I Have a Confession to Make

by CindyUSA

Caution: This Coming of Age Sex Story contains strong sexual content, including Consensual, CrossDressing, Fiction, First, Masturbation, .

Desc: Coming of Age Sex Story: This is a story of fiction but based on facts researched from the Internet. Many men start cross-dressing pre-teen. Many cross-dressers starts by using woman's clothing to jack their cocks. From there man men enjoy putting on the cloths of woman and enjoy looking like them and the relaxing feeling the derive cross-dressing

I do not claim to be a grammar expert, and as such you will find some grammatical errors in this story. The errors can be the switching of tense, spelling errors, or typos. I ask if you find an error please to send me an email, so I can correct and make the story enjoyable for others.

This is a story of fiction based on facts researched on the Internet.


This text file contains sexually explicit

material. If you do not wish to read this

type of literature, or you are under age



I have a confession to make

I have a confession to make. I am a male, and I like to dress in woman clothing. I started cross-dressing when I was a teenager. My father had a garage office. My father's office, it was off-limits. As any teenager, I was curious about my father's office, so one day, I sneaked in order to look around. I open one of the desk drawers and found a stack of magazines. The cover shown a skimpy clad woman. The name of the magazine was in Playboy. When I opened the magazine, there were pictures of the naked women. My eyes glued to the pictures, first was my time I saw naked breasts. I took one of the Playboy going to my room to look at pictures of the naked women. The Playboy had cartoons with captions that I did not understand. A few nights later something strange happened.

The details of the dream remained vague. The dream I remember was an impression something or someone had touched my penis. I woke up shaking. Half asleep I slowly became conscious of my disturbing dream. My dream was of the naked women shown in the Playboy. My parents told me it was bad to see a nude woman. Telling my parents about my weird dream would be inviting their displeasure. I turned the desk lamp on to see the wetness between my legs. My PJ front was wet, and the sheets were wet. I panic and thought I had wet the bed. I felt afraid because the last time I wet my bed was in first grade, and now I was in the seventh grade. Last time I wet my bed I resulted in a spanking.

Pulling my PJ off, I saw the wetness as white and gooey. Touching the white and gooey stuff it felt more sticky than wet. At first, I thought I had peed. I bent over and smelled my PJ. It did not smell like pee. Whatever it was; it was all over my PJ and sheet. I removed the wet sheet and draped it over a chair to dry. I wrapped myself in a blanket, turned off the desk lamp and fell asleep. The next morning the sheets were dry; I made the bed as if nothing happened. My PJ went into the dirty clothes hamper. Embarrassed about wetting my PJ, I did not want anyone to know.

My dream was confusing and disturbing to me. My first dream, was of a woman with big breasts with pink centers, just as the Playboy pictures. The curious event, the woman in my dream had a little penis. I had never seen an actual live naked woman and did not know what they had between their legs. The Playboy pictures showed the woman with their legs shut and lacked any detail what a woman was like there. Years later I realized it was my mind filling in the blanks for what I did not know. My mind remembered the naked woman pictures I had seen in Playboy magazine. My dream was a combination what I have seen in the Playboy and what I knew about my body. Looking back on my first wet dream the vision of a naked woman with a penis was puzzling.

In later dreams, I remembered my penis touching a blanket; another time it was a hand. I was not sure whose hand, just a hand from nowhere. Another time I dreamed I was in the shower and when the water touched my penis. Each time I woke with this creamy gooey wetness between my legs. These dreams did not happen every night but several nights a week. One dream had me standing next to my teacher was wearing an azure dress, as the last time I saw her. In the dream, I was pushed into her, my penis contacting the azure dress. I woke up drenched again. Another wet dream was about my older cousin Amy. She was three years older than I and was already in high school. The strange dream was not about Amy but her clothing. I do not remember much it was something about her clothes. I realized the dreams had something in common. I woke up at the moment my penis touched something. What my penis touched was clothing.

I had these dreams several times a week. The dreams were vivid then faded into an unclear memory. I remember my dreams were of naked women but with little penis. My dreams were not about sexual intercourse; I had no knowledge anything intercourse. The dream was what I knew, naked Playboy woman and some with little penises like mine.

