Why Do Men Enjoy Cuckolding?

Cuckolding has helped my relationship with my wife (I will call her Jessica). I am unable to provide Jessica, with the physicality which she needs. If I had not been okay with our relationship becoming open on her end, it would have been very unfair to my wife. She is a woman who enjoys sex, inclusive of intercourse. And she requires a large penis, which stays hard. Had we had not talked this out, I very much doubt we would still be together today. And I truly love her so much. I do believe that she does love me. My being okay with her having other lovers, was actually a very fair solution for she and me to make.

While dating, she told me that size did not matter to her; later, I learned that her mother and her sister encouraged her to “take-on” this stance. Jessica had been with guys who were more endowed that I, and she better enjoyed sex with each guy, but they were “bad-boy types”; and, they had less potential than me, for becoming a good money earner. She swore to me that my small size (a little over 4 inches) had no bearing on the amount of pleasure she received, and, as she said, it was more important that I knew better, how to make love (than the others she had been with).

Even at a young age, in addition to my small penis, I already had issues staying hard, and even achieving an erection. Now years later, it has gotten much worse. In fact, once we were married even less than a year, it had already gotten worse. I went to several doctors. The best I could find, going to doctors, was Viagra. But Viagra did not help as much as my wife needed.

I sensed Jessica’s dissatisfaction. And after about 10 months of marriage, I asked her about the level of satisfaction. I pressed her gently, with sincerity, to level with me. Prior to this, she insisted all was okay. But things did not feel right for me. And my continued feeling of inadequacy, felt based in reality. As it turned out, Jessica actually was very dissatisfied sexually. And she came clean, telling me that she was not honest with me from the beginning; and that, her sister and mother encouraged her greatly, to marry me. She insisted, and still insists, that she loves me, and loved me while we dated. But she admitted that prior sex partners, before we dated, were more endowed and satisfied her well. And that our sex was inferior to the sex she had with others, before we met.

While Viagra helped some, as I mentioned above, it still was not enough for me to really satisfy my wife. And my lack of size was a problem, even when I had an erection. We discussed many options. We agreed we wanted to stay together. We agreed that we could truly trust one another. We discussed cuckolding, and agreed it seemed like the best option. I was not wanting, by any means, sex with anyone else. But clearly Jessica was desiring another sex partner, or partners. And we agreed to try cuckolding. I told her about my therapy. And she came to several sessions. My therapist supported our decision to try cuckolding, as a dynamic of our marriage.

Jessica and I made some rules. We agreed to stop, if either one of us wanted to discontinue. We agreed on a list of other things; inclusive of me watching each time. Recently, we agreed to amend this so that a minority of the time (up to no more than 20% of the time), she can be alone with her lover. We agreed to “no kissing”. But, before the first-time, we rescinded this rule (she said that without kissing she could not have sex, and I understood and agreed). We agreed that if I did not like a particular “Third”, she would no longer be with him, nor communicate with him. We agreed to a few other rules too. And some rules, in addition to the no-solo rule mentioned above, have since been amended, and a few other rules, besides the no-kissing rule, were canceled.

As I mentioned above, without telling my wife, even before I approached her and asked if she were satisfied, I had sought out a therapist. I found a female therapist who really helped me. She was not a “kink therapist”, by any means. But I felt her sensitivity and true desire to really help me. I had explained that at a young age (15 years of age), my first girlfriend had cheated. I explained that at that time, I was mad and upset, and felt worthless sexually, but nonetheless, I was also, turned-on and very stimulated. And I told my therapist that I would masturbate with my former girlfriend and her lover, as my fantasy. And I explained to the therapist other early experiences which caused my cuckold feelings, to actually surface. In other words, before meeting my Jessica, I had some cuckolding experiences. And those experiences, were rather confusing, but in another way, beneficial. Upon meeting Jessica I wanted to leave any cuckold feelings and desires behind me. Somehow this was not easy. And even during our first time having sex, I was already thinking of her having sex with someone else. I did not let-on to Jessica, as we dated, that I had feelings of being sexually inadequate (but she knew something was off and kept quiet about it).

