The Conscripted Bridesmaid          by: Alyssa Davis

 

What would you do if you were threatened with disclosure of your covert crossdressing activity? How far would you go to keep it secret? Especially if it involved crossdressing in public! Well, I yielded, and it had a lasting effect on my life.

 

Background

My real name is Alan, but to my family and close friends, I’ve always been called "Ali," an abbreviated version, an acquired childish name that never left me. "Sis," as I refer to her, is my older sister Shirley. I have just completed high school, while Sis has been out of school for the past three years and, after two years of business school, is working in a local hospital doing clerical work in the business office. Now that she’s gainfully employed and living on her own, her apartment has provided me with a good place to ‘crash’ when I need a respite from the parents. I sometimes even sleep on her "hide-a-bed" when I wish to stay overnight, which has become rather common. She otherwise lives alone so she enjoys my company, and we are very close friends…. kinda rare for siblings, especially those of opposing gender, but we’ve always had a close relationship.

It was a Friday afternoon, on one of my usual weekend visits, that Sis, having just gotten off the telephone, confronted me with an unusual request. Request, or was it a command?

"You want me to do what?" I asked. I had to hear this again. This was incredible!

"You heard me…I said I want you to fill in as a bridesmaid at Dee’s wedding!

I began to shake my head "no." Me? A bridesmaid?…this was completely out of context, I mean where did she get such an idea? Posing as a girl….unless….

"Oh c’mon, Little Brother, I know you’ve been sneaking in my underwear drawer for years. Now ‘fess up…you’ve been trying on my clothes, right? I assume you must enjoy wearing girl’s things. I’ve never said anything to anybody to embarrass you, but now, I’m calling in a favor for my silence."

I was speechless!

"As you know, Delores is getting married and now, she needs a replacement bridesmaid. Her cousin Bonnie, who was supposed to be in the bridal party, was in a car accident recently and can’t make it to the wedding, so Dee is one girl short. She’s my best friend and I want to help her, so I sort’a volunteered you to fill in. You’ll be with me since I’m one also. "

"BUT WHY ME?" is all I could manage to get out. I was stunned…shocked…embarrassed! She knew!

I felt like a deer caught in the headlights of a car full of poachers. Frozen in place…doomed!

But how could she? I had always been so careful. Oh my gosh….how embarrassing!

"Why you? Cuz you’re about the right size…short and stocky, same as Bonnie, that’s why I thought of you for this, and frankly, I really do think you’d make a passable young lady what with your petite, hairless body and smooth skin…and furthermore, I think you might actually want to be one," Sis snickered. She had to get that last remark in. "I’ve often envisioned how you’d look as a grown woman…goodness knows, by now you’ve had enough practice. Remember how we used to play dress-up? You loved it."

Sure….the right size. At 5’3" tall and 130 lb., so I am a little ‘vertically challenged’ for a guy, but fine, if maybe a bit "chubby," for a girl. I’ve always been teased about my size and figure, and have been called many demeaning names such as "Pear Shape," "Coke Bottle," etc., painful slurs for a small, overweight boy. OK, so I am shaped more like a girl…slender limbs, narrow shoulders, broad hips and butt. But gee, is it that bad? Even my voice isn’t very manly. I would sound rather sultry as a girl.

Yes, I have tried on her clothes and admittedly, I do appear very nice in them…perhaps too much so. Even my legs are shapely in hose. And I do have "breasts," well, as much as any flabby, pubescent boy would have, and maybe even a little more. They do fill Sis’s brassieres nicely, much to my pleasure. She is small breasted and wears padded bras.

As she talked, I sensed I was crimson red from blushing. That last comment stung! "Want to be one?" Oh yeah…I was trapped between the proverbial rock and a hard place. Had she discovered my clandestine crossdressing? When… How? And I thought I had always been so careful, so crafty. Aren’t all closet cross-dressers like thieves in the night?

Of course, I would dearly love to be a bridesmaid…what cross-dresser wouldn’t…it’s the stuff dreams are made of…being fully attired in a delightfully feminine gown with all the accessories, makeup, styled hair, looking like a princess…but I’d die if anyone I knew learned I was doing it. For that matter, I’d also die if anyone knew what I had been secretly doing all these years.

"You’re mistaken….I never did that!" Denial, my last bastion of defense. What did she really know? Was she testing me?

"Oh sure…deny it, Little Brother…I set traps for you, and I know what you’ve been doing! I’ve got proof…new stockings with runs, dresses with ripped seams. Zippers jammed…you’ve left things unbuttoned where I purposefully kept them buttoned in a certain way. Things not properly folded in their original position. I’ve even placed transparent Scotch tape on my closet door and my underwear drawers, and you’ve unknowingly broken the tape. Didn’t see it, huh? I don’t think mother was into my things. Oh yes….I know what you’ve been up to…I’ve suspected you for years…actually it was kind’a interesting to think of you dressed as a girl. So…what’s it going to be?"

How could I refuse her now without retribution, yet how could I accept and still save face? And Sis was dead serious about this. We have always had a close relationship as brother and sister, even though she’s three years older. And yes, I’ve always envied her for being a girl. Now, I’m trapped! Funny, she’s never said anything before about my "special interest." Had she told anyone else? Would she tell? She was always one to trick me into doing her bidding one way or another. This was the supreme trap.

My silence was getting her frustrated.

"Well, what’s it going to take for you to do it? I could blackmail you, ya’know. I’m committed to Dee to help her so I wont take NO for an answer!"

