My Life as a Sissy Step-Son Ch. 01

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[ This is a work of fiction, events, and characters are entirely fictitious and any resemblance to actual persons, living or dead, is purely coincidental. This should be read only as a work of fantasy]


Charles’ wife Kathy died five years ago, in an automobile accident. He was married to her for twenty years. When he lost he never thought he would love anyone again. Charles found himself after five years of mourning, feeling lonely, and felt he needed to start looking for the next love of his life. Charles soon met Becky, she was wonderful, she reminded him of Kathy, but not in a way that made her a replacement. Becky was different, first of all she was white. Charles never felt he would be attracted to a white woman, but soon fell in love, and married soon after.

Becky had a 19 year old son, by the name of Chris. Charles knew that Chris didn’t like him that much. He knew it was because, it was now final that his mother and father were not getting back together. Charles understood how Chris felt, it felt familiar to the way his life changed when his wife died. His life had changed and it would not ever go back.

The first thing that Charles got to know about Chris, is how lazy he was. He was 19, he didn’t have a job. He dropped out of college. He lived off his mother’s enormous income. Chris pretty much laid around the house in his underwear, and if he did go out it was to his friend Reggie’s house to get drunk all day. Charles’ though would always wonder what the hell was the kid’s interests. Charles wanted to connect with Chris, but every time he tried, he got the cold shoulder.

Charles worked at the lumber yard, of course he didn’t really have to work, because of his wife’s income. He felt he needed to contribute, though, and plus the work kept him strong, and fit. he knew Becky loved his physique, and being held in his arms when he made love to her. His job kept he and his wife happy.

It was summertime, and working in the lumber yard was hot and tough work. The lumber yard bosses decided to shut down early one day, due to the day reaching record temperatures of triple digits. Charles clocked out said goodbye to Jerry, and King, his co-workers and best friends.

Charles knew when he got home, he would have to deal with Chris laying around in his underwear. Playing video games; probably already drunk off his ass. He really felt bad that he couldn’t connect, but I guess he would need to give it time.

Charles drove in to the driveway, and got out of his car. Charles instead of going through the front, and went to the back gate, to check out the pool to see if it had been cleaned by the pool man. It was so hot out, a dip would make him feel a lot better. Charles saw the pool was clean and then went into the house through the back door. Charles went into the kitchen to grab some water, and he thought he heard some noise in the living room.

The sounds coming from the living room sounded like someone was having loud sex. The sound actually sounded like two men having sex. Charles walked quietly into the living room, and peeked around the corner. Charles was taken aback at what he was seeing in the living room.

Charles saw in the living room, a gay porn playing on TV. The scene was of a large black man, fucking a small white guy from behind. He did not notice Chris at first, but when he looked at he saw him right there watching the action going down on the TV.

Chris was on all fours on the couch, fucking his as with a huge dildo. Sliding it in and out of his ass, as he jerked his cock. He was moaning loudly. That was not the most shocking thing he was seeing. Chris was dressed up like a girl

Chris wasn’t just dressed up, he was dressed up in a schoolgirl uniform. He was wearing white thigh high stockings, black shoes, a plaid skirt, and a white blouse. Chris was wearing panties which were pulled to the side so that his ass and cock were fully exposed. Chris’ long hair was tied up into pig tails, and he could tell he was wearing full on make-up. He just couldn’t believe what he was seeing happening.

Charles also couldn’t believe that the scene was making him aroused. Charles felt guilty.

“This is my step-son for god’s sake, get a hold of yourself,” he thought.

His hand though kept going back to his hardening cock, in his pants. Charles decided he needed to do something about this.

Charles walked into the room quietly, and stood there watching Chris pleasuring himself. He was so into it he didn’t notice him standing over him. Charles could tell Chris was getting close to cumming. Charles began rubbing his cock more, and more.

Suddenly, Chris let out a girly sounding moan, and began shooting his load onto the floor.

Charles thought, “Thank god, this is tile floor”.

Chris laid there panting hard, and slowly removing the dildo from his ass. He laid there for a few minutes. Charles knew it was time to reveal he was not alone.

Charles cleared his throat, and said “I hope you are beylikdüzü escort going to clean that mess up you made”.

Chris jumped up, and pulled his panties up quicker than Charles had ever seen someone do it before. He was red faced, and shocked.

