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2. When playing in panties in a warm bath wasn't available when away from home, I took to exercising naked to stimulate myself. This was because I hadn't yet got the idea of manipulating my own penis to make me feel good. In those days, I was far more flexible and found the best way to bring my excitement to a conclusion was to cycle my legs over me head. This of course meant that, when the wonderful feelings took over, my cock would dribble it's white sticky load directly on to my face and in to my mouth, which I lapped up as my reward. I took great pleasure in catching as much of my fluid in my mouth as I could, and enjoyed it's salty taste as I swallowed it.

3. It was a chance encounter in a school toilet that took my self entertainment to a whole new level. One of my classmates told me that his older brother had told him about how to wank - with his hand. He showed me the action of his hand, and left me to my imagination. When I got home that day, I remember I couldn't wait to try out the new information.
Now using my hand to manipulate my penis, I found it far more satisfying than letting the friction of my mother and also sisters panties bring me off, or cycling naked with legs in the air. I found it immensely reassuring I was doing something right, when I could direct streams of my ejaculation great distances in front of my or over my head. I also combined my new found method of masturbation with wearing pretty panties, and found I could make myself cum many times a day, whilst producing significant loads of sperm, to my massive satisfaction.

To this day, I masturbate every day and sometimes more. For example, this is the sixth time in a twenty-four hour period that I have wanked myself off - though these days I shave my genitals completely, and am wearing two steel cock rings as I masturbate in my panties. Old habits die hard.

4. Having eventually discovered the are of wanking and the pleasures of crossdressing, my next revelation was in the discovery of porn. It started quite mildly, with me wanking over 'page three' beauties in newspapers. Shooting loads of spunk over their faces and tits was a great thrill. Later on, jerking for hours over men's magazines that showed models with their legs splayed, revealing first hairy twats then later shaved cunts gave me immense pleasure, as I also admired the sexy lingerie and panties these lovely women wore.

Now, the internet, with it's unending list of fetishes, brings hard core porn to me all the time, and I find myself spunking uncontrollably sometimes at new perversions I am discovering. When only a beginner transvestite, I had no idea there were sites like this, that show I am not alone in my desire to dress in women's clothes and make myself cum, thinking of being used by similarly dressed men, in the most lewd and explicit way I can imagine. Like-minded people, enjoying the same interests, as we make ourselves spunk over explicit pictures and stories. Our minds are truly our greatest sex organ.

5. Masturbation took on another exciting level for me, when I discovered my asshole. I've always enjoyed playing with my anus, but things got way more exciting when I started to push things up my rectum.
First it was my fingers, then hairbrush handles and toothbrushes, then I soon discovered candles, and placing them in a condom meant I could leave them inside me for ages. I used to love plugging myself like this, dressing in stockings, suspenders and panties, then going for long walks with the object deep inside me. By the time I got home I would be gagging to shoot my load as quickly as possible.
Nowadays, I like to add a cock ring or strap to my butt plug (like I am wearing now), and go shopping for lingerie whilst dressed in some sexy items. Chatting with salespeople in the shops about lingerie, whilst I was plugged, ringed and en femme underneath my every day clothes, is an immense pleasure, and usually has me masturbating and eating my cum in changing cubicles, with others nearby.
Thank you to all the devices I have had up my bumhole, pressing on my prostate, maintaining my erection and urging me on to yet another ejaculation.

My first time and exposure to masturbation was at 12 yo on my first weekend at a boarding school. Some older guys, 13, 14, 15, talked about porn and a guy had some magazines , I was amazed at the real hard cocks and guys stroking and cumming. I tasted some errant drops and wanted to grab their cocks and pump them and feel them. My dick was tiny, and had maybe 3 pubes and I was convinced of a beta status early. When I saw a porn movie and some magazines a month or so later I wanted to be the girl sucking the cocks

I had jacked, stroked and pumped my little dick many times for a bit of pre cum. Was 12 and close to 13 when I shot my first few drops. It actually hurt a bit, I got it with my finger and enjoyed it. It was in a bathroom in a hotel room in Miami Beach long ago. Waited a bit and got nothing on the second try.

