After the incident, I endeavored to analyze the events that led up to it, concluding that I'd made four mistakes. The first was reporting a leaky water heater to building maintenance, the second forgetting the day and time, they said they would come, and my third calling in to work and reporting sick just so I could take a day off.

I lay in bed until nine, playing with myself and generally feeling horny. Having masturbated to an unsatisfying climax the night before I made my fourth and last mistake.

The feeling had been coming over me for a long time, and I knew this day would come eventually after I received the last item I'd ordered. That was days ago, and I think I knew when I called in sick that I would actually do it. Not that I was about to rush into it. My planning, or procrastination, as the case may be, was meticulous.

For weeks now I used an 'Epilady' to remove all leg hair until they were silky smooth, also the underarms, really painful at first, now mildly irritating. With one application of 'Sally Hanson' Cream hair remover, the remainder of my body hair around my middle vanished down the drain, and having no hair at all on the rest of my body to speak of I was smooth and clean from the neck down.

Hours of practice in front of the mirror with the make-up kit and an instruction booklet produced the desired look I wanted, until the instructions were no longer necessary.

I carefully placed all the clothes on the bed, each picked carefully for this day. The underwear was all black, except one pair of panties, black being the most exciting and erotic color that came to my mind. The camesette with attached garter strap was a virtually transparent black nylon and lace thing, lightly padded to give a nice shape to the breasts, tight and sheer, while the laces in the front allowing it to be pulled snug and tight around the body.

Two pair of panties, one a skimpy pair of black crotchless panties, sheer nylon and lace, the second pair of so called French cut, all white lace. This one was nothing more than two wide ribbons for a waistband, with a wide strip of lace going down the front, through the crotch and up the rear, flaring slightly to cover my bottom. A pair of sheer, jet black stocking with lace tops lay beside the other things, their color and silky feel arousing to the body and mind, and a short black nylon slip lay out between the underwear and the outer clothes as if dividing the two sets.

For outerwear, I'd picked a short suede mini skirt and a long sleeve, high collar; white silk blouse with peal buttons up at the back. The peal buttons gleamed softly in the overhead light, as if winking invitingly at me. To complete the outfit I'd brought a pair of black high-heels, open toed shoes with a high back and a wide ankle strap. These had large silver 'D' rings on each side of the ankle band, and just looking at them brought up imaged of bondage and seduction, making me shiver.

The shoe were the hardest thing to get, and I had to buy three pairs through the mail order catalog before I got the right size and fit. Three other items lay on the bed that started my heart pounding just looking at them. A silver studded black leather collar and matching wrist cuffs that locked when put on and three gold chains, a long one for around my waist and two short one for each ankle.

The make-up case lay open on the dressing table, ready, beckoning; beside it nail polish, perfume, hairbrush, and spray. Everything needed was there, meticulously chosen for this day, all laid out to see at once, instead of each piece as it arrived. Most I did this though catalogs, as some of the items I was too embarrassed to go in and buy, and now they all lay there, ready, waiting for me to put on, except for two things, one as important as the other, myself and courage.

This day was a long time coming as before I'd only worn panties stocking and a bra when I 'played', but today I was going to go all the way and dress up complete no matter what the consequences. So why am I standing here looking at all these sexy clothes and trying to work up the courage to put them on? Curiosity I suppose, it had gotten me into trouble ever since I could remember. Why now? That I couldn't say for sure. I rented a couple of bondage crossdressing videos a few months ago and I couldn't get the images out of my mind. I even managed to buy a great Bondage and Domination tape, a few months back watching it over and over again until I couldn't stop thinking about it.

For years, my mild curiosity about sexy or erotic lingerie had turned into a passion. Rejecting all other types of underwear out of hand. The other kind looked and felt terrible, being about a sexy to a man as cold porridge and about as exciting as kissing your dead grandmother. But as I said, today was a long time coming, first because I was living at home, and second because my mother would have gone wild had she seen me wearing anything but 'normal' underwear.

