tagToys & MasturbationThe Bio of a Masturbator

The Bio of a Masturbator


Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital.


This story is not about love, nor about romance, or even about hard core sex. This is a tale about my adventures with masturbation. Although most of you will find that this story to be boring, that is okay to me, but this is the account of all of my solo adventures from when I was a younger man. I felt that this part was needed to give you, the readers a foundation on which some of my adventures were based on.

I have shot more sperm from the tip of my cock from solo play then I had when I had sex with women. So much sperm, that I could have impregnated thousands of women, but I am no where close to stopping yet.

My tale began long before my eighteenth birthday, but during that time, it was pretty boring and routine, when I look back at it. But the true adventures began just shortly after I turned eighteen. That is when I was also introduced to the joys of women's clothing.

Before you say, 'oh, you are coming out of the closet.', I have to say, a closet is where you keep your clothing and I do not get dressed in the closet. So, no I am not coming out, I am here to tell my tale of my life time of masturbation and it just happens to be that I am a crossdresser also. But, crossdressing was the starting point of it all.

I was, at the time, a senior in high school and most of the kids in my class were either thinking about what collage that they wanted to go to, making memories for themselves, being in every conceivable club possible, or all of the above. Myself, I had decided to just lay low. At that time, I just did not care about all of that stuff.

No don't get me wrong, I was not a loser or a loner, I really did not care about those things and it got worse after one special night.

But I am getting a head of myself.

At the time that I started my senior year, my masturbation routine consisted of the use of my pillow. How I did this was I would lay down on my stomach with my pillow under my hips. With both hands under and on both sides of the pillow, it created a crevasse that allowed me to thrust my hard cock along. Because one of my friends was of legal age before I had turned eighteen, I had already had an impressive magazine collection. So with my head hanging over the side of the bed, I would pillow fuck until I came on the pillow while looking at the pictures.

I have always thought of myself as being adventurous when it came to masturbation. I was proud of myself when I came up with a new idea and it worked out, but there were times that when I look back at and wonder to myself, 'what the hell was I thinking of'. I have decided to add those times to my story and when ever you see (WHIT) in this story, you will know that this is one of those 'What the Hell was I Thinking of' times. Anyway, throughout my life, I also would get new (and sometimes) exciting new ways of getting off, from just a mere suggestion or idea from someone else, even they would not have known it. When the power of the internet came to being, those suggestions came even more frequently and it was hard to keep up, but some how I did manage.

So, enjoy my successes and please do not cringe at my failures.


Chapter One In The Beginning There Was... (Fall 1984-Fall 1985)

Even though my story began long before I was eighteen, I did not start exploratory masturbation until after I turned eighteen back in 1984.

I lived in a two story house on a farm, located in the Midwest, with my father, brother and grandparents. My mother had died when I was around two years old, but I do not remember much of her.

Things were kept simple with my self pleasure life. Waking up sometime after midnight and humping my pillow to one of the magazines from my collection. Things were just nice and simple. But if I had to say, nice and boring. Little did I know, but my nice and dull routine was about to come to an end.

It was about the beginning part of fall in 1984. I was in my bedroom on the second floor when I, for some strange reason, stepped out into the hallway. What I saw next, shocked the hell out of me, but now that I look back at it, it was the turning point of my life. What I saw was my brother, who walked out of his bedroom, wearing our grandmother's nightgown.

You must be saying, 'Now how does something like that change a person?' Well even the littlest suggestion has had an influence on me, even if it was not intentional. But, even if my brother did not intended for me to like wearing women's clothing, it happened and I am glad it did.

When I saw him standing there with the nightgown on, my jaw must have hit the floor. All he could say was, "How do I look?" and went back into his room. I didn't give it much thought, but little did I know, the seeds of crossdressing were planted in my mind.

