As I would like to contribute to the discussion, I believe I have something close to reality in which I have experienced related to the concept of this thread “Biggest Cuckold Fantasy, Some Jerk Guy”.
Yes this guy that I am going to write about was indeed a very obnoxious and yes you could consider this guy a loud JERK kind of a guy. For the sake of this post, we are going to call the guy “Dan”, not his real name.
I was initially introduced to Dan over 25 years ago as he was brought into a circle of friends that I was a part of at the time by one of my than close female friends (Lets call her Tina), (FwB). From the first time I met Dan I really did not care to be around him for any period of time beyond the minimal time require for respectable social interactions. He was the stereo typical confident alpha type and yes he tended to be extremely obnoxious more often than not. Rather quickly I realized that Dan and I had a similar taste in woman, some of the woman found him a bit over the top and did not take to his ego very well while some of the other woman were seemingly attracted to his arrogant confidence and ego. When I say this guy had an ego, he was very sure of himself and would occasionally boast that he could get any of the women within the group into bed. Dan and I had the occasional clash as our dispositions were a bit different. As the years progress, Dan developed a sexual relationship with one of my close female friends (FwB), the same friend that brought him into our circle. A short time later Dan joined the military (army) and married the woman that first introduced us. They had two (2) kids together and also become involved within the swinging lifestyle. During their occasional visits to our area, Dan would still hit on virtual anyone that I was dating and or in a relationship with. While I really did not care to be around him, his wife, my former FwB would tell me about how good he was sexually and how big his cock was. With that said, I did have a secret fantasy of Dan actually being successful with getting my girl-friend at the time in bed and therefore cuckolding me. Unfortunately all the women I was dating in those day were all turned off (so they claimed) by Dan’s arrogance and obnoxious side.
As the years went by, I had married and also divorced although my ex-wife (Lets call her Jenn) were on very good terms as our divorce was amicable so we remained friends and occasional enjoyed a continued sexual relationship. As would have it, Dan was also going through a divorce and his soon to be ex-wife moved back to her home town not far from our area. Dan contacted me as he was going to be coming to our area to visit his kids which were now living nearby and he was looking for a place to stay. I was initially reluctant although after some consideration I agreed to allow him to stay in my guest room while he was in town. Dan was also joking about me arranging a hookup for him while he was in town, in reality he was very serious about me arranging a hookup for him. Dan made it very clear that he would like for me to arrange a meeting between him and my than ex-wife, I did not hesitate, I reached out to and I spoke with my ex-wife about Dan. So I arranged for Dan and my than ex-wife to communicate (chat online & talk on the phone) in advance of him coming into town for a face to face over dinner. When the day come for Dan’s visit, I had actually made arrangements for the three of us to go out for dinner at a local restaurant and prepared post dinner snacks with drinks for us have on return to the residence. As you can image, Dan took the lead for the evening, my ex-wife was very much into him, we spent a good bit of time at dinner. Dan and my ex-wife was so much into each other that when we arrived back to the residence they become very intimate as I prepared everyone some post dinner drinks. I have to say, that he fucked her right there in my living room for the first time and for the rest of the weekend he fucked her multiple time in my guest room and was not very quiet about it. While she was my ex-wife and was still one of my sexual partners up until he fucked her that weekend, he made it clear to her that he would continue to fuck her for the foreseeable future if she would stop having intercourse with me. Over the next 8 to 9 months when Dan would come to town he and my ex-wife would stay in my guest room together. After a couple of months I also introduced Dan to another woman (Lets call her Lisa) that I was dating which I also had a sexual relationship with. While Lisa also found Dan arrogant and obnoxious, she was taken by his confidence and very interested in seeing if he is all that he claims to be. The same night I introduced Lisa and Dan there was an extended amount of very open discussion between myself, Lisa, Dan and Jenn. Dan expressed to Lisa and Jenn his view point about me, it was a bit humbling and on some levels humiliating although I was open in my replies to his view points and in the areas where he was correct I freely admitted to the same to the ladies. That same night we all ended up naked, I ended up sucking Dan’s cock in front of both of the women and Dan fucked BOTH of them in front of me. During the next 6 months that followed, each time Dan would visit he would have exclusive access to both (Lisa & Jenn) women and I would do anything either of the three wanted from me. Dan eventually married my than ex-wife (Jenn) and Lisa simply moved on.
