From Son to Sissy

A little backstory to this, alot of this story is based on one of my friends and what their journey was like as they were coming to understand their true sexuality, and a lot of it is their fantasy. All characters in this story are 18 years of age or older.

I had always known i was different from all my other friends. It was when i turned 18 that i had really started taking the leap towards my fantasy. I had discovered sissy/feminization videos online and i was instantly hooked. The barrage of images and videos of woman being taken by men in every which way had almost melted my brain. I would watch in fascination as these women would be ravaged by cocks in every hole, all the while screaming and grinning with pleasure. It began to pique my curiosity on how good it might feel for me to be taken in the same way. The thought of being degraded and used freely gave me a sort of sick satisfaction. Soon enough i had moved onto Jerk off instructional and Cum Eating instructional. It started off delicate with very soothing and reassuring models calmly telling me how good it was to do these things, but soon enough i moved further towards more humiliating ones calling me things such as "sissy" "faggot" "cockslut" and "cumdump". While these names were meant to be degrading and offensive every time i heard them my little cock would begin to throb and turn rock hard.

My experimentation had then brought me to crossdressing, the first time i slipped on a pair of frilly panties and felt them ride gently up my crack and nuzzle softly against my anus I had truly felt like i was myself, no more lying, no more hiding i was just who i was always meant to be, a sissy.

Now my dad had always been an old school type of guy, he tried relentlessly to get me into sports, interested in cars, hell he had even tried to take me to the strip club on my 18th birthday, which to his pleasure he saw I was in awe of the women there, but little did he know it was for completely different reasons than his own. I know my dad had suspected i was different years ago and had made many futile attempts to "straighten me out" in his image, and while it hurt that I always imagined he would never accept me for who I truly was I will say that he was never a cruel man and always treated me with respect and dignity.

With that being said that brings me to the main topic of this tale, My dad was a very social guy and had many friends who would pay visits to our house. They were all the same type as him, very rugged all american men with strong jawlines and well built bodies. While i would say they did have a sort of masculine attractiveness about them i was never really to intrigued by any of them, that is except for my fathers friend Mark.

Mark was the same kind of rugged man the one thing that always set him apart from the others was his unwavering kindness and overall gentle sweetness. My fathers other friends had never been mean in any way but there was a general aloofness about them, they were pretty much in their own heads the entire time but Mark was different. He would always ask how i was, tell me how great i looked (even if it was under the context of me being a lady killer) and try his best to take interest in what i was doing. The point at where i really knew i had an unbridled attraction to Mark was one day we had just finished up a game of football and he patted me gently on the butt exclaiming

"Good game sport."

As soon as his hand had grazed my bottom my cock had turned to rock instantly. I had turned beet red and excused myself to the bathroom, with my boner still raging i had stroked my cock furiously at the thought of Mark's hands touching me all over my body until i had furiously came, it was the most intense orgasm i have ever felt.

My thought about Mark grew more intense and i began to find myself longing for his hand to touch my ass once again. I would imagine his gentle hands caressing every inch of my body and wonder how safe i would feel contained in his hulking grasp.

One day when my parents were out i had decided to go all out with one of my outfits. I had slipped into some nice bridal white stockings, with a matching garter belt and bra, and of course my favorite pink frilly panties covering my soft undercarriage. I began to prance around the house jovially imagining what kind of reactions i would get from the boys, I was truly encapsulated in my own little world. I had taken my phone out and bent over the couch, pressing my tiny little bum out and arching my back. I took photo after photo of my backside arched out wearing a naughty expression on my face and hanging my fingertip from my bottom lip.

In all the excitement i had not heard the front door open and my stomach dropped as i realized what was now a reality. With my back arched and my ass pressing seductively towards the door and had craned my head back to see a figure standing there staring right at me. It was Mark.

Frozen with fear in continued there with my butt pointed right at him in almost some form of mating ritual, once i came back to my senses i had immediately scrambled for a pillow and yanked it in front of me, curling myself into a ball and shrinking as small as i possibly could, emulating how small i felt in that very moment.

