Stepmother Knows Best free porn video

I know it sounds kind of pathetic when I tell people I'm twenty-five years old and still living at home, but it really isn't my fault. After graduating high school I had drifted through a number of meaningless dead end jobs before finally deciding to go back to college part time. My life certainly wasn't what my dad hoped for, but he has always let me make my own choices. While my family has a lot of money my dad firmly believed in people standing on their own two feet, meaning once I turned twenty-one he felt I should make my own way in the world just like he did. I figured the only reason he was letting me still live at home at my age was because of the memory of my late mother. She had died a number of years earlier and because I was an only child I suspect dad was unwilling to be quite as harsh towards my situation as he would be if my mother were still alive or if I had brothers and sisters. Being an only child from a rich family I had really liked to party as a teenager, and had found the transition to adulthood difficult. To this day I wanted to live better than I could afford to on my own, and I felt some resentment that my father wasn't more accommodating to my preferred lifestyle. He could certainly afford the money, however he had made it clear he was only willing to pay for my college tuition and books and nothing else. If I wanted any spending money it was up to me to earn it, and I did like my spending money. That's why I was only going to college part time. If I had gone full time as my dad wanted I wouldn't have had any time or money to do anything or go anywhere. Actually it is the same reason I had gotten a number of jobs after high school. To be perfectly honest the only reason I ended up at college in the first place was my dad had threatened to kick me out of the house once I stopped being a student. Going to college part time was a compromise that allowed me to stay in the house and still have at least some piece of the kind of life I craved. Unfortunately there was other strife in the house besides that between me and my dad. I got the strong impression my stepmother Jordan really wasn't happy with the situation. She was ten years older than me, with my dad having married Jordan a few months back. I have to admit Jordan was a very good looking woman, and I could see why my dad was attracted to her. So much so in fact that late at night I sometimes fantasized about her. While I liked having her around so I could fantasize, from her perspective I think she would have preferred to have the house all to herself, just her and her maid Marta doing their own thing while my dad was at work. Several times I had stumbled on her by the pool as she was sunbathing in the nude. Although she had been face down both times, it still gave me a lot of fuel for my fantasies and caused her a lot of embarrassment. I don't think she hated me as such, just really didn't want me around when my dad wasn't at home. In hindsight I should have paid more attention to the situation once I found out my dad was leaving the country for a couple of years. My family had money primarily because my dad had started his own very successful business, and right now he had to go overseas for a while to guide the company's expansion. He called me into his study one night shortly before his departure. Although my stepmother apparently volunteered to go with him, dad explained to me "Steven, I'll be working all the time and wouldn't see much of her. Her friends and her life are here, and because of all of those factors I believe she will be happier and more comfortable if she stays home and just visits me occasionally while I'm gone". As my dad was telling me this I got the impression there was another unstated reason for the separation. I had a feeling she was supposed to watch over me, making sure I didn't take advantage of having the house all to myself. He certainly left no doubt that she was in charge while he was away, both with the house and my college money. "Steven, I've asked Jordan to pay your tuition every semester, and give you money for books as needed," my dad informed me. "You had better remember she's in charge of this house, so behave yourself and do as she says. I've discussed your situation with Jordan and it's okay with her if you continue to live here while I'm gone, as long as you realize she is the boss around here. If that is too difficult for you, you can move out right now," my dad concluded harshly. Needless to say I decided to continue to live in the house, and figured I would just avoid Jordan for the most part so the thing about her being the boss would never be a factor. The following Monday was my first day at college, however I was so preoccupied with my home situation I hadn't given it much thought. Even walking through college campus on the way to my first class I was still so lost in my own thoughts about the home situation that I didn't even notice Amy. While not close, I had been in the same grades as her throughout high school and we did know each other somewhat. My first indication I knew someone on campus was a shout from behind. "Steve, how have you been?" Turning around I spotted Amy immediately. The fact we were not close in school had nothing to do with me. I had always thought she was very pretty, and had tried to get to know her better numerous times. During high school she had never been interested, telling me I was too shallow and had too much money. Because of her opinion of me I was a little surprised at how she had just greeted me. "I'm good Amy, how about you?" I asked, finding myself very interested in her response. Maybe I had changed since high school or she had. "I've been great," she informed me. "I finished my masters degree last year, and am currently working towards my PhD in social science. I am so happy about the whole thing. It's been a dream of mine for years and I'm finally getting close. How about you? I don't remember seeing you on campus before. Are you in one of the graduate programs?" she asked, much to his embarrassment. "Not a graduate program, no," I replied. "I started working right after high school, and decided just this year to go to college. I guess that makes me a freshman," I finished, not knowing how she would take this bit of honesty. ? Much to my relief she took it exceedingly well. Looking back I probably shouldn't have been too surprised. Amy had always been like that in high school, and there was no reason to expect her to have changed. It turned out both of us were early for where we had to be, and we were still chatting away an hour later. Finally it was time for me to get to class, but I decided not to leave without asking Amy the question that had been bothering me for the last hour. "Before I go to class there is one thing I have to ask you," I started off. "In high school I got the impression you didn't really approve of me," I finished, waiting for her reaction. "I didn't really dislike you, but I thought you could have made more of yourself. You're smart and you had a lot of advantages growing up, but didn't seem to be interested in anything other than a good time. But I believe people can change. Besides it was nice seeing someone from the old school," she explained, amazing me yet again. We parted on that note, with each of us giving the other contact information. I have to admit I spent a lot of time thinking about her when I should have been paying attention to what was being taught in my class. It was about a week later that I had another parental discussion. The discussion started as soon as I arrived back home from school, with Marta telling me Jordan would like to see me. I found myself back in my dads study for the second time this month, this time waiting to hear what Jordan had to say. Wasting no time, she laid down her law for me living at home. "Steven, for starters I'm telling your right now you are going to have to be on your best behavior. Second, I want you to