I Have a Confession to Make

by CindyUSA

Copyright© 2013 by CindyUSA

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

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

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.

I worried that I was doing something wrong when trying to masturbate. Not long after my wet dreams started I was over at my Aunt's house. I went to take a leak and standing there I noticed the laundry hamper overflowing with mostly my Aunt's clothes and what looked to be Amy's clothes. When I saw her pink lace panties with bows, I got an immediate erection. I could not think or understand the visual stimulation and my erection. I finished peeing allowing me to reach for the colorful panties. The touch was so soft, then I grab the panties. I cannot explain why, but I rubbed them on my erection. Wow my penis tingled. The feeling was almost electrifying, and I know that I had to take them home and use them for masturbation.

That night with the door shut and on top of the covers, I bought out of hiding my stolen panties. Not sure if it were the fact, I stole them, or they were Amy's, or they felt so smooth, when it touched my penis but I got an immediate erection. I draped my penis in the panties and moved my hand up and down. Less than a minute I had my first wake orgasm. This time I wanted to watch my ejaculation. I did; I had my penis enclosed in the panty with the tip showing and pointed up toward my chest. I simply moved my hand up and down a few times when I felt something strange occurring, as if I were going to pee but not like peeing. I orgasm; semen squirted from my pee hole. I was surprised when my semen hit my chest and fist, it happened so fast. The semen was warm, white, and sticky. I wiped my semen with the panties in my hand. An indescribable feeling enveloped my body; I felt so relaxed. Reaching up I turned off the desk lamp making my room dark and slipped under the covers savoring my first awake orgasm. Before falling asleep, I remembered hiding the panties under the mattress.

Sunlight touched my face as I tried to remember my actions from the night before. I jumped out of bed, showered, brushed my teeth, dressed, and had breakfast. Today was Saturday and I had agreed to meet my friends at the playground. When I arrived back at home, I found my bed made. Shit, I forgot about the panties. I looked under the mattress, and the panty was gone. Shit. My mother knows. She is going to yell at me. My clean clothes placed on my dresser ready to put away. Between my T-shirts, underwear was something pink. Sure enough, Mom had found the panties, washed them and put them with my clean clothes. She never said anything. I never asked.

From the first time that stole my cousin panties and used them to masturbate I knew I would do it again. At first, I used the panties to rub against my erection. I visited my Aunts again making an excuse to go to the bathroom again. This time I found on top of the hamper a black bra with red bows with matching panties. I had gym shorts on with no pockets. I had to think, how to get them home? I slipped out of my shorts, slipped on the panties. I took off my T-shirt tried to put on the bra. I did not know how to put a bra on; I slipped my arms through the straps when, knock, knock on the door. Shit, I jumped, "Just a minute." I put on my shirt and shorts feeling the material rubbing my nipples and penis. I walked out of the bathroom. Amy was there tapping her foot and looking at me strangely.

She said, "What were you doing in the bathroom for so long?"

Oh God, I said under my breath. She is going to know I took her panties and bra. Maybe, she can see the bra under my T-shirt. I told Amy, "Nothing, just took a leak." I turned and walked away. As I did, the bra strap slipped off my shoulder and was hanging out from my shirt sleeve. When I felt the strap slipped my hand swiftly moved to cover my thief. Oh God did she see? Just keep walking. Amy went into the bathroom and shut the door. I kept walking, said good-bye to my Aunt, got on my bike and headed home with my stolen goods.

I noticed as I was peddling home the excitement I felt for almost getting caught. I felt my heart pounding. I felt the panties rubbing my penis, which made it hard and the bra was rubbing my nipples making them hard. I peddled faster resulting in the silk and lace panties to rub my penis. I pictured my penis rubbing the parties, and it happened. I orgasm; I creamed in my gym shorts. I almost lost control of my bike. My head was spinning while my penis squirting semen inside the stolen panties. Looking down was a visible wetness growing between my legs. I could not go home; I would go somewhere to wait until was dry.

"Hey Matt," I heard a voice approaching from behind me. I recognized the voice as Zack my best friend. Oh shit. I could not let him see the wet spot; he would ask what happened. I did not want to explain the stolen panties, the rubbing of my penis, and then squirting. Zack was on his bike, pulling up beside me; he asked, "What's up Matt,"

I pedaled ahead of Zack trying to think how to cover up my wet spot. Looking around I saw my salvation, the playground sprinklers were squirting water into the air. I could ride my bike into the sprinkles soaking my clothes, covering the wet spot. I said to Zack, "Hey, follow me." Riding my bike into the sprinkler, I made sure I was completely wet, including my gym shorts. Yes, that worked, I was soaked from head to toe. I looked over my shoulder to see if Zack followed me. He was wet as I was. Back on the sidewalk I stopped waiting for Zack to catch me. Oh God, I realized the water had made my T-shirt wet, and I could see the black bar under my T-shirt. Oh God, would Zack notice.

