My First Session With Her free porn video

My First Session with Her By humbleslave Let me start out by describing who I was. I am 24 years old, 5'6" about 150 pounds, fair skin and short hair. I'd been cross-dressing for about seven years, and had quite a collection. I was living with a roommate, Jane, who had no idea about my hobby. In fact, I'm pretty sure she'd have been freaked out if she found out, so I'd kept it secret. I consider myself to be straight, but my roommate and I were just friends. For a few years now, I've wanted a woman to dress me up as a girl and dominate me. Sometimes, I'd look on various websites, and get very close to actually going through with it, only to have something happen at the end. Something always happened though: I found out it's a bogus offer, the woman is totally unattractive, or I decided not to go through with it. (I always let them know beforehand, as it's rude to stand people up.) My roommate was gone for the weekend, and the weather was getting warmer, so I decided to try something a little daring. I glued my DD breasts to my chest, and then bent down to slide some white stay up thigh highs up my legs, feeling my new tits pull me forward as I did so. Next, I strapped on my black seven inch platform stripper heels, and stood up and walked over to my dresser, where I hid my bras and thongs. My white thong that ties at the sides and has the word "SLUT" in rhinestones in the back was calling my name, so I grabbed it and put it on, moaning as the soft material found its way between my ass cheeks. I put on a white lace push up bra, and sauntered over to my closet and took out my school girl outfit. The white blouse tied right below my boobs and showed a ton of cleavage, and the short red and black pleated skirt barely covered my ass. I gave the strings of my thong a tug so that they showed above the waistband of the skirt, and then I grabbed my favorite dildo and strode out to the front porch! It was super dark outside, so I figured this would be a good chance to do something a little daring, and then hopefully work my way up to actually going through with my plans to let a real woman dominate me. The first few minutes, I just walked back and forth on the porch, and got used to the thrill of being outside dressed up, and enjoyed the feeling of walking in the heels. Then I got a little braver, and started sucking the dildo, right there on the porch. Once it was wet, I went over to the porch railing and bent over it. I flipped up my tiny skirt, and moved my thong to the side. A few swats to my backside really increased the mood for me, and before I knew it, I had shoved the dildo all the way up my ass! I used one hand to work the dildo, while the other hand played with my tits. I started rocking back and forth, and then I stood up and turned around and started ramming my ass against the porch railing, which drove the dildo in and out for me, and left both my hands to spread my ass or play with my tits, which I alternated doing. At that point, I was so worked up; I stood back up, and climbed up on the porch railing. It was cement, and kind of wide, so I knew this would work. I balanced on the heels, squatted down and used my ass muscles to push the dildo most of the way out. Then I squatted ALL THE WAY down, driving the dildo all the way back into my ass, and then pulled myself up a bit, and started fucking myself that way really fast to get my tits bouncing. After awhile I was so worked up, I came in my thong, stepped down, and pulled the dildo out of my ass. The night was still young though, and I wanted to enjoy the weather a bit, so I adjusted my skirt, and sat up on the porch railing and crossed my legs like a girl. I looked around a bit, and out of the corner of my eye, I saw our big black neighbor sitting on his porch! Now, he is old and hard of hearing and vision, but it gave me such a scare, I jumped up and ran into the house and shut the door! I have no idea if he saw me or not, but I was super scared and quite a bit turned on. At that point, I battled it out in my head and decided that if I could do that, then I was ready for a real life experience. Since I was already in the mood, and dressed the part, I wasted no time in logging onto my computer and starting my search. After some searching, I found a woman in my area that seemed to fit the bill. She was a little older than me, attractive, and interested in the same fetishes. We sent a few e mails back and forth, and then she called me. Once everything was in order, she told me to meet her at her house tomorrow, wearing exactly what I was wearing right now, except to add a pink jeweled metal anal plug. I set to work getting my outfit cleaned for the big day. I took off my breasts, and washed all the outfit pieces. The adult store wasn't far from our house, so I went and bought the required anal