The Law of Attraction

Story Info
Jamie's story: attraction to the feminine.
10.6k words
4.68
70.3k
50

Part 1 of the 8 part series

Updated 10/29/2022
Created 08/12/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
hottchic
hottchic
258 Followers

This story is a transsexual fantasy.

It is the story of a woman who was born in a man's body, even though, for many years, she did not recognize this, and a mystical transformation that allowed her to become her true self.

This story is for all those people who have ever felt they were cheated by fate, in terms of their gender, and daydreamed of waking up having all the attributes of their desired orientation...

*

"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."

I guess my situation would have been thought by most as very bizarre.

My name is, or should I say was, James, 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.

Let me explain, although I considered myself to be a straight guy, I found women just as attractive as the next guy, I just seemed to find it impossible to relate to a woman as a guy is supposed to. Apart from being just below average height, 5'9", and having a low level of muscle development, not much body hair, and a relatively high pitched voice for a guy, I had always been very shy around women.

I was shy, because I just didn't know what to say around them that might get them to show some interest in me as a guy, and whenever I had made an attempt on the occasional date I had been on, I had invariably ended up embarrassing myself.

Most women simply ignored me after the first date, and a few who were at least honest with me, complained that the main problem I had was that I did not have the strong decisive image and strong gestures that a man was supposed to have. Some even said, more cuttingly, that my gestures were even effeminate.

You could say by the time I moved into an apartment with Ashley, I had just about given up on women, and resigned to living my life as a single guy, with no sex life.

Believe it or not I was the perfect person to share an apartment with Ashley, because Ashley's history was one of a string of disastrous relationships with women who were just no good for her.

The only woman who was constant in her life, was her bisexual friend Jackie, who you could say acted as a rebound partner for Ashley, following getting her heart broken in yet another failed relationship.

The problem was that although Jackie liked to have fun with women from time to time, especially with Ashley, the love of Jackie's life was her long term boyfriend Jeff.

Jeff was a great guy and also loved Jackie very much and lately there had been a lot of talk of Jackie and Jeff getting married. Often I wished that I could be more like Jeff, I looked up to him a lot. Somehow he managed to pull off being both manly and sensitive at the same time.

Anyway where was I? Oh yes, I was the best person to share an apartment with Ashley, because she considered me to be completely non threatening, and the fact that I was not a woman meant that there was no possibility of sexual tension and the prospect of another failed relationship.

It's sad to say this but I think that one of the reasons that Ashley liked sharing an apartment with me was that the fact that I had resigned myself to being alone and not getting any sex, made Ashley, in comparison feel less depressed about her own situation.

The fact that there was no tension of any sort between Ashley and myself, and the fact that we both had a relatively laid back attitude to life (apart from in the area of intimate relationships), meant that we got on really well together.

Unlike most guys, I wasn't into sports, or drinking beers, or spending a lot of time hanging out with other guys. I also liked many activities that women like, like: going to the mall, devising new recipes, fashion, particularly women's fashion, reading romantic novels, and chick flicks.

Many a time, after splitting up with her latest lover, Ashley would rent a movie like, 'When Harry met Sally', or 'Sleepless in Seattle', or 'You've got mail', and we would watch it together, passing a box of Kleenex between us.

Ashley and I could chat to each other about anything and we had a very similar sense of humor, and often she would use me as a shoulder to cry on, cheering her up a bit with a few humorous remarks about her latest ex.

Our life was a tough one, we always seemed to struggle to pay the rent but somehow we always got by.

Ashley was an aspiring actress, who occasionally played minor parts on Broadway and made her income up by waitressing. I was a struggling artist who occasionally sold one of my works and I made my income up by working at Starbucks.

Apart from our sexual frustrations, and the lack on both our parts of an intimate relationship, you could say that Ashley and I were quite happy, and we were happy spending time together, and while there was no intimate or sexual contact, we did give each other a lot of hugs and stuff.

I said that there was nothing that Ashley and I couldn't talk about. Well there was one thing about myself that I had never told her about, in fact I had never told anybody about it, and that was that I was a cross dresser.

