Annie Taes Over

After Annie left that day things went back to normal for the most part. Colin and Cassie saw each other in school and in passing. Annie stayed in her dark place. I just filed the events of that day away as a strange dream that would be replayed in the shower or late at night when I needed a quick fix. Other than that my days went back to being vanilla.

That was up until a week before Christmas. Colin asked what he should get the girls. He wanted to get Cassie a promise ring. His issue was with Annie. I told him, " I would think about it and get back to him".

At that moment I wanted to keep Annie as the farthest thing from my mind. Tired of being lonely and being pushed by my friends and coworkers, I had just set up an online dating profile. I was more concerned with swiping left and right than to worry about Miss Annie's gift.

I got wrapped up in a few vanilla conversations on this app when a new person who liked me and a conversation icon lit up. I opened the new conversation and there staring at me was that familiar dark, pale, nerdy, dominant familiar face. Her message read "nice profile too bad it isn't the true inner you. Don't make for this Friday as we will be spending the day together. I hope you will like your Christmas gift as much as I do."

I was instantly aroused but also scared. What did she have planned and what gift? I responded with a simple, " Yes Miss Annie".

The rest of the week was a blur. Colin bought Cassie her promise ring and we decided to get Annie a ps5 game and a gift card for online play. He took the presents with him to school on Friday and I was left to my thoughts when a message came on my phone from that dating site. "By now you should be all alone. I hope you are ready for me to bring your present."

Not five minutes later there was a knock at my door and there she was standing with a wrapped gift in hand. Annie was wearing a long black dress past her knees, and black converse all stars. I politely opened the door and greeted her. She pushed past me and took a seat on the couch and feet up on my table. She snapped her fingers and pointed to her shoes. I knew the drill and hit all fours crawling to her. Annie said "Good boy, Bradley. At least today we have all day and won't be distracted by my sister and your loser boy."

I reached her shoes and asked, "may I remove your shoes Ma'am".

She nodded and I removed her shoes and breathed in a deep breath. She smiled, rubbing her bare feet all around my face and on my tongue as I opened my mouth. Annie seemed to approve saying, "my my my you are such a fast learner. So eager to please me. I think you might be falling for me."

I knew better than to speak as I kissed, licked and sucked on her amazing feet. She grabbed my phone off the table and started reading the conversations I had with other women on the dating app. Laughing, she said, " these conversations are so funny and boring. How do you expect to get anywhere with this boring drab. Let me help you out."

I sat there in a trance licking between each toe as I saw the flash go off and heard messages coming in. She spread her legs and I saw those plain granny panties and the wet spot forming. She commanded that I remove them and start licking softly. I obeyed right away as more pictures were taken. More messages came in followed by more evil laughter. Miss Annie was squirming from my oral skills. The more messages that came in,the harder I got, the deeper I buried my tongue in her hairy teen pussy.

This went on for at least fifteen minutes when she finally spoke. She said, "It seems to me Kristen and Amanda are no longer interested in any more texts but Jordan said she loves guys paying to suck her toes."

Her taking control over my conversations made me eat her pussy as hard as I could to make her squirt on my face. As she did she slapped me making her orgasm more intense. Annie asked, "Do you not realize who is in charge? What makes you think I was ready to cover your face with my juices?"

She ordered me to get dressed and get my keys. I went to question her but thought better of it. She used her panties to wipe my face and waited for me to open the door for her and start the car. I asked, " May I ask where we are going ma'am."

She explained that we are going to go to the mall for something. We drove most of the way in silence. As we got close to the mall I felt her hand rubbing my dick. As she rubbed faster I knew I was in trouble. She started talking in this sweet innocent voice saying, "You are about to learn a valuable lesson and might be the luckiest man alive by the end of today."

I was so hard as she stroked harder and faster. As she got me right on edge I started begging, "Please Miss Annie you are driving me crazy please don't!!! Stop Please."

I saw the mall in sight and thought it was my salvation but I was dead wrong. She laughed and said, " as you wish I won't stop and you will cum NOW!"

A big hot load shot out of me and I watched as a wet spot formed on my khakis. I didn't know what to do to conceal it as we entered the mall. I followed behind Annie as I did not know where we were headed. She walked to the first jewelry store we saw and went straight to the engagement rings. As the sales person approached us Annie started to play Miss innocent. She turned to the sales woman and said, "Hi, my daddy is proposing to a special woman today and he needs a nice ring in a size 5. Do you have anything that might work?"