write out a schedule of when you are working and when you are at school, so I know where you are going to be. Thirdly, you are going to have to help out around the house if you want to stay here. You are not paying any rent, you are getting full use of the house, you get all your meals cooked for you, and frankly are continually making a mess of the place. From now on I'm going to have Marta supervise you in your chores and report back to me on how well you did them. For now I think ten hours a week of your time is fair payback for everything you are getting. And before you get all worked up about the changes as I know you are likely to, you should step back and think about what I am asking. Don't think of this as some kind of punishment, but rather as your way of pulling your own weight around here. One last thing. I don't expect to be getting any bad reports from Marta on your performance, but if I do I will have to punish you. Now do you have any questions on anything I've just told you?" she finished, looking at me for a reply. I was honestly too shocked to react, and just stood there until she asked me a second time if I had any questions. I still didn't speak but did manage to shake my head no to her question. "Why don't you go ask Marta for your first chore then Steven. You don't want to fall behind on your work, especially as it is so early in the school year. It should be much easier to find the time now than it will be later in the school year," Jordan observed as I stood there stunned. I had actually been planning on a swim just now, so was really unhappy with this change in my schedule. Deciding there was no point in creating a fuss at this point I meekly left the room and went in search of Marta. I spent the next few hours vacuuming the upper floor of the house, finally knocking off close to dinnertime. Having just enough time for a quick swim before dinner, I quickly changed into my swim trunks and headed for the pool. I was a little surprised to find Jordan already there, lounging poolside wearing a very sexy black bikini. I headed straight into the pool, hoping she hadn't noticed the erection pushing at the front of my swim trunks. I spent the next ten minutes swimming around trying to distract myself, trying to get my penis under control through sheer force of will. I finally managed to settle down a little, and headed for the side of the pool before I lost control again. I didn't anticipate Jordan would stand up and offer me a towel. As it was obvious I had been about to get out of the pool there was no way I could start swimming again without possibly insulting Jordan. Trying to think pure thoughts I grabbed the side and hoisted myself out of the pool. While handing me the towel I noticed Jordan's eyes were focused on the front of my trunks. I realized I was losing control again, and could feel my erection growing even as I was grabbing the towel from her. As fast as I could I draped the towel over myself, letting it hang down my front to cover up my growing erection. Once I was covered Jordan's eyes slowly moved up my body before stopping at my eyes. A smile crept across her lips as our eyes locked for what must have been a quarter of a minute. Finally she spoke. "Why don't we go inside and get ready for dinner Steve," she suggested. "We don't want to insult Marta by letting the food get cold. By the way, I hope it didn't sound like I was being hard on you earlier. I do want you to do your share around the house, but I understand you have both school and work as well which means I'll try not to make your schedule too difficult for you," she told me, as I stood there trying to stay mad at her. In the end my hormones won out as I was far too attracted to her to stay mad for long. One look at her proud breasts thrust forward in that skimpy bikini top of hers, or her nicely rounded ass encased in the bikini bottoms, and my knees turned to jelly. Almost involuntarily I found myself telling her everything was fine. "It's no problem at all Jordan. I want to do my share around here," I heard myself saying, even though it wasn't really true. I really wanted to be able to hang around the house and have someone else do all the work, but certain women turn me into a babbling idiot. Apparently Jordan was one of those women even if she was my stepmother. I almost ran into the house before I could say any other stupid things, afraid of what I might commit myself to in a moment of weakness. Dinner was a little strange, as Jordan spent most of the time asking me questions about my life. She wanted to know how school was going, how I liked my job, whether I was seeing anyone, and similar sorts of things. She seemed to be making a real effort to get to know me better, something she had never done in the past. We actually ended up sitting there for more than an hour after we had finished our food, engrossed in the conversation we were having. I have to admit Jordan really charmed me with the way she was paying attention to me. After interacting with her like that I began to better understand how she had ended up enticing my dad into marriage. It wasn't only her physical beauty she had going for her, but something much deeper. She had a way of making you feel like you were the most important person in the world, and I was genuinely sorry when she got up from the table, thanked me for my company at dinner, and told me she had things she needed to do. I had difficulty failing asleep that night, as every time I started to drift off I would start thinking of her again. I finally sank into a troubled sleep, having dreams a young man probably shouldn't have about his stepmother. I slept late the next morning, not having any classes till after lunch. Getting up around 10 o'clock, I jumped into the shower and was soon clean and ready to face the day. At least I thought so until I ran into a bit of a snag. I went to my underwear drawer looking for briefs and there was nothing there. It looks like I had used all my clean underwear without realizing it. 'Oh well' I thought, 'I'll have to use the ones I had on yesterday'. While not my preferred option it would do in an emergency. However when I went to retrieve them from the pile of clothes of yesterday's clothes they were gone. Putting on a bathrobe I went in search of Marta, eventually locating her in the laundry room poking at the washing machine. "What happened to all my underwear," I asked her as soon as I spotted her. "There is problem Mr. Steve," she told me as I approached her and the machine. "What kind of problem?" I asked, not sure if I was going to like the answer. "Machine stop working," she told me, pointing at the washing machine. "That is a problem," I replied "But for now I just need one pair of underwear," I told her. "Underwear in machine," she answered back to me, pointing to the machine as she was speaking. Stepping over to the machine I lifted the lid, expecting to see a pile of dry, dirty clothes. Instead I found a washing machine completely full of very wet dirty clothes and soap suds. To say I was upset would be an understatement. I have to admit I lost my temper with Marta, yelling at her for making it so every pair of briefs I owned was soaking wet. It took me a few minutes to wind down, during which Marta never stopped staring at me. I couldn't figure out what was going through her mind as she listened to my tirade, but she was far too quiet for my piece of mind. I finally stopped yelling and accusing, and stood there mute for a minute. "You not deserve it, but I can help you problem Mr. Steve," she told me. "You come," she motioned to me as she left the laundry room. I reluctantly followed her upstairs, ending up at her room. "You wait in hall," you told me as she went into her room. I didn't have long to wait before Marta reappeared carrying a package. "I buy for Miss Jordan. Not give her yet. You use." she told me handing me the package. It turned out to be a new pair of panties still in the original packaging. "There