From Jack to Jacquie – Part 2

Adult story Editor October 8, 2015 Leave a Comment

Virginity story: From Jack to Jacquie – Part 2

Now if you think the hair was a surprise to me it was nothing to the next stop. We were at the jewelers and standing at the end of the counter under a sign proclaiming “Ear Piercing”. I wanted to turn and run but Mia grabbed my elbow and turned me to the mirror. There were the 2 Mias looking out at us.

She showed me that one had pretty pierced ears and the other one looked plain. Surprisingly the process was completely painless. I came away with gold loops in my ears a tube of cream and instructions to keep turning them and not to take them out for at least 2 weeks. I looked in the mirror and thought I looked ….well…..cute. Like magic Megs reappeared and paid the bill.

Next stop was lingerie Megs stayed this time and picked out all sorts of sexy things for me. Then off to casual clothes for little skirts, shorts and tops and a new yellow bikini that I think is smaller than the one Josh bought me. Again Megs paid the bill and we moved on with my growing wardrobe. Next stop was shoes.

Pretty casual sandals with flat heels, some more dressy sandals with straps up my legs and shoes with a little heel. Then a pair of bright red dress shoes with high heels that I thought I’d never be able to walk in. Once again Megs paid for everything. We made our way over to the more formal ware section of the store and my two new girlfriends selected the perfect Little Black Dress for me. Then accessories to match a gold purse a gold chain for my throat.

By then we were all starving so we went to get food and drinks in the food hall. We chatted girl talk about our shopping and about what we had planned for the next weeks. I felt more at home than I had in my life. I also felt sad that Josh wasn’t here with us. When I told the girls I was missing him, they reminded me that he would be home tonight.

Mia burst into laughter for no apparent reason and Megs and I sat waiting to hear the joke. “No joke” she said “I have just had the most brilliant idea of my life’. “Ok out with it” I said. She said nothing but picked up her phone and dialled. When the call answered I heard her say “Hi Josh its Mia”. “I have a huge favor to ask” we waited while he responded then she carried on “There is a dinner date with a few friends tonight and I don’t have anyone to take me”.” Would you be my date”.

Silence again while he replied. Then she hung up. Just as I was about to ask what that was all about my phone rang and I saw it was Josh calling me. I picked up and said “hi honey, are you missing me” he answered “yes always”. “But that’s not what I’m calling about”. He then told me everything Mia had just said and asked if I knew anything about it. I said I knew she was going out but didn’t know she was desperate and dateless. That got me a kick under the table. Josh was quiet and then asked “she wants me to ring back, what should I do”.

I tried to sound cross and asked if he wanted to date my big sister “ I could hear the pain in his voice as he denied it. He said “hell no. You know I love you. What should I do?” I waited, partly for effect and partly to stop myself from giggling then replied “Well she is desperate and dateless, I guess once wouldn’t hurt”. He asked if I was really sure so I replied “only once and keep your hands off her….and keep your cock out of her” Mia and Megs had to get up and move away and I had to bite my tongue. “Just kidding Josh baby”

I hung up and looked to Mia for an explanation. Mia was laughing so hard she couldn’t talk for a while then said “don’t you get it sis, your man will be meeting the new you not”. “How long do you think it will take him to find out it is not Mia he is with”. I was …..well…..speechless. Megs declared Mia the most devious woman in Australia if not the world then said we had to call in at her place on the way home. We caught a cab to her place waited while she ran inside then headed home.

What Megs had picked up at her place just wrapped up a day of surprises for me. She had a pair of soft silicone false breasts to wear under my new bras and when she pushed them on my chest they stayed in place because of their suction cup design. Mia cupped one and laughed “there you go sis almost as cute as mine” I laughed, admitted that they looked great but said “ real ones would be better”. Megs gave me a funny look.

The plan was to meet Josh at his place at 7 and then head off to the restaurant to meet the phantom diners. We spent the afternoon getting me ready for my first real date. The hardest thing was the shoes but by the time we heard the neighbors pull into the drive at 6 I had just about mastered them. The next hour was hell I must have begged Mia to go instead of me a dozen times before I headed out to the hole in the fence to meet my fate.

Rather than barge in through the back door as Jack would have done I knocked and waited. Josh’s mom saw me and called out “come in Mia darling, he will be down soon” I stepped inside and into the room. Josh’s dad let out a long whistle and said “what ever happened to that skinny girl next door” I smiled and replied “I guess she grew up a little” Josh’s Dad shook his head and said “He doesn’t deserve a date with a gorgeous little thing like you”. Just in time Josh appeared at the top of the stairs.

