1 comments/ 273340 views/ 47 favorites Stepmom's Sex Shocker By: StephanieSeymour My stepmother is the hottest, wildest piece of ass in town, and I've wanted to bury my nose into her musty pussy since we first met. She's literally twice my age. I'm 20. She's 40. But I know she's a freak. When my dad fucks her, she screams, "Owie! Owie! Owie!" You can hear it across the hall in my bedroom. It's better than a porno movie. I picture my stepmother taking it hard and fast in the ass. Then I jerk off while fucking my own ass with a lubricated dildo. My favorite way to finish is to cum in a cup and drizzle the contents on my face. Her name is Ann. She's not the type of woman you'd expect to be a Level Five butt slut. I mean, it's not like she's an ex-stripper or anything. Ann runs corporate accounts for a Fortune 500 company. You can tell she's a powerful woman by the way she dresses for work. Business suits. White collared blouses. Short skirts. She keeps her fingers sparkling with diamonds and gold, her neck draped in pearls. And, oh, how she smells! Ann wears this French perfume that leaves a wisp of dick-rising wind wherever she goes. Her attire is sexy, probably too sexy for middle management. The top brass might send her home to change some days, if she didn't rake in so much cash. I had to have her, but any move on her would be highly risky. She and my dad have an "open marriage," meaning they fuck other people. But it would be more than my dad could take if he found out I tried to bone his wife. I could kiss the family fortune good-bye. No more Ferrari, beach house on St. Bart's or high-class hookers. I would even have to do the unthinkable. Get a job. I eventually decided it wasn't worth the risk. I'd have to be content with my fantasies. But it turns out, I wasn't the only one with an unholy tryst on my mind. Ann made her move when my dad went to Europe with one of his mistresses. We were the only ones in the house on a Friday night. I was downloading cum shot movies when Ann opened my door without knocking. "What ya doin'?" she asked. I tried to play off my rock-hard boner and the hardcore porn playing on my computer screen. Moans oozed out of the speakers. "Uh, nothing," I said. Ann snickered. She looked hot as ever. A half-unbuttoned blouse revealed a Grand Canyon of cleavage. She was wearing a lacy, black bra. "Yeah, I'd probably say the same thing," Ann said. "It's OK. I'm glad you've been getting yourself in the mood." "What do you mean?" I asked. "Well," she said while twirling a few strands of blonde hair around her finger. "Want to play?" With her flowery breeze drifting into my nostrils, Ann led me by the hand to her bedroom. She went directly to the walk-in closet. When she came out, a lacy, blue teddy dangled from her fingertips by a pair of thin straps. Ann held the teddy in front of her body, so I could imagine what she would like in it. "You like?" she asked with raised eyebrows. "Yes, very much," I said. "Good, put it on," Ann said. She flung the teddy at me. I caught it at my chest. My heart started to pound like a series of bombs exploding beneath my breast. Every fantasy I'd ever had was melding together and coming true at once. Ann's bedroom screams left no doubt she was sexually adventurous. But this was a surprise -- a beautiful, bi-sexual surprise. With a huge grin, Ann put her hands on her hips and watched me slip into her underwear. The teddy was the kind of slutty lingerie you find in Fredrick's of Hollywood but was definitely too racy for Victoria's Secret. It fit perfectly, like a dozen hands squeezing and caressing all of my most sensual body parts. The straps gently touched my shoulders. The bra cupped my tits. The thong backside slipped up my rear end. My balls and cock barely fit into the front, but I made it work. "Very hot," Ann said, dipping back into the closet. "Now put these on." She handed me a pair of white six-inch heels. They were size 13. I don't know why she had shoes that big, but I didn't care. My feet slipped into the shoes with ease. Then Ann swooped back into the closet and emerged with a black wig. I put it on and looked at myself in the closet door mirror. The wig looked natural. It was the style the flappers wore in the 1920s and Goth chicks have co-opted for the 2000s. The bangs barely touched the eyebrows, while hair on the sides fell straight to the neck, framing my face. "Are you having fun?" Ann asked. I gulped and nodded. "Good," she said. "You look beautiful. Now come with me." She led me to the bathroom. A tray filled with makeup sat next to the sink. "Time to put on your face," she said. I chose candy-apple red lipstick, charcoal eyeliner and sea mist gray eye shadow. As I painted my face, Ann pressed her body against my back. She put her hands on my waist and slid them upwards until she found my tits. Her thumb and forefinger pinched my nipples. We gazed lustily into the reflection of each other's eyes. "I'm going to treat you like a little cunt," Ann whispered. Her breath smelled like spearmint. She rolled my nipples between her fingers. My cock felt like a shaken can of Coke. It could've popped at any moment. But I held back. I wanted to save myself for whatever Ann had in store next. She brushed some rouge on my cheeks, then stepped back. We both took stock in her handiwork. I wasn't going to win the Miss America pageant, but I felt sexy. And that's what mattered. "Very nice," Ann said. "Now, go to the bed and pose like a lingerie model for me. I'll be right there." I slid onto the white satin sheets feeling like a beautiful woman. Pictures of my favorite lingerie models turned over in my head. How did I want to present myself? On all fours and ready for back door action? Or on my back with a feminine arm over the head? I decided to compromise and go with a pose I'd seen in Victoria's Secret. Lying on my side, I propped myself up with my left elbow and leaned forward to