Synopsis:They say that New Years is a time for a fresh start, a new time in people’s lives, a time for new experiences. That whole new experiences thing took on a whole new meaning a few years ago at a New Years party I will never forget.

It all started when I went up to my girlfriend’s house for New Years. She lives about an hour away from home so we don’t get to spend as much time together as we would have liked. I got to the door and was greeted by Hannah. God! She looks so much hotter since the last time I saw her.

I’ll admit, I was a teenage guy and the fact that I’d be basically spending the night at my girlfriend’s house was not lost on me. The party started at 8 but I’d got there at around 6. Hannah’s dad had died and I tried to fix things up around the house whenever I visited. I walked into the kitchen and found Mrs. John fixing something in the kitchen.

“Hey Eli, how’s it going?”

“Going all right Mrs. John? How’s the party prep coming?”

“Between Hannah and I we’re pretty much ready. I just have to make a few refreshments, maybe tidy the house up a bit, and then we’ll be all set.”

“Well is there anything I can do to help?”

“Well,…now that you mention it. A few of the boards on our fence by the pool have come loose. I know it probably won’t happen but I’m worried that some little kid will climb through the hole and fall into the pool. If it’s not too much trouble would you mind replacing them. There’s still some spare wood in the garage.”

“Sure thing. Happy to help!”

I walked out to the back. Boy was she right! The Johns’ pool has a fence that separates it from the rest of the yard. Most of the boards were actually gone. Knowing that I had my work cut out for me, I grabbed the wood from the garage along with the tools and started work.

I was just finishing up when I heard Hannah opening the screen door to come outside. Smiling mischievously I grabbed the nearby hose and positioned myself behind a bush.

“Eli? Hey, if you’re almost done you- AUGH!”

“Ha! Gotcha Babe! You looked like you could use a shower anyway!”

There’s a reason I love my girlfriend. She quickly grabbed another hose and the two of us started going at it. I vaulted over the fence and from my cover I started spraying Hannah. She took cover behind the porch fence but that still didn’t provide her with much cover. I stood up to spray her when BAM! She got me right in the face! Disoriented for a second, I stumbled backwards and fell into the pool! Luckily I’m a good swimmer and managed to drag myself out of the pool.

“Oh my gosh! Eli are you ok?”

“Yeah I’m fine, thanks. Hey can I get a towel?”

“Sure, yeah. Come inside.”

I stepped just inside, still dripping.

“Eli! What happened to you?”

“I kinda fell into the pool Mrs. John.”

“Well go upstairs and into the bathroom. You can’t be at the party with your clothes soaking wet like that! Put them outside the bathroom door and we’ll try to find something for you.”

So I rushed upstairs and peeled my wet clothes off. Hannah knocked a little later, she didn’t have a towel but she had found one of her dad’s old robes. I put it on and walked into their living room.

Hannah walked in and joined me on the couch. With a frown and a worried look on her face she said, “Well Eli, I have some bad news. I couldn’t find anything of my dad’s for you to wear. I’ve been trying to think of something to do but the only thing I can think of is for you to wear a pair of my jeans and a T-shirt or something, then you can change once you’re clothes are out of the wash.”

“That sounds fine, is your mom ok with it?”

“Well she doesn’t see any other solution as well. We could go to a store and find you something but neither of us has the money for that and even if we did, by the time we got back the guests would be here and we need to be home.”

“Sounds pretty straight forward to me beautiful, what have you got upstairs?”

I headed up to Hannah’s room. She started rifling through her closet. Finally she handed me a pair of her panties, some jeans, and an Aeropostale t-shirt.

“Panties? What the hell Hannah! I’m not wearing your underwear!”

“Why not? You’re not going commando in my clothes and you’ll be wearing my clothes anyway. What’s one more?”

So after grumbling a bit I slid the cotton panties up my legs and started to put on the rest of the clothes. My girlfriend is many things but unfortunately for me, she’s much skinnier than I am. After struggling with the pants for a few minutes I gave up.

“Hannah, do you have anything else?”

“The only thing I have with an elastic waist is a skirt.” Just as she said it, I could hear the doorbell ringing and I could hear people being welcomed in.

