Nicky Bliss (A Shemale’s Journey)

Nicky Bliss (A Shemale’s Journey)
A tribute to the most beautiful creatures and most perfect humans that ever walked the earth.

My name is Nicky Bliss. I am a self-made millionaire and business woman. I don’t care for the money so much but I care very much for the industries that have earned it for me. You see by day I am a model of fine women’s clothing and by night I work as an exotic escort mostly to very wealthy clientele. It has not always been this way, I come from very humble beginnings which I will tell throughout my story but I have always been fascinated by the human body and from a very early age I have adored sex.

I was Born Nicklaus Shtick to father Berndt and mother Kira. I was born in the United States the year after they migrated from Germany. I don’t know exactly where as they have always refused to discuss it. My father was a high school Phys Ed teacher and my mother was a dancer trying hard to break into the big time. I enjoyed a fantastic relationship with my mother early on but I felt like an interruption to my father’s plans right from the start I guess.

The real story begins when I was 5 years old. My mom and Dad were hosting a fancy dress party for New Year’s Eve. There were around 50 guests crammed into our modest home and yard and they had not even stopped arriving yet. It was around 8 o’clock and mom had forgotten to put me to bed. I didn’t mind though, I was having fun snooping around in the background taking in all the sights and smells without being noticed. There was one other child there who I had started playing hide and seek with, only I had been hiding in the same spot in my parents’ bedroom cupboard for close to 40 minutes now and had figured he had fallen asleep. I was just about to step out when the bedroom door opened. Excited I quickly pulled back into the cupboard and pulled the door closed again ready for Edmund to find me.

Then I heard the door close and heard some strange noises began. There was heavy breathing and someone changing their clothes or something. Curiosity got the better of me and I opened the door just enough for me to see out. I saw a man from my mom’s dance school and mom was kneeling in front of him. We were not religious people at all and even if we were why would she be praying here in her bedroom in front of this man. The man now closed his eyes but instead of words of prayer I heard sucking noises. I opened the cupboard just a little more and could now see the front of my mom in the reflection from the mirror. She was putting the man’s penis between her lips and then sucking on his penis. She licked it like a lollipop and sucked it some more. I was amazed at the size of the man’s penis. It was so big, so long and so round. It fit just perfectly in mom’s mouth. She looked so hungry for it, like it was the best tasting lollipop in the world and he enjoyed it so much that is until some white cream came out of the end. He grunted a few times like it hurt a bit and then smiled a huge smile. My mom licked the cream and rose from her knees and they both went back to the party. Edmund never did come looking for me and I never forgot what I saw from that cupboard, it was to me the most beautiful thing I had ever seen.

When I was 7 years old I found some clips on my Dad’s computer of himself and some of his students at school. There was a little bit of talk about sex by then amongst the kids in my year level so I kind of knew what I was looking at. He was sucking their small boobs and licking between their legs and of course they were putting his penis in their mouths. The girls were so pretty, I wanted to grow up pretty, and they sucked my dad’s penis so nicely. I hoped that my penis wouldn’t always be small and looked forward to pretty girls like that sucking it. There was something about those girls or pretty women in general that I adored and began to long for even at that young age. I convinced my mom to let me grow my hair longer and I started mucking around from time to time dressing in girls clothes. My friends at school were all girls and I had a couple of good friends that would love to have sleepovers and dress me up and stuff, it was our little secret. We got so good at it that one day the girls dressed me up and their mom did not recognise me and asked them to introduce me. It was so funny and even funnier when I left and said goodbye and Mrs Wilson (Lucy’s Mom) said

“Oh goodbye Nicky I didn’t even know you were here”

My Dad found me one day at home dressed up and went berserk. He had predicted I would grow up ‘queer’ from early on and blamed my mom and her ‘gay dancer friends’ for it. Mom was able to convince him it was for a school play or perhaps not convince him but give him a lie that he could live with. He made me cut my hair though and I was completely devastated. My friends Lucy and Melinda were good to me and managed to find some wigs for me to use at our ‘dress up’ parties that were really very ordinary but at that age it was enough.

