Maddy's Got a Secret Vol. 01

Meeting The Family

Hello! My name is Dylan. I'm 21 years old, and I live in a small town in southern Ontario with my Mom and Dad. Growing up as an only child, I was always close with my parents, specifically my Mom. I didn't have many friends, and I was always excluded at school. I never had the opportunity to play sports; though my tiny build wouldn't have helped me in sports all that much anyways. Despite feeling alone, or excluded; my Mom and Dad always loved me, and tried their hardest to provide for me and make me happy.

My Mom is a beautiful woman; arguably the most beautiful woman I've ever seen. Her tall figure makes her seem powerful; standing at 5'10" my mom has a dominant figure. Yet, her busty, voluptuous curves hold the balance with femininity and beauty. Her large breasts sit up perky and full on her chest. But that's shadowed by the immense size and shape of her phenomenal ass. My mom has the widest hips on a woman I've seen, and they lead perfectly to her huge, round ass. I know I shouldn't stare at my Mom, especially in a sexual way - but I just can't help it. Mom is always wearing leggings and shorts to keep up with her athletic lifestyle, and I can't help but look every time she walks by; just to watch her ass jiggle and shake with each step. Her long, blonde hair is always straightened and seems like there's never a single hair out of place.

My dad is a hard working man; working as a civil engineer managing bridge construction and development. He is often traveling for work, sometimes spending weeks at a time away. I always missed dad when he was gone for work; it felt like something was missing at home. But he always made sure to call when he could, he would take lots of photos to show me the bridges he was building, and he would usually bring me back a souvenir from his trips. One year, when I was 11 or 12, dad brought me back a stuffed animal from Arizona. It was a plushy of a ring-tailed cat, something I had never heard of before - and I absolutely fell in love with it! I slept with it every night, and even to this day, when I get sad, or lonely, I still sleep with the now tattered and worn plush. Despite missing dad when he was on his trips, it allowed me to be alone with Mom, which made us grow closer and more connected over the years.

Being 21 years old, I often feel confused and embarrassed about my body and appearance. I never really had much of the stereotypical puberty like the other boys my age. I never grew hair on my face or body. My body didn't really grow much, maintaining a 5'7" height throughout my entire teen years; and I still only weigh 125lbs - the same weight I was when I was 13. This led to a lot of bullying and harassment in school. I guess I have a "feminine" face and body; and my shoulder length brown hair doesn't help either. I was often called a 'girl', a 'sissy', or even at times 'gay' or a 'faggot'. This of course made me much more reserved and quiet at school. I hated being there, and I hated my appearance. But no matter what, Mom always loved me and supported me. She never failed to call me her 'handsome young man'. She always wanted me to be happy with who I was, and accept myself and my appearance. Over the years, it was hard; but since graduating High School and spending most of my time at home with Mom, I've grown to love myself and my body. And that's all thanks to Mom!

As I'm trying to find my life, and form my career, I spend most of my time at home in my room on my computer. My main job is being an indie game developer. I was always inspired by my dad and the amazing things he got to do and see with his work, and I wanted to find my own way to experience that. So I turned towards creating games when I was around 16. I work from home in a small development team called 'Mooncloud Productions', and even though we haven't had too much success, I still love being able to create worlds and see my designs come to life!

Mom and Dad have both been very supportive of my development job, and have pushed me to continue living at home while we work on developing bigger and better games. Mom loves seeing my games and the stuff we are working on everyday. She's always asking questions and giving me ideas for things to add, or how to fix bugs we've been stuck on. Whenever I'm not working, Mom is always asking to spend time together. Whether it's watching a movie, going out for lunch, or just playing games together - we both love the quality time we get to spend together. Despite being close, our relationship was always simple. Until a recent event caused a rift in our relationship - one that I don't think we can work past and forget about anytime soon.

Day Plans Ruined

Early this morning I was in my room working on our most recent game. Dad had just left for a trip down south to Tennessee, and was going to be gone for another 3 weeks or so. While I'm bug-testing an issue with a revolving door in our latest game, mom knocks on the door:

"Hi honey, I'm heading to the gym for an hour or two. Afterwards I'm going to head to the grocery store to pick up some stuff for dinner. Since it's just us, how do you feel about some chicken?"