must be some other choice Marta!" I exclaimed after seeing what she had in mind. "There has to be some mens underwear somewhere in the house," I continued. "Sorry Mr. Steve, your dad take all clothes with him. Your underwear all in wash," she told me, spreading her arms in the typical gesture of helplessness. I didn't want to wear panties, but didn't seem to have much choice. Looking at the picture on the box they didn't look that bad. Finally admitting defeat I headed for my room, panties in hand. Stripping off my bathrobe, I pulled the panties out of their box and sat down on the bed. Although they didn't look all that different from my usual briefs, I noticed right away that the material felt quite a bit different. They had a much silkier feel to them than my normal underwear. Stepping into them, I slid them up my legs and stood up to settle them into place. I couldn't believe the feeling of the panties against my penis. The silky material seemed to caress my privates, and I actually started to get excited. Almost involuntarily I found myself lying down on the bed before reaching into the panties to stroke myself. I started masturbating like crazy, pulling the panties down just in time to avoid making a mess of them. I could just imagine trying to explain to Marta that I needed a second pair of panties because I had gotten the first pair dirty within five minutes of getting them. I lay there panting for a while, trying to understand what had just happened to me. I didn't like the implication of what had just happened. Stripping the panties off, I headed into the bathroom to have another shower. While showering for the second time that morning I halfway convinced myself I must have been fantasizing about Amy or Jordan while masturbating, and the panties had nothing to do with what happened. Having finished my shower, my resolve was shaken as I put the panties on for a second time. The feeling was the same as before, and I started to get an erection once again. This time I managed to distract myself, and finished dressing without any further incidents. That was not the end of my problems however. Driving to school the material rubbing against my penis was a constant reminder I was wearing panties instead of my normal underwear. It wasn't any better sitting in class, and I ended up paying a lot more attention to my underwear than to the lecture. In due course the class was over, leaving me to face the next and biggest hurdle of all. I was supposed to meet up with Amy after class, as per the plans we made the previous week. Our meeting point was an old oak true at one end of the quad. I must have been a little early, as Amy was nowhere in sight. Unsure as to how long I would have to wait, I decided to sit down on a convenient bench. I had only been waiting a few minutes before Amy arrived at our rendezvous point. I must have jumped a foot when she came up behind me and put her hand on my shoulder. I had been trying to imagine everything that could possibly happen over the next few hours, trying to make sure none of the possibilities could lead to Amy finding out I was wearing panties. I realized I had become so engrossed in my speculations I had completely tuned out the rest of the world. I also realized that is exactly the kind of thing that could trip me up, and determined to stop worrying so much about things that could go wrong and concentrate more on making things go right. I felt a lot better after making that decision, and happily started debating with Amy on where we should go to talk. We ended going to a little cafe on campus that Amy patronized frequently. Over the next hour we chatted about our childhoods, people and events in high school, and finally our plans for the future. I was surprised at how easy it was to talk to her, and I got the impression she felt the same way. What was supposed to have been a short one hour chat soon turned into an all afternoon talk fest. I have to admit I was so interested in the descriptions she gave of events from her perspective that I lost all track of time. For my part I believe I managed to convince her there was more to me than a rich spoiled kid out for a good time. I tried to project the idea that I may not have found my way in the world yet, but I was trying my best. The funny thing is, while it wasn't exactly true that I was trying as hard as I could, being with Amy made me want to put more effort into my life than I had been until now. In a way she made me want to improve myself so that I would feel worthy of asking her out on a date. I think she was the first woman to ever have that kind of effect on me, and it left me a bit unsettled. Although our get together had gone very well, I still was uncomfortable taking the next logical step. Fortunately for me I it wasn't left up to me to make the next move. Amy actually suggested we get together for dinner the following weekend, which I happily agreed to. I would have preferred to do something the coming weekend but Amy mentioned something about going out of town to visit her parents. The asking out part was a new experience for me, specifically having a woman take the initiative, but I was actually enjoying that aspect of our budding relationship. I headed for home singing some song that had popped into my head, something that wasn't like me at all. Sad to say my happiness was to be cut short as soon as I arrived home. I had completely forgotten about getting mad and yelling at Marta, but Jordan had found out and had her own take on the incident. I was walking through the house, still singing that silly song when Jordan must have heard my voice. She called out, or should I say yelled out from the study "Steven, please come into my study immediately. You and I need to have a little chat," From her tone of voice she didn't sound very happy, so I immediately headed for her study not wanting to make her mood any worse. As soon as I stepped across the threshold of her study she lit into me "I thought you understood the ground rules around here, and knew your place in this household. Apparently I was mistaken. Don't worry though, I will make sure you understand the rules by the time I'm finished with you," Jordan told me, somewhat ominously. Now that I was really worried she proceeded to tell me what I had done wrong. "I heard what happened in the laundry room, and I warn you speaking that way to Marta is completely unacceptable, Steven," she yelled at me. "I'm afraid you'll have to be punished for your behavior. To be honest I think it only fair to allow Marta to decide what that punishment should be," Jordan added in a slightly lower voice. To say I wasn't happy about how this had turned out would be an understatement, but there wasn't a lot I could do about it. I was trapped not only by my desire to live in the house, but also by my physical attraction to Jordan. "Marta, would you come in here please," Jordan called out as she walked out of the study. Marta must have been close by because she appeared almost immediately. "Yes Miss Jordan?" she asked. "Marta, I've just finished explaining to Steven that the way he spoke to you is unacceptable, and I don't want it to ever happen again. I've also informed him that as you are the wronged party, you will be the one to decide his punishment," she informed Marta. After reflecting for a moment Marta gave my punishment. "In my country we have way fixing bad boys," she said as I stood there with a sense of foreboding. "Boys wear girl clothes until behave better," she finished. I was too shocked to say anything, and almost missed her next statement. "Mr. Steve not like wear panties he borrow other day, so Mr. Steve wear panties each day for rest of week. That I think is good punishment for him," Marta finished. "That is an excellent idea, Marta," Jordan encouraged her. "I'm sure that will allow Steven to recognize the error of his ways, and stop him from making the same mistake a second time," she added, likely for my benefit. "Marta please go out this