As the years past, I had remarried (Lets call her Anne), Anne was a woman from the original circle of friends mentioned above so Dan knew a lot about her. He had continued to stay in touch and considering he was now married to my ex-wife (Jenn) Dan was present during a number of family gatherings throughout the years. Dan would make very regular advances, flirting with Anne. Anne claimed that she was always turned off by Dan’s arrogance and obnoxious side although I looking back now I think she simply did not want to cross any lines with Dan & Jenn that could come back to cause issues. After a few years of Dan and Jenn divorced, it would seem that Jenn found another man that she and Dan met through their time within the swinging lifestyle, so they decided to call it quiets. As they were going through their divorce, Dan began spending even more time at our home and he continued to make advances towards Anne. It got to a point when Anne told Dan that she would not ever cross that line with him unless I give her my approval and blessing. So after about a week or so, I assume that Dan must have been thinking about what Anne had said because I received a chat message followed up by a phone call from Dan. Dan said that he wanted to have a serious talk and that I should listen closely to him, he then proceeded to tell me that he wanted to enjoy my current wife (Anne) sexually and if the chemistry was there between the two of them that he would desire to develop an ongoing sexual relationship with her. Dan than told me that I should, than Dan paused, he then said that YOU will tell Anne in detail what he wanted from her. There was a very slight hesitation, then Dan told me that I would be giving Anne my approval and blessing for her to explore anything and everything with him. It was as if Dan knew without a doubt that I would do just as he instructed. So yes I did as I was told, I immediately approached Anne and spoke with her in considerable detail. I let her know that Dan had reached out to me and that he expressed a great level of desire for her, at which she just laughed, saying that she knew that he was a flirt and teased a lot although she really did not think he was truly interested in her. I looked into her eyes, than spoke in a serious manner as I let her know that Dan made it very clear that he seriously would like take her and be with her sexually. I also let her know that Dan said that if they have good sexual chemistry between the two of them that he would also desire to develop an ongoing sexual relationship with her. Anne than asked me, what did you tell him? I replied back to Anne by saying that that Dan did not really give me an opportunity to give him my opinion or view point on the matter, I then expressed to her that Dan told me that I would be giving you my approval and blessing for you to explore anything and everything with him. Anne was quite for a very brief moment, as the processed what she just heard, then she said that she still felt that Dan was arrogant and even obnoxious at times, she than did follow up by saying that if Dan was so confident and arrogant enough to come to her husband and be so bold as to put his desires out there that she owed it to herself to give Dan the opportunity as she had heard about his sexual ability. She looked back at me than asked, so Dan told you to give me your approval and blessing to explore anything and everything sexually with him? She then said, I take it that I have your complete approval and blessing to do this with Dan? I looked at Anne and with a serious yet generally playful expression and said yes, you have my approval and blessing to take this opportunity has far as you would like to take it. She then asked, are you giving me your approval & blessing only because Dan said to, or are you giving it freely because you desire for me your wife to have what could be an amazing sexual experience with Dan? Without hesitation, I said YES, I am giving you my complete approval and blessing freely because I desire and encourage you to explore, enjoy what could be an amazing sexual experience with Dan and YES I am also giving you this because Dan said to. Anne smiled, than ask one more time if I was sure about this because she knew of my past experiences involving Dan and some of my prior relationships, she did clearly state that this could be relationship altering if she does have sexual chemistry with Dan. I than said YES that I understood what it could mean for each of us. Anne again smiled and said that I should reach out to Dan to let him know that we had spoken and that she would be waiting for his call.
With Anne direction I reached out to Dan to let him know that I did what he had told me to do and that she is currently waiting for his call, the ball is now in his court. The next day, I received a message from Anne letting me know that Dan had called her and that they had talked for several hours on the phone and had been chatting online most of the day. Anne told me that they had decided that Dan would come by the upcoming Saturday afternoon for a cookout. The two of them continued to chat online and talk on the phone throughout the week and the Friday night before the planned Saturday meeting, Anne come to me and asked if I would go shopping with her to find something new to wear for Dan. She was not talking about outwear, we went to one of the local lingerie stores were she picked up a few new items while asking me my opinion on style, color, etc she made the final decision on each item and proceed to tease me as she told me that she was going to be wearing them for Dan. Yes I paid for the Lingerie. It was very clear that Dan was getting what he wanted, Dan was going to have Anne. I knew that he had wanted his chance with Anne since the day he first met her so many years back.
