Virginity story: From Jack to Jacquie. Author: newpublisher2010. Hi. It has been a few years since I published anything so thought it was time to try again. Thanks for keeping my earlier stories so high in the rankings and for all your comments. If your not into transgender stories you would better to skip this one. The story is including Fiction, Anal, Body modification, Boy, First Time, Masturbation, Oral Sex, Transgendered, Virginity theme.
Virginity story: From Jack to Jacquie – Part 1
Author: newpublisher2010
Background.
My name is Jacqui. It hasn’t always been that, I was christened John but for some reason was called Jack or Jacky since I was a toddler. I am 18 years old and I live on the Northern Beaches in Sydney Australia. I haven’t always lived here and this is a rather long story, I’ll try to keep it short.
The house I lived in most of my life with my Sister Mia, my Mother and Grandmother was built by my Great Grandfather in the 1940’s on land he was granted as a WW2 veteran. Back then the northern Beaches was considered remote and there were mainly fishing shacks and weekenders up here. These days the houses sell for millions of dollars. Nan is always fending off developers and real-estate people who want our land.
The next generation to live here was my Nan and Grandpa Nan was born in the main bedroom in 1951 and has lived here all her life, she says she will leave in a box. My Mother and Uncle were the next generation Gran says Mom was a 21st birthday gift in 1972.
My sister and I break the tradition we were both born in Bangkok, Thailand. I won’t go into the detail here. Just to set the scene Mom is a nurse and was working on a humanitarian mission when she met, fell in love with and married my Father. Dad was a Thai doctor also doing humanitarian work. Mia was born in 1996 and me a year later. When I was just 3 may Dad was killed in some sort of military incident. Mom was heartbroken, returned to Australia and raised us girls alone.
The Early Years John/Jack
Growing up in a quite beachside suburb was pretty uneventful. Mia being 4 when we got back to Australia had a bit of a hard time with English as she was already speaking fluent Thai. Apparently I just went from learning to speak one new language to another one hardly noticing the change. I think Mia is the lucky one as she has kept up with Thai so is bilingual.
Our house is only one row of houses from the beach. Next door, facing the ocean is a modern family home 2 or 3 times the size of ours. This is where my best friend Josh comes into the story. Josh is a year and a half older than Mia.
Despite the age difference Josh and I became close friends. When I turned 5 and it was time to head off to school he was also like my big brother. Being mixed Anglo/Asian Mia and I were “different” so we came in for some unwanted attention and bullying. Josh stepped in and threatened to break the nose of anyone who picked on his kid sister and brother. He then became my hero as well.
As we grew Josh was always the tall, strong, athletic one. He played football, swam on the school and state team and was always winning trophies for some new achievement. The one sporting thing we had in common was surfing and it drove Josh nuts that I was actually as good as and sometimes better than he was.
I’m jumping ahead a bit so back to primary school, Josh was first to move on to high school leaving Mia and I to fend for ourselves but by that time the other kids had forgotten that we were different and had found something else to waste their time on. The last year at primary school was the worst as I found myself without my big Sis and my best mate.
We would still walk to and from school together and hang out on the weekends. Mia started to hang out with her new girlfriend more often so Josh and I had more time alone.
In summer we would spend our time at the beach or if the surf was bad we would just hang by their backyard pool. In winter we only hit the surf if the waves were really good and spent most of our spare time surfing the Net instead.
Transformation 1, Josh and Jacky.
Half way through my 12th year things started to change. It was the winter school holidays, which is July down here in the southern hemisphere. We would only surf if the waves were really good because the water was freezing. After one cold surfing session Josh and I were back in the change room. We pulled off our wet suits and board shorts ready to hit the shower.
Josh looked and me and said “look Jacky’s back” looking down I saw what he meant. The cold water had caused my genitals to shrink, my scrotum had pulled my balls up so tight they were gone and my little cock had shrivelled so much that it was just a tiny nub with my foreskin looking like a little slit. We both laughed and headed for the hot showers.
When we came out I was back to normal. Normal for me was small anyway. When limp I’m 2 inches and hard is not much different but I was only 12 after all. Josh on the other hand was going on 15 and puberty had changed him dramatically. His chest was broader, his voice changed, body and facial hair was starting to appear and most impressive his balls swing lower his cock had grown to about 6 inches and 3 times the thickness of mine.
