That was this summer. I had very long relationship and last year i got ridden of it. So I sex occasionally wit various girls till then. One night this September I was very very tired of everything. Job went finally better and some private investing also, but I had being working for 14 hours a day at time. It was About 1 am in the morning and was just went of from long shower and about to lay down on my bad.The voice from the other side of cell phone was very pleasant, some kind of baby talking voice. Voice said" Annnn' what what do want from me now?...LOL.. i said "who is this?&... Continue»
I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly f***ed blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own stories and beginnings, and this one is mine.
I am a very intelligent, personable person, eager to please but not overly so, and I get along with everyone that I meet. I stand at 5' 8" tall and I weigh 155 lbs, almost shoulder length brown hair but not feminine at first, big bright blue eyes, long eyelashes and absolutely no body hair except around my cock.
Growing up I never had any problem making friends and being sociable with both men and women. I have always been attracted to women, but around age 10, one of my friends’ older s****r had sex with her boyfriend in their basement and had left a pair of her silk bikini panties behind a sofa cushion. I had gone over my friend’s house for a sl**pover and found them during the middle of the night. They were black silk, string bikini panties with bright pink hearts all over them and a delicate lace trim. They were from Victoria ’s Secret. I had a very big crush on Denise (my friend’s s****r) and when I found those panties, I just knew that I had stumbled onto something that would be a landmark for the rest of my life. I of course kept them hidden until I got home, and would take them out and just stare at them and imagine her wearing them. After a few days of this, I tried masturbating for the first time and was hooked. For the next few years I would find any chance that I could get to sneak into her room and go through her top drawer and sometimes take a pair of panties or a bra. I managed to get a bikini of hers as well. But that's as far as it went.
As I got older, I had a very embarrassing problem that just got worse as time went by. I got bigger and began to mature but my penis stayed small. I mean really small, when I am hard as a rock I am about 4 inches long. Unbeknownst to everybody, I was extremely self conscious about anything relating to real relationships or sex with a woman. I kept it very well hidden because I’m so outgoing and had tons of friends. I always lied when my male friends and I would talk about experiences with sex; but, never enough that is seemed suspicious like I was covering something up or hiding something. And I do love women, so I would make just as many comments with my friends about hot girls in school, and what I wanted to do to them, etc. But I was terrified of actually doing anything with any of them because of what they would say about the size of my little cock. This behavior continued into my twenties with me still being a virgin, and developing quite a fetish for lingerie and sexy female attire.
Over time I began having fantasies of shemales, probably because in my mind they weren't nearly as much as a threat as a real girl when it came to being devastatingly humiliating if my secret was discovered. No matter who was the first to see my tiny cock, I knew that there would definitely be a lot of humiliation, and so even in my fantasies I was becoming submissive. I began to think about the fact that I would only be able to satisfy anyone orally, and so my shemale fantasies slowly but surely involved to include some oral on my part, but it was strongly tied to lingerie and being f***ed into it. All of my sexual release was from internet stories occasionally, and phone sex lines.
I moved to Florida in my early twenties. I had moved down there with a couple of friends from home. We couldn't believe the amount of gorgeous girls that were everywhere down there. It was bikini season all year long and most girls made sure that they looked amazing in their skimpy swimwear. And the clothes of most girls in day to day life was much sexier and more revealing than up north as well. For someone with a fetish for sexy outfits like I have, it was an amazing place. And this just added to my secret problem, and made me even more self conscious. What added to that was the fact that because of all the time that girls spent staying in great shape, and maintaining perfect year round tans, for the most part they aren't the most well read or educated women to converse with. And this was the one area that I had something to offer in any hope of a relationship. My wit, sense of humor and ability to carry an intelligent conversation had no outlet with girls my own age.
I got a good job at an office and I was dealing with computers and account management for clients all over the country and was doing well for myself financially. My friends that had moved down with me ended up moving back due to lack of decent employment after about a year and a half, but I had made some friends and was moving up at work, so I stayed. Then the job market really crashed and the company that I worked for went belly up after the owner embezzled millions of dollars and fled the country. I was out of work and miserable for about five months. I was applying everywhere, and could not find a job that paid what I needed and had opportunity for advancement. I was quickly running out of money just to keep a roof over my head and food on my table, and I knew that what I had left wouldn't last much longer. Then I went for an interview that changed my life severely.
The ad was for a small company with amazing potential that was looking for one person to help with the overload of financial and computer analysis and maintenance that would free up the owner for more customer relations and sales. This was right up my alley. To say that I was surprised when I met the owner would be a drastic understatement. She was absolutely gorgeous and in her early thirties. She introduced herself as Kim and was a complete knockout. She stood at 5ft 8in tall with long wavy brown hair that fell past her shoulders and smoky grey eyes that hinted at something mischievous, but in a playful way it seemed. She was impeccably dressed in a tight, black, form fitting leather skirt that ended just past her knees as well as a obviously expensive ivory silk blouse that wasn’t inappropriate for a business woman but revealed plenty of what appeared to be a full C cup chest to get the imagination going crazy. She had on 3 in black open toed sandals and black stockings that did nothing to mask her perfect legs. Her makeup was light; but, accented her features in a sultry manner that drew your eyes to her full, light cherry colored lips covered with a gloss that gave the appearance of being wet, which is a look that has always driven me into a frenzy. I became a blubbering idiot immediately and was doing everything in my power to keep my jaw from hanging open as well as try to interview for a much needed job.
