Blog : A Day with Mistress Anna

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11/16/2023 9:40 am

A Day with Mistress Anna

This is an example of a typical day with Mistress Anna. Mistress Anna is 52 years old. She is white, 5-8, about 175, 40D, furry pussy.
This Friday I arrived at her home with the expectation of staying with her until Monday Morning. As usual, when I entered her living room, I undressed and put my clothing in a box. Then I stood naked, hands at my side, head bowed, eyes lowered. Miss Anna came over, did not say anything, kissed me on my lips, and handle my penis and ass. After about 15 minutes she led me into the bedroom. She sat on the bed and had me stand in front of her. She handled my penis which is very small and uncut. She pushed the foreskin back which is very uncomfortable for me. When I pulled away a bit, she slapped me and scolded me. Then I had to lay on the bed face down. She said that I needed a dose of discipline to begin the weekend. Miss Anna spread my arms and legs and tied my ankles and wrists to the bed frame. My penis and scrotum were exposed between my spread thighs. Miss Anna then put clips on my scrotum and my foreskin. My penis is incredibly small and uncut. Miss Anna often handled my penis and scrotum and she would handle the foreskin - pinching it, biting it, pushing it back and leaving it pushed back. This was a bit uncomfortable and painful.
Miss Anna sat on the edge of the bed and lubed my anus with her fingers and then inserted a 5-inch butt plug. She restrained my ankles and wrists tied to the bed frame. My ass was totally exposed to my mistress. Then she told me that the best way for us to begin this weekend was with a serious spanking that would establish my full submission. I had been spanked by Miss Anna quite frequently. This visit, this session, she increased the intensity of the spanking. She started with a heavy plastic hairbrush, slapping on my ass from cheek to cheek. I could feel my cheeks begin to get red. Then Miss Anna switch to a heavy leather belt. After about 10 minutes, I was begging her to stop. She told me to STFU and told me to put my face in the pillow. She stopped to get herself a cup of coffee. She also switched out the butt plug and used 7in plug that was very wide. It hurt as she pushed it into my ass. Mistress went back to her disciplining, and she was re-invigorated. I began to get teary eyed and then I did cry - which was a first for me. After she released me, removed the butt plug, and made me stand facing the wall hands at my side.
Anna took me into the bedroom. She took off her robe and lay face down and naked on the bed. Mistress is a natural blonde with very pale white skin. She has long slender legs and a very small ass. She spread her legs and told me to get busy. I spent over an hour eating Miss Annas ass and pussy. Throughout the weekend she had my tongue in one of her holes often. She wore sweats and no underwear. When she wanted my tongue she pulled the pants down and I served her as commanded. She had me serve her always after she used the toilet.
Miss Anna particularly enjoyed using her strapon with me. She had a 7in white one and 8 in black one. Each day, mid-morning, I had to lay naked, on a towel, on the bathroom floor. Miss Anna wanted me clean for the strapon play. She used a 2+ quart enema in me and then made me hold it for a few minutes. This was humiliating and uncomfortable. I would beg her to allow me to release the enema but she would slap my ass, she would tell me to be a good boy and to trust mistress. When I was allowed to release the enema Mistress would observe me and comment. She would tell me how pathetic I am and that I had an ass like a girl. It usually took more than 45 minutes to totally get all of the fluid out. then mistress washed me in the shower.
Usually, we would get on the bed, and I would eat her ass until she was ready to use the strapon. I would kneel, head down, ass up, Mistress would lube me and then she would put on the strapon. She would start with the white one and after about 30 minutes switch to the black one. This activity always made her get a bit sweaty. So, after I would have to lick her - underarms, and tits first, then her thighs and pussy, finally her ass, cheeks first, crack next, finally I had to insert my tongue into her anus. Often, she would fall asleep with my tongue in her ass and my fingers on her pussy.
When we went to bed at night, I had to please her orally and we woke up in the morning I had to put my tongue in her ass and in her pussy.
Miss Anna believed that oral service, especially anal service, correctly believed that this is an indication of a sub's deep submission and her strong dominance. On demand when she presented her anus to me I had to hold her cheeks and lick her crack and anus and then push the tip of tongue into her ass. Pussy worship and pee play were also indicators of my submission to her.
Miss Anna enjoyed restraining me and spanking me to tears. I would lay naked on the bed face down and she would tie my ankles together, then my knees. and tie my hands. This made my ass plumper and my ass remained still during the spanking.
This allowed her to spank me for as long as she wished and as harshly as she wished. She usually started a spanking with a hairbrush and then went to the belt. Depending on the time of day she would pause during the spanking to get a coffee or a glass of wine. My ass was usually red and scarlet red with welts. I had to keep my face in a pillow and she did make me cry. She would stop and lube my ass and finger it and put toys or veggies in it, some of the objects were quite wide and thick. After the spanking she would release me, and she would lay naked, and I had to eat her ass and eat her pussy. She believed the oral service was enhanced after I was spanked.
Miss Anna was fixated on abusing my ass. She really enjoyed strapon play. However I had to be super clean for her. I would get naked and lay on the bathroom floor face down. Miss Anna would fill the enema bag with liquid hand soap and warm water. The enema bag held 2 plus quarts of water. Miss Anna had a 1-quart container with additional fluid. She would lube the nozzle and finger my ass with more lube. She always started the lube with one finger, then a second, then a third. Miss Anna has big hands and long fingers. She always referred to my ass as the boy cunt and the fag cunt. She knew how humiliating this was and how uncomfortable it is to have 3 fingers in my ass. Miss Anna would tell me that as her bitch boy she had total control over me and that she owned the ass inside and out. She would slip the nozzle into me when she was ready and release the water. When the bag was about half empty, she would add the additional water. I was allowed to raise my hips slightly to accommodate the soapy solution. If I squirmed too much or raised my hips too much Miss Anna would hit my bare ass with a plastic hairbrush. The last half quart always took at least 5 minutes to get into me. Since I am a small person 2 quarts of warm water made me filled. The final quart took time to empty into me and I would start to cramp and have to release. I would beg to be able to get on the toilet and Miss Anna would slap my ass with the hairbrush and tell me to please STFU and be a good little boy. When she gave me permission I scrambled to sit on the toilet. Miss Anna sat on the edge of the tub while I released the enema. she would comment about my small ass, my small penis, and the smell, then make me stand to check me and the toilet which was all humiliating. It usually took over 40 minutes to completely get the enema totally out of me. After she would wash me in the shower. Then I had to go kneel on the bed ass up head down. Miss Anna would get her strapon and dildos and work on my ass for long periods of time of an hour or more.
Miss Anna also enjoyed pee play. There were different levels of pee. The first level was I would kneel while she peed then she would stand, and I would lick her pussy. The next level was I knelt in the tub, and she peed on me. And the most intense level of pee play was I would kneel, put my mouth on her pussy, my tongue extended and my mouth open and Miss anna would release her bladder. In bed at night or early morning after Miss Anna peed, she would come back to bed, lay face up, and I had to lick her wet pussy.


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