Evolving as a cuckold - through the seasons of life

For cuckoldresses and the men who serve them.
subtoall
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Re: Evolving as a cuckold - through the seasons of life

Unread post by subtoall » Sat Mar 29, 2025 11:47 am

The Owl wrote:
Sat Mar 29, 2025 11:21 am
(Anybody interested in hearing how the night unfolded from there? If so, to be continued...")
Hell yeah!

venus-can99
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Re: Evolving as a cuckold - through the seasons of life

Unread post by venus-can99 » Sat Mar 29, 2025 3:01 pm

Wow that sounds like a wonderful house warming! Would love to hear if you have Tiffany's b&w nudes in your new house !

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Sat Mar 29, 2025 9:19 pm

She warmed the house... nude... but there was no photo hung. More later.

shadowtantra
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Re: Evolving as a cuckold - through the seasons of life

Unread post by shadowtantra » Mon Mar 31, 2025 12:02 pm

Great to have you back owl! Love the story.....

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Sun Apr 13, 2025 7:07 am

"You can touch me" Tiffany whispered.

I hadn't been on the dating scene for 20+ years and had no idea what I could or should do with her. But she was giving me the green light and I wanted to enter the intersection, so to speak.

As we stood and kissed, tongue caressing tongue, I began running my hands up and down her back... down to the top of her tight ass and up to her neck. There was exposed skin above her pants and below her top. Her skin felt hot... almost electric.

My new home had been recently remodeled and its best feature was a soaker tub.

To get things moving, I whispered to Tiffany, "Let's take a bath together."

She smiled and said, "Ok.""

I drew a tub, lit some candles to create the ambience and got us both a glass of wine to savor in the tub.

We both doffed our clothes. I stepped in first and lowered myself in the steam. She had her back to me as she lowered her torso into the water. Then she leaned back against my chest. My erection was between my belly and her back. She could fee I was aroused.

We talked about this and that, giggling now and then.

She turned and rose, as if she was going to mount me. But first, she spent a few moments fondling and inspecting my cock. She looked up. Our eyes locked and she said, "Nice cock."

"Thank you. I love your body."

"My tits are too small."

"They're perfect for my taste."

She rose and positioned my cock near her pussy and then things got weird.

In an almost angry tone she said, "You just want me for my pussy, don't you?"

I rose up a bit in the water so I could look her in the eye and said, "If there is anything about what we are doing that makes you feel even slightly uncomfortable, let's stop."

She softened and said, "Fuck it..." as she lowered herself on my cock. The intersection and been entered. A gentle collision between cock and pussy had begun.

She rode me for a few minutes and seemed to be enjoying herself. Then Tiffany said, "Let's move to your bed. We can have more fun there."

Drying off with her was erotic. Once in bed, she was on her back and I was inside her again, gently pushing in, parrying, and gently thrusting again.

After a few minutes of gentle sex, Tiffany suprised me by saying, "Fuck me hard... don't hurt me... but fuck me like you mean it."

And I did. She was my introduction into the world of dating and sex post divorce. There is more to her story, which I will tell another time. Bottomline, I was serving as her Bull while she cuckolded her boyfriend. I had no idea at the moment of the tryst.

Suffice it to say, I was entering "The Owl's Wild Years."

Thoughts? Want to hear more?

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Sun Apr 13, 2025 7:26 am

The Owl wrote:
Sun Apr 13, 2025 7:07 am
"You can touch me" Tiffany whispered.

I hadn't been on the dating scene for 20+ years and had no idea what I could or should do with her. But she was giving me the green light and I wanted to enter the intersection, so to speak.

As we stood and kissed, tongue caressing tongue, I began running my hands up and down her back... down to the top of her tight ass and up to her neck. Skin was exposed above her pants and below her top. Her skin felt hot... almost electric.

My new home had been recently remodeled and its best feature was a soaker tub.

To get things moving, I whispered to Tiffany, "Let's take a bath together."

She smiled and said, "Ok.""

I drew a tub, lit some candles to create the ambience and poured each of us a glass of wine to savor in the tub.

We both doffed our clothes. I stepped in first and lowered myself in the steam. She had her back to me as she lowered her torso into the water. Then she leaned back against my chest. My erection was between my belly and her back. She could feel that I was aroused. My cock had risen but my state of arousal did not surface explicitly during our follow-along conversation in the tub.

