My First Session with Her

She grabbed me by the hand and led me out to the pool. "Rub some lotion on me, little girl," she commanded me, as she lay down on her stomach on a lounge chair. I did as I was told, carefully rubbing lotion on every part of her. Then I rubbed lotion all over myself, since I am fair skinned, Ms. Andrea did not want me to burn. "I just want you to have some nice girly tan lines," she informed me. "Guess you won't be going shirtless or wearing shorts anytime soon, will you, sissy boy," she laughed, as she tossed me the latest edition of Cosmo magazine.

After awhile, she had me jump in the pool. She told me she wanted me to come out and, "Look sexy." I jumped in, surprised at how my tits felt in the water. I came up slowly, and ran my hands through my long hair. I walked up the steps, and back over to the longue chair. Ms. Andrea led me by the hand over to the hot tub, and she told me to get in and close my eyes. A few minutes later, I could feel something poking at my mouth, and looked up to see Ms. Andrea standing over me, outside the hot tub, and that the strapon was back around her waist and ready for action!

"Right here, outside?" I asked.

"Of course, right here, and RIGHT NOW!" she barked. I turned my head to the side, and craned my neck as far as it would go, and began to give her another blowjob. "You are a quick learner," she complimented me. "This blowjob is MUCH better than the last one; you are a true natural, slut. What do you say, bitch?"

"Thhhnk ooo Mittth Andreaaaa," I mumbled, with my mouth full of cock.

"You're welcome, sissy," she laughed, as she grabbed my head and forced me all the way down her shaft, which made me gag. She let go and rejoined me in the hot tub. "Lift your ass," she commanded. I hooked my arms around the rim of the hot tub, as she lifted my legs and had me hook them around her waist. Again, she slowly sank the cock into my well-used ass. Once it was all the way in, she started really slamming me! It was super difficult to hold this position, and my arms and thighs quickly began to burn! I started to cry, but Ms. Andrea paid no heed, and continued to buck and thrust her hips. I could feel my tits really bouncing on my chest, and in no time, they were free of the tiny top, and bouncing all over my chest.

All of a sudden, my arms gave out, and I lost my grip and briefly went under water. She let me stay for a few seconds, as I struggled to get up, and then placed her arms underneath my back and lifted me up. "You are so tiny and weak," she said, as I put my arms around her neck, my legs still wrapped around her waist. I gripped tighter around her waist and neck, which allowed her further in my ass. I was so lost in ecstasy, that I threw my head back and began to moan and grunt, and shake. "You may cum, slave," Ms. Andrea informed me. I shook and came like I've never cum before in my life! I cried out, and grabbed onto her, as she held me tightly and kept her cock buried in my ass.

She ran her hands through my hair and said, "Oh baby. I'm glad it was good for you, little one, but I have not cum yet!" With that, she sat down and told me, "Start riding." It took a moment to gather myself, but I loosened my grip around her neck, and swung my legs out so that they were outside of hers, and my knees and lower legs rested on the bench. As I look back, I'm not sure if it was because I was exhausted, or because I had finally been broken, and had accepted my feminine role, but I looked Ms. Andrea in the eyes, batted mine, pushed my hair back with one hand, and started rocking my hips! I placed my hands lightly on her shoulders and worked her cock, keeping it deep in my ass. She smiled and grabbed my ass and softly guided me up and down.

"Turn around," she whispered to me. I stood up, which briefly left my ass empty. In one motion, I spun around, grabbed the cock, bent over, and sat back down, flawlessly guiding her cock back into my waiting ass. That felt so wonderful! It was as if my ass actually missed being full. Ms. Andrea reached around and cupped my tits, as I rode her. "I've never seen anything like this," she exclaimed. "Just a few hours ago, you wouldn't suck my cock, and now look at you, you horny little slut! Bouncing on my cock like a pro! I think we've found your new calling in life: depraved anal slut!" She grabbed my hips and lifted me up, then slammed me back down. "Keep riding," she growled. I placed my hands on her thighs to keep my balance, as she kept her hands on my hips and continued to slam me up and down. Instinctively, my hands went up to cup my bouncing tits, and I pinched the fake nipples and came again!