afternoon and buy Steven enough pairs of panties to get him through the rest of the week. I'll leave it up to you to pick the styles and colors. One piece of advice however; I know these days some pairs of plain panties look very similar to men's briefs. I suggest you avoid that type and instead buy him panties that are much more feminine. I think the lesson will stick with him much better if he can't pretend he is wearing anything except womens underwear." She told Marta, pronouncing my doom, as far as I was concerned. I couldn't believe my only choices were either wear womens panties everyday for a week or move out of the house. Exiting the study, I headed upstairs to my room. I still had about an hour until dinner, probably more as Marta was even now leaving to go shopping for my new panties. I tried to use the time to catch up on my studying, but my mind kept straying towards my punishment. I was so unsuccessful at concentrating on my schoolwork that I easily heard Marta's car as it pulled up into the driveway. Within a few minutes I heard her clumping up the stairs, before headed down the hallway towards my room. I was already turned and facing the door as she knocked. I was tempted to pretend I wasn't here, but decided in the end that would only make things worse. "Come in please Marta," I called out. She immediately entered my room, brandishing a bag from the most exclusive lingerie store in town. Walking over to my bed, she dumped the contents of the bag on top of the covers. "I buy pretty panties for you. Also buy bras that match panties, in case you bad again," she told me. I was in shock as I looked at the lingerie on the bed. For starters the panties were incredibly feminine. I saw pink and red, baby blue, black and purple. All of the panties seemed to be made mostly of lace and ribbons. By far the worst part however, was the pile of bras sitting on the bed. When Marta noticed me focusing on that part of her purchase she immediately bent over and picked one of the bras up by its straps. The bra she picked up seemed to be a match for the pink panties. It was the same color as the panties and used the same style of lace. Even more disturbing was the fact the bra seemed to have heavy padding in the cups. Wearing it would definitely make it look like I had breasts, something I wanted no part of. Seeing my look of horror caused Marta to walk towards me still carrying the bra. "Marta please no," was all that came out of my mouth, when what I really wanted to do was yell at her and tell her there was no way I would ever wear a bra. She seemed to be holding the bra up in such a way that she could see how it would look on me if I was wearing it. "You can try bra now if like. I help." she told me. "You see if fit you, if like to wear woman's bra," Marta added as she came within a couple of feet of me holding the bra at chest level . She moved to hand me the bra so that I could try it on. Of course I knew I would never agree to wear a bra, and quickly stepped back out of her reach to make my intentions clear to her. Seeing my reaction she decided not to push it, instead turning around and walking back to the bed to deal with my new lingerie. "I put away. Can try on bra later when alone," Marta informed me as she scooped the lingerie off the bed and brought it over to my dresser. Placing the pile of dainties on top of my dresser, she started shuffling my clothes around as she moved what I already had from one drawer to another. As far as I could tell she was freeing up the top drawer of my dresser where I usually kept my boxers and T-shirts. Within a few minutes it looked like she had created enough space in the drawer, and started loading the drawers with the bras and panties. "I finished," she informed me as she closed the drawer and turned away from my dresser. "You wear panties tomorrow. Me check. You decide if wear matching bra. Wear bra two days, you only have to wear panties two days not six," she informed me as she headed for the bedroom door. I really couldn't see going for that deal even if it would allow me to end my punishment quickly. I didn't even want to look at my new underwear never mind wear it, but found myself walking to the dresser and opening the top drawer anyway. Looking inside I couldn't believe there were a bunch of very feminine looking bra and panty sets sitting in my dresser drawer, and all of them belonged to me. I appeared to have more bras then most women had, however I vowed right then it would only ever be the panties I would ever wear, and only this week. I didn't sleep very well that night, my dreams continually going back to the theme of being on a date with Amy. Sometime during the course of each dream date Amy would discover I was wearing panties. In one dream sequence I actually put on a matching bra and panty set when getting ready for the date, somehow managing the put on the bra as if I had been doing it my entire life. I never did find out what Amy's reaction in the dream was to my secret, as I kept partially waking up every time she was about to discover my lingerie. After a seemingly endless night it was almost a relief when morning came and it was time to get out of bed. After taking my usual shower I pulled open my underwear drawer, the same way I did every morning. This morning however, I stood frozen staring at the new contents of the drawer. I finally reached in a pulled out a pair of panties. There wasn't much to choose from, as other than being different colors they all looked alike to me. I ended up grabbing the purple panties, causing my eyes to be involuntarily drawn to the matching purple bra folded neatly in the same drawer. Right at that moment I found myself wondering what wearing the matching bra would feel like, my mind going back to my dream. "No, don't do this," I told myself, before I managed to pull my gaze away from the contents of the drawer. I quickly shoved the drawer closed and proceeded to step into the panties. Once I had them pulled into place over my crotch I was in trouble yet again. Between the snug feel of the panties and the sensual material they were made of, I found myself getting an erection again. Mentally I told myself there was no reason to get an erection every time I wore panties, but my body wasn't listening. It took me a few minutes, but finally I managed to lose my erection by ignoring the sensations the panties were sending through my body. In spite of the nervousness I felt due to my forced choice in underwear, that day and in fact the entire week passed uneventfully. Every morning I stared at the neatly folded bras for a few minutes, a small part of me wanted to try one on. And every morning I convinced myself I would never wear a bra and turned away from my drawer without picking one up. Just like that it was suddenly Saturday, and I realized I had real no plans whatsoever for this weekend. In fact I had really been looking forward to having a day off. Between school, work and helping around the house, it seemed like I was busy most of the time these days. Sleeping late and spending the rest of the day hanging around the pool sounded really good to me at the moment. Unfortunately my plans were derailed before I had even gotten up. I was still dozing in bed, not quite asleep but not quite awake when Marta came bursting in to my room. "Time get up," she told me in her usual stilted English. "Go away Marta, I'm trying to sleep," I complained, trying to shut her out and get some more sleep. Of course with her, it's never that easy. Next thing I knew she was grabbing my leg and pulling me our from under the covers. Now as it happens I don't wear pajamas, so being pulled out of bed by older German maid is not my idea of fun. I managed to grab a handful of sheets just before landing on the floor. Of course being pulled out of bed and dumped on the floor had brought me from dozing to fully awake. I glared at her for a moment, but that didn't seem to be having any effect. I gave up and decided to find