We talked about this and that, giggling now and then as we got to know one another.

After a while, she turned and rose, as if she was going to mount me. But first, she spent a few moments fondling and inspecting my cock. She looked up. Our eyes locked and she said, "Nice cock."

"Thank you. I love your body."

"My tits are too small."

"They're perfect for my taste. I like your firm breasts and your nipples. They're all my mouth and eyes need for pleasure."

She rose and positioned my cock near her pussy and then things got weird.

In an almost angry tone she said, "You just want me for my pussy, don't you?"

I rose up a bit in the water so I could look her in the eye and said, "If there is anything that we are doing that makes you feel even slightly uncomfortable, let's stop now."

She softened and said, "Fuck it..." as she lowered herself on my cock. The intersection had been entered - after a brief pause caused by the light flashing red, ever so briefly. The gentle collision between cock and pussy had begun. I was in pussy heaven.

She rode me for a few minutes and seemed to be enjoying herself. Then Tiffany said, "Let's move to your bed. We'll be more comfortable there."

I used a towel to help dry her off. Rubbing the towel over every inch of her body was intensely erotic. We both smelled fresh. The only scent in the air was a blend of pheromones. My nostrils flared from natures perfume. Once in bed, she was on her back and I was inside her again missionary style - gently pushing in, parrying, then thrusting again. The movements were those I knew from being in bed with my ex thousands of times in the past.

After a few minutes of gentle sex, Tiffany surprised with a sincere request: "Fuck me hard... don't hurt me... but fuck me like you mean it."

And I did. She was my introduction into the world of sex post divorce. There is more to her story, which I will tell another time. Bottomline, I later learned that I was her Bull. She was cuckolding her boyfriend. I had no idea about this context until a week or two later.

Suffice it to say, I was entering "The Owl's Wild Years."

We fucked in the middle of the night, and again in the morning.... like two famished travelers who had found their way to a fully stocked buffet table. Practicing our night moves... together as one.

Thoughts? Want to hear more?

hornedhubby
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Re: Evolving as a cuckold - through the seasons of life

Unread post by hornedhubby » Sun Apr 13, 2025 4:19 pm

Great update, Wise Old Owl. :up: :up:

Really enjoying your thread.

Best wishes and thanks for sharing.

venus-can99
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Re: Evolving as a cuckold - through the seasons of life

Unread post by venus-can99 » Sun Apr 13, 2025 7:53 pm

Your turn as the “bull” for Tiffany while she chucked her bf sounds like a rather interesting turn of events… would be great to hear more about “the Owl’s wild years”

shadowtantra
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Re: Evolving as a cuckold - through the seasons of life

Unread post by shadowtantra » Tue Apr 15, 2025 12:40 pm

I think we would like to hear more about Owl's wild years after your teaser!

sixpack

Re: Evolving as a cuckold - through the seasons of life

Unread post by sixpack » Wed Apr 16, 2025 12:41 am

Terrific re-telling of your experiences. Tell us more

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Fri Apr 25, 2025 8:22 pm

Tiffany continued...

In the morning, after our early morning tryst, Tiffany fell back into a slumber. I rolled out of bed and brewed some coffee. Tiffany was fast asleep in my bed. It felt a bit strange to have a woman fast asleep in my bed - a woman whom I had just met about 12 hours earlier. She looked peaceful as she breathed deeply through the land of nod.

It had been a very enjoyable and erotic night, but I knew I wasn't ready to lock down in a relationship with her. She felt like a bridge leading toward the land of the erotic, not an island on which to set up camp. The flash of anger she showed when she had blurted out, "You only want me for my pussy" was a tell-tale sign that a relationship with Tiffany would not only be wild, it would be rocky.

As I got my bearings over that first cup of motivation, I realized I didn't have an exit strategy.

I was using a pager in those days. So, I went to the landline in the kitchen and called my pager in the bedroom. The ring of the pager woke Tiffany up. I went into the bedroom and retrieved the pager. I called a random number on the land line and acted like I was talking to somebody. I was listening to nothing but acted as if somebody was talking to me. After a few moments, I replied to the phone saying, "I'll be there as soon as possible. Thanks for letting me know."

