Sissy Finishing School

Category: Cross Dressing

  • Sissy Gaff Revolutionizes Crossdressing

    Sissy Gaff Revolutionizes Crossdressing

    Introducing The Sissy Gaff

    How To Use A Sissy Gaff
    Sissy Gaff Revolutionizes Crossdressing

    Many sissy boys have a desire to appear more and more feminine as time passes. They find themselves longing to wear tight miniskirts and skin tight jeans. Some find that “tucking” isn’t enough and are excited to find out about the sissy gaff. The sissy gaff revolutionizes the way a sissy boy/crossdresser can dress.

     Tips To Remember When Using A Sissy Gaff

    Once you have picked out the perfect sissy gaff and pulled it up to your thighs, you are going to have to tuck your balls back gently to the place they first dropped from and push them up. This should not be painful, and if it is, you are definitely doing something wrong. Next you will tuck your penis between your balls and back. Be sure to hold everything in place neatly.

    Tucking can be uncomfortable at first, but overtime it will become much more tolerable. Now you can pull the sissy gaff up and over your hips, letting it hold everything in place nicely and leaving you with a smooth “vagina.”

     Purchasing The Sissy Gaff

    One important tip to remember when purchasing a sissy gaff is to make sure that it is nice and tight. The sissy gaff is most effective when it is extra tight. The tightness of the gaff will make you seem extra smooth under even the tightest of jeans.

    The sissy gaff should also be tall enough to smooth out your waist so that you can dress up in that hot mini dress you have always been fantasizing about. You want to smooth out your body from the waist down so that you can look more feminine and sexy.

     Tucking Your Cock & Balls In The Sissy Gaff

    If you are having trouble with your cock and balls staying tucked in the sissy gaff, you can use some tape to hold them in place. Remember to shave before using tape though! Tape can be useful in training your body to accept tucking and thus can help you when you first start using the sissy gaff.

    These are just a few tips to remember when using the sissy gaff and there is so much more for you to learn! The sissy gaff will have you looking extremely feminine and wearing all the clothes that you so desperately want to wear. Need some advice on choosing the perfect sissy gaff? Give Ms Lily or I a call, you know we’d be happy to help with your sissification process.

    Until then……

    Ms Isabelle

  • Project Runway – The Stylish Cross Dresser

    Project Runway – The Stylish Cross Dresser

    Be a stylish crossdresser for meIf you aren’t already, now is the time of year when a cross dresser really must bring her game face, and transform from a mere mortal into a stylish cross dresser.  Awards season is in full swing, and the New York Fashion Week (NYFW) is underway, so now is not the time to be frumpish and dowdy. Not that there is ever a time for that, but especially not now.  It’s time for you to tap into your inner fashionistas! And once you have, of course, you must share with Ms Isbaelle and me.

    Expressing Your Stylish Cross Dresser Self

    Odds are, you don’t have an invitation to any of the shows. And if you do, you need to FedEx it to me post haste. But assuming you are not fashion royalty, and you won’t be sitting in the front row of Lincoln Center, you are going to have to be creative, and let us see what kind of panache you have.  I’ve got a few ideas, and you are free to take them and embellish them, or come up with something to dazzle us.

    Whatever approach you take, your assignment is to come as close to creating a red-carpet or runway experience as possible.  You needn’t drop a lot of cash for this project.  You can take a note from Macklemore and Lewis, and pop tags at your local “Thrift Shop“, if you are going to actually dress the part.

    That won’t be possible for all of you, and that is fine.  You can make a collage of what you’d wear, and send a picture of it in.  You can create your favorite ensemble at Polyvore, and share it with us there.  You can draw your vision, paint it, or write a story, chock-full of rich detail, describing what you have on as you strut your stuff.  Whatever means that allows you to fully immerse in your stylish cross dresser self is fine.   You just need to share the outcome.  And you need to remember that we love swag bags, so do your part toward filling ours to the brim.  In the immortal words of Madonna…”Express Yourself!”

  • College Crossdressing Turns Into Lifetime Crossdressing

    College Crossdressing Turns Into Lifetime Crossdressing

    When Did You Begin Crossdressing

    When Did You Begin Crossdressing?
    When Did You Begin Crossdressing?

    I know there are many ways that a person can find themselves having a love for crossdressing phone sex. As a fashionista and experienced crossdressing Mistress, I know much about the crossdressing fetish.  I have met and are acquainted with many men that choose to crossdress. One of the things that I have found interesting is that many men didn’t really get into crossdressing until college. For some of them it started with the woman-less beauty pageants for local fundraisers and for others it was a growing interest in fashion and admiration for the beauty of women.

