I began my day as usual, got up, showered and shaved my body; Kay liked me to be free of body hair. I really never had a lot in the first place, so shaving was easy. I applied lavender lotion to my breast, which started forming, Kay told me that lavender was her favorite smell, and it help the breast form, plus the hormones she has been feeding me helped quite a bit. My hips have rounded to what she called perfect for her new sexy personnel assistance, Jamie was happy for me on the promotion. Today I was looking forward to servicing Kay and her boyfriend. I went into my room and I dressed in a pair of black nylon’s matching garter belt, high cut black satin panties, black 3 inch heels and a black camisole.
I sat down at my pink vanity, that her boyfriend had gotten me, and started with my make-up, blue eye liner, David liked it on me, a soft skin tone foundation, a light rose colored powder on my checks, ruby red lip stick. Just something simple this morning I thought after applying my eyelash enhancer. I walked into Kay’s room, they were both asleep. The other girls living there took turns we loved it!
I walked over to the bed, and pulled the covers, back, David stirred, opening his eye’s he smiled, and said “ah I see you’re ready for breakfast Karen”. I smiled back him; I knew I wasn’t to speak. I got on my knees and took his semi ridged cock in my mouth. The feeling was intense, his cock began to grow. David had the perfect cock, 7 inches, about 2 inches round, the perfect mouth full, when he would cum, he would fill my mouth with so much that it was hard to swallow it all, but Kay had made sure that I had gotten very good at it, practice, practice she would say, and I did practice quite a bit, Our clients loved it!
David’s cock tasted so good especially after he had fucked Kay, her taste and his mixed drove me crazy. I knew that after I had finished draining David’s ball’s, that I would have eat Kay until she came, and then make them breakfast.
I felt David’s hand grab hold of my head as I swirled my tongue around the head of his cock, lick up the pre-cum that was seeping out, umm was my only thought. He pushed my head down, I engulfed his cock, and began to bob up and down on his hard shaft, gently running my long finger nails, around his ball’s he loved it, he would be Cumming soon.
He let out a moan, and stiffened up, I felt the first shot of his cum hit the back of my throat, I keep bobbing up and down on his cock, sucking every bit of cum juice he had for me, I swallowed every bit of it! I pulled back after his cock went limp. He smiled, and said “time for a shower Karen, service Kay while I’m gone, and then make us some bacon, eggs, toast, and coffee”, he got up. I stayed on my knees and lowered my head.
“Karen crawl over here”, Kay commanded. I did as she told, she spread her legs, and smiled, “Taste this sweet pussy, David left you desert”. I went to her pussy, and began to lick her outer lips. Working my tongue slowly into her hot pussy, “Umm you turned out so good Karen”, she moaned. I loved it when she talks to me like that. I was there to service her today. Kay had hit a spot in me when she gave me her panties to wear, I’m so glad that I went to work for her and David, and them showing me what I really wanted to be.
I worked my tongue deep in her pussy; I could taste her juices as well as David’s sweet cum. I began to dart my tongue in and out Kay, trying my best to get all of it. “Stop Karen”, Kay commanded. “Lay on your back, in David’s place”. I did as she said. Kay squatted over my face, and grabbed my head, saying “Now that’s a good girl, clean me up”. She pulled my head to her waiting pussy, and I began to suck on her sweet pussy, gobs of David’s cum came rolling out in to my waiting mouth. “Ummm so very good Karen, I’m cummming”, moaned Kay. I felt her pussy quiver and spasm as I pushed my tongue deep into her. Kay’s body went limp. Her pussy covered my mouth and nose she sat there looked down at me, smiling and said “Karen dear you will go clean up, change into something sexy we are having company today.” Be sure to have breakfast ready dear girl!” I left the bedroom and went back to my room to change. I chose a light blue mini skit, a matching top, making sure that my panties and matched what I was wearing. I slipped on a tan pair of panty hose, and white pumps. I fixed my make-up and hair, then went off to kitchen, as I walked by Kay and David’s room I heard her moaning, “Fuck me harder, fuck me baby”.
