My Development As A Cuckold by Happy Cuckoo at Inkitt
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My Development as a cuckold

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Summary

Stories of experiences in an erotic lifestyle. A marriage with cuckholding, BDSM, and humiliation.

Status
Excerpt
Chapters
11
Rating
n/a
Age Rating
18+

Foundation

When I was a young boy growing into puberty, I’m sure I was much like any other boy. The size of my penis was always a concern to me and of course I measured it often, hoping that each time it would be a little bit larger than the last. To my disappointment I saw no growth spirt that would put my mind at ease. It probably wouldn’t have been such a concern for me at that age but having an older brother by three years, who had pornography magazines for my viewing pleasure. This was a time before the internet so porn magazines were a very hot item for many youngsters growing up. Within the pages were both men and women and as stimulating as it was for me to see the beautiful women, I was a bit distraught to see the men with semi-erections that made me very envious when I compared them to my full erection. I soon realized that the penis I had was all that I was going to get, and what I had wasn’t very much. However, as a pubescent fourteen-year-old, it didn’t stifle my constant urge to masturbate!

Even with a small penis my testosterone was in overdrive. I was an attractive young man with a sense of humor that filled a room. In grade school I had girlfriends that occupied most of my time. Homework, chores, and sports took a back seat to my girl crazed mind! My girlfriends were typical teen crushes with Spring Dances and make out sessions. Although I was very successful with having girlfriends, the size of my penis made me feel uncomfortable with exposing myself to any of them. Even when the opportunity came available at birthday parties when we played sex games like “Spin the bottle” or “Seven minutes in heaven”. Games that many young teenagers play to ignite their fiery rage of hormones. Other couples came out of the closet with experiences to boast about, but I withdrew.

My first three years of high school I was smitten by a girl named Tammy who I met at a lake the summer before our freshman year. She lived in the next town over and I was determined to continue seeing her. She was my first serious girlfriend and she was the girl that took my heart and my virginity. We were fifteen and our hormones were racing. I was in love and every thought was consumed with wanting to be with her. When school started, I would hitchhike twenty-five miles to her house every weekend to be with her. Every day during lunch hour we would talk on the pay phones that were located in our school hallways, and every night we would talk for hours at a time. In some cases, we would be on the phone from the time we got home from school until the time we went to bed. I was absolutely under her spell and she knew it. I was a very jealous guy and so afraid of losing her to another, that I actually believed that if I could keep her on the phone, she would not be able to cheat on me.

Tammy was a highly attractive girl. The type of girl that was built like a woman at the age of fifteen. She was hot and she was wild. She may have taken my virginity but it wasn’t me that took hers. She was experienced and she was a slut. After our freshman year we spent most of the summer at her house. Her mom was a bar maid in a lounge club and was rarely home. We had the house to ourselves and we took advantage of it. There were periods of time we had sex four or five times a day. I was under the belief that she had all she needed. My stamina and constant state of horniness was unmatchable. I hoped that there was no need for her to want anyone else. I found out before too long, that was not the case. As it was, she baby sat for a family in her town that happen to be a neighbor of guy named Tony whom she went to school with. He would go over to visit her during her baby-sitting job and after she put the kid to bed, they would fuck. When I called her at the house she was babysitting at, she told me he would sometimes drop by to say hello. I would ask intensively if she was fucking him and She always denied that anything ever happened between them. She admitted he visited but they only sat and just talked. This happened every time she babysat there. I knew what was really going on and although it caused me to be very jealous and distrusting, I still couldn’t live without her. As I laid in my own bed all those nights while she babysat throughout our sophomore and junior years, and knowing Ronnie was there fucking her, gave me the feeling of deep anguish.

On a night Tammy and I went out to a pizza place with another couple from her school. It was a couple that we often went to the movies with or other various events. When the girls left the table to play music on the jukebox, the guy informed me that Tammy was fucking her neighbor Tony who lived two streets down. He was another guy that Tammy went to school with. When I was told this information, my heart dropped! When they got back to the table I leaned over and whispered “Tony” into her ear. She was taken back with surprise as her face went red and her anxiety level sky rocketed. Needless to say, the night was ruined and we went home to her house to fight about it, saying the typical lines of “how could you do this to me?” and “I thought you loved me”. She of course responded in the typical manner… “I do love you, it was just a mistake” and “It will never happen again.” I had to do something! I knew I couldn’t live without her, but I couldn’t let this go without some kind of action. The next day I walked over to Tony’s house and called him out. I said to him that Tammy told me about the two of you. He said,” you can only believe half of what you hear”. I said half is too much and threw a swing that landed on his jaw. We each through a few more punches with both us connecting. After that, there really wasn’t much I could do short of killing him. Which of course was beyond insane. I said a few choice words to him and went back to Tammy’s. Nothing ever came from that fight. Tony continued to fuck her and I accepted it. It was the feeling of anguish I felt before. Only this time, it felt much easier to accept. She was still my girlfriend that I loved and she knew I wasn’t going anywhere. This went on for the rest of our junior year until she started pushing me away with less time to spend with me. She was ready to move on and there wasn’t anything I could do. I moped for a while but I had friends to hang out with that filled my nights with alcohol and pot that eventually helped me get over her.

