This started out as a piece of fluff. Then it became unfluffy.

Kelly was my newish girlfriend, and a very exciting person to be with. I wasn’t quite sure how we ever ended up together, as she was not only pretty and popular, but also looked like the sort of young woman who would be on the arm of a tall, muscled, handsome jock type—the very opposite of me. She was bursting with energy and was a lot of fun. She got me to go places and do things I had never even considered. I wasn’t that sure of myself, thanks to my childhood, and she tried to pull me out of that way of thinking. She was definitely the dominant partner in our relationship, and although we were close to the same size, I thought she was probably stronger than I was; she kept her body in excellent condition. I, on the other hand, was, well, spindly.

We slept together at her place last night, but when I woke up this morning she was gone, and, looking around, so were my clothes. Hers were still there where she left them last night. I found a short note on the bedside table saying:

Tim,
My friend Nancy really needs me. Be back in a few hours.
xxx, Kelly

Wonder what time that happened. I wasn’t even aware she left.

After I used the bathroom, I looked around for a robe, but there was nothing. I really didn’t want to violate her privacy by looking in her closet or drawers. I also didn’t want to wear a towel or the blanket, so for a laugh I put her clothes on, as she was evidently wearing mine. She had left her bra, panties (strange, that), black pantyhose and a short-sleeved blue mini-dress with a full skirt. I figured what the heck, and went whole hog, even stuffing the bra. I even parted my hair in the middle to make the picture a bit less jarring. To my surprise her two-inch wedge sandals fit me, so I tottered out of the bedroom and went to the kitchen. Knowing her, I was sure she would appreciate this joke.

I was able to find some cereal, and sat down to eat, noting that while seated there seemed to be hardly any fabric under my butt. It meant I had to sit up at the edge of the chair. I was on my first mouthful when Kelly suddenly returned.

“Ooohh! Look at you! You look fabulous! I was just about to ask why you were wearing my clothes when I remembered I was wearing yours. I think you look better than I do in that dress!”

“Uh uh. No way I could ever look better than you!” I said.

“I don’t know–whoa,” she kind of sing-songed. “You’re a lot prettier than I would have imagined. Let me just do a few things…” and so saying she ran into her room to get her cosmetics. Returning, she moved me away from my cereal bowl and quickly and expertly applied eyeliner, foundation, mascara and a bit of blush. She also fussed with my hair some, and put some CZ screw-post earrings on me. Not sure why she had them, as her ears were pierced.

As you can probably tell, we were in the early stages of our romance, meaning I would do almost anything she asked.

“Yes. Very nice! Come with me,” she said, pulling me to my feet. “Ooh! Wedges and hose too!” She stopped for a moment, as if thinking of something, then pulled up my skirt. “Aha! Panties as well. You went all out!”

I did think about asking what other choice I had, but kept my mouth shut.

We went into the bedroom so she could show me her handiwork in the full-length mirror. I was dumbstruck. With what seemed like very little work she’d made me look a lot like a girl. She was obviously at the master’s level with makeup, since I could hardly recognize myself.

“I should have asked you to do this before now. You look so good!”

“Um, you didn’t ask me to do it this time!” I sputtered. “You just took my clothes. I didn’t want to invade your privacy by rooting around in your closet.”

“Well, that was very thoughtful of you, but I wouldn’t have minded, especially having stolen your clothes. I just needed to get to my friend, Nancy, and your clothes were handier and easier. She was having a crisis and needed someone to listen. I thought I was going to be back here before you woke up.”

“It’s fine, Kelly. I hope things turned out okay with her. Can I have my clothes back now?”

“What?! Now that I’ve prettied you up? No way! I want to enjoy you looking like this. Hey, did you eat a lot?” she asked, switching subjects rapid-fire.

“Well, no, I didn’t get very far.”

“Great. I’m starving. Here,” she said, reaching for her jacket and handing it to me.

“What… Wait, do you expect me to go outside like this??” I said.

“Sure! As I said, you look fabulous. I want to take my new girlfriend out to breakfast!”

“Well, couldn’t I at least put on something a little longer, like, say, a maxi dress?”

“Hah! Are you kidding? With those sexy legs? You need to show them off!”

