The Experiment (crossdressing, feminization, BDSM)

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Contents

  1. Join Kobo & start eReading today
  2. Subscribe to receive new stories
  3. Your Kinky Bucket List: 10 Things to Try Tonight
  4. Podcast #131 – Crossdressing!

One great trick is to be light and sensual with some caressing in between slaps. Hands work great to begin with. Start out with light smacks and increase the force to increase the sensation. Warm up that lovely bottom before going full force on it. For those who seek heavier pain, a paddle or strap can be used. Role-Play Think back to when you were a kid and the games you played, such as cops and robbers or cowboys and Indians.

Bring this imagination into your sexual encounters as an adult by engaging in some role-play. Go see the doctor for an exam. Play boss and secretary. No matter what you choose, role-play is a fun way to start experimenting with being in a different head space. Just think: We can now play pretend and have orgasms!

Written by Simone Worthington. Related Articles. Want to tie up your partner? Here's how to tell them. On Top: How to Be a Dominant. Related Terms. Should my partner and I choose a male or female to create our first threesome? What is the swing lifestyle? What's the difference between a wood, leather or silicone spanking paddle? Change into your new blouse and slacks. You will walk back to your car like this.

Now that you have bought yourself a nice, casual, feminine outfit, you have the perfect costume for another shopping trip. You will be completely, freshly shaved. Your toenails will be red, your fingernails will be glittery. You will wear black bra and panties, nude pantyhose, your floral blouse and black slacks and subtle lipstick. You will carry your compact mirror, both your lipsticks, spare pantyhose, your high-heeled sandals, your dildo and your breasts. When you have completed your shopping, find a quiet restroom, maybe in a department store.

Hang your new suit on the back of the door. Put your sandals on the floor. Take off your shoes, slacks, blouse, and lipstick. Fit your breasts into your bra cups. Spray a little perfume on your wrists and rub them together. Spray behind your ears, between your breasts, and between your legs, too. Put your vest on. Does it emphasize your cleavage? Now put your suit on. Relish the sensation of that slippery lining on your pantyhose. Maybe you can tuck and a liner will prevent any nasty stains.

Put your sandals on. Less chance to make a mistake that way. Press a little of the powder all over your face, using a rolling motion with the pad. Position the eyelash curlers at the base of your upper lashes and squeeze for a few seconds, then release and gently squeeze again a little further out. Hold the mirror at your chest so you are looking down into it. Now apply mascara to the outer two-thirds of your top lashes. Next, apply a coat of red lipstick and blot. Now a second coat of mascara, then a second coat of lipstick and blot. Now do your bottom lashes whilst looking up at the mirror.

Add a third coat of lipstick, for luck. See how long and feminine your lashes look. Put your watch on. How long do you think it will be before you are dressing like this for work? Go to a bookstore and buy a book on hair, makeup and beauty. You are going to read this from cover to cover when you get home.

From now on you will wear a bra, panties, and pantyhose on your shaved body every day and sandals every moment at home. You will maintain red toenails and will also wear clear polish on your fingernails. Hopefully, you have been using your initiative and letting your fingernails grow. You will continue your cocksucking, but only once a day now. Every evening you will wear one of your two female outfits and apply full makeup before sucking cock. This will give you daily practice at doing your make up. Believe me, you will need it. Most real girls have been experimenting with makeup since long before puberty, so you have a lot of catching up to do.

Try a different look every day. Remember, you are a sissy, not a tart. This goes for makeup more than anything. A girl must learn to have a light touch. Satisfy yourself that you can make yourself up proficiently before you progress to your next assignment. This is very important. This will be short and sweet. Two simple tasks with the most enduring consequences of any of your assignments so far. You will hire a sunbed, one that will tan you both sides at once, like a piece of bread in a toaster.

Twice a day, you will dress in a bikini or panties and a filled bra and build up a delightful, feminine tan on your sunbed. Be careful to position your bra straps in the same place every day so that the outline is crystal clear. Do not even consider returning the sunbed to the store until you have done this for a week and have very obvious, sissy tanlines, front and back.

How feminine do you dare go? Delicate, pencil-thin arches will make your face much sexier. Much more room for eyeshadow, too. Do it, sissygirl. From now on you will pluck your eyebrows every week. Stand naked before a mirror and look at that indelible lingerie burnt onto your skin.

