Feminizing My Little Brother

That little pervert! How dare he spy on me. I was going to give him a piece of my mind. I rushed out of there, still completely topless with my face, neck and boobs covered in Nick's cum. I ran down the hall after Alex. I didn't want to shout and get Nick involved but I wanted to catch him before he hid in his room.

"Alex?! What the hell!?" I whisper yelled at him when I turned the corner. He looked scared, exactly as scared as you can imagine having just been caught spying on his sister and her boyfriend having sex. He also had a noticeable tent in his pants.

"Lynne, I'm sorry. I just heard you two and I couldn't help it. I was... curious." He stammered out his words on the brink of tears. He turned away from me and covered his eyes with his hands.

"Alex this is really not cool. Don't spy in on me like that. I'm your sister and that's not okay." I put my hand on him to make him face me.

"But it wasn't you I wanted to spy on." He whispered, I wasn't even sure I heard him right.

"What? If you weren't spying on me then why the heck were you watching?" I watched as his face got all red and his eyes went down to the floor. He didn't say anything but I had an idea of who he was thinking about.

"Nick? You were spying on Nick, weren't you? Oh Alex. I'm sorry I was mad at you." I let go of him and backed up a little bit.

"I'm just so jealous. Of you, of Ellie, of Mom. Why couldn't I have been a girl too? You get to be all girly and dress cute and like boys. It's not fair. I want to do those things too." Alex cried as he spilled all of his pent up feelings to me. I reached out and pulled him in for a hug. I didn't care that I was half naked and soaked in cum. Alex returned the hug.

"It's ok to be girly and dress cute and like boys, Alex. I'm not going to judge you. I wish you'd told me sooner though instead of spying on me." I said as I held him close.

"I'm sorry, Lynne. I just really wanted to see Nick in action. You're so lucky, I wish he'd do that to me." Alex spoke with a level of confidence I wasn't expecting. I broke the hug and held him at arm's length again.

"Wait. All of it?" I asked.

He nodded.

"Even the part where he called me names and slapped me?" I asked again.

He nodded again.

"Even the part where he came on my face?" I looked at him, puzzled.

"Yeah that's actually the part I'm most excited about." He said sheepishly, looking away and blushing.

A light bulb went off above my head. I had to test this though before I made it real. "Alex would you like to lick the cum off of me?" I looked closely at him, trying to gauge a reaction.

His whole face lit up. "Really!? You'd let me do that!? Yes, please." His eyes widened and his erection stood firmer in his pants.

"Well go ahead then." I said as I pulled my hair back over my shoulder and justed out my perky tits.

Once Alex had permission his tongue was on my boobs lightning fast. His hands held me in place as he slurped up all the cum from my chest, then my neck and then my face. He was like a little puppy, it was adorable. He was swallowing it all right away without any hesitation.

After I felt he got it all I put my hand on his head and gently backed him off of me. "Was that fun? Would you like more?" I asked him.

He looked so cute when he got excited, his eyes lit up and he smiled wide. "Yes please." He had such an innocence about him that was only made more charming because we were talking about him eating cum.

"Well too bad for you but Nick can't cum more than once a night." I teased him. His smile drooped. I quickly added. "But you're going to wake him up in the morning with your lips wrapped around his cock. Would you like that?"

His smile was back. "Yes, yes please." He looked so happy at the idea.

"Okay wait here a minute, I'll be right back." I said before turning around and heading to my bedroom. When I got there Nick was passed out and snoring on my bed. Ignoring him I went to my dresser and collected a few articles of clothing, stuff that was a little small on me but also a bit slutty. I also grabbed some makeup. I was beginning to get just as excited as Alex was about my idea. I was going to turn him into the perfect little whore so Nick could take all of his dominance out on Alex.

I went back to where Alex was standing in the hall. His hand was down his pants and he was furiously stroking his cock.

"Eh eh eh. No. Girls don't have cocks and they don't play with themselves like that." I scolded him. "From now on you're a girl so no more touching yourself like a boy. Understand?"

He looked surprised but he nodded. His hand slid out of his pants but his bulge remand.

"Now strip." I commanded him. He did what I said without question. As he took his clothes off I sorted through the clothes I'd brought for him.