However, I knew that as soon as I was on my own I would buy and wear the sexiest lingerie that I could find. The feel of the material they used in them was fantastic, so soft, so erotic to look at, even the colors of girl's panties was so different from the plane white or solid colors of men's underwear. Slowly in an unending chain, I forged the links that let me to this point. From convincing my mother that I wanted to live by myself, to finding a nice quiet apartment in another part of the city where no one knew me, then to stop getting my hair cut to the point I had to wear it in a ponytail to work. So all I needed now was the courage to start.

Sex isn't really taught in school, not real sex, you learn that at first partly by a sort of osmosis from locker room dirty talk, finding out things like, do something to big girls, and women, they 'fucked ' them... but had very little idea what that was. One of the problems with dirty talk was that none of us had ever done 'it' and really had no idea of what 'it' was or how you do 'it'. The picture of one finger moving back and forth between a circle made of a thumb and forefinger doesn't really tell you a lot.

Thinking about the way big girls dressed is what started me thinking what it must be like to dress the same way and why it looked and felt so sexy. I knew my mother kept her underwear and other sexy clothes in one special drew in her closet, equating the wearing of sexy underwear as a prelude to sex itself. Steadily, my curiosity got the better of me that draw pulling me like a magnet, first a look, then a touch, until one day when she and my father were at work I decided to see for myself what was in there. I didn't just go in there and grab them.

My mother, being a careful person always folded her things up before putting them away, so the first thing I did was to open the drew and see how they were arranged, knowing I must return them the same way or she would instantly know I'd been in there. One by one, I took them out and laid them on the bed, noting the way they were folded. At first I was not very impressed, plain cotton one not much different from the ones I was wearing, but as I worked my way down into the draw I started coming up with thin nylon ones in different colors, some blue, some yellow and a few pink and red. Then I hit pay dirt. Lacy black, sheer transparent, in mainly white and black, some no more than a small triangle of cloth in the front and back, all spotlessly clean and faintly smelling of some perfume or another. A tingle of excitement ran through me, thinking what it was like to wear them and what it would look like wearing them.

I knew I dare not take any, knowing my mother would miss them instantly, parents have a sixth sense when it comes to things like that, and being an only child I knew she would know it was me that took them.

Somewhat half-hearted I started putting them back in the same order, finding as I did that the draw seemed to be a bit stuck. Looking in under the shelf something caught my eye, something black that seemed to be jammed between the top part at the back of the draw and the next one up. Carefully working the draw out and placing it on the floor I looked in. There was another pair of panties in the back, black and lacy. Heart pounding I reached in and took them out. Holding them up for examination.

At first, I felt disappointment, sheer black nylon and black lace met my gaze, but they were torn. Shaking the dust off, I laid them on the bed, replacing everything else just as I found them. Sitting on the bed I looked at the pair I'd found again, examining them closely. It was not that they were torn as I first thought, as, upon closer examination, I could see no rips or torn cloth, just neat sewing around each edge, but they had too many holes. I kept turning them around and around, trying to make sense of them. One part was obviously the waist because there was the tag, and that always goes at the back. Suddenly I had an idea.

Quickly checking the room for any evidence of my presents, finding were none, and closing the draw and closet I retreated to my room with the prize, excitement starting to rise. Quickly undressing I held them up one more time. The label told me which was the back and inside, and holding the waist band open placed first one leg then the other through the first and second opening and slowly pulled them up. The waistband came up over my hips and I settled it into pace around my waist, my excitement rising. The panties had been designed that way, without a crotch, the thought shocked and excited me, thinking of the possibilities, but then I heard the front door open and knew my mother was home.

In a panic, I pulled them off and dressed as quickly as possible, looking desperately for a place to hide them, at last picking on a sneaker. It would be the last place my mother would ever look.

That night I played with myself, visions of girls in panties like those flashing through my mind, this must be what they wore to have sex, or did they wear it to get sex? I wasn't sure and couldn't really fill in the details. Were their chests like mine, except with bumps? Did it hurt when they grew, or if you touched them? Maybe that's why they wore a bra, to protect them. I'd only seem a few girls with flat chest, and never having seen a girl nude I had no real idea what they looked like. I also had no idea of what a man actually did to a girl to 'fuck' her. Ignorance is bliss, so they say, but to me it was more frustrating not knowing.

