Conquered

Chapter 1:

My name is Jacob Smith (but I go by Jake). I was a student at the University of Alabama in my junior year. I didn’t like my roommates and wanted to get a new living arrangement. The day before the grace period for housing cancellations expired, I ran into an old lady who suggested I live with her. She would keep me for free and pay for my meals with her in exchange for some limited domestic services, such as cooking, cleaning, and “whatever other things might come up”. I hastily canceled my existing rent agreement and moved in with this woman. My first week in her house was fairly routine. I moved in all my stuff with no issues. There were two closets in my room and a full-sized bed. The food supplies she had were fantastic and she taught me how to cook. She was very nice. Her name was Jennifer. One day, about a week into my time with her, she asked me to paint a room for her. She suggested I take my shirt off to do it. Afterwards she gave me a few more tasks to do, which I proceeded to do without my shirt. She gave me a ten dollar “tip” for having done such a great job and then asked me to do my chores without my shirt on from then on. She asked so cutely that I agreed. And that was the beginning of the end.

Within two weeks, she asked me to wear this cute little pair of shorts instead of my normal ones. They were tight as heck and had no pockets… I figured out later they were women’s shorts and were several sizes too small. I accepted her offer and from then on that’s what I wore whenever I did work for her. One day I forgot my chores and as a punishment, she suggested that I change into my work shorts as soon as I came home from school each day; that way I would be sure not to forget. I accepted her “suggestion”. One day she brought home an outfit for me to try… a French maid outfit. For kicks and giggles I put it on and started cleaning. She took a picture of me in it. I protested but she just grinned. At that moment I thought I might be in trouble.

The next day when I went to change she had replaced my work shorts with a tutu. No suggestions here… just an unspoken order. What did I do? I put it on! After I was cleaning for a while, she came in, delighted with me. She told me that it was ridiculous for me to be cleaning in a tutu with boy’s underwear. I said with a sarcastic grin “do you have any other suggestions? I am a boy after all”… to which she just grinned and motioned me to come over. She had laid out a set of panties for me to choose from. “Change”, she said. “Not with you here!”, I replied. She rolled her eyes and walked out. What did I do? I took off my tutu and underwear, put on a bright peach pair of panties, and put my tutu back on… when she took another picture of me. “Sorry, you just look so darn cute in that outfit!” she squealed. This was a sixty-five year-old woman!

I was furious, but she called me out. “Admit it, you’re enjoying this.” “Yeah but that doesn’t mean I want pictures taken of this!” She gave that look to me again. “Tell you what, Jake. I’ll delete this picture and the other one if you promise that when you come home from now on, you’ll change into a dress for me.” “And you won’t take any more pictures or let anybody else know about this?” “Of course not!” “Okay, that’s a deal.” And we shook on it.

Chapter 2

When I got back from school the next day, a Thursday, Jennifer was gone but half my wardrobe (one of my closets) had been replaced with dresses, blouses, skirts, tutus, and that French maid outfit. My drawers were filled with panties, and I noticed a pile of boxers in my other closet. There was a safe in the hallway coming right in from outside and a note from Jennifer on my door. “Please place the clothes you’re wearing today and that you plan to wear tomorrow (including your shoes) in the safe and close it. I will be home by tomorrow morning to unlock it for you. Please remove the padlock inside the safe and use it to lock shut the closet with your old clothes. I hold the key, so don’t waste time trying to find it. I expect to find you cleaning the house in your French maid outfit when I return at 6:00.” I followed her instructions, feeling dread but excitement.

She returned quietly and snuck up behind me as I vacuumed the basement. She grabbed me from behind and whispered “you were a good boy, I have a surprise for you”. I went upstairs with her and She (I think I’ll use that capitalization from here on out) introduced me to a collar. It was shiny, red, and beautiful. It had a dog tag and everything. I put it on, fastening it without reading it and smiled at how delightfully it fit. She said, “Jake, this perfectly symbolizes our relationship. I’m in charge, and you follow my commands like my little bitch.” I opened my mouth to disagree and She slapped me. “Jake! I am wearing a shirt and pants. You are wearing women’s panties, a French maid outfit, and a collar that says ‘Jennifer’s Bitch’! What do you think you are? You’re my fucking little bitch, that’s what you are! Now get in the kitchen and make me a sandwich!”

