Evolving as a cuckold - through the seasons of life

[The Owl]

I am loving your story. I come to this site to learn, not for wank material so your writing is exactly what I hope to find here. Thank you for making the time to recount your experiences.

Jeff

I'm delighted you are enjoying the tale.

[venus-can99]

Thanks Owl for the insight into your cuck desires and relationship with Caroline. What I am curious about is did you openly bring up your cuck desires with Caroline and the foundation of a strong marriage ?

[The Owl]

Thanks Owl for the insight into your cuck desires and relationship with Caroline. What I am curious about is did you openly bring up your cuck desires with Caroline and the foundation of a strong marriage ?

Hi Venus-Can99...

Yes and no. I don't think I even knew the word "cuckold" at the time we were still married. I knew what I felt but I didn't have words to wrap around it. Caroline knew what she felt. It was an ongoing struggle for her... the ambivalence of being in a committed relationship - meeting the expectations of others (e.g., her parents, me) - versus following her dream of being an independent woman, unconstrained by the boundaries of marriage. She didn't know how to be inside a marriage and assert her autonomy in the sexual arena. And I didn't feel safe enough within the relationship to fully encourage her to follow her erotic urges.

I hope that answers your question. During the last few years of our marriage, the internet was just getting traction. I remember reading Penthouse Letters and being fascinated by the wife-watching letters. Sometimes, Caroline would read those Penthouse Letters while I lay under the sheets watching her labia swell with arousal as she digested the words on those pages. I had a small flashlight in hand so I could see the beads of her clear fluid exuding from the pink tissue between her labia as she became increasingly aroused. Then, she would reach down and begin touching herself, making herself orgasm while I watched from a few inches away. I could smell her arousal, and I knew what fantasy material she was reading that excited her. Beyond sharing such fantasies, we never got to the point of acting them out together - as a couple.

[venus-can99]

Thanks for the answer Owl. It is interesting that sometimes finding the right label helps and the internet certainly helps with the "research"

[shadowtantra]

Hi Owl,

I so enjoy your story and sharing of your evolution in a compassionate and thoughtful way. You asked if it all makes sense - indeed it does and resonates deeply with me and my journey. This quote in particular resonated with my own awareness - "Each experience of this nature planted more seeds of the eroticism of being a cuckold in the landscape of my consciousness". Like you I did not have the words to speak to that feeling of angst and arousal that for years confused me.

Thank you and look forward to hearing more of your story in 2025. Wishing you all the best for 2025!

[The Owl]

Fast forward two years from the summer fling with her hiking buddy.

Caroline's ambivalence about being in a relationship had caused her to pull away more and more. I felt strong enough to tell her I wasn't going to live like this any longer. I moved into a room in another house full of university students - three women and two men. I knew some of them but not all of them. About three months later, Caroline asked me to come back. I did. The room I had been occupying was rented to a male graduate student named Blake who was doing research on ethology. He was a strong, rugged, and handsome chap. None of us had ever met him before but he seemed like somebody who would fit in nicely with the other people living in the house.

A week after I had moved back in with Caroline, the house I had been living in was having a big potluck dinner party. Caroline and I attended. As the party progressed, I was in the kitchen talking with a couple of friends. Caroline was fin the living room where people were scattered around on chairs and the floor. Caroline was seated cross-legged on the floor next to Blake. Just like everybody else at the party, they were enjoying a lively conversation.

Caroline came into the kitchen looking perky with a slight blush in her cheeks. She smiled and asked how I was doing?

"Fine... you?"

"I'm enjoying chatting with Blake. But I didn't know where you were and wanted to make sure you're doing ok. I didn't want you to feel left out while Blake and I were getting to know each other."

"I'm fine. We're just catching up with each other here in the kitchen. It's fine with me that you are having a good time. Enjoy."

Caroline had a mischievous smile on her lips and a twinkle in her eye as she said, "Ok..." and turned to return to the living room.

Later that evening, Caroline and I left the party and headed back to our house.

Caroline told me that Blake had shown her my old room upstairs where he was now living. I didn't think much of it.

