This story is a transsexual fantasy.

Before reading this chapter I highly recommend that you read chapters 1 to 3.


Now as a complete woman Jamie has to contend with everything that being a woman entails. Already an emotional person she is even more emotional now and she also has to contend with the effects of having a monthly period.

Ashley of course is very supportive of her lover…

“Imagine starting to believe in yourself and your infinite possibilities. Imagine believing you deserve everything you want out of life. Imagine getting everything you want out of life.

“Once you apply the ‘Law of Attraction’ everything is possible.”

My name is, or should I say was, James (now Jamie), and there I was, a 30 year old guy, who was a virgin, sharing a New York, rent controlled apartment with a 25 year old lesbian, Ashley, and she was a hot looking lesbian at that.

Ashley, although a lesbian had started to help me explore my feminine side, and it was becoming clearer to me with each passing day that Ashley was starting to fall in love with me as a woman.

I had mixed feelings about this because although from the moment I laid eyes on Ashley I fell for her, I felt that in the end our relationship could only ever be a disappointment to Ashley as I was not a biological woman.

Then in a surprise gesture Ashley had paid for a very expensive therapy for me called deblock therapy, and this therapy was supposed to help me realize my true potential.

Now it appeared that the result of deblock therapy was going to be fame and fortune way beyond my expectation and it was all happening so fast.

My launch as a major New York artist had been spectacular and at the same time I had been thrust onto the New York social scene mixing with celebrities and people in entertainment, due in large part to Annabel (my artistic agent) and her expert promotion of my inspired art.

My success also appeared to hinge on the fact that ever since the deblock therapy, my body, attitude and mannerisms were becoming ever more feminine, so much so that I was introduced to New York society as a beautiful woman in a lesbian relationship.

As the changes in my body continued Ashley took more and more interest in me and started fucking me with a strapon and letting me fuck her in her pussy.

Then my body changed completely and my dick was replaced by a perfectly formed pussy, much of course to Ashley’s delight.

That morning as on most mornings now I awoke to the feeling of my pussy being eaten. And looking down I saw Ashley’s long black hair spread across my thighs, as she sucked my clit and every so often pushed her tongue into my pussy.

I had come to love the sensation of being eaten out by this beautiful woman, the immense pleasure it gave me to have my beautiful vulva licked. The stimulation was not the tense localized sensation that I had experienced in male form but instead it appeared to spread though my whole body.

I was beginning to make little mewing sounds that I knew were music to Ashley’s ears and resulted in her increasing the activity of her tongue on my clit and inside my pussy. My hands as if of their own volition moved down to grab Ashley’s head and I started to push her head harder into my pussy as I began to approach orgasm.

Now I bit my lip in response to that wave of sexual tension spreading through my body, I knew it would be coming any moment now. And when it did come I cried out with the most incredible feeling of joy as one wave of pleasure after another coursed through my beautiful female form.

“Fuck…. I love you Ashley,” I cried out as she took me to places I could never have imagined with her tongue in my most intimate of places. The orgasm just seemed to go on and on, and just as it began to subside, Ashley pushed her tongue into my pussy forcefully, causing further waves of pleasure to rush through my body.

As the waves of my orgasm continued to flood through my body, Ashley now moved up my body until her lips contacted my own, kissing me hard, her tongue probing deeply into my mouth, it felt like my mouth was full of her tongue as it probed the back of my mouth. And as she kissed me she started to rub her soaking wet pussy against my own urgently grinding her hips against me.

At this moment I felt over powered by Ashley as she pushed her body hard against mine; lips to lips, tits to tits and pussy to pussy. She grabbed my wrists and pushed them down pinning me to the bed as she writhed against my body concentrating on bringing herself to orgasm the way she had brought me to orgasm only minutes before.

Then it came, and Ashley shuddered as her orgasm raced through her body, and in this moment of total surrender to her senses I took my chance. Grabbing Ashley’s wrists and pushing them above her head, I forcefully rolled her over, not breaking from our kiss.

Now on top myself I started to writhe against Ashley, taking charge of our movements and pushing harder against her, turning her orgasm into multiples and grinding hard against her until I finally came myself again shuddering all over.

