Evolving as a cuckold - through the seasons of life

[The Owl]

Thanks Owl for the erotic memory and ongoing evolution.

You're most welcome. It's an interesting process to capture the past. And, the past defines the present.

[nnjcpl2002]

Thanks for sharing your experience here, Owl. We are eager to learn more about your cuckold desires and experience. That is where we may have a greater intersection of interest. So....more please?

[The Owl]

Thanks for sharing your experience here, Owl. We are eager to learn more about your cuckold desires and experience. That is where we may have a greater intersection of interest. So....more please?

The true tale - as true as can be told - is always long, delicate, and nuanced.

Between black and white, is the land we all live in... the gray zone... where just noticeable differences sometimes go unnoticed.

More to come.

[shadowtantra]

The true tale - as true as can be told - is always long, delicate, and nuanced.

Between black and white, is the land we all live in... the gray zone... where just noticeable differences sometimes go unnoticed.

More to come.

Words to live by....

[The Owl]

And the wave of women who wanted more than a one-night stand but less than a commitment kept rolling through the front door in response to my Yahoo! personals ad. It was working its magic. Likewise, I was responding to ads posted by women who were looking for a no-strings date.

I went hiking ocasionally with one of the women I met. Another, Lily, just wanted to get together and talk and have sex. Both of these women had one thing in common. A strange thing in common...

The first time I was lying on the couch... kissing, cuddling, and caressing with each of them on different evenings during the same week, something strange happened. In each case, I had removed their tops. My shirt came off as well. We were enjoying some skin on skin time, getting hotter by the moment. Now it was time to unbutton the pants, unzip, and slip my hand down the front to touch each of their pussies.

As I began unbuttoning the first, she said, "Be careful, I have a cock down there." The first woman's comment threw me off for a moment.

"What do you mean?"

She smiled and said, "If you want to feel my cock, keep going."

Her breasts were full sized and everything else about her was very feminine. I decided to keep exploring. Quickly, my middle finger was slipping between two engorged labia into her sticky wetness. I gently caressed her clitoris with my fingertip and said, "Your cock is small and wet."

She giggled and our tongues found each other again. We moved to the bedroom and the sex was good. We got together a few times. She was raising her two sons and wasn't looking for anything permanent.

Within the same week, I was on the same couch with the other woman, Lily. As I progressed toward unbuttoning her pants and moving my hand inside her knickers, she said almost the exact same thing as the first woman. "Brace yourself. I have a cock."

"What?"

"I hope you like cock because that's what you're going to find down there."

"I'll risk it." And I proceeded to push further inside her underwear. Once again, I found a wet and welcoming pussy. She gasped slightly when I began making little circles on her slippery clit with my fingertips. She caught her breath and said, "You found it... you found my cock." The sex was great with Lily.

I never had a woman say, "I have a cock" before or after that specific week with those two different women who didn't know each other.

I never could figure out why they each said the same thing to me at the same point in the mutual seduction. My best guess is that Cosmopolitan magazine or the equivalent had an article that month titled "How to surprise your new lover when he is trying to get in your panties for the first time" or something like that. Maybe they had each independently read the same magazine article, and each of them decided to try the line on me.

I wonder how I would have responded if one of them would have had an erection inside their panties? I was spared that dilemma in both cases.

There is more to tell about Lilly. She had a couple of other surprises to share with me as we continued meeting for sex during the next few months.

[venus-can99]

I wonder I that line threw you for a loop unless you thought Lily may have been wearing a strapo.
Looking forward to hearing more about Lily and her surprises

[shadowtantra]

Thanks Owl. Great story! I know for me, in my 20s I would have upped and left if she said she had a clock. With experience, I would have given it a try - try anything once.

[The Owl]

Thanks Owl. Great story! I know for me, in my 20s I would have upped and left if she said she had a clock. With experience, I would have given it a try - try anything once.

