Cunt! Ch. 04

After our fun in the kitchen, Derek stayed and made himself breakfast and I headed upstairs to get ready for the day. I pulled out all of my clothes from duffel bag and laid them out on top of my comforter. I had so much new clothing! I decided on wearing a thong this time as I had yet to wear one out besides the brief moment trying it on when it arrived in the mail. I perused my options amongst the skirts, blouses, shirts, shorts, pants, leggings, and dresses. I hadn't worn a dress yet and I had a cute black, ballet-back dress with a flared bottom that i could wear with some white leggings. I could be a ballerina for the day! I looked over all my clothes again to make sure of my decision. My makeup was still on my dresser, ready to go.

Being sticky and sweaty from my morning fuck, I decided I would have to take a shower or I would feel gross all day. I stripped off my pink panties and t-shirt and looked at my femme self in the mirror. I swear if I keep this up I am going to become vain! But it is just so hard not to stare at yourself when you feel so pretty. I turned and looked at my freshly fucked ass. I truly felt like a woman. Derek couldn't seem to resist how sexy I had become. I love how much he desired me; how he couldn't control himself around me.

I turned the shower on and waited for the water to become hot and then I stepped in. I looked down at my petite frame and watched the water slide down my body, off the head of my penis. My dick seemed so much smaller to me now that I had spent so much time with Derek's cock. Mine was little and dainty. I reached down and started to masturbate. Slowly it rose to its full size and yet was still less than half the size of Derek's. I grabbed the shampoo bottle when I heard a knock at the door.

"Come in!" I yelled.

"Hey, Ash!"

"Yeah?"

"I am going to the gym to meet friends for some basketball!"

"Okay!" I replied. I was a little disappointed. I was hoping to show off my new outfit for him and watch his reaction as he ogled me. Then, I realized I had never heard the door close and suddenly the shower curtain slid back. Derek and I stood in front of each other completely naked. I had my small erection and he had a quickly rising, large one. "So Ash... Would you mind if I got a blowjob real quick before the gym?"

"You're insatiable! We just did it like an hour ago."

"I know but I saw your beautiful figure in the shower and I got horny again!"

God, he knew what to say.

"Okay! But only because your cock looks so delicious!"

Derek stepped into the shower opposite the shower head. I turned my back to the water and got onto my knees. Derek's cock was right in front of my eyes. I looked at it, then up at him, and then back to that marvelous piece of meat. I took my hand and gave him a few long tugs. It was as hard as ever, no preparation needed. "Did I do this to you? Are you this hard because of me?" I asked seductively.

"Of Course! Ashley, you are one of the most beautiful girls I have ever seen!"

I smiled and blushed at his statement. We never broke eye contact as I closed my lips around the head of his cock. "Oh god!" he groaned. I kept just the head in my mouth and used my tongue to lick all around it. Then, I put my tongue at his urethra and twisted it all around. His body jerked in response. I pulled him out of my mouth and took his cock head and dragged it across my tongue with long, hard strokes. Again, never breaking eye contact. "You're amazing! Ohhhhh!" I put him back into my mouth and slowly went down as far as I could go, until he hit the back of my throat and then just as slowly, applying pressure with my tongue and my lips, I pulled back until he came out of my mouth with a pop.

I took a hold of his dick again and pressed it upward toward his stomach. Then I pressed his scrotum against my face. His big balls grazed my lips and I kissed all around them gently. I pulled one of his testicles into my mouth and massaged it with my tongue while gently sucking. Then I moved to his other one. I alternated on each ball for about two minutes and then I moved back to his shaft and took him as deeply as I could. I pulled back all the way to the tip and then attempted again to take him to the base. I kept doing this slowly, while I massaged his balls. After a minute of this, I noticed he was going deeper into my throat and after another minute or two I felt his pubes against my nose. I had still never broken eye contact with him. His eyes were wide with pleasure and amazement. I reached in between my legs and began to stroke my aching cock.

I wanted to please him so much. I wanted his cum to fill my mouth and I wanted him to feel drunk in sexual euphoria. I took him to his base again, and then I held him there. I hummed a little tune and watched him squirm. In my hand, I felt his testicles began to twitch, I knew that he was beginning to get close. But I was in charge here and I would say when this whole ordeal ended. I pulled off his cock and grabbed it tightly. "What are you doing, Ashley?" He asked desperately.

"Taking my time. Are you in a hurry?"

"I want to cum so badly! Put your mouth back on my cock!"

"Like this?" I ask as I licked up the head of his penis.

He shook. "Oohhhh Fuck. Please just put me back in your mouth!"

"Like this?" I ask as I licked along his shaft toward the tip and then kissed my way back down to his balls, all while lightly stroking him.

"Ashley.. Uh - ah.. plea - "

I pulled him back into my mouth and swirled my tongue around the head of his penis. Then I pulled him from my mouth, kissing the tip as it left. "Who is the greatest?" I ask him sweetly.

"You are!"

"Who has you in the palm of her hand"

"You do!"

"Who do you want more than anyone in this world?"

"You Ashley! I want you so bad!" He was really squirming now.

"And who is the greatest fuck in the world?"

"Ashley, it's you! It's you, forever! Now, please let me cum!"

I smiled sexily up at Derek and then I put him back into my mouth. I moved up and down his shaft rapidly as he began to tremble and moan. I returned my hand to his sack and massaged it as well. He was getting twitchy and I could feel him shaking all over. His scrotum began to retract and I knew he was almost there. I watched his face, his eyes were closed and he was whimpering for release. I released his balls from my hand and let go of my dick. Then I grabbed him around his ass and pulled him as deeply into my mouth as I could and hummed. "Oh, I am cumming!" He yelled, his legs trembling violently.

He opened his eyes and looked down at me. I stared into his eyes and pulled back to just the tip and then I opened my mouth and let him rest against my tongue. I moved my right hand back to his shaft and held him in place. We never broke eye contact as his load blasted against the roof of my open mouth. He shot five times, and then began heavily leaking. I squeezed his cock from the base to the tip, guaranteeing me to all of my reward. He was panting for air, exhausted, looking down at me. I smiled seductively at him and closed my mouth and then I swallowed a mouthful of his cum. "Mmm... You are so delicious. I love the taste of your cum." He hadn't caught his breath yet. I put the head of his deflating cock back in my mouth and sucked gently until he had gotten control of himself. When he stood up, I pulled him from my mouth and lightly planted kisses all over his big, spent dick. "That was amazing... I don't know if I will be able to play now." He said.

"You'll certainly be slower than usual." I said in between kisses.

"I would finish you off, but I don't think I have time."

"Well, get going! I'll take care of myself. You can make it up to me later."

I stood up and Derek gave me a quick peck on the lips. He is such a sweetheart. Derek stepped out of the shower and dried off. Then he dressed in his athletic clothes and left the bathroom. I began stroking my little dick rapidly as I savored the taste of Derek on my tongue. I took my left hand and grabbed my chest and began to play with my nipple. After a while, I took my hand from my chest and began to finger my asshole. As I felt my orgasm approaching, I moved my hand around and cupped it at the head of my cock. I trembled violently: moaning and whining as I came into my hand a sizable puddle. I squeezed every drop I could out of it and then brought my hand to my mouth. I poured the cum onto my tongue and swirled it around in my mouth. I enjoyed it as long as I could and then swallowed. Immediately, I began licking the remnants off of my hand until I could no longer taste anything. Then I smiled naughtily as I started washing my hair.

After I finished my shower, I grabbed my makeup set and my laptop. I had seen a makeup tutorial online I wanted to try it out. The tutorial used more natural colors to bring out your eyes and facial features. I used the purple and pink eye shadow and faded them together with the pink on the outside. For my mascara I went with a thick line wing tipped. I used a deep shade of red for my lipstick and just the tiniest bit of blush.

I blew my hair dry, straightened it, and braided it into a long single braid draped over my right shoulder. I gathered my things and walked to my bedroom. I put on a white thong, my white leggings, and then my black dress. I didn't have a bra that would work under the dress so I just went without one. I didn't have any jewelry but I wanted to wear some so I raided my mom's jewelry box. I found a thin gold necklace and a few gold bracelets to go with it. After a few quick spurts of perfume I was ready for my evening. I felt pretty! Now, if only I was going somewhere!

I was posing in the mirror when an idea came to me. I had never even take a picture of myself like this. I grabbed my camera and began snapping pictures of myself. I did various poses and I flirted with camera the entire time. After a series of pictures in the mirror, I set the camera on my desk and used the self-timer. I took them all over the room, working on the best shot. Then, I took some pictures of myself in bed. I probably took over three hundred pictures before I finally quit.

I laid in bed and reviewed the pictures, deleting most of them. It made me really happy looking through the pictures of this happy, playful girl! She looked so comfortable with herself and she look so beautiful... And she was me! I thought briefly about creating a MySpace profile for my femme persona, but then I heard the front door down stairs close. Derek had just gotten home.

I heard him running up the stairs and approaching my door, two knocks and he entered. "Hey Ash! I was thinking — Wow, you look beautiful!"

"Thank you!" I blushed. He stared at me a while longer.

"Oh! I was thinking, and especially more so now that I have seen you, we should go out on a date!"

"A date! Are you nuts? I can't go out like this. Someone will recognize me!"

"That police officer didn't..."

"It was dark out, he probably couldn't see."

"Well, it is getting dark out now and I think you are girly enough to pass anywhere without question." I looked at him with a frown. "Come on! I want to take you out. I want the world to see how gorgeous you are."

"I don't know."

"We will keep it simple, dinner and a movie. And we can go one town over so that no one knows you!"

"...Okay I guess if we go one town over. But if I say I want to go home you have to take me!"

"Deal. I am going to go get ready."

Derek ran to his room and got ready for the evening while I became a ball of nerves in anticipation of tonight's events. I thought I looked good and he thinks I can pass, but what if he is just being biased? This would ruin me at school! I'd be a crossdressing faggot weirdo! But still, going on that date sounded nice and I wanted to do it; I wanted somewhere to go.

After a quick shower, Derek dressed, and we headed to the car. I didn't have a jacket so I borrowed one of my mother's black coats and a pair of her heels. I had to walk slowly as I had rarely walked in heels but I didn't find it to be too difficult. Derek opened the passenger side door for me like a true gentlemen and I smirked at him as I entered the car. When he got in the car, he fumbled with the radio and began playing a Death Cab for Cutie album. Once we were on the road, he reached for my hand. "What are you doing?" I asked.

"Holding your hand while I drive. I want this to feel like a date and when I'm on a date, I hold the hand of the girl I like."

I blushed but also began to worry a bit. I enjoy being treated as a girl, I enjoy the lifestyle, and I enjoy being submissive. But I don't know if I want to be in a relationship with my brother. I just like the sex, I like his cock. I thought he was on the same page. I was quickly realizing that we would have to have a serious talk about this, but for now I would just have to worry about what will happen when we get to the restaurant. After about a thirty minutes, we had arrived. It was a nicer place called Madeline's; a local restaurant that was the perfect location for a high schooler to take a fancy date.

Derek got out of the car and insisted on opening my door for me; He was so happy and excited as he ran around the car to open my door. I was so nervous as we approached the restaurant. Derek opened the door and we went inside. I looked at the floor the entire time; being careful to avoid eye contact with anyone. I heard the hostess ask, "Welcome to Madeline's! How many?"

"Just two!" Derek Answered.

"Right this way."

She led us to a small table for two in the corner of the restaurant. Luckily for me, the restaurant had dim lighting. It made me feel a bit more at ease. After we had taken our seat, the hostess turned around and said to me, "Hey! I love your outfit!" I froze in a panic. Surely, here is where I get caught. Here is where I realize that I am a boy and my life falls to shambles as I am outed as a crossdresser! And yet I mustered my girliest voice and replied, "Oh thank you!" The girl smiled, turned around, and walked away. My heart was beating out of my chest and I was probably beet red. Derek looked at me and said, "See! Nothing to worry about. She thought you were a girl and she even loved your outfit. You can relax."

I took a deep breath and calmed myself down. Derek was right! When the waiter came and took our orders, it seemed perfectly natural. Everything about the dinner seemed normal and I received no strange stares or any clues that people knew my secret. I started to have fun and by the time the check came Derek and I were laughing loudly about some story of his friend trying to ask a senior to prom. It was nice! After our dinner, we went to the theatre and saw the film, King Kong (2005 version). During the film, Derek did the classic date move and put his arm around me while we watched. I was really enjoying being treated like this. I felt pretty, desired, and adored. I liked his arm around me too, it made me feel protected and cared after. I looked over at him halfway through the film and gave him a kiss on the cheek. He turned and we kissed each other on the lips and before long we were making out. We did this for about twenty minutes, before realizing that we both had erections in this semi-crowded theatre. It wasn't very lady like. We both worked on calming down while we finished the rest of the movie, his arm still around me.

After the movie, we hurried out of the theatre to avoid any glares or judgments from the other movie goers for our impromptu make out session. I had to use the bathroom on the way out and realized I would have to use the women's restroom. A new kind of nervousness imbued me as I feared adding "pervert" to the list of my labels if I was discovered. And yet, having been seen by plenty of people tonight, I was less nervous than when we entered the restaurant. I walked into the bathroom and went directly to a stall. I finished my business and decided to check my appearance. I lingered at the sink while checking to make sure my makeup was good and touch up my lipstick. A few girls shuffled in and a few examined me as they passed, but they quickly moved on, nothing amiss. I was just a fellow woman to them and that thought made me happy. Derek was waiting for me outside and we left from home.

As soon as we entered the car, Derek looked at me and said, "So, was I right? No one could tell you aren't a girl. People thought you were pretty! And we had a great time!"

"You were right! And I had a lot of fun. It was pretty stressful at first but the rest of the night as thrilling!"

"So do you think you will want to go out more?"

"Yeah, actually. It is really nice and people get to see all the hard work I put into my appearance. Not that they care, but still."

"Well, you look beautiful and I saw plenty of guys checking you out!"

"Really? I guess I didn't notice! They were checking me out?"

"Yeah they were. And I noticed them! It makes a guy feel good noticing all the jealous stares. Also, I have to know who to fight off, if need be!"

I began to blush. "Well, I wasn't looking but I bet the girls were awfully jealous of me also! Getting to go out with such a stud."

"Hey! Since, you know, we got all excited in the theatre... and we have about a half an hour drive... Would you want to give me head?"

"While you're driving? That doesn't sound safe! And what if someone pulls up next to us and sees us?"

"Well, it is dark out and the all they'll see is a girl pleasing a guy. People do it all the time!"

"Still though, I don't know!"

"Come on! I won our little argument about you passing in public and I was a great date. This is the least you could do!"

"What kind of girl do you think I am, giving head on the first date?"

"We did it ALL before the first date. A couple of times!"

I teasingly acted embarrassed. "Asshole!" I replied pouting. And then with a Victorian accent I said, "Well, I have had a great time and you were quite a gentleman. I guess just this once, as long as you don't go blabbing to the other boys."

I reached over and unbuttoned his jeans. He raised up and helped me slide his pants and boxers down and adjusted his seat slightly to allow for more room. His penis was slightly plump but nowhere near fully erect. I leaned down and took his deflated, squishy cock into my mouth and began to pull it upward with my lips, all while swirling my tongue strongly around the head. I released and eased back down, fitting all of his soft cock into my mouth, holding it there as it became thicker and thicker with his pubes resting against my left cheek. Again, I pulled my taut lips up and his expanding shaft along with me. And when I reached the top, I opened my mouth, and went back down as far as I could until I felt the head resting against my tonsils. I repeated doing this until his pubic hair became harder and harder to reach. Eventually, he had reached his full size. I backed off and looked at my handy(mouthy?)work. His cock stood strong, bulging, and covered from my saliva.

I leaned down and pressed my face into his crotch, his hard dick warm against my cheek. I pulled back and took a hold of it lightly with my left hand. Then, I began playfully nibbling the the skin on his sac and then moving my way up his cock with pursed, lingering kisses. Still holding him with my left hand, I licked all around his cock head with big, long licks, before placing my tongue at his pee slit and licking lightly. Then I sucked down again until I reached the base and Derek rested against the back of my throat and repeated that motion at a consistent pace. Derek commented, "God this is so good! I love watching you work!"

"Hochus on ha woad!" I mumbled harshly with a mouth full of cock.

"Haha! Okay! Okay! I am." He replied.

I continued sucking with long, slow motions taking him as deeply as I could every time. Derek was breathing heavy and moaning. I was listening to him and taking in all of the praise! I was alternating between deep throating, focusing on the crown with heavy tongue play, planting kisses all over his shaft, and generally worshiping this gorgeous phallus as god intended. My hands were busy caressing and teasing his balls or tracing invisible lines along his thighs. But through my best efforts, I wasn't getting any of the signs that he was close to an orgasm. I guess the three orgasms in the past 24 hours had made him a little desensitized. I continued on until my jaw became sore and my eyes were watering from holding him against my throat for so long.