Zack pulled up beside me dripping wet staring at me. I felt his eyes looking at my chest knowing he would ask what was wearing under my T-shirt. How could I explain to my best friend that I stole my cousin's bar and panties? How could I tell Zack my wearing Amy's underwear was so exciting I had an orgasm? I was not sure if Zack knew about wet dreams, ejaculation, semen, orgasm and masturbation. Zack did not say anything. I crossed my arms over my chest to hide my embarrassment. Looking at Zack told me why he had not said anything. His glasses had drops of water all over them. He was farsighted needing glasses to see up close. With his glasses wet, he could not see. Fortunate for me Zack did not discover the wet spot nor the stolen bra and panty. Before I met anyone else, I needed to get home to take off the bra and panties. I told Zack, "I am going home to get into dry things, meet you back here in fifteen minutes."

Zack responded, "OK, Matt." As I paddled away I heard Zack said, "I need to ask you a question when we meet." What question? Did he notice and was waiting to make fun of me? All the way home I worried about what Zack would ask. At home, I went into my room, shut the door and removed my soaked clothes. The bra and panties were dripping soaked. I could not leave the bra and panties wet laying on the floor. My mother did not ask about my first pink panties, but having a matching bra and panties she would have questioned. I was going to have to find a place to hide my stolen girl clothing.

Looking around my room, I looked for a hiding place. Looking at the dresser, I pulled out the bottom drawer. Beneath the drawer was a void three inches deep. A perfect place to hide the bar and panties. The silk material dried fast and now was about dry. I placed the bar and panties in my newly discovered hiding place. My mother would never look here.

I agreed to meet Zack back at the park. Zack said he had a question, but he did not tell me what it was about. Was he going to ask me why was wearing a bar? I had to meet him so if it were about the bra, I would have to stop him from telling others. I do not think Zack would tell anyone, we were friends and friends kept secrets. I met Zack at the playground. No one else was around allowing us some privacy. I asked Zack, "What did you want to ask me." Almost dreading his question.

Zack spoke slowly and clearly as if he did not know how to ask, "Matt, promise not to tell anyone?"

I responded, "Sure Zack, what is it?"

Zack stutters, "Well, uhm; I do not know how to ask or where to start." "I need to ask you, if uhm, if you, well you know, had any weird dreams?"

I was relieved; Zack did not mention noticing me wearing a black bra. I said, "Zack, did you wake and had wet the bed?"

Zack looked surprised then relieved, "Yes; it was not pee'd, but was white and gooey. I had a dream about girls, about my sister. I was in a crowd we were bumping into each other, and I woke up squirting into my shorts."

I smiled at Zack explaining what little I knew. Zack sat there his mouth open, not believing what I was saying, he did not understand the words but was relieved that I knew about the dreams and had them myself. Zack had a hundred questions, which I tried to provide answers. Zack's face showed relief thinking that he was not crazy, that someone else had these wet dreams, and all boys had wet dreams. He worried about having a wet dream about his sister. He was not sure whether this meant he wanted sex with her. I told Zack almost everything but did not mention masturbating with panties and wearing a bra and panties, which has to remain my secret. The next day, Zack was smiling, and I asked him, "Why are you smiling Zack?"

He said that he tried that masturbating, and it worked. He said that he shot loads of seeeeman. Sounding as though he did was not sure how to say the word.

I was almost caught by Amy my older cousin and Zack my best friend. I stole and wore my cousin's bar and panties, as a result I had a wonderful orgasm. I had discovered that wearing woman silky panties and bar and the chance of getting caught had increased my sexual release. I found if masturbate before bed that I would not have a wet dream, and I would sleep soundly.

I was a typical horny teenage masturbating nightly. As my understanding of the women body and sex increased so did my fantasies, and I need to ejaculate. I could get off wrapping my penis in the panties but wearing panties and bra was more stimulating. I would put on the black silk panties and matching bra then would walk in front of the bathroom mirror. I would image me as a woman, with breasts, makeup and a wig.

Sometimes I would picture myself in a dress and heels pretending to be a woman. I found that dressing was an outlet for stress. I felt relaxed from the tension of school reduced. I never wanted to be a woman. A woman did not have a penis, and I liked my penis. I could make my penis have an orgasm, which was the most enjoyable. I was too young to have a girlfriend and in additions, girls were scary.

