The Office Party - Part 3

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The following Saturday, I took the train into the area just north of the Chicago Loop, where Heather had an apartment. Theresa and Megan were to join us.

“Let if we can outfit you to be a pretty girl,”  Heather said. “I got some outfits that you can wear for the occasion, Shelly, I know Megan will be bringing some.”

“Oh, I’m so excited,”  Theresa giggled when I agreed to the fitting. My rational mind told me I was crazy for going along with the two girls’ idea; I would have enjoyed staying at home for an extra day since I was somewhat behind in working on mom’s business. What I couldn’t fathom now as I boarded the bus from our northside bungalow was why I agreed to it? Yet, I knew deep down I truly wanted to see how I’d look all fixed up to be a girl.

Heather lived in a second-story apartment in a posh neighborhood, just a block west of Lake Shore Dr. I tied my hoodie tightly about my face as I walked the several blocks from the bus stop to her building, heading into a brisk, damp, chilly wind off Lake Michigan that bit into my face. I loved Chicago, particularly its vitality and energy, but on days like this, I wondered why we continued to live in this challenging climate.

I knew Heather came from wealth and guessed that she could afford to live here because of support from her family. Certainly, she couldn’t do it on her wages from WEI. Her apartment was in a red-brick building that had clearly been renovated in recent years, complete with a well-painted black iron fence, cleanly manicured landscaping, and neat front steps. I pressed her buzzer at the entryway, and when I heard Heather’s eager voice I announced myself.

“I’ll buzz you in girl and I’m on the first apartment to your right at the top of the stairs. No. 3,” she said cheerfully.

“Girl?” I said to myself, as the door buzzer sounded. It bothered me: maybe I should leave, but I opened the door to enter, anyway.

Heather and Theresa both were waiting for me at the top of the stairs, smiling broadly. “Here’s our girl,” Heather said.

“Yes, there she is,” Theresa said, with a grin.

“Girl” and “she.” More of that nonsense, I thought.

Nonetheless, I smiled, did a mock limp wrist movement, and followed that with a slight curtsey once I reached the top of the stairs where I was quickly hugged by Heather and then by Theresa, who also added a kiss. It was just the kind of hugs and kisses that girls so often exchange with each other.

Heather’s apartment was surprisingly roomy with a broad front window that looked South and even on this gloomy Chicago day was cheerful and bright. The walls were painted with a light, peach-colored tint, and modern prints, many in bright colors hung on the walls. The furniture was light-framed with accented colors. Along one wall was a bookcase, though stuffed to near-overflowing with books, was broken with fluffy animals. I had thought of Heather as being a bit flighty but could see now she was a serious, intelligent girl who was not afraid to show her femininity.

“I thought Megan was going to be here, too,” I said.

“Oh, she called me and told me she had to take her mother to the doctor and the grocery store today,” Theresa said “But she and I are about the same size, and we found three outfits for you to try on today, Shelly,” Heather said. “I think you’d look darling in any of them, but we think you should try them on to see what you like, honey,” Theresa said.

They led me into the bedroom. What a lovely room, I thought. Everything was a mixture of pinks and whites, with some highlights of violet providing accents. A fluffy duvet covered a double bed, with three white stuffed bunnies gathered together atop pillows; gauzy curtains framed the one large window, and the same materials covered the cushions of a rocking chair and vanity.

“First, honey, we want you to take a nice warm bath,” Heather said.

“But I shaved and showered this morning,” I protested. For me, shaving is kind of a joke, since I grew hardly any beard on my face and little fuzzy strands of hair on my legs and underarms.

“Oh, poor girl,” Theresa said. “To be truly pretty, a girl needs to feel sweet and smell nice to start with.”

I scowled at both of them. What was I getting myself into?

Yet, I agreed and soon found myself in a tub covered with puffy bubbles and scented water, where I sat in warm comfort for about ten minutes, before Heather rapped on the door. “Time to get out and dry yourself, Shelly girl,” she said. There was that “girl” thing again.

