It had been two weeks since the incident with the police officer and my brother Derek. Christmas had come and gone, and things were starting to move away from the holiday cheer. Ever since I had received the makeover from my cousin Jenny, I have found myself oddly attracted to feminine things. I took some of the money I had gotten for Christmas from various relatives and decided to indulge my fetish. I bought various panties and bras from Victoria Secret, anything that I found to be pretty, mostly lacy, sexy, things. I bought leggings, skirt, shorts, dresses, and tops from Old Navy and Forever 21. I also had purchased an all-inclusive makeup kit. I ordered it all online, express shipping, and yes, I watched the door like a fiend to make sure the packages weren't intercepted by one of my parents or my brother. I had been studying YouTube tutorials online to learn had to apply my makeup. I was getting pretty good, I feel like I could compete with most twelve-year-old girls who were learning the same thing. I would wait until late at night or when I knew I'd be alone to practice and then I'd dress in various outfits and model myself in front of the mirror. I really enjoyed living this feminine double life.
Derek and I haven't spoken about the incident, and I am very happy about that. I am already questioning myself and my newfound love of cross-dressing; I don't need to be reminded of my possible homosexuality. Still I'd be lying if I said it hadn't been at the forefront of my mind since it happened. There is something about being able to satisfy someone with such intensity that it causes them to erupt from the pleasure. The compliments I received from him and the officer, the taboo of the situation, the pure eroticism, it was all so invigorating; I can't deny that. I have tried to masturbate since it happened but I can't bring myself to do it. As I approach climax, all I can think about is Derek's hard cock, in all its beauty. I don't want to cum to that image, I want to be straight and yet, here I admitting I love to cross-dress and mentally worshipping my brother's penis. I am conflicted to say the very least.
I was sitting in the living room watching reruns of Futurama when my brother came in the room. In his hand he was holding a thin, long jewelry box. He sat it down and front of me on the coffee table and said, "Would you look at this and tell me what you think?" I opened the box and inside was a gorgeous silver chain necklace. At the end of it was a small charm that studded with ruby. My brother had good taste. "It's pretty awesome bro, I am sure Karrie will love it." Tonight was Karrie and Derek's one-year anniversary; I guessed this was for her. "I sure hope so, it wasn't cheap."
"So where are you taking her for dinner?"
"We are going to that hibachi place she loves."
"Cool, man. Well aren't you quite the romantic?"
"I've been known to show a girl a good time."
"Haha, yeah, whatever. Well have fun! Mom and Dad are leaving for Iowa to visit Grandpa tonight, so don't forget to tell them goodbye."
"Oh yeah, I forgot, hopefully Grandpa will give us some cash instead of those crappy presents he gives every year."
"Hey! I love my Billy Bass singing fish plaque thing."
"Haha, yeah. Alright, well I am going to go get ready."
I was very excited. This meant I would have most of the evening to myself, maybe, even the night if my brother got lucky. I was already planning the outfit I would wear in my head. Maybe I would be able to rub one out without thinking about that beautiful dick of Derek's that had plagued my fantasies. While my brother was busy getting ready I helped my parents move their bags to the car and received the usual no party, be careful speech that is given every time they leave the house for an extended period of time. Derek yelled his goodbyes to them from the top of the stairs in his bath towel. I watched them pull out of the driveway and went to the kitchen and made myself some dinner; nothing special, just a chicken salad sandwich. Derek came downstairs wearing a dark pair of jeans and a faded purple button-down. He has on cologne, maybe a bit too much, but it would probably fade by the time he picked up Karrie. "Well bro, I am off." he stated.
"Have fun!" I replied.
When he left I headed upstairs for preparatory maintenance. I pulled from beneath my sink my hidden bottle of Nair, my razor, and body lotion. I applied the Nair and waited five minutes and hopped into the shower, washing away all the short hairs from the two-week accumulation since the last time I had Naired. I made sure every bit of my body was smooth and then I applied the lotion. I loved the feeling of my hairless body. It was so girly, so soft. Then I blew my hair dry and combed it in the girliest fashion I could manage. After I finished, I hid away all of the items and walked out of the bathroom in my towel towards my room. Then I heard the front door open and slam. Derek walked straight up stairs and went into his room, shutting the door fairly hard there as well. I don't think he even noticed me. I walked into my room disappointed that I would no longer get to have my evening fun, but also confused by why my brother was home so early. Had something bad happened with dinner? Did Karrie not like the necklace?
