Confessions - my past

So I have never really thought about where my fascination for cross dressing started or how I ended up down this path.

My first time ever seeing anything pornographic was before I was in my teens. I had been playing some hide and seek and hid under my parents bed. There was a shoebox that was full of magazines and I saw so many things I didn't understand yet. But I was fascinated by boobs and that there was no penis... every once and a while I would imagine while laying in bed with my sheets pressed on top of me that I was in some kind of machine or magical blanket that would turn me into a girl. I would imagine the pleasure my cock being sucked inside my body and my chest expanding to grow beautiful breasts.. I felt such a wave of pleasure when this would happen. I would get also a sense of pleasure and shame when I would think this way in the back seat of my parents car. Thinking that my body would change and the pleasure from my penis was actually it melting into me to form a vagina.

It wasn't for a while that I would find my mom or my sisters clothes. I was skinny in middle and high school but when I found my sister's swim suits. I would regularly try them on and pose while nobody was home. I also found my mom's panties and bras... and even her thong. Ahhhhh it gave me such a rush when I would try them on wishing I had the figure to fill out the lingerie. I would regularly steal 1 or 2 pair just to wear. It always turned me on to feel the smooth silk. I would tuck myself to see what I would look like without a cock all the time and i would constantly have to release the pleasure. I would use the vacuum on my nipples imagining that they would grow breasts or put my cock in a vacuum thinking it would pull it off leaving me a girl. Omg remembering all this makes me so horny.

But it really started when I found my parents toys. Especially my moms dildos. Now I know it may not have been sanitary or whatever but I was captivated. Holding them felt so nice. They felt bigger than I had expected and it made me so excited. It took a while but I would jerk myself off holding it against my cock. I then tried it in my mouth. It felt so natural, so inviting, so fun. Combine that with the panties and bras and I was euphoric. At the time I had no idea what this meant, I just knew it felt so good. It wasn't until later that I started toying around with my ass. At first I just slipped a finger. But 1 became 2. 2 became a marker and other objects. Finally I remembered the dildo and thought let's try. It was such a wild sensation. I didn't know what to think about it, but I did know how to move and how it felt. I would try it every once and a while along with dressing up and I would cum so much. Thinking of how I am now... i was definitely dreaming of being a sissy girl at an early age

Let me know if you want details or to continue...
Published by redheaddynamo
2 years ago
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twitchums
twitchums 14 days ago
lovely memories. Thanks for sharing them.
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Bi-sub_n_son 7 months ago
I also had a really good time after i found mommy's hidden dildo collection
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Roadnok3 10 months ago
Love it! Definitely want to hear more!
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Chaz352 10 months ago
mmmm...just discovered your page...wonderful!! xoxo
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megahurtz68
megahurtz68 1 year ago
tell me moreĀ 
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YuiMinami
YuiMinami 1 year ago
Oh please continue!
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Lingerieboy71
Lingerieboy71 1 year ago
Great early recollections. You must have gone into hyperdrive in your teenage years..?!
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peterjones1234 1 year ago
Hi Toni, This is great, please continue :smile:
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badboyt99
badboyt99 1 year ago
Very brave and honest of you to share your feelings x
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alisonangel22
alisonangel22 2 years ago
so honest true and beautiful im the same to a certain extent but still so beautiful xxxxxxxxxx
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Pervytvlover
Beautifully written. Would be nice to see more.
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