plug, much to my embarrassment, as I had previously just bought everything over the internet. After finishing up the laundry and making sure everything was ready for the big day, I went to sleep, although I didn't sleep very well, as I was so excited. I woke up and put on everything as instructed. She told me to wear my tits, but not glue them on, so I did as she said. A quick check in the mirror revealed that everything was in place, except the anal plug. I bent over, spread my ass cheeks and pushed the smooth plug into my ass. It was a bit cold, and kind of big, but I managed to get it all the way in, sliding my thong string back into my ass to hold the plug in place. A sweatshirt and sweatpants over top the outfit, and I shuffled out to the car and drove over to her house. When I got there, I was astounded by how big and nice the house was. She told me her father was very rich and had a condition that required a caretaker. So, he had built her a private wing of the house, which she designed, in exchange for her living there and caring for him. I pulled into her driveway, as directed, and took off the sweatshirt and sweatpants before she could see me. Nervously, I stepped out of the car, and walked up to the door, my hips swaying from the super high heels and the plug in my ass. I was met at the door by Ms. Andrea. She was even better looking in person, and I instinctively knelt down in the doorway. Before I looked down, I took in that she was about 30, as she said, with beautiful brunette hair, and perfect C cup sized breasts, and clearly in great shape from frequent workouts. "My my, aren't you a cute little sissy?" she remarked as she collared and leashed me. "Thank you, Ms. Andrea," I replied. "Do a little spin for me, and bend over, I want to see that ass," she commanded. I did as I was told, spinning around, and then stopping to bend at the waist. She pulled up my skirt and upon seeing the jeweled plug firmly in place said, "Very good, slut, you have followed my first command. However, you won't need these," she said, as she pulled my hands behind my back and cuffed them together. "Oh I like that," she laughed, as she noticed that with my hands cuffed behind me, I was forced to thrust my breasts out. She then blindfolded me, told me to stand, and led me down some stairs. It felt colder and darker, but I knew better than to ask any questions. I felt my breasts being lifted away from my chest, a cool liquid applied and then her hands pressed my breasts firmly against my chest. She then spend a few minutes near my ankles and I heard a few "clicks." Then I felt the cool liquid on my head, followed by what had to be a wig. She removed my blindfold and I saw myself in the mirror. I had long blonde hair, and my shoes had been locked onto my feet! I looked around and saw a fully equipped dungeon and Ms. Andrea in the corner walking toward me in full leather attire. Her brunette hair was pulled back in a ponytail, and she was wearing a black leather corset that supported, but did not cover her beautiful breasts. She was wearing tight black leather pants and black platform heels. She was carrying a paddle in one hand, and as she got closer, I could tell she had a strapon belted around her waist! "Do you like my dungeon, slave?" she teased, as she stroked her cock. "Daddy doesn't know about it," she giggled. "I designed it, and had it built without his knowledge. I've been training slaves down her for almost ten years, and he's none the wiser." "As for you, slave, you told me you've backed out before, so I've taken some measures to ensure that you don't do that to me. First of all, your shoes are locked to your feet. Only I know where the key is, so you will have to please me in order to ever have them taken off. Also, both your breasts and wig are glued on with special glue that will keep them on for a minimum of two days, and after that, can be removed with a special solvent that I have. So, not only will you need to please me, it looks like your weekend just got a little bit longer. Tomorrow morning we will call your boss and let him know you are unable to make it to work. You better please me, or you'll have to make the call with my cock up your ass!" Needless to say, I was simultaneously scared and aroused. Ms. Andrea pointed, and I obediently got down on my knees, which was difficult in the heels and with my hands still cuffed behind me. She circled me a few times, and then stopped behind me. She pushed my head to the ground and told me to hold my hands up in the air behind me, which gave her total access to my ass. Next, she lifted my skirt off of my ass, and flipped it up onto my back, and I started to shake in anticipation of what was coming next. All of a sudden, I felt a breeze and then a WHACK on my ass! I screamed and lurched forward, but she laughed and I got another WHACK! I started to