Tiffany didn't suspect the page was bogus. She got up giving me one more glimpse of her perfect body before she slipped into her clothes, moving as smoothly as a cat.

I drove Tiffany to her apartment building. We hugged and kissed goodbye. I had given her my number the night before and she had given me hers.

Several days later, Tiffany made the first move. She called to tell me she had a confession to make. I encouraged her to... well, confess.

She told me, "I hope you're not disappointed or upset but I need to tell you I have a boyfriend. I thought you should know."

Silence hung on the line.

I asked, "Does he know about me?"

"Yes... I told him everything."

I was startled... and worried.

"Are you ok? Is he angry? Should I be worried?"

"No, no... nothing like that... don't worry. I didn't tell him your name, just what happened between us."

She paused, "I can tell you more if it would help."

"Please do."

"He and I have been dating for about two years. We began living together about six months ago. Our relationship has been a little different than most."

"What do you mean?"

"Well... he seems to like it when I flirt with other men. Early in our relationship, we were at a cowboy bar together. He doesn't like to dance but I do.. Anyway, a handsome guy walked up to us at the bar and boldly asked me to dance. I was a little surprised when my boyfriend nodded his approval. The guy was a great dancer. My boyfriend told me he liked watching us dance - especially during a slow song. It's kind of embarrassing to talk about."

"Don't be embarrassed. So, why did you tell him about me, about our night together?"

"When you and I were together that night, I kept thinking about how I was going to tell him that I had finally done what we had been fantasizing about. Sometimes, when we are in bed I tell him my fantasies about having sex with other men. He likes it when I whisper those stories in his ear while we are making love. When you drove me home, he was still sleeping at our apartment. I crawled in bed with him. He woke up and asked me where I had been. I told him the truth. Again, don't worry... I didn't tell him who you are. He wasn't angry. Just the opposite. He was very excited."

Pause... "I feel like I'm talking too much."

"No... I'm listening. I understand what you are saying."

"Anyway, I don't think he would be happy if you and I got together again. That's not part of his fantasy. I think he might feel threatened. And, I worry that if we continued seeing each other, I may begin having feelings for you. Forget all the other stuff. I just wanted to call you and let you know that I really enjoyed our evening together. It was great."

"I enjoyed it too, Tiffany. Thank you for letting me know about your situation. You have my number if you ever want to talk again."

She never called nor did I reach out to her.

About a year later, I was walking through a Mexican restaurant in town looking for a friend whom I was suppose to meet for dinner. Bam... there she was, looking hot as ever eating dinner with a guy - presumably her boyfriend. As I was walking toward her table while looking for my friend, she noticed me immediately after I noticed her. Our eyes met. Memories flooded back for each of us.

I was surprised and felt awkward. All I could muster was, "Hi. How are you?"

She replied, "Hi." and then diverted her eyes to look at her boyfriend. She quickly glanced back at me.

The wheels were turning in all three of our minds. I quickly said, "Take care..." and kept moving in search of my friend.

I privately wondered if she told him who I was... that I was the guy from that night that she had told him about?

My gut told me that he knew intuitively by the way Tiffany and I had gazed at each other. A cuckold know when his partner is posturing with her Bull.

I never saw her again. But what a great bridge she was, into the land of the erotic as a newly divorced man.

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Fri Apr 25, 2025 8:27 pm

Feel free to ask questions. Happy to answer. And, the story continues. I'll tell more when the erotic muse strikes.

guitarman
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Re: Evolving as a cuckold - through the seasons of life

Unread post by guitarman » Sat Apr 26, 2025 6:35 am

Owl,

Once again a wonderfully told story through which I find myself reflecting on my own times between marriages. I remained single for nearly 7 years following my divorce during which time my current wife refers to as "my extensive interview process", that is, before I met her! Keep the stories coming.

