Comments on: Crossdressers Talk About the First Time They were caught Crossdressing

By: Janine

Janine — Thu, 11 May 2023 14:04:01 +0000

I got caught by my sister, when I was about fourteen, wearing her petticoats, that I was infatuated with. There were three of them. A white one, a pink one and my favorite, was a baby blue one. I would layer them to look like I was wearing a formal gown and look at myself in the mirror. To me, I looked amazingly feminine and I’d parade in front of the mirror, acting like I was a girl, at her prom. After doing this for awhile, I’d sit in a chair in front of the full length mirror and pretend that I was being felt up, by a guy and I’d get so excited and hard, that I’d pretend that I gave in to him and let him fuck me until I ejaculated from jerking off
One day I thought that my sister was going to be staying late after school and I would be alone in the house
I was wearing her petticoats and lost track of time. All of a sudden, I heard her climbing the stairs and I was walking in the hallway. There’s wasn’t any place that I could go to hide from her and she saw me standing there wearing her petticoats, with a big erection sticking out from the petticoats.
What are you doing, she asked me?
I knew that I had been caught, so I admitted to her that I liked wearing her petticoats.
She said that I didn’t look very much like a girl and told me that it I wanted to wear girls clothes, to get my own and leave hers alone
I was scared that she was going to tell our parents about finding me wearing her petticoats, but she didn’t. From then on I stayed out of her bedroom and didn’t wear anything of hers again

By: JCarroll

JCarroll — Sat, 07 Jan 2023 22:36:40 +0000

In reply to Aniee💃. I like feminism too. It's such an exciting experience to be hold.

By: Gary

Gary — Tue, 23 Aug 2022 17:02:26 +0000

In reply to Susan Darwin. Very nice story...

By: Aniee💃

Aniee💃 — Thu, 31 Mar 2022 19:09:49 +0000

In reply to Madelynn Fox. I liked feminise 💃👠👗💄

By: YORO

YORO — Wed, 16 Feb 2022 22:39:31 +0000

i am women now

By: Ann

Ann — Mon, 30 Aug 2021 03:00:48 +0000

I started to dress when I lived in Germany. One night, while sat back on my couch in a cute outfit playing video games, someone walked into my room. I immediately channeled the deepest guy voice I could and told them to get out.
The next few days were awkward, because I had no idea who walked in on me. I had no idea how much they saw, or how many people they had told. Did they see anything at all, or did they just open the wrong door and hear yelling? Did they hear my heels as I went to get up and confront them? I should have just locked my door. And I was always careful about locking my door, but that was the one night I forgot.
In hindsight, my downstairs neighbor HAD to know that I was dressing. The click-clack of heels would have been a dead giveaway.

The only other time I think I have been caught, was today. Walking on my porch (which is surrounded by tall hedges), I came into a high visibility area just as a neighbor was driving by. I wasn’t paying attention like I should have been.
Now, this neighbor probably didn’t see me. But it’s still worrisome to think that they know, and might tell others.

By: Cid

Cid — Fri, 09 Jul 2021 22:36:34 +0000

The time I was caught, but not confronted:

I was in the house alone in the evening, dressing in my mother’s bedroom. It was located just as you entered the front door. All of a sudden, the front door opened and my mother moved swiftly past. I immediately started undressing. She yelled out for me, and I remember telling her I was naked. “Why are you naked?” she asked. Of course, I had no answer. I came out of her room as soon as I was decent. The conversation moved on, and the incident was never discussed.

There is no way she didn’t know what I was doing. For whatever reason, she never addressed it.

Sometimes I wish I’d come out to her then about my dressing, but all things considered that would probably have been selfish. She allowed me to continue. There was no call to put something on her.

By: alipants

alipants — Wed, 19 May 2021 14:53:44 +0000

I had a similar experience when I rented a room in a house.
In a matter of months, I was dressing as Alison more and more with the active encouragement of Steve. We were both turned on by my increasing femininity – no body hair, more make-up, a professional wig and extremely sexy, erotic clothing and silicone 38C breast forms.
We would have a cuddle then a kiss. Much later he would caress me and touch me up – both of us getting very turned on. I bought an enema kit for the night he wined and dined me Knowing / Hoping that IT would happen.
Huge turn on but we took our time. He was very gentle and considerate. After a few minutes of a bit of pain I had the best orgasm EVER.
That was me hooked forever.
Sorry to say he moved abroad after 14 months so it all ended.