accentuate my breasts. Ann loved it. She strutted into the bedroom moments later wearing a lacy white ensemble that showed off her best curves with a bra, thong panties, thigh-high stockings and heels. Ann gripped a chrome dildo about six inches long in her right hand and a "Larry's Lube" tube in her left. "You look like you're ready for a fucking," she said. "Get on all fours." I obeyed. Ann stood in front of me as she unscrewed the tube of lube. She squirted a glob in her hand and rubbed it on the dildo like she was stroking it off. The rod looked like a model of a next-generation ICBM. It was about as wide as two fingers pressed together and had a blunt top. "Move that thong out of the way and spread your cheeks, bitch," Ann said. "It's time for the silver bullet." She twisted the bottom of the dildo. It hummed like a set of clippers. But this was no haircut. Ann set the humming dildo on the outside of my asshole. It was a little tight because I was nervous. But the gentle vibrations put me at ease. Ann knew exactly when I was ready. She slowly started slipping it in. First, just the tip. Then, deeper. Finally, the entire width of the dildo was stretching my ass. I watched in the mirror as she started pumping my ass. Ann was entirely focused on my rear. She took shallow strokes at first. But she went deeper as I began to moan. My cock felt like a boiler under pressure. But there was no chance of slowly letting the steam whistle off. I was working toward an explosion, but I forced myself to hold back. Ann got on her knees behind me and held the dildo to her pelvis. She drove the rod all the way into me as if it were her own cock. Ann finally couldn't stand it anymore. "On your back, slut!" she yelled. Ann took off her panties so fast, she tore them. She flung them to the floor where they laid in tatters. The last thing I saw before squeezing shut my eyes was her leaping at me. When I opened them, her knees were by my ears and her dripping pussy was an inch from my nose. The musty smell mixed with her sweet perfume as it drifted into my nostrils. She had a thin Mohawk of a bush. Everything else was completely hairless. I licked all around the pussy, starting with the thighs and working inward. She groaned with ecstasy. When I went for the outer folds of pussy flesh, she moaned. Her legs gave way when I thrust my tongue inside her. Ann began grinding fanatically as I moved to the clit. "Owie! Owie! Owie!" she yelped. But she wasn't hurt. Quite the contrary. I didn't have to lick long. She juiced all over my face with a shudder that seemed to last forever. When she composed herself, Ann flopped onto her back. "OK baby," Ann said. "Your turn. Cum on me me." I kneeled beside her and whipped my cock out the teddy. All it took was three strokes. I must've shot ten gallons of cum. The first spurt landed in her cleavage. The second splattered across her cheeks. The third hit her mouth and chin. She looked like a "Got Milk" commercials gone mad by the time I was done. Ann laughed. I was nearly out of breath. "Come on, baby," she said. "Clean up your mess." I licked every drop of jizz off of her, starting with the puddle in her cleavage. My own warm, salty cum slid down my throat. I loved it. When I was done, I laid on my back next to her. But she wasn't in the mood for cuddling. Ann jumped up and slid on a fresh pair of panties. "Thanks, hon," she said. "I've got a dinner meeting. Let's do this again sometime. I'll save the outfit just for you." Ann winked and disappeared into the bathroom. And that's how our relationship has gone since then. We get into all kinds of nasty, little adventures. One time we even brought the gardener, Juan, into bed with us. The best part is my dad hasn't figured it out. As far as I know. Stepmom's Sex Shocker Ch. 02 My stepmother, Ann, was straddling me and leaning forward when I woke up. Her tits dangled in my face. "Remember these?" she asked. How could I forget? I was staring directly at the freckles in her cleavage where I'd shot my cum and licked it up just two days earlier. Ann had seduced me by dressing me in her sexiest lingerie. "You did so well the other day, we're going to have another nasty, little adventure," Ann said. "Are you ready?" I gulped and nodded. My parents kept an "open marriage," but acting out perverse fantasies with your step mom was taboo, even in my family. If Dad ever found out, I'd lose everything - my inheritance, my Ferrari and probably even my weekly allowance. But it was impossible to resist. Ann's soft, Texas drawl put a lasso around me. She dropped a handful of black lace and straps on my chest. "Put these on," she said. Ann sat in my favorite chair, the one shaped like an oversized catcher's mitt, and crossed her legs seductively. At 40, she was twice my age but still built like a college cheerleader. Her tight, blue sundress showed off every curve. With her watching, I rose out of bed and stripped off my boxer shorts. Ann had picked out a sexy ensemble for me. The package included a push-up bra, thong panties, fishnet stockings and a garter belt. All of it came from her lingerie drawer. I could tell because it smelled like her sweet perfume. The clothes made me feel like a slut the moment I touched them. The bra was my favorite. The cups squeezed my tits like a horny set of hands. Lingerie is way more complicated than men's clothes, but I managed to hook and strap everything myself. Years of studying lingerie shots while jacking off to Victoria's Secret had finally paid off. But it didn't teach me everything. The girls in lingerie catalogs wear panties under the garter. But I know from strip clubs that the garter's straps can get in the way when you're trying to tear off the panties to access the genitals. So, I slipped the thong over the garter. Ann seemed pleased. "Very nice," she said. "Now, put on a white T-shirt and jeans and meet me in the garage." Ten minutes later, Ann