Cunt! Ch. 05

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Ashley begins moving forward with or without...
3.5k words
4.68
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Part 5 of the 8 part series

Updated 06/07/2023
Created 07/18/2011
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Editor's note: this story contains scenes of incest or incest content.

***

I awoke the next morning; Derek was still in bed with me. We had both drifted apart as we slept and were no longer in the cuddled embrace of the night before. I groggily raised my arms above my head, pointed my toes, and arched my back, elongating my body; stretching out anything that needed stretched. I yawned deeply then turned to stare at the still sleeping Derek who was completely naked and uncovered, his heavy cock sleeping as peacefully as he was. After admiring him for a bit, I made myself get out of bed and move around.

I headed straight to the bathroom and hopped into the shower and washed off all of the bodily fluid that had dried on my skin. I gently caressed my body with the soap and washcloth then spent nearly twenty minutes just standing under the shower, letting the hot water run over my sore body as the conditioner set in my hair. Finally, I collected myself, I washed the conditioner out, and turned off the shower. I threw on a pair of my Victoria's Secret lace-trim hipster panties with the black and white stripe pattern, a pair of black Nike women's running shorts, and a white camisole top.

I headed to the kitchen, poured myself some cereal, and sat down carefully on my tender bottom. Derek had been particularly rough last night and my cheeks were paying for it today. But still last night had been an amazing experience, I was so happy that I had been able to go out dressed as woman and no one, that I could tell, noticed I wasn't. I was feminine enough to pass if I wanted! It was so very satisfying and exciting to me. I wanted to go out dressed more often, I wanted everyone to see the woman I had become. The beautiful woman that I am!

After I had finished breakfast, I ran upstairs and laid out something pretty to wear. I decided that for the second day in a row I was going to wear a dress! The dress was an off white floral sleeveless dress with a pattern of blue and purple flowers with black stems. It zipped up in the back and the bottom of the dress flared out. I went with a white pushup bra to wear underneath to give my chest more shape and hopefully fill the dress out a bit more. I also grabbed a blue headband that I had bought to go with the outfit. Unfortunately, I was running low on new clothes! I hadn't purchased much to begin with, just enough to play around.

I gathered all of my makeup and put it on the bed. I wanted the color theme of this outfit to revolve around blue. I climbed onto the bed and spent the next hour reading make up tutorials and practicing my makeup in my small travel mirror. I was getting better. My application and blending was improving, and I felt like I could draw on a decent wing tip. But, my contouring and eyeshadow could use some work. I made my eyelids a medium blue that faded into a lighter electric blue as it approached my brow, then finished with light pink lip gloss and just a hint of blush.

Once I was satisfied with my makeup, I went to the bathroom and straightened my hair, then headed back to my room to get dressed. I absolutely loved my outfit! First off, I love dresses. I do! I love how they drape over my body. I love the feeling of my bare legs rubbing together. I love the freedom and lack of constraint. And most of all, I love the thrill of knowing that I am not supposed to be wearing one! Secondly, I looked like an innocent church girl. I looked as though I was getting ready to go join my family for a lovely Easter service. It is an incredible feeling, staring at the beautiful woman I could transform into, admiring my handy work. It felt almost unbelievable.

I grabbed my camera, set up my tripod, and began modeling my new outfit. But despite my best efforts I wasn't excited with any of the pictures and I blamed the lighting. It was a beautiful day outside and particularly warm for a day in January, so I thought myself, 'why not at least go outside for a few minutes and take some shots and see if you can get the picture you are looking for?" So I grabbed the camera equipment and headed out onto the back porch. I tried posing seated on the porch furniture, I posed leaning against a wooden beam that supported the patio roof. I took a few dozen on the porch steps. Then, I walked deeper into the backyard and took a few shots posed in the gazebo. And even more shots, kneeling in the grass, looking at an upward angle at the camera. Basically, I was trying to imitate all of the girl's senior pictures from my class that I had seen earlier in the year.

