Dressing My Sister Up Like A Whore

I probably knew from the time I picked up my little sister at the airport that trouble was brewing. I was twenty-five and she was a nubile twenty-one, freshly graduated from college with a degree in women's studies. I was a struggling artist and, yes, I still lived at home with mom and dad. It was Saturday and they wouldn't be home from vacation until Wednesday. I didn't know Cara's plans in terms of how long she thought she'd be staying with us.

She started in on me almost as soon as we got into the SUV. First, she interrogated me on why I was still living at home (because I had no money). Then, she quizzed me on my love life (no, I didn't have a girlfriend and no, I hadn't turned gay). Then, she really went off the deep end.

"Do you know what really burns me up?" she asked.

I stared out the windows and got distracted by two women in tank tops and short shorts walking their Pomeranian.

"That," she said.

"What?" I asked.

"Those women. They're begging to be treated as sex objects. How does that make me seem?"

I looked over at Cara for a moment. She was in her usual baggy tee-shirt and men's jeans. Her short hair was uncombed and her face unmade. She wasn't a lesbian as far as I knew, but she did dress like a boy.

"I didn't notice," I said.

She snorted. "Your eyes were practically hanging out of their sockets. You definitely noticed."

I was silent. The light turned green and we were soon far away from the offending ladies. Cara crossed her arms and stuck her lower lip out.

"How am I supposed to have sex with anyone when all men want is superficial looks?"

I seriously almost said,

I'm sure your pussy looks as sexy as anyone's

, but I was certain she'd take that the wrong way. Actually, coming from her brother, it was hard to see how she could possibly have taken that the right way. So, I just kept my mouth shut.

"Would you have sex with me?" she asked.

A massive adrenaline dump from the base of my neck flooded my scalp and spine. Was my sister seriously asking me to have sex with her? I wondered if I was hallucinating all of a sudden. I stared at her.

"Car. Car!" she yelled, pointing out the windshield.

I turned and slammed on the brakes just in time to avoid hitting a left-turner who had come to a stop but didn't bother signaling. The ABS came on and everything.

"Jeez, David," she said. "Are you trying to get us killed?"

"Sorry," I said.

The other car turned and we continued on our way. We were about five minutes out from home.

"Well, would you?" Cara asked.

"Would I what?" I asked.

"Have sex with me?"

"Cara, I'm your brother. I know we fooled around sometimes, but we were little, and it didn't matter."

She stared at me. "What are you talking about?" she asked.

I shook my head. "We can't have sex."

She guffawed. "God, David. Seriously? I wasn't asking you to have sex. I was asking you, from a man's perspective, would you have sex with me if you met me somewhere?"

"Uh . . ."

My mind raced. There really wasn't any answer I could give that wouldn't get me in trouble. If I said yes, I was a pervert. If I said no, I'd wreck her self-esteem.

"Maybe," I said.

"What the hell does that mean?" she asked.

"It means, I guess it would depend on the situation," I said.

"That's a weasel's answer," she said.

I sighed.

* * *

That evening, we went to a bar and grill down the road for dinner because we were both too lazy to cook. They were full, so we showed them our IDs, sat at the bar, and had pub food with a shit ton of alcohol on the side. I had two beers and a whiskey in a little over an hour and Cara had two wine coolers and a shot of tequila. I didn't know why we were drinking so heavily. I guessed it was only because we could, now that she was legal.

Cara freaked out when I said I'd drive us home, so we walked the two miles back to the house. I was pretty sober by the time we got home. Cara was still blasted. She tripped over a crack in the sidewalk in front of our house but fortunately I caught her before she fell. She sagged against me and laughed; her hot breath smelled like alcohol. The back of her tee-shirt was smooth and I realized she wasn't wearing a bra. The realization went right to my groin, in spite of the fact she was my sister and dressed like a man.

"David, I can't walk any more. Carry me," she said.

"Dude," I said. "We're right in front of our house. It's, like, twenty feet away."

She stayed in my arms and stared up at me, an odd expression on her face.

"What?" I asked.

She shook her head. "Do you think of me as a dude?"

I had no idea what to say to that. I'd just been thinking of her tits a moment ago, but, in general, yeah, I thought of her as one of the guys.

I shrugged. "I guess so."

