PDA

View Full Version : Fiction: "Sissy"


Dkaren
11-29-2010, 05:28 PM
(no dares yet, but rest assured they're coming in the next chapter. I just need an overly long intro)

Before I get into any interesting stories or adventures, I first want to shine some light on myself. My birth name is Brad, but I dont identity by that name at all. I go by Naomi most of the time, and I'd love to get my name changed one day legally. Maybe not to a girl's name per se, something like Alex perhaps, just so aslong as it's not such a "manly" name like Brad.

Anyway, I am a sissy. Or a crossdresser, what have you. I wear women's underwear. Infact, female underwear is the only underwear that I own. I have male shirts and pants which I wear when I go out in public, but underneath whatever I have on, will always be something feminine. I dont own one single pair of boy's underwear, and no matter what I will have to wear panties. Have I ever been caught? Well of course, but more on that a little later.

Whenever I get back to my home however, I will strip off my male clothing and become the real me. Stockings, garner belts, fitted bras, skirts, dresses, blouses, you name it, I wear it. Alot of crossdressers are very unappealing, because they look to manly or muscled or hairy. Me? I weigh barely over 140 pounds, I am incredibly skinny, have very long hair and crystal blue eyes. My hair is straight and dyed pitch black, and is always brushed perfectly. I dress my hair to have heavy bangs in the front to compliment my blue eyes, and I am also very pale.

I work out alot running, so I have a lean body. I have a better hourglass figure than most girls, with somewhat wide hips and a petite build. I live on a very strict diet, so my arms and legs are never very buff and I have a figure exactly like a girl. My face is very round, and with long, girly hair, which I usually tie back into a ponytail publicly, which makes me look very convincingly like a girl. I make sure to shave my entire body, which is alot of work obviously, though I have been waxed at times. I wear alot of make-up to, which even further brings out my eyes and girly face structure.

Back to the underwear for a moment. I figured to live my life I needed male shirts and pants and suits and whatnot, but under no condition did I need male underwear. Even at work while I am forced to wear long shirts and trimmed pants, I can rest easy knowing underneath it all lies a sexy thong, pair of french boyshorts, or bikini-style pair. I like my panties tight as possible, and as frilly and skimpy as possible. I own many see-through pairs, and pairs with nothing on the backside are very common.

You may be wondering though, how can I wear fully female underwear, dont my balls and penis get in the way? Not at all. Why? Because I've been blessed, or cursed as you may believe, with a very tiny penis. How small? When it's erect, it's barely five inches. When it's flaccid? Microscopic. So my pathetic male parts are always safely covered by the panties, even the thongs, and I never have to worry about it flopping around or getting out of place. No matter how skimpy or tight one of my g-strings may be, I can rest assured my parts will be cradled inside of it.

So I wake up in the morning, usually in my nightie and panties, get up, shower, wash my hair, get dressed in male's clothing, survive through my desk job, and then the fun begins. I get back to my home and quickly strip off my clothing, shower again, and begin my real day. All my windows and doors are see-through proof, so no one can ever watch what I do, thought I doubt I'd mind if they did. Then I'll slip on a pair of sexy panties and a nice bra, and put on my stockings and a garner-belt. After that I'll fix my hair and put on some make-up, and perfume.

I'll spend the remainder of the day as a girl, and sometimes I'll go on the track machine and get some exercise, in usually a bra and panties. Sometimes I do some cleaning around the house in my french maid dress, sometimes I'll do the dishes and some laundry. I'll watch some television, maybe a movie, use the internet, what have you. Like anyone else, except every waking moment I will be dressed head to toe in frills, with my petite penis usually soluting the world, its hard not to when I'm so turned on. But I always have panties on, to keep that boy at bay.

And since I'm constantly turned on, I have a way of dealing with that too. I own a pair (or three) of vibrating panties. When I'm just to too turned on to bare it any further, I'll bring out a pair. I have a ritual. I get dressed up in the prettiest stuff I own, and get into position I have a very large mirror in my bedroom, which I always face when I do this, to make me watch my self as I do this. The added humiliation always make sit more kinky. I have a pair of handcuffs with a timer built in, they will only lock for ten minutes, which is more than long enough. I will cuff myself to the leg of my bed, which weighs a ton, with the remote to the vibrating panties in my hand.

The panties have a belt, so they cant be pulled down unless you have control over both hands. So when I'm cuffed there's no way to remove them until the timer runs out. When all that is in position, I set the remote to high, toss it away onto the pillow places beyond my reach, and lay back as the vibration in the panties buils. I always try to hold my orgarms at bay, which helps it feel better when it finally if let out. However, even with all my will I can only prevent it from coming for about 5 minutes, meaning I will often have to bare another few minutes, which actually improves the experience.

Afterwards I turn the panties off and clean myself off, and change. I lived like that for quite a few years. See, my father passed away at a very young age, and he was a very wealthy man. My mom is still alive, so she sends me alot of money every once in a while meaning I have unlimited funds for buying all the sissy gear I wish. Sometimes I'll rent out a "pal's" apartment when my mom comes to visit or whatever, so she doesn't find any of my sissy gear or clothing, which fills every inch of my place.

But I was not alone, ateast, not always.

MeasinToday
11-29-2010, 09:55 PM
Very Nice. :) Keep it up

packrat
12-05-2010, 08:56 AM
Please continue. This is great.

Dkaren
12-05-2010, 05:01 PM
So there I am, in nothing but my red lacy bikini-cut panties and a matching see-through bra, with stockings that went up over my knees. My pretty pitch black hair down my back and my make-up applied perfectly, I examined myself in the mirror. I looked great. I worked out constanly to remain my feminie figure, I demanded I not end up looking like those disgusting hairy freeks. I prided myself in genuinely looking like a real girl; I was the perfect trap. You could never tell I was even a guy, unless you checked my chest or slight bulge within my delicate underwear.

