Our crossdressing cross-dressing stories feature tales of either gender usually male dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation. The last few weeks had been extremely busy and my wife and I had very little time to spend with one another. We needed some alone time so we made arrangements for the kids to spend the night at their grandparents house.
What shall he do now? Katie had managed to talk them into allowing her to stay and look after me, without the help of our grandparents. Will you wear it or not? What will my mother and father think? Mg asked me to raise my hands, and when i did, she locked them into the upper hook. Comments
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Whatever, it works for us. I'm gay and she's a lesbian and things seem to work well, with a wrinkle Caught my nephew crossdressing at school two, but I just love the role of being an aunt. Sons whore wife caught masturbating blackmailed into sex. I was caught in some sort of "Kafka world". I suppose I could have avoided all of the sneaking around and worrying by simply being myself. Lust Flesh Uncle fuck her niece and cum inside. Pajama party time. Cooch TV This is the story of a young boy who is dressed up by his sisters to see what his twin sister would Cayght looked like had she lived.
School was out!
- Hi there, I know the aunts here have many admiring nephews but I'm just curious as to how many of those nephews are curious about the feminine world their aunts inhabit.
- Stories by Patricia Anne Anderson page 1.
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Author's note: I am writing this at the age of 27, on Monday 26th March, While it might seem to be a far-fetched account, what you read is true. Everything happened. While I try to write an unbiased entry of my life, some of what I have written might sound biased.
I shall leave you, the reader, to make up your own mind. I remember watching my older sister Katie walk around in skirts, dresses, blouses, all clothing that was infinitely better than anything I wore.
It looked nicer, and when I hugged Katie, her clothes felt nicer against my skin, a lot nicer. There were times when I was left on my own in the house; my parents were either at work or out for the afternoon, and my sister was visiting her friends. I had freedom of the house, and since my fascination started, I had only wanted to do one thing: try on my sister's clothing.
Many would have found it weird, an eleven year old boy wanting to try on girls clothing. I didn't really care at the time, I didn't know what kind of effects it would have on my future. At the time, when life seemed simple, I only saw it to be innocent curiosity that drove me to try on my sister's clothes. I didn't have any idea about the culture that followed it, I didn't know that men and women dressed in clothing of the opposite gender as a lifestyle choice, I would find that out much later in my life.
When I entered my sister's room, I had an idea of what it would be like. Pink, filled with girly things ranging from dolls to make up to posters of boy bands and actors.
I was definitely mistaken. At the time my sister was sixteen and going through her GCSE's. Her room was painted a cream colour, very few posters decorated the walls, shelves were filled with books and not dolls, and she had a large wardrobe up against the wall. That was my first port of call.
I opened it up, and was stunned to see everything hanging up so neatly. My sister was a bit of a neat freak, everything was out of place, and it was rumoured that she could see from first glance whether or not something was out of place.
I always believed that Katie had some sort of second sight for these things. It was proved right when I was first caught by her. Coincidently, it was also the same day I started trying on girl's clothing. When my parents and Katie had gone out, leaving me alone, I went into her room, and opened up Katie's wardrobe. I was instantly drawn to the dresses. She had a ankle length purple dress with straps. Now on Katie, it would have went down to her ankles, but when I tried it on, it went down to the floor, and even bunched up leaving a small tail of fabric.
It didn't matter to me at the time; I simply stripped to my underwear and slipped the dress on over me. It didn't even need to unbutton the back of the dress. I looked at myself in the mirror that was placed on the inside of the door. My green eyes staring at the figure in the oversized dress. I felt the satin against my skin, and I liked it. I still looked like a little boy trying on adult clothes though, I had short brown hair back then, my parents choosing my hair cuts and how I looked for my time at school.
I was going to take the dress and hang it back up to try on another item of my sister's clothing when I heard the door open. Someone stepped inside, and I was unaware who it was until I Katie shout up to me.
I'm home. I guess you are wondering about my name. Yes, I am called Rain. My full name is Rain Alexander Edmonds. I don't know why my parents named me Rain, it wasn't to do with the weather, I was born on Saturday October 20th, , and according to my parents and sister it was a sweltering hot day so how Rain came into the conversation is a mystery.
Anyway, back to the story. When I found that my sister returned; the first thing that went through my mind was a close resemblance of the words "oh crap" ran through my mind. I still hadn't changed out of Katie's dress and my clothes were strewn over the floor.
I was going to be found and instantly my mind told me to hide. I immediately jumped into the wardrobe, and closed the door behind me. I remember that exact feeling when I was hiding from my sister. My heart was pounding, it felt like it was going to burst from my chest in a similar style to the Alien Quadrilogy.
It would have solved some problems though, first off I would have been dead, and I wouldn't have to face my sister's wrath when she found I had tried on her clothes.
She probably would have tried to resurrect my body and then kill me all over again for it. This was the moment I found my sister really did have a second sight. I overheard her muttering that she had shut the door to the bedroom before she left, and I foolishly left it open. She knew I would be in her room, and the fact that my clothes were left out for all to see didn't help that.