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Sat Apr 26, 2025 6:21 pm

When all of this was happening, Yahoo Personals were the thing. Anything and everything had a green light. No filters. And, there were no photos being posted... yet. So, the only bait you could use to attract a woman was words. I saved what I posted at that time ~25 years ago (how time flies when you're having fun...). Here it is:

"Hi... I am a 40ish year old guy who enjoys outdoor activities (biking, running, hiking, etc.). I was married for 19 years and divorced about a year ago. I have high school-age children who stay with me part-time. I am in good physical condition with a healthy libido, a good sense of humor, and a twinkle in my eye. I am not seeking commitment or a soulmate... I am simply looking for a woman who would enjoy spending an occasional evening together for some good conversation and mutual pleasure in the context of a friendship premised on a foundation of mutual respect. I am vasectomy safe and D/D free. I enjoy an occasional glass of wine, sitting by the fire chatting, and savoring the company of a woman. I am not looking for somebody who wants to get involved with my high school age kids (they already have a mother and don't need the confusion of another mother-figure in their lives) or a full-time partner in life. But I'm also not looking for a one night fling.

If you are a busy independent woman, looking for a busy professional man with whom you can occasionally enjoy the pleasure of a safe harbor for an evening/night, I may be the right man for you. I enjoy pleasing my partner and am a gentle spirit with lots of enthusiasm. Write if you're intrigued. Tell me about yourself. Maybe we can move toward spending some time hunkered down around the fireplace sharing our thoughts and joys of the day. I want to keep it lighthearted... but not superficial. I look forward to hearing from you. If you take the time to write more than a one-liner and tell me something of substance about yourself, I promise I'll reply."

I couldn't believe how many responses I got. It amazed me at the time how many women were looking for exactly what I described. And the first to come to my door was married, and looking for a Bull. She was beautiful, hot, and creative (from a relationship perspective).

Let's call her Ginger... she had red hair above and below, piercing blue eyes, perfect breasts, and a couple of tattoos strategically placed.

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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Sun Apr 27, 2025 3:54 pm

Is there interest in hearing about Ginger... the hot redhead?

hornedhubby
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Re: Evolving as a cuckold - through the seasons of life

Unread post by hornedhubby » Sun Apr 27, 2025 5:09 pm

Absolutely.

Smart marketing plan on your part. Nice branding.

Still little sign of why you went cucky but I'll be patient.

Fly on, Owl.

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Re: Evolving as a cuckold - through the seasons of life

Unread post by Rogueuser1 » Sun Apr 27, 2025 5:44 pm

Definitely - would love to hear about her.... love that the curtains matched the drapes :) and of course what to hear about where the ink was placed.
My Tumblr: hopetobecucked.tumblr.com/
My BDSMLR: https://bdsmlr.com/blog/hopetobecucked

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Mon Apr 28, 2025 7:56 am

hornedhubby wrote:
Sun Apr 27, 2025 5:09 pm
Absolutely.

Smart marketing plan on your part. Nice branding.

Still little sign of why you went cucky but I'll be patient.

Fly on, Owl.
Who said anything about getting branded? :whip:

She had tattoos.

Seriously, you raise a good point about going "cucky."

If you've read the full thread, you know that there was some "cucky" eroticism in the warp and weft of my character from an early age.

People seem to want to categorize everything including themselves (e.g., "I'm ********." fill in the blank with whatever). My belief is that most human characteristics are on a continuum and are mutlifactorial - not just linear, and certainly not just binary. Some people heavily identify with a role (e.g., gay or lesbian), but that's not all that they are. And, even those people are typically on a continuum, even if their modal placement on the continuum is fairly close to the endpoint.

For me, life is more like a diamond with many facets, all of which are true - so to speak. As you spin the diamond, it sparkles in different ways at different times. When I was going through my post-divorce wild years, I was open to everything - including being a woman's Bull. But I eventually discovered the eroticism of being a cuckold. We'll get there.

And, I'm not just a cuckold. I'm a human with many facets to my eroticism, as are all of us. But I know with certainty that being with a woman who invites the Third to pleasure her is a source of pleasure for me. When I'm looking through the cuck facet of the diamond, the refraction is dazzling.

I'll get there... eventually. In the mean time, being on the Bull side of things (even though I had no name for that role then) was interesting and erotic as well.

More to cum.

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Mon Apr 28, 2025 8:14 am

Rogueuser1 wrote:
Sun Apr 27, 2025 5:44 pm
Definitely - would love to hear about her.... love that the curtains matched the drapes :) and of course what to hear about where the ink was placed.
The ink...

This was about 25 years ago when tattoos were much less common than today.

