Secretary’s Day                              by: Rachel Ann Cooper                       © 1998

 

I suppose Mom was right. Since I first began high school, we had known that I didn’t want to go to college and probably wouldn’t have the opportunity anyway, considering she was our only support. She made a good living though, as a secretary to the president of her company. She had invited him and his wife to dinner a few times and it was obvious that he appreciated her both for her skills and for herself as a person. That rapport she had with her boss really impressed me. Since she was his personal secretary, she got to travel with him to conferences and such as his personal assistant. One night early in my freshman year in high school, Mom sat me down for a heart to heart chat about my future.

"Conrad,"she said, "you really have to think about a major for high school so you will have something, some skill that you can sell when you graduate. Heaven knows it’s a dog eat dog world out there and high school diplomas aren’t worth what they used to be. You need to have a specialized skill." "They really don’t have that much to offer, Mom," I replied. Of the courses they offer, well, just listen: auto mechanics, wood shop, metal shop, science and math, biology, home economics and secretarial. I can’t stand the first five and the last two are for girls and I’m not a girl."

"Where in the world did you ever get the idea that secretarial skills are just for girls honey?" "I don’t know. Aren’t they? I mean I’ve never seen a male secretary." "Conrad, there are millions of things you haven’t seen or heard of yet and there are lots of male secretaries now. They’re still a minority, but they are certainly out there and making a good living at it too, better than us women doing the same work, more’s the pity. That really makes me mad, but there’s nothing I can do about it and things I can’t do anything about aren’t worth my time."

"Honey, I’ve already taught you to type. All you’d need to do to get your secretarial degree would be to learn shorthand. It’s like a language but with practice, I’m sure you could master it." "But a male secretary Mom? C’mon. How many of those do you see?" "Not enough honey. Not nearly enough. You could become a secretary to a bigshot like your Mom is. You could get to travel and stay in nice hotels and see the world. Doesn’t that sound like fun?"

"Well, yeah, it does, and since I really don’t care for the others, I guess I’m sort of stuck unless I just drift through without a major. You aren’t going to let me get away with that, are you?" "No dear." " All right, I’ll take the secretarial course with a minor in home ec. Boy, am I going to take some razzing about this, as small as I am. It’s going to be like being stuck in a time warp with all girls in my classes." "Honey, you’re 5'6" tall. I don’t think Dustin Hoffman is much taller than that." "You like girls don’t you?"

"Of course I like them Mom. Maybe not like some of the guys do. I’m not always talking about taking them to bed at least. I don’t really know HOW I feel about them. I like to look at them though. I guess I’ll really have to develop some friends among them considering my major." "That sounds like a fine idea honey. A friend is a friend. It doesn’t matter what sex they are." And so I went to the office and applied for a major in secretarial skills with a minor in home economics.

As expected, my majoring in ‘women’s work’ caused a bit of a stir. Oh, it wasn’t anything gigantic, I suppose. I mean, it wasn’t like I was getting picked on or called a sissy or anything like that, although that’s what I’d expected. I did catch some flack from Roy. He was the star of the wrestling team. Not very much in stature himself except for all those rippling muscles and outweighing me by 40 pounds, he thought just because we were the same height, I should be as macho as him. He rarely missed an opportunity to give me a dig and even punched me once in the arm. It sent me flying into a wall in the hallway. He and the guys he was with had a good laugh and then, it was pretty much over. He didn’t pursue me relentlessly like I feared he would.

For some reason, that never materialized and while my typing, shorthand and home ec teachers were a little astounded at a boy in their class who was actually there to learn, they got over it and began treating me like any other student in the classes. Than meant, for the most part, they were treating me like a girl, talking to me like a girl, reacting to me like a girl. Mom had tried to prepare me for this. There was really no way I really could be prepared for being treated like a girl in boy’s clothes though.

I was getting some teasing from the girls in my home ec class especially. I think it was just a game to them. I was a novelty to be played with regardless of my feelings. I have to admit, there were a few nights when I cried myself to sleep over the lack of respect my classmates showed me. Nevertheless, I was determined to be a good student and to learn what was taught, just like the girls, maybe BETTER than the girls. I’d show them! As I had mentioned to Mom, I needed to make some girl type friends and after a few months of them getting used to the idea, I did make a couple. I think some of the guys were actually jealous that I was always in the company of some of the cutest girls in school. They probably thought I was getting something from my relationships that I wasn’t but this helped to buoy up my image a little. That didn’t last long though, not once I really found some girl ‘friends.’

Shirley and Anita were definitely two of the cutest and they were in my classes. I decided that if I had to keep company with girls, it might as well be the cute ones and made a concerted effort to win their friendship.

It wasn’t easy. They quite naturally questioned my motives, but by the end of the second quarter, Shirley and Anita were my closest pals. They were both cheerleaders and hung out with Barbara, who was head majorette. I don’t know if it was the fact that I was soft spoken and polite or what, but they sort of adopted me. Since I began the secretarial course, there weren’t many guys who wanted to hang with me anyway, so I was grateful for the company. I spent quite a bit of time at Anita’s house and her folks seemed to like me. They must have. They let me be alone with her any old time and they didn’t do that with any other boys.

I suppose I had become obviously non-threatening as a boy, too well mannered, polite and considerate. I even helped Anita with some of her household chores for which she made me wear a frilly, full cover apron.