I would often post and browse random websites of interest, and amongst them I eventually came to GetDare. There crossdressing was accepted and openly encouraged, and even the straight men could be talked into taboo and otherwise naughty things with a simple response of "dare". It was fascinating, and with the help of my webcam, I quickly made friends with quite a few of the users. I was unafraid of my online decadence coming to haunt me or my real life situation, my female and male personnas could never be matched. No one would ever believe "Brad" was "Naomi". I was safe from ever being found.

I came across this cute looking girl who listed crossdressing a turn-on, and decided to message her out of curiousity. We chatted on webcam and she was a real pretty-looking girl I must admit, dark brown hair, blue eyes, and a rather fantastic body. I moslty associated myself as straight so I valued a decent body on a girl, infact, if a girl wasn't atleast a C-cup I wouldn't even bother with her. But this one? Atleast a C-34, and legs and ass that beat even my own. We posed in our sluttiest outfits for eachother on webcam, and enjoyed every minute of it.

This went on for a few days until eventually I asked a question I was afraid to. "Where do you live?" She answered. I was shocked! We lived in the same city. Perhaps we could meet she asked, and I jumped at the chance. I gave her the directions on my house and asked her to come over on a long weekend, instructing her to bring a suitcase or two of her more feminie outfits. I assured her there was little need to bring casual clothing as she could wear mine, and we were also the same fit and size. It all came together perfectly!

We were to meet on Friday morning at my house. I woke up early to get myself ready, I straightened my hair and washed up. I fixed my make-up, did my nails, and slipped on some nice full-cut panties and a matching frilly pink bra and a fully-body night-gown that was see-through. I insected myself in the mirror; today was the day. My fantasies may finally come true I thought. I looked like more a girl than she did I thought out loud, would she even recognize me as a boy? But my train of thought was shortly derailed, as I heard a knock on the door.

She was here.

dounowhoiam
12-19-2010, 10:33 PM
Brilliant story, and I'm loving the suspense. I just cannot wait for the next post.

slutpup
12-20-2010, 09:09 PM
did this story die?

Dkaren
12-23-2010, 03:59 PM
Things hadn't gone the way I had wanted.

It all seemed so simple. When Ashley had come to my house and adored my levels of naughtiness, I was having a blast. I had never been seen in women's clothing before, and here was a stunning girl who demanded to see me in evert outfit I owned. She was clearly the dominant one in the relationship, telling me what to wear and how long to wear it. She would punish me when I would not obey, and she would punish me in any way she saw fit. One time I didn't want to wear a thong and instead picked a less revealing pair, and she stripped me of my panties and forced the thong onto me. Afterwards for not doing what I was told I was given 100 spankings with my hands tied behind my back.

Sure, I pretended not to enjoy it. I moaned in pain at every smack that hit my bottom. I cryed after a while, yet she did not let up. But we both knew that I was loving every minute of my humiliation. My cock was stiff as a board, and it wasn't hidden well by the thong. After my 100 spanks, she ordered me into the backyward where she tied my hands behind my back, locked against a tree. I was forced to stand there in nothing but the skimpy thong in public, though no one saw because my backyard is hidden semi-well. She could make me do anything, as I was to weak to fight against her. She was just simply stronger than me, and there was nothing I could do. And I loved it.

Things like that continued for a while. I would do all the chores and laundry, and still continued with my job. Ashley moved in, and did nothing around the house. She demanded I did everything for her, and I was nothing less than a slave. It was hell, but I enjoyed it nontheless. She saw me as so pathetic I wasn't allowed to even touch her, and I had to beg to use my vibrating panties, which she had since adapted as her own, to pleasure herself when she wanted. This kept up for a little while, until one say she ordered me into full drag.

I pulled on a long skirt, and a pair of stockings. I was told to wear a blouse and fixed my hair and make-up so no one could even tell I was a boy. Underneath I had tight pink panties and a matching silk bra, and I was told to gather as much as I could and pack it into suitcases. My female clothing filled eight entire pieces of luggage, and shortly after, a car appeared in out drive way. I had no choice but to walk out in public in full drag, but I wasn't afraid of anyone noticing I was a boy. I dragged all eight of the heavy suitcases into the trunk and back seat of the car, and then I had to get it next to the luggage.

Ashley sat in the front seat, and next to her, was a very sexy blonde. They discussed who I was and what they were going to do to me. The blonde, named Cassie, was amazed that I was actually a boy under my feminine outside. She ordered me just as Ashley had, and told me to lift up my skirt. She gasped at my small dick, and made a demeaning joke concerning how I actually was a girl. Both of them laughed at my humiliation, and my face went deeper in red than it already was.

Shortly after, they drove off. When I asked where we were heading, I was told we were going to "A cabin in the woods to meet a few more girls". My stomach turned further, but there was little I could do. We had an almost endless supply of female clothing, but I was told not to pack a sinlge thing a boy would wear, meaning I had little chance of escape. I was going to be the slave of many, many cruel girls. And you know what? My dick was throbbing. I was so excited my panties got a bit wet.

And then, we were "there".

d0rf47
01-13-2011, 11:58 AM
you have to tell the rest

Demon Thief
01-20-2011, 09:32 AM
Oh, wow, this is pretty good.

shavedrachel rocks!
02-20-2011, 04:53 PM
more plz do more
plz im beging more

DareOnMat
04-13-2011, 07:02 PM
wow this is so exciting....my **** is hard now ^^....tell more about it...i love crossdressing/sissy dares stories.