Things were happening too fast for me, but I was caught in the whirlwind that was Kelly. She held out the jacket and I dazedly slipped into it. She bustled around a little bit, putting my things into a small purse, and grabbed another for herself, and pulled me out the door before I could think how to tactfully protest. My brain really wasn’t awake yet!

There was a diner about a block away, so we walked, and she gave me all sorts of tips about taking smaller steps, swinging my hips, what to do with my arms. My legs felt cold and exposed, and I was scared out of my mind, but somehow couldn’t resist her. It was kind of exciting, in a horrifying way.

“Kelly,” I begged, “couldn’t we at least go somewhere farther away, where we’re less likely to run into anyone we know?”

“Listen, um… Jessica, no one is going to recognize you. I know who you are and I hardly recognize you! Try to relax. You look very pretty and very natural,” she said, trying to calm me down but not succeeding much.

We entered the diner and seated ourselves. I made sure my back was to the door, and I kept the jacket on, as a kind of extra layer of protection. Kelly reminded me to keep my legs closed. My appetite had all but vanished, so when the waitress came around I just asked for coffee. Kelly ordered a hearty breakfast.

“Are you sure you don’t want anything, Jessie?”

A girl for five minutes and I’ve already got a nickname!

“No, somehow I don’t think anything would stay down,” I replied.

I sat and watched her eat, while taking the occasional sip of my drink. She kept up a running monologue between bites, about pretty much everything. I found myself relaxing a bit, listening to her; she had a very pleasant voice. When she was done, she paid for us, and then pulled me over to the boutique next door, where she looked at various skirts and dresses. She’d ask my opinion, but I was so clueless about fashion and what went with what, that I had little to offer.

She eventually found a pretty nice dress, that even I had to admit looked good, and she tried it on.

“You know, this would look super on you,” she said, as she modeled it in the mirror.

The saleslady, who was passing by at that moment, chipped in, “She’s right, you know. With your coloring it would look very good.”

After she was out of earshot, I said, “Kelly… honey?, I wasn’t really planning on wearing dresses. I did this because my clothes were gone and to give you a good laugh.”

“I’m not laughing, Jessie. Now that I’ve seen you in a dress, you absolutely have to wear them! You look too good not to wear them! I’m getting this one for you.”

I really didn’t want her to waste her money on women’s clothes for me, but I also didn’t want to torpedo our relationship, so I said nothing.

She paid for it and we walked back to her place. As soon as we got in the door she was all over me. She got the jacket off me somehow, while at the same time kissing me, and pulled me to the bedroom. She flipped up the tiny skirt of my dress, pulled down the pantyhose and panty, extracted Junior and pushed me down on the bed and got me involved in hot, luscious, passionate sex. I was powerless to resist (not that I wanted to!). She cooed to me, and kissed me and called me her girl, and felt up my stuffed, illusory breasts. It was all pretty arousing and sexy, and I liked it a LOT.

Afterward she lay on her back and had me put my head on her shoulder while I lay on my side, her arm around me. My hand was gently lying on her breast.

“Jessie, that was wonderful! I don’t think it was ever that good before.”

I nodded my head in agreement, and kissed her cheek.

We lay like that for fifteen more minutes and then got up and took a shower together. I felt closer than ever to her, even if she did keep calling me Jessie, and her girl.

After we had dried off, she smelled my own clothes and pronounced them “stinky.” She said I couldn’t possibly wear them. So she got out some fresh lingerie and had me put on the new dress, then made up my face again.

“Aha! I was right about that dress. It looks wonderful on you!”

“Well, um, thank you, but how am I supposed to go home like this?”

“What? You have no roommate. It’ll be fine.”

I kept thinking “famous last words” every time she used that phrase.

-o0o-

When I finally left I drove myself home, as slow as the proverbial little old lady, being very careful so I wouldn’t get stopped and have to show my license. Getting inside to my little studio apartment turned out not to be a problem. The one other resident I passed on the stairs, a woman in her forties from the floor above, looked startled to see me, then complimented me on the dress and asked where I had gotten it.

I thanked her and told her where. She looked at me just a little longer and continued up the stairs.

Inside I was about to change to my own clothes when it occurred to me I didn’t know how to get the makeup off. I called Kelly to discuss it. She first suggested I go out to the stores and buy some makeup remover or cold cream. When I nixed that she thought about it a bit. Most of the things she then named (Cocoanut oil, baby oil, jojoba oil) I didn’t have or had never heard of. But she said olive oil would work, so I used that. Then I smelled like olive oil, so I used soap and water.