I had asked the therapist to help me NOT to be a cuckold (as if this made any sense). But she told me that all she could do was to try to help me understand why I have these feelings. However, she really did do more than just that. In fact, she sent me to another professional for hypnosis (she was not trained for this). The hypnosis did help with some childhood trauma, but not with diminishing my cuckold feelings. Meanwhile, whenever Jessica and I had sex, I was secretly thinking of her have sex with someone else, and with me watching. It seems, as the therapist explained to me, that the childhood trauma helped mold me into an individual who would be rather open to cuckold feelings and desires. But additionally, my therapist felt that I was somehow accepting of these feelings in a very natural way. My therapist had told me that it would be my decision, whether to tell my wife that I had these feelings, or whether, I wanted to continue my marriage, without even mentioning this aspect of me, to Jessica. One thing for sure, I wanted to stay married. But it did seem that Jessica was only satisfied, if I gave her oral pleasure, and not with intercourse. I should add that my wife really enjoys penetration and intercourse, or at least she wanted to enjoy it with me. She told me in the very beginning that she loved intercourse. With my size on the smaller side; I was actually very concerned about not pleasing her. Although my wife had stated that size meant nothing to her; I found this difficult to believe (before our discussion). She somehow seemed to crave larger. And it was during the 10th month of our marriage that Jessica told me the truth, in response to my very serious questions, which were asked in a very loving way. I had assured her, that no matter what she told me, I would not be upset, nor hold it against her in any way. And she told me how she really felt.

I was most concerned about how I should handle my jealousy. I should point out, that I’m a very jealous individual. And my cuckolding experiences prior to meeting Jessica, were confusing and had some difficulty, because of my jealousy. But my therapist spoke with me over and over, about my managing of my feelings, inclusive of jealousy. And she helped me with other cuckold feelings, like those, which come with Angst.

The first experience we had together, as a married couple, concerning cuckolding, happened while we were away. My wife had told me that she wanted to be with a guy in his early 20’s, or even younger, as long as he was of legal age. She was in the first half of her 30’s, during that first experience. We never had children, and her body was firm and beautiful. And her face at that time was so pretty (both are still true). She is 36C (at times 36D) and those breasts are gorgeous, and she loves having them kissed and sucked. Men constantly look at her. Prior to marriage, she did have some encounters with females, and she always considered herself bisexual.

To keep this from becoming too long, and too boring; I will try and cut to the chase. While we were away, my wife saw a young guy who was desirable to her. And she wanted me to approach him. She had watched him while he was working, and she liked him and how he interacted with people. He was 22 years old, blondish hair, muscular, handsome, well spoken, polite, and hopefully well endowed (I was not able to bring this question up to him……it was beyond what I am capable of)). And I did approach him on his break-time and told him our idea. It was as if he won a million-dollar slot machine. I motioned for my wife to come over and we spoke to him together. We set a time for him to come to our hotel suite, after work. He wanted to go home first and shower and change his clothes. We agreed.

My wife and I went to buy her new lingerie. Somehow shopping for bras and panties for her to wear for another man, was so exciting. Already I was feeling envious of him. And already, my feelings of jealousy we being felt within me. And I felt embarrassed in front of my wife, for letting this happen in the first place. Back at our hotel suite, I helped Jessica prepare for her time with her new lover. I helped with her shower, and with her hair and makeup. And we would discuss what would happen. I had on only a T-shirt, and my wife could see me with an almost full erection, or at times, with a full erection. And she commented on how it took this, for me to get hard, and even to the point of “almost fully hard”. She wanted me to speak with him once he arrived, man to man. She wanted me to tell him that only she could remove any of her clothing, but that he could remove an article of her clothing, including her bra and panties, if she directed him to. And I needed to tell him, “No-Anal”. And that he must use a condom. And I placed a bunch of condoms on the coffee table. And I told him that he could not stay beyond 4 hours. He agreed to all. I asked if he had any question, and he asked, why we were doing this? I then explained that I had erection issues (although I used more simplistic terms). I explained that Jessica needed some good sex, inclusive of good intercourse. And he said that he understood. And I told him, as she had wanted me to, that Jessica enjoyed kissing, and lots of affection.

