When the gay community put the "T" in the LBGTQ I thought, "How great. now we have a community." How wrong I was. The gay men I have shared this with absolutely do not understand the conduct and have no desire to hangout or be friends on that basis alone. This also applies, in my direct experience, to Lesbians who think we are crazy to even imagine that they would be a part of anything we do. If you share with a girlfriend - the minute you do she is already thinking in her head of how fun it will be to tell all of her girlfriends that you are a sissy. Don't share it just because you need to deal with it - it is a huge mistake, and you can never take it back.
The best way to deal with this "hobby" is to seek out and attend crossdresser events and conferences around the country. Wild Side weekend in Las Vegas is full-on feminine immersion experience once a year and there are others including the First Event in Boston.
My adventure started with finally committing to a photo session with a Crossdressing Service in Long Island near home. I had wanted to go for years and when I turned 40, I was like, "Well, if not now, probably never." I was determined not to die without experiencing a full transformation.
I was so nervous when I arrived, but "Austin" was so cool and an old tranny himself, so I relaxed as we picked out an outfit from the stash at the studio. Gold high heels (size 12) opaque Capezio tights in light suntan to completely hide the hair on my legs and then a slinky purple dress with a short bolero coat to hide my arms. Naturally, the corset came first, and Austin tightened me in so I could barely breathe. He made sure that I could not look in the full wall-mirror until he said so; keeping the blue curtain closed over the mirror while he performed his magic.
Sitting in the makeup chair he started with a lotion all over my face than used small alcohol prep pads to clean away the areas on my upper cheeks by the sideburns and also along the forehead about 4 inches above my eyebrows. Using a flexible surgical tape, he pulled the skin on my face up until it was very tight then used the same tape over my eyebrows, pulling upwards and securing the tape against the wig cap. I could feel my eyebrows arching upwards, and all my wrinkles and lines smoothing out. That technique takes years and years off your face.
Then the makeup began, and it took almost 40 minutes. Finally, Austin had me stand up and when he opened the curtain on the mirrored wall I was amazed and I actually I got turned on by my own image! I hear that that is not unusual as so many people think that a strong tendency to narcissism is part of the crossdresser's quiver. I looked amazing - he had quaffed a strawberry blonde wig that fell just blew my shoulders and my figure was so sexy with that corset the foam hip pads and the silicone breast forms he inserted in my dress. I could have walked right past my mother and she would never have recognized me.
The next hour we spent taking pictures. He was excellent at posing me and at the conclusion I left with a CD with about 50 pictures and feeling that I had really changed my perspective on my crossdressing. For the first time, I thought that maybe I could actually go out to a club or a meet-up fully dressed. When I left, I learned that I had become one of "Austin's Angels" as he called his clients.
The thought of going out as a girl and those pictures dominated me but, that old fear had never left so months went by while I returned to my secret dressing at home when I could steal the time.
Eventually, I heard about a "Tranny Night" at a gay bath house 45 minutes away. It was upstairs with a rabbit warren feel and small open rooms, corners and closets as well as a fairly big "playroom" with a swing.
I nearly backed out when I had to give my ID to the door, but it did make it safer and the locked doors kept it private and it was just far enough from home to feel that I would not be discovered. On entering, there were at least 5 other "Girls" like me already there and dressed. By the end of the hour there were 6 more. They walked and preened about for the many men who admired and fantasied about Trannys who were also milling around. It took me 30 minutes to do my makeup in the bathroom - using the tricks I had learned from Austin - it wasn't perfect, but it was very dimly lighted in the club and we are looking for progress not perfection!
I came out and joined the 'parade' of girls and spoke with a few and moved through the club several times. Once I stopped and sat in a small room it was only minutes before an Asian guy came in and showed his cock. Now - my dressing, up to now, had never been about sex. I am not gay, and I had never in my life even touched another man's penis. I felt reluctant and frankly ashamed but again - "if not now when" - so I took him in my mouth and felt him grow and warm up as I sucked him gently. I'll admit to being surprised when I found my own cock getting rapidly hard at this and I relaxed into my work. The feel of the skin in my mouth and his taste was delicious to me. He came without any warning and I gagged at the thought of his cum in my mouth and spit it all on the floor. I quickly changed and showered and drove the 30 minutes back to the house where my wife was already in bed.