After I put on a pair of sweatpants and a t-shirt, I headed to Derek's room and knocked on the door. "Yeah?" Derek asked.
"Hey, everything okay?" Derek opened the door. He had obviously been crying.
"No, we were on our way to the restaurant when Karrie started crying and said that we needed to break up. I ask her why and she said that she had cheated with another guy and had really strong feelings for him. So she wants to see him now and not me. Then she told me we could still be friends."
"What did you say?"
"No, I don't want to be friends."
"So that is it."
"I guess so. It sucks man, I really liked for her."
"Well, I am sorry to hear that. If there is anything I can do, just let me know."
"I just need to be alone right now, thanks though."
Derek shut the door and I headed to my room, feeling sorry my brother. He was an asshole but only to me, everyone else would think he is kind of nice. Hell, ever since the incident he has been nicer to me. He didn't deserve this. I sat in my room and went online looking through various women’s clothing websites. If I couldn't dress tonight, I would at least indulge my imagination. After a bit, thinking of dressing up had gotten me pretty horny. That combination of my arousal coupled with my hung and vulnerable brother in the next room led to me developing a sinister plan. I would dress up as I planned to and go into Derek's room and cheer him up by modeling my new outfit. Hopefully, this will excite him, one thing will lead to another and I can get another go around with his enormous cock. It was such a devious plan, but I was far too horny to resist.
I grabbed my duffel bag full of my girl clothes and makeup, and sat down in front of the mirror. I brushed my hair, and applied a light foundation, followed by mascara, blush, green eye shadow, and a light pink lip-gloss. I grabbed my bag and grabbed my neon yellow lace hip huggers and white push-up bra. I decided on wearing these under my white, khaki skirt and blue-and-white striped, off the shoulder, v-neck tunic. I looked in the mirror and was so proud of myself; I looked so cute. The skirt was growing tighter, however, from all the naughtiness transpiring. I was so turned on by the thought of getting to suck off my brother again. Any more excitement and may have possibly came in my skirt prematurely. My heart was beating fast as headed towards the Derek's door. I lightly knocked. "Yeah?"
"Can I come in for a minute?"
I walked into the room and saw my brother lying on the bed stating at the ceiling. He looked over at me. “Ash? What are you doing?”
“You seemed so down, I thought I would come cheer you up!
“You look amazing. I didn’t even know it was you.”
“Well, thank you.”
“Have you been doing this a lot lately?”
“No, just today” I lied.
“Well, you really do look incredible. I know what we should do…”
I paused, waiting for Derek to say, those magic, sexual words.
“We should go downstairs and watch a movie, you can stay dressed and it will take my mind off of things for a while.”
That was not what I was hoping to hear at all, but I didn’t want to press the issue and I did want to cheer up my little brother, so be it. “Sounds good!” I said. We headed downstairs and turned on the movie, Slither. About thirty minutes later, disheartened, I went and made some popcorn. I came back in the room and set it down on the coffee table. I noticed Derek checking me out set it down. “I could work with this,” I thought, “I’ll just have to be a little flirtatious.” I sat next to Derek and began eating some of the popcorn. I then took a handful and laid my head on his shoulder. Slowly, as the movie progressed I moved my head down to his lap. He started playing with my hair, which felt amazing. Twenty minutes later, he looked down at me and said, “Ashley, you look so beautiful. You don’t look like a guy at all. You even smell like a girl.”
“Well, good. I hope this cheering you up.”
