The Bet

I had always been curious about feminine clothing. How, for example, girls' jeans are shaped differently on girls compared to men's jeans on men. Both were jeans, yet somehow, they were vastly different from one another. I had never publicly admitted my curiosity to anyone, though, so when Lisa mentioned wanting to give me a feminine makeover for a day if she won a bet, I couldn't help but to lose on purpose...

"Come on in!" Lisa said cheerfully as she opened the door. I had only barely gotten inside before she rushed me to the bathroom. "Did you remove your body hair, as I asked you to?" she asked.

"Yeah. I even bought a body trimmer for it.  Made it look all nice and smooth, no razor burns," I replied, entering the bathroom.

"Good. Then let's get you out of those pesky boy clothes and see what we're dealing with," Lisa said. 

As requested, I took off all of my clothing, aside from my underwear.

"You do indeed look hairless. Very good," Lisa said, inspecting my body carefully. "But you still smell like a man, so I'm making you shower again." Lisa pointed at the bottles in the corner of the shower and said, "Use the soap, shampoo, and conditioner I left for you in the shower. They'll make you smell sweet, like bubblegum." She then left the room.

I got in the shower and shampooed my hair. The shampoo smelled so sweet. Why couldn't men's shampoo ever smell like that? Men's shampoo was always some odd smell that only conveyed that you showered, but it never smelled as amazing as this... I knew at this point that I had to start switching out my shampoos.

As I let the shampoo do its thing, I soaped up a washcloth and lathered myself in soap, making sure I was fully clean before rinsing it off and washing out the shampoo. Then I applied the conditioner. My hair was only shoulder-length, so it wasn't feminine per se, but it also wasn't the typical manly short cut. There was plenty of reason to use conditioner, but I just never bothered with it before. Another extra step in cleaning hair? Ugh. At least, that's what I used to think. Until today, as I experienced the effects of a good conditioner. Within seconds, my hair started feeling very soft and smooth. I had difficulty keeping myself from brushing through my hair forever. It just felt and smelled so good...

After I finished showering, I carefully dried my hair, first with a towel, and then with the hairdryer Lisa had left for me. When I turned the hairdryer back off, Lisa knocked on the door. "Do you see a spray bottle of argan oil?" She asked. "Give a spray or two on your hands, rub them together, and comb through your hair with your fingers. It'll make your hair look so much better."

I did as she asked and applied some argan oil to my hair. Afterward, I looked in the mirror. It was partially fogged up, but even in the foggy reflection, I could confirm that my hair was looking smooth and straight, as opposed to my natural curls. This stuff was amazing! It was like a whole new world had opened up to me.

Having finished with my hair, I turned to where I had placed my clothing, only to find my clothing was no longer there. "Uhm, Lisa?" I asked. "What happened to my clothes?"

"The makeover cannot be completed if you're not dressed femininely!" Lisa replied. "I left you something more appropriate to wear. It's on top of the laundry machine. Put it on, and when you're done, you can find me in the living room."

I turned to the laundry machine and saw some neatly folded clothing on top of it. Blue denim shorts and a white crop top. Lifting the crop top, I also discovered something that made my face flush. Lisa had actually left black lace panties for me to put on. It was even decorated with a small, white bow on the front.

I had to take a minute to regain my composure. When I had managed to calm down, I slowly put on the panties. They were soft, a little bit tight, but still stretchy enough for it not to be an issue. Was it just in my head, or were these panties really that much different from the boxer shorts I was wearing before? These felt so soft, so comfortable, so luxurious. It's strange to say, especially with how the back of the panties left my cheeks rather exposed, but they made me feel like royalty, and most of all, desirable.

"How's it going in there?" Lisa yelled from the living room.

"Getting there! Just a minute! I replied.

Time for the shorts... I grabbed and held them in front of me. At first, I thought they might not fit, but the material seemed to be a lot more stretchy than the denim I was used to. So I proceeded to try and put them on. While doing so, I finally realized that these shorts were not regular shorts. These were high-waist shorts, that rose to just above my belly button and hugged my skin tightly. I looked in the mirror. Not only did they look different from the shorts I was used to, but they also made me look different! They accentuated my shape and left me in shock as I discovered my body had curves I was never even aware of due to my own baggy men's jeans.