Several years later Caroline disclosed to me that Blake had done more than show her his room. He had been touchy with her in the living room but was only slightly flirtatious. Caroline had responded warmly to his touch. When he invited her to see my old room, she welcomed the invitation. In the room, Blake took a risk and hugged Caroline. She hugged him back.

Blake whispered in her ear, "I've enjoyed chatting with you. I'd like to get to know you better."

"That would be nice."

Caroline sealed the deal by giving Blake a quick kiss on his cheek. They both knew where they were headed but this was not the time to take it further.

I was completely oblivious that I was about to be cuckolded almost immediately after getting back together with Caroline.

About a month later, a woman (Ruth) who lived in the house where I had been living saw me on campus. She knew that I had moved out to get back together with Caroline. Ruth was engaged to a man who was living in the Midwest. He came to visit her from time to time. Ruth kept tight boundaries around her long-distance relationship, and was never flirtatious with other men, although she was attractive.

Ruth confided, "Caroline dropped by the house to visit Blake recently. I just wanted to make sure you are aware."

I replied, "Oh... yeah... Caroline told me they enjoyed chatting with each other at the party."

Ruth replied, "I just want to make sure you are ok."

"No worries, Ruth. Caroline has lots of friends. She visits friends from time to time."

Ruth seemed slightly skeptical - as if she knew more than she was disclosing - but also didn't want to be inserting herself in my business. Ruth was fairly certain I was being cuckolded and was trying to give me a heads up. But I remained oblivious.

She said, "Ok... good to see you. Say hi to Caroline for me."

"Will do. Nice to see you too."

***********************************************

There's more to this story... more that I learned years later from Caroline. Would you like to hear... the rest of the story?

[venus-can99]

Certainly woud like to hear more about Caroline's visit with Blake. From Ruth's tone seems like she knew you were cuckolded...

[The Owl]

Certainly woud like to hear more about Caroline's visit with Blake. From Ruth's tone seems like she knew you were cuckolded...

I'm sure she did.

I learned much later that Ruth and Caroline saw each other near the staircase in the house. Ruth's bedroom door opened close to the bottom of the staircase. Blake's door was immediately to the left of the top of the staircase. Ruth came out of her room late one evening and saw Caroline emerging from Blake's room. Caroline probably looked like the cat that had eaten the canary. She knew that I knew Ruth and she knew that she had not yet told me what she was up to with Blake.

Apparently, this brief encounter was what led Ruth to hint to me that Caroline had been "visiting" Blake at their house. Ruth was an open-minded young woman - not judgmental. So, she didn't feel compelled to tattle on Caroline. But she also didn't want to be hiding the truth from me when she saw me on campus. I'm sure it was a somewhat awkward issue for Ruth. In retrospect, I admire the way she handled it.

More to come regarding Caroline and Blake taking the tumble together. In short, it was not a one-night tryst. I was enjoying silky seconds several times during the rest of that school year, even though I remained naive about their affair, or why her pussy was so wet from time to time.

[venus-can99]

Interesting that Caroline decided to play the cheating wife with Blake and let you know later about the “affair “. If she had been open with you how do you think you’d have reacted? Jealousy? Anger? Excitement? Would you have been ok with it ?

[The Owl]

The Blake saga continued... Note that I learned about the following events during Caroline's late night confession... about a decade later. Interesting that it took her that long to disclose the following. She kept it as her secret for years.

*************************

During the week following the party where Caroline and Blake met, I needed to leave town on Friday morning, and would be returning on Saturday evening.

Seeing an opportunity to get to know Blake better, Caroline dropped a note off for Blake at his house on Friday inviting him to drop by for lunch on Saturday. Blake showed up at our house as Caroline had hoped.

Caroline had made some soup and bread which they both savored. They enjoyed chatting and got to know each other better. Blake saw that there was some wood outside the back door that needed to be chopped and stacked. He jumped right in and helped with that chore. Caroline was impressed.

Blake was experienced and confident with women. He knew that a seduction needed to proceed slowly... at Caroline's pace rather than his. When Blake finished chopping the wood, he came back inside and told Caroline "Thank you for lunch... I hope to see you again soon... come by and visit me at the house sometime if you'd like."

