Tag Archives: sissification

Chronicles of a chastity slave – pain and the sissy

Installment #28 – On Becoming a Pain, Anal and Sissy Slut – by slaveboy

The transformation from being a bondage slut to becoming a pain, anal and sissy slut has been gradual but steady under the skilled hands of Mistress Ayn.  A slut = a person with a seemingly insatiable but often undiscerning desire to do or have something specified (Dictionary.com).  It is what i am becoming and i love it.  Each area was once a limit yet is now welcomed and desired.

Pain Slut – Initially i would avoid any serious pain, accepting only light spankings.  Then was introduced to serious flogging and loved it; then came whipping and caning and i cannot get enough now.  i have learned to “welcome and embrace” the pain, rather than fight it, which means i can take more.  i have had back-to-back days of whipping and had body orgasms from the pain.  Afterwards i want to see the marks and am sad when they dissipate.  Still a long way to go but definitely on the journey to becoming a pain slut.

Anal Slut – My hard limit was “no anal,” then i tried it and realized that i craved it, badly.  Dildo penetration is amazing as Mistress Ayn controls me, whether from behind on a bondage bench or facing me when in a sling.  Multiple Mistresses gang banging me is intense.  Being spitroasted is both humiliating and exciting.  When Mistress Ultra Violet was concerned that Her dildo was too thick, i was silently wishing, “please try it.”  She did, it was not, and it was incredible.

Sissy Slut – Feminization was “not my thing” and is now what i am looking forward to during each slave training session.  Mistress Ayn’s smile after applying my makeup, other Mistresses laughing as They dress me, the feel of a nightie when in bed at hotel between slave training sessions, pictures of me as the blushing bride at my collaring ceremony dressed in white, or looking so humiliated as slave “nana” to serve Mistresses dinner.  i am so comfortable, it feels so natural while sissified.

Most importantly, becoming a pain, anal and sissy slut is what Mistress Ayn wants for me as Her slaveboy and that is more than enough for me.

Luxury FemDom event

FemDom Mansion

For a full photo gallery of this 48 hour event, visit The Events page of FemDom Mansion.

The age of Covid-19 has proven to be challenging on many fronts and it basically put an end to FemDom Mansion events at least the way we have been doing them.  A FemDom cocktail party and overflowing dungeon play is not in the cards for now, but we did manage to pull off a small, safe event this December with the recurring guest, slaveboy.

I needed an event.  He needed an event.  So we made it happen.  This event only included a total of 5 people including Me and slaveboy.  Three had traveled recently so a negative Covid test for them put everyone’s mind at ease.  slaveboy did provide an extra challenge – he injured his back shorty before his visit and that had us revamping a good number of activities.  Goddess Samantha and I had to play nurse a bit and I ended up cooking dinner (while wearing a corset and heels), but hey we managed to have an awesome time despite the 2020 curse.

In FemDom Mansion tradition, slaveboy has provided his top 13 experiences from his 48 hours f servitude.  You can find his highlights of the event and a full photo gallery on the Events page of the FemDom Mansion website.

Mistress Ayn’s slaveboy Top 13 Terrible and Terrific Experiences from weekend #7

slaveboy’s FDM #7 experience presented a few challenges for Mistress Ayn: COVID safety precautions and slaveboy twisted his back a few days before leaving for Atlanta. Expertly, Mistress Ayn designed a “COVID safe and limited” weekend and adjusted some planned torments to not further aggravate slaveboy’s bad back. Nonetheless, She still managed to further slaveboy’s training, incorporating many of the new elements of slaveboy’s expanding life – sissification. While limiting the number of participants at the Mansion, Mistress Ayn did not hold back on the intensity and variety in store for slaveboy.

#13 – A video appearance by Goddess B, who wanted to be there in person, but just had to show off Her new short haircut.

#12 – A stimulating Friday evening conversation on a range of fascinating topics with Mistress Ayn and Goddess Samantha was a rare treat for slaveboy, who typically is not permitted to speak freely in Their presence.

#11 – Mistress Ayn arranged for Her chiropractor to see slaveboy who was diagnosed with a pinched nerve in his lower back.

#10 – A brief outdoor shower on the patio for slaveboy with Mistress Ayn at the garden hose controls.

#9 – After many months of no punishment, slaveboy was subjected to a sound flogging from Mistress Ayn with arms and legs spread at the St. Andrew’s cross.

#8 – Dressed in two different pink party dresses, one with a lot of bling, slaveboy had the honor of sitting at the dining room table on Friday and Saturday night with Mistress Ayn, Goddess Samantha and Mistress Riley for a meal prepared by Mistress Ayn the first night and Chef Sean the second night.

#7 – Mistress Ayn played Santa, distributing wonderful holiday gifts to all in attendance. slaveboy received assorted gifts for a future, decadent bubble bath.

#6 – Dressed up for an evening with the FDM Dommes, complete with a pink lips gag that caused him to drool down the front of his party dress, slaveboy learned how to “sit like a lady.”

#5 – In the FemDom Mansion’s Christmas spirit, Goddess Samantha and Mistress Riley used their new Christmas paddles on slaveboy’s ass as he bent over before the decorated Christmas tree.

#4 – Sissified and strapped to the new bondage chair slaveboy received intense teasing, nipple and ball torture from Goddess Samantha and Mistress Ayn.