He looked great in black trousers and jacket with a white open neck shirt. He had even managed to get this curly blond hair under some semblance of control. He stood there looking at me and then said “Wow Mia you look great”. Josh’s dad offered to drive us to the restaurant. As he got the car out I took Josh’s hand and lead him out the front to meet his dad in the drive.

Josh and I got in the back seat and I snuggled up to him. He seemed a little uncomfortable. I leant in and whispered “what’s wrong handsome”. Josh whispered back “I promised my girlfriend that I wouldn’t touch you”. I whispered in his ear “it’s Jackie” he looked at me with a concerned look and replied “what about Jackie is she..

I mean he ok” I squeezed his hand and whispered “I am Jackie”. His mouth opened and closed a couple of times but no words cane out so I leant up and kissed him full on the lips. He put his arm around me and whispered in my ear “I want to kill you big sister for her trick but if she had anything to do with this transformation I will love her forever”. We kissed again and I saw Josh’s dad watching us in the mirror while the lights changed. I’m not sure but I think he reached down to adjust something in his pants.

We stepped out of the car and into the restaurant. A waiter led us back to a table for two in a nice quiet area. Josh said “where are the others babe” I giggled and told him it was just us. Josh slowly turned me around. The dress had a low V at the back to just above my bottom. It was less revealing at the front and the silicone breasts filled it out perfectly.

Josh brushed his fingers across my nipple and whispered “Mia?” I just smiled and said “sorry babe there not real” he leaned into my ear again and whispered “my erection is real I’m likely to cream my pants”. The waiter came to our table and Josh ordered a bottle of champagne when it was poured Josh raised his glass in a toast “to the most beautiful girl in the world.

We took a sip. I raised my glass again and said “to the luckiest girl in the world” our first course came and went and the band started playing soft music. A few people were on the dance floor so I grabbed Josh’s and said “Dance with me” he looked up at me in panic and said “I can’t”. We had often danced at home so I didn’t understand why he wouldn’t want to dance with me now.

He beckoned me down and whispered in my ear “I’m still as hard as a rock I can’t walk out there” I smiled and said “just follow me closely and it won’t show”. We made it to the dance floor. He held me close he was right about one thing he couldn’t get any harder. His cock was pushing up in his pants and threatening to break out as we swayed together.

The next song was very soft and slow I held Josh closer and swayed against his body even more. I could feel his cock against my stomach. I was loving it. Just before the end of the song I felt him go tense he nibbled my earlobe and groaned softly and I felt his orgasm surge through him. As the song ended I guided us towards the men’s room.

As we got there I whispered “go clean up, you bad boy” I made my way into the ladies to check my dress, luckily there was only a little wet patch that I was able to dry with the hand dryer. As I walked back across the room I could feel eyes on me. I wondered if they could see the outline of my suspenders under my dress.

I felt …..well…..naughty. When Josh got back to our table with a sheepish grin our next course was just arriving. We ate quietly listening to the music and looking into each other’s eyes. Josh smiled and said softly “you are going to pay for that you know” “pay for what” I asked innocently. Josh chuckled “for the dry-cleaning bill at least”.

I had eaten so much that by the time desert arrived I could only nibble at it. We finished the bottle and decided to go for a walk on the sand. We got to the cashier but found that the young lady who had made the booking had paid in advance. I smiled. Megs again.

We walked across the road to the sand and I slipped my heels of, it was a relief to be without them. Then I told Josh he had to take my stockings of so they wouldn’t get ruined. He knelt on one knee and I put my foot up so he could undo my clips and roll my stockings down. Then the other. We walked down to the water and he pulled me into his arms and kissed me deeply I could feel that his erection had returned. When he broke his kiss he told me that while he was on one knee he had thought about asking me to marry him. I rested my head against his shoulder and whispered “one day my prince”.

We caught a cab home and tiptoed up to Josh’s room. He slowly undressed my laying each article of clothing neatly across the back of his chair. When he got down to my suspender belt and panties he asked if he could leave then on. I said “of course you can, you naughty boy” he was very gentle and caring, kissing me all over and making sure I had cum at least once before he entered me.

It felt almost like the first time we had made love, sweet, gentle and loving. I felt so feminine that no trace of John/Jack remained. It may have been because of the dance floor incident, Josh was very slow to cum and we made love for ages. He eventually gasped and came deep inside me. We feel asleep in a warm embrace and didn’t wake until the sun was coming up.

