From Jack to Jacquie – by newpublisher2010

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.

“What is it” I asked. “Look inside an see” he laughed. I opened the bag and slipped my hand inside, soft fabric met my touch. I could hardly believe my eyes when in realised I was holding a tiny white bikini. “Well” he said “put it on”. “I have been thinking about this since Friday”. I quickly slipped out of my T shirt and jeans standing in my underwear I suddenly fell so nervous I couldn’t move.

Josh slipped his fingers into my shorts and slipped them down so I could step out of them. He handed me the bottoms and I stepped into them sliding them up my legs and wriggling to get them on. The tiny triangle barely covered me but I adjusted them a little and Josh nodded in approval. The top was just as small. I slipped it over my head and turned for Josh to tie the little strings at the back. I stepped back and span around to give him a better look. I guess he liked what he saw because he was tenting the front of his pants.

He took me by the hand and led me up to his room where he has mirrors on his closet doors. I stood looking at myself and a whole new feeling of awareness swept over me. Josh was still grinning from ear to ear. “Well do you like them” I pulled him down to my lips and kissed him “God yes babe I love them’. “I feel so…..well…..sexy”.

“Josh, where can I were them?” I asked. He smiled and said “any time we are alone and any time we go somewhere where no one knows us.”

I then asked where he got the idea of buying me a bikini. He blushed and said “if you promise not to tell anyone I will show you” I promised and Josh went to his computer. I followed and sat beside him. He went to his browser and clicked on a link in his favorites. What came up next was a beautiful young Thai girl, she looked a lot like Mia. As she swayed in front of her mirror she slowly stripped out of her shirt and then her bra.

Her hands covered her chest but slowly she let them fall to hers sides to reveal her perfect breasts they were paler than the rest of her skin as she had tan marks from a very small bikini. I looked at Josh and asked “have you been up here masturbating to my big sister” he blushed and answered “maybe” I was somewhere between angry and jealous but he said “watch”. The girl on the screen was wriggling her but at us and reached behind to undo her skirt. She let it slip down her shapely legs and stepped out of it.

Now the only thing she had on was a tiny pair of panties as she slowly slipped them off I watched her gorgeous arse and could kinda understand how Josh could think of Mia and jerk his big cock for her. The girl on the screen turned to face us. She had her hands covering her pussy. As she swayed she let them fall back to her sides. What I was now looking at almost took my breath away. Instead of her pussy I was looking at her cock. She was bigger than me but smaller than Josh and she looked stunning. Josh had his arm around my shoulders and squeezed me closer. It slowly dawned on me that it wasn’t Mia Josh had been wanking to. It was me.

Then Josh picked me up and carried me to his bed. He lay down beside me and stated to kiss me all over. When he got to my nipples he slipped the tiny triangles aside and licked and sucked them. I’m amazed how sensitive my nipples are. They were instantly hard and his tongue and lips felt amazing. He then kissed down to my navel and repeated his attention.

My little cock was straining at my bikini bottoms but not escaping. When Josh kissed down my stomach to my mound I thought I was going to pass out. He kissed me through the soft material then slipped it aside letting my rock hard little cock spring out at him. “My what a big clitty you have” I closed my eyes and felt his tongue on the tip.

He swirled it round before taking me into his mouth. Because I’m so tiny he could take all of me into his mouth with no problem. It felt so good I couldn’t help rocking my hips into his face and in less than a minute I knew I couldn’t hold out much longer. I told him to stop because I was about to cum but he just sucked harder and swirled his tongue faster until I squirted my little load into his mouth. I was still panting when he came up and kissed me deeply, I could taste myself in his mouth.

The sun was now almost at its’ peak in the winter sky so we made our way out into the yard and lay down in the sun. Josh slipped out of the clothes he was wearing but I kept my beautiful new suit on. We talked for ages just soaking up the warmth and loving each other’s company. In a way it was the way we had always been but now with a whole new depth. Josh chuckled.

I looked to see what he thought was so funny “what” I asked “you are going to look so hot with tan lines” he replied. I slapped him on the arse and giggled. That was strange I thought, I haven’t giggled since I was 5. “I mean it” he said, “when the spring gets here we are going to spend time in the sun until you have them”.

Josh was as hard as a rock. I guess the thought of my tan lines was turning him on. I moved over him and copied everything he had done to me earlier in the day. When I reached his cock there was a glistening bead of pre cum on the tip. I slipped my tongue out and licked it off. It was immediately replaced with another.