was behind the wheel of her white Mercedes. I got in the passenger side. A Burberry overnight bag sat in the backseat. "Where are we going?" I asked. "I'm going to teach you about something all girls love," she said. "Shopping!" I had a feeling she had something more in mind. Ann slipped on a pair of cat-eye sunglasses and shifted the car into reverse. We headed out along Van Buren Drive, then hopped on the interstate, heading north. Madonna's greatest hits blasted out of the speakers. Ann sang along in her best girlish voice, "We are living in a material world, and I am a material girl." We pulled the into a mall parking lot about 45 minutes later. We were in an upscale suburb on the other side of the city where no one would know us. Ann slid the car into a spot near the food court. "We're here," Ann said. "What are we shopping for?" I asked. "I'm glad you asked," Ann said. "We're going to get you a new dress." My cock rose at the idea. But there was just one problem. "Look at my shirt," I said. "The bra shows right through this white fabric. People might see and know I'm cross-dressing." Ann frowned thoughtfully, tilting her head to the right. Then her eyes suddenly lit up. "You're right," she said. "I've got an idea." Ann pulled a black eyeliner pencil out of her purse. I looked at the ceiling while she traced the bottom of my eyes and shut them when she penciled over the lids. Ann did nice work. The reflection in the vanity mirror reflected flirty but not slutty eyes. It was still too early to be slutty. "I'm wearing make-up!" I said. "Now people really are going to know something's up." Ann giggled. "I know," she said. "The bra was way too subtle." A teen clerk at Gadzooks was the first to notice my feminine fashion. It was the kind of store Britney Spears wannabes go back-to-school shopping. The clerk, a blond with big tits, whispered in a manager's ear. They both giggled. The clerk could still barely keep from bursting with laughter in our faces when she came over to ask if we needed help. "Yes," Ann said. "My stepson needs a new dress." The techno music thumping in the background came to an abrupt halt. Every eye in the store turned on me. At least a dozen shoppers - all women -- watched my cheeks turn pink. But what they didn't see was my dick stiffening even more under my panties. I was so humiliated - and I loved it. The clerk's attitude changed sharply. You could tell she was shocked. She must've thought she was being Punk'd when we first walked in. "Um, did you have anything in mind?" she asked. Ann pulled a black and white tube dress off the rack. "Do you have this in a large?" Ann asked. "It's spandex," the clerk said. "One size fits all…well, most." "Good," Ann said. She shoved the garment at my chest. "Go try it on," she said. The dressing room didn't have a door. All it had was a curtain that covered me from the knee to the neck. Anyone watching would be able to tell I was wearing fishnet stockings. More humiliation. This shopping trip was getting better by the minute. I stripped to my lingerie and slid the dress over my head. The fabric hugged my body like a warm, silky pussy around a stiff dick. I was so excited, I popped out of the dressing room and struck my best supermodel pose. "Wow!" Ann said. "Very sexy! Very slutty!" By then, most of the decent people had sensed the perversity of our show and had decided to leave. But a pair of teen girls looking like Jessica Simpson and Christina Aguilera kept the humiliation going. They pointed and laughed at me without even trying to hide it. Ann ignored them. "I like this outfit," Ann said. "But it's not quite what I had in mind. Let's check Victoria's Secret. But, first, come here and give mommy a kiss." She pulled my body against hers and French kissed me for the world to see. Our shopping trip lasted another two hours. We put on a show every time we went into a store. Teen-agers thought it was funny. Some adults found us repulsive, while others seemed entertained. Ann dropped a few hundred dollars on me. She bought me a string of pearls, a black wig, six-inch heels and a black cocktail dress. "Every girl's got to have one," she said. Whenever she bought me something, I'd add it to my ensemble. I was fully dressed in female clothing and make-up by 2 p.m. To get back to the car, I had to walk from one end of the mall to the other in drag. We might have fooled a few people, but almost everyone could tell I was no woman. One guy sporting a Confederate flag cap and walking the other direction, bumped into my shoulder and said, "Take the freak show back to Atlanta, faggot." "Maybe you'd like to come," I said. He just kept walking. Ann and I cackled like crazy. We got back into the car and drove to a hotel on the other side of the suburb. Ann parked by the front door, went to the front desk and returned a minute later with a key to an executive suite. "Boy, have I got a surprise for you," she said. My cock was pulsing by now. The slightest breeze could've made it squirt. I had to hold back with everything I had, especially in the elevator on the way up to the room. A group of six businessmen looking very serious in their Brooks Brothers suits slid in just before the doors closed. They were so focused they didn't notice the transsexual and beautiful woman standing in their midst. But Ann wouldn't let them get away that easy. "You sure are looking pretty today, girlfriend," she said. "You are, too," I said. Ann dropped the Burberry bag, leaned into me and sucked on my neck. I moaned like a foghorn. That got their attention. They crowded to the front of the elevator as if we had a catchy disease. Maybe we did. But I never had so much fun being sick in my life. When the door opened on the 11th floor, they sprinted out. We went all the way to the top. The penthouse. Ann was bouncing with excitement as she slipped the key in the lock. "You aren't going to believe this," she