At sixteen I got to saw my porno movie, not that I was supposed to, my father having brought it and locked it in his desk, the trouble was I knew of a second key that fitted the lock. He made the mistake of telling me to take the trash out. Dumping it in the trash can, my eye caught the colorful artwork on the cover of the box, and it wasn't long before I was gazing hungrily at the front cover in the security of my room. Thirty minutes after they were out of the house one evening, and giving them time to arrive at their friend house for dinner. I unlocked the draw and soon had the tape in the machine.

At sixteen I had a pretty fair idea what went on between boy and girl, having done a little of it myself, now hopefully I was going to see it all and complete my education. To tell you the truth I was shocked at some of the things they were doing, unbelievable. I saw girls and boys similar in age to me, some half undressed in the most exciting underwear it was possible to imagine, just looking at them sent chills through me. There were scenes of men undressing and touching girls all over without them complaining. In one scene, a man played with a woman's pussy. I watched in fascination as the camera moved in close and I got my first real look at a girl's cunt.

I saw a hand opening it, the middle finger of another hand gradually slip inside with a pumping motion. I couldn't believe it, the hand gently stroking up and down between the lips sent uncontrollable shivers through me and I could feel I was close to cumming. Then the scene changed and I saw something I would have thought impossible until then. A man stood in a bedroom, telling a young girl how bad she'd been and that he was going to have to punish her.

Taking her dress off I saw she was wearing stocking and a garter belt, seeing the panties were black lace, as was the bra. She wore a gold chain around her waist and ankles, and I learned later that they were called slave chain. I can image why. The girl must have been eighteen to nineteen, with make-up on that my mother would have said the only whore would wear. She stood there a few moments while the man walked over and came back with a chair, which he placed in the middle of the floor. The image of her standing there and the way she was dressed stayed with me a long time, and even today I can remember it in details, only having added a few more here and there over the years.

He pulled her across his knee, telling her what a naughty girl she had been and that she must be spanked as punishment. She begged not to be and I was glad that the man didn't listen, I wanted to see her get spanked, hoping it would be on her bare bottom, the same way I got spanked by my father a few times. Pulling her panties down, he exposing her bottom and began to spank her, first with his hand, then with a wooden hairbrush, her bottom jumping every time it landed, she cried and cried but he didn't stop until her bottom was completely red. Next, he stood her up, asking what she was going to do to say she was sorry. The answer was anything he wanted. The man then took his trousers off, then his underpants, telling the girl to kneel down and to suck him off. She did with no argument at all and I finally saw someone getting a 'blow job' for the first time. The scene changed just after that, now the girl had gone to the bed, kneeling down on elbows and knees, her legs spread apart. The man climbed on to the bed behind her, stroking her bottom, saying that now she would get the rest of her punishment. He talked while he did this, and for the first time I really took notice of what they were saying.

"You been a bad girl haven't you." He said stroking of her bottom, transferring his hand between her legs. "You been a bad little bitch and you needed to be spanked, don't you?"

"No...Yes." The girl said, and I heard a note of desperation in her voice as if wanting it to be over.

He roughly jerked her panties down and I got my last shock. It wasn't a girl at all, it was a... I didn't know the name then, a girlyboy was the best I could come up with. Reaching down between his legs, he placed the tip of his big tool between the lips of 'her' pussy, continued to stroke 'her' bottom as he did, the girlyboy starting to pant, then moan and he started spanking her again, hard slaps to 'her' red bottom.

I had been spanked before by my father, quite a few times, but nothing like this. When my father spanked me, it hurt. On screen the man had the head of his big cock inside 'her' and she squealed, but he didn't stop.

"That's it pantyboy, let me hear you squeal!" He moaned pushing harder. 'She' did, moaning and begging him to stop, but he didn't.

"Oh yeah, just what the crossdressing little faggot bitch needs, a hard cock inside her." He moaned out loud. I almost came myself at that point.

