When Master and i began our relationship i was not a fan of anal sex. In fact, i hated it and flinched at the mere mention of it. He was respectful of my distaste but told me that it was something that He wished to change and as it had not been specified as a hard limit (my choice) then it was something that would be up for re-evaluation. He never demanded it of me, instead He explained why it was something that He desired. He allowed me to take my time in processing the idea of it and slowly i began to show curiosity.
For me, as a submissive, it was important that He be happy so i started looking at why i disliked it so. Self-evaluation has been a large part of our dynamic as it leads to self-awareness and personal growth. So why did i hate/fear anal sex? i had little to no previous experience with it and truthfully hadn’t been asked to do it very often with previous partners. What it all came down to was the fear that i would make a mess and that it would hurt. (pretty funny coming from a masochist, right?) Once the root was identified we were able to move forward. His first anal assignment was for me to research the physical act. i was to learn as much as i could about proper preparation, relaxation techniques, and positions that would allow for me to be comfortable during penetration. Daily reports of what i had learned were implemented and slowly my fears began to dissipate.
The first anal penetration i experienced with Master was my own finger. The end of each required edging was to be me playing with His ass. Every successful penetration was met with praise and often a reward. One finger turned into two fingers and the praise continued to come. When i didn’t meet the expectation, Master didn’t punish me. Instead, He expressed disappointment but encouraged me to do better the next time. He was patient, understanding of setbacks, and listened intently as i explained the sensations my body felt. He asked what was happening in my mind as my finger(s) slid inside me and allowed me to process those thoughts openly with Him.
Slowly, i came to accept the sensation of being penetrated although i can’t honestly say that i enjoyed it a great deal. When He felt that i had mastered 3 fingers in His ass it was time to up my training. A set of penis shaped anal plugs progressing in size from 1 inch in width to 1.5 inches to 2 inches in width were presented to me. i was to wear the smallest plug while doing the dishes. i can remember the panic that washed over me and the feeling of fullness as He slid it inside me and sent me on my way with a gentle pat on the ass. Mentally, i was frantic but my body was drinking in the sensation of the plug and i began to drip with excitement. i was rewarded with an earth shattering orgasm and the knowledge that each day i would wear the plug for a longer period until it was in place around the clock.
Anal whore life lesson #1; When you first walk into a public place with a plug in your ass you are quite certain that everyone in the room is aware of its presence and you will immediately feel a wave of embarrassment hit you. When you are told to excuse yourself to the ladies room to edge with that plug in you feel the flash of panic that makes you debate calling “Red”. When you don’t, and you instead choose to complete the assigned task you will walk back into the public eye with juices running down your thighs and needing fucked so badly that you are borderline stupid. This was His clue to up the training yet again and this is the moment that i was no longer allowed to touch His pussy.
Anal whore life lesson #2; When you go without something long enough you realize one of two things. You find out how much you miss it or how much you don’t need it. i realized the latter and found myself happily edging His ass every hour. The sensation of an aching dripping wet pussy became my normal and i thrived in it. The plug size had increased, and Master used only my mouth to pleasure Himself. He had made pussy obsolete and i no longer missed its use.
As He knew would happen, i began begging to be fucked. my greed for orgasm had become so strong that i groveled to have His cock inside me knowing full well which hole He would use. He had made certain that the plug i was accustomed to was smaller than Him. He knew that i would revert to fear and panic as He slid inside me, and He knew that He’d trained me to accept it anyway. The first time Master entered me can only be described as a whirlwind of terror and ecstasy. He was patient and allowed me to control the depth and rhythm. Feeling the girth of His cock stretch His hole further than it had ever been stretched made me cry out and yet i leaned into Him pushing Him deeper inside me. This was a bliss i had never felt before and the orgasms came crashing in one after another. This would be the only way i would be used for weeks to come.
As the time passed my love for anal sex grew. There was something ultimately submissive about it and seeing how much pleasure He derived from it made me feel accomplished and useful. Through months of positive reinforcement, He had trained me to not only accept it but to truly appreciate it. It took quite some time for me to be able to wear the largest plug in the set and in fact i still flinch and whimper when it slides in. i still wear a plug around the clock and find that without it i feel anxious and unfocused. He no longer forbids me to touch His pussy as a form of reprimand. Instead, He will have me remove His plug. Because He was patient and allowed me the illusion of control throughout the process, i now crave anal sex. He molded my thinking and trained my body to need it. He made me just as He wanted me, i am His anal whore.
I love when people are honest and open about process and journey! It’s such a teaching moment in so many ways, and it takes guts to bare one’s feelings and most intimate acts. Bravo to @shelivesfortheache, this was a fun and enlightening read.
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