It all started when I went to work with a new advertising agency in town. I had been out of work for about two months, and was getting bored at doing nothing. I could have stayed out of work for the next five years; I had saved every penny I could, for the dry times. I had work as a graphic artist for my last company, but like I said I got bored with it, everyone in the office seemed like sticks in the mud. So I left, figure I would free lance, did a little side work. During the down time I would find myself on line watching porn, like most males my age 21. I had dated a on and off, but the women never seemed to want to go any further than a couple of dates. I’m your average looking guy, a little on the short side, 5’ 6” 120 pounds, nothing special. One day as I was browsing through a couple of porn site’s, I come across a transvestite web site, I figured why not. So I opened it. I was surprised; a lot of the men looked like real girls, so much so that you wouldn’t know what type of web site it was if you just happen up on it by mistake, some of them were beautiful looking. I pushed away from computer and went to get some coffee. Came back and decided to investigate this further. I googled transvestite; I found tons of material on the subject, from how to do make-up, to hypnotic videos, even dieting. I booked marked the site’s, and signed off.
I finished off a piece of work that I had been doing, and e-mailed off to company that wanted it. I went back to my book marks. I opened the one about transvestite clothing, they had a few videos, I found them interesting, and they had clothing for all occasions. Off to the side on the main was another of site marked “vids”, my curiosity got me and I went to it. I clicked on video, and it showed a guy getting a blow job, the camera panned out and it was a guy dressed up, you could his cock hanging below his miniskirt. I got a hard on watching this, and began to jackoff I looked below the video, and there were others, I choose one titled:” you like panties”, what I didn’t realize was that it was hypnotic video, that lasted fifteen minutes, I watched as different types of panties were flashed across the screen, and the back audio was supposed to suggest that you like to wear panties. I continued to jack off watching this video, and came a few seconds before it ended. I cleaned up myself, but found it amazing that the two videos had turned me on! I went back to my E-mail, the company had liked what I had submitted, and was going to deposit 2500 in my account, but they first wanted a face to face interview with me, they gave me the time, and place. It was in town, so I knew it wouldn’t be a problem. I responded yes.
That night I tried to sleep, the video keep flashing in my mind. I finally fell asleep around midnight. I got up showered, shaved, and dressed. I made the interview on time. I introduced myself to Mary the receptionist, and told her that I had an interview with Mr. Gladden. She called him, hung the phone, and pointed to the doors. I walked in there was another woman in there with him. I walked over to her, and introduced myself, “Kavin Jones”, I extended my hand to her, “Kay Stevens”, nice to meet you ma’am. I turned and looked at the man, He stood up, and he appeared to be a little 6 foot, large frame. He smiled “David Gladden, please sit Kavin, Ms. Stevens is part owner so I ask her to be here”. I took a set in front of the desk. He began to tell all about the company and how they were looking for young talent, and the work I had sent them, was just the type they wanted.
“Kavin, I need someone with your fresh ideas”, Ms. Stevens said, and both David and are willing to offer you an attractive sum to work here. I waited a moment, “How much ma’am?” I ask her. She smiled at me, then said, “how about 32k with commission of course, that’s just the first year, from what we seen of your talent, who knows after that”. I didn’t know what to say, I knew that I could have gotten more out of them, but what the hell, I could quit anytime I wanted to. So I accepted their offer.
“Kavin could you wait outside for a moment, I need to confer with Mr. Evans”, Ms. Stevens said. “Sure” I replied. I walked into the outer office, and waited. “Hi, so you’re going to take the job”, Mary asks me. “I think so ma’am” “Don’t call me ma’am Mary will do, I think you’re going to like it here, all the girls have fun”. I frowned a bit, “All the girls”, I ask. “Yep, the only other male here is David and he so sweet to all of us, as is Kay also”. Before I could say anything Kay had come out David’s office and my tour began. I was shown where I would work a cubical fair size one. It had the work table, computer, and the whole nine yards. “I take it that Mary told that the only other male is David”, Kay asks. “Yes ma’am she did”, I replied. “Now Kavin we are all informal here, I insist you call me Kay”, She said
“Girls, come here I want you all to meet Kavin the new guy”, Kay said aloud, four other girls came out of cubicle’s, and surrounded me. “This is Lindsey, Jamie, Joan, and Missy”, Lindsey was a blonde, nice figure, Jamie was a redhead, Joan dishwater blonde, and Missy auburn hair, but what I really noticed about them, is that there clothing, make-up, everything about them was impeccable, they all each greeted me, Jamie told me that I would love it here, as did the other three. “Okay girls, there will be time to chatter later,” Kay said. The girls went back to respective cubicles. “They’ll chatter your ear off if you let them”, Kay said with a slight laugh.
