My Sissy Journey Ch. 01

Everyone involved is 18+

Hi my names is Oliver and this is my story about my journey and how my family helped me out along the way. I was 18 and a half about 2 months away from finishing school and I was living at home with my Mom, Dad and Brother. My mom Kelly was 45 and an absolute stunner, she still looked in her 20's. She is very tall for a women about 6 foot 2. She had long blonde hair that fell down to her lower back, she always wore light makeup even if she was just lounging around the house. Mom kept her body in amazing shape, she had a very trim stomach with a hint of abs. The thing about my Mom is that she has got huge boobs. They are EE. She compliments her huge boobs with a massive ass. I've always had a thing for my mom because she would always wear stocking with a short skirt and a tight top, I think my dad picks her wardrobe because he can't keep her hands off her.

My mom helps my dad stay in great shape too. My dad Marcus is about 6 foot 6 and has got muscles all over his body. He always wear very fitted pants and shirts so you can see all his muscles through his shirts. He has short black hair and some stubble on his face. My Dad is very hot, he gets hit on by ladies all the time but he only has eyes for mom.

My Brother Ben is a spitting image of my dad, He is about 6 foot 4 and very muscular, he has got short brown hair and a clean shaven face. He is an amateur bodybuilder so he is very dedicated to his body and making sure he is in tip too shape. He currently has no girlfriend because he say he wants to focus on bodybuilding. I have heard him fucking girls in his too though, once I even walked in on him fucking and boy dressed up as girl. It was hot, I had to quickly run out before I got hard.

Now about me, i'm sort of the dark horse of my family, I don't get treated poorly or anything, I am loved the same as my brother but while everyone else is 6 foot and above I'm only 5 foot 5. Everyone else in my family is very confident and outgoing where I am more introverted, my brother loves going out drinking whereas I would rather stay at home and read a book. I have got medium length blonde hair and I can't grow any facial hair ( not that I want to ). I have always been very slim and petite, I have a flat stomach and chest, thin arms but I was given my mothers ass. My ass is huge, I get mistaken for a girl from behind nearly every day. I was also blessed with what I believe is my dad's cock because despite being so small I have a 9 and a half inch cock, thick too, when I'm really hard I can't get my fingers around it. I'm also very submissive, I don't like being in charge and making decisions, I like to be told what to do. My mom still picks out what I wear and buys me all my clothes. Mostly I wear tight skinny jeans, t-shirt and runners.

At school because of my big bum I get a lot of smacks on the ass from guys mistaking me for a girl. The last guy to do it said to me " You have got a nice ass for a sissy ". I asked him " What's a Sissy?". As he walks away he yelled " google it ". I was curious to find out what it was so that night while I was on my laptop doing homework I decided to stop for a minute and google sissy. I was not expecting what came up which was a bunch of small feminine boys dressed up like girls, one of them even had fake boobs. I came across a definition which was ' A sissy is a biological male; who acts really feminine, slutty, horny, also really bimbo like, etc. They tend to be really submissive and are generally attracted to men but some are attracted to women '. The more I read about them the more I saw similarities between me and a sissy. I have never really been into men but the idea never put me off. I kept reading and came across something called sissy hypno. There was a video and it said underneath ' Watch this video to start your sissy journey '. My curiosity got the better of me and pressed on it, the screen came up flashing pictures of sissy boy's sucking cock or taking cock up ass, it's kept repeating' be a girl, it's what your meant to be '. I was entranced by this video so I decided to keep watching.

I kept watching for what felt like 5 minutes until the video stopped by itself and I looked at the clock and I had been watching for 3 hours. I looked down, I was naked which shocked me because I was fully clothed when the video started, I have no recollection of taking my clothes off. My cock was rock hard and I was jerking off without even realising. I don't think my cock has ever been this hard I couldn't get my fingers around it. I started jerking off hard thinking about the video, the words ' be a girl, it what you're meant to be ' kept circling around in my head. I jerked off for about 30 seconds and I exploded everywhere, it went all over my face, body and computer. Some went on my mouth and I was stunned because it actually tasted good, I couldn't believe it. I scooped some more off my computer and put my fingers in to my mouth and started sucking. My cum tasted amazing. I quickly grabbed my computer and started licking all the cum off it then scooped up all the cum off my body and face and put it in my mouth. My god it tasted amazing. I made a mental note to buy condoms so I can cum into them and drink it.

