Evolving as a cuckold - through the seasons of life

[venus-can99]

IMO your version is way better more authentic. The AI version has more flowery language perhaps best suited to romantsy writings

[The Owl]

IMO your version is way better more authentic. The AI version has more flowery language perhaps best suited to romantsy writings

venus-can99... At the risk of sounding narcissistic, I have to agree. But it was an interesting experiment. AI will be writing a lot of documents in the future. The AI version of my experience at the restaurant sounded more candy-coated, and less raw and visceral than what it felt like - in the moment - waiting for Scarlett at the restaurant.

Thanks for the feedback.

I'll get on with the story of Scarlett and The Owl... in due time. The beginning was a slow sizzle... a very hot and very slow sizzle.

[The Owl]

Scarlett and I spent several weeks together - flirting and petting - before she succumbed and allowed me to undress her completely.

We spent a lot of time on my couch, kissing, caressing, fondling, and grinding. When I was on top of her, kissing, and pushing myself against her jeans, she would begin moaning intensely. When our lips separated, she would moan "Oh God..." or "Fuck... oh fuck..." as if she was on the brink of orgasm or actually having an orgasm.

(When we had more history together, I asked her what she remembered about those petting sessions. She told me that she would have little bursts of orgasmic pleasure arising from her crotch into her gut, but not full release. Those bursts felt very good but did not give her the deep pleasure and relief that comes from one of her orgasms.)

During this time on the couch, over time she began allowing me slip my hands under her top, but whenever I went for the buttons on her jeans, she would gently pull my hand away.

Over the span of several weeks, I finally got access to her naked torso and discovered that her nipples were highly sensitive. She moaned and groaned intensely while I sucked on her nipples. Interestingly, her left nipple was even more sensitive than her right nipple, but I had fun with both. She enjoyed both nipples being licked, nibbled, and sucked. Her tits were a perfect size - my favorite... full, pert, but not huge. She was trim and athletic, but her body felt soft and welcoming - as long as I played above the belt.

One lazy Sunday afternoon, we were petting on the couch. I had her top off and was enjoying her breasts. She had tugged my shirt off as well so we could enjoy some "vitamin skin" together.

Scarlett wiggled out from under me and stood up next to the couch - hair tousled and breasts exposed proudly on her chest. Her nipples were erect and moist with my saliva. She extended her hand and said, "Come." She led me to my bedroom. This time, my hand was not brushed away when began manipulating the button and zipper of her pants. She allowed me to remove her pants before laying on the bed. She was still wearing her panties which were very petite, and had lacy trim. It was as if she had selected her most erotic panties when dressing that morning in anticipation of the fuck to come later in the day.

My shirt was beside the couch in the living room but I was still wearing pants. I boldly removed my pants and then my underwear. Scarlett's eyes were focused on my erection. She smiled and seemed pleased about this first presentation of my cock.

I moved onto the bed and was quickly on top of her. She could feel my erect cock pushing against her panties. Her kisses suggested she was on fire with anticipation. I rolled to her side and continued kissing her. I slipped my fingers down the top of her panties, while our tongues remained entwined. My fingers found a very wet jungle of lust. My middle finger slipped between her labia. As I pushed gently into her pussy, I could feel that she was tight but welcoming. Our kissing intensified. I could smell her sex - nostrils flared.

I gently pulled my hand out of her panties and began tugging them down. Scarlett raised her hips to accommodate my efforts. Once I got her panties off her ankles, I twirled them on my fingers and flung them high in the air, toward a chair in the corner of the bedroom. Scarlett giggled, suggesting she was enjoying what I was doing and where this was headed.

Despite her arousal, Scarlett held her legs tightly together. I began using my hands to pry them apart. She initially resisted but we both wanted the same outcome. Scarlett seemed to enjoy resisting and I enjoyed asserting myself. Over time, I learned that Scarlett is a natural submissive and likes it when a man confidently demonstrates that he will have a firm hand with her. She didn't want to submit too soon. She wanted to enjoy me firmly going for what I wanted. She wanted me to take charge... to take what I desired... to push my way through her resistance... into her submission.