I was definitely taken aback the first time. Then to have another woman independently say the same thing that same week felt bizarre... as if they were in cahoots!!! Both were very feminine. So, I was pretty sure neither was a lady boy. Again, I think there must have been a magazine article that month that they each read. But who knows?

[frank12]

Ah, Owl you've reminded me now of the two women I enjoyed who were blessed by the naturally larger clit. Both were very aware of the differences they possessed, though neither referred to her clit as a "cock" except in playful banter. Both were very sexual in their lives, admitting to rejoicing in frequent masturbation play from early on. One was married and living a prim and proper life of wife, mom and secretly eager vixen, the other had divested herself of a husband some years before when she decided to NOT be held back, and enjoyed dalliances with women (several of whom LOVED being penetrated even that tiny bit with her clit).

[The Owl]

Ah, Owl you've reminded me now of the two women I enjoyed who were blessed by the naturally larger clit. Both were very aware of the differences they possessed, though neither referred to her clit as a "cock" except in playful banter. Both were very sexual in their lives, admitting to rejoicing in frequent masturbation play from early on. One was married and living a prim and proper life of wife, mom and secretly eager vixen, the other had divested herself of a husband some years before when she decided to NOT be held back, and enjoyed dalliances with women (several of whom LOVED being penetrated even that tiny bit with her clit).

Frank12... interesting. In the case of these two women who definitely did not know one another and were not in cahoots, both had very normal labia and clits. Nothing oversized. They were just looking for a reaction from me. Maybe they were also metaphorically asserting some dominance by claiming to have a cock. It's so hard to know how and why those comments emerged from each of their mouths in such close proximity. It was the first time (but not the last time) either of them had gotten naked with me.

Life is a long series of very interesting moments... interspersed with a lot of routine activities that comprise the flywheel of daily life, the flywheel of civilization.

I never encountered a supersized clitoris. Ontologically during fetal development, the clitoris and penis are thought to emerge from the same embryonic tissue. In the case of females, I think the concentration of nerve endings is greater than in the male penis. Women are designed to get as much, if not a lot more pleasure from sex than men. If women did not have to deal with the vulnerability of being entered and the vulnerability of pregnancy, then women would probably be seducing men (and women) more frequently than any of us can imagine. I wonder if a woman with a large clit gets even more pleasure from her clit than the average woman? Could you feel each large clit against your pubis when you were fully inserted in each of these women. How large were these clits?

[frank12]

...
Life is a long series of very interesting moments... interspersed with a lot of routine activities that comprise the flywheel of daily life, the flywheel of civilization.
...

If women did not have to deal with the vulnerability of being entered and the vulnerability of pregnancy, then women would probably be seducing men (and women) more frequently than any of us can imagine. I wonder if a woman with a large clit gets even more pleasure from her clit than the average woman? Could you feel each large clit against your pubis when you were fully inserted in each of these women. How large were these clits?

I have heard arguments that without the well-placed bundles of nerves in and around the feminine anatomy that women would not so eagerly choose to engage in any of the necessary behaviors of procreation - but I would differ with those arguments and side with you: It is primarily the deserved cautions that cultures heap upon their women to avoid difficult early pregnancies that hold them back.

I was myself fascinated with the enlarged clits that were revealed. In the first case she was somewhat shy and self-conscious of the differences from other women even though hers only became obvious when she was aroused. Hers lifted itself and could be quite prominent with a tip that emerged rather well out of her hood when aroused. Lifting out of her otherwise prim labia he clit was "proud" and she was *very* aware of the pleasure she could give herself with minimal stimulation - including simpliy moving just the right way. She admitted to discovering early the surreptitious approaches to masturbation primarily enabled by how her clit protrudes from between her labia once teased. And yes, even I could feel the swollen clit pressing against me.