“Very much!” He began caressing my legs with his fingers, enjoying their smoothness. Then, suddenly, he began tickling my sides. In a panic, I jumped up and yelled, “Oh, you better not start this game!” He smiled and returned his attack, pinning me on the couch, I was stuck and hysterically laughing while my brother lay on top of me, tickling the shit out of me. He stopped and looked down at me, our eyes met, and then he leaned in and kissed me. I hadn’t expected this, yet I found myself kissing back. Slowly, kissing led to making out, our tongues exploring each other violently and passionately. As we kissed, I felt his crotch against mine, more importantly, his cock hardening in his pants. He rose up quickly and removed his shirt, and we resumed making out. All of this felt so very wrong and yet I was enjoying every second of it. My hard bodied younger brother taking control and treating me as though I was a beautiful woman he desired. I began growing hard in my panties. My brother once again arose, and said, “Let’s go to my room!”
We ran upstairs as fast as we could. My brother stripped off his pants and jumped into his bed. I was about to get in fully clothed when he told me that my clothes didn’t look too comfortable to sleep in. “Well then, I’ll be sure to give him a show,” I thought. With my back to him, I raised my shirt above my head and let it fall to the floor. Then, my back still to him, lowered my skirt while bending over, letting his eyes linger on my girly, lacey panties hugging tightly to my ass. I turned around and he pulled me onto the bed, rolling me over. We, again, began making out. I could feel his hard cock begging to escape from its confinement. Something had to be done. I broke away from the kiss and began kissing down his neck, then his chest, then his abdomen, until finally I had reached the top of his boxers. “Ash, You don’t have to,” he told me. And with that, his boxers came off.
His dick stood tall and proud, veins bulging from the shaft all the way to his beautiful swollen head. His balls looked large and tasty hanging between his legs. At the top of his cock was a large glob of precum. God, my brother had such a beautiful penis. I leaned down slowly and kissed his balls, pressing his dick against my face. It felt so warm. Then I took one ball into my mouth and massaged it with my tongue, and then I moved to the other. Derek was moaning loudly. I softly bit his scrotum and then began to lick from the bottom of his balls to the tip of his shaft. When I reached the tip, I kissed it, pulling his precum into my mouth. It tasted as good as the last time I had tried this. I then lightly traced my tongue down and up his cock, but when I reached the tip this time, I engulfed his cock into my mouth. Derek gasped. I lowered myself as low as I could go, being sure to cover my teeth with my lips and using my tongue to create pressure on the underside of the shaft. Then, I rose up leaving the head in my mouth before diving down once again, all while massaging his balls with my hand. I had a goal in mind this time; I wanted to feel his pubes against my nose. I wanted to take his entire cock into my mouth and make him unload into my throat. I wanted him to cringe with pleasure; shaking violently as he erupted from the euphoria I was able to bring him. I continued this pattern until suddenly Derek grabbed my hair and pulled me away from my joyful work. “I think it’s time I reciprocated!” he said.
Derek pulled me on top of him and we began kissing once again. Slowly, he rolled me over to where he was on top, still kissing. Then he began kissing my neck, moving down to my bra he began groping my chest. He pulled aside one of the cups and took my nipple into his mouth, then he moved to the other. It was electrifying; I gasped for air at the surprising amount of pleasure it brought me. He alternated between them and then moved back to my face and kissed me again, and then I felt him tugging at my panties. I rose up and let him pull them down, my dick flopping onto my stomach. Even though I knew it was there, I wasn’t a guy at that moment, I was a hot and horny girl. My brother kissed down my chest again and the down my stomach, when he reached my petite cock, he gave it a quick kiss. Then, unexpectedly, Derek rolled me onto my stomach and began worshipping my ass. He rubbed it with strong hands, kissed it, and traced his tongue over the mounds. Then he kissed the small of my back, kissing down to my crack. Using his hands he pulled apart my cheeks and slid his tongue my smooth crack. I had not anticipated this at all. Finally, he reached the hole and with that, gave it a deep and loving, long lick. Again, I gasped, I had never in my life felt anything like that before. He returned his tongue, slowly tracing the ring before pressing it in as far in as it would go. I moaned loudly as my brother continued eating my asshole, his tongue expertly darting in and out of my anus, licking everything, not missing a spot. I couldn’t help it, my moans grew loader and loader and my body began to shake. It was incredible.
