D Is for Dress-Up

by Alison Tyler

  I took a drag off the cigarette, walked over to the couch, and sat down. “Over my lap, Michelle.”

  She began to pull her skirt down and I said, “Leave your skirt up.” Nervously, she came over to the couch and lay across my lap, her skirt pulled up so that her pretty derrière was exposed.

  “Legs spread.”

  “Sir?”

  “Legs open, Michelle. I don’t want to tell you again.”

  She parted her thighs. I set the ruler in the small of her back and let my hand trail up her inner thigh. I was still holding the cigarette.

  I placed it close to her pussy, so close she could feel the heat, but not close enough to burn her. She squirmed, her belly pressing against my hard cock.

  “Can you feel that, Michelle?”

  “Uh-huh,” she said.

  “Does it scare you?”

  She nodded.

  “I’m going to spank you, Michelle. But the next time I catch you smoking, do you know where I’m going to put out this cigarette, Michelle?”

  She shook her head.

  I chuckled. “Oh, I think you know.’’

  I dropped the cigarette on the floor and crushed it out with my foot. My hand returned to her thigh and lingered an inch from her pussy.

  The first blow shocked her, made her yelp. She squirmed as I hit her sweet spot again, my fingers curving under to give her exactly the right amount of thud, an amount I’d calibrated in years of spanking her—though never in a schoolgirl’s skirt.

  “Say, ‘Thank you,’ Michelle.”

  “Th... thank you, sir.”

  I spanked her again, my hand beating her firm ass in a slow, mounting rhythm. Michelle began to squirm in earnest, writhing and wriggling in my lap with each blow on her butt. I spanked her faster until she was moaning in pain, whimpering with each blow.

  “Th... thank you, sir,” she said, without being prompted.

  I slipped my hand between her legs, touched her there. She gasped as I slid one finger into her. A thin dribble of juice ran onto my hand.

  “You’re not a virgin,” I said.

  She shook her head.

  “And you’re very, very wet,” I said.

  She didn’t nod.

  “Was Andy your first?”

  Michelle shook her head again.

  I slipped two fingers inside her, curving my hand to massage her G-spot. She gasped and then moaned, pushing her ass against me, forcing her pussy onto my hand.

  “You’re enjoying this, aren’t you?”

  Shaking her head, she quickly replied, “No, sir. Please stop.”

  I worked my fingers in and out of her pussy, making sure that the pads of my fingers hit her G-spot with every thrust. Her wriggling felt incredible on my cock, and I knew I would come before she did if I wasn’t careful. When I eased my thumb down to touch her clit, she let out a wild, uncontrolled moan of pleasure and looked up at me with her bright-blue eyes.

  “You want it, don’t you? Want me to do to you what Andy did?”

  “No, sir,” she said. “Please...”

  “If you don’t want it, Michelle, why are you so wet?”

  “I...I don’t know, sir!”

  I started spanking her again—slow at first, then faster and faster as she whimpered and squirmed. I could tell she was very close—she could come from spanking alone if I did it right, but I wasn’t about to let my schoolgirl get off that easy.

  “Ask for it, Michelle. Ask for it or I’ll tell Andy you tattled on him.”

  “No, sir, please...”

  “Then ask for it.”

  “P...please, sir. Please do it to me...”

  “Do what? You know the word, don’t you, Michelle? Surely a slut who gives head for cigarettes knows the word for what she wants done to her?”

  She said it so softly I almost couldn’t hear her: “Fuck.”

  “Louder.”

  “Fuck, sir.” Louder.

  “Ask me for it.”

  Again, so soft I couldn’t hear: “Please fuck me, sir.”

  “Ask me!”

  Louder, almost a groan: “Please fuck me, sir!”

  “You want it from me the way you got it from Andy? Then beg for it!” “I want it, sir! Please fuck me, sir!” She seemed to break through a barrier and whimpered hungrily, “Please, sir! Stick your thing in me, sir! I want it, sir!”

  “Show me what you did to his cock before he put it in you! Show me what you did to Andy and his friends in the boys’ room!”

