How I Became a Cuckold Pt. 01

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How I started exploring being a real life cuckold.
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Part 1 of the 11 part series

Updated 06/11/2023
Created 03/10/2022
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"She will meet you there tomorrow at 8 PM." I looked at the line I had just typed for a few minutes, felt my cock throb and my chest ache, and then pushed send. How I got to this point is a story in itself, but let me share some of the highlights.

Looking back, I think I always had the roots of this fetish in me. When I was younger I didn't know it. I was actually a pretty jealous boyfriend and was even kind of paranoid about cheating. I do remember discovering interracial porn and having many good wanks in college... oddly thinking about sending my girlfriend over to the two black football players across the hall and what they would do to her.

The girlfriend eventually did something that broke us up. She spent a few weeks as a camp counselor. There were two groups of kids with a day in between, so there were just the "grown ups" at the camp for a night. The other counselors, five guys college age to 40's, had a bet going that they would see her in full frontal nudity before the camp was over for the summer. She found out about it and of course was offended (or at least wanted to be) but apparently was more intrigued and a little flattered than anything else.

One thing led to another and she found herself very drunk with the guys on that in between night with no residents in the camp, and to make a long story short, she ended up stripping to her bra and panties for the roomfull of them. Apparently no one touched her and nothing else happened but when I found out about it I couldn't handle the jealousy. We broke up a few weeks later.

When I met Michelle, the woman I would eventually marry I knew I had a catch. She was an average height brunette with a stunning pretty face. She was curvy but slender and muscular. (Curvy is often code for overweight but not at all the case here.) Her most striking feature was a set of oddly firm large breasts that complemented the rest of her curves perfectly. It's no exaggeration to say she was a solid 8/10 and could have made a living modeling.

Personality wise, she was a classic good girl. She had a few boyfriends before me, but didn't do much. (Yes I know most of you reading will doubt that and sometimes I wish it wasn't true, but I'm almost sure it was.) Only one boyfriend had even touched her tits and my cock was the first she played with. She remained a virgin while we dated and was a virgin on her wedding day.) She had a healthy attitude toward sex and was extremely sensitive and orgasmic... a rare quality for a woman, I know. Perhaps due to her heavy religious upbringing she also had more than a touch of natural submission.

Myself, I'm average height and build. My cock is a bit on the small side I guess but not ridiculously so. I'm 5" when fully hard, but as I dated Michelle I started to have more and more trouble staying hard. Looking back I guess I always had some trouble with girlfriends but it became more and more until there were many times I just made her cum with my mouth or hands. This also lined up with me fantasizing more and more about seeing my woman with other men.

At first this fetish was just me thinking about old girlfriends, especially the girl who stripped at the camp. I thought about her being touched, maybe even encouraged to do sexual things. This became my go to fantasy when I would masturbate and I found myself masturbating a lot. But this soon grew to include Michelle and I started thinking about seeing her fucked by another man. Because she was a virgin and we dated a while before marriage I also really started liking porn that simply featured men cumming inside women. You wouldn't think that could be a fetish but it practically became one for me... maybe because I wasn't doing it.

I started chatting in some cuckold chatrooms and eventually met a guy who I had many late night sessions with. (This was after I was engaged but before married.) We talked about fantasies and interests and he was patient since he knew I had no experience. We chatted many nights and I found myself thinking about the cuckold fantasy almost constantly during the day. It became that only thing I thought about when I stroked myself... almost my only fantasy.

This also lined up with me having even more trouble staying hard when I was with Michelle. I was even unable to perform on our wedding night and ended up making her cum four times with my fingers and my mouth. The first time I was inside her was actually several weeks after we were married and then we proceeded to have a fairly lackluster sex life. When we did fuck, I was almost never fully hard. Even though i was only 5" I think she must have a fairly shallow vagina because when I was deep inside her I felt the head of my cock against what must have been her cervix one time. I thought I wished another man was in her and came instantly.

I continue to talk to the guy online and things progressed. He suggested that he would like to see my now wife. I found myself incredibly excited by the idea. I bought a camera he suggested, and then he picked out lingerie for her. I also bought the lingerie and then suggested to her she dress and pose for me.

She was excited and eager to do so, and I was rock hard taking pics that I knew I would share with him. He gave me specific instructions for poses he wanted to see, and also gave me specific instructions that I was not to fuck or cum while taking the pics. (I was however allowed to make her cum which i did... over and over... again mostly with my mouth and hands. I was becoming very good with my mouth I guess.) At first, he allowed me to crop the pics to not show her face.