I was apparently able to maintain myself well enough so that the interview continued because she asked me if we could continue this over lunch. Of course I didn’t object, a gorgeous woman who could give me a job was asking me out to lunch. This was a new experience for me, regardless that it was because of an interview. Inside I felt thrilled and just grateful to be in her presence and very much intimidated. She had me completely under her thumb and I didn’t even realize it. The lunch went well and I really did have the skills needed that she required, and I ended up getting the job. I was on cloud nine.
The first few months were a typical working environment with some subtle exceptions. I didn’t see anything unusual and if I noticed anything, I just figured that you deal with different types of working relationships in an office with two people. Plus we were very busy, which kept my mind off the small peculiarities. Kim was definitely the boss, and her commands were to be followed when it came to business matters. I just naturally accepted the submissive role between us with no question. She had certain rules for the office that began appearing during that time. She said that she was constantly on a diet to maintain her figure and she would not tolerate anything that she couldn’t eat to be in the office, so I started eating the same diet that she did, mostly salads with small amounts of protein. Also she said that to keep up the pace that we were going with the hours that we worked we should be in the best shape possible, so she got me a membership to her gym and it just made sense for us to go together every morning. I thought this was great because I got to see her in usually a spandex leotard or shorts and sports bra every morning while we were on the treadmill together. Her toned and tantalizing body kept me in a dazed stupor constantly. Kim said that endurance was the most important thing to health, so only cardio was really necessary for our workout. She would joke about the muscle heads with the weights and how she didn’t find that look attractive at all. I agreed with her obviously, because I had lost about 15 pounds in the first few months alone due to the diet and workout regiment and had slimmed down to a thin frame. Working in a desk all day left the only little bit of excess weight in the thighs, hips and butt area. She had set me on a course to slowly feminize my body and I was clueless.
For the most part we got along great, and really did share the same likes and dislikes when it came to entertainment and style. When it came to style, it was more like I saw the impeccable taste and style that she had, and wanted to attain the same level as she did in regards to clothing, home décor, etc. She knew exactly what she was doing and occasionally she would make random concerned suggestions about something in my life. I thought it was very sincere when she said that I should let my hair grow even longer (at the time it was just touching my shoulder.) I was hesitant because I had never let it grow further so that I would not draw any more attention to my slight build and fairly feminine features; however, I knew she had an amazingly fantastic sense of style and I also had an hypnotic infatuation with this goddess. So I agreed and let it grow. Every now and then she would give me a well timed and placed compliment about my changing figure or longer hair which would make me proud but even more intimidated.
Since I was her only employee, I also took on many assistant duties, such as picking up and dropping off dry cleaning if necessary (and I loved the chance to see her sexy dresses and outfits), making appointments for her at salons, and spas. Things that I had not been familiar with previously because they are more female oriented things; but, I was becoming quite used to them and finding them less intimidating and more normal as time went on. Kim also had a look that would come out whenever she was displeased or upset about something. The look clearly meant that I or whoever else it happened to be directed at was wrong and there was no room for discussion. If I had made an error or failed her in any way, sometimes she wouldn’t say anything but just give me her look and I would feel ashamed and a little worried. I never even considered arguing, I just profusely apologized and vowed to do my best to please her with my work.
I had been doing well for the most part for quite some time until I came home to my apartment complex from work to find that there had been a fire in my building and two thirds of my apartment was completely ruined. I was told that I had to gather whatever I wanted to keep and leave that day, because the building couldn’t be occupied at all. The only things that I could salvage were half of my clothes which also happened to include my small collection of lingerie that I had with me to occasionally jerk off into. I phoned Kim to let her know what the situation was. She didn't hesitate and said to me as if i were a worthless idiot "you obviously have no place else to go, so be over here within the half hour, i'm busy and you need to hurry." This wasn't a negotiation and I didn't even consider disobeying her.
I arrived completely disheveled, feeling helpless, weak and feeling pretty low about my scenario. Kim on the other hand was the exact opposite, standing tall in her 4 in heels and a tight, light purple mini skirt with matching halter top. She said that I had already wasted her day and that if I'll be living with her then there are groundrules that need to be laid out. She showed me to her spare room that had once belonged to her rommate a few years ago. It was extremely feminine, light pink walls, a four poster canopy bed with sheer light pink canopy. There was a dresser and make up table that she kept alot of her excess makeup and clothing in. She told me that later on i could get a few boxes to put her clothes into in order to move what I had in.
