Like many sixteen-year-old boys, I was at that age where I had moved on from department store magazine bra and panties pages to the pages of Playboy magazine. There was not much left to the imagination in these pictures, and I quickly became fascinated by the female form. As much as I admired the female body, I couldn't help but be drawn to their makeup, hair, and everything satin, lacy, and sexy that gave them that alluring look. I started imagining what it would be like to wear some of the things they had on, especially the bras and panties.
It was on a dare from my buddy Jimmy that I put a bra on for the first time. Jimmy's seventeen-year-old sister Missy had left it on the bathroom floor, and he caught me admiring it. As soon as he dared me, I quickly took off my shirt, slid my arms through the straps, and connected the front closure. I paused for a moment to admire how it looked in the mirror before taking it off. I was very athletic for sixteen but not shredded by any means. The little bit of fat around my chest helped fill out each cup. Before getting too lost in the moment, I removed the bra and tossed it back on the floor, grabbing the five-dollar bill Jimmy was holding out. It wasn’t until later that night that I started thinking about the experience and how that bra felt. I definitely wanted to try one on again but had no idea when or how that would happen.
It was three weeks later that Missy saw me at their house. She and I were friendly but certainly not close friends. After all, she was older than us and always reminded us that she was "almost eighteen". Missy was really cute, and all of us secretly had a crush on her. She called down that Jimmy wasn’t home yet, but to come upstairs. She needed to talk to me. I walked into her room to find her casually reading a magazine on her bed.
“So, I heard you like wearing my stuff?” she asked quite bluntly.
“I’m really not sure I know what you’re talking about.” I felt my face getting red in embarrassment.
“Does this look familiar?” she asked, twirling the same lacy white bra I had tried on around her finger. “Jimmy told me you decided to try on a few of my things. I really don’t care but next time, just ask.”
“I’m really sorry. And it was just that bra. It was on the bathroom floor. And there was a bet. It won’t happen again.”
“That’s too bad. I was hoping you might want to try it on again. Jimmy never lets me dress him up for fun, but he’d be an ugly girl anyway. Let me know,” she said as she waved the bra in front of me. “I think you’d look cute as a girl.”
Part of me wanted to accept her offer right away. Part of me was still way too embarrassed. Part of me was pissed at Jimmy for even saying anything. Then I realized I was standing there, saying nothing and feeling really awkward. I heard Jimmy come in the door downstairs and told Missy I’d catch her later. I spent the next hour or so being pissed at my buddy for telling her. At one point, as we bantered back and forth, I suggested that I might take her up on the offer. Jimmy laughed and threatened to tell her. I told him to go ahead. I figured it was playful banter at best. However, at some point, while we were hanging out that night, Jimmy had told her sister that I had agreed. As I was leaving, Missy asked when I was coming for my makeover.
“Why not tomorrow night? But I expect a full makeover, right?” I said jokingly. “I mean, I want makeup, hair, a cute outfit. The works.”
“No problem,” she confidently replied. “See you tomorrow night.”
My mind was racing as I walked home. Holy shit! Was this really going to happen? I went from calm and cool to nervous as all hell when I started thinking of what may happen. By the time I got home and got into bed, I couldn’t wait for the next day to get here. I was up early, wanting to get everything I had lined up for the day out of the way so I could be ready. Then Jimmy called and bummed me out. His sister forgot she was going out with their mom and had to cancel. I was dejected. I moped around the house all day and the rest of the weekend. My parents asked if I was sick. My anticipation was so high that when she canceled, I crashed and burned.
With Jimmy and all my friends teasing me about my makeover (yes, Jimmy was nice enough to spread the news) and my disappointment that this would probably never happen, it was a long, dreadful week. That was until Thursday, after school, when I ran into Missy in the parking lot.
“Jimmy said you guys will be done with your game by three, and I’ll be home shortly after that. So are we going to do it this Saturday or not? I told him to have all the guys over. All your friends should see you. You’ll be so cute; they’ll all want to make out with you. Are you up for it?”
I was speechless, excited, and nervous again as I mumbled out, “I guess I’ll see you Saturday. But, I’m not making out with my friends.” She laughed and said she’d see me Saturday.
Saturday couldn’t come soon enough. I got there right as Jimmy’s mom and dad were leaving.
“You have fun tonight. Don’t get into any trouble," his mother said.
Missy was at the door, giggling with her mom, pulling me into the house. “Jimmy! Your friend is here! He’s coming upstairs with me.”
We went up the stairs. As I walked into her room, I realized how much she was really into this. Her makeup kit was out on her desk, she had a variety of clothes spread out on the bed, and many of her bras and panties lying out for me. I literally stopped just inside the door of her room to take this all in. Jimmy came up behind me and pushed me in. Laughing and said he’d be watching TV, waiting for the guys. He just wanted to see “the final product”, questioning his sister’s ability to make me look like a girl.
She pulled me in, telling me how fun this was going to be, pushed Jimmy out, and closed the door behind her. All I really remember is her telling me a million things she was going to do, about how she had an idea how to dress me to look cute, how she didn’t have shoes that would fit, but she had outfits that would work, and on and on. She had clearly put some thought into this. While my exterior was showing a reluctant participant, inside I was giddy with excitement. She looked at me and told me to relax and have fun. So I did. And boy was she was right.
It was nearly ninety minutes or so later when Jimmy and two of our other buddies started knocking on her bedroom door to check out her work. She let them in, and both she and I laughed as their jaws hit the floor. Their buddy, who they played football and baseball with, who shot hoops in the front yard with them, and talked about girls with was now a super cute “girl”. They were speechless. Jimmy could only mutter a “Holy Shit.”