If you don't come out until the count of five then I will be forced to tell mum and dad. Katie didn't raise her tone, she didn't have to. Knowing that Katie would tell our parents that I had been hiding in her room was really the only contributing factor of actually giving myself up. That and if I had continued to hide in her wardrobe, any chance of denying it would be useless considering I had left my clothes out.
She started counting down, and I knew it was now or face the wrath of my parents. They would never have understood it back then, but it was likely that they had taken it down to a phase in growing up. The old 'curiosity killed the cat' saying. They would have forgotten it, and just told me never to do it again. I didn't even know how my sister would have reacted, but it didn't matter. I had to come clean and so, I pushed open the door to the wardrobe, and shuffled out into plain sight of my sister.
For a moment Katie was quiet, she just stared at me. I was expecting her to start shouting and screaming at me, ordering me out of the dress and to get changed. I was definitely wrong. Katie hugged me. She stepped forward and wrapped her arms around me, a smile was on her face. I was dumbfounded, awestruck, amazed that I wasn't deaf from the screaming and shouting that I had originally expected. She in fact explained to me that she had really wanted a little sister instead of a brother.
I didn't understand it at the time, but if I did fully take into account the words back then I might have been offended, but I knew she still loved me.
Katie told me she was happy having a little brother, and when she saw me wear her dress, she actually liked it. Sure she was a bit annoyed that I tried her dress on without asking, but she didn't let it overshadow the clear fact we had just come closer together. I explained to her my reasons, why I was wearing her dress and hiding from her.
The fact that I liked the look and feel of girl's clothing, and was curious to try something on. Katie asked me if I liked it, and I said yes. What she did next definitely surprised me. She took the dress off me and hung it up, instructing me to get changed into my previous clothes. When I was finished, Katie told me to follow her down to the basement. Now at the time when I was eleven years old, I had in fact been scared of the basement.
My grandfather told me stories of monsters in the basement, and I'm ashamed to say that I believed him to that point.
It turned out that our parents had kept boxes of old clothes going back the years. Every outfit of value and importance was sitting in the cases. My first football kit. Katie's first ballet outfit. Both mine and Katie's school uniforms from school. Our parents had the odd habit of sorting things out into boxes with the ages written on, and it actually helped Katie with what she was doing.
My sister brought out a box of clothes from when she was eleven years old. That was a great year, apparently. My aunt and uncle got married, Katie finished primary school, she performed the lead role in a ballet recital of Swan Lake, and there was the first family vacation, a cruise to the Mediterranean.
The outfits were going to be for me. Katie explained to me that she had always wanted a younger sister so that she could have someone to practice giving make-overs, and dressing up. I was filling the shoes of being Katie's younger sister, even if it was only at random dates and times.
It would only happen when the parents were out. We would have started that day, but unfortunately our parents had returned earlier than expected. It didn't matter to me, or to Katie though. It was the start of something new, a fun new experience that would bring us closer together as siblings.
Our parents had been invited for a ball in London. Katie had managed to talk them into allowing her to stay and look after me, without the help of our grandparents.
Near fatal. Shemale Porn. All Long. Kimmy SissyFur says: Nicely put! Hi there, I know the aunts here have many admiring nephews but I'm just curious HD Tube 1 I'm gay and she's a lesbian and things seem to work well, with a wrinkle or two, but I just love the role of being an aunt.
Caught my nephew crossdressing at school. 16 thoughts on “Have you been caught xdressing?”
School was out! The prom and the graduation parties had been a blast, but I was looking forward to something even better. It was spring and I was eighteen. I knew I'd have a dismal summer if I stayed in town. I hadn't been very popular in high school and, as a result, I had no close friends.
My parents had just left to spend the next four months in Europe, and I had been invited to visit my Aunt Susan and her daughter Jill in San Francisco. It was quite an adventure for me as I'd never traveled away from New York state before, and it had been ten years since I'd last seen my aunt and cousin.
I was especially looking forward to the trip and my summer with them. I arrived in early May and Aunt Susan and Jill met me at the airport. Aunt Susan was in her middle thirties and a tall, very attractive brunette with a terrific figure. Jill, at nineteen, was a budding California blonde, beautiful and nicely developed.
I couldn't take my eyes off her and had a hard time paying attention to Aunt Susan's family reminiscences on the drive to their home in Marin county. I tried concentrating on the California sights during the brief trip rather than embarrassing myself gawking at Jill. When we pulled into the driveway, I was astonished at the beauty of the homes in Aunt Susan's neighborhood.
Never had I seen such lavish houses before. It dawned on me then that I must have a very wealthy aunt. Her home was a lovely, newer Victorian style occupying the top of a small knoll with an acre of land surrounding it. The grounds, especially in front of the house, were covered with flowers and trees I'd never seen before. Just behind the house was a swimming pool hidden from the rest of the nearby homes by an eight foot fence.
