tagTranssexuals & CrossdressersKim's My Best Friend

Kim's My Best Friend


I sit here in my room stroking my 6" uncut cock watching my best friend gently fingering and playing with hers.

Yes I said her. I've known Kim for years what I didn't know was that she was originally a boy. This information is all new to me and after 14yrs of knowing her she finally told me the story.

When Kim was little her parents noticed she was very feminine. Her parents took her to the usual doctors and were referred off to specialists when they found that her hormone levels were not normal for a boy.

Well to make a long story short they found that Ken (her legal name) was I guess was supposed to be a girl but was born a boy. I don't really know anything about this sort of stuff it's all too complicated for me to understand. The general gist of it is that when she was younger they started Ken on hormone treatments and started dressing and treating her as a girl and now at 18yrs old she is a beautiful girl.

I've heard of t-girl, transsexuals and such from the internet I've even jacked off to pictures and short free videos of them but I always thought it was fake. What is weird to me is that Kim and I have always talked about dating, girlfriends and boyfriends but Kim never once has said anything to me.

Things today have changed and this is how it happened.

It's a beautiful summer day and Kim came to my house to hangout at our pool. Kim was always just one of the guys to me someone I could talk to and just hangout with. Until today, today when Kim came over I was out at the pool already soaking up the warm summer sun. I heard the gate and looked over to see her arrive we said our usual hi's and just kicked back for a few.

Asking Kim if she wanted a drink I went inside to get us a couple of sodas. As I was about to go back outside I saw her stripping off her t-shirt and shorts. Today Kim was wearing one of the sexiest bikinis I have ever seen. Unusual for her, she always wore a plain black one piece suit. I stood inside suddenly confronted with my best friend being a sexy girl, one I now realized that I wanted.

I walked back outside as Kim reached into her bag to retrieve to lotion. She looked over at me and smiled, and I notice what a beautiful smile it was. I handed her the soda and just stared.

"Anything wrong?" She said.

"Umm nothing I just have never seen you in a bikini," I replied.

"Yes well I'm a little self-conscious," she says taking the lotion and rubbing it into her arms, "and anyway it's just us."

"Yeah well you look great," I said trying to sound normal, "so you shouldn't be worried about what anyone thinks."

Kim sat down on the lounger and started rubbing lotion into her legs I just sat mesmerized as her hands ran up and down her smooth sexy legs until it all disappeared.

"So you like what you see?" She says

"Ohhh yeah," I replied sounding a little more like a sex starved guy than I intended.

She giggled and laid back as I watched her slide on her sunglasses. We were outside for over an hour not saying anything as I tried to steal glances at her sexy legs and her b cup breasts trying to figure out how I hadn't noticed all these years how beautiful she was.

"If you keep staring at me I'll start to think you want something," she said as she looked over her glasses and smiled at me.

"Huh!" I was caught.

"Well you've been looking at me like your want to say something since I got here," she says.

"Well I've never seen you in a bikini before and I have to say that I've never noticed that you have an extremely hot body," I stated as a matter of fact.

Kim seemed to be embarrassed, "well I normally wear sweats and t-shirts so I guess you wouldn't notice much."

The more I looked at her and the more we talked I knew my feelings were changing for her.

"Y'know Kim we've been friends for a long time and well...," she cuts me off.

"Mike we can't go there," she said very bluntly and no longer smiling.

I asked her what she was talking about.

"Mike there are things about me you don't know," she was now talking quietly and no longer looking at me.

"Mike there is a big secret about me that no one knows but my family," now I was feeling a little betrayed as we had been friends for 14yrs.

"Mike, look I'm just going to say it," I was almost too scared to hear it.

"Have you ever heard of transsexuals," I nodded dumbly at her.

"Well I'm a MtF transsexual," she sat looking at me for my reaction but I don't think there was one.

"I always thought transsexuals were like a myth like big foot and shit," I sounded so stupid.

Once again Kim giggled at me, "no Mike transsexuals are real and I am one."

I sat back in my lounger to maul over what she had just told me. We sat for what seemed like hours but it wasn't. I kept looking over at her and her sexy body and reliving the pictures on the net. I couldn't figure out how I hadn't noticed. I sat back up and turned to her.

"I don't care," I stated very bluntly and to the point, "I don't care what you are to me you are still Kim and I think that I am in love with you."