Love Ali xx

By: Gwen

Gwen — Fri, 23 Apr 2021 04:40:15 +0000

I’ve been crossdressing for a long time,,but it wasn’t until a few years ago that I got made by a coworker..I was at a sex club in Las Vegas on New Years Eve,and a friend that I worked with walked in without me seeing him..He looked at me and smiled..I kinda got nervous,and walked out of the club to my car..His car was parked right along side mine..I have some bumper stickers on my car that I know he recognized,since he’s been in my car before. All of a sudden I really didn’t give a crap about being caught..I knew someday,someone I know would see me..We eventually talked inside,and actually told me I looked really sweet..Kinda made me feel weird,but hey I like compliments,and I do look rather nice all dressed up..I later found out from one of the other CD’s there that he frequents the place regularly,and has a thing for girls like me..I don’t think he ever said anything to any of the guys I work with,maybe because he’s an admirer,and wants to keep that hushed

By: Charlotte Cooper

Charlotte Cooper — Sat, 13 Mar 2021 20:15:26 +0000

I’ve been there Susan. I was dating a woman whom I told that I crossdressed. She was ok with it and didn’t place any restrictions on my dressing. I used to go out from time to time but mostly for my personal pleasure and occasionally we’d make love while I was wearing a bra, panties and thigh high stockings.

After we married she let me continue for a while but after about 3 months told me that it disgusted her and I had to stop. She also thought that she was worried I was gay and that my constant crossdressing was a manifestation of that. I quickly purged my feminine wardrobe and fit a few months I got by but soon afterwards I went back to dressing with a vengeance. I obviously kept this hidden from my wife but after a number of years she caught me through my internet browser history. I agreed to stop once more but a few weeks later I was going crazy not dressing so I placed a Craigslist ad for a spare bedroom with a closet to keep my things and dress up and maybe venture out.

I got a few positive as responses but the best situation was one that made me uncomfortable because it was from a man and I felt uncomfortable being in a man’s house while I dressed up. I just felt ‘weird’ but I really needed to dress up and his place was close and clean, and he only asked $100/month and he was a non-smoker.

We met and agreed and I paid two months, one month security and a month in advance. I started going to his place a couple times a week and the first few times he was away but on the second week he was there. He was good though and I dressed up and stayed in my room for a while while I admired my female appearance and frankly I was considering pleasuring myself.

After maybe 20-30 minutes he spoke up through the door and said I was more than welcome to come out and we could sit and chat or I could go out and come back or if I didn’t want to I could just stay in my room but that I was welcome to be social.

A few minutes later I decided that since he knew what I was doing and he seemed like an ok guy plus he wasn’t too old, young, weird or anything that I would take him up on that and I went out and we talked. He was super cool and complemented me on my appearance which was nice. I went out for a while but came back soon afterwards. We talked for what I thought was a few minutes then I realized another hour had passed and I had to scoot!

The next times I went there we spent more and more time together and at some point within the first month I let him hug me. I found myself confused and also I noticed he was aroused. I also noticed that both of our hearts were beating very fast! This went on for a few minutes and then almost at the same time we kissed! All of a sudden both of us were aroused and we were all over each other, I had never done this before! We went to his bedroom and started becoming passionate.

Long story short I put my hand down his pants and he unbuckled them and he was hard as steel. I found myself going down on him and after a few minutes of me giving him oral he stopped me and asked if I’d be willing to let him try to penetrate me. I told him I was willing to try but if I couldn’t do it or I changed my mind that he would stop. In any event it was amazing. It took a few tries but he was able to enter me and make love to me.

After a year I finally decided I couldn’t keep going like this and asked my wife for a divorce. When we separated she confronted me with ‘have you been having an affair?’ ‘do you have a girlfriend/boyfriend?’ I paused for about a minute and began to think she already knew so I told her I had a boyfriend. She told me she was shocked that I told the truth but that she already knew everything which she did. Apparently I left my Yahoo account logged on on her laptop and she read and saw everything I had been doing for the past year and a half.

The good news is that I am now living with the man I was renting from and that we are now in the same bed.