out what the heck was going on. "Exactly why did you barge into my room and out me out of bed," I asked, still mad but trying not to show it too much. I still vividly remembered the last time I had yelled at Marta, and more specifically the punishment that had followed. In fact today was the last day of that punishment, and I certainly didn't want it extended for any reason. "You get dressed, help Miss Jordan," she informed me. "It's my day off," I replied, more by rote than for any other reason, as I knew I had already lost this argument. Not even bothering to respond, Marta headed over to my dresser and pulled the red pair of panties out of my underwear drawer. "You want bra?" she asked, pulling the matching red bra out of the drawer and holding it out towards me. A small part of me actually considered the idea briefly, but the rest of me quickly told Marta "No thanks. In fact maybe we could skip the panties as well, as it's my last day and I have behaved myself all week," I ventured, hoping she would show some flexibility. "No. You shower, then you put on clothes," she told me, dropping the bra on my bed and tossing me the panties. "Put on nice shirt and pants, come downstairs. Have 10 minutes," she said as she left the room. Deciding to tread carefully that is exactly what I did of course, showing up downstairs before the deadline. "You help in kitchen now," Marta ordered me as I presented myself to her. "Turn around and I put apron on, not mess clothes," she added to my discomfort, indicating with her finger that I should turn around. Not wanting to cause problems I did so, standing there while she fastened an apron on me. Looking down I couldn't believe the apron she had me wearing. It was a deep pink color, with a lot of lace and ruffles running all up and down it. It was the kind of apron being worn by housewives in old TV shows over top of their big flared skirts. Once I realized the kind of apron I was wearing I started to feel very sarcastic and a bit angry, causing me to say something to Marta I shouldn't have. "Why don't you put me in a dress and high heels and finish the job," was what came out of my mouth in exasperation. Of course, I regretted saying it instantly. "You want dress and high heels Mr. Steve?" was her reply "not problem. I buy for you. You wear with bra, make feel pretty. Look like woman. Feel like woman," she predicted. "No, no Marta, I was only kidding. You know, making a little joke," I explained, hoping the whole thing would be forgotten. "I tell Miss Jordan you want woman clothes. I sure she say yes, tell me buy dresses for you," Marta continued on as if I hadn't tried to explain my statement. "No Marta, please don't do that. I'd appreciate it if we could just drop the whole subject," I replied, still hoping to put this whole thing to rest. "You leave to me Mr. Steve, I fix with Miss Jordan. Get you pretty dress, very sexy. Make you feel like woman. I sure you like new clothes I get you very much," she replied, eliciting a groan from deep inside me. "Now we work," she added, handing me a potato peeler and a bowl of potatoes. We spent the next few hours preparing food, followed by hours of cleaning the kitchen, dining room and bathrooms. Finally Marta released me from servitude, not before telling me I would have to help serve the food later today however. Discarding the apron I had been wearing, I felt very weary as I headed up to my room for a quick snooze. As I entered my room I noticed the red bra was still sitting on my bed exactly where Marta had dropped it earlier in the day. In hindsight it seems silly, but right that second I didn't really want to touch it. It was almost as if by picking it up I would be accepting the bra as my own. On the other hand I couldn't very well leave it sitting on the bed forever, so I reluctantly took the bra off my bed and walked it over to my dresser. It felt heavier than I would have expected, probably from the heavy padding in the bra cups. Opening the drawer, I folded it neatly and went to place it beside the rest of the lingerie. For some reason I didn't quite understand I was fascinated with the pile of neatly folded bras nestled in my underwear drawer. I ended up standing there for a few minutes holding the red bra and staring at the pile of lingerie nestled in my dresser. I finally broke out of my trance, placed the bra carefully on top of the pile of my bras and closed the dresser. After plopping down on the bed the next thing I was aware of was Marta standing over me shaking me awake. "Get dressed now," Marta told me as I gained consciousness. Although I was awake I didn't understand what she wanted. I was already dressed from before my nap. Marta quickly clarified the situation for me. "Miss Jordan want you neat, proper," she explained. "Clothes for tonight," she said as she handed me a bag heavy with some kind of clothing. Sitting up I dumped the contents out on the bed. The first thing I focused on was a pair of black pantyhose, still in its packaging. Next my eyes were drawn to the pair of shorts sitting beside the pantyhose. Picking them up I was stuck by how satiny they looked and felt. While not precisely feminine, they certainly didn't strike me as all that masculine either. There was a white shirt/blouse as part of the package as well, and finally a pair of shoes I was having a hard time describing. The overall effect was the same as the shorts. Other than the pantyhose to rest of the clothes weren't exactly woman's clothes, but all them were what I can only describe as 'fussy' or 'prissy' for a man. To be honest I wasn't the least bit interested in wearing the outfit Jordan had come up with. Of course Jordan picked that exact moment to appear in the doorway, directing her first statement at Marta. "Marta, I thought you would have Steve in his new clothes by now!" she exclaimed, somewhat to my annoyance as I felt she should be talking directly to me. "Jordan, I don't like the clothes you picked out, and I certainly don't want to wear woman's pantyhose," I told Jordan before Marta could respond to her. "Steven, please don't interrupt me when I'm speaking with Marta. As to the clothes they are perfectly fine, and I expect you to wear them when helping with my dinner party tonight. The pantyhose aren't specifically made for a woman, they're just regular stockings and will make your legs look much better in your shorts. There are many men who wear something similar in certain situations. As for the rest of the clothes, all of them are very nice and will look better on you than the usual sloppy clothes you wear. However regardless of how you feel about the outfit, I've wasted enough time explaining this to you. Please be kind enough to get changed as there is a lot of work still to be done before my guests arrive," she concluded. "I'm sorry Jordan, but I just don't feel comfortable wearing the clothes. I have no problem wearing my normal clothes and helping out with your party," I replied, very reasonably I thought. "I'm sorry Steven, but this is non-negotiable. You helping around the house is part of our deal, and you being dressed appropriately is a necessary part of that help. If you don't like the deal you can always move out. If on the other hand you want to stay, then I want no more back talk from you and I want you to immediately get dressed as I asked." Jordan told me, leaving no doubts as to her stand on this issue. Not being willing to move out, I found myself stripping down to my panties before opening the package of pantyhose. "Help Steven with his stockings please Marta," Jordan directed before leaving the room. Listening to Jordan's stern words took all the fight out of me. I meekly allowed Marta to sit me on the bed and pantyhose in hand, let her roll the pantyhose up my legs, one leg at a time. She then had me stand up, and after placing my hands on the top of the pantyhose, had me pull them up over my crotch. The feeling of wearing pantyhose was quite odd, unlike anything I had felt