About a week later, I was looking for something in one of my dresser drawer (I can't even remember what I was looking for), I had opened the one drawer that I had hardly ever opened and there was one of my grandmother's bra, that was laid right on top of everything. I stood there for some time, just staring at it. Although I had seen many women in bras and in the nude (from all of those magazines I had), I had never seen a bra up close and personal.

Yes, I was still a virgin at that time and I had lost it to another virgin. But that is for another story, not this one.

Anyway, without thinking, I went and shut my bedroom door. After locking it, I went back to the open dresser drawer. It took me a few minutes more to gather the courage to pick up the bra. As I held it in my hands, I remember that my hands shook. Not your tremors that you read from most erotic stories, this was a pure terrified shake. I was shaking so badly, that I had dropped the bra at least a half of dozen times. Some how, I had managed to stop shaking and got the courage to try it on. I took my shirt off and with a lot of trouble, I managed to put the bra on. Even without the knowledge of bra sizing, it fit me nicely, except for the cups. I didn't have the boobs for it. But despites not having the chest for it, it wrapped my upper torso just nicely.

I looked at myself in the mirror and I found myself completely turned on. I was hooked. My cock ached to be released from my pants as the feelings from wearing that bra was almost more then my young mind could take. Back then, I really could not describe the feelings that I was experiencing at the time, but now, it only feels natural to wear one.

As I gazed at my reflection in the mirror, I really wanted to take my hard cock out and bring myself to an orgasm. But, luck was just not on my side at that moment. I heard my father call out that supper was ready. I would have to wait for another time.

I reluctantly took the bra off and got my shirt on. The bra was returned back to the place that I had found it and went downstairs for supper.

I had forgotten that the bra was there, in my dresser drawer, for about a week. It just happened that I was getting ready to go into town to hang out with my friends for our normal Saturday night routine. Bowling. I just happen to open up that one drawer and there it was. The bra. But it had some friends with it. There was a pair of nylons, a garter belt and girdle with it. And I swear to this day that they were calling me. Taunting me to wear them. I quickly shut the drawer and realized that my cock was harder then it had ever been. I sat down on my bed and tried to will it down. But the more I tried, the more I thought about the bra. I just could not simply jerk off to take care of the problem. My father was in the bathroom, which was next to my room. I needed to get going before I was late and could not go downstairs sporting a raging hard on.

As I sat there, my mind started to formulate a plan to get off. Not just any plan, to really get off.

My curfew had been moved to 1 am since I was a senior and I had decided that I would come home a lot earlier then that. My brother, since he had been out of high school for some time, did not arrive home until sometime when the sun came up. Now my father, he did not arrive home until around 7 or 8 in the morning, depending if he was getting a piece. So, that actually gave me a few hours of fun, without any interruptions. Oh, as for my grandparents, their bedroom was on the first floor, and they could have slept through a hurricane.

My cock must have be satisfied with the plan, for it had finally went down and I quickly left the house before it decided to wake up again.

Around eleven that night, I told my friends during the second game of bowling that I was feeling pretty tired and was going home. They argued that I was being a spoil sport, because I had come in last on the first game and was doing pretty shitty on the second game. Normally, I would had been leading the pack, but my mind just wasn't into the game. It was some where else. It was in that dresser drawer.

After the game was over, I packed up my ball and shoes, told my friends that I'd see them on Monday and left the bowling alley. As I drove home, I found that I was speeding several times. Normally, I would have obeyed the speed limit, but excitement was really clouding my judgment.

Once I was home, I quietly crept into the house, I did not want to take the chance, although slim, of waking my grandparents. I made my way to the second floor and locked the door to my room. This time, I did not have any fear, I was just completely horny. I tore off my cloths and began to put on the undergarments. I still had problems with the bra, but managed to get it on. The girdle, I decided to leave it off, mainly because it really restricted access to my already raging hard cock. The nylons were easy to put on, but when I stood up, I had realized what the garter belt was for. I got it on, after figuring out how it went on and secured the nylons to the straps.