By the end of my sophomore year, I was up to 80 words per minute (WPM) in both typing and shorthand. My only problem seemed to be that I was having somewhat of an identity crisis. I was spending so much time going to school with and hanging out with girls, I’m afraid I began to act like one of them. Honestly. I couldn’t believe some of the things I’d said lately and the way I was acting, GAWD! I became animated in my conversations and giggly, my voice rising and falling and reaching higher registers. I began to walk and talk and carry my books like them.

If I didn’t know better, I’d think I was gay which, of course, I wasn’t, but it was easy to see a shift in the boy’s attitudes toward me. It hadn’t been good. Now they definitely looked down at me like the lesser creature they thought girls to be, objects to be pursued and conquered for their pleasure. The other girls..., whoa, see what I mean? I wasn’t even thinking like a boy anymore. Shirley and Anita had begun treating me like a sister instead of a brother and I swear I was beginning to envy them, the way their bodies were changing and the cute clothes they got to wear. I became worried and a bit withdrawn, even from my pals.

One thing I found out in a hurry. If I didn’t want to be embarrassed, I shouldn’t go shopping with those two. I mean, really! Instead of letting me goof off in the isle of the mall like they would with any other boy, they’d haul me into the stores with them and hold up things, intimate things, and skirts and dresses and stuff to my body and try and coax me into the stuff, as if I really cared. Maybe they thought I really did care. I suppose it would have been better if they were in teasing mode, but they definitely were not having giggle fits. "I could never pass myself off as a girl no matter how I talked or acted," I said. "We don’t agree, Conrad. In fact, Shirley and I have decided that you’d make a really cute girl with that shoulder length hair and we want you to let us dress you up and prove it to you, give you a make over."

"Are you serious? I’m not a Sissie!" "We never said you were Conrad. Girls aren’t sissies. We’re just being ourselves, our feminine selves. We think there may be a feminine self in you too Conrad." "We’ve never been more serious, and we aren’t trying to be mean or anything either. Since we’ve been friends, you’ve come to act like us and talk like us and well, haven’t you ever wondered what it would be like to look like us and wear all these soft, pretty things?" "Do I have to answer that?" "Yes, you do. You HAVE, haven’t you?" "Gee, Anita, you’re really putting me on the spot. You’ll have it all over school if you get me all fixed up and I find out that I like it." "No Conrad, we WON’T. Friends don’t do that kind of thing to each other. We ARE friends, aren’t we?" "Of course we are. Best friends, I hope." "Good. Then it’s settled."

"Be at my house after the game Friday night. Mom and Dad are going to a play and then out with some friends bar hopping and won’t be home until they close someplace." "OK Anita. I guess it won’t kill me and I am curious. I’ll admit to that much." "See you then CONNIE." ‘Hooboy! That’s all they have to do is start calling me Connie around school and I’m dead meat. I kind of like it though. Has a nice ring to it. It COULD be a contraction of Constantine, a boy’s name.’

The fateful Friday came and I dutifully kept my rendevous. They were waiting and had all sorts of stuff laid out on the bed and vanity. I wasn’t expecting the very first thing out of their mouths. "First the bath Connie.

Be sure and get your legs and underarms nice and smooth." "Are you kidding?" Shirley said, "does this face look like I’m kidding?" "No ma’am. Right away ma’am, sir" I kidded back. I went to the bath, already drawn, and lowered myself into the luxurious bubbles and fragrance. It was very relaxing. I just lay there and closed my eyes as I’d never taken a bubble bath before. "We don’t hear any splashing. What are you doing in there?" That woke me up and I began doing the expected, denuding my almost hairless, soft and flabby little body.

When they heard me working, Shirley zoomed in and grabbed my clothes, leaving me nothing but a filmy robe and a pair of panties. Great. Now I’ve entered the lion’s den for sure! Thank heaven for the bubbles covering my nakedness.

I just knew they were going to do a number on me, so after I dried off, I put some lotion on my legs and dusted myself with bath powder. I’d show them I wasn’t afraid. HA! I was afraid. Once they had their hands on me, they treated me just like another girl. Well, that was nothing new anymore, but I still had some modesty left. "Connie, girls see each other all the time. It’s no biggie so reach in there and tuck that little thing away. My ten year old brother has one just like it, same size even."

"Hey, that hurt." "Sorry. Sometimes I’m too truthful for my own good," Anita said apologetically. Take this garter belt and put it around your waist and snap it closed then spin it around and pull the garters through the panties. Now sit and put on your hose like this." Shirley showed me and I rolled them up my now slick legs all the while feeling new sensations as the silky film encased my now feminized feet and ‘gams’.

"Now this bra with shelves in it over your arms." Anita fastened it and reached down behind the cups and pulled my fat up into the cups. The effect gave me weak knees and an instant bosom. I wasn’t really at all fat in the usual sense, just soft. I had never realized just how soft until she did that to me. "Now sit at the vanity and we’ll do your makeup for you this time. Pay attention." They tweezed and penciled and lined and mascara’d, blushed and put a creamy mocha colored lipstick on me after first outlining my mouth with a brush. They hot rolled my hair, back combing it into a fluffy girl’s style with tendrils coming down beside my ears.