  She had definitely broken through the barrier. She was down on her knees in an instant, between my spread legs, groping at my belt and pants. She took my cock out and began sucking it fiercely, leaving lipstick traces down the length of it. Michelle was an expert. I knew I would come soon if I didn’t hold back. I fought my orgasm, not wanting to lose it before I fucked my naughty schoolgirl. She lavished her love on my prick, sucking desperately.

  I knew it was coming soon—I couldn’t hold back any longer. It was hard to pull her off my cock. She was so desperate for it, her breasts heaving under the open blouse as she sought my hard prick. “Turn around,” I told her. “Turn around and put your ass in the air.” She scrambled around, getting on all fours and wriggling her ass back toward me. Her gorgeous ass curved around my cock as I fitted the head between the lips of her shaved sex and pushed it in, hearing her gasp of release.

  She came before I did—just. I heard her moaning, felt her spasms as she gripped my cock, as I drove it into her rhythmically, and the contractions inside her milked the orgasm right out of my cock. I came, moaning myself as my cock spent itself in her.

  My cock slipped out of her. Michelle remained on her knees, moaning, her ass swaying back and forth as she begged for more.

  “You’re headed right back to the boys’ room, aren’t you?” I asked. “You can’t wait to get back there.”

  She looked over her shoulder, and smiled.

  RaGs To RIcHes

  DAMN,” I SAID, PEERING INTO THE BEDROOM window from the ladder I was on.

  Chris stopped painting and looked over from his own ladder. “What do you see?”

  “That’s quite the crib.” I was looking into a huge room with a gigantic canopied bed in the middle. Must be nice, I thought. Until I was fifteen, I shared a tiny bedroom with my younger sister. Then I left home.

  I kept painting, working on the trim around the window. The Florida sun was baking hot, but despite my Irish blood I’d gotten used to it, having grown up here. I just had to watch my skin—it still burned easily. No bikini tops for me—I had a T-shirt, shorts, and hat on for this job.

  Chris didn’t have to worry so much—he was black and didn’t burn so easily. Right now his bare chest was glistening with sweat and speckled with white paint. Not that I cared much—girls were more my thing. I looked back into the bedroom.

  “What kind of a kid has a room like this?” I asked.

  “A seriously foxy one,” Chris said. I gave him a look.

  “Oh yeah. Isabel Fuentes. A couple years older than us,’bout twentytwo, I think. Smokin’ hot Latina. Her daddy’s a lawyer, her momma’s a head doctor, and she’s an only child. They got some cash.”

  I whistled. “Yeah, that would help explain the mansion here.”

  By the end of the day I still hadn’t seen a soul at the house. “Where are they?” I asked Chris.

  “I heard they’re outta town, not that we’re supposed to know. Rafael knows the guy who maintains their irrigation system. He said the three of them are chillin’ in St. Vincent til Sunday.

  “Must be nice,” I said, a bit bummed I wasn’t going to see this Isabel Fuentes.

  The next day Chris had to cut out early. After he left, I moved my ladder back to that bedroom window. The backyard was remarkably private, and the previous day I’d noticed the window wasn’t locked. I took a good look for motion sensors, but didn’t figure there’d be any in an upstairs bedroom. I hopped inside.

  I’m not a thief, but I wan
ted to be rich for a day. Or at least an afternoon or two. I peeled off my sweaty clothes and took a quick shower in an adjoining bathroom that was bigger than my studio apartment. I knew the cleaning ladies came on Saturday, before the family got back, so I wasn’t too worried. Naked, I checked myself out in the full-length mirrors—not too bad. Arms a little red from the sun, but body doing fine. Dark tattoos contrasted with my pale skin. My hair, which was naturally Irish red, I kept cut short and dyed black. It stood up when it was wet, giving me a punkish look.

  Normally I went for a grunge/goth mix, but this was my chance to try something a little more upscale. I walked into Isabel’s closet, marveling at how many clothes she had. I went over to one of the rows of dresses.

  I never wore dresses.

