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My cuckold experience.

  • Thread starterJimmyHCO
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JimmyHCO

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May 18, 2010
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Those of you who read my previous posts, know that I'm actively trying to persuade my wife into cuckolding lifestyle. But in fact, I actually experienced cuckoldry in the past. It was actually my first girlfriend who cuckolded me and trained me to become a good cuckold. We were both 16 when we met, and started dating. We were both virgins at that time, she was very conservative, and we never did anything sexual - nothing more than a kiss on the cheek and holding hands. Then, after maybe a few months of us dating, she met this guy who was older than us, and started having sex with him right from the first date. He deflowered her right on their first date, and they were fucking like rabbits from that point on.

At first she didn't tell me about it. She introduced him to me as a relative, and I didn't suspect anything. It didn't even cross my mind that my beautiful, conservative virgin girlfriend was no longer a virgin and was already enjoying sex with an experienced guy. However she didn't hide it from me for very long. She was incredibly mature for her young age and lying, or sugar coating things was just not her nature. One day she just plain out told me whats going on. She didn't do it in any kind of apologetic way, she just put me in front of the fact. She told me she loves me, that I have a ton of positive things about me, but she doesn't see me as sexual, and would not be interested in having sex with me, ever.

Being a young guy, in love with her, I didn't take it easy at all. I was extremely upset and jealous. I even though about breaking up with her, and I did for a short while. However I couldn't resist for too long. Maybe a week or two later we were all hanging out in the company of mutual friends. In fact, we were cutting classes in a nearby park. I was sitting on a bench, and she came to me, sat in my lap, and let me hug her and hold her. This was the first time she (or any other girl for that matter) let me do that, this was the first time I felt a girl this close, and this was an incredible turn on for me. No words were even said, it was just clear from that point on that the break up was over.

I came to accept the situation at hand, and we started dating again. Just like she promised, she wasn't interested in me sexually, and never did anything sexual with me, but we would always hang out together, go places, and so on. Another important reason was the fact that she was a very hot girl, and it gave me bragging rights before my friends to be dating someone as hot as her. Of course I didn't advertise to them that she was sleeping and enjoying sex with someone else and keeping me as her cuck boyfriend. She however didn't hide it at all from anybody. She would openly speak about it in front of all our friends, and soon enough most of them knew exactly what was going on. I still have not met or been introduced to her Bull (should I call him that?). I saw him a couple times from the distance when he picked her up in his car, but we were never directly introduced. Things went on the same way until her 17th birthday.
 
On the morning of her birthday we met at the regular spot in the morning, from where we walked to school. We usually walked in the company of 4 people, us two and another couple. I had a little present for her, precisely a nice perfume. Might not seem like much these days, but back in high school it took me a lot of savings to be able to get it for her. She was so happy when I handed her the gift! She gave me a French kiss, or more like just a kiss on the lips, right there and then! Right in front of the other couple too! I was so happy! It was the first time I received a kiss like that. All day I was in such great mood, I was the happiest person alive.

However that evening came remorse. She was throwing her birthday party that evening, her parents left her the house for the whole night. Everybody was invited, all of our friends, but most importantly, so was he....

This was going to be the moment of truth. The cuck was about to meet his Bull. Not only that, but there were also a lot of people that still weren't aware of our situation, and they were about to find out. This was one of the hardest things for me to handle.

I was at her place early, helping her prepare for the party. Then people started arriving, fun began, music was blasting, etc. But I was just waiting for Him to arrive. Finally he did. As he walked in, I couldn't help but notice that he was far superior male than me. Athletic built, with that cocky look, there was just something manly and sexy about him.

He walked in, they hugged and kissed passionately, he grabbed her ass while kissing. When they were done cuddling, she introduced him to everyone as her boyfriend. He looked at me with a smirk, shook my hand and said "You must be Jimmy, she tells me a lot about you". Then he proceeded back to hugging and kissing with my girl. Soon after they said they needed privacy and went to her bedroom.

All during the time they were locked up in the bedroom, I was just sitting on the couch in the living room, and feeling spaced out. Luckily the music was on pretty loud, so no sounds from the bedroom were heard. Still it was obvious to everyone to what was going on in there. I could feel that some people at the party were pitying me, and some probably found it funny. Luckily there were a lot of guys and girls at the party, and they were all too busy with themselves and just didn't pay much attention to me.

When my girl and her Bull were finally done in the bedroom, they came out, and she walked into the living room. I was still just sitting on the couch. She came up to me, and gave me a long, passionate French kiss. Right in front of everybody, including her Bull. I can't even tell you guys how great it felt. It almost felt like I was cucking him, not the other way around. I looked at him and he was smiling.

