Gay crossdressing stories

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That kinda thing. I’d say it took probably 4 hours with putting on the nails, making sure the makeup looked good, doing the hair, putting on the clothes, making sure I felt confident enough, and of course getting down the walk because I had not really worn high heels before that. Maybe I just need to dress up more often...

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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.

No names, no back and forth banter, no "do you have a significant other" etc etc. Well. I wasn't about to be shown up, so I floored it and caught up to him. We sat there a second making out and I was just in heaven.

gay crossdressing stories

After a little while of his cock sliding in and out slowly, I start pushing back on it and he picks up the pace. I totally slutted myself up, going all out. I let you grow your hair longer and watched as your body emerged so lovely. "Honey, don't you remember when Brian started carrying your books home, and how you let him do that. And watching Josh smile at you, I knew."

"I told him you liked him and wanted to know how he felt.

I think I changed back into my boy clothing before I went home, but I still had the face on and they asked “how did it go?” and all I said was “it was great, it was great” and I went to my room and didn’t talk to anyone the rest of the night. He said you were so cute, he had feelings for you. I was no longer a virgin and I could honestly say I loved every bit of it.

My family was really pushing the Mormon beliefs. There was something different about their relationship, however. You didn't know what they were."

"That's like 5 years ago, and I thought you only gave me them for two years, and they were to help control my temper?"

"Well, I fibbed," she smiled. He flips me around and lubes himself and my ass up and just presses his cock against my quasi-virgin hole.

"Tell me how much you want it sweetheart..."

"I want it bad, I NEED it, fuck my ass"

He pushes into me and its just pain at first.

I had oil problems and acne. Now, I had been crossdressing for a few years, so I had a few outfits, heels, a wig, etc. Meanwhile your hair grew, and look at you, tonight!"

Crossdresser's Unexpected First Time

Just want to say firstly, that this story is 100% true. For the Christmas party with my family, all the pictures I had full out eye shadow, I loved the eyeshadow.

Its just the head that's in right now and I'm now really re-considering this whole ordeal. I recognize that I don't know this guy, I'll never see him again and I'm already dolled up a lil bit and had been fucking my ass just earlier that day with my 6in dildo...why the hell not now? 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.