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  • The Ties That Bind – Forming a Relationship with Your Mistress

    The Ties That Bind – Forming a Relationship with Your Mistress

    A Mistress for Sissy 855-727-4779Aren’t those adorable shoes? They belong to a feminized sissy that I play with.  For purposes of this post, we’ll call her JA.

    JA loves surrounding herself with things that emphasize her feminized faggotry.  Things like these pink high-heeled shoes.  She is a true sissygirl at heart when it comes to shopping, and she regularly sends me pictures of new acquisitions.

    She and I have been in a relationship for roughly a year and a half.  It didn’t start off as one, of course.  There was some getting-to-know time involved to see if we were a good match.  But before long, JA came to the realization that I was indeed the person to guide her on her feminization journey, and she began to relax into that safe, perfumed, pink place that I create for her.  She began to share more, and, at my urging, she began to peel back the layers of herself for my examination. It hasn’t always been easy for her, but over time, JA has come to accept her destiny.  She knows that whether she is taking small, measured steps in these pink shoes and a tight skirt or whether she has on rugged boots that she is not a real man, and she never has been.  She is a self-proclaimed sissy fag, and at my direction, she has become more and more accepting of that truth. Instead of trying to hide from her destiny, she now embraces it.

    JA has more than a few things that make her fluttery, and the lace ups of these shoes represent one of them.  But those same laces also represent the ties that bind her to me.  She has made great progress in our time together, and she no longer journeys alone. She knows that because of the relationship that has formed between us…because she is committed to submitting to me… her tie to me simultaneously binds her, grounds her, tethers her, leads her back home, and sets her free

  • Happy National Lipstick Day!

    Happy National Lipstick Day!

    Sissy Cocksucking Phone Sex 1-855-387-2669Hello Sissys! I hope that all of my makeup loving sissy wenches have their lips properly painted for National Lipstick Day! Send me pictures! I want to see who does the best application. I might post the winning lips on my blog.

  • Direct Dial Sissy Phone Sex

    Direct Dial Sissy Phone Sex

    Get Sissy Training with Ms LilyI recently finished a long project, and that is to your benefit, as it means that I have more time to spend time with you than I did during the winter months.  Since I last updated here, I’ve acquired several new sissy playthings.  Some need someone to process all their longings to be feminine with.  For them, I’ve a listening ear, and heartfelt guidance.  Some crave cock so bad that they’ll tremble merely reading the words.  For them, there are assignments geared toward them being used for the receptacle hole that they are.  Others will want something entirely different. But no matter what the desire, I’ve enjoyed getting to know each of them.

    Since it’s been awhile, I need to update and remind everyone of how things work with me.  Going forward, you can view my Schedule page for more specific information.

    General Availability for Feminization Phone Fun

    I am on EST and I do not take late night calls.  It is rare that you’ll fine my line turned on after 8:00 p.m.  I have a vanilla career that I very much enjoy.  That is always my priority, and I have phone sessions around it.  That said, I do have a great deal of flexibility with my work schedule.  So you’ll find me in and out over the course of a day. If you don’t catch me when you ring, either try again later, leave a voice mail or send an email.  In general, at this time I don’t have much weekend availability, and what I do have is usually taken up by previously arranged sessions.  If that changes, it will be on the Schedule page.

    A Word About Voice Messages

    If you leave a voice mail requesting a call back, be sure to leave your name, number, and your hours of availability in EST.  I do not return messages that don’t have all three of those components.  Some people have a great deal of freedom in their lives.  Others need a great deal of discretion.  When I don’t know which situation applies, I err on the side of caution, and simply don’t return the call.

    Sessions by Appointment

    When my schedule allows it, I do take sessions by appointment.  Note that because I do not take late night calls that my evening hours tend to fill up quickly.  To that end,  same-day scheduling often doesn’t work for me.  Sissy Finishing School Gold Star Students always have have priority status in regards to scheduling sessions.  Once scheduled, you will not be bumped by them, but they will have first dibs on any unclaimed appointment slots.

    New Clients

    I am currently accepting new clients. However, all new clients are subject to time caps on their sessions until they become established callers.  When that happens is solely at my discretion.

    I am someone who enjoys building relationships.  I don’t do what I do because I have to, I do it because I enjoy it.  So if you’d prefer a one-and-done, please find someone else to call.  If I don’t think we are going to be a good match, I will tell you.

    I offer a direct dial service.  That means that when you call, you will immediately speak directly with me.  You should have your card information ready at that time.  If you have further questions, I do welcome pre/between-session communication, providing it is not abused.

    I look forward to a sissy-filled summer, spending time with all my darling playthings!  Let’s enjoy the sultry heat!