That morning to show how pleased she was with me and to help both of us recuperate our energies after our session earlier, Ashley had cooked a big breakfast consisting of eggs, cheese, potato cakes, tomatoes and mushrooms.

As we ate our food Ashley talked excitedly about the new Broadway production in which she would be starring, for the first time she would be playing the lead role in a major production and they would be starting rehearsals in 3 days time.

“Well that’s certainly something to celebrate,” I said.

“Yeah,” replied Ashley, “in fact Jeff and his brother Alex have to visit home because their grandfather died, which leaves Jackie and Annabel home alone with nothing to do, so I invited them to join us at a new lesbian night club which recently opened to celebrate with us.”

“Cool,” I said, “I haven’t seen either of them for a while and I miss them.”

“Yeah,” Ashley said, “I think Jeff and Alex keep them occupied a lot and since you got your new pussy I haven’t been able to keep my hands off you.” As she said this she squeezed my left nipple hard. So it was that that evening Ashley and I got ready for a night on the town. I wore a bright red minidress with an ultra short skirt which flared out just below my waist pared with red pumps with 4 inch heels and Ashley wore an ultra short black leather skin tight minidress paired with black velvet boots also with 4 inch heels.

As we got into our black BMW convertible, we both looked at each other with lustful stares and Ashley said, “We look fucking hot!!”

I responded to this comment by kissing Ashley hard on the lips.

As we drove to the club, I leant against Ashley pushing my hand under her tight leather dress to feel her delicious pussy, I discovered that it was sopping wet.

“Fuck, you are such a turn on,” Ashley declared.

The night club had valet parking and a young woman in a denim miniskirt and revealing top took our keys to park our car.

In the club we found that Annabel and Jackie had already arrived and were chatting animatedly to each other. Annabel was wearing a pretty white mini sundress with a tiered skirt and Jackie had on a figure hugging black cashmere minidress.

Annabel and Jackie both stood up to greet us and we all admired each other saying how hot all of us looked before sitting down and ordering cocktails for Ashley and I, we both had a white Russian.

As we chatted we noticed a group of pretty young women looking over in our direction. One of them came over to our table and asked if they could sit with us for a while. When we said they could, they told us that they had read about Ashley and myself in a magazine article and that they thought we were inspiring figures in the lesbian community, one girl said, “And of course you make real hot lovers.”

At this remark Ashley and I obligingly leaned into each other kissing deeply and filling each other with our tongues as we felt up each other’s tits.

“Oh fuck, that’s so hot,” another girl said.

Later they started playing music in the club and Ashley got up to dance with Jackie, at the same time Annabel led me onto the dance floor and when it came to a slow dance she was really feeling up my tits and ass so I responded in kind.

Looking over at Ashley and Jackie I realized that they were also feeling each other up.

Later Ashley and I danced together while Annabel danced with Jackie. As Ashley and I held each other close Ashley said to me, “It’s still hard to believe how far we have come, right from the start I felt that there was a spark between us, but you were a guy, it seemed impossible.

Now when I see you, you are the most beautiful girl in the world to me. The most caring loving person I could ever imagine.”

As Ashley spoke I suddenly became aware that there were tears streaming from my eyes. “I love you Ashley,” I said, “more than you can know.”

Ashley replied, “I love you too, and I want you to be my wife, civil partner, whatever you want to call it.”

“Yes I will,” I said without hesitation, “you have just made me the happiest girl in the world.”

That evening the four of us returned to our apartment, and after Ashley had shown Jackie and Annabel around our new apartment with its harbor view we opened a bottle of Baileys and we all had a glass of Baileys on the rocks.

As we drank we all got comfortable removing our clothes and when I removed my panties both Annabel and Jackie were mesmerized, they hadn’t seen my pussy. Then as I lay down on the sofa both Annabel and Jackie honed in on my new pussy, one of them sucking my clit while the other probed my depths.

As my excitement built I could not help but be blown away by the way the sensations rushed through my body. And as Jackie and Annabel worked on my pussy, Ashley kissed me hard whilst grabbing my tits in her hands. My new female form was taking some getting used to but every day I was loving it more, particularly the great satisfaction I gained from my new female orgasms which ripped right through my body.