What more humiliations can be in store for you, sissy? You are going to buy a new toy. You are going to a sex shop to buy yourself a buttplug. Clever girl. You are going to be shaved and perfumed and in bra, panties, and hose, as you are every day. You need not to fill your bra. You will wear your choice of male clothes and shoes. You will also wear foundation, lipstick, mascara, eyeliner and at least one shade of eyeshadow. The choice of colors is up to you. Take your sissy, feminized self to a sex shop and buy not one but three buttplugs in different sizes. Pull down your pantyhose and panties.

Smear some lubricant against your hole and slowly work a greased finger inside. Fuck yourself with your finger.

Does it feel good, sissy buttboy? Get the smallest plug and slowly fuck yourself with it. Do you feel full? Start sucking your dildo and masturbate. Notice how your sphincter tightens around the plug as you play with yourself. Do you feel hot? Increase your plugging time by an hour a day. Imagine a full working day — shaved, perfumed, bra, panties, pantyhose, nail varnish and now a buttplug. No real man would even dream of doing this. You are such a sissy. Has anyone else noticed how much of a sissy you are these days?

Your work colleagues, for example? Plugged, shaved, plucked, tanned and perfumed, you wear a bra, panties and hose all the time and your fingernails are growing longer and sport clear varnish. They will certainly be curious about what you get up to away from work.

You are going to get a professional makeover. You owe it to yourself. Start ringing round. Ask if they would accept a male customer and if they have any objections to you arriving dressed as a woman. When you are successful, book an appointment. Take a day off work for this. You will ask for:. You will ask them for the most feminine style they can create with your hair. You will give them total free reign.

Sissy Porn and Forced Feminization aka Sissification

They may want you to help by choosing something from a magazine. Be true to your self. You must also get it colored. Obviously, this will depend on your current color, but there is little to touch a strong henna red or a soft, chili purple for outright femininity. You will be offered a huge choice of colors for your nails. Choose the best, dark red to go with your new hair. If they are not at least a quarter inch beyond your fingertips, you must get half-inch glass fibre extensions to punish yourself.

And can you picture yourself getting ready for your pedicure? Unfastening the dainty buckles to step out of your high-heeled sandals, hitching up your tiny skirt and rolling down those delicious nylons you wear 24 hours a day. Then having a nail technician remove your nail varnish and add a new, dark red polish? Get a single piercing in each ear. Leave the style and extent of your eyebrow shaping to the experts. Just ask for something suitable for the shape of your face and your hairstyle and more feminine than what you have done already.

For your make up lesson, tell them you want an evening makeup, no matter what time of day it is. Remember: do not cum. When you leave the salon, linger at the local stores. Go for a coffee. Show the world the glamorous sissy you have become. Get out your little compact mirror and study the new you.

Do you like what you see? Play with your earrings. You paid a professional to do your face, nails and hair. Nor those eyebrows. Maybe you need to stop pretending and out yourself as the true sissy you really are. That must be so difficult when you look so gorgeous. Undo your jacket. Look at the way your breasts stretch your top. Look down at your lap. A miniskirt barely covers your nylon-clad thighs and your professionally- painted toenails glint back at you past the delicate straps of your high-heeled sandals.

Wiggle your toes. You are nothing but a feminized sissy girl. Give up your last pretenses at manhood and start living as a woman — full-time. These assignments have helped you find your true self. You can now graduate. EMAIL your final report. Or is this too much for you? Perhaps you need some more assignments, then. Was your last assignment too much? Were you not able to do it? There can be no other reason for you wanting more assignments.

If you had done it, you would now be so obviously feminized that everyone would know. Very well, sissy. I hope you have done everything else, though; shaving, painting, tanning, clothing, sucking, chastity. If not, go back and start from the beginning. Obviously, you will want to fit in with all the ladies there, so you need the right outfit.

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Go to your nearest dancewear shop. Look it up in the phonebook if necessary. As a special reward for your devotion to these assignments, you have free reign on your outfit for this trip… but you might want to be feminine. You will buy a pink leotard. Buy a pair of nude, fishnet pantyhose.

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These are very expensive but superb quality and have cotton soles for comfort. Lastly, some pink grips for your hair. Try on your new outfit at home. Wear a pair of thong panties underneath everything to protect your balls from the grip of the fishnet. Does the scoop neck reveal your bra tan?

Check your back in the mirror. Does your tan show there? In front of dozens of women. Is that humiliating enough? What will be more humiliating is turning up in your pink sweats, showing just a hint of nude fishnet, which might go unnoticed, then stripping down to this. Even this is not enough. Now, is that humiliating enough? You wimped out of your last assignment, but you WILL do this.

What are you waiting for? Email your report. Choose two from the following —. Needless to say, you are going to wear your new tops, over your bra, every time you go out of the house, except to work. You will be so humiliated as your heels click-clack up and down the aisles, reaching out for grocery items with your feminine hands.