"Alright, stand up Connie. Now the slip. Good. Now this brocade party dress with a full skirt. I think your first time should be something special and I love this dress. I think you will too." She zipped me up the back. I was locked in with no way out until they let me out now. "Alright Connie. Try on your first pair of high heels." I held on to Shirley and stepped into them. Oh, wow! What a feeling! I was so flushed all of a sudden, I thought I was going to faint. Waves of femininity that must be in the atmosphere all the time washed over me bathing me in warm, fuzzy ecstasy. They stood back to admire their handiwork. They didn’t say a word. I was afraid they were disappointed. Then out of Anita’s mouth came, "Damn, girl. You are a fox. Go look." I did my best to walk over to the full length mirror gracefully and halfway succeeded in the 3" pumps.

I looked. All I could see was Connie in a lovely party dress. All I could FEEL was Connie. If Conrad was in there somewhere, he was hiding really, really well. I was mesmerized by this creature I had become. "Like it, asked Shirley?"

"I...can’t...believe..."was all I got out before they caught me on the way to becoming a crumpled mess on the floor. I came to on the bed and the girls help me to my feet again. I tottered unsteadily but they seemed determined to see me through this experience. The weird thing was, everything fit me. It might have been my own clothes I was wearing.

I half expected my date to be showing up at the front door any minute, I felt that feminine.

I felt so strange, yet somehow wonderful and more closely connected to my friends than ever. "Come on Connie. We’re going to pop some corn and watch a movie. Come on girl." I woke up and began to move into the living room where I gratefully found a chair and, receiving instant instruction on sitting in a skirt, relaxed as best I could. This was...great!

What a feeling. I was truly jealous of my friends for the first time. There weren’t any boys at this gathering and we had a great time cutting up until it was time for me to go home. I got undone down to the panties and Anita said, "Connie, I want you to keep those as a little remembrance of your first time. It WAS your first, wasn’t it?" "Yes, but I have a feeling not my last with you two around." "You’re probably right. Go home and get your beauty sleep Connie. We’ll see you later."

(Author’s note: this area of interest could be plumped up a lot more but I’m tired.)

"Well Shirley,"said Anita, "what do you think?" "I think our friend is going to be a lovely bride someday. I hope she invites us to the wedding." "Me too!" "Let’s not keep her waiting so long for her next time. I think we could really turn her into a girl, what do you think Shirl?" "I think I can get her some hormones. Why don’t we try?" "I’m up for it. All she needs is some properly placed fat and some training."

When I got home, Mom was up doing her worrying mother routine and on seeing me said, "well, you look...interesting. How was the game?" "Great Mom. We won." "And what did you do after" she asked with a most peculiar look on her face? "Went over to Anita’s for popcorn and a movie." Well, it was true. I just didn’t volunteer anything. You’d have to know my Mom. I didn’t have to volunteer. "You’ve still got some eyeliner on honey and there’s still some foundation up by your left ear. Better go clean it off." I swear, that’s all she said. Nothing more. I went and looked in the mirror and saw what she saw, an imitation of Connie in drag as Conrad. Now the fat was in the fire.

My next screwup came when I threw the panties in with my washing and Mom found them. Being much too small for her, she knew exactly who they belonged to, ME. She had purposely put them on the top of the pile she handed me to put away. "Conrad, is there something you’d like to tell your mother?" There they were, staring me right in the face, not six inches from my nose and I said, "I’d rather not, Mom, if I can get away with not."

"Alright dear. Just let me worry. I’ll be fine." Oh great! We weren’t even Jewish and she was doing the Jewish mother bit on me.

"OK Mom. The girls dressed me up, alright?" "Did they make fun of you?" "No. They wanted to confirm their suspicions." "And did they?"

"Yes." "You liked it?" "I was overwhelmed. It was incredible. Yes. Is that enough?" "OK honey. You’re going to do it again, aren’t you?" "Probably." "Goodnight sweetheart." "Goodnight Mom." Boy, was THAT strange or WHAT? She didn’t bat and eyelash.

"Anita?" "Yes?" "This is Mrs. Wells, Conrad’s mother. Could you come over for a few minutes for a chat?" "Sure, I guess so. Is there something wrong?" "Not exactly dear. I just want to talk to you and clear up a few things." "Alright. I’ll be right over."

Upon Anita’s arrival:

"Hello dear. Come in and have a cup of tea." Anita sat at the kitchen table and Mrs. Wells put the water to boil. "Anita, Conrad has been looking and acting quite girlish for quite some time and now I understand that you dressed him up completely from head to toe. Is that true?" "I’m sorry Mrs..." "No, no dear. You misunderstand. I think you may have done him a favor. What were his reactions?" "He fainted." "Oh, the poor dear. It must have hit him like a ton of bricks. Is he attractive?"

"I can hardly begin to tell you how beautiful your, if you’ll pardon me, daughter is, Mrs. Wells. She’s a knockout. I’m considered pretty but she blows me out of the box." "I see. Had you any further plans?" "I don’t think..." "Come now, be candid." "Alright. We were wondering if we could get her on some hormones to help her realize herself. She’s already so feminine that all she has anymore is girlfriends anyway." "I see. Alright. Perhaps that would be best after all. You needn’t concern yourselves with that end of it. I have a ready source and a delivery system in place. It’s called ‘breakfast.’ (Giggle)"

"Why, Mrs. Wells, I never thought you’d go along with this." "Oh, I’m afraid I agree with you dear. Connie is much too much a girl now. I will move very slowly, but you will see some changes next year I’m sure. I’ve never chided him about the makeup he misses cleaning off or about his girlish conduct. I’m sure he doesn’t know what to make of my attitude and for now, I’m just going to leave it that way. Will you be dressing him up in the future?" "We were hoping to Mrs. Wells."