He then reached out and gave Caroline a firm hug, using one hand hand to pull her neck and head into the nape of his neck, his other arm held her torso tightly to his. She could feel Blake breathing deeply as they hugged. Caroline's nostrils were filled with his scent - fresh sweat on his neck from chopping wood. He smelled and felt good. Caroline felt aroused, and a bit confused by his announcement that he was leaving so soon. She wanted him to linger. Mostly, she wanted him - all of him. And he was off, down the street headed home.

I knew nothing about the lunch. When I got home, I assumed Caroline had chopped and stacked the wooed. She was athletic and enjoyed swinging the axe from time to time.

The following Thursday evening, Caroline came home very late. The house was dark and I was fast asleep. I didn't wake up when she crawled into bed. The next morning, we made love before getting up. There was nothing unusual about our interaction in bed. As we were rolling out of the bed to start the day, I asked Caroline where she had been the night before. She reminded me that she was working on a research paper and that she had stayed at the library quite late to read some journal articles. It all sounded credible to me and I didn't ask any more questions.

About a decade later, I learned that Caroline had taken matters of seduction into her own hands. She dropped by Blake's house to say hi on Thursday evening. He was delighted to see her and invited her up to his room where they could talk privately... the same room where I had been living while Caroline and I were separated for a while.

Blake had a mattress on the floor and only one chair in his room. They both got comfortable on the mattress. Blake and Caroline felt the sexual energy in the room. They both leaned in to kiss. Lips opened... tongues met. Blake slid his tongue between Caroline's lips. She was his for the taking. Breasts were caressed. Shirts came off. Caroline reached down and began releasing Blake's belt buckle. Soon they were both naked. Bodies were hot with anticipation. Blake's body was buff and his sizeable cock was fully erect. Blake had just the right edge of dominance in his style. Caroline felt the sheets on her back. She spread her legs as Blake moved his torso over her. Caroline reached down and used her hand to guide Blake into her wetness. His cock was bigger than mine but not so large that it caused Caroline pain. Caroline groaned with pleasure as Blake pressed himself deeper and deeper inside her. Blake rode Caroline to and through an intense orgasm before his body tensed as he squirted inside her. They rested and talked for a while and then made love again, this time more slowly and tenderly.

Eventually, Caroline realized that it was getting late. She donned her clothes, kissed Blake goodbye, and climbed on her bicycle. While riding home in the darkness, she felt post-orgasmic bliss. Given that Caroline and I had talked fairly openly about our respective fantasies, Caroline knew that I had some cuckold tendencies, even though we didn't have a name for it. She contemplated telling me exactly what she had been up to once she got home. She imagined telling me that she had been freshly fucked. She imagined letting me slip my cock into her very wet pussy. However, I was already fast asleep when she rolled into the yard and entered the house. So, she quietly crawled in next to me, trying not to wake me up. I may have stirred momentarily. If I did, I fell back to sleep in seconds.

In the morning, Caroline was less confident about telling me about her tryst the night before. She knew that what she had done was something that fit within our shared fantasies. But she also thought I might react badly when I was told that she had acted upon this fantasy with Blake - without any forewarning or mutual agreement. Additionally, Caroline's motivation when she went to Blake was not driven by a desire to cuckold me. Rather, she wanted to carve out her own space - her independent space - beyond our relationship. She wasn't trying to increase our intimacy by cuckolding me. She was exploring the independent side of her relationship ambivalence.

And, at a personal level, she had found sex with Blake to be more enjoyable than she had ever imagined. Caroline didn't want to risk the possibility of not being free to climb into Blake's bed again. If she told me and I reacted poorly, she was worried that she may run into problems when she wanted to visit the candy store again.

So, Caroline kept the tryst with Blake to herself. During the rest of that semester, Caroline paid Blake's bed several late evening visits. Each time she came home later, I assumed she had been studying at the library. It was during this time that Ruth approached me and asked about Caroline and Blake's friendship. I naively assumed that nothing sexual was going on between them. I shut Ruth down before she could tell me what she knew.