The second amazing clit was thickly and prominently protruding along with large and meaty inner and outer labia. This thick (9 mm?) clit and its hood (11 mm?) were more permanently "on display" thanks to the form of her anatomy. She was much more eager to show it off too, enjoying the reactions she would get from the girls at the salon when she went for her bikini waxings. She was adept at making it "dance" and when playfully naked could hardly keep her hands off of herself. Clearly she focused on her pleasure from her clit and loved to be somewhat roughly "banged" or to have my balls swinging against her clit when taken from behind to involve her clit with each stroke.

[The Owl]

Closure was reached in my brief relationship with the first of these two women when she wrote me an email a couple of months after she warned me about her "cock." Basically, I had not reached out to her for about five days. She apparently became anxious and felt a need to define our relationship. After those five days had elapsed, she wrote an email and told me that she had concluded that I wanted to break up with her. She said that that she understood, wasn't angry, and accepted my decision. I was a bit surprised by her email, but then decided to accept her message. I didn't want an exclusive relationship with her and was comfortable with using her email as an exit strategy from the relationship. We corresponded a few times after that and remained friendly but never got together for another fling. She was a good woman who was looking for a more committed relationship. My Yahoo ad was not misleading about what I was seeking.

And then there was Lily. She lived in a different town but traveled to my community every few weeks. When she came, we would cum... so to speak. We each knew what we wanted from the relationship - erotic tension, erotic release.

We knew this was not a relationship that was going to lead to a commitment, so there was a level of comfort to openly talk about sexual histories and fantasies with each other. There was also comfort with teasing and being teased - for our mutual erotic pleasure. She had an administrative job but her passion was art. She was creative and erotically wild. I won't tell her sexual history stories... those are her stories, not mine. But she had explored bisexuality and was very open-minded about all matters involving the erotic, involving sexuality.

One evening, Lily and I were laying in my bed naked. I was on my back. She was cuddled up beside me, nibbling my ear, caressing my body, my balls and my relaxed cock. I could tell she wanted to arouse me as she began telling me one of her fantasies. She wrapped her fingers around my cock to directly feel my erotic reaction, to feel what fantasy was going to get me erect. Fairly soon, she was whispering in my ear, "Would you like me to tell you about my other lover in town who is a mountain climber, well built, with a larger cock? He knows how to use that cock of his." I had no idea if she was talking about a fantasy lover or somebody she was actually seeing recently. We both knew our relationship was not exclusively.

Feeling my cock growing firmer between her fingers, Lily asked, "Would you like to meet him? Would you like to watch him kiss and caress me? Perhaps you would like to watch him push his cock inside me and fuck me. If you'd like, you would be welcome to kiss me while he fucks me."

My cock was becoming more and more turgid and was beginning to ooze with pre-cum. She continued with her fantasy while using her middle finger to play with the clear pre-cum oozing from the tip of my cock. Little did I know that she was lubricating her finger with a devious plan in mind.

She continued telling me how well he had fucked her last time time they had sex. She told me that he was very fit, and very dominant. But she claimed that she was sure he would be open to letting me watch them fuck, as long as I didn't interfere... as long as I was willing to remain submissive in his presence. She said, "I'd bet that he would actually enjoy showing you how dominant he can be... how he makes me moan with pleasure as his cock gives me orgasms."

"I've told him about you... not your name... but that you're my regular lover when I'm in town. He finds it hot that from time to time, I also want what he can deliver... sexually."

"Maybe you'd like to be there, but you would have to be completely submissive toward him. Perhaps he would let you use your hand to help guide his cock into my pussy. Would you do that for me... for my pleasure? Would you do that for your pleasure... for your submissive pleasure... would you get off watching me being fucked by a young mountain climber?"

All the while, her middle finger was getting slicker and slicker with my pre-cum that was now dripping on my belly from the tip of my cock.

Before I had time to answer her provocative questions, she pulled her hand away from my hard cock and quickly moved her hand between my legs, below my scrotum. Her hand was clenched in a fist with her middle finger extended, as if she was giving my ass the finger - which was her devious plan all along. The tip of her middle finger found its target - the bud of my ass. Without hesitation, she thrust her finger deep into my ass, all the way to the last knuckle in one firm and quick motion. In a flash, Lily's entire finger was deeply embedded in my ass.