I looked into the mirror at myself and my already hard cock began to throb from the sight I saw. My cock's head was a raging purple from the results of me being completely turned on. But, I realized that I did not have any boobs to fill out the bra cups. I reached into the sock drawer and pulled out several pairs of socks and proceeded to fill each cup until I was satisfied that they looked right. I continued to gaze at my reflection in the mirror and then it dawned on me, what should I do?

I sat down on the bed and grabbed a couple of my magazines (my raging hard on not helping me to reach them). I flipped through the pages of one of them and came to a story that somehow I had missed. There it was, a self blow job. But not a guy giving himself one, but a shemale (at the time, I did not know what a Transsexual was much less what crossdressing was).

The story had me so turned on, that I wanted to try it myself. As I sat there on the bed, I tried to figure out how I was going to attempt this. Then it came to me. My bed was a bunk bed. My brother and I use to share the same room when we were younger and when he moved into his own room when he got into junior high, the upper bunk was never taken down.

I figured out that if I used the upper bunk to hold my legs in the correct position, I should be able to get me cock into my mouth.

I laid on the bottom bunk and in a few minutes of adjusting and re-adjusting myself, I had found myself staring, more like having an up and really close encounter with my throbbing cock.

The next few moments were almost a blur to me. I parted my lips and the head of my cock slipped in. The head of my cock felt spongy to me. My head was spinning I sucked on the head for the first time. My balls tightened and ached to release my sperm into my mouth. My hips, instinctively thrust forward and I found that my mouth fuller with my cock. The more my hips jerked, the more of my cock made it into my mouth.

Now that I look back at it, I wonder how in the hell did I not gag and I really wish that I was a limber as I was then.

It didn't seem very long, but I had found myself sucking all of my cock and I was so turned on by it, that I had started to shoot my sperm into my throat. I gagged a little at that time, but managed to swallow the most of my load.

When my orgasm had subsided, I slowly let my legs down and laid there on my bed and just simply relaxed. My mind raced. Guilt flooded my mind, but soon the feeling of total bliss overcame me. Somehow, I felt that it was right to me.

I looked at the clock and only a half hour had passed and I found myself still horny. Then a wicked little thought came to me. Outside of my window was the porch roof and it wrapped around to my other window that was painted shut. Without thinking, I grabbed a blanket and my pillow. I opened the one window and propped it open. Carefully, I stepped out on to the roof and turned to grab the blanket. It must have been a funny sight if anyone would have, me wearing a padded bra, stockings and garter belt, on top of the porch roof, on top of that, on a full moon night. As I look back at that night, I am so glad that I did not get caught.

I spread that blanket on the roof and placed the pillow as if I were going to fuck it, but I wanted to suck my cock again. I was hooked on it.

I tossed the pillow to the side and laid down on my back. I wondered if I would be able to get my cock into my mouth with out the aid of something to hold my legs in place. I flipped my legs over my head and found that I had no trouble with being able to suck my cock.

As I thrust my cock in and out of my mouth, another little wicked thought came to me. I stopped just for a little moment as I wet one of my fingers. I placed it on my anus as I continued to suck my hard cock and just simply played with it. Rubbing my saliva around the rim caused a new pleasurable sensation that I found to love. After wetting my anus several times with my saliva, I inserted my finger into my anus and came immediately into my mouth. A cry escaped from around my cock filled lips as sperm flooded my eager mouth. I rapidly fingered my ass as I continued to flood my mouth with my sperm.

Once my orgasm had subsided, I did not move from that position. My cock was still hard and I wanted more. I continued to suck my cock and fingered my ass with my finger. I did not have to use anymore saliva to lube my ass. It was wet and at first I thought that I had shit myself, but the what I had excreted was a thick sticky glob. It wasn't until the internet had come around that I had found out that this is very normal for men who enjoy anal play.

I continued to suck myself to several orgasms that night.

It was around four that morning that I finally decided that I should stop and reluctantly, went back into my room. I really did not want to take off any of the undergarments, but I did not want to be caught, especially by my brother.

