tagTranssexuals & CrossdressersMy Best Friend's Sister Ch. 01

My Best Friend's Sister Ch. 01


I'm looking for someone who might be willing to help me out with editing. E-mail me if you're interested, or leave a comment after you have read the story. I hope you enjoy. This is the first in a new series I am starting.


Every kid usually has a crush on their babysitter, at some point or another. It's almost kind of cliche, and a pretty popular setting for some porn videos, too. It's not very often that you grow up though, and end up actually having the chance to hook up with the girl who use to play the role of your babysitter. So, I guess I'm lucky, because I never imagined that someday, I would be in an actual relationship with Christy, my best friend Mike's older sister.

Christy was a good seven years older than myself, and her brother. She use to watch the both of us when we were kids, all the way up to the time we were thirteen years old when she moved away. She was probably the best babysitter out there, or at least that's what I always told her whenever she would come over.

She loved to play video games with me and her brother, she would always order pizza for us when watching us, and it was really easy to get along with her. Never picked on her younger brother; she just wasn't that type of sister.

It wasn't until I was a little older, and could really understand what a crush was, that I realized that was what I had on Christy. Mike laughed about it, when I told him that I liked his big sister, and made fun of me...I didn't take it personal though. I laughed along with him, and made me promise he would not tell her. Of course, he did end up saying something to her one day, and she too laughed and told me that she was flattered.

Then, the day came when Mike told me that Christy was moving. The truth was, it made sense, really. She had graduated high school almost three whole years earlier, and had stayed with her parents after. She worked, and paid bills, and rent to her mother and father...but now, she wanted to go back to school. To further her education, and was moving to New York City to do that.

Apparently, she had been accepted into a really good college out there and seemed really excited to be going.

I knew I was going to miss her. I brushed it off though. Of course, I understood there was no real chance of me getting with Christy, considering the fact that she was seven years older then me. Now that I was older, I didn't need a babysitter anymore anyway...so, at least my parents probably wouldn't bother trying to replace her with some annoying old lady or something.

The day Christy left, she gave me a big hug and told me to take care of myself...and that was the last time I would see her, for five years.

I was in my senior year of high school, the last few weeks to be exact. I had just turned eighteen years old, and could hardly wait to graduate. Prom was right around the corner, and I was taking my smoking hot girlfriend Sara with me. Mike was bringing Sara's cousin, Michelle, and we were going to be riding in a limo together. All four of us were going to have a great night, I was sure of that much.

I would find out though, that I was quite wrong.

The night of prom, everything was playing out good at first, until I stepped outside with Mike to smoke a cigarette. We stood out there talking for a few minutes, and when we decided to go back inside, I walked right in on Sara and a friend of ours named Steve. They were on the dance floor, moving about to a slow song, and making out.

Immediately, I was filled with rage, but I did nothing about it; I didn't want to make a scene. Instead, I turned around and stormed out of the place, with Mike and Michelle trying to catch up to me.

"Nick, wait up!" Mike yelled, behind me.

When I finally stopped, and my two friends caught up with me, we were all out of breath. Mike placed his hand on my shoulder, shaking his head in disbelief; I could tell he felt sorry for me.

"Dude, that was...that was fucked up man. I'm sorry..."

"I can't believe she would do something like this," I said, shaking with anger.

"I really feel bad myself," Michelle chimed in.

"She's my cousin, and I am almost embarrassed to say that now."

"It's nobodies fault," I said, with a heavy sigh. "Except my own, for trusting her."

Mike shook his head, "Dude, you were in love with her; you trust the people your in love with. It's not your fault man, don't blame this on yourself. You don't deserve this shit."

He was right; I didn't deserve this. I sat down on a bench, and lit a cigarette, taking a drag and blowing the smoke out. Mike and Michelle sat down beside me, and we were silent for a few minutes. Nobody knew what to say, now. I was hurt, pissed off and confused, so I had nothing to say either. Suddenly though, Mike cleared his throat, and gave me a pat on the back.

"Nick, I think I know what might cheer you up."

"Oh yeah? Lay it on me; I'd love to hear something that could make me happy, right now."

I didn't think anything my friend said would make me feel any better, really.