Although her finger was lubed a little with pre-cum, my ass was not and the abrupt penetration caused a slight tinge of pain. My ass was not accustomed to being penetrated. It didn't feel like she had torn any tissue but having her finger pushed into my ass so quickly and unexpectedly came as a bit of a shock - unfamiliar sensations... a twinge of pain and a rush of feelings that admittedly were erotically pleasing.

My body twitched as she penetrated and I reflexively said, "Be careful. That tissue feels very sensitive."

"Did I hurt you?"

"No... but I felt a twinge of pain when you pushed in. My ass had no lubrication."

She laughed devilishly and replied, "But my finger did."

Then, Lily began moving the tip of her finger inside my ass... rhythmically massaging my prostate gland. I moaned in response to the previously unknown carnal pleasure she was creating very deep in my ass... feelings deep inside me that I had never felt before.

Lilly continued stimulating my prostate as if she was rubbing her own clitoris in search of orgasm. She began nibbling my earlobe again, biting hard enough to border on painful but not hard enough to cause any damage. She knew how to take it right to the edge... to the razor's edge between pain and pleasure.

As she let up on my ear with her teeth, she teasingly whispered, "Now you're gay. Your ass is mine."

I looked at her and said, "What you are doing feels good. And, I admit I am very open-minded. But I think we both know I'm not gay."

To which she replied, "You don't have to be gay to touch his cock for me... to kiss his cock for me... to let me guide his cock into your ass for his pleasure. You just have to be open-minded... which you are."

Soon, her finger came out of my ass and we fucked.

As we climbed the wall toward our orgasms, Lily asked, "Did you like having my finger in your ass?"

"Yes."

"Did you like my fantasy of having you watch me having sex with another man?"

"Yes."

"Good... be ready... be ready for anything."

We both crested into oblivion - consciousness momentarily shattered as we leapt across the abyss called orgasm.

To the best of my knowledge, her mountain climber was actually a former lover whom she hadn't seen for several years. But she enjoyed teasing me about him that night. She enjoyed teasing me about playing the role of her submissive cuckold - although we didn't have that label to describe that role in those days. The internet was new and words "hotwife" and "submissive cuckold" were not in common use at that time.

A few years later, I was having a business dinner with a group of men near the door leading into the restaurant. Mid-dinner, Lily entered the restaurant and was followed by a man who was obviously with her. He presented as a somewhat passive beta male. Perhaps she had found a willing cuckold to nurture her and to be affectionate, while supporting her desire to enjoy trysts with alpha males. I'll never know where her trail led her.

A few years after seeing her in the restaurant, a person I know was attending an art show. He met a woman who told him she had dated me several years earlier. The guy told me that Lily had told him, "He was a lot of fun. But I think I was too wild for him."

Lily came and Lily went... She was sizzling hot... but our chemistry would not have worked long-term for handling day to day life as a couple.

[venus-can99]

Thanks Owl for this erotic re-telling of yet another episode in your journey. Looking forward to the next episodes.

[The Owl]

Thanks Owl for this erotic re-telling of yet another episode in your journey. Looking forward to the next episodes.

Thank you for the feedback. The tale shall continue.

[Rogueuser1]

Wow that was an amazing night with lily - do you wish the mountain climber had been a real, current lover you could have watched with you? Even if she wanted you to be "open minded"?

[The Owl]

Wow that was an amazing night with lily - do you wish the mountain climber had been a real, current lover you could have watched with you? Even if she wanted you to be "open minded"?

Most eroticism is between the ears. She inserted her finger in my ass and her fantasy between my ears. That was good enough for the moment.

[venus-can99]

Most eroticism is between the ears. She inserted her finger in my ass and her fantasy between my ears. That was good enough for the moment.

Don't they say that the brain is the most important sex organ ?