As I often did, as Ashley went on shift as a waitress I went to my room and got out my secret stash of clothes. For a moment I felt a tinge of guilt, thinking that I should be working on my art, but it didn't last for long. To be honest I had not been feeling very inspired lately, so sitting in front of a blank canvas would just have frustrated and depressed me. In fact if I had been feeling inspired to paint, then that is exactly what I would be doing, partly I dressed to make myself feel better and take my mind off my frustrations.

My cross dressing did not generate much in the way of guilt, rather, it was feelings of shame that were aroused. This was unnatural, who was I kidding, a guy trying to make myself look like a woman? What would people think if they knew? That I was an abomination, or perhaps they would just laugh at me because knowing what I did allowed them to think that there was at least somebody who was lower on the rung of life than they were.

Even while I had these thoughts though, even while I was ashamed, I could still not help feeling aroused by the idea of being in those silken panties, that frilly bra, the short strapless dress puffed out by layers of tulle, and the strappy shoes with 4 inch heels.

As I walked up and down my bedroom, looking at myself in the mirror, I could not help but become aroused. I could feel the strength of my erection as I repeatedly brushed my hands down the puffed out skirt of my short prom dress, delighting in the feel, both the texture of the dress on my hands and the feel of the material against my rock hard dick under the dress.

Eventually I could bare it no longer, and I threw myself on the bed, lifting the skirt of my dress and releasing my dick from my panties, and vigorously jerking myself off until I came spurting cum over my skin.

Then reality kicked in again and grabbing a tissue from the box to wipe off the mess I had made of myself, I looked in the mirror at the same depressing sight. Despite my shapely legs, my small feet, my under developed arms (for a man anyway), and my thin wrists, despite my delicate facial features, I still looked like a guy in a dress.

I had considered wearing a wig, but that seemed like faking it, and I didn't see the point in wearing makeup just for a few minutes of self pleasure.

I sometimes imagined letting my hair grow long, I was an artist after all. Many artists had a bohemian look.

Yet I wasn't an outgoing type like many of my artist friends, and I told myself it was because I had a deep introverted personality, which to some extent was true, but I could still have had long hair. The truth of it was that I was afraid to express myself, afraid what people might think, afraid of rejection.

I had grown up in a very religious household, and learnt from a young age about the natural order of things. I was born a man, so there was never any argument in my mind about being anything else.

Yet as far back as I could remember, I had had dreams where I cross dressed or where I was a girl. It seemed inevitable that I would start cross dressing, sneaking around 'borrowing' my sisters clothes.

After leaving home as a disappointment to my father, he wanted me to be a preacher. I had disassociated myself from the religion of my family. It was not so much that I did not believe in God, but rather that I believed that God would want nothing to do with me, principally because of my addiction to cross dressing as I saw it.

You see I had finally come to a position where I would tolerate my cross dressing, because I could not stop it. Oh I had tried to stop it hard enough, I had certainly tried, throwing out my stash of clothes several times, and yet the 'compulsion' as I saw it, had me firmly in its grip, but that did not mean that I had to accept it.

In the end the only thing I could do was to justify my behavior, by reminding myself that at least I was not harming anybody. The problem was that I used fantasies when I crossed dressed and jacked off and I had 3 fantasies that I used:

1.A lesbian fantasy where I would imagine that I had a pussy, and was doing 69 with a woman

2.A fantasy where I was myself but dressed and a woman pushed me on the bed, lifted my skirt, pushed my dick into her pussy and rode me while looking down on me wearing a dress

3.A fantasy where I was a woman with a pussy and a guy was fucking me doggy style

The real problem was that lately I had been imagining real people in my fantasies. In the first 2 fantasies I imagined the woman was Ashley, and in the third fantasy I imagined the guy was Jeff.

Finally I started becoming a little more courageous and letting my hair grow out a bit, and now it was about shoulder length. I had started tying it in a pony tail like some people I had seen connected with the arts, and as I expected some guys teased me about it. On the other hand many people would explain it away, pointing out that I was, after all an artist.