"Well, I made a phone call to someone in New York a few days ago," he started. "I called my sister."

I perked up, with a bit of interest now, at the mention of Christy.

"I told her we're getting ready to graduate. I wasn't sure if she would be able to make it or not, but she promised me she's going to be there. Actually...she's moving back here, to Philadelphia. Right in time for our graduation, too."

"No shit," I said, surprised.

"No, it's true. Apparently, she just broke it off with some guy she was seeing for about a year. She can't stand it out there anymore, says there are to many memories about him. She's been done college for a couple years now, so she's coming home for good."

That was to good to be true. I had to admit, he really had managed to snap me out of my little anger induced trance. I was definitely excited for a chance to see Christy; especially, now that I was eighteen and old enough to actually try and make a move. I laughed, thinking about how easily I had forgotten about Sara and her cheating on me, at the mere mention of Christy.

I walked with Mike and Michelle back to my place, and we hung out for the rest of the night.

It was really nice of them to ditch the prom, just to make sure I was okay; most people wouldn't think about doing that kind of thing for someone. I was lucky to have friends like them, though.

The last three weeks of school went by fast. We didn't have much to do after prom, it was all just preparing for graduation. I saw Sara, and she ignored me...I didn't care. Or, at least part of me did, and I tried to hide that part of me the best that I could. Apparently, word had gotten back to her that I saw her with Steve and that was why I had ditched her. She knew it was over, and there was no need to discuss anything.

Still, the fact that she had not tried to explain herself to me, even though she knew it was pointless, showed me how much she had cared. I felt like our relationship was based on a load of shit. I was excited to be seeing Christy, but I had been dating Sara for just over a year...I couldn't get past it, as quickly as I had hoped I could.

When graduation day finally came around, everything was chaos. Running around to make last minute preparations, trying to drive with heavy traffic to the ceremony...it was crazy. I just wanted to get it over with, party, and see Christy. We got to the school, made our way to the auditorium and lined up behind the stage. Side by side, girls on the left and boys on the right, just as we had practiced a hundred times over the past month.

After walking out on stage and receiving our diplomas, we made our way outside, in front of the building to regroup with our families. I met up with my parents, and a few aunts and uncles along with Mike and his family. The process of picture taking began, and there was laughter and joking as everyone congratulated us for our accomplishments.

When it was all over, I told my parents I would be going back to Mike's house for a party that we were going to have. They were okay with it, since they were planning a party of their own for me at a later date. We got in Mike's car, with Michelle in the back seat, and arrived at his house within minutes. As we walked up to the front door, the door opened and there she was...Christy, with that same old big smile, I remembered.

"Mike!" She shouted, embracing her little brother in a hug.


Mike laughed, as she squeezed him before giving him a kiss on the cheek and turning her attention to me. She looked different, but definitely not in a bad way. She had gotten a little taller.

Her breasts seemed to have gotten a bit larger, then the last time I had seen her, which was only about three years earlier at Mike's birthday. She had also grown her hair out.

I remembered her being a little on the tomboy side back when she was younger. She had always kept her blonde curly hair short, about neck length.

I thought it made her look even more attractive, but I had always had a thing for girls with short hair. Regardless, she still looked smoking hot, even now that her curly blonde hair was down to her shoulders. She also looked like she had some muscle to her now. Maybe she had started lifting weights? Some would think it strange, for a girl to lift weights.

I didn't mind it though, if that was something that she enjoyed.

For a moment, it looked like she might not recognize me. She just stood there smiling at me and I was starting to panic, thinking she may have forgotten who I was. Then, she perked up and gave me the same big smile she gave her brother, and I knew she remembered me.


Moments later, she had thrown her arms around me and was squeezing me as she had done to her brother. She had me in a bear hug, and I was pretty sure she had to be working out with that kinda strength. I laughed, hugging her back as she congratulated me and took a step back to smile at me.

"God, you've gotten so big," she exclaimed.

"You really grew up nice, didn't you?"

"Thanks," I said. "So have you."

"Well, congratulations; come on inside!"

