My personal cuckolding history — Part 5, Series Finale

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My personal cuckolding history - part 4

So I finally had my first cuckolding moment... I drove off on a Sunday morning to go fuck some guy 40 miles away. I came back and told my sissy cuck all about it. I had finally crossed the bridge, I was truly cuckolding him.

I was somewhat flustered in the beginning, a whirlwind of emotions. On one hand I still had the fears that he was going to change his mind or that he was really lying to me about all of this and testing me to see how far I would go when it comes to sleeping with other men. I also didn't know my limits, what I could do or what I should do, or even what I wanted to do at that point. But at the same time, seeing him help me pick out clothes to wear and getting me ready for dates, him taking pictures of me for the world to see, giving me ideas when it comes to what to put on my profile for the dating site or him listening to me gripe about some of the messages these morons would send... I knew he wanted this for me. He wanted me to be happy more than I could ever imagine.

I was also bad about sharing with my cuck. Like most cuckolds, aside from craving the humiliation that comes from other men servicing their beautiful lady, they are dying to know what their cuckoldress is thinking and feeling. My fears and hesitations made it hard to communicate my thoughts and feelings about the experience to my adoring cuckold. It's true, Jinxypie isn't perfect... but I know since the sissy has to put up with me doing as I please, he deserves to hear those things from time to time... he's such a good boy for making sure I'm taken care of!

In the beginning I told him I had no interest in fucking a black guy. No matter what I said, my cuck kept bringing it up, because he swore they could do this better than white guys. (He had a wife that cuckolded him before, remember? Apparently she'd had quite a few big black cocks.) Of course, after being with so many guys I wanted something different... I have had my first (and so far only) black bull. He's awesome enough to be featured in multiple pictures and even videos on this very website! ;) I've had lots of offers, but for now I've found the black bull that can satisfy me like no other. Don't get me wrong, I still fuck other guys... sometimes multiple guys a day. But I only have ONE black bull.

As a cuckoldress, I am much different from when I started this. I'm becoming more dominant with my sissy cuck. I am more confident than I have ever been, in and out of the bedroom. Luckily, since I'm a webmistress by profession, I have had the knowledge and opportunity to create a pretty nice personal site for myself. I've also gained some insight on reading people... in my position I chat with a LOT of people. You can usually spot some fakes right away, but others take a few moments before showing their true colors. If you're fake, I can usually spot you pretty easily... don't think you can fool me.

Stay tuned for more...

~Jinxypie

My personal cuckolding history - part 3

So you've read parts 1 and 2. You've been eagerly awaiting the next part, haven't you? ;)

As I ended part 2, I had found a decent-looking guy that was sort of close by. I gave him my Yahoo screen name and we started chatting on a Sunday morning. My cuck was sitting at the desktop computer, working, while I had one of the laptops, flirting online with this sexy stranger.

Sunday mornings are usually very quiet at our house. No real interruptions. The guy I was chatting with was really wanting me to come visit him, right then. Understanding that it was about a 40 minute drive, I told him that I probably wouldn' t be able to stay very long. So I tell the guy I will "brb" and I walk over to my cuck. I told him that the guy wanted me to come over, right then, and that I wanted to go. Since this was the first time I was ever going and having sex with someone while married to him, I think I was kind of asking permission. (That didn't happen many times afterwards...)

He assured me that everything would be ok, and that he wanted me to go fuck this guy. Still nervous about it, I told the guy I would get ready to go, and that I'd be on my way soon. I gave him my cell, got directions, and started the "getting ready" process. My husband was right beside me the whole time, helping me pick out clothes and telling me how beautiful I looked... also telling me how excited he was and that he promised that he would still feel the same once I got back.

I sure hoped he was right. I wasn't completely convinced.

