I never liked the way that people would look at me. It was almost as if they were reading my mind, and somehow were able to judge my greatest secrets.
To my readers, I thank you and perhaps you will understand when I write that the feeling of female clothing was the powerful aphrodisiac that was responsible for my first dressing as a girl as a child.
That's where it all began, really; a little make-up here and there, growing up with only women, wearing my mother's and my sister's clothes, their dresses, their heels, and underwear, and next thing you know I was secretly shopping on my own in the women's department.
I never made eye contact with anyone in the stores, but the girl's at the register always knew I was buying the clothes for myself, not, as I fibbed, for a girlfriend, or something. Some of the women, as they were all beautiful to me, I recall, noted my purchases with interest, and appeared rather curious as to what I was up to, or maybe even how I might look, having already a girly appearance, anyhow, in the lingerie and heels I bought.
One clerk had said, you know those garter belts won't go with these pantyhose, right? To which, at sixteen, I replied that I did know that very well, and smiled a warm thank you.
After those nervous days, when relief only came when I was done shopping, out of the store, and back in my car on the way home had, over the years, begun my obsession with cross dressing, which progressed into something now sensual and erotic: fulfilling.
But it was still just a hobby of mine, dressing up in pretty things, eventually graduating into more mature, sophisticated items as I developed an insatiable taste for more, acquiring more skill in applying my own makeup, styling my hair and nails, but never a full-blown lifestyle choice.
I, James, worked a steady job in human resources during the week, disguising myself as the young man my co-workers saw me as, but on the weekends I would venture to the trans-clubs and sit alone at the bar, dressed up and introducing myself as Mary.
Mary, I always fancied the name Mary. It suited the way I presented myself. I'm Native American by blood, with soft, feminine features to start. My body is lithe, smooth-shaven, and nubile. I do aerobics, and butt-workouts, for a well-rounded behind. The tone of my skin is a light-coco; I stand about 5'6; weigh about 140 pounds, and my feet have always been a little narrow and petite, a size 7 in men's, actually, but I can manage an 8 1/2 in women's heels. My hair was my pride. It was thick and black, and I always kept it well passed my shoulders in a braid. But when I started dressing up I knew I wanted to style it in whatever way possible. I went through various looks over the years, but eventually settled on bangs over my brow line as my go to look.
Remembering back some years, now that I am writing this, I did get caught a few times, but nothing too extreme.
The first time was when I was about ten and my mother caught me with a whole heap of my sister's missing clothes, and shoes. She didn't say much, and didn't punish me either. She just told my sister that she had found the missing clothes, and that was it. Thank god, but I was so young then, even I didn't understand what it meant to me.
The second time was when I spent the summer with my aunt on our reservation, and my beautiful cousin walked in on me changing in the bathroom.
I was sixteen and she had just turned eighteen, and I was trying to get the seams straight on the stockings I brought with me to try on for the first time. I thought no body was home, but I guess she was. I didn't even hear her walk into the bathroom until I heard her throat clear, and ask, "what the hell are you doing?"
I didn't say anything. I didn't know what to say. I just gazed at her, frozen. She stood there for a good minute; sizing me up, I guess. Luckily, I wore panties. But, after a moment, she smiled like it was funny, then closed the door, and walked out. We never said a word about it ever again.
The last time I was caught, and this little tale still excites me to this day. It's a bit longer, but it was one of the most memberable moments of my secret life. It was the first time my fantasy actually became a reality.
It happened when I was in college, and my roommate Teddy at the time had left to visit his family over winter break. I had no family near enough to visit, so I planned a whole month of fun for myself.
By then, I had amassed a pretty decent sized collection that now included some more X-rated items: a butt plug, a cage for my cock, a long brown dildo, some bondage cuffs and a ball gag.
At that time, I used to record my damsel in distress bondage sessions regularly so that I could edit them, and post them online, but I was never brave enough to actually post them. I was too paranoid that someone I knew would see them, and expose me.
Anyways, the days must have flown by, because next thing I knew I was in the middle of filming one of these sessions when Teddy walked in.
I wore my pleated navy skirt, white blouse and Mary Jane pumps that I bought online. My thong clad ass was up in the air as I inched forward to reach for the keys to the cuffs. I heard the door close, and looked back to see Teddy just standing there, speechless, processing what he had just walked into. I recoiled back in shock, trying to hide, but how could I? I was tied up on the floor with a gag in my mouth, and Teddy just stared. I mumbled through the gag at him, trying to explain, but it was all gibberish, which, ironically, was what I bought the big ball gag for.
Teddy said nothing. He closed the door, locked it, and walked over to me, but he stepped over me and picked up the key. I thought he was going to release me, but he put the key in his back pocket, and sat on his bed. He looked me up and down, eyes taking in all of what he saw.