Next, I ran back inside and grabbed some props to pose with; I grabbed a Jane Austen novel, a blanket, a basket, a pencil, and the flowers that sat in the vase on our kitchen counter. I took more photographs posed as if I were at a picnic or reading a book. My favorite picture ended up being of me draped over this big wooden chair, my legs dangling over one arm rest and my head leaned back over the other, smelling the bouquet of flowers, my locks dangling towards the ground. Also, the sun flared the lens a bit, making the picture look very artsy.

I was having a ton of fun modeling but then noticed our neighbors were starting to mosey about in their backyards. So I headed inside, just in case they recognized me. I'd rather not have to explain that to my parents! I ran straight up to my room, uploaded the pictures, and started messing with them in PhotoShop. After a few hours, I had the pictures exactly as I wanted them. I was so happy with the photos that I decided I had to put them somewhere. So, I created a MySpace page!

I spent the next hour creating a profile for my female persona, Ashley XOXO. I know, real original! I uploaded a few of my favorite pictures that I had taken in the past few days and for my profile picture, I posted the picture I had just taken off me draped over the chair. My quote was "Young Kentucky girl in a push-up bra!" from the Red Hot Chili Pepper song - "Scar tissue." In the interests section, I put all the guilty pleasure things that enjoyed but couldn't freely admit to: shopping, clothes, dancing, flirting, Love Actually, P!nk, The O.C., One Tree Hill, Maroon 5, Victoria's secret, etc. I did have a lot of crossover answers too, like my love of Linkin Park, and my favorite novels being Frankenstein and To Kill a Mockingbird. In my about me section, I just put a brief description, "Hey guys! My name is Ashley. I'm an 18-year-old girl from KY who loves socializing, randomness, and having a good time. I'm in highschool but you'll never know which one. in my spare time I do photography and strive to create beauty in this sometimes ugly world. I hope you enjoy my pictures and welcome to MY space! <3"

I debated adding some people from my high school, so that I would have more friends than just Tom from MySpace. None of the photos really looked like the male version of me, none were really close enough to be able to see the minor confirmations that I was one of their fellow classmates in drag. Ultimately, I decided to add a few of the girls from freshman to seniors that I thought had the best style or had the best makeup, then I added a few girls from the grades above me that were in college now. I guess if I got caught, it was meant to be. Oh well! I'm almost done with high school anyways!

It had been around four hours since I had gotten out of bed and grabbed breakfast, and my tummy was starting to growl. I headed down to the kitchen and made myself a grilled cheese with a glass of milk. While I was eating, a freshly showered Derek entered the kitchen, wrapped only in a towel. "Wow! Don't you look pretty! Why are you so dressed up?"

"I'm just trying out some new looks! So you like?"

"Yes! You look very girl next door. A good girl!"

I grinned and blushed remembering all the naughty things we had done. "Even if I have been a little bad lately?"

"I only said you look like a good girl! You have been neither good nor are you a girl!"

I laughed, "Very true! And I have to say that I have had so much fun with it all!"

"Well, we had a ton of fun last night. I was exhausted!"

"It was wonderful! We will have to go out more often. I can't believe that no one recognized me as a guy."

"Well, you're not the manliest guy I know and you have pretty delicate features. Honestly, you make a much better girl than a guy! You're nicer and more appealing to look at. And, I don't know, you just seem..." Derek held his tongue while he thought of a word that he felt described me best, "Lovely! That's it! You just seem so lovely!"

I smiled and blushed and turned my head from him!

"Oh, shut up!"

"No seriously! I think that is the best way to describe you."

"Well, thank you! That's very sweet of you to say"

"And you don't even have a guy body. Your skin is so soft and your ass is gorgeous and your dick doesn't even look like a man's dick. It looks smaller, softer and more delicate."

"I should deck you for that, but I can't help but agree. I have never been very well endowed."

"And you don't need to be. You're beautiful and perfect the way you are."

Derek leaned over and kissed me on the lips. Then he put his hand around the back of my head and pulled deeper into our kiss. Our tongues began dancing in and out of each others mouths and our breathing became louder, deeper, and irregular. He tasted minty fresh and his lips were soft and moist. I reached out my hand and felt the large bulge that was slowly raising the front of the towel. Derek moaned as my hand grazed against his package. He broke from this kiss.

"These last few days have been so good, Ash! But where do we go from here? How does this work?"