What could I do? Jennifer was right and it was my responsibility to cook for Her. I nodded out of sarcasm and said “yes Ma’am.” She slapped me and said “How about “yes master” from here on out?” I looked at Her, and was about to tell Her where She could shove that “yes master”, but then I thought… deeply. She stepped back a bit while She let me think this over. I was in a French maid outfit with a collar on and it was clearly because She was in charge. I was… happy about this? I had an erection and I was hoping this whole thing would just slip right on by. I nodded again, and said without a hint of sarcasm “yes, Master.” She didn’t change Her expression at all. I went off slowly towards the kitchen and started making Her a sandwich.

When I returned with it, Jennifer was sitting on the couch. She was not very pretty, given that She was old enough to be my grandmother. She motioned me over and then stopped me when I was about three feet away from Her. “Kneel”, She commanded. I had no choice, really. I knelt. “Hand me the sandwich”, She commanded again. I did so. “Crawl over her and stay on your hands and knees. I mean to use you as a table.” Humiliated, I crawled over… and She kicked me in the face with the boots She was wearing. “I didn’t hear a ‘Yes, master’ in there!” “Yes, Master” I muttered. “ ‘Yes, master what?’ ” She was not amused. “Yes, Master, I would love to crawl over towards you and be your table for you.” “And why would that be?” She asked with a deceptive tone of honey in her voice. “Because I’m Your bitch.” Her praise flowed out. “Very good, my little slave. You are my bitch and I am in charge of you.” “Yes you are, Mistress” I said as I crawled in front of her, my dress squeaking under me. She didn’t respond but simply placed the plate on my back. Some few minutes later She lifted it and replaced it with a small, light object. I heard a “click” and I was hooked. “Slave?” “Yes, Mistress?” “That is a dog leash to go with your collar. From now on for all of your days here, you will be forced to put on your leash the moment you return from school till the moment you leave here. If I don’t desire it at the moment you can simply clip it onto the back of your collar. I expect you to wear that collar at all times, here or at school.” “Yes, Master” I replied, more out of shock than anything. She clipped on my leash and sent me on my way to finish the chores.

When I had completed them, I went to do homework in my room. She had taped a white, frilly bra to the bedroom door with a note ordering me to put it on under my outfit, and I hurriedly did so. She summoned me shortly afterwards to Her bedroom. I ran up, heart racing. It wasn’t just externally that She had begun to take control. Certainly, the outward signs were there—I was responding to Her beck and call, I was calling Her my Master, and lest we forget I, a red-blooded, totally straight, conservative American man, was all dressed in frills and lace, with a collar on top of it all proclaiming my submission and humiliation for all the world to see. But it was the mental domination that was really taking place. I would, at that moment, have died for that Woman, though I didn’t realize it yet. The feelings I fought with on my way up were anxiety, yes, but most of all a sense of giddiness. Above all else, I had total faith that She would take care of me and ensure that our relationship would be the best one possible between a landlady and a boy.  I reached Her room and opened the door to see Her standing there.