    These men would crossdress occasionally throughout college, but they would tell no one of their inherent desires to become a full-time crossdresser. Perhaps they didn’t even realize just how much their desire to crossdress was growing themselves until after they had been relieved of the pressures of college social acceptance.

     

    Crossdressing Emerges

    Once these men had found stable jobs and lives that brought on stress, they started to feel that need to crossdress emerging with a brand new force. This force grew and grew until they found themselves crossdressing every night as they returned home from their jobs, hidden away in the secret of their private homes.

    This was the moment when they realized that they needed and desired to be full-time crossdresser’s, finding safety, comfort and release in the activity. This is perhaps the first time they sought out a Mistress for guidance and to share their long harbored secret.

    Crossdressing Guidance

    Over time and with the guidance of an experienced crossdressing phone sex mistress such as myself, these men grow into the perfect images of woman and are at last happy in their lives and with themselves. Does this sound familiar to you? Do you need the assistance a phone sex Mistress? Ms Lily and myself are here at Sissy Finishing School for you and would be happy to guide you on your crossdressing journey.

     

    Until later…….

    Ms Isabelle

  • A Crossdressing Assignment

    A Crossdressing Assignment

    A Crossdressing Assignment From Ms Isabelle
    A Crossdressing Assignment From Ms Isabelle

    This crossdressing assignment will be a three day assignment for those of you that are into the crossdressing fetish. You will have THREE challenges to complete for this crossdressing assignment. Please do each one in order before moving on to the next day/step.

    Items that you will need for the crossdressing assignment: panties, bra, thigh highs and garter belt. You will need a pair of high heel shoes. Matching items are the best, if you have them. You will also need a light foundation make-up, blush and lip gloss.

     

    Day ONE: Getting Started With The Crossdressing Assignment

    This will be the first day that you experiment with taking your crossdressing fetish from the bedroom to the workplace. You will wake up early and find your perfect pair of panties and slip them on. You are then to apply a light coat of foundation, just enough so that you know but not enough that it will be overly noticed in public. Try Smashbox BB cream, it’s fantastic!

    During your lunch break, you are to find a quiet, private place and rub yourself through your panties until you cum inside of your panties. The only alternative to cumming in your panties is to cum in your hand and lick up every last drop of cum.

     

    Day TWO: Upping The Stakes For Your Crossdressing Assignment

    When you awake on day two, you will spend your morning in heels getting ready for your day. For this crossdressing assignment you will wear your bra and panties under your normal work clothing. You will apply a light coat of foundation and just enough blush to enhance your natural color, but not enough to be noticed by co-workers to much.

    You will likely be distracted by the feeling of your panties and bra under your normal clothing all day. During lunch you will again find a private place to rub yourself through your panties. Cum will only be deposited in your panties or in your hand to be eaten.

     

    Day THREE: Crossdressing Undercover Assignment

     

    Day three’s crossdressing assignment requires you to awake nice and early so that you can spend at least 10 minutes in your high heels as you apply your foundation, blush and lip gloss. You will also make sure to take a good look at yourself in the mirror as you slip on the panties, the bra, the garter belt and thigh highs. You will spin slowly, admiring yourself in the mirror. You are to ignore a stiff cock at this point.

    You will spend your day immersed in the feelings of being more feminine than normal. Every movement reminds you of the silky garments that hide beneath your normal daily work clothes, arousing you with each slight brush. At lunch you will masturbate just like you have each day before, but you will not orgasm. You will push yourself to the edge then stop.

    You will spend the rest of your day on the verge of arousal. You will be allowed to orgasm once you have gotten home and slowly masturbated for 20 minutes. You will NOT cum till you have masturbated for the entire 20 minutes. You will cum into your panties or into your hand, and it is to be licked up like a good little slut. I do hope you enjoyed your crossdressing assignment.

     

    Until later…..

    Ms Isabelle

     

     

  • Crossdressing Mate

    Crossdressing Mate

    I Love Having A Crossdressing Mate
    I Love Having A Crossdressing Mate

    I Love Crossdressing Mates

    I know it may be hard to imagine what life is like when you have a mate that is a crossdresser. Many people may even have a hard time understanding that there are some positive aspects to having a crossdressing mate.

    I have spent much of my time around crossdressers in a variety of ways from having them as mates to roommates and I have learned much about the advantages. There are many advantages of having a mate that is a crossdresser and I would like to cover just a few of the major perks!

     Advantages To Having Crossdressing Mates

    First of all, you and your crossdressing mate will possibly be able to share some clothes, shoes, handbags, and/or accessories! It’s hard to not be excited about having double the inventory when you are getting dressed for that hot date. You also have someone that can help you decide on outfits and to pick out the perfect shoes for an event. Having a crossdressing mate is like having the perfect friend available all the time!