"Aw Sis, C’mon…I’d be too ashamed to even attempt it. What if someone recognized me, even if I could pass as a girl? Besides, why me? Doesn’t she have other girlfriends?"

"Look, the wedding is only two weeks away. No one’s available on such short notice…certainly no one the right size for the dress, especially, and major alterations or a new dress is out of the question. These things take time. I think you’d be perfect for it, and the closest one to Bonnie’s size…unfortunately, you’re the wrong gender, but it’s a minor detail that can be dealt with. Right now, only Dee knows of my idea. No one else involved in the wedding knows you personally, as far as I know. It’s mostly all her relatives and friends from her work, people we haven’t met. You can stay here with me till after the wedding, so I can transform you into a presentable young lady. You’ve got the time. You graduated high school only last week; you don’t have a job yet….so it’s perfect. And, frankly, I think you’ve got the inclination."

"Sure, and I don’t have any spending money either…I need a job."

"I know that, but you won’t need money. We’ll cover your living expenses and whatever it takes to transform you. It’s a big favor Dee and I are asking, and, after all, I’ve kept your secret all these years. I think you owe me something. So, now will you do it?"

Gee, now she’s almost begging me to dress like a girl. That’s a switch! After all those years of sneaking to cross-dress. Hiding…always hiding. I suppose I could make the sacrifice of doing something I’ve fantasized doing for years. But I needed to offer some token resistance to save face.

"Couldn’t she just go with one bridesmaid less?" I was stretching.

"Not an option…family politics…the groomsmen are all selected and fitted with their Tux’s. Who would they dump? Do you realize the hard feelings that would create?"

Further discussion was futile. She had good arguments. Actually, all the better for me.

"Oh well, okay…so, what do I have to do?" I said, sounding condescending while my heart was pounding with excitement.

 

"Good!…Let’s start now. I’ll tell mom and dad you’re staying here with me for a while….ostensibly while you job hunt. Meanwhile, I want you to begin your cross-training."

"Cross-training?"

"Well yeah….learning to look and act like a lady. This is more than just sneaking around in my undies behind closed doors or in an empty house. You’ve got to become a reasonably convincing young lady in a very short time. So, that means, you’re going to live as one full time for the next two weeks…HA! I’ll bet you’ll hate that! You’ll also have to get fitted for the bridesmaid’s dress. It’ll likely have to be altered for you, but only slightly, I’m sure. Maybe the shoes will have to be re-formed also. Luckily, you’re a little guy, so maybe not. There’s also a groom’s dinner to attend as well as the wedding itself, and the reception. You must be completely convincing, or else…

Start by taking a nice, soaking, hot bath, now, and shave any superfluous hair you have where a girl shouldn’t have," Sis said, winking.

She was serious! This was both a dream and a nightmare coming true for me….to cross-dress full time, even for a little while…but in full view of everyone? Attending dinners? Close encounters with strangers and maybe friends? As a woman!!!

Yes, I’ve envied Sis being a girl ever since I can remember. All her pretty clothes, nice toys…and all the attention she seemed to get from people when she was dressed nicely. More than I ever got, or so it appeared through the eyes of a child. I felt she always got the best of everything. And all the extra privileges she got! (Of course, now, I realize it was because she was older, but at the time, I thought it was cuz she was a girl.)

When very young, we commonly played together with her dolls, doll houses, and all it’s miniature furniture…I loved those miniatures…as well as many other girl’s toys, because they were more fun than my toys…(yes, even the dolls,) but as I got older, I was limited access to "girl things" in favor of more traditionally male orientated toys…cars, airplanes, sport games, things I actually had little interest in. I found them mostly boring. Oh yes, we played the usual "dress-up" games with Sis using me for her model or maid, and I always submitted. We would have pretend tea parties, using her tiny tea sets, all very formal. And we’d be two "proper" ladies. She was always the hostess and I was always the guest. It evolved into more advanced dress-up affairs at which I never resisted wearing mom’s dresses, shoes, and make-up. At the time, mom thought it was cute that we played so well together. That was like an endorsement for us.

As I entered puberty, I found myself attracted to magazine ads and catalog pictures of lingerie and women’s clothing in general. I wasn’t looking at the models, but rather their attire. I admired their styles and wondered how they’d look and feel on me. I sincerely wanted to try. Being attracted to Sis’s clothes, I first briefly tried some on, and ultimately wore articles of Sis’s underclothes for prolonged intervals, secretly, of course, at every opportunity, pretending I was a girl, enjoying the appearance and savoring the silky comfort of feminine things.

It seemed to be around the time she started developing and began wearing a bra and other pretty undies. Boy’s things are so drab by comparison. Plain cotton garments while Sis’s were pretty satin and nylon. Once I had tried hers, I was hooked! I don’t know why, but I grew to really love the sensation of fem things against my skin. The tight fitting, silky panties caressing my organ and creating tremendous erections, the look and caress of a bra, forming my ample flab into girlish looking breasts denoting a female figure. I was so proud of them. Then, the whole package contained in a formfitting, lace trimmed slip! And the nylon stockings, shaping my legs! All of which were the source of many fantasies. Those garments had an overall effect on my body and seemed to mold me into a girl, both physically and mentally, which I loved.

And now, I was being given the opportunity to fully and openly present myself as a woman, a radical change from my past clandestine experiences. A dream come true. It was, at the same time, scary and exciting. But, how, I wondered, did she know I roamed an empty house in her clothes? Did she plant a camera?

 

The Transformation

I soaked in the warm, bubble bath, for what seemed like hours, shaving the few errant hairs on my legs as well as my underarms. I routinely kept my body free from what little hair it had, so it was easy to comply with her directions. I disliked body hair.