I overheard two older boys mentioned wet dreams and reasoned that my dream was a wet dream and what I experienced. The two boys' conservations didn't say anything about what wet dreams were.

I had always enjoyed reading and loved going to the library. I knew the library would have information about a wet dream.

Definition: "wet dream."

Wet dream: an erotic dream resulting in orgasm and in the male with ejaculating semen

I did not know what some of the words meant.

Orgasm: intense or paroxysmal excitement; especially: an explosive discharge of neuromuscular tensions at the height of sexual arousal. Usually with ejaculating semen in the male and by vaginal contractions in the female.

The word ejaculation repeated; I looked up that meaning.

Ejaculation: an act of ejaculating; specifically: a sudden discharging of a fluid from a duct

And semen another word I did not know.

Semen: a viscid whitish fluid of the male reproductive tract consisting of spermatozoa suspended in secretions of accessory glands (as of the prostate and Cowper's glands)

At least, I knew that my wetting the bed was semen. I would have the most vivid and weird dream, which caused me to wake to an orgasm ejaculating semen. I still was not sure what all the words meant. The words were defined in the dictionary; I reasoned that it was something normal and must happen to other boys. I needed to learn more about wet dreams.

In a book called A Boy's Book About Growing Up, I read this,

Boys sometimes release semen or "ejaculate" while they are asleep. This is called a wet dream. For many boys, the first wet dream is the first-time semen comes out of their body. They will probably wake up and find a damp patch in the bed or on their clothes.

If you do not know about wet dreams, this can be confusing and worrisome. You might think that you have wet your bed, or that you are bleeding or sick. However, you will see the fluid is milky white, not like blood or urine.

Wet dreams only happen when you are asleep. If you nap during the day, you could possibly have a wet dream, but most boys have wet dreams at night when they are asleep. Many boys who wake up to find that they have ejaculated recall that they were dreaming about something sexual. Nevertheless, you can have a wet dream even if you have not been having a sexy dream.

Most boys find wet dreams embarrassing. It's okay to feel embarrassed, but remembers that wet dreams are common during adolescence. Not every adolescent boy has wet dreams, but most do.

A boy cannot stop himself from having wet dreams. They are natural and normal. They are the way that your body makes room for new sperm from the testicles. Having wet dreams does not mean that you should have sex.

In the same book I read about masturbation

Masturbation is the act of touching one's own sexual organs, the penis, vagina, breasts or other parts of the body that are sensitive to sexual stimulation. Masturbation is another way that people sometimes express their sexual feelings.

Both men and women can relieve sexual feelings and experience sexual pleasure through masturbation. In fact, most people masturbate during their lives, but boys masturbate more often than girls. Some girls and boys start masturbating when they are children and continue to do so all their lives. Some start during puberty; others start when they are adults. Other people never masturbate, and some people feel that having sexual fantasies and masturbating is in conflict with their religious or moral beliefs.

In my teenage mind, I was beginning to understand. I would get erections all-day long, sometimes when the classroom and I would be embarrassed should someone know, especially a girl. But my penis was not that large, and it was easy to hide.

After I read about masturbation, I wanted to try it. I wanted to watch my orgasm when awake and to see an ejaculation. Until now, I ejaculated when asleep. With the bedroom door shut and the desk lamp on, I was ready try this masturbating thing. The first touch of my hand to my penis instantly made me hard. Touching my little erect penis felt strange causing my penis to tingle. My finger rubbed the penis tip, called the glan. The glan was purple with the shaft pink. Being twelve my balls did not hang far, with my nuts still close to my body. Moving my hand in various ways kept my penis tingling, but nothing happened.

After a few minutes of masturbation and nothing happened, I gave up, turned the light off and went to sleep. Drifting off to sleep, I wondered why I did not have an orgasm. Minutes later I had a vivid dream waking with wet PJ. The next day was Saturday; wash day so took off my PJ but left the sheet on the bed. I slept next to the wet spot.

.... There is more of this story ...

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Story tagged with:
Consensual / CrossDressing / Fiction / First / Masturbation /