I firmly separated her legs and positioned myself over her, between them. I reached down and positioned the tip of my cock at the opening of her pussy. I moved my cock up and down between her labia a few times to lubricate it, and perhaps to tease her for a moment. Then, I slowly began pushing in through the tight opening of her pussy.

Scarlett's head turned sideways and she gasped with pleasure. I lowered my head and kissed her neck, while pushing in a bit further.

Scarlett turned her head toward mine and whispered in my ear, "Go slowly. I haven't had a cock as large as yours inside me for several years. It feels good but go slowly so I have time to get used to your size."

My cock is average size, both in length and girth. I was a bit surprised to hear her say "...as large as yours..." and that her recent partners were smaller. No wonder her pussy was so deliciously tight.

Once I was fully inside her, I began slowly using my cock and pelvis to arouse her. Having sex with Scarlett felt completely natural, intuitive. Her bodily responses - including her breathing - let me know exactly what movements she enjoyed the most. After a few minutes of mutual pleasure, Scarlett's eyes became almost vacant, her head turned to the side, and she began moaning "Oh God... Oh God..." more intensely than I had ever heard. Her entire body began spasming rhythmically. She was in the midst of a very intense full-body orgasm - her consciousness shattered into a million shards of pure pleasure. I could feel her pussy throbbing on my cock. Her breath was deep and fast, with guttural groans coming from her chest and throat. Her orgasm seemed to go on for a long time - much longer and more intense than any woman I had experienced before Scarlett. Slowly, she began to relax, coming down off of the extended plateau of release. Her eyes re-focused on me. Our lips met again. She whispered in my ear, "Thank you. You're good. Very good."

Scarlett knew that I had a vasectomy, and was shooting with blanks. As she was recovering from her intense orgasm, I confidently stated, "I'm going to cum deep inside you."

Scarlett's pussy immediately pulsed once more around the base of my cock. I couldn't tell if the pulse was the final spasm or orgasm or if she had deliberately "winked" her pussy on my cock to nonverbally grant permission to fill her pussy with my cum. Her only verbal response was to whisper in my ear, "I could only resist you for so long."

She reached down and caressed my ass, encouraging me to enjoy myself inside her very satisfied pussy. I began thrusting my way to and through an intense orgasm. We cuddled, kissed, and savored the smell of sex on our skin.

[nnjcpl2002]

Very nice, Owl! I think this woman is a keeper.

[The Owl]

Very nice, Owl! I think this woman is a keeper.

Thanks for the feedback nnjcp2002.

Out of respect for her privacy (and mine), I have and will switch up a few details (e.g., names, geographical locations, etc). But it is important to me to keep the basic truth of the story.... well, true. Jumping from the erotic truth to a pornographic "tall tale" becomes tin-plated quickly. Sticking with the truth underlying a relationship is the path to understanding the erotic - to feeling the erotic.

[The Owl]

Shall I continue telling the story of the evolution of my romantic connection with Scarlett and how we led each other down the path to the point that she cuckolded me, while I quietly watching the action from bedside? I don't want to be writing into a vacuum. Thoughts and reactions are welcome.

[wannabecUKold]

Shall I continue telling the story of the evolution of my romantic connection with Scarlett and how we led each other down the path to the point that she cuckolded me, while I quietly watching the action from bedside? I don't want to be writing into a vacuum. Thoughts and reactions are welcome.

Yes of course, please continue. Especially as she was taken (literally) by your size and hadn't had that size previously. So how she came to cuckold you is a very interesting question. I like it that she did. It is very sweet for a woman to love you deeply and cuckold you. Feels right.

[venus-can99]

Shall I continue telling the story of the evolution of my romantic connection with Scarlett and how we led each other down the path to the point that she cuckolded me, while I quietly watching the action from bedside? I don't want to be writing into a vacuum. Thoughts and reactions are welcome.