"Fine. Do it with my blessing. Whatever you decide is fine. Just don’t get her arrested. I doubt you’ll ever get him to do it, but bring him home dressed sometime if you can. I’d love to see my daughter." "You really love Connie, don’t you Mrs. Wells?" "Her happiness means everything to me dear, everything." "Thank you for the tea Mrs. Wells. We’ll just play it by ear on our end. We really are fond of Connie in either gender. Goodbye"

Over the next few months, my friends found excuses to dress me up at least 8 times that I can remember. The last two times, they even convinced me to go out with them shopping and bought me a skirt and blouse and the last time, took me to the piercing booth and had my ears pierced and studs put in. What WAS I going to do with these two?

I was doing pretty well in home ec too except it included a sewing project and the project was designing and making a dress. The teacher wouldn’t make an exception for me just because I was a boy. So, I did it. After that session with Shirley and Anita out in public, what with getting my ears pierced and all, it didn’t seem so scary, and I knew what I could look like as a girl now. I got some fashion magazines from the library and found a couple dresses that I liked and drew out a plan based on what I liked in both of them. Then I turned that into a full sized pattern based on my own measurements, cut it and pinned it and had Mom help me with the final fitting before I cut the cloth and sewed it. And again, Mom didn’t bat an eyelash. "Is this your project for sewing class?" "Yes, Mom and no, I didn’t pick it. The teacher made me do a dress just like the oth... I mean..." "I know what you mean, dear." Boy, was this going to be embarrassing. But you know what? None of the girls laughed at me when I had to model my creation, not one. I didn’t get all dolled up like the girls did me, but that didn’t keep Connie from showing through. They were all very appreciative and supportive, well, except for Mandy. She was one tough girl. She should have been a boy for sure.

She was a pain in the neck anyway so I just wrote that one off. I gave the dress to a friend who was about my size and could alter it to fit her just so the kids at school wouldn’t think I really wore dresses. I really hated giving that dress away. (Sigh) At least they saw me give the dress away. It was a soft nylon jersey with raglan full sleeves, a high neck with set in collar and belted waist over a full skirt. I thought it was quite pretty in the mist green shade I’d chosen. At least that was over and I got an A on that project. Then it was on to cooking and decorating. I was pretty happy about never getting less than a B from Mrs. Porter in those classes.

Before surrendering the dress, I had gone over to Anita’s and modeled it for her and Shirley. They were really bummed that I was going to give it away but they understood. If I’d been seen wearing it, the jig would have been up. Even though I had become quite girlish, if I kept that dress, I might as well just wear it to school and give up my pretense at being a boy and they knew it. Actually, that idea had a certain appeal to it though. No more pretense. And since Mom had started me on St. Johns Wort and some other stuff for my health and nerves, my excess fat had begun to look rather nice when Anita and Shirley dressed me. I was just the least bit ‘jiggly’ is all.

Finally, as a senior, I had managed to raise my typing speed a little and was near the top of my class in shorthand at 125 WPM. Surely I’d find a good job. I got a flash of being secretary to some mobster but it was just a flash. A mobster probably wouldn’t want a secretary as effeminate as I had become. Employers didn’t come visiting schools looking for entry level people in high school, at least not at MY high school. It was only an A rated school, which meant we had a small student body and therefore not much to offer, so I went looking in the paper and pounding the pavement looking for a job. I knew Mom could keep supporting me as long as I needed it but it was time to do my share. I was ready. Or so I thought.

I was walking downtown one day in late June and spotted a sign in a real estate office. It said, "help wanted-secretary to office manager. Good skills a must. EOE." ‘Well, I thought, if they are really an equal opportunity employer, then maybe this might be good. Looks like a busy office.’ And so I went inside and inquired of the first person I saw who was the receptionist, Peggy. Understand, by this time, the best I could do was an androgynous imitation of Conrad and Mom, bless her, had never said another word about my appearance no matter what I forgot to wash off, even the lipstick. I was a bit more ‘jiggly’ now too even though I’d lost 5 pounds.

"Hello, my name is Conrad Wells and I’m here to apply for the secretarial position." "She looked up at me with those big blue eyes and said, "really?" "Yes, really. What’s the matter? Haven’t you ever met a male secretary before?" "Not in THIS office honey," she said rather emphatically. She was SO emphatic in fact, that she made me wonder if the sign was for real. Maybe they only SAID they were equal opportunity. Then again, maybe that look I got from her said, ‘you’re not really going to try and convince me you’re a male, are you?’

"Here," she said. "Fill this out and give it back and I’ll see how soon Mrs. Rule can see you." I did as instructed, filling out the paper on both sides and signing it in my best girlish script which had become my normal handwriting. Peggy told me I was the seventh applicant and that all the others had failed either the typing or shorthand tests. With that information, I became a little more confident. My skills were first rate. I sat there with my hands in my lap, knees and ankles locked together as if wearing a skirt, and waited. I heard something over the intercom on Peggy’s desk and she said, "Mrs. Rule will see you now." I had on my best suit and with an air of false confidence, marched rather timidly, I’m afraid, into her office. Well, I didn’t really march, glided would be more accurate. In boy clothes, I suppose my movements were definitely suspicious becoming more so ever since Mom had started me on that new regimen. I wonder...! No, that’s silly.

