he had done, I didn’t let him get away with it when he did. I knew a part of him contacted me because he really wanted me to do it to him again.

He was still a sucker for the suggestion that we try it one more time…to see if he got aroused again being fagged…with the vodka too. Do it to prove to himself that it was just that one time that had him in heat…unless he was too scared. I simply gave him the fig leaf he unconsciously craved to let him once more release his inner bitch. This second time it was even easier to get him to follow whatever I asked, including sending me another small gift. I watched as he masturbated into another explosive geyser of spunk. Once again recorded for posterity thanks to my computer. Having succumbed to being my little fuckdog a second time in that chat, he surrendered to the obvious. I followed up by offering him the opportunity to let out his inner bitch in future discreet chats with me. It took about a week, but he reached out. The powerful sexual arousals that he had experienced in fagging overcame any reluctance. Pretty soon his cyber submissions became a regular thing.

After that, he was my bitch. An ex-alpha cop squirting his cash, along with his spunk, for me. I brought out his suppressed kink for humiliation making him use his handcuffs as a cock ring during cyber play or screw himself with his baton while dressed in his uniform (accomplished courtesy of a slit in the inseam covering that bubble butt). Soon it became something he craved on a regular basis. Of course, being a charitable person, I was happy to provide what he needed. He particularly got off appearing on cam in his uniform after finishing his shift. He would sit there with his cock out stroking while I mocked him.

Ward: out there, pretending to be this macho cop when we both know that you’re just a little pussy boy aren’t you

Dean: (taking a few drinks while masturbating himself into a frenzy) yes sir.

Ward: yeah, that’s right. Fuck boy. Out there acting like a man. If that was true, why are you here sitting in your chair with your dick out stroking, right.

Dean: aw fuck yes Sir.

Ward: the next time you go out for speed trap duty, I want you to give a pass to a hot guy that you stop. Even better, be respectful and call him Sir.

Dean: fuck, yes sir

Ward: listen bitch, if he looks interested, offer to give him a blowjob. you would like that wouldn’t you. Imagine going behind the bushes where you stop a guy…dropping to your knees in your uniform and sucking him off.

Dean: fuck yrs..aw fuck yes.…shit I’m creaming

Those sessions always ended with him screaming out that he was a pussy and shooting his load on the keyboard.

Slowly, I introduced him to the idea of the overwhelming thrills he could experience while acting the bitch on cam during “invite only” private live group chats. It took a while of fantasy role-play with this concept before he finally surrendered to doing it online in front of others. I let him wear a mask the first few times. The crowd mocking got him so hot, he shot a wad across his computer screen. Once I’d truly broken him into this facet of his sexuality, I had him unmask and fag out in from of a few special invitees (guys who eagerly paid me for the privilege). It was a grand show where he shaved off his below the neck body hair in front of them using his collected jism as the shaving cream. During our initial chat he had once mocked guys who had little chest hair. Removing all of it stripped away what he considered as fundamental to his manliness. In the end, I went for the decisive step in collaring him. I ordered him into a chastity device between our encounters. The full details of how I did all this and his reactions as it went down, is a whole other set of stories. However, I’m following a policy of don’t ask, don’t tell with them.

The End


Authors note: stories are not written in a vacuum. I would like to thank a few people who helped “inspire” or encouraged this endeavor. Fred W, PJ (Peter), JT, Netherlands Jev, & the sexy M. Wei. Tip of the hat to Jack Parker and his stories. Kyle Cicero too, who really encouraged me and made a few suggestions. If you enjoyed this story, reach out and let me know (email/comment/ rate). It’s always good to know if you’re doing something wrong or something right. At the very least, knowing someone is reading it encourages a writer to do more.

To Telemachus who gave me a place.