Thursday, December 13, 2012

why am i a sissy? (part 1)

Why am I a sissy?

after reading the excellent guys who wish they were girls blog (  it got me thinking a little about how or why i had become a sissy.  i have looked back at my life and i now ask you if the following series of events etc sounds like someone who has just stumbled on been a sissy, or someone who was destined to be a sissy.

i have split this over two posts as there are two distinct categories - one before i met my wife and the other afterwards.  the reasons will become clear as you read.

Pre Wife (from the age 0-28)

I was a popular boy in school up to the age of 13 when i left my usual school and attended a boy only school until i passed my a-levels at over 19 years old.  (note - nothing sexual happened at school in case you was wondering)  my confidence took a beating there though.

i was dressing in female clothes (my mothers) before i had ever masturbated.

The first time i ever masturbated was when i was 17 while watching miami vice (but not dressed), and i almost didn't know what was happening and i just laid on my bed using my thumb and finger as i had seen people call each other.  the second time that i had an orgasm i was wearing some of my mothers underwear and a black skirt.

i actually own more bras than i have had female lovers

As a teenager i went out fully dressed as a girl before I slept with a girl or even touched a boob

Used a vibrator before touching a girl

Used make up regularly before been with a girl

used to wear panties, tights and a bra etc to university beneath my male clothes. (i lived at home while at University)

i am not sure about the actual timings, but i don't think i ever kissed a girl while i was in university.

Bought female clothes before been with a girl

Bought various items of female underwear before been with a girl

Visited a tv shop several times before been with a girl

Had a wig fitting before been with a girl

bought various shape garments including padded panties, waist clinchers and silicone breast forms before been with a girl

used cock shaped objects in my mouth and pussy

Bought books and magazines for tv and sissy

i did not lose my virginity until i was 25

not including the wife i have slept with 4 women, including 1 prostitute on holiday

i only ever had sex with the women once. and never saw them again for various reasons (1st was unbalanced, 2nd never wanted to see me again after my failure in bed, 3rd i was not attracted to her (beer goggles on), 4th prostitute)  my wife is the only woman i have had sex with more than once.

i think the most telling ones are that i was masturbating at a young age in womens clothes, i went out dressed a as woman before touching a woman, and the fact that none of my girlfriends had sex with me more than once.  been at an all boys school through my teens didn't help.

looking back though, i can't believe that i went out dressed in a skirt etc before i had even got close to a woman!


Sissy Slut Michelle said...

Interesting evolution. Glad you are here.

JamieLin said...

In an all boys school, with all the sex talk and kidding about wanking that must have floated around, you still didn't have a go until you were 17? That's amazing.

You were much more courageous than I. My few clothing items were pilfered. I wouldn't have dared appeared in public, but otherwise your story sounds similar, until I got laid at 17. Then the gurlishness went largly latent until girl-trouble (as in the trouble is there are no girls) came back.

Please, do tell more!