Evolving as a cuckold - through the seasons of life

For cuckoldresses and the men who serve them.
The Owl
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Evolving as a cuckold - through the seasons of life

Unread post by The Owl » Tue Jul 09, 2024 3:12 pm

I'm 69 now... the autumn of my life. When I was 16, I was madly in love with my HS sweetheart in a small Midwest town of about 3,000 people. My girlfriend (I'll call her "S") was 15. We were both virgins. Looking back at our HS pictures, I was reasonably handsome. She was beautiful, vivacious, and exuded female erotic appeal.

My dad was a minister and had given me a lot of religious messages about sex, such as "I expect you and the woman you marry to be a virgins until after you are wed..." that sort of thing. I did not feel deeply connected with the church, but I had absorbed enough fundamentalist morality to integrate what he was telling me about sex into my personal moral code.

My girlfriend had not been raised in a very religious family. Her mother got pregnant when with her older sister when the mother was about 17 years old. Three months later, her parents got married and had their first baby six months after the wedding. Having a baby out of wedlock in those days was verboten. In those days, it wasn't unusual for the first child to be the result of a shorter pregnancy than each follow-along child. Everybody knew what had happened but everybody pretended as if it hadn't.

During our first three months of dating, S and I spent a lot of time "parking." We discovered the pleasures of French kissing. Our lips and tongues discovered each others necks and ear lobes. We were torturing each other with arousal, without release.

After about three months of restricting ourselves to kissing, my hands began to roam. She let me know she enjoyed what I was doing. Over time, more and more clothing was removed and we enjoyed the pleasure of being chest to breast. Eventually, my hand slipped into her panties and my fingers discovered the musky wetness between her legs. Her hands discovered my cock. We began giving each other orgasms through touch. She trained me how to touch her and I told her how firmly to grasp my erection and how quickly to move her hand. We were practicing our night moves. I was bold and began kissing her pussy. She found the idea of kissing my cock "gross" and couldn't bring herself to do it. But she loved feeling my tongue on her labia and clitoris. She rubbed me the right way and I teased her clitoris with the tip of my tongue, to and through orgasms.

Six months into dating, S began urging me to enter her. My instincts told me to go for it. My moral code gave me pause. My hormones won. I justified intercourse by telling myself that she would eventually be my wife. She needed no such justification. She just wanted me inside her. She wanted to lose her virginity now.

The first time we tried, I only got my cock about halfway in before the pain was overwhelming for her. I didn't want to hurt her. Despite the pain, S encouraged me to stay inside her, but not to push any deeper. After some gentle movement near the entrance, I pulled out and we gave each other pleasure in our usual fashion.

The following weekend, we found ourselves in the backseat of my dad's Oldsmobile. The clothes fell off quickly. We were both very aroused. She knew what she wanted, and so did I. But I did not want to cause her any pain. S spread her legs and held my cock in position with one hand while pushing on my buttocks with the other - encouraging me to enter her.

She whispered in my ear, "Go slowly, please."

My cock began to enter and S gasped.

"Am I hurting you?"

"No... your cock feels wonderful. Keep pushing."

She was wet and I was hard. I pushed in as far as I had been the week before and checked with her. No pain. I withdrew slightly and gently thrust inside her again. After several more slow but firm thrusts, my cock was fully buried inside her receptive pussy. We shared a kiss and then began moving our hips, engaing in the primordial dance that requires no lessons.

During the next few months, we enjoyed making the beast with two backs every chance we could find. S took to sex like a duckling takes to water. We were both loving the experience of NRE.

A couple of months later, my family took a two week vacation to Florida. When I returned, I went on a date with my girlfriend as soon as possible. She was delighted to see me. I told her about my trip and she told me about what she had been up to during my absence. During the weekend I was gone, she had been invited by some of her girlfriends to go to a "kegger" down by the river, just outside of town. She began telling me about an 18 year old "football star" who was at the kegger. He had been drinking beer and began flirting with her in the flickering light of the bonfire. I knew who he was but we weren't friends, or even acquaintances. I'm not sure whether he knew she had a boyfriend. All he knew for sure is that she was looking good beside the fire.

As her story progressed, she told me that after some chitchat he became very direct and asked her to have sex with him.