  So it was weird that a cocktail dress caught my eye, a white one. I carefully took the dress off the rack and slipped into it. The material clung to my skin—I wondered what it was. The dress was strapless, with a satin tie that went under my breasts. But the best part was the back. I have a great ass, and the dress showed it off, clinging to my cheeks. Either commando or a thong with this one, I thought, spinning in front of the mirror. I grabbed some gold pumps from the closet—my feet were a bit narrow for the heels, but otherwise they fit okay. Isabel and I seemed to be about the same size.

  Back in front of the mirror, I wondered why I was doing this. I looked so different—what was this little ensemble worth? Probably a month or more of painting. I was spinning around in front of the mirror again when somebody walked into the bedroom.

  “Shit!” I yelled, and whoever it was screamed. A young woman stood in the doorway, frozen for a second. She was wearing a nice outfit and had dropped a small travel bag. Isabel.

  “Who the hell are you?” she demanded. Her eyes widened more. “And what are you doing in my bedroom? In my dress!”

  I held my hands out and babbled. “I’m sorry, you aren’t supposed to be here. I’m not stealing anything, I won’t come back, don’t fire Chris, he doesn’t know.”

  She gave me a blank look. I pointed to the open window. “I’ve been painting your house. I noticed your bedroom window was open. I—uh, I’ve never really worn anything like this before, and I guess...”

  I shut up, hoping she wouldn’t call the cops.

  She walked into the bedroom. “I got into a fight with Father and decided to come back early,” she said. Chris was right—she was gorgeous.

  “I’m really sorry,” I said, feeling stupid. “Let me just get my clothes and...”

  Isabel straightened up, looking less upset. But the gleam in her eye worried me.

  “Take my dress off. Now.”

  I’m normally a dominant person, but Isabel spoke like a queen. Not like a spoiled rich girl, but like a woman used to getting her way. I started toward the bathroom.

  “No. Right here.”

  I stopped. “I’m not really wearing anything underneath…”

  Isabel walked over to the bathroom and grabbed my painting clothes off the counter. “I take it these rags are yours?”

  I nodded, feeling embarrassed. Shit—I was painting, not going out for dinner. Why should I feel bad?

  She walked back into the bedroom. Her nostrils flared. I watched her closely, still wondering how busted I was. She brought my shirt closer to her face. “They smell like…”

  “Like paint and sweat,” I said. “I’ve been painting all day, honest, and it’s hot out there.”

  Isabel nodded. A change was coming over her. I took a step forward and reached for my clothes, but those full lips of hers curled into a half smile and she stepped away.

  “Not just yet,” she said. She motioned toward the mirror. “So, do you like my dress?”

  I wasn’t sure what to say. Finally I just nodded.

  “Well, fair’s fair. I’m going to try on your clothes.”

  “Ummm...” I couldn’t finish my sentence because Isabel started stripping. Her body was just as attractive as her face, with creamy brown skin and curves in all the right places. She took off her pretty travel ensemble and paused only briefly in her lacy bra and panties before removing them as well. Just as quickly, she pulled on my sweaty painting shirt and shorts.

  I stood frozen by the mirror as she strutted around the room, walking like a guy. She stopped right next to me, her eyes burning bright. “Go ahead,” she said. “Look at yourself in the mirror. You really do look lovely in that dress.”

  I didn’t want to turn my back on her, but she grabbed my shoulder and spun me around. My mind raced—at least she hasn’t called the cops, I thought, but this was getting weirder by the second.

  Suddenly her body pressed against me from behind. She was warm and strong, shoving me forward against the big dresser. It didn’t help that I was a bit tipsy in her shoes. A hand grabbed my hair, pulling my head back. Her teeth brushed against my ear, making my legs even more wobbly.

  “Arch your back,” she whispered. She pushed my head forward— I had to steady myself with both hands on the dresser. Isabel kept pressing my head down. I could smell my own sweat on the clothes she was wearing. A thigh pressed firmly into my ass, pushing me forward even more.

  “I said arch,” Isabel hissed, yanking my hair backward while shoving her leg between mine. I stumbled slightly, my legs spreading farther apart. I arched.

  “God, what an ass,” she said, running her free hand over the tight fabric of the dress. Although the tension on my hair lessened, I kept arching my back—her fingers and the leg jammed against me felt too good. Isabelle pressed tight, her hand coming around to squeeze my breast, her mons grinding against my ass.

