A Crossdressing Experience...(Fiction)

LOL ? What have I done I thought as I sat in front of my small brand new laptop computer, I was just about to turn it off when a short message appeared on the screen....

It said "Hi Loved what you wrote on here, I am up for a face to face meeting IF you wanted to go through with it that is ? "

The details shown of the person on the profile was = Male, 55 years of age, Clean, healthy, Fun to be with, Open Minded, Truthful.
Plus a body shot but NOT a face view of the person ? He looked neatly dressed in Black Pant's a Nice Shirt & even a tie too.

I sat and thought long and hard about this, here I was a lonely Male living in a big house in Texas, far from my homeland of England, sort of enjoying my work and my play times as well, and added to that was the fact that I loved to Cross Dress, I spent hours doing it all alone at the house, Wig's by the dozen were all placed upon a special holder for them all, dresses of all types, blouses, Lingerie of both the old style type ? you know what I mean here OK ? Open Bottom Girdles, Garter Belt's, Briefers (with the snap or hook-an-eye ) Crotch closer's, along with Bra's that I had filled with Silicon Breast Inserts to fill them out to a nice size DD ? I love big Tits always have.

However, ALL of this was just for MY own benefit and not for others to see or know about ? I just felt that it was my private secret in life and that whatever I did would be just done alone and not involving anyone else.

Some late evenings after my work was over at the hospital I would get all dressed up and in the process of doing so I would get so horny doing it that my cock would be as hard as a rock, and as I stripped off my day clothes and then laid out what I wanted to wear for that night it was such fun I loved it all and only I knew of it all it was my own private special lovely adventure.

As soon as I started to pull on and then up my legs the Black Open Bottom Girdle with it's 6 Garter hook's attached to it for the Stockings to be attached to it, I would already be getting a warm lovely feeling deep in my groin area, this is what I loved.... that erotic naughty sensual Turn-On from doing what I was doing, it was like I had just opened a Birthday Gift Box or something ? It was that special to me, and then I got each Black Lace topped Stocking and slowly pulled them up my shaved legs, and went through the kinky moves of attaching them to the garter hooks mmmmmm I was in a seventh heaven now, the outside world was gone, I was in my own private fantasy land.

I would always try and hook my Pretty & Sheer Bra up at the back, but it always seemed so hard to do it that way (now I know why women do it by holding it in front and then pulling it around afterwards to cover and hold their Breast's ?) BUT I always personally hated to see it done that way ? and wanted to see it done as I felt that it should be done ? and what was from the Back with your hands fiddling with the 2 or even 4 hooks that the Bra might have, for me to see a really Wide Back Bra Strap was a big Turn-On LOL ? I really have no idea just why ? maybe it was because that meant that the woman had Big Tits ? but of course that's not always the case I have found out ? and in fact lots of Bra's have wide back straps and are maybe only a size 32 A ? mmmmmm.

When you wear an Open Bottom Girdle it's hard to wear a Panty or Brief over it ? or even Under it too ? and anyway knowing that the woman is NOT wearing any panties makes the idea of her wearing that Sexy item al the more erotic I feel ? and at times in the past when I was a young horny teenager back in my small village in England, I user to catch a glimpse of my Aunty Dora when she was dressing in our guest room upstairs and her door was left just slightly open.... I would love watching her clipping her Stocking's onto the Garter Hooks of her White Open Bottom Girdle mmmmmm, and she never wore any panties (Knickers) either LOL ? I even saw her Full Black Bush of Pubic Hair at times too, and goodness me she really did have a huge Bush down there too.

Later on I even felt that she knew she was showing herself to me ? and maybe I should have taken more steps to have seen what would have happened if I had been less shy around her ? She sure did a lot of "flashing" when she came to stay with us at the house my parents owned, and OMG one time she even sat on the sofa with her leg's apart so that from my position opposite her in the lounge I could see right UP her dress and even at some of her long pussy hairs all showing..... when that happened I had to find a way of leaving the room and going to my bedroom and stroke my hard young cock with a soft nylon petticoat that I had stolen from my mothers underwear drawer as i laid down on my bed, pant's down and shirt pulled right up, I would slide along the lovely soft material of the lingerie and just "cum" almost within minutes.....!!! It's strange because just using my hands on my Cock to stroke it up and down ? never ever worked for me, I had to use a soft piece of lingerie to get hard and then release.

