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Author's Chapter Notes:

The apprentice tiny lover has the job of making sure it goes better than when the Mistress lost her first one. 

The first few months after I shrank Jacob, I was so busy with the joys of my first vagina that I hadn't given any thought to the lust building in my second. Of course, as I get closer and closer to 30, my second fertility is looming closer and my back door is starting to tell me that it needs attention and pleasure too. I started thinking about losing my back door virginity. 


When you were big, you had asked me about 'anal', and I turned you down. Of course, with the anatomy I possessed then, it was likely to be quite painful. The transformation the Goddess of Love gave to women that turned our back doors into places of joy changed the equation. But not completely. I was still dealing with baggage from the time I lost my first virginity. 


It was in my freshman year of college. It was a guy I met at a sorority event. (I sometimes feel like the Goddess has rearranged the world of women into a very naughty sorority!) I had dreamed of my first time being a deeply romantic event. Instead, it was kind of awkward and clumsy. It was disappointing, and it bothered me that I couldn't get a do-over of my first time. 


Now, of course, I was in much more control of my sexuality and my lovers, and I wanted to see if it was indeed possible to lose my second virginity with more pleasure than my first. 


I have this way I visualize the erogenous zones of my body. My areolas are like girls who live in the sun in northern Italy, and pick grapes, and are always sunny and happy. My clitoris is this sophisticated New York woman, like somebody from Sex and the City. My ass and my second vagina -- they're like my innocent little sister, or my younger version of myself. I just want them to be loved tenderly and respectfully. I'm a little shy about them, and most of all I don't want them to be hurt. I know it's hard to believe, given how powerful and all-encompassing my booty looks to you. 


My feelings about my ass and backdoor became mildly embarrassing as she (yes, I call her she) began to let me know that she was ready for some action in the twerk zone. You smile every time I bring up how the Goddess signals that women are ready for some backdoor sex by spreading their buttocks apart, giving anyone who can see them a clear view of their needy (and perhaps wide open and sopping wet!) organ formerly known as a butthole. You know how much of a problem this is, since microskirts and No Panties Days became standard business attire in the all-female workplace. I even had friends ask me if I needed to borrow one of their spare men for the night. They thought you were lying down on the job! I had to assure them that wasn't the case. 


So I knew it was time and I started planning my first time in back. I imagined myself wearing something like a cheerleader or Catholic school outfit, and wearing a pair of matching lace panties for my lover to pull down and stretch off me before plunging into my Southern Hemisphere, my Tropic of Capricorn if you wil. 


I was full of lust and ready to talk dirty with you about the idea. Just describing it was arousing me. I was squeezing my nipples and shifting in my seat when you presented me with this idea: 


"What about if we get Jacob to take your back virginity?"


I wasn't sure what to think. You saw the look in my eyes and got scared, and started thinking fast. "Please believe me... I have always wanted your ass! I asked you for anal before I got small. Since then, I've dreamed of plunging between your butt cheeks!"


"Then why do you want Jacob to take me in back? Are you afraid you're not good enough for my first time!"


"OK, mistress, here's where I'm coming from. You told me how let down you were the first time you lost your virginity to a young guy who didn't know what he was doing. Here is a guy who's not much older than you were then, still learning, but who's learning from the right guys -- namely, me. I think this is a great chance to reverse your bad memory and replace it with a good one of beginning a new realm of experience with a good, hard-working guy who honestly worships you, the way I do -- only a little crazier. 


"Not to mention he OBSESSES about your ass. He can't help but bring it up every time we talk about you. "Has she ever done it in the back? I want to lose myself in her ass cheeks." I think he is really motivated to give you a good experience. Not to mention, being the younger guy, he's more likely to make you a mom back there once you enter that phase of your life."


"Just to hedge my bet, I'll be there to work your front-clitoris. Hopefully, we can get that ping pong of passion between front and back that they talk about on the internet. But with your permission, the night will really be all about exploring the new sensations that the Goddess has given all of you women with your new vaginas."


The night came, and you made it extra-special. Lighting up the bedroom by candlelight must have been so hard at your size. Pillows were set up to allow me to elevate and spread my buttocks, thank you, and to allow Jacob to climb up and meet them. Both my clits were getting tingly and both my vaginas were getting wet just thinking about it. I pulled my beautiful red lace panties up over my ass, after ditching the costume idea because I know I couldn't wait long enough to unbutton and unzip. You even set up a little camera pointing at my ass so I could watch Jacob approach. 


I saw him climb over the bed. He had his beautiful curly fade haircut back. (I am so glad barbers shrank too!) He was gloriously naked and oiled down in the juices of his own desire to serve me. His cock was pointing straight out and had swelled to a size and form that I thought would do the job nicely, thank you. "Twelve inches," I whispered. The maximum size allowed for a man in this reality. 


Jacob shot up, doubling in height. He was now big enough to tower over my buttocks, to make them feel like the little woman needing his protection. You had told him to be stereotypically romantic. I felt him pull down the elastic. I shuddered when the cool breeze swept down along my buttcrack and tickled my rear labia. I put on my best damsel-in-distress voice and cried out to my tiny apprentice. 


"Oh my, toy Jacob, my bottom is so shy but I have been having naughty thoughts, and they have spread my cheeks so wide that my precious little backdoor and its needs are exposed for all the world to see! I need you to fill up the space between them! I need you to place your sweet little cock in that precious tiny little place and cover my backdoor up and make me a proper, respectable woman again! My ass dreams of taking your cock inside and making an experience we'll both remember forever! But...


"I need respect. I need tenderness. I need you to speak sweetly and seduce my buttocks and my backdoor so that they can achieve relief and collapse around you, and my girly crack will again cover my naughty place. Please talk to me, and tell me that you desire me, Toy Jacob, as my backdoor desires you. 


Jacob began to run kisses up and down each buttock, on the line where the general round curve dips into the crack. "I love your ass so much! I love you so much! When you made me small, I fell in love the first time I saw this soft and powerful cloud looming above me! I've wanted to make you a woman in back ever since I met you! I've wanted to pump my hot chocolate inside you there and kiss your back clitoris, and your back vulva, and your tiny, tiny sunburst..."


Sunburst! That was your private word for my backdoor, the one that I thought about the most when I decided to take the chance. You taught him well, my toy. I couldn't resist him after that. I laughed and giggled as he swept his tiny tongue along the crinkles that led down to my backpussy. 

My buttocks, spread and inviting for way too long, began spasming and squeezing Jacob. I was twerking for him, almost involuntarily! He didn't let up on his licks at first, but then he straightened out and began to edge his cock into my steamy, tropical backdoor. It felt every bit as good as other-vagina sex, even better. He had given me the foreplay and tenderness that had been denied me in my first deflowering. I was so so ready for him. My twerk became a mighty hug that squeezed his body harder and harder until he came in my backdoor. I didn't want the fun to end. "One inch," I moaned. Jacob shrank down from dominating my ass, to being dominated by it. My mighty squeezes and tightening buttocks forced him down to my rear vagina, where he was the perfect size to slide in. I laughed and laughed at the incongruity of this new sexuality the Goddess has given us, and then I cried when I thought of my lovers' creativity in responding to it. Their love and tenderness told me it's never too late for a better first time, and that 'happy endings' are for ladies too! Thank you, toy, and the apprentice toy you brought into my world and my body.  

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