She led all three of us into the house, where the party already seemed to be in motion. Mike's parents were going out of town, and had left immediately after the ceremony. So, there were no adults at this party. Well, technically Christy was an adult, and I joked with her as we stood in the kitchen, saying that she was babysitting her brother and I again like the old days.

"Oh, you two are all grown up now," she said.

"No more babysitters for either of you. Now,

I'm just Mike's big sister, and hopefully a friend to you."

"Of course," I said, smiling.

"Let's drink to it?"

I was surprised, as she pulled out two beers and handed one to me. I had no problem with it, though I wasn't expecting her to give me one, since I wasn't twenty one yet. Regardless, I cracked open the beer, held it up and clanked the can against hers, before we both took a big swig. In the other room, the stereo was blasting. Christy and I went out and sat down with Mike, his girlfriend and a few other friends of ours who had come over to party with us.

After about an hour, we took the party out into the backyard, where Mike had a pool that his parents had just set up the previous weekend for the summer.

I joined everyone in the pool, the water felt great in the hot afternoon air. I dunked my head under, coming back up and wiping the hair out of my face. Mike swam over to me, leaning against the wall behind us and looking up at the sky.

"Dude," I started. "I think I may actually have a chance."

"A chance to what," he asked, looking confused.

"You know...with your sister," I whispered, not wanting anyone...especially Christy, to overhear me.

Mike looked surprised, and laughed, moving closer to me and whispering back.

"Dude...you know I was only joking, when I suggested that you make a move, man."


"Nick...I figured hanging out with her, would cheer you up. I didn't really expect you to try and make a move on her."

I was shocked. I thought that I had Mike's blessing, as far as making a move on his sister. It was starting to look like I may have been wrong, though. I wasn't sure how I managed to miss the fact that he had not been serious, but I worried that I may have pissed him off now.

That was the last thing I wanted.

"Mike, if your against it," I started. "I'll back off. I wouldn't make a move on her, if it's something you're not okay with."

"It's not that I'm against it," he said, looking a little uneasy now.

"Then...what's the problem?"

Mike hesitated, for a long time. He looked like he was in thought, like there was definitely something he wanted to tell me about his sister. If it wasn't the whole "that's my big sister" thing, keeping him from letting make a move, what was it?

"Christy is a little different from most girls," he finally spoke up again. "She's actually, REALLY different from other girls."

"Different? Different how?"

"I can't get into it man," he said, looking like he wanted to tell me, but still holding back.

"It's just, there are some things about my sister that you're not aware of, and if you knew, I don't really think you would be as interested in her as you are right now."

With that said, he turned and swam back to the other side of the pool, obviously not willing to continue the conversation. What was he talking about, I wondered. I couldn't make sense of anything that he had just said to me. What could possibly be so different about Christy, that Mike didn't think I would like her the way I did right now, if I found out? At that moment, I noticed her coming out of the house and walking down towards the pool. She was wearing a two piece, pink bikini; she looked absolutely beautiful.

Her blonde hair hung over her shoulders, and her pale skin looked smooth and soft. I bit my lip, admiring the sight of my long time crush, but trying not to go against the promise I had made to Mike just a few minutes earlier.

She stopped by one of the lawn chairs, and went to lay her towel on the chair but dropped it.

Then, turned around and bent over to pick it up, giving me the perfect view of that beautiful, bubble butt. I shivered, as I felt myself getting hard.

She turned back and smiled at me, taking off her sun glasses, and then started running towards the pool. I quickly moved back, realizing that she was about to dive into the water. She jumped into the air just before she reached the edge of the pool, and came down, splashing into the water. It splashed on everyone else around in there, and we all laughed as Christy came back up and moved her blonde hair out of her face.

I started making a few laps back and forth across the pool, trying to clear my head and figure out what Mike was talking about.

I had known Christy as long as I had known him; what secret could she possibly have, that I did not already know about?

Her pale wet skin, glistened from the sunlight as she smiled over at me, and started moving in my direction. I tensed up some, when I realized she was coming over to me; what would I do, now that Mike had made it clear that he didn't want me messing with his older sister?

"Having fun, Nick?"


I jumped, surprised by her voice as I had spaced out apparently.

"Uh...y-yeah, yeah I'm having a lot of fun."