They had left a pair of satiny-looking white panties with a cute pink ribbon in the front and lace trim for me to put on, but that was all I would wear before I would reenter the bedroom. My long hair was in a ponytail, but when I looked at myself in the mirror, wearing only the panties, I saw how puny my upper body looked and suddenly was ashamed at how unmanly it must appear. It would be humiliating to appear before these girls almost nude. So I wrapped a towel around my body, covering from it the breasts on down, realizing that’s how I’d seen my mom as she would leave the bathroom. I must have looked quite girlish, I figured.

“Wow, what a girl!” Heather exclaimed as I moved into the bedroom with the towel draped over my breasts.

“What girl wouldn’t kill for a lovely body like that!” cried an enthused Theresa. “I’m jealous.”

There praise prompted me to sashay about in mock feminine form, bringing giggles to all of us and causing me to lose hold on the towel, letting it fall to the floor, and leaving me standing there totally bare-skinned, except for the panties. The whole exercise had so stimulated me that my penis grew hard, creating a tiny tent in my panties, which I quickly covered with my two hands.

“You don’t need to cover that up,” Heather teased. “There’s not much there anyway, is there?”

“No,” I said, a bit humiliated by the whole episode. My male appendage certainly wasn’t terribly manly, I knew, but it did cause a noticeable bulge in my panties.

“Nonetheless, we’ll have to make sure we do something about that,” Theresa said.

“Don’t worry, I thought of that and I have a gaff for her to wear,” Heather said.

“You thought of everything, haven’t you?” I said.

After the girls had put a bra on me and stuffed it with sponge rubber filler, I tried on the three outfits they had chosen from Heather’s closet. The first was a faux-wrap dress of a soft stretch violet-colored material that seemed to cling to my body. It had three-quarter length sleeves and ended at just above the knee. It fit like a glove I was surprised to feel it felt so comfortable on me.

“You have such lovely legs, Shelly,” Theresa remarked.

“The dress creates such a feminine silhouette,” Heather continued. “You appear to have such a naturally girlish body, Shelly.”

I moved over to the full-length mirror affixed to a closet door to see myself, astonished at realizing I did indeed — even without makeup and with my hair tied back — look convincingly female. My shoulders were narrow and my arms lacked muscle mass, creating a truly feminine shape.

“I love the dress,” I said.

They helped me out of the dress, and assisted me to step into a salmon-colored cocktail dress with thin straps over the shoulders, exposing them and my arms. It was of a more satiny material with dark red piping placed discreetly at the hemline and across the bodice.

“I think that’s better for her,” Heather said. “I think she should wear something a bit more formal.”

“Oooooh,” gushed Theresa. “I wished I had pretty arms like you Shelly so I could wear something like that.”

“Oh you do have pretty arms,” I argued.

“Nah, not like yours which are so soft. My muscles show too much.”

She was right, of course, since she had such a pert, compact figure, her sinewy body showed prominently when she wore sleeveless dresses in the office.

“But isn’t this dress only for summer?” I asked. It could be below zero on the day of the party since we lived in such a snowy, northern city.

“Not with this,” Heather said, producing a short black jacket that would be worn to cover the shoulders. It looked divine on me.

The other outfit was a pleated, plaid skirt with prominent red and greens, with a white blouse and topped off with a Christmassy sweater jacket. I loved it, but the girls thought the cocktail dress would be just right for the occasion.

Later that afternoon, after the girls had worked on my hair, brushing it and leaving it to flow freely with bangs, they dragged me out with them to a bar on Division Street that seemed to be populated by stylish 20-somethings. I wore the skirt, blouse, and sweater combination, but covered it with a warm, light grey jacket and a pink wool cap. On my feet I wore flats, and as I walked with them easily mimicked their short steps and girlish mannerisms.

We found a table near the entrance, and all three of us ordered cosmos, a fitting drink for young ladies, I guessed. I had turned 21 a few months earlier, but normally I was carded; I worried that if that occurred I’d have trouble explaining why a young lady would have a driver’s license for a “Shelton McBride,” whose gender was listed as “m.” The male waiter, obviously a graduate student or even a law student at one of the colleges who did the job for money, was courteous and friendly but didn’t bother with IDs. I thought he look most closely at me, and I wondered whether he realized — or suspected — I was really a boy. Or, maybe, he didn’t think I was 21.