In moments, he had his big tool all the way inside and was now fucking and spanking 'her' as he did. I couldn't help myself. I played with stiff cock and spanking my own bottom at the same time. The harder he spanked her in the movie the more excited I became and the more I spanked myself. Each slap felt and sounded like the hardest spank I had ever had, it was painful yet not painful at the same time, I wanted it to go on and on, but it couldn't and in the end I came, the last painful slap sending me over the edge. Almost the moment it was over, I stopped the tape, rewinding it and put it back in the draw. Part of it I think was fear of what my father might do if he found out I'd watched it. Now I was in the scary position of dressing like the girlyboy in the video.

It took a while, but in the end, I told myself that I would dress up and stay indoors. If all the curtains were closed, no one could see me, or suspect what I was doing. Later I could change back. The decision made I didn't rush, wanting to experience each moment to the fullest.

I showered, shampooed my hair slowly over and over again, the scent of the herbal shampoo filling the bathroom with its fragrance. That done the conditioner went on, twice taking time to wash again with the scented soap to allow the condition to do its work. That done I rinsed, dried, and used a female antiperspirant under the arms and between my legs. Time seemed to fly as I blow-dried my hair and between the dryer and a hairbrush had my naturally wavy hair flowing down around my shoulders. Already the feeling of excited was beginning to grow, but held it in check, knowing that if I didn't I would rush and spoil it, but finger and toe nails were soon trimmed, buffed and painted, the color, bright red. The make-up went on easy, the hours of practice paying off.

I found that by paying strict attention on each detail, eyebrows, eyelashes, eye shadow, eyeliner, and so forth my attention did not take in the overall effect, not wanting to see it until completely dressed.

With the make-up done, holding off the inevitability of getting dressed couldn't be held off any longer, and standing there looking at the clothes my heart began to pound, air passing in and out in of my lungs in long trembling breaths, even my legs started to shake as I picked up the first item. The long gold chain felt ice cold against my warm skin, but it soon warmed as it lay around my waist on my hips. The shameful crotchless black panties slid up my legs without a hint of a snag, thanks to the 'Epilady', and I pulled them up over my hips and settling them in place, feeling wicked. They were snug but not tight, the nylon and lace contrasting with the white skin beneath. My arms went through thin shoulder straps of the camesette, feeling it slithering down my body in a way that sent electric tingles down my spine. I smoothed it into place around my hips with trembling fingers, my mind whirling with pleasure as I draw the laces tight, then tighter, and tighter still, until the two side almost came together, pulling my waist in and emphasizing my hips. The nylon stocking were the real test of the effectiveness of the 'Epilady', the silky smooth nylon feeling hot and cold at the same time, didn't snag at all as I slowly worked them legs, feeling them tighten as they coved my thighs, close and comfortable, as if it was the most natural thing in the world to wear them.

One by one the straps were hooked to the tops of the stockings and adjusted until it felt as if the camesette and the socking were one garment. It felt odd to wear panties, yet not wear them, the missing piece in the crotchless panties, giving me an insecure, vulnerable feeling. It went away as soon as the French cut panties were on and tied in place. The trouble was I was started to get an erection.

That spoiled the look of the panties, so I used a glass of ice-cold water and counting numbers in the kitchen until it went down. Then I was able to smooth the panties into place around my bottom, waist, and crotch without my hands shaking too much. The black nylon slip didn't help matter, the material sending shivers over my body as I slipped it on. It took me a while and some odd contortions to get all the button on the back of the silk blouse done up, but at last I did it. The mini skirt had to be wiggled into so as not to damage the zipper, finding it was easier to zip it up in front then turn the skirt around than to try and zip it up at the back. Carefully tucking the blouse in I reached up under the skirt to pull it down, puffing it out slightly at the waist. The six remained items on the bed took additional courage to put on the first time. Taking the easiest one first, the two gold chains were placed around each ankle, gleaming softly in the light, their meaning clear. Undoing each cuff I looked at the last items, until finally my trembling fingers closed the leather cuffs around each wrist, hearing the lock click shut as I did.

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byDennis_St_John© 7 comments/ 101966 views/ 22 favorites

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