said. Ann swung open the door. She was right. I never would've guessed. Rico, our pool guy, was lying naked on the couch, almost in a statuesque pose. Sun pouring through the window bathed his rippling stomach muscles in light. "You, me and Rico," Ann said, "we're going to have some fun." Rico smiled devilishly and leapt off the couch. He and Ann dove into each other's arms. They kissed madly as Rico pulled up her dress and squeezed her ass. She started grinding her pussy against his cock before he could take off her panties. They didn't stop until Rico literally ripped Ann's silky underwear right off her hips. Ann chomped playfully at him and shot him a "grrrr." Rico flipped his tongue suggestively. "Rico," Ann said, "after five years you've still got it. I knew there was a reason we hired you, 'cause you sure can't clean a pool worth a shit." Rico either didn't understand or pretended he didn't. Ann brushed back her tussled hair and lugged the suitcase to the bed. She unzipped it. "Take off your panties and come here," Ann said. I daintily slipped the panties off my hips and let them fall to floor. Ann had a pink dildo in one hand and a jar of Vaseline in the other. Rico was grinning like he'd seen all this before. His six-inch pecker stuck straight out. "Good girl," Ann said. "Now, hike up your dress and get on the bed, doggy style. Rico, you go sit on the couch and keep your dick hard. We'll need you later." I could feel my tits hanging down in the bra as Ann twisted the bottom of the dildo to turn it on. A gentle hum filled the room. My cock stiffened. I stared directly into the headboard and waited, but nothing happened. I began to wonder if something was wrong. "Hey, Ann," I said. "What's the ma---" Then she did it. Ann softly, but quickly, shoved the dildo up my ass. She took long, deep thrusts. Ann touched parts of me I didn't know existed. I always knew that someone could fuck you with a dildo. But I never imagined someone could make love to you with one. Ann did. I was almost ready to cum when Ann pulled out. "My turn," she said. "Don't move." Ann put the Vaseline in front of me. "First, eat my ass," she said. "Then lube it up for Rico." Ann slipped her dress over her head, got on all fours and spread open her cheeks in front of me. She had the cutest little button for a hole - and it smelled like a rose. No, really. I know the only people who will believe me are the ones who've eaten my stepmom's ass, but it's true. Ann groaned as I worked on her. I licked her crack from her pussy to the small of her back. Then I stuck my tongue as far up the hole as I could. It might sound sick, but I wanted to crawl up inside her. "Now, the lube," Ann said. She was so out of breath, she could barely get it out. I scooped out a blob of Vaseline and fingered Ann's ass. Once she was lubed up, Ann crawled next to me, so our asses and faces were right next to each other. Rico knew exactly what to do. He popped off the couch without Ann saying a single word and kneeled behind her. "Ladies first," he said in that beautiful Costa Rican accent. Ann winced. I looked back. Rico was pumping her ass. He was doing her good and hard but not in a mean way. Ann's face unfolded into a slight smile. Her eyes were half-lidded and rolling back. "Uhh!" she said. "Rico, you're the best!" "I like you, too, baby," Rico said. He pulled out his cock and kissed the small of her back. "But I like the girly men, too," he said. Ann stayed next to me as Rico playfully slapped my left ass cheek and positioned himself behind me. His hands fell firmly on my hips. I gripped the sheets in my fists. This was it. My first cock up the ass. There was no turning back after this. I would be officially part homo. I thought about running. Rico must've sensed it because that's when he used his thumbs to spread me open and shoved his cock inside me. A painful shock ripped through my virgin hole. But it quickly faded and gave way to an indescribable ecstasy. I felt like Rico and Ann - and maybe even the whole world-truly loved me. My body pulsed with energy. Rico must've felt the energy, too. He trembled and tightened his grip on my hips. He was going to cum! Yes, I wanted him to do it inside me so bad. But then he yanked out. I opened my eyes and turned around in time to see Rico cumming on Ann's arched back. The goo shot for a very long time. When he was done, he and I watched it run into a puddle in the small of Ann's back. She didn't have to tell me what to do. As Rico slid back, I slid forward and leaned over. My nose hovered over the jizz lake for a few seconds so I could take in the aroma. Then I dove in, lapping the gooey mess into my mouth and swallowing it down like a cat does a bowl of milk. Rico was putting on his Speedo-style underwear when Ann flipped me onto my back. She deep-throated my entire stiff cock without saying a word. Her head bobbed. On every down stroke, she dug her nose into my pubic hair. Her lips puckered at the very tip each time she pulled her head back. Ann had to take only about a dozen strokes before I came. I could tell be the way she looked at me that she knew it was on the way. But Ann didn't pull back and let me squirt in the air. She took every last drop into her mouth, held it and positioned her mouth a couple inches above mine. I opened and let the cum slowly drip into my mouth like Ann was a coffee maker and I was the cup. Rico clapped. "Good show," he said, "good show." So, that's how my stepmom got me into my first homosexual experience. My dad hasn't found out. As far as I know. Stepmom's Sex Shocker Ch. 03 I was spreading peanut butter on a slice of white bread when Ann snuck up behind me. She pressed her tits into my back and slid her hands up my shirt. Her thumbs and forefingers pinched my nipples and rolled back and forth. I knew it was my stepmother, Ann, because of the perfume. She wears this sexy French stuff that smells like daisies. "You