As I thought this I found myself cumming in response to the insistent tongues on my pussy and my first orgasm was followed by another and yet another making me feel so loved and cared for by my beautiful companions.

Later when we retired to the bedroom, Ashley got me to get in the doggy position where she proceeded to lick my pussy and ass, while I in turn ate out Jackie as she ate out Annabel. Then I did 69 with Annabel while Ashley did 69 with Jackie and later we all lay back down on the bed rubbing our hands over each other’s bodies and sucking each other’s tits. Shortly after we all fell into a deep sleep.

Ashley started rehearsing for the new play where she was playing the lead, and while she did I would produce new works of art, continuing to develop my style, there seemed to be no limit to my creative energies.

Then Ashley would return from her rehearsals in the evening full of positive energy full of lust for me and wanting to make use of my beautiful female body, I of course was only too happy to oblige.

One night she pushed me face down onto the bed and proceeded to give me a wonderful back massage, after which, lying against my back, she grabbed one of my tits, and with the other hand rubbed my clit and pushed two fingers into my pussy, making me cum hard. In that position I felt so dominated by Ashley.

Some days after feeling inspired and producing some brilliant highly sexually charged art I would sit on a chair naked staring in wonder at my beautiful new pussy and probing it with my fingers. Sometimes I would use a silver bullet to stimulate my clit as I did this.

Watching me stimulate myself and cumming in waves of feminine orgasms was incredible to behold, daily reminding me of my new, highly sexual female form.

Finally the date arrived when I would have to start my national tour showing my art work at galleries around the country. As Ashley was in the middle of rehearsals she could not come with me but Annabel would be accompanying me.

They night before I was due to go on tour, and Ashley and I spent the evening with Jeff and Jackie in order to celebrate my upcoming tour, we had a delicious meal at one of New York’s best Sushi restaurants and later we all went back to our apartment to continue our celebration.

On arriving at our apartment we had a few drinks and Jeff came over and sat by me while Ashley and Jamie were feeling each other up. I had always felt attracted to Jeff and this night I was feeling the attraction more than ever.

I remember the fantasies I had had of having a pussy and being fucked by Jeff, and suddenly I began to realize that now as I had a pussy I could make this fantasy a reality.

Like a woman possessed I suddenly started kissing Jeff and although initially surprised by my forwardness Jeff started responding in kind, grabbing my tits as he kissed me. Then, as if it had a mind of its own my hand went to Jeff’s dick and I circled it through his pants causing him to make a sharp intake of breath.

At this point Ashley announced that we should all retire to the bedroom, and in the bedroom quickly all our clothes were came off.

When Jeff saw me naked, when he saw my pussy he gasped, to the amusement of Jackie who had already seen and tasted my pussy.

Still feeling attracted to Jeff, more so seeing him naked, I again took his dick in my hand and almost on auto pilot I brought it gently to my mouth, and as I started to lick the head of his dick, Ashley and Jackie looked on mesmerized by what I was doing.

Soon I was licking down the whole length of Jeff’s dick and now I started to take him in my mouth, Jeff was groaning with pleasure as I did this. Soon I was bobbing up and down on Jeff’s dick and he was rock hard, and now I started to become aware of the wetness in my pussy and my urgent need.

Now I got on my hands and knees on the bed and pointing my sweet ass towards Jeff, I said, “Fuck me, please fuck me.”

I felt Jeff grabbing my ass and pulling me towards his dick, and as he did so Ashley said softly and full of care for me, “Jeff, please be gentle, remember that Jamie is a virgin.”

Then I felt Jeff’s dick against the lips of my pussy, and then he pushed the head inside, the feeling was incredible, but also hurt a little. As Jeff pushed further inside me I was suddenly aware of a pressure building up, and then suddenly there was a rip, resulting in a sharp pain which brought tears to my eyes.

Suddenly Ashley was next to me consoling me saying it was ok, and now as Jeff pushed further forward the pain slowly began to wear off. Now as Ashley saw that I was starting to moan with pleasure, she grabbed my hair, pulling me down on her sopping pussy as Jeff built up a rhythm fucking me, and as I ate out Ashley, Jackie sat on her face, giving Ashley full access to her pussy.

