biggest cuckold fantasy , some jerk guy

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It's funny to read this story. I was/am in a similar situation to you. There is a guy that these days I'm really good friends with, but it certainly didn't start off that way! Towards the middle of our 9 year marriage my ex and I were living the hotwife lifestyle and dabbling into cuckolding when she met this guy while she was out of town at a convention. She had been flirting with him throughout the day and by our phone conversation that first evening of 3 it was pretty obvious that she had the hots for him. She asked if it was turning me on to hear she'd been flirting around with him. To which I of course readily admitted to her that it was immensely. So in her sultry voice she asked me if I would mind her getting to know him more intimately. My hard dick won out the night and as a result I would hardly hear from her for the rest of her trip.

She had played alone before, but these adventures had been on evenings out with girlfriends, or drinks at a bar with coworkers that she stayed behind at where she met a flirty guy she took a fancy to. I Knew she was out alone but never expected anything to happen and it didn't happen all the time. So I never knew when something could conspire and she might role in around 3 in the morning. She always told me about the things that she got up to because she knew how much it excited me. She loved to tease me with her going it alone and teasing all these other men. Because it was something we had always done together to get each other off, it made it all the more exciting that she would just do it without me even being around, just enjoying being a slut all by herself.

So when she called me about him I figured it was gonna be another hot experience that she was going to use to tease my cock hard with her vivid descriptions. Except this time I was aware it was happening and it drove me to distraction trying to imagine what might be going on. She had described him as kind of rude and a little arrogant, a gross understatement as it would turn out, but I wasn't paying to that anyway. All I could hear in my head was she's fooling around alone and gone for days and my hard cock had me in heaven. Then a bunch of shit went down and I finally met him!

He was crude, obnoxious and generally an asshole. I thought to myself that she had dug deep in the slumming pit to come up with this one! I wouldn't know all that for a couple of months as she was secretly seeing him behind my back. Yes I was a true cuckold. She went so far as to help him move to our town so it was easier for them to see each other. Then trained him not to like me with a bunch of lies she told him. I hated him for so enamoring my wife and taking her away from me like that. Yet it turned me on so much that he had that kind of control over her, us that she would do anything for him, no matter what!

After the air cleared a little and I got to know him it occurred to me that he was nothing more that a man child! He reminded me of the 14 year old punk that used to terrorize the neighborhood kids. Except they all grew up and he didn't. He had the looks! Long wavy brown hair to the middle of his back, chiseled features, a tradesman's body and a deep Florida tan. But the man was a crude pig with an adolescent mentality and if the truth be told he really sucked with women. He had this animal charm he could work on them once he got to know them, but most women were put off by him at the first meet.

He cuckolded me for 3 or 4 years until my marriage ended and not to, or because of him. We remained good friends that drifted in and out of each others lives. Now he is one of my oldest and closest friends. Was my best man at my second wedding and has also slept with my new wife too! Only one time a couple of years back, but he's still a rude pig and hits on my wife and likes to play grab ass with her. These days his hair is very short and very thin. What he lacks in hair he's made up for in a skinny man big belly. Most women don't even give him a second look and some might think him a little creepy! Plus he has a really small cock, maybe four and a half inches (a cuckold mental mind fuck) So when he gets to fucking around with my wife it gives me such a hardon. He's such a rude pig that to see him treating my wife with such disrespect really tickles my cucky bone. I would let him have her anyway he wanted her even to this day!
 
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fk2546 said:
Are Dan and Anne still each others primary lovers? Do you get any sex from Anne or is she exclusive to Dan?
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Anne and I divorced a few years back, not related to the chose of lifestyle. As to your question, yes Dan and Anne continued to be primary lovers well over a year and during this time Dan had become Anne primary partners when it come to intercourse. During this time frame I did not have intercourse with Anne unless she wanted it.
 
jaggu008 said:
Yes I fantasise about my Boss, who has such a dominating personality and uses his authority to the fullest in the office, coming home one day and after seeing my wife, starts flirting with her and seeing her response, asks her to lead him to our bedroom and fucking her vigorously and i hearing her voice urging him to fuck harder and he grunting. After sometime, he comes out and telling me to go to my wife and clean her. By that time i would have ejaculated.
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I’ve been in trouble before with my boss , he’s a real jerk and nobody likes him . But after being suspended and begging this asshole boss and almost losing my job I starting getting these REAL STRONG submissive cuckboy bitch fantasies . I even thought of him calling me in his office after hours , him making me get on my knees and blow his fat gut cock .