    Secondly, your crossdressing mate will be happy to go out for massages, mani’s and pedi’s with you on a whim. While you both get pampered you can gossip about the hottest trends and Hollywood gossip. There is nothing better than having someone there, especially your crossdressing mate. You both have a connection and understanding of one another that makes it easy to talk for hours.

    Your crossdressing mate will even be willing to help you do your make-up in the sexiest styles, not to mention the amount of make-up that will be available!  You can also share lipgloss and perfume.

    Sharing A Special Connection With A Crossdressing Mate

    The last reason I want to touch on is the fact that you and your crossdressing mate will have a very special connection that you will share. Your crossdressing mate will be much more sensitive than your normal mate would be and will be very attentive to your girly needs.

    These are just a few of the reasons that having a crossdressing mate is a major perk to your life! Are you a crossdressing mate? Give us a call and share your advantages and perks with Ms Lily or myself and let us know what a great mate you are.

     

    Until then,

    Ms Isabelle

  • Sissy Fall Fashion

    Sissy Fall Fashion

    Sissy Fall Fashion
    Call us for a fashion consultation, crossdressers!

    With Labor Day weekend upon us, it’s time to turn our thoughts to sissy fall fashion.  Fall is a great time of year for sissies and crossdressers.  It allows for extra layering to give the illusion of curves that nature didn’t bless you with, and is more forgiving than summer fashion.  I’ve just come back from snagging a huge haul that I got on vacation, and here are some things you can pick up if you want to feminize yourself in my likeness.

    Leggings and Tights – Two Sissy Fall Fashion Musts

    Genetic girls are crazy for leggings and tights, and there is a reason for that. They are versatile and oh-so-comfortable!  They come in every imaginable color and texture.  Is your sissy brain addled by trying to figure out the difference between them?  Just remember that tights are like a sister to pantyhose.  They are thinner and more sheer than leggings.  Never wear tights alone, or your otherwise great feminization will be uncovered by your sissy stick being on full display.  Depending on the opacity of the fabric, leggings can be worn as pants.  That said, I do advise that you wear a top, mini-dress, etc, that comes down long enough to cover your ass.  Not everyone can really pull off looking fabulous in leggings and a short top.  It gets more difficult when you have that unsightly sissy bulge in front.

    Jewel Tones Are Our Friend

    Forget pink. You can come back to it later. Step up your sissy diva fashion game by getting bold. Think emerald green, pumpkin orange, golden leaves, and a crisp blue autumn sky.  Let Mother Nature, in her infinite wisdom, guide your palette selections.

    Be a Pinup Queen – Sweater Time!

    Every girl needs one really amazing sweater that clings in just the right places.  Ideally, you’d know your body style, and would pick according to that.  But if you don’t know your body style and you naturally have a smooth chest,  go for a scoop or V neck.  If waxing, etc doesn’t work in your life, then go for something with a higher neckline.  If you want to *really* accentuate the bust-line, go for a turtleneck.

    Once you have put together your sissy fall fashion ensemble, it’s time to call in and give me a cam show so that I can enjoy your feminized creativity.

  • Hot To Spot A Crossdresser

    Hot To Spot A Crossdresser

    Ways To Spot A Crossdresser

    Ways To Spot A Crossdresser
    Ways To Spot A Crossdresser

    There are several ways that one can spot out a crossdresser, some are much more obvious than others. One has to have a careful eye to spot a crossdresser out in public while he is in his male ensemble.

    I often notice the little things first. For example, are his eyebrows shaped or does he have shaved legs? Does he frequently apply and wear lip gloss, this could be a tell-tail sign that he is a crossdresser. Is his handwriting soft and frivolous like that of a females?

    Sometimes I have even spotted the garter tab pressing against his dress pants as he tried to hide the fact that he was in woman’s  undergarments. Some crossdressers may be be found out by the type of cologne or perfume that he chooses to wear out. These are all subtle signs, but they can help one to find out which men would be into crossdressing.

    More Tell-Tail Signs Of A Crossdresser 

    Another tell-tail sign of a crossdresser would be to find him shopping for lingerie, but when engaged in small chat he frequently blushes and never once mentions a wife or girlfriend that he is shopping for. If you encounter a crossdresser such as this he may be new, nervous and even a bit humiliated about his new-found fetish.

    These are all just a few ways to spot a crossdresser without him actually telling you right out that he enjoys the crossdressing fetish. Each crossdresser is different, unique and some may be much harder to spot than others.

    Some crossdressing men work very hard to maintain a macho image during the day, while fullfilling his crossdressing desires each night in private. It takes years of experience to really be able to “spot” a crossdresser from afar. With the right skills, a Mistress will be able to spot a crossdresser anytime, any place, anywhere.  Smile….I may be looking at you!