Please do... I for one feel that we are looking at an inflection point where Scarlett transitioned from admiring your huge cock and lovemaking skills to making you a cuckold

[Kaunissaari]

My first wife, who repeatedly cucked me from the beginning in our early years in the early 80's even though there was not a common name for it back then but everybody seemed to know, had sensitive nipples as you describe Scarlett has. I took immense pleasure in pleasing her nipples back in the day. I connected with her through her nipples as your describe... I lost my first wife to reasons beyond sex relating to my love of work and being a workaholic. Success at work does not equal love of life. Started out on different foot with my second wife... to whom I am still married...
Owl, I have enjoyed your stories of your life. Read most of them but I would fail a detailed test on the details. I urge you to continue to bless us with your stories so as I might be able to draw upon your experiences to provide future council to my younger friends and relatives should they ask for it.. Who knows what life will bring us... Carry On...

[The Owl]

My first wife, who repeatedly cucked me from the beginning in our early years in the early 80's even though there was not a common name for it back then but everybody seemed to know, had sensitive nipples as you describe Scarlett has. I took immense pleasure in pleasing her nipples back in the day. I connected with her through her nipples as your describe... I lost my first wife to reasons beyond sex relating to my love of work and being a workaholic. Success at work does not equal love of life. Started out on different foot with my second wife... to whom I am still married...
Owl, I have enjoyed your stories of your life. Read most of them but I would fail a detailed test on the details. I urge you to continue to bless us with your stories so as I might be able to draw upon your experiences to provide future council to my younger friends and relatives should they ask for it.. Who knows what life will bring us... Carry On...

Thanks for the feedback wannabecUKold and venuscan99.

And Kaunissaari... are you actually a beautiful island located in the Gulf of Finland? Geography lessons aside, thank you for your thoughts and memories.

I'm curious, did you find being cucked by your first wife in the early 1980s erotic, or as it only painful for you? Does your current wife cuck you as well? If not, do you desire to be cucked by her? There are so many layers to each relationship. Each relationship is like a fingerprint... unique. But there are some themes that seem to be universal across all relationships.

I can relate to the "workaholic" issue. When a person is competent at something, and receives a lot of positive reinforcement when engaged in that activity, it is hard to to feel encouraged to do MORE... and more... and MORE. You are right: Success at work does not equal love of life.

[The Owl]

Kaunissaari... I saw your previous posts on other threads. It sounds like you are not being cucked by your current wife. Do you miss some aspects of the lifestyle?

[The Owl]

Scarlett continued...

Scarlett and I continued making love several times per week. We each had busy lives but we enjoyed getting together whenver we could. We especially enjoyed our naked time together.

We were very comfortable telling each other about our respective sexual histories and previous relationships. She was very clear about being fully heterosexual. She was not homophobic but she did not find women to be of interest from a sexual perspective. Rather, she found men both attractive and sexually satisfying. She was able to orgasm directly from intercourse without any additional stimulation of her clitoris. She enjoyed sex with the few men with whom she had been historically. She was open-minded but her sexual experiences were limited to a few relationships.

Scarlett lost her virginity when she was about 18 years old. She wanted to see what all the fuss was about and allowed a guy at a party she was at to have his way with her in one of the dark rooms at the house where the party was occurring. She enjoyed the experience, and was relieved that she no longer had to tell anybody that she was a virgin. She also knew that she had no interest in developing a relationship with the guy with whom she had her first experience with intercourse. He served well as party (and pussy) filler, but the intrigue was gone by the time the party was over.

A bit after that, Scarlett briefly dated a guy in college with whom she felt an interpersonal and intellectual connection. He was reasonably handsome. They enjoyed each other's company on a series of dates. But, the first time she got naked with him, she discovered he was cursed with a micro-penis. She described it as being smaller than her pinky in length and girth, even when erect. She decided to go through with having sex with him. Almost immediately after he entered her, he had an orgasm. She told me that she could barely feel him while he was briefly inside of her - his cock barely reaching beyond her labia, inside her vagina. After he came he rolled off her and fairly quickly put his underwear back on. He seemed to have no awareness that she had not experienced any pleasure. He did not demonstrate any interest in pleasing her with his fingers or tongue. She liked him personally but knew that she would never be sexually satisfied by him so she decided to stop dating him. She felt sorry for him but saw no reason to sacrifice her pleasure out of pity regarding his tiny cock and his lack of sexual skills.