She sat up and turned towards me; I looked down and suddenly noticed the small bulge in her bikini. Kim saw where I was looking and quickly closed her legs.

"Mike, there's a reason I'm still a virgin. Boys want pussy and I just don't have one," I could see tears welling up.

I reached out and put my hand under her chin lifting her head. I pulled her to me as she gently sobbed into my shoulder.

"We should go inside," I said as I took her hand and led her into the house.

We got into my room and I sat in the chair in the corner leaving Kim to sit on the bed.

"Y'know Kim there are other ways to have sex," I said almost whispering.

Kim came over and kneeled in front of me, "Mike I have a fucking cock and I will want to be sexually pleased too, are you willing to do that?"

I though about her question and thought about the hours of jacking off to the videos and felt my briefs started to stir.

"Yes," I said.

She kneeled and looked trying to read me, to see if I was being honest I think. Kim stood, her bikini clad crotch inches from my face. Her hands moved to the waistband and her thumbs hooked onto the sides. I sat watching with anticipation for her next move. Kim slowly pulled down the band stopping at where there should have been hair, but there was none. She continued on bending as she lower her bikini to her ankles. She was blocking my view.

Kim looked up at me and slowly stood back up; I followed her eyes as she did. She smiled and I looked back down. There in front of me was a tiny flaccid completely shaved cock. Kim looked on nervously as I reached out and took it in my hand feeling its softness.

Kim was circumcised. Of course I had seen one before in the locker room at school and on the net but I had never touched one. It was so sexy, warm and soft. Kim's cock started to grow. I stroked my fingers up and down her shaft as it got longer and longer. I looked up to see her pretty blue eyes closed as she enjoyed my ministrations.

Unconsciously I leaned forward and placed my lips around the head of her cock. I licked the sensitive glands and it twitched on my tongue. I swirled around the head as it continued to grow. Kim moaned as her cock just continued to get bigger. My hand was wrapped around the shaft slowly stroking and I had at least 4 inches in my mouth, "how much bigger," I thought to myself.

Kim pulled away from me and I reluctantly released her and I watched as she went and sat on the bed. She took off her bikini top leaving her completely naked. I admired how sexy she was and realized I did love her.

I eased my shorts and briefs down and off never taking my eyes of her. Kim rolled over onto her side; pushing her cock between her legs she showed me it all. Her cock and balls nestled in place trapped between her legs she reached over her hip and pulled her ass open showing me the tender place I wanted to be.

I sat there in my room stroking my 6" uncut cock watching my best friend gently fingering and playing with hers.

I crawled over to her and placed my face in between her cheeks smelling the sexy aroma of her ass. I slithered my tongue out and lapped at her precious hole. Kim let go of a deep groan that I'm sure came from the deepest depths. I reached up and stroked her cock. It was pulsing so hard that I'm sure she wouldn't last long. I wetted my thumb and rubbed vigorously on her glands my hand wrapped tightly around her shaft. I buried my tongue in her crack again and probed her ass.

With my other hand I blindly reached up and pulled her ass open. My tongue slid inside tasting the tangy sweet flavor. I tongue fucked her ass my thumb worked faster on her cock. Kim went stiff and her cock erupted all over her legs and my hand. I kept my tongue inside savoring her as her cock slowly started to shrink.

Kim rolled over easing herself to the edge of the bed. I lowered down on top of her my cock poked and probed down below as my tongue eased into her mouth. She pushed her hand between us grabbing my cock. She knew how close I was and guided it inside. My cock slid in extremely easy and I sank all the way in. I enjoyed her warmth as I started to slide back out and in. I made love to my Kim staring into her face as I felt her cock come back to life between us.

My cum was boiling it wouldn't be long now. I closed my eyes and cuddled the side of her beautiful face. My cum covered hand was right there. I brought it to my mouth sucking her cum onto my tongue. I swirled it inside my mouth enjoying her taste.

My cum exploded inside her filling her up as I continued to pound her tight little hole. I looked into her eyes as I realized a sticky mess in between us. Kim had had her second orgasm and laid gazing lazily into my eyes.

"Yes," I said.

"Yes what?" She answered.

"Yes I will sexually please you," I replied laughing.

We both rolled over giggling together until we both fell asleep in each others arms for an afternoon nap.

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