From Son to Sissy

I regained my confidence and continued my walk towards the table. As we arrived Mark had began to introduce me.

"Hey fellas this is Maya."

The men had all eyed me up and down, they definitely liked what they saw. One by one they introduced themselves until it came to my father.

"Sheesh Mark, this ones young enough to be my son's age, how do you do it?"

That comment had made me chuckle internally.

"Oh you know i have my ways, anywho fellas i just wanted you to meet Maya, hate to cut and run but we have quite the evening ahead of us."

"Well don't get too wild with the young lady." My father had chuckled.

With that being said Mark had placed his hand at the small of my back and lead me out of the bar, we entered his car and began to drive.

"Thank you so much for that Mark, that gave me more confidence than i have ever had in my life."

"Ah don't mention it sweetheart, i knew you would absolutely nail it."

We continued to drive when a question had popped into my head

"So... Mark do you really have an evening planned tonight?"

"As a matter of fact i do, but it's a surprise so i'm gonna need you to play along for just a little while okay?"

"Okay"

My mind began to race, what could he possibly have in store, my heart practically beat out of my chest.

When we arrived at marks place he showed me to the living room, he had lit the fire place and a few candles to set the lighting.

"Can you excuse me for a few minutes?"

"Of course" I replied nervously.

I sat in anticipation waiting for what was to come next and then i heard footsteps. My heart began to race harder than it ever has before, Mark had entered the living room in nothing but his boxer briefs, his bulge begging to escape and he handed me one final box.

"Here i want you to open this."

"O... okay" i mumbled with my jaw basically touching the floor.

As i unfurled the ribbon and slid the box open i saw what appeared to be bright white bridal lingerie, I gazed upon it intently admiring every little detail.

"I want you to put that on, i will return in a few minutes that should give you plenty of time."

As Mark left the room i began to furiously strip all my clothes off, once i was fully naked i began to place every piece of lingerie on my body with fine care. The stocking rode smoothly up my legs, the garter belt fit snug around my waist and the frilly white panties had snuggled up perfectly against my bum. As i made the final adjustments Mark had returned.

"Now sweetheart i want you to drop to your knees, close your eyes and stick your tongue out."

I did exactly what was asked of me. My knees pressed gently against the floor and i opened my mouth wide with my tongue protruding hungrily out.

"That's a good girl."

I heard footsteps moving closer towards me and finally they stopped, then there was a gentle thud of fabric hitting the floor. With my tongue pressed out and the cool air pressing against it I could feel a warm sensation coming closer. Soon there was an unmistakable feeling against my tongue. A warm and slick object had rested itself on my tongue.

"Now sweetheart i don't want you to do anything but breath for these next few seconds, I really want all your senses to understand."

I inhaled sharply and was overwhelmed with and insatiable scent, there was an intoxicating must overtaking my brain, I waited patiently adoring the smells until Mark's next instructions.

"Mmmm that's a good girl. Now i want you to take your tongue and glide it gently side to side."

As instructed my tongue began to gently slide side to side against Mark's glands, they felt amazing, they tasted delicious, i was slipping further and further into a lustful brain fog.

"Oh yeah that's reaaally good Maya."

I loved that he called me that, it was such a beautiful name. My tongue continued back and forth, thoughts rushing through my mind with every flick of my tongue, the taste became stronger and stronger and with it my appetite grew fiercer and fiercer.

"Alright now i want you to swirl your tongue around."

My tongue began to wrap around his throbbing head, I puckered my lips around hugging his head and with my tongue swirled round and round. I started counting laps, one, two, three, with every lap I memorized Mark's head more. The swollen glands on the top, the split at the bottom of his mushroom head, i found myself drawn to that spot in particular, I would keep my tongue pressed firmly against there for seconds.

"Oh my you're a natural at this Maya,"

I couldn't help but feel pride in that comment.

"Alright now i want you to slowly take the tip in your mouth."

I slid my lips down until Mark's massive head rested gently in my mouth i held it there for a while tantalizing it with my tongue. Mark placed his hand firmly on the back of my head and gripped a hand full of hair.

"Now for this next part don't you worry i'm going to help you out step by step, all you need to do is relax your jaw and relax your throat."

With a hand full of hair Mark began to slide my mouth slowly down his shaft, deeper and deeper until he began to reach my throat. The tip of his cock began to jab my uvula and i choked back tears, i couldn't fail Mark, not now and not ever. With tears beginning to stream down my face and saliva pooling around my cheeks i had felt my nose press against Mark's navel. Once we had made that contact Mark had hastily pulled my head from his cock and i couldn't help but feel a tinge of disappointment.

"Don't worry sweetheart, there's plenty more for ya, just gotta give you some air haha."

