I'm 37 and have been a cuckold for the past nine years. I have been with my girlfriend for the past nine years straight and on and off for the five years before that. We don't plan to get married. For my personal taste cuckoldry is better as bf/gf than it would be as h/w. Anyway I'd like to tell about our history and our brand of cuckoldry.
Ramona is an attractive woman of Asian-Indian descent, though she comes from Guyana. I am a tall, handsome white guy, but I am timid and ineffectual. I have been submissive since I can remember. In my late teens and early 20's I had lots of fantasies of being physically dominated by women or of giving money to women. I found some outlet for those fantasies through prostitutes. I also had some cuckold fantasies, but they were just used occasionally for masturbating.
Ramona and I started going out when I was 23. She was very into me and saw me as more of a man than I really was. She was very shy and passive and was kind of a sadsack. Within two years I had become overcome with an incontrollable urge for her to cheat on me. I approached this topic as fantasy first, and she would talk me through them while we made love. Then I started asking if she would really cheat on me, if I wanted her to. She said she would. That brought the excitement to a whole other level. We still hadn't taken the plunge yet, but our love making sessions filled with talk about her cheating on me were even more exciting, knowing that she would really do it. Yet when it came time to actually put the plan into motion, I would always back out. I had that ambivalence that probably 95% of us have the first time.
So for two years the cheating remained a fantasy. Then one day when we were 27 we went to a party at her friend's house, and there was this guy there named Mike who was all over her. Apparently she knew him from previous times there, and she had told me about him but had made everything seem like he was just a big brother type who occasionally put his arm around her. Well now seeing it live in front of me, I could tell that his thoughts were not brotherly. He would not let her out of his grasp. He was constantly hugging her, more and more suggestively. She didn't seem to like it, but I could tell that her shyness made it impossible for her to get away from him. I was not in cuckold mode, so I was embarassed and didn't know what to do. He was an unattractive, slovenly, out of shape guy in glasses, but I was too wimpy to make a stand. So we both beared it for an hour or so and then made a quick exit. On the drive home I scolded her for not speaking up and telling him to get off of her, but I knew that I was just as guilty as she was. Our relationship became slightly strained after that, and within a couple of weeks we had split up.
Then about a month after that, I found myself in high cuckold mode and started fantasising several times a day about Mike touching her and about my own humiliation. I called Ramona and started making amends. I had decided that we were going to enter the cuckold lifestyle, but I knew I had to keep this to myelf until she was more sure of us as a couple. I treated her like a princess for three weeks and said nothing about Mike or cheating fantasies or anything. Then when I was sure that I had her back 100%, I made a comment out of the blue that we should invite Mike over for cocktails. At first she thought I was kidding. Then she thought I wanted some kind of revenge on Mike. But I just kept telling her that I didn't want there to be any hard feelings between us and Mike (ridiculous logic because he was only a friend of her friend). And I told her that I wanted to show her that I was with her through thick and thin - to give me a chance to redeem myself for being so inconsiderate after that party. She relented.
She got Mike's number from her friend, who was very surprised by the request to say the least. Then she called and invited him over to her apartment on a Friday night for drinks with her and me. She assured Mike that this was not a setup for revenge. Like I told her to, she told him that I would be wearing wimpy blue soft slippers and once he takes a look at me in them he'll see I'm just a "big softy". (Side note: I have found that wearing soft slippers, especially ones that stand out, are very conducive to getting in touch with your wimpiness.) Mike agreed to come. When she hung up she saw the big grin on my face, and I just couldn't help but say "I bet he's really excited". She smiled and shook her head like I was some kind of cute but incorrigible little kid, and with that small exchange my cuckold persona came back into the relationship fullfold. At that point she realized one hundred percent what I was expecting for Mike's visit.
Sure enough Mike saw me in my slippers and gave a chuckle. I could also tell that he really liked how Ramona looked in her big fuzzy slippers, as did I. I told him and Ramona to into the living room and that I would bring the drinks. Sure enough by the time I reached the room, he was snuggled up next to her on the couch, though not with his arm around her. I sat on the recliner. We watched tv and drank and chatted about this and that, and within a half hour his arm was around her. I made sure to leave the room for something or other every fifteen minutes or so, to give him every opportunity to have some fun with her. After about an hour he started massaging her feet. He also snuck in some grabs at her breasts when he thought I wouldn't notice. After about three very enjoyable hours of this, I told them that I wasn't feeling well and would be going to bed but that by all means Mike should stay longer. I went off to the bedroom and turned on a fan to drown out noise. I didn't want to hear anything. I wanted to wait for Ramona to tell me whatever happened.