ready to go hardcore?" she whispered into my ear. I dropped the knife and bread on the marble counter as she teased my nipples. "Oh fuck," I moaned. I was lucky to get that much out. I was breathing hard and could barely speak. Ann playfully licked my earlobe. "I'll take that as a yes," she said. Ann grabbed me by the hips and spun me around. Although she was 40-- literally twice my age -- she was looking as fine as ever. Her wavy brown hair flowed just beyond her shoulders. She had on fire red lipstick. Her cantaloupe-size tits were wrapped in a lacy, white bra. Her curves fit nicely into the matching panties, garter and stockings. But the part of the outfit that really drove me wild was the shoes -- fuck me pumps with six-inch heels. Ann's lusty gaze pierced me. She pressed her lips against mine and thrust her tongue into my mouth. Our tongues sparred. But I was no match for Ann. Her aggressive tongue-jousts overpowered me. My knees started to buckle. "You look like you're ready for some more nasty fun," Ann said. I couldn't find the words to respond, so I let her know by sucking on her neck. She pushed me away before I could give her a hickey. "Good," Ann said. "Your -- how should I say? -- uniform is laid out on your bed. Put it on and await further instructions." Ann pivoted and click-clacked out of the kitchen. My stepmother and I had been carrying on a twisted sexual relationship for months. Whenever my dad went out of town, I dressed up in Ann's lingerie -- and she treated me like a wicked slut. Sometimes, she brought other men in the bedroom with us. Sometimes, it was other women. Ann always had control, and she always made sure I went through savage sexual humiliation. I loved every second of it. So, I couldn't wait to see what she had in store this time. A lacy, black corset was draped neatly across my unmade bed. Ann had also left me black wig and a make-up bag. I flung my guy clothes across the room. I don't know how women put on corsets, but I had to start by buckling the dozen clasps at the back, then slipping it over my head. This may seem ass-backwards, but it worked for me. The corset squeezed my entire torso. It was like getting a hug from Arnold Schwarzenegger. The bra-top made it feel like his hands were on my tits. I leaned forward and looked at myself in the bedroom mirror. If I let my arms hang down, I had the slightest bit of cleavage. I suddenly decided I needed music. I rifled my CD case until I found my 80s and 90s mix. When I went to my computer to insert the disc, I noticed something odd: the computer was on. I could've sworn I'd turned it off after downloading bukkake videos the night before. But I didn't feel like concerning myself with such trifles at the moment, so I just opened the drive and hit play. The first song was "Too Sexy" by Right Said Fred. I stepped into the thong panties. Nothing matches the feeling of having that string up your butt. Before I tried wearing one, I thought it would be uncomfortable. But it's not. It constantly reminds me of my demented brand of sexuality. After tucking my cock and balls into the silky panties, I slid the fishnet stockings up my legs. They clung lovingly to my skin. I was starting to feel like a woman. And I was getting better at being one. My masculine fingers usually fumble with garter straps. But I was able to hook all four straps on the corsets to my fishnets on the first try. Ann had also left me a pair of spike heels just like hers, except black. They fit perfectly. I've got to give her credit. It can be tough to find sexy shoes in women's size 13. I put on my wig and make-up in front of the dresser mirror, doing my best to make myself look like the porn star Devin Lane. The wig's straight, black locks fell just short of my shoulders in a page boy style. Reaching into the make-up bag, I went for the fire engine red lipstick. My lips seemed to light up as I traced it on. With dark eyeliner and eye shadow, I penciled sharp edges to the outer corners of my eyes to give them the sexy, almond shape guys love. When I was all made up, I stepped over to the full-size mirror on my closet door to check myself out. I hate to brag, but I have to say I was looking damn sexy for a slightly overweight guy dressed in women's lingerie. No way would I pass for a woman. But I didn't care. That wasn't the point. I felt sexy. I kicked aside some dirty clothes to give myself some dancing room. As if on cue, "Shook Me All Night Long" by AC/DC started playing. The music took control of my body. It made me gyrate my hips and caress my nipples. I was performing for an imaginary audience. In my mind, dozens of horny men in a loud, smoky strip club were watching me like a pride of hungry lions. Ann interrupted about halfway through the song. "I'm impressed," she said. Caught up in the fantasy, I jumped back and nearly tripped over my X box. I don't know how I managed to stay on my feet with those six-inch heels on. Ann was standing in the door way with a gold vibrator in her hand and my stepsister, Jasmine behind her. Jasmine was smiling devilishly to herself. "We're going to join your party," Ann said. She and Jasmine stepped into the room. I thought Jasmine was supposed to be away at college, but there she was. I didn't ask questions. It didn't seem appropriate as she stood there in a slutty, white outfit that matched the one her mother was wearing. All girls are cute at 19, but Jasmine was especially hot. She was tall, thin and chesty like her mother. Long, blonde hair fell half way down her back. Ann had never brought Jasmine into the bedroom, but I sure as hell didn't mind. Ann looked knowingly at Jasmine. "Why don't you show him what it feels like to be a woman?" she asked. Jasmine didn't answer. She just stepped within arm's reach and squeezed my tits. I thrust my chest forward and let her do it. She pressed my flesh together and licked my cleavage. I couldn't help but