How I Became a Cuckold, Episode 1: You Never Forget Your First Time

Prolog

This story is very much true. Only the names and some minor details have been changed to protect the privacy of myself and others. If you have some questions about what is or isn't precisely true, feel free to e-mail me to politely ask. I prefer to answer your questions privately by e-mail rather than in comments. But general comments are very much encouraged and greatly appreciated.

You Never Forget Your First Time

The summer after my senior year of high school, about 2 weeks before I was to leave for college. My girlfriend of 3 years, my first love (and first sexual experience) introduced me to the intense emotional experience of being a cuckold.

We'll call her Kimmy. She was a very sweet, cute blonde cheerleader, competitive swimmer, and pool lifeguard. She had recently blossomed into a hottie who was attracting loads of male attention in her Speedo racing swimsuit, sitting in her elevated lifeguard post at the community pool. It seemed like every guy I knew felt they should come to me to let me know that my girl had become a hottie -- even family members and neighbors. I always filtered their comments and passed them along to my girlfriend because I cared about her and I wanted her to have confidence -- a reality-based confidence.

But I knew I was in trouble when my friend ("frenemy"), Fabio took an opportunity to give me his evaluation of how hot my girl had become in the past year.

Fabio was a year younger than me -- my girlfriend's classmate -- and was far and away the most hunky heart-throb that existed in our town in any age group. He was also a star athlete. Every girl wanted to be with him and every guy wanted to be him. You could feel girls getting wet every time he walked by.

Fabio and I grew up within 500 yds of each other and had known each other our entire lives. We played sports together, our parents knew each other. He was naturally a part of a very tight-knit circle of my neighborhood pals, who were all a year older than him. But because Fabio was SO popular and ... so sought-after, he felt it necessary to eschew the friendship of us older boys in favor of a group his own age in order to protect his public image.

Our group actually had a beer-fueled late-night conversation while camping about how Fabio should be careful not to appear to associate exclusively with seniors but should probably spend more time with his own classmates (juniors). Like some drunken, teenaged Board of Directors, the entire group arrived at this consensus and we gave Fabio our blessing to hang out in public with his classmates and only spend time with us in private.

He was, at times, a vicious rival and at other times a close confidant. Although I never understood why he might see me as a rival and he confided in me but I never confided in him.

There was one incident between Fabio and me that needs to be told to fully understand the events that were about to occur. It happened about 7 years earlier when we were visiting a friend who had moved far away. After a fun day of exploring woods together, four of us were relaxing in our friend's bedroom and Fabio unleashed a polemic directed at me about what a loser I was and how I would always be a loser ... and he would always be superior to me in every way.

It was such an blistering, unprovoked, and ridiculous attack that it didn't even hurt my feelings. It was just bizarre. To this day I cannot imagine what triggered him to attack me in that way. As an adult, I can only guess that he was harboring anger at me simply for my lack of self-confidence and this was his ham-fisted way of communicating to me that my low self-esteem would reduce my prospects in life, which was true. I conquered that beast some decades ago.

But when he started confiding to me about how hot my girlfriend had become, I KNEW I was really in trouble.

About 2 weeks later, my girlfriend told me she had an evening tennis date with her friend, Beth. That was fine with me since I was going out with my friends. But none of that panned out the way I expected.

Around 9:00 pm, after my friends group collapsed, I took spin by the tennis courts to drop in on Kimmy and her friend. Her circle of friends were usually happy to see me drop by, but I usually tried to keep it short so as not to wear out my welcome.

But on this night, I did not find Kimmy with her friend, Beth, at the tennis courts. Instead, I found Kimmy and Fabio playing tennis -- or rather hitting balls back and forth and laughing. Kimmie spotted me and looked alarmed. Fabio looked also.

I immediately knew that this was the end of my run as Kimmy's boyfriend and that from this moment on I would have a different role ... if any at all. It might have been easier if not for my intimate knowledge of Fabio and his motives.

