My Obsession

I was babysitting for my sister the night my life changed forever. I was simply looking for something to read when I went into their bedroom. She'd left her lingerie drawer open and suddenly all my attention was focused on the lacy white corset on top. Nothing else mattered, nothing else existed, nothing could have torn my attention away from it. I just HAD to put it on! Then, of course, I needed nylons and panties to look right. Girls didn't run around in just lingerie so a dress and heels followed and at the age of eleven I became obsessed with dressing myself femininely!

At home it was too crowded to have any privacy usually and I just knew that everyone would ostracize me if they found out. Boys didn't wear girl's or women's clothes! But every chance I got I eagerly found myself dressing from the skin out in female clothing! It was never enough just to wear one item or only lingerie', I had to dress fully! When I was dressed there was just the serenity and peacefulness of feeling feminine while time seemingly stood still and nothing else mattered.

Why I'd ask myself after, why was I so different, but there was never any good answer. It was a part of me that took a long time to accept. A part that gripped me and held me captive in a compulsive obsession I couldn't fight or resist in any way. And as I was to discover a part that would last the rest of my life no matter how I might try to resist or stop myself from dressing up.

As the years passed it wasn't enough to simply wear women's clothing. Women did so much more and now I had to as well. Long hair for males was the norm at the time so I learned to style mine into a very feminine pageboy. I polished my nails, both fingers and toes. I experimented with make up till I was able to do my face as well as any thirteen year old girl. I'd shave my body and legs to be as femininely smooth as possible; never once stopping to think about or remembering that it wouldn't grow back overnight.

When I moved out on my own it became easier to indulge but also harder to hide my obsession. Friends and family don't always call before they drop over and there were a few scary moments when I was nearly caught. Sometimes I left something out in my rush to change back or discovered that I hadn't quite removed my make up or my nail polish fully after I'd let them in! I prayed that they wouldn't notice.

It was a rewarding part of my life but still a very lonely one in many ways. Then came the time I found myself peeking out the door at two in the morning, daring myself to walk down to the other end of the hall and back. Rushing out the door and stumbling along the hall, all my femininely graceful ways forgotten at first until a part of my mind reminded me that I was supposed to be feminine. Slowing down, adding a feminine sway and gait as my heart pounded so rapidly then walking carefully down to the end of the hallway and back until I was within ten feet of my door. Rushing to get behind it again and close it. Feeling so exhilarated and thrilled that I'd actually done it.

From there I increased my self dares to actually having to go onto the landing and stand there for a whole minute or two; to go as far as the front or rear door and stand there at first, to stepping outside and walking around to the other door while dressed! It was so very, very intoxicating to savor the sensations of being outside dressed. Like the swirl of cool air around my legs and under my short skirt, the tug and stretch of my garter straps along my thighs, the way my nylons felt as they rasped together with each step, hearing the click of my heels against the concrete!

Eventually I dared myself to go as far as to walk around the block. Even more exciting, more intoxicating and oh so nuch more scary all wrapped together! Not that anyone else was there to share it with or see me. Daring myself to go further, to add another block to my walk, and another until during one late night walk someone came out of a house and looked my way. I ran like the frightened little girl I was aping and hid behind some trees till I was sure I was alone again.

The world didn't come to an end the next day! There was no headline in the paper revealing my secret to the world! My friends and family still didn't know and confront me. Why had I thought they would and been so scared? Was I that ashamed of what I was doing? If I was why did I continue to do it? Still my world hadn't ended from that brief encounter, if you could even call it that, and I felt better now about being seen from a distance.

Not that I became more brazen immediately or went out of my way to be seen but I pushed my limits harder and started going out for walks earlier and earlier. I forced myself not to run when someone was within half a block, stall for time by looking in my purse or turn around and go back. It wasn't easy to do I was so nervous but as no hue and cry or crowds chased me it did help me to relax and become more confident.

Confident enough that I was able to walk past a parked car with someone in it without rushing by. Confident enough to bravely enter a store and buy a chocolate bar. Confident enough to walk past other people walking down the same sidewalk without hesitating or dithering or turning my head. Heady stuff!

Not quite confident enough to do more than smile at a passing wolf whistle or offer of a ride. Not for another few weeks anyway. A further dare to myself made me get into a car and try to appear relaxed enough to talk with the driver. He accepted me as a female, even my voice. Not that I did much of the talking. My confidence and self esteem soared!

When he parked in front of the house I was supposedly living in I started to get out but he grabbed my arm and pulled me across the seat for a goodnight kiss. His lips were pressed against mine, his tongue teasing my lips apart before I knew what was happening. Wonder of wonders I responded eagerly; teasing the tip of his tongue with mine as it slid between my lips. Pressing my nonexistent chest out by arching my back, moaning softly as his hand fondled my leg and slid up under my skirt to caress the bare thigh above my nylon top.

His kisses were intoxicating and I didn't want him to stop! I wanted to go further but common sense finally kicked in before he discovered that this girl had different equipment inside her panties. I jumped out of the car and ran thru the backyard, then cut thru another yard, crossed the street and did the same to get to the alley behind the apartment building I lived in.

Inside my apartment I shivered in delight at my daring while silently kicking myself for doing it! If his hand had made it an inch higher things would have gotten very ugly I was sure. He might have accepted me wearing the heavily padded bra but not the surprise inside my panties.

Or would he have? I now knew such things happened all the time with gay guys tho I wasn't sure if any of them wore dresses and lingerie' but how do you tell? (Living in a smaller town before the internet I had no idea of the real world and what went on. I had no clue that there were others like me or that some not only dressed but lived as women and even became totally female after GRS.)