  • Coached Cock Suckers

    Coached Cock Suckers

    You Need a Cock Sucking CoachIt’s recently come to my attention that most sissies need to be coached to be good cock suckers.  I’ve talked to many silly sissies that use this type of logic:

    a)  You have a penis

    b)  Therefore, you know how to suck one well.

    As the veteran viewer of many, many cam shows, I can assure you that this is false logic.  So what’s a poor sissy to do when she thinks her technique might be lacking?

    Become a Coached Cock Sucker, of course!

    For a limited time, I’ll be accepting applicants for a coached Cock Sucker Curriculum.  The coursework will be tailored to the individual, and all levels of cock suckers are welcome to apply. There are a few prerequisites:

    a)  You must be an established caller.  This is not open to new clients.  Do you want to be eligible for my next round of coaching?  Then establish yourself as a regular caller now.  VIP Gold Star Students always receive preferential treatment.

    b)  Ideally, you will be able to appear on Skype for me.  It is necessary for me to see you in order to evaluate you and develop your coached Cock Sucker Curriculum.

    c)  If you cannot appear on Skype, but still wish to enroll,  you will need to send an email detailing why you are a good candidate for instruction.  If accepted, demerits for not appearing on cam will be marked on your permanent record.

    d) Coursework will consist of no less than six 30 minute blocks of  coached cock sucker instruction.  As always, that will be booked to suit my schedule.

    e)  A one-time Enrollment Fee of $50 will be assessed on the first day of class.

    I will determine when sissy students have demonstrated sufficient academic progress to complete the course. All successful sissy cock sucker trainees will receive a Ms. Lily Certificate of Continuing Sissy Education.   Sissies who maintain a GPA of higher than 3.5 will also receive a special cock sucker audio.

    A limited number of students will be accepted.  A reminder…I am on EST, and do not take calls late at night.  So plan accordingly.

  • Calling All Sissy Divas

    Calling All Sissy Divas

    go-on-cam-for-ms-lily-855-7ASISSYIt’s been awhile since I handed out a group sissy assignment, and I’ve decided that this one should keep sissy divas busy, as well as amuse  me.

    Not long ago, I missed a connecting flight, and spent the downtime doing what most people do…watching transformational videos on YouTube.  I always enjoy watching boys turn into girls, and thankfully, the Internet offers a plethora of sissy divas putting it out there for all to see.

    After awhile, I got bored of that, and moved on to actual performances.  I skipped the “Frozen” video, as I am sick of that movie, and I’ve never seen it.   I was drawn like a moth to flame to watch Devana DeMille as Gwen Stefani, because I like Gwen.  Devana did a good job, and I spent some time clicking around her performances.  If there are other Gwen fans in the house, Trixie Mattel is fun to watch as well.

    The more that I surfed around, the more I felt that while I was seeing some good acts, that I wasn’t seeing true sissy divas in action.  That was until I found this video, and that was my inspiration for your assignment.

    Sissy Divas – Time to Walk that Sissy Walk

    I decided that with all the eager-to-please sissy divas that I know that I should be able to watch shows that are tailored to my preference. That is, of course, where you come in.  It’s time to put on your heels, start singing into the handle of your hair brush, turn on the cam, and entertain me.

    You’ll need to pick from one of the following songs.

    Since we’ve already talked about her –  Hollaback Girl – Gwen Stefani

    Telephone – Lady Gaga ft Beyonce

    Roar – Katy Perry

    What’s Love Got to Do With It – Tina Turner

    Express Yourself – Madonna

    Run the World (Girls) – Beyonce

    You can also go to the source of my delight, and do “Sissy That Walk”.

    While the actual task is to convincingly lip sync the song, you will get extra points for getting any dance moves right.  So get busy, sissy divas, and get your groove on!

  • A Ruined Orgasm For Ms Isabelle

    I Love A Good Ruined Orgasm

    Did you come to this site thinking you could click around and find a Mistress who’d take pity on you?  She’d give you some guided masturbation instructions, have you edge a few times, then let you explode and shoot that load?  Well, those aren’t the rules.  You need to listen to your Mistress, and accept your fate.  And your fate today is a ruined orgasm. Yes, even sissies love a good a ruined orgasm.

    Masturbation Instructions

    Get a plate, then get naked and kneel, with your little dicklett right over that plate.  Now, start stroking.  I don’t care how, that’s not the point.  The point here is to edge you until you can’t hold back.  So, bring yourself to and edge, then stop, take your hand off that slutty dicklett, and rest for 30 seconds.  Wipe off any pre-cum that didn’t drip into that plate, and suck it off your fingers.

    Edge To A Ruined Orgasm

    Did you enjoy that rest?  It’s the last you’re going to get – sort of.  Start stroking again.  When you get to the next edge, ride it for ten seconds, then rest again for 30 seconds, licking up the pre-cum.  Keep stroking and edging, adding 10 seconds to the “ride” time, with 30 seconds of resting and  pre-cum licking in between.