  The grinding became frantic. She pulled harder on my hair again. Ass up-thrust and body jammed against the dresser, I realized she was using me, that she was going to get off on me, here and now.

  I was right. Isabel came, grunting and grinding, squeezing my breast so hard it brought tears to my eyes. Despite the pain, I nearly got off myself, thanks to her leg, which was pressed hard between my cheeks, mashing the clingy dress material into my wet pussy. Isabel finished too quickly though, and abruptly let me go and stepped back.

  Sore and horny as hell, I slowly straightened up and turned around. She was lounging on the bed, already smoking a cigarette. Smoking a fucking cigarette!

  “Don’t say anything,” she said, and her eyes meant it. “You shouldn’t have been in here. You’ll get fired and maybe arrested if people find out.”

  I stood quietly, wondering where this was going. She got up and peeled off my clothing, shorts first and then the shirt. She really did have a fantastic body, toned and strong, and she moved like a dancer. She tossed the dirty clothes at me. I caught a whiff of a new smell added to the paint and my sweat. It made me even hornier.

  “You can keep the dress,” Isabel said as she walked to the bedroom door. Still completely naked, she turned. “I’m sure you can see yourself out,” she said, nodding toward the open window. “Maybe I’ll see you tomorrow,” she added before leaving the room.

  Chris and I were doing the side of the house the next day when Isabel came out to the backyard wearing a minimalist bikini. She gave us both a nod and stretched out on a beach chair. I’m not sure who was more distracted—me or Chris.

  Shortly after he reluctantly left, there came a tapping on my ladder. I looked down.

  “Back door’s open,” she said. “C’mon upstairs.”

  I finished painting, slid down the ladder, and in record time put the brushes away and closed the paint cans. The staircase was just inside the back patio doors—I headed up.

  She held out a thick bath towel when I got to her room.

  “Trade you this for your clothes,” she said.

  I stripped and took a shower. When I came out of the bathroom there were clothes displayed on the bed. Pumps, long stockings, a thong, and a lavender dress. The dress was spectacular.

  “Go ahead,” Isabel said, from over by the window. “Get dressed.” Wearing a universi
ty T-shirt and a classy looking pair of capris, she looked like a pretty, young woman home from college.

  I walked over to the bed and picked up the thong. It wasn’t lacy at all and felt smooth as silk, but thicker.

  “Microfiber,” she said. “You’ll like it.”

  I let the towel fall to the floor and pulled on the thong. It felt very nice, and left my ass completely bare. Next were the stockings. They matched the dress perfectly and came to just over my knees.

  “Don’t get too attached to those,” Isabel said. “They might get wrecked.” I shuddered a bit at the implication, and tried to focus on the dress.

  It wasn’t difficult. This one was a corset dress, the bottom long and billowy, with a delicate net over the thick lavender fabric and white lace underneath. The top would fit tightly, thanks to rows of pink satin straps on the front, sides, and back. I had never held a piece of clothing that felt so... luxurious. Extravagant. Expensive.

  “Lovely, isn’t it?” Isabel whispered, closer now. Although I was standing in front of her, wearing just thigh-high stockings and a thong, I noticed she was deliberately not staring, like a man trying to be polite.

  I held the dress to my chest. “Will you help?” I asked.

  Isabel smiled. “Of course.”

  Moving behind me, she helped me into the dress and then laced up the top tightly. When she was done, my breasts bulged upward and I could only take shallow breaths. Isabel stepped back, and now she stared.

  “Dazzling,” she said. “You look like.”

  I blushed and walked to the mirror, then gasped. “Like a princess,” I said softly.

  “Yes,” Isabel agreed. “My princess.”

  I stared at myself, moving slightly to change the angle. What would my friends say if they saw me like this? It was so different. I spun, and the dress billowed outward. I turned to every angle I could think of, dazzled.

  Isabel interrupted my reverie with a small cough. I turned toward her, wondering how long I’d been looking into the mirror. She was close, and I was not entirely surprised to see she had put on my painting clothes.

  “It’s the smell,” she said. “I’m really turned on by smells.” She pulled my shirt up, breathed it in.