My mind was occupied with the upcoming scenario of what I was getting involved in. I should’ve been ecstatic over what was happening, but I was too apprehensive to get aroused. Apprehensive? Hell, I was scared! It’s funny how the mind will do that. This was for real, now. Not just a brief fantasy to masturbate over. I was committed! What if I was discovered to be a boy in drag? What if someone recognized me? What if our parents found out what I was doing, or had been doing? Or, if anyone learns of this little game in the future.

Oh my gosh!….

When I emerged from the warm water, I dabbed myself dry with a large, bath towel, and slowly rubbed a pleasant, skin softening, lotion all over. Putting my fears aside for the moment, I felt very relaxed from the bath and the very feminine fragrance from whatever she used in the water. My resistance to this project was beginning to fade, slightly.

The hair on my head is black, naturally curly, tight curls, and being well overdue for a haircut, it was especially full, thick, and fluffy from the shampoo and conditioner she left for me, a look most women would spend hours to achieve, yet mine was natural. Some gentle brushing would even improve upon that. It already looked "girlish." It contrasted my fair complexion very well.

I entered Sis’s bedroom, wrapped in the towel, which was finally now slightly tented below my waist in anticipation of what I was about to do. I tried to conceal my embarrassment. The towel was wrapped under my arms in the fashion of a woman. Somehow, I felt that was now appropriate.

"Oh good, you’re done. I’ve laid out an outfit for you to wear. Start getting dressed, please," Sis directed, as she exited her room. "I’m sure you know how," she threw at me over her shoulder.

On her bed was the ensemble she had selected for me. A set of, by now, very familiar undies…new panties, a one piece, girdle-bra combo with attached garters (called a "Bustier"), a slip, tan stockings, and a below the knee length skirt and matching sweater combination. A form-fitting outfit that was to make me look very feminine.

I dressed in everything with no problem, from years of experience, well, that is, except that I had to manage my "manhood" inside the panties. Thankfully, the girdle’s crotch retained it in position as I pushed it up into my abdominal cavity, resulting in a very flat outward appearance, and not at all uncomfortable.

The padded bra cups supplemented my own breasts. I didn’t need any additional stuffing, since my own flesh, when molded, could nicely fill the cups. Sis wasn’t large breasted hence she wore slightly padded bras, and I, a bit overweight, actually wound up with as much bosom as she showed when I was formed into her bras, even producing a little cleavage in this garment.

Being slightly smaller than her, her clothes always did fit me fairly well. I skillfully attached the stockings to the garters. I love wearing hose…they feel so nice, and they shape my legs so well. The Bustier gave me an hourglass shape by cinching my waist, accentuating my hips and bust, (adding to the "Coke bottle" shape, now considered a feminine figure) allowing the skirt and sweater to hang properly. There was no denying it; I really enjoyed dressing like this. Enjoy is an understatement, I was a different person in this persona. More content; happier.

I located the shoes she left for me by the bed; sling-pumps with two inch high heels. Very stylish, and in combination with the hose, gave my legs a nice shape and color. I always felt I had unusually nice legs for a boy. Nice? Pretty is a better word. Being very comfortable, I had no problem walking in the heels, especially since I had gotten experience with them as well, through the years. They gave me a very girlish gait, which I had developed with practice.

I paused for a minute, in front of the long mirror attached to the closet door. I tugged at gently at my skirt, to remove a wrinkle from the waistband. I took a deep breath, while holding my shoulders slightly back. My "breasts" became all the more prominent. The light rose pink of my sweater seemed to throw a warm light onto my freshly bathed skin. My dark curls were still damp and shiny. I had seen myself almost like this many times before. But this time was different.

I heard my sister moving around in the next room, but instead of the cold fear of discovery, I felt warmth.
I looked and felt like a pretty girl, and my older sister was helping me grow up.

Fully dressed, and now feeling in the "mood," I presented myself to my sister for the first time, fully enfemme. I guess I got carried away with the moment.

"Ta Da! Here I am…" I announced as I burst into her presence maybe a little too theatrical.

 

"Oh MY! You do look nice! In fact, VERY NICE! I knew you could dress yourself, Little ‘Sister’, proof that you’ve done all this before!….I always wanted a sister, ya’know. And everything fits you so well…" She studied me all over. "You look very content dressed that way. I should’ve known you wouldn’t be too shy about it."

I thought she would be at least a little angry with me for being into her things, invading her privacy, but instead, under the circumstances, she seemed to be gushing at what she was seeing! After all, I was getting her off the hook, wasn’t I?

I started to blush, again. Yes, I loved this, but maybe I should’ve been a bit more reticent. I’m not supposed to be so overtly happy wearing girl’s clothes, but I felt like a wild bird being released from captivity. Free at last! Free to express my feminine side.

"Okay, let’s try some makeup on you now. I’m sure you’ll love that also."

‘Of course I would…I thought you’d never ask!’ I said to myself.

Gee, I hope she can’t read my thoughts…she’s pretty crafty! She’s read me pretty well, so far. Somehow, she always could…

Sis proceeded to apply all the necessary cosmetics to make me beautiful, explaining each step as she progressed. It was as if I was really her sister! This was something I had very little experience with, since I had limited time or opportunity as a closet cross-dresser, so I was intrigued with the whole process and observed closely.

The metamorphosis was complete and I had been transformed into a very passable young lady! We were both surprised, and pleased. I had never gone this far before, and I loved the results as I admired myself in the mirror, finding it difficult to hide my delight.