moan. But Jasmine was just starting. She pinched my nipples through the fabric and rolled back and forth, as she gave me a long, sloppy tongue kiss. Ann watched from the doorway. She stood at attention like a security guard. "Very nice," she said. "Now work on that bitch's ass." Jasmine slid around to my backside and fell to her knees. I felt her push aside my thong. My eyes locked onto Ann's knowing gaze as I listened to "Come on Eileen" play on the computer. But nothing else happened. I started to turn around to see what was wrong. That's when she spread my cheeks and hit me with the tongue. I was amazed at how fast she did it. Jasmine worked my ass-crack hard, licking from my back to my balls, then digging deep into my hole with her tongue. When my ass was loose, Jasmine elevated things: She shoved her finger up my hole. One knuckle first. Then two. Soon, she was pumping me with her whole finger. She continuously lubed with her own saliva. As my knees began to buckle, Ann said, "Enough!" and ordered me to get into doggy style position on the bed. She reached under the bed and got my secret stash of Vaseline. I don't know how she knew about it, but I didn't ask. Ann put a glob on the blunt-nose of the gold vibrator. She turned it on the lowest speed and pressed the tip against my ass without inserting it. At the same time, Jasmine yanked at the Velcro strap on her panties and let them fall to the floor. She positioned herself doggy style in front of me. She shoved her sweet, round ass in my face. "Eat her out," Ann said. I decided to offer Jasmine the same service she'd given me. As Jasmine spread her cheeks, I pushed my face into her crack. She smelled musty like a woman should with a hint of perfume. As I licked Jasmine's outer bunghole, Ann slowly pushed the vibrator inside me. She worked me gently. I moaned. When she saw I could take it, Ann cranked the dildo up to full speed and shoved all the way inside me. Then she did the weirdest thing. Ann said, "Come on over." My face was buried in Jasmine's ass so couldn't tell who the hell she was talking to. I turned my head and asked, "Huh?" "Never mind," she said while shoving the dildo far up inside me. I let out an involuntary grunt. My cock was harder than it's ever been. No one had even touched it, and I already felt like cumming. But I held it back. It wasn't time. Not yet. I wanted to keep this thing going as long as possible. Jasmine was moaning and Ann was tickling parts deep inside me when our neighbor, Carolyn, walked into the room, followed by her gardener, Ramon. Ann pulled out the dildo. Jasmine sat on the edge of the bed. "You put on a good show," Carolyn said. "We were watching on the computer." That's when it hit me. Ann had set up the mini video camera on top of the computer while I was downstairs making a sandwich. Carolyn and Ramon had been watching from across the street until Ann gave them the OK to come over. Carolyn was a 40-year-old hottie like Ann. But Carolyn had bigger tits. And like Ann, she was a brunette with a reputation for screwing around on her husband. Carolyn let her robe drop to the ground. She was wearing a purple sequin bra and matching panties. Ramon smiled at the scene: three mostly naked women and a cross-dressing homo. He seemed to be in heaven. Ramon stripped off his jeans and black T-shirt. He had six-pack stomach muscles and huge biceps. His erect cock stood at half of a foot. His neatly combed hair shined in the sunlight. "You got her ready for us," he said in heavily accented English. "Oh, I think so," Ann said. She grabbed me by the arm and led me to the floor. We kneeled in front of Ramon. Ann wrapped her lips around the head of his cock. She slid slowly down his pole. He flipped back his head and let out an "ahhhh." "You try," Ann said. I copied Ann exactly. My tongue caressed the underside of Ramon's cock as my head went down. I took about half of his rod on the first stroke. On the second, a little more. As I sucked Ramon, I saw out of the corner of my eye that Jasmine was stripping off Carolyn's underwear. They got on the bed and went at it in a 69. Carolyn was on top and braless, allowing her massive boobs to swing freely. Ann took over after my lips stroked Ramon's cock about two dozen times. "Here's how you deep throat," she said. Ann opened wide and effortlessly consumed all of Ramon's throbbing dick. Then she pulled back and did it again. And again. I was amazed. "Your turn," she said. I wasn't sure I could do it. Ramon had a lot of fuck muscle. But I had to give it a try. I opened wide, let my throat muscles hang loose and went down. My nose dug into Ramon's pubic hair. He smelled like Brut. Before I knew it, I was pulling back up. I'd done it! And I didn't even gag. After that, I thought I was going to suck him until he came in my mouth, but he pulled out. Ann was lying on her back next to Carolyn and Jasmine on the bed. Ramon topped Ann and started pounding her hard in the missionary position. Ann was saying, "owie, owie, owie," but not like it hurt. She was loving every second of it. Veins popped out of Ramon's forehead as he pounded her. Carolyn and Jasmine were clearly catching vibes from the action. They never looked over, but they were licking themselves faster all the time. I watched quietly on my knees while diddling my nipples. Ramon was simply amazing. I thought he was going to cum inside Ann, but he didn't. Instead, he pulled out of her pussy and came over to me. He pushed me down, so I was back in the doggy style position. He didn't fuck me slowly like Ann. He shoved all eight inches of himself inside all at once. The thrust gave me an amazing jolt. It was like electricity, flowing from ass straight to the tip of my cock. I thought was going to cum but was able to hold back. Ramon rocked my ass for a long time. He squeezed my hips hard and thrust harder each time. He grunted as his balls slapped against my leg. Ann