As I ran my tongue around the head of his shaft I wondered how much if any of it I could get into my mouth. I stretched my lips and pressed down. About an inch slipped in and I bobbed my head and twirled my tongue the way Josh had. Josh groaned and pumped and slowly more and more of his manhood sipped into my mouth. There was about 2 inches that I couldn’t manage.

When it touched the back of my throat I gagged and I had to pull back. I sucked and bobbed and Josh whispered how good it felt. He began to spasm and I gently squeezed his balls. “Oh Fuck Jacky I’m going to cum babe”. I thought I was prepared this time but the first rope filled my mouth and dribbled down my chin before I could swallow.

The second came as Josh rocked his hips up, I bobbed my head down. I swallowed his first load. The combined effect was that my nose was against his balls and he came in my throat without any gag reflex. I took the next the same way then pulled back to let him fill my mouth. I was now swallowing as fast as he was pumping his cum into me. As his ejaculations came to a stop I slipped down and swallowed hard. He was in my throat again. I had discovered how to deep throat him by accident. I tightened my lips around the base of his shaft and sucked my way to the top milking him for every last precious drop.

Mia and her friend Megan were home the next day so Josh and Jack had to behave as they always had, although more than once I saw Josh looking at me in ways he never had before. Wednesday was raining. Mia and Megs asked if we wanted to take in a movie, we declined. By the time they were out of the street we were back in Josh’s room and he was undressing me and laying me on his bed. He was soon naked and joining me.

We kissed and writhed against each other, both as hard as we could ever be. Josh reached into his bedside table and retrieved a tube of lube. He spread some on his cock and my hand and I stroked him gently. Then Josh lubed up his fingers and slipped them to my virgin hole. I tensed up at his touch. He rubbed gently with soft circular motions until I relaxed again.

I concentrated on his wonderful cock while he continued to stimulate me. Soon I felt his fingertip slide into me. It felt…..well……nice. While he finger fucked me I rocked up to him and stroked him. He moved up and kissed me deeply and whispered “are you ready babe” I nodded “I think so”. “Be gentle honey”. He moved back down between my legs and began to massage me with the tip of his cock. I think his pre cum was making me even more slippery. I felt myself being opened for the first time. I held my breath.

Suddenly the tip of my lovers cock popped through and I screamed. Josh stopped immediately while I panted under him. I tried to get myself under control. I thought I would split in two. Slowly I relaxed and the pain started to subside. “Wow, I guess I’m not a virgin anymore”. I smiled and moved a little. Josh stayed still and let me make the moves.

Soon I was able to move easily enough on his shaft and whispered “now fuck your little girl”. Slowly Josh started to slide back and forward getting a little deeper with each forward thrust. The pain quickly changed to pleasure and I was rocking up to meet each move. After a few minutes we were both breathing hard. Josh was fucking me like there was no tomorrow and I knew I was going to cum. I wrapped my legs around him and pulled him into me and came harder than I ever had before. I think my muscle spasm around him pulled him over the edge because he thrust balls deep and erupted deep inside me.

The rest of winter was much of the same. Every chance we got to be alone we would lie in the sun and make love. Some weekends I would sleep over at Josh’s house and we would sleep together. We would always make the spare bed look like it had been slept in so nobody would get suspicious.

Our next school break was late September. I had already developed a very faint tan line but now that it was spring Josh was determined to work on it more. Instead of heading off to the surf beach each day we would sometimes catch a bus to Manly and find a quiet spot on the harbor side beach where we were sure nobody we knew would find us. I soon found that wearing my Bikini on a public beach was a huge turn on for both of us. Needless to say Josh soon got his way and I had very distinct bikini marks. Sometime our lovemaking after a day at the beach was so intense I’d find myself at the point of blacking out.

Transformation 2, Mia, Megan and Jackie.

It was a Saturday morning in mid November, Josh was away with his parents visiting his Grandmother. Mom and Nan were out shopping. Mia and I were at home alone.

As I walked past her bedroom on the way to the kitchen I looked in. She was sitting at her dressing table painting her nails. I stopped to watch. She was only wearing her panties. That was unusual as she was pretty shy around me. She looked up and smiled then said “Hello little sister, do you want me to do your nails for you”.