I tried to collapse, as I was exhausted from the number of times I'd been fucked, but Ms. Andrea was not done with me yet. She ripped my hands away from my tits and replaced them with her own. She grabbed my shoulders and slammed me down really hard, one last time on her cock, and I felt her shake and cum as well. We rested for a few minutes, her arms around my waist, and my ass still full of her cock. After what seemed like eternity, she lifted me up, and I stood up, and we went back over to our longue chairs and lay down. I stuffed my fake tits back inside my bikini top, and adjusted the thong so that the string was back between my cheeks, and I could really tell my ass was gaping!

It was getting late in the afternoon, and Ms. Andrea had a butler deliver dinner for us. We each had a nice chicken salad and she had a glass of wine, but I got water. I noticed that she was still wearing the strapon, and as she drank her second glass of wine, she simply pointed down. Without hesitation, I got under the table and began to suck her off. My hand slid up and down the big black shaft as I stroked and sucked her cock. It was so big; I couldn't help but bury it all the way down my throat, just to prove that I could. I swirled my tongue around the tip, and pulled it all the way out to slap my own face with it. Then, I dropped a long trail of drool on it, and stuck it back in my eager mouth.

All of a sudden, I heard another person! I looked over and saw the feet, and then the leg of the butler, clearing our dishes! For a split second, I felt a bit ashamed, and I could tell my face started to get a little red, but I quickly suppressed it, and got back to work on the blowjob. "Mmmmm, that feels really good!" Ms. Andrea cooed. "You don't even care anymore if others see what a dirty whore you are, do you?" she said. "Does my depraved anal slut want a nice little good-night fuck?"

"Oh yes, Ms. Andrea. Your depraved anal slut would love your cock in her ass one more time tonight," I said coquettishly. I stood up, and kneeled down on all fours on a towel near the pool. As she strode toward me, I looked back over my shoulder and saw her big black cock bobbing menacingly up and down, and I licked my lips and pulled my thong string to the side for her. She knelt down behind me, parted my ass cheeks, and spit directly into my asshole. I heard her spit again, and then a few seconds later, I felt the head of her slippery strapon work its way past my rosebud. "Thank you for using lube, Ms. Andrea," I said.

"You're very welcome, slave," she answered. She worked her way slowly into my ass, and stopped when her hips came to rest against mine. I reached up and untied the strings behind my neck, letting my tits fall out of the top and hang down below me. I looked back at Ms. Andrea, and she smiled and leaned over and cupped my big tits in her hands. A sigh escaped my lips, and I looked up and saw the sun setting on a perfect evening. She placed her hands on my hips and fucked me with long slow stokes. Then she grabbed my hair with both hands, yanked my head back and fucked me faster! After a few minutes, she slowed back down again, and gently tugged my hair as she stroked in and out of my well-used ass. I grunted as she started the "screwing motion," and I bore down and pushed back as she did. Without warning, she came, and I felt what little cum I had left oozing into my thong, as I screamed in bliss!

Ms. Andrea pulled out of my ass and told me to put the black stripper heels back on. I struggled for a bit, but finally got them on, and she locked them back into place. I was so super tired; I had no idea how I was even going to make it back to the house, let alone in those heels! I took a few wobbly steps, and felt like I was going to fall, but she kept walking and I had no choice but to keep up. My tits bounced the whole way, and my legs were shaking and my ass was sore, but somehow we made it back to her wing of the house.

Once there, she had me shower and clean up, and she provided me with a black silk and lace baby doll that barely covered my tits or ass, as well as a black thong that had "BITCH" in rhinestones (like my white "SLUT" one), and a black collar. She had me lick her pussy to orgasm, then chained me to the foot of the bed and turned out the lights. I could feel the cool silk soothing my burning ass as I drifted off to sleep.

The next morning, I awoke to the sunlight streaming into the room, and Ms. Andrea no where in sight. The clock said 7 a.m., so I wasn't late for work, yet. On the table was a note that said, "Slave, you are not going to your regular job today, but that doesn't mean that there isn't work to do. Put on the outfit I've left for you, and meet me in my office. It's the third door on the left. Work starts at 7:30 a.m. Do not be late!"

On the door, there was a hanger with a black outfit. It was black pinstriped, and appeared to be a woman's business suit. There was also a white blouse and black lacy push up bra. I took off the baby doll and put on the bra, expertly clasping it behind me, like a real woman. It felt a little tight, and created a ton of cleavage, and I saw the tag in the mirror said "36D," so it was, in fact, a size too small. Next, I put on the skirt; it was very tight, and very short. The blouse barely reached the waistband of the skirt, so there was no way I could tuck it in. It was also very low cut; the top button was still below my cleavage and barely covered my bra. Lastly, I put on the jacket, which also barely touched the skirt and only buttoned up to enhance my already extensive bust. I went into the bathroom and fixed my hair into a bun, put on some red lipstick, and red press on nails that she left for me, and sashayed down the hall. I knocked and was told to enter.