Missy had done a great job. Her makeup and hair work was incredible. I had a typical part down the middle, 1980’s hairstyle, that sandy brown and had a little length. She had something natural to work with. Using a little hair spray and a cute headband, my hair looked like any typical sixteen-year-old girl’s. She had pulled out a number of outfits for me to try on, but since most didn’t fit very well, we settled on a black sweater dress. This worked with my gym shoes since she didn’t have any shoes that would even come close to fitting. It was a simple, kind of preppy look. And while we argued over it, Missy was right in convincing me to shave my legs. I knew she was right when I caught one of the guys staring at them, asking me, "dude, did you shave your legs?"
What the boys couldn’t see were the black bra and panties I was wearing under the dress. Missy had actually purchased the set for me and gave them to me “in case I ever had the urge on my own." She also used a little padding to round them out a little. It was one of several small details that did not go unnoticed by my friends who wanted to know how suddenly "I grew boobs." I checked myself out in the mirror and couldn’t believe how great she had done. Yes, I was adorable. My buddies were all amazed.
Missy whispered in my ear, “I told you they would all want to make out with you. I think I was wrong. I think they would all want to fuck you tonight.”
I was a little caught off guard, but I giggled and told her she was totally right.
“What was that? A giggle?” asked Jimmy. His sister quickly replied.
“Jenni can giggle all she wants, boys. Now get out of my room! But not you just yet,” she said, grabbing my hand.
“Thanks for being a good sport. None of your friends, and certainly not my brother, would have ever done this. You look adorable.”
“I can’t thank YOU enough. This was an incredible experience. I have to admit, I like being dressed like this a lot more than I thought I would. Would you help me again sometime?"
“Wow! That was quick. Not a problem. I’d love to help you. And of course, I’ll help you with other things you may have questions about. You may not think about it now, but you are really cute. If you ever went out like this, a boy would definitely want to kiss you, or maybe more. But let's save that conversation for another day.”
Jimmy popped his head back into the room. “Come on, let's go. Get changed and meet us in the basement.”
“No. I’m ready. Let’s go,” walking right past him. I poked my head back in and blew Missy a kiss.
“Jimmy, your sister is the best.”
“Dude, you’re not going to change?”
“So tell me this, Jimmy, who was the one who pushed me to do this? You. And now you want me back as your ‘guy’ buddy so quickly? That’s not going to happen tonight, pal. In fact, I bet I can even sound a little more like a girl by lowering my voice a tone or two.
“So guess what? Tonight Jenni is going to hang with the guys. Are you ok with that?” I asked in a softer, more feminine tone.
“Hell ya! Dude, seriously. You are hot. I can’t even believe I just said that.”
And off we went downstairs to hang out with our buddies. After what seemed like a million questions from the guys, the night became just like most others. Jimmy’s mom and dad came home later that night. We were all huddled around the TV watching a movie in the basement when we heard them coming down the stairs. “Holy shit!” I thought to myself. I thought his mom knew, but maybe not. I’m sure Jimmy’s dad had no idea. There was really no hiding it at this point.
“So Jimmy, I hear you have a new friend over. Is it Jenni?” his dad asked as he made his way over to the couch to say hi.
“WOW!” His mom couldn’t believe her eyes. A second later, Missy came downstairs.
“Missy, honey, you did a great job! I’m stunned.”
His dad told me to make sure these boys minded their manners. If they started anything, I could come and let him know. We all had a good laugh.
Any fear or nervousness I had been feeling had long gone away. I was way more comfortable than I would have ever imagined I would be. A feeling of femininity had overcome me for the first time, and I really liked it. I hung with the boys that night and watched as each of them tried to sneak a peek at me, always trying to make it look as inconspicuous as possible. It was around eleven pm when Missy came down and asked if I wanted help removing my makeup and transforming back. I told the boys I was off for the night and reminded them to keep this on the down-low.
Upstairs with Missy, I felt a little sadness changing into my own clothes and having my makeup removed. I thanked Missy again and again, and she couldn’t stop gushing over her protégé.
“You were unbelievable. I never, ever imagined we… no, you, would ever pull this off like you did. Did you see the way your buddies were checking you out? By the time the night was done, none of them thought of you as a dude. You were awesome.”
“Thanks. It was amazing to feel the way I did. I know it was a one-time dare, but if I ever wanted to do that again, were you serious that you would be willing to help me?”
“Hell yeah I would. I was hoping you would say that. There is a lot I can teach you if you wanted. Have you ever thought about being with a guy?”
That question really caught me off guard, and I think Missy saw that I wasn’t quite sure how to answer that.
“I’m sorry. That was really straight forward, wasn’t it?” she asked.
“No, it’s ok. I never would have until tonight. Sitting down there with the boys, knowing they were looking at ME, I caught myself a few times thinking some really weird things. But thinking of myself as a girl and checking them, checking me out? I think we definitely need to have some of those conversations."
“Like, what were you wondering? If they were hard for you?”
I laughed. “Well, no. Like are they good kissers, and what would it be like if one of them tried? But now that you say THAT, I wonder if they were?”
“All topics for another night, my dear. You better get home before your mama comes looking for you. And don’t forget these,” she said, tossing my bra and panties to me.
Once I was at home and in bed, my mind was racing, thinking about the night. Never in a million years would I have ever thought about dressing the way I was dressed, acting the way I was acting, and thinking about some of the things I was thinking about. But Missy was right. Tonight was an incredible night. Everything else would be for another day.
