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This is a story of fiction based on facts researched on the Internet.
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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 snuck to look around. I open one of the desk drawers and found a stack of magazines. The cover of the magazine pictured 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 naked women. 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 aware of my disturbing dream. My dream was of the naked women shown in the Playboy. My parents told me it was terrible 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. The front of my PJ were wet and the sheets. 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 pee’d. I bent over and smelled my PJ. It did not smell like pee. The icky stuff was all over my PJ and sheet. I removed the moist 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 troubling to me. My original dream was of a woman with enormous 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 a real live nude 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 seen in Playboy magazine and what I knew about my body. Looking back on my first wet dream, the vision of a nude woman with a penis was puzzling.
In following dreams, I remembered my penis touching a blanket; another time it was a hand. I was not sure whose hand it was 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 who was wearing an azure dress, just as the last time I saw her. In the dream, I remember being pushed into her, my penis contacting azure dress, and then 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 remembered there was something girls clothing that made me wake up wet. 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 undressed women but with little penis. My dreams were not about sexual intercourse; I had no knowledge anything intercourse. The dream was what I knew, pictures of 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. Typically 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. I read the definitions in the dictionary then reasoned this wet dream was something normal, happening 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 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 finding 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 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 erotic 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 boys and girls masturbate during their lives. 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. Additional, some boys and girls 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. My penis was not large, it was easy to hide in my pants.
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 masturbating. 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 thinking of seeing girls panties for the first time. I could not grasped the connection between the visual stimulation and my erection. I finished peeing then reach for the colorful panties. The panties felt soft to the touch then I grab them. 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 brought 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 uncanny occurring, as if I were going to pee but not like peeing. I orgasm; semen squirted from my pee hole. The orgasm happened so fast, I was surprised when my semen hit my chest and fist. 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 were 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 consider, 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 breathe. 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, rubbing 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 soaked, including my gym shorts. Yes, that worked, I was drenched 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, my T-shirt was wet. I realized Zack might 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 bra 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. Zack was farsighted and 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. Not wanting to meet anyone else, I needed to go home to remove 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 soaked. I could not leave the bra and panties wet laying 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 bra and panties. The silk material dried fast and now was about dry. I placed the bra 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 to see if he noticed the bra. If he did I needed 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, hum; I do not know how to ask or where to start.” “I need to ask you, if um, if you, well you know, had any weird dreams?”
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 squirting in 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 have 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. Zack sounding as though he did was not sure how to say the word.
Amy my older cousin and Zack my best friend almost had caught me under dressing. I stole and wore my cousin’s bra 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 woman’s body and sex increased so did my fantasies and I need to ejaculate. I felt a tingling when wrapping my penis in the panties but wearing panties and bra were 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.
I would picture me in a dress with heels, pretending to be a girl. I found that dressing was an outlet for stress. I felt relaxed from the tension of school reduced. I liked my penis. My penis provided pleasure by having an orgasm, a most enjoyable feeling. My young body was trying to tell me something. My body was telling me I needed a girl. A girl to see naked, to touch, to rub with my penis and orgasm. What I became when dressed a girl was what my body needed. I became to object of my desire, a girl and later a woman.
On some days when I was alone in 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 window 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 undressed 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 shares 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, “Hum, 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 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 occasionally 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 pedal 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 vital 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.”
He responded, “Sorry kid, procedure. First, you need to sit-up?” I started to sit up with his help. He placed his hands on my arms, shoulders then my back. I know he felt the bra strap. He patted my back again. He told me to lie down. He hands checked my neck, arms then my chest and stomach. As he touched me, he asked whether it hurts or not. I told him no. I know he felt the bra; you cannot have missed feeling the bra. The female nurse came back questioning why my shorts and shirt had not been removed. The male nurse said he checked, and I had no other injuries and no need to remove his clothes looking directly not her eyes. He told her. “No need to embarrass the patient by removing his clothes, it is not something we need to do.”
The doctor arrived, looked at the wound on my leg. He said, “Son, you are going to need stitches. I am going to give you two shots. One will be for Tetanus and one to numb the leg.” He loads the syringes with something telling me he would have to inject in your backside. I panic again. When it could not get any worse, the male nurse asked the doctor, whom he could give the injection. The Doctor said OK. The male nurse pulled down my shorts and panties with one motion, swabbed the area with alcohol and injected me quickly. The injections were all over in seconds. No one noticed the black panties. I was not sure if the male nurse knew, I think he did, but he never said anything. The male nurse provided a pair of crutches, told to stay off my leg for a few days and return to have the stitches removed.