“What the hell are you doing home so early,” Chris stammered. it was all he could think of to say.

“I got off work early, due to the heat. Now do you mind me what the hell you are doing dressed like that, and watching porn in the living room. I don’t think your mother would be very happy with this situation,” Charles stated firmly.

Chris looked down and felt ashamed. “Please Charles, don’t tell anyone, please. This is something I have just gotten into recently. I promise I won’t do it again. I actually don’t really even like it,” Chris explained.

“That’s not what it looked like from here, it looks like you were enjoying it plenty.” Charles chuckled. Charles lifted up Chris’ skirt, and could tell that some felt over cum was pooling in Chris’ pink panties. “Where did you get the idea to get dressed up like this, and who’s clothes are these,” Charles asked.

Chris answered shyly, “Well, I don’t know I saw some porn on the internet, and started going to crossdressing forums, and then went from there. I bought the clothes at Goodwill, during Halloween. I thought it was a sexy outfit.”

Charles ogled Chris some more, and said, “Well I guess it couldn’t have been too hard to find an outfit in your size you are a pretty small guy” Charles thought, he can’t be much taller than 5’3″, and weigh more than 120lbs. “I must say though you are right about one thing, you do look sexy in that outfit,” Charles stated coyly.

Chris was shocked in what Charles had said. His own step-father was calling him sexy. He should have felt aversion, he hated the man for replacing his father. What happened though was arousal and interest.

Chris’ cock jumped and tingled in response. Chris looked at Charles’s crotch and could see his hardness growing, and growing. Chris’ saw that his step-father’s cock was as big or bigger than the guy in the porno, that was still playing in the background. Chris was hard and aroused once again, making his skirt tent up.

Charles smiled and saw Chris look at his bulge, and see his skirt tent up. “Well, it looks like you are ready for more, I remember being 19 like you, I was always fucking horny. If I wasn’t fucking some hot pussy, I was stroking my cock,” Charles stated.

“Yeah, I just can’t help myself, I guess, I am always looking for something more arousing than the last, and I guess that is why I am dressed like this. I think I have the best orgasms dressed like this, while watching some hot guys go at each other,” Chris admitted.

“So, your mother, knows nothing about this, and you don’t want her to know, so how about we come up with a deal,” Charles said.

Chris replies, “Yes Please! I do not want mom to know about this, I think she would worry too much about me, and I think she might even kick me out of the house.”

“Yeah I don’t think she would be very happy with you dressed up like this, and making a mess on her floor, so I intend on keeping this a secret but you are going to have to do something for me,” Charles replied.

Chris says, “Okay, what do you want me to do, I will do it, I vow it.”

Charles laughs, and says, “You vow it, now that is what I am talking about. Okay I want you to first start respecting me, I am your step-father, I love your mother. I am not going anywhere, and second I want to spend more time with, get to know you, and connect with you. Are you willing to do that for me?”

Chris has look of relief on his face and says, “Yes I can definitely do that. I am sorry about disrespecting you , I won’t do it anymore. I will definitely make more of an effort to get to know you.”

Charles looked at Chris and says, ” You look relieved, about this?”

Chris replies, “Yeah, I thought you were going to make me do something else, like make me have sex with you or something.”

Charles smiles slyly and says, “Well, that is kinda what I meant by quality time, Chris.” Charles unzips his pants, and pulls his large 10″ cock out, stroking it to hardness, again.

Chris is shocked at the sight, he hasn’t seen one this size even in a porno. It actually makes him kind of afraid. “I don’t know Charles, that thing is much too big, plus I am your Step-Son, don’t you think that is a little bit gross.”

Charles responds strongly, “Now look Chris, you just made a vow to do as I say, this is how I want to get to know you, I don’t think this is a gross thing to do. Chris I want you to start calling me father, dad, or daddy, no more of that Charles , shit.”

Chris felt ashamed and looked down at the floor and replies, “Yes Dad.”

“Good, now how about you give me a little twirl and show me your outfit,” Charles says as he goes to sit on the couch.

Chris spins slowly around, with his beyoğlu escort hands behind his head. Chris decides to have fun with it, and arches his back, giving a slutty pose. Chris then bends over and shows off his pink panties.