Blake needed to go back East at the end of that semester. He had no plans to return to the Rocky Mountain region. Caroline told me about a decade later about her torrid affair with Blake. She told me that Blake had tried to talk her into going with him when he departed. Blake had fallen hard for Caroline. He wanted more of her sweetness. Caroline had fallen for him as well. But she decided she wanted to stay with me and to complete her studies in the Rockies. I am guessing she gave his invitation serious consideration before she declined. He was her type - strong, intelligent, and quiet. But she wasn't willing to throw caution to the wind.

I do not think they stayed in touch after Blake left. But who knows? There's always more to the story.

[The Owl]

Feedback, reactions welcomed.

Assuming interest... I'll tell you what happened during the summer after Blake, before moving to the Twin Cities.

[venus-can99]

Thanks for the update owl. What caused Caroline to confess her affair with Blake? I suppose she also knew what she wanted

[The Owl]

What caused Caroline to confess her affair with Blake?

If I recall correctly, we were having one of those moments when Carikube decided to take a trip through the relationship confessional booth. She was in the mood to speak the truth about her trysts with Blake many years before. To the best of my knowledge that was the only secret cuckolding that occurred during our relationship about which I did not know soon after the trysting and moaning began. Basically, she just wanted to clean the air between us. She wasn't trying to humiliate me by disclosing her affair. At this point in life, I'm not sure whether this type of disclosure has any upside... but it was her decision to disclose, and I listened.

But long before the confession, and shortly after the "tryst and moan" with Blake semester... the west got wild for two or three months. Caroline traveled west to he with her older sister who lived in California.

More on that when I'm rested and my mind is clear!!! Any other feedback or questions. A writer such as The Owl enjoys interaction with his readers!!!












!!!!!!!!!

[dnic]

Hi Owl,

Thanks for the continuation with Caroline.

For context how long were you and Caroline together?
Assuming the confession about Blake was nearer the end of your time together?

Ruth's talk to you didn't generate any questioning of Caroline on your part? Even if you didn't suspect her didn't it generate fantasy talk in bed?

D

[The Owl]

The story after Blake, before wedding is yet to come.

I've told most of the married stories... but not all.

The post marriage stories are the point where i got full immersion in being a Bull for a short while, and then a cuckold... even though I had no names for the roles.

[The Owl]

Hi Owl,

Thanks for the continuation with Caroline.

For context how long were you and Caroline together?
Assuming the confession about Blake was nearer the end of your time together?

Ruth's talk to you didn't generate any questioning of Caroline on your part? Even if you didn't suspect her didn't it generate fantasy talk in bed?

D

The first time we met was two years before we transitioned to being romantic. We were friends for two years - without benefits, so to speak. We moved into rooms in the same group student house in a University town and she entered my room one night and fireworks ensued.

From the fireworks to the wedding took five years. She was very ambivalent about getting married to ANYBODY. She viewed herself as a free agent, not a franchise player. Blake was about a year before marriage. Disclosure about Blake was probably 14 or 15 years after marriage. Our mutual agreement to seek a divorce was about another 3 or 4 years later.

I don't see the blake confession as a significant conributor to the divorce. The bigger issue was Caroline's eternal ambivalence about b eing married. She eventually claimed to want to be married but a zebra usually doesn't change its stripes. The dye had been set between the two of us. It was very difficult for either of us to change our behavioral patterns.

The hilarious outcome was that Caroline dated a couple of guys after the divorce and finally landed on one she wanted to marry. She thought he wanted to marry her. She moved communities and began living with him, only to discover he had as much ambivalnece about being married as Caroline had when she was younger. In short, she got a taste of her own medicine!!! She came to me and disclosed her frustration with his ambivalence. I almost started laughing and talking about karma biting her on the ass, but I didn't. Eventually, she talked him into marrying her. From a distance, it looks like he got over his ambivalence. I think they are a much better match than Caroline and I were. But only the two people behind the closed bedroom door know what is going on in that room (metaphorically and literally speaking) . And somettimes the two people involved in a relationship have no clue what is going on between the two of them. Relationship is a labyrinth.

