Angel's Sissy Boi
Anal sex and forced feminization

So, this is a few days old as I have been really worn out the past coupe days by my Mistress. This was back on Tuesday, the day after the best orgasms of my life. Took me a couple days to recover from it. So here it goes, as best as I can recall it.

So I get home fairly early and we watched a little tv while we ate dinner. It didn’t take to long after that I was instructed to get a large plastic box from the second bedroom. After talking about it at work, my mistress decided that it would be the perfect height to fuck me over. It was also the perfect way to restrict me from getting away from her raping my ass. She also gave me a safe word to say if I can’t take any more. I get the box and place it in front of me, followed by getting a dildo and lube. She puts on a glove, lubes it up and demands that I bend over the box. I do as I am told, and the box was the perfect height, I was completely open to her, and had no where to go. She started off by luring up my ass crack and cheeks, followed by a finger slipping inside. It is quickly removed and e toy is thrust deep inside, I gasped out with supprise. She wastes no time and goes right into super fast strokes. Thrusting deep inside it’s not even a minute before my first huge orgasm rock my body, I yell out as she relentlessly thrust inside me. I squirm and twitch under her, but I have no where to go, all I can do is take it like a good sissy boi. I chose a smaller dildo than the day before, because I was still sore, but that didn’t help at all. My mistress simply fucked my ass longer, faster and deeper. She would thrust all the way in and hit my ass with the base of the dildo. Orgasm after orgasm rolled over me like a tsunami of pleasure. She knows exactly how my anus behaves when I have an orgasm. I push out, flowering my anus. She uses that to make my orgasms even bigger. She will fuck me for a while and when my anus flowers she goes really fast wi the strokes. Which just makes me push harder with bigger orgasms, followed by her going even faster. Until I have massive orgasms that cause me to squirt all over the place.

After about half an hour, yeah that’s right she raped my ass for half and hour. She pulled out the toy, lubed me up and started to finger me. Two fingers, slowly turning and thrusting, followed by three. Then four, she pushes them deep inside, twisting and turning them losing me up. I knew what was coming, she was going to try and fist me. If had been a while since I have been fisted, and after the raping I just got I’ll be eve tighter. Anywyas, she continued stretching my ass out with four fingers, slowly pushing in and twisting all around. My moans and groans louder and louder. She moves to the side of me so she is able to finger me easier. Then she asked me if I can take it, I said I will try mistress. So she folded in the thumb and started in. I felt my sphincters slowly expanding around her hand as is inched deeper and deeper. It was almost in, just a fraction to go, and I couldn’t take any more, I called out my safety word. I couldn’t do it, she was visibly upset with me.

She went into the closet and got out a skirt, some sissy panties, a spagetti strap shirt and heels. She demanded I put them all on, and had me go into the living room. I put all the items on and stood there, she told me to place a book on my head and walk around. With each fail, dropping the book, she slapped me vey hard on my ass, which usually resulted in another spanking. After finally two successful passes from wall to wall she took the book. Went into the bedroom and got her camera. She told me to stand up. Against the wall, like I was being arrested. She took several pictures of me then bound my hands. She then started to pose me in many different positions taking photos of me, including some with a butt plug in. She says if I am a good sissy boi I can post some of those pictures on here.

  1. angelssissyboi posted this