You see, Kimmy was, indeed, a hottie, and I don't doubt that Fabio sincerely found her desirable. But she wasn't exactly in Fabio's league. (I don't generally put people into "leagues", but I knew Fabio well and ... he was very image-conscious.) And I knew that Fabio only had 1 or 2 motives here:  To leave his mark on this new "rookie hottie" and/or to demonstrate that he was superior to me -- that he could take or borrow my girl any time he wanted and there was not a thing I could do about it. And I would take her back.

Kimmy would later tell me that Beth bailed out on their tennis date and Fabio happened to be passing by -- which was totally believable due to the location of the tennis courts between the school and the pool.

There was no question in my mind that Fabio was going to take her someplace and make himself the second guy she would ever lay with -- no question whatsoever.

I was so distraught that I simply turned my car around and headed home. 

When I got home, there was a gathering at my house and my family wanted me to hang out with them. But I was so intensely distracted that I couldn't function and after about 5 minutes I burst into tears and ran to my room.

I was certain that at that very moment, my sweet Kimmy was getting busy with Fabio. And I knew that he would do more that just have sex with her. I knew that he would try to get her pregnant just to assert his superiority over me.

I was right. That night, Fabio took Kimmy back to his sister's apartment, got her drunk and high and they got busy -- very busy. Then he took her home and never called her again.

In the days that followed, Kimmy realized that she had been taken advantage of and attempted to repair our relationship. I couldn't but forgive her. And in retrospect, what Fabio did was simply a repeat of what good-looking guys have been doing for thousands of years. It also happens to be a class-C felony. So I was right to forgive her. She was a victim of a ploy.

But here's where the story gets interesting. Several days later, I still didn't know for sure what had happened. She came to my house, ostensibly to return some things that were mine, as if we were breaking up. But one of my favorite things that I had left at her house were my old cut-off football shorts -- part of a practice uniform. They were snug and laced up the front and looked extremely sexy both on guys and girls -- especially on girls. (Even I had gotten shouts from passing girls when I was jogging in them.)

She showed up wearing my old football cutoffs with nothing underneath. She knew it would both arouse me to see her in them, but also signaled that I was her guy if I still wanted her -- she was wearing my clothing. 

We talked, we both cried, she begged me to forgive her and we kissed.

Kimmy claimed that she couldn't remember much from that night. She wasn't sure if they had had sex or not. She was terribly ashamed because she was a good girl -- an A student, an athlete. I wasn't sure whether to believe her or not. But when she tearfully confessed that she thought she had lost me forever, I knew I would forgive her.

And at that moment -- my feelings somewhat assuaged -- I realized that I had a painful hardon. And I realized I had had that hardon for days since the very first moment I saw her with Fabio. I had been rock-hard the entire time.

Kimmy noticed and put her hand on it and kissed me deeply. "I'll do anything if you won't leave me. I love you so much." she said. She began rubbing my hardon.

"I want to move forward, but I can't stop thinking about him fucking you on the sofa," I confessed.

"Is that why you are so hard right now?" (No denial, just a deflection.)

"Yes, I don't understand it. It hurts, and it burns, but it also makes me so hard."

Kimmy took my hand and moved it toward the laces of my football shorts she was wearing. "Is there anything I can do to make it better? Please, I'll do anything to make it better."

Our kissing intensified and soon I was kissing her breasts and working my way down to her tanned bellybutton with my tongue. Kimmy was moaning softly. I began to undo the belt and laces of the shorts. My heart skipped a beat when I saw she wasn't wearing any underwear.

My penis was throbbing knowing what she had done but what was about to come would fuel my fantasies for many decades afterward.

With only the slightest effort, Kimmy's shorts (my shorts) slipped down to her knees and when I moved to go down on her, her only act of resistance was to stop me and ask, "Wait ... are you sure you can forgive me? Really?"

I continued to go down on her and she was ecstatic, both emotionally and physically. She moaned and wiggled and told me how much she loved me.

