The air was cool with the first whispers of autumn when my roommate/girlfriend, Kate, came through the front door of our shared, rural house. She was flushed from a workout, her short brown hair tousled in a way that made her look more strikingly handsome than feminine.

Let me explain our relationship. Since high school, we have had an unusual relationship. Part friendship, part relationship. Everyone in school thought I was gay, and that Kate was a butch lesbian. Somehow, that brought us together. I’m not sure either of us fits in some neat category. Kate was six feet tall. I was five-eight. Nevertheless, we got along, even had sex occasionally. We seemed to complement each other.

“I’m excited,” she said, dropping onto the couch beside me. “We’ve been invited to a big, exclusive Halloween party. Costumes, contests, and big cash prizes. Some people from my gym will be there, friends, friends of friends. It’ll be fun.”

I smiled. “Okay… sounds fun. So we need costumes?”

Kate grinned, a mischievous spark in her eye. “Of course. That’s the best part. And I have an idea. What if we… swapped genders?”

I blinked. “Swap genders?”

“You go as a woman. I go as a man. I think it’s a great idea. I’m tall, muscular, and, face it, masculine. And you’re, well…”

“Well, what?” I asked.

“Let me put it this way. You have features that would lend themselves to, well, coming across as a woman.”

I flushed. “I’m not sure how to take that. You mean I have feminine features?”

“To be honest - yes. I don’t mean it negatively. It’s part of what attracted me to you in the first place. You know I think you’re cute. You have a slim body and a pretty face.”

She was right. I had even been mistaken for a girl at times. What Kate didn’t know was that I had crossdressed before I met her, but I had put that behind me. Or so I thought.

“Come on. It’ll be fun. Everyone will be witches, vampires, superheroes. But us? We could win because there is a big cash prize for the most imaginative couple costumes.”

My stomach fluttered in a way I didn’t expect. I suddenly recalled my feminine dressing with fondness.

“So would this be a drag thing?” I asked.

Katie shook her head. “If we’re going to do it, we’ll do it right. You’ll be a girl, and I’ll be a man.” She laughed at the thought.

“That’s crazy,” I said, while actually being excited about the idea.

“No, not at all,” she said. “Let’s be honest. What drew us to each other was that we’re the opposite of a normal couple. You are much shorter than I, have a slight build, and, don’t take this the wrong way, you’re a bit effeminate. You probably would be a really pretty girl. And me? I’m tall, muscular, and masculine. I already get mistaken for a guy.” She laughed.

She was right. I wasn’t masculine at all. “You really think I can come off as a girl?”

“Absolutely,” she said with confidence. “Of course, it’ll take some work, and practice. You need makeup, clothes, a wig, and shoes. But if we start right now, by Halloween we’ll be ready.” She mischievously grinned.

“Wait a minute. It’s a couple of weeks until Halloween. You want me to start now?” I said, a bit incredulous, but also excited.

She leaned back, already plotting. “Yep. We’re going to win this.”

The next day, Katie came home with bags and boxes.

“Okay, Chris, time to start practicing. We’re not waiting until the last minute.”

I had a mix of emotions. I was apprehensive, but the idea of dressing as a woman again was irresistible.

She pulled items from a bag and laid them across the bed: bras, panties, a dress, skirts, blouses, and a pair of patent leather pumps. Finally, a box with a wig, and various makeup items.

“Geez, Katie. Don’t you think you’re getting carried away here? Wouldn’t one outfit be enough?”

“You must be convincing, so you need to try different looks,” she said. “I even got you breast forms. Let’s get started.”

“You mean right now?” I said.

“Yes. Take off your clothes,” she ordered. I did as told, soon standing in front of my girlfriend stark naked. She handed me a bra. As she did, I got an erection.

“Well, well. I see you’re excited about this.” She laughed as she fondled my stiff cock.

I slipped the bra over my shoulders. Katie fastened it behind me. It felt so natural. She giggled as she placed breast forms in the cups. “Hmm, nice tits. You look fantastic in that 38D bra.”