“Hannah, couldn’t I just stay up here? Then when my clothes dry I’ll come down.”

“That would work except my friends will probably come up here and how am I supposed to explain a boy in nothing but a robe sitting up here in my room?”

“I could think of a few ways.”

“I’m sure you would handsome, but nothing that would keep my reputation intact. Really Eli, you have no other options. Besides,” she added with a mischievous smile, “I think you’d look really cute as a girl, I’d love to have a girlfriend with me for the day!”

Seeing no other options, I reluctantly agreed. “Fine. Go ahead and doll me up.” She reached into her closet and started pulling out items. First there was a white skirt with a lace trim, followed by a violet tank top with a ruffled front. I started to put them on when Hannah interrupted me.

“What are you doing?”

“Putting them on. Why?”

“Look, think about it for a sec. A skirt and obviously feminine top is not something that a man wears. If you’re going to do this you’ll have to be a girl.”

“So? Your point is…?

“My point is that no girl just throws that stuff on. You’ve got to get a bra and then we have to do your makeup! Not to mention that you’ve got to shave your legs and wash your hair”

O.K we were definitely crossing a line here. I hadn’t really thought about that. Hannah led me over to her bathroom and I started to shave and wash my hair. I always kept my hair in a long ponytail, it made me seem cool and rebellious in the circles I ran in. It took a little while to wash but I was in a hurry. After I finished shaving and washing I walked into her room.
“Well?”

“Well what?”

“Well how did it go? It couldn’t have been easy shaving your body like that.”

“It wasn’t that much different than shaving my face.”

“If you say so, let me get you a bra and then we can do your hair and makeup.”

I kinda sat there in nothing but those pink panties while my girlfriend walked over to her dresser and pulled out a matching bra. She walked over to me and put my arms through the straps and reached behind me to fasten it. I should have protested the bra a little more but as soon as she finished hooking the bra, then stuffing it with socks, she tackled me backwards onto her bed and we began the greatest makeout session ever. I couldn’t tell you how long it lasted but I wanted her so much! I was about to make my move when she broke it off.

“We can’t do this here. Not now.” She hastily got up and began straightening her clothes up a bit. Almost in a daze I let her lead me over to her vanity where she began doing my makeup. As she was doing it I could hear more and more people arriving. I knew Hannah’s mom would be waiting for us to come down so we could help get all the food served and everyone situated but I knew that we couldn’t rush this. After she finished with my makeup, Hannah began working on my hair. I wasn’t sure what she was doing but finally she announced that she was done. I turned to look at the mirror but she quickly stopped me.

“Heels or flats?”

“Say what now?”

“Would you rather wear heels or flats? You’d look great in heels and they’d definitely help you look more feminine. On the other hand flats might be easier for you to handle and would keep you at average height for a girl. Still it’s your call.”

“Well…I really don’t know. I trust you, you decide.” I really won boyfriend points with that one. She brought out a pair of black strappy sandals with about a 2 or 3 inch heel.

“I think you’ll look great in these! Put them on and then let’s take a look at you.” So I put them on and looked in the mirror and what I saw stunned me. I saw a relatively pretty girl. Her long wavy black hair falling onto her shoulders, her white skirt making her light brown legs that much more beautiful. She had boobs that were not outrageously large or small but pretty average for her size. In short, she was beautiful!
Hannah cut off my staring pretty quickly. “Alright that’s enough of that. Stare any longer and I’ll start getting jealous!”

“You know I only have eyes for you babe!” I leaned over to give her a kiss but she crossed the room to the vanity before I could plant it.

“There’s just one thing that would make this perfect: you need nail polish!”

I just sat there on her bed as she swiftly painted my finger and toenails a lovely shade of light pink.

“There we go, now it’s perfect. All right c’mon let’s go down and mingle with the guests. Mom’ll get worried if we’re gone too much longer.”

She quickly opened the door and scampered downstairs. I took a deep breath and walked out the door still not entirely sure what I’d gotten myself into.

Thanks for reading this! I was working on the next part of A Senior Year to Remember when this story hit me and I started working on this instead. It was intended to be just a one part story but I think I'll make it two. As always comments, criticism, and kudos are appreciated!