Must Be Dreaming - 3 New for Christmas

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Must Be Dreaming - 3 New for Christmas

By Jessica C

The guys and women were back together having breakfast, this time near Chicago… Friends in high school, some longer… together for a weekend away from college or work... The guys were pumped up for a weekend of football and pub jumping… When Jennifer asked, “Josh come with us…” Jenn figured on Josh as Josey staying with the women that day…


Mom and I were both glad that Miya would go shopping with us. I selected the clothes that I like. Miya was nice enough to say diplomatically that not everything looked good on me. “Josey, it might be helpful to have someone who is good at it, figure out what are your colors.”

Momma said, “Aunt Cathy mentioned a store that is supposed to be good at just that. It’s called Fashion By Design. It was north of our campus; Miya knew where it was on Michigan Avenue. Miya said, “Whenever I go there, I loved their clothes but can’t afford their clothes except when they’re on a big sale. That’s usually when we’re usually back to begin the spring semester.”

Once we were in the store Mom asked for Doris, hoping she could help us. Mom introduced us saying, “Doris, my sister Catherine Hampton suggested I ask for your help. My daughter Josey goes to Northwestern and has finally outgrown her tomboy stage. She needs some help in knowing her colors and the styles of clothes that might be good for her. Her friend Miya goes to the same university and is looking to get something nice for her mother. Do you have someone who could help us?”

She introduces herself, “I’m Doris Malone and while I’d be glad to help you. Cyndi is our sales associate that I’d recommend we use. She is gifted in figuring out a person’s colors and work with you to find out what you like most.”

While Doris waved Cyndi over to help us. Miya said, “Mrs. Greene, This store might be a great place for ideas, but I don’t think I can afford getting a jacket for my mother here.”

Momma said, “Well let’s see if they can give us a good idea then about what to look for in an evening jacket.”

Cyndi’s a one of those cheerful sales people who make you feel good just coming in, without being overpowering. She showed me that I look nice in a light mint green as well as certain yellows but not greens with a yellow tint. Suggesting I could use makeup to give myself added color. She also showed us a red dress that flared out, giving my body the feminine look of having girl more hips than I really do. She says, “There are times you want to show of your petite frame. But I think when it comes to your little red dress, you probably want to emphasize a classy way to say, you’re a young woman here to have a fun evening.”

She was amused as I was shaking my head yes, when I like her ideas. She tested me a little by suggesting an old fashion lace dress that many like. I didn’t even need to try it on, to determine it wasn’t my style. Cyndi said, “You did well in speaking up. This would look very nice on your friend here.” She had lifted the dress holding in front of Miya so she could see it in a mirror.

“Miya dear, this designer usually has a good sale on their merchandise come the third week of January. If you mother would come and visit you then, it will probably be reasonably priced.

She said, “I suggest that both of you women include some nice quality dresses and gowns for when you put together your professional wardrobe. It will be worth it when you work with those who have ample dollars to help fund some of your environmental projects.”

Cyndi says, “And oh by the way, come early spring if you would show Doris and I some ideas on how a person with a small estate of 20 to two hundred acres. Could tackle a project of renewing their estate while being environmentally sound; we might be able to help line you up with a summer project that would also pay well.”

I did not expect we’d get the red dress I liked, nor the long mint green skirt that is nicely lined for winter wear. The skirt is more for everyday wear, but pending on how it is coordinated with other clothes it could be very versatile.

Well my mother agree to the red a dress and two skirt outfits, including the mint green skirt. Cyndi and Mia helped me select two sweaters, a camisole and three more blouses. That would broaden my wardrobe.


My Mom had Miya and I visited among ourselves, while she talked to Cyndi

Mom came back saying, “Miya, Cyndi says, she’s met you and your mother before. She asked me if it was true that your Mom is a professor out east. I had to confess that we hadn’t met and I didn’t know.”

Miya turned to my mother, “She’s an Associate Professor; she’s been on their college staff for seven years. She’s very good, but the university would need to pay her at least another $7,000 a year if she’s a full professor. The past two years students have petitioned for her to become a professor. Mom says the university is looking for someone to give the minimum of $250,000 to fund a chair for her.”

“Well Cyndi said she’s sure your mother is under paid, despite being a good instructor and a great human being. She saw you eyeing a silver evening jacket.”

Mia responded though not very enthusiastically, “Yes, my mom has two black gowns for more formal affairs for their college as well as special times she goes out with my dad. They’re still nice though she had them for a while. I thought a silver dinner jacket would spice them up a little and given her a fresh look. I was planning on spending some good money to buy a nice one. The ones here are great but more than I can spend.”