Jessica came out of the bedroom. She wore a black dress with beautiful cleavage. And she wore high heels and a necklace. She looked so hot and stunning. She walked over to him to where he was sitting with me. I got up and sat away from them. He stood up. She extended her hands, and he extended his hands. She kissed him on the side of his face. She asked him how he was doing. He said fine and asked her the same question. He and my wife then sat on the couch, in the living area of our hotel suite. She asked if he were nervous, and he said yes. She told him that she too, were nervous. She asked him his zodiac sign and told him her sign. Their hands were touching. I was jealous. I was envious of him. And I already felt left out. Looking at them, it appeared as if they were out on a date. An older woman, and a younger guy, on a date. I felt teary eyed. I wanted my wife back. But I knew that it was me and my issues which caused this to happen in the first place. I thought of things the therapist told me, and I tried to manage my feelings. And I knew that soon I would need to process my feelings as something erotic, because that is what my therapist told me to do. But first, as my therapist told me, I needed to feel my feelings.

As I watched and heard their small talk, I saw them kiss. It was a soft and gentle kiss. Tears came down my eyes. I was feeling so left out. They kissed again, and again. But for now, it was closed mouth kisses. And after a few kisses, she and he, would stare at one another. And in the next moment, the kisses would continue. As I sat at the other end of the room, my penis became really hard. I was jealous and upset but very stimulated and excited. Tears would come down my face intermittently. As I stayed in my place, I saw my wife’s tongue coming close to him, and then saw him accepting her tongue, by touch his tongue to her tongue. And they sat together, their tongues touching outside their mouths. Somehow, I had not expected to see this kind of intimacy. I could feel their chemistry. It was an energy with a sexualized excitement, and it felt as if Jessica truly needed another man for sex, and that she was now with him. And it felt as if he were so happy to be involved with foreplay, especially with a woman who is older. And he seemed somehow, as if he felt extra charged, because Jessica’s husband was present, while he took his place. I observed my wife and her new friend, as I sat in a state of some confusion, feeling lots of excitement, with an very hard erection (which I probably would not otherwise have), and I listened to the moaning of my lovely wife, and some additional moaning noises made by him, and I watched as her tongue push into his mouth, and their mouths kind of stuck together for a moment, until I saw their tongues once again, until his tongue pushed into the mouth of my beautiful wife. I sat there, alone and ignored, and felt so left out. I was rubbing my penis thru my pants. In the next moment, I remembered that my therapist told me to try to feel her pleasure and his pleasure too. And for me to accept that my wife and her lover, are enjoying each other sexually and intimately. And for me to enjoy their pleasure together. And to feel my jealousy and all my other feelings, even my really hurtful feelings, as something very erotic. As I continued to observe my wife and her younger lover kissing deeply, I felt so inadequate. And I knew that this handsome young guy was the man that was sexually adequate. And that he would be able to provide her the pleasure she needs to reach a climax, thru intercourse. And deep inside me, I knew that the oral that he would provide to my wife, would be better than the oral I had ever provided to my wife. As they embraced and kissed, I could see that she accepted him, as the better and more masculine man.

My wife broke from their kissing and told him to take off everything he was wearing. I tried to make eye contact with Jessica as he removed his clothing. But she was not looking at me. When his underwear bottoms came off, an incredibly huge cock was revealed. I was envious beyond anything I ever felt before, as far as feeling envy. And my jealousy was more powerful than ever before. Although I knew how I was told to manage my jealousy, I was feeling overpowered by it. And overpowered by whatever else I was feeling. I was so humiliated and embarrassed, when my wife told him: “Oh my, now, that is a really great cock, your cock is actually gorgeous, you are so lucky to have that; I want it so bad inside me”.