When I showed him the photos later that night, he instructed me to edge my cock but not to cum. I had to work hard to not cum. I had never been harder and my cock was dripping precum down to my balls as I sat on the sofa late at night showing him photos. He loved her body and said he came twice before he allowed me to cum. I've never cum so hard and shot so much cum on my chest that it got on my chin.

This went on for a few months and I ended up doing about ten photoshoots for him. She never had any idea. She thought she was posing for me and had no idea I would show the photos to another man.

Eventually we drifted away but I continued to frequent cuckold chatrooms sometimes talking about my wife and sometimes showing a few of the photos. It was there, in one of those chatrooms, that I met Tim. He messaged me with some complimentary words on one of her photos, which showed her magnificent breasts in a nice support bra.

He said he was looking for real time rather than just online and understood if I wasn't. I was honest with him. I told him that my experience had been only online but I wanted to make it real. He asked a few questions and asked if I had told her. Again I was honest and said I had but I didn't think she had any idea how big of a deal this was or how much I wanted it. He said he understood when I said I didn't want to lead him on... and he said no problem he was enjoying talking to me.

He told me that he had a few specific interests and asked if I wanted to know about them. When i said of course he said are you sure? Said that some of them might seem pretty far out there to me. I said try me... who am I to judge?

So then it really began to get serious. I asked if I could stroke while he told me. He said yes but tell him whenever I was going to cum... tell him first... and that he appreciated I already knew how to obey. (Through all of this I was beginning to get the idea that submission was very exciting to me. If you're reading this it's probably pretty obvious to you I guess.)

He told me that a lot of his interests were flexible with partners but the one that wasn't was that he enjoyed owning and using married couples. Not wives... married couples. Not simply couples... married couples. He said that he had done this with two couples before and that each time was a good experience for everyone... the couples were still together after the experience even though it was sometimes a wild ride... and that he was looking to do it again... that he had learned a lot each time and now knew exactly what he wanted.

He said that he supposed this was a Dominant/submissive relationship but not like many people would think. He asked if my wife had ever been spanked and I said no. He said that he was not really into inflicting pain, but most women enjoyed a spanking and being handled by a man who knew what he was doing on the control front. It wasn't about leather and chains (though he said sometimes restraints might be used and the couples would end up wearing slave collars quickly). But the whole point of all of this was that he was in charge.

He asked if I had ever done anything with a man or was bisexual. Of course given my inabiity to perform sexually I had thought about this but told him what I thought was the truth, that I wasn't bisexual. But I had thought about my wife being fucked in enough settings that I knew that me serving the man would likely be part of it and that I was wiling to explore. He lol d and said that yes it would be part of it. He said that if a label had to be applied to himself he guessed bisexual applied but he didn't think of it like that. When he fucked or used husbands he basically thought of them as girls and the husbands learned to think of themselves like that too. This was the first point where I came, but I couldn't tell if it was from fear anxiety or excitement. To be honest it was all mixed up in my head. He told me I was a good girl (?) and to clean up the mess and then we would continue.

I asked him about himself. He told me that he was African American. I should stress here that the interracial aspect of the cuckold fantasy was not a key thing for me. I had thought about it both ways with and without the interracial aspect even though much of the online cuckold porn leaned strongly toward interracial. I was certainly open and interested and maybe even turned on by that aspect, but it wasn't a big thing for me before I started talking to Tim.

He told me that he was a large guy, 6'8" in his late 30's, and very muscular... spent time several days a week at the gym... former college athlete. He also was independently wealthy from a lottery ticket when he was in college so he didn't really have to work and had lots of time to play. He sent me a few pics just in case it sounded like he was describing a fantasy, including one of his cock. His cock basically looked like a porn cock. 9" and thick with a flared head.

I told him honestly I didn't think she could take it as my five inches sometimes was hard for her and that she was very tight. He said that it was a myth that all women liked large cocks but he found all could take his size and most really truly enjoyed it. He was confident and very mildly dominant all through our talk and my cock responded by getting hard again.

We went on with him describing his fetishes and interests. I guess I'm not sure what the difference is but he said that one of his was really changing his partners' interests... seeing them become turned on by things that excited him... seeing them discover new erogenous zones and triggers. That this was a deep and real ownership that excited him very much. Breathlessly I told him I understood and could see how that was exciting.

