Crossdressing Stories


Caught crossdressing story

“My name is Roger. I am a 29 years old, white, a little skinny , and a married (secret) crossdresser. I really love wearing women’s clothes and I am crazy about pantyhose (and tights. I love the total coverage and the sensation that pantyhose gives me.

One afternoon my friend, Bob called me and asked to house-sit while he went on vacation. The house was empty, save for a table and four very comfy chairs. It had been renovated and listed for sale, so it was all new, but empty. He asked if I could keep an eye on things, take calls from realtors if they called, and go make sure everything was okay.

He gave me a key, and said I could do whatever I wanted while he was gone. I could ‘hang out’ or whatever. He knew I was studying for a certification, and mentioned it would be a nice, quiet place to get away. Immediately I formed a plan, seeing this as a golden opportunity unlike any other I’ve had in a very long time. I already knew what I wanted to wear, and I couldn’t wait until late at night when I could leave home, go to this empty house, change into my female persona, and enjoy some ‘me’ time.

I love dressing completely from head to toe and always put on a wig, makeup, nails and the clothes when I dress up. It’s an exhilarating feeling. I had just bought some purple patterned pantyhose on clearance as well as a beautiful pink bustier with black lace. I would wear that under a shiny black 3/4 sleeve top, and a very tight, sexy, ribbed black tube skirt. I would of course finish off the ensemble with bright red nails to match the hooker-red lipstick I would apply, and a pair of patent black Mary Jane’s with a 4″ heel. I was already hard just thinking about it.

I got everything together, making sure I had what I needed, including a spare pair of hose (always have a spare, I hate runs), my makeup, lube, and the rest of the outfit that I couldn’t easily wear under my man clothes. With that all done, all I had to do was wait…for two more days! That’s like two MONTHS for my level of excitement and anticipation. I wasn’t simply planning on dressing up and prancing around an empty house at night…I wasn’t planning on being the only one to enjoy what I would be wearing!

With plenty of time to plan and wait, I crafted an ad online. I had always fantasized to spend some time with other crossdresser. Having a place to host, in this case the empty house, while not glamorous, gives me a much better chance than I would otherwise have had. So as you might imagine, I got quite a few more replies than usual…of course, that means nothing if they’re all flakes who just want dirty talk and pictures to get them off.

I eliminated most of the replies and narrowed it down to two that seemed promising. One of the ‘finalists’ was only available that night, which was not possible, so now I was down to one. I was hoping this would pan out. I’d hate to miss out on this opportunity. I only had a few days. So this last prospect sounded really serious. He just needed 20 minutes notice to get there, and promised he would show up. Believe it when I see it, but nonetheless, I was pumped, excited, nervous, scared… all the normal emotions I always feel when arranging a meet up with a complete stranger.

My biggest fantasy is to find a regular who lives alone and lives really close to me, like walking distance, where I could keep a closet full of clothes and shoes at his place, and a drawer full of makeup in the bathroom. I guess I’m looking for a ‘double life.’ So far, this is still just a fantasy. Back to reality…

We agreed on a time, and he wanted me waiting inside the house, where he would come fully dressed up as well. We would simply both enjoy the moment as pretty women. The next two days dragged on and on…

The day had finally arrived. I had been imagining to the scene in my head for the last 48 hours, and finally the day, or more accurately, the night, was finally here. At about 8 pm I put everything I needed.. my makeup, wig, fake tits, shoes, dresses etc. in my gym bag. I told my wife I was going to a get together with school friends. I threw the bag in my car and drove the short distance to the empty house. Letting myself in with the key my friend had given me, I locked the door behind me and went upstairs to the bathroom.

In the bathroom I removed my outer clothes, put on the bra and panty, my fake breast form and applied my makeup. I felt really sexy and hot while I was feminizing myself fully from head to toe. After my foundation, bronzer and blush, I applied my eye shadow, eye liner, and hooker red lipstick. Then I put on the red dress and black pantyhose that I just brought recently.

I then put on my wig, clipped on a pair of dangly earrings, and slipped into my Mary Jane heels, my legs looking hot as they maneuvered into the shoes. Looking at myself in the mirror, I was exploding with feminine sensation throughout my body. I would so love to go out like this any time I wanted, day, night, to a mall, Wal-Mart, around town…but obviously, that’s not a reality.

Then, I get a text from him. He asked if I was there. I told him I was, I was ready too. He said he was leaving his house now, which would put him about a half hour later than what we had set up, already being ten minutes late. I have hours, so it’s not a huge deal, but I hate waiting around for someone. Then of course I start to think he’s just playing games, it’s happened before…I’d be all ready, fully done up, guy said he was on his way, never hear from him again. Some people just like playing games.