Regarding Ruth's talk on campus, I was in complete denial - whistling through the graveyard as it were - denying that there was anything for me to pay attention to in what she was saying. She hinted, gave me a tell at the poker table. I explained it away as fast as she tipped her hand and gave me the tell. She pulled back quickly once I said "It's nothing." Perhaps she thought i already knew and she didn't want to get further into my business. Who knows? But no further questions or discussion ensued with Ruth.

[venus-can99]

Did you have any interaction with Ruth after Caroline's confessions or had you both (you and Ruth) moved on?

[The Owl]

Did you have any interaction with Ruth after Caroline's confessions or had you both (you and Ruth) moved on?

I won't go back and look right now, but I think I mentioned a while back that I found Ruth on social media and communicated with her briefly in recent years. I asked her if she recalled anything about our brief conversation on campus or any other details from that time pertaining to the relationships between and among me, Caroline, and/or Blake. When I asked the question, Ruth knew I was divorced and that my question was premised on curiousity, with no relationship implications.

Ruth convincingly told me she had absolutely no memory for any of that history, and hadn't thought about those people for a very long time. The ancient saga was significant to me, not to Ruth. As is the case with many trivial experiences during day to day life, she recalled none of what I was talking about. Ruth told me that she married the guy with whom she had been in a long distance relationship at that time. Ruth and he were divorced many years later. Her ex-husband was a very nice guy but he became a severe and chronic alcoholic. She told me he died a few years after they divorced from liver failure. Sad.

Short answer is: Yes, Ruth and I interacted a couple of times online to catch up with each other. But Ruth did not recall anything about the details of this history. I poked around in the ashes. She didn't remember that there had once been a fire where the ashes are now strewn.

[The Owl]

Although not yet asked, some of you may wonder whether The Owl (me, myself, and I) was ever enjoying sex with other women during the years I was with Caroline.

The answer is "occasionally" although I believe I declined more offers from women than I accepted. I don't want to sound like Mr. Handsome or try to make you think I'm God's gift to women. I'm reasonably handsome but not a Fabio or the like.

Interestingly, Caroline seemed to be relieved whenever I told her about me having sex with another woman . I think it gave her relief from feeling completely trapped in the confines of a marriage. It also gave her the quid pro quo to jump the fence and to try a bit of the green grass in yonder pasture.

Irrespective of the reason, Caroline was never distressed when I told her I had roamed. And, for whatever reason, every time I roamed, I quickly disclosed to Caroline. There weren't a lot of women beyond Caroline, but a few.

I'm happy to share a bit about those encounters if there is interest. I could describe the missed opportunities as well. The incomplete experience is most firmly recalled... and can sometimes be the most erotic!!!

What I know with certainty from a life full of experiences is that men and women are not hardwired for monogamy. Monogamy can be a choice, but it is not a biological imperative for survival of the species. With regard to biological imperative, there is a LOT of evidence to suggest that women are hardwired to be promiscuous Hotwives (Hot girlfriends) rather than sexually repressed monogamists!!!

Which reminds me... why did the 35 yo married woman with the plain dress and head scarf get excommunicated from her church?

Answer: Two-Men-A-Night (you might have to say the answer aloud to catch the joke...).

[venus-can99]

I thought the answer was going to be Men-A-Nite

[venus-can99]

Defintely curious about your "bull" experiences Owl. Were any of the women you bedded/offered were wives (hotwives?) ?

[The Owl]

Defintely curious about your "bull" experiences Owl. Were any of the women you bedded/offered were wives (hotwives?) ?

Yes.

[dnic]

Which reminds me... why did the 35 yo married woman with the plain dress and head scarf get excommunicated from her church?

Answer: Two-Men-A-Night (you might have to say the answer aloud to catch the joke...).

I happen to know a Men a Nite lady very well!

[The Owl]

Humans are humans... and overall, we're pretty dumb... but we're still animals!!!

[The Owl]

Caroline cuckolded me fairly intensely the summer after Blake, with a young "farmer" named Tab in Northern California while worked but ass off getting things wrapped up so we could leave the Rockies and head to the Twin Cities - the next step n the adventure of life.

Wanna hear the tale?