It was a large office, probably 20 feet square, and nicely appointed if not somewhat starkly furnished. It was mostly mahogany, rich and polished to perfection. Her desk was over near a corner while the secretary’s desk was positioned between hers and the door. Obviously, her secretary was privy to all the goings on and had to work with her closely. I liked a challenge. "Sit down young man. I understand you graduated with honors from high school and that your secretarial skills are excellent."

"How would you know that, Mrs. Rule?" "I already called your school, dear. I don’t waste my time talking to unqualified people. Here." She handed me a transcription pad. I knew what was next. She began to dictate a letter rather rapidly, at least 100 words a minute. I had no difficulty keeping up with her however. "Now, she said, sit down at this desk and type it up for me. You are on a stopwatch. Go"

I began transcribing and had the letter done correctly in five minutes flat, despite my longish, tapered nails. "Well, she said. You could have taken seven minutes and I would have been happy. And you got it right, too. Congratulations. The salary is $400 a week to start. Would you like the job?" "I certainly would. When can I start?" "Tomorrow, if you like. The position is empty. As you learn your way around here, there will be more responsibilities, but for now, just show up ready for work at 8:30 and dress neatly. I assume you know how to make coffee?" "Yes, Ma’am. I took home ec too with cooking, sewing and decorating."

"Well, she said, it sounds like you’d make someone a perfect wife, she said with a big grin. You certainly have the manner for it." Was that a dig? "I...uh...suppose I would at that Ma’am. Thank you. How do you like your coffee?" "Black, one sugar, but I have to drink decaffeinated." "Really? Me too, one sugar, except the decaf part!" "You can have the regular for yourself. You and I have our own coffee service in here so you don’t need to stand around outside wasting valuable time talking to the salesmen." "Well then Conrad, we already have something in common. We’ll work on the other things later." What other things, I wondered.

I’d been to my Mom’s office many times over the years and had seen what she did and how she did it and did my best to copy her style. She was very efficient and business like. I always wore a nice suit or sport coat and Mrs. Rule never offered to let me take them off either. It also became a rule that I never buttoned my jacket, as that would accentuate my small waist and somewhat peculiar shape. I’d long ago taken to wearing ladies panties and hose sometimes and always wore a pair of feminine casual shoes. Mom knew about my liking for feminine clothing and while never actually getting any, she never said anything further when something showed up in the wash either and I think she knew where the girls were taking me to get my shoes.

I suppose being Mrs. Rule’s secretary and receiving her clients, she wanted me to look my best. She never criticized me for the amount of coffee I drank either and I’m afraid I almost always had a cup on my desk. I don’t know where she gets her coffee but it was certainly delicious. It was robust and yet a little sweet even without the sugar, ‘probably a special gourmet blend’ I thought. Since I always put a sugar in it however, I didn’t really know what it tasted like without.

I was there about three months and we were getting along just fine and the receptionist, Peggy, and I were getting along well too. I seemed to gravitate to her just like Anita. The sales reps were in and out of the office and handled most of their own paper work as it had a lot of legal stuff in it in which I was not trained. Mrs. Rule was teaching me though how to handle things at the top. By the time I’d been there another month, I was feeling a little peculiar, about myself, I mean. I was surrounded by women, being taught by a woman once again and spending idle time with Peggy. It was De Ja’vu.

"Mom?" "Yes honey?" "Have you noticed anything, well, different about me lately?" "Like what hon?" "I don’t know. I feel different somehow and I look different to me in the mirror and I seem to act different down at the office, almost like I was, I don’t know, a girl secretary instead of a male secretary. My body is a bit strange too. Am I acting funny?" "You mean as in peculiar?" "Yes." "Well, you did pick up some girlish traits in high school honey."

"Yes, I suppose your job may be influencing your behavior a little but you ARE a secretary after all and we really haven’t discussed your femininity level. Mrs. Rule isn’t on your case about it is she?" "No, if anything she seems to be even nicer to me lately and that’s not all the changes Mom. You almost never see me without my suit or sports coat on anymore do you?" "Why dear, I hadn’t thought about that but no. Is there a reason?"

"I think there may be three of them Mom." At this point, I took off my coat to reveal a dress shirt that had very definite, prominent bumps in it and a rump that filled my slacks to capacity, accentuating my small waist. "My heavens, dear. Being a secretary seems to be hazardous to your health (giggle). I’m sorry honey. It’s just that you look so...well... ...secretarial all of a sudden. (Giggle)" I’m sorry honey. It’s just that after all your escapades with the girls in school and now just look at you. You look very sweet."

Mrs. Rule hasn’t said anything about this?" "No. She seems quite cordial and oblivious to both my shift in conduct and my, uh, weight gain." "Well, it’s probably nothing dear. A good secretary takes everything in stride. Don’t worry about it. I’m sure it will all work out." But MOM, aren’t I kind of acting like a girl lately, sort of...really feminine? And just look at this body!" " I did dear. What do you want me to say?"