She stood up straight and walked away from me. I followed her into the house. Mom and dad's liquor cabinet was locked, but we both knew where the keys were so it was pointless. I went for the vodka, Cara went for the Irish cream liqueur. We did a couple of shots and picked a movie, some shoot-em-upper that had come out earlier that year.

Cara did two more shots, then slid off of the couch into a puddle on the floor, laughing like crazy. I picked her up and pulled her back onto the couch and she snuggled up against me. That made me feel weird. I didn't say anything, though, until she rested her hand on my crotch. I jumped up and paused the movie.

"Cara, what are you doing?"

She giggled. "What are you doing?"

I stared at her. I didn't imagine it. She definitely put her hand on my cock. I shook my head and sat back down, but one seat away from her. I restarted the movie.

A minute later, she said, "David."

I was almost afraid to turn and look at her. When I did, I saw she was crying. I felt like an ass. I paused the movie again.

"Aw, Cara. Don't cry. What's wrong?"

She scooted over to me and straddled my lap. I froze solid with my hands up, as if I were under arrest. She wrapped her arms around my torso, rested her head against my chest, and cried. Slowly, I lowered my arms and patted her back chastely. It was hard not to think of her pussy against my cock, even though multiple layers of thick clothing were in the way.

"It's okay, Cara," I said. "Why are you crying?"

"Guys don't like me," she blubbered.

"Come on," I said. "I'm sure they do. You've got to give us a chance."

She hung her head back and looked up at me. "Can you help me?"

I guessed that depended on what she wanted me to do. "I don't know," I said.

"Dress me up like a whore," she said.

I swallowed heavily. "What?"

"Teach me how to look like someone you'd want to fuck," she said.

"How?" I asked.

She stood up and extended her hand. "Come with me."

I hesitated, but then took her hand. "Where are we going?"

She dragged me to mom and dad's suite. She threw open the doors to mom's half of the closet.

"Dress me," she said. "Make me sexy."

This was freaking me out. I was supposed to dress my sister up in my mom's clothes so I wanted to fuck her? The whole thing just sounded wrong. But . . . God help me, part of me was a little intrigued.

She pulled her baggy tee-shirt off over her head, revealing her naked breasts. My eyes widened, then I squeezed them shut and whirled so my back was to her.

"Jesus, Cara."

"Look at me," she said. "How are you going to dress me up if you can't look at me?"

"I really don't think we should be doing this," I said.

"David, I'm asking for your help. I need you to help me be sexy."

Slowly, I turned around. Her hands were under her breasts, holding them up so they pointed directly at me. She swayed a little on her feet, reminding me she was drunk as shit.

"You need underwear," I said. "Like, a bra."

She stalked over to mom's dresser and opened the drawers until she found bras. "Here," she said. "Which one?"

I moved as if I was underwater. I was lightheaded and seemed to float over to the dresser to stand beside her. I looked into the drawer. Mom had her bras separated out in little cubbies. I pointed to a black lace one. "Like, that one," I said.

She took the bra out and slid it over her arms. It cupped her breasts and covered them completely. She turned her back to me. "Hook me up," she said.

I stared at the scene in front of me: my sister in my mom's bra, asking me to touch her. I felt like I'd entered a twilight zone, as if this couldn't possibly be reality. I reached out and took the bra straps in my hands, then hooked them together in the middle of her back. She turned around.

"Well?" she asked. "What do you think?"

I was as hard as a rock, but there was no way I was going to tell her that -- as if it wasn't obvious. Still, the bra had full coverage cups, whereas I wanted to see the tops of her tits, and maybe a little nipple, too. I looked into the bra drawer again and thumbed the other offerings. I found a whore-red bra that looked like it would only go about halfway up her mounds. I pulled it out. My sister stared at it.

"Seriously?" she asked.

"Seriously," I said.

She turned her back to me again and I unhooked the black bra. She shrugged out of it and passed it behind her to me. I returned it to the drawer and handed her the red one. She kept her back to me and slid it over her shoulders.

"Do me," she said.

I wanted badly to throw her down and stick my throbbing cock in her. What was wrong with me? Instead, I gingerly took her bra straps and hooked them together. She arranged herself in the bra, then turned around and faced me. I held my breath.

The bra covered the bottom half of her tits, pushing them up and out so they were as inviting as possible. Her dark pink nipples showed clearly above the bra, fully erect and screaming to be sucked. Her creamy cleavage seemed to go on forever and I imagined a low neckline over those full melons would promise nothing but endless ecstasy.