"Okay I'm done." He said. I looked up from my sorting and saw my little brother naked for the first time since we were kids. He had pale white skin with a thin frame, he was completely free of body hair save for a little patch above his equally small penis. Even fully erect he didn't have more than 4 inches to work with. I smiled at him and picked up a little black thong I'd brought. I went over and walked around him, inspecting him.

"Not bad, little brother, you are going to make an excellent cum slut. But first." I got behind him and squared with the thong. "Lift your feet one at a time." I instructed him. He did what I said and I got the thong around his ankles. With care I slid the underwear up his legs and settled it up on his hips. I went around to his front and saw his pathetic tiny dick sticking out of the waistband.

"We're going to have to do something about that." I said as I got down on my knees in front of him.

"Lynne? What are you doing?" Alex asked with fear and a hint of arousal in his voice.

"Well I'm not about to suck your dick if that's what your dirty mind is thinking." I scolded him. I reached for his penis and the waistband of the thong and with a bit of effort I tucked the little monster in where it was covered. Anyone could still see a penis beneath the fabric but it at least looked like I tried to hide it.

Next I went for a corset that was among the things that Ellie left behind when she moved out. I tried it once and didn't like it. It would be perfect for Alex though. He was skinny but he still had the frame of a boy, this would help make him curvier. I undid the lace and went over to him and wrapped it around his stomach. He looked nervous about this.

"You're gonna be fine, Alex. This is going to help you." I secured it in place and began lacing it up. I pulled it tight and Alex squirmed a bit.

"It's hard to breathe in this, it's too tight." Alex whined.

"Hush, the price of beauty is not cheap." Alex and I giggled at the way I'd parodied words our mother often said. "And trust me, this is going to make you look like a curvy little slut."

Next I went for his hair. He always kept his long orange hair tied up in a ponytail that one could argue was masculine enough. I pulled the scrunchy off and ran my fingers through his hair, trying to make it just a bit more feminine. I wasn't a stylist or anything but I was satisfied it looked good enough.

I went back to the pile of clothes I'd grabbed and sorted through the two dresses I'd brought. One was a skin tight black club dress that hardly covered my butt when I wore it. The other was a very thin sundress that was way too bright and colorful to go with my wannabe goth style. I propped them both up so Alex could see.

"Lady's choice?" I asked. Alex looked at both of them and I held them in front of my body to help give him a better idea of what each of them looked like.

"Can I try them both and then decide?" He asked nervously.

"That's fine, arms up." I said as I put the club dress down and went over to him with the sundress. He put his hands up and I threw the dress over him and helped him slide into it. After a bit of smoothing and straightening he had it on just right. It looked alright on him. He had no cleavage whatsoever but the corset gave him a slim waist that made it feminine looking. The bright dress paired well with his hair.

"You wanna see how it looks?" I asked him. "Cause I think you look pretty good." He nodded his head with a big smile and went to the bathroom to look in the mirror.

He took in the full sight of himself and happiness radiated off of him. He did a little twirl and looked at himself from behind. I came over and stood in the doorway and watched him enjoy the view.

"Do you want to try the other dress? If not I can teach you makeup now." I was sincerely very happy helping Alex with this, his happiness was making it so much fun. Thoughts filled my head of turning him into my personal Barbie doll.

"What do you think, Lynne? I really like this one but I think the other one would look sexier." He kept his eyes on himself when he spoke to me.

"I'll tell you what. I'll put the other one on and you can see what it looks like on someone's body. I think you look adorably cute in that one though." He nodded and I went back for the other dress. It had been at least a few years since I last tried this dress on and it felt shorter than I remembered, and I remembered it being really short. I pulled my sweatpants off and slid the dress on. I could tell right away that anyone who wasn't too much taller than me had an angel where they could see my panties when I stood still in the dress. And if I walked at all anyone of any height would get a full view of my panties.

I went back to Alex, who never stopped checking himself out in the mirror.

"Thoughts?" I asked before striking a runway pose with my hand on my hip and one leg straight with the other knee bent. He turned to look at me and his smile turned into an embarrassed blush.

"I could never wear something like that. It's too, uh-"

"Slutty?"

"Yeah..."

