My Best Friends Ch. 01

~The following is the true story of my awakening as a male to female transsexual which never would've been possible without all of my friends. Names and ages have been changed to protect the privacy of those friends.~

Eighteen. A tender age. I'm just a young boy finishing up my senior year in high school. My name is James, or as my friends just call me, Jimmy. It was the last day before summer vacation and I couldn't wait to get home for two reasons. Reason one, Im now a high school grad, and reason two was a secret known only to myself and my cousin Michelle (my mother and I lived with my aunt, uncle, and cousin). I secretly have had the desire to be female. My cousin found me out one day when I fell asleep crossdressed in my room and she came in to talk to me about trouble with her boyfriend. Despite being a "guy" up until now, I was always more like a big sister to her. And now she knew the truth. I was small for a guy of my age and me and my cousin were both around 5'9 and 120 lbs. She gave me many of her old clothes (bras and panties included) and made me a deal.

"If you really want to be a girl, I'll help you as much as I can but first, you need to throw out all those boxers. From now on, it's panties only missy!"

"Okay," I say, "But I'm not coming completely out with this for a while."

"That's fine but you know your friends will have to find out sooner or later."

"Yeah, yeah."

"I have a question for you though. Do you like guys or girls?"

"I haven't really thought much about it..." Truthfully' I had never really shown THAT much of an interest in girls. I had one or two "girlfriends" but it never lasted. I was never quite comfortable with them. On the other hand, I've had no active interest in guys either.

"Hey! Aren't you going to spend the night with Ryan tonight?" She changes the subject.

"Yeah I am." After remembering this, I took a bag out of my closet and packed it up with guy clothes and the likes. My body hair was completely shaven even though I was only a girl in secret. My guy friends thankfully never noticed this.

While on the subject of my appearance, I also must mention I have blue eyes and medium-length blonde hair. I kept it mostly straight and, even though discretely, in a feminine style. Michelle loved brushing my hair and I knew she would enjoy it even more now that she knew her cousin was a girl too. My friends would tease me about my hair a bit but never said anything about it. But for now, I was hungry and decided to go eat while Michelle fixed up my underwear drawers.

* * *

Later that night, it was time for me to walk around the corner and head to Ryan's house for the evening. Ryan and I decided that since we were there alone, we would celebrate the first night of summer in the real world by staying up all night tonight just being guys. However, things did not go according to plan. There would only be one guy here tonight.

"So Jimmy, how've the fish been biting lately?" His metaphor for me finding the right girl. He always said I was picky and careful, like a fisherman always throwing them back.

"Same as usual. Not even a nibble..."

"That's too bad man. Oh well who needs 'em anyway. It's guys only tonight!"

"Yeah!"

Throughout the evening, we had hung out as originally planned. We ordered some pizzas, drank sodas, and played a bunch of video games, in which of course I was ALWAYS a female character. Eventually, we got onto the topic I would hope never came up between us.

"Hey I'm just wondering but... Well it's kind of embarassing to say but... have you, well you know, ever thought about BEING a girl? I mean you're small, not great at many sports, and are always the female character in our games..."

ONLY EVERYDAY OF MY LIFE!! I wanted to scream, but what came out was "Nah not really. I'm happy the way I am. I couldn't see myself as a girl."

"Well I could. You're hair blowing back in the breeze while sunbathing on the beach, sun shining off of your smooth skin, bathing suit perfectly conforming around your tits and down there too..."

I noticed a bulge in his pants making them into a tent. Was the thought of me as a woman getting my best friend hard??

"Umm Ryan... I kinda lied. I've wanted to be a girl as long as I can remember... I just didn't want to say anything because I thought you would, you would..." I began to almost cry.

"Look Jimmy, you're my best friend. If you want to be a girl, you be a girl. I don't care. You'll still be my best friend. Hell, I'll start treating you like a girl if you want."

"I would like that. A lot..." I yawned loudly and stretched out, "I know we were gonna stay up tonight but do you mind if I get some sleep?"

"Sure. You can use my sister's room for tonight if you want." His sister moved out last year and took all of her things with her. All that was left was her beautiful four-poster bed and silky pink sheet set. Just knowing I was going to sleep here made me feel like a princess.

"Hey Ry, I'm gonna get a shower and get changed for bed. I'll come back out after I'm done." I went into his room and got my bag and went into the bathroom. It was in here that I opened my bag to find a surprise. Michelle had switched the clothes and shampoo and everything I packed with the new ones she had given me! And what I found in the bottom of the bag surprised me even more.