My phone was almost dead, so I hoped it lasts long enough to continue communicating with him, that is if he’s really coming. About 20 minutes later he texts me again…he’s pulling in the long driveway. He finally arrived at the doorstep, I went to greet him, a bit nervous but excited at the same time. He seemed to be excited and a bit nervous to see me as well. He was looking hot in a beautiful red flouncing dress with nice heels. He was slim and looked quite feminine indeed. I was happy with what I was seeing.

“Hi, you look lovely. Thanks for having me.” He said.

“You look great too and it’s a pleasure.” I replied.

We go inside and sit on the chair. We start our conversation by telling each other a bit about ourselves. He tells me her feminine name is Samantha and he has been cross-dressing for the past 10 years. It was really exciting to have another crossdresser to talk with. I was really enjoying the moment and I had a lot in my mind about what to do next. But then, all of sudden, he comes really close to me and kiss my lips.

I get shocked not knowing what to do but it felt good. I wanted to stop him but he was just too good to resist. I did fantasize about making out with another crossdresser but that was just a thought. Now, it was happening right before my eyes.

He then slides his hands inside my dress. I was turned on immediately and my feminine senses go off the roof. We kiss each other passionately.
Then, he puts his hands around me and unzips my dress. I feel very submissive at that moment; Samantha was really good at this I thought. Then he grabs my fake breast and the sensation was something I had never felt before. He gets me out of my dress and makes me sit on his lap. He then starts caressing my legs and my chest very gently.

Then as he was going for the back of my bra, the front door opens suddenly. It was Bob; he was back from his vacation early. He instantly turns red with anger realizing there was unwanted visitor in his house. He starts yelling. He doesn’t realize it is me, his old friend. I don’t know how I would ever get out this situation now, I thought inside my head. I was caught.. caught in the act.

I picked up my dress, put in on as fast as I could. Bob was still yelling. He was threatening to call the police now. I had no other choice but to admit that it was actually me.

“Bob, It’s me.. Roger! I am sorry but I didn’t expect you to come back this early” I said in an ashamed tone.

“WHAT?? What the hell Roger, what is all this?” He replied, still very angry.

“It’s okay Bob; I will explain everything to you.” I said, feeling very ashamed.

I push Samantha to go and he leaves immediately. Now, I had to face Bob and explain everything to him. I was never so embarrassed in my life. Bob had calmed down a bit. Then, I sit down on the chair and with a deep breath, I start explaining everything to Bob about me being a crossdresser and what I had planned to do this evening. Bob then comes a bit closer.

“I will forget everything that happened today if you do a favor to me.” Bob speaks.

“YES! I will do anything” I reply back immediately.

Then Bob comes really close to me and holds my hand. I look at him, I was nearly about to cry with guilt. Then with a smile on his face, he says “Well, actually.. I did fantasize about making out with a crossdresser someday. Are you up for it?”

I was shocked. ““No.. Bob, please don’t do this.” I cried, trembling. But it was already too late.
“You actually do make a beautiful woman, Roger.” Bob then holds me in his arm. This was going to be a long night for me, something that turned out to be even crazier. ”

The End

Facebook Comments


  1. story was very erotic and sensual. As a crossdresser myself, I can identify with the main character. It is really a wonderful moment when you can become the person you were meant to be. I LOVE BECOMING A WOMAN!!!!!!! As I write this I am totally dressed and feel as feminine as I can be.

    1. i would enjoy meeting you some day.

  2. I would love to meet another cross dresser who would dress me up and make me into a sissy girl and give me some tips and advice

    1. Hey Gerald! I’m also a crossdresser, looking for another friend to dress up with :3 What area do you live at?

    2. I’m her

  3. Would love to meet a fellow crossdresser and makeout

  4. I can relate some. I started cross dressing at age 16. I lived close to the redwoods in N California. I had my private spot I would go to and wear my moms panty and bra and spend about an hour walking around and then get dressed and go home. I had been doing this once or twice a week for about 6 months. I had walked around and when I returned my Cousin Lisa was standing there. She and my uncle lived at the opposite end of my block.

    She told me she had seen me for weeks heading into the trees and decided to find out what I was doing. She was also 16.. She smiled and continued to look and began asking questions about my dressing. She promised to keep my secret if when I came to my spot she came with me
    Every day at school she would ask if I was going to the trees. I would say no but after about 5 days she told me that if I would go the next day she would have a surprise for me. She even rode home with me. We got into the trees and I pulled out my moms panty and bra when She told me to wait. She reached in her purse and pulled out a pair of sky blue bikini panties. To that tome I had worn my moms granny panties.. She loved them on me. I started to put on moms bar and Lisa stopped me again. She pulls off her blouse and takes off her bra and hands me it and even helped me put it on. This was the first time I had see real tits. I was getting hard and she loved that. She ran her hand over my hardening cock and asked if I jack off and I admitted I do. She wanted to see me do it so I did. Her eyes sort of glazed over until I shot my load.