A couple of days later the wind was blowing onshore and messing up the surf so we decided we would take a swim at home. We were alone and Josh’s back yard is completely private so we decided to skinny-dip. The pool was only slightly warmer than the ocean so we didn’t stay in long. It was a clear sunny day and we thought the sun would warm us up a bit.
Josh spread his beach towel on the grass. He was lying down on his back with his hands behind his head. Something weird in me said “wow he looks Hot”. While I was wondering where that thought came from he patted the grass beside him and said “Hey Jacky, come and warm up”. I didn’t need to look to see why he called me Jacky, I was shivering.
I spread my towel next to Josh and lay beside him on my side, admiring his new physique. As I shivered Josh put an arm around me and pulled me to his chest, I made no attempt to resist and snuggled into his strong body. Lying on his chest the way I was meant that I was looking towards his feet. As I watched, fascinated, his cock began to harden.
It was lying against his stomach almost looking back at me. I took my right hand from my side and let my index finger trace along the underside. It immediately jumped and Josh let out a loud breath. I let my fingers wrap around the hard shaft and marveled at how different it felt to my own. Josh rocked his hips and his hard cock slid in my fingers, it felt much warmer than I expected, it felt….well….nice. I started stroking up and down, slowly at first, then Josh started pumping his hips faster so I matched his pace.
It was only a couple of minutes before his movements were becoming more erratic, his breathing hard moaning louder. A few more strokes and he gasp “Fuck Jacky I’m going to cum”. I should have known what to expect but when I masturbated all my orgasm produced was a little squirt and a few dribbles of clear fluid. Josh went off like a fountain.
The first rope went up in the air about 18 inches and splattered on my face the second under my chin the next 2 or 3 across his stomach and a series of after eruptions trickled down his cock and coated my fingers. While I was lying there contemplating what I had just done and the consequences I felt Josh starting to chuckle under me.
He whispered in a slightly shaky voice “Holly shit Jacky that was fucking amazing”. I turned to look at him and he saw where his first 2 loads had landed. By that time it was trickling down my face to my mouth, looking him in the eyes I licked my lips and swallowed. It tasted…..well…..nice. Josh scooped another blob of my nose and held it to my lips. I sucked his fingers clean. Josh then pulled me on top of him and up his body, our lips met and we kissed passionately. His tongue traced my cum coated lips before pushing into my mouth.
I was sucking gently, our tongues danced and twirled and it was my turn to rock my hips against his hard abbs and softening cock. Josh was still slick from his stomach shots and I slid smoothly against him until my own, somewhat less spectacular orgasm. We lay there for a while in the afterglow, kissing and holding each other. Josh stood up pulled me to my feet and lead me by the hand to the outdoor shower. The hot water felt wonderful and josh gently washed me then grabbed a big fluffy towel and patted me dry. I was tingling all over. The next day was Saturday Josh and his parents had gone to visit his grandmother at a retirement village about an hour north and I wouldn’t see him all weekend.
On Monday morning I saw Josh drive off with his mother on her way to work and my heart sank. I thought I had ruined the best friendship I had ever had and that Josh probably hated me for what I had done. It was over an hour later, I was still sitting on my bed with my phone in my hand trying to think of what to put into a text to Josh when a cab pulled into his drive. He jumped out. I almost jumped off the bed when my phone rang in my hand and I saw Josh’s name. I held the phone to my ear but no words came to mind then Josh said “hey babe it’s me. Where are you”. Hearing him call me Babe made my heart jumped and pound in my chest. I managed to get out “At home” he said “well get over here fast I have got something for you”.
Years ago Josh’s dad had taken some paneling out of the fence between the 2 yards so we could easily get to each other’s homes. I raced out the back through the gateway and in the back door. Josh was standing there with a silly grin on his face “what took you so long”. I rushed to him and he swept me into his arm and kissed me deeply. Tears trickled down my cheeks and I whispered “I thought you hated me” he held me back and looked at me “God Jacky I have been thinking about you all weekend” I snuggled into his chest and whispered “I missed you Josh”. He kissed the tears from my eyes and handed me a small package.
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