My mother picked me up, drove me to pick up my bike then home. All the way she was questioning me what happen. How did I run into the curb and trash cans? I finally had to admit what happen. I looked at my mother and said that a cat ran across the street, I swerved, hit the curb and flew into the trash cans, but I did not hit the cat. She told me to be more careful. I limped to my room; shut the door subsequently removed my bra and panties hiding them in my safe location.
What if I one of the bystanders discovered I had panties on. What if the nurses or doctor found my panties or bra? Would they say I was weird, immoral, or plain silly? Maybe my friends would call me a pervert, or I was not normal, or a sexual deviant? I felt ashamed, guilt and fear for having gone to under dress in panties and bra. I had two panties and one bra, but I needed to toss them in the garbage. I gathered my girly underwear, wrapped them plastic bag then tossed them in the kitchen trash. I returned to my room and cried. I felt as if I had lost part of me. I felt naked without my girly underwear. As I sat in my room, I began to hate me. Underdressing was my escape something I enjoyed. Immediately I wondered was I crazy and worthless?
The next morning I took the trash out to the curb. When I did, I rescued my girly things. I just could not give up something that allowed me to stroke my penis and to orgasm. A few days later I returned to the emergency room to have the stitches removed. I was walking with a slight limp and not needing the crutches; I returned them. The same male nurse was on duty. He was the one who removed the stitches. When he was done, he said that he was waiting for me to return. He handed me a small plastic bag. He put some bandages and a tube of cream into the plastic bag. He said, “I have put a few things into the bag that you might have an interest. If anyone asks what is in the bag, simply say it is extra bandages. Only look inside when you are alone.” I did not understand, just nodded my hand yes.
When I arrived home, I went to my room and shut the door. In the plastic bag on the top were the bandages and cream. Below that wrapped in tissue paper was something soft. I slowly unwrapped the package, finding several brightly-colored panties and matching bras, with lace and bows. The bras were small, like what most girls would get for the first time, training bras. There was a note which said, “Please accept this present from someone who understands. I know how hard it is for you to find lovely things to wear. Please enjoy Paul.”
I rubbed the panties on my face, nevertheless felt so soft. I swore yesterday I was going to give up using woman’s clothing to rub my penis but with this new lovely clothing. I could not help but to slip into them. A few days later, the doorbell rang.
It was Mr. Reed from next door. He has a small box that he gave me. I thought it was for my parents, but he said, “This is for you. Our grandchildren have left a few things over at our house over the years. They have outgrown these items, and you might get some use out of the. If not just take them to Goodwill.” With that said he turned to go home.
I said without looking into the box, “Thanks, Mr. Reed.” I took the box to my room, shut the door then opened the box. On top of the box were boy shorts and T-shirts. Underneath were a couple of schools skirts and white blouses. On the bottom was black girl’s shoes and white knee-high stocking. My parents were not to be home for hours; I decided to try on what Mr. Reed had given me. The clothes were so lovely. I had my panty and bra from Paul now I put on the school shirt, white blouse, white knee-high stocking and shoes from Mr. Reed. In my room, I looked in the mirror, prancing around pretending as a girl would pretend. I looked like some of the girls at school only flat-chested. I stuffed my bra with one sock then smile at my newly developed girly figure.
That weekend I went to the mall to meet Zack. He was late so decided to walk in the department store woman’s sections to look at the clothing. As I walked by, someone tapped me on the shoulder. Turning around I saw the salesperson that I almost bumped into. She asked, “Do you need any help?”
Surprised by her questions I just stammered, “Well, no. I was just looking. I mean I was not looking.”
She smiles, “Well, maybe you can help me. I have been several returned items that cannot be put back on the shelf. They would be put in the trash, and I would ask that you take them home and see if you know anyone that can use them.”
I said, “OK, I will make sure someone can use them.” She ushered me back to the checkout counter. Next she reached down for a package. She gave me the package smiled saying, “I have been other returned items available should you find others that might like them.” I left the department store wanting to see what was in the package. Just as I was to peek inside, I saw Zack walking towards me.
Zack said, “What are you up to, Matt? What is in the bag?”
I responded quickly. “Oh, well… my mother asked me to pick up this package.” As I closed the package to make sure he would not peek inside.
I was anxious to see what was in the package, I told Zack, “I have to go now; I need to take the package home, will see you tomorrow.” When I arrived home, I could not wait to see what the salesperson placed in the bag. Opening the bag, there were several items each wrapped in smaller bags. I opened the first bag discovering something I had seen in Playboy, called a corset. The corset similar to a bra, but it had the lace material down to the waist. From the bottom were several strips of material with some sort of clips. The corset had a zipper down the front and lace up the back like a shoe. In the next small, package was women’s stockings, thigh high, and size small. In the last small, package was a blond hair wig. The wig had shoulder length, bangs in front. This was the most exciting of all of my gifts. With this, I would look just like a girl.