It's just the same now when I need to 'cum" I use this lovely large housecoat made of nylon that I have had for years and years now and still have to wash every morning after a sensual night of self satisfaction....

BUT !!! This is not addressing the event's of my getting a computer message is it ? sorry for that, so I will continue onwards here.

I looked at the message for what must have been at least an hour before I finally plucked up the courage to reply back ? and even then I was blushing like crazy sitting like I was wearing all my sexy girly clothes and sporting a VERY hard Erection too.

His name was Anthony, but he wanted to be called "Toni" which was fine with me of course because why would I care about that.

I replied back with lots of respect, and told him that I was not really into meeting anyone at all ? and that I just enjoyed doing the dressing up part alone and for simply my own enjoyment, but that I did like to send to others who also held my sort of views of doing such things and it never ever entered my head that I would be asked to meet any of them.

It was then that the Bomb really dropped....? He replied back to me within seconds and said "I loved your shy reply to me, and would simply love to see you in person because your a lot like me I feel ? and I am sure that WE will have a most Beautiful time with each other ? and just by the way I have a woman's body by birth but also have a Cock too !!!!.

I read and reread the message several times over, Did he/she say they were a woman and that they had a COCK too ??? It almost seemed to be impossible but of course nature does do odd and strange things and in this case it had happened I guess.

In some way's I was already getting a sort of mild turn On from what I was reading ? and as I thought about it some more ? the idea of a meeting was getting to be more of a reality LOL !!!!

HOW do you handle something like that Intimately I asked myself ? I mean do they get aroused both in and around their Pussy area AND their Cock's too ???? I was now left wondering just HOW I was going to approach this meeting with "Toni" ? how far will we go with all of this ? I mean.... well ? I am sure that I don't have to draw any pictures here for you readers do I now ??? You sort of have the best of BOTH word's right ? a woman and a man all rolled into one.

Now "Toni" had told me that "She" dresses as a woman, after all why not ? seeing as she's got Boobs and has very pretty looks too (or so she's told me a anyway ?) but she also adds that she has fantasies of using "her" cock too ?

So now I have a New Friend who's a Woman, but also has a Man's appendage too ? and who want's to meet ME personally !!!!!

My next reply back is to say YES to the meeting waaaaaaaa ? goodness me this is so out of this world and I am just asking myself What am I going to do when we meet ? Kiss, Hold Hands, Hug, or simply shake hands and go from there ? It's going to be a real challenge and that's for sure.

I am doing my best NOT to think of the Sexual Intimate Romantic side to ALL of this ? and yet that's almost impossible of course seeing as "Toni" is who she say's that she is ? and I am who she already knows that I am too ? but WHY does "she' wish to meet me ? is she seeing something that I have failed so far to see in myself ? NO that can't be the case goodness me we have not even met as yet and so she can't tell anything.

So anyway after a few more messages sent between us, a meeting is arranged at a nice up scale restaurant in the city close to where I live, however "Toni" has a long drive to get their so I feel badly for that part of course ? but feel that it's either I do the long drive or 'she' does ? and in this case "Toni" wanted to do it.

The "Date" is set for the Saturday on the coming week-end and all I can do is sit and think of WHAT else can I do to try and make this as lovely a "date" as i am able too, I had already told her that I will NOT be dressing up as a "Girl" for a thousand reason's and she accepted that fact straight away too ? I did say that IF she did NOT like ME in person ? then I would not bear any bad feelings, and she in turn said the very same thing back to me too.

She did NOT want to send a picture of herself to me, but in saying that to me she also added that maybe I would just send her one of myself from the shoulders upwards to her just so at least one of us could find the other in the restaurant ? so after thinking about it for a few moment's I said OK and sent her a recent picture of myself that I cropped first.

That night after we had first chatted I laid in my bed still wearing my lingerie and had the biggest orgasm of my entire life !!!!!

My thought's of being Dressed as a "Woman" in doors someplace ? with "Toni" was just sending me into orbit, and to do it for the FIRST time with someone actually seeing me and..... doing it with another "woman" who was part "Male" too ? was simply too wild to even think about.

Life at times seems so hard to understand ? and for me right then and there ? it was far too odd, strange, weird, and kinky to accept.