But OH YES he comes around and fucks my wife to save my job , and I too become his clean up bitch . I end up eating my asshole boss’s nasty slimy cum from my wife who yelled to him how much bigger his cock was and better. Then I’m sucking him clean in front of her . I HATE MY BOSS . But I’m his clean up bitch in my fantasies.
 
I was so pissed when I found out, but after a while I realized it turned me on. We stayed friends, fucked some more (she wound up cheating on another guy with me). And I got more details out of her, which turn me on to this day, more than a decade later.
 
My wife has been fucked by a couple of guys I dislike, and for reasons I can't explain, it turns me on more than any of her other partners. Apparently it turns her on to because she keeps going back for more.

She has also gotten fucked by a guy that she absolutely hates. During a friends house party late one night, after much alcohol, she found herself alone outside with him, He began kissing her and feeling her up, which led to him fucking her up against the side of the house. She claims she still detests him, but she has gone back for more several times. Go figure...........
 
Last week something funny happened. I saw a guy from high school I haven't seen in 15 years. He was a big jerk back then. Once we got interested in the same girl, but the thing was, she was one the hottest girls in school and we were out of her league. I was average looking and shy and he was very aggressive but really ugly though.

Then I see a hot woman coming to meet him with 2 kids by her side, and it was the same hot girl from high school. She still looked awesome.

As soon as I saw them together, I was surprised, but immediately imagined him fucking my current girlfriend.
 
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I've had stuff like that happen too! I've run into ex girlfriends, or heard about them from others long after we had been together. All had cheated on me, some with assholes that I didn't like even before they cheated with her! The difference is that these women and their lives had gone to total shit as a result of the affiliation to the men they chose. Kind of a karmic revenge, of sorts.
 
4winds04 said:
I've had stuff like that happen too! I've run into ex girlfriends, or heard about them from others long after we had been together. All had cheated on me, some with assholes that I didn't like even before they cheated with her! The difference is that these women and their lives had gone to total shit as a result of the affiliation to the men they chose. Kind of a karmic revenge, of sorts.
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not even karmic imo. cheating is stupid and usually a smart mind does not do it. that these fuck-choices are not smart and easily result in crap and not ending up with a good partner but just other stupid liars is not unusual - mingling with the same..... the next thing is that if you like to fuck cheating women as a guy it reflects something of yourself. i got repulsed when i was younger on a girl saying to me at a dinner that she has to get rid of her bf because he is annoying and like a baby. that guy is actually a 2 faced prick which was a virgin when he met her or at least very inexperienced.
nevertheless i did not fuck this girl that many guys would have love to bonk - her shitty attitude repulsed me
 
This really did happen to me. My boss at my part time job was loud and obnoxious like that. Alqays talking about sex and how goos he was and how much pussy he got. ONe time at work when we were not busy he had me come behind the counter. He had his cock out and I admitted it was a very attractive big cock. I felt warm all over and weak in the knees.. He said,"go ahead, do what you want". He used to ask me questions about my sex life. I got married REALLY young. But he could tell I wanted to try sucking a MAN's cock. Not just another boy's. He was 6'6 and he bent down to kiss me and he said Go A Head. He put a pad down for my knees. -ever since I have though it very polite when a man had a pillow or a pad for my knees.
I stroked him for a couple minute and he shot this good sized load of cum. I thought it was over but he said no way. It was pre-cum but a load the size of most boys' full loads. He was 46, I was 19 at the time.
I started sucking that beautiful cock and I knew I was falling in love with him. His cock and the pre-cum were delicious. About 10 minutes later he said "Are you ready?" I nodded and said um hmmm. He held my head to his crotch and pumped his full load into my mouth. It was twice the size O f any boy load i had swallowed .
He told me I would be doing this any time HE wanted. I never thought of him as a Bully before , just a leader and successful in his little business. But now I like him even more. Adored him really. And i was ready to do what he told me. Not just on the job.
Lobe, Heather Dishwater Blonde sissy boi in upstate NY now 52.
 