The drive was not very eventful, but the fact that my cell was nearly dead and I had no car charger was very intense. I didn't want to waste much battery life, yet I wanted to talk to my cuck to see how he was and to get another pep talk. (Haha.) I called the guy when I neared his house. He met me outside his apartment, then showed me inside. We sat on the couch and talked for about three minutes... then he was all over me - a nice surprise! I wasn't sure what kind of guy this would be... he seemed nice, he looked great, but you still never know what kind of person you're going to end up with when you do the picking and choosing online.

We had been fucking for about five or ten minutes when I noticed my cell was ringing. I had to run and get it; my cuck was checking up on me because I had broken our "rules". (I call when I get there and I text within a certain period of time to let him know everything is OK.) When he didn't hear from me he was worried... I was nervous because the first time I got out of the house to see someone, I broke the rules... and I didn't know how my cuck would feel about me doing it again. But I told him we had already been screwing our brains out and he let me get back to it.

After we finished, we layed around talking for a bit. Then I got dressed, told him I had a great time, and left. On my way home, I called my husband to let him know I had started the drive back. He asked how it was and, being nervous, I told him that it was OK. Wondering why it was "just OK," he assured me he was fine and if it was better than "OK" I should say so. Telling him the complete truth is the way to go. I told him that I did have fun, and "OK" wasn't a bad thing! Hubby accepted it, and asked why I wasn't talking much. I explained that even though he says he's ok with what I'm doing, I'm still leery of his reactions and wondered if he would REALLY be OK with it when I got home...

When I arrived, my cuck greeted me at the door. He asked how I was and of course I was good. So we went to the bedroom to talk about the experience I just had... see, with my cuck (and most others), we don't have regular sex. It's me talking to him about what I did or what I'm thinking or feeling and him getting excited by it so he can jerk off... (Some cucks don't even get that pleasure, they're locked up in chastity devices or just denied.) Anyway, we talked and I still needed his assurances that everything was great. After all, I had just went out and had sex with someone. Could he really be happy with me? Of course he was. He wanted this for me. He wants me out fucking anyone that I want because he knows I'm getting exactly what I need!

This first experience showed me that he meant exactly what he said. I was still a little hesitant, but things were getting easier...

Part 4 coming soon!

~Jinxypie

My personal cuckolding history - part 2

After reading part 1 of this series, you found out that both my cuck and I had been married before. He had been cuckolded pretty much that entire time, while I had to settle down from my wild teenager days.

After my marriage ended, I started easing back into my old ways... flirting non-stop and trying to find guys to have sex with. Life was fun again! My cuck's marriage ended just after he moved to a new town. It's like he got a fresh start as well.

We are both "nerds" in the respect that we deal with technology and we're pretty dang good at our jobs. I love a smart man, I can't deny that. I was immediately attracted to his smarts... He vividly remembers the first time he saw me, down to exactly what I was wearing and how I wouldn't really look at him (what can I say, I can be a little shy). We hit it off and started dating.

What's a cuck to do when I start getting hot-and-heavy on him, kissing and rubbing and talking about how I wanted to fuck. What any good sissy boy does, he tried his best to give it to me. When I first saw how small he was, I was a little disappointed. I had hoped for a huge surprise, but all I got was a tiny revelation. I did my best to "enjoy" it (I didn't want to hurt the boy's feelings). There was so much more that he could do for me, that I put up with the bad sex. I mean, I had a vibrator at home that was becoming my best friend anyway... I would get lost in daydreams while he was trying so hard to fuck me and make me feel anything, I would start thinking about guys I had been with in the past or I would have him talk to me about different fetishes so I could daydream about that too.

Then one day we started talking about what his ex did to him - having sex with other men, sometimes right in front of him. Immediately my reaction was to condemn her for what she did to him and how that must have made him feel. I'm pretty sure my quick reaction is what made him hold off in telling me how he actually enjoyed what she did.

We got pregnant, and I lost some of my sex drive. Once I had the baby and the "waiting time" was over, I wasn't even really excited about sex then. I mean, look what I had to fuck! Something that wasn't even three inches. Where's the fun in that!? My cuck could tell that I was unhappy when it came to sex, and we started having more and more discussions about his previous marriage, and how she would have sex with other men. The more we talked about it, the easier it was for me to understand.