"Umm... I wasn't really thinking that far ahead." I paused for a while, really unsure of what to say next. "I thought we were just having fun."

"We are having fun! But I just wanted to make sure that we are on the same page. Ashley, I still like girls and I want to be in a relationship with one. I'm not gay."

"I do as well and I am not gay either, It's just that when I dress I take on a female role. I do what a girl would do! And I don't think you need to worry, it's not like I am going to start telling people that I enjoy getting fucked by my younger brother."

"That's true... but what happens when a girl comes into the pic..."

I pressed my finger to my brother's lips and shushed him until he stopped talking. "Don't worry about that now, we will cross that bridge when we come to it." I reached into the opening of the towel and took a hold of his semi-erect penis and stroked it lightly.

"But for now, know that I like taking care of you and I love what we are doing. Let me show you just how much." I pulled the towel away and sank down to my knees in front of Derek's long, thick cock. Grasping it firmly I pulled it to my lips and placed a gentle kiss on the very tip. Holding it there, I pushed my tongue out and tickled his head, all while my pursed lips slowly engulfed him. Derek jerked and released a euphoric yelp!

"Oh shit! Ah!"

I released my grip and rested my hands on my thighs. Then, I took his cock as far as I could into my mouth, pulled back slowly, and again dove down until I felt him press against the back of my throat. I pressed firmly against him with my tongue as I moved back and forth on his shaft. Soon, his precum was leaking into my mouth. "Mmmmmm..." I moaned. I raised my hands up and began to tickle the back of Derek's legs and ass as I sucked him. I grew louder with my moans, Every time I tasted his precum, I would moan like it was the greatest thing I have ever tasted. I looked up at him with the biggest eyes I could make as I nursed on his penis. He was looking down at me with that look of pure lust and excitement that I very, very quickly grew to love. I fluttered my eyelashes at him and smiled wide with my mouth full of his beautiful cock.

Suddenly, Derek twitched and he made a funny noise and a stupid face. I giggled around his cock, tightened my lips, grabbed his shaft, and pulled him from my mouth. I jerked him aggressively as I said, "You have such a big, beautiful delicious cock! I can't get enough of it." Then I pressed it up against his stomach as I dragged my tongue firmly from the bottom of his balls up to the tippy top of the head. Then, while still holding, I kissed my way back down and playfully pulled on his sack with my lips. I let go of his dick and let it slap me in the face. Then, I grabbed it again and slapped it repeatedly against my puckered lips. "Owww... you get me so hot!" I whined like a horny girl in a porno.

"Oh Ashley! You're so good!"

I licked up and down his rod. "I could worship your cock all day!"

I put him back into my mouth and slammed my head down taking his dick down my throat and my nose pressing into his bush. I started to gag. I pulled back and did it again, drool spilled from the sides of my mouth as I choked on his cock and my eyes started watering. I eased off until just the tip rested against my tongue and then sucked with more pressure until the my cheeks were pulled inward. Again, I looked up at him with my red, watery eyes and my lips taut as I rapidly pleasured his dick.

Then, I pulled back until about a third of his shaft was in my mouth, gripped the bottom two-thirds, and strongly circled his mushroom tip with my tongue while giving him an aggressive handjob. "Mmmmmmmm" I moaned as he leaked more and more into my hungry mouth. I could tell he was close. His body was beginning to quiver and his boner was as hard as a rock, the head swollen, smooth, purple and angry.

I released my grip and moved my hands to his balls and began lightly dragging my fingers over the skin of his big testicles. Then I dropped my mouth back down and took him all the way once more. He was trembling now, his cock as hard as it could be. I sucked him up and down faster and faster, licking wildly as I did. I looked up at Derek and he gazed back into my eyes. "Oh Ashley! Oh Ashley! I'm going to cum. I'm cumming." He panted as I felt his balls tighten and his thick shaft begin to groan and lurch. I pulled back until just the head was in my mouth and gripped and jerked his pole.