before. Marta didn't give me time to think about it however, as she urged me to put on the shorts, shirt and shoes. Once I was fully decked out I felt even more odd. Looking at myself in the mirror and thinking about the way the clothes felt, the best description I could come up with is I felt 'feminine'. Marta broke into my introspection by hustling me downstairs, and once again put me to work. I had only been performing tasks for about an hour before the doorbell rang. Marta suddenly appeared beside me and ordered me to answer the door. "You greet Miss Jordan guests," she told me. I was a little ashamed of the way I was dressed, but after Jordan's earlier lecture I felt like I had little choice. Almost involuntarily I found myself going to the front door and pulling it open. Framed in the doorway was a woman who looked to be the same age as Jordan, and was equally attractive. Digging into my brain I can up with dialogue from old movies that I thought would be appropriate for the current situation. "Good evening Madam, please come in and I will escort you to Jordan," I said in my best butler tone of voice. "That's very nice of you Steven, thank you," she replied. "Have we met before?" I inquired, genuinely puzzled as to when I may have been introduced to this lady. "No, not at all. Jordan mentioned her stepson Steven would be helping her this evening and would be nicely dressed, so I assumed that you were him," she replied. "Incidentally, my name is Julia," she added. I blushed a little at her compliment, but quickly regained my composure and escorted her to the living room where Jordan was waiting. I had barely finished that task before the doorbell rang again. Hurrying back to the front of the house, I opened the door for two more guests my stepmother was obviously expecting. Again they were both around the same age as Jordan and were as attractive as her first guest. If I wouldn't have been dressed as I was and acting as a servant I would have been very happy to mingle with these women. "I'm Bonny, and this is Catherine," the blonde woman told me as she pointed to herself first and then her brunette companion. "He is so pretty," Catherine commented, causing me to both blush and want to sink through the floor. "Yes his legs are darling in those pantyhose," Bonny responded "I wonder if he ever puts on a dress and wears it around the house? What do you say Steven? Do you have a closet full of pretty dresses that you wear when you are alone? Really I have no problem with a young man who wants to express his feminine side, in fact as far as I'm concerned feel free to wear one of your prettiest dresses next time you help out at one of these dinner parties"she commented. I shook my head no as I replied "no ma'am, I really don't own any dresses and wouldn't be able to wear something like that next time I help out" "How sweet. He's too shy to admit he wants to dress as a girl," Bonny commented to her friend. "We'll have to get the truth from Jordon, however it wouldn't surprise me at all if he likes to get dressed all nice and pretty and prance around the house," she commented to Catherine as the two made their way into the house. I was stuck speechless for a moment, but hurrying to catch them I regained my composure and asked the ladies to accompany me to where Jordan and Julia were talking. Once all four women were together Jordan instructed me to bring out the hors d'oeuvres, and get a drink for each of them. They chatted for about an hour, with me running around serving them drinks and finger food, before they seated themselves in preparation for dinner. I was bringing out the soup course when their topic of conversation turned towards me. "He is very sweet Jordan," Bonny commented. ," Does he serve at dinner parties for anyone besides you?" she queried Jordan. "To be honest I hadn't given it any thought. I could always ask him if he is interested, that is if you are serious about this," Jordan replied. I had stepped into the dining room with the soup, but was actually hidden from the table at the moment by a bend in the long room. If I were to take one more step I would be spotted by those at the table, and I really wanted to hear what they were saying about me. I stood perfectly still trying not to think of the weight of the four soups on the tray I was carrying. "I'm perfectly serious," Bonny continued. "Of course he would have to be dressed appropriately," she added. "I think he looks very nice right now," Julia chimed in. "Yes he does look nice, but for my dinner party he would be doing the work a maid does, so I would want him to be properly dressed as a maid," Bonny replied. "You don't mean ...." Catherine started to say. "Yes of course. That is exactly what I mean. He's already half way there from the look of him. For my party I would want him to present fully as a woman. I would expect him to wear a nice dress, a fully padded bra with breast forms, high heels, makeup, the works," Bonny explained to the others "To wear the correct earrings he would have to have his ears pierced, and something would have to be done about his eyebrows and hairstyle. I have a hairdresser who could quickly fix those eyebrows and give him a proper feminine hairstyle in a hurry," she continued musing to the group. "Believe me, by the time I was done with him he would look like a very pretty girl, even if he was still wearing his boy clothes," she finished. I decided I had heard enough, and walked towards the dining table carrying the tray of soup. "Ladies, your soup is served," I announced as I placed a bowl in front of each of the women. "We were just discussing you," Bonny told me, something I well knew. "I was so impressed with your work tonight that I was wondering if you might be interested in some doing similar work for me from time to time?" "I'm afraid between work, school and the help I give around here, I'm just too busy to take on anything else," I replied, hoping that would be the end of the idea. I certainly did not want to dress as a Bonny's maid, especially not the way she had been describing it. It was bad enough that I had to dress as I was without making my clothes three times as feminine. "We will have to see," Jordan said, jumping into a conversation I thought was finished. "I have been wondering if Steven shouldn't quit his job, as more help is needed around here than he can give at the moment," she added for my benefit. "What would I do for money?" I asked, worried about what Jordan was suggesting. "I would pay you honey. I could easily match the amount of money they give you in that so called job of yours," she responded. "In fact the more I think about it the more I like the idea. Steven, I want you to call them up tomorrow and tell them you are quitting. You work about twenty hours a week for that place, which I can easily give you around this house. And Bonny, seeing as Steven will have more time on his hands starting tomorrow, the next time you are going to have one of your dinner parties we can talk about you using his services. I can decide right then whether I can do without him for the day or not." Jordan finished. "And how would he be dressed if he works at one of my parties?" Bonny inquired. Of course from my eavesdropping I knew exactly what she had in mind for me even if Bonny thought she was being coy about it in front of me. "That would be completely up to you dear. After all, it would be your party and he would be one of the hired help for that party. Traditionally the hostess dictates exactly how the help is dressed," Jordan replied, effectively telling Bonny that she could dress me head to toe as a woman if I worked at her party. I could feel shivers going down my spine as I imagined what working one of Bonny's parties would be like dressed like that and serving a large number of guests. I have to admit I was stunned at the turn this had taken in such a small amount of time. Further I certainly didn't like the look Bonny was giving me all of a sudden. I realized that not