Charles gets up and closes the blinds in the room, dims the lights lows, so the only light is some sun shining through the curtains, and the glow of the porn showing a small white guy now taking it from two large black studs. Charles turns up the porn louder, the porn music is thumping in the speakers, and the men’s moans vibrate through the walls. Charles goes to the a/c and shuts it off. Charles goes back to the couch and starts stroking his cock again.

“MMMMM, this is so awesome, Dad, I just love hearing these guys moans fill the house, and the room is now nice and dim. it makes me feel sexier,” Chris says in a girlish voice.

“You bet, sweetheart. Now come over here and sit with your daddy. Let’s watch these guys fuck for a little bit,” Charles replies.

Chris walks slowly over to the couch, sits prettily down next to Charles. Chris begins watching the porn, all the while his cock his getting harder and harder. Chris is not sure if its the idea of what is going on in the porn, or if it is having his step-dads watching it with him. Chris looks over at Charles, and can see his dad’s cock is now rock hard. Charles looks back over at him and smiles. Chris goes to reach for his own cock, in his pink panties. Charles suddenly slaps his hand away.

Charles puts his finger in Chris’s face, and says,”No way, you already came today, its my turn. Plus girls like you are whores, and are here to be used. I never heard of a whore deserving of getting off. So, how about you don’t touch that tiny white thing you got in your panties, until I say so.”

Chris is shocked, and takes his hand away.

Charles pets Chris’s head, “its okay, I am didn’t mean to get angry, I just think this is the way it should be, if you are going to be dressed up like that. Oh and one other thing, since you are a dressed up like such sissy slut schoolgirl, we will now call that thing of yours a clitty, and that ass of yours a pussy. God knows, that thing is probably small enough to be considered one,” Charles says laughingly.

Chris nods, and says, “okay, but if you are going to do this, you have to treat me nice, like you would your own daughter.”

Charles says, ” Okay, I can see that is fair.” I kisses Chris on the cheek, and smiles. Now since we had that talk, let’s get back to our quality movie time.”

Chris and Charles put there attention back on the porn. The scene has evolved into a huge five man gangbang. Four black guys are taking turns on the white boy, and moans are getting louder and louder. Charles is hard again, and then takes Chris’s hand, and wraps it around his cock.

Chris looks down at his hand holding the huge cock. His boyish hand looks quite small when wrapped it. Chris then takes his other hand and massages his step-father’s balls. Charles lets out a moan. Chris then begins slowly massaging Charles’ cock. The cock is so silky and smooth in his hand.

Chris begins pumping his step-father’s cock, at first he starts out slow, and then speeds up. Charles is in total ecstasy. Chris hands are so soft and smooth, just like a girls hands. Charles isn’t sure how much more he can take.

Charles removes Chris’ hand, and then shoves Chris’ head down into his crotch. Chris smells the sweaty must coming from his daddy’s balls, and it smells so good.

” It’s time now, you learned how to suck big cock. I assure you it will help you in the future.” Charles said with a wink and a smile.

Chris nods his head, and begins licking the huge shaft up and down, flicking his tongue across the head. Chris then goes down to Charles’ balls and begins sucking them as hard as he can. Chris had never done anything like this before, but he sure as hell learned a lot from watching porn.

Chris then stares up at Charles, and then sticks the head of his step-father’s cock in his mouth. Charles lets out a grown, and puts his hands on the back of Chris’ head. Chris takes a big breath and inserts more than half of Charles’s cock in his mouth, and begins moving his mouth up and down, sucking on the huge black cock. Chris moans, and hums as he moves his mouth. Chris can taste the salty pre-cum, oozing from the cock. The taste of his step-dad’s cock is making him hot, along with the smell of sweaty sex in the room makes Chris feel like he is going to cum without being touched at all.

The living room is now warming up. The hot summer day and the a/c being turned off has turned the room into a sauna. Chris and Charles are sweating profusely. The sound of the porn playing is overtaken by the moans and groans of Charles.

Charles takes his cock out of Chris’s mouth. Charles can see that Chris’ makeup is ruined. His mascara is running down his face from sweating, and the lipstick he was wearing has been smeared bomonti escort around his mouth.

“Okay Chris, its time my pretty little girl, its time for you to lose your virginity. Don’t worry my sweetheart, I will be gentle.” Charles says to Chris.

Chris replies, “okay daddy, please be nice, I have never had the real thing, and I have never had anything that big inside of me.”