Derek sensing my approaching orgasm withdrew his tongue and rolled me back over. There was a wet spot on my stomach where my cock had pressed against it, drooling precum from my brother’s anal onslaught. We returned to kissing. My brother ground his cock against mine as we made out, then he rose up taking my legs and placing them over his shoulders, he pressed his cock against my asshole. I wasn’t so sure about that; it seemed like a big step. “Derek, don’t!” I said. He replied, “Don’t worry. This will massage you there while we continue. I won’t actually go inside.” Being as horny as I was, I just went with it. The pressure there did feel quite pleasing. I think I was a bit curious of what would happen if he did penetrate me as well. Derek leaned forward and we returned to kissing, groping my breast and lightly grinding against me. And then, I felt it. My anus started to give; all of the saliva and precum was making a natural lubricant. I started to speak, but Derek just kissed me harder. Slowly his cock went deeper and deeper inside of me. I could feel it’s heat, it texture, its size as he penetrated further and further into my body. There was a slight pain, but I was so distracted from the kissing, I didn’t notice it too much. The pain started turning into an itch, then a tickle, and finally a delightful pressure.
Once my brother saw I was no longer wincing and distracted, he pushed the rest of his monster shaft inside of me. I let out a moan of celebration as I felt his pubes against my body. Derek pulled away from my lips and looked down at his accomplishment of being all the way inside of me. Slowly, he pulled out to the tip and then slowly pushed back in. He continued this pattern, eventually leaning forward and sucking on my nipple. My little penis was pinned between us, oozing precum with every thrust of my brother. His dick felt better and better,
“Do you want me to keep going?” He ask.
“I want you to beg! What do you want?”
“I want me you to fuck me with your giant cock!”
“Fuck me Derek! Please fuck me.” Derek started thrusting harder, driving into me faster and faster. I was shaking and moaning uncontrollably, I was a girl losing her mind in euphoria! My brother was going in and out of my asshole, leaving just the tip in before driving himself to the hilt. “Mmm… oh oh oh…. Oooo!” I sounded like a slut getting railed like she never had before. Finally, after ten minutes of constant assault on my ass, I felt the most incredible sensation I have ever felt in my entire life. I closed my eyes. “I’m cumming!” I yelped out naturally girlish. Between us, I unloaded what felt like all the semen in my entire body. And given the fact I hadn’t masturbated in two weeks, it was a fair amount. “Eh, Eh, Eh, Uh, Uh, Uh...” I squeaked as my brother pounded into me, my dick oozing what remained of the semen inside of me. I couldn’t believe I came like that, I had never felt something so incredible. I could feel the massive puddle of cum squirming between us as my brother continued fucking me.
I opened my eyes and looked up, he had a giant satisfied smile, like he had just conquered a mountain. I smiled back. Then, he leaned down and kissed me. As we kissed, I felt him tensing up. “Come inside of me, Derek. I want all of you inside of me.” With that Derek slowed his rhythm and his body began to shake as he unloaded into my ass. He pressed his cock as hard and deep as he could into me. I could feel the warmth of his cum flooding me. I savored the feeling. I felt so conquered and so feminine. I treasured those moments, those moments where I truly felt like a woman. My brother lay on top of me exhausted from his conquest, his penis still inside me, and my ass full of his cum. I rolled him over onto his side and pulled him out of me. “ Derek, let’s go take a shower,” I whispered. We rose from the bed and I led him into our shower, where I washed his body and he washed mine. We embraced under the water, kissing as it fell over our shoulders and down our bodies. “You’re the most incredible girl, Ashley!” he said. “Thanks!” I replied with a smile. Then after we were clean, we dried off. Derek headed to his room as I dried my hair. I went into my room and grabbed a pair of pink, lacey, panties and a long t-shirt. I walked back into Derek’s room, he was already asleep, and so I crawled into bed next to him and cuddled up. Why not finish off the night completely girly?