Sissy Finishing School

Author: Ms Lily

The Ties That Bind – Forming a Relationship with Your Mistress

Aren’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

October 27, 2016
Happy National Lipstick Day!

Hello 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.

July 29, 2016
Direct Dial Sissy Phone Sex

I 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!

April 14, 2015
Coached Cock Suckers

It’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.

February 17, 2015
Calling All Sissy Divas

It’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!

December 4, 2014
Ballet Boot Training for Sissies

A 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.

August 29, 2014
Ask a Femdom – Dear Ms Lily

I’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.

June 28, 2014
When I am Not the Right Sissy Phone Sex Mistress for You

Now that I have a little more time to call my own, I wanted to cover some ways you can tell if I am not the right sissy phone sex Mistress for you. In the year since we opened the virtual doors of Sissy Finishing School, I’ve garnered some really fantastic clients. I’ve also been approached by an equal amount that were not a good fit for me. If you’ve not contacted me yet, and you are wondering if I would be the right sissy phone sex Mistress for you, read on.    In no particular order…

You Block Your Number When You Call

I’ve recently changed the settings on my phone system to not allow blocked numbers to ring through. To call me from a blocked number is illogical. You’re going to give me your credit card information, but not your phone number? That doesn’t make sense. Additionally, my billing platform requires me to enter it when I bill you.   So I’ve decided to save time, and disallow that practice. That said, if you are a regular caller, and you have some pressing reason to block your number for a few calls, then let me know in advance, and we’ll work it out. But otherwise….no.

You Need to Call Late at Night

I’m currently on a very early morning schedule. That will change slightly in late summer, but there is no time in the foreseeable future that I will be taking late night calls. I know that isn’t convenient for PST callers. If we can’t work something out that allows for a weekend call, then I’m not the right sissy phone sex Mistress for you. We might have had wonderful sessions, but the timing just isn’t good.

You Want to Haggle

I understand that everyone should pay attention as to how they are spending money, and I understand that the value that I place on my time is higher than what others have chosen to put on theirs.. However, this is not “Let’s Make a Deal”. I provide a premium service to those that understand the value of what I bring to the table and who can afford it. If that is more than your circumstances allow, or than you are willing to spend, there is a vast plethora of ladies to chose from that are better suited to you than I am. I am sure one of them will be a great match for you!

You Like to Play the Field…A Lot

Boys will be boys, and gurls will be gurls, and I certainly do not expect that every client that sessions with me will session with me and only me. That said, I really like relationships, and the dynamics that can form when sexuality and selves are explored. To that end, I really prefer situations that have depth, and I find that is easier to achieve when efforts are focused. In most instances, it’s really not possible to serve more than one Mistress well.

Personality Mismatch

It happens. Sometimes people just don’t click. I do what I do because I love doing it. If I don’t feel like you and I are going to work, I will tell you. I want to love what I do, and I want you to love the experiences you have. If the magic is not there, it’s just not there. It doesn’t mean you aren’t a great sissy for someone else!

My Sissy Stable is Full

In spite of all the charms I possess, just like everyone else in the world, I get 24 hours to fill a day. If you’ve done your homework, (and you should have) you know that I have an encompassing vanilla career. I also have personal play time. And hobbies. And friends, family, appointments, etc. The end result of that is that I can only be a sissy phone sex Mistress to a finite number of sissies.

You are a High Maintenance Sissy

This is tied in to the above, and my personal style. I love brief emails that let me know that you are thinking of me. For regular clients, I enjoy giving out between-session assignments. I am fine with building anticipation leading up to sessions, looking at your pictures, etc. The connection with me does not begin and end with a call.

However, I do not have time, nor am I otherwise inclined to deal with sissies who have me confused with being their own personal journal. They should start blogging instead. I am not a good sissy phone sex Mistress for someone who wants to send me reams and reams of information on a daily basis and expects me to read it, let alone reply. Respect my time.   I also do not do any type of instant messaging. The exception to that is VIP callers who can text me.

I May Make Recommendations

In some of the above instances, I may make recommendations as to who you might consider. It’s likely that one of my first recommendations would be my partner-in-crime, Ms Isabelle. If for some reason that isn’t workable, there are a select few other ladies that I may suggest you contact. Please do not ask for recommendations. If I feel one is appropriate and fitting, I will let you know. I want you to have fun with your sissy self, even if it is not with me!

June 5, 2014
Phone Sex Therapy for Sissies

I’m glad to be back home, and ready to soon start practicing more phone sex therapy for sissies. It’s been awhile since I’ve had the pleasure of kicking back, picking up the phone, and listening as some cuckold, panty boy, cocksucker, or other type of sissy pours all their need into the receiver. Whether it is the first time we’ve talked or the hundredth, I so enjoy seeing what each new client brings to the table in terms of kink, devotion, etc.

The mind is my favorite playground. I know that people that like to just grunt and jerk off for a few minutes don’t think of what I do as being therapy. They think of it in purely sexual terms. They are unable to see how therapeutic it is to talk to someone who really understands and enjoys the dark, hidden places in your soul. That’s why I chose not to engage with those types of callers.

Sissy Rehab with a Twist

I offer many of the same services as traditional therapy. We talk, and we explore. However, traditional therapist may try to rehabilitate you. They may not be empathetic to alternative sexuality, gender identification, cross dressing, or sissy fantasies. They might wince if you wished to discuss becoming a sissy eunuch, and they likely have no clue why talking about a certain style of panty is guaranteed to get your motor running. They also can’t discuss cream pies with you, or tell you that yes, dear, you *will* suck a cock for them.

Traditional therapy just isn’t fun, darlings. Not like phone sex therapy for sissies! Not only am I knowledgeable and caring, but I also like to toy with you, and if you’ve been especially good, I’ll let you make a mess in your panties. Which is something that a traditional therapist certainly won’t do.

I’ll be taking calls again next week, so get your appointments in. Dr. Lily will be in session!

May 1, 2014
Sissy Gynecologist Exam

It’s a right of passage for young ladies, and sissies are no exception; you must get a sissy gynecologist exam. Luckily for you, I enjoy poking, prodding and exploring you, especially when you are in a vulnerable state. That means that I most likely won’t be sending you out to an actual gynecologist.

Most Likely. One can never safely discount that possibility. But for today, let’s talk about the fun that I’ll be having while I examine you.

Preparing for Your Sissy Gynecologist Exam

Preparing for your trip to see me for a sissy gyno exam is really no different than the preparations that you should make any time you will be spending time with me. Your personal hygiene should be impeccable, and your mental state should be that in which my pleasure is your utmost concern.

What To Expect

Silly sissy. Did you really think that I was going to tell you *exactly* what to expect? How is that fun for me? I prefer to keep you guessing. However, I can tell you that sissies with a CFNM (or CFNSissy, in your case) fetish will be happy. You’ll disrobe, and slide into a paper gown that will seem two sizes too small. Eventually, that will be removed. To get in the spirit of things, I might don a latex nurses uniform, or a crisp, short white lab coat with very high heels.

Once my office door closes, every inch of you will be inspected. The aforementioned sissy gynecologist exam will be conducted. A wide variety of other tests and procedures may be ordered as well, depending on my mood. I’ll consult my chart, and select from an array of possibilities all designed to please me. Your role will be to do exactly as you are told, and to keep your legs steady in the stirrups.

One other thing…you’ll need to bring cash. Your HMO won’t cover the things I’ll do to you.

March 28, 2014