    At some point, you won’t be able to ride that edge and you’ll feel that orgasm building…unstoppable. Now squelch the head of that dicklette of yours and ruin that orgasm!  Just watch the jizz dribble out with no feeling of an explosive orgasm.  No satisfaction for you sissy!  I love a good ruined orgasm and you will learn to love them too.

    You’re Not Done

    Lick up all that warm cream – but don’t swallow it yet!  How long did you ride that edge before you had that ruined orgasm?   30 seconds, 50, a whole minute?  That’s how long you’re going to let that spooge sit in your mouth, savoring all the flavor, before you swallow it down like a good little cum slurping sissy.

    And don’t Ms Lily and I know how all of you little sissy bitches love to slurp cum!   Ready for some ruined orgasm fun?  You know where to find me.  Until then,

    Ciao,

    Ms Isabelle

  • Ballet Boot Training for Sissies

    Ballet Boot Training for Sissies

    Get Trained by Ms Lily 855-7ASISSYA sissy recently scheduled a session with me, and wanted to know if I would assist with her ballet boot training. Of course the answer was yes! I love pretty fetish gear, and ballet boots are the height of feminine grace.

    Providing one doesn’t topple over face first in them, that is!

    The facts are that while a perfectly poised sissy in ballet boots serving ladies is indeed a sight to see, they are not shoes that you simply cram your foot into and go.  Safety in playtime is of utmost importance, and being fit is the first step in ballet boot training.  In this instance, fit does not exclusively mean weight.  It means increased muscle strength, and balance.

    It is also necessary to be very honest about your own body.  How flexible are you?  How strong are your ankles?  What shape are your feet in?  Somethings are best left in fantasy, and for some of you, that is true of ballet boots.

    Beginning Ballet Boot Training

    Do not run our and buy the ballet boots of your fetish dreams.  While your mind may hold visions of you of prancing about in 8 inch stilettos while en pointe, the reality is that the boots of your dreams may simply not work for you.  Unless you are a sissy with a small foot, you are going to want to steer clear of popular brands on fetish sites.  You will also want to go with ankle boots.  Again, the brands found on popular, big-box Internet fetish stores will likely not accommodate your calves for a knee (or higher) boot.  When you are ready to make the investment, Punitive Shoes have a great reputation among fetishists.

    However, it will be some time before you are actually a sissy in ballet boots.  This is not an endeavor for those without patience, or the ability to listen to instruction.  You will spend time preparing your body prior to ever slipping your foot into ballet boots.  Your posture and core strength are very important toward preventing injury. If you’ve read all this, and are still eager to learn how to, give me a ring, and we’ll chat about it.  If it’s one of those things that you enjoy thinking about, but really isn’t for you, you can always vicariously enjoy what others are doing, and we’ll enjoy the fantasy together without the pain.

  • Cock Control For Sissies

    Cock Control For Sissies

    Many of my precious little sissy callers have been asking me about Cock Control, so I thought it was time to write a blog about Cock Control.  Yes darling sissy, you too can experience Cock Control; you already have and perhaps haven’t realized it yet ~wicked laugh~

    Cock Control, What is it?

     

    Cock Control For Submissive Sissies
    You Need Cock Control

    Cock control is a combination of both mental and physical tactics that are utilized in gaining control over the male submissive’s cock. During cock control, the male is no longer allowed to touch his cock or cum without permission from his Mistress.

    The male submissive will be prick teased and tested over and over. Cock control is a special type of training that will increase your stamina and teach you to have more control over your body and orgasms.

    Being cock teased during cock control is one of the first steps to learning control. Don’t worry though, cock teasing will remain prominent throughout your cock control training. You will learn to hold back your orgasms as you are thoroughly teased and tormented by your cock control Mistress.

    You Mistress is sure to find each and every one of your erogenous zones as she explores and teases your body and cock. During the cock tease portion of cock control, you will be stimulated with a variety of different sensations as your cock is stroked, rubbed and fondled. You must remember that you are not allowed to cum without permission!

    Chastity and Cock Control

    Another prominent part of cock control is the use of chastity. Chastity can teach the man to focus less on his cock and sexual needs and more on the desires of his Mistress. Chastity can really solidify the ideas and principles of cock control since there is an actual device that literally controls the cock. Chastity changes the mental processes of pretty much any man that has an overactive or overly sensitive sex drive.

    Once the male is in the right state of mind from all the cock tease and chastity, there is another important type of cock control for him to experience; coerced orgasms.

    Coerced Orgasm and Cock Control

    Coerced orgasms means that your Mistress will very slowly and deliberately bring you to the edge of orgasm, often many times before you are allowed to cum. Your Mistress will have you begging for release as you are coerced to orgasm time and time again. Once you think you can’t take any more, your mistress will push you even further during this form of cock control.

