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Caught by the Neighbor Crossdressing While Home Alone – Crossdreser Society | An Online Resource for Crossdressers | Transgender

Caught by the Neighbor Crossdressing While Home Alone

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Crossdresser Caught by Neighbor

Do you know a crossdresser who got caught in the act?

This is a real life story of a crossdresser caught in the act!

This happened around when I was 15 yrs. old.

As my sisters were off at college and it was just my mom and I at our apt.  I was home from school as we didn’t have any school that day.  But my mom was still at work.  So I got myself all dressed up looking pretty.  As I thought I will make it a girl’s day in.  I decided to wear a pair of my mom’s dark navy pantyhose with one of my sister’s jean skirts and a blue and white sweater with some black 3 1/2 heels.

I put my makeup and wig on.  I felt so sexy en femme.  I just couldn’t believe I was getting a chance to crossdress and not have to worry for a while as my mom was at work.  I just ended up crossdressing, doing the things I normally would, which felt so good hearing my heels and hose rub together and my heels on the floor when I would walk.

After a bit I decided to go out into the hall way for a bit and see how far I could get without anyone paying any attention to me or even noticing me.  It was nice as I liked hearing my heels crossdresser dressed upin the hall way.  After a few walking the hall attempts,  I decided to go down and check the mail in our mail box.  Our apt complex had its own mail box.  So I went down the flight of steps as we were 4 stories up.  I was a bet cautious as I didn’t want to get caught.  I made it down to the mail box and took the mail.  There was a guy there that was checking his but he didn’t see my face.  I could tell he was looking at me though, which I did like.

After I collected the mail I went into the elevator and headed back up to my floor.  When I got there I went to my apt.  You guessed it I was locked out.  I forgot to grab the apt key when I walked out.  I just had my mail box key.  I was thinking how stupid.  And then to make things worse here is our neighbor who is an older gentlemen walking down the hall way.  I tried to turn away but I couldn’t fast enough.  He stopped and was looking at me.  I just stood with my back to him.  I could feel him walking up behind me.

He said are locked out of your apt miss.  I said yeah I am.  I was so freaking scared.  He giggled and said here come with me to mine.  I followed him.  Now I was trying not to have my heels make such a loud noise on the floor.  I followed him in and stood by the door.  He called the apt manager who had all the keys for the apt.  Everyone pretty much knew each other so it was a real safe building.  He came up and opened up the door for me.  But my neighbor said that he thought he heard something and wanted to check it out as he didn’t think we were there and wanted to drop off our mail for us.

The apt manager bought it.  As he left I went from my neighbors apt to mine.  I told him thanx he said no problem.  Smiled and gave me my mail.  I was so relieved but nervous as I didn’t know what to make of it.  I finished out the crossdresser session with a j/o session and then called it.

Later on my mom came home and we had dinner and just lounged around for a while.  Then I went to bed as I was exhausted from the scare that day.  The next day was a normal Saturday nothing much happened.  But on Sunday my mom was going to church with her new boyfriend.  So I was going to be home alone for at least 3 hrs.

red-dress-crossdresserI thought why not dress up again.  So I put on some beige hose white bra.  Jean skirt knee length and a white top   make up and wig.  And put on some black heels that were 4 inch.  They were my mom’s.  As I was just getting done,   the phone rang.  I answered it and it was my neighbor who wanted to know if I wanted to come over.  I thought sure why not.  I don’t know why but I decided to come over dressed as I was.  I grabbed my apt key this time and walked next door.  I knocked and he opened the door.  He smiled and told me to come in.  I did and sat on the couch, which is where it all took off from here.

He was talking to me about my dressing.  When I started and why I did.  He also said that he seen others who are crossdressers or dress n drag as well.  He said that is a huge turn on to him.  Hearing that got me turned on.  I crossed my hosed legs in front of him.  And begin to caress my legs with my fingertips.  I noticed he liked that.  I decided to make the first move and leaned in and kissed him.  He took me in his arms and we must have been kissing for a while.

Feeling his hands on my legs, rubbing them, I decided to return the favor for getting me back into my apt, so I went down on him which was my first.  I was so horny and nervous as I never had done this before.  I undid his pants, and pulled his under wear down along with his pants.  His cock was right in my face.  I started to kiss it and then licked it.  And then came of putting it in my mouth.  I started to suck on it slowly, with a little trial and error as my teeth getting in the way.  I gaged a few times, but I started to get the knack of it.  I started to hear him tell me to not stop and keep going, which was getting me excited.  I started to rub my hosed cock while I was sucking on his.  The he came and it was a lot I could only handle so much and ended up spitting out the rest of it.

Then I came in my hose.  Oh did that ever feel so good.  After my first sucking encounter he said I should probably get back to my apt I agreed.  As I got back to my apt,  I got undressed and cleaned up.  The phone rang shortly after and my neighbor told me he wanted to see me again sometime all dressed up again soon.  I thought we could do that.

After which my mom got home with her new boyfriend.

November 29th, 2009

By: pantyhoseslut


About the Author:

Hi, I’m Marcy Simpson, the founder and creator of Crossdresser Society. I have been a crossdresser for over 25 years and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.


  1. Marshall  January 17, 2013

    I seriously love your site.. Great colors & theme. Did you create this site yourself? Please reply back as I’m hoping to create my own blog and would love to find out where you got this from or exactly what the theme is named. Thank you!

    • admin  January 17, 2013

      Hi Marshall,

      thank you for the comment. i am using a theme from Themeforest called PoserinkA. I love this theme as well and i am very happy with it so far. What sort of site are you building?
      Let me know if this helps and what you like about my site.


  2. Brittany  June 27, 2015

    Great site March. I’ve been cross dressing for20 years now. I was delighted when I told my fiancé and she said she has no problem with it

  3. Brittany  June 27, 2015

    Sorry that last post should say Marcy not March

  4. Dorothy Thomas  August 7, 2015

    Every time I open my PC there’s a site I haven’t visited before. Nice to meet you? I’m an old queen and have a story to tell also. In fact at my age, I have a few stories to tell.

    The young layde who’s story takes us to a locked apartment in very interesting indeed. Being invited to the neighbors Apt. and getting it on with the man is probably every CD’s secret dream. I never wanted to get caught dressing in my younger day so I didn’t get caught. Today? I’m completely out of the closet as an old man and there’s more people in this neighborhood who know me as Dorothy than as Tom. But I have never “bobbed the root” and I wonder what I’m waiting for. No balls I guess.
    Be back soon


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