We made love again before I got up and got dressed. Tiptoeing downstairs with my red heals in one hand and my purse in the other I almost ran into Josh’s dad. I blushed and mumbled “good morning” then he smiled and looked me up and down. He didn’t seem surprised to find me sneaking out of his son’s bedroom and asked how the night had been. I answered, maybe too dreamily, that it had been “wonderful”. As I passed I glanced sideways at him I couldn’t help but notice the huge bulge in his pajamas. I felt….well…..Very naughty.

As I was making my way quietly to my room Mia’s door opened and she pulled me into her bedroom. She was naked and looking great. Megs was sitting up in Mia’s bed and as she sat up and slipped her feet over the side I saw she was also naked. Before I could process all this my new girlfriends were demanding to know how the night went. We all sat on Mia’s bed and I told them how wonderful it was and how grateful I was for their help.

It was Megs who pointed out the obvious problem we now had. 2 Mias and no Jack. Mia came up with the brilliant solution. Mia speaks Thai with a slight Aussie accent but she can also speak Aussie with a Thai accent. In the latter she declared that she was Mia’s cousin visiting Sydney for the summer while Jack was visiting with her family in Bangkok.

That afternoon when Mom came home Mia and I were waiting for her. I thought this was going to be the hardest thing I had ever done in my life. It was actually quite the opposite. Mom came in and looked at us and smiled. She hugged us both and said we looked great. While Mia and I sat stunned Mom went to her room then showered and came back out. I finally found the words to ask her if she was angry or shocked.

It was me who was shocked when she said she wondered why it had taken so long. She told me how she had worked with a lot of nurses in Thailand who were Kathoey. Mia and I had no idea so Mom explained that in Thailand there is almost an accepted third gender and that she had seen it in me since I was very young and even more since I turned 10.

The rest of the summer holidays spun by in a blur. The 4 of us went everywhere together Josh and his harem. It was the best summer of my life so far. Josh and the new Mia slept together most nights and so did Megs and Mia’s new cousin.

Transformation 3, Doctor Johnston and Jacqui.

My 13th Birthday came and went, a year older but no real changes. I was pretty pleased as I hated the idea of my body suddenly changing. I would be happy if it was to be looking more like Mia’s but I knew Jacks hormones were lurking somewhere ready to strike.

One Saturday a couple of weeks before we were due to go back to school Megs told me her father wanted to talk to me. I asked why and she told me she had been talking to him about me and he just wanted to make sure I was ok. Mia and I caught a bus up to Megs’ house and we went inside. After a bit of chat Megs’ day said “come with me Jackie I want a quick word with you”

I was nervous as I followed him to his office. Megs’ dad is a doctor, he specializes in early childhood cancer research and is rather famous. He sat behind his desk and I sat in front. Then he told me that Megs had told him a lot about me and that he had a few questions for me himself. For the next 30 minutes he asked me all sorts of things from my earliest memories to my current feelings.

When he seemed to have finished and was sitting very quietly thinking I finally asked what all the questioning was about. He came back to the real world and smiled at me “well Jackie, I’m not qualified to help you as you are not my field of study. What I was trying to do with the examination was to determine if you are genuinely gender misaligned of it this is just a phase you are going through”.

I wasn’t really sure what he meant so I sat waiting until he went on “I am not a specialist but from what you have openly told me I believe you”. “I want to refer you to a colleague of mine who does specialise in people with your condition and didn’t want to waste his time if this was just a game” He picked up his desk phone and pushed a button then listened while he spoke to his friend and colleague about me.

It felt strange sitting listening to their conversation about me. Megs’ dad looked up from the call and said “can you see Doctor Johnston tomorrow’. Somehow I felt that something significant was happening and without knowing what I nodded “yes”. Megs’ dad hung up and said “you will like Brian and Mary they have been family friends for years”. “I’m sure Megan will be happy to take you there”. It made me smile to hear my girlfriend called Megan instead of Megs.

Megs slept over that night so we were read to set off bright and early the next day. We caught a bus to Manly then a ferry to the city and another bus to the Johnston’s. Mr Johnston answered the door, and Megs rushed into his arms for a big hug. “Come in guys meet my uncle Brian” I stepped in and said “hello Doctor Johnston I’m Jackie”. He hugged me too and said “Call me Brian”. After a little while Brian and I went off to his surgery and Megs went off to find Mary.