As i caught my breath Mark had instructed me to open my eyes, i had completely forgotten that i had them closed this entire time, i was consumed with my thoughts. The wonder of all these sensations without visualization really did add to the experience. As I opened my eyes I was in awe at what stood in front of me. Mark had the perfect cock, the head was swollen with a hint of red begged to be sucked, His shaft was girthy with plenty of healthy veins protruding out and his length was more than endowed. I couldn't help but stare which gave Mark a chuckle.

"Alright sweetheart are you ready?"

"Yes!" I Replied with almost too much excitement

Mark's cock once again invaded my mouth, in and out, back and forth, i had finally become comfortable with it in my throat. At one point his full length was down my throat and i managed to take my tongue and tease his balls while his cock prodded my uvula. Mark began to tense up and instructed me.

"Oh god, alright sweetheart i'm almost there now i'm gonna pull my cock out and rest the head on your tongue, all i want you to do is tease the underside of my head with your tongue."

With my eyes glued to Mark's I stared into his soul as i flicked my tongue furiously. His body tensed further and further until he let out one final groan.

"OH SHIT! here it comes!"

With his throbbing head rested on my tongue Mark's cock began to flood my mouth. The first powerful stream shot right to the roof of my mouth, the second to the back of my throat, then stream after stream coated my mouth. It was a life changing sensation, i couldn't believe how much I enjoyed it. With one final twitch Mark had emptied the rest of his balls into my eager mouth. He pulled away to catch his breath and collect his thoughts and i sat there patiently. I wouldn't dare swallow his seed yet, i wanted him to see. Mark had turned around.

"Now that's a good girl, you don't swallow until daddy tells you to."

I continued on my knees, time seemed to sit still, I waited patiently for my next instructions.

"Now open wide and show daddy your treat."

I opened my mouth and proudly displayed Mark's cum that coated my entire mouth, Mark grinned to himself.

"That's right, now be a good girl and swallow all of it, don't waste a single drop."

I swallowed instantly and on instinct opened my mouth to show Mark that there was nothing left, his seed had now filled my belly with a warm sensation. Without thought i brought my lips back to Mark's cock and swirled my tongue around one final time. Mark tensed up once again and grabbed my head.

"My my aren't we eager." Mark had commented.

"You said don't waste a drop" I said with a cheeky grin.

Mark had grabbed a fist full of hair and brought me to my feet, he pointed at the couch and directed me there. As i made my way towards the couch i felt his palm strike firmly across my ass, leaving a pleasant sting.

"I always knew you were a good little slut, now get on the couch and point your butt towards me."

That comment made me blush, I made my way to the couch and climbed it, on my knees i pointed my butt right at Mark.

"Good now you're going to press your head into the couch and arch your back."

My head had rested against the pillow as my backside raised up.

"Perfect Maya, Perfect."

Sitting with my ass vulnerable i waited anxiously for Mark's next order. He began to walk towards me, his cock swinging side to side elegantly with every step.

"Now what you're going to do is pull that frilly thong to the side, reach both your hands back and spread that cute little hole of yours."

With my thong pulled aside i began to reach my hands back and slowly spread my ass. There was something embarrassing about presenting myself so easily to Mark but he easily washed away those thoughts.

"Mmmmm that's right, that's what good sluts do, they present their holes to their daddies on command."

Mark had placed his and on my ass and began to rub soothingly. As his hand wandered i felt his finger begin to prod my hole.

"Now Maya do you know what this is called?"

"My butthole..?" I answered nervously.

He smacked me bottom hard.

"No no, that's your boy pussy."

His hands wandered further to my little cock hidden behind the silk panties.

"Now what about this, what is this called?"

"M...my penis?"

Another hand came firmly across my butt, it began to sting but i longed for further punishment.

"No Maya, that's your boy clitty."

His hands wandered back to my asshole. He began to slide his finger inside as i shuddered in a mix of anxiety and anticipation.

"Now this should be an easy one Maya, who does this hole belong to?"

"Y...you daddy?"

A much gentler smack had come across my backside.

"That's right sweetie, i knew you'd get that one." Mark chimed devilishly.

Mark had studied my backside intently, gazing at me up and down before he had dropped to his knees. His face moved closer and i could feel the warmth of his breath tantalizing my butthole. I waited anxiously and i think Mark knew that as he proceeded to tease me, breath after breath greeting my quivering hole.

Finally i felt a wet sensation followed by a prodding. Mark had began to run his tongue along every crease of my anus. The feeling was overwhelming, i had never felt something so good in my entire life. Every flick of his tongue exploring every inch of my tight little boy pussy. Mark's tongue went back and forth, swirled around and finally he began to push it inside of me. At first my butt had tightened up and my body froze but soon enough i was able to relax into it. Mark's tongue moved in and out of me, thoroughly tasting around my insides. It was euphoric, i had never felt this brain fogged in my life, i was truly experiencing what they call "cum brain".

After what felt like an eternity Mark had pulled his mouth away from my backside and i felt a long strand of saliva that still connected our orifices together. I had then felt something massive press against my tight little ring. I looked behind me to see Mark positioned, holding his cock and directing it towards my ass. This was it, what i had always dreamt about, it was finally coming true. Before Mark had started he leaned in and whispered softly in my ear.