Cyndi is coming back with two long black evening gowns. Miya saddens even more, though the gowns are quite attractive. I’m surprised, so I ask, “What gives, the gowns look beautiful.” I can tell Miya wants to walk away as she’s ready to cry.

I overhear her muttering, “Damn, this is embarrassing.” I’m certain she did not intend on me or anyone else hearing her. “It’s my fault, if I’d gone to the university there it wouldn’t be so hard on her.”

We talked, it was true that she could have gone to the university her mother teaches at, and with scholarships, books and board would have been all she’d have to pay. Their own counselor however said she should apply to be accepted at Northwestern and two other highly recommended schools. It was here at Northwestern that I got accepted and offered a major scholarship.

“Well said,” Cyndi agreed, “But we’re not here to embarrass you. What we’re offering you is the chance to purchase the evening jacket as well as a new evening dress to go with it. Our expectation is that in the future when you can afford it. Fashions by Design will be one of your shopping places in Chicago.”

Miya reluctantly looked at the dresses and asked, “Would it be possible for me to try on both dresses as well as the jacket? My mother and I share the same built, we wear a size six dress, though we need to go up to a size 8 in the jacket for her.” While both gowns were very beautiful, it was easy to tell which one would look best on Miya thus her mother.

Cyndi offered the jacket to Miya for $125 a far cry from the price tag that was just under $300. It was, however, still fifty dollars above what Miya had to spend. Miya paid ninety dollars, agreeing she would owe my mother thirty five dollars plus the tax. That left nothing for the beautiful evening gown.

My mother and Doris the manager said they would each cover a hundred twenty-five dollars for the discounted price of the black evening dress that Miya chose. My parents are not rich people, but mom rationalized it to me saying, “This young woman is my opportunity to pass on the blessing of you coming out along her being a new friend.”

Finally done shopping there, we went to a regular department store where my mother had me select a half-dozen pairs of panties and a couple of bras. My mother asked, “Josey, how did you decide on the size of bra to wear.”

I smiled, “I chose this bra with Jenn’s help. We decided, I would look better with a B cup. It is different enough with breasts this size. They feel nice to me, but I’m still getting used to having them.”

I heard a slight giggle and turned to see Miya with a hand over her mouth. She said, “I’m sorry but I’m not use to someone describing their breasts quite like this.”

Mom stepped to me, making sure she had my attention, “Josey, I want you to begin to be more intentional about what you’re saying. You need to think about how want you say to others comes across. If you begin doing that around family and friends; it will be the fastest way to make it Josey’s style to do so.”

Our last stop, I was fitted with an expensive pair of breast forms. I was tickled by how they looked and felt.


Mom dropped us off at our residence hall along with our packages. Patti thanked my mother for the meal as well as helping with her mother’s gifts. We were in the elevator and Patti asked, Could we talk when I get off on my floor?”

Off the elevator Patti said, “Tell me to mind my own business if you want. But my suggestion is as you transition don’t rush to any conclusions about who you’re in love with. I know you have strong feelings for Jenn. But once you begin hormones in being Josey you or Jenn could change.” I looked at Patti as though she was crazy if not hurtful.

She said, “When my brother embraced his feminine side with his girlfriend’s help Teri was so sure they’d love each other forever. She was the first to fall out of love and Teri has since jumped back and forth if she loves this guy or that girl more.

“I can’t claim to be overly objective, if you come back as Josh or Josey, I’m interested in you.” Patti gave me a quick kiss like she was stealing an opportunity. I was surprised by how much I liked it.

I stared at her, “I’d like being your friend. But I can’t imagine me ever changing that way.” I gave her twenty-five dollars back like my mom asked me. “My mom was afraid you used your expense money to get home. She didn’t want you traveling with nothing.” Looking at her expression, I’m sure my mother was right. Patti stepped up gave me a hug and I knew she was deeply moved. I got back on the elevator and for some reason couldn’t put her thoughts out of my mind.

I did spend three hours reviewing noted and studying for my last final exam. I was happy to see Dr. Saunders in the morning and her warm smile when I went in to take my exam. She said, “I appreciated you letting me know who’s taking the exam. Please sign it for Joshua. I look forward to having this new you for class in the future. You look very happy and content.”

When I was done the exam and handed it in; Dr. Saunders gave me a small gift. By its shape I was sure it was a pen, but it ended up being a lip-gloss. There was a note, “I think you commented on this color when I wore it. It should go well with your complexion. Merry Christmas.”


