My Cross Dressing Awakening

CHAPTER 1

So, here I am, in my mid 40s dressed in a short skirt, translucent blouse, black lace bra, sheer black panties, black stockings and a garter belt. Probably not that unusual, except I'm not a woman. My friend, Fia, is dressed similarly as we hold and kiss each other.

Perhaps I should go back a bit to explain how I ended up in this situation.

I had always enjoyed buying lingerie for my wife and often wondered what it would be like to wear. But, she being somewhat more petite than myself, the opportunity never arose. I often mentioned that I liked the feeling of women's underwear and wondered what it would be like to wear. She, typically, laughed off my comments.

We had recently changed locations and I had commenced a new job as a metal fabricator. A job usually performed by "masculine men", not the sort who would wear women's underwear. An older man, Mick< who leased a corner of the fabrication shed became a good friend and I'd often spend time with him. He was an interesting person having qualifications in car mechanics, panel beating and spray painting. We'd often sit around after I'd finished work and talk. To be honest, I felt somewhat attracted to him. One day the owner of the business made the comment that I should be careful of my new friend as he dressed up in women's clothes. I said, "sure, I'll watch out for him," but secretly hoped that our relationship would get more intimate.

I didn't let on that I knew of his penchant for cross dressing but hoped he would come out to me at some time. During this period, I had also been experimenting with gay experiences. Something that had not really interested me since I was much younger. I ended up coming out to my friend in the hope he would do the same with me. Unfortunately, he didn't for quite some time.

Eventually, Mick leased a shed of his own and moved all he possessions into it. I attended there regularly and each time I hoped would be the time for Mick to come out. Finally, some months after Mick moved we were sitting around his table having a coffee and a chat, when he said he enjoyed wearing women's clothes. I feigned surprise and encouragement, telling him that I didn't think there was anything wrong with that. Asking if I'd mind if he dressed right then, I told him I'd be honoured if he were to do so.

Retiring to his dressing room for some time, Mick finally returned dressed sedately in a nice medium length dark blue skirt and light blue blouse with black stockings. To be honest, I was totally smitten and felt a stirring in my pants. She now introduced herself as Fia and sat demurely at the table. Fia was adamant that she was straight and not interested in men. After all, Mick had been married for decades and had six children. Unfortunately, his wife objected to his cross dressing so he had left home to live in his new shed.

This scenario repeated itself for some weeks with Fia's choice of attire becoming more seductive. She would often sit on my lap, grinding herself into my lap; obviously feeling my growing erection as she did so. The feeling of her stocking clad legs as I ran my hand up and down them was, to me, exquisite.

One afternoon as we were cuddling on her couch, Fia asked if I'd be interested in trying something on, say a pair of panties. I immediately agreed that I would like to do that. Leading me into her dressing room, a space filled with wardrobes, cupboards and mirrors, Fia picked out a pair of white satin panties and asked if I'd like to try them. I nodded my ascent as I quickly removed my jeans and underwear. I noticed that Fia was staring at my semi-rigid penis. As I pulled the panties up my legs, my erection grew harder until I finally enclosed myself in those lovely satin panties. Fia rubbed her hands over my buttocks admiring the fit, then briefly against my cock. "Perhaps some stocking would be nice as well," she suggested. At this point I was somewhat lost for words, this being the first time I'd worn anything like this. Fia showed me how to pull on the stockings and spent some time running her hands up and down my legs. "Mmmm," she said. "I think you are going to need a garter belt to keep those stockings up." With this fia told me to remove my panties while she fitted the garter belt. "Panties always go over the straps, you know. Don't want anything getting in the road if you want to take them off in a hurry."

At this point I was unable to resist the urge to play with my rock hard cock and continued rubbing it through my panties. Looking over, I noticed Fia doing the same to herself. "I thought you said you weren't interested in men?" I said.

"But now we are just two ladies having some fun together. Speaking of which, I can't call you Paul when you are dressed like that. What would you like your femme name to be?"

"I guess I'm not overly imaginative, but do you think Pauline would be acceptable?" I replied.

"Pauline it is then, my darling."

We continued to stand there masturbating ourselves until I asked if I could feel her panties. "Only if I can feel yours," she replied. Moving closer we gently held and stroked each other. While I had been with a few men before, this was the most astounding and sensual experience I had had. Eventually we both filled our panties with hot cum and collapsed against each other laughing gently as we recovered from explosive orgasms. "This is the first time I've done this," Fia said.

"I'm overjoyed that I could be your first, Fia. And I hope there will be more experiences in the future."