I dated a few more high school sweethearts to finish out my senior year. After graduating I decided to become a hairdresser. My Uncle owned a top salon in the city and once I got my cosmetology license, I was feeling great as a single man in a salon full of women. They were everywhere and I was happy! I went out with many of the stylist there. I had many one-night stands with them. My personality was a magnet. I always enjoyed being witty and making the people around me laugh. As I was making my way through the employee line up, I overheard a few of them talking about me in the break room. They were comparing notes and at the top was, “Trey has a really small dick”. Well, it wasn’t any surprise to me, but it was difficult to hold my head high when I was among them.

At this time, I was casually dating Sarina the make-up girl at the counter. She was a tall pretty blonde with a fun personality. I was falling for her and enjoyed our relationship. I had an apartment in the city and she would often come over and I would make dinner for her and of course end up in bed. One night while I was making dinner for her and waiting for her to show up, she called me from her classmate’s house. They were in a college art class together and she happened to be at his house doing body paint on each other. Well, I’m no artist but I did know that body paint art meant creating murals on a naked body. She said they were drinking wine and she wouldn’t be able to make it over to my apartment that night. As I heard them laughing and enjoying themselves, she said she would see me tomorrow as we hung up the phone. Then that familiar feeling of anguish crept in.

She had left her coat at my house from her prior visit. It had her scent all over it and I laid in my bed smelling her scent on the coat and imaging what they were doing. It started to become more than a feeling I’ve learned to accept. I started to realize that I enjoyed the adrenalin that the anguish provided. A kind of angst that filled me with excitement. Not the kind of excitement that brings on an erection, but an excitement that made me drip massive amounts of precum out of my very small limp dick! I remember rubbing my slick natural lubricant over my tip until I got hard. I then masturbated thinking of her getting fucked by her classmate. It was an intense orgasm and I contributed to the anguish I was feeling and the angst that built up inside of me. It occurred to me that there is something that I crave from this feeling of anguish. I was more than willing to accept her art projects with her classmate as long as we could continue seeing each other. We did go out for a little while longer after that night, but a couple more dates went by, then she decided to go her own way.

Soon after, I started dating a client named Carry. She was full of life and lit up a room to the point that she was stealing my thunder. We made a good comedy team. We bounced jokes off each other when we were out and we seemed to be the center of attention. Once again, I was falling hard. She worked at TGI Fridays and did very well in tips with that personality radiating from her. We were very close and I thought I was in love. It was a different feeling for me than any girls I’ve dated before. She worked nights and usually didn’t get out until 2 a.m. Yet I had no concern of her cheating. No jealousy that weighed on my mind. We eventually moved in together and started making long term plans. One morning while lying in bed, she brought up to me that she wanted to take advantage of the TGIF travel program. It was a program that allowed employees to work at other branches while traveling the country. The concept is that an employee simply goes in and asks the manager to put them on an available shift. Since all TGIFs were run the exact same way, no training was necessary. It was a way to travel and make your way while in route. It’s an outstanding program and after hearing her plan to do this with a co-worker, I told her it was a great idea! She was planning on it being for about a month and it sounded like a lot of fun. Then… she dropped the bomb. Her co-worker was a dude she worked nights with. I never met him but I’ve seen him on occasion when I would go in for dinner to visit her. He was a tall good looking guy and like most employees of TGIF, he was outgoing. It was a surprise to her that I was still on board with the idea. I knew I would be jealous thinking about them together, but the thought of the two of them traveling many miles getting to know each other, then stopping at hotels for the night and sharing a room really excited me. It brought back memories of my past when I felt that anguish. A feeling I now actually wished I embraced back then, as I have learned to do now.

The two of them set off on their journey. She called me often and let me know where they stopped for the night as they traveled across country. Her calls had always come at the time he was in the shower. We had our small talk of her travel experiences and the different TGIF stores she worked at. We usually ended the call with it being her turn to jump in the shower. I knew they were fucking into a sweat every night. She was a sex maniac with me, so I didn’t expect her to change her ways. I never let on to the obvious, instead I let her continue to believe that I was so naïve to think that they were just friends. Every night when she called, I capitalized on the angst that was building up in me after thinking about them through the day. After we finished our very pleasant conversation, she hung up knowing she had a green light to have sex without concern of hurting me. As for me, my juices were flowing like they had in the past. I masturbated to the thought of them having a steamy fuck session fresh out of the shower or possibly in the shower. It was extremely exciting for me during that time. After about a month when she got home, we talked about her travels and the fun she had going to parties with other TGIF employees throughout the country. I asked her if she and (her co-worker who I don’t remember his name) had sex. She basically said, “don’t be silly.” Nothing more was brought up about it. Our sex together was more intense for me after her trip. I worked hard to please her, but without prevail. She often told me to go deeper. Unfortunately for me, it was a depth I couldn’t reach for her. She soon got bored with me and my little dick. She moved out of our apartment because she wanted to date other people. It hurt to lose her, however many a times I rubbed it out thinking of those nights when she was getting fucked while I laid alone in our bed. I understood she needed more than I had to give in the cock department. Like every other relationship I had, I was an attentive, loving and loyal boyfriend. I had always been subservient to their needs domestically; I was just unable to satisfy them with a powerful cock. I’m sure the thought of spending the rest of their life not having that satisfaction is more than any woman would want to have to compromise. A sexually fun woman anyways!

It was about a year later when I decided I needed a career change in my life. So, I packed up and joined the military. It was a bold move going from a hairdresser to a structured military life, but something drew me to that change. It was quite different for me, but it ended up being the best move of my life. Not only did I grow as a person, but I met my wife and soul-mate.

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