Step-Sissy

Ok so… my mom does this thing. She falls completely head over heels with a guy that is no good for her, or me for that matter, then gives him everything in the world like that’s going to help her mental stability or save her from her horrible life. This changed when Damian came into the picture though. He was this really sexy man that for the life of me, I could not understand what he saw in my mother. He was really sweet and looked like he cared for her a lot. He’s a tech billionaire in his mid 50s who retired early and owned a mansion which we moved into as soon as they got married, and he always cared to know how my day was and wanted to get to know me better. And immediately I felt that there must have been something wrong with him. And to prove my point, soon after I met Damon. Damian’s 22-year-old son, who looked like he cared more about the amount of weed he smoked than anything else. Damian was a high school dropout with nothing else to do with his life, not saying I had anything to do with my life either but at least I graduated high school and had the audacity to drop out of college with a good excuse of not knowing yet what I wanted to do with my life! There was something about him though. Something I could not understand. The way he looked at me with his intense eyes or made a pouty lipped kissy face whenever I passed him made me swoon for some reason. Let me just say, I am as straight as they come, as men come, I mean, and no not like that. Ok we’re going off topic; the point is I have only ever fucked pussy in my life. I had no desire to be used by a man. Until Damon. I was 18 at this point, and a late bloomer for that matter, and this made me short, which I made up for by going to gym. And as a result, I was in fairly decent shape. My shoulders were broad and made my torso look triangular as it went down to my naturally well-arched back and narrow waist, which harbored a fairly good representation of what some girls call a bubble butt.

But Damon towered over me at almost 7 feet high, the same could be said for his dad who I was sure cleared 7 feet, easily. And both of them had ridiculously good looking bodies, to the point that I almost drooled when either of them were shirtless. They were built like tanks. And almost all the time, either of them wore tight shorts that exposed thick bulges. If I looked closely enough, I could see that they were both uncut. I made sure I only took glimpses, what I was seeing was hard to look away from, even for a straight man. There were times when Damon noticed I was looking and grabbed his bulge as if to advertise it to me, but I would quickly avert my gaze and act as if it did not phase me.

The entire situation changed when my mother was working late. Damian was watching a football game downstairs while I took a shower. That’s when Damon came in, shirtless and rocking a clear bulge that pushed against his sweatpants. It was so big the tip of his dick was tenting out to the right side of him, past his waist. I had no idea dicks curved like that. It must have been at least 10 inches. I had a few seconds to regain my composure as I noticed he was holding up his phone.

“Aww look at that sissy penis, I should send this video to everyone at school so they can see what a little girl you are. I’ve seen clits bigger than that!”, he laughed loudly.

Now let me be clear, I’m a grower not a shower! As he so clearly wasn’t.

“What the fuck are you doing Damon?!”

“Just want everyone to know that my little step-sissy has a clit, unless you don’t want me to share this?”, he feigned concern with a devious smile.

“Of course, I don’t want anyone to see me naked dumbass, what the fuck is wrong with you?!”

I instantly regretted that, because as soon as I said it, he dropped his phone, rushed up to me and slapped me so hard I slipped and hit the floor tiles hard.

“Speak to me like that again and I will send this video to everyone you know!” he growled. Then, as quick as a blink, his demeanor changed, and he looked down at me somewhat caringly. He placed his thick hand on my cheek and fingered my lips opened with his thumb.

“Such pretty lips”, he said as he licked his. “Why don’t you put them to good use?” he placed both of his large hands behind my head and forced me forward to position my lips at the head of his thick bulge jutting out through his pants. He was strong and I did not want to get hit again or have the video of me sent out to people, so I obliged. He used his firm grip to move my head from side to side across the thick ridge of his penis.

“MMMmmh, now be a good sissy and suck your big brother’s cock”, letting go of my head he pulled his pants down and off to reveal something bigger than what I imagined with his pants on. It was long, thick, veiny with a pink head and when I placed my lips around it, I realized he was only semi-hard! Semi-hard and I could barely swallow half of it!

“Good sissy, show me how much you appreciate me letting you suck me off”

Once again, his hands were at the back of my head and he was forcing his cock down my throat, choking me. He took grip of my hair and began face fucking me. Rough and fast. Tears strolled down my cheeks as I gagged and gulped for air. It went on for what seemed like hours when his body tensed up, flexing every muscle and he shot rope after rope of thick, sultry cum down my throat. It was so much I began spitting it out.

“NO” he roared when he finished and pulled me off him, once again slapping me hard across the face, “lick it up”. With that he forced my head down to the floor tiles to lick up every drop I spilled and when I was done, he made sure I swallowed by forcing open my mouth and spitting down my throat, then blocking my nose so I had no choice but to swallow and breath in through my mouth.

