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You are here: Home / Virginity sex stories / From Jack to Jacquie – by newpublisher2010

From Jack to Jacquie – by newpublisher2010

Adult story Editor July 18, 2018 Leave a Comment

“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”.

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Filed Under: Virginity sex stories Tagged With: Author: newpublisher2010, breaking virginity, first intercourse, girl losing virginity, girls losing their virginity, how i lost my virginity, i lost my virginity, loosing virginity, lose virginity, losing her virginity, losing my virginity, losing of virginity, losing virginity, losing virginity age, losing virginity stories, losing virginity story, losing your virginity, lost my virginity, lost virginity, newpublisher2010, virginity loss, virginity lost, virginity sex, virginity stories

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From Jack to Jacquie – Part 2

Adult story Editor October 8, 2015 Leave a Comment

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”.

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