I started cross-dressing by under dressing. So far, I was not caught. If my father found out about my secret, I would have been spanked for sure and told that this was improper to do. I had to keep my under dressing a secret. I kept my women’s clothing hidden in several places so if something was discovered I could probably explain. I was always afraid that my parents or friends would discover my secret, but the longer I was afraid, the further I would dress. I was so stressed by the fear of getting caught; I had to have a dress to have an orgasm to reduce the stress.
Over the rest of my middle school and to my senior year, I suffered from low self-esteem, constant guilt, and depression and felt I wanted to die. I completed suicide a few times, and presently in my senior year of high school ended in a psychiatric hospital. When I found the right help, and I figured out what this crazy cross-dressing was all about. I realized the demon inside me was not a demon. Cross-dressing was an active misunderstanding by society. Cross-dressing was a gift to some men. To me, cross-dressing was a way I explored my feminine self-expression and effectively satisfied in my closet cross-dressing actions. Instead of hating myself for being this way, I decided to embrace this part of my life. I found a great sense of happiness and relief. By allowing myself to be myself, I finally achieved a sense of peace and calmness. Before receiving help, there was once confusion, self-loathing, and pain. The personal price I paid for trying to conform to society’s gender role was substantial. A few years of my youth were needlessly wasted in confusion.
After college, I continued to underdress. I was older, had money and picked up my fetish for lace, satin, silk with bows. Thongs, boy shorts, French cut, push up, under wire, corsets I like to under dress and anything else that looks sexy to me. I was a single working in a large office. I am underdressed daily and no one noticed. Mostly, I wore panties but could not wear any of my tops at work, too much of a chance of getting discovered. I under dress daily hoping I am not caught. I enjoyed feeling my panties rubbing my cock during the day. I would not wait until I could get home and finish dressing. Living alone allowed me the privacy to dress.
Cross-dressing gives me a feeling of relief, as if I had been tense or anxious and when dressed now I could relax. Over the years cross-dressing has provided me a sense of naturalness as if being dresses were my proper state. I felt more attracted to me when cross-dressed than when dressed as a man.
I realized there was a connection between how attractive I feel and how I am dressed. My feeling was heightened by feeling satin or lace or other flimsy, sensuous fabrics against my skin. I felt sexual arousal by the sight of my own body; in stocking, a skirt pulled taut across my thighs, with my painted fingernails, all of the visual that would arouse me if I saw them on a woman.
Over the years’ women’s clothing that I wore has been associated with sex. Items like bras and panties have become fetish objects by a simple process of association. I am aroused by the sight or feel of women’s clothing worn by a desirable woman, and if I were wearing them. Wearing inherently arousing garments leads to arousal.
For me, the sight of a stocking foot in five-inch heels, or a satin dress pulled taut across a soft belly, evokes the same sexual arousal whether on a woman or another man.
My cross-dressing habit has turned me into the object of my longing, seeking the look like the perfect woman, thus the need to gain expertness of it. Cross-dressing for me was like having an eager and willing woman to touch and admire. A woman who would pose for you who would let you watch her touches her and fondles her as much as you like.
One afternoon one of my male coworker Randy wanted to go to the local sports bar for an after work drink. This bar was next to a Harley Davison motorcycle shop where you found a few bikers. Countless women from our office would also go to this bar. People referred the action at the bar to be mild to wild. Randy and I order a couple of beers. Randy challenged me to a game of eight ball. Halfway through the game a couple of bikers came over asking if they could have the next game. They sat at the end of the bar next to the pool table watching Randy and I. I felt uncomfortable being watched by the bikers. One of the bikers was looking at me with more interest than finishing the game. Although Randy was taking his shots, I checked my shirt to see if it were still tucked inside my pants. I was tucked in, but I notice my thong moved up on my hip and above my belt line. The thong was blue and could be seen through my white T-shirt and my white dress shirt. I had not had this problem at work but reasoned the bending over playing pool had caused the biker guy may have noticed I was underdressed in a woman’s blue thong. I have met some men whom the prospect of a man who dresses in a woman’s clothes is a turn on. Worse, some of these men treat cross-dresser as sluts, whore, or bitches. These men liked to dominate a cross-dresser with erotic verbal humiliation. These dominate men sometimes develop into BDSM play (BD=Bondage and Discipline; SM=Sadomasochism) with a cross-dresser. The cross-dresser plays the submissive role by being bound, often gagged and force fellatio or sodomy.