I didn't know where her story was going next, but that was my first taste of the angst and the razor's edge of eroticism associated with the possibility of being a cuckold. I had no words for what I felt but when she told me he asked her to have sex with him, my cock became erect. I was anxious but also very aroused by her story.

She went on to tell me that she declined his offer, which I'm sure was true... but her story planted a seed... the first seed of erotic pleasure created by imagining my partner enjoying sex with another man.

Assuming readers are interested, I would be happy to continue my tale about my erotic evolution toward being a cuckold. Feedback appreciated.

Long Lurker 34
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Re: Evolving as a cuckold - through the seasons of life

Unread post by Long Lurker 34 » Tue Jul 09, 2024 3:36 pm

The Owl wrote:
Tue Jul 09, 2024 3:12 pm
I'm 69 now... the autumn of my life. When I was 16, I was madly in love with my HS sweetheart in a small Midwest town of about 3,000 people. My girlfriend (I'll call her "S") was 15. We were both virgins. Looking back at our HS pictures, I was reasonably handsome. She was beautiful, vivacious, and exuded female erotic appeal.

My dad was a minister and had given me a lot of religious messages about sex, such as "I expect you and the woman you marry to be a virgins until after you are wed..." that sort of thing. I did not feel deeply connected with the church, but I had absorbed enough fundamentalist morality to integrate what he was telling me about sex into my personal moral code.

My girlfriend had not been raised in a very religious family. Her mother got pregnant when with her older sister when the mother was about 17 years old. Three months later, her parents got married and had their first baby six months after the wedding. Having a baby out of wedlock in those days was verboten. In those days, it wasn't unusual for the first child to be the result of a shorter pregnancy than each follow-along child. Everybody knew what had happened but everybody pretended as if it hadn't.

During our first three months of dating, S and I spent a lot of time "parking." We discovered the pleasures of French kissing. Our lips and tongues discovered each others necks and ear lobes. We were torturing each other with arousal, without release.

After about three months of restricting ourselves to kissing, my hands began to roam. She let me know she enjoyed what I was doing. Over time, more and more clothing was removed and we enjoyed the pleasure of being chest to breast. Eventually, my hand slipped into her panties and my fingers discovered the musky wetness between her legs. Her hands discovered my cock. We began giving each other orgasms through touch. She trained me how to touch her and I told her how firmly to grasp my erection and how quickly to move her hand. We were practicing our night moves. I was bold and began kissing her pussy. She found the idea of kissing my cock "gross" and couldn't bring herself to do it. But she loved feeling my tongue on her labia and clitoris. She rubbed me the right way and I teased her clitoris with the tip of my tongue, to and through orgasms.

Six months into dating, S began urging me to enter her. My instincts told me to go for it. My moral code gave me pause. My hormones won. I justified intercourse by telling myself that she would eventually be my wife. She needed no such justification. She just wanted me inside her. She wanted to lose her virginity now.

The first time we tried, I only got my cock about halfway in before the pain was overwhelming for her. I didn't want to hurt her. Despite the pain, S encouraged me to stay inside her, but not to push any deeper. After some gentle movement near the entrance, I pulled out and we gave each other pleasure in our usual fashion.

The following weekend, we found ourselves in the backseat of my dad's Oldsmobile. The clothes fell off quickly. We were both very aroused. She knew what she wanted, and so did I. But I did not want to cause her any pain. S spread her legs and held my cock in position with one hand while pushing on my buttocks with the other - encouraging me to enter her.

She whispered in my ear, "Go slowly, please."

My cock began to enter and S gasped.

"Am I hurting you?"

"No... your cock feels wonderful. Keep pushing."

She was wet and I was hard. I pushed in as far as I had been the week before and checked with her. No pain. I withdrew slightly and gently thrust inside her again. After several more slow but firm thrusts, my cock was fully buried inside her receptive pussy. We shared a kiss and then began moving our hips, engaing in the primordial dance that requires no lessons.

During the next few months, we enjoyed making the beast with two backs every chance we could find. S took to sex like a duckling takes to water. We were both loving the experience of NRE.