Mom is wearing her neon pink sports bra, which seemed to be just a size or two too small for her. Her slim stomach and toned abs lead down to a tight pair of black Lululemon leggings nearly suffocating her thick thighs. Long blonde hair tied up in a ponytail, she seems to have just the thinnest layer of makeup on. Her plump lips are the softest shade of pink, just enough to compliment the subtle mascara she is sporting.

"Chicken would be great mom! Could you maybe get us something for dessert afterwards as well? You choose, keep it a surprise."

"Of course I can sweetie. I think I already know what to get!"

"Awesome, thank you mom! You're the best!"

"Awww, you're welcome honey. Well I'm going to head out now, I'll see you in a few hours. If you need anything, text me!"

"Okay mom, be safe. I love you!"

"I love you too, my handsome young man. I'll be back shortly."

And with that, Mom was gone - leaving me alone in the house for a few hours. As soon as I hear Moms car pull out of the driveway, I immediately open up Discord on my computer, get up out of my chair and nearly sprint to Mom and Dads room. Because with Mom and Dad both out of the house. I could be my true self for a couple hours. A little secret that I've been hiding from my family for the past 2 years. The little secret that I like to dress up in girls clothes and call myself a sissy.

It seemed to have started out of nowhere. One day when I was 19, mom had left for the gym like always, and dad was on another work trip. I went to grab a snack from the kitchen when I walked past Mom's room, and saw a used pair of her black lacy panties sitting on the floor of her bedroom. I don't know what compelled me, but I was drawn to them. I slowly creeped into Mom and Dad's room, cautious but curious. I bent down and picked up Mom's used panties, shakily holding them in my hand. I noticed the inside of the panties were moist, mom just had these on! I don't know why, but without thinking; I gently lifted the moist crotch of Mom's soft panties to my nose, and took a deep inhale.

The smell was intoxicating. I nearly fell to my knees as soon as the delicious scent hit my nostrils. In seconds my cock was rock hard as I sniffed my Mom's wet, used panties. I couldn't stop - I just had to keep inhaling Mom's scent. In & Out, In & Out, all I could think of was how I needed more. I wanted to just flood my mind with the scent of my Mom's pussy. After many minutes of smelling the panties, the smell began to fade, and I was only growing more insatiable. I looked down and saw my throbbing erection sticking out farther than ever before. I reached down, and wrapped Moms wet panties around my cock. Gently squeezing, I started slowly stroking my hard cock up and down, using Mom's panties as a barrier between my hand and my cock. As I stroked, all I could think of was the taboo of how dirty what I was doing was.

"Omg, I can feel the wet spot of Mom's panties on my cock!" I thought to myself.

Realising how good the wetness of Mom's panties felt on my cock, I had the craziest idea of my life... What if I put mom's panties on?

In one short movement, I slipped the panties off of my cock, and slowly lowered them down towards the floor. I step one foot in, and then shakily raise the other leg. As I lower my other foot into Mom's panties, my entire body begins to shake. "This is so dirty, so wrong!" was all I could think about. Gently, I lift them up, and slowly feel the soft material rise up my legs. As I get them up, I feel the soft back lift up over my tiny ass, and I place my cock just sitting up over the top of the panty waistline - feeling the remaining wetness pressed up firmly against my aching balls. While they may be a little big on me, they still rest comfortably on my hips. Realising I'm now wearing my Mom's used panties, I decide to slowly head to the bathroom so I can see what I look like. I make my way into Mom and Dads bathroom. Standing in front of the mirror, I see myself wearing my Mom's panties for the first time. And at that moment, I don't know what happened. I felt my body shiver, butterflies filled my stomach, as I began to feel my heart beat nearly out of my chest. My tiny body, and soft skin looked so feminine while wearing Mom's panties. My hips looked like they were wider, my legs appeared thick and sexy. I looked just like a girl!

As soon as I saw myself as a girl, I felt it. The deep throbbing in my cock finally erupted. I felt my whole body tense, my legs shaking harder than before. My eyes closed as I gasped aloud. I began shooting a huge load from my cock. Cum flying everywhere, it landed all over my soft tummy, all over Mom's panties, and even covered the floor. This hands-free orgasm seemed to never end. I could only lean over, grabbing the counter, and wait for it to end. Finally as the last spurts settled, I looked up from the counter, and saw my face in the mirror. My shoulder length hair was a mess, face beet-red while I was completely covered in my own cum. I looked like such a whore. Such a sissy slut. And it was at this moment that I knew; this was my life now. I had to keep doing this whenever I had a chance. I loved how I looked when I looked 'like a girl'. I loved feeling like a whore. I loved being a sissy. And ever since that day, I've been taking every opportunity to dress like a girl and be sexual in secret. Just like I was going to do today.