She had ink wrapping around the top of her left arm. A small tasteful tattoo of a butterfly was placed just above her pubis and slightly offset.
The butterfly appeared to be flying off the red bush toward places unknown.

Ginger also had an artistic tattoo in the center of her lower back. When I entered her from behind. while grabbing a handful of her mane to hang onto during the ride, I enjoyed focusing on that tattoo. I could also see my cock, just below her firm ass, as it emerged from her pussy, slick with her fluids, as we both prepared for the next thrust. She moved her ass (and tattoo) firmly backward as I pushed forward. It wasn't clear if I was the fucker or the fuckee as she gracefully pushed back onto my cock , seeking her pleasure. Her moans told me all I needed to know about why she was there... what was in it for her. She wanted raw animal sex away from the confines of her marriage.

But I have gotten ahead of myself. I missed the introduction.

vicg
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Re: Evolving as a cuckold - through the seasons of life

Unread post by vicg » Mon Apr 28, 2025 9:38 am

I can't wait for that introduction!

venus-can99
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Re: Evolving as a cuckold - through the seasons of life

Unread post by venus-can99 » Fri May 02, 2025 10:29 pm

Ginger sounds spicy ;) looking forward to hearing the fun times with Ginger

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Mon May 12, 2025 10:18 pm

Hotter than Ginger.

She was 27 yo, married, three children from two dads (never met the kids or husband). Natural red head. Beautiful light complexion that matched her red hair perfectly. Slender with curves in all the right places. Strong and supple, but soft and welcoming where it counts. Perky breasts with ruddy nipples that stood proud, begging to be licked, nibbled, and sucked. Everything about her was perfect. She had a submissive quality about her but had no difficulty letting me know what she wanted - sex.

When she showed up at my door for our planned breakfast date, I didn't know what to expect. There were no pictures with Yahoo personals at that time. She could have been anybody. I was almost breathless when I opened the door to her radiant youthful beauty and her sweet smile. We had corresponded a few times via email. She told me she wanted to meet me as soon as possible to find out whether the match would work for her. It certainly did for me.

At the door, we shook hands. After stepping across the threshold, we gave each other a telling hug - a signal that I met her minimum criteria.

I fixed her breakfast and we chatted. We both knew that this was not a sex date. It was a "no-expectations" time to get to know each other a bit better. Ginger's tale about herself and what I learned about her during the next several weeks turned out to be… well, different. In the mean time, sparks flew - in the flesh.

Over breakfast, Ginger told me that she and her husband had an "open relationship." She said that each of them were looking for sexual partners outside the marriage to enliven their relationship. Ginger said she was comfortable with her husband having sex with another woman. In hindsight, I think she would have been happy to have her husband spend all of his time with another woman. She had fallen out of love with him. Ginger also said that her husband was comfortable with her having sex with another man. It all sounded good on the face of it.

Much later, I learned that Ginger's husband's actual fantasy was for her to have sex with another woman. He was hoping for a MFF threesome, but was willing to live with Ginger having a private female lover on the side – so he could partially enjoy his fantasy – imagining her savoring sapphic love, returning home with the hint of pussy on her lips and tongue.

Her husband was looking for a female lover for himself on Yahoo personals. Ginger told me that he had found two women with whom he had ongoing email exchanges. One woman had a physical disability but was very engaging online. I don't think they ever met in person but they spent a lot of time corresponding. Over time, I learned that the other woman with whom Ginger’s husband was corresponding was GINGER!!! She had set up a bogus female account and responded to her husband's Yahoo Personals ad surreptitiously. Yes, Ginger could be sneaky.

Ginger learned a lot about her husband's fantasies and about his thoughts regarding their marriage by corresponding with him as if she was a young hottie who may want to get in the sack with him. She decided to pretend to be bisexual and fed into his fantasy of a MFF threesome with his wife. Eventually, Ginger felt guilty about duping him in this way and decided to ghost him. Ghosting was not a verb in those days but that's what she did... disappeared into the ether, never to be found again. All the while, I was her lover, hiding behind her ruse that she was spending the day with her female lover - a facade which aroused her husband.

Ginger and I enjoyed that first breakfast in my home. Then she departed. We kissed briefly as she left my house. Her maple sweet lips and the light – but sizzling - touch of our tongues during the kiss told me that we would be making hotcakes together soon - and that I would be sharing another link sausage with her, hot from the zipper.

