Ana Le Babe - Becoming A Cross Dresser

Prologue

My name is Geoff (not my real name of course) and I would like to introduce you to someone who changed my life. She is my alter ego, Ana Le Babe.

Geoff The Heterosexual

As Geoff, I am a loving father of two step daughters and a husband to a fantastic wife.

And although my wife is aware of my previous bisexual experiences, she is not at all aware about Ana Le Babe.

Ana Le Babe

Ana, on the other hand, well let’s say she started life as a virgin, hungry for cock.

She then progressed into and anal queen, enjoying either a vibrating dildo of a decent size or a real cock or two, handled by people who know what they are doing with them...!

She has now moved on to being a truly bisexual person who is game for just about anything with either sex.

Discovering Cross Dressing

This story  begins in a place called Croydon, in the south east of London, England.

It began way before I hit my teens, when I was only 4 or 5 years old.

At first I just thought about sneaking into my mother’s bedroom and trying on some of her underwear, but one day, when everyone was downstairs, I actually did it. I open her top draw and grabbed a pair of tights. I fumbled with them until I got them on and felt my first cross dressing experience and LOVED IT.

Next I pulled out a large bra and managed to do up the hooks before slipping it over my head. I pranced around the room, revelling in the way it made me feel.

I put everything away and left the room, desperate for the next time I would be able to dress up again.

This happened from time to time between the ages of 4/5 to when we left England in 1987.

Discovering My Sexuality

The second part of this story starts in the suburbs of Western Australia in 1987 when I was 14 and continues to today. Other stories will include specific encounters.

Over the years in England I had been "borrowing" knickers, skirts and dresses and also trying on my mothers high heels.

This was all fun at the time, a kid playing dress ups, but then puberty set in and masturbation became a huge part of my life, which has never really left me.

I graduated to "borrowing" my sisters clothes when she got old enough as her clothes seemed more sexy to me, tighter and smoother on my body.

This cycle of patiently waiting until my sister was out  was becoming more and more frustrating as my urge to slip into sexy clothes grew more every year.

Finding Ana Le Babe

By my late teens my sisters clothes had got pretty sexy and I had also started to play with make-up. I was getting better and better at it and begaing thinking "You could just about pull this off with the right group of people".

It got to a point where I knew I was going to get caught "borrowing" the clothes so I decided it was time for me to build my wardrobe and make Ana into the dirty slut she desperatly wanted to be, but how to go about it. I couldn't just walk into a department store and buy what I wanted....! I didn't have a lot of money at the time and the dressing up was still a "hobby".

One day I had a brain wave, second hand clothes stores. A great range of clothing, jewellery, shoes, everything I wanted, and cheap too. I just had to get the confidence to walk in and buy the things I desperately wanted.

So one day I plucked up the courage to go and do some shopping . How Invigorating...!

I spent nearly the whole morning driving around various suburbs, popping into Good Sammie’s and Salvation Army second hand clothes shops, marvelling at the variety of stuff I could get for Ana.

My first purchase was in a Salvation Army second hand shop in Gosnells. Here I found a lovely little black lycra dress that was a few sizes too small. It was really short and just covered my butt.

Nervously I took it to the counter and waited for the looks of disgust I thought I was going to get. To my surprise, a pleasant lady just said "Is that all dear?". I paid for the dress and headed out to my car. As I drove off I thought "I can do this, I can really do this...!" I was elated.

The dress I had picked had a high front neck line but was very low in the back. "Excellent" I thought. "Good access from the back to play with my nipples (I REALLY love that), and so short I thought my butt was going to pop out of the bottom, not that I minded and it made me feel amazing.

My second stop was around the corner, in Maddington, where I found a Good Sammie’s shop and some surprisingly helpful ladies.

I told them I was looking for some high heel shoes, as big as possible, for a dress up party and they were eager to help. They offered me advice on everything from clip on earrings to make-up tips.

They found me a pair of black heels and asked me if I wanted to try them on out the back, so I didn't get embarrassed. They were very apologetic when they wouldn't fit properly but I bought them anyway. They were my first pair of heels…!

At a later date I modified them to fit my big feet and become quite accomplished in walking in heels.

As I walked out of Good Sammie’s I was looking straight at the sign for Adult Shop…… I had never been into and adult shop before but I was game for anything now.

I nervously went through the door to be confronted with every kind of toy and outfit you can imagine. I was stunned but new I was in the right place.

My first port of call was the dildos. I wanted something very realistic and big. I had experienced cock before, a few times, and knew I wanted something around the eight inches mark with a decent girth. Within 5 minutes I was holding on to my new best friend.

Next I went for underwear. I looked at G-strings and, although they felt great, I wanted something more adventurous. I found the perfect black one-piece teddy. With a high neck line and g-string bum, it was perfect. The staff member had helpfully pointed out the larger sizes as she guessed it would be for me and I didn't argue the point.