tear up a bit, and I must have moved a little, because she took one hand and grabbed the chain to my handcuffs and yanked my hands up further as she continued to paddle my poor ass. I started to cry and begged her to stop, but she kept going. My ass felt like it was on fire, and yet still she persisted. "Would you like me to stop, slave," she teased. "Yes, Ms. Andrea, please stop," I sobbed. "Not yet," she stated. She let go of my cuffs again and started hitting me even harder. I was sure I couldn't take much more. I started to collapse onto the floor. I felt totally broken. She asked me again, "Do you want me to stop, slave?" "Only if it pleases you, Ms. Andrea," I managed to cry. "Very good, slave, you are a pretty quick learner," she said. "That is the answer I was looking for," she said, as she put down the paddle and began to rub my poor inflamed ass. "It didn't take very long to break you, did it? No, I think we're going to have a lot of fun this weekend," she laughed. She held up a mirror for me to see what she had done to my ass. Her paddle was engraved with the word "SLUT," so that had been imprinted on my backside. She tugged at my leash and I obediently crawled after her, even though it was really hard just shuffling on my knees. "Up," she said. I climbed up onto a padded sawhorse, and Ms. Andrea cuffed my legs to two of the legs. Then, she un-cuffed my hands, and cuffed them to the remaining legs, so that I was propped up on all fours, with easy access to both my mouth and ass, my upper body hanging off the end, so my tits were tugging at my chest. She stepped in front of me, her strapon cock right at eye level. She removed my blouse, and I lunged forward for her cock, and she pulled it away and laughed. "Such an eager little cock slut," she laughed. To prove her control, she stepped away and did a few more laps around me. Then she stepped up again. For some reason, this time, I kept my mouth closed. I immediately knew this was a mistake, and expected a terrible punishment, but instead, Ms. Andrea simply laughed, and pinched my nose closed with two of her delicate fingers. After about thirty seconds, I was forced to open my mouth, and she laughed again and sunk her cock all the way down my throat! I started to gag and drool, and she grabbed me by my hair and held me there until I gagged and thought I'd puke, then she let me go, before cramming her cock all the way back in. "You are not smarter than me, slave, do you understand? Do not try to pull that with me again, I own you, and you do what I want when I want," she said calmly but firmly. "Now let's see about that pretty little ass of yours," she cooed, as she pulled out of my mouth and stepped behind me. I felt her lightly scratch my back with her nails as she paced around me. "My cock is a bit bigger than your plug, so you're going to feel something, but trust me, you'll be glad you had that in there to get you warmed up." I felt her hands at my ass, as she flipped my tiny skirt up onto my back. She slowly slid the plug out. Right as it left my ass, the tip of her cock replaced it! I screamed and thrashed in my bonds, and tried to get away, but to no avail. Ms. Andrea spread my ass cheeks with her hands, and fed her cock slowly into my asshole. "I do enjoy taking a girl's anal virginity," she said. "It's another notch on my bedpost. Another little boy conquered. I will add you to the others. Oh, look! I'm all the way in!" she exclaimed, as I felt her hips touch my ass. "That was pretty easy," she laughed. "You must have been practicing on yourself in your room for a long time. That's pretty pathetic. At least now you are getting what you need and deserve, you naughty little sissy," she said as she started to saw in and out of me faster and faster. I continued to try and get away, and dislodge her cock from my ass, but was unsuccessful. As she slammed me, she reached forward and mauled my tits with her hands. I squealed as the fucking shook my tits loose of the bra and tugged on my chest, as I'd always imagined they would. She took her forearm and dug it into the back of my neck, forcing herself in and out of me at top speed, burying the cock all the way in and taking it almost all the way out, over and over again. I started to scream and moan, I couldn't take it anymore!! "Scream as loud as you want, you little bitch, no one can hear you down here," Ms. Andrea laughed. "In fact, no one even knows there's anything down here. I can keep you down here as long as I like and do whatever I want to do," she said. "Please, Ms. Andrea, may I please cum?" I begged. "No, you may not," she said. I thought I couldn't take any more, but then she pulled out a bit and made a twisting motion as she shoved it back in. She started twisting her hips as she drove in and out. I swore I was going to lose it! "Please Ms. Andrea may I PLEASE cum, please