Next came lace panties. “Here’s something that will give you a feminine figure.” She handed me a pair of additional panties with very robust foam hip pads. Suddenly I had female hips. Then a girdle, cinching me in, followed by stockings, fastening neatly to six garters.

I caught my reflection in the mirror. Pleasant memories of my prior experience danced in my head. “Good for the contest, right?”

“Very good,” she murmured.

Next came a pencil skirt and a satin beige blouse with a bow. The skirt hugged my waist and hips, the blouse floated against the bra beneath. Katie helped me into the three-inch heels. “You’ll need a lot of practice walking in these.”

Katie whistled. “You’re getting there. But it needs more.”

She sat me down and started putting makeup on my face. I had done this before, so I knew what was coming: concealer, eyeliner, eye shadow, black mascara on my long eyelashes, and finally, bright red lipstick. She brushed out the shoulder-length, wavy wig that matched my natural color. She carefully placed it on my head.

“Okay, go look in the full-length mirror."

I wobbled a bit in the heels, but when I looked in the mirror, all I saw was an attractive woman staring back at me.

Kate suggested, almost casually, “Start letting your hair grow. Maybe we can get it to a feminine style, and forget the wig.”

I flushed. “Wait a minute. Are you thinking of something beyond Halloween?” She just smiled.

I looked at her in the mirror, then back at myself. I felt feminine. I realized this was always there, but had been suppressed.

She had me try different outfits. “You’re a very convincing woman,” she said. “You definitely pass.”

“Oh, come on, Kate. You’re kidding.”

“Not at all. I mean it. I’m surprised, but I like you like this. How do you feel?”

“I hope this is okay, but I like it,” I smiled. “It seems to have brought something out that maybe was there all along.” But, of course, I realized that she had reawakened the girl in me.

“I had a feeling you’d like it. Now I’m going to go male. She left the room. A bit later, she came out of our bedroom, wearing pleated slacks, a button-down shirt, and brown loafers. She had combed her already short hair in a male fashion. She had very small breasts and had put on a tight T-shirt. There was no evidence of female breasts. Of course, no makeup. Due to her regular workouts, she had broad shoulders and muscular arms. She was four inches taller than I and I realized she could easily be mistaken for a handsome man.

She had me try on different outfits on Saturday, and the ease of walking in heels returned. She instructed me on the fine points of acting feminine. I was surprised how easy it came back. On Sunday, Kate told me to put on a dress. She did my makeup. “My goodness, you really are a lovely woman. Since you’re between jobs, I want you in girl mode every day until the party.”

“Don’t you think that’s overdoing it?” I said, but without any conviction.

“Not at all. Practice makes perfect. Anyway, I’m getting used to you like this. And be honest, it’s obvious you like it, don’t you?”

I blushed. “Kind of,” I lied. I was loving it.

Every day after showering, I got into my feminine attire and practiced my makeup. I was becoming accustomed to wearing lingerie, makeup, and women’s clothes. Katie instructed me on the fine points of carrying myself in a feminine manner. She had me shave my entire body. I went the whole week without wearing any male clothing, occasionally going for a walk down the road.

On Friday, I took a shower and shaved my legs. I put on my lingerie, did my makeup, and slipped on a black skirt and a burgundy sweater. I put on my wig and admired my handiwork in the mirror. “Not bad,” I said in a surprisingly feminine voice. I walked around in my pumps. I was getting good at this. Feeling confident, I decided to venture out for a drive. I stopped at a mall. I walked around. It was clear that anyone who saw me thought I was a woman. I got some smiles from a couple of men. I smiled back.

When I got home, Katie was there. As I walked in, she smiled from ear to ear. “Well, hello girl! You look fabulous. Where did you go?”

In my best feminine tone, “Oh, just out.”

“I’m glad you went out. How did it go? How did you feel?” Katie inquired.