"That's okay, move over. I'm going to show you how I do my makeup and then we're going to work together on yours. Tomorrow morning you're going to have to do this yourself before you wake me up. Understand?" I pulled out my makeup bag and dumped its contents on the sink counter.

Alex watched in awe as I applied my foundation and eyeshadow. I'll admit I was going a little off the deep end when it came to the amount of makeup I was using. By the time I finished with my lipstick I looked like a street hooker. I figured if I went extreme with it then Alex would have a better chance of picking up all the techniques.

When it came to Alex's turn for his makeup I started him off but I made him tell me exactly what I was doing and how I was supposed to be doing it. Quizzing him on what I'd just showed him. He seemed to have paid attention and I had him doing it on his own after not too long. When he was finished we looked at each other in the mirror. He definitely wasn't a passable female but he was certainly pretty.

"Okay so here's my plan, I'm going to go to sleep now, you should too. Don't sleep in your makeup or that corset. Try and wake up early and doll yourself up again. When you're ready come into my room, quietly so you don't wake up Nick. Wake me up so I can get his dick out and you're going to suck it till he cums in your mouth. Got it?" I laid out my detailed plan for Alex, who once again looked really nervous.

"What if Nick gets mad I'm the one sucking him off? I'm scared of what he might do." Alex looked away as he spoke.

"Nick isn't going to get mad. He loves it when I give him blowjobs and he's going to think it's me doing it this time too. I'm going to straddle him with my crotch in his face like we're 69ing. He's still going to be half asleep and it'll seem like I'm the one whose mouth he's in. And if he wakes up and realizes what's actually happening you're dressed like a girl so that totally makes it straight for him. I'll make sure nothing bad happens. He'll cum in your mouth and that will likely be it." I put my arms around his shoulders for a mini hug.

"Okay, I'm really nervous but I'm also really excited. I can't believe I'm finally getting to do this, I've dreamed about this for so long." Alex looked down and my eyes followed his gaze. His cock was bulging out from under the dress. The tight thong was holding it back a little but he was so excited it was still peaking through.

"Don't you dare touch that cock, Alex. In the morning if I think you've masterbated at all tonight I won't let you touch Nick." I said firmly.

Alex looked distraught. "Why not? It's so hard, I just want to play with it a little." He reached under his dress to grab his penis. I yanked his hand back.

"You will not touch that pathetic little baby dick ever again. If you really want to be a girl then you need to act like it isn't there. Trust me, you're not going to need it to have fun anymore." I started that speech firmly but ended it was a reassuring tone that made Alex smile.

"Now take your makeup off and go to bed." I left him in the bathroom and went back to my room. Nick was still asleep, his cock was slumped up against his thigh. Even completely flaccid he was bigger than Alex's full erection. This was going to be fun.

I went to my desk and removed my makeup. Then I crawled in bed next to Nick, I still had the black club dress on. It made me feel sexy to sleep in it. It was late and I was tired, within 5 minutes I was asleep.

"Lynne. Lynne, wake up." My slumber was disturbed by Alex, who was standing over me wearing the sundress. And speaking of the sun it was bright out. I was still super groggy and it almost surprised me that it was morning already. At some point in the night a sleeping Nick had decided to spoon me. I felt his powerful arms pull me close and I felt his equally powerful erection pushed up against my lower back.

He was still asleep, thank god. I blinked a few times trying to wake myself up as much as I could. When I got a better look at Alex I noticed that he had done a much worse job on his makeup then we'd done together last night. The corset also didn't look as tight. But he was here and that's what counts.

"Let me see your penis. I need to know you didn't play with yourself last night." I whispered at him, careful not to disturb Nick. He blushed a little but lifted the front of his dress and I saw his pointy cock was still hard in his thong, there wasn't a white stain on the black fabric so that was a good sign.

"Take it out and bring it here." I tried to slip out of Nick's unconscious grib so I could see better. Alex was very hesitant but did what I asked. He pulled the thong down and his penis sprung free. It looked almost inflamed, he was so hard. I was fairly certain he hadn't played with himself but he definitely stayed hard the entire night. I wanted to be a little more sure so I got close to it and gave a sniff. It smelled like sweat but not like cum, he was clean.

