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How I Became a Cuckold
16/10/2021
I wrote this down a few years back, but it's the true story of how I became a cuckold (or at least how I realized I was one). Forgive any typos.


Part 1: High School Crush

When I was about 15 or so, I’d just started seeing
someone. I was still in a puppy dog phase where I was
crushing on her. I was a virgin at the time, of course... so she and I just kissed, mostly (a little touching). I had a friend named Paul who was definitely not a virgin. He did well with the girls. Good looking guy. Charming. He and I were at a mutual friend’s party (there, separately; I came with my girlfriend).

I lost track of her at one point and ended up looking
for her, eventually finding my way upstairs. I saw Paul come out of the master bedroom. He was zipping up his pants. Had a big grin on his face. He put his hand on my shoulder, said “Hey” and headed downstairs. I quickly checked the upstairs bathroom. No sign of her... and then it happened. She came out of the master bedroom, her hair a mess. My heart sank. She saw me, gave me a big kiss and said she was ready to go when I was. Ok. So we left.

I knew, of course... that they’d messed around (or
sensed that they had), but I didn’t say anything. I was hurt... and jealous, but (and I obviously had no idea why at the time)... I was turned on, as well. Massively so. I found out, days later (through the rumor mill), that she’d sucked his cock... and that he came in her mouth (the same mouth that had just kissed me).

We never did talk about it. We dated for another 3-4
months... and, during that time, I replayed that night each time I masturbated. Knowing I’d kissed her
moments after she sucked him. The taboo of it had me
tremendously hard. I felt a bit emasculated, but god... I’d never been so turned on in my life.

Part 2: My Boss

The next event that shaped me (but also the most
intense and impactful) was in my late 20s. My
girlfriend at the time was a little younger than me
(early 20s). Cute. Super high sex drive. I’d just started working for the company I’m with today. My boss, at the time (Charles), was in his early 50s. Tall. Former athlete. A bit of a beer gut as he wasn’t the type to hit the gym. A little arrogant. Intimidating in a way. There was just an inherent dominance about him... where it felt natural to refer to him as “Sir.”

Anyway... there was an event that he wanted me to
attend. It was far enough out that he was fine with me getting a hotel room. He was planning on attending, as well (along with a few others). I was there for a few nights. My girlfriend joined me on the last night. The show wrapped and everyone from the convention gathered in the lobby bar area (inside and outside). She and I had some drinks and mingled. I introduced her to Charles (he’d commented on her photo once, which I had on my desk, so I knew he thought she was attractive). She was immediately taken with him (I knew he was her type, as well; she’d confessed once about having a thing for older men), though it seemed innocent enough at the time. Much like what happened in high school... we separated at one point. She had gone outside to chat with a friend’s wife and some of the women from work. I continued to mingle. The last time I recall seeing her, she was chatting with him, again... alone. Didn’t think much of it, though.

Maybe a little over an hour and a half later, I wanted to go up. I looked around for her, but... nowhere in sight. I figured she went up to rest and to wait for me. When I got there, I opened the door and... got the shock of my life (and still resonates with me, all these years later). They were on the couch. Well... he was. His dress slacks were down (shirt unbuttoned) and she was sucking him. He didn’t freak out. He just looked at me, grinned, and told me that I could stay or go... but to “shut the damn door.” She didn’t acknowledge me (later found out she was both highly inebriated and just... completely lost in sub space). I was honestly... speechless. The whole thing was surreal. I remember shaking as I closed the door behind me and walked over to the chair. I sat down and... just watched. Didn’t
say a word. I didn’t touch myself. Nothing. Just...
watched, my heart, pounding. He stopped her after
awhile and led her to the bed. She looked over at me,
briefly... but didn’t say anything. She was in a trance. I watched them fuck for... what seemed like forever, but was probably an hour.

I came in my pants, watching them... without even
touching myself. It was that intense (and wouldn’t be
the last time).

He left and.. she and I didn’t talk that night (she
passed out somewhere around her third orgasm,
mainly from the alcohol). We actually didn’t bring it up all week. We just... glossed over it. As if it didn’t happen. When we finally did speak (a week later), everything came out. She started to cry, apologizing profusely. I apologized, as well. She said she was afraid I was going to break up with her. I told her I was afraid she was going to break up with me for not having stopped him... for being such a little bitch (in so many words). Once she realized that it turned me on, she relaxed and said things just got carried away. She’d had too many drinks. He was kind in seeing her up to the room, but... he didn’t leave. They talked on the couch for a bit and... it just sort of happened. She admitted that
she couldn’t stop thinking about that night... and him. As for my boss, he had been traveling. I didn’t see him until a couple weeks later. He called me into his office. We talked about an email and then the trade show. He said it was a success... and then he addressed the elephant in the room. He said she was “lovely”, then a long pause... before adding, “and a great fuck.” I started shaking. He said he wanted to see her, again. I think this was the moment that I became a true cuckold. “Yes, Sir”... was my reply. I didn’t even question it. I mean... I was jealous, absolutely... but also turned on. She and I talked about it that night. She admitted that she’d like to see him again... but only if I was ok with it. We both knew it turned us on, so... I invited him over a week later and watched it happen all over again. They fucked off/on for a little over a year. He got off on making me watch and... she (we) grew more and more submissive to him. He eventually became her Master.

It was a power trip for him, making me watch.

It was around that time that I did some research and
realized cuckolding was a thing. Men who typically
leaned a bit dominant or were alpha in their daily lives (like me) who, behind closed doors, got off on their wives/girlfriends being with someone more alpha than them... where they became a bit submissive in that context. Watching her with someone bigger and better in bed. Being made to watch. Being teased.


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