    The next day at school she again wanted to go to the trees and promised another surprise. I could hardly wait. Went straight to my spot after school. As I started stripping down so did she. First she took her bra off and put it on me and then took off her panties and put them on me. We walked around for awhile lie that and she wanted to see me jack off. I started jacking off and she took hold of my cock and just hed it. I figured what the hell and grabbed her tits. She held my hand on top of her tit as she started stroking my cock
    This went o a few times a week until after graduation and I left for the military. We got to the point that I would finger her pussy as she stroked me. Over the years e mails and phone calls continued about or time playing. we a few times a year made attempts to get together and do the same thing. We are both 68. I retired 5 years ago and she is retiring in about 6 months. We live 9 hundred miles apart. The past few months her emails have started hinting about us living together and she has described how she wants to have sex

  5. When i was in my early twenties I was caught in a neighbor’s yard trying on her bikini off her clothes line by her other neighbor. to keep my secret it started a secret relationship that lasted 10 years until he moved away. we made frequent romantic getaways on his boat. I’m 60 now and i still miss those weekends

  6. I would love to meet I have been looking for a cross dressing to so me how I live in whaltham mass just outside of Boston mass USA

    1. Haverhill, MA here. Love to play
      Are you on Fetlife? If not, you need to try it… it’s free.

  7. I wear some panties and bras sometimes…and so does my friend but no makeup…don’t know how… just ordered a a breast plate with c tits hope it works out…. would love to be with another cross dresser….

  8. I also love dressing up, as read this story I’m in makeup wig and still in my jammies. My fem name is Barbie and my wife knows of my cross dressing and fully supports it. We’ve gone out together to buy me clothes and has taken me on car rides fully dressed. But much like other cross dressers I too imagine what it would be like to make out with another cross dresser. Some times I’ll come in close to the mirror on my bedroom door and pretend I’m looking at another Beautiful cross dresser. I’ll talk to her in my best and sexiest female voice, most times I can’t resist kissing her.

  9. loved the story… meeting another dressers unexpectedly is exciting. Love to dress amd have my body rubbed all over by another T girl… Charlene near philly pa.

  10. I’ve Been Dressing Up For Years.. Many Dresses.. Skirts.. Heels.. Tights.. Bras & Panties.. I’m Very Well Hooked:))Enjoy Shopping With The Ladies…

  11. I’d been crossdressing for a few years borrowing my mother’s clothes & thinking I’d never be caught dressed but I carried on regardless, then after I left school & began working, I began buying my own clothes/wigs makeup etc. & Saturday afternoon when I was about 20 I decided to get a little more adventuress, have a long bath & rid myself of all that ugly male hair from my body, then spending ages getting dressed & made-up, & go outside take some photos wearing different outfits, I was caught dressed as a schoolgirl wearing a pleated miniskirt & 4″ high heels by 1 of our neighbours sons (& god he was handsome) who just happen to call to check the house as they knew my parents were away, & like Roger he didn’t recognize as I was fully made up false eyelashes & red false nails the lot, I don’t know who was shocked the most but seeing the bulge in his jeans I knew he’d been watching me for a while, All I could bring myself to say was “hi” as he stood there with his mouth open as he realised it was me, then telling me he’d seen me sneak outside dressed a few times in the past, Feeling I was in a tight corner I found myself saying “come in for a coffee Andy & I’ll explain” sounds corny but that’s all I could think to say & grabbing his hand I lead him into the kitchen where upon Andy spun me around & pulled me close to him, gazing into each other’s eyes I could feel my feminine instincts take over & even though i was wearing 4″ heels I to stand on my tiptoes I kissed him on the lips, OMG I thought as a shudder of excitement ran though my body as he put 1 hand up my miniskirt & grabbed my lace covered ass & with the other grabbing the back of my head as he fervently kissed me for what seemed ages, I’d never kissed a man before but somehow it felt natural to me & from the way his hands were exploring my body I knew I was in for more than a kiss, I was right & not long after I found myself stripped to lingerie & high heels & bent over the kitchen table with my knickers around my ankles been given what a girl like me needed in his words,

  12. Great story. I thought it was going to turn out to be Bob who was the visiting tv. That might make a good alternative ending.
    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. 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 bra 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

Leave a reply

Your email address will not be published. Required fields are marked *

You may also like