Brian already had a folder of notes that Megs’ dad had written up and sent through. He asked me a lot of the same questions then got down to the physical side of things.
He asked me about what happened when I orgasm, if I was sexually active and a bunch of other horrible things. He then asked me to get undressed. I was embarrassed for some reason but did as he asked. He took measurements and weighed me. He spent a lot of time examining my genitals and my breasts. After what seemed ages to me he said “that’s all sweetie, you can get dressed now”.

The pile of notes was growing as he was adding to it and looking up things on his computer while I dressed. When I sat down on the chair next to his desk he looked at me and said “you are a very special young lady”. He led me to a couple of charts on his wall to series of images from child to adult for male and female.

He explained that these were Tanner stages and that at my age I should be at stage 3 of either one or the other. I looked at him and he was deep in thought. I asked “where am I then” He turned back and said “sweetie I’m not sure and will need more tests but you seem to be about stage 2 in the Male scale and almost 3 in the Female.

Then we went back to his desk and he took 3 vials of blood and wrote notes on a pathology test sheet. He then passed me two specimen and told me he needed a urine and sperm sample. Then he talked to me about male and female hormones and how puberty is triggered and other gender defining things in the body. He told me that very rarely there are cases where the mind is so strongly convinced that it is different to the genetics of the body that the two fight for control. While he couldn’t be sure without the test results he thought I was one of those rare cases. My chromosomes were XY while my mind was firmly convinced they should be XX.

I then jumped right to the point and blurted out “can I have the hormones to make me female” . Brian smiled and patted me on the knee “be patient little one”. He said he couldn’t just give someone my age HRT and that I’d need a lot of physical and mental testing before that could happen. He must have seen the disappointment in my face because he said “there may be better news”. He explained that if he was right and I was one of those rare people then it might be possible to just give my XX side a helping hand and things could go my way. Brian explained that Mary was a Psychotherapist‎ in the field and she would talk to me next.

I spent most of the afternoon with Mary. If I thought Megs’ dad and Brian had lots of questions they was nothing compared to Mary’s. By the time we were finished it was late in the afternoon and Marys notes added to the pile already in my record. I ate late lunch with Brian and Mary and we talked about me. Mary was convinced that I was genuinely gender misaligned Brian was convinced that my mind was fighting my chromosomes to determine my secondary sexual features and they would both like to work with me and study my progress. I asked what to do next and Brian said the tests should be back by Tuesday but he would give me something to help. When I asked what it was he told me it wasn’t HRT but it was a testosterone inhibitor that would let the estrogens being created gain the balance of power.

Brian and Mary had sent Megs off somewhere and she got back about 4 and we headed home. Josh and Mia were waiting for us at the ferry terminal. I ran into Josh’s arms and broke into tears. He held me close until I had calmed down. We all sat and talked. I tried to tell the 3 of them what Brian and Mary has said but could remember hardly any detail mainly that the girl in me was fighting the boy and they were going to help he win. That night in bed Josh held me close and asked me if I was absolutely sure I wanted to do this and that he didn’t care which way I wanted to go. I snuggled close and told him I was absolutely sure I wanted to be his girl.

On Tuesday afternoon Brian called to say my tests were back and he wanted to see me in the morning. I tried to get him to tell me on the phone but he just said “everything is fine sweetie see me in the morning” Josh and I were outside Brian’s front door by 9am. I introduced Josh. Brian led us both through to his surgery.

He pulled out my records that seemed to have grown by another couple of inches. I noticed that the title on the folder just said Jacquie. Brian took the top sheet of paper. He smiled at me and said “I was right Jacqui you are a very unusual young lady” Josh chuckled and said “now tell us something we didn’t already know” Brian ignored him and continued “your body is managing to produce more oestrogen than testosterone so your puberty is almost stalled”.

“What now” I asked. He smiled and said “Now we wait. The inhibitors I gave you can continue, they have no known side effects and you should start to see and feel changes”. “How soon I asked” again he smiled and said “I can’t tell you. There are only 3 case studies like this that I can find and they vary in time and degree of change.

In one case the girls development caught up to her age in months and in another her development started and followed normal development pace”. Then Mary joined us, she gave me a kiss and I introduced my boyfriend. Mary said she was glad we were both there because she wanted to talk to us about going back to school. She explained that it would be better for me to go back as Jacquie instead of Jack because I was going to be changing.

She also talked about some of the reactions to expect in other people for me and Josh. Josh smiled and told Mary he had been looking after me since I was a little girl and wasn’t going to stop any time soon. Mary asked Josh if he would talk to her, and they left Brian and me to talk about my results.

