Journey to Freedom  

rm_LisaJ16 52T
8 posts
3/28/2006 8:58 am

Last Read:
5/24/2008 10:37 pm

Journey to Freedom


I've written a story - that will be both for fellow T-girls as they relate to my story and also very sensual for all you T-girl lovers out there. Each day will be a little bit more - enjoy and send your comments.



Chapter One
The woman I can't shake

It was the last straw for my wife. I had persuaded her that things had changed; my cross dressing days were over for good. In fact, I really wanted them to be over. Why on earth would an above average looking middle aged man want to dress up as a woman? It didn’t make sense; it should be an easy thing to just quit - right?

While I had mostly stopped the cross-dressing and tried my best to suppress my urges ‒ the reality of how things really were is that when ever I took a moment to think abut it, I still very much longed to be a woman. When I see beautiful women on television or in a magazine I am stirred with envy, wishing I could be so beautiful. When I walk through a woman’s clothing store or past the women’s shoe section I am always ‘looking for myself’.

After nearly three years of working hard to kick my habit, I was once again caught, undeniably guilty of putting expression to my inner urges to be a woman. It meant it was over between us. I t also opened up a new chapter in my life. It was up to me how I would fill in the details of who I was and where I would go with the rest of my life.

When I wear a bra; just a simple bra, I shift from general apathy to experiencing very deep joy and satisfaction just at the sensation of having real breasts. I literally feel empty without a bra and when I do have a chance to wear a bra for hours and even days on end, I feel very calmed by it. The sensation of being a woman, even in casual cloths doing casual activity is truly comforting to me.

Every once in a while, I feel the greater urge to wear a dress, and in order to do that I also need to wear panties, a girdle, panty hose, high heels, and then I might as well take the next steps of makeup and a wig and a few other items to ‘finish the course’. The euphoria of getting dressed and then going out for a drive or a walk is more than anyone can imagine, except for other girls like me ‒ they know.

I’ve even developed and kept for myself a persona, a personality of a woman named Lisa Julia Casper; a family person who wishes to be married and have children and would gladly take care of the home front in a relationship. I love cooking and a clean house, am comfortable dressing in sophisticated or sexy outfits. Very much enjoy party dresses and gowns as well as business skirt-suits. She really loves shoes, loves shopping for herself, but also enjoys casual cloths, in women’s jeans or shorts and fun times including cross country skiing and walks, hiking and camping in the mountains. I also love the beach and holidays in the sun. I enjoy a drink of wine or dark ale watching the women’s or discovery channel and my favorite TV sport to watch on TV is the NFL for reasons that many women’s would relate to.

I recently built up a ‘stash’ and spent an evening in Vancouver as a lady. I wore a padded girdle and then stretch jeans and a nice soft shirt over a fully stuffed B cup bra. I finished the transformation with makeup, very carefully applied, a wig and jewelry and after taking my purse and placing items like lip stick, blush, mascara, keys, room entry card and a few other things, I was ready to go out. Only thing, I had to walk down the hallway in a busy hotel, walk down four flights of stairs (elevator was too risky) and then come out of a back exit from the second floor, knowing that cameras were trained on me as I walked out, with purse in hand and car keys and room entry cards inside.

I walked around the hotel, to the front parking lot and got into my rented car, again noticing cameras on the parking lot. After getting in the car, I went for a drive and found a good place, with adequate traffic for safety to go for a walk and feel the breeze past my flowing hair. The black pumps I was wearing had three inch heals, but they were also very comfortable for walking, almost as easy for me as walking in running shoes. I really loved those shoes. That night was a home coming after nearly two years of not going this far.

Later, I had to find my way back into the hotel, waiting for the front desk staff and porter to be occupied with checking-in other guests and then walking into the lobby and up the open stair case to the second floor, and then across a very big room to the stair well and then up the stairs and down the hallway, to finally get to my room. I breathe a sigh of relief ‒ I made it without getting caught. Of course quite a few people saw me, but they would have no idea, even if they knew I was a guy, who I was.

But that just wasn’t enough. I had ‘cased out the joint’ now and felt I could be a little more ‘conspicuous’. I had to do the same again, this time in a skirt, wearing fishnet pantyhose and in higher sexy heels. While tempted to wear my much shorter black party dress, with fishnets I looked too much like a hooker. That would likely get the hotel staff coming after me.

My new high heels were black, open sandal, with 3 ½ inch spikes and ankle straps ‒ super sexy. I also added a silver anklet to provide extra ‘bling’ for anyone taking a close look. The heel bottom, being very small made for a much greater challenge to walk, but I was so good in even those high heels. The shoes actually forced me to take more deliberate, delicate, feminine steps with the added bonus of a bit of a swing in my hips as I walked. My skirt was very feminine with a ton of material and hung just past my knees. I loved those shoes too but they sure were not for long walks. I might walk as much as a mile in them and then have to stop.