That experience stayed with me. My disgust slowly changed to desire and I waited for the stars to align so I could have an excuse to be out until 10 and try it again. The next time was much the same but more girls this time. Pretty and talented crossdressers who all looked great to me.
I ventured into the "Playroom and it was very dark taking a few minutes to become accustomed to the darkness, I eventually made out that there was a bench with several guys in towels, a round bed with a plastic sheet cover, and what was the "sex swing' hanging from the ceiling. I just took a seat on leather ottoman and watched to see what would happen and again, in minutes, one of those guys was in front of me holding his cock out. There was no hesitation this time and this poor guy, must have been a premature ejaculator as he came in my mouth in less than one minute. I savored the cum this time and waited a few seconds before I swallowed it all warm and running down my throat.
By the time I had gone back to "Tranny Night for the 4th time, I was a hopeless slut - I was counting the cock I had sucked and had a goal of ten in one night. I made it to seven before the seventh turned me and fucked me as I held on to the wall balancing unsteadily in my high heels. He came quickly too, and I stumbled out in my heels, back into the comparative light of the center lounge when I noticed that I had cum dripping down my legs. Thank God I saw that and did not go home with my trousers full of cum dripping from my ass - what if my wife could see that? The record for me was finally ten cocks sucked and then fucked by four guys, two of them came inside me.
Honestly, this all started because of the makeover and photo shoot I had done - I believe that without that I never would have escalated to the filthy behavior I now enjoyed so much.
I was in a period when I had to travel to New York for business once a month and I kept the habit by claiming I needed a hotel so as not to drive through the tunnel to long island after a drunken client meeting. The hotels were a great refuge for me - you can take your time with your makeup in a hotel and for most of us girls the makeup table is a wonderful part of the ritual. I satisfied myself with taking pictures on a timer and posting to my new identity on Flickr. Soon enough this was not enough and the first night out from the hotel, I wore a long overcoat and braved the walk through the lobby jumping a cab to the 7th Avenue Adult store. I put the coat over my arm and exposed my super short metallic mini dress and preened right though the store to the video Arcade in the back. I did not know that there were black men there who make a living with those beautiful African cocks, but it was good news to me.
Slipping into a booth with the door unlocked soon one of those black guys pushed the door open and gave me a look - instantly I handed him a twenty and he came in, unzipped and I saw my first BBC, what a gift from God. I sucked him only until he was hard and then stood up indicating with no words what I wanted. He turned me and inch by inch buried that cock up inside me. It was insane. Just insane. My eyes rolled back as he quietly rocked me back and forth going for full penetration. He stopped and pulled out just as I was fully lubricated and dilated and he looked at me knowingly - I reached for another 20 and with that he slid back inside me and finished himself off.
The New York experiences were dangerous, so to avoid the public spaces I cultivated the habit of posting my girlie pics on Grindr and I always had at least one hot guy come to my room for sex.
The work trips to New York ended because of my job and I did not get to go out again for months. The desire to dress was building and building. Recently I had seen a number of cars in a wooded rest area on the highway and heard it referred to as a "Pickle Park". I went for a drive at lunchtime to see if there might be something there for me.
Remember that I had only sucked cocks when I was dressed as a girl. Again, I was put off, fearful, and reluctant to join the men in the woods with my street clothes on.
I became a regular at the rest stop - sucking hundreds of cocks over the following year and, once in a while, getting lucky enough to find a man to fuck me. I always left there with at least one good load down my throat.
I realized that now I was a full-blown cocksucker faggot. I no longer had to be dressed like a girl to take cock.. I had crossed over.
I still like to dress when I can but nowhere near like before - You see this habit escalates and escalates and we take more and more risks to get what we want what we need. The addiction had become real for me and now I am afraid I can't stop, and my fantasies have escalated yet again, now I dream of being a tranny street whore -Well, I do know a place on 10th avenue...
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