laid in front of me and fingered her glistening clit while he fucked me. Carolyn and Jasmine joined her. Three hot chicks were masturbating in front of me. A hot Latin guy was fucking me in the ass. It's tough to get any better. But it did. When Ramon pulled out of my ass, he went straight for Jasmine's lips. A dam broke as soon as she opened her mouth. Loads of cum flooded her face. The jizz overflowed her lips and ran down her cheeks. She let Ramon fill her up until he shook the last drop from the tip of his cock. Ann took me by the arm and led me to Jasmine. "Your turn," she said. With two strokes of my cock, I exploded onto Jasmine's face. The first spurt hit her cheek. The next one drew a line from her eyebrow to her chin. By the time I was done, Jasmine's face was a gooey mess. All the while Jasmine was careful to not let any of Ramon's jizz spill from her mouth. Carolyn kneeled next to Jasmine and started licking the jizz off her face, starting at the drops on her neck and working her way up. Jasmine kept her cum-filled lips sealed, careful not to spill any of Ramon's sweet love juice. When Jasmine's face was clean, Carolyn pushed away and tilted back her head. Jasmine positioned her face over Carolyn's open mouth and let Ramon's jizz slowly dribble down. Carolyn took it all without swallowing. Carolyn did the same to Ann. Her face absolutely lit up at the first taste of jizz. It wasn't tough to figure out the pattern. I was next. I kneeled next to Ann, tilted back my head and opened wide. She gave me the jizz and saliva mix in a steady stream. It tasted salty and smelled like the sea. Hardly any cum had been lost in the transfer around the room. Ann had enough to fill my mouth. "OK," she said. "Swallow." I let the jizz slide down my throat. Sound gross? Hardly. It's the most erotic thing I've ever done. Stepmom's Sex Shocker Ch. 04 David Letterman was just about to end his interview with Madonna when my step-mother, Ann, stepped in front of the living room television. She wore nothing but a lacy, white teddy that barely covered her cantaloupe-size tits. Her poofy, brown muff showed through the thin fabric. "Tonight," she said, "we're going to see how much you can take." Ann and I had been carrying on a twisted sexual relationship behind my dad's back for months. But this time she had something really wicked planned. I could tell because her nipples were already standing straight up, and we hadn't even kissed yet. I turned off the TV. Ann stepped seductively toward me, gliding gracefully, even though she was wearing six-inch stripper heels. Ann straddled my lap and tore open my button-down shirt. Her fingers pinched my nipples, as she dry humped my cock. "I'm gonna make you my bitch tonight," she breathed into my ear. "I'm pimpin' you out, bitch. I'm gonna fuckin' use you and abuse you, and you're going to be fucked so hard you'll still be feelin' it a week from now. That OK with you?" I moaned and tried to kiss her neck. But Ann did something I never would've expected: She slapped my right cheek. Hard. "Answer me," she said. "Is that OK with you, bitch?" "Yes, ma'am," I said, while doing my best to catch my breath. "Good," Ann said. "Your outfit is in your bedroom. Get dressed up and meet me in the guest house." A teddy and high-heels that matched the ones Ann was wearing were lay out on my bed, along with a makeup kit. I quickly slipped out of my jeans and torn shirt, then slid on the teddy. My cock and balls fit up front better than I thought they would. The lacy top squeezed my tits ever so slightly. A G-string in back slid up my ass. I felt like a real woman. But it wasn't time to get fucked yet. The heels were a perfect fit. Don't ask me how, but Ann always managed to find size 13 women's shoes. My first few steps were clumsy, but I eventually made it over to my dresser mirror with the makeup bag. I lay on the charcoal eyeliner and mascara. It made me look and feel like a whore. I looked even sluttier once I applied the cherry-red lipstick. I had the hang of walking in heels by the time I made it to the guest house behind our home. As I made my way up the walk, I could hear voices behind the front door. It sounded like a party. When I opened the door, I couldn't believe my eyes. The living room of the guest house was full of naked men. They were all shapes and sizes. A couple of them were old and fat. But most were young, healthy guys that Ann may have picked up at the gym. I recognized most of our guests, including my dad's accountant, Mr. Jones from across the street and a clerk who works the counter at a nearby convenience store. Ann was on her knees in front of a frat-guy type I didn't recognize. He was leaning back into the couch. She was sucking his cock while the others watched. A few whooped and howled, as they sat in chairs and leaned against the wall. A guy I vaguely recognized -- maybe Ann's tennis instructor -- leaned back into the sofa and stroked himself. I watched unnoticed for a few seconds, but then the clerk noticed me. "Hey!" he yelled. "She's here!" All eyes turned on me. A loud cheer went up in the room. Ann stopped sucking the frat guy's cock and stepped over to me. The room fell silent. "These 15 men paid a lot of money to be in a gang bang," she said. "And guess who gets to be the star of the show?" I tipped my head flirtatiously. "Me?" I asked as innocently as possible. "That's right," she said. "Fuck the shit out of her boys." They fell on me like a pack of lions. The frat boy lunged at me. He leaned into me with a long, hard kiss. A pair of hands reached around me from behind and squeezed my tits. Someone pushed aside my G-string and shoved a lubed finger up my ass. Seconds later, I was wrestled me to my hands and knees. The accountant kneeled in front of me and shoved his cock in my face. He had at least seven inches with a helmet on top that would make Darth Vader jealous. The second I opened