Ms. Andrea was at a big wooden desk, filled with important looking papers. She was wearing a similar, more conservative, but still sexy, version of the suit I was wearing. There was a smaller desk in the corner, with files on it, a computer and a few filing cabinets off to the side. I went over and took my seat. It was really hard sitting in that short skirt, and I really had to tug to get it to cover my ass. I crossed my legs and turned on the computer screen. There was a "To Do" list that popped up on the screen.

1. Bring Ms. Andrea coffee.

2. Finish filing what is on the desk.

3. Attend and take notes on morning meeting.

4. Type up and mail letters to prospective clients.

I stood up and went to the little kitchen and brewed a pot of coffee. While I was waiting, I raised my skirt a little and noticed that the "SLUT" was still paddled into my ass, but was becoming a bit less noticeable. The fabric of the skirt rubbed against it when I walked, and irritated it a bit more. Once the coffee maker was done, I filled a cup and took it back to Ms. Andrea. She took a sip and smiled, and sent me back to my desk.

I got to work filing immediately, as there were many files, and much work to get done. The filing cabinets were low to the ground, and as such, I had to bend over to put away most of the files. Each time, I felt my jacket and blouse ride up, which exposed my lower back. I also felt the skirt ride up to show off my ass. "Ah hem," Ms. Andrea cleared her voice behind me, and I snapped out of my trace with a jump. How long had she been standing there?

"You are a sexy little girl, I must say," she said. "What a great set of tits! You have a great ass too, I bet you like it back there, don't you?" she continued. "Don't answer that, I already know," she winked at me. "I think you can go far in this company," she added.

"Thank you Ms. Andrea," I giggled. "I'd really like to get a head in this company, and I'll do whatever it takes," I responded. Just then, I saw a large bulge under her skirt, and she smiled when she saw the look in my eyes. Without hesitation, I walked confidently over to her, and rubbed the bulge a bit. Then I got down on my knees, rolled her skirt up, and took the monster strapon in my mouth. It was the biggest one I'd ever taken! She moaned as she ran her fingers through my hair, and my mouth reached the balls of her cock. I looked up at her, from my place on the floor, and she smiled down at me.

"I think it's time to call your other boss," she said firmly. I reluctantly stood and made my way over to the telephone on my desk. I made sure to bend all the way over the desk to reach it, and I looked back at Ms. Andrea, and shook my ass a bit to tempt her. The phone was harder to dial with the fake nails, and it took me a few tries to get it right. I looked back one last time at her, and she had the big black cock at the entrance of my ass again! She nodded and said, "Decide what you want, my depraved anal slut." I nodded my head yes, and she plunged into my ass, right as my other boss answered the phone.

"Ahhh, oh my God," I cried in a high pitched voice.

"Um, hello?" my boss Mr. Sanders said.

"Oh, oh, ohhhh!!" I moaned, as Ms. Andrea impaled me. "Hello Mr. Sanders, this is Brian calling. I've, oh!!! Ahhh! Ohhhh!!! Oh my God!" I screamed.

"Brian? That doesn't sound like you, are you ok?" he said.

"Yesssss, Mr. Sanders, I'm ok. I can't make it into work today," I stammered.

"And why is that, my depraved anal slut?" Ms. Andrea mocked. "Tell him why. Tell him what choice you've made. Tell him who owns your ass," she said, as she slammed back into me.

"I can't make it because I'm dressed as a sexy secretary with long hair, fake nails, stripper heels and big tits, bent over a desk and taking it in the ass from my new boss, Ms. Andrea. I work for her. She owns my ass now."

"Brian, what the hell are you talking about? Is this some kind of sick joke?"

"No, Mr. Sanders! It's the truth! OH MY GODDD!!!" I moaned. "Oh, ohhhh, ughh!!" Holy shit! Wow, oh Ms. Andrea, thank you for putting your big cock in my slutty ass, ohhhh!!!

"Brian, you are fired, you disgusting pervert!" he shouted, and slammed down the phone.