Brian and Mary then set up a series of appointments for me every Saturday for the next 3 month. Mary wrote a letter for the school and we were done.

On the bus I asked what he and Mary had spoken about. Apparently she had asked a lot of the same questions she has asked me. I asked if he knew why. The answer came as a bit of a surprise. Apparently she confirmed that Josh is a heterosexual male and consciously and subconsciously considers me female. Strangely I think I already knew that.

It was still early so Josh and I went shopping, not the usual shopping but the school uniform shop. We bought all my new stuff for the start of the new term. As we were walking around the city we came to a body piercing place. I grabbed Josh’s hand and asked “can I have a belly button piercing babe” Josh looked at me surprised and said “I think that would look cool but don’t they hurt”.

I dragged him inside and spoke with the assistant who showed us the process and a number of pins, rings and things to choose from. The girl told us that surgical stainless steel was the best. I found one that would have a beautiful diamond dangling to the middle of my belly button. I held it to my navel. Josh smiled and nodded his agreement.

Obviously by the price it was Cubic Zirconia but I didn’t care it was a diamond to me. The girl led me through to a small but clinically clean room. She scrubbed her hands pulled on surgical gloves and took out the piercing needle. I had to look away but there was just a quick, sharp pain When I looked back she was inserting my jewellery. I looked in the mirror and it looked….well…..Hot.

It may have been my imagination but I started feeling different almost immediately after starting on my inhibitors. My breasts were even more sensitive and when Josh was fucking me the feelings seemed to spread further through my body. When I orgasmed my whole body tingled. On only the 3rd regular visit Brian reported that my last week’s blood tests showed significant drop in testosterone he measured my chest and hips and also noted that I was developing nicely.

The first week back at school was pretty horrible. Mary had warned us it would be, People soon got used to the Idea of identical twins Mia and Jacquie and left us alone. I think Josh got worse than I did but he never complained and we walked home hand in hand every day.

By the end of February my breasts were little mounds under my nipples. My nipples and areola had grown and were a little darker. My hips had also faired I loved my new shape and so did Josh. We were home in the back yard one Saturday morning Josh was laying on his back with his eyes closed I slipped his Board shorts down and stroked his cock.

He had grown about another inch over summer and was now just less than 7 inches. Luckily I hadn’t changed so my bikini was still a perfect fit. I slipped out of it and straddled him. With a bit of lube I lowered myself onto him opening easily now to take him in. The exquisite pain of penetration quickly changing to waves pleasure.

My hands were on his chest as I slid up and down taking him deeper with each move. Josh was staring into my eyes as he thrust up to meet my downward pushes. We fucked wildly for about ten minutes until I felt my orgasm rising, Josh reached up and cupped my breasts rolling my nipples. I came, squirting my little girly cum on his stomach.

My muscles squeezed his hard cock in waves. He shuddered, pushed up and pumped his sweet load into me. I collapsed onto his chest and he held me close while I trembled through several smaller orgasms. Josh kissed me and whispered “I love the way your tits sway when you ride me like that”. I smiled and thought “I do too”.

Conclusion.

As I told you at the start of this story I am now a happy 18 year old girl. The six year journey I have been on since turning twelve has been remarkable. Coming through puberty with the help of Brian and Mary has given me predominantly female secondary sexual development. Until I take my panties off Mia and I are identical twins.

Even naked I look and feel famine. My little girly cock is just part of who I am. It grew a little during puberty but still hides neatly in my panties. When erect it is less than 4 inches and quite thin. Josh on the other hand is now almost 7 ½ inches and I can’t close my hand around him. Thank goodness he has stopped developing.

Josh and I live together, just down the road from our parents. Josh bought me an engagement ring for my 18th birthday and as soon as the Australian government passes the Marriage Equity legislation, we will start to plan our wedding.

I am in my first year of university studying medicine. Doctor Brian is my mentor. He and Mary published a paper on their case study of me. I am the only one in my class who is already famous. I am hoping to specialise in Brian’s field and join his practice. Mia and Megs are still together and my best friends. Life is wonderful.

From Jack to Jacquie – by newpublisher2010

Adult story Editor October 8, 2015 Leave a Comment

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.

Virginity story: From Jack to Jacquie – Part 2

Leave a Reply Cancel reply

Virginity story: From Jack to Jacquie – Part 1

Author: newpublisher2010

Leave a Reply Cancel reply