Mom picked me up at 12:30 and we were soon on our way home. I did pick up my dirty clothes at my old room and some books and the gifts I desired to take home.

We were half way home, I received a text from my older sister Andrea, “Call me, I have good news for you Josey.”

I quickly called as my Mom and I were both anxious in different ways about her good news. I forgot to change my voice to Josh’s but Andrea was happy to hear it. “Hey Sis, I like your voice. I told Mom I was expecting Arnie to ask me to marry him, but I beat him to the punch. I love you and my friends too much to change to his ways. I need to raise my standards a little and not fall for guys like that.”

I wasn’t sure if I should say, ‘I was happy or sad for her.’ “I’m kind of sorry Andi, Mom said you fell hard for him.”

She asked, “Are you wearing home something Mom bought for you? I really want to see what you look like now.”

“Yes, I’m coming home as Josey. But if you want to see a picture of me go to Jenn’s FB page.” Mom and I heard Robin and Andrea say “Wow.”

Mom took the phone, “So what do you two think?”

Robin took the phone there, “We can see how much she looks like us. We were afraid she wouldn’t look quite like a girl. Needless to say we like how she looks.”

During the rest of our trip home, I talked to Mom about what Patti said about me possibly changing. Mom said, “If it is like when your sisters hormones kicked in; there might be something to what she says. I expect you and Jenn are so close that won’t change.”

Mom said, “After I heard from Jennifer. I did make an appointment for you on Friday with our doctor.”

“Yuck, I don’t want to see Dr. Tilleson quite yet.”

Mom half giggled, “Not Tilleson, your sisters and my doctor. I know you haven’t met Dr. Sarah yet, but I expect you’ll get along fine. Her warm nature has helped girls like you through their change into womanhood.” That surprised me as I didn’t think that stuff didn’t happen where I grew up.

Once we’re home, it is the first time seeing my sisters rush out to help bring in my stuff. Andrea hurriedly found the dress bag and carried it up to my room. Robin was delighted to find my new shoes and to help carry them in. I was carrying in my biggest case when my feet slipped on the light coating of snow. My feet went flying into the air and I fell on my bottom with my skirt flying up. The back of my skirt must have flown up or skidded back. When I landed my panty and butt were fully in the snow.

I remembered times that happened to my sisters and once to my mother and each time I laughed. It didn’t seem so funny today. I cautiously made my way into the house retrieving and carrying what I had. Jenn was soon over as well as another shopping friend.

It seemed everyone who knew about me wanted to see the new clothes I had and if I changed into more of a girl since they last saw me. Robin was bringing out and showing some of my new clothes faster than I could. Jenn insisted I try two dresses that with my nice bra that would show off some cleavage with my new breast forms.

“Wow Mom, you’ve blessed Josey with some nice boobs. You know cute babies like that could get her in trouble with boyfriends.” Several there were teasing me and asking what I was looking for in the way of a boyfriend.

I hastily said, “I’m not interested in boyfriends!”

I was surprised and a bit saddened to hear Jenn say, “She’s says that now, but what will happen when the hormones kick in?”

It was shortly after that I complained of being tired saying I needed to rest. Most had gone downstairs and were soon leaving. I was lying on my bed sulking when I heard the door creak open. I soon knew it was Andrea and Jenn. They each sat on different sides of my bed and Jenn’s hand was sliding up one of my legs. “Did I touch a nerve, when I said something about your hormones? …You know that I love the new you even more than Josh. But it doesn’t mean you’ll be the same once you’re on hormone replacement therapy.”

I turned to sit up and had to scoot my feet in to me. Andrea and Jennifer both had caring expressions as they smiled. Andrea lifted my chin to get me to look up. It was a family habit that we were to look up and not sulk when talking about problems. Andrea said, “You know this is what you want. You can’t expect to go through it with all roses and no growing pains. Jenn and I will be there to help you through.”

Jenn used a tissue to dab some of my tear drops. She said, “Josey it scares me too. The idea of you attracted some dick guy is unnerving, but we both need to accept it is possible.”

I changed my skirt and fixed my makeup and we went downstairs as my father had come home. He wasn’t quite ready to see me as Josey sitting next to Jenn. There I was pulling at the hem of my skirt to hold it in place.


It wasn’t until I went up to bed to sleep that I realized the comforter on my bed was changed to one of my sister’s with red and pink waving stripes. There was even a poster that Andrea had that she knew I liked. I looked for a pair of old pajamas and found a satin nightie with a Hersey kiss on top of it. “From your loving sisters.” I had cleaned my face taking my makeup off, but did not yet have a moisturizer.