"You really do enjoy this, don’t you?" she observed.

"Yes, I guess I do," I finally admitted, quietly. "It’s really rather interesting," I added, still trying to be nonchalant.

"Yeah…right…interesting! You love it! C’mon, admit it. You’d really rather be a girl, wouldn’t you?"

 

My skin was smooth and clear from the foundation she had applied to cover my slight beard shadow, my cheeks were lightly tinted with blush, my eyelids tinted, mascara on my lashes, my lips perfectly outlined and filled in with red color. Even my hair was brushed and teased into a natural style, perhaps referred to as that "Grecian" look, with all the tight curls. The look that real women pay lots of money to achieve. It was even long enough to cover my ears and collar. Now, I was glad I had delayed getting a haircut.

Yes, I felt like a lady, and yes, I did love that feeling very much. The taste and fragrance of the cosmetics, the tactile sensation of the form-fitting and lacy underclothing, the female form of my body acquired by the foundation garment and lingerie, the feel of a skirt, the tug of the gartered hosiery. I was committed to all this! No more hiding, yet I had to play it cool. Dare I like it too much?

Would I rather be a girl? My lack of response to her question spoke volumes.

"You should know that the makeup I used is fairly permanent and difficult to remove, especially the lipstick. It’s water resistant. I buy good stuff since I must wear it everyday."

Was that supposed to be a threat?

"I wont need to remove it completely for a while, now will I?" I said, almost seductively. I was hoping, like never!

Sis sensed a change in me….I seemed to move differently, sound differently as I spoke to her, (I lowered my voice, speaking softly), even act differently. More confident, more relaxed…more mature. Well, it was as if an aura had come over me…..I felt totally feminine now…her sister, and she now seemed to accept me as that person. Not like a kid brother anymore.

"So, honestly, how do you like seeing me like this?" I had to ask.

"Well, I’m not surprised that you look so nice, and that you enjoy it, after what you’ve been doing. And actually, I think it’s kinda nice to have a sister."

"Aren’t you angry that I "borrowed" your things behind your back?"

Maybe I shouldn’t open old wounds, and I felt strange asking, but I was curious and had to know.

"Oh sure, at first, I was furious, but then, I began to wonder why you did it and what you actually looked like in them. Remember, we used to play dress-up as kids and you always enjoyed it. I just wish you’d have been more careful with my things. And then, after all, I did borrow your clothes too, after you’d leave for school. You never complained, if you even knew. And now, if doing this makes you happy, then I’m happy, Little Sister. Too bad you had to be so secretive…we could’ve had fun together."

"Yeah, as if I could tell you." We dropped the subject.

 

Sis began to coach me on effeminate mannerisms such as proper sitting, walking, body language, etc., especially while wearing a skirt, but it hardly seemed necessary. It all just came natural to me. I had practiced on my own for years…the desire had been strong.

Strange, Sis, herself, wasn’t a very feminine girl, both in appearance and those mannerisms, yet here she is training me to be what she is not! And actually, I think I’m doing a better job…guess I’m more motivated. So many women seem to take their birth gender for granted.

I volunteered to color my own nails, and proceeded to do so with patience and skill, to her amazement. They now matched my lips, and I liked that, too!

"Well, ‘Little Sister’….are you ready to go out in public? Let’s go get some dinner."

"I don’t know…yes….I guess so," I replied, softly, with hesitation.

I had confidence in my new persona (at home). This was something I always dreamed of doing, but I was scared! This was a major step for me. I was brave at home, alone, but out in public, dressed as a girl, was another thing.

"By the way, we need a girl’s name for you, Ali. Do you have one yet?"

Why would I have one? She’s still assuming I’d gotten that far.

"No…never thought of it," I lied, "but what about Alana?"

"Oh…yes, I like that. Alana it shall be, then. So, Alana…let’s go eat."

Borrowing a purse from Sis, and a few other items, we departed to a restaurant. It was just another meal for her, but the beginning of a whole new experience for me. It felt so strange to be outdoors and in public totally dressed as a girl, and with my own sister! I would have never done this alone.

The breeze blowing up my skirt, which billowed around my legs, was delightful. The whole sensation was exhilarating. I loved the freedom of skirts and the silkiness of hose, especially with garters. And walking in the heels was a constant reminder of how I was dressed. I did my best to create a feminine illusion, something I’d fantasized for years.

I remembered to sit with my legs together, ankles crossed, my elbows against my body, and my back straight. Always aware of what and where I was. Sis insisted I order my own meal. Looking into the server’s eyes, I spoke softly and smiled a lot. I must’ve sounded convincingly feminine because I received no unusual response from her. Maybe she was being kind. Or not very observant, but then, she likely wasn’t expecting a boy in a dress. Of course, I looked hot, too. Sis praised me for my ladylike demeanor, which further enhanced my self-confidence.

During dinner, she asked me for more details of my clandestine cross-dressing past, especially my motivation for doing so. I still couldn’t disclose everything…my innermost feelings...after all, I wasn’t so sure of them, myself. I still felt some shame and guilt associated with what I had been doing, especially with her things. Sneaking into her sanctuary, her wardrobe, like a thief…talk about guilt!

Maybe someday, I’ll tell her all of my feelings, but not yet. I did admit that I always enjoyed dressing as a girl…even as a child. Feeling pretty, wearing nice things, feeling feminine, more than that, I was driven to it as if I belonged that way. And I did so at every opportunity, but always in private. No, I had never left the house until now.