-o0o-

A few days later Kelly called and said she wanted to go to dinner and a movie with me, and told me she’d pick me up at 7, on Friday. “Make yourself pretty for me,” she said, and hung up.

Uh oh. Why couldn’t I have just stayed in bed that day?

-o0o-

On Friday I was arriving home after work, and the woman I had met on the stairs the other day was coming up behind me. At my floor I turned to see who it was, and said hello, with a little smile. She was a tall woman, kind of regal-looking, and very attractive.

She smiled also and said hello, but then stopped and kind of stared at me. Kelly had assured me I looked nothing like my male self while dressed up, but I was getting a bit uneasy under her look.

“Did you need something?” I asked.

“No, no. You just reminded me of someone.”

“Ah. Oh, okay. Have a nice day,” I said, and started down the hall. I was aware that she was still watching me, as I didn’t hear her footsteps on the stairs.

-o0o-

When Kelly and I talked on the phone later that day, I mentioned to her about this woman on the stairs. She assured me no one would be able to tell who I was.

“But then why was she staring at me, and why’d she keep watching me?” I asked.

“Maybe she just thought you were a good-looking guy,” Kelly joked. “So, are you going to wear your new dress tonight?”

“Kelly…” I started.

“Jessie, I really want to have a nice night out with my girl. It’ll be cozy and romantic. You’ll do this for me, won’t you?”

Of course I caved in. Like I said, she’s hard to resist.

-o0o-

When Kelly arrived at seven I was wearing the dress, and the lingerie she’d put me in. She got right to work on my face and hair. She also put a necklace on me, along with the earrings, and a delicate bracelet. I would have thought it wouldn’t go over my hand, but I guess it was smaller than I realized.

Kelly was wearing some loose black dress pants that went with a black jacket. She looked amazing, as always.

She made sure I had the purse, with my wallet and phone in it, held the jacket for me as I slipped into it, and we went out the door.

Curiously the woman from upstairs was just coming down as we reached the stairs. She said hello to us, and gave me the once over again.

Addressing me, she asked, “Hello, my dear. Are you by chance related to the young man who lives on this floor?”

“What young man is that? What’s his name?” I said, in my best Jessie voice.

“Unfortunately I don’t know it, but you remind me of him. And he reminds me of someone else.”

“As far as I know I don’t have any relatives in this building,” I said.

“Would you please excuse us?” Kelly put in. “We have reservations to get to.”

“Of course. Sorry to detain you.”

“No problem. Byeee!”

Once in the car we began to discuss her.

“What do you think is going on with her? I thought you told me even you didn’t recognize me.”

“I might have exaggerated that part just a tiny bit, but you really do look like a different person when you’re my girl. She might be someone with a photographic memory for faces. Don’t let it worry you. What’s she going to do?”

That was what was worrying me. What could she do?

-o0o-

The dinner and movie were very nice. Kelly treated me like a lady and opened the car door for me. At the movie she put her arm around me and pulled me close. We couldn’t help kissing now and then. I found the whole experience very heady and eye-opening. Growing up, no one really cared about me, and to have all this attention was rather overwhelming. Kelly took me home afterwards, necking with me on the couch/bed. She really took control and made me feel like a woman with her attention. I was lapping it up.

“Jessie, Baby, I just love you like this. You’re so natural and sweet and you really turn me on,” she said, while working her way around my neck with kisses. “It’s hard to believe you turned out so delightful, given the way you grew up. The day you put on my clothes was a wonderful day! Why not give up your Tim existence, and move in with me as Jessie?”

It was hard to concentrate as she kissed and nibbled at me.

“I’ll… I’ll give it some thought,” I was finally able to say, although in reality I had no intention of tossing Tim away.

Since it was Friday night, she stayed over. She had brought a babydoll for me and one for herself, and went to sleep with her arms around me, making me feel safe and loved.

-o0o-

On Saturday she would have liked me to remain as Jessie, but that dress was the only thing I had. I had a couple tasks to do at home, and she said she had a couple of errands to run. When she returned we spent the rest of the day together and both drove back to her place, where she again got me Jessie-ed up. But this time she produced a pair of realistic-looking breast forms to stick in the bra. I had to admit they sure looked a lot better than tissues, which lacked nipples, although the weight was startling at first.