When we were around 11 our interests started changing. We talked about sex and were very curious about the topic and decided to do some experimenting. One night at a dress up party the girls suggested we all take off our tops, so we did. They had both started to form cute little breasts, I knew this as it was visible in their clothing, but to see them naked immediately made my dick hard. All of a sudden I felt awkward, like a knife had been plunged into my stomach. I was so jealous of their breasts and their changing bodies. Lucy noticed and tried to comfort me

“Oh Nicky, you are beautiful. We love how you look and well… think of the advantages” She said looking at the bulge in my skirt.

“Would you like to feel them?” Melinda added

“I would love to, I guess. I mean, sure”

I touched a nipple each of the girls with the palm of my hand softly making them gasp. I began to squeeze and roll them around in my hands. They were incredible; they were all I had dreamt of. I spent a long time just rubbing and kissing them. When I stopped I looked at my own flat chest and then at theirs and began to cry.

“Aw Nicky look at the bright side, if you had boobs you wouldn’t have that gorgeous dick sticking up under your skirt” Melinda said.

It was the perfect thing to say. Reading each other’s minds we all shed the rest of our clothes and sat staring for a few minutes. They had very cute little pussies, all tight with a little tuft of pubic hair. I wanted to lick them as I had seen on Dad’s movies.

“C can we touch it? Lucy gasped looking at my dick

“Um…ok” I replied

By this stage in life I had played with it plenty and had even made myself orgasm but the feeling of someone else caressing it so softly felt amazing. First Lucy stroked it and rubbed it and then Melinda had a turn. My eyes rolled back in my head and I just wanted to die in that perfect moment. Just then I felt it coming and wanted to warn the girls but could not think of how.

“look out” i managed to scream.

Despite the warning my cum went all over the girls hands and a little on Lucy’s tummy. There was a knock at the door.

“Everything ok in there?”

“Fine mum we are just playing” Lucy yelled.

We fell over the floor laughing and decided that was enough for today so we all dressed and I went home. I had the most wonderful and emotional time but something still did not seem right. The feeling of someone else playing with my dick was incredible and had made me happier to be male for now. I went to bed that night with a warm feeling in my stomach remembering the girl’s soft hands on my penis and the taste and smell and feel of their soft delicious boobs. I very much looked forward to our next time and hoped I would dream about it as I drifted off to sleep.

The next time I was with the girls we jumped straight in and took things to the next level. I licked and sucked the girls’ pussies one at a time while the other sucked my penis. They tasted so delicious and I couldn’t get enough of exploring the depths of their vaginas. Lucy’s mouth around my cock was so wonderful that I accidentally came and filled her mouth. She choked and spat it out onto my stomach and then took me by surprise as she put her finger in it and tasted it.

“Hmm, not too bad, a little salty but I like it” she beamed.

Melinda bent forward and gave a big lick and just watching her made me want a cock of my own to suck. I loved the way the girls moved up and down on my hard dick, my dick was warm and slippery inside their mouth and their tongues danced around the surface of my cock driving me wild.

It was a couple of years later, on a hot summer night that I crawled out of bed in the middle of the night to get a drink to quench my raging thirst. I was just finishing up in the kitchen when I heard some noises coming from the lounge room. I peered around the overhead cupboards convinced I would see someone having sex. I was right; two of my Mom’s male friends Carlo and Mark were at it, one giving the other a blowjob. I had never seen anything like this in real life only on the net. I stood silently watching only a little surprised but quite intrigued and a little horny. I began daydreaming about myself being the one receiving the blowjob from both of these strong athletic men. I was quickly snapped out of my dream by one of them calling out to me

“Come over here Nicky”

I froze and looked away considering running to my room.

“Don’t be scared, come and sit with us”

With my heart pumping almost out of my chest I went and stood in front of them

“Why were you watching us Nicky?” Carlo asked patting the seat next to him.

“I um…well you…” nothing brilliant came to me.

“You liked it? Is that what you’re trying to say?”

“Uh… yeah” I answered nervously

“Would you like to try it Nicky?” Mark asked backing away from Carlos to let me in

“Oh wow, um ok” Prehistoric sized butterflies were going nuts in my stomach as I knelt before Carlo.