only was I supposed to spend three times as much time working around the house as I had been previously, but Jordan was actually entertaining the idea of lending me this friend of hers who would then put me in a dress. I passed the rest of the dinner party in a haze, desperately trying to figure out a way of stopping the insanity my life was becoming. Between serving the different courses of the meal I even spent some time figuring out whether I could afford to move out of here if I kept my job. I kept coming back to the fact that I wasn't earning enough money to become independent, and the only way to change that would be to give up school. Giving up school however, would likely also mean giving up Amy. Although we weren't really dating as yet, things were going really well and I was looking forward to things going even better in the future. The bottom line was I wasn't willing to give that potential future up. That meant my only real choice was living with my stepmother and hoping I could exert some control over her decisions concerning me. Not an ideal situation, as far as I was concerned, but it was the best I had at the moment. The evening went by in its own time, and I eventually found myself escorting the ladies to the front door and bidding them a good evening. Heading up to my room, I was tired and more than ready to get some sleep. This day had completely changed from one where I had planned on relaxing all day to one that had me working all day, and I was happy to see it end. Arriving in my room, I started getting ready for bed. As I was stripping off my shirt and shorts, I caught a glimpse of myself in the mirror. Turning towards my own image, I was standing there wearing just black pantyhose and red panties. For a second I was intrigued, as my first glance in the mirror had shown me this enticing femininity. Then my brain caught up with my vision and realized I was looking at myself. At that point my excitement turned to disgust, as it sank in that I had been attracted to the 'woman' in the mirror. That combined with the plans Bonny had been contemplating were too much for me to handle. Quickly stripping off the pantyhose and panties, I practically dove into bed and huddled under the covers, hoping somehow to hide from my own thoughts and reactions. It took me hours to finally get to sleep. I had originally thought that the panty punishment decreed by Marta had been a spur of the moment kind of thing, but now I was wondering if it could be part of some plot created by Jordan. The pantyhose and other parts of last nights outfit, the bras Marta had purchased and put in my dresser drawer, and Jordan's possible support of Bonny's maid proposal was making me wonder exactly what Jordan had in mind for me. When I eventually did fall asleep I ended up having a restless night haunted by bad dreams. Things didn't seem to work out any better for me the next day. While I was now finished with my punishment and could go back to wearing my normal underwear, I felt groggy and out of sorts as a result of how poorly I had slept. To make things worse Jordan came looking for me shortly after I was up and around. "Marta tells me you are interested in having your own dress and high heels so you can doll yourself up when the mood strikes you. I'd be more than happy to buy you all the clothes you'll need to express your feminine side. We could start with a few different dresses and matching high heels for each of the dresses, and from there see how many different outfits you will need for day to day use. I think four or five dresses will be good start for you, letting you chose somewhat based on your mood that day. Once you start wearing dresses on a daily basis you will need more than that of course, however we can easily deal with that when the time comes," Jordan told me as soon as she spotted me that Sunday morning. "No, Marta is mistaken," I answered, hoping to avert a potential problem. "What do you mean she is mistaken? Either you told her you wanted a dress and high heels for yourself or you didn't. Which is it?" Jordan shot back, not dropping the matter as I had hoped. As this conversation wasn't going very well I decided the only way out was to lie about it. In hindsight I likely should have confessed to Jordan that I said that but was actually joking. Instead I did something I was sure to regret, which was lie to Jordan. Unfortunately my next words were "No I never said anything like that and I never would. Marta is lying about me wanting a dress and high heels," I declared firmly. "OK we'll drop this until I can get to the bottom of it," Jordan replied. Not exactly a ringing endorsement, but I was happy to leave the whole issue alone. "One other thing, Steven," she told my as I was getting ready to head to the kitchen for some breakfast. "I gave some thought to Bonny's proposal and have decided to leave it up to you whether you want to work for her or not. There is enough work in this house to keep you busy, plus there are some things about working for Bonny that you might not like," she told me without elaborating, thinking I wouldn't really understand what she was referring to. Fortunately as a result of my earlier eavesdropping I did know about the maid role Bonny had in mind for me and was therefore relieved I wouldn't have to work for her. "In that case if she asks again please decline on my behalf," I told Jordan, trying to handle this as gracefully as possible. "I will do that for you Steven," Jordan replied as she was leaving, making it sound like she was doing me a big favor by talking to Bonny when it was Jordan that had gotten me into the situation in the first place. After breakfast I called my manager at work and resigned. After that I started in on some of the work that needed doing around the house. The new agreement was thirty hours a week, which I was going to try and break down into ten hours each on Saturday and Sunday, and the remaining ten hours spread evenly between Monday and Friday, or two hours per day. That would still leave me time to attend class, study and hopefully see Amy on occasion. The work wasn't particularly hard, mostly consisting of some cleaning, some gardening, some pool maintenance and the like. Sunday passed uneventfully, as did the following week. I attended my classes, did my homework, and performed my chores at home. As the week drew to a close I was pleasantly surprised when I ran into Amy after Friday's class. "Hi Steve," she called out across campus. Turning I quickly spotted her and shouted back "Amy," while hurrying towards her. "We had talked about a date this weekend, how about tonight," she asked once we were within easy talking distance of one another. "That would be wonderful," I replied, thinking my luck was definitely taking a turn for the better. "Great, why don't we meet at the little coffee place on Main Street at 8 o'clock, and we'll go from there. I have the perfect place for us to go," she told me, taking the initiative once again. "Sounds good, I'll see you at eight," I replied, and headed for the bus. Although the week had gone smoothly I was still glad to finally make it home, and I wanted nothing better than to relax beside the pool before my date with Amy. It didn't take me long to change, and within about ten minutes of arriving home I was dropping myself into one of the poolside loungers. Jordan was already there, so in the interests of being polite I gave her a quick "hello, how was your day". She gave me a brief, non- specific answer and having exchanged pleasantries she went back to painting her toenails a bright red. Being really tired is the only way I can explain what happened next. I must have fallen asleep literally right after I finished exchanging words with Jordan. It felt like hours later when I woke up, and might well have been. Certainly it was still light out when I lay down, and it was now so dark someone had turned the poolside lights on. I was still trying to get my bearings when I noticed something