The sales woman showed Annie a few rings and one she really seemed to like. I truly did not know where she was going with this. But I learned soon enough about her game. She picked out a few and tried them on and said, " Daddy, picking out the Christmas gift excite you that much that you made a spot in your pants."

I was mortified there I was hard again and her pointing out my cum soaked spot to a sales woman in the middle of the mall. She laughed, gave the ring back and off we went to the next store. At the second store she found the engagement ring and made sure to point out that it was the perfect one. I got the price and she said that we will be right back. She led me to the family restroom and had me go in with her. She ordered me to my knees and kneel as she peed. As she sat there she said, "Bradley you are the perfect man for what I plan to do. You have been a good sport and a perfect submissive. Here is your chance to prove yourself as my slave. First I want you to lick me clean which will make me squirt again I am sure and then I want that ring as my Christmas present from you. Do these two things and you will be greatly rewarded. "

I buried my face in her pussy and licked her to a quick orgasm like she said and was proud to be wearing her juice on my face again for the second time that day. I headed back to the jewelry store and she changed it to a size smaller which again I did not understand but blindly obeyed. After buying the ring we headed back to my house. Annie entered the house and grabbed the present she brought earlier and headed straight to the bedroom and undressed. She laid on her stomach naked and ordered me to eat her ass. I buried my face in her ass and listened to her moans of pleasure.

As I did this I wondered what my present was. She stopped my ass eating and rolled over and kissed me passionately. She asked if I was ready for our future. This really confused me. She said, "You did buy an expensive engagement ring for me did you not? I am waiting."

I realized what she wanted and quickly fell to my knee. I said, "Mistress Annie I know I am just a lowly slave but I would be honored if I could spend the rest of my life serving and obeying your every command for as long as you will let me."

With that I opened the ring box and presented her with it and instead of holding out her hand she stretched out her left foot and had me place the ring on her toe. I was so pleased when she said yes and slid this $2800 ring on. She said, "We will be taking care of this later but it is time for my once in a lifetime moment."

She had me lay down and proceeded to climb on top and ride me like a wild woman having multiple orgasms and shaking non stop. I was in heaven and did not want it to stop. Again she presented me with two options. The first was to cum deep in my future wife/mistress or to prove my love by asking her to stop and use my present on me. I was not going to disappoint Miss Annie and begged for the second choice. There was her laugh and she got off me and handed me my present. As I opened it I was face to face with the tiniest cock cage I have ever seen. She said, "it seems we both got permanent rings today."

She took the cock cage and placed it on my dick and secured it. As she closed the lock she asked, " Do you Bradley take me to be your forever mistress, to always obey and worship no matter what the circumstances for all the days of your life?"

"I definitely do" I said as the lock clicked in place.

She snapped more pictures and off went more messages. This went on for the remainder of the day until about an hour before Colin was due home. Then there was a knock on the door and she said, "it was time to make it official" and she grabbed the key to the lock and a small tube of crazy glue and went to the front room with me following.

As I got there in my living room was a guy with a folder in his hand. Annie gave him a smile and a nod. She then pointed to the ground next to her feet and I knelt next to her. He began a modified version of a wedding ceremony. She kept her ring on her toe and I was presented with a dog collar to match my cock cage with a pink tag that read property of Annie if uncaged return to her.

I kissed her foot and we signed all the paperwork to make it legally binding. She proceeded to open the crazy glue and put a few drops in the lock. The guy left and we went back to the bedroom to "consummate" the wedding. This consisted of me eating her to multiple orgasms and attaching a strap on above the cage and fucking her for a couple more.

After she had had enough she dressed and went up front to the couch. I started to dress but was told I was in my house clothes and didn't need anything else. I assumed my position as Miss Annie's footstool in just my cage and collar. After a few minutes of relaxing watching tv I heard Colin's car pull up and two doors close and I started to panic but Miss Annie held me in place.

The two entered and were in shock to see this site and behind me was a laugh. Annie said, "welcome home son. I told you I would do anything to ruin your chance to be with my sister and I did. You are now officially my son and so that means you can't marry your aunt. Merry Christmas to you both. "