For our next meeting, Ginger wanted to go to lunch. We sat in a private booth at a nice restaurant and enjoyed light entrees. About halfway through the lunch, Ginger looked flushed – gazed into my eyes, and said in a breathy tone, "I want you... now."

I was new to the dating game and wasn't used to any woman being so direct. But I loved it.

I paid the bill and we each drove to my house. We quickly seduced one another - first on the couch and then in the bedroom. She spread her naked legs and welcomed me inside her. We fucked with abandon. She came first. The intensity of her orgasm helped throw me over the precipice. Bodies still locked together, we kissed, cuddled and talked. Then, Ginger needed to leave to finish her errands and to get home to her family where she would make dinner using the frying pan her husband had given her for her birthday – a gift that repulsed her.

I told Ginger I harbored a fantasy of a woman sneaking in through my backdoor in the middle of the night, getting naked, and crawling in bed with me – waking me up with sex, not foreplay. Ginger fulfilled that fantasy. We made love several times over the next two months, and explored every position I could imagine, although we never tried anal. I’m guessing she would have been open to anal had I asked. But her pussy was so tight and enjoyable, anal never crossed my mind when I was with her.

I knew that I was serving as her Bull (not a word used at that time), but I also knew that I had some cuckold tendencies even though I had no word for that role at that time. After we had grown familiar with one another, I asked her to make love with her husband at home and then to come directly to my house and make love with me... without cleaning herself up. She was kinky enough to fulfill that fantasy too.

As I dipped my tongue between her lower lips, she asked, "Can you taste him?"

I pulled my mouth back from her welcoming pussy and said, “I'm not sure. You certainly are very wet and slippery down here. But I’m not sure I an actually taste any semen."

"He might have masturbated before we fucked. His orgasm wasn't very intense. I hope I didn't disappoint you."

"No... I am very satisfied. Thank you for accommodating my fantasy."

"My pleasure. Now slide up here and fuck my well-fucked pussy with that handsome cock of yours. I came with my husband, so I am not certain I can cum again. But I would like to."

I did… She did.

I told Ginger that if she and I were partners, I would love to watch her having sex with another man. She smiled and said she would be happy to give me pleasure in that way. But, the fact was... she was married. We were not.

Ginger worked in the health field as a patient assistant. She worked along side an attractive co-worker in her late 20s who had two young children and was recently divorced. Ginger playfully told me that she may introduce the co-worker to me, "After I am done with you." But Ginger was getting increasingly attached to me and wasn't going to toss me aside as a gift to another woman just yet.

Ginger also conjured a very kinky plan. The plan never came to pass but it was kinky enough that it warrants being told. Specifically, Ginger told me that she had discussed going on a double date with her husband. The other couple on this date was going to be her female coworker and me. Her husband still thought she was spending time with a female lover, so he would have had no idea that she was actually spending time with a man, and that this man was actually me.

When talking about the proposed date, Ginger imagined us going to a strip club that she and her husband had been to a few times where we could each get lap dances to get our motors running. After that, we could all go to Ginger's house where we could safely have a few more drinks and get tipsy. Ginger had introduced her husband to her coworker. He found her to be remarkably attractive. And, Ginger was pretty sure that she could prime the pump and get her coworker to seduce her husband – to take one for the team. Ginger thought we could have a "swingers party." The coworker would have sex with the husband, and Ginger would have sex with me, in front of her husband.

The idea aroused me but I wasn't as convinced as Ginger that she (we) could pull it off. I'm not into duping people and am prone to tell the truth if confronted.

One day after one of our afternoon trysts, I made a comment to Ginger about making sure that we both maintain boundaries. She took it badly. She was angry and left my house abruptly. We communicated via email and a couple of phone calls after that but we each moved on. We never had the double date, and I never was introduced to her coworker. As newly divorced parents (she had two kids), we could have had some no-strings fun together.

Ginger told me that she had begun to date another guy. He was married but had no children. Their relationship grew to the point that Ginger introduced her youngest child to him. His wife figured out that her husband was having an affair with Ginger. She found Ginger's husband and told him about the affair. Ginger's lover was a man, not a woman. Their marriage blew up soon thereafter. I lost touch with Ginger completely soon thereafter.