I made back home, around four p.m. grabbed a bite to eat, and sat down at the computer. I turned it on, but then I realized here I was surrounded by all these beautiful women, and all’s I could really think about was what type of panties they had on. I shook my head on that one. I clicked back on the web site that I was on earlier. I watched the same video over, trying to figure it out, that night the same thing again, panties on the brain.
Well after about 4 months, and a dozen other video’s I was getting rather confused, about a lot of things, it was starting to affect my work, that’s when Kay approached me, “Kavin is everything okay, you seem to be out of sorts a bit”, she said. I don’t what it is about Kay, but she has a way to bring whatever is bothering you out, and not make you feel like bad whatever it is, I seen her do it with the other girls’, so I just broke down and told it to her all. Kay was quite for a moment, then said, “Let’s go I want you to show me these videos”, “what about work Kay?” I replied. “Look Kavin I’m the boss, what I say goes, so let’s go now!” I didn’t respond just got up and walked to the door, Kay drove me to my apartment.
“Nice place you have Kavin”, Kay said, “Thanks Kay” I replied. “Now Kavin show me all this web site”, without a word I took her to my spare room, turned the computer on, and brought up the web site, and started the videos for her, after about an hour. Kay pushed back from my desk, looked up at me smiled and said “Is this stuff bothering you?” I hung my head a bit and mumbled “yes”. Kay let a laugh, and then asks me “have you ever worn women’s panties before Kavin?” “No Kay I haven’t, but the thought of them is driving me crazy, I mean I don’t think about having sex with the girls in the office, I think about wearing their panties, I find myself each night going back this one video, and it has me all confused”, I cried out. Kay smiled and then said “seems to me that you should act on what you’re feeling, I think if you do, you will find all the confusion go away”. “I don’t know, if I can”, I replied. “Look Kavin, you live here alone right, so who’s going to know, me that’s about it, so try it, get it out of your system sweetie”, She said. I looked at her not knowing what to say or do, I think she seen it in my eyes, when she said “excuse me I need to use your bath room”. I pointed to it and waited about five minutes later Kay came out. She walked up to me hugged me, and handed me something, it was red satin, “Go ahead Kavin they are mine I want you confront what is bothering you, give me your keys, and I will have Jamie drop your car off, and pay her cab fare home, I will expect you back at work day after tomorrow sweetie”, Kay turned and left my apartment.
I stood there holding a rad pair of women’s panties, I put them to my nose, the scent of Kay was over powering, she smelled so sweet, and the smell of lavender overwhelmed me then. I felt myself getting hard. Was it from the scent of Kay’s pussy, and lavender mixed or the idea of putting on her panties?
It took a moment, but having someone know what was bothering me, made me feel at ease. I stripped down, right there in my spare room, and slipped Kay’s panties on, I almost came when the soft fabric encased my cock, it was then that any resistance that I had to wearing women’s panties was gone, Something inside me told me that I would never wear anything else. I turned on my computer again, and went back to web site. Noticed that a video had been saved I clicked on it. This one went further; it was dressing as woman, panties, nylon, bras, and shoes, all of it. I watched transfixed by it all.
I began to rub my cock again the feeling of the satin against was more than I could take, I came hard filling the red panties full of cum, the release of tension was what I had been waiting on. I got up and went to the bath room. I took them off and put them in the sink cleaned up. It had felt so good to cum like that, I was in seventh heaven. The knocking on the door brought me back to reality. I opened it and there stood Jamie. “Hi Kavin, Kay wanted me to bring you your ride back, it’s parked out front”, I smiled “thanks Jamie, want to come in?” I said. “Sure why not, off for the rest of the day anyway”, Jamie said as she came in. We sat and talked for thirty minutes when Jamie got up and went to the bathroom, it was then that it struck me, I have left the cum filled panties in the sink. Jamie came back out and didn’t say a word about them. Apparently she didn’t see them, or didn’t care if they were there. Jamie had told me she had moved here, when she got an offer to come to work for David and Kay, that was two years ago and she has loved every minute of it. Kay especially, ensured that Jamie’s transition went smooth. I was perplexed by Jamie telling me that, what transition?
“Jamie I have question I know that it may sound a little out there, but what transition are you talking about?” I ask her. Jamie smiled, “You don’t know do you Kavin?” Jamie sat there for a moment, and then she began to tell me her story.