Kelly decided to teach me how to do my own makeup, and we spent some hours on that, the end of which time I was able to apply makeup and not look too much like a clown.

There was very satisfying sex again that night, and on Sunday she took Jessie to the stores to get me a makeup kit and remover, my own lingerie and some more clothes. She really had a thing for Jessie. And I found myself more in love with her as she fell more in love with Jessie.

I was looking forward to going home to think about what she wanted from me, and how it might be resolved. It was hard to think deeply about it when we were together.

She sent me home in a dress. I had a lot of packages to bring in, and kept dropping some. Strangely enough, there was the lady from upstairs yet again.

“Can I help you with those packages, dear?” she asked.

“Oh, that’s very kind of you to offer. Thank you!” I handed her two of the bags, and we climbed the stairs. Not thinking, I led her right to my door, and thanked her again.

“It was my pleasure. I’m Carol Walker.”

“Nice to meet you, Carol. I’m Jessie…” I hadn’t considered up to this point, but should I give my real last name? She already seemed to have some interest in me, so maybe a fake name??

“What’s your last name, dear?”

“Oh! It’s Collins.” I said, thinking of Jesse Colin Young. “Thank you so much for your help.”

“Well, it’s my pleasure. I’ll be seeing you,” she said, and walked back to the stairs.

I got all the bags inside and went to work putting things away. But it occurred to me that now I had two things to consider: One, what about Kelly and her request? Two, what was really the story with this woman, Carol?

-o0o-

Lying in bed that night I considered these two conundrums. I was certainly in love with Kelly, but there were ramifications in giving up my male identity. What about my job as a graphic designer? I knew nothing about my employer’s LGBT policy, or how they’d react if I just happened to change sex one day.

How would I handle my legal identity?

I didn’t know my parents, having been raised in foster care, not the happiest way to grew up. None of the families were abusive, but they were not very warm either. It did teach me I couldn’t rely on anyone else, though I found myself relying a lot on Kelly. But she was so strong! So easy to defer to. I felt she really wanted to take care of me, which was something I found myself strongly attracted to.

But I was also concerned that once she got me too feminine she’d lose interest in me, and then look for a “real man.”

As for Problem Two, Carol Walker, I just didn’t know what to think. If she thought she knew I was really Jessie as well as Tim, what was she going to do about it? She didn’t act as though she was just waiting to out me to the world. No, she seemed like a genuinely nice person. Well, that one would have to await further developments. It was certainly odd how she seemed to be on the stairs at the same time I was so often.

-o0o-

Over the next two weeks Kelly convinced me to go out with her as Jessie several times. I have to admit it was fun, as well as romantic. She kept adding to my clothing collection, and gave me pointers. She really took good care of me.

During the same period I almost felt like Carol was stalking me. I was too dumb to realize she was trying to catch me when I went to my mailbox to see my apartment number, but that’s exactly what she did manage to do.

And then one day she knocked at my door. She tried to look surprised when Tim answered it, but I could tell she wasn’t.

“Hello again. I’m Carol Walker, from upstairs. Is Jessie at home?”

“Um, no, she isn’t here now. Something I can help you with?

“Well,” she said slowly, “maybe there is. I brought this photo to show her. Perhaps you could look at it too.”

She handed me a studio portrait of a teenaged girl. She looked eerily like Jessie. I looked up at Carol.

“Wh… who is this? She looks just like Jessie.”

“It’s my sister. Oddly enough, her name was also Jessie. Quite a resemblance, don’t you think?”

“Wow, they could practically be twins!” I said.

“Yes, I agree. I wanted to show this to Jessie and ask her about her family.”

“Oh, well, I can answer that. Her parents dumped her at an orphanage when she was born, and she grew up in foster care.” I said, trying not to sound too bitter.

Carol looked very sad at that.

“May I come in? Oh, I don’t even know your name.”

“Oh, sorry. Yes, please come in and have a seat. I’m Tim Waters.”

She took the one chair, and I sat on the couch/bed.