"Ryan!" I called, "Looks like Michelle switched what I had in my bag... Looks like I'm dressing the part tonight."

"Oh! Okay. I can't wait to see how you look."

After taking my shower, I dried myself off and rummaged through the bag finding what I needed. There it was! A short pink nighty with a black bow on the bust line. If I bent over, it left my ass completely showing. I also picked out a black lacy bra and matching panties to wear under it. When I unfolded my panties I found another surprise from Michelle... A Trojan brand condom. It was a "Her Pleasure" lubed style... Her idea of a joke...

"Okay Ryan!" I yell from his sister's room as I put my bag down and layed across her bed getting into as sexy of a pose as I could muster.

"DAMN! I never expected this!" Ryan exclaims when he enters the room. "So anyway," he says sitting on the bed next to me,"if you're going to be a girl tonight... are you going to do some girly things?"

"Like?"

"Well like... umm... well this is embarassing to ask but... would you blow me? Please? I haven't had a good blow-job in so long. Please?"

"Umm... I don't know. I mean well, it isn't something I've done before..."

"It's okay. I'll guide you this time. Please?"

"Hmmm... Well I guess it wouldn't hurt." He unzipped his jeans, pulled down his boxers, and his already erect dick sprung forth. I couldn't believe my eyes! It was the biggest thing I had ever seen! He had to be at least 8 or 9 inches long and it was thick too! I didn't know how I was going to fit that whole thing into my mouth!

"Now you're going to want to breathe through your nose while sucking." He instructs as I get off the bed and position myself on my knees in front of his cock. I opened my mouth and I put the head in. I couldn't believe what I was doing! I started today like any other as an eighteen year old high-school grad and hear I was in lingerie with my lips around the head of my best friend's cock! Evnetually. I relaxed an began to bob my head up and down, taking in more and more of his cock with each time my head came down.

"You're sure this is your fisrt time? If so you're a natural. Hey stop for a minute."

I did but looked up at him silently with the look on my face saying everything for me. Why?

"You're doing a good job but I was thinking... why don't you go all the way tonight? Just let me go grab some lube and..."

I knew where this was going. "Wait! One, I don't know if I'm ready for that and two, look in the top pocket of my bag. He pulled out the condom with a curious look on his face.

"Michelle's idea of a joke."

"Oh. Well, it'll do." He opened the wrapper and amazingly, the condom covered his whole cock! I knew where this was going but still didn't know if I could take that whole thing into another certain part of my body.

"Look I know this a lot to take in all at once but..." he cracks a smile and snorts a bit at his own pun, "but I think you can do it."

I hoped he was right. I positioned myself on the bed on all fours and he got behind me and the tip of his 8 inch cock teased the small opening to my asshole. He pulled back and I felt him put his finger in, and then two, three, four, and then pulled out. I was about to ask why he stopped but I got my answer as his cock penetrated my now semi-opened hole. I whimpered and my eyes watered for the first few minutes or so but eventually the pain passed and I let out a moan that even suprised myself. I didn't know I oculd make that feminine of a sound. He was easing in and out slowly and passionately which I enjoyed and then he sped up, and again sped up, and again until his thighs were pounding against my ass. After what was about forty-five minutes, i felt the condom snap and he pushed all the way in pushing his thighs into my ass-cheeks and I moaned so femininely and even louder than before as I felt his cock twicth and spasm and then it happened. He cummed full force and I felt jet after jet being pumped in to me. I felt my body shaking all over as i began to cum as well. It was unlike anything I had ever experienced. After he was finished he fell over, his dick coming out with a "pop".

"Wow! You took that pretty well for not being ready!"

"Oh. My. God." I said, "That was amazing! This was quite possibly the BEST time I've had in my life!!"

"I'm glad you enjoyed it! Now you should go clean up and then get some sleep. We'll have more fun tomorrow. Good night Jim... I mean.. well did you ever pick a name for yourself?"

"No, I guess I haven't. Wait! I know! I like... hmmm well I guess I don't know..."

"Molly." He stated suddenly. "You're definitely a Molly."

"Hmmm... Molly.... I like it! Well good night Ry. See you in the morning."

"Right. Good night Molly." He says as he exits the room shutting the door softly. I cleaned myself up and jumped under the covers and began to contemplate what I had just done. And then it hit me... There was no going back. I had accepted the name Molly and just got ass-fucked by my best friend after giving him a blow-job. Not the way I planned my night when I woke up this morning as James Lee Taylor and was now falling asleep as Molly Elizabeth Taylor. Did I just give myself a middle name? I began to cry silently confused... Was I Jimmy? Or was I Molly?

To Be Continued...