It was then I heard a knock on the door and my sisters invited themselves in saying, “We’re inviting ourselves to your room for our own sleep in.” Robin spritzed a fragrant perfume she has.

“Thank you for the nightgown that was nice of you,” I said.

Andrea looked at me closely, saying, “It appears you forgot to use a moisturizer as well as pinning up your hair.” …The paused saying, “That is alright, we’ll help you do it. It’s the least we can do for sleeping in your room tonight.

“This is all pretty new for our younger sister. Me on the other hand, I’ve known you as I caught you and helped you to dress better. But I never thought that would come to this. But, we’re both happy to have you as a sister.”

I said, “No, you should tell us about Arnie. I heard you were hot and heavy for each other. So why aren’t you getting engaged like everyone thought?”

“Well,” she said, “He took me home for Thanksgiving as you knew that was the beginning of the end. They are so prim and proper as well as judgmental toward anyone not up to their standards. I was surprised that I was passing their approval in being good enough for their beloved son. His Daddy even went so far as to say I would be good for their gene pool.”

“It was when Arnie said, ‘While I’m as proper as I might be that he was sure I would come around and fit well with the family.’ Heck, I would have gagged on my own vomit before I would give to their ways. Body wise he was a nice stud, but I guess it ended with his outward appearance. The past few weeks he sought opportunity after opportunity to propose to me. I avoided trying to say no or anything mean, but he wouldn’t take a hint. Finally when I told him, I was sure I would never measure up to their standards. He still didn’t get it. Finally I said, ‘F*** off Arnie, you don’t get it. I like my life and truthfully I won’t lower my standards to your family’s mindset.”

“Does that satisfy you? I know Mom thought it might have been on account of you. But I did it before you ever came out as Josey. You being Josey, just makes me feel that much better about my decision and our family.”

I told my sister about my friends and me getting together before the exams. My sisters knew about that from other years. But I had previously stayed with the guys as expected. Jenn and Cora pushed for me to be with them and Ainsley and Megan liked the idea as well. I hadn’t expected I would be dressing as a woman, but I ended up being the only one of us who was surprised.”

Robin asked, “Did you ever get to feeling you were another one of the girls?”

“Yes, but I can’t remember trying or when it happened. They were calling me Josey and somewhere that day Josey was there and Josh was invisible. When I was ready to dress back as Josh and return to the guys. They gave the option of Josey staying with them. I was in love with Jenn and being Josey.”

It was three o’clock in the morning and we were settling down when Robin remembered a time. “I remember a time when I was thirteen and we were out as a group. I really didn’t think boys were that big of a deal? Dean surprised my with a kiss and my panty went warm and moist in one second. I wonder if that might happen to you Josey.”


I was kept busy Thursday changing over my room, wrapping gifts and I was having fun. I chose a dusty rose and yellow for my main colors of the room. Somehow it being important sound silly as I am rarely home.

Come Friday morning Andrea couldn’t go with me to the doctor, and somehow Jenn came with my mother and me instead. Mom and Jenn assured me I looked like the other women there, but I was sure I was seen as a guy. I was sure I stuck out as a boy. Alas even my deodorant had a lite feminine fragrance. Nurse Meg called me back, “Josey would you please come with me. First we need to weigh you and get your height.”

Nurse Meg asked, “You’re happy when most girls aren’t. What gives you’re happy to hear how much they weigh.”

“If your scales as correct I’ve lost another three pounds.”

“Dr. Cooling will be like hearing about that from you.” Meg takes the vitals a part of my history before the doctor comes in and introduces herself.

Dr. Cooling came in to the exam room, “Hello Josey, it is nice to meet you. Your mother informed me a while ago that I might meet you some day. She didn’t know your name then.

“Now I’d like to hear directly from you on your seeing yourself as a young woman.”

I say, “I think I’ve been Josey a long time, maybe forever. I remember as a young boy I was taken in a women’s restroom because my father wasn’t around. I acted embarrassed and kind of was. That was a long time ago before another Christmas. Now I’m in college but not as Josey and I want to be. I’d like to look like and become the woman I am. I guess seeing you is needed to do that…”

We talked for more than ten minutes; it was actually closer to a half hour, but I didn’t realize it. Dr. Sarah as she invited me to call her said she’d give me a testosterone blocker as a women’s hormone shot. But I needed to begin talking to a counselor and a specialist in transitioning. She was fairly sure I could do it at the university. She was wanting to see me after Christmas. She and her office would help to get me recognized as Josey.

