Gay crossdressing stories

Then I remembered a bunch of the sissy hypno videos I had watched earlier and started to wonder if they really had gotten to me after all, and then the second thoughts of "do I really wanna do this" rolled in. Then he said, "But mom, I was just trying them on because they were pretty."

"And of course, I noticed that your little boy thing was all in a tither, remember/"

"But mom, that had nothing to do with it."

Of course, what Brian didn't know was that his mother had seen him walking home from school every day with Josh, whom he had known his whole life.

I saw him pull over into the far right lane so I was about to make my move to pass him and noticed he was slowing down a lot; too much to just give a casual wave, he was going to take the next exit. Almost always though, after I came, I lost interest and went back to being 100% straight.

Trick-Or-Treating

We went from house to house through two different neighborhoods.

I was at my friend’s house and I got all dressed up and I took some pictures in her bedroom cuz she was in the bathroom getting ready and so used her room. The second I put on that “dress,” all I knew was that I liked how I looked. I had always had a craving or tendencies towards being a little bi, and had only every played with myself; anything i could use for a dildo from time to time, jerking off to sissy and CD porn.

He smiled and said "my my...today was a lucky day indeed."

He starts to go to work on my semi-hard cock and to my surprise...nothing. I had some gloves from Hot Topic and my dress is actually a skirt from White House Black Market, I had borrowed it from my aunt. I borrowed the majority of my outfit from my aunt with a necklace and such.

"You were so sweet, and you never grew all that body hair, and it was great guiding you.

As the moaning increases and his panting starts to increase I just unload, cum gushing from me, harder than I've came before and all I can do is scoop it up. Remember when I came home one day and discovered you wearing my clothes. He said he would help.

I just thought I looked awful all the time. There was something different about their relationship, however.

About 10 mins go by of us driving down some small city streets, I see him point his arm out the window signaling to park along the street. That kinda thing. It all clicks for me, the stockings, the slutty moans I'm making and this guy just pushing in and out of my ass; my cock had gone back to being semi-hard, but I realize as he's hitting my prostate that my cock is starting to involuntarily spasm and leak.

I let you grow your hair longer and watched as your body emerged so lovely. Next thing I realize, I'm moaning like a real girl, getting railed by this good looking dude. If it wasn’t for my friends pushing me to do it, I feel like I would have never felt like I had finally found myself. Totally closeted. Secondly, it was much better in person.