“I went to the mall and walked around. Everyone obviously thought I was a woman. You’re right. I pass,” I said with a big smile.

“Did you like feeling like a woman? “ Kate asked with a mischievous smile.

“I loved it,” I blurted, without thinking. “I hope that’s okay.”

“Of course it’s okay. I’m getting to like you like this. I think it’s time for a real test. I’m taking my girl out to dinner.”

“Oh geez, Kate. No way.”

“I’m totally serious. You look great. You’re acting more and more feminine. Even your voice has changed.”

Kate didn’t have to do much. She put on a sports coat and a pair of loafers. She combed her hair. She looked like an attractive man.

“How do I look?” I asked nervously.

“Beautiful. You’ll turn heads. But you need a feminine name. She looked me over. “From now on, you’re Christine, not Chris. What do you think?”

I nodded. “Sure. Why not? How about you? I can’t call you Kate.”

“You’re right. From now on, call me Karl. How’s that?”

“Yes sir.” I smiled.

“Okay, Christine. Freshen your lipstick, oh, and I’ll get you a purse to put your lipstick in.” She smiled.

I was confident in my newfound femininity. Walking into the restaurant felt comfortable.

The host looked up, smiled politely, and asked, “Good evening sir, a table for you and the lady?”

Kate didn’t miss a beat. She lowered her voice just enough, nodded, and said, “Yes, please.”

“Right this way,” the host said, menus in hand.

My cheeks burned. The world saw me as a woman and Kate as a man. We indeed had swapped genders.

Once seated, I leaned close, whispering, “He thought you were a man!”

“And obviously, he knew you were a lady. We’re pulling it off.”

I smiled shyly, fiddling with my bracelet. “I hope you understand, but I am getting comfortable being Christine. It’s fun.”

She tilted her head, studying me. “Good, I like Christine.”

At one point, I told her I had to pee. “Well, go to the Ladies' Room silly. And freshen your lipstick. Oh, and don’t forget to sit when you pee,” she giggled.

The drive home was quiet. “You did so well tonight,” she said softly.

“I couldn’t have done it without you.”

When we reached home, Kate turned off the car and faced me. “I think I like this side of us. I like being him. And I like you being here.”

I swallowed hard, my voice trembling. “So, am I now just Christine?” I asked.

“As much as you want, honey. I like her.”

Kate reached under my skirt and found my aroused “clit.”

“Too bad I don’t have a big cock. I’d have my girl suck me off. You’d do it. Wouldn’t you?”

I smiled. “Of course I would.”

“Good girl. Now that I think of it, maybe that should be part of your training.” She smiled.

“What should be part of my training?” I asked.

“Sucking a cock, having sex with a man,” she calmly responded. “That would make you all girl.”

“Now, you’re getting carried away.” But the suggestion excited me.

“It’s becoming obvious you love being a girl. I’m fine with that. So, you should do everything a woman your age would do.”

Back home, when we reached the bedroom, Katie pulled out a package I hadn’t seen. She handed it to me with a little smile.

Inside was a pale pink satin nightgown.

“I got this for you,” Kate said, “because I want you to be Christine 24/7.”

I got undressed. “Leave your bra on,” she instructed. I slipped the satin gown on.

Kate removed her masculine clothes, climbed into bed beside me. She wrapped her arms around me. I felt wholly feminine. “Now I’m going to fuck my little girl.”

I smiled, assuming she’d mount me. She was always on top if she felt like sex. But instead, she went to the bathroom. She returned shortly, wearing a very realistic strap-on cock. “Tonight you get fucked like the girl you are. My big cock is going in my girl’s pussy.”

I was nervous. She told me to get on all fours as she lubed up the eight-inch cock. She very slowly probed my anus with a gel. Then she started to insert the life-like penis a little at a time. At first, it hurt, but then it suddenly slid in. She started fucking me harder and harder. At the same time, she reached around and stroked me.

“Does my girl like a big, hard cock in her pussy?”

