Part 1 - Becoming A Professional Secretary
This week's short story.
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 major 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. That meant, for the most part, they were treating me like a girl, talking to me like a girl, and 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 the 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 is 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 makeover."
"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 to 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 the 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, the 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 garter 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 blushed, and put a creamy mocha-colored lipstick on me after first outlining my mouth with a brush. The hot rolled my hair, backcombing 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 an 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 sometimes 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"