Pay by credit card, sissy, so you have to sign your male name whilst holding the pen between those pretty, feminine nails. You need to expand your sissy wardrobe and you need jewelry. Your fingernails will be glittery. For now, make do with your male shoes. You will wear foundation, powder, eyebrow pencil, eye pencil, eyeshadow, mascara, blusher, and lipstick, but in subtle colors that, from a distance, make your face look unpainted.

Besides, they will notice your nails and your bra and your perfume and the side zip on your slacks, so why be embarrassed about a little makeup? First stop is a jeweler. Jewelry stores offer great scope for sissy humiliation. They always offer such personal attention. Try to go at a quiet time so you get this attention. You will almost certainly be offered a seat, which means you will expose your ankles in their pantyhose. Then you will have to point out your choices on a selection of trays, drawing attention to your painted nails.

The ring you are looking for is a solitaire; a thin band with a single stone, possibly an engagement ring. When you have made your choice, you will be asked the size. You must tell the jeweler it is for your own ring finger. You will then wear your ring. You also want an ankle chain which you will put on in the shop over your pantyhose. Drawing attention to your shaved legs and nylons. If they offer to engrave, ask for your sissy name to be added. In the future, you will wear your anklet under your pantyhose, next to your skin.

You will never take it off. You also want a bracelet. Choose the most delicate chain available, something a real man would never wear. Your next purchase is a necklace. Not gold or silver this time, but a string of fake pearls unless you can afford the real thing. Wear them now, too. They will look lovely with your open shirt. Finally, a pair of earrings.

If not, you will do it today. You MUST ask to try them on. Slip off your male shoes to expose your red toenails behind the reinforced toe of your pantyhose, your anklet glinting at you. Taste your lipstick as you bite your lip in shame. Slip your feet into the new shoes.

Walk in them. Does it feel good to be back in heels? Wear your loafers for the rest of your shopping. Apologies to those of you with enormous feet. You will have to do your shoe shopping online and miss all this humiliation. Go to your favorite sissy changing room aka public bathroom. Strip down to your bra and panties. Now would be a good time to put your ankle chain in its proper place. Put on your thick tights. Put your roll-neck top on. Now your new shorts and your loafers.

This is the look you are aiming for. Are you ready to go out like this? Perhaps you should refresh your make up. Redo your eyes with some darker shadow and a black pencil. Run your favorite red lipstick over your girlish mouth. Put on lots of blusher. Now go for it, sissy. You will wear your loafers to work. They are you new work shoes, sissygirl. Wear them with pride. And a little sway in your step. I hope you look a little like Catherine at work.

And you have to buy them. Take your handbag. You must dress like this for your trip, or you will not get to wear stockings. To feel the tug of taut nylon on your suspender straps garter straps, American sissy as you walk and sit, the stretched strap sliding over your hips as you move, the slightly sagged stocking top rubbing your inner thigh, the teasing femininity of buckles and clips under your hands as they rest in your lap, the visible bulges of lingerie on your thighs. To experience all of this, you must first humiliate yourself.

In your pretty outfit, your new court shoes will look very feminine and make it obvious you are wearing nylons. Your bra will be obvious, as will all your sissy jewelry. But you will be rummaging through racks of stockings with painted nails. That will be deliciously embarrassing.


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And all with no makeup to hide behind. Perhaps you did, you naughty little sissy. Go to your favourite lingerie store, where you buy your bras and panties. Treat yourself to a complete set of matching bra, panties and suspenders. A good tip is to look for metal buckles on your suspender straps because of these grips much better than cheap plastic.

As ever, invest in your femininity. You may well learn to your cost how much of a nuisance this is. You will also buy a basque. Buy on bust size, but check for the quality of all the straps and fastenings. There will probably be some matching panties for you to buy, too. Now go to your hosiery supplier and buy fifteen yes, 15 pairs of stockings in a variety of styles and shades.

You may indulge yourself with lace-tops if you wish. You may buy hold-ups thigh highs, I believe you Americans say but you must still wear them with suspenders. This is actually quite a sexy feeling; because the stockings are fixed in position, the suspender straps tense and relax much more when you walk. You are such a good sissy for wearing such a humiliating outfit for your lingerie shopping. You might think your purchases are their own reward, but no! You will give yourself an even greater reward.

Go to a coffee bar and order a drink. Slide the plug in and out your ass with the pressure of your buttocks. Discretely, beneath the table, stroke yourself like a girl, gently, with one of your painted nails. Stroke your aching boyclit. Cum before your drink arrives. Feel the hot semen fill your liner and maybe leak out into your panties.