We reminisced how we played as children and how I commonly took a girl’s role, with her assistance. How, being a physically small boy, I was always teased about my size. How our parents used to frequently say I should’ve been born a girl…that they’d planned on having two daughters, then a boy came along. Then later, as I was growing up, that I was too pretty to be a boy with my black curly hair and long eyelashes. I used to be embarrassed by that but later, I liked hearing it.

We tried to determine the cause for my proclivity to cross-dress, now that I’ve disclosed it. No rationale seemed to come to mind. But she agreed with everything I had said, and related to my feelings.

After eating, I took the initiative to touch up my lips using the back of a spoon for a mirror. Sis was impressed that I handled the lipstick so well. The game was over…yes; I loved pretending to be a girl and wasn’t going to try to fool her into thinking otherwise anymore. I was constantly aware of what I was doing and I tried hard to improve upon my feminine persona. I would happily be a bridesmaid, and a very pretty one, at that!

That first night, sleeping in a nightgown, I dreamed I was a bride. Such a wild fantasy I had!!!! My groom was so tall and handsome. I was petite, pretty, and feminine. Oh….and the wedding night! I’ve had homosexual fantasies before, but never with such realism. Must’ve been the nightgown or what I was getting involved in. But really, was it homosexual? I was a woman with something a little extra, after all, giving herself to her husband, consummating their marriage and enjoying every moment. I had an erection all night.

The next day, Saturday, I awoke to the realization that this wasn’t a game! It wasn’t just another too-short dress-up session while home alone. I had committed to living as a woman for an extended period of time, and actually appearing in public! What had I done? Was I ready for this?

We set out for a fitting of my bridesmaid gown and check into necessary alterations. Dee had the gown at her house so she met us at the dressmaker’s shop. I was wearing casual, daytime attire for a woman my age, with the addition of the Bustier as a foundation garment, my makeup was done (by myself) and my hair was properly arranged (I’m lucky, all it needs is a gentle brushing and arranging and it’s in place!) I was comfortable.

Sis introduced me to Dee as Alana. Now, Dee has known Alan (or Ali) for several years, but she didn’t immediately recognize me, as a girl….and she was delightfully surprised and impressed with my transformation. I was immediately welcomed as "one of the girls" and received a big kiss and hug of gratitude from her for what I was doing. I couldn’t tell her, but I was equally grateful for the opportunity.

We tried the dress. It was beautiful; a powder blue, ankle length, slim fitted, brocaded satin gown with a jewel neckline. An otherwise good fit for me, it needed only slight alteration in the bosom to conform to the bust cups of my Bustier. It seemed that Bonnie was fuller in the breast area so the dress needed some "bodice reduction" else it would reveal my bra and everything I didn’t have! I now could see why they’d have a problem finding someone to fit the dress. From it’s style, it needed to fit perfectly and Bonnie was otherwise the same size as me. (I’ll definitely need the Bustier to mold me.) And for walking, it had a rather lengthy slit up the back. I’ll need a matching blue slip, too, and blue shaded hose. The dressmaker had no idea that I was other than a genetic female. To her, we were simply three young ladies in for a fitting. Even seeing me in my lingerie. That pleased me and was a real boost to my confidence.

The shoes were a perfect fit. But they were 3" heels so I’d need some practice wearing them. I took them home with me to wear around the apartment.

We stopped at a mall to do a little shopping before going home. Sis wanted to get me some of my own lingerie to wear since I was to remain as a girl for a while, at least till the wedding (and maybe longer). She felt it was time. We selected nylon briefs and matching bras with minimal padding, (no underwires), and wide shoulder straps for comfort since I’d be wearing a bra regularly from now on. Of course, I chose bras with lace trim…I like pretty things. We also stocked up on assorted hosiery. Also, she persuaded me to have my ears pierced, something I did not object to. She wanted my ears healed by the date of the wedding so I could wear pretty, pendent earrings to match the other girls.

For the first time in my life, I now possessed my very own hose, bras, and panties…no more "borrowing" from my sister. Well, that was a milestone for me, and it meant a lot. Other items, she was okay with my sharing. These were what she considered "intimate apparel" and didn’t wish to share. I could understand that, and it only made me feel more guilty for all the years I did sneak into her things. I intended to wear lingerie no matter what gender I was presenting, from now on. What’s the harm?

Back at the apartment, Sis changed to a sweat outfit, while I slipped into a different casual skirt, a shorter one, and the new shoes. She wanted me to remain in skirts until I was perfectly at ease and maneuvered effortlessly in them, which was fine with me. I also commenced my training in the high heels. Not the easiest in 3" heels, but I was determined to learn and so I remained in them all afternoon. Both my feet and the shoes got broken in, that day.

Saturday night, Sis wanted to go out to dinner and a movie. I declined. My feet were a bit tired, and I was still not confident to go out in crowds in drag. I knew she’d encounter some friends and I wasn’t ready for that, so I stayed home, alone. But it was so nice to be alone, fully crossdressed, without fear of being caught! I just curled up with some magazines, and the television, and relaxed. I had a totally renewed interest in women’s fashion magazines. My mind was fantasizing like videotape on fast forward…creating all kinds of scenarios of myself in drag, and making me very horny. Couldn’t wait for bedtime.