Charles takes the lube Chris was using for his dildo, and squirts a liberal amount and rubs it all over his massive cock. “Okay Chris, I need for you to get on all fours, it will be easier on that cute pussy of yours” Charles says.

Chris pulls his panties all the way off, and then gets on all fours on the floor. Chris hikes up his plaid schoolgirl skirt, showing his ass off to Charles.

“My god, Chris, I must say you really take after your mother. I could possibly say your ass might look even more girly than hers. It is so nice and smooth, and I can tell you are still nice and tight.” Charles says, while rubbing Chris’ ass, and fondling his asshole.

Charles crouches down low, rubs some lube on Chris’ asshole. Charles rubs his cock head on Chris’ entry, teasing it. Then, Suddenly, Charles pushes his cock into Chris, Slowly fro the first few inches. Charles lets Chris’s ass get used to his girth, and then plunges the rest of the way in quickly.

Chris gasps, as he feels the large member enter his ass. “Oh god, daddy! I can’t take that much! I though you were going to take it easy for my first time.” Chris stutters in anguish.

Charles replies, “I did take it easy, but I saw that you were taking it well, so I jumped on in. Anyways, I am your fucking father, and I basically get to do whatever I want, in my own house.”

Chris resigns himself and doesn’t reply. He just relaxes his ass, and begins feeling the pleasure of fullness.

Charles begins pumping his cock in and out, at a standard pace. Moving his body up and down like a pile-driver into his sissy son’s tight ass pussy. Charles can’t believe how tight it is, and how good it feels to have something like this to fuck.

Chris is shuddering now from pleasure, and small amounts of cum is leaking out of his tiny 4″ cock. He has never cum before like this, and he is sure it is not the last time he will cum like this. he moves his hand to his cock, in order to increase his pleasure, when Charles grabs his hands, and pulls them behind his back. Charles says, “Oh hell, no, you don’t get to cum like a man no more, you will cum like a sissy only. That means no more stroking your cock. The only time I want cum to come out of that tiny thing of yours, is if you are being fucked in the ass. You got that or do I have to pull this arm back harder.”

Chris’ arm feels like it is going to break it is being bent back so hard. Tears roll down his cheeks, and Chris says, “Yes, Sir.”

Charles smiles, gives back Chris his arm, and says, “Good Girl, Now let’s finish this up.”

Charles begins pumping faster and faster. Chris moans uncontrollably. Charles grunts loudly, as he drives his cock into Chris’ ass, his balls slapping against Chris’s ass cheeks. Chris can feel Charles’ cock twitch, and can tell he is about to cum.

Charles yells, “here it comes baby, daddy’s going to fill up this ass…”

Before Charles can finish his sentence, he shoots his load. Chris can feel the warm cum filling up his ass, and filling it up rather quickly. Chris can feel the massive load, leaking from his ass, and dripping down to his balls. Charles pumps his cock in and out, making sure he deposits the whole load into Chris’ sissy ass.

Chris can’t believe how much cum that is being shot into his ass. Charles finally finishes, and removes his cock.

Chris turns around and takes Charles’ cock and begins cleaning it off with his tongues. He has never tasted cum before, and immediately he is addicted. He loves the salty, warm taste. Chris wishes more was there on the cock, but he has cleaned Charles’ cock entirely. Chris can feel cum dripping from his ass, puts his hand to catch some, and puts it in his mouth, swallowing the dirty cum. Chris licks his hands clean, and looks up at Charles smiling.

“mmmmmm, so yummy, I never thought it would taste so good.” Chris says in a cute girly voice.

Charles says, “Wow darling, you are such a hot dirty slut. I am so glad you enjoyed that as much as I did.”

“Daddy, now remember since I did that for you, you can’t tell Mommy,” Chris says.

“Well Chris, here is the thing about that, I won’t tell your Mother, but from here on out, you gotta do your part around the house. You gotta clean up around here, do all the duties of a woman in a household. I don’t want you going out late with your buddies drinking anymore. If you go out, you need to be dressed up like a sissy, and have a man who can protect you. I don’t expect you to dress up when your Mom is around, but whenever she is not, you must be dressed as a sissy. Those are the rules, do you think you can follow them” Charles replies

Chris doesn’t know what to say, but he feels in his heart, that he has stepped into being a part-time sissy. “Yes, Sir. I will do whatever you want me to.”

Charles replies, “good, now clean up this mess you made in the living room, before your Mother gets home.”

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