“He’s a hunk,” Heather said. I had begun to realize that Heather always seemed to be on the lookout for new boyfriends, as I noticed her eyes wander often.

“But he only had eyes for Shelly here,” Theresa said.

“I noticed that,” Heather said. “Looks like we’ve created a monster.”

“But a mighty pretty one,” Theresa giggled.

As the hunk presented our check, he looked directly at me and asked: “You girls from around here?”

I blushed, too surprised to answer, and was pleased when Theresa told him: “Just Heather here.”

“You all students?” he pressed on.

Theresa said we all worked at Women’s Equality Illinois. The information seemed to set him back, and I’m sure he must have figured the three of us were hardened feminists, maybe even lesbians. That often was a misconception about the girls who worked there, but in my uneducated observations, I believed virtually all of the staffers seemed to be married, have boyfriends, or were searching for boyfriends.

“Don’t worry, waiter,” Heather plunged in. “We’re all perfectly normal girls who like guys.”

I was shocked to hear such frank talk; Heather seemed to have no shame.

He smiled: “Well I hope to see you all again soon.” He walked away, but not before giving me a slight wink.

“Damn, he was only interested in you, Shelly,” Heather said.

The girls insisted I continue to wear the outfit I wore to the bar on the bus trip back home. “Let your mom see what a pretty girl you are,” Theresa said. I protested, saying mom might be shocked at me arriving home dressed as a girl. My protests, of course, weren’t too strong, since I was excited to show off how pretty Heather and Theresa had made me. Actually, mom may not have been too shocked, since I had become such an accomplished makeup artist and she had seen my “silk purse” routine many times, usually commenting on what a lovely face I had. Once she had even remarked that I would have made a “pretty daughter.”

As I boarded the bus, the driver, a jovial, round-faced African-American man, greeted me: “Welcome aboard, miss, on Chicagoland’s premiere bus route.”=

I smiled back at him as I slid my $2.10 fare into the farebox. “You certainly bring a bit on sunshine onto this humble bus,” he quipped, speaking loud enough for the passengers in the front rows to smile.

Naturally, I got looks from virtually all the passengers as I ventured forward, fortunately finding an aisle seat next to a middle-aged, gray-haired woman who was holding packages on her lap.

I carried a large plastic shopping bag that held my boy clothes, which I placed on my lap as I sat down, hoping I didn’t look too awkward as I attempted to smooth the back of my skirt as I sat.

The woman moved more tightly toward the window as if to give me more space, and I instinctively said “thank you.”

“Been shopping, too, young lady?” the woman said as I settled in.

“No,” I smiled at her. “Just visiting girlfriends today.”

“Oh,” the woman said. “Seems like I spent the whole day looking for Christmas gifts for my grandkids.”

“Bet you enjoyed that,” I volunteered.

“Yes, but you don’t know how much toys cost these days. Just wait ‘til you have grandkids.”

I giggled, picturing myself as a 50-plus-year-old woman bragging about my grandchildren.

“Time goes fast, darling,” the woman said. “Pretty soon you’ll be a married woman with kids. You must have a boyfriend, I bet.”

“No, not really.”

“Such a pretty girl. I figured you’d have boys hounding you. But, that’s good, dear. You don’t want to rush things. We get old so soon.”

What a weird conversation, but I joined it willingly, playing the part of a young woman, who though being pretty, was without a boyfriend. It seemed so natural.

“Merry Christmas, dear,” the woman said as I rose to get out at my stop.

“Have great holidays, young lady,” the bus driver said as I was about to step off his bus.

I halted at the top step, looked back at the bus driver, gave him a flirtatious smile, and said: “Thank you, sir, for a ride on Chicagoland’s premiere bus route.”

He burst out with a jovial laugh. Was he not Santa Claus in disguise?