Ms. Andrea?" I pleaded. She pulled out of my ass and positioned her cock directly under mine. "You may cum now, slave," she directed me. I came harder than I'd ever cum in my life, and it was directly onto her strapon. I'd see enough female domination movies and read enough stories to know what was probably coming next. That did not mean I was ready for it, or that I wanted it. The strapon was right at my mouth again, and I clamped my lips shut and refused to open them. Ms. Andrea just kept walking forward, until the cum-covered cock touched my face. I recoiled in disgust and moved my head, which just succeeded in smearing my face with cum. She moved, and I moved again, which smeared cum all over my other cheek. "Well slave, you have a choice," she stated. "Your face is now full of your own cum. The only way that is coming off is by your own tongue. We are going somewhere in a little bit. You can either go with your cum on your face, or lick it off, like a good little bitch, what will it be?" "I will lick my own cum, Ms. Andrea," I said, as I opened my mouth as a sign of my submission. She used the strapon to scoop the cum from my face into my mouth. I swallowed the entire load, and licked my lips to make sure I got it all. My face started to feel a bit crusty and I moved my jaws and Ms. Andrea laughed. "It's impossible to get all of it. I guess you should have just sucked it off my cock in the first place, huh, sissy? That's an important lesson for you," she laughed, as she undid my bindings. "Stand up, and strip," she commanded. I stripped down to my bra and thong, and waited for her next instruction. Ms. Andrea went to the corner and came back with a short white outfit on a hanger. She handed it to me, and I realized it was a nurse's outfit! I put it on, and buttoned it up as far as I could, but it was obviously made for someone with smaller tits; my DDs barely fit, and showed tremendous cleavage. To make matters worse, the hem barely covered my still red ass, and as I walked around the dungeon, I swore anyone looking could see the "SLUT" still paddled onto my ass cheeks. "It's time for daddy's medication," Ms. Andrea informed me. "You are convincing enough for his level of vision, and I expect you to give him a little show," she continued. "Pretend to drop something, and bend over to pick it up. Learn over him while he's taking his pills, you know, things like that," she offered, as she put a sweatshirt and sweatpants on over her domme attire. Then, she turned and started up the stairs, and I stayed at the bottom of the stairs. "You better get up here FAST slave," she barked, and I hesitantly followed her up the steps. By the time we got to the main wing of the house, my feet were killing me! I was not used to doing so much walking in my heels. I usually just took a few steps around my room, posed and then flopped down on my bed and stuck something in my ass. All the walking really wore out my legs and feet! We got to an office where an older, dignified looking gentleman was listening to some music. "Hi daddy," she smiled sweetly to the old man. She giggled and gave him a kiss on the cheek. "I thought you might enjoy a little treat today," she said, as she motioned to me. "Ashleigh will give you your medicine and take your temperature," she told him, as I shuffled over to him, face as red as the cross on my uniform! I hesitated, and she gave me a discreet, but convincing swat on the ass! I dropped the pen that was in my hand, and bent over at the waist to get it. "Well, young lady, it looks like nurse's outfits are a bit shorter than they were in my day," he laughed as I brushed my ass against his hand. "Oops, my mistake," I said in my highest voice. I handed him his medication and a glass of water, which he took without incident. Then I reached into my bra and grabbed the thermometer. I leaned over him, so my tits were in his face, and stuck the thermometer in his mouth. Once it registered, I said, "Looks normal," and shook it back and forth, causing my tits to jiggle. My face was so red; I felt that maybe someone should take my temperature. I wanted to crawl into a corner and cry. "Ok, we'll be off now, daddy, see you later," Ms. Andrea giggled as we left the room. Once we were out of the room, she turned to me and said, "You are such a natural girl, my little slave! Your face was so red the whole time, though. I could tell you were so humiliated! I am so impressed, though. I think I will reward you!" We had walked all the way back over to her part of the property, and I saw a large pool. "We're going swimming," she informed me, as she led me into the changing room. She handed me the key to my shoes, and told me to get completely naked and get in the shower. I looked at my tits, and Ms. Andrea assured me that both my tits and my hair would be fine. I did as I was told, and she handed me a