A couple of months later, my family took a two week vacation to Florida. When I returned, I went on a date with my girlfriend as soon as possible. She was delighted to see me. I told her about my trip and she told me about what she had been up to during my absence. During the weekend I was gone, she had been invited by some of her girlfriends to go to a "kegger" down by the river, just outside of town. She began telling me about an 18 year old "football star" who was at the kegger. He had been drinking beer and began flirting with her in the flickering light of the bonfire. I knew who he was but we weren't friends, or even acquaintances. I'm not sure whether he knew she had a boyfriend. All he knew for sure is that she was looking good beside the fire.

As her story progressed, she told me that after some chitchat he became very direct and asked her to have sex with him.

I didn't know where her story was going next, but that was my first taste of the angst and the razor's edge of eroticism associated with the possibility of being a cuckold. I had no words for what I felt but when she told me he asked her to have sex with him, my cock became erect. I was anxious but also very aroused by her story.

She went on to tell me that she declined his offer, which I'm sure was true... but her story planted a seed... the first seed of erotic pleasure created by imagining my partner enjoying sex with another man.

Assuming readers are interested, I would be happy to continue my tale about my erotic evolution toward being a cuckold. Feedback appreciated.
TO - Always enjoy learning of posters 'origin' stories. Please continue. :up: :up: :D

Handsome63
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Re: Evolving as a cuckold - through the seasons of life

Unread post by Handsome63 » Tue Jul 09, 2024 5:19 pm

I'm all ears...or eyes. Yes, I'd like to learn more. I'm wired the same way and I can't figure out why.

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

Unread post by guitarman » Wed Jul 10, 2024 5:14 am

I love your writing style. Your story is reminiscent of my teenage years. I would love to hear more from that time in your life.

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

Unread post by The Owl » Wed Jul 10, 2024 5:48 am

It looks like my story posted twice in the Cuckold Forum and a total of six people have commented (three to each of the two posting).

I have asked the moderator to take down one of the two threads, one to leave just one.

My apologies for the technological glitch. I hope it gets fixed soon to avoid confusion.

In any case, thanks for reading the first "chapter" of my retrospective.

The Owl

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

Unread post by Lucky Dog » Wed Jul 10, 2024 5:49 am

Glad you got that fixed - it's a great start to your long time story!
Good sex is usually the best and quickest way to end marital virginity.

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

Unread post by ucaneffher » Wed Jul 10, 2024 6:04 am

That sounds incredibly similar to my story. Would love to hear the rest!

US31
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Re: Evolving as a cuckold - through the seasons of life

Unread post by US31 » Wed Jul 10, 2024 6:07 am

Very well written. You have written my story.
I will stay tuned!

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

Unread post by shadowtantra » Wed Jul 10, 2024 10:53 am

echoing others and appreciate the time that you can take to share your story!

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

Unread post by The Owl » Thu Jul 11, 2024 12:35 pm

I accidentally posted this story twice. I am going to use this thread to continue the story (when I get to it). I am not going to post to the other thread. Thank you for using this thread for any responses.

The Owl

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

Unread post by The Owl » Fri Jul 12, 2024 12:45 pm

Thanks for the feedback and encouragement to continue.

I have decided to tell my tale in bits and pieces... not in pure chronological order. Some of the bits and pieces will have a strong cuckold theme. Some will simply be erotic experiences along the path of life. Some involve incomplete erotic experiences... flirtations that were never consummated. The common denominator will be "through the seasons of life."

Fast forward about 3-4 years from my high school sweetheart story. We broke up before I went to college. I’ll save that story for another time.

I had been in college for two years in the midwest and then decided to take a year off to live in Holland... long before a "semester abroad" was stylish. Upon my return, I lived for a few months with some male friends in an old rental house in a neighborhood a mile or two from the university. Three of us from the house had met two "belly dancers" from California who had come to town to dance at a local bar. The dancers liked our male energy and playfulness. We asked them if they would like to join us at a park in town in the next few days for a picnic outing, some frisbee throwing, etc. They loved the idea. One of the dancers was clearly interested in one of my friends. The other dancer remained a free agent, without picking me or the other friend as a fling partner.

At the end of the day, we ended up back at the rental house... two women and three men. The "couple" who had already paired off headed to his room for a night of mutual pleasure. Both dancers were beautiful and engaging. The one who wasn't paired up had dark hair and coffee colored skin, suggesting a Mediterranean heritage, although she spoke English as her first and only language. She was slender, exotic, and very attractive. Her belly dancing had aroused me at the bar. She had also aroused my friend who was also still in the mix. My friend had grown up in New York City. He was street tough, and very athletic. I had more of a thoughtful, mellower presentation, with shoulder length hair and a kicked back style of dealing with the world around me. Stated differently, he was alpha. I was beta.