He told me that he was into the breeding fetish but quickly explained what that meant. It did not mean getting a woman pregnant (though he admitted he had done that for a couple who could not conceive) but meant that he was always in her without a condom and usually came in a married woman's pussy. He said that STDs were obviously a concern and that he did not have casual sex... that he had not had a sexual partner in several months as he looked for a new couple. He said that once he had a couple he did not have random sex but that everyone would have regular std tests so he would not use a condom. He said this was absolutely non negotiable. If he had my wife he would be cumming inside her regularly.

Of course I came here again. As I was cleaning up and recovering I asked him where he was located. He told me... and it was the same city where we lived. (Which was a big city, but still I did not think this was likely.) I felt my heart almost explode out of my chest and I think I froze up because next thing I knew I had a few messages from him asking if I was still there and everything was ok. I told him yes sorry and then that we were in the same city... He said interesting ok let's continue.

He told me that one fetish he had that might seem strange was that he loved women's armpits. I had been aware of this fetish and had thought of it in the same way as a foot fetish, but never really gave it much thought. As he explained more it started to make sense. He pointed out the visual side of it... that a woman with her arms up lifts her breast and lengthens her torso. He also said that a woman with her arms up is submitting... saying do anything you wish to me... and that it is hard for a man to understand how vulnerable she feels.

He also said that a woman's sweat especially when she is sexually excited contains pheremones and hormones and that it's not hard to train her to cum when she tastes herself... or to train a man to do the same. He also said this was an erogenous zone and that women genuinely liked to be touched there and the right kind of touch at the right time could arouse a woman or increase the strength of an orgasm.

He also said he enjoyed sharing women with a group of friends who had similar interests (and again stressed the importance of regular STD tests for everyone)... and he reminded me that the husband would serve him much as the wife would... that his interest was owning a couple and not just fucking a married woman.

There was more, but it was lost to me at the time. He told me to stop cumming... I had cum four times already and was working on another... and then he asked if I wanted to explore submission and vulnerability. He told me to edge and to be sure not to cum... I told him yes... yes Sir... and then he asked me to show him a photo that I had never shown anyone. He wanted to see Michelle completely naked, legs spread showing her pussy, her face, armpits, and tits in one photo. He asked if I had a photo like that... I said yes Sir... I do...

We were chatting in a fairly public chat room and he told me to do two things. One share that pic with him. Two tell him he could do anything he wanted with it... anything that excited him... he could share it or post it or do anything. He said I didn't have to do this but it would please him if I did.

I pulled up the pic and looked at it... knowing I had never shared it even with the man I took the pic for... I fought... I wanted to not do it... I wasn't touching my cock but it was throbbing... jumping... literally dripping precum down to my balls... I had to sit on my t shirt that I had taken off so I didn't get a mess on the sofa... Finally, impulsively, I sent the pic to him and typed "Here is my wife Michelle ____ exposed for you. You may do anything you wish with this photo, Sir. I am a submissive cuckold husband."

I sent it... waited breathlessly... and he wrote back Good boy... you may cum for me... cum for me and say please fuck my wife Sir while you do. I obeyed and came after stroking my cock two pumps... and even though it was the fifth time in two hours I came and came and came so hard I thought I would pass out... there was surprisingly much liquid in there after so many cums.

As I came down from my high, I became a little horrified at what I had done in sharing that picture. He assured me that he deleted it and had not shared it. (As far as I know that was true and I now have plenty of reason to believe him.)

It was getting late and I needed to go. He asked me if I had any interest in making this real. Said no pressure he understood if it was just online. I said yes I wanted it to be real but I was scared and didn't know how to do it. He said let's meet for a drink, just the two of us, and talk it through... no pressure and no expectations. A few days later, we would meet. A few weeks after that, I would be sending Michelle to meet him for a drink after shaving her and dressing her for their date. And I'll tell you about all of that next.

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16 Comments
1509196215091962about 1 month ago

Love where this is headed. Thanks for writing.

malejktmalejktalmost 2 years ago

I want to see pic of your wife exposing her armpits. Post it on your profile page. You can blur her face of course.

liz33ndliz33ndabout 2 years ago

this is extremely hot, wow, i love the seduction ad submission

AnonymousAnonymousabout 2 years ago

I loved all of your entries…we all have similar fetishes as cuckolds (nylon, interracial, breeding, humiliation)….we must all share some kind of gene. Anyway, very sexy story

AnonymousAnonymousabout 2 years ago

Ever taking a thing of his cock I asked him if you want me to go ahead and suck his cock too

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