"Are you ready for me baby?"

"Y...yes."

"Are you sure?"

"Yes! i want to feel every inch of you inside my body!"

"That's my girl" Mark had commented reassuringly.

With Mark's throbbing cock in position to ravage my tight hole, he began to press his hips forward. My body resisted at first but soon enough the tip of Mark's head had breached my defenses, my body was in shock. I was being stretched beyond what i thought was humanly possible, the pain was intense, but I knew I had to bare through it, for Mark. Soon enough his entire head had entered my hole and i could feel his head throbbing against my tight muscle. I grit my teeth and continued to allow Mark's glorious appendage in to my sacred hole.

As he slowly pushed forward he continued to ask me "is this okay" and i always nodded my head like the good girl he wanted me to be. Soon enough i had felt his beautiful balls nestle gently against my ass. He was all the way inside me. That moment brought a great amount of pride, I had fully accepted Mark into my body. With his cock buried inside my ass he paused for a moment and began to speak.

"Now i want you to commit to this moment Zack."

Using the name Zack had left me confused and a little sad, he had been calling me Maya for the entire night.

"This is going to be the most important moment of your life because these are your final moments as a boy, as Zack. With every thrust of my cock you will lose more and more masculinity until you are truly a girl, Zack will cease to exist and Maya will take his place, do you understand?"

I nodded my head

"Now are you sure you want to go through with this?"

"More than anything." I purred seductively, biting my lip.

"Alright then sweetheart, it's time for your final transformation from regular caterpillar to beautiful butterfly."

With that Mark had begun to slide his penis out of me, The pain still remained but there was a tinge of pleasure on the way out. Slowly Mark had pressed his cock back inside me, then back out, then back in. He was right, i could feel the masculinity melting away, like a caterpillar shedding its cocoon. His strokes became faster and harder. Every thrust of his magnificent cock had lifted weight off my shoulders, the weight of being a man, the weight of being masculine, I felt as though i could finally just let it all wash away and embrace true self. His cock continued to pound inside me and i felt my transformation to womanhood almost complete. As he ravaged my insides his head prodded furiously against my prostate. I was almost ready to soil these beautiful panties he had gifted me. As my insides burned with lust and my cock grew harder Mark had once again brought his lips to my ear.

"Alright sweetheart we're almost there, this is the most important part. Once i cum inside you this is no longer a butthole but a fully fledged boy womb. I am going to fill you up and when i do you are going to be a woman, my woman, when my seed fills your womb you will cum and that will signify your final step into womanhood, are you ready?"

"Yes! Yes! please fill me up, make me yours, i want all your babies inside my boy womb!"

With that sentence Mark's cock had exploded inside me. His seed had flooded my womb and i was sent into a state of euphoria. As his cock sprayed stream after stream of hot semen into my body my senses were overloaded and my cock began to squirt pitifully inside my panties. When Mark's cock had made its final pulse he collapsed on top of me, his warm glistening chest rested perfectly atop my smooth back. We laid there for a few minutes and once Mark had finally regained his composure he had began to remove his still hard cock from my backside. Once removed his cum had began to flow out of me, streaming down my silk stockings. The feeling of Mark's cum all over my body filled me with a warm sensation. I had collapsed on the couch like a ragdoll, totally exhausted from my transformation. With cum still leaking down my legs Mark had curled up beside me and caressed me in his big strong arms. I had fallen asleep instantly in the warm embrace of his comforting arms.

The next day i had awoken alone, confused i searched around the house for Mark but there was no sign of him. Finally by the front door there was a box and a note.

'This should make it easier on your way home.'

Inside were some generic male clothes. I was upset because all the talk me and Mark had made of my final transformation and he leaves me clothes for a boy. I thought on it and understood he was right, there were still certain appearances that Zack had to make.

When i arrived home i was shocked to see Mark sitting with my father at our dinner table having coffee.

"Zack where have you been all night?" My father inquired.

"Probably out on a hot date." Mark had said with a cheeky grin, winking at me.

"Speaking of hot dates, my goodness Zack you should have seen Mark's last night, what a smoke show! you should really take some pointers from him son, Mark's got a lot to teach."

"Oh I can only imagine." I said while grinning at Mark.

As i made my way to my room i could only imagine what the future had in store for me, i never could have dreamed that this would be the outcome of Mark finding me in lingerie but i could only smile to myself on how well it turned out.

As the years passed i became more and more comfortable with myself as a woman. After a year i had finally came out to my parents and although there was pushback at first, they had both accepted me for who i truly was. Mark had moved away to the coast, i decided to go with him. We have a happy comfortable life and a more than adequate sex life. Every day Mark fills my womb with his sweet seed after a more than satisfying pounding of my boy-pussy.

Thank you for reading! as always comments and critiques are always appreciated!