Toolman,

Good to see someone bringing this thread back up. There is indeed something exciting, erotically humbling, even at times erotically humiliating when the wife does take on lover that she would not typically connect with. While this thread was titled as “biggest cuckold fantasy , some jerk guy”, several of us have had real life experiences with our spouses connecting with guys that they would not have been previously attracted to. In our case, this was a mutual friend (not a very close friend) and I knew him better then my wife at the time although we both always considered him to be arrogant and obnoxious more often than not. I was actually a bit surprised that my than wife actually finally gave into his advances as his attitude was generally a turn off for her.

Something that caught my eye when I went back to look at this thread today, was reading back through it, reading what “4winds04” said about his than wife going as far as to help her lover move to their town so that it would be easier for them to see each other. It reminded me of the serious discussions my than wife and I had about our mutual friend (her lover) possibly moving into our house after they had been together for more than a year as primary partner when it came to intercourse. Unlike “4winds04” situation, they (my wife and her lover) were not hiding it behind my back as they both made sure that it was in my face in a reasonably respective way yet they were discrete when it had to be until they actually come out publicly as a couple. It started similar to a hotwife model, than transitioned to something more consistent with a cuckold model, and eventually began to be much more Poly overall which is when we began to speak seriously about him moving into the house with us and when they become public.

While as a couple we would agree that he was the stereo typical confident alpha type, arrogant, crude, and obnoxious early on our view point began to change on some levels the longer he was very much involved within our household. During this relationship my than wife realized just much she could actually love two men in different way, Dan was the confident alpha that she needed and I was her more supportive caring intimate beta. The longer they were involved the deeper her emotional connect became and her feeling grew even stronger.

I think it would be good to see other post additional follow up to their initial post.
 
4winds04 said:
I've had stuff like that happen too! I've run into ex girlfriends, or heard about them from others long after we had been together. All had cheated on me, some with assholes that I didn't like even before they cheated with her! The difference is that these women and their lives had gone to total shit as a result of the affiliation to the men they chose. Kind of a karmic revenge, of sorts.
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4winds, THAT is a really nice cock
tell me more please
love, heather
 
I have many fantasies, and yes one fantasy does include a dude who is a complete arrogant asshole just taking over the evening my gf and i had planned and then fucking her hard, then they both blatantly ignore me when i protest about it.
 
Looking back, I see an aspect of this i had forgotten. WE went to a retirement party for a co-worker my wife did not care for. Always dissing on him. He was able to retire in late 50's
There is a hot tub at the friend's who hosted. I know nothing about the sex life of the hostess BUT, Ted, the man I am talking about managed to get my wife Jean to fit next to him in the hot tub. He had taken a Viagara and he told her. asked if any of her lovers (which he knew there were a few besides me, her hubby). WE divorced when i was 28. At least she though I was good at sex.. Aanyway, Ted asked if she had had any lovers use Viagara or the ED pills like it. Her eyes gave a exaction, shock that he would ask bu talso excitement at what he was getting at. HE asked he to feel his cock. She though it would just be thru his bathing sit. She reached over and felt it but he had taken his suit off. She was in a Tankini. Ted knew that the bottoms from that would be easy to take off her. She was shocked at how big and hard he was. She had never heard about him being a stud or anything. I think Jean, my EX had just turned 50. Ted sat up on the side of the tub and asked her to suck his cock. She did and she is VERY good at it. AS she bent over a friend and co-worker she likes pull the bottoms of her suit down and off. He is mark. Mark started fingering her pussy. He did not comment on how loose she had become. I was there as her date,her plus 1< but was not expecting sex for myself. Ted was really getting turned on now. He held her head and tensed up. Shot a first load into her mouth and throat. She was able to relx somehow and swallow it all down. She said "That's a Meal for your Money, Not a Snack" an old ad compaign from a sub shop near us. Mark pusche her up on the edge of the tub. where the wider part of the deck was. Ted pulled her up to him and nodded down at his lap, his crotch. If she were just a little younger it would shave been preg rush but she lowered herself down onto his COCK. Ted's wife came in when she heard what was going on. Jean hesitated and The wife gave a nod. Jean took that whole cock in one more stroke. She winced as if He had gone up past her cervix. Ted's oorgasm took even less time than from the blow job. As Ted got dressed, We sang for "he's a jolly good fellow." It started spontaneous ly. A few of them including hostess are music teachers. Ted's wife spoke to Jean briefly, Of course SHE knew him better than anybody, sexually! Aminute later jean told me she was going home with Ted and his wife. The bulge in his pants was showing that he could and would fuck at least one more time. Next time I talk to Jean, she said, "You know I still do not like Ted"