Unknown to me but my mom was watching me through a crack in my door, Her hand were in her pants rubbing herself and when she saw me eat my own cum she exploded. She had to bite down on her finger to stop from moaning, Kelly though to herself ' That's was so fucking hot I can't believe my little boy is a sissy eating his own cum, I might accidentally leave some panties in his room to see what he does, why does my little boy have such a big cock, I think it's bigger than mine '. What no one knows about Kelly except for her husband and a string of lovers is that she was blessed with both sex organs. She has a beautiful tight pussy plus a 9inch cock and huge tennis ball sized balls filled with cum. Her husband never touches her cock, while she loves him and loves there sex life she needs someone to hold down and fuck and I think she just found someone.

The next day after school I went straight to my computer to watch that video again, I could not get it out of my head, all I could think of all day was what I would look like in girls clothes. I opened up that video and I was taken by the video like last night, the video closes by itself, it felt like 10 minutes had past but was two hours. I ended up naked again, on my knees with a hand on my cock and a finger in my ass. I pulled my finger out of my ass slowly reveling in the feeling, as my finger comes out I cum into my palm and on my computer. I start eating the cum out of my hand when mom yells out " Oliver and Ben dinner is ready ". I quickly slurp down all that tasty cum in my hand, close my computer and get dressed hoping my cock goes down.

Dinner went by uneventfully, everyone just finished eating when my mom turned to me and said " Oliver honey why don't you do the dishes why I go get your clothes out for tomorrow? ". I said " Yes mom " and went about collecting all the plates and started the dishes.

Kelly POV

I quickly rushed up stairs and got one of my panties out of the draw and rushed to Oliver's room. I got him out some tight shorts for him to show off that bulge, a t shirt that's just a tiny bit cropped to show off a bit of stomach, some socks and shoes. The last thing I got was one of my panties and I also got one of his normal underwear, I want to see which one he picks. I was just about to leave when I saw how messy his desk was and started to clean it for him, curiosity got the better of me and I opened his laptop and I gasped when o saw all his cum on the the screen. I couldn't help myself I reached a finger out and scooped some up, it's was so thick, I put it in my mouth and what I tasted was the best cum I'm ever tasted in my life. I have sucked a lot of cock in my life but nothing compares to this, it's was rich, creamy and delicious. There was a wet spot on the ground because I was creaming my panties so hard I was dripping. I heard him coming up the stairs so I quickly closed his laptop, ducked out of his door and ran for the bathroom. I got in the bathroom and leaned my back on the wall, pulled my panties to the side and stuck 3 fingers up my pussy and started furiously jerking off, i have never been so turned on in my life, all I kept thinking about was how good his cum tasted and how I need more. I was so close to cumming so when I stuck a 4th finger in my pussy I exploded and fell to the floor spasming with the best orgasm I have ever had, all because of my little boy.

Oliver POV

Once I had finished doing the dishes I went up stairs to my bed room to find my clothes laid out and that first thing I noticed was there was my normal underwear and some girly panties. I walked over to the dresser and picked them up, they were so soft I could only imagine what they would feel like. So I quickly ripped my pants and underwear off and I put on the panties. They were so comfortable, I felt more comfortable in these than in normal underwear. I went and looked in the mirror and my ass looked amazing in them, they fit me perfectly and my cock was nice and snug in them. I was checking my self then I realised that I had some cum left on my laptop so I quickly opened it to see that it looked like someone has wiped a finger across the screen and wiped some cum off. The only person in here was mom and surely she wouldn't off scooped some cum up. I decided to not think about it and focus on eating the rest of cum, I slurped it all down and cleaned my laptop up. I went back on to my computer to watch the hypno video again but it said not allowed must watch next video. So I scrolled down the webpage and saw another video and I clicked on it. The pictures showed more boys dressed up as girls riding dildos with the words ' don't touch your sissy clit, cum like a girl, ride cocks like a slut '.

Again the video stopped and about 2 hours has past, I was on my knee's with 3 fingers jammed up my ass, my cock was rock hard. I slowly started to pull my fingers out and it felt so good that I slowly pushed them back in. The words from the video in my head ' don't touch your sissy clit and cum like a girl '. So I removed my hand from cock and and focused on my fingers and started going faster and faster till I was jamming my fingers as fast as a I can in my ass, I could feel it building so I quickly put a condom on my cock and after a couple of minutes I came, I extracted my finger from my ass and I had a overwhelming feeling of emptiness. I check the condom and it was full to the brim, I had never cum that much before. I decided to have a little sip of my cum then tie the condom off and leave it for later, I need to clean up so I wondered off to the bathroom to clean up.

Kelly POV

That was the hottest thing I have ever seen, he has 3 fingers up his ass and his cock was absolutely massive, about 10 inches long and the amount of cum in his balls, my god I need that condom. I quickly went into his room and grabbed the condom and ran down the hall and into the other bathroom. I closed the door, put my back to it, opened the condom and drank down all of the delicious cum. It tasted like heaven and made my knees weak. I think I need to get this from the source. Hold on Oliver mommy is taking you.

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