My Crossed Life – Chapter 11: Jenni Gives All Of Herself To Her First True Love

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 Escort Side 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, manavgat escort 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. alanya escort bayan 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.”