Then I moved up to mount her and as I attempted to penetrate her she stopped me cold. "No. Wait. We can't ... I can't do that with you right now. I'm so sorry. Please forgive me."

That's when I realized that my worst fears were a reality. She was worried that Fabio had gotten her pregnant and wanted to defer our sex until she knew for sure.

"Please ... I can't do that right now. I'll do anything else," she rubbed my penis feverishly. It throbbed harder than I had ever felt it with the realization that my sweetie had gotten VERY busy with Fabio and he might still be inside her.

I rubbed the head of my penis against her abdomen and clitoris in an effort to persuade her, but she held fast and denied me actual sex, "Oh god ... please your making me so turned on but you can't be inside me."

She reached over to her purse and pulled out a bottle of hand lotion and quickly slathered it all over my penis. She began stroking it gently.

"Did you do it with him? Did he wear a condom? Did he cum in you?" I fired off questions as she stroked my hardon.

"I ... I don't ... I don't know ... I can't remember everything," she said. I knew she was just trying to protect my feelings.

I was rapidly approaching an orgasm. She took both hands and formed a slippery pocket around my penis pressing it against her pubic area. I began thrusting into her hand and my hips began to buck uncontrollably.

"I can't stop thinking about him being inside you. And getting you pregnant."

No denial came. Her only response was, "Is that why your dick is so hard? Do you like thinking about him doing me? It's Ok ... you can tell me. Please, I'll do anything you like."

"Did he make you pregnant?", I asked, panting as my hips bucked uncontrollably.

"Is that what's making you so hard and excited? Are you thinking about Fabio impregnating me?"

I could tell the idea also made her excited.

"Did he cum in you? Are you pregnant?"

She responded only with moans and intensified rubbing.

Within seconds I shot my load into her hands and collapsed at her side. She seemed to relish having my load in her hands. She collected it all in one hand as I panted and she threw her other arm around my neck and kissed me deeply.

"I'm so happy you still want me. I thought we might never be together again," she said, staring at the evidence in her hand as if she were looking at my desire for her. She had denied me sex and had maneuvered me into doing a tribute for her ... in her hand. Even though I was spent, that detail still aroused me.

"I love you and I can forgive you, but I don't know if I'll be able to stop thinking about you having sex with Fabio," I confessed.

"I've never seen you so worked up and aroused. Is that what made you squirt in my hand?"

"I think so. I've had that hardon from the moment I saw you with him. When I got home I was distraught, and I knew you were having sex with him at that very moment ... but my dick was rock-hard and has been for days."

"Is it bad if you think about that? Does it hurt you?"

"Yes, but it also makes me super turned on. Is that terrible that I get SO aroused thinking about you fucking him?"

"It's ok, sweetie. You can fantasize about whatever you like," she said.

"He's the local hear-throb, every girl wants to be with him. Do YOU like to think about him fucking you on his sisters sofa? About him impregnating you?" I asked teasingly.

"What do you think?" she said with a smirk.

And so things returned to normal. We resumed our dating and had lots of steamy car petting but no actual sex for some weeks. I accepted that she might be pregnant from Fabio. I accepted hand-jobs only for a few weeks. I accepted that my girlfriend would fantasize about fucking Fabio when she was aroused. And I accepted that I would fantasize about her fucking Fabio 100 times a day.

I also accepted that everyone in town knew that Fabio had fucked my Kimmy and many knew that she might be pregnant. The humiliation made me burn every time we were out in public.

But Kimmy was good at comforting me if the humiliation became too much. She would take my arm and snuggle up to me if gossipy people looked at us in that way.

On many occasions, Kimmy would lean in to me in a theater or in the car and feel my hardon. She would ask, "Are you thinking about me and Fabio again? You are, aren't you? You're thinking about him fucking me on his sisters sofa, aren't you?"

And so it was for several more years for us. But for decades these events fueled my sweaty fantasies every time I rubbed one out -- all through college.

In college, however, a new accidental cuckoldress would take Kimmy's place in my fantasies.

But that's for another story.