"I suppose you are acting more girlish again dear, but a little temperance in your conduct won’t hurt you as much as losing your job will. She’s already given you a $25 raise. Pretty soon you’ll be making $26 thousand a year. That’s not bad for someone just out of high school. Am I right?" "Of course you are Mom, but I’m a little concerned over what’s going on with me personally." "As I said, it will all work out for the best. I don’t mind if you gain a little weight nor act a little, well, feminine. You’re only 5'6½" tall and 130 pounds after all." "Perhaps you should start dressing...differently."

"Don’t rub it in Mom. Mrs. Rule is taller than me too. She must be 5'8" in her stocking feet although she always wears attractive heels. She dresses very well."

"I saw some material the other day that would look great on her with her coloring." "Why don’t you tell her about it dear? Maybe she’d let you make her a dress or suit or something with it!" "Oh, Mom. I COULDN’T. What would she think of me?" "Exceptionally talented, for starters, I’d say. A way to a man’s heart may be through his stomach but to a woman’s it is definitely though her wardrobe. Tell her about the material and see what she says. You’re her secretary after all. That is a close relationship. Any bettering of that bond is to your advantage dear."

"Oh, alright. But I can’t believe she’d actually let me do something like that. I mean, I’d have to measure her and everything and I’m a boy." "A technicality dear. Tell her." "OK." It took me three more weeks to summon up the courage to tell Mrs. Rule about the material I’d found and that I’d like to make her a dress or suit out of it. She was very gracious but in the end, declined my offer, telling me she got all of her better clothing from Dillard’s right off the rack. "However, Conrad, why don’t you make yourSELF a suit of out it?" "Oh, it’s lovely cranberry wool worsted Mrs. Rule. It’s only good for women’s wear." "I understand you had to design and make yourself a dress in school." (Blush) "Yes Ma’am. I had to. It was a class project." "Did you enjoy doing it?" "Yes, Ma’am. I guess it would probably fit me now very well too. I seem to be...better endowed than I was then." "Oh, yes. Well, I have noticed that Conrad, but I didn’t want to make you nervous. Your work seems to be improving and you seem more at ease although you do appear to be taking on a little different flavor lately, both physically and mentally. Does that bother you dear?"

"Mom and I have talked about it Mrs. Rule and she thinks I should just sort of ‘go with the flow’ as long as you are happy with me, regardless of whatever else is going on." "Good. Then it’s resolved. Buy the cloth and make yourself a nice business suit then." "But, Mrs Rule. When would I ever wear it, I mean with a skirt and all?" "Just look at it as a class project; something to keep you in practice. You don’t want to lose your skills do you?" "I suppose not but a skirt suit for ME? When would I wear it?"

"Just humor me Conrad. I’m sorry dear, but I think you will have to admit that you seem very girlish lately in appearance, body image and deportment. Now, before you start but, butting me, just listen. I really didn’t want to hire a male for this job but you were qualified and did well in the tests and I needed a good secretary. You’ve been here six months now and that is just what you’ve become, a good secretary. I depend on you and you make great coffee dear. I’m glad you like the blend I buy for you. Now, here is what I propose."

"Go home and tell your mother what I want you to do and get her to measure YOU for the suit, alright?" "Oh, alright. I don’t suppose it will be that bad. You won’t laugh at me?" "No dear. I won’t laugh." I went home and told Mom all about it. She listened rather intently, I thought, as if she were crunching numbers all the while I was telling her. Then she said, "come on honey. Let’s get you a nice pattern and buy that cloth." And so, after dinner that night, Mom had me disrobe and put on her light silk dressing gown and she measured me. I was no longer the stick that graduated from high school. My measurements said I took a 34B bra, a 26 inch waist and I had 35 inch hips. GAWD! I was a bit overwhelmed. My body apparently got tired of me acting like a girl and decided to make me actually BE one and I don’t even want to get into what had happened to my original equipment.

Mom, on the other hand, seemed, I don’t know, almost pleased with what she found. I had found myself acting openly feminine around both she and Mrs. Rule this past month, even Peggy. It was like I couldn’t help myself and didn’t really care. With each vocal intonation or gesture that crossed the line of masculinity, I somehow felt closer to both of them and certainly to my buddy Peggy. We had taken to going to lunch together. My hands and gestures seemed to have a mind of their own. I even window shopped with her and she’d ask my opinion on absolutely everything. She had begun treating me just like a girlfriend, poor thing, just like Shirley and Anita. I was the closest thing to another girl in the office, I guess, being the boss’s secretary. I certainly was coming ever closer to feeling like a girl too.

Mom and I took off for the cloth shop and finally decided on a Butterick pattern. While they aren’t the easiest to work with, they do have some smart designs. It would take 2 ½ yards of cloth plus interfacing and silk lining. While I was pouring over the books, Mom had gone to another department for something and threw it in the basket. I noted the size. 34B. It was a bra and it was for ME! I just knew it! I said nothing in the store. I’d have at least $50 just in the materials for this suit and that bra was for ME.

"This seems like a waste of money on an exercise, Mom." "I don’t think so hon. Six months ago I might have agreed but not anymore." Now, why did she say that, I wonder? The work on the suit progressed slowly. I was in no hurry and wanted to get it right the first time. I had gotten a size 10 pattern but was a little afraid I was going to have to let it out some before I was finished.