Love, heather
 
MsGary said:
Looking back, I see an aspect of this i had forgotten. WE went to a retirement party for a co-worker my wife did not care for. Always dissing on him. He was able to retire in late 50's
There is a hot tub at the friend's who hosted. I know nothing about the sex life of the hostess BUT, Ted, the man I am talking about managed to get my wife Jean to fit next to him in the hot tub. He had taken a Viagara and he told her. asked if any of her lovers (which he knew there were a few besides me, her hubby). WE divorced when i was 28. At least she though I was good at sex.. Aanyway, Ted asked if she had had any lovers use Viagara or the ED pills like it. Her eyes gave a exaction, shock that he would ask bu talso excitement at what he was getting at. HE asked he to feel his cock. She though it would just be thru his bathing sit. She reached over and felt it but he had taken his suit off. She was in a Tankini. Ted knew that the bottoms from that would be easy to take off her. She was shocked at how big and hard he was. She had never heard about him being a stud or anything. I think Jean, my EX had just turned 50. Ted sat up on the side of the tub and asked her to suck his cock. She did and she is VERY good at it. AS she bent over a friend and co-worker she likes pull the bottoms of her suit down and off. He is mark. Mark started fingering her pussy. He did not comment on how loose she had become. I was there as her date,her plus 1< but was not expecting sex for myself. Ted was really getting turned on now. He held her head and tensed up. Shot a first load into her mouth and throat. She was able to relx somehow and swallow it all down. She said "That's a Meal for your Money, Not a Snack" an old ad compaign from a sub shop near us. Mark pusche her up on the edge of the tub. where the wider part of the deck was. Ted pulled her up to him and nodded down at his lap, his crotch. If she were just a little younger it would shave been preg rush but she lowered herself down onto his COCK. Ted's wife came in when she heard what was going on. Jean hesitated and The wife gave a nod. Jean took that whole cock in one more stroke. She winced as if He had gone up past her cervix. Ted's oorgasm took even less time than from the blow job. As Ted got dressed, We sang for "he's a jolly good fellow." It started spontaneous ly. A few of them including hostess are music teachers. Ted's wife spoke to Jean briefly, Of course SHE knew him better than anybody, sexually! Aminute later jean told me she was going home with Ted and his wife. The bulge in his pants was showing that he could and would fuck at least one more time. Next time I talk to Jean, she said, "You know I still do not like Ted"

Love, heather
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Heather,

There is something to be said about when wives and or ex-wives engage in sexual activities with another person (man or woman) that we as husbands/ex-husbands do not like.

SS
 
jayla said:
I crave the humiliation so the other guy being a jerk to me is added bonus to my cuckold life.
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It has become the most dominant fantasy in my life, to be a submissive wimp faggot for a bully who's fucking my wife. I know my wife gets turned on looking at these rugged unshaved good looking guys , AND! guys that are just nice guys. So I can get excited thinking of a couple guys we know like that, fucking my wife, because I know that would be her wet panty turn on. But for me, it's the asshole cocky ass bully that gets me excited , because of my submissive cuckold bi fantasies. For me to swallow my pride and get on my knees calling him Master in front of my wife, WOW! what a submissive rush.
 
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