I wonder if he eventually found a hotwife to marry... a woman who wanted relationship with him but wanted sex with other men? Scarlett lost track of him after that date, and had no idea what became of him - a nice, handsome, and intelligent guy with a minuscule cock.

She dated another guy briefly during college with whom she had sex a couple of times. His cock was big - quite long and thick. I'm not certain how large he was but his cock was certainly bigger than mine - or so she said. Both times she had sex with him, Scarlett felt pain more than pleasure. He seemed to enjoy being inside her but his cock felt too large for her comfort. She knew that she could probably adapt to the size of his cock over time, but she didn't feel like this guy was going to be a good long-term match for her in other ways, so she decided to end that relationship rather than work on stretching out her pussy for him.

Mr. Tiny and Mr. Big were history. During college, she dated a few other guys with whom she enjoyed one or more sexual encounters. During college, she learned that she enjoyed giving oral sex. She was not as keen about receiving oral sex. She didn't think that most guys enjoyed licking her pussy. And, besides, why have a clitoral orgasm when she knew that inviting a guy's cock into her pussy would result in a much deeper and more satisfying orgasm.

To be continued...

[Rogueuser1]

Poor guy - I wonder if he knew and that is why he got dressed so quickly.
Hopefully he at least learn to get good with his tongue and fingers - that can make up for a lot. Though I agree, I do hope his wife is cuckolding him and getting a real cock not just his micropenis.

[The Owl]

Poor guy - I wonder if he knew and that is why he got dressed so quickly.
Hopefully he at least learn to get good with his tongue and fingers - that can make up for a lot. Though I agree, I do hope his wife is cuckolding him and getting a real cock not just his micropenis.

Although she was in school in Scotland, my experience is that pubescent boys become fascinated with their cocks when public hair starts to grow and erections pop up several times per day - on the heels of a slightly sexual thought or a siting of a bra strap, etc. In the locker room or with a group of guys behind the bushes looking at a Playboy magazine (now they are probably looking at pictures on a phone), an adolescent boy typically knows if his cock is extremely large or extremely small. But I suppose Mr. Small may have been ignorant about his penis being tiny. And I suppose he could have been ignorant about the fact that women can enjoy sex too and that giving a woman pleasure can be fun. Who knows?

Men... and women... come in all sizes and shapes. Accepting one's body for what it is, is one of the important challenges in each person's life. Sometimes that challenge is very hard for a person - for one reason or many. Some people appear to have little or no challenge accepting their natural characteristics.

Thankfully, Scarlett was blessed with very nice features and she took care of herself. She generally liked herself and her body. Men of all sizes and shapes (assuming they are hetero) found her visually attractive in her youth - and beyond. And a few got the chance to take her out for a test drive. Some figured out how to rev her engine. Others did not. One thing she liked was a man with a firm hand... a confident man who knew what he wanted and knew how to go for it. When a man was wishy washy or too hesitant, it was time for her to go home. She was particularly attracted to well dressed men, in good shape, who didn't shy away from satisfying their lust desire. A man who knew what he was doing and how to "go for it" was a man who could get past the first button with Scarlett. She didn't want to be raped, but she didn't want to have to guide a man through each step of seduction. If she said no, she meant it. But if she was just being coy, she wanted a man to take a dominant role so she could savor the pleasure of submissively experiencing a man's lust Being submissive was natural to her, a source of erotic pleasure. If a man knew what he was doing with a normal sized cock, Scarlett could easily be brought to a full orgasm by way of firmly thrusting his cock inside her pussy. She was bright and wanted more than just sex in a relationship. She was a bit of a sapiophile - a woman who finds intelligence arousing. But that intelligent man needed to have a dominant streak as well to fully arouse her.