Maybe your shorts will be wet, maybe your pantyhose will be wet below the hem of your shorts as your cum leaks away. Wear stockings every day and night for a calendar month. Wear your basque and your three-piece set on alternate days. Remember, wear your panties over the suspender straps so you can pull your panties down when you sit to pee.

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Do not cum, no matter how horny you feel. Save one pair of stockings for a special purpose in your next assignment. Have you enjoyed your month in stockings? Not nearly so thrilling when you wear them every day, are they? You may have been wondering why you had to save a brand new pair of stockings. Get them out now.

Strip naked. Naked except for your jewelry, perfume, nail polish and full, heavy makeup, of course. And your biggest buttplug. Masturbate until your boyclit is hard. You may want to suck your trusty dildo if you need inspiration. You know how horny that makes you feel. Put your condom on. Now bunch up one of the stockings and put this over your boyclit, like a large, nylon condom. Pull it right down over your sissyballs. Twist the stocking behind your sissyballs and pass the bunched nylon back over your balls. Twist again and pass this, much tighter, pocket of nylon back over your balls.

You now have your boyclit covered in latex and nylon and three layers of nylon compressing your sissyballs. Masturbate slowly. Tease yourself. Attach the clothespins to each of your nipples. Feel them bite into your tender flesh. Have you ever experienced a sensation like that? Now put your bra on and fill the cups.

The extra pressure on your nipples will heighten the sensation. Now choose your silkiest pair of panties and a pair of slippery, high-lycra pantyhose. Choose a blouse and a pair of slacks and put your sandals on. You may not hide behind an overcoat or sweater. You should look quite passable, apart from that prominent bulge in your slacks. If the weather is cool, your nipples will be rock hard, making those clothespins bite even harder. When you get back home, suck your dildo while you pull on your tightly constrained sissyballs through your clothes.

But when you have spent your disgusting sissy mess you will carefully remove your condom, collecting as much cum as possible from your boyclit, then pour your cum into the ice cube tray and put it in the freezer. Every working day, just as you leave the house, you will put a cumcube in your mouth and suck it until it has all melted down your throat. You will NOT use gum, breath freshener, toothpaste or any other subversive means to undermining the humiliation of arriving at work with the smell of cum on your breath and the taste in your mouth all morning.

A shaved and perfumed sissy wearing lingerie, jewelry and nail polish, complete with the smell of fresh cum on her breath. And not just once, but for days on end, until you have used up all your cumcubes. Deliciously humiliating. It should take you at least two weeks to use up your cumcubes. If you enjoy the taste of your cum after your cocksucking training, then you may find your first, frozen cumcube thrilling, but two weeks later you will be wishing you never started this.

But you must do it, because this is the cost of your sexual release from now on. Congratulations on reaching your twentieth assignment. As a special treat, your new task involves going to the cosmetics section of a large department store. Start masturbating now, sissygirl. Start with your basque and a pair of black stockings. Bind your boyclit and sissyballs with one of your special stockings. This way, your unsightly bulge will be more prominent and you risk a wet mark in your slacks as your boyclit becomes slick with pre-cum. Wear your palest slacks and a sissy blouse.

Your Kinky Bucket List: 10 Things to Try Tonight

Wear perfume and jewelry as usual. Wear your loafers. Wear glittery polish on your fingernails. Go to a large department store. Make a few circuits of the makeup area. Establish who is offering makeup demonstrations. Chose the demonstrator you think is wearing the sexiest makeup. They are always heavily made up but some look better than others. Tell her you would like to be able to copy the way she has done her eyes or lips, if you prefer. By now particularly if she has noticed your sissy appearance , she will probably have guessed where this is going and, if she is obliging, she may offer to demonstrate on your face.

Otherwise, perch your sissy ass on her stool and prepare for the thrill of being made up in public by a willing female. Thank her profusely. Buy everything she suggests. Wear your pretty, new makeup with pride as you go to the checkout to pay for your cosmetics. Better spend your drabtime wisely.

Podcast #131 – Crossdressing!

Grocery shopping? The gym? Buying replacements for your snagged pantyhose? If you have to go out to work, you may for now, at least wear drab from when you leave your house until your return. Calculate how many hours this is each week and add it to your drabtime allowance. I suggest you carry a timer with you — find one that will countdown the required number of hours and has an alarm. Set it to your total drabtime at the start of your week and start the counter the moment you are improperly dressed as a man. You are only cheating yourself.