Of course, mom was shocked, but it didn’t last long. She wouldn’t let me change into my boy clothes, suggesting I continue to wear the skirt, blouse, and sweater for the rest of the evening.

“Now you must tell me all about it, dear,” she said, suggesting that we share a bottle of wine together before she fixed supper. She couldn’t take her eyes off me, as I told how the girls had me try on various outfits. She wanted to know the details of each one; when I explained that I would be wearing a salmon-colored cocktail dress to the Christmas party, she smiled.

“That’s exquisite. You’ll look just divine, darling.”

That night as I prepared for bed, mom walked into my room with a pink girl’s pajamas on her arm.

 “You better wear these tonight, Shelly,” she said. “These are more suitable for a girl.”

“Oh mom, I love you,” I said, running to hug her.

I was so happy and excited that sleep came slowly that night. Mom had accepted me as her daughter!

I don’t know how Heather, Megan, and Theresa did it, but they told no one about my transition, so things at the office continued to be continuing as normal. I continued to assist the staff with their computer problems, the girls continued to be grateful to me and Penny Hartshorn kept her scowling visage. Virtually all of the girls put some form of Christmas decoration in their cubicle. As the only male in the office, I did as well, stringing some garlands around the top of my four-foot walls with a few ornaments hanging from them. I resurrected a tiny lighted Christmas tree from our storage area, and set that up as well, even wrapping a few small boxes in holiday paper with bows.

Theresa giggled at my fastidious decorating and teased me quietly, telling me I gave my workspace a real ‘” woman’s touch.” She was right, of course.

The three of us told Carolyn about the plan to make it possible for me to attend the Christmas party since her approval would be needed. She accepted the idea readily, though all five of us were uncomfortable with the need to lie about me by misleading everyone into thinking I was a girl.

“Oh well,” Carolyn said. “It’s a silly rule anyway. You may come as Michelle McBride. I’ll inform Penny to add your name. She may not like it, but I’m the boss here.”

Later that same day, I was surprised to have Penny drop by my cubicle; her soft-featured face, a layer of fat under her jawline, was actually smiling. I couldn’t ever remember this woman smiling before. I was struck suddenly with the fact that this overweight woman had such a pretty face. I had never noticed that before, and I realized that it was her warm smile that suddenly made her beautiful.

“Welcome aboard, Michelle,” she said softly to me, so as to not be overheard. “Of course, we’ll be glad to have Michelle McBride join us at the party.”

I almost slipped out of my chair at the woman’s complete about-face in her attitude toward me. I mumbled some form of thank you, and she moved off, leaving me wondering what was going on with the woman, who had seemingly despised Shelton McBride in the six months I had been with WEI.

I guess you could say I came “out” at the Christmas Party. I doubt if I’ll ever forget how warmly all of the women on the staff of Women’s Equality Illinois treated me. They gathered about me as I entered along with Heather, Megan, and Theresa, my sweetest girlfriends. Fortunately, the room was warm — a rarity in many buildings in Chicago in the cold December weather — and I was able to take off the light jacket and show off my pretty shoulders, neck, and arms.

Mom had trained me well in the week leading up to the party, showing me how a proper young lady sits, walks, eats, holds her cup, and sips her wine. “You do this all so naturally, Shelly,” she said.

It was true, I guess since I had basically been in all-female environments most of my life, and obviously, the mannerisms must have been etched into me. I remember, too, the many times I had been called a fag, sissy, or girl by bullying boys.

Needless to say, I had a lovely time at the party, enjoying the fashion show and the shopping for bargains afterward, even buying a lingerie set and a lovely evening dress at unbelievable bargain prices.

Penny Hartshorn surprised me by joining us younger girls at our table as we ate our buffet lunch, even sitting next to me. I could not believe that this dour woman could be such a lively companion; she thrilled the girls at the table (including Heather, Theresa, and Megan) at stories that seemed to make fun of herself and her weight.

I found myself sitting next to her at the table, and noticed that several times her knee and mine seemed to touch. She also touched my arm as she talked, leaning over at times to whisper in my ear. As we began to leave, she called me aside and suggested that maybe I’d like to join her for dinner some night at her apartment. “I’d love to cook for you,” she said.