[venus-can99]

Thanks for describing Scarlett in such glowing terms - an intelligent beautiful woman who needed more than just a big cock in her men. From sounds of it Mr Small was intelligent and good looking but not very smart when it came to sex. From your retelling it seems that you got to "park her in your garage" after the test drive.

[Kaunissaari]

"The Owl" posted
Kaunissaari... I saw your previous posts on other threads. It sounds like you are not being cucked by your current wife. Do you miss some aspects of the lifestyle?

---------
My second wife knows my first wife and witnessed her activities with respect to me and made it clear she did not approve. So no the cucking ended with the first wife's divorce from me. I really don't miss the drama of it all but find the stories found on this web site to be interesting and varying...

[The Owl]

There's so much more to tell with Scarlett.

We evolved...

D/s play...

S/m play...

Internal boundary play...

External boundary play...

Ass play...

So much to write...

Love... eroticism...

And... cuckolding...

[venus-can99]

Looking forward to the Scarlett tales

[The Owl]

After finishing college in Scotland, she married an "adventurer" from the USA. He expected Scarlett to support him and his adventures. He was fit, handsome, and charming but had a very poor work ethic. She grew increasingly disenchanted with supporting him and they began drifting apart. In case you're wondering, her husband's cock was on the small side of average but he was well able to satisfy Scarlett sexually despite his size. Scarlett's pussy was quite tight and she was very sexually responsive to him during intercourse. Although he wasn't big, he knew how to use his cock. Their sexual chemistry was good. Beyond that, she grew weary of his lack of ambition and his ongoing dependence on her to support him and his adventures.

Near the end of their marriage, Scarlett was about 29 yo. She decided to invite a 21 yo male intern from her office out for drinks to celebrate his last day of his summer internship. He was flying back to the East Coast to start his last year of college a day or two later. Scarlett had grown increasingly fond of the intern during the summer. He knew that Scarlett was married and never behaved as if anything beyond friendly banter was to be exchanged between them.

After two martinis, Scarlett seduced him in her car on the way home. She took the long way home. Through the woods where the wild things roam! They didn't have intercourse but he enjoyed a blow job that he probably remembers to this day. She is good with her lips, tongue, and mouth... and swallowed every drop that she could extract from him. He saw her lick a bit of semen off the side of her lip... and swallow again... while gazing into his satisfied eyes. Pleasuring him with her mouth was very satisfying to Scarlett. She didn't need more from him. As a natural submissive, she was satisfied knowing that she had given him so much pleasure with her mouth. He was young and was somewhat surprised to be seduced by Scarlett, and even more surprised when Scarlett swallowed his cum. He had never experienced a woman who was so skillful with her mouth and who seemed to relish giving oral sex.

When Scarlett got home later that evening, her husband knew something was up. She smelled of alcohol and may have tasted like fresh semen when he tried to kiss her. He asked a lot of pointed questions. She was feeling defiant and hid nothing. She fully disclosed that she had cuckolded him with the intern. Her husband kept asking her for more and more details. After telling him about the oral sex, she closed out the conversation by saying, "I've told you all I am going to tell you about what I did with him this evening." She added in her enchanting Scottish accent, "I gave him a proper send off."

Their marriage ended during the following months. But the marriage was probably over well before Scarlett enjoyed drinks with the intern.

Scarlett was once again a free agent. Her ex-husband was on his own. She was no longer going to fund his adventures.

Scarlett decided to remain in the US after the divorce. She kept her job and moved forward with her life as a single woman.

[shadowtantra]

Owl, so sorry to have lost your longer piece. I too have had that problem and then I started to write it up in a document and cut and paste it into the thread so that I would not lose it if the site crashed. Love your stories.

[The Owl]

Owl, so sorry to have lost your longer piece. I too have had that problem and then I started to write it up in a document and cut and paste it into the thread so that I would not lose it if the site crashed. Love your stories.