I sat there listening to Jamie, her story sounded similar to mine, a point in her life were she wasn’t sure what to do. I found that very interesting, that your employers were willing to help a person with such a personal problem. Jamie seemed frustrated, so she stood up, and pulled her skirt up, she had on a pink pair of low cut panties, and a noticeable bulge, I was stunned. She sat back down. “I never knew Jamie, by looking at you” I said. Jamie smiled saying, “I saw the pair of panties in your sink Kavin, and from the looks of it you had a good time, that is how it all started with me, Both Kay and David took time to help me, as they did with the other girls, my boy name was James, Lindsey was Larry, Joan, was John, Missy was Matt, and Mary was George. We all came to this company with expectations of doing good, and we are, but Kay and David did something for us that no one ever took time to do and, that I’m thankful for, how did they know? at first I wanted to know, but as time went on I didn’t care how it happen, I’m just glad that it did, don’t get me wrong both of them can be very strict, but at the same time you come to appreciate that, and even like it”.
I was totally stunned at this revelation from Jamie; I didn’t know what to say to her. “Look Kavin, why do I spend the night here, and we can talk about it, but first I need to get something’s from my apartment, can I use your car?” “Sure why not”, I replied.
Jamie had left, I went into the bathroom, and grabbed Kay’s panties and hand washed them, and hung them on the shower rod to dry. I went back in my spare room, sat down in front of the computer, and saw that a message was waiting for me. It was from Kay. “Kavin I know that it seemed strange that I left my panties there for you, but I do understand what you are going through, as I’m sure that Jamie explained to you, she is so sweet isn’t she, any way I did ask her if she spend the night with you, and maybe she could help you over some of the rough spots, and yes dear you can keep the panties, I think you look good in red…will see you and Jamie next Monday, I know I said the day after tomorrow, but I talked with David and he agrees with me, that you need a little time to get your thoughts together, dear, and yes here are websites that may help you out, be sure to watch them…ta ta..Kay”
I book marked the sites, may as well, see what they are all about. By the time I had finished making snacks for Jamie and myself Jamie had gotten back, she had two medium size suit case’s, for an over nighter that was a lot of things. “Kavin, where can I put these?” Jamie asks me, “Just in the bedroom, I’ll sleep on the sofa” I replied. Jamie gave me a big smile, and walked to my room. She came back out, and sat at the kitchen table, and started eating. We talked about everything, she told me about the other girls at the office, and how they got excited when they learned that a new girl was going to start. I stopped her at that and ask her why they thought I was a girl? Jamie smiled and said “Kay and David don’t hire men at all sweetie, come on want to show you something”, Jamie jumped up and I followed her to my bedroom.
Jamie opened both case’s and they were full of all kinds girl things, “You will need these things a gift from David, he wants you to start dressing now, nothing fancy, he wants to keep it simple”, Jamie said with a laugh. I didn’t know what to do at first, but then I said, “Jamie let me show you something”, as I went from the bedroom to the spare room, and clicked on my bookmarks. Jamie smiled “all excellent sites, we will go through them later, but first let’s play dress up”. She grabbed my hand and led me back to my room, and proceeded to take all my male clothing from the drawers and toss them out, and neatly packed them with my new things. I know I should have put a stop to it, but something inside me keep from doing anything but stand there and watch Jamie. She had three bottles of pills, and a vial and a small box of disable syringes. Jamie turned and said “these are for you, Kay had went to her doctor and got them the doctor said for you to take one pill daily, and tonight I’m going to give a few shots, to boost the start of the new you, so drop your pants sweetie, time to get started”. “A Shot”, I thought to myself.
I stood there, again I knew I shouldn’t, but something inside caused me to comply, I dropped my pants, and Jamie swabbed my buttock, and stuck me, It really didn’t hurt, but a warm feeling came over me in an instant. It actually felt good. She had me take a pill, I was to find out later that I was given a massive shot of estrogen, and that would continue throughout Jamie’s time with me, and that the pills were hormones.