I nodded in apparent agreement but wondered whether I should have stifled such a notion on her part. Nonetheless, she sounded sincere; it seemed obvious, too, that she may just be yearning for companionship. I was sure she was at least ten years older than me, and couldn’t see why she was suddenly so interested in Michelle McBride.

I hugged just about every girl in the place as we broke up. It was the merriest of Christmases.

One Year Later

The committee planning the Christmas Party for the following Christmas included Penny Hartshorne, Heather, Theresa, Kathleen, Megan, and me. Carolyn had prevailed upon the sponsor of our party to pressure the Women’s Club to change its policy to permit men in its ballroom. It took some legal maneuvering, but it was accomplished.

Again this year, we had a young man, and young Irish immigrant name Kevin O’Shea who turned out to be a whiz as both IT guy and website manager. I have to admit he may even been better than I was.

Early in the year, Carolyn had been convinced that the agency should take up the cause of providing equal rights to transgendered persons, based largely on my experiences in trying to obtain a name change to Michelle Marie McBride (three m’s, don’t you think that’s cute?) and getting an Illinois driver’s license as Michelle. She recognized, too, how difficult it might be for transgendered men or women to get jobs.

“Shelly,” she said one day in June, “Shelly, you will lead our campaign for transgendered person rights. That means no more IT work for you.”

To be truthful, I was overjoyed. Once I had assumed a fulltime role as a woman — which I did in early January after the Christmas Party — I seemed to have come out of my shell. I had joined an advocacy group for gay rights but was upset that they seemed to care little about women and men like me who had transitioned. I told Carolyn about the issue and to her credit she agreed to bring it up before the board of the agency, even inviting me to tell me the story to the board to dramatize it.

I must have done a good job since they approved the idea quickly. I even cried when doing so, but it wasn’t an act: the tears were real.

In July, I moved in with Penny Hartshorn. We were lovers — women lovers. She wanted no part of me as a male, it developed, and with the hormones I was taking I know I couldn’t have been much of a man anyway — if I ever was. Within a couple of years, I knew I’d be having sexual reassignment surgery. I could hardly wait.

Penny was love-struck and kept telling me how feminine and dainty I was. She loved to lie in bed with me, drawing me tightly into a soft, warm body, as she caressed my tiny shoulders and slender arms. Our kisses were wet and sweet.

I enjoyed the task of making Penny over, which she had accepted with eagerness. We both stayed on a strict low calorie, low salt diet, and took almost daily advantage of the fitness room in her apartment complex. I loved working on her face; she was truly pretty. By the time we began planning the Christmas party, she had lost weight and lost much of the fat under her chin. She was truly a beautiful woman, and I was in love with her.

The only regret I had was that mom seemed hurt at first that I moved out, but that quickly changed. I continued to help her with her business, with assistance from Penny, who truly was great with the details of running a business. A month after I moved out, an old boyfriend of mom’s called; they had dated for a while in high school, and he had recently become widowed. They soon became constant companions. Mom was so happy to introduce him to her lovely daughter … me!

And then in September, Heather and I were bridesmaids for Theresa’s wedding, which was a huge event in a Catholic parish frequented by Mexican families. I had been used to Polish weddings, which were always elaborate affairs, but this seemed only bigger. The bridal party all wore gauzy dresses in yellow with an off the shoulder drape. I loved looking at the pictures: the girls were all so lovely. It may have been my shameless vanity, but I honestly thought I was the most feminine and most beautiful of the entire party.

We were so happy for Theresa: her boyfriend was a doll and a very accomplished music teacher in the Chicago Public Schools. He played a mean guitar and keyboard for several songs at the dance afterward. I was pleased when Heather caught Theresa’s tossed garter, and thus soon might be ready for a wedding, too.

I continue to get flirting looks from men of all ages, which is flattering. However, when I’m out with Penny, she gets a bit testy if men look at me too closely. I really wasn’t interested in men; I was in love with Penny.

We were going to have a marvelous holiday together, I was convinced. Merry Christmas to all!