    This is just a start about what there is to know about cock control. The world of cock control can be a scary but exciting place as you learn just how far that you can be pushed before tipping over the edge into an orgasm that you will never forget.   And remember Sissies, you don’t have orgasms without permission from Ms Lily or myself, so don’t get any silly ideas of cumming without permission!

     

    Until later,

    Ms Isabelle

  • Ask a Femdom – Dear Ms Lily

    Ask a Femdom – Dear Ms Lily

    Ask A Femdom 855-7ASISSYI’ve gotten a few advice-seeking calls recently, so I’ve decided to do a now-and-then feature called “Ask a Femdom”.  When the mood strikes, I’ll select a topic that has been discussed with a client, and give my input on it here.  Consider it a kinky advice column. Issues will range from the more mundane to those that you could discuss with a psychologist.  But they are so much more fun to discuss with me, darlings!

    And speaking of discussing, if you call, get my voice mail, and leave a call back number, please leave your availability.   I need to know when you can accept and be ready for my call.  Without that information, I don’t do callbacks.  I prefer to be discrete, and know that I am not calling you in the middle of a meeting, family dinner, etc. Unless, of course, you are in to that sort of thing, and if so we can discuss.

    Back on topic…

    A caller wants to know ways that he can begin to introduce a slight amount of feminization fun into his relationship with his wife.  They have an exceedingly traditional marriage, and she is very conservative.  He knows that the vast majority of his play time will still happen with me, but is willing to take anything that he can get at home that is not vanilla, missionary sex.  He’s not sure she’s ever had an authentic orgasm.

    It is clear from what the caller has told me that his wife is not comfortable with her sexuality, and that the first thing he needs to do is to get her to relax.  A great deal of patience will be necessary on his part, as it will take time for her to overcome what has been ingrained into her about sex, sexuality, and her role.  He simply needs to focus on her pleasure in bed, and get her to the point where she is freely enjoying sensation, and hopefully orgasm.  The more pleasure she feels, the more emboldened she’ll be to ask for specific things she likes.  Though it should be noted that it will likely need to be coaxed from her in the beginning.  All this will lead to more emotional intimacy, and with time, it is very possible that she’ll actually take the lead in initiating a sexual encounter, which is one of his fondest wishes.

    This will not happen overnight, and cannot be rushed.  But with time, it is possible. While his fetish and kink activities will still take place with me,  by following my detailed advice, he stands a good chance of getting her to be more assertive.

  • Cum Eating For Sissy Bitches

    How Do You Eat Cum?

     

    Cum eating is a very submissive act.  Many Mistresses, yours truly included, love to use it as the denouement of our session together.  Part of the price you pay to play.  Upfront, you need to go through teasing and edging, maybe some corporal punishment, perhaps some humiliation.

    Then, when it’s all done, when you’ve gotten the reward of a mind blowing orgasm – or maybe not, maybe I decided your reward was a ruined orgasm! – you have to pay the cum tax – by swallowing a nice, warm load!  So, I want to know, when your Mistress makes you swallow a warm creamy load, how do you like to do it?

    Just You And Your Hand To Make You Cum

    Do you shoot off in your hand?  Spurt after spurt into your palm, forming a sticky, warm puddle of spooge.  Tell, me, do you cup your hand and just pour it into your waiting mouth?  Or are you a “finger lickin’ good” kind of sissy bitch?

    Don’t be afraid to talk about it sissy.  I have witnessed many sissies gobbling up the nice hot load of dick gravy they get from sucking a real mans cock.  I have also watch and laughed at a sissy cleaning up her fingers from her own fairy juice.  Either way, it’s all about cleaning up the cum!

    Formal Cum Eating

    Do you prefer some class with your cock cream?  Perhaps you jerk that cock off onto a plate or a saucer or into a cup.  I have one sub who does it this way, and as she bends over to lick up all that jizz, I spank her beautifully presented ass, adding some punishment to her humiliation!  What about you sissy bitches who love to fill up a shot glass.  That’s a new take on “taking it neat”…

    Self Sucking

    If you’re going to eat cum for me on cam, there’s nothing like watching you stroke under my guidance, right until you get to the edge.  Then you quickly throw those legs up and over your head, and I get to watch as you furiously pound that sissy stick and cum flies everywhere as you try to suck your own little nub!  I know you’re trying to  get it in your mouth, but it usually ends up on your sissy face or in your hair.  Don’t turn that camera off until I’m sure you’ve licked it all up!

    Just look at all the fun we can have with cum!  Go grab your phone, turn on your cam and let’s have some fun with cum.

    Until later,

    Ms Isabelle