My friend and the dancer remained standing in the living room. He was flirting with her, including touching and tickling her to the point she would occasionally withdraw and ask him to stop. Their interaction was playful. Her withdrawals didn't communicate "no" to anybody in the room. I sat on the couch, listening to music while watching their flirtation.

Without any specific action on my part, she withdrew from him and snuggled up next to me on the couch. I put my arm around her, quietly welcoming her closer. The moment felt good to both of us. But my friend was relentless. He kept touching her and tickling her. She tucked in closer to me, suggesting she had chosen me over him. He didn’t stop. He grabbed her hands and somehow got her to stand back up. He moved in close to her and told her in a very dominant voice, "Come with me to my room." His alpha moves prevailed. She said nothing more, glanced at me and made eye contact with her tender eyes as she walked hand in hand with him to his room, leaving me alone on the couch. Soon, I could hear the sounds of their sex coming from his room. She was very vocal during sex and through her orgasms. I was alone, but the experience was very arousing. I wondered if she was having any thoughts about me as he gave her pleasure.

She and the other dancer went home later that night. I never saw her again after she walked toward the bedroom with my friend. My friend told me the next morning, “That’s how its done” or something to that effect. The competition for her attention, and his eventual success, didn’t disrupt our friendship in any way. He had played the alpha role and I had been the beta. He savored the pleasure of her pussy. I was left on a lower branch of the tree, without access to the pleasure of a woman’s pussy. I wasn’t exactly a cuckold in that situation because there was no ongoing relationship between her and me. Nonetheless, there was a very clear dynamic of being the beta, the cuckold at the end of that evening.

I wonder what would have happened if I would have said to her, “Enjoy… I’ll wait here for you to return to me…” when she left the living room. I might have had my first reclamation experience… silky seconds. Who knows? I was too inexperienced to even begin to think along those lines as she walked away with the alpha. But I’m guessing if I had spoken up, she would have come back to me after she had tamed the alpha, and we would have enjoyed a tender tryst with each other.

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

Unread post by isinlarsa » Fri Jul 12, 2024 1:42 pm

Ah yes, The missed opportunity. Could've, would've, should've. It's also coupled with the fantasy of having "your girl" taken away and fucked by an alpha male before you have had sex with her. Your first time having sex with her is to reclaim her after another man has fucked her.

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

Unread post by gruenberg » Fri Jul 12, 2024 10:12 pm

It is interesting how many different ways exist that brought us here. By "here" I mean the forum, on the one hand, but also the life in which we find ourselves. In the Owl`s case it was already developed in his teens, when starting this wounderful path of sexuality.

In my case it was completly different. If a girl had told me in my youth that she would have liked to, or had, made out with someone else, it would have been a disaster for me and I would have been far from arroused. In my student days i had lots of sex with different girls and this all came because i was cheated by my girlfriend and immidiately left her, as i found out.

What brought me here was my now wife and her evolution to a hotwife.
the long stony way: viewtopic.php?f=6&t=57837

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

Unread post by wannabecUKold » Sat Jul 13, 2024 1:54 am

The Owl wrote:
Tue Jul 09, 2024 3:12 pm

The following weekend, we found ourselves in the backseat of my dad's Oldsmobile. The clothes fell off quickly. We were both very aroused. She knew what she wanted, and so did I. But I did not want to cause her any pain. S spread her legs and held my cock in position with one hand while pushing on my buttocks with the other - encouraging me to enter her.

She whispered in my ear, "Go slowly, please."

My cock began to enter and S gasped.

"Am I hurting you?"

"No... your cock feels wonderful. Keep pushing."

She was wet and I was hard. I pushed in as far as I had been the week before and checked with her. No pain. I withdrew slightly and gently thrust inside her again. After several more slow but firm thrusts, my cock was fully buried inside her receptive pussy. We shared a kiss and then began moving our hips, engaing in the primordial dance that requires no lessons.
I thought this was a beautiful description of a young girl losing her virginity to her boyfriend in a loving context.