"Mom. Why did you get me a bra?" "Aren’t you tired of bouncing like that yet?" "Jeeze Mom! Alright. Not only am I tired of bouncing, it’s very irritating too. My nipples are raw." "Oh, I’m so sorry dear. I couldn’t see that through my robe. It’s difficult to ignore nipples that are standing at attention, but I had no way of knowing you were sore. Here", handing me one of her camisoles, "try this and see if it doesn’t help." "It feels really slinky Mom. I’m sure it will help." "And rub some body lotion on them morning and night." "OK."

It helped alright. It helped my burgeoning bosom to another double peaked erection. It was downright erotic, the feeling of that satin against my tender skin. And rubbing my nipples, well, that elicited all sorts of new sensations, nice ones! I decided to try the bra on too. It was a perfect fit and I couldn’t help admire my reflection. It really enhanced my figure. This wasn’t just sedentary fat. My body was changing right before my eyes. They look good I thought; not too big for my size. What are you THINKING? Get a GRIP! The problem was, I was losing the grip, Conrad’s grip at least. All I could do was say, "thank you Mom. It fits great." She smiled.

I went in to show Mom how I looked in my bra and her cami.

"Honey that looks nice on you, except for the shorts, of course. I know Mom. I’m having a hard time finding enough to pull through the placket anyway." "When did you start wearing shorts instead of your panties? Maybe panties would be more to the point. You do have some don’t you?" "Yes, I admitted." "Conrad, I think it’s time we had a little talk." ‘Here it comes,’ I thought. "I don’t know what’s become of my son, but you don’t resemble him much anymore. Maybe becoming a secretary wasn’t such a good idea after all."

"Oh, I love my job Mom. Mrs. Rule depends on me. I like it there." "Well then darling, I’m afraid we’ll have to get you some clothing that fits both your body and your mind. You’ve adapted to being a secretary very well sweetie, but I really think you’ve taken on more of the flavor of a daughter lately. There doesn’t seem to be much boy left in you. I think I’d better have a little talk with your boss." "I do feel kind of all swishy inside Mom. Maybe you should talk with her. I don’t know how to act around people any more. I’m sure I’m giving out mixed signals and for sure I’m getting them back."

So Mom had a chat with Mrs. Rule. She came in person during my lunch hour and was still there when I got back. A fly on the wall told me a little of their conversation. Actually, I was a little sneaky. I left my dictating machine on record while I was out. How careless of me. Oops!

"Mrs. Wells, do come in. Conrad has told me a great deal about you. I understand you are a secretary as well." "Yes, for many years to Mr. Dale at Consolidated Aluminum." "Very prestigious. I see where Conrad gets his talent then. Please have a seat." "Mrs. Rule, I think you are well aware of the changes that have befallen Conrad since he began working here." "Yes, it would be hard to miss them, wouldn’t it? Frankly, Mrs. Wells, he has become a bit disconcerting in both manner and dress. He would look better IN a dress, I think, don’t you?"

"That’s why I’m here. I’m having him make that suit you discussed for himself and I just bought him his first bra, a 34B." "My, my. Our little cherub is growing, isn’t she?" "Yes, Mrs. Rule, ‘she’ is. Mind you, I have no objection to having a daughter. Actually, I had wanted one to spoil but then Conrad came along instead and I have had him on a very mild regimen of herbs and hormones for a couple years. Have you been feeding him something as well to bring this about?" "He drinks a lot of coffee, Mrs. Wells." "Yes, at home too, more than he should but...!"

"He’s been feeding it to himself and determining the dosage as well." "How?" "His sugar isn’t sugar. Quite simple really. Not being run through the coffee maker, it remains unharmed and he ingests it all day long. Since you’ve already admitted you wanted a daughter, I assume you are not terribly upset with me?" "Not at all Mrs. Rule. I’m the one who started him. Conrad’s father, God rest his soul, was a lovely man, a size 14, but a lovely man nonetheless."

"So, Conrad comes by his sweet disposition and talents quite naturally. I am a little surprised to hear of your husband." "He was sweet and gentile and I’m afraid I did much the same thing to him. We buried him in a lovely gown. I’m going to do a little shopping after work today. There is no need for you to have my incongruous son in your office any longer than necessary. I believe he is ready to graduate again. We must start him off slowly though."

"I agree. No abrupt shocks to the system. We’ll transition him right here as well as home and I’ll be as helpful as I can in making him, pardon me, her feel welcome and comfortable," said Mrs. Rule.

So, the sugar is it? I do feel better about myself lately though and now I know why I’ve had these wild urges when I pass lingerie shops and shoe stores and dress shops for so long. Hell, I may as well get my ears double pierced and pluck my eyebrows. That WOULD be fun. Start bringing on more changes before Mom can get to me. Maybe a little eye makeup. I’ll just play along and let her think she is doing a number on me. That coffee must be sweet all by itself.

A few days after ‘the visit,’ I went to the mall and had my ears pierced again and brilliant emerald studs put in. They sparkled like the sun and even though my hair was in a pony tail and I could have hidden them by letting it loose, I wanted Mom and Mrs. Rule to notice this escalation of my femininity. I got small hoops for the bottom holes.

"Honey, I have a present for you." "What’s in the box Mom?" "Open it and see." "Oh, wonderful, I screamed. There must be two dozen there."

"Good guess hon. They’re size six. That should leave you just a little room to grow." "Please Mom. I don’t want to be a heifer." "I got you a few of your own cami’s and a couple more bras and some really pretty nighties. I hope you don’t mind."