On some days when I was alone at my house, I would put on the panties and bra walk around pretending to act like the silly girls at school. I would then dress walking around feeling the silky panties rubbing my penis, which makes me hard and the bra fastened around my chest rubbing around my nipples. I would walk around the house rubbing my legs together hoping I would have an orgasm. One day I was alone dressed in my panties and bra, I was sitting on the toilet rubbing my panties like what I imaged a girl would. I had a feeling of being watched and looked around; the bathroom door was shut, and no one was home. At this point, I looked out the window, which faced the house next door but could see an upstairs window. I looked up at our neighborhood widow but saw no one. Our neighbor was a retiree and his wife. Their children would visit. I do not know if anyone saw me dressed.

Ding dong the doorbell rang. Shit, who can that be. I pulled on my shorts and T-shirts. I did not have time to take off my panties or bra. Maybe I should pretend no one was home. However, whoever it was at the door might tell my parents and asked me where I was. OK, I had to answer.

I opened the door to see Mr. Reed my next-door neighbor. He had a package that he gave me saying that it was delivered to his house by mistake. I took the package and said thanks telling him I would give it to my parents. He asked, "Matt, are you home alone?"

I looked down, not wanted to see Mr. Reed in the eyes. "Yea," I replied, "Just hanging around the house."

Mr. Reed said, "Just wondering, you took a long time to answer the door I hope I did not disturb you." With that comment, Mr. Reed turned and went back to his house.

Was he watching me, did he see me in panties and bra, or maybe he saw me naked playing with my penis? I blushed thinking what if he did. I came close again being caught, maybe I was and Mr. Reed did not say anything. Those nights I made sure the shades were down when I reclined on my bed in my panties and bar, thinking about someone watching me pretend to be a girl.

I was tired with the pink panties and my black bra and panties. I needed to find another place to get my girly things. I have stolen from my cousin Amy and could not go there again. I went to the local mall looking at some department stores. I walked down the aisles in the woman's department. The aisles had rows of panties, bras, slips as well as skirts, dresses and blouses. I looked out the side of my eye, not wanting anyone to notice my interest. I was so intent on seeing what was on display I almost bumped into a salesperson. I started when she asked if she could help me find something.

I respond, "Aum, well, no, not really, just looking."

She asked, "What are you looking for, maybe something for your Mother, Grandmother. You are too young to have a girlfriend," as she smiled at me. "Well sweetie, if you find something to be sure to find me. I can help you to find the perfect item for you." She said that in such as way it was almost as she knew I was looking for something for me. I had two choices I would have to pay for what I needed, or I would have to shoplift what I needed. I decided to do neither.

I would be bold sometimes wearing the black bra and panties around the house. I took chances that my neighbors might catch me or my parents. One summer day I was horny deciding to take a bike ride dressed in the bra and panties. This time I wore a black T-shirt and black shorts to hide out under the outfit. If I were fortunate, my paddling would cause the silky panties to rub my penis, and I would orgasm. I would peddle my bike so the panties would rub my penis. It took fifteen minutes for me to orgasm. I closed my eyes for a second but lost control of my bike, crashing into trash cans sitting on the curb. The sudden stop tossed me over the handlebars and landing in the middle of the trash cans. I must have hit my head because I woke up with many looking at me. One called out to call 911; another was kneeling pushing on my leg. I saw red, blood, my blood. I felt woozy, dizzy and a buzzing my ear. I heard, in the distance, the siren of the rescue squad. I panic when I realized that my bra or panties might be revealed and with a group of people looking. I was a twelve-year-old boy wearing black bra and panties under my shorts and T-shirt. Shit, Shit Oh God, the shame to be discovered. The students at school would laugh at me.

I had to escape; I tried to move, but the cut on my leg started to bleed. The emergency unit arrived; they looked at my leg and told me I needed stitches. They cleaned the wound, applied a compress, checked my vitals' signs and received approval to transport. All of this occurred in a few minutes. They loaded me onto a stretcher transporting me to the hospital. On the way, they called my mother saying I was OK but needed stitches. She would meet me at the hospital.

At the emergency room and placed on a table. One male nurse and one female nurse each on either side of the table started to take my shoes off. Next, I knew they would take off my shorts or shirt discovering my secret. The female nurse started to cut off my shorts. I said, "No, do not take them off." She stopped and I was thinking she understood, but she gave the male nurse the scissors and said, "Get him out of his clothes, so we a check for other injuries." She left the room. I looked at the male nurse saying, "I am OK, no other bump, that is OK; you do not need to remove my shorts or shirt. Pleaseeee."

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