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

Unread post by The Owl » Sat Jul 13, 2024 9:55 am

Thank you wannabecUKold...

She was not the only one losing her virginity. We were both complete novices. But we found our way.

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

Unread post by The Owl » Sat Jul 13, 2024 12:12 pm

Back to high school.

S and I continued making love with one another like bunny rabbits. Thankfully, she didn’t get pregnant. Then August came. I was going away to college in September and she still had a year of HS to complete. I started picking up a strange vibe from her… distance I suppose. A week after I began experiencing a feeling of distance, we went on a date and she told me we are done… finished… over. She told me not to call her or come to her door. Basically, I was banished from her life. Using today’s vernacular, I was ghosted. I felt crestfallen… deeply saddened… abandoned.

I went on a date a few weeks later with another girl who had expressed some interest in me. The experience felt empty, staged, meaningless. There was nothing romantic, or even slightly erotic about the date. I was relieved when that date was over.

I went to college, wrote S a letter, and never heard back. I missed her deeply. In October, I went back to my hometown. I happened to see S’s cousin, Amy, whom I didn’t know all that well. S was slender and moved like a cat - she was a dancer by nature. Her cousin was Rubenesque… not obese but volumptuous. Amy invited me to join her, her female friend (Ann - an attractive blond), and Amy’s older boyfriend for a gathering at the boyfriend’s house on Saturday evening. I thought I might learn more about how S was doing and why she had broken up with me from Amy so I gladly accepted.

Ann’s boyfriend had apparently experienced a brain injury in a MC accident a few months earlier. The four of us drank a few beers and were feeling no pain. The alcohol seemed to hit Ann's boyfriend quicker and harder than the rest of us - probably due to his recent brain injury. Amy said she wanted to talk with me alone. We stood up and she led me by the hand into a tiny spare bedroom that wasn't much larger than the queen-sized mattress on the floor. We lay on the bed, propped our heads on the pillows, and began talking.

"How is S doing?" and “Why did S break up with me.”

Amy patiently replied, “She’s young and doesn’t want to be tied down. She wants to fuck every attractive guy in the county before she graduates from HS. This is her time to be free, to explore.”

I learned many years later that Amy and S were not close and that Amy didn't have any idea why S broke up with me. Amy was talking more about herself than about S. But at that moment, I was sure Amy knew exactly what S was thinking, feeling, and doing. It all sounded credible.

I was stunned and didn’t know what to say or do.

Amy rolled in closer and said, “And I want you tonight.”

We began kissing and touching each other intimately.

Things got weird.

Ann opened the door and entered the bedroom. She said,

“He’s in his bed asleep. Looks like you two are having fun. I’m going home now. You two can stay as long as you want.”

Amy repied, “Come over her Liz and give me a hug.” I was confused by the name “Liz.”

Ann immediately climbed onto the bed, supporting herself with her arms while perched above us.

“I’d love to Ashley.” Again, more confusion. "Ashley?" I thought to myself.

As I was processing the names, Ann leaned in and kissed Amy on her lips - an erotic French kiss. She then moved her head over and kissed me on the lips. The kiss felt delightful but I was stunned and fearful that Ann’s boyfriend would wake up, find the three of us in the spare bedroom, and lose his shit. He was bigger and stronger than me and I knew nothing about him except that he had been drinking and had a history of a brain injury. This was his house and I was on his mattress kissed his girlfriend.

Amy said, “You are welcome to stay. We're just getting started.”

My anxiety rose and I said, “What if he wakes up and hears us?”

Ann replied, “Once he’s asleep, he doesn’t wake up until morning. But don't worry, I’m leaving so you two can enjoy each other.” Ann kissed Amy again, slight longer and more passionately than the first kiss. Then, she pulled back, giggled, and told Amy, “Have fun, Ahsley!”

She slipped out of the bedroom and we both heard the front door close behind her.

I turned to Amy and said, “Liz? Ashley? I’m confused.”

“Oh that... we’ve been reading an erotic novel together. The two women in the book are named Liz and Ashley.”

Amy went on to explain the novel was about two women who enjoy seducing men to join them in threesomes. I asked whether she and Ann had every done so, for example with Ann’s boyfriend. Amy replied, “No... but we almost did tonight.” Amy was in the mood to kiss, not to talk. Our lips and tongues met again.