About an hour later Ramona came into the bedroom, and I asked if Mike had left. She said yes. I wanted her to come talk to me, but she laughed and told me to be patient and wait till she got ready for bed. After what seemed like an eternity (maybe four minutes), she came into bed and with a satisfied smile on her face said very coyly "what do you want to know?" I could barely contain my excitement and yelled "EVERYTHING!". She laughed and told me that every time I left the room Mike was squeezing her breasts and sticking his tongue on her mouth. She said that I soon as I went to the bedroom Mike grabbed her hard and started making out with her. She said that he was trying for sex but that she took out his dick and sucked it. She said that as she walked him out, he was grabbing her breasts and ass like she was a piece of meat and that a woman who lives in the next apartment saw the whole thing. At that point I grabbed Ramona and fucked her like I never had before.
After that there was no going back. We never called Mike to come over again, but whenever there was a get-together at her friend's house she went alone and would see him. We weren't sure how much Mike told people about what had happened at her apartment, but they definitely knew what was going on in front of their eyes. Ramona said that Mike was more blatant than ever in his fondling of her. She also said that they would steal away together for short periods of time and that she would suck him. She said that only an idiot wouldn't know that there was something going on between them. As far as me, she told Mike that I was mad that she had given in to him and mad that she was still carrying on with hime, but that since I loved her I would allow it.
That has been the theme through the rest of our cuckold relationship. I always play the part of the fool who lets his horny girlfriend cheat on him. Only a couple times, while staying at hotels, have we made it obvious to someone that I am really into it. As of now Ramona has a regular lover who she sees every Friday night and sometimes Saturday night too. Al is her third regular lover. She had one in 2000-01 and one in 2003-2004, and in between she has had her assortment of one night stands. She has made it a point to tell everyone that she has been with that she has a boyfriend. All of her regular lovers met me in person, and none of them were very nice to me, which makes it all the better. Ramona and I live together now, and occasionally Al comes over to pick her up and I feel like I'm going to faint from excitement, humiliation, fear, anger, and confusion. He has made it no secret that he hates me. It is an incredible feeling to be face to face with a guy who hates you for no reason, who is going to fuck your girlfriend. And the cherry on top is when Ramona hugs me goodbye and gives me the softest kiss on the cheek saying that she doesn't want to smudge her lipstick.
I am a cuckold forever. If anyone actually had the patience to read this whole, please feel free to contact me with any questions or comments.
Ramona is an attractive woman of Asian-Indian descent, though she comes from Guyana. I am a tall, handsome white guy, but I am timid and ineffectual. I have been submissive since I can remember. In my late teens and early 20's I had lots of fantasies of being physically dominated by women or of giving money to women. I found some outlet for those fantasies through prostitutes. I also had some cuckold fantasies, but they were just used occasionally for masturbating.
Ramona and I started going out when I was 23. She was very into me and saw me as more of a man than I really was. She was very shy and passive and was kind of a sadsack. Within two years I had become overcome with an incontrollable urge for her to cheat on me. I approached this topic as fantasy first, and she would talk me through them while we made love. Then I started asking if she would really cheat on me, if I wanted her to. She said she would. That brought the excitement to a whole other level. We still hadn't taken the plunge yet, but our love making sessions filled with talk about her cheating on me were even more exciting, knowing that she would really do it. Yet when it came time to actually put the plan into motion, I would always back out. I had that ambivalence that probably 95% of us have the first time.
So for two years the cheating remained a fantasy. Then one day when we were 27 we went to a party at her friend's house, and there was this guy there named Mike who was all over her. Apparently she knew him from previous times there, and she had told me about him but had made everything seem like he was just a big brother type who occasionally put his arm around her. Well now seeing it live in front of me, I could tell that his thoughts were not brotherly. He would not let her out of his grasp. He was constantly hugging her, more and more suggestively. She didn't seem to like it, but I could tell that her shyness made it impossible for her to get away from him. I was not in cuckold mode, so I was embarassed and didn't know what to do. He was an unattractive, slovenly, out of shape guy in glasses, but I was too wimpy to make a stand. So we both beared it for an hour or so and then made a quick exit. On the drive home I scolded her for not speaking up and telling him to get off of her, but I knew that I was just as guilty as she was. Our relationship became slightly strained after that, and within a couple of weeks we had split up.