My wife stood up and told him: “Take off my dress”. And he took off her dress and she stood there in front of him, for a moment, in her new bra and panties. His cock reacted, upon him seeing her in her new lingerie, by getting more color and by his hard erection, showing even more stiffness. She looked so beautiful and sexy in her bra and panties, heels, and her necklace. Before they sat again together on the couch, he told my wife: “You are so beautiful, and you are the sexiest lady I have even seen, if you were mind, I would not share you with anyone”. Never did I feel as humiliated, as that particular moment. It was at this point, that I removed my pants and undershorts. And I could now directly touch my penis. During what transpired I found that I was able to have good erections, and because of the level of excitement, and the roller-coaster of feelings, I was able to masturbate myself after I would climax, and again achieve an erection. It was counterintuitive. Because under everyday conditions, I had erection difficulties.

They embraced as they sat together, and they kissed deeply. He then kissed Jessica’s face all over, and her neck and down to the cleavage, just above her bra. He then kissed her breasts thru her bra. And then he kissed the stomach of my wife. She told him to stop, and he did. And then my wife told him to undo her bra. And he went behind her and unfastened her bra. And she told him: “Take it off”. And her bra came away and revealed the most beautiful breasts he even had seen. She extended her arms, as she had done for me so many times, and she placed her hands at the back of his head, and he placed his mouth at her left breast, kissing all over that breast, and then, he sucked. My wife moaned deeply as she held him there, nursing him. He needed to keep sucking. He made noises as he sucked. As I saw this, I knew that they had feelings towards one another. He then moved his mouth to her right breast. Again, he kissed her breast all over, and then he sucked. I knew how wonderful it felt to be at each breast of my wife, while she embraces the back of his head, as if pulling him even closer to her. I was so envious of him. I wanted to have my mouth in that same spot, and to be held by my wife. He absolutely loved her tits and with his mouth, he marked them all over. My wife and him, continued making out, and I watched, as she whispered something in his ear. Seeing this I felt betrayed. She then looked over to me, and she said, “We’re going to the bed, come with us, and you can keep watching”.

My wife then held him by this hand, and she led him to the bedroom of our hotel suite. As they walked, him slightly behind her, his cock was in a proud state of erection. I’m not gay at all, but his whole body was beautiful. He had no fat on him, and he was muscular. His balls were large, and for now, they were tight and near his body. His face was handsome and symmetrical. He was 5’9″ in height. Next to the bed, with him standing, my wife kissed his chest and then his stomach, and she got on her knees and kissed his erection, and next his balls. She kissed his legs, down to his feet and then she kissed her way back to his erection. She then placed a little of it in her mouth, but soon she could fit no more. She was never big on blow jobs. And I knew not to ask. But he did not need to ask. My wife was sucking on his big penis. And he was moaning. Then she looked up at him, and she said: “Please I need to get fucked now”. He then picked her up and placed my wife on the bed. Jessica immediately took of her panties, and then spread her legs. And he got into position, on top of my wife, and then his giant penis was at the opening of her vagina. Her hand went to his cock, and tried to guide it in. And he gently and so slowly, thrust into my wife, and his cock guided by her hand, entered my wife’s vagina. She let out a moan. And then she said: “It’s so good, so big and good, I love your cock, I’m in love with your cock, please fuck me hard”. He pushed his cock all the way inside. And then took it almost all the way out. And then pushed it back in. He then pushed his tongue inside his lover’s mouth. My wife was having sexual intercourse with another man, as they deep kissed, and I was powerless. And I came to realize that he did not place a condom on his penis. But I knew I should not say a word. They continued in intercourse, both reaching a climax.