Soon we were naked and having sex with me on top. Amy was very orgasmic and I had no difficulty staying hard. But I was nowhere near having an orgasm. She kept cumming and I kept pumping. After we had been fucking for at least a half hour, Amy sucked on my earlobe and said, "God you're good. Now it's your turn to cum. I've never been fucked so long and well in my life. Thank you."

I wasn’t sure if I was going to be able to cum inside Amy. But then I started fantasizing that I was having sex with S. I quickly started climbing the wall of orgasm and was finally thrown over the cliff, into the abyss of pleasure. As my body spasmed, I heard myself groaning S’s name near Amy’s ear. She didn’t respond and I was never certain whether she heard me utter her cousin’s name or not.

After we came to our senses, Amy said, “That was fun. Let’s do it again sometime.” We never did.

During Christmas break, I saw Ann at a church gathering and we chatted superficially. We did not speak about my evening with Amy, but I’m sure the two of them talked all about it. At the end of our conversation Ann flirtatiously said, “You and I should get together and do something fun.” I replied, “Sounds good…” We never did. I don’t think I ever saw Amy or Ann again after that.

I was still deeply attached to S emotionally and was crestfallen about her decision to end our romance. The seed had been planted in my mind by Amy that S was fucking other guys and that she wanted to be fucked by every attractive guy in the county. I couldn’t make sense of any of it.

45 years later, S and I began communicating again through the internet. She told me things that I never knew that helped it all make sense. But I’ll save those details for another time.

Regarding the cuckold dynamic, I'm not certain I found Amy's news about S (which was inaccurate) arousing. I undoubtedly fantasized about S while masturbating at that age. And, I'm certain I fantasized about her having sex with those other guys. But a dominant them was my feelings of sadness that our relationship was over. Each experience we have in life contributes to who we became over time, who I am today.

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

Unread post by The Owl » Sat Jul 13, 2024 12:21 pm

My apologies for the length of my tale. If you're enjoying reading it, let me know. I don't want to be posting stuff that others feel is irrelevant to the "cuckold forum". Feedback appreciated.

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

Unread post by sdbuffalo » Sat Jul 13, 2024 3:47 pm

My apologies for the length of my tale.
Don't apologize. Please continue with as much information as you feel comfortable! Very interesting history, and enjoyable. Thank you.
In my Universe, any question may be asked.... But, answers are always optional.

lanceHarden25

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

Unread post by lanceHarden25 » Sun Jul 14, 2024 1:31 am

The Owl wrote:
Sat Jul 13, 2024 12:21 pm
My apologies for the length of my tale. If you're enjoying reading it, let me know. I don't want to be posting stuff that others feel is irrelevant to the "cuckold forum". Feedback appreciated.
This is a terrific retelling of your story and it gives insight into how your cuckold yearnings might have originated. Please continue and don’t spare any detail.

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

Unread post by The Owl » Sun Jul 14, 2024 5:09 pm

As a freshman in college (and a young one at that), my sex life primarily came in two sizes:

1. Regular-size (which amounted to virtually no accesss to pussy); and,
2. Fanta-size.

As is true for many if not most young males suffering from testosterone poisoning, I spent a lot of time fantasizing. I continued to yearn for my HS sweetheart and did my best not to feel too despondent about her "fucking every attractive guy in the county." I missed her deeply. I had justified losing my virginity by seeing her as my future wife. She certainly had no intention of being my future wife, not even my friend.

I didn't want to rub salt in the wound in my heart by going back home for the summer, so I decided to get a job in the city where I was attending the university. An acquaintance from college got an apartment and invited me to share it with him. It was on the second floor of an old brick building that had never been renovated since it was built decades earlier. My bedroom was the living room. My bed was in the wall - a fold down Murphy Bed. I never found Murphy in the bed, but everybody told me it was his!

The roomate - Juan - had the only bedroom. He was a suave Hispanic guy who successfully flirted with the woman - Jen - living across the hall. Soon, he started bedding her. I was relegated to the living room where I got to listen through the wall to Jen moaning with pleasure, while enjoying sex with Juan.