When I told her about Jenn being the love of my life. I also expressed concern about the hormones causing me to change who I was attracted too. She smiled, but I knew she wanted to laugh. “Josey, I am going to be truthful with you. I hope you will focus on finding out who you are as Josey. Your feelings for Jennifer may in fact remain, but I can’t say they will or if things will change. You were happy that you lost another three pounds because of an image you have of what a girl should be.

“I hope you will put out of your mind the girl stereo types your male brain has. You’re not a little girl or a boy’s image of what a girl should be. You’re a young woman at a university. Boys tease girls for being very intelligent. A young woman, however, often finds her intelligence to be an asset in not being dependent upon a man. Even with a special friend like Jennifer, I want you to take responsibility for the woman you’re becoming. Do you understand me?”

I know tears have come to my eyes but I’m holding them back. Dr. Sara asks, “This is a very important question, please think before you answer. Are those tears of disappointment or tears of joy?”

I think and then respond, “I’m not supposed to cry. I’m happy deep inside but emotions scare me.” I see Dr. Sarah smile and I know I’m safe to cry. I’m soon crying and I even lean over to cry on her holding her in a hug. It takes me a moment to remember she’s a doctor and I shouldn’t. I pull back and now I’m crying into my hands when she gives me a handful of tissues.


My mother was invited back before Sarah gave me my shots. Mom confirms I’m still on their insurance until I’m twenty one. By that time I will have graduated from NW University. Mom says, “We’re not sure if our insurance however will cover her surgeries to transition. They may not qualify them as a medical necessity.”

Dr. Cooling says, “I believe the University’s women’s center as well as their diversity groups will lend weight that is needed. Even if it means the Northwestern Medical Center bears much of the cost. That might be a drawn out affair but I am fairly sure it will eventually be approved.”

I have mixed emotions about all I’m hearing: I’m excited and yet frustrated.

Dr. Cooling asks, “Josey, may I share more fully with your mother this once.” I shook my head in affirmation “…Christine, I will not be calling you back during her appointments, nor tell you anything about her situation that will be up to her. But she agreed before she wanted you to know so she could talk to someone who understood and could help her.

“She needs to experience her womanhood beyond the stereotypes that society has filled her head with. While she appears well as a woman, she’ll not be the most beautiful woman in the world. She will be flawed in the eyes of some including herself. This might be hard on her psyche; it is but one of many challenges she’ll face in becoming Josey more fully. I hope you’ll gain the wisdom to know when and how to be there for her.”

“Josey, you must be very intelligent to be a junior in college already. It will take more than academic intelligence for the days, months and year ahead. You will need the help of good people around you. You are as beautiful as any other person, you need to measure it in new ways. If you develop as a woman taking after your mother and sisters, there will have some natural beauty. Before any breast augmentation, I encourage you to allow your body to develop on its own.”

There was much more said, as Sarah met with my mother and me into the lunch time.

When we were back out to the waiting area, Jenn was happy to finally see us. She gave me a hug saying, “Dr. Cooling must have taken time to explain the bigger picture of all that you could be in for. Did she indicate if she would be open to you beginning treatment soon?”

Jenn was pleasantly surprised I already had a testosterone blocker and an injection of female hormones. She said, “I’m not surprised that she would, but that you already agreed to it.”

I shook my head, I knew the past week has been different for me. You, my parents and sisters have said I’ve been in denial and stubborn in acknowledging this part of me. It has been so freeing, I’ve known I need to continue saying yes to what I need as Josey. None of you can imagine how scared I am on the inside.”


Come Christmas, I received my usual share of gifts, thankfully they were very different from Christmases past. Whenever I received a skirt and blouse, or jeans or leggings I usually received a gift card to help purchase more for my wardrobe.

Jenn and I exchanged gifts. Her gifts included a statement that my new residence was approved for me to live in their suite when I’m back at the university.

Mom and Dad gave me the best gift last. It was not a gift as such but a Christmas card.
Dearest Josey Megan,
Whenever you and your doctors say you are ready to transition. We want you to know you are free to become our daughter in the fullest ways you desire. Insurance will not have the last word. We, as your parents, have agreed to pay for the needed operations if insurance would not approve paying for it. You are already our daughter and we are in full support of you being you.
Mr. Collins our lawyer, will have all documents needed for your signature come Wednesday to make your application for your new identity with a driver license and birth certificate complete.
We wish you not only a happy new year, but a whole new life. We loved you as Josh and our love will continue.

Love, Mom and Dad

It was as though I woke up on Christmas and found out I wasn’t dreaming.

The End of the Beginning

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