I left my only remaining possessions there and continued the tour of her home. We would be sharing a bathroom, it was huge and richly decorated, but there was only a large jacuzzi tub and no shower. I asked her and she said that she only took baths, and from now on I would have to as well. Who was I to complain?
Then she showed me the kitchen, dining room and living room, and said that as part of my rent she wanted me to do the cooking and help with most of the cleaning. I still had no choice and so i just meekly agreed. Kim said "Good Boy" in a casual tone, but that struck a nerve with my submissive side, and I kept my mouth shut but started thinking about fantasies that involed Kim being dominant. The she dropped the biggest bomb on me when she said that part of the household chores would be our laundry. Not the drycleaning obviously but mainly her delicates. I pretended that I wasn't sure as I'd never done that before. She just smiled and said pretty soon I would be very familiar with lace, silk and satin. My reaction to her saying that, though not blatantly joyous, was enough to give my interest in lingerie away. She didn't say anything, she just stared me dead in the eyes until I had to look down.
She took me upstairs and said she'd help me unpack since I didn't have too much. I was still in shock and couldn't think of anything plausible why I didn't want her to go through my things. In my new room she opened a bag that didn't have any female clothes in it and started unpacking, the only other bag was the one with my entire stash of sexy lingerie. I just stood there and couldn't open it. After a minute she stood upright and told me help and unpack my bag. I didn't say anything yet again. She gave me her fierce stare and said she wasn't going to do my work and that I had better start to unpack. I just said I couldn't. She came over and slapped me across the face really hard. I made no defensive move. She said "when I tell you to do something you had better do it, or else, do you understand?"
I said very softly yes. "Are you hiding something in that bag?" she demanded to know. I couldn't meet her eyes or answer her, so she just took the bag and unzipped it. She immediately saw all the panties, bras and bikins that I had managed to acquire throughout the years. I was so ashamed. She just started laughing cruelly. I stammered that I would leave. "You're not going anywhere darling! Sit down on the bed right now."
Of course I instantly sat down. "We are going to have a long talk honey" Kim stated.
"It's not what you think"
"It's exactly what I think. I think that you like to dress up like a little slut in all these sexy, soft panties, bras. You even have a bikini. Hand that to me honey"
I handed her the bikini that was on top. It was a white string bikini with a triangle top and the bottoms tied on the side.
I said that i don't dress up in this stuff, that i just like the way it looks on girls and that feeling of the materials.
She told me to look at her and said "Well you are going to start wearing these, aren't you?"
I made no reply.
"Yes, but I don't want to."
"What you want means nothing to me now, but I bet that you secretly do want to wear this stuff."
Kim told me to go downstairs and get a bottle of white wine and somefruit, that we were going to up here for a while. I followed her commands and went downstairs to the kitchen. i was in a panic about what just happened and how I could fix it. I came up with nothing. I was broke, with no other place to go. Plus she knew one of my humilating secrets and I was incredibly attracted to her.
I brought the things upstairs and she showed me the hall closet where my remaining male clothes were. "I am going to talk and you are going to listen, understand?"
"Yes I do" I whispered.
"These are where you only male clothes will go. This new situation has changed everything. Go back and sit down on the bed."
I did so and watched her saunter back into the room. She sat in the chair for the makeup table and faced me. She noticed that I kept looking down and said that I needed to listen to her exactly and that wasn't to ask any questions until she said so.
"I have noticed over the past few months how well you take orders at work, and never gave it a second thought. I just assumed that you weren't the alpha male type and I've enjoyed having an employee that would follow my orders. As you know I'm a dominant woman and have slowly began to manipulate you to be more feminine, especially with your longer hair and your slimmed down figure. I have always wanted to feminize a man and have really had fun with you up until now. I never thought it would go any further.
Then you called today and said that you needed a place to live and I couldn't believe that I might actually have an opportunity here. Your fate was sealed when I told you that you would wash my lingerie, and I could see the excitement no matter how you tried to hide it. But I didn't for a second believe that I would be so lucky as to discover your stash like I did. This moves my plan along way ahead of schedule. Consider your life as you know it over."
I was shaking visibly when I stammered "What do you mean?"
First off, you will continue to work for me; however, you are now my official secretary. At the office you can continue to wear male clothing for now, but that will change. When we are alone you will call me Mistress, and if anyone else is around you will refer to me as Miss Kim. Is this understood?"
"Yes what? Don't start off by misbehaving girl."
"Yes Mistress Kim"
"Good girl. I have a very big lingerie fetish, and clothing fetish. Plus I've wanted to feminize a man. I don't have the time to find a real man as my boyfriend and you're going to satisfy a lot of my needs. At home you will never wear male clothes. The minute you get home you will change into something appropriate. All of these drawers in the dresser are filled with sexy, slutty, frilly little underthings and some even naughtier ones with leather, vinyl and rubber.
to be cont'd...