bottle and told me to lather up. I noticed it burned a bit, and as the water washed the soap off of me, I noticed I was totally hairless from the neck down! Ms. Andrea saw me and said, "There, that's much better! I can't have my girl all full of nasty hair now, can I? You need to look good in a bikini," she said, as she handed me what appeared to be a ball of pink string. I untwisted it, and found that it was a tiny thong string bikini. I wasted no time tying the strings at the side, and sliding the thong into place. I had to shift my hips a bit to make sure the material was properly up my ass, and that my cock was tucked back and out of the way. Next, I tied the top two strings of the top around my neck, while Ms. Andrea tied the remaining two behind my back. She put on a similar a blue bikini that looked stunning with her dark hair and tanned skin. 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. When I got there, Jane was waiting for me at the door. At first, she didn't know how to react. The look on her face was a mixture of shock and amusement. I can tell you the look on her boyfriend's face was a little different! Anyway, I walked in and gave her a hug, and noticed they had kindly packed up all my stuff! "Aw, thanks Jane," I squealed as I squeezed. The boxes were even in one spot, and I walked over and bent down to pick one up. "Nice tat," Jane said. "I never thought you were the type. Although, I guess I was wrong about a lot of things!" "What?" I replied. "On your back, nice tattoo," she repeated. "A nice little tramp stamp, it seems fitting. You didn't know about it? What kind of arrangement do you have with this woman?" In all my primping and preening and staring at myself, I guess I'd never really taken a good look at my lower back. I went into the bathroom and took a look. It was a nice tribal design, with some chains subtly worked in. There was a butterfly as well, and it looked very well done. On closer inspection, though, the body of the butterfly was really a cock, and on either side was a woman's head and neck, bent at an angle to look like wings! I took a few steps from the mirror, and decided one would have to be very, very close to me to see that, but still! Ms. Andrea had truly marked me as her own. I went back out and tried to pick up another box, but it was too heavy. I called the butler at Ms. Andrea's, and he said he would send a few guys to pick up the rest of my stuff. Ms. Andrea told me to get home, because she had an important meeting in a few hours, and required my services. Jane and I hugged goodbye, and I gave her boyfriend an awkward "ass out" hug, and he tried to cling too long! Then I got in my car and drove away. When I got home, I rushed into my room and put on the lacy black push up bra, "BITCH" thong, heels, and short blouse, skirt and jacket I had worn to the office on my first day. I felt bad that I had nothing else, but my specially ordered suits had not been delivered yet. Ms. Andrea wanted to wait until after the surgery to ensure that the new ones would be a proper fit. My new tits actually were bigger than my inserts, somehow, and stuck out even further in the suit. My ass and legs looked stunning in the little skirt! I put some large dangling hoop earrings in my newly pierced ears. There was a shiny piece of metal that said, "SLAVE," which I quickly figured out was a dangling navel ring. I put it on and tugged my blouse down as well as I could. Then I swept my hair up into a bun and right as I was about to leave, I remembered something I though Ms. Andrea would like. The pink jeweled butt plug would be a great addition to my outfit! I bent over, slid the cool metal plug into place, tugged down my skirt, and tottered into Ms. Andrea's office. My hips swayed and my tits bounced with each step! Ms. Andrea was happy to see me, but also very stern. "Listen, Ashleigh. This meeting is very important. Ms. Gilbert is a tough negotiator, and I'm going to need you to be on top of your game, do you understand? I need her to know that I am in control around here." "Yes Ms. Andrea," I replied. Just then, there was a knock at the door. I bounced over and answered it. The woman at the door was about thirty, medium height, medium build. She was wearing a power suit and sensible heels. "Hello, Ma'am, my name is Ashleigh. Let me show you to Ms. Andrea," I said politely. The two women went to the conference room, and sat down at the big table. I let them talk for about five minutes, and then came in with some coffee for each. Ten minutes later, I went in to check on them, and see if they needed anything else. While I was picking up Ms. Andrea's empty cup, she told me it was time. I went over to pick up Ms. Gilbert's cup, bending down to reach it. My short jacket and blouse rode up, exposing my tattoo. I reached back to cover it, but Ms. Andrea stopped me. "Take a closer look," she said to Ms. Gilbert. Ms. Gilbert craned her neck over to examine my tattoo, and gasped. "That's right," Ms. Andrea said. "Those are chains, and that butterfly is really two women sucking a cock. I made her get that. Check out her navel ring!" I obediently showed her the "SLAVE" jewelry that adorned my belly button. "Actually, I made many changes to 'her.'" 