“Oh yes. I love it,” I whispered. I began shooting a load of cum without even being touched.

The closer Halloween got, the less we talked about the actual party. Every morning, I dressed in female clothing and did my makeup. I started doing my nails. It became routine. I was living as a woman.

One Saturday, Kate told me we were having dinner that evening with our friend, Megan.

“I want to see how it feels,” she admitted. “I told Megan about our ‘costumes’ so she knows how we’ll be dressed. She’s excited.”

At the restaurant, Megan walked right up to us. “Well, this is interesting. I knew I was meeting a male and a female friend, but I didn’t realize which ones.” She giggled.

“Nice to meet you, Christine,” Megan said.

The evening flowed more easily than I could have imagined. Megan chatted with me as though I were simply another woman.

We started going out. I went shopping as Christine.

One night, over wine, Kate admitted, “I don’t think this is about Halloween anymore.”

I smiled into my glass. “Neither do I.”

We hosted a small dinner party with friends. Again, we told them we wanted to test out our “costumes.” They saw the transformation in full. Kate was in a collared shirt, greeting people with a firm handshake. I wore a flowing dress.

Laughter over wine smoothed over hesitation. By dessert, the guys were flirting with me. Another female friend casually asked where I bought the dress I was wearing. Another teased Kate about “finally looking the part.”

Megan and I started doing things together, as girlfriends. Kate had to travel a lot. One evening, Megan and I went to a bar. She suggested we change our approach. “There is no question you love being Christine. I don’t even think of you as a male.” She smiled. Megan told me she had a date coming, and had one for me.

“Megan, you’re kidding, right?”

“No I’m not. It’s a guy I know. And he knows you’re male, or at least was a male,” she giggled. “He has dated trans women like you and he’s excited to meet you. My date thinks you’re just a girlfriend.”

“Am I trans?” I thought. The idea of being with a man excited me. “I don’t know, Megan. What if Kate finds out?”

She smiled broadly. “It was her idea.”

“You’re kidding!” But I recalled Kate mentioning sucking a guy off, and even getting fucked, as part of my “practice.”

“Come on, Christine. Let’s face it. You look like a girl, you act like a girl, and, well, to me you are a girl. I know you want to.”

“Um, well, okay, you’re right. I do.”

“Great, it’ll be fun. He’s nice, good-looking, and you’ll like him.”

I was nervous, but Megan was right.

Soon after, an attractive man walked up. Megan introduced me to Jim, my date. We exchanged pleasantries. “Megan, you didn’t tell me how pretty Christine was.”

Within a few minutes, Megan’s date, Tom, appeared. She introduced me. “So nice to meet you, Christine.” He clearly had no clue.

We went to dinner, then for a walk. Jim put his arm around me. I felt wonderful. We walked to a bar and had a couple of glasses of wine. In the Ladies' Room, Megan told me she was going with Tom to his place and that Jim would take me home. She smiled. “Invite him in for a nightcap. Have fun.”

I did as Megan suggested. As soon as we walked in, Jim grabbed me and started kissing me. I fell into my womanly role. Before long we were passionately making out on the couch. I couldn’t help but rub his crotch. “Oh my,” I thought. “He’s huge.”

Jim reached down and unzipped his pants. Out sprang an erection bigger than the dildo Kate had. I got on my knees and took him into my mouth. I sucked voraciously. This was all coming so naturally. Suddenly my mouth was filled with warm, salty cum. I swallowed and licked my lips. I looked up at Jim and smiled.

“Oh, Christine. That was incredible. Can I do you now?”

I smiled. We exchanged positions. I pulled up my skirt and spread my legs. Jim pulled down my panties and took my clit in his mouth. It didn’t take long before I launched a load into his warm mouth. He moved up and kissed me, sharing my semen.

Jim told me he had to work early but asked me out the following night. “Would Kate be okay with me dating a guy?” I thought. She did say that it would be part of my practice. Kate was still out of town.