"Alright, tuck it away. Let's get started." I wiggled out all the way from under Nick. Alex secured himself back in the fabric prison. The first thing I did once free was take my panties off. I handed them to Alex, who looked confused, happy but confused. I continued my plan and climbed on top of Nick. I placed my pussy over his face and got where I could see his cock. I motioned for Alex to come over and join me. He scurried over and leaned over the bed. It was an awkward angle for him, bent at the waist over the bed.

Nick must have woken up at some point during the night because he was actually wearing boxers now when I remembered seeing his exposed penis when we went to bed. I gripped the waistband of Nick's boxers and looked up at Alex.

"Moment of truth, are you ready to be a slut?" I gave him my most encouraging smile. He gulped nervously but nodded his head. His eyes transfixed on Nick's morning wood erection. I pulled down the boxers and freed Nick's sizable cock. I held his meat with one hand and beckoned Alex with the other. He got close and I pulled his hand over to Nick's throbbing member. I started to jerk Nick with Alex's hand, after a few strokes I let go and Alex kept going on his own.

Nick may have been asleep but his cock was very awake. I could see how quickly it was growing under Alex's care. He continued to use only his hands for longer than I would have liked.

"This is supposed to be a morning blowjob, not a morning handjob. Put some tongue into it or get out." I whisper yelled at Alex. How eyes got scared at the thought of being kicked out so he stuck his tongue out and nervously began licking the head of Nick's penis.

"Tastes good, doesn't it? Don't be afraid to put it in your mouth." I encouraged him. I'll admit that watching my brother dressed as a girl sucking my boyfriend's dick was having a tremendous effect on me. I could feel my pussy moisten watching Alex explore his first penis.

When Alex worked up the conference to take it in his mouth I felt Nick ster in his sleep. His body was finally catching up with the signals his penis was sending his brain. I felt his weight shift as he came to consciousness.

The idea that this first thing he'd see would be my dripping wet vagina in his face and the first thing he'd feel would be Alex's lips and tongue on his cock was turning me on in a way I'd never felt before. I'd found the excitement I'd been searching for. Whether it was the deception of exciting Nick or the manipulation of Alex, I knew I wanted more.

Alex kept sucking, growing more confident with each mouthful. He wasn't going very deep though, only getting the first 3 inches in his mouth. He was using his hands to jerk the rest of the shaft which I knew Nick prefers.

Suddenly I felt a tongue invade my pussy, I probably should have expected it but it caught me completely off guard. I shuddered and moaned as Nick's tongue worked my pussy with the same enthusiasm Alex was giving his cock. He grabbed my hips and grinded his face against my sex, practically tongue fucking me. He pulled his tongue far enough out so he could speak directly into my vagina.

"I knew you liked what I did last night, you really are a slutty little whore. Aren't you, Lynne?" His words were slightly muffled by my labia flaps but I was able to understand enough to send him back an "mmhmm." I think he really believed that I was the one sucking him off and I wanted it to stay that way. I knew he'd eventually be awake enough to notice that the head he was getting was backwards based on where I was.

Nick really went to work licking my pussy, like more work than he'd ever done in the past. His fingers found their way to my clit and I had to seriously hold back some moans and possibly screams from how good it felt. I knew if I was too loud then Nick could realize I didn't have his cock in my mouth.

I felt his tongue slid out of my pussy and his fingers leave my clit, giving me a second to catch my breath. It was a short moment because I felt his tongue push against my clit and his fingers probe my vagina. A cry escaped me and I rocked my hips back onto his fingers. Something unfamiliar was happening inside me, I felt as if all this pressure was building up in my abdomen and the more Nick fingered me the more intense it got until he put his lips around my clit and sucked real hard.

The pressure released as my first ever orgasm violently coursed through my body, causing a scream and lots of spasms. I threw my head back and yowled in the same way I'd heard Mom and Ellie do through the walls when they had "guests" over. I moaned and grinded my pussy against Nick's fingers. I never wanted this feeling to end.

Of course it did though and once my climax started to die down I felt drained and I had to rest my head on Nick's thigh. My breath was gone and I was breathing heavily trying to get it back.

Alex being the little trooper he was, never let up on his sucking and was still going strong. My brain started working again and I realized if Nick was paying any attention at all he'd notice that someone else was truly sucking him off.