I had knots in my stomach. Did she know? I had been letting my nails and hair grow and they were both getting fairly long. I shrugged and said “yes, I guess so”. Mia patted the bed beside her and I walked in and sat down. She took my hand and looking at my nails said “you have a lot to learn about being a girl Jackie”. I guess I was bright red because she squeezed my hand and said “ssssshh it is ok. I know”. I thought there was no point denying it so I just asked “How”. Mia explained that she could seem me becoming more feminine over the months, even my giggle. She said that the way Josh and I were when we were together was a dead giveaway. Then she giggled and said “and I got a glimpse of your tan lines the other morning. “Show me”.

I lifted my top over my head and propped it on her bed. “Wow how cute sis”. “Now the bottoms”. I slipped out of my shorts and spun around slowly. I was kind of proud of my naked body but admitted that I’d much rather have hers. Her hips were curved. Her breasts were beautiful, not big but a wonderful shape that looked so good on her that I wanted to touch them.

I reached out and cupped one in my hand. It felt…. well…..awesome. “That’s enough of that” she smiled and passed me a pair of pale blue lace panties to put on. Then she started to work on my nails. First the cuticles were pushed back then the tops buffed and finally the emery board to shape them. It had taken ages but they looked amazing and during the process I had confided everything from the past 4 months.

Mia just kissed me softly on the lips and said “I always knew I had a little sister. I have been waiting for you to come back”. “Now what color do you want”. I looked at hers, they were bright red so I asked for the same. As she painted my nails she recalled how we had played together when we were little and how I preferred her dolls to my cars and trucks. She reminded that when we played I always was the Mommy not the Daddy. I smiled and thought – big sisters know everything.

After the nails were done we went to the kitchen for toast and fruit juice. It felt nice walking about with my big sister in just our panties. I suspected my were a little damp and wondered if hers were too. After breakfast we went back to her room and she sat me in front of the mirror where she had been sitting. “Makeup” she said. We went through lipstick, blusher eye liner Mascara and a whole lot of other things I had no idea about. After the first attempt we fell into each other’s arms in fits of giggles. Mia looked at me and said “pretty good…. If you are looking for the clown look. I wasn’t” I then learnt the secrets of makeup removal and stated again. By the fourth attempt Mia admitted that I looked “Hot”. I felt…..well……Hot.

We were sitting there comparing our makeup when I heard the back door. Panic set in, I guessed Mom and Nan were home, I was in Mia’s room wearing nothing but panties, bright red nail polish and makeup. Mia put her hand on my arm and said “it’s ok that will be Megs” Meg’s is Mia’s best friend Megan, everyone except her dad calls her Megs.

I was still in a panic until Mia said “she knows too” I relaxed just a little and held my breath until Megs arrived at the door. Her face broke into a huge smile and she said “YES twins at last”. She swept over to Mia and they kissed. Mmmm that seemed a little more than a friendly kiss I thought. Before that thought had time to sink in Megs was turning me each and every way to get a look. Finally she stopped and stepped away. Mia looked at her and asked “well what do you think” Megs gave a very serious look and responded “not a bad start’. ‘Let’s shop”.

Megan is the only child of a famous Sydney doctor and is spoilt rotten. Mia and I met Megs through Mom’s work.

“Ok” Megs declared “let’s get dressed and hit the shops” I went to pull my T shirt back on but she grabbed it from my hands and threw it away. “Not Jack’s clothes silly” I just smiled and admitted that “the bikini is the only thing that Jackie owns”. Mia and Megs stepped to her closet and started pulling out clothes until they had selected my outfit. I was wearing short white skirt and little pink top leaving me with bare midriff and lots of bare leg. Mia found a pair of flat sandals to match and we were ready to go.

We got to the mall and the first place we went to was the hairdresser. The staff obviously knew Mia and Megs and there were cuddles all round. They sat me in a chair and examined me like some sort of show animal. It was finally decided that my hair was to look as much like Mia’s as possible. For the next hour or more I was shampooed, snipped clipped, combed, and generally groomed to within an inch of my life. When they were finally done I stood beside Mia at the mirror.

I thought it was a trick. There were 2 of Mia’s reflections and none of mine I reached up and touched my hair and the reflection did the same I was ……
well…… shocked. Just then Megs came bounding back in. Took a look and declared “much better”. “Let’s shop”. Meg’s paid the bill and we moved back out into the mall.

Also in this series:

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