Finally, the crop top. It looked so simple, yet also so scary. It exposed my midriff, but also my collarbone and a large portion of my upper chest due to the top having thin straps. Seeing myself in my new look felt a little weird at first. I guess it's because I simply wasn't used to seeing myself like that. But at the same time, I felt like a new person. It was very freeing.

I opened the bathroom door and shyly walked out. Lisa looked at me and started clapping. "Whoo! You go, girl" she cheered. "You look even better than I expected. Have you done this before?"

"Thanks, and, no," I replied, evading eye contact as my face turned red once again.

"Aw, don't be shy. You look great, I mean it," Lisa said, grabbing my hand and holding it gently. She looked up at my chest. "I know. Your eyes are up there," She joked and let go of a short laugh. "I didn't want to overdo it, embarrass you, and scare you off, so I didn't include a bra in your outfit... but, if you want to..."

"Maybe later?" I replied. "I'm still getting used to everything that's already going on."

"Well, it's better than a 'no', I'll take it," Lisa said, smiling. "Come, sit down. Your body and hair already look great, but we still need to do a few little things before we're done." She tapped the seat of the couch.

I sat down next to her, and without a word, she got up and procured a hair tie and a brush. She wrapped the hair tie around her wrist and started brushing my hair together until she was satisfied with it, and then removed the hair tie from her wrist, twisting it a couple of times, until it securely held the newly formed ponytail in place.

"One down, two to go," Lisa said, sitting back down next to me. She grabbed a perfume bottle from the table and spritzed a little on the palm of her hand for me to sniff it. I would describe it as being a typically girly perfume smell. The kind I would associate with innocence, youth, and cuteness. The fragrance was noticeable, but not overpowering. Besides that, it was also a pleasant smell, as opposed to men's cologne, which was often pungent and rather unpleasant.

"It smells good," I said. I had closed my eyes and breathed calmly, as I imagined being in a field, surrounded by thousands of flowers giving off this smell. I opened my eyes again and made eye contact with Lisa. She smiled at me, as she probably imagined what I was going through, now experiencing all these moments of feminine delights first-hand.

Lisa lightly spritzed some perfume on me. "There you go," she said proudly. "I love your new smell, it's a huge improvement." She put the perfume back down, grabbed her makeup kit from the table, and turned her body fully toward me.

"Close your eyes... Open... Look up... Now look down... Close your eyes again, pucker up!" Lisa instructed. She applied makeup to my face with dedicated concentration. With more effort than I usually had when I washed my face before heading out to attend our university classes. Foundation, concealer, eye pencils, mascara, and even lipstick. Lisa spared no expenses. The time she put into my transformation made me both scared and excited to see the final result.

"Done!" Lisa said, contentedly. "Have a look in the mirror."

I got up and walked into the hallway. Looking at my reflection in the wall-mounted mirror, I could hardly recognize myself. My eyelashes looked thicker, the impurities of my skin were smoothed out, and my eyes drew more attention because of the eye pencil darkening the edges, I felt like a movie star! I never knew I could look this good.

"Like what you see?" Lisa asked, peeking around the corner from within the living room. "I know I do." She winked and blew me a kiss.

"Are you kidding me? I love it!" I replied. "Though I do think my eyebrows ruin the illusion," I added with a hint of disappointment.

"Illusion? Babe. If you wanna be a girl, you can," She said. "I only didn't use my eyebrow razor on you because I thought it might be too much. It's not something you can just undo when we're done today."

"It's okay... do it" I replied, a slight hesitation in my voice. I knew it might be a little difficult to explain to others later, but I wanted to be part of this experience, and I wasn't going to let my eyebrows get in the way of that.

"You're perfect, you know that?" Lisa said, walking off to get her eyebrow razor. When she came back, it didn't take her long to shave my eyebrows into a thinner, more femininely styled shape. "How about this?" She asked.

I looked into the mirror again. "Who's that girl?" I asked rhetorically.

Lisa chuckled. "I'm just happy you're enjoying this as much as I am," she responded. "C'mon, let's lie down on the couch, cuddle, and watch some TV for a bit... Oh, and if you want to do this again someday, don't hesitate to ask," she said, as she looked lovingly into my eyes.