besides the change in lighting. All of my toenails had bright red nail polish on them. I immediately looked around for Jordan, but she was no longer on the lounger she had occupied earlier. The only conclusion I could draw was she had painted my toenails after finishing with her own, as it appeared to be the exact color she had been using earlier. I headed into the house in search of her, looking for some kind of explanation as to why she had done this. It was lucky it took me a few minutes to find her, giving me a chance to calm down. If not for the delay it's very possible I would have started yelling at her, and been out on the street shortly thereafter. I finally tracked her down in the kitchen, almost the last place I would usually look as that was Marta's domain. Jordan and Marta were both there, working away at some kind of food preparation. Much to my embarrassment Marta was the first one to turn around, and she seemed to immediately notice my painted toenails if the direction of her gaze was any indication. After giving me something that seemed to be a cross between a smile and a smirk, she turned back to her work. As soon as Jordan turned towards me I plunged right in. "Jordan, was it you who painted my toenails?" I asked. "You didn't paint them yourself?" Jordan replied, in what I can only describe in an innocent sounding voice. "After all, you have been wearing panties lately. I thought you might have decided to become a little more feminine," she added, unnecessarily as far as I was concerned. "No I didn't do this to myself," I replied, struggling to keep my temper. "That's why I asked if you were responsible". "Yes, now that you mention it I do remember painting your toenails a few hours ago," she told me with a smile. "I thought it would look cute on you, and since you didn't say anything while I was doing it I thought wearing nail polish met with your approval," she explained, never taking her eyes off of mine. "I didn't say anything because I was asleep," I informed her in my best authoritative tone. "How was I to know that," she countered. "Besides, no harm done. We can take the polish off your toenails once Marta picks up some nail polish remover tomorrow. That is unless you want to keep it on for a few days. Maybe spend a little time deciding if you like the look of wearing nail polish or not," Jordan suggested as she closely watched my reaction to her suggestion. To say I was stunned is an understatement. I had assumed the nail polish could be removed right away, and had been having this conversation with Jordan in an attempt to make sure this never happened again. Now it looked like I would be wearing nail polish until at least tomorrow. Still I tried to maintain my composure, asking Jordan "please never do that again". Her reply stunned me as she informed me "I might do it again or might not. This is my house and it really depends on what I feel like doing at the time. Next time it could be your fingernails if that pleases me. By the way stop being such a spoilsport. It isn't an attractive quality in you" It was at this moment that I looked at the time and realized I didn't have any left before my date. In fact it was so late that I needed to get changed and then immediately leave to meet Amy. I realized I wouldn't have time to do anything about the nail polish I was wearing on my toenails. No use crying about it, I would just have to make sure Amy didn't see my toenails tonight if I didn't want to have a heck of job explaining why they were like that. Dashing upstairs, I donned some of my best casual clothes and headed out of the house. I barely made our eight o'clock meeting time, but I did make it. Amy was already there, dressed in a flattering sweater and skirt set. She was happy with how punctual I had been, and we started out in good spirits. "There is this wonderful little Jazz club just down the block. I know you are going to love it," she told me as we walked holding hands. I wasn't all that worried about whether we went to the club or not, but was just happy to spend some time with her. After a few hours at the first club we moved on to a second club, and by midnight I was walking with Amy back to her apartment. She lived just off of campus, and I wanted to make sure she got home safely. "I had a great time," I told her as we arrived at her front door. "Me too. In fact it doesn't have to end," Amy replied, motioning towards the apartment with her head. I was completely caught up in the moment, with the minor detail of my painted toenails temporarily forgotten. Amy turned the key and we went inside. I have to say, her apartment didn't look anything like I had imagined it. I thought of her as something of a modern woman, very assertive and sure of herself. The apartment struck me as very frilly and feminine. While assertive and frilly weren't mutually exclusive, they weren't two things I typically connected together as a matter of course. "Why don't you sit down and I'll get us some wine," Amy suggested. Sitting down on her couch, I waited until she reappeared with a couple of full wine glasses. Turning down the lights, she placed the glasses on the nearby coffee table and sat down beside me. We started talking about our lives again, our hopes and aspirations, with the original wine glasses being emptied in favor of second and third glasses for each of us. We had both started to get a little tipsy when, without warning, Amy reached over and started to stroke my cheek. She then positioned her body even closer to me, and her lips moved towards mine. Before I could react she was kissing me on the lips, followed by her tongue thrusting into my mouth as her kiss quickly turned into a French kiss. Meanwhile her hands started to unbutton my shirt, and having accomplished that job they then darted inside my shirt and started rubbing my chest. I found myself placing kisses along her neck, while my hands started to remove her sweater. Once I had removed her sweater her pink bra was revealed, which turned me on even more. My hands moved to her breasts, and started massaging her nipples through the material of her bra cups. Amy seemed to be enjoying that so much I then reached inside her bra to play with her nipples directly. At this point she started to get really aroused, her entire body squirming and thrashing around. I didn't feel as if we were ready to have sex as yet, but I had soon removed her bra so I could take her nipples in my mouth and suck on each in turn. With my mouth was busy up top my hands moved to her vagina to start their own task. While all this was happening Amy was in the process of stripping off my clothes. Once I was naked her hands roamed my body before coming to rest on my penis. Soon I was squirming as much as she was, and found myself ejaculating across the bed. She was equally horny, and soon my manipulation of her vagina and nipples caused her to orgasm multiple times. While we hadn't actually had intercourse it was still an intense experience for both of us. We both lay panting on the bed for minutes afterward, before moving to the bathroom to get cleaned up. Once Amy turned on the bathroom light I suddenly realized the nail polish I was wearing on my toes was clearly visible. It was quite a dance I went through to make sure we both weren't in the lighted bathroom at the same time. She would be in the bathroom cleaned herself up, while I waited in the other room in the dim light. Then I had to time it carefully so that I didn't enter the bathroom until she completely out of it, and if it looked like she was suddenly coming back into the bathroom I had to make exiting the bathroom look completely natural. After ten minutes of that kind of to and fro I was a nervous wreck, but we were finally both cleaned up and I gratefully crawled into her bed. I was asleep within seconds of my head hitting the pillow. It being Saturday I didn't wake up until mid morning. Amy looked so sweet and peaceful sleeping beside me, I was tempted to wake her up