With mom gone for the next few hours, I know I have loads of time to indulge in my secret persona. As I trip over myself rushing into Mom's room, I head straight for Mom's dresser. Opening the top drawer, I start riffling through her underwear. Thongs, panties, g-strings, all of them worn by me in secret at some point over the past years. As I'm digging through, I find one of my favourite pairs. Mom's tiny pink Victoria Secret thong. The black lace embroidery compliments the soft pink of the fabric. This pair fits me just a little tighter than the rest, allowing me to feel like they're really my panties, and that they're not too big.

As I slip them on, I instinctively reach for Mom's black stockings. I grab the pair and begin pulling them up my legs. Now with the stockings and panties on, I reach for Mom's most vibrant red lipstick, and head straight to the bathroom. Leaning over the counter, I apply the lipstick - carefully, but sloppily. I'm still not great at applying my own makeup while I dress in my sissy outfit. Finishing with my look for today, I put Mom's makeup back, and I head back to my room.

I get to my computer and as I sit down, I begin looking through my messages and tags on my Discord Server.

'Noodle Daddy': "Damn Maddy, you look incredible in that one!"

'S L E E P': "Madison I want to fuck your tight ass so bad"

'Cyka Blyat': "Maddy literally has the best girlcock I've ever seen. She's always hard"

'PhOeNiX': "Does anyone else vote Madison as e-whore of the year?"

Seeing this, I immediately get this warm tingling feeling throughout my body, the feeling that I've grown to know and love over the past 2 years of fulfilling my naughty secret. I love showing myself off like this, especially when I'm covered in my cum or fingering my ass. It makes me feel so feminine and dirty. And when I get this much attention, it's like it consumes me. All I want is more. The positive attention to my appearance lights a fire in me everytime I post a new pic to the server. I am Madison, I am a sissy who posts my slutty life online for the world to see, and I love it.

When I'm in my Madison character, nothing else seems to matter. My only purpose is to be a good sissy girl. Cumming all over myself, finger fucking my ass, posing for pictures. No matter what it is, I love it. I love sharing it. I try to take as many pictures and videos as I can as Madison, so I can share them to my Discord fans. I have so many loyal fans, and for once in my life I feel popular. I feel like I have friends, and I'm allowed to be my true self no matter what. Sometimes my Discord followers have even paid me for specific videos or to wear certain clothes in my photos. I love making my fans feel good, and helping them get off. Knowing that a bunch of people are jerking off and cumming while looking at my pictures and videos turns me on and makes me want to go deeper, be filthier. I want to just truly submit to being an e-whore for these men.

As soon as I sit down in my computer chair, I open my webcam to start taking pictures. With my webcam open, I see myself in my girl form. In this moment, I'm no longer Dylan, I'm Madison; a sissy femboy who exists to please people online. Upon seeing myself in my webcam, my cock starts immediately growing. A slow, throbbing begins at the base of my cock. I feel it pumping, each heartbeat gently raising my cock higher, and harder. After what seems like only seconds, my girlcock is hard enough to cut diamonds - standing up outside of moms panties while pressed against my soft tummy. At this point, I hit record on my webcam, and lean-back in my chair. With lipstick on, panties tight against my throbbing cock, and stockings perfectly framing my thin legs - I reach down to my now aching girl-cock, and begin ever so softly stroking up-and-down.

Watching myself in the webcam, I begin to fall deep into the sensations. I tilt my head back, and begin moaning aloud. As I'm moaning, my pace quickens; precum drips from my cock - making a mess of my Moms panties. I keep stroking, eyes-closed as I begin to lose control of my senses. All that mattered was this moment, this pleasure. As I felt my orgasm beginning to rise, I began speaking to myself between moans; "I'm a good slut", "I want to cum so bad", "I can take it, I'm a good whore!". Feeling myself getting close to the edge, I'm finally ready to cover myself in my big load; when the chilling shriek from my bedroom door snaps me out of my trance:

"Dylan! What the hell do you think you're doing!"

This is the end of

Maddy's Got a Secret: Volume 1. Early Beginnings

Feedback and criticism is much appreciated. If you enjoyed it, please be sure to like and comment your thoughts. I have plenty more stories with Maddy to come if the interest is there. Thank you for reading!

Patrick Wallen