Then about a month after that, I found myself in high cuckold mode and started fantasising several times a day about Mike touching her and about my own humiliation. I called Ramona and started making amends. I had decided that we were going to enter the cuckold lifestyle, but I knew I had to keep this to myelf until she was more sure of us as a couple. I treated her like a princess for three weeks and said nothing about Mike or cheating fantasies or anything. Then when I was sure that I had her back 100%, I made a comment out of the blue that we should invite Mike over for cocktails. At first she thought I was kidding. Then she thought I wanted some kind of revenge on Mike. But I just kept telling her that I didn't want there to be any hard feelings between us and Mike (ridiculous logic because he was only a friend of her friend). And I told her that I wanted to show her that I was with her through thick and thin - to give me a chance to redeem myself for being so inconsiderate after that party. She relented.
She got Mike's number from her friend, who was very surprised by the request to say the least. Then she called and invited him over to her apartment on a Friday night for drinks with her and me. She assured Mike that this was not a setup for revenge. Like I told her to, she told him that I would be wearing wimpy blue soft slippers and once he takes a look at me in them he'll see I'm just a "big softy". (Side note: I have found that wearing soft slippers, especially ones that stand out, are very conducive to getting in touch with your wimpiness.) Mike agreed to come. When she hung up she saw the big grin on my face, and I just couldn't help but say "I bet he's really excited". She smiled and shook her head like I was some kind of cute but incorrigible little kid, and with that small exchange my cuckold persona came back into the relationship fullfold. At that point she realized one hundred percent what I was expecting for Mike's visit.
Sure enough Mike saw me in my slippers and gave a chuckle. I could also tell that he really liked how Ramona looked in her big fuzzy slippers, as did I. I told him and Ramona to into the living room and that I would bring the drinks. Sure enough by the time I reached the room, he was snuggled up next to her on the couch, though not with his arm around her. I sat on the recliner. We watched tv and drank and chatted about this and that, and within a half hour his arm was around her. I made sure to leave the room for something or other every fifteen minutes or so, to give him every opportunity to have some fun with her. After about an hour he started massaging her feet. He also snuck in some grabs at her breasts when he thought I wouldn't notice. After about three very enjoyable hours of this, I told them that I wasn't feeling well and would be going to bed but that by all means Mike should stay longer. I went off to the bedroom and turned on a fan to drown out noise. I didn't want to hear anything. I wanted to wait for Ramona to tell me whatever happened.
About an hour later Ramona came into the bedroom, and I asked if Mike had left. She said yes. I wanted her to come talk to me, but she laughed and told me to be patient and wait till she got ready for bed. After what seemed like an eternity (maybe four minutes), she came into bed and with a satisfied smile on her face said very coyly "what do you want to know?" I could barely contain my excitement and yelled "EVERYTHING!". She laughed and told me that every time I left the room Mike was squeezing her breasts and sticking his tongue on her mouth. She said that I soon as I went to the bedroom Mike grabbed her hard and started making out with her. She said that he was trying for sex but that she took out his dick and sucked it. She said that as she walked him out, he was grabbing her breasts and ass like she was a piece of meat and that a woman who lives in the next apartment saw the whole thing. At that point I grabbed Ramona and fucked her like I never had before.
After that there was no going back. We never called Mike to come over again, but whenever there was a get-together at her friend's house she went alone and would see him. We weren't sure how much Mike told people about what had happened at her apartment, but they definitely knew what was going on in front of their eyes. Ramona said that Mike was more blatant than ever in his fondling of her. She also said that they would steal away together for short periods of time and that she would suck him. She said that only an idiot wouldn't know that there was something going on between them. As far as me, she told Mike that I was mad that she had given in to him and mad that she was still carrying on with hime, but that since I loved her I would allow it.
That has been the theme through the rest of our cuckold relationship. I always play the part of the fool who lets his horny girlfriend cheat on him. Only a couple times, while staying at hotels, have we made it obvious to someone that I am really into it. As of now Ramona has a regular lover who she sees every Friday night and sometimes Saturday night too. Al is her third regular lover. She had one in 2000-01 and one in 2003-2004, and in between she has had her assortment of one night stands. She has made it a point to tell everyone that she has been with that she has a boyfriend. All of her regular lovers met me in person, and none of them were very nice to me, which makes it all the better. Ramona and I live together now, and occasionally Al comes over to pick her up and I feel like I'm going to faint from excitement, humiliation, fear, anger, and confusion. He has made it no secret that he hates me. It is an incredible feeling to be face to face with a guy who hates you for no reason, who is going to fuck your girlfriend. And the cherry on top is when Ramona hugs me goodbye and gives me the softest kiss on the cheek saying that she doesn't want to smudge her lipstick.
I am a cuckold forever. If anyone actually had the patience to read this whole, please feel free to contact me with any questions or comments.