Derek unloaded into my mouth his salty, delicious, love potion. After the first two big spurts, I opened my mouth and held him against me my tongue and let him watch as his cock shot cum against the roof of my mouth. Due to the force, a bit splashed out and rested on my upper lip. his jizz dribbled out slower and slower until I couldn't squeeze any more semen from his cock. I held my mouth open making sure he saw how much cum I had taken from him and using my tongue, I moved his seed all around my mouth. Then without ever taking my eyes off of his, I closed my mouth, swished around his warm load a bit more, savoring his wonderful flavor, and swallowed with a large gulp. Immediately I opened my mouth and showed him it was empty and that his sperm was inside of me, digesting in my tummy. I let go of him, and he stumbled over to the couch and fell onto it. "Holy shit! Holy shit..."

I licked the last of his cum from my lips. "Mmm... I take it you liked my my blow job!"

"Wow. You keep getting better. Oh. Wow!"

"Thank you. I still can't believe how much fun I have doing it"

I reached under my dress and began rubbing myself through my panties. I felt so wonderfully girly and terribly horny. I stared at Derek, watching as he recovered from my handy work. It was so erotic to me knowing that I could do that to him, bring him to cloud nine with my body. That he lusted after me and desired me. That he wanted this girl that I'd become! Then, just as I was about to take out my dainty, little, cocklette and finish myself off, the doorbell rang. DING DONG!

Derek jumped up and grabbed his towel. I ran upstairs and waited by my bedroom door to see who was here. it was probably just a delivery guy but still, I needed to be able to change quickly if needed. DING DONG! The doorbell rang a second time. This time Derek approached the door, he had gone to the laundry room and thrown on a pair of sweatpants and a t-shirt. I watched as Derek answered the door, I couldn't see who it was but I could see my brother was surprised. Then I heard her speak. She was crying. "Derek, I want to continue or conversation from this morning. Can you forgive me and take me back or not?" It was Karrie. the girl who had dumped him just a few days earlier. Now, I understand why we had our odd, little discussion earlier!

Derek invited her in and I could hear them talking in the living room. She apologized for breaking up with him and that she'd realized her mistake, that she was nervous about being in a serious relationship, yada, yada, yada... at first Derek seemed unaffected by her advances and did not wish to get back into the relationship. But after about fifteen minutes of her crying, I could tell he was getting emotional. Slowly, his position changed and by the end of it, they had agreed to get back together. I sat at the top of the stairs and listened to all of it. When it was finally over, they got up to leave and I quickly ducked into my room. I watched from the window as he and Karrie got into his car and they drove off together. I sat back on the bed, jealous and disappointed.

I wasn't certain of it, but I had a feeling that would be the last time that Derek and I would ever do anything sexual together. He seemed to be having doubts before this and I don't know if he would ever stop having them. He had left me with a hunger for cock that could no longer be satiated. I stared a while longer out the window, just thinking about what had transpired and what would be.

I never changed out of my dress that day. Everything I did, I did dressed as a girl. And that night, I took off all my clothes. I took a shower, washing all the makeup off of my face. I pulled out the duffel I kept all my girl clothes in and put today's clothes inside. I grabbed a guy's t-shirt and some basketball shorts and a pair of boxers and threw them on the bed. And then, just as I went to grab the boxers to put on, my hand wandered over to the bag and began to search around. I pulled out a pair of light blue panties and my baby blue nightie from L.L. Bean. I threw the guy's clothes off the bed and I put on the panties and the nightie. I crawled into bed and went to sleep, not knowing what it meant but knowing that dressing as a girl made me happy.

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4 Comments
oshirixxxaioshirixxxaiover 5 years ago
Flutter

Thanks for this story, my second favourite one here, and who knows, by the time you're finished it might be my favourite. It gives me so many flutters, I can't get enough of this story, and am deeply saddened thinking I might have to wait years for the next chapter, but if that's what I have to do I will!

Love you.

christieamberleechristieamberleeover 5 years ago
Wow!

I love this story. The combination of incest and transgender makes it that much more enjoyable. I hope you don't wait as long between writings as you did for the other chapters ... I would love to read about Ashley getting an understanding boyfriend to replace her brother.

AnonymousAnonymousover 5 years ago
Hi

Love your story. Cant wait for the next chapter

AnonymousAnonymousover 5 years ago
Welcome back, Ash!

Welcome back, sweet, hot Ash!

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Cunt Series Info

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