This is a print version of story Sissy Slut Amanda Part 1: The Beginning by TheSissyFucker from

Sissy Slut Amanda Part 1: The Beginning

The Story of Sissy Slut Amanda

This is a story of fiction

Part 1: The Beginning

When I was twenty-three I meet my Sissy Slut Amanda for the first time. Now he was only eleven at the time and it would be many years before I would know him as Sissy Slut Amanda, but still funny to look back at now. The first time I met my future sissy slut, he was Mark, son of the woman I was dating. He seemed like a nice k**, very shy and timid but sweet nonetheless. It’s wasn’t too long after our first meeting that I would be asking his mother to marry me. We had a good marriage and although I never felt like Mark’s father, I did my best to support him. I never understood his interests, he was always watching anime and listen to pop music and he was in so many different dance classes. Now even though I didn’t understand, I still worked hard to afford all those dance classes and enjoyed how happy they made him. Looking back at it I am surprised I didn’t notice his sissy side sooner.

After 5 years of marriage the terrible happened, my wife Jill, died in a car accident. Mark and I were just devastated and never thought that anything like this would happen. Now here I was, twenty-eight, with a sixteen year old stepson. Needless to say I wasn’t much of a parent to Mark, I worked a lot once his mom was gone. I provided everything he needed, including a big allowance, but I was kind of neglectful and he pretty much raised himself his last couple years of high school. He even started to take care of me, he would cook dinner, do the laundry and any other housework.

However, during those last couple years of high school, I did notice changes in Mark. Mark was always a thinner guy but after his mom died he started doing these work out videos and dieting. Now I wouldn’t have taken notice of this expect the work out videos were work out videos for strippers. Even said so on the package, the video was meant to make your butt more round. I also noticed that his style of cloths was starting to change and he began to wear very tight jeans, I believe he was actual wearing girl’s jeans, and very feminine looking shirts. Mark also let his hair go out and it was very girly shoulder length hair. He told me that it was just the style and that I was just too old to understand, so I just believed him and went with it.

Once Mark graduated High School I had the impression that he would get a job and move out or go to college. However, he didn’t, for almost a year after his graduation he still hadn’t done anything. Now, I was willing to be patient but I really wasn’t seeing any effort out of Mark. He would sl**p all day and be out all night, so I assumed the worse…d**gs. So I get Mark out of the house one day by yelling at him to check out the community college, which he hesitantly agrees to go. The moment I see his car pull away I am in his room looking around. At first I don’t find anything, as a person who use to do a lot of d**gs, I know the best places to hide them and all a bust. I was about done when I see it, a black storage box hidden under a pile of dirty cloths.
I grab the black storage bin out of the closet and was thinking, what kind of d**gs would need this big of a box? I lifted up the lid and was hit with a strong perfume fragrance and then I began to see the contents. On the top there was about a dozen pairs of panties of all different kinds. I have to admit when I saw all those panties at first I really thought Mark had fucked a bunch of woman. As I dug deeper that changed, I then found stockings, skirts and other lingerie. After I pulled out all the lingerie, wigs and cloths, the items at the bottom of the bin would reveal the truth about my stepson. At the bottom of the bin I found one shoe box filled with make ups and another shoe box filled with dildos, buttplugs and lubes. As soon as I opened the boxes I knew that Mark wore and used all this stuff, but I was shocked. I was just sitting there in dismay when I looked down into the storage bin again and saw a couple of discs. I grabbed them and quickly had them in my computer and was checking the contents. When my computer loaded the disc up, I saw hundreds of pictures of my stepson dressed up like a little sissy bitch.

At first the pictures were just Mark in slutty looking girls cloths, short skirts, stockings, make up and wigs. I kept telling myself, you’ve seen enough you can put this stuff back, but I didn’t. I kept scrolling through my sissy stepson’s pictures seeing them become more explicit as I went on. By the time I reached the end of Mark’s pictures he was fucking himself hard with a dildo and by the looks of the picture seemed to be loving it.

I couldn’t believe it, I was looking at a picture of my stepson dressed up like a girl, fucking himself with a dildo and worse of all…my cock was rock from looking at it. I quickly grabbed all his stuff and tried to put it back the way I found it in his room. What the hell was I going to do, how do you confront your stepson about this kind of thing. Not to mention the fact, that it turned me on to see him dressed up acting like a slut.

A while later Mark returned home and sure enough seemed unenthused about the community college. He chatted about it for a bit but I couldn’t look at him without seeing him dressed up like a little slutty girl.
“Alright…well, I guess I’ll hang out in my room until I need to start making dinner.” Mark said to me as I quickly nodded and let him run off to his room to do god knows what. I stood there in the kitchen listening to him thump around in his room above when it all of sudden it went dead quite. I knew right then that Mark knew I had been through his stuff. I was expecting Mark to try and come explain, give me some kind of excuse and hope I hadn’t seen the pictures but he didn’t. Eventually Mark came down to start making dinner but he was very quiet but then again so was I. He made dinner and called me over when it was ready. We both sat there in awkward silence and Mark had this look of utter defeat.

“Well, we might as well clear the air since we both knows what’s up?” I announce trying to just rip this band aid off quickly.

“What did you see, cause it’s probably not what you think.” Mark responded and then began to construct reasoning as to why he would have his sissy stuff.

“Mark!...I know.” I interrupted him and his eyes began to swell up with tears.

“I’m sorry…I’m sooo sorry!” Mark said as the tears began to pour down his face.

“Sorry, what do you have to be sorry for. Mark, I don’t care what you do in your sex life as long as its with consenting adults.” I replied quickly trying to get his crying to stop.

