Trials and tribulations of a chastity slave – Installment #22

Installment #21 – My favorite reply: “Yes! … What?” in my developing life as Mistress Ayn’s slaveboy

i often encounter challenging situations and quickly, say: “Yes,” but begin to realize i do not truly understand what i said Yes to, thus add: “What?”  Thankfully my “Yes … What?” responses to Mistress Ayn is based on developing trust and has resulted in amazing experiences as i grow as Mistress Ayn’s slaveboy.

In summer 2017, i arranged for two, two-hour BDSM sessions with Mistress Ayn, based on Her website.  W/we seemed like a good fit, thus the “Yes.”  But, i had no idea what i was getting myself into – giving up complete control to a new Mistress that was only a website persona.  When W/we met i accepted bondage, discipline, chastity between the sessions, and much more.  It was wonderful new path for me to travel.

After reading the FemDom Mansion website, i surrendered to a weekend with Mistress Ayn and the Ladies at the Fem Dom Mansion.  i said “Yes” but clearly had no idea what was in store for me.  Rather than a few hours of submission, 48 continuous hours as a slave was incredible and life changing.  Now understanding the “What?”, i committed to serve at the Mansion again and have three more times with more weekends planned.

After the first weekend and as O/our relationship deepened, i asked Mistress Ayn to be my Keyholder, but did not know what i was getting into at the time, thus another “Yes … What?” experience.  She agreed to “try it out for two weeks.”  That was a year ago and She has not mentioned any ending date, nor have i asked.  “Indefinite” chastity appears to be Her preference.  i had no idea where my “Yes” would take me; i am delighted where it has.

Indefinite chastity had led to pantie wearing, nipple piercing, and long distance anal play.  With each new opportunity, i am saying “Yes!” and then learning “what” this truly means.  Never any regrets and it is getting easier to say “Yes” to my Mistress.

She instructed me to begin a Twitter account.  i have never been this “public” with my submissiveness or my experiences with Mistress Ayn, but again said “Yes” and then “What?”.  It was incredible to open up to hundreds of people who are “following” me and Mistress Ayn often re-tweets my posts to Her 10,000 followers.  i have submitted selfies and shared much about my life as Mistress Ayn’s slaveboy.

i suppose others might find my approach to be questionable, risky, or simply poor judgment, but my “Yes! … What?” seems to work for me as Mistress Ayn’s slaveboy.  i cannot wait for the next question posed and am ready with my response.

By slave boy