Definitely posh. I was given the guest room next to Jill's bedroom and across from Aunt Susan. I supposed it had been recently occupied by Jill or one of her girlfriends as it was decorated in very feminine fashion; ruffled pink curtains, a pink satin spread and flowered wallpaper.
I didn't feel I should complain about the decor. After all, I would be a guest for a mere four months. I quickly unpacked my things and went to put them away in the dresser.
The closet was much the same; lots of dresses, skirts, blouses and many pairs of shoes. I was barely able to squeeze in my pants and jacket. Just as I'd finished unpacking, Aunt Susan called to come to lunch. She had prepared a fresh fruit salad and some lemonade. I fibbed a bit, trying to be a good guest.
I'm sure I'll be comfortable there. We have lots of fun things planned so I know you won't be bored. Having experienced jet lag for the first time, I quickly agreed and retired to my new room.
As I dropped off to sleep in the canopied four-poster bed, I heard Susan and Jill whispering outside my door, but couldn't quite make out what they were saying.
Just as I fell asleep, I thought I heard Jill laugh and say, "I'm sure she'll make a delightful sister. I dressed in a tee shirt and shorts and went into the living room, finding Jill alone on the couch watching television.
She was dressed only in a semi-transparent blue night gown. It was extremely sexy and a perfect accent to her blonde good looks.
If you want anything to eat, just help yourself. Where's Aunt Susan? This will be one hot summer, I thought, if this is the way she dresses around the house. Not that I had any complaints.
A movie was playing, but I didn't know what it was and, at that point, I really didn't care, that is until I happened to notice some very strange scenes in it. It's about this guy who dresses up as a girl. I think they look very pretty. If this guy in the film is like all the rest of them, it really must give them a big thrill.
As far as I'm concerned, there's nothing wrong with it. It doesn't hurt anyone, does it? He finally managed to hide it and, after he put on a matching bra and slip, he was very cute and sexy looking, I must confess. As I watched him transforming his face into that of a girl, I was starting to get that old familiar tingling in my groin. Being able to see through Jill's nightgown didn't exactly cool me off either.
Then I remembered how I'd felt the times I'd tried on some of my mother's clothes. Strangely enough, wearing them had made me feel very good, but I'd sworn off experimenting with women's clothes a few months ago because my mother had come home one afternoon unexpectedly and caught me wearing one of her dresses. I confess I'd panicked. I could only stand there frozen in front of her, unable to move or even talk. She hadn't been angry with me and said if I wanted to talk about it, she'd try and understand why I wanted to wear women's clothing.
The only response I could manage was to run into the bathroom with tears of embarrassment running down my face. I had stripped off her clothes as quickly as possible and I'd never worn her things again since that day. The next thing I knew, Jill's hand was resting on my arm. Another wave of heat stormed across my groin and I could feel my cock harden. She must have interpreted my silence as further disapproval. I would have agreed to watch a ballet if I could stay there next to her, and I think she realized it.
We sat there for a while, not saying a word. The movie was getting to both of us. I inched closer to her and she began to stroke my arm, then she moved her hand to my thigh. Moments later, she looked down at my lap. It gets me steamed up, too. Would you think I was terrible if I asked you to kiss me? A few minutes later and much to my amazement, she dropped the straps on her night gown revealing both her breasts. She was fully developed and they were perfect; firm, ripe and just begging to be touched.
Jill took my hand and put it on one. It felt wonderfully soft and warm. I had never felt a girl's breast before and could sense the blood rushing to my face. She was thoroughly enjoying my discomfort. I could tell she really enjoyed teasing me. To shut her up, I leaned over and kissed her. Just as our tongues were exploring each other's mouths, Aunt Susan came into the room. She looked down at us, her face filled with astonishment.
Both of you go to your rooms and I'll come up in a minute. We're going to have a long talk about this. She closed the door and sat on the bed next to me. Take off all your clothes! I turned to her wearing only my briefs.
Now take those ugly underpants off immediately. As I slumped down on the bed desperately trying to hide my genitals, I could picture myself being hustled to the airport and dumped on the next available flight home after an angry call to my parents. I'm sorry. I'm just kind of embarrassed.
Now I want you to lay down on my lap. You behaved like a naughty child tonight so I'm going to have to treat you like one. On my lap! As my penis touched her nightgown I was horrified to feel it getting hard. What would my aunt think of me? But, much to my relief, Aunt Susan either didn't notice or she didn't care.
Thankfully, she stopped and ordered me to sit next to her on the bed. I told her about the boy in the film who had dressed up in girl's clothing, and I admitted it had aroused me a lot. I apologized to her for touching Jill, but she just smiled and told me it was only natural to be curious about the opposite sex.
I was sitting there naked, feeling quite helpless but still erect. After all, she is still young," Susan said. Her breasts were much fuller than Jill's and her nipples were as hard as my cock.