Living alone for quite some time jacking off to regular porn just wasn’t doing it anymore, I started watching humiliation porn, cross dressing, and sissy.
Reading about these guys wearing womens panties, stockings, guarders and such was a real turn on, they even had life like tits, I was very excited at all this, so I ordered some. I got so comfortable with this I would clean house all dressed up. I started wearing panties under my clothes going to the store.
I got such a turn watching men dressed as women sucking cock, being ordered around, treated like a bitch. I ordered 3 different life like dildos, and started sucking them while jacking off, and I even started fucking myself with them, it was super hot sitting on one while sucking the other one.
One day while leaving for work I noticed this guy sleeping by the wall that separated our apartment building from a wooded area, then I seen him when I came home, he hung out there for about 3 days. That Friday night I put my panties and stalking on under my pants, and off to the beer store I went.
I stopped at the video store picked up a few sissy humiliation videos and headed home. I started drinking and watching those videos, then I went and got my fake tits, put them on and I was a sight. About then I thought I herd something outside so I looked out the window, and there he stood.
I thought what the hell, so I opened the door in all my glory and said yes? He was very polite and younger than I thought, he said excuse me sir, I mean ma’am, is there anything I can do for you to earn some money?
How could I refuse? With sissy porn on the TV, me wearing red and black panties, stockings, with a guarder to hold them up, and my fake life like tits exposed. I said sure, come in mr. Sir. Mr. Sir was something I seen from the videos, more of a proper way for a sissy to answer.
I was shocked that he wasn’t shocked at the whole scene, then I offered him a beer, he started saying he seen me around and thought I may help him, I just answered with yes sir, then I asked him if he would like to take a shower, he jumped at the chance, so I directed him to the restroom, pointed out all the soaps and such, he started undressing as I ran the water.
His clothes were old, and they stank, so I gathered them up and took them to the washing machine, he showered while I waited sitting on the toilet with a towel. When he got finished he pulled the curtain back revealing his cock right even with my eyes, “and mouth” I stood up wrapping him with the towel.
As he dried himself off, he asked where’s my clothes? I said I’m sorry mr.sir, they smelled so I’m washing them like a good girl! He chuckled a bit and said thanks. He dried off and we went back to the living room, where the porn was playing and I handed him another beer.
We drank for a while, then I got my nerve up and said that I would like to see what it’s like to suck a dick. He said ok, as he spread his legs, removing the towel, he scooted to the edge of the chair allowing his hard cock to stick straight out. I didn’t think twice, this was my chance. I jumped down from my seat. Sat right in front of him, and took his cock full in my Mouth.