'She' used to be a man. I lured him to me, and then took over his life." "Raise your skirt bitch," she growled at me. I did as I was told, and rolled up my skirt enough to show a little bulge in my thong, and the plug in my ass. Ms. Gilbert gasped again, as I took off my blouse and jacket, and pulled down my bra, to bare my tits, per Ms. Andrea's command. "She's totally mine now," she laughed. "I own her, and I control what goes on around here. Make no mistake about my abilities. Now, I am willing to make this deal with you, but it is going to be a fair deal. What does she need to do to convince you?" Ms. Gilbert started to get her bearings back, and a smile crossed her face. "You know I'm a sucker for slutty blondes with big tits. Congratulations, you did your homework. I think she can convince me to make this deal," she said, as she eyed me up and down. I dropped to my knees, and looked up at her. "How may I convince you, Ma'am," I whispered sexily, as I rubbed her nylon covered thighs. She simply rolled up her skirt the rest of the way, pushed her thong to the side, and pushed my head into her pussy. In no time, I had her moaning, and she came all over my face. Not satisfied with my own efforts, I went back in for round two. Ms. Andrea laughed behind me. Very close behind me. In fact, as I was licking, I felt her hands tweaking my nipples. I moaned into Ms. Gilbert's pussy, and then I screamed as something bit into my nipples! Looking down, I saw that Ms. Andrea had attached clamps to each of my nipples! Ms. Gilbert laughed and smiled, and started tugging on them, to encourage me to eat her faster or slower. Just as I got used to that, I felt the sting of the paddle, and Ms. Andrea was back there paddling my ass, as Ms. Gilbert continued to torture my nipples! They kept it up until Ms. Gilbert came again, and said she needed a moment to recover. For a few minutes, I just knelt there, in heels, a skirt, thong, and tits pushed over the top of my bra and clamped, face plastered with cum. I looked over and saw Ms. Andrea coming toward me with two strapons. "Let's seal this deal by double teaming the bitch," she said to Ms. Gilbert. Ms. Gilbert nodded, and I dutifully fitted them both with the cocks that would soon be destroying me. Ms. Andrea grabbed me and told me, "Do your duty, bitch." I stood up and bent over the table, reaching back to roll up my skirt, pull my thong to the side and spread my ass cheeks. Ms. Andrea took her place behind me, laughed, and slid her cock into my ass. No matter how many times I'd taken it, it still felt amazing, and I moaned as she fucked me. Ms. Gilbert got up on the table and as soon as her cock was at the right level, I moved forward and took it gently into my mouth. Ms. Andrea must have felt that she wasn't demonstrating enough control over me, so she gave the nipple clamp chain a sharp tug, which caused me to cry out, but I did manage to keep Ms. Gilbert's cock in my mouth. "You have such a well trained slave," Ms. Gilbert commented. "It's best we keep her in her place, though," she continued; as she started to really skull fuck me. I gagged a little, and she pulled out and slapped me in the face with her cock and then jammed it back down my throat. I felt the two women really got into a good back and forth motion and I rocked with them, trying to maximize their pleasure, as I knew was my duty. Ms. Andrea had taken off my bra. The chain of the nipple clamps, as well as my tits, brushed against the table as they bounced beneath me. My "SLAVE" chain also scraped along the table, and my hoop earrings hit my face and shoulders as they slammed me back and forth. "I really do think the terms of the deal are fair," Ms. Gilbert stated. "I would love to do business with your company. This deal will benefit both of us greatly, now, and into the future." "I agree," Ms. Andrea said. "Our companies compliment each other very well, and together we can really make some moves in this market." "Let's switch." I enjoyed a moment of emptiness in my mouth and ass, before they switched, and Ms. Gilbert took my ass, and Ms. Andrea filled my mouth. "She even does ass to mouth. What a depraved anal slut," Ms. Gilbert commented, before they went back to their business talk. They were using me, and talking like I wasn't even there! As odd as it may sound, it turned me on even more. This is the life I chose, this is the life I wanted, and now I had it. How many other people can say they enjoy their job like I do?