“Kavin I really need you to help me here, I want you to go the shower, and start it, I will be there, to help you with what needs to be done next”, Jamie said. What the hell I though I’ve went this far may as well go the rest of the way” could it have been shot Jamie had just given me or what? Off to the shower I went, the warm water felt good running over my body, it must have been ten minutes when Jamie walked in. She pushed the curtain back, I just stood there. Jamie was naked, she had the perfect body, but she also had a penis, which I could stop staring at. “Stop that now, we need to fix you dear”, Jamie said as she stepped into the shower. She had in carried with a couple of bottles. “Now Kavin these are hair removers, they won’t sting, but it will easier to if I apply them don’t want to miss any spots, turn the shower head away, the lotion will have to sat a few minutes to work”. I did as Jamie ask me, she began to rub the lotion on my arms, armpits, stomach, back, she squatted down and started on my legs. Jamie worked her way my legs, it felt good, but the higher she got, she couldn’t help but notice that I was getting a hard on. Jamie cupped my balls, and rubbed the lotion on them. “What do we have here girl? Seems like your clitty is getting aroused, I think we will take care of that later” she said. I felt embarrassed, by what was what happening, she had finished my body, and then turned the shower head back on me. I looked down, and watched what body hair I had gather around the drain, the scent of lavender filled my nostrils, it seemed to relax me. “Okay Kavin, time to get out”. I reached over and shut the shower off, the sensation of not having any body hair was overwhelming, cool air hit me, but the feeling was sexy, I thought. Jamie dried me off, she stood there naked, wand wet, “Well Kavin your turn”. I started drying her off her hair, arms, shoulders, back, front; I squatted down, and started with her legs, working my way up. I saw that she was excited Jamie had a hard on, I just stared. “Go ahead Kavin touch me, it’s okay, my clitty needs to be dry also”. I was nervous, I had never touched another man’s cock, but with the shot, the bath I just reached up and began to dry her of. “Um feels good, sure you never done this before’ Jamie said with a slight moan. I just looked up at her and smiled.
“Kavin you need to stop now, time for that later babe”, Jamie said. I stopped. Get up girl, time to dress do hair and makeup. I followed her back into my bedroom. She sat me down on the side of the bed, got me a pair of black satin panties, “Put these on Kavin”, she said. The coolness, and sensation of them sliding against my legs, and them slipping them up on my waist, was too much, I knew then why women loved to be hairless. My little cock started to get hard again. Jamie smiled; she knew what was happening to me, that first time sensation of wearing silk and satin. She began to fix my hair, “you’re so lucky, I had to wait for my hair to grow out”, she keep priming and fixing it. It took her about fifteen minutes, to finish, “perfect” she said. Jamie had gotten out a small bag from the dresser, and opened it; in side were all sorts of things. “Let’s do the eyebrows first, and Jamie plucked away, it didn’t take her long to accomplished it all. “ You know I think to make it all work, Kavin, I want to call you Karen is that all right? “I sat quite for a moment, then answered her, “that will be fine Jamie”, Jamie giggled “great I love it Karen”. I sat there as Jamie applied foundation, eyeliner, eyelash liner, powder, and then red lipstick with a gloss. Jamie stood back, “oh my, Karen you look absolute beautiful”, Jamie said as she held the mirror up for me to see. I was shocked, needless to say it appeared that any traces of Kavin were gone, all I saw was a pretty young woman named Karen. “Well Karen what do you think?” Jamie asks me. I was speechless. “What’s the matter can’t say anything about the real you dear?” Jamie said. I finally said “WOW”!
“Let’s get you dressed hun”, Jamie said. She continued speaking, “seeing’s that we aren’t going anywhere tonight I think a nice sexy black camisole will do for now”. I put it on again the feeling of silk against my naked body, began to arouse me. Jamie got up and put on a pair of powder panties, and a matching camisole. “Come on Karen let’s go watch some video’s that Kay wants us to watch, this is going to be fun”. Jamie gave me another shot, before we started, and what a night it turned out to be. We watch four videos, each one was specific, how to walk, talk. How to caress you man, what the first steps of anal sex, and how to give a blow job, after that, Jamie and I went to bed. That night I gave Jamie a blowjob, I chocked when she came, but she told me that was alright the first time she gave a blowjob she did the same thing. Jamie played with my cock, teasing me, by that time she was hard again. “Roll over Karen, I want your sweet virgin ass” Jamie said. I did it, with her cock not being large it hurt just a little, but soon I was finding pleasure in it. I felt Jamie cum. when did. She reached around squeezed my little hard and I came hard. I had to get up and change panties, as did Jamie. I was hoping that Jamie would fuck again, but it didn’t happen that night, it happens the next day when Missy came over.
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