Mark had remained where he was with a shocked look on his face, he had not spoken a word. To break the awkward silence i began to speak up

"Oh my goodness Mark i don't know what to say, this is so embarrassing."

I had basically sulked.

Mark had began to make his way over to me and sat down beside me, i had clutched the couch pillow even firmer now. He had taken a deep breath and began to speak up.

"Now Zack i want you to know there's nothing to be ashamed of here, i apologize for my reaction but you can understand my shock in the moment."

I sheepishly nodded my head, slightly releasing my grip of the pillow.

"But i must say, I am not overly shocked of what i saw, just how i saw it if that makes sense?"

I stared with confused but with great interest into Mark's soft hazel eyes.

"Let me just start off by saying i have always known you were a little different Zack, and in knowing that I have always tried to be as kind as I could with you, I'm sure just being who you are bring lots of discomfort and harsh remarks, which is completely unfair."

My grip of the pillow had released further and I relaxed, I listened on as Zack continued to speak.

"I just want you to know that there's nothing wrong with what you're doing or who you are. Even though people may say it is you mustn't listen to them. You know who you are better than anyone else in this world and you must follow what you know to be true."

Mark's words had brought an air of reassurance and i had began to feel much better.

"So how long have you been interested in this?"

"Well i always knew something was different but i have only been dressing up for a few months now."

"Well i'd say the look suits you." Mark had replied with a grin

I began to blush furiously once again gripping the pillow and bringing it closer to my flush face.

"T...thank you."

"Now i can see you are aiming for a certain feminine beauty, if you like i could definitely give you some tips."

"That would be lovely." I had replied sheepishly.

"Well first thing although you do have a natural sort of beauty to you, i think make up would really help you see the person you are yearning to see in the mirror. I can send you some Youtube links on make up tutorials."

"That would be amazing, please do!"

"And if you're interested i can definitely coach you on certain things like walking, speaking and general ladylike behavior."

"I would love that Mark, are you sure that wouldn't be asking too much?"

"Of course not, i am more than happy to help you in your quest to be who you truly are."

"T...thank you so much!"

I hugged Mark tight as tears streamed down my face, i had finally felt free. My voice had broken as i peered deeply into Mark's eyes.

"C..can i ask you a question Mark?"

"Of course you can."

"And please don't take this the wrong way, but how do you know so much about this... specific topic?"

"Oh sweetheart i have 3 daughters! and their mother has always been obsessed with those silly beauty pagents so i've picked up quite a bit from those, i guess that knowledge can finally pay off." Mark chuckled

I hugged Mark tighter and thanked him profusely for his help and understanding. Mark had placed his hand gently on my head and began to soothingly run it down, caressing my silky blonde hair down to my shoulders.

Mark had stood up, given me a kind smile and began to make his way to the door.

"Well i have your cell number, ill shoot you those videos and we can talk about getting things on track."

Mark had turned the doorknob and began his walk outside my house, with one last glimpse out my front window he turned around and shot me one more pleasant grin. I had fallen back into my couch almost featherlike, I had felt a massive weight lift off my shoulders. There was finally someone that i could confide, someone i could be myself around and of all people it was Mark. I returned to my room and changed to avoid any other unwanted intrusions and made my way to my bed. I had rested my head on my pillow and lay there peacefully with how well that unexpected interaction had gone.

I had spent the next few days rigorously studying the make-up tutorials Mark had sent me. I was now confident in applying my own mascara, foundation, lipstick and toner. I would put on my outfit every time i had completed my make-up and it always made me feel wonderful. I waited in anticipation for Marks next message, i wanted desperately to learn the fine points he had to offer, but even more so i longed just to be near him.

The next day my phone dinged and my face lit up with excitement, it was Mark!

"Hey i wanted to see if you're still interested in our lessons, if so are you free tomorrow night?"

I replied almost instantly.

"Yes! tomorrow night works perfect."