Sunday was another day of leisure except my "coach" was on me constantly to further improve my feminine presentation in encounters with other women. After all, I hadn’t had a lifetime of female socialization. And I was soon to be in the limelight as a bridesmaid in full public view. This meant at the groom’s dinner, the wedding itself, and the following reception. A full day, and two nights, of social activities. The thought scared me again…

Sis also added feminine vocabulary and intonations to her lessons. These included eye and hand movements. I wasn’t aware there were such gender differences. They’re just things guys take for granted, I guess. It was a long day for me, but I learned a lot. Too bad she didn’t practice what she preached. I think she could be a prettier lady if she was more feminine in her actions. Seems my desire to be a woman is stronger than hers….isn’t that strange, or is that typical of the transgendered? Anyway, lots more to practice.

Sis was gone to work on Monday by the time I woke up. In fact the phone woke me up. It was she calling to inform me that she had mentioned to her manager about her unemployed sister, and they offered me a job doing entry level office work over the summer, if I wanted it, as a vacation fill-in. This, of course, meant I would be working as a girl…all summer! I replied that I’d consider it and we could discuss it when she got home. I needed to give that a lot of thought.

I went through all the effort of making myself appear feminine again…shaving closely, applying foundation and makeup, arranging my hair. It’s a lot of effort to become pretty, even more to maintain it, yet still a lot of fun (or a novelty), but would I want to do this everyday? Well, practice makes perfect. This was not just a treat…I now was committed for at least a couple of weeks, and a bit nervous. How long do I want to continue?

Still not brave enough to venture out alone, I remained sequestered indoors for the remainder of the day, during which time I tidied and cleaned the apartment while wearing the 3" heeled shoes. Now that was a feat! I enjoyed working in a skirt…I was fully dressed…but the heels were a struggle, but also a necessity for me, feeling I needed the practice. I became quite adept at maneuvering in them though they did slow me down radically. My leg muscles also adjusted to them to the point of being somewhat comfortable in high heels. I must’ve resembled June Cleaver as seen in a 60’s TV show, the dutiful housewife in a bouffant dress, high heels, and pearl necklace. Well, my dress was straight, but lovely, and my legs were very shapely in the heels and hose. Oh, and I didn’t wear a necklace. But it was fun playing housewife and lady of the house.

 

The Job Prospect

We discussed the job offer over dinner, which I had prepared. Coming home to a clean apartment and dinner on the table put Sis in a very good mood. She had mentioned to her supervisor about having a younger sister needing a job over the summer after which, her sister might go back to school. It happened that there was a summer entry-level position open for a file clerk, which would be ideal for me if I wanted it.

If I accepted the job, I’d be committed to remain as a woman full time at least through the summer. This would require some serious consideration. Did I want to do it for that long? Could I get away with it? What about our parents? This would no longer be a two-week arrangement.

But then, it was a job, the salary and benefits were suitable, and at this point, the prospect seemed attractive. And yes, I loved being a girl. (Would I love it after several months?)

Since I had no work experience, finding a job might be difficult no matter what gender I was.

I decided to go for an interview the next day. What could it hurt? The appointment was made for Tuesday.

I found a business suit outfit in Sis’s closet, a mid-length skirt and matching jacket, something I felt appropriate for the occasion. With dark shaded p’hose, black hi-heeled shoes, and a silk blouse, it made a nice looking ensemble. For a foundation, I put a little extra padding in my bra and wore a high-topped panty-girdle, which cinched my waist to accentuate my hips. I looked sharp. After all, I wanted to present a good impression for my sister. Oh, I knew I was setting precedence for myself if I got the job. I’d be expected to dress like this forever after…but then, didn’t I want to?

I had become really psyched into being a girl. Completing my makeup, which I applied sparingly, I played with my hair to arrange it as nicely as possible. I fluffed up my natural curls with a comb and brush, happy that they were so long, now. Some small loop earrings finished the look.

 

The Interview

I entered the clinic, approached the receptionist and identified myself. It was as if they all expected me. My sister must’ve made an advance announcement of my arrival. Well, I did have an appointment. I wondered what else she had said about me.

"Oh yes, you’re Shirley’s sister Alana. She’s waiting for you."

Was I that obvious? Sis came out to the front desk with Mary, her supervisor, to whom I was introduced and made to feel welcome. We all then went into an office for some small talk to put me at ease. Admittedly, I was very nervous, both because I was to be interviewed for a job, and because I was presenting as a woman to a real woman who didn’t know me, something still somewhat new to me. That, alone, made me feel very vulnerable. I wasn’t yet completely secure in my newly adopted gender.

 

Sis departed and the conversation turned to my scholastic background, work experience, and future plans. I had to be very careful. Everything I said was about Alan’s background except, I used the female persona, so, in essence, I was telling half-truths. I must’ve been convincing because Mary seemed to show no suspicion of my birth gender. She then focused on the open position and what it entailed, the salary, benefits, and details about the facility. As Alan, I already knew many details about the clinic from Sis, but as Alana, I had to appear as if it was all new information.

Since it was only an entry level, seasonal position, the interview mostly was concerned about my interests and personality traits such as how I’d likely fit in with others, and since my sister was so well known and respected at the clinic, I was offered the job immediately, which I, caught up in the moment, accepted. I was to start on the following Monday.

As for dress code, it was explained that the professional staff wore white lab coats, nurses and assistants wore scrubs, and the office staff (who happened to be all female) were to wear appropriate business casual attire…skirts, dresses, slacks, etc., meaning no jeans or shorts and sandals. I had no problem with that. It also accounted for the nice wardrobe Sis had in her closet, which she was now graciously sharing with me. It also meant I would have to start buying my own things since the sharing was limited. That day, after work, Sis and I went shopping in Thrift and Consignment stores for a wardrobe for me. She advanced the money to purchase several new outfits. The prices were extremely attractive making it easy to buy many items, including shoes.