I edited the post after you read it the first time. You might enjoy re-reading. I included the story of Bart and Scarlett. That was a very unusual relationship. I still don't get it. But when it comes to sexuality, there are a lot of fetishes... a lot of variations... Bart's preferences were inconsistent with Scarlett's preferences. I wonder if Bart even found somebody who shared his fetish. There are women who find intercourse very painful and unpleasant. Such a woman may enjoy a partner like Bart.

As long as those involved are consenting adults, and as long as nobody is getting seriously hurt or being exploited, to each their own.

Thanks for the feedback regarding the story of my evolution.

[The Owl]

Scarlett's next relationship was with Bart. That relationship was perplexing to say the least. After they had been dating for a few weeks, they ended up on Scarlett's bed naked together for the first time. Bart rolled onto his back and began masturbating. He encouraged Scarlett to hold him while he brought himself to orgasm. Scarlett was surprised by what he was doing but was not offended. She liked him and held her body close to his as he used his hand to give himself an orgasm.

She enjoyed his company but didn't understand what was happening from a sexual perspective. Bart explained that he enjoyed his sexuality but that he was not comfortable having intercourse with a woman because he didn't want to enter into an exclusive commitment with anybody. Scarlett wasn't a woman who demanded exclusivity just because she had sex with somebody. Nonetheless, she did not want to force Bart to do something that made him uncomfortable.

She enjoyed everything else about him and they continued dating for a while. When they were naked together, she continued holding him while he stroked his cock to orgasm She imagined that he would eventually want to try intercourse with her, but he never did. She was allowed to touch his balls and to kiss him while he aroused himself. But he wanted to masturbate - nothing more and nothing less. He did not want her to use her hand or any other body part to bring him to orgasm.

Bart encouraged Scarlett to masturbate with him. She followed his lead a time or two and used her hand to bring herself to orgasm while she was on her back next to him. One time, she even tried to time her orgasm so they could cum together. Scarlett is a very open-minded woman, but she did not find mutual masturbation to be satisfying or arousing. She was willing to try it as an experiment. But she knew that a long-term relationship with Bart was not for her. They drifted apart without ever enjoying intercourse, or even oral sex. This was a very perplexing relationship for Scarlett. She ran into Bart in the community a few years later. He was still single. She assumed that he was still looking for female partners to hold him while he masturbated. Nice enough guy... but not the guy for Scarlett.

[The Owl]

In her next relationship before ours, Scarlett dated and lived with a highly educated professional. They had the best conversations and were very supportive of one another. But they had NO sexual chemistry. It was if they were very good friends. But they were not lovers. They both understood that there were parts of their time together that they cherished but there were parts that felt empty as a turned out pocket. They both decided to go their separate ways. There was no cuckolding because there was no sexual relationship. If nothing - no sexual tension - is happening internally, it is by definition hard to do something externally that creates the hotwife-cuckold dynamic. Esther Perel referred to the hotwife/cuckold tension in a relationship as "Inviting the Third." But inviting the Third adds no sexual tension where there is none to begin with. Scarlett did not relish ending that relationship because it felt like she was ending a friendship. But she didn't want pasta alone. She wanted a rich sauce to add flavor and spice to the dish of her relationship.

And then we met... as previously described. The sexual tension in our relationship was immediate and strong. Scarlett held off getting naked with me because she didn't want to lose herself in the relationship. I held off out of respect for the boundaries she was setting. I didn't know why she was setting boundaries on getting naked and being sexual. But I knew I wanted to respect those boundries... until the day she led me into the bedroom and the laundry landed on the floor. A memorable experience that I shared previously.

And next the evolution within the relationship.

[Rogueuser1]

Bart sounds like a strange guy - I wonder what had him so turned off from sex? That is quite the evolution for poor Scarlett, she probably started doubting herself a little after all that!

[The Owl]

Bart sounds like a strange guy - I wonder what had him so turned off from sex? That is quite the evolution for poor Scarlett, she probably started doubting herself a little after all that!

Sexually strange... Interpersonally pleasant... or so I am told