"You'll be much happier here, as my secretary, my little girl," Ms. Andrea said matter-of-factly. "I've never offered this position to a sissy before, but I've never had such a natural born sissy as you. I knew the second that you nodded your head yes to take it in the ass while you were making that call, that you were the one for this job," she continued. "Just think of how far you've come in just the short time you've been here! Yesterday morning, you had to be coerced to suck my cock, and were embarrassed to act like a slut in front of my father. Just now, you called your old boss while dressed like a slut, bent over a desk, with a fat cock in your ass, and TOLD HIM ABOUT IT!"

I smiled, because I knew she was right. "Thank you, Ms. Andrea, for choosing meee!!" I squealed. "Is there anything I can do to please you even more?"

"Yes, there is. I want you to forget about the rest of the "To Do" list for today, and prepare for your new life with me. I have a friend who is the best plastic surgeon in the area. You will call her and tell her who you are, and that you will require some face work, electrolysis, and breast implants. We will pay her extra if she can get you in this week, do you understand? You also need to make arrangements with your roommate to go get your stuff, although you won't need any of it anyway."

"Yes, Ms. Andrea, I understand!" I said excitedly. I didn't even give it a second thought. This is what I wanted; it is what I've wanted for so long! I squealed in joy as she pulled out of my ass and I turned around to hug her, and our tits mashed together! One day soon, I knew it would feel even better to do that.

The next few days flew by, with doctor appointments and other things. I told Jane what was going on, and she actually wasn't surprised. Apparently, she had found a few pieces of my female clothing and looked at my computer, and put two and two together. We made arrangements for me to get my stuff in a few weeks, after I healed from my surgeries. Then it was time to go to the hospital. They got me all hooked up, and then I went out.

When I woke up, I was in a little pain, but mostly everything was really foggy. Ms. Andrea was there and she told me about my new body. "Hello, Ashleigh! Everything went very well, my little slave. You look great. You've lost about thirty pounds, and your stomach is nice and flat! I'm going to get a lot of use out of that ass, and everything else for that matter, which is good, because I paid for all of it! As you can see, your legs are smooth and tan. All of the hair has been permanently removed from your body, from the neck down. I have left your tiny penis, as a reminder of who you are, and what you are, my feminized little slave. The doctor added a little bit of fat to your hips and ass, so you have nice curves. You will be working out regularly to keep your ass and legs firm and toned. I do not like big asses!"

"I do, however like big tits. While I'd never do anything so outrageously whorish, submissive, and attention seeking to myself, I figured a nice big set of high-profile DDs would be perfect for you! They look even bigger on your slim build. There is no doubt what those babies are there for! She went in through your armpit, so there should be no scarring, and you should be fully recovered in less than a week."

"Also, she did some work on your face. She filled in your cheeks, and gave you a more feminine nose. She didn't have to do much, as you were already had nice soft features. In fact, she worked with what you had, so you don't look like a totally new person, but rather, a prettier version of your old self. The swelling will go down later today, and I'll let you look in the mirror then."

I went back to sleep, and woke up some time later. I felt much better, and Ms. Andrea informed me that it was time to go, and wheeled me out to the car and strapped me in. The next few days, I mostly rested and ate (light healthy meals, of course!) Ms. Andrea took me to get my ears and belly button pierced. I also walked around a lot, getting used to my new body and new center of gravity. My new tits were heavy, but they looked and felt awesome! My face looked beautiful, and was framed by my long blonde hair. I couldn't wait until my hair grew out, and it was all me! Ms. Andrea told me to take a shower, so I stripped down and stepped into the water. It felt amazing, cascading down my body, and I reached up and rubbed my nipples and played with my new tits a bit. I ran my hands through my hair, and gave my ass a playful slap.

I got out of the shower, and got dressed. I had a full closet of clothes now, all sorts of dresses, costumes for role-play, short skirts, and scandalous tops. Of course there was no shortage of lingerie, and certainly tons of super high heels and thigh highs. My only casual clothes were my gym clothes, and even those were pretty sexy. Today is the day we were moving my stuff out of Jane's house. It was the last vestige of my old life, and I was really looking forward to it. I put on a white bra, white thong, white tank top, and sexy pink "Pink" sweats shorts. My pink and white striped knee socks and pink and white gym shoes matched my little outfit perfectly. I put my hair in a ponytail, put on some light makeup and headed over to Jane's.