We extended our stay, by 6 days, so they could spend more time together. Because she so enjoyed him and their lovemaking, and because he enjoyed it too. He stayed all night, and the next day also, and half the next night (but returned after a few hours). And they were together most of the time, thereafter, until we left. He missed days at his job, so he could spend time with Jessica. And I gave him some money, to make up for what he lost. After their first intercourse, she opened her legs and asked me to provide oral. Upon opening her legs, sperm leaked out of her vagina. She did not use the term “clean me”, she later told me, so that I would not feel more humiliated than I already felt. And I licked inside of her vagina, which was soaked from his sperm and from her own wetness. I was also kissing her vagina, and the inside of her thighs. Knowing that she just finished intercourse with her lover, caused me to passionately provide oral to my wife. As I licked and kissed her vagina, I could hear she and he, kissing. And I looked up, and also saw my wife and her lover kissing. Feeling as if they were a couple, and like I was the single guy, the one being, more or less, left out; felt very erotic to me. And providing oral, to her soaked vagina felt very appealing. During that first episode, after I provided oral, my wife asked me if they could have some private time together (she and I had amended our agreement previously, so that she could be alone with her lover, at times). I could see that they wanted to sleep, holding one another, and I agreed to leave the room. They were alone together for about 8 hours. I slept in the living area during that time.

My wife and I had a favorite position, during the times when we did (almost) enjoy intercourse together (the year and a half, while we dated, and after we were first married) And that position was the sitting position, facing on another. And we’d rock back and forth, with my penis inside my wife. We’d be kissing, and/or, I would be sucking her breasts, as our bodies were joined together. As time went by, like after we married, because of my erection issues, this kind of lovemaking, no longer worker for she and for me. During the time with her new lover, she told him about our favorite position one evening during dinner. And she asked me, if I would enjoy watching she and he, enjoying the position that she and I loved the most. I responded positively. But deep inside I was somewhat hurt. But I kept silent and wanted to somehow enjoy it. Later back at home, I was honest with her about my first reaction. Her lover was interested in doing this. And of course, Jessica wanted it to happen. I asked her, if she would tell us, whom this position was more pleasure with (me or him?). And she agreed. Before they engaged in the act itself, I needed to ask him to make love to my wife in the sitting position…….and how I had failed……and I would need to kind of beg him to make love to Jessica, my wife………and when he told me to do it to her…….I would need to insist that I can’t do it……..and that she and I really need him to do it…….

During that time at dinner, she and he sat next to one another. And I sat across from them. Before the food came, she and he engaged in some kissing. And my wife and he, knew that seeing them kiss was exciting to me, and caused me to feel jealous, and then, I needed to manage my feelings in a way that was erotic, as the therapist had directed me to. And they actually teased me, by kissing really fast, and asking if I enjoyed it. And I would then feel compelled to see them kiss again, so I would need to ask them to keep kissing. And they’d ask me why I wanted to see them kiss again. And I need to say that it feels so erotic, and it turns me on. And I would tell them that the jealousy feels so good and erotic. And soon I would be just about begging she and her lover to kiss one another, deeply and passionately. I would tell them how good it feels for me to be left out.

As we were eating, he asked if I would help them rock back and forth, by actually rocking their bodies as they were embracing and were locked together. I agreed to do this. Later, after we returned to the hotel suite, they had a shower together, after we each used the bathroom privately.

As they were in the shower together, I watched them together. They would embrace and kiss. I sat on the floor of the bathroom, not allowed to touch myself, as I watched (my hands we bound behind me). And it would turn into teasing, and then I would be begging them to kiss and to embrace. He would say things like: “I’m not kissing your wife anymore”. And she would ask me to tell him to kiss her. And I would soon be begging him to kiss her. And to make love to her. And when he would ask why………I would tell him that I had erection issues……..and how sorry I am……..

when it was time for their lovemaking, while facing one another, I had to explain to him how to do it…….and he would tell me to do it…….and I would need to explain why I can’t do it………and how much she loves it………

By the way, we had all along, a safe word, in case I really wanted the game to stop.

This was the start of our cuckold relationship. And she has enjoyed many lovers. And this works for my wife and for me. There is nothing I would not do for my wife.

And so, yes, some men, do enjoy cuckolding.

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