On Saturday, we had a few friends over in attendance of cookout which was planned well in advance of the invite of Dan to join us for the day. As we prepared the items for the cook out, Anne walked out to where I was doing the prep and said handed a digital camera to a woman friend of ours. I looked at her with a questioning look at which point she said that she wanted our friend to take some pictures of her (teasing shots of her in what she would be wearing for the cook out itself. Anne was wearing a skimpy sun dress with no panties which made for some very productive teasing images as our friend took the images for her. After the impromptu photo session they went inside to email a few of them to Dan. When Dan arrived, he walked up to me and we exchange some brief words which includes the general hi how are you stuff and just before he walked away he did say that he was going to show Anne a great time tonight. For the most part the cookout when just as it was previously planned with the exception that Dan and Anne spent a good bit of face to face time talking, laughing and sharing ideas, etc. As the day transitioned from afternoon into the evening some of our guest began to depart with exception to a couple of our friends which were lifestyle friendly. This couple knew what was planned for the tonight and they stayed late playing cards and drinking with the three of us. As we approached mid-night we wrapped up the g-rated entertainment and the couple departed. Dan and Anne moved into the bedroom to get more physical acquainted with each other as I took some time to clean up from the evenings entertainment. Once I was done, I prepared three adult drinks along with three waters then made my way into the bedroom. Once I was into the room I found the two of them embracing each other, passionately kissing and running their hands over each other. A short time later both of them were undressing each other and I began to undress myself. I watched on as Dan and Anne explored each other’s naked bodies, changing positions multiple times including time within a 69 before moving back into a missionary position. Dan teased Anne with his cock on the outer edge of her pussy, not penetrating her as the two spoke quietly to each other. A short time later they both looked over at me with a questioning look at wanted me to say it out loud, to say that I approved.
Without hesitation I calmly stated out loud that yes I completely and fully approve of the two of them being together sexually and expressed by blessing of the same. Anne than looked at Dan and they both looked back over at me, followed up by both saying almost in unison that if I truly approved that Anne wanted me to show both of them that I was truly OK with what was to come next, at which point they said that they wanted me to guide Dan’s very erect penis into Anne for the first time he penetrates her. Anne had the biggest smile on her face, I had been the only man she had been with since we married, before we married she had a sexual past that was very exploratory, yes she knew of my past and she knew a lot about Dan’s past as well. She made it clear in the look that she was giving me that this was point where things would change. So yes, I crawled over from where I was and sat next to them on the bed, all of us naked, I kissed Anne, then looked Dan in the eyes at which point he said that if I approved that they both wanted me to guide his cock into her pussy. Without any additional hesitation I did just that, I reached down between there naked bodies, I reached for his cock with one hand, used the other hand to open her pussy up slightly then guided his cock head into her pussy. I was in awe and has his cock started to go into her slowly opening her wet pussy up to accept this thick cock, I sat back and again verbally made it clear that with my actions of guiding his cock into her that there could be no doubt that I approved and blessed their sexual unification. Throughout the remember of the night, they would kiss each other, touch each other, they would give each other oral and he would penetrate her and release into her multiple times until the sun come up. Yes at some point during the night I did clean them up between some of their more intense sessions as they recovered. As I prepared some breakfast for everyone, Dan and Anne took a shower together to freshen up. The start of a new chapter for Anne and myself, as well as a developing relationship for Anne and Dan. Their sexual relationship last well over a year and during this time Dan had become Anne primary partner when it come to intercourse. When Anne was not available he would also have me suck him to completion.
Tina (Prior girl-friend and friend with benefits at other points), Jenn (Ex-wife and friend with benefits at other points), Lisa (Girl-friend at the time of the encounter) and Anne (Wife at the time of the encounter)
While there is so many more details that could be conveyed about even prior to and following what I have shared here I am sure that you all get the point with this one. In summary Dan has had sexual relations with at least four (4) woman from my past and to this day makes it clear that he is much better in bed due to his sexually dominate and aggressive nature.