"Alright come by my place around 6 :)"

That little smile at the end really added so much to the message, I had hugged my phone and dreamed about what was in store for me tomorrow. While lying in bed i decided to turn on my laptop and browse for some encouragement. Tonight i didn't feel like my usual sissy/JOI, tonight felt different. I browsed the net for nearly 30 minutes to find a video of a man who resembled Mark, at first it was just solo videos, i watched in awe as the man stroked his cock, i was fascinated by every detail. The way it rose and grew, i wonder how Mark's would feel growing in my hand? The veins that protruded triumphantly, i wonder how they would feel against my tongue? The way it throbbed, i wonder how it would feel throbbing in my tight little hole?

My hands began to wander and something had overtaken me, the began exploring a foreign area. While i was accustomed to usually stroking my tiny cock my hands now had an urge to go underneath and i began to rub my tight hole. i swirled my finger gently, sending waves of pleasure throughout my body. Soon i slowly began to slide my finger up, curiously exploring my insides. Deeper and deeper my finger ventured until i felt a node, i tickled it gently and it sent waves of euphoria through my body. Instinctively i began teasing it harder and harder until one final press had sent me over the edge. Semen had began to flood out of me in what would be one of the most life changing orgasms of my life, for the first time i had cum strictly from my butt.

As i lay there covered in my own cum i could only feel a slight disappointment that it wasn't Mark's, I began imagining his throbbing cock spraying my whole body with his sweet silky strands. With that thought i had drifted softly into a slumber, still covered in my mess and fully inserted inside myself.

The next day seemed to drag on endlessly, i just wanted time to flash by so i could arrive at Mark's already, i spent an hour before nervously pacing in my room before i built up the courage to send the text.

"On my way now, see you soon!"

"Can't wait :)" Mark had answered back.

As i made my way there i couldn't help but wonder what he might have in store for me. My mind raced and wandered with multiple scenarios of what might happen, I couldn't help but hope he was waiting for me naked but that was merely a fantasy. As i arrived i pressed my finger to the doorbell and was pleasantly surprised as the door swung open. Mark had appeared in front of me wearing a tight tank top and grey sweatpants that did very little to hide a bulge. I stared intently at it until i snapped back to my senses.

"Hey Mark!" I squealed awkwardly

"Hey there, you ready to get started?"

I nodded sheepishly.

I followed Mark through his house until we had reached his living room, It was beautiful, the carpet was a nice white shag, he had very luxurious furniture, The walls were painted a very calming beige and he had a nice classic brick style fire place to tie the room together. I sat down with my knees together and tried my best not to act too shy. Mark had walked in front of me and for a split second i was face to face with his gorgeous bulge. He continued walking and gestured for me to come to him.

"Alright now today i really just want to focus on the walk, it's going to be the toughest so we can take extra time with it."

I began to walk and Mark immediately started with pointers.

"Alright first thing is you are really slouching your shoulders, now you don't want to press them too high but you do want to have a certain dignity to you if you know what i mean."

Mark had placed his hands on my shoulders and instantly i felt shivers down my spine, with his hands against my shoulder blades he raised them slightly and followed me as i walked.

"Alright now try that on your own."

I walked now with my shoulders held higher, Mark was right there was a sort of dignity in this.

"Alright now i want you to take longer more elegant strides, lead with the front of your feet not the back."

I began to follow my toes instead of my heels and found much more grace in my step.

"Perfect! Now try to sway your hips a bit more, swaying of the hips is a huge turn on for a lot of men."

Mark had placed his hands on my hips and swayed them back and forth as i walked forward, his touch was beginning to send me over the edge, My face turning brighter with every movement.

"Now finally you need to raise your butt a bit, It will help give your walk a more natural feel."

As mark said that he pressed his palm to my bum and began to lift, then there was an unmistakable feeling, his finger had prodded ever so gently between my cheeks against my hole. My cock had shot up instantly and my face turned beet red. With that i had completely lost my walk and almost fallen over.

"Everything OK?" Mark inquired

"Yes! Sorry! i just got a little overwhelmed."

"Did i touch you inappropriately? I am sincerely sorry if i did i can get carried away sometimes and forget what i'm doing" Mark had chuckled confidently

"NO! i enjoy the touching.. i mean i don't mind it." I began to nervously garble

"Alright as long as you're comfortable." Mark gestured.