I still had a few days before starting to work, still time to back out. Once I showed up to work, I was committed for the duration. I couldn’t jeopardize Sis’s position there by hastily quitting. That was my motivation to succeed. Also, I couldn’t disclose my true gender at some later date should I want to make it a permanent position. That would be the worst thing for both of us, especially Sis who set this all up.

 

The Groom’s Dinner

Friday night we attended the Groom’s Dinner. This was for the bridal party and all the out of town guests to meet and be together one last time before the wedding. It was here that I met the groomsman who was to be my escort walking down the aisle. Sis and I both wore business -casual outfits of skirt, blouse, and jacket, with high-heeled shoes. My confidence level was rapidly growing. I knew I looked good and hence, felt very relaxed. Introductions were made for both Sis and I since we were strangers to most in attendance. I was introduced to my escort. He was tall and handsome, just like the man in my dream! Strangely, I seemed to be looking at him through the eyes of a woman, admiring his features, his charm, his smile…just "checking him out" in general. Why would I consider him handsome and charming? I found myself actually trying to impress him!

To my amazement, I recognized a familiar person…Elaine, a girl I had dated a few times. I had assumed everyone there would be total strangers to me. It seemed that Elaine was a good friend of the bride, Dee, and was also a bridesmaid. (I should’ve known!)

She didn’t immediately recognize me, in drag, so I was safe, for the moment. After all, she wasn’t expecting to see me, either, and certainly not as a girl. But I feared that would change when she saw me with my sister and associated the two of us, and it happened! About midway through the evening, she approached me when I was alone.

"Excuse me…Ali…is that you?" she said, with hesitation.

"Um…Hello Elaine."

I could’ve played dumb and denied it with some lame comment, but I thought better of that.

"Why are you here? And why are you dressed like that?"

"It’s a long story, Elaine…" I said, blushing. What could I say?

I led her to a table away from the others and proceeded to tell her the details of my situation, at least about being conscripted to fill in for Bonnie as a favor to Dee. It seemed Bonnie and I were approximately the same size, the dress, etc. She patiently listened, then praised me for being such a good sport to be doing this while complimenting me on my fem appearance. I was blushing noticeably. I had expected her to laugh or even make some unfriendly comments. Guess I didn’t know her that well.

We had dated, but I was never romantic with her…it was just a casual friendship. There didn’t seem to be any "chemistry" between us, though she is a nice girl. Then, maybe it was my fault for not pursuing a relationship. I had little experience with dating and was shy with girls. So it went nowhere.

 

But here, I was a "guy in a dress" and fully expected to be teased now that I had been discovered. Elaine was actually very understanding and impressed at my feminine presentation, how well I walked in heels, and talked with female gestures and expressions, my make-up, and natural hairstyle. She praised me highly for learning so much in such a short time, and promised to keep my secret. In fact, she treated me with great warmth, actually more so than when we had dated. We became instant girl friends and she stayed with me for the remainder of the evening. Sis noticed us together and was a bit concerned until I informed her of what had just happened.

Elaine and I spent the next day together, having lunch (her treat) and window-shopping. We had a lot of catching up to do, only this time I was a girl and had to maintain that image. I told her of my circumstance…that I had originally committed to remain as a girl only through the wedding, but that I accepted a job for the rest of the summer, working en femme. She was actually delighted to hear that and hoped we could remain as close friends…girl friends. My situation intrigued her and she found it all very attractive…found ME very attractive as Alana.

Odd, she was never this friendly towards me as a boy. Now, there was "chemistry."

 

 

The Wedding

Sunday afternoon, we arrived at the chapel for the wedding service. Wearing street attire, we changed into our gowns in a room designated for the bride and her attendants. Upon arrival, I noticed the other girls in all stages of dress or undress. Now, being one of them, I related to the others and proceeded to change into my dress. Even Elaine was semi-undressed yet treated me as a female peer. In fact, we zipped each other’s dresses, made other minor adjustments, and I helped her with her hair. Sis smiled her approval.

By now, I was very relaxed.

We took our respective places ready for the procession. I hadn’t attended any rehearsals but felt I would just observe and follow the others. At the proper moment, I took my escort’s arm and walked down the aisle to the bride’s position with the other girls, eyes straight ahead, stepping with the measured beat of the music. I sensed all eyes upon me as walked carefully with my bouquet in one hand and the other, held by a tall, handsome gentleman. No doubt, we made a nice looking couple. I’ll bet many people wondered who this strange young lady was.

I heard not one word of the ceremony. My mind was focused on the thought of what I was doing here…standing in front of a crowd of people fully attired as a woman…suddenly aware of the tactile sensations of this very feminine gown and the delightful caress of my undergarments. The embrace of the bustier…the tug of my hose and attached garters…the lift of my heels. I almost felt as though I was standing here in my underwear like a Maidenform ad. I felt myself begin to blush. What if I was the bride?

And then it occurred to me, where will all this lead me? Why did I commit to this? More importantly, why do I enjoy this role so much? What’s wrong with me? What will my parents say? What will anyone say?

I was jarred back to reality by the sound of breaking glass as the groom stomped the traditional wine glass ending the ceremony. (Customary at a Jewish wedding). The spectators began to cheer and applaud as the newlyweds rapidly departed up the aisle. The service was over. My escort took my hand and we quickly followed the others to join the receiving line in the lobby where we greeted all the guests, remaining until everyone had departed for the reception. Joining my sister and Elaine, we three stopped to freshen ourselves and our makeup to be ready for the next phase.