#3 – slaveboy experienced “figging” – ginger root was inserted three times, the last time lubed with Capsazin.

#2 – While in full body bag bondage, Mistress Ayn relentlessly played with slaveboy using a vibrator, nipple stimulation, sensory deprivation and the tease of mounting Mistress’ owned cock.

#1 – With Goddess Samantha and Mistress Ayn’s assistance, slaveboy was bound tightly in a corset, an hourglass figure began to appear, and the “slut slaveboy” emerged.

The full review of this event can be seen on the third party site Domina.ms

 

Trials and tribulations of a chastity slave – Morning routine

Atlanta Key HolderInstallment #26 – My morning routine as Mistress Ayn’s slaveboy

After more than a year in indefinite chastity as Mistress Ayn’s slaveboy, my morning routine was become quite comfortable for me, well, as comfortable as it can be.

i awake and reach down to feel Mistress Ayn’s chastity cage. She controls me especially through my cock and balls and it is a good reminder to me of what is truly important in my life.  Since it usually has been weeks since my last orgasm, i am frustrated and start to tease my nipples.  As i get more awake and aroused i can feel my cock starting to get longer and harder.  Quickly the pleasurable sensation is replaced with the frustration of realizing that my cock cannot get erect, barely half erect, while in the chastity cage.  This reminds me how i treasure feeling controlled and restricted by Mistress Ayn.  It is Her cock and She decides if it gets out of the cage – which is rare since She relishes my indefinite chastity.  When i cannot take any more frustration, i get out of bed and face the day knowing physically, as well as mentally, that i am Mistress Ayn’s chastity-caged slaveboy.

Each morning Mistress Ayn orders me to perform maintenance on Her chastity cage.  i remove the cage with the key She permits me to have to thoroughly wash the cage.  i shower and pay special attention to clean Mistress Ayn’s controlled genitals.  Then, without any thought of disobeying my Mistress, i never touch Her cock or balls when out of the chastity cage and immediately replace the chastity cage on Her cock and balls and lock it up.

Before i dress, i am required to check the nipple piercings Mistress Ayn compelled me to receive to make sure that the caps are securely on the ends of the pink posts.  i also make sure the piercings are sanitized.

When getting dressed i select the sexiest panties from my wardrobe to make sure that Mistress Ayn’s sissy slaveboy is properly adorned.  i love my assortment of pink panties, G-string pouched panties and other frilly underwear.

i am off to work or some other task wearing my panties, feeling my nipple piercings through my shirt, and the secure and tight chastity cage around Her cock and balls.

This is my new life and i am loving it.  Every day i am reminded that i am Mistress Ayn’s chastity-caged, sissy slaveboy.

The Sissy Studio at FemDom Mansion

FemDom Mansion caters to a lot of submissive interests, fetishes and fantasies.  One of them is forced feminization and sissy maid training.  To that end, we have designed an area we call the Sissy Studio.  The Sissy Studio has everything needed to transform even the manliest sub into a naughty little tart, a glamour girl or sissy maid.  Indulge your feminine side at FemDom Mansion’s Sissy Studio.

Actual events of sissy maid training and m/F transformations are documented in the Events section of the FemDom Mansion website. Consider booking your event and unleash the sissy slut in you.  Visit the official site of Atlanta’s FemDom Mansion for more details.

 

Trials and tribulations of a chastity slave – Installment #21

Installment # 21 – How Can i Please a Woman?

While i do not claim to know the universal answer to this question, i have learned much as Mistress Ayn’s slaveboy.  Unlike what some men still believe, it is clear to me that i cannot please a Woman with my cock.  Thankfully Mistress Ayn took total control on my – now Her – cock and i am in indefinite chastity.  Thus, i needed to learn what other “tools” were available to me to please a Woman, specifically Mistress Ayn.

Mistress Ayn has educated and trained me to understand many things but two stand out for me.  First, i need to submit – completely and without reservation – to Her.  As Her slave i am better attuned to Her desires and better able to follow Her commands.  i am often surprised by what She asks of me but have learned to not question any command or hesitate in being compliant with any order.

Second, i am learning how to be more attentive to Her needs by listening and not talking.  While She may infrequently desire a conversation with me, most often i need to not talk and to listen carefully to what She is telling me to do or how to act.

By honing in on these two elements of my personal slave training, often at the FemDom Mansion, i found that i am pleasing Mistress Ayn and other Mistresses She requires me to serve. For example, Goddess B’s beaming smile as She administers my morning shower on the patio with the garden hose on the jet setting, paying particular attention to my genitals and asshole.  Or, the roar of laughter as i enter the dining room in ridiculous sissy attire to serve the guest Mistresses and Mistress Ayn dinner for the evening.  Or, during the evening festivities, pleasing many Mistresses as They administered my birthday gang bang, with a dozen other Mistresses looking on approvingly.  Or, when i was ordered to perform a burlesque dance routine so that all of the Mistresses in attendance could be amused by my gyrations, evidence by Their cheers, smiles, and catcalls – all caught on video for viewing later and more pleasure for the Mistresses.

i could go on since there are many ways that Mistress Ayn has instructed me to please Her – including the indefinite wearing of Her chastity cage and frilly panties, and Her latest command – a remote controlled vibrating anal plug.  While men may find different ways to please the Women in their lives, i know with confidence that my ability to please Mistress Ayn and other Mistresses is through my obedience and submissive to the Superior Women in my life.

 

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