One thing that I liked a lot was that Ashley liked my hair, saying that it made me look very bohemian, which was a good look for an artist.

Then, one day, came that fateful night, and little did I know that my life would never be the same again.

It all started with Ashley getting ready to go on a date. She really wanted to make an impression and had dolled herself up in a pretty, sundress. I loved how she looked in the dress, it really turned me on to be honest, and I told her so.

"You're always so sweet James," Ashley said, "you would make somebody a great girlfriend, I mean boyfriend."

"Why did you say girlfriend first," I said, a little embarrassed.

Ashley said, "Oh, nothing really, it's just that guys don't talk the way you do as a rule, talking to you is more like talking to a woman."

As soon as Ashley left, I went up and ran myself a bath with sweet smelling lavender and herbal oils and as I bathed I completely shaved my arms, legs and my chest, not that I had much body hair to start with. Particularly I paid attention to under my arms because I had started to hate the idea of hair under my arms.

Once I had bathed and my skin was clean shaven, I went to my room and got out my secret stash of clothes. The panties slid luxuriously up my clean shaven legs and I hooked up my bra from behind, I was becoming quite good at putting a bra on myself. I then put on a white semitransparent blouse and a black, super short, mini skirt. The look was topped off with a pair of shiny black pumps with 4 inch heels.

As always I followed my usual routine of walking up and down looking at myself in the mirror, before finally throwing myself on the bed and jacking myself to one of my favorite fantasies. This time I was a lesbian in a 69 position with another woman, and this case I could not help Ashley's face from coming into my mind.

As I came panting exhaustedly on the bed, I had a twinge of guilt as I realized that I had just brought myself to orgasm thinking about Ashley.

At that moment I heard somebody entering the house, it must be Ashley, but she had told me not to expect her back before 1:00 AM.

"Shit," I thought to myself, quickly wiping the mess off me and then removing my blouse, skirt, bra and panties. I quickly threw on a T-shirt and a pair of Bermuda shorts hid my stash of clothes and went out to meet Ashley.

Ashley had been crying, there were tears streaming down her face.

Without saying anything I went up to her arms outstretched and embraced her in a hug. It seemed like we stood there for ages, she just didn't want to move.

Eventually, I asked the inevitable question. "What happened?"

Slumping down on the sofa Ashley told me that her new friend Gillian, who she had fixed the date with had stood her up, dumping her with a text message which said she had decided to get back together with her ex, this after leaving Ashley waiting an hour in the restaurant.

As I had done before on these occasions, I lay back on the sofa inviting Ashley to snuggle in my arms. This seemed to comfort Ashley a lot, and eventually I said, "You must be hungry, let me make you something."

It was late, so I just made us both an omelet which we both started to eat with relish. Ashley opened a bottle of red wine to drink with the omelet saying, "I still want my evening date, and who better to have it with than my loyal girlfriend 'Jamie'."

There it was again, she was calling me a girlfriend again, and this time she had called me Jamie, "What the hell was going on I thought to myself."

As we ate Ashley said, "Why are none of the women I seem to hook up with more like you? You would make the perfect girlfriend, so understanding and caring, so emotionally supportive, it's just not fair that you're a guy, it seems like a cruel twist of fate."

Soon we had almost consumed a second bottle of wine, Ashley consuming rather more than myself, and she pushed me back on to the sofa, a little aggressively even, snuggling up to me as she had before.

After a little while like that, Ashley suddenly said, "Ooooh... you smell so nice, like a woman, I think you must have been bathing in my lavender scented bath oils." Then she continued, "And your arms feel so smooth and feminine, they feel so great around me.

I suddenly remembered how I had bathed in Ashley's lavender scented bath oils, and shaved my body, thinking of course that I would be alone all evening, how the fuck was I going to explain my sweet smelling smooth skin. Right now Ashley was a little drunk, but tomorrow I anticipated many questions from her.

As if reading my mind Ashley's hands moved to my legs, running her fingers over my now super smooth legs. "Oooooh, your legs are sooo smooth also, actually your legs look great, too good to be on a guy."