 

 

The Reception

At the head table, I was seated next to my escort during the reception dinner. I was cordial to him, but not overly friendly, not wishing to send any signals that I couldn’t handle later on, yet he was a very nice guy and it was tempting… I think he got the message. I would be lying if I said I didn’t have a few carnal thoughts about him, after all, I was in the role of a woman.

After the meal, we separated, and I joined Elaine for socializing and dancing. It doesn’t seem to bother anyone to see two girls dancing together (we weren’t the only ones) and otherwise staying together, behavior certainly not common among boys.

During the few hours of the reception, we got re-acquainted and grew closer than we had after several dates as boy/girl. Elaine felt noticeably more relaxed with me as a girl, and I certainly felt more natural as one in her company.

I saw Sis with some people, enjoying herself, so I kept my distance. Why complicate matters with introductions? I felt it wise to remain at a distance. Confidence?

 

The Workplace

I reported to work on the following Monday. Attired appropriately in a skirt, blouse, and hose. I chose low-heeled shoes not knowing what my duties were to be or how much walking I’d be doing. The long, full, skirt was for the same reason.

The day went well. Everyone was friendly and made me feel welcome. At no time did I sense any suspicion of my not being female. Perhaps due to my appearance and adopted mannerisms or to my feeling so naturally feminine. I had really adapted to this new lifestyle.

I learned my duties quickly. They involved many things since I was a "fill-in" worker. Everything from answering phones to filing, billing, and delivering mail. I enjoyed the variety and it afforded me the opportunity to meet all the staff. They were very nice to "Shirley’s little sister." She was obviously well liked.

One day, at lunch, Sis and I were chatting about cosmetics and makeup tips. She asked me if I would consider having my facial hair permanently removed. It seemed there were people on staff who perform cosmetic surgery and modifications such as hair removal. It hadn’t occurred to me but seemed like a good idea. Having to daily, sometimes twice daily, shave closely was such a nuisance yet a necessity, so I talked to a specialist who agreed to do it for me at no cost since insurance would cover it. She felt my problem was glandular, not uncommon for some girls, and permanent depilation would be very beneficial to my mental health. She’d submit it to the insurance people.

"No girl should have to live with facial hair. It’s so depressing."

I totally agreed, and the treatments began.

It was wonderful not to have to shave daily and sometimes twice daily. The smooth skin definitely improved my appearance.

Elaine was delighted with this modification. She and my sister were constantly working on me to improve my female appearance. What more could I do? I looked, sounded, acted, and felt like a woman. Well, there was talk of breast implants. I drew the line at that point. I was sure at some time I must revert back to a male existence.

 

Discovery

It had to happen. Not having heard from me for a while, Mom paid us a visit, unannounced. We arrived at the apartment after work one day to find Mom waiting for us. At first, she didn’t recognize me and assumed I was Sis’s friend or maybe a new roommate, but upon closer scrutiny, that quickly changed. When she regained her composure, she asked for an explanation of my appearance. I was not only dressed in my work attire, which was delightfully feminine, but I looked too good for an occasional crossdressing event. Hair and makeup done perfectly, pierced earrings, natural girlish mannerisms.

So we sat down over coffee and told her the whole story. From events leading up to the wedding, to the present time, and eventually regressing back to my childhood covert crossdressing and even before that. She took it all in stride with few comments other than how pretty I turned out. She remembered how I frequently played at dressing like a girl as a child and how much I enjoyed it. But she had never given it a second thought. It was just harmless play, she assumed. Many young boys play in dresses, jewelry, and lipstick, at times. It’s just a phase they go through, she said. Actually, I really think she was pleased at having another daughter.

We were a bit concerned about Dad and his reaction, but Mom didn’t think he’d be too alarmed. He never considered me to be a "jock," but rather, in fact, more like a sissy, so my turning feminine wouldn’t surprise him. Gee…sorry to disappoint him!

I told Mom about Elaine and how we’ve established a relationship albeit girl/girl. Where it will go, we don’t know yet. She raised an eyebrow over that bit of news. She knew we had dated and parted company. Now, Elaine liked me as a girl? That got a raised eyebrow from Mom. I wont attempt to interpret that.

Where it goes from here, I don’t know. I’m very happy now. My life as Alana is good…My job is good…it may become prolonged as I attend business college part-time. I’ve settled into this lifestyle as a woman and being accepted as one. I’ve even established new ID, bank account, and driver’s license as Alana. Elaine prefers me this way and intends to remain with me. We’ve talked of living together. We haven’t had sex yet, but have had several "close encounters."

Neither of us are interested in boys although Sis is, and maybe I’m in the way, living with her.

I’m sure I’ll have to resume a male existence at some point though it wont be easy. I’ve gotten so very feminine. I’d need to re-learn how to be a guy. Elaine and I have established a social life with other girls. It would be difficult to give that up and start over as a traditional couple.

And if I don’t?

 

Epilogue

I did revert back to the male mode eventually when I made a career move. I had hit the glass ceiling as Alana so, remorsefully, it was time to bring Alan back, not without some difficulty. My appearance had become so feminine…no beard, pierced ears, permanently trimmed eyebrows…as well as established fem mannerisms and speech patterns, it was a major transition to be a man again, and not a happy one..

 

I knew I couldn’t maintain this female identity forever, but I do bring Alana out as much as possible, and my wife, Elaine, still prefers her presence. It seems, as I get older, Alana’s visits are longer. Even our children enjoy her company. Someday she’ll return permanently.

 

 

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