“You’re not disappointed….that…that I like to dress up like a girl”, Mark said wiping tears from his cheeks.

“Heh, I’d be lying if I said I didn’t find it a little weird but disappointed…no I’m not disappointed. Besides you make a cute girl.” I said and regretted immediately. I couldn’t believe I just said that and as Mark heard what I said, a smile spread across his face.

“You think I make a cute girl”, Mark said and I could see his mood just suddenly change. He began to relax more and his smile had grown.

“Uh, well…lets just put this aside for now and enjoy dinner”, I mumbled and we went back to sitting in an awkward silence. We finished dinner and then watched TV for a while and although things had change, by the time I went to bed it felt relatively normal. I crawled into bed and tried to sl**p but I couldn't stop thinking about my stepson dressed up like a slut and riding a dildo. My cock was rock hard and I kept telling myself, you are not going to jerk off thinking about your stepson in drag.

“Daddy, are you up daddy?” I suddenly heard coming the door way and then the lights came on and there she was, Sissy Slut Amanda.

“Mark, what the hell are you doing?” I yelled out and began to sit up as I used a pillow to cover my erect cock.

“Ugh, Don’t call me that. Call me sissy or Amanda or something derogatory but not Mark.” She said as she walked up to the foot of my bed. As she walked up closer and I saw the little lingerie she was wearing my cock began to throb.

“Mark, seriously. What the hell are you doing? Get out and go to your room.” I replied as I held blankets and a pillow over my hard cock.

“I can help you with that daddy. I have been practicing a lot on my toys”, the sissy said as she bit her lip and pointed at my crotch. Images of her sucking my cock flooded my mind and my cock starts to ache for this sissy slut in front of me. “You know daddy, I have been watching you for a long time. I still remember when I was younger the first time I saw your cock. You had fallen asl**p in your boxers on the couch and you rolled just the perfect way and your cock fell out of the fly hole. I stared at it for a good twenty minutes and saw it become fully erect…Daddy when I saw your hard cock in all its glory, I knew one day I would please that cock.” Amanda added as she walked around to the side of the bed. I don’t know why but I let my guard down and she began to easily grab the blankets and pillow and exposed my massive erection straining against the fabric of my boxers. Amanda gazed at my crotch and began to lick her lips as she slowly lowered herself onto the bed. She lowered herself so her head was over my crotch and her cute little sissy ass was up in my face.

“Fuck, am I really about to do this.” I said as Amanda’s panty covered sissy ass positions itself in front of my face.

“Don’t worry daddy, you don’t have to do a thing. You can just lie back while your sissy girl takes care of your manly cock”, Amanda utters in a very feminine voice. “Or you can play with my sissy pussy, it all belongs to you anyway.” She added. I didn’t know what to think as she said this stuff but feeling her body against mine felt great. Soon I felt a warm little hand reach in my boxers and grab a hold of my cock. “Oh, Daddy…yours is so much bigger then my toys”, she said as she pulled my plump pink headed long shafted cock out of my boxers.
Sissy Slut Amanda licked her lips as she eyed my cock, and then she leaned in and just gently kissed the head of my cock. She then began to lick and suckle at the head of my cock. If felt great for a while and then I realized that this must be her first time sucking a real cock. So now I am not only getting my cock sucked by my cross dressing stepson but I am his first as well.

“Have you ever sucked a real cock…Sissy?” I said as she slide off me and got on her knees at the side of the bed.

“No, daddy. I’m sorry I am not a better cocksucker for you”, the sissy responded.

“It’s alright, sissy. Daddy will show you how he likes his cock sucked”, I couldn't believe I just said that. I reposition myself, so Amanda was on her knees in front of me as I sat on the bed. “Now daddy does love that tongue and kisses you been giving the head of my cock, but there is a lot more you need to please, Sissy.” I said as I lifted my cock back exposing my balls and underside of the shaft of my penis. Amanda knew just what to do and leaned in and licked me from my balls all the way up my cock and would flicker her tongue once she reach the head of my dick. She did this over and over only stopping a few times to fully suck on my balls. She would suck on one ball, twirl her tongue all over and then lick up my cock. It felt amazing but this wasn't going to make me cum. “Good job my sissy girl, now you need to learn to suck right, and not just the head. Let’s teach you to take this down your throat”, I said as I grabbed Amanda by the back of her neck. Amanda had a look of worry in her face and slowly opened her mouth, she had just barely exposed her tongue when I rammed cock into her mouth and f***ed her jaw open. She quickly began to gag and choke. Amanda’s spit and slobber started to fling and spread all over the two of us. Amanda began to tear up and her mascara began to run down her face and slobber and pre-cum was running down her chin and chest. As I final felt her throat stop resisting and my cock just slide down, I was shocked at myself…I was face fucking my sissy stepson and he was about to make me cum. I pulled my cock out of her greedy little cock-sucking mouth and began to squirt my load on to his sissy face but as the first spurt came out I felt her mouth quickly wrap around the head of my cock and then slide down her throat where I blew the next few ropes of jizz and I was in a state of complete bliss. I slowly slid my cock out of her sissy mouth and saw that only a little bit of my cum was on her face.

“Yummy, Daddy you have the best man milk”, She said and quickly scooped up the rest of my cum off her face with her finger and sucked it off. Amanda then walked to the bathroom and got a warm wash cloth and came back and cleaned me up. I started to fantasize about all the different things Icould do with this cute little sissy and as Sissy Slut Amanda cleaned my cock I knew that this was only the beginning.

This story is a work of fiction. The pictures belong to naughty_amanda, all I did was write a story about her. I was considering making this an ongoing story, not sure yet. Why don’t you leave some comments and tell me what you think.

Story URL: