My Best Friends Ch. 03

~ Author's Note: Ch. 01 and 02 were based entirely on true events from my own life with names of the people involved, including my own, changed for privacy reasons. Every chapter from this one forward will be a mixture of true events and fantasy experiences. Enjoy!! ~

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I woke up the next morning from a dream different than any other I had ever had. I was laying on a four-poster bed with pink satin sheets, wearing my pink and black babydoll, and being fucked senseless by my best friend, Ryan. We were constantly shifting into different positions. It started with a slow and careful doggy-style until he had my ass stretched as far as it could go before he started just pounding away. He then pulled out long enough for me to lay down on my back with my legs in the air, spreading my tight asshole for him, longing for his 8.5 inch dick to re-enter its rightful place inside of me. He obliged my wish within seconds and I moaned and sighed as femininely as any girl I had ever watched get fucked in any porn video I had ever watched. Before long, he had laid down on his back, forcing me on top of him and grabbing my hips. He began to bounce me up and down on his cock for what felt like almost thirty minutes before he thrusted all the way into my ass and came full force, shooting jet after jet of warm, sticky semen up in my prostate. It was a feeling I would never forget and had come to love.

It was soon after waking up that I had remembered that part of that was a memory and not a dream. It was hard to believe that only two days ago, Ryan had me on all fours on his estranged sister's bed fucking me for the very first time. It was even harder to believe that the day before that, I graduated High School as an 18 year-old guy named Jimmy. I preferred Molly now. Molly Elizabeth Taylor to be exact.

I looked down at myself and realized where I was. I was sleeping in the guest bedroom at my other best friend, Amanda's, house. I was still wearing her bra from the night before, my own panties that matched it, a black camisole, and silky pink Capri-styled pajama pants that frilled at the bottom that I had borrowed from her last night.

Right. Last night. I recalled the events of the aforementioned when I felt the soreness in my ass again. This time, I had tried to have a sexual experience with Amanda, but realized I just didn't have it in me (no pun intended) to do it. Realizing this, she had me wear her bra and fucked me in the ass with a lifelike strap-on dildo she had in a box somewhere from the time when she went through a bi-curious phase. It was at that time, that I had realized her and Ryan had sex before, as she fucked my ass the EXACT same way he had. The thought of her being with him, for some reason, made me so jealous I couldn't even stand it. As I was lost in thought about the last two days, I heard a knock on the door.

"Oh, Molly! Are you up yet, girlie? I told you last night we're gonna hit the club tonight so I want to get you ready." It was Amanda. She couldn't wait to take me out to the only 21 and under dance club we had near our town.

"You can open the door, you know. I'm decent."

"Aw. You look so cute in those jammies. You can keep them if you want. You need to start building a wardrobe anyway."

"I know. I can't wait to be Molly full-time. I've already planned out my transition."

"On that topic, I have a present for you. My mom used to take these estrogen pills but she doesn't anymore. They are still in date and will help you out."

"Thanks but I'm not supposed to take anything until the doctors and counselors tell me it's clear."

"Oh come on, Molly. A little extra estrogen in your system won't hurt. I promise. If you start now, you can be prettier than me!"

"That's a long-shot..."

"Thank you! But anyway, here take a shower and then take these and get dressed. They're all clean and ready for you. When you get done I'll do your hair and makeup. We need to go shopping for tonight." She smiled kind of slyly as she slipped out of the room so I could proceed to do what I was told.

While in the shower, I borrowed one of Amanda's razors and some shaving cream to keep my body silky smooth. I was supposed to go back to Ryan's tonight, and I wanted to have more fun than the night before. It was a weird feeling I hadn't experienced until now. For some reason, I wanted him to want me more than anything in the world.

I stepped out of the shower and toweled myself off. After being dry, I leaned over to grab the fresh panties and bra Amanda had set out for me. A note slipped out of them that said these were for me to keep from now on too. I was thrilled. I just loved the look of them. I slid the silky, black panties with purple polka-dots and little bows on the hips up my smooth legs and proceeded to tuck my little unwanted member away inside. I fastened the matching bra behind my back and used a little clip to bring the straps together, forcing what little bit of breast tissue I had into passable cleavage. Next I stepped into the black skinny jeans she had laid out for me and then grabbed the red and black striped blouse and put it on over top of a fresh black camisole as well. The satin-esque material of the blouse felt so soft and inviting.

"Okay I'm ready for you now, Amanda." She came into the bathroom and sat me down on the toilet while she went to work. When I stood up, and looked in the mirror, I couldn't believe what I saw. My hair fell lightly on my shoulders and framed my face perfectly. With the makeup on, I looked like the eighteen year old girl I felt like. I could have gone to the club like this and been turning heads in a good way. I couldn't imagine what we would be buying that was better than this.

"Ready to go shopping, Molly? I'm paying this time, but next time you have to buy me something, okay?"

"Okay. I love this outfit though. Why do I need something else?"

"It's little black dress night. All the single girls will be wearing little black dresses so the boys know they're available. So wee need to go get you a little black dress and some cute heels. I've got some jewelry for you too."

"Little black dress? Oh my god. You know how long I've wanted one? I think tonight is going to be fun."

"Not to mention that as cute as you are, we'll find a guy for you in a few seconds flat."

With that, I slipped a pair of black ballet flats on, and headed out after Amanda. Molly had officially stepped out into the world for the first time. It was a great feeling. I wasn't hiding anymore. I was finally free.

***

When we got back to Amanda's place, I couldn't wait to get my new dress on. I stripped right in her living room and stepped into it, pulling it up to my chest. I had to stop though, because it was strapless and I had to let Amanda get me into my new black strapless bra. It fit snugly around my chest and back and pushed my chest up into passable cleavage. The cups were too big but Amanda quickly rectified that problem. She had secretly gone into one of the oddities shops and found me a pair of breast forms. When she stuck them onto my chest, they filled the C cups of the bra nicely. Now I got to pull my new little dress up to my chest, and Amanda zipped me up. I instantly loved the way it felt; pulled tight up against my skin, hugging my breast forms, my hips, and my ass. It covered just enough that I wasn't fully exposed, but after tonight was over I had a feeling I would be anyway.

When that was finished, Amanda brought me out a necklace that matched my new diamond studded earrings that I just gotten done at the mall. I looked and felt like a real girl and was ready to go be Molly Elizabeth Taylor, eighteen, single, and ready to party. I strapped my new black, three inch stilletos onto my feet. The open toe showed off my newly pedicured and painted toenails perfectly. My newly manicured and french tipped fingernails brought the whole look together nicely. I helped Amanda get her dress on, grabbed my new purse and headed back out into the world.

When we got to the club, I knew tonight was going to be a good night. It was seven o'clock and people were just starting to roll in. Amanda and I waited up by the "bar" where they served cold sodas and tea. It wasn't long before two guys came up to us and asked our names.

"Hey. I'm Deandre. Or just Dre. What's your name, babe?" Dre was about six foot four, black, and built. I could just get lost in this man.

"I'm Molly." I said, in my best female voice. "I'm a little new to the area." I could hear Amanda's conversation but all I got out of it was the guy talking to her was named Daniel and was Dre's best friend. I was too busy thinking about Dre to pay attention to much else.

"That's a pretty name. Well Miss Molly, you're too hot to be single. Why are you, if you don't mind me asking?"

"Like I said, I'm new to the area. I'm a childhood friend of Amanda's over here. The two of us are pretty close."

"Cool. It's about to get noisy in here. You mind if the four of us take it to the VIP room? Don't worry, we won't do anything you don't want us to."

"Okay." With that, Amanda and I followed Dre and Daniel back to the VIP section they had rented. We talked to the two guys until about eight thirty, telling stories about Amanda's childhood and bending them to include a young Molly. Before I knew it, we had these guys infatuated with us.

"Hey..." Dre began, "You girls know that no one can see us back here right? Do you two wanna.. you know.. do anything?"

Amanda and I looked at each other and it was like we had a psychic connection. We both scooted down onto the floor; her in front of Daniel and me in front of Dre. She slid Daniel's pants down to his knees, exposing his semi-erect cock and I did the same to Dre. What was in front of my face I almost couldn't believe. Dre's dick was about an inch longer than Ryan's and about two inches thicker. I was so glad I was only going to give him a blowjob. He would split me in half!

Dre looked down into my eyes and I smiled slyly before kissing the head of his cock. I parted my lips as Amanda was doing to Daniel and began to slowly take more and more of Dre's cock into my mouth. I almost gagged at first, but I managed to control the reflex and I slowly took the rest of his nearly ten inch penis into my mouth. I slowly began to bob my head up and down running the length of his cock with my tongue. I took my mouth off of his dick long enough to move underneath of it and licked the shaft from balls to tip twice before going back to bobbing for apples. I kept this pattern up for about twenty minutes until Dre put his hand on the back of my head and guided his cock all the way into my mouth. He held me there for about thirty seconds before I felt a familiar spazzing sensation. What happened next, I almost wasn't prepared for. He came in my mouth, shooting jets directly into the back of my throat. I swallowed by reflex but after a few seconds, began to do it willingly. The taste was unlike anything I had ever imagined. I loved it. When he stopped, he pulled his cock out of my mouth and pulled up his pants. My first taste of cum was one of the most unforgettable experiences of my life.

"Wow Molly. That was probably the best blowjob I've ever gotten. Let me get your number, girl. We gotta do this again sometime." I looked over and winked at Amanda who had finished Daniel off quickly and had been watching me with a mix of shock and pride.To think three days ago, she never would have thought she'd see what she just saw, or thought that she would fuck me with a strap-on either for that matter. I gave Dre my number and Amanda decided she wanted to leave. I tried to tell her I was super horny right now and was almost willing to let Dre fuck me raw. I kept my self from cumming and blowing my cover and I was still ready to go for a ride, just not in a car.

When we got back to Amanda's, I took everything she gave to me or bought for me, including the bottle of estrogen pills, and got it into a bag. I decided to leave my dress on. After all, I was going back to Ryan's tonight and I wanted to surprise him. I told Amanda this and she led me to her lingerie drawer to let me pick out something to borrow. I ended up choosing a red bra and matching thong that game with a matching sheer white babydoll that showed them off. I grabbed a pair of white stockings with red bows on them. I remembered seeing a box of things under Ryan's sister's bed and there were these red stilettos that looked almost like my black ones. This ensemble gave me an idea.

"Hey Amanda. Do you have a nurse's hat?"

"Actually, let me check my old Halloween box." Sure enough, she did. I was going to play naughty little nurse for Ryan tonight after he got to see me in my little black dress. I put my little "nurse uniform" on the top of the bag, and a few packs of condoms. I was going to make my dream a reality tonight. I wanted Ryan to have sex with me just like in my dream and I was going to accomplish that. He always said he had a thing for cute girls in sexy nurse costumes.

"Okay. I'm going back to Ryan's. I'll call you tomorrow."

"Okay. But we need to have a talk, girl. You can't be with Ryan and mess around with Dre too."

"I know. I'll figure something out." And with that, I walked out to my car, my heels clicking on Amanda's walkway. I pulled out of her driveway in my car, and when I turned to look, I realized another car pull off the sidewalk and follow me. I didn't think anything of it at all. I was ready to go get my little ass fucked by my best friend all night tonight. Molly was in full control now. Jimmy was gone. Besides, the car pulled off around the corner from Ryan's house before I pulled up there, anyway. I walked up to Ryan's door and rang the bell.

When Ryan opened the door I thought his jaw was going to hit the floor.

"Hey! Amanda took me shopping today. So what do you think? Like my little black dress?" He looked at me still in a little bit of disbelief. He scanned me from head to toe, stopping at my hips, breasts, and finally my eyes. He leaned out of the door, and pressed his lips to mine, kissing me passionately. I felt a wave of heat rush over my body as I reached up to kiss him back. He broke our embrace to say something and I really wish he hadn't.

"You look beautiful, Molly. In fact, maybe we should make this a weekend thing." He leaned back in and our passionate kissing continued. I nearly pushed him in the door as it closed behind us. At this moment, I heard footsteps walking towards us.

"Hey. I thought you said this Molly girl was your friend, Ryan. But here you are making out with her like she was your trophy wife." I recognized the boy's face and hoped he didn't recognize mine. It was Steven, a boy who we graduated with and was close friends with Ryan. All I could think about was hoping he wouldn't recognize Jimmy underneath all of this Molly. My fear was soon to be proven unnecessary and what would happen next, would turn out to be the best night of my new life so far.

To be continued...