How I got started dressing
I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just used sites like google or yahoo to find videos by typing in whatever I was into that day. It started out with just words like "blonde getting fucked" or "girlfriend giving blowjob." Once I started to get bored my words started to get more descriptive "Slut takes huge cock in ass."I was skimming through videos until I found a thumbnail that caught my interest. The thumbnail was of a girl that was tied up with her ass in the air just asking to get fucked. Of course I immediately watched the video was so turned on that I shot my load within a minute. The fact that someone was tied up and helpless taking a cock in there ass was the hottest thing I had ever seen. I wasn't exactly so sure at the time why I got so horny but I was about to complain.
I continued watching bondage porn for months and months realizing it took a lot longer to get bored of it then the other porn I had watched. I discovered more of the humiliating type of bondage videos which kept me watching more and more porn. By now I started typing my keywords even more descriptive then before and thats where it all really started. I searched for "little helpless bitch fucked hard" and thats exactly what the search gave me. The second video in the list was titled word for word what I had typed in the search box so I figured I'd give it a shot. The video started with a side view of what I thought was a fairly attractive woman tied up in her panties on a table. The master was spanking her ass with his bare hand (which is a huge turn on for me) and demanded that she tell him how much she liked it. Being verbal is another huge turn on for me so I was already about to explode and it just started but after about a minute of spanking the master pulled the panties down and out popped a cock. Mine was bigger then that and I wasn't even out of high school yet! I almost clicked out of the video because I wasn't into guys but I was so horny that I just kept watching...she was so hot before I found out she had a penis. The master then whipped out one of the biggest nicest cocks I had ever seen and shoved it right in "her" hole. She screamed in pain the entire fucking and then when master pulled his cock out he f***ed the slut to suck him off and exploded right in her face and mouth. I forgot I had been stroking my cock and exploded right at that moment. It was so humiliating to watch I loved it! To top it off when the master was walked out of the room he said good girl and gave "her" one slap on the ass. This drove me crazy! How could one video be this hot?! Thats when it all came to me finally after so long of watching porn I found out what really got me going.
After watching that video I started wondering why a boy would ever want to wear womens clothing. I watched more and more videos and really got into shemales at first and then started to like even the crossdresser videos. As time went on it just became natural for me to watch shemale porn and I figured that was all that I had needed to be fully aroused. Boy was I wrong about that!
I went to my friends house that lived around the block one day in the summer. His gf and b*****r were there and he asked me if I could watch his b*****r while him and his gf went to go do something. I said yea and when they left the house I wasn't sure what to do. The little b*****r was playing video games so I could really do whatever I wanted and soon realized that. I always found his mom attractive and I knew her room was the only room upstairs so I immediately ran up there like any horny teenager would. I was looking through the closet looking to see if she had any toys and then I looked across the room and a pair of pink striped panties caught my eye. All the images of the porn I had been watching ran through my head and I knew I had to atleast try them on and put them back. So I grabbed them out of the dirty clothes pile and ran back downstairs and went in the bathroom. I smelled the panties and they still had the sweet scent of dirty pussy on them. I had never smelled anything so amazing EVER! It made my cock extremely hard but I knew I was short on time so I gently started sliding the panties on. I could feel the soft fabric getting more and more tight as I raised them higher. I was so aroused that when I raised them over my cock just feeling the slightest touch made me climax. I couldn't control myself and squeeled with ecstasy. It had never felt so good before! I realized that I got cum all over the panties and knew that I couldn't put them back now because I wouldn't want to get caught so I left them on and put my clothes back on over them. I had so many images running through my mind but I felt so good that I paid little attention to them. All I was thinking about was how good that orgasm felt and then my friend and his gf returned to the house.
I made up a lie and told him that I had to go home to do chores and I was already late because I was watching his b*****r. He told me I better leave then and he would talk to me later. I ran home as fast as I could! I was so excited! Noone was home and I realized that I had already started to get hard again and started stroking myself through the semen filled panties. It felt just as good as the first time maybe even better! It never felt better the second time, this was amazing! In well under a minute I had cum again right in those dirty little panties, it felt so good and naughty. I finally began to realize why those boys liked to dress up like little sluts as I laid there in my cum filled panties dreaming of what its like to be a real girl...
I will have a part 2 up in the future it shouldn't be too long I got really turned on by reliving this. Tell me if you like it or not so I know if I should make another.