I licked my lips. My throat was dry as fuck. "That's the one," I said hoarsely.

She stared at me. A smirk slowly crossed her face. "Do you want to fuck me now?"

Hell yes.

I barely managed to keep myself under control. "Don't ask me that," I said.

"What about panties?" she asked. She turned to the dresser and found mom's panties in another drawer. She browsed through them until she found a matching red thong. She held it up. "Maybe this?"

Dread settled into my shoulders and my heart dropped into my shoes. I was going to fuck my sister. I saw that clearly now, and there was no way around it. I gaped at her helplessly as she unbuttoned her jeans and slid them down to her ankles. She stepped out of the jeans, then worked her granny-style panties down her legs and over her feet. She tossed the panties at me. They hit my chest and I caught a whiff of pussy before I brushed them away.

I couldn't have been more aroused if I'd been facing Miss Universe. My cock ached and my mind clouded. I stared at her bush in a trance as she pulled the red thong over her knees and up her thighs. The thin triangle of material didn't nearly cover her pubic hair but I was way beyond caring.

"Close enough," I said.

"Why brother dear," she said. "You look like you've seen a ghost. Are you feeling all right?"

For someone so naive, she knew exactly the right things to say to needle me ferociously. I sat down on the bed and stared at her slender curvaceous figure. My cock burned for attention and I desperately wanted to touch it or, better yet, get her to touch it.

"I'm fucking fantastic," I said softly. "Why don't you pick a dress and model it for me?"

She turned to the closet and pushed mom's dresses around, looking for something to torture me. She pulled out a black and white dress, turned, and held it up to herself. The neckline was high. I slowly shook my head. She put the dress back and shuffled through them again. She came out with a yellow dress that was a little better, but it was a maxi-dress - way too long. I shook my head.

She returned the yellow dress to the closet and pushed the dresses back and forth on their hangers for a while. Finally, she found the crimson dress I'd noticed as a flash of red as she was sliding everything around. She turned to me and held it up to herself. It had a low neckline, a cinched waist, and a flare skirt that fell above my sister's knees. I nodded.

She took the dress off of the hanger, unzipped it, and stepped into it. She pulled it up over her back and shoulders and turned so the open zipper faced me.

"Do me," she said. I was positive she meant what she said in every sense of the phrase.

"Come here," I said.

She did a one-eighty, took the two steps to the bed, and stood between my legs. I reached my arms around her and slowly raised the zipper along its teeth until the dress was closed. She rested her hands lightly on my shoulders and looked down at me.

"What do you think?" she asked quietly.

Her tits were at face level and I and struggled to keep my eyes on her face. My hands lay on her waist. I pulled her to me and my chin brushed the tops of her breasts. She smelled like plain soap and feminine sweat. I would probably not have minded at this point if she smelled like donkey shit.

"Do you want to fuck me?" she asked, in that same quiet husky voice.

"Yes," I said, breaking through the last barrier in my head.

I was going to fuck my sister. So what? I loved her, she loved me, we were both drunk and horny, it made sense. I bet it would give her self-esteem a huge boost so, really, I was doing her a favor, right?

"You naughty boy," she said. "Wanting to fuck your sister. Are you a pervert?"

"Apparently, I am," I said. "Cara, are you a virgin?" It would make a difference in how I fucked her.

She turned pink. "Yes."

I pulled her face to me and kissed her. She closed her eyes and returned my kiss while my hands roved over her body, feeling the silky dress and her heat and curves. I lay back but brought her with me so she was lying on top of me on the bed. We kissed again and she caressed my face. I rolled us over so I was on top now and scooted us up so all of us was on our parents' bed. She ran her hands over my back and even my ass. I kissed her for all I was worth, using plenty of tongue. It was not at all a family kiss. This was pure lust.

"David," she said.

"Mm?"

"Can we talk about this?"

I propped myself up on my elbows and looked into her suddenly serious face.

No, we can't talk about this. Now, shut the fuck up and spread your legs.

"What do you want me to say?" I asked.

"Do you love me?"

"Of course," I said.

"I only want to fuck a man if he loves me," she said. "That's why I thought of you."

I was going to lose my erection if she kept talking at me. I kissed her and ran my hands under her back so I could unzip her dress. I thought of how her tits looked in the red bra and how much I was going to enjoy sucking on her nipples.