"Good," she said. "You should be; you just graduated and all, today is the beginning of a new era for you."

"Yeah, I'm looking forward to the rest of my life," I laughed. "Whatever happens next."

"That's good to know. You know, I have to admit, I've kind of missed you, kid."

"I'm not much of a kid anymore, am I?"

"No," she smiled, and then moved in and gave me a hug.

Our wet skin pressing together, I felt my cheeks turning hot. I hugged her back though, hoping she wouldn't notice my cock, which was currently hard as a rock.

"Tell me Nick; you got a girlfriend?"

"Uh...no, well not anymore, anyway."

"Oh? That's a shame," she said, and it almost sounded like she was trying to sound disappointed.

"Hey, do you wanna go have a cigarette with me?"

"Sure," I agreed, and she took my hand and led me out of the pool.

As we climbed the latter out of the water, I looked back and noticed Mike staring at me; he looked a bit annoyed. I didn't want to piss my friend off, but at the same time, it was only a cigarette. Why should I ignore her all together, just because Mike didn't want me trying to hook up with her?

We walked to the patio, and I sat down at the glass picnic table. As Christy moved around to the other side to sit down across from me, I took note of something strange; something very out of place. In her bottoms, I could see something poking out. Like an outline of something in a spot where there shouldn't be something sticking out. A bit confused, I brushed it off, trying to convince myself that my eyes were probably just playing some cruel trick on me.

I couldn't possibly be seeing what I thought I was seeing, and that was that.

Christy sat down, pulled out a pack of Marlboro Cigarettes, and handed me one. She lit up hers, then passed me her lighter so I could light my own. I took a drag, blew the smoke out and she smirked at me.

"So, tell me Nick; why doesn't a guy like you have a girlfriend?"

"Oh, uh...well, things just sort of went down hill for us."

I didn't feel like going into details, but Christy wasn't feeling like backing off that easily, either.

"What happened, if you don't mind me asking?"

"Well, to make a long story short; I caught her cheating on me, at the Prom."

"Oh my god, Nick; that's fucked up!"

She seemed pretty sad to hear me tell her what had happened. I found myself going into details, and forgetting about the fact that I had not originally wanted to do that. I had forgotten, how easy it was to talk to Christy. Things always just seemed to flow so easily, when you were having a full on conversation with this girl.

That's what had made it so easy for us to get along, when I was younger. If something was wrong, she could always tell, and most of the time I didn't feel comfortable talking to anyone else about whatever was going wrong at that time.

"What a bitch," Christy said, when I finished telling the story.

I laughed, and took a drag of my cigarette.

"No, your laughing; I mean it, Nick. Sara is a bitch. You deserve so much better then a girl like that. Someone out there is waiting for you, and when you find that girl...I'm sure she'll treat you the way you deserve to be treated."

"Thanks Christy; I hope so...what about you? You got yourself a boyfriend?"

She smiled sadly, lowering her head for a few moments. I forgot, Mike had already told me when he first said she was coming home; she had just broken it off with some guy, out in New York. I felt bad for even asking, now.

"I'm sorry," I said. "I shouldn't have-"

"No, no it's okay," she insisted. "I asked you, so it's only fair."

I lit up a fresh cigarette, and waited for her to continue.

"I was seeing this guy out in New York, for a few years. He was a good guy; at least, I thought he was. I thought we were in love, and that we would be together forever, but...it just didn't work out that way."

"His loss, right?"

She smiled, and nodded her head as she put out her nearly finished cigarette. "Might be your gain."

She winked, and I blushed, surprised at what she had said. We continued talking and catching up on lost time. Before I knew it, it was starting to get dark outside. A lot of our friends who came to the party, had already gone home by now. Mike and Michelle finally came up from the pool area, walking into the house.

As they passed us, Mike glanced over at me, looking curious. I still wondered what exactly he had meant earlier, but could not figure it out. I wasn't about to end my conversation with Christy, to go ask him either. Besides, he was in the house with Michelle...I didn't want to disturb the two of them, while they had some time to themselves, all alone inside.

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byWhiskeyIsGood© 22 comments/ 86679 views/ 188 favorites

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