"Why would I mind Mom. I’m turning into your little fairy princess, aren’t I ?" "That will be enough of that young lady. I’ve never demeaned you and neither has Mrs. Rule." "I’m sorry. I shouldn’t have said that. I just needed to throw a punch. I’m sorry it was you who caught it Mom. Please forgive me." "That’s alright honey. We all know what’s happening here and you ARE becoming my daughter, so it’s time you began dressing the part. I really think you should wear a bra all the time now hon. You’re too young to be droopy."

"Thanks. I will. Oh, if the guys at the pool hall could see me now." "They’d be trying for a date honey. Would you like to experiment with some makeup?" "Guess I’d better huh? It’s been a long time since I’ve done it myself." I’d expected that remark to take Mom back a little. She didn’t even acknowledge that I said it. "Well, you won’t learn it over night. Let’s put you in a blouse and jeans, let your hair down and take you to a makeup counter in a department store so we can get proper colors for you." "Oh boy. This is like, really a commitment, isn’t it?"

"I suppose so. It doesn’t scare you does it?" "If Daddy liked it, why shouldn’t I? Oops!!" "How did you know about your father? You should have been too young to remember that." "Must have overheard it Mom. I don’t know." Almost blew that one. Gotta be more careful.

"Mom?" "Yes?" "My...you know when I was younger and I’d leave spots on the sheets, sticky spots?" "Yes. That’s perfectly normal." "Well, I still have those feelings during a dream but it’s like, everything except the neat sensation has shut down and I haven’t even been interested in myself lately except for my breasts and they’re really neat." "That’s normal too, dear. Your boy hormones aren’t working anymore." "Does that mean I’m really going to turn into a girl?" "You can’t just ‘turn into’ a girl. You have become very feminine and you look like a girl, but if you want to really become one, that is a surgical procedure and you have to decided on that yourself. You’ve reached legal age." "I think we’d better stick with the clothes for awhile." "Fine dear. We don’t want to rush you."

So I began going to work dressed in a blouse under my jacket with my bra on and ladies slacks as men’s didn’t fit anymore, and girl’s flats and low heels. My hair got styled, washed, cut, set, permed and lightened and my nails were shaped to accentuate the femininity of my smallish hands. I wore girl’s rings and bracelets and hoop and dangle earrings. Then one day, Mom came home with several packages containing garter belts, hose, and a merry widow. Wow, was that ever neat. It gave me a really cute shape. Mrs. Rule never said a word about all this, of course. I knew she was in on it.

Just listen to yourself, wimp!’ ‘Aw, shut up dude. I’m beginning to really enjoy this side of me so bug off. I began to wear the hose and the merry widow, then Mom came by after work and took me to a shoe store. My new fantasy got a little more serious with the addition of slippers and flats and sandals and heels of every height, especially the sexy high ones. I must have bought a dozen pairs at least. When I got home, I put on a pair of the 3" heels with my slacks. They looked nice. I really liked them and they looked sexy peeking out from under my trouser legs.

"Mom, can I wear these with slacks to the office?" "Sure honey. Dress heels are fine with dress slacks. That’s going to make a defining statement, you know. No matter how androgynous a boy is these days, only girls wear spikes to the office and you’ve got the walk down perfect." "Yeah, I hadn’t thought about that. OK. Let me go put on my makeup and some perfume and you check me out, OK?" "Fine. Just saunter in when you’re ready dear."

It was time to pluck. I shaved my sparse beard and gave my eyebrows that distinctive feminine arch. Then I applied liner, shadow and mascara, some blusher and lipstick. Then I painted my nails and gave them a coat of Kwik Dry and was off to the living room. "Well, what do you think?" I left myself wide open with that one but..."oh, honey. I think you look darling. How could you have ever been a boy? No one will ever make that mistake again unless...well...you know."

"You really like?" "Yes CONNIE, I like. I think we need to talk to our attorney and get your birth certificate changed to Constance, don’t you?"

"Wait until the suit is finished Mom. Maybe then. We haven’t seen me in a dress yet." I began putting extra time in on the suit. And when Connie showed up at work in her slacks and heels, both Peggy and Mrs. Rule gave me a big hug. I’d swear Mrs. Rule had a tear in her eye. Naw! Probably my imagination. She’s too tough for that. From that time on, I was Connie however, and it flowed off everyone’s lips so much more easily than ‘Conrad’ ever did. A week later, I had the suit finished. The lining was lovingly sewn in by hand. Everything was basted and double stitched and the collar was perfect. It had a form fitting straight skirt that ended just at my knees.

It was a good thing I had cut generously. Mom had to let out the skirt a little. I was really turning into ‘a broad.’ I wore my black patent belt and black patent spikes and a demure white poet’s blouse with it and it looked smashing, if I do say so myself. Mom just couldn’t resist taking several pictures of me in my new suit. My feminine confidence level was high as I walked in that day. There was bounce in my step. I was young and pretty and very happy. It was April 22, Secretary’s day and Mrs. Rule was taking me to lunch at a fancy restaurant. As I walked into the inner office, I heard a little gasp come from Mrs. Rule. "Oh, Connie, she said, you’re everything I knew you could be." And I have been--- ever since.

 

The end.

 

© 1998
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