Reset Password
If you've forgotten your password, you can enter your email address below. An email will then be sent with a link to set up a new password.
Reset Link Sent
If the email is registered with our site, you will receive an email with instructions to reset your password. Password reset link sent to:
Check your email and enter the confirmation code:
Don't see the email?
  • Resend Confirmation Link
  • Start Over
If you have any questions, please contact Customer Service

First Time Crossdressing! Part 1  

KatieLegz 51T
0 posts
9/15/2022 3:47 pm
First Time Crossdressing! Part 1

So, it was the late 80's, I was 14 years old, and it was the school summer holidays. I was home alone and to be honest bored.
I decided to go through my older brothers draws looking for his porn mags as I knew he had some hidden. He was at work, and I had to be careful not to disturb stuff too much as he was a very tidy person and would kill me if he found out.
Well while looking in his draws I found a pair of large black patent high heels?!?!? I thought it odd, but he was dating at the time and thought they were his girlfriends. Just behind them was a black plastic carrier bag. I opened the bag and there was a black Basque, suspenders, lace knickers and a few pairs of stockings. More shocking was some polaroid pictures of his girlfriend in similar underwear but not this stuff. On looking at the pictures it dawned on me that it was from when they both had gone to the Rocky Horror Show a few months back and had dressed up.
I do not know why but I had a massive urge to try this stuff on. I figured it would be hours before anyone would be home so why not?
I had a quick shower and started to get dressed. I was shaking with excitement and my cock was rock hard and already weeping a bit from the tip so decided best not put the knickers on as I did not want to make a mess and get found out by my brother.
Once I had figured out how to put the Basque on and tie it tight, I was amazed how it changed my shape. I sat on his bed and rolled the fishnet stocking up my legs and spent ages trying to connect them to the suspenders. Once on I looked in the mirror and felt so girly, excited and fucking horny but could not explain why. I had never felt this good. Was I gay? should I have been a girl? and so on. Loads of thoughts flying through my head!! I just knew I loved doing this.
Last of all I put on the High Heels and once again my body look different. They made me stand up straight and my bum was sticking out. I just felt so horny, and I actually thought my cock would burst.
Well now what do I do I thought? I know let's go downstairs and have a walk about so that's what I did. Having never walked in heels this was a bit of a challenge. I ended up going down the stairs on my bum like you do when you're a . Once downstairs I carefully started to learn to walk in heels. I must have looked a fair sight tootling up and down the hallway with my raging hard on bobbing around. After a while I started to get the hang of it and started to strut my stuff. It felt fantastic, that was until.............

I suddenly heard the back door of the house close; my mind was all over the place, who could this be? My parents and brother would not be home for hours!! Then I heard a familiar young girl's voice shouting my name. Fuck! it was a of one of my mother's friends, she had come around to drop something off for my mum. I couldn't move and even if I wanted to run, I couldn't and there was nowhere go! In a split second she was stood in front of me and all I could do was cover my rock-hard cock as best I could.
I didn't say anything. I just couldn't. What could I say?
She stood for a minute, looked me up and down and just said "You look nice, although you could have put a pair of panties on if you were expecting people!"
I couldn't believe how chilled out she was, I thought she would have run out screaming. Thank the lord she didn't.
She was two years older than me and went to a different school, so we only ever saw each other through family events or the odd time in town. She was not my type but a very nice girl who always dressed trendy.
She carried on by saying "You actually would make a great girl but not in that tarty get up. I can see that you must love doing it judging by the throbbing thing in your hands"
I started to almost cry with shame and embarrassment and she could see I was upset. She came over to me and gave me a hug. She said, "I can help you look just like a girl if you really want?"
I told her I didn't know what I wanted. I said I had all these strange feelings flooding through my mind and body.
"Right" she said, "Follow me upstairs if you can and let's go to your bedroom"
I did what I was told which was hard trying to steady myself with one hand on the stair rail while the other had still trying my best to cover my cock.
She saw me struggling and took my hand away from my cock and held it to help me up the stairs. She said "You could just take your heels off, but you don't want to do you? I can see it turns you on" and with that she slapped by bobbling cock. Fuck, I thought I was going to spunk all over the stairs. Nobody had ever touched my cock and even though it was just a slap it felt great.
Once in the bedroom she shut the door and sat on the bed telling me to stay standing. She said "I am going to ask you some questions and I do not want you to think about the answers. I just want you to say yes or no. From your answers we will decide what we are going to do!"
Okay I said still standing there dressed as a little sissy tart with a raging hard on.
"Okay here we go, remember do not think just yes or no, okay?"
"Do you want me to help you become a girl for a day?"
"Do you want me to bring some of my clothes around to try?"
"Do you want to go out dressed as a girl?"
"Have you ever seen a girl naked in the flesh?"
"Would you like to?"
With that she just stood up, slipped off her trainers and sexy little white socks, peeled down her leggings and knickers and took off her oversized jumper and sat back on the bed completely naked. Well, that was it I started to dribble pre-cum and she could see I was. She said "I can tell you like what you see, however we are girls together here and I am not a lesbian. You can look but not touch"
I said that's fair enough, but can I touch myself?
She said, "I was going to suggest that because whilst you have a nice cock it certainly looks like it needs relief. I tell you what, I will get on all fours on the bed so you can get a good close look at a real pussy, and you can wank off over it. Just don't make a mess all over me!"
With that she turned around and bent over. I started rubbing my cock and with seconds shot the biggest amount of cum I have ever done all over her back.
I am so sorry; I couldn't stop myself. She said "No matter, we need to get you in the shower anyway to shave those legs and balls of yours. So, I might as well join you, so I show you how best to do it."
I cleaned up as best I could, took off the shoes and underwear and followed her to the bathroom........

To be cont...........

Become a member to create a blog