Many men consider all cross-dressers are gay, queer, fag cock suckers. No definitive research has been conducted to survey the cross-dressing population. The estimated numbers of gay or bisexual transvestites are about the same as the general population-or about ten percent. This means ninety percent of cross-dressers are heterosexual. Some heterosexual cross-dressers fantasize having sex with men and dressed as women as an extension of the role of a woman. To characterize the sexuality of these men, bisexual would probably be the best term. However, many cross-dressers chose to have sex, or fantasize about sex, with women.
Randy called the eight ball in the side pocket and won the game. I told Randy I had to go pee. But I had to pull the thong down so it would not be seen. I went to the stall, shut the door and unzipped my pants. I heard the restroom door slam; someone entered. I peeked out between the stall doors. One of the bikers, the one was looking at me. He walked out of sight, toward the urinals. Trapped in the stall, my pants were around ankles, with my blue thong riding high on my hips. I adjusted the thong to be below my belt, and my hand moved to touch the material covering my cock. I felt the same tingling sensation as when the first time I put on the pink silk panties. My cock instantly got hard stretching the thong. My balls slipped out of their resting place hanging to one side of the gusset and my cock flat across my pubic area. I knew the biker guy was going to discover me. I expected being told get on your knees sissy. I heard the biker footsteps; he came toward the stall. I was ready for the stall door to swing open. The footsteps came closer then changed directions rest room door opened with the footsteps of the biker disappearing. Alone in the stall, pants down, cock up expecting the worst, afterward I felt rejected.
I pulled up my pants, adjusted my bulge, adjusted my thong low on my hips, zipped and buckled my belt. I washed my hands then returned to the bar where Randy was talking to two gorgeous women. The four of us found an empty table with Randy and I being the women a couple of round’s drinks. The two women Sara and Mary said they were in town for a sales meeting and suggested that we followed them to their motel, a few blocks away. A few minutes later I found myself alone with Mary. She led me by my hand to the bed pushing me onto my back. She hiked up her skirt showing off her black high stockings with a matching garter then climbed on top of me. She took each of my hands in hers holding them above my head the learning flat on my chest, she started to kiss my neck, ears, cheek then my lips.
Mary was hot being on top acting dominating. Mary sat directly over my now hard cock and started to grind back and forth for a few minutes. Swiftly moving Mary moved to an on top position she was now sitting on my face, and her face was over my zipper. Her hands were fumbling with the belt and zipper while her moist slit moved over my lips. My instinctive reaction was to open my lips and stick out my tongue so to lick her pussy lips. A woman’s anatomy had been always a mystery, I did not know where to lick or what to suck. I licked and sucked anything that was in my face. Amazingly, by accident I hit the right spot because she stopped trying to get my cock out of my pants and started to moan. I pulled her body tight against my face with my tongue buried as deep as possible. In turn, she pulled my zipper down allowing my cock to spring over the thong. I was sure that Mary had not been noticed as she swallowed my hard cock. As swiftly as I could tongue her pussy, she moved her head pumping my cock. With one swift move; I rolled her over on her back, and now I was on top in the six-nine position. Mary reached up to unbuckle my belt. I was seconds away from being discovered by this fiery passionate woman, discovered that I was wearing a woman’s blue thong.
She would discover I was a cross-dresser. Few women supported male cross-dressers, and I did wish rejection with Mary. She might have been turned off by a man in panties. She had the belt unbuckled; the pants were slipping over my ass. Within seconds, I was going to be caught. The only thing I could do, I reached up and turned off the lights. I slipped off my pants and the same. Motion removed the thong. In the equivalent motion, I changed from the six-nine position to the missionary position. I placed each leg on my shoulder where my cock was opposite here now dripping pussy. I teased her by rubbing my cock on her moist slit. She started to beg me to fuck her. I took it slow with putting the tip of my cock into her pussy. Her stocking’s leg now was rubbing my neck and on my upper body. I felt Mary’s breasts through her blouse, then in the darkness. I started to unbutton her blouse. I could feel her silky bra with lace and bows; the touch of Mary’s clothing was increasing my need to orgasm. I was glad the lights were off, seeing Mary’s sexy stockings, garter; bar would be too much for my sight and touch. I adore the sight of a woman and wish that someday could find a woman that would understand, but I did not want to take a chance with Mary. I was horny for sex; Mary was willing, and we fell asleep in each other arms.