Crossdressing Storieslatest

Nearly Got Caught Crossdressing

almost caught crossdressingAnyone been caught out wearing saucy lingerie or more? I’d love to hear your near miss or caught red handed story. And the aftermath lol. The story below is tame but true.

I once had the responsibility of watering a friends plants while he was away with his Mrs. I went round one Friday evening around 5pm and the sun was still on the pots so I thought I would water them once the shade came over them.



My friends wife was a slim hottie called Tina and I thought my pal was punching above his weight. I had even heard that she had cheated on my pal with some local younger guys and she always seemed interested in talking to me when I met them out. Like holding that eye contact a little longer with a glint in her eye, that would make you feel horny. Yes, for a 50yr old+ woman Tina was a sexy lady.

I could not stop myself wondering what was in her lingerie drawer. I guess I had built up an image of Tina being a bit of a cougar. I knew my friends bedroom was in the loft so I headed up.



It was not long before I had found a sexy pair of sheer to waist pantyhose, a little red sparkly sleeveless cocktail dress, some cute wee sling back heels with peep toes and ‘joy of joys’ a pretty shoulder length, dark brown wig. I quickly stripped off the summer shorts and tee shirt I was wearing and slipped the pantyhose up my smooth legs and straight away got that thrill as I pulled them up and felt the nylon encase me. I put on one of Tina’s bras and padded it out then slipped on the red dress. Then the heels. I could see my figure instantly transformed as the heels fixed a different profile to my outline.



I dabbed on some make up then positioned my hairdo (I hate the word wig lol). I felt absolutely incredible and took selfie after selfie. It was extra thrilling knowing I was wearing Tina’s things. I wondered if my friend might prefer how I look in the outfit rather than Tina. That led me to thinking about being in a threesome with them and I don’t need to tell you what affect that had on a certain part of my body. So I pleasured myself accordingly.

As always the dressed up episode had to end and after an hour or so I was putting Tina’s items away where I’d found them and headed down to water the garden. I was stunned to see that they had just been watered. Tina’s brother was also charged with watering the plants while Tina was away, and had stopped by on his way home from work to undertake the task.



It still gives me jitters to think of how close I came to getting caught. I even had the radio on up in the loft room whilst I was dressed which is maybe why I didn’t hear him come in but it amazes me that he didn’t hear music coming from the upper floors and go to investigate.

I knew him and we always got on well. I had been in the pub with all of them in the past and Tina’s brother was always very friendly towards me so it might have finished well had he caught me. It might be that he sneaked up and saw me otherwise engaged and oblivious and decided to let me get on with it. Maybe that’s why he was always very friendly to me. It if is I wish he’d say something or make a pass at me.

One can dream. True story though xx

Submitted by Sasha Fontaine

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8 Comments

  1. I’ve always wondered what it would be like to get caught. I fantasize about being intimate with another gurl and have her partner walk in on us and force us to finish and then she makes me their sissy maid

    1. That sounds nice. I have this fantasy about one of my friends. I fancy him so much and my wife is very fond of him because he is a genuinely lovely man. It just so happens that he is slim and handsome. Fair blonde-ish hair, blue eyes and well spoken. We are close pals and it makes me feel fraudulent that I secretly xdress and meet other tgurls, am secretly bisexual, fancy him, and fantasise about dressing up with him. I feel I need to fess up to him about being bi but we live quite far apart now and do not see so much of each other. Both got kids etc now. But I always go back to the fantasy of dressing him up as a pretty tgirl. There was once that I stayed overnight with him a few years back and he wore just a bath robe at one point before. I fantasise vividly about him slipping it open to reveal a sexy, semi hard, fully shaved cock, and me swooning to slobber my lips and tongue all around it. If that ever happened I would definitely coax him into a pair of nude pantyhose with some skimpy pink satin knickers on underneath. With a micro short pleated skirt, lace neglacé, loose white blouse and sling back heels. My tongue would get cramp licking every part of my new sissy sexdoll mmmmmmmmmm xx

  2. Fear of getting busted Was a turn on for a long time then it happened an let me tell U it was not at all fun infact for me it turned out very bad at first nobody understood but it’s getting better slowly
    I still won’t go public because of it though a small number of very close friends know an have seen

  3. If you enjoy crossdressing to the point were you think you would like to be caught but!! as I always thought it would be simpler to come out of the closet but I could never pluck up the courage to do so, but been caught fully dressed as I did turned out to be much simpler instead as the guy who caught me made me realise why I preferred been dressed as a girl
    ,

  4. I have ben cross dressing for a long time i buy thing at stores locally , I am now going out at night dressed up and i have been hit on, by men and they were turnd on i helped them out too. i am going to the beach this summer wearing a bikini and girl things i hope it gets some attention .

    1. If you get hit on by men when you are out there dressed up, your sure going to be hit on when you’re wearing a bikini.
      You will probably have your pick of guys, so be sure that you pick a good one and go with your feeling about how far you want to take it
      Good luck, girl. I know that your going to have a good time

  5. Many years ago, when I started being interested in wearing girls clothes, I was alone in the house and went into my sister’s room to look around and see what there was that would fit me.
    In her closet, I found three petticoats. On was white, one was pink and my favorite was the one that was light blue.
    I stripped down until I was completely undressed. I looked in a drawer and found a pair of panties that fit me. After putting them on, I layered the petticoats on, like it was a gown. I couldn’t believe how girly I looked, when I looked at myself in the mirror.
    My manhood was hard as nails and I was leaking pre cum into her panties.
    I lost track of time as I walked around her room, looking at myself in various poses in the mirror
    All of a sudden, her bedroom door opened and there was my sister ,looking at me wearing her petticoats and acting like I was a girl.
    She told me that I didn’t look much like a girl and if I wanted to continue dressing as a girl, to find my own clothes and leave hers alone.
    I apologized and told her that I wouldn’t wear her clothes again
    I cut lots of lawns after that, so I could make enough money to buy my own clothes and lingerie
    That was the first time I was caught dressed in girls clothes.
    The next time I got caught was years later and I was married.
    I usually went to a motel to get dressed, but I was home and my wife went shopping with her mother. They usually were gone for two hours or more, so I decided to get dressed.
    I got my stash of women’s clothes and lingerie from my car and took them into the bedroom where we lived.
    I had a prosthetic vagina to hide my male parts and I was wearing it. I had my breast forms on and a bra holding them in place.
    I was sitting on the bed and had on thigh high stocking on and fastened to a garter belt.
    I was pulling the other stocking on, when the door opened and there was my wife standing there looking at me in disbelief.
    Of course we had a huge argument and she never forgot or forgave me.
    We got divorced soon after that and I learned a hard lesson.
    Never dress en femme, until you are in the privacy of your own home or motel room and your sure that you won’t be found out that you are a crossdresser
    It works for me, as I’ve never been embarrassed by crossdressing since my ex wife caught me many years ago

    1. Very true. Totally agree.

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