“Good pussyboy”, he said with a satisfied smile and pat on my head, like I was a dog!

The whole experience was so much, that only when it was over did I notice that I was rockhard and dripping from my 5-inch penis, only when it was over did I notice the door was open and Damian was standing there with his thick, rockhard, almost 13-inch appendage in his hand! He was butt naked and by all the men I could have imagined, I have never imagined any man this sexy. Damon definitely got his talents from somewhere. Damian was muscled for sure, but his body was covered in hair and there was a thin layer of fat over his muscle that made me drool with desire.

“He’s ready for you father, I’m sure the sissyboy won’t resist now”, Damon said with a smile that almost begged for his father’s approval.

“Good man Damon, now go downstairs so I can teach this sissyboy how to take a man’s cock”, Damian said with a devious grin.

As soon as Damon left Damian threw me a pair of red lace panties.

“Put these on sissyboy”

“Wh- why are y’all doing this to me?”

“Put them on and be grateful! You think I am going to let you live under my roof for free!? Your tramp mother works all day and always comes home tired, and apart from that cannot cook decently or even feign any interest in trying to please me. But I realized that’s all and well if I can use a sissyboy like you all day while she’s away. And don’t start whimpering like that! I know you won’t tell her anything because she barely holds it together and the two of you were lucky to have found me, now stop wasting valuable playtime and put these panties on!”

As he was speaking, I realized that everything he said was true. We were lucky to have found a man like him and my mother works all the time even though he’s a billionaire and they’re married, that can only mean one thing, she’s doing coke again. So, I decided for my self-preservation that I am going to please this man the best I can.

“Yes sir”, I said with an eager smile and put the panties on. I must say I felt quite sexy in them, the material felt good on my skin.

‘Good sissy, now bend over the sink’. I go to the sink and bend over, when I’m there he roughly rips a hole in the panties and squirts some soft liquid on my hole which must have been lube and begins fingering me with a thick finger.

‘ahhhhhh’ I moan, this felt so good even with the slight amount of pain I was feeling.

He gets closer to put his arm around my neck and look into my eyes in the mirror, ‘Good boy’ he whispers into my ear, which he bites soon after, making me whine but also sending jolts to my dick, which was now jutting out of the top of the panties and leaking precum. He squirts more lube and adds another finger into me, sending me into a daze of pain and pleasure, as he starts to finger my hole more roughly with an intense speed. My cock starts leaking uncontrollably and the same can be said for the moans, almost screams, coming out of my mouth. Which is why he puts his hand not inside me over my mouth and growls “Shut up sissy!”, after which he adds another finger and increases the intensity further. The pleasure is immense at this point, and I can’t control my legs which are shaking and flailing under me, making me realize the only things holding me up are his fingers and my weakening arms on the sink. And then suddenly he pulls his fingers out of me fast sending torrents of cum spewing all over the sink and floor.

Noticing this he smiles deviously, ‘Pick up all that cum boy and lube up your owner’s dick,’ noticing my confusion he says, ‘that right, I own you and this pussy’. For some reason being owned by this rough, extremely wealthy man turns me on and excites me. So, I even more so eagerly, scoop up the cum as best I can and turn around to lube his rock hard almost 14-inch cock, which required both of my hands to do so. As I’m doing it, he moans and pulls me close to him with both of his thick strong hands and kisses me roughly, taking the air out of my lungs and almost crushing my body. He then pushes me away, sweeps my leg so I crash onto the floor on my hands and knees and within seconds his thick cock pops into me, making me cry out in pain. As he starts pumping his cock into me, he also moves it further and further each time, the pace at which he is going gets me accustomed to the huge size of his manhood and the pain melts away into complete pleasure, so much so that I start moaning again and begin pushing back into him. This makes him go deeper and harder and faster. Making me feel more pleasure and moan louder and louder. He starts fucking me with intense speed making my whole body vibrate with pleasure and I beg him not to step, never to stop even when he begins slapping my ass hard which only makes me want it more. And as my eyes roll back into my head and I feel like I’m going to have an out of body experience his hands gripping my waist tense and so does the thick, long, veiny cock inside me, sending torrents of cum so deep into me that I almost taste it in my mouth, which is impossible right?!

As he finishes cumming, he gets up, leaving me on the floor, and runs a bubble bath. Following this he picks me up into his muscular arms and without ever breaking eye contact walks me over to the bath and gently places me inside. Once I’m in he kisses me again, deeply, passionately, almost making me forget who I am. ‘You’re such a good boy, and I will always take care of you as long as you always obey me, okay?’

I’ve never had a father figure in my life I could look up to much less aspire to be like, so when he told me that I began having this fluttering feeling in my stomach and realized that I would do anything he asks, always. “Yes, daddy” and with that he kissed me again and got up to leave the bathroom.