I was thinking to myself, "Why the fuck did I just throw on a T-shirt and Bermudas, allowing her to notice my smooth arms and legs, rather than a track suit, what a complete idiot I am.

Then just when I thought I couldn't be embarrassed further, Ashley started removing the band securing my ponytail and shaking my hair loose. "You know, you really do have some potential Jamie." She said. "Wait one minute."

Ashley left and was back quickly with a hair brush and her makeup kit.

"What the fuck," I said, but then Ashley started to cry.

"Please humor me," Ashley said, "I have just been dumped in a horrible way, please let me do this, it will really help cheer me up."

I had never been able to refuse Ashley when she pleaded with me like this, I guess somewhere in my subconscious I knew that I had fallen hard for Ashley since the first moment we met even though it would have to be forever an unrequited love, the truth was that I would do anything for her.

So Ashley started to do my face up applying makeup around the eyes, mascara, blusher and a pale pink lipstick.

"WOW," said Ashley, admiring her handy work, you look really cute.

"Come with me," she said virtually dragging me into her bedroom.

When she had pulled me into her room, she said, "I want you to wear this." And she pulled out of her wardrobe the prom dress she had worn to her prom and lovingly kept.

Part of me seemed to leap for joy, when I saw that she wanted me to wear the dress that I had envied her having for so long. The dress was beautiful, it was white and strapless with an incredible full skirt that only came down to mid thigh, designed to really show off the legs.

I protested of course, saying that I was a guy and I couldn't wear a dress, especially a beautiful one like this, but it was all to no avail, it was as if she knew that part of me really wanted to do this. When Ashley knew she had me she got out a matching white lace panty and bra set telling, really it was more like ordering me to remove my clothes and put on this very pretty underwear.

Being a little drunk myself I was operating in semi automatic mode and Ashley saw me expertly fastening the back of the strapless bra and said, "Looks like you've had practice Jamie, or maybe it's just because you were meant to be a woman."

Ashley then pushed some panties into the cups of the bra to fill me out a bit and finally slid the dress up my body, snugly encasing my body in the beautiful dress as she pulled up the back zip. As I experienced the wonderful feeling of being encased inside this wondrous dress with it's incredible full skirt, and with Ashley looking on, I was harder than I had ever been in my life, leaking a bit of precum into the panties.

Then Ashley pulled me in front of the mirror saying, "Now Jaime, look at yourself."

The sight I was met with looking back at me from the mirror literally took my breath away. This was no guy, instead I was looking at a beautiful woman. If I had not known it was me, I would have fancied her.

Uncharacteristically Ashley then pushed me onto the bed and started kissing me hard, pushing her tongue deep into my mouth. "You know," said Ashley, "you look so much better like this, oh fuck I wish you were a real girl."

After much more kissing, Ashley taking a dominant role, we finally fell asleep.

The following morning Ashley apologized for her behavior, the way she thrust herself upon me, saying it must have been the drink. She made it clear that what she wanted was a woman, and that while we had become very close in many ways we could never be sexually compatible because of my gender.

For the next two weeks Ashley tiptoed around each other, it was like you could cut the atmosphere with a knife. At one point I asked her if she wanted me to move out.

"Nooo, please no," Ashley said. "We click so well together, who would I talk to the next time I have a failed relationship," she commented light heartedly.

A week later when we were eating together Ashley suddenly said, "You know Jamie," she called me that all the time now, "I accidently discovered your secret stash of clothes before that night when I dressed you, I knew you had this desire. There is no reason for you to go sneaking around and only dressing when I am out."

I was shocked that she had known this but also relieved, it was like a great burden was lifted from me that I didn't need to sneak around.

Ashley continued, "I was thinking I could help you to look more feminine, you looked so pretty when I made you up that night."

And so it started that quite regularly Ashley would help me look very feminine, teaching me about makeup, hair styling, and doing my nails, but also teaching me about other things like how to develop more feminine movements and gestures. She even found some videos on you tube instructing me how to develop a female voice.

hottchic
hottchic
258 Followers