We started talking about how it would be for me to fuck other men. At first, I was very uncomfortable with the idea. I mean, all the talk before was about his ex doing this... now we're talking about ME going to have sex with random guys. (It was fine and dandy when I was unattached, but now I'm married... married women don't go fuck random guys!) Not to mention, I had the fear that maybe he really didn't want me to be this way and was just trying to see how far I would go with it... Again, the more we talked about it, the more reassuring he was and the more it seemed like the best situation. I could get satisfied by a man with a big dick and my cuck would be happy that I got fucked just like I needed. I still needed some convincing though. There were nights we would sit and look at porn together, he would talk to me about which guys I liked and what turned me on... and after we'd both finish, he would say something along the lines of "See? I'm not upset, and everything is ok."

It wasn't long before he suggested I sign up for a few adult dating websites and we started hunting for online Cuckolding forums. One night we took the plunge and found a few, but that meant we had to take a few pictures for the webpages. It was fun getting all dolled-up, trying to make sure I looked good enough to make someone want to come fuck me. We took a few of my favorite pictures that night (look for the Navy football jersey in the gallery).

Lo and behold, the messages started coming via the adult dating website. I'm extremely picky, so I would weed through each message with a fine-toothed comb. The decent messages I would reply to, and give them my Yahoo so we could chat. I found a few chatters, but one was kind of close by...

Next up, part 3.

~Jinxypie

My personal cuckolding history - Part 1

This idea came from a cuck who found my website and decided to send me a message. I figure if he's curious about this topic, others probably are as well...

This is going to be a series of posts, talking about how I started cuckolding my husband, but going back to before I even knew what cuckolding was.

Both my cuck and I were married to other people for years before finding each other. Being young, I loved sex just as much as (if not more than) the next girl, never getting enough. I got married right out of high school and, as with most people, life changed. No going out and fucking whomever I wished. No excitement, flirting, or fun times to be had with random strangers, or even guys I had known for a while. I felt that every woman that got married had to change like this, as it is supposedly "normal". Normal married people don't go out and have that kind of fun anymore. Marriage is supposed to mean sex with one person for the rest of your life. (Or so I thought...) Needless to say I got very sexually frustrated and very bored. Same sex, every time, and sometimes it wasn't enough for me. There was one time that I did stray - I caught up with an old friend, we flirted and before ya know it we were all over each other and fucking like crazy. Anyway, towards the end of that marriage he had brought up the idea of having one of his friends coming over and fucking me. At the time I saw that as him not wanting me, he would rather have one of his friends come fuck me so he wouldn't have to. That put me in a bad place, mentally. When the marriage ended, I started flirting with old friends and a couple new people, fucking guys like I did back before I was married. No one could ever give me enough, attention or sex. I was turning in to quite the horny slut.

For my cuck, his ex was cuckolding him before they were ever married, when they first started dating. She was fucking guys left and right, not telling him a thing. He's not a dumb man by any means, so it didn't take him long to figure it out. I'm not saying they never had sex, I'm just saying more often than not she was with other people and either lying to him about it or leaving off details. He came to love the excitement and humiliation from knowing his girlfriend/wife fucking all kinds of men. He knew from a young age that he had a very small penis, and accepted the fact that he'd never be able to please a woman like she deserved. After learning what a cuckold is, he quickly realized that was him, exactly. He not only had a woman that went out and fucked other men, but he got pleasure in knowing she was satisfied by her lovers and was so humiliated and turned on at the same time. She liked that he allowed her to go see anybody that she wanted, not that she ever asked for permission... but she wasn't very receptive to talking to him, giving him details. Cucks crave the details, the specifics of what the woman is feeling, her desires... and she wasn't willing to give him the satisfaction of knowing. Due to other issues (not related at all to cuckolding), their marriage eventually ended.

Part 2 of the series coming soon. :)

~Jinxypie