I glanced up at him from the floor, blinking in confusion, and then remembered then that I wore mascara, and a little eyeliner. My hair was in a ponytail and my bangs hung over my forehead. I must of looked ridiculous to Teddy, all dolled up and helpless, wearing a schoolgirl uniform, and heels. I felt my cheeks reddening. Teddy wasn't say anything. His poker face gave nothing away. He just stared. All I could do was gaze unknowingly back. I didn't know if he was going to call security, or tell someone to come see this, or beat me up for being a faggot roommate.
The answer finally came when Teddy smiled and said, "You look pretty like that, James. I didn't know you liked this sort of thing. You're really, really good at it. You surprised the hell out of me when I walked in, though. I thought you were your girlfriend," he chuckled. "You looked that good, then I realized it was you, and you still look good. Wow." Teddy smiled at me.
My heart raced, beating too many beats too fast. I couldn't believe it. He wasn't freaked out. He didn't judge me, and shoo me away. This was the first time I ever felt secure, both figuratively, and literally secure at the moment.
I smiled timidly back at him behind the gag.
Teddy got down on one knee, and turned me on my right side. My short skirt rode up my smooth thighs, and the v of my panties peaked from under the pleats.
"May I?" Teddy asked.
I didn't know what he was asking, and I didn't care. I just nodded yes.
Teddy slid my thong panties down to my knees.
I closed my eyes, feeling my cheeks red hot. I didn't want Teddy to see my cock crammed in its little cage, dripping at the tip.
But... Teddy didn't skip a beat.
"Do you want me to take that off?" He asked.
I opened my eyes. Teddy's face looked worried. He asked me about the cage with concern. I shook my head no.
"Okay," he said, smiling. He reached into his back pocket and took out the key, and unlocked the short chain locking the wrist cuffs to the ankle cuffs.
I straightened out long toned legs across the carpet, sighing in relief.
Teddy smiled. "Come here."
He hoisted me up, and plopped me on the bed, sitting me eye to eye dead center with the middle of his tight blue jeans.
His bulge, I gazed; He was turned on as well.
I looked up at him. He was much, much taller than me to start, but from my view he towered. The body of an athlete, who didn't play sports, a lover of literature, a writer of poetry in his spare time.
Teddy rubbed the back of his neck, looking down at me, unsure what to do next.
I gazed at him, feeling as though I could read his thoughts. He still hadn't uncuffed me, or un-gagged me, either. So, he definitely had something on his mind.
"Do you want to have a little fun with me?" He asked, slight hesitation in his tone.
Now it seemed to me like he felt like he was the one out of place.
But, still I nodded my head yes - again.
"Okay." Teddy breathed in relief. "I'm going to take this off now." He reached around my head. His firm bicep grazed my cheek. I smelt his skin, freshly washed with Old Spice. He unbelted the ball gag. He gave it a good tug, but it was lodged pretty deep inside of my big mouth. Finally, it gave with a wet popping sound. Drool fell out onto my chin. My red lipstick smeared the ball. My jaw ached, but I had gotten used to it by then.
I waited, watching, as Teddy unbuttoned his shirt, and tossed it behind me. His stomach muscles, smooth and flexed, beckoned to me. I watched, patient, not speaking, as he lowered his jeans, and then his briefs. His cock revealed to me, long and shapely.
This was the first time I'd seen it free.
I'd seen him in tight Jockey's before, around the dorm room, but never like this, and so close at that.
The smooth shaft loomed just inches from my mouth.
I still waited, batting my eyes at him.
Teddy smirked.
He picked up on the game I played, that I was waiting for his permission to blow him. He nodded to me that I could begin.
I closed my eyes and leaned forward, smelling the manly skin of his cock, elated now that Henry walked in on me.
I softly kissed the mushroom head, introducing myself so to speak. Then, I pounced, and covered his member with my mouth, and began to suck, and pull back on it, letting my tongue flick out and feel the small slit at its bulbous end.
Teddy shifted his stance, widening his legs, enjoying the soft feeling of my lips.
A moment prior, when I measured up the cock's length in a glance, I knew I could swallow Teddy all the way down to his clean-shaven scrotum. I don't think he expected me to have so much practice, but I was secretly ready for my first time.
My nose pressed against his pubis and my chin grazed his balls each time I deep throated Henry. His moans grew louder as I held the cock in my mouth for a moment, then withdrew, dragging my wet lips over the shaft, never taking my mouth off to breathe before I buried my face right back down again to the base.
I continued quietly, and efficiently, satisfying this man. Soon Teddy's cock was slick with saliva and slipped down my throat with ease.
Teddy's body tightened. His moans rose as his breath became heavy, and yearning. I felt a strong hand place itself on my head, and usher me up and down so that he fucked my open mouth. But, the tension must have been too much for Teddy to bear as he released my head. He pulled his cock free of my mouth, a strand of drool hanging from the head. He placed his slick throbbing shaft against my cheek, and offered his balls to my mouth. I suckled at them, pulling, releasing, and licking them up with my tongue.
