Monthly Archives: January 2022

Trials and Tribulations of a chastity slave – Installment #34 – Cuckolding a collared, chaste, sissy slaveboy

Installment #34 – Cuckolding a collared, chaste, sissy slaveboy – by slaveboy jaime

As many people know, cuckolding is often when the dominant female has sexual relations with a male that is not Her husband or partner.  She may also subject Her husband or partner, often serving Her as Her slave or sub, to watch or hear about these activities to further humiliate or dominate the sub.

As Mistress Ayn’s collared, chaste, sissy slaveboy, sexual activity is not part of O/our Mistress-slaver relationship.  i could never satisfy Her in that way – as She reminds me, my (now Her owned and caged) penis is too small to satisfy Her.  And, i will never be Mistress Ayn’s husband or partner.  Yet, cuckolding is present in O/our relationship in a unique way.

Each time She dominates another one of Her collared slaves or any submissive, i feel a sense of jealousy.  When She describes what She did to a slave, i am envious of what the other slave experienced.  i want to be there for Her, suffering at Her hands, being humiliated by Her words or actions, just serving Her and pleasing Her as She wishes – not hearing about another slave having that privilege.

i know Mistress Ayn does everything for a purpose and while She is not disciplining, humiliating or sissifying another one of Her slaves because of me specifically, it may also be a way She choose to cuckold me – to show me Her dominance and control over me by dominating and controlling another slave.

i have learned that my place as Her collared, chaste, sissy slave is to be there when She wants me and to accept that She has other collared, chaste or submissive slaves available to Her that i must accept as Her slaveboy.

Interview with Simone Justice on the ethics of BDSM public play

Just before Dom Con New Orleans in 2019, Simone Justice asked if She could interview Me regarding My thoughts on public play.  She was preparing to lead a DomCon Parade down Bourbon Street and the topic of public play, consent and ethics came up.  I don’t think this interview was ever published so I thought I would post it here.

SJ: What is your opinion as to the limits of public play?

MA: I love public play, but it means different things to different people. Some people think the simple act of wearing a visible collar is public play. Others don’t consider play to be public unless it’s more of a scene. It’s important to understand the limits of the person you are playing with in each situation. My only real limit to what I will do in public has to do with the respect of people that could view the play. I don’t like to involve people that haven’t consented and might find what I do with a submissive offensive.

SM: What do you do with your own clients in public?

MA: I have done all kinds of discreet and indiscreet public play. I’ve had shoe fetishists put shoes on me in a shoe store. I’ve taken sissies to have bra fittings at lingerie stores, mani/pedis, in store makeover, etc. I’ve wired subs up with electro or remote plugs and stimulated them in public with no one the wiser. I’ve also done full blown scenes in kink friendly venues.

SJ: What would you never do in public with a client?

MA: I would never do anything that was offensive to on lookers. I’ve outgrown the need for shock value. If I am going to do something with a sub that might offend a shop employee, I call ahead first and clue them in. It’s amazing how often people are good sports and will play into your scene if you just give them the respect of letting them know what is going on. Anything done in front of children that would require an explanation from parents is definitely off limits.

SJ:  How did you develop your rules of what you will do in public?

MA:  Experience. It just evolved over time. I’ve learned the most from listening to my subs and what their concerns are and I understand that everyone’s limits are different.

SJ: Have your limits changed over the years?

MA: Absolutely. I used to have little regard for the “vanillas”. When I was less mature as Domme I found it fun to shock the public. Now I just see it as disrespectful to those not a part of the scene and disrespectful to the concept of BDSM in general.

SJ: Anything else you would like to say about The Ethics of Public Play?

MA: There are tons of opportunities to play in public if you handle it correctly. Consider your surroundings and act accordingly. A venue like Bourbon Street is very different from the neighborhood mall on Saturday. For many subs it is about the idea that things are happening to them in public whether anyone else is aware of it or not. Don’t push the envelope so far that you end up giving BDSM a bad name. BDSM is about consent. Everyone’s consent. Not just you and your play partner.

 

FAQs about Gender Play

What is the difference between a crossdresser and a sissy?

Gender play raises a lot of questions and people often get stuck on the labels.  In general, crossdressing is more of a positive transformation from male to female, experiencing all the wonderful female energy that goes with being pretty and pursued.  Sissy play is more about humiliation; stripping away the male ego and replacing it with a caricature of a woman or a girl.  This humiliation can be extreme and harsh or more benevolent and nurturing, like dealing with a child.

Both scenarios can be emotionally complex.  This underscores the importance in choosing the right Mistress or partner to help you with the exploration.

Does desiring to be feminized mean that I am gay or bi-sexual? 

Absolutely not!  Some men get fully dressed for the first time and declare themselves lesbians.  Others crave to suck cock, but I don’t think it’s done anything more than bring to the surface what has been swirling around underneath.

What happens in a feminization session?

There is no “typical” session when it comes to gender play.  Sessions that involve feminization are as wide and varied as you can possibly imagine.  They may involve forced feminization where the man is made to dress and behave like a slut and involve humiliation or it may be the opposite where a man wants to embrace his feminine side and feel the empowerment that comes from being a woman.  The spectrum between these extremes is where we normally play.

Here are some possible activities:

  • Dressing – from sissy to slutty to elegant.
  • Makeup – trans makeup to full drag queen and anything between.
  • Manicure/Pedicure – out at a salon or in the privacy of the feminization area
  • Esthetician services:  waxing, eyebrow threading, shaving, facial, etc.
  • Full transformations that include makeup, wig, outfits, heels, etc.
  • Sissy training – teaching you to act like a proper sissy, learning to curtsy, talk, walk, etc.
  • Sissy maid training – learning to serve dominant females in various ways.
  • Slut training – learning to suck a strap on, strap on training, etc.
  • Medical scenes – enemas (getting your period), pussy/anal training, mock castrations/gender reassignment, etc.
  • Public outings – this can include salon visits, dance clubs, dinner outings, shopping, etc.

As you can see, the options and combination of activities are almost endless and are defined by your imagination.

Here are links to reviews of sessions that involved gender play, crossdressing and sissy play.

Crossdressing help and feminization session

Pressing “Candy” into service at FemDom Mansion

Training sissy slut “Martina”

Transforming “Dianna”

Panty Slut Pamela’s overnight in the Dungeon

“Vanessa’s” gender reassignment

I also suggest read this interview at Simply Sxy about How to Explore and Enjoy Gender Play.

To set up your feminization session, visit MistressAyn.com, read through the and complete the experience/fetish form when you are ready to book. I also offer phone consultations and distance training for crossdresser and sissies.

 

 

 

 

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