We spent the next hour finely tuning my walk, Mark's hands had been caressing my body and I couldn't get enough of it. 9 PM had rolled around and Mark suggested we call it for the night.

"Honestly i think you've made amazing progress, I think this will come naturally to you sooner than you think."

"I'm glad we can do this together, it's been awful lonely in the house since my divorce so it feels good to just have companionship in my home."

I couldn't help but shoot Mark a proud smile as I followed him to the door.

"What are your nights like? Would you like to do this every night at 6? My evenings are pretty open these days and i enjoy the company."

"Yes!" i shouted excitedly.

Mark had shot me a grin and chuckled.

"Alright perfect i will see you tomorrow at 6."

"Great! thanks again for doing this Mark i really can't explain how much it means to me."

"Don't mention it, I am more than happy to help you in any way I can."

As i reached the door mark had given me a few links to tutorials that could help me tune my voice, i turned around and took one final glimpse of Mark's contagious smile and couldn't help but smile to myself. As i made my way home i practically skipped with joy until i had arrived in my bedroom. Once again i had fallen effortlessly into a pleasant sleep, with dreams filled by Mark.

For the next few weeks we had spent hours training my walk. First on flat feet, than my tippy toes and finally in a pair of heel's that Mark had surprised me with. We trained my voice, tuned my make up and even tried on a few outfits. After 3 months i felt confident in who i was when i peered into the mirror. My hair had reached my shoulders, my eyelashes fluttered effortlessly, my lips were crimson with lipstick and my voice was subtle yet sultry. I finally did it, I didn't need to dream about being beautiful anymore, I was beautiful.

I had reached Mark's house ready for another session when he presented me with a box. It was a beautiful red satin dress. I gazed upon it with wonder, I couldn't wait to put it on.

"Can i try it on now Mark!?" I squealed with glee.

"Not quite yet sweetheart there's a few other things i want you to see."

Mark then presented me with earrings, a necklace, perfume, and brand new heels.

"Oh my goodness Mark, I can't accept this."

"Don't worry it's part of your final training. You're going to put all this on and do everything we practiced, from your walk, to your voice, to your make-up. You're going to do all that and you're going to meet me at the bar as my date."

"Y...you're date?" My heart began to pound.

"Yea what better practice than that, and it wouldn't hurt my reputation to have such a stunning young beauty to show off now would it?"

My heart fluttered at that sentence, Mark thought i was beautiful?

"A...alright i'm ready."

"Perfect, tomorrow i want you to meet me at sliders at 7 PM"

"7 PM at sliders... Okay."

Mark had began to walk me to the door, as he opened it for me he tapped me gently on the bottom.

"Can't wait." He said with a devilish grin.

I walked out in a state of disbelief, I couldn't believe this was all happening. As i arrived at home for the first time in months i didn't fall effortlessly into sleep. Tonight i was wide awake with anticipation.

I spent the next day completely focused, i practiced my walk and my voice all day and when the time came i began my transformation. With my hair done, my make-up on point and my new accessories i was confident in my look. I began my walk out, thankfully i lived in the basement and there was a separate door so i didn't need to sneak by anyone. I made my way to Sliders with absolute confidence, swaying my hips with every stride. I began to notice all the looks i got and i couldn't help but feel empowered. All this attention, all these men giving me a second look, it was amazing.

When i had finally arrived at Sliders i saw Mark standing by the bar, He was wearing a tight black T-shirt and blue jeans, he looked incredible! I approached him and his expression turned instantly with joy.

"Well don't you look beautiful!"

"Thank you." I answered jovially

Mark had ordered a beer and motioned me towards him

"Come here there's a few people i want you to meet."

As we walked through the bar my stomach had dropped to my knees, sitting there was my father and the rest of his friends. I panicked, I wasn't sure what to do when Mark had whispered in my ear.

"Don't worry, i wanted to show you that i'm so confident in you that your own father couldn't recognize you."