In any case, she proceeded to entertain herself and the guests, and he went into the kitchen. I don't exactly remember all the details at this point, but somehow later I ended up in the kitchen too, and he offered me a drink, then another. This was the first time I drank alcohol in my life, and I quickly started feeling sick. I rushed outside and walked home.

From that point on our relationship took a new turn. Her Bull actually turned out to be a very friendly, decent guy. Me and him became friends, and he persuaded me to start going to the gym together. We also shared interest for computers.

Very often I would walk my girl to his place. The three of us would hang out together, then the two of them would have sex. I never got to participate or watch of course. At best I would be in the other room fixing his computer, but most of them time I would go back home and then she would call me to come and pick her up. It was so painful to be in this position, but I was already starting to enjoy it.

There were however still two biggest fears to deal with. Her parents and mine. They knew me and her were dating, but they didn't know about him. I don't remember exactly how, but somehow her parents did find out at some point. They were upset about the age difference between her and him, but ultimately they had to deal with this. Their attitude towards me didn't change, I was still their sweetheart, and was always welcome to their house. Ironically, her dad was a life long cuck to her mom as well. I actually walked into them about a year ago in a store, and we yapped a little bit. They are still together, and her mom is still hot, despite being about 55.

But the biggest and hardest thing to swallow was my parents finding out. I really didn't want that. But I knew it was inevitable. She came by my place with him several times, but they never did anything overly suspicious in front of my parents, and I kept using the good old "her uncle" excuse".

One day my girl came to my place, with a big smile on her face. She said "you would never guess what happened. He just drove me by to drop me off at your place, just as your parents were walking out of the house. I pretended that I didn't see them, and proceeded to give my boyfriends a long, wet kiss, right in your parents sight!" That was it. Now my cuckoldry was know to everyone. My parents never mentioned it to me directly, but one day I was talking about things with my dad, and my girlfriends name came up, and he said, "You know, I don't think you guys are right for each other, she really should be dating someone older." We left this conversation at that.

My relationship with her lasted for probably another two years or so. During all this time she never had sex with me. She gave me two hand-jobs during the whole course of our relationship, and never all the way to the end. She would just prep me and then tell me to masturbate and cum in front of her. During this whole time I never had sex with any other girls. I did however have a one night stand with a guy, that she didn't know about.

Then after a while she got bored of her Bull and started seeking sex with other guys as well. She started having sex with guys our age, and then she found somebody that she felt in love with. Our relationship was unfortunately over.

I am however very grateful for the things she did for me, and for training me as such good cuckold. The thing with her, she never sugar coated anything. She told me right off the bat that I am a nice, caring, guy, with tons of positive qualities, but as a male I just don't come off sexual, that women wont desire me in a sexual way, that my cock is small and that I'll never be able to properly satisfy a woman. I realize that she is completely right, and I'm perfectly fine with that. I mean, how many many men suffer from not being very good sexually, and make their women miserable? Luckily for me, I'm not miserable like them, I came to accept the fact that I'm a lousy sexual partner, and I'm perfectly fine with being cuckolded and my woman fucking superior men for her pleasure. In fact, not only I accept it, I enjoy it.

After she broke up with me, I didn't take it easy. It was very difficult for me to handle. I couldn't believe she was gone, but thats life. At that point I still haven't had sex with a woman, and I didn't lose my virginity until a long while after. I was already 20 years old when I met this woman. She was 54 and married. Her husband was older than her, and according to her he couldn't get it up anymore. I finally had sex with her, for the first time. I was very lousy of course, and she didn't seem to enjoy it much at all. She also had another lover, about her age. She said he had a huge cock and was an amazingly good fucker, much better than me. However she enjoyed my company and kept having sex with me, saying that once I gain some experience I'll be better and it wont be so lousy.

Experience or not however, the sex was still lousy. I obviously couldn't satisfy her and it just wasn't even worth continuing having sex with her. It was much easier to masturbate. After a pretty short while I met this guy, and became his bottom. I don't really consider myself gay or bisexual, but I really enjoyed having gay sex and being submissive. We didn't have a relationship, but we had regular sex for around two years, until he moved to California. I had some more one night gay encounters since then, before I met my wife.

My wife is really a wonderful woman and I am very lucky to have her. She is one of those rare types for whom size, and vaginal intercourse are not very important. She is a multi cummer, and she gets most of her pleasure from oral sex. And I'm very willing to perform oral sex on her as much as she wants. I passionately lick her until she comes time after time after time. Of course, the vaginal sex we have after I have orally satisfied her isn't the greatest shes had. I don't last long, and have a small cock, so I can't properly please her. Hopefully I will persuade her into cuckolding, so that she can start having sex with men that can fuck her much better than I.