I planned to repeat the same route; went down the hallway, down the stair well, through the hotel second floor area, BUT this time I was noticed seen by a hotel worker who asked if he could help me. I panicked and pretended to not hear him and was forced to avoid a face to face confrontation by walking down the front stairs (big and open) and into the open main lobby area with a dozen of so people in it and then out the front door exit, for a quick walk to my car ‒ I was totally freaked, heart racing. I got to the car and turned around to look if anyone was around. My heart was pounding and I was breathless from the shock, but then the thrill hit me, I would never had done that except I was forced and it really was not so bad.

I got in the car and thought about what just happened and realized, I probably was completely accepted as being a woman going out for the evening. I had to remind myself that I actually looked very ‘womanly’ when fully and carefully transformed like I was. I even walked and ran like a woman. I’ll just need to stay away for an hour or so and then wait for the right moment to go back up to my room.

An hour later, I arrived at the hotel again and decided I’d just walk around the area for a while. I also was looking for a good moment to get back into the hotel. I ended up having to wait a long time for new guests to arrive to take up the attention of the hotel staff. When that moment finally arrived (about 45 minutes later) I walked calmly but also quickly through the front door and straight up the stairs so as to not be noticed. I knew by backside including fishnets on my legs, could easily be seen by the staff or guests as I walked up those very open stairs but I did not look back to see. If they caught a glance big deal; if no one noticed, even better. The objective right now was to get back to my room and my heart was racing like crazy. I walked more slowly across the second floor lobby; I wanted to be able to turn around if someone came from around the corner. I watched and listened to make sure no one else was there. I finally got to the stair well and walked up to the fifth floor and finally back to my room. Why do I do that to myself?

I know the adrenalin rush is one reason, but there is also this amazing satisfaction of being seen by others, passing as a woman. When walking on the street, I like being looked at and even leered at by the poor helpless men who drive by and can’t help themselves. Men are wired for looking and I enjoy being looked at. It was only a couple weeks later in Regina I was doing the same thing. I had a car load of 3 or 4 guys drive by and then after seeing me, tooting their horn and then decide to turn the next corner and come back to pick me up. I ran hard the other way and hid. The guys in this part of the world might end up killing me if they realized I was a transsexual. But they were looking for me. What a hoot.

On another occasion, I was in Calgary, having transformed myself into a rather good looking woman, I decided to go our for a late evening walk around the hotel area wearing a pair of tight fitting, low cut ladies jeans. They really look good on me and the fact is I do have a rather feminine butt ‒ big, round and inviting.

I had shorter healed sling back shoes what fit very well and wore a jacket, with a long, straight, flowing light amber colored hair. I was a ‘looker’ and as I went for a walk I suddenly noticed a car pulling up behind me and slowing down. I turned and took a glance and realized it was the police. The two of them drove by very slowly and then drove away about a block.

I thought I was so lucky that they didn’t stop but then the car suddenly turned around coming back for me. I could't believe it - they were after me...I ran. I was so fortunate that I was right next to my hotel. I managed to get into the doors just as they pulled up and once I was inside I knew they would not be able to find out who I was. If I had been a block away from the hotel, as I was only 5 minutes earlier ‒ at the very least I would have been very embarrassed being caught by a couple Calgary cops in a dress. But what a rush!

A few weeks later I once again purged myself of my latest stash but my heart was not truly in the purge. I took the professional counseling route and the religious guilt route and tried everything else, only to find myself again and again in the same place, knowing that in my heart I was very much wanting to be a woman and also, as a woman to be with a man who loved me.

More and more, after three years of trying hard to ‘be good’, I longed once more, just one more time to transform myself more completely, to shave my legs and body, to find a cute wig, to do my face, to wear a gorgeous dress and some knockout heels, to do myself up as a really good looking woman; to spend days at a time being a woman; morning, noon and night.

But now my desires have taken another step - I sooooo much want to be with a man...

tazzerman2000 60M
18958 posts
3/28/2006 12:07 pm

Can't wait... -tm

These blogs are only fun if you LEAVE comments!!!

Please visit my blog tazzerman2000

LisaTSforU 72F
1 post
4/2/2006 10:22 pm

Look forward to that hun....drop me a line lisa-michaels at the place that's HOT!
Hugs, Lisa

rm_jram55 63M

4/18/2006 9:06 pm

Very, very interested.

rm_jram55 63M

7/27/2006 7:53 pm

It will be a joy to read. I look forward to it. jmac

joejoe69er1000 50M
22 posts
8/2/2006 9:12 am

I totally understand in a way that you might be surprised to hear.

Talk to ya (hope to be with ya) soon baby.


johnsheppguy 53M

1/31/2011 11:32 am


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