I suppose I haven’t really described Her very well yet. She is 5’3, a full eight inches shorter than me. She has gray hair with just a hint of its former brown. Her eyes are fiery and Her smile is the sort that most men would kill to see. I was struck as I entered the room by how unimpressive She seemed. If She was controlling me, it sure wasn’t through Her sheer beauty or charm. She emphasized that with a harsh command. “Bend over and touch your toes”, She asked. “Yes, Master”, I responded. She regarded my tail end diligently as I maintained the position. “We will be proceeding shortly with your two main jobs as a slave. The first one is quite simple. Hand me your leash.” “Yes, Master.” I responded as I stayed bent over, reaching out my leash to Her. She took it and quickly led me to Her king-sized bed. “Spread out, face down” She commanded. “Yes, Master.” She sat in front of me and gently removed Her pants and underwear (boxers, I noticed). “Come here are lick me until I come in your pretty little face, bitch.” “Yes, Master” I responded, and crawled forward. Once I stuck my tongue into Her, I heard the leash lock. There was now no way out except to break the cord of the leash (which, I must admit, I had already tried to do and failed miserably) or wait until my Owner released me, which She was in no mood to do. She passively sat there as I tried to make something happen, but I wasn’t very good at it and She was not getting excited. I thought I noticed a flash of light a couple times, but I assumed I had imagined it and even if I hadn’t there was nothing I could do. After about a half hour (I wasn’t keeping track but She was and told me later), mercifully She began to get wet and start grinding into my face. She came about ten minutes later. She left me there with a stern command: “Don’t you dare move a muscle.” I froze, the taste of Her juice still on my lips. “Hands and knees, and hike up your dress,” Jennifer ordered. I felt a wave of dread as I obeyed Her mandate. “Pull down your panties”, She demanded. I complied, feeling incredibly scared. She walked in front of me and tied my leash around the headboards of the bed so I couldn’t run away but would have plenty of room to move around. “Jake, earlier today I noticed you called me your Mistress. Now why would you say something like that?” “Umm…” I didn’t know how to reply… “because that’s… well… You’re a woman, aren’t You? Isn’t that what people are supposed to call women masters?” “Jake, to the world, I am a woman. But you are my little bitch, a dog, a slave, a tool, a slut for dressing up like a girl. I am your MASTER, for two reasons. A dog knows neither man nor woman, only his master. You are my little puppy dog, and I am simply your master. But the other reason is much sweeter,” She added as She reached underneath my ass and tied a little blue ribbon around my exposed penis. “I am wearing a shirt, no bra, boxers, and jean pants. You, my sweet little puppy, are wearing a bra, panties, and a fucking French maid outfit. Now, who dressed you? Was it me? Or did I just tell you what to do and you did it your fucking self?” “I did what you told me to, Master”. “Exactly. A mistress is someone you respect, someone you fuck, but a master is someone you obey. Now you get what I’m talking about. Here’s the real deal. I’m the man right now in this relationship; you are my woman, as far as status is concerned. I know, you biologically have a penis—which I have just claimed with my ribbon—but metaphorically I have the penis… and as I’m sure you’ve guessed by now, I’m lubing up a pretty good replica for you to try out for size. I of course have a vagina, you just had a very personal encounter with it of course, but… how to say this… I have a cunt, you ARE a cunt!” “I’m Your cunt, Master.” “Ha, so you are. Anyway, enough talking.” She slapped my ass and grinned. “Grab the headboard with one hand and jack off with the other, I’m not stopping the rape till I see your come, bitch. You’re going to learn to like getting fucked and used. You’re my slave, remember?” “Yes, Master”. She grinned and flicked on the lights. “Oh yeah, and one more thing”, She added as my eyes followed Her towards Her place behind me. “Face forward, dearie, and smile for the camera.” “What--?” I started to say, as She plunged into me. “AHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH!!!!!!!!!”

Inward and outward, out and in, the blood spilling out of my crack, Her laughter, my tears, and all the while I was trying to jack off as quickly as possible. “What’s your name, slave?” “My name is Jacob Smith!” “And what are you?” “I’m Jennifer’s bitch!” “Scream it at the top of your lungs, baby!” “I’M JENNIFER’S SISSY LITTLE BITCH!!!!!” I screamed as I came. “YEAH BABY YEAH!” She screamed as She dug into me one last time, then removed it slowly. She walked over to me and offered Her strap-on. “Suck it clean, bitch, and thank me for the opportunity.” “Thank you very much, Master, for letting me lick your strap-on” I said as I took it into my mouth. The disgusting flavor didn’t even phase me after the events of the day, though I cringed at the sight of the blood from my own cherry.

She took me up from Her bed after She had fucked me and brought me downstairs. I didn’t know what to do. Suddenly, she grabbed me and hurled me down to the floor. I laid flat on my back. She quickly and roughly stripped me of the little clothing I was still wearing and whipped out four pairs of handcuffs and chained me to the furniture. “Sweet dreams, bitch. When you wake up we’ll have a full discussion of what just happened. Until then, sleep tight and know that you are owned.”

(To be continued…)