Evolving as a cuckold - through the seasons of life

[The Owl]

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.

[NSEW1]

Fascinating story. Please tell us about the next seasons.

[Cancun]

Yes, please tell us the whole story.

[takemoment]

I would love to hear your story

[The Owl]

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

[hotpastdawn]

I am looking forward to reading more!

[Hawthorne34]

I’d love to hear more from you.

[venus-can99]

A fascinating start and you paint a wonderful picture with words. Looking forward to reading more

[The Owl]

As mentioned previously, I accidentally posted this story twice. I am going to use the other thread to post the follow-along story. Please respond to that thread rather than this one.

Thank you.