“Thank you, Tim. I wanted to tell Jessie all about my sister, Jessie. She had gotten pregnant her last year in high school and was unfortunately forced to give up the baby. She was heartbroken to have to do so. She really wanted to keep it but our parents gave her an ultimatum: an abortion or the orphanage. Marriage was out of the question.”

“That’s an awful choice for a girl to have to make,” I said, sympathetically.

“Yes, I agree,” she said, sniffling a bit. “Jessie felt so guilt-ridden and angry about this that she became very depressed and neglected herself. Our parents tried to ignore what was happening, but when they chose to notice it was too late. She was by then so weak she had to be hospitalized, and after she gave birth there she caught a bug that carried her off within a week. The baby, a little boy, was born a month early and was very frail.”

I didn’t know what to say. This was pretty sad, but I wasn’t sure what it had to do with me.

“I’m very sorry for your loss, Ms. Walker,” was all I could manage.

“Thank you, dear. What I was wondering… was whether Jessie might not in actuality be my niece, seeing as the resemblance is so strong.”

My eyes nearly popped out of my head at that, and I felt a little faint.

“Now Jessie, do you know the name of hospital where you were born?”

“I’m not sure. I think I was told it was City Hospital,” I said, completely failing to notice in my state that she’d called me Jessie.

“That fits. Now, my sister gave birth on June 15th. Is that your birthdate?”

My ears were starting to ring, and I was feeling very odd, as if the room was tilting.

“I, um, yes, that’s my birthdate. I, I can’t believe this.”

She moved over to sit next to me and put her arm around me.

“This means I am your aunt,” she said, smiling at me. “You look a bit pale, dear.”

I slowly looked at her, still in shock. I’d never had any family.

“I don’t know what to say,” I said.

Hugging me a little tighter, she said, “And if you hadn’t been walking around dressed as Jessie, I would never have even thought about it.”

If I thought I was in shock before, I felt positively woozy now. How did she know? My mouth fell open.

“Dear, I already asked you a question as Jessie and you answered without even thinking about it. I don’t mind at all if you like to dress up. And you look so much like my sister, I was just amazed. It was like seeing her come back to life.”

I took a few moments to digest this, then a question occurred to me.

“Do you know who my father is?”

“I’m sorry, but my sister refused to say. We never knew whether it was some boy at school or if she had been raped. Seeing as she wanted to keep the baby, I think it was a boy she knew.”

That made sense to me, too. Who would want to be told their father was a rapist?

“Tell me, how did you end up with the name Jessie?”

“Oh, Kelly—my girlfriend—just pulled it out of thin air.”

“What a strange coincidence,” she said.

There was a silence as we both thought about that.

“I’ve never had any real family. I’m not sure how to feel… What about your parents?”

“They are both deceased. We had a falling out over this affair and I’m sorry to say we never got along that well afterwards.”

We talked for a while more, with her telling me some things about her and her family. It didn’t seem real to think of them as my family. I surprised myself with how happy I was to know that my mother hadn’t just abandoned me, as I had been told. She actually wanted me!

Carol eventually left me to my thoughts, and it wasn’t long before I called Kelly to tell her I really needed to see her. She said she’d be over as soon as she could.

-o0o-

“And that’s the story, Kelly. That woman is actually my aunt. I can’t get over how the name you picked is the same name as my mother!”

“Yeah, kind of freaky. But maybe it showed I was tuned in to you and what’s going on.”

“I forgot to tell you that she kind of tricked me into admitting I was Jessie. We were just talking, and she asked me a question. I think it was, ‘So where were you born, Jessie?’ And I’m so dumb I didn’t even notice.”

“Nah, Baby, you’re just an innocent is all. Hey, I don’t suppose you gave any thought to my suggestion about becoming Jessie all the time?”

“Oh Kelly…”

“What?”

“I really didn’t think too much about it. Mostly I thought that once I became too girly, you’d just dump me and find a quote/unquote ‘real man.’”

She looked shocked. “Oh honey. No, I’d never dump you like that! You are exactly the type of guy I go for, and that you have this wonderful female side is such a great bonus.”

That made me feel better, for sure, and eased some of my anxiety.

“Still, becoming Jessie full time is a pretty big step. I mean, I’ve been enjoying it, but I don’t know much about being female.”

“But that’s the great part! You are such a natural that you won’t have to make a huge effort to learn. As soon as you put the clothes on you change in ways you probably aren’t even aware of.”