After taking them off, I carefully placed them back into the drawer that I found them in. I then went into the bathroom and wiped the anal cum off of my anus and ass cheeks. Once I was satisfied that I was clean, I went back to my room and after putting the magazines back into their hiding space, I crawled into bed and it did not take me long to fall a sleep.

I could not wait until the next Saturday, but what happened to me during the week, completely devastated me and it would be a few weeks before I would be able to put a bra on again.

I came home from school one afternoon and my grandmother was really pissed. She had found the undergarments in my drawer and demanded to know why they were in My drawer. I told her the truth. I did not know and I did not put them there. I was grounded and she disowned me.

My self pleasure life was down the tubes and it wasn't until one evening that she had pulled me to the side and told me that she realized that I had told her the truth and she found out that my brother had planted the garments there in order to get me in trouble.

I was off of the hook, but, I no longer had them to wear. Sucking myself off with out them, did not seem right anymore. But a week after that, I had the opportunity to get them back and then some.

During the time when I was in the dog house, masturbation really didn't appeal to me. Of course, I got myself off, but my heart really wasn't into it. Also, since it was fall, it was getting colder out and my treks to the porch roof were no longer an option. Since the only room on the second floor that had any heat was the bathroom, my nightly pillow humping sessions were limited also. This was one of the reason I really hated winter.

After being 'let off the hook' with my grandmother, I had an excellent opportunity to retrieve the articles of clothing that I had lost. My grandmother had went into town one day and when I had gotten home from school, I had found that I had the house to myself. Most teens would had raided the fridge, but not me. My dick did the thinking for me. I went and took back the bra, girdle, stockings and garter belt. But my eyes caught sight of some other outfits that I would enjoy wearing, that I knew that she would not even miss.

With my new treasures, I ran upstairs to my room and stashed them in a place that I knew no one would even bother to look in. I thought that I would be able to fun again, but I was wrong. I had even more fun then I had ever imagined.

I had limited my dressings to the weekends and even then it was pretty restricted. Fall had turned into winter and with no heat in my room, wearing just undergarments just didn't cut it. The one time that I attempted to suck myself off, my teeth were chattering so much, I was afraid that I would had chomped my dick off.

Christmas came and gone. New Years eve and day came and went. Not much I had done, but then something came over me. I had began to wear the undergarments almost on a nightly bias. Crossdressing had become a part of me and I was not ashamed of it, but back in those times, you did not flaunt it.

It was some time after the New Year and with the ground well covered with snow. I had gotten home from school and I was outside hanging around the large hay bales. For once, I had gotten my chores done early and had nothing to do. I do not know why I was hanging around the bales, but I had been. I was thinking about something when out of the blue, I was horny. My cock harden rapidly and there I stood with my dick sticking straight out in front of me. I could had just whipped it out and jerked off, but oh no, I had to come up with a different idea (WHIT). I knelt down and made a hole in the snow about the size of my cock. When I stood up, I looked around to see if anyone else was around. Once I was satisfied that no one was, I pulled my pants down to my ankles and laid down on the ground with my cock in the hole. I did not take me long to achieve an orgasm, but I can say although it was a mind blowing experience. What makes me think back on it, I am surprise that my cock did not get frostbitten.

When spring came and the weather was warm enough, I picked up with my activities with more vigor. I had really missed giving myself a blowjob and the first time I had tried to do so, I found that I was not a limber as I was before.

Stretching soon became my best friend and I had done so on a daily bias. It wasn't very long that I was able to stick my cock in my hungry mouth and savored the feeling every chance I got.

When things seemed to fall into a routine, tragedy struck the family. My grandmother became ill and moved in with my aunt until she had gotten better. But right before she had fully recovered, my grandfather had bought a house in town and I found their things being moved out. That was also the time that my father took over their bedroom. My brother, even though he kept his room at the house, he was hardly ever home anymore. So that had left me alone on the second floor.

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