     

    Until later……..

    Ms. Isabelle

  • Crossdresser Fantasies

    Crossdresser Fantasies

    Indulge your crossdresser fantasies with Ms Lily!
    Indulge your crossdresser fantasies with Ms Lily!

    The weekend is almost upon us, and it’s time to escape into your crossdresser fantasies. To start that off, we are going to set the mood with a mini-feminization assignment.   There are many of you, and each of you have your own life story to work around.  So just do the parts of the assignment that you are able to do, and don’t get caught up in getting the details perfect.  We’ll let you know when that is necessary, but for today’s purposes, you are going to relax, and enjoy your crossdresser fantasies.

    Femininization – Surround Yourself in Scent

    Though there are tons and tons of really wonderful perfumes on the market, we are going to turn to Mother Earth, and focus on the divinely feminine scent of lavender.  Not only is the scent gloriously girlie, but the tiny blossoms are exquisite, and the color is certainly not going to be confused with anything that reeks of masculinity.

    Need To Keep Your Crossdresser Fantasies Discrete?

    If you aren’t able to dive into this fully, you can still participate. All you need to do is make one purchase, and carve out 15 minutes of uninterrupted time. You can do it in your car on the way home from work, if necessary.

    I want you to stop at your nearest drug store, dollar store, etc.  You are to find a lavender candle, and buy it.  It doesn’t need to be a big one, since you’ll probably want to throw it away, and a votive will do splendidly.  What’s that?  You don’t know what a votive candle is?  Go sit in the corner.  You simply must know these things!  How on earth will you see to decorating and entertaining?

    Alright, back on track…as I was saying, you don’t need to purchase a large candle.  But it *must* be lavender scented.

    If You Can Explore Your Cross Dresser Fantasies in Private

    If nothing in your life prevents it, you are to also buy a lavender scented candle. But you can buy a larger size, and more than one. You can also buy lavender body lotion, and lavender spritz for your sheets. If you have a tub, buy lavender bath salts or lavender bubble bath. If you shower instead, get lavender body wash, and I do want you to get the Ivory brand, if possible.  This is a mini-assignment, not an excursion to Bath & Body Works.

    Now, Time to Immerse in Your Crossdresser Fantasies!

    Whether you are sitting in your parked car, with your candle held up to your nose or you are shoulder deep in a bubble bath, I want you to close your eyes.  Inhale.  Let the cares of the day slip away, and just relax into that pleasing, feminine scent.  As you inhale, visualize the feminine aura entering your body, and weaving it’s tendrils through you.

    When you are feeling loose, I want you to focus on what your most treasured crossdressing fantasy is.  Maybe you’ve experienced it.  Maybe not.  All that matters is that it lives in your mind.  See the details…whatever makes it uniquely yours…and keep inhaling that feminine aroma.

    Relax.  Enjoy.  You’ve earned it.

    And you want to share it with us.  So pick up the phone, and let us know what your perfect crossdressing fantasy is!

  • Night Time Crossdressing and Feminization

    Night Time Crossdressing and Feminization

    The Secret Crossdresser

    Are You A Night Time Crossdresser?
    Are You A Night Time Crossdresser?

    I especially like men that are top level executives that maintain a very macho image during the day, but you have a very well kept secret behind your locked bedroom doors. You are a night time crossdresser.

    You adore and fantasize about crossdressing. You even find yourself longing to be dressed as a woman during the day, but know that you must wait till you get home. You work hard, watching the clock ticking away, longing and waiting for that time when you get to be truly free to be yourself, donned in the garbs of a gorgeous and sexy woman.

    Crossdressing and Feminization

    As a crossdressing phone sex Mistress, I understand exactly what it is that you need during distant feminization phone sex. You need a feminine and fashionable crossdressing phone sex Mistress that can teach and guide you to become the best woman possible each and every night.

    We will work together to keep you up to date on the latest trends in make-up, lingerie, clothing and shoes. You will stay waxed at all times and over time you will start to wear you lingerie underneath your executive business suit.

    Distant Feminization Crossdressing Mistress

    I know that you desire to be the best woman possible each and every time that you dress up, donning only the finest of clothing and constantly lusting to learn more about how to portray yourself as a proper, seductive and sexy lady.

    As your crossdressing Mistress, I will be your teacher. The sound of my voice guiding you to move deeper into your desires and embrace the crossdresser within you. You will, under my guidance and care, become the best woman you could ever imagine.

    Embrace Your Crossdressing Desires

    If you want to learn more about how to become the woman that you have always desired to be then you should contact me. I am an experienced, knowledgeable and fashionable crossdressing phone sex Mistress and I would love to join you on your crossdressing journey.

     

    Until then……

    Ms Isabelle