I felt dazed hearing this. Did I know anything about myself??

“What about my job?”

“If they don’t have a tolerance policy you’ll find another job. You’re talented. Don’t worry so much. I want to take care of you.”

I felt overloaded with all this information, even if none of it was bad. I felt tired, but didn’t know if I’d be able to sleep.

“So, about your aunt -- is she just looking to connect with you? Or does she want something more?”

“You know, I was wondering that too, but she didn’t seem to want anything more than to connect. I’m still kind of in shock. I never had a family, so I don’t know what to do with the information. It’s supposed to be a good thing, I know that.”

“It is, Baby. I think it’s great that you have at least one other family member. I always thought it was so sad that you were orphaned so young. And it sounds like it’s probably just as well you never met your grandparents!”

I put my head on her shoulder and we just sat there for a long time.

-o0o-

The next day, after work, for some reason I don’t even understand myself, I made myself into Jessie, put on a dress, and went upstairs to Carol’s apartment. I knocked and waited.

She opened the door and her face lit up.

“Jessie, my dear! I’m so happy to see you!” and she drew me in and gave me a nice, tight hug.

“I swear, it’s just like seeing my little sister,” she said, tearing up a little. “I still miss her, and it’s been twenty-four years.”

I was feeling pretty emotional myself.

“Is there anything special you wanted, my dear? And can I offer you tea or coffee?”

“Um, Aunt Carol… wow, that sounds weird to me… I’m not really sure why I came up here. Maybe… maybe you could tell me more about my mother?”

“Of course, dear.”

She had a full-sized apartment, and led me into the kitchen by the hand.

She had me sit down at the table, and started preparing tea. She described her sister in glowing terms: good student, did well at art (!), mostly happy. It was nice to hear these things to flesh her out in my head a little.

Once she put my tea in front of me she went and retrieved a photo album, then, side by side we looked at her family pictures together while we drank our tea.

“Jessie, my dear, you’re such a sweet girl. You remind me so much of my sister. I can’t tell you how happy I am to have you as my niece. I was married once, but only for two years, and have been alone ever since. You are like a ray of sunshine in my life.”

I was embarrassed. No one ever described me, Tim, as a ray of sunshine, and I wasn’t doing anything special here and now. But I smiled at her and then, to my amazement, I started to cry.

“Oh honey! I hope those are happy tears,” she said, and held me.

“I think they are. No one has ever described me as a ray of sunshine before.”

“Well, you are, and I still can’t believe the chain of events that led to us being in the same building. It’s a miracle. Why don’t you tell me more about yourself?”

“Well, you know I was brought up in the foster care system, which sucked. I lost count of how many families I was placed with. Some of them were pleasant. Others were in it just for the money. As soon as I got to my eighteenth birthday I was turned loose. I applied for and received a scholarship to a two-year college and got an associate’s degree in graphic design. Now I work at a small printing house doing the odd graphics job. Oh, and by some miracle, I met Kelly and she somehow liked me and became my girlfriend. That’s me in a nutshell.”

“Jessie, I’m an editor for a big publishing house, and I might be able to find a graphics job for you within the company, which would probably pay more than you get now. Would that interest you?”

That sounded enticing. But…

“Suppose… suppose I were to keep on being Jessie? Would they still hire me?”

“My company has a very tolerant attitude towards the LGBT community, and does not discriminate, so yes, you’d still be able to be employed. Is this something you’re thinking of doing?”

“I’m mulling things over. Kelly is all for it, and I don’t exactly feel like I have much to lose. But the truth is, I haven’t done it very much. The first time was only something like a month ago. In fact, you saw me that day! It seems a little premature to make a decision like that so soon. Also, before a few days ago I didn’t have any family to worry about, as far as negative reactions,” I said, looking her in the eye.

“I would be very happy to have my niece around all the time!” she said, beaming, and gave me another hug. “It’s hard to believe you’re new at this. Would you be ‘going all the way?’”

“Oh! No! I’m not unhappy with my male equipment. I’d just present as Jessie and leave it at that.”

“Well, either way you decide to go, I will support you. I hope we can build a close relationship.”

I looked at her and smiled. “Me too.”

...Continued in Ms. Walker and Jessie, Part II