One evening Jen brought a girl with her to our apartment - Felicity. She was 18 yo, attractive with a very comely body. There was a toughness to her - a demeanor that suggested she was streetwise, if not hardened. She disclcosed that she had spent the last couple of years in a girl's reform school (kiddie jail for females). She had done something bad enough to be locked up for two years. I did not ask what she had done nor did she talk about it. She knew Jen from before doing time and had sought Jen out in the community immediately after her release. Felicity hadn't been with a guy for two years and made it clear that she was ready to catch up on lost time. After the usual chitchat as a group, Jen and my roommate headed to his bedroom. I was on the couch with Felicity. I was attracted to her, but was also very inexperienced. Would she be offended if I made a move? She knew exactly what she wanted and took the lead. She asked me to show her the Murphy Bed. I pulled it down. She pulled me down and giggled. We kissed and began disrobing. Soon enough, Felicity and Jen were each moaning through the thin walls between sex, as each of us savored the pleasures of that hot summer night.

About an hour or two later, Felicity and Jen departed our apartment and walked four feet across the hall to Jen's apartment where they slept.

I didn't see Felicity again during the following week. I asked Jen about her and she assured me, "She'll be back, I'm sure."

The following weekend evening, there was a knock on our door. Jen and Felicity were at the door with smiles on their faces. Behind them was a tall streetwise black guy whom I had never seen before. All three entered. My roommate and Jen engaged in their usual flirtation. I wasn't sure what to assume about Felicity, but it didn't take long for Felicity to tip her hand. She began flirting with the other guy. He began putting his hands on her, including touching her ass which was covered by a hot miniskirt. His touch and her responses to him let me know that the two of them had already enjoyed sex together, and that they were going to do so again... soon. No pussy for me.

Jen and my roommate headed to his bedroom. Felicity asked Jen for the key to Jen's apartment so she could head back over with her new lover. Moments later, I was left in the living room alone. My roommate and Jen were making their familiar noises through the wall, and Felicity and her streetwise lover were next door, singing from the same sheet of erotic music.

I saw Felicity in the hall a few times after that. She was friendly toward me but her behavior made it very clear that my ticket had already been punched - it was a one-way ticket, with no return fare to be punched. She was now getting what she wanted, what she needed, from her new streetwise guy, who was bigger and tougher than me.

I moved back to the dormitory in the fall. Felicity was far too hardened, streetwise, and experienced in comparison with me. At that point in my development, I was still wet behind the ears, and barely knew how to interact with females other than my HS sweetheart who was no longer part of my life. Felicity and I enjoyed one night of pleasure, and then she flagrantly paraded her new lover in front of me. He seemed to be giving her what she wanted... which turned out to be one more tiny step down the path of cuckoldry.

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

Unread post by jane » Sun Jul 14, 2024 6:03 pm

so interesting and i'm on the edge of my seat, even though it's real and not theatrical.

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

Unread post by The Owl » Sun Jul 14, 2024 9:31 pm

Thank you Jane... More to cum...

The names have been changed to protect the guilty. But the truth is the truth.

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

Unread post by The Owl » Sun Jul 14, 2024 9:42 pm

"Owl... remove my panties.
Spread my legs.
Guide him to my waiting labia.
watch him pleasure me.
Let it be your pleasure
Let you balls be blue
And your libido be hot.
Maybe you'll cum... or maybe just me.
Stay on your limb and hoot as you smell sex on the floor of the forest.
It's silky... It's musky... a bucket of fuck.
enjoy.
then lick up the mess.
try to understand why, why I am the watcher, the smeller, the taster.

Johng1953
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Re: Evolving as a cuckold - through the seasons of life

Unread post by Johng1953 » Sun Jul 14, 2024 11:44 pm

I'm enjoying your story and the way you are telling it, thank you.

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

Unread post by Long Lurker 34 » Mon Jul 15, 2024 7:18 am

The Owl wrote:
Sat Jul 13, 2024 12:21 pm
My apologies for the length of my tale. If you're enjoying reading it, let me know. I don't want to be posting stuff that others feel is irrelevant to the "cuckold forum". Feedback appreciated.
TO - Quite. I find it really interesting how people get to where they got. There many different paths that have been taken and none are identical.
- I can truly empathize with you for when you were a young guy and lost S, really cutting to the quick. I had something happen too that caused tremendous hurt at that age.
- Please continue.

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