First I reached out nervously and grabbed his cock in my hand and jerked it nervously.

“Easy Nicky, like this” Carlo said grabbing Mark’s cock and stroking up and down a few times.

Mark moved closer in beside us.

“Now watch” Carlo said

He put the end of Mark’s cock to his lips and ran his tongue up the slit in the middle and then swallowed his entire cock. He closed his eyes and started sliding back and forth and rotating his head a little. I wasted no time and tried to mirror his actions on his own cock. I felt a little clumsy at first and then got lost in another dream except this time I was me but I was female. I stopped suddenly and gasped at the picture in my mind.

“You’re ok Nicky, you’re doing fine” Carlo said

“I was a woman” I gasped

“Uh…what?” Mark said

“I was daydreaming and I was a woman” I clumsily tried to explain

“What like a different woman or a shemale or something?” Mark asked

“Huh? Shemale?” I asked looking for clarification

“A chick with a dick, have you never seen one you little perv?” Mark said insensitively

“Mark, take it easy “Carlo said. “A man who has basically become a woman through surgery and treatment but still has a penis” Carlo explained

“Wow that sounds weird” I giggled

“Enough talking” Carlo said rubbing my cheek.

I resumed licking and sucking his cock briefly before my Dad burst in.

“Out of my house, fucking fags. Nicky… what the fuck are you doing. You are a disgrace”

“Easy, easy” Carlo said getting dressed

“I’ll kill you, you little poof” Dad said grabbing my arm and nearly twisting out of the socket.

Mark went to restrain him but Dad hit him hard in the face sending him crashing across a sofa. Carlo dropped Dad with a blow right between the eyes. Dad raised his head looked at me and said

“Get out the lot of you; you fucking queers are not welcome in my home”

By this time I was bawling.

“Come on kid, we will get this sorted” Carlo said reassuringly.

I left and stayed with them that night but did not sleep at all. I just wanted to be home with my Mom. I think I cried myself empty that night.

My Mom rocked up the following morning with suitcase in hand. She had left Dad and it was no real surprise to me. They had never been real passionate, or at least not with each other. After thanking the boys for looking after me we had a real good talk and mom assured me that whatever I went through in life she would be there to support me. This was good because I was a mass of confusion at this point but one thing stood out in my head, the term shemale. I knew I had to look into this. I had looked at plenty of porn on the net but I did not remember seeing any ‘chicks with dicks’ and it intrigued me.

For the time being we decided to stay with Carlo and Mark and Mom had her friend move into her room with her. Mom and Bianca had been friends for a long time, since they were in high school actually. I always thought it was funny actually, that Mom and Bianca were best friends but they didn’t have any pictures or anything. I mean, she must have been homecoming queen or something; she was the most beautiful woman I had ever seen. I had always had a huge crush on her and now that I knew Mom and her were sharing a bed I was a little jealous myself. Dad hated her. For some reason he seemed jealous and pretended to be nice but Mom and I knew deep down he hated her.

One night Mom had a performance that restrictions stopped me from attending and she was stuck for a baby sitter. Bianca volunteered although she had never missed a single show Mom had been in.

“I’m so sorry B” I said to her.

“Don’t be silly gorgeous, we’ll have a great time together”

“Did you really mean it” I asked nervously

“Um sure Hun, What would you like to do?”

“No not about the great time, you called me gorgeous”

“Baby you take after your Mom, how could you be anything other than gorgeous. Don’t you like the way you look?”

“Well sort of, I guess” I responded. Inside I wanted the conversation to go on but I was afraid of how I felt. I was completely messed up.

“You know I love you Nicky, If you would like to talk about anything I will do all I can to help” she offered.

I pulled out some old photo albums and dropped them on the table and sat down next to Bianca.

“You read my mind only I feel like we are missing something”

“What” I asked curiously, but she was already on the phone ordering pizza and munchies.

As we flipped through photos talking and laughing about Mom and her school days I started to explain or at least try to explain how I was feeling, which I did not really know if I knew myself.

“B I have a lot of secrets I think for someone my age.