"David," she said.

I managed to stop myself from rolling my eyes. "Yeah?" I asked.

"Do you have protection?"

I froze. Fuck protection. Why did she have to bring that up now?

"David?"

"I don't know," I said.

Maybe dad had some condoms somewhere. I couldn't exactly text him and ask him.

Yeah, dad, I'm about to fuck Cara, can you tell me where you hide your rubbers so I don't give you a deformed grandbaby?

"What are we going to do?" she asked.

"I'll pull out," I said.

"What?"

"I'll cum on your tummy," I said. "Don't worry about it."

She giggled. "This is so nasty. I can't believe I'm going to have my first time with my brother."

You will if you manage to shut up and let me get to work here.

"Yeah," I said.

I slid the zipper down and rolled off of her so she could shimmy out of mom's dress. I pulled my tee-shirt off so my chest was naked. She fondled the peace sign I wore around my neck. I grabbed her breasts and massaged them inside the half-bra. She reached behind herself and unhooked the bra. She had never needed any help from me in that regard. She took the bra off and I tossed it away. She lay on her back and I got on top of her again and kissed her tits. I sucked on her nipples and tickled them with my tongue and fingertips until she arched her back and moaned.

I kissed and licked my way down her belly, then grabbed her panties and pulled them off of her. She bent her knees and I spread her legs so her cunt flapped open in front of me. I buried my face in her moist folds and polished her vulva with my tongue. She shivered and ran her hands through my hair. I nosed her clitoris and stuck my tongue inside her. She gasped.

"David!"

I raised my head and looked at her. "What?"

She grimaced. "Isn't that . . . gross down there?"

I plucked a pubic hair from my tongue and flicked it away. "Not at all. I find it very sexy."

"You're crazy."

"Mm," I said, face down in her crack.

I licked and sucked her until her legs shook and she moaned constantly. She pressed my head into her core and I increased my pace until she squealed like a barnyard animal. I lifted myself onto her and kissed her mouth. She turned her head away.

"You taste like pussy now," she said.

"Get used to it," I said. "I'll want you to lick your cunt honey off my cock after I fuck you."

Her eyes went really wide. "David! How can you talk like that?"

"You like it, don't you?"

Her cheeks were flushed red with her desire. She looked away demurely. "Yes," she said.

"Slut," I said.

She quivered under my hands and I smiled wickedly. She could be as coy as she wanted, but deep down all she craved was my cock in her pussy. I undid my pants and slipped them off so I was naked. I slid my index finger into her swollen cunt. She moaned. I felt around and found a slightly thicker part on the top wall of her vagina. I stroked it with my fingertip. Her legs shook wildly and her head thrashed from side to side as she moaned loudly.

"God, what are you doing to me?" she asked.

"That's your G-spot," I said. "Do you masturbate?"

She giggled. "No, of course not."

I bent my thumb onto her clitoris and stroked both inside and outside of her gushing vagina. I couldn't believe she was twenty-one and had never masturbated. Maybe she was lying. Or, were girls really that out of touch with their bodies? The ones I'd been with up until now had healthy solo sex frequently.

"Oh-h, David," she said. "I want you inside me."

A spasm of pure desire ripped through me when she said that and I had to work to keep myself from losing it right there. I moved my hand from her pussy to my cock and stroked it a couple of times to make sure it was a hundred percent. It actually felt more like a hundred and ten percent. I shifted further onto her and teased her hole with my crown. She stared up at me, nervousness in her features. I locked gazes with her so I could watch the effect of my penetration in her eyes.

I guided my tip through her opening. She gasped and I grabbed her face so she stayed with me. Slowly, I pushed my girth through her entrance, keeping the pressure up until all seven and a half inches of me was inside her. I kissed her mouth, massaging her tongue with mine while I pulled out a little then thrust deep. I started up an easy rhythm, one that I hoped I could keep for more than just a couple of minutes. I wanted to make this last.

"David," she said when I came up briefly for air.

I lowered my face to her ear and nibbled on her lobe. "Mm?" I asked.

"I'm not a virgin anymore," she said.

"Nope," I said. "You're not."

"It didn't even hurt."

"That's good," I said.

I rubbed my face against hers and focused on the feel of my fat cock abrading her tight pussy. I fondled her breast with one hand, supporting myself on my other elbow. She moaned and I dropped my lips to her nipple and sucked on her teat.