Lovely to read about your early masturbation discovery. I have always enjoyed the smell and taste of my own precum, and it amazed me how long I could lick it up before shooting my load.
From the very first time of seeing hard core porn with guys ejaculating, I always wanted to be on the receiving end of their spunky cocks - where the girls mouths, tits, cunts and assholes usually were. I still love a man cumming over me, emptying his balls because of his lust and desire. It is also such a thrill to wank off for others to see, as I enjoy their reaction to my spurting penis.
Happy masturbating.

Would imagine for most, the first real load is memorable event. The weekends became a time to look at Playboy, nude mags and sometimes 8mm movies, as lots of guys went away or home for weekends. Looking at guys in the showers i became more and more fascinated with cocks, especially circumcision scars. While my tiny balls were still tight, seeing real balls swaying while guys walked and fucked in movies made me want to play with them and I wondered if mine would ever get like that. My small penis and tiny balls, coupled with the desire to look at, play with and be used by a cock led me to the next step.
When I was home on a vacation from school, saw one of my mother's one piece bathing suits hanging in the bathroom drying, next thing I knew I was wearing it and my little dick was hard and dripping in an instant. My young mind was over whelmed. I jacked like a zoo monkey , caught the load in my hand and was weak. Ate some and washed the rest away. Cleaned up and knew i had crossed a bridge, what might be next.

Lovely hearing of your first time wearing and wanking in your mothers swimming costume. Wish I'd been with you to watch and wank with you and maybe catch your cum from your tiny cock as you spurted into my mouth.
I remember being at a school friends house and discovering his sisters two piece swimming costume (bikini style with pretty frills). I stole it and took it home with me, desperate to dress in it, to see how it made me feel. I couldn't believe how sexy and horny it made me, with the tight material holding and rubbing me in all the right places. I loved feeling like a horny girls with a rock hard penis. I masturbated so much in her costume, spunking in the lower half of the bikini so much it made the material crusty with my sperm as it dried. I also loved to watch my cum shooting out of my throbbing cock, over my belly and chest as I imagined her watching me ejaculate.
What fun I had wanking in her swimming costume.

Once I had tried my mother's bathing suit it was on to some other items I found in the laundry,, never did try panties until I was much older and those were a girl friend's.
The big next step was playing with my butt and finally sticking a finger then objects. Screwdriver handles , glass test tubes in different sizes were my favorite. Of course i inadvertently learned I had a prostate and the true joy of anal play came into my life

Oh, Evelyn, I so agree that one of the most important discoveries when masturbating, was my asshole.
After finding that simply fingering my bumhole was so pleasurable, I quickly moved on to candles, candles in condoms, hair brush handles, toothbrush handles, necks of beer bottles and wine bottles. Nowadays, I love to slide a butt plug up my rectum and go shopping, or have long sessions of ramming my ass with dildos and vibrators, stretching my anal sphincter to its limit as I pump my sissy shaved penis (like I am now). It makes making myself cum so much more pleasurable, wanking in panties with something stuffed up my ass. Enjoy.

i remember stroking myself in the shower even before i knew what stroking was or what cum was. Then one time i stroked myself to an orgasm - i thought it was churned piss.
the some time later, id jerk off in my socks, not knowing where to put it. i never jerked off in my mom's panties or pantyhose, but i would often use them as stimulation. and im still masturbating today!

I actually stopped masturbating altogether after my first lover had feminized me sexually. When he would orgasm inside me I found that far more satisfying and fulfilling. And ever since I have needed a male to cum inside me to feel sexually satisfied. That said I do very much enjoy masturbating a man's penis for him. It always feels like a privilege and afterward to lick his semen off his penis and pubic hair and belly for him. My own penis has atrophied and is fully retracted so I am anatomically unable to function sexually as a male though my orgasms are more intense than ever. They tend to be spontaneous without touching myself when I am super horny and sexed up. Don't know if any of you other girls can relate to what I've said.