I had seen, and now wanted, some fishnet stockings and fishnet gloves to finish off my "outfit". The staff member, again pointed out the right size for my body type.

At her suggestion, I grabbed some condoms and lube and thank her for all her help. She winked with a smile and said "Enjoy yourself".

I was now kitted up and off on my adventure.

Finding The Right Place

I headed south out of Maddington and aimed for Brookton Highway and up into the hills of Perth.

Just as you pass the last signs of civilisation, about 20km or so from the start of the Brookton Highway in Kelmscott,  there is a sign post, barley visable, for a rest area. Once you drive in, it is a bit of a maze of gravel roads and parking bays.

I found a secluded spot hand waited for my hands to stop shaking.

I opened the door, lit a cigarette, and wandered to the boot of the car. Carefully I took each item I had purchased and unpacked them from the bag. My ears were on high alert for any cars or bush walkers coming my way.

Becoming Ana Le Babe - The First Time

When my confidence returned, I stripped off my shorts, boxers and socks and slipped on the stockings. It felt amazing. I was standing in the middle of the bush with just stockings and a t-shirt on but I felt great.

Next came the gloves. I was felling more and more like the Ana I wanted to be with every piece of clothing.

I unpacked the one-piece teddy and made sure I had it around the right way. I had to put my arms through the bottom, then pull it down until my head popped through the neck hole and my arms through theirs. I struggled with it for a few minutes until I had got the bottom part down far enough in the front and back to be able to clip the crutch together. With a couple of adjustments I stood up straight and ran my hand over my body. I felt amazing.

I slipped into the dress easily and then looked at the shoes. I put my toes in but knew I wasn't going to be able to do them up. Still, it was a tuning point in my life and Ana Le Babe was born.

I pottered about the clearing trying out different poses and tweaking my nipples, sending shock waves through my body, then suddenly remembered.... The dildo...!

Sauntering back to the car, I grabbed the package the dildo came in in unwrapped it. It felt deliciously like the real thing as I played with it in my hands and licked the tip.

I was feeling euphoric by this time and wishing some guy would just drive in an take me on the bonnet of my car, but it was not to be.

I pulled out a condom and the lube. Unwrapping the condom I had the idea of trying to put in on the dildo with my mouth. Not a bad attempt and it gave me my first "fake: cock it mouth experience.

By this time I was so delirious with sexual tension that I grabbed the lube, squeezed some onto the dildo and rubbed it all over with my hand.

I lit and smoked a cigarette while I massaged the lube onto the dildo.

Flicking the cigarette to the ground, I turned and leant over the dildo standing upright from the bonnet of my car. My lips opened and I felt the lube touch then as my mouth stretched open to take the girth. I slid my lips up down, going a little deeper each time until I couldn't contain myself any longer. With the silky lubbed up dildo between my teeth, I took a breath and forced down as much as I could. I felt the head pass the point where I had always stopped before and keep going to the back of my throat.

My God... What a feeling. I took another breath and did it again, and again, and again, until my throat was sore. I gave it one last gag and forced it all in until I felt my nose rubbing on the pretend balls and new I was deep throating.

My nipples were hard as a rock and so sensitive. I used some lube and rubbed them both with my fingers, then squeezed my breasts together.

Suddenly I knew it was time. I yanked down on the clipped join on the teddy and flipped the clasps open with one hand. My butt sprang out of it's black, sexy enclosure and my hole throbbed with anticipation.

After positioning the dildo on the bonnet of my car, I turned and backed up until I could feel the head line up with my hole. I eased back, totally relaxed and let the eight inches slide easily inside me, right up to the base.

I stayed there, dildo fully sunk into my hole, feeling my blood pulse. I lit another cigarette and just enjoyed the feeling of the big cock inside me and the clothes on my body. I felt so dirty, so slutty, so...... amazing.....!

After ditching the cigarette, I placed one hand on the dildo and slowly moved up and down the shaft, feeling every centimetre as it went. As the feeling grew I started moving faster and faster. Within half a dozen thrusts I was literally pounding my hole and feeling ecstatic.

I wanted to keep it up for ever but my cock was so hard I knew it was time to blow. 

Grabbing my cock, I thrust back and fourth a couple of times, then exploded. Cum shot out over the bush, harder and more than I have ever cum before.

I had left the dildo in while I came and slowly lifted my self off it. I yanked of the condom, threw it in the bush, then slammed the dildo and my body onto the bonnet. I deep throated the dildo without effort for a few seconds as my body slowly came down of cloud nine. As the minutes went by, i gently sucked, then lapped at my dildo until I was totally spent.

I had become Ana Le Babe.

I slowly took my Ana's clothes off, regretting I had to return to the real world, but feeling that I had finally found my other self.

I folded every piece individually and neatly and placed it in the bag I had. Regretfully I put on my "normal" clothes, lit up a cigarette and started the car.

My ass was throbbing but I felt fantastic and had already started planning my next outing.

The End - For Now

Next Story - Ana Le Babe Goes To The Beach