This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.
I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also.
I usually liked the mysterious and seductive' look. I wore mostly black – tight dresses or skirts, of which I would usually tie up one side of the bottom into a knot so as to show some leg. My wig usually straight black with a fringe. I also liked to wear a black beret hat (or a black crotchet hat in colder months) pulled right down to flatten my hair, and do my hair slightly pinned back to one side and with strands of hair covering my eyes to give that mysterious peek-a-boo' look.
I did the full make-up, also - usually a blue eye shadow, eyeliner, mascara, rouge, a deep red lip gloss. During my evening prowls when the weather turned a bit chilly, I would also wear a black medium-lengthed trench coat, with the belt tied around my waist. I would make sure there was some frilly slip showing at the bottom, usually dangling off to one side so it would feel so sexy as I walked. I looked sexy as hell, and quite passable, as I was often told.
I had been crossdressing for many years in the medium-sized city I was from that had been LGBT friendly. I would be fully smooth, shaven top to bottom, dress often in black sheer tights, slips, a variety of black skirts or dresses - usually evening wear type, heels, wigs, and even a dildo inserted and get brave and walk around my suburban neighbourhood at night.
It was bordered by a tough neighbourhood and we would get many of these people walking and driving down our streets. I would even venture in to `their' neighbourhood and get whistled at and motioned over to join them. I rarely had the courage to do so. But once I did – that's another story. I would often have cars pull up to me and the driver (and sometimes another passenger) asking if I needed a ride. I always got such a rush walking and swishing along!
Many times I would drive into the city at night, sometimes go to a gay dance club, but mostly go to an adult store in another part of town. I would always have had a few drinks and smoke some weed to get in the mood. You could drive around the area where the adult store was and see many on the prowl looking for some action. I would go into the store, fully dressed in my sensual outfit of choice with makeup, purchase some tokens and go into a booth. I would almost immediately get company from strangers looking for action. I would often give blow jobs in the booth, making sure they drained themselves fully into my mouth.
I would also walk around in this area and get picked up by guys looking for some action. This usually amounted to blow jobs in their cars while they caressed my nylon covered legs. One time, I met a black man. I was wearing a jean skirt, white blouse, sheer black tights and low cut boots. He invited me back to his place in a block of flats. We drove separately but met in the car park at his place. It was exhilarating walking with him with his arm around my waist, me feeling soft and feminine walking in my tights and jean skirt and walking into this very public block of flats, down the hallway, and into his place.
He made us drinks, smoked weed and kissed passionately while he groped me all over. We finally made it to his bedroom where I lost my ass pussy virginity, with my sheer black tights pulled down only far enough to for him to insert his cock into me, and me on my back with my nylon-clad legs and heels in the air resting on his shoulders as he fucked me hard. He came in me multiple times that night.
I've continued to crossdress and seek action throughout the years. One time I was prowling a dark, small car park outside a suburban gay club, again dressed fully in my sheer, seductive outfit and heels and makeup and wig. I was already well lubed from having a dildo inside me earlier and fucking myself with it. Eventually, I was approached by one young gentleman who deposited his full load into my mouth.
Later, still on the prowl, another man came over to me while I was sitting on some steps near the club with my sheer tights-clad legs crossed - one leg dangling over the other and wearing my black pumps with a strap across the ankle as I was leaning back in a seductive pose. He took his cock out and pushed it into my mouth and I sucked him off – still sitting back with crossed legs and one dangling over the other and taking a full load of sweet tasting cum into my mouth. I swallowed it all.
He left, but I hadn't had enough. While walking along in the back of the club, I was stopped by a black man who grabbed me from behind. What an arousing moment – I nearly came right then. While he held tightly against my back, he rubbed my ass from behind, grabbed my neck and kissed me with deep thrusting tongue. He turned me around and made go to my knees and as he pulled out his cock for me to suck. I loved sucking black cock.
He said he wanted to fuck me so we walked across a small bit of car park behind another building when a car came with its lights shining on us. The driver looked stunned. So we quickly walked off to the back of the building in a corner where there were two chairs sitting – probably for smokers. We embraced and kissed passionately some more while his hand made its way to my ass and he poked his finger into my ass pussy through my tights. I was so turned on as we pushed our tongues deeper into each other's mouths.
All of a sudden we hear `I like what I'm seeing'. It was the driver from the car we just saw. He asked if he could join us. I was up for it as was the black gentleman. So, both were now groping me as I traded kissing them and each of my hands rubbing their cocks. I went down to my knees and took turns sucking each of them off. The new guy sat down on one of the chairs and pulled me over to him. I stood bent over sucking his cock.
The black man now had his hand inside my tights and his finger inserted into my ass pussy. I reached behind me and stroked his cock. I then felt the back of my tights get pulled down slightly. I guided his cock, rubbing it across my ass, and then finally guided it to my ass pussy, already well lubed from earlier. Then I felt him enter me. It was unbelievable. Here I am dressed fully in my sexy black outfit feeling sexy and feminine, sucking off one guy while another is fucking me from behind. The man sitting was starting to show signs of cumming, groaning and telling me what a sexy bitch I was, and suddenly my mouth was full of cum accompanying the man's loud groans. As usual, I swallowed most of the cum, but let a little seductively dribble out of the side of my mouth.
He stood up and watched as I continued to get fucked from behind. He started to stroke his cock as he watched. The black man was pumping me from behind and slapping my ass with one hand while clenching my hair in the other. He started to groan, calling me a sexy dirty whore who liked a good fuck. And then he groaned loudly and I felt his cum fill up my ass pussy. It felt so good.
I felt proud and feminine – like a real woman – I had pleased so many men this evening. They both thanked me, asked me to come around more often and left. I pull up my tights with my bits tucked away again, strightend myself out, applied more make-up and swished away proudly, feeling the cum ooze out my ass pussy and into my tights and down my legs.