Remembering my teenage crossdressing fun
After assembling my first full outfit from my cousins wardrobe. At a young age, I knew I wanted to dress like a girl. After the first time wearing a bra, panties, dress, and pantyhose and waking around the house, feeling the dress swing around and my nyloned legs touch together...I was hooked. As I was getting older my crossdressing hobby was growing more serious. I was graduating from wearing just panties and bras to fully dressing and experimenting with makeup. It was easy access because my sister and I shared a bathroom. I would dress every chance I was home alone...
Around age 17 I remember my step sister went to some event wearing a black dress and black stockings all made up. I was always jealous when I saw her wear sexy outfits like that.... After the event she came home and changed clothes and went back out with friends. I was playing video games when she left again. I went to her bathroom and there was the black dress on the floor and stockings hanging on the towel rod. I didn't know how long she would be out but knowing her it would be late. Our parents were out of town for the weekend and I instantly knew this was an opportunity. I picked out a baby pink bra and panties and went strait into the bathroom. It seemed like in one quick motion I was out of my boy wear and stepping into panties hooking the bra on. I grabbed the stockings and sat on her bed wearing her panties. Rolled on each stocking up, then stepped into her black rouched dress and pulled it up. The Instant sensation wearing womanly bliss hit me... Next some makeup and perfume, put on my wig. This is my happy place. The only thing I didn't have of my own at the time was heels....anyway I spent the night dressed and played video games. Funny I chuckled to myself as I played call of duty kicking the shit out of people playing online and here I was this teenage boy crossdressing sissy transvestite dressed fully in his sisters clothes playing online games. Only if they knew they were getting their ass kicks by a crossdressed sissy boy.
I jerked off a couple times and layed down on my bed. I must have fallen asleep for a bit but was woken up by the dog barking at the front door. I looked at the clock and it was almost 3 am. My sister was home, but it didn't matter.I just closed and locked the door to my room and started surfing Tgirl porn. I heard her come upstairs and go into her room. I layed in bed still wearing her pink sheer Victoria secret panties and matching bra. Her black thigh hi stockings, and dress while jerking off. While pleasuring myself and rubbing my stockinged legs together I was almost about to cum when I hear my sister tap on my door and ask are you still awake? I freez and say nothing. only if she know her step brother was right there on the other side of the door wearing her earlier outfit with an erection sticking out and pre cum dripping off the tip. I almost wanted to open the door and show her what a sick fuck I am. She went back to her room and I exploded cum into my hand and layed backdown licking my fingers clean. I slept the rest of the night in her bra, panties and stockings.
Next morning I was up befor she was, one last jerk and took off her cloths. I put them in the dirty pile and took it all down to the laundry room...she wouldn't think twice about it. I always feel guilty after behaving that way...but then again I can't wait for the next chance....
Around age 17 I remember my step sister went to some event wearing a black dress and black stockings all made up. I was always jealous when I saw her wear sexy outfits like that.... After the event she came home and changed clothes and went back out with friends. I was playing video games when she left again. I went to her bathroom and there was the black dress on the floor and stockings hanging on the towel rod. I didn't know how long she would be out but knowing her it would be late. Our parents were out of town for the weekend and I instantly knew this was an opportunity. I picked out a baby pink bra and panties and went strait into the bathroom. It seemed like in one quick motion I was out of my boy wear and stepping into panties hooking the bra on. I grabbed the stockings and sat on her bed wearing her panties. Rolled on each stocking up, then stepped into her black rouched dress and pulled it up. The Instant sensation wearing womanly bliss hit me... Next some makeup and perfume, put on my wig. This is my happy place. The only thing I didn't have of my own at the time was heels....anyway I spent the night dressed and played video games. Funny I chuckled to myself as I played call of duty kicking the shit out of people playing online and here I was this teenage boy crossdressing sissy transvestite dressed fully in his sisters clothes playing online games. Only if they knew they were getting their ass kicks by a crossdressed sissy boy.
I jerked off a couple times and layed down on my bed. I must have fallen asleep for a bit but was woken up by the dog barking at the front door. I looked at the clock and it was almost 3 am. My sister was home, but it didn't matter.I just closed and locked the door to my room and started surfing Tgirl porn. I heard her come upstairs and go into her room. I layed in bed still wearing her pink sheer Victoria secret panties and matching bra. Her black thigh hi stockings, and dress while jerking off. While pleasuring myself and rubbing my stockinged legs together I was almost about to cum when I hear my sister tap on my door and ask are you still awake? I freez and say nothing. only if she know her step brother was right there on the other side of the door wearing her earlier outfit with an erection sticking out and pre cum dripping off the tip. I almost wanted to open the door and show her what a sick fuck I am. She went back to her room and I exploded cum into my hand and layed backdown licking my fingers clean. I slept the rest of the night in her bra, panties and stockings.
Next morning I was up befor she was, one last jerk and took off her cloths. I put them in the dirty pile and took it all down to the laundry room...she wouldn't think twice about it. I always feel guilty after behaving that way...but then again I can't wait for the next chance....
6 years ago