Knowing that my voice had passed I did place an ad on an adult line using the name Amanda. I responded to messages and had a few live chats posing as a female, exulting in the idea that I could excite men into masturbating and even cumming just from the sound of my voice. I did get into it and became fairly excited myself quite often but never did more than rub myself thru my panties or pinch my nipples under my bra after the one time a guy wanted me to and I discovered how sensitive my nipples were and how sensual it was.

Things might have stayed the way they were if I hadn't pushed the limits again and confessed to a few selected others that I wasn't completely kosher. Only one seemed shocked and hung up on me. The rest seemed to not only accept my obsession but became even more excited by the idea! I was in heaven. I even got brave enough to agree to meet someone.

Kevin could only meet me in the early evening as he was married. We arranged for him to pick me up when I was out for a walk that Saturday. I spent the whole day getting ready, showering, shaving my body and face as close as possible, doing and redoing my face for hours until I'd used up half my bottle of foundation. Selecting just the right lingerie to wear, the right perfume, the perfect dress and heels.

I was so extremely excited, so incredibly turned on, so utterly scared and nervous. Was I really going to do this, let someone see me dressed? Yes I was I told myself sternly. Was I really going to meet someone I'd had sex with over the phone? Would he be expecting me to have sex with him today? Was I ready for this? Of course he would and well I might not be completely ready and back out of the sex part at least I'd actually meet somone who knew I was dressed femininely for him and get his opinion as to how feminine I looked and acted.

I needn't have worried so much it seemed after I got into his car. He drove around and talked to me till I settled down then asked me to slide closer so he could put his arm around me. It felt good and I rested my head on his shoulder. Leaving town he drove out into the country to a secluded spot and parked. Holding hands we went for a walk and talked some more.

At the far end of our walk, when he was sure I was ready, he turned to face me, pulled me close and kissed me deeply. My mind went blank I was so into that kiss. If a brass band had passed us I wouldn't have noticed! Nothing but that kiss mattered! Nothing but his lips on mine, his tongue flicking against mine so sensually, so overpoweringly, existed in my consciousness! The feel of his lips on mine lingered as he broke that kiss and smiled down at me. He kissed me again with the same result.

He was smiling down at me when I became aware of my surroundings again. Shaken by the intensity of my reaction I just stood there stupidly as he disentangled himself and took my hand to go back to his car. My first few steps were taken on very rubbery knees and he had to steady me till I was able to walk properly. When we got back to the car he leaned me against a front fender and kissed me again.

I have no idea how my dress ended up on the hood of the car or when my bra was unhooked and the stuffing fell to the ground. No idea at all, just vague recollections of lifting my arms and twisting a bit to help him undo and remove them. His lips on my nipples as he kissed and nibbled them sent firey waves of sensation rippling thru my belly to center inside my panties. His lips on my neck made my pulse race even more. My cock was hard and throbbing, ready to explode. I didn't, couldn't, have resisted in the slightest as he slid my panties down my legs and wrapped his hand around it to stroke me.

I expolded in his hand after a few strokes and briefly came to my senses feeling so revolted and ashamed of myself that I wanted to break free and run but Kevin leaned forward to kiss me once more. I was lost again in the overwhelming sensuality and gasped as his one hand spread my cheeks and a finger, slippery with my own juices, slid into me. I gasped and squirmed at the intrusion but that just eased it deeper.

A second finger spread me further then a third even more. It was hurting me to be spread that wide but his kisses still sent a conflicting message to my brain until he wriggled his fingers inside me and something changed. My cock was hard again and I no longer wanted to break free or run. His free hand undid his pants, lowered them and his shorts before he removed his fingers. I felt the head of his cock press against me then easily slide inside me. Half lying across the hood of his car, in just my heels, garter belt and nylons, Kevin took my virginity gently and easily.

He lasted a long time. At first I felt like I was being stretched so much I must have been torn open. Is this what girls felt like? If it was how did the human race survive? Then just as the wriggling of his fingers had done before, it stopped being painful when his balls slapped lightly against me. I began to welcome each thrust, rocking my hips forward to meet them and wrapping my thighs around his waist.

One final deep thrust he held deep inside as I moaned softly then louder as I felt his cock erupt inside me, filling me with his cum.

My body convulsed around him, every muscle tightening and releasing with each spurt I felt and welcomed. I didn't even realise I'd cum again until after, when I saw the residue splattered across our bellies.

He held me and left his cock inside me giving me a gentler kiss, barely brushing my lips with his. I was in a state of confused blissful shock and unsure of what to say or do or how to react. It had been so different yet so similar to what I'd experienced with the first girl I'd ever done it with, not that long ago.

Kevin stepped back leaving me half on the hood as my mind whirled. I just laid there in baffled wonderment as he straightened himself up. He helped me down, used some tissues to wipe my belly dry and like an automaton I put my clothes back on and got into his car.

He talked but I never really heard what he was saying as he drove me home, just nodded at various times as I tried to comprehend what had happened. I'd been fucked like a girl! I'd lost my virginity at the edge of some farmers field! Was this what I had been dressing up for? Was this the reason I'd learned to paint my face and nails? Was this why I'd practised walking in heels for so long, learned to speak in a feminine voice? Was it? On the other hand, wasn't it?

I walked home from where he dropped me in a daze. It wasn't till I was half a block from home that I realised I was automatically still femininely swaying with each step and smiling a more feminine smile when I passed someone and they smiled at me. I wasn't rushing, I wasn't worried about being seen, I wasn't my usual half scared self; just completely feminine inside and at ease.

I showered as soon as I was home, looked disdainfully at my normal pj's and slipped on the sheer babydoll nitie I'd planned to wear the night I lost my virginity. (While I had done that, just not while wearing it, or in a bed the way I'd thought it'd be.)