The feeling of having my pussy filled with a live throbbing dick for the first time was incredible, and now Jeff started to grab my tit as he fucked me, his own moans of pleasure only being eclipsed by my own as I raised my head from Ashley’s pussy for a moment, only to have it firmly pushed back in her soaking snatch.

The orgasm was incredible spreading through my entire body as I had come to expect and causing me to literally shake with pleasure.

I came in waves of orgasms one after another, knowing this was only something that I could experience as a woman. Then finally after I must have cum at least six times, Jeff filled me with his seed, his love juice seemed to squirt inside me for ages, although in fact it could only have been a few minutes, my pussy rippling with pleasure ravenously sucking it all up.

Jackie and Ashley were also screaming with pleasure, also experiencing multiple orgasms. I almost felt sorry for Jeff that he could not experience the type of multiple orgasms that we women could, but then I remembered back to the time when I had had a dick myself and fucked Ashley in her tight snatch, I knew that the feeling for Jeff inside me must be incredible and feeling my tit in his hand.

And it gave me the most incredible feeling of power, knowing that Jeff felt so good inside me. He was dominating, fucking me strongly and rigorously and grabbing my tit and pulling my hair as he fucked me, yet in reality I knew I had the power because right now I was the source of all his pleasure, and I knew I looked and felt incredible to him.

After Jeff had cum inside me we all sprawled on the bed catching our breaths. Fortunately Ashley had put some towels on the bed which avoided me messing up the bed clothes with the blood from my newly popped cherry. As Ashley cleaned me up by unashamedly licking the blood from my pussy I reflected on the fact that I had lost my virginity twice in the space of a few weeks, once when I had a dick and then again as a true woman.

Later that night Jackie sucked Jeff to make him hard and he fucked her doggie style with her crying out like I had. I shuffled in front of her and she proceeded to eat me out while Jeff fucked her and the feeling for me was great, as I in turn ate out Ashley who was now sitting on my face.

Still later I wanted to have Jeff’s dick in me a second time but I was still feeling sore from my first, virgin, penetration, so Jackie suggested that I ride Jeff cowgirl style where I would have more control over the fucking and could be more comfortable.

As I rode Jeff’s dick he grabbed my tits enjoying the feeling of being in me and feeling my tits at the same time. After a while of riding his dick cowgirl, I moved forward adjusting my legs so that I could kiss Jeff as he fucked me.

I was enjoying the feeling of Jeff’s dick inside me while I kissed him hard on the mouth, my tits pressed against his chest when suddenly I felt that my ass was being invaded, it was Ashley who was fucking me in the ass with a strapon and as she fucked me hard while I was still being fucked by Jeff, she moved her hand around me to grab my tit, saying, “This is so hot.”

The feeling of having both holes filled at the same time was exquisite, causing me to cum very hard and then again and again, until Jeff finally came again inside me.

That night I slept very soundly in Ashley’s arms as Jeff embraced Jackie. For the next three weeks I toured the US with my art work with Annabel. I was missing Ashley who had to stay in New York preparing for the Broadway play where she had the leading role. Annabel was also missing Alex who was an architect designing a new luxury apartment complex in New York. Fortunately Annabel and myself had each other for company, and we certainly had fun.

After one week on tour I got what I thought must be a stomach upset. I was often nauseous particularly in the morning. Yeah, I know what you are thinking, call me innocent if you like, but I didn’t attach any significance to this at the time.

Apart from my bouts of nausea, the tour went very well for me. I was interviewed by for many periodicals both inside and outside the art world and even got a spot on national television where I was hailed as the new Salvador Dali. The fact that I was a woman in a lesbian relationship only seemed to generate more interest, it seemed like hot lesbians were all the rage.

On my triumphant return to New York, I returned in time to see the opening night of the play where Ashley was playing the lead. I arrived back one day earlier than expected, so Ashley was not expecting me to be there.

I even managed to twist the producer’s arm into letting me go up on stage and present Ashley with a massive bouquet of flowers after she had taken her bow. Seeing me there as well as the emotion of giving an exceptional first night performance was overwhelming for Ashley and tears flooded her eyes as she took the flowers on behalf of herself and the rest of the cast.

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June 2018
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