“I’d love to see you again, Jim.”

Before he picked me up, I decided to douche, just in case. And I put a nightie in my purse. Jim took me to a nice restaurant. We had a nice time. This time he invited me back to his place, as I thought he might.

We ended up in his bedroom. I got my pink nightie and went to the bathroom. I slipped it over my bra.

When I walked out, Jim was standing, completely naked, with his cock standing at attention.

“Oh my, Jim,” I giggled.

We fell into bed, bodies entangled. Jim moved on top of me. I smiled up at him as he reached over and grabbed a condom. He slipped it on. Then he reached for a tube of KY. He pulled off my panties. He then lubed my hole as well as his big cock. He lifted my hips as he guided his massive rod into me. He was gentle, nudging me open bit by bit. It took a few minutes, but he was finally inside me. My legs were on his shoulders as he began a rhythm of sliding in and out of my tight pussy.

“Oh, Christine. You feel so good.” I smiled up at this handsome man as he grasped my throbbing girly cock. He simultaneously stroked me while increasing the speed of his thrusts.

After at least five minutes of our bodies joining, Jim began pulling almost all the way out, and then strongly penetrating all the way in me. “Oh, Jim. Fuck me good,” I whispered. He held my legs in the air as he banged me harder and harder. Suddenly, a final insertion as he let loose his load. I felt the warmth of his juice. Five more thrusts and he was finished. I was no longer a virgin.

We fell asleep spooning. I was awakened in the morning, by his stiff rod rubbing between my cheeks. I pushed myself into him. Without a word, he reached for some KY. I felt him insert a lubed finger in me. He whispered, “Christine, I was just tested. Is this okay?”

“Yes, dear. I want it,” I whispered.

I felt his incredibly stiff cock start to find its way into my tight hole. He was gentle, but persistent. After a few gentle shoves, I felt him slide all the way into me. We fell into a rhythm. He reached around and gently began stroking my clit as he fucked me. I realized I wanted this, and I wanted it often. After ten minutes, Jim sped up his motion. He simultaneously stroked me harder. Suddenly, I erupted, shooting my girly cum. Within seconds, I felt his full insertion as my pussy filled with warm semen.

We lay for a few minutes. Jim whispered, “Christine, I think I’m in love with you. I want you to move in with me. Don’t answer yet.” We kissed passionately.

I suddenly realized that Kate was returning this morning. I rushed to get dressed. Was this her plan?

Jim dropped me off. When I walked in, Kate was sitting there. She smiled wickedly. “Well hello, Christine. How was your night?”

I didn’t know what to say. I turned red. I started to say something.

Kate cut in. “I know where you were, and I think I know what happened. So don’t worry.” She smiled benevolently.

“Look, Christine. I know this started as a costume thing, but obviously it’s come to something completely. You’ve become a woman. And it’s clear you love it.”

I still didn’t know what to say, but I knew she was right. I didn’t want to go back.

“The party is tomorrow night. We’ll go. I know we will win. But after that, I think we will have to have a serious talk.” She smiled.

The next day, Megan came over. I got dressed in a skirt and sweater. Megan looked at me.

“I don’t even think of this as a costume, Christine.” She giggled.

“Neither do I,” I laughed.

Kate wore a crisply pressed blue sport jacket, dark navy slacks, and a white button-down shirt. A little tonic on her hair and we were a reverse couple.

Megan showed up as Princess Leia. I was jealous. I wanted to be a princess.

“Perfect,” Megan said with approval. “You two look like a couple. No one will know.”

And they didn’t. We were asked a number of times why we hadn’t worn costumes. I just smiled.

When it came time, Kate and I went to the stage. A judge asked what we were doing. “It’s a costume contest,” she said.

Kate whispered to her. She smiled in amazement.

Suffice to say, we won easily, with the crowd cheering when the announcement was made.

We went out to celebrate with Megan. She whispered to me, “I assume Christine will remain my girlfriend.”

I smiled.