Many years later, I was standing near a shop in the Seattle airport. I looked over and about 15 feet to my left, there stood Ginger. She was looking into the shop as if she hadn't noticed me. She was older and heavier. I was older too. We each stood there behaving as if we hadn't noticed each other. After about a minute, she turned and walked toward the gates. I have no idea if she noticed me and positioned herself to be in my path or if it was a completely random circumstance. I'll never know if she noticed me or not.

If Ginger ever found a man whom she loved, and he was a natural cuckold, she would have been in 7th heaven. However, Ginger had a tendency to become romantically attached to each of her sexual partners. She may have had a difficult time staying true to her cuckold - emotionally. But she certainly was hot, loved sex, and did not want to be restricted to sex with one man.

We fantasized about being a hotwife-cuckold couple by way of her coming to my bed immediately after she had sex with her husband. Likewise, we both resonated with the fantasy of me watching her have sex with another man. She clearly liked that fantasy. But I did not want to take on the responsibility of her children, nor did I want to be the catalyst for her divorce. So, the Ginger chapter ended.

And along came Kara... a brilliant blond hottie.

venus-can99
OHW Addict
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Re: Evolving as a cuckold - through the seasons of life

Unread post by venus-can99 » Tue May 13, 2025 6:21 am

Thanks for that very spicy update with Ginger Owl. Looking forward to your encounters with Kara

The Owl
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Re: Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Wed May 14, 2025 6:47 pm

Actually... there's not a long story to tell about Kara. We met at a conference and enjoyed flirting with one another. A couple of months later, I was flying to the Midwest for a family gathering. She was about a one-hour flight away and decided to join me at the gathering.

We didn't know each other all that well so we decided to reserve two rooms in the small town motel where the gathering was held. The first night of sleep was uneventful. The second evening, after turning in, there was a knock on my door... Kara.

I welcomed her in and we quickly found ourselves petting heavily on the bed. Lots of passionate kissing and touching. Kara resisted when I began trying to remove her blouse. Strangely, she turned the table and began tugging at my belt while we continued to kiss. She pushed me onto my back and told me stay in that position and not to move unless she gave me permission. Soon, she had my belt open. She proceeded to unzip me and asked me to raise my hips as she pulled down my pants. I was fully erect. She pulled my underwear down and hovered above my cock. I could tell she was aroused by the way she was touching my torso. She used her hand to lightly caress my cock. Her face was less than a foot above my cock. I couldn't tell if she was visually inspecting me or whether she was on the brink of giving me a blow job.

I reached up and began to caress the top and back of her head, not pushing her down but encouraging her - if she so desired - to give me pleasure with her mouth. She told me once again to be still. I pulled my hand away.

She continued touching me... around the penis and on the penis. She stroked me a few times but not nearly enough to get close to release. I had never had an encounter like this with a woman before. I was a bit flummoxed.

Although I had never heard of denial or ruined orgasms at that time, it was if she was being dominant... arousing me but restricting me from release.

She pulled my underwear back up over my frustrated erection and encouraged me to pull my pants back up.

She said, "You passed..."

I playfully asked her, "Was that a test?"

She replied, "You have a handsome cock. And, you didn't force yourself on me. You followed the rules."

We continued making out but there were no orgasms that evening.

The next night was our final night together. She spent the night in my motel room. This time, she donned some lingerie in the bathroom.

When she emerged, she told me, "Show me what I saw last night. Get naked."

I did. She made sure I savored her in her lingerie on the bed for quite some time before we were both naked.

After entering her, our bodies worked together nicely. She came... and encouraged me to cum. I didn't resist.

Kara told me that she didn't cum from intercourse most of the time but that our bodies fit together nicely.

We bid each other goodbye the next morning. We communicated occasionally after that. She wanted to remain a free agent and was not looking to lock down with a partner. But we certainly had a good time during that weekend together. And, my family was impressed that a bright beautiful hottie traveled to spend time with me. My extended family decided they did not need to worry about me being recently divorced. They could see I was able to make hay... in the hay!

shadowtantra
Experienced
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Re: Evolving as a cuckold - through the seasons of life

Unread post by shadowtantra » Fri May 16, 2025 9:50 am

Thanks Owl for the erotic memory and ongoing evolution.

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