up, he grabbed me by the back of the head and forced his entire meat pole into my mouth. As the accountant fucked my face, I felt someone tearing off my G-string off, leaving my ass exposed. And so the train-fuck began. The first thrust hurt. I still don't know who gave it to me, but he must've been packing a canon. Imagine a broomstick being shoved up your ass. It took a few strokes to warm up, but the pain soon turned to pleasure. I began to moan. My cock turned to stone. The guys off to the side were hollering. The accountant plunged his flesh into my face with rising intensity. His cock spat a small splash of pre-cum as his enormous dickhead knocked against the back of my throat. I just relaxed and let him do it. When his body suddenly tensed, I knew what was coming. The accountant pulled out. I threw back my head. He shot his load all over my face. Streams of jizz covered my cheeks, lips and chin. I lapped up whatever my tongue could reach. With a guy fucking my ass and cum on my face, I'd never felt so violated in my life. And I loved it. The guys were going crazy. Most were beating their cocks in a semi-circle around me. All I could eke was one word. "More." It sent them into a tizzy. The guy behind me pulled out and flipped me onto my back. It was the convenience store clerk. He climbed across my body, then put his knees by my ears. His cock was pointing into my face. "Open up," he said. His jizz shot hard into my mouth. He tasted warm and salty. I decided not to swallow right away, so everyone could see how much he was squirting. The clerk's cum filled my mouth. I flipped my tongue so that just a little ran out the corners, mingling with the accountant's cum. I closed my mouth and let the rest slide down my throat. When I opened up to show the guy's what I'd done, they cheered. Ann interrupted them. "Hey guys!" she yelled. "Before anyone else cums, you should know about something I have for you." Ann held up an oversized margarita glass. "You can fill this thing with jizz," she said before motioning to me, "and make this bitch drink it!" They hooted like drunken pirates. Mr. Jones, our neighbor from across the street, grabbed my ankles and hoisted my legs into the air, spreading them far apart. His cock nudged around my ass crack until he found my hole. Then he thrust his six-inch rod inside me. Mr. Jones fucked me hard, shooting me a stern, laser beam glare the whole time. He was clearly getting off on dominating me. He pulled out as his face began to tense. Ann handed him the glass. Mr. Jones deposited a monster glob of jizz. One of the guys I didn't recognize lifted me back to my knees and slammed his cock inside me. This guy was rough. I suspect he was angry at something, but I never learned what. He grabbed the back of my hair and pulled hard. Each thrust was fiercer than the next. It probably should've hurt. But it didn't. Instead, I felt an ecstasy I'd never imagined possible. My dick was on the brink of exploding, but I held back. The guys took turn plugging my ass for what seemed like 10 pleasure-filled hours. I lost count around seven, but I know some guys went twice. Each time, they pulled out and came in the glass. From my hands and knees, I watched them fill it to the brim. When the last guy shook the last dribble of cum into the glass, Ann picked it off of the coffee table and carefully carried over to me without spilling a drop. "OK, bitch," she said, "on your knees and open up." I got into position, peeled off the tattered teddy and threw back my head. Ann poured slowly into my mouth. The warm goo covered my tongue. My mouth quickly reached capacity. I let the jizz run down my chin and neck. The little streams trickled as they trickled over my tits. Just when I thought it was over, the dam broke. Cum flooded my body. It was like a hundred mudslides all over my flesh. Ann finished me off when the glass was empty. She lay between my legs and wrapped her lips around my cock. I blasted my load immediately. Ann didn't even have to bob her head. She's a pro, so she swallowed every drop. Her lips didn't leave my flesh until my balls were empty. The guys took it all in without applause. I understood. No one is every happy they spent their hard-earned money on sex, no matter how good it is. They pulled on their pants without talking and left quietly. After I showered, Ann walked into the bathroom and handed me a wad of cash as I dried off. "Three grand," she said. "Not bad for a night's work." "You know," I said. "I could get used to this." Stepmom's Sex Shocker Ch. 05 My stepmother, Ann, always seems to catch me in my most vulnerable moments. Nothing startled me more than her surprise visit last weekend. I was in my tenth hour of downloading cum-shot videos when she kicked open my bedroom door. I tried to tuck my cock back into my pants, but there was no hiding what I'd been doing. Moans oozed out of my computer speakers. On the screen, a petite blonde begged seven guys to cum on her face. Ann smiled. "I knew I could count on you," she said. "Always looking at porn." Ann looked sexier than ever. Her tits bulged out of a hot-pink bikini. She wore a matching thong that left it absolutely clear that she'd just gotten a bikini wax. Sweat and suntan oil glistened off of her smooth skin. She'd just come in from the pool. If it weren't for the subtle crinkles at the corners of her eyes, no one could've guessed she was 40 -- exactly twice my age. She stepped into the room uninvited. I didn't mind. Not that I could've done anything anyway. She had video tapes of me dressed like a woman that would destroy me forever. "Ready to get weird, bitch?" Ann asked. I stammered something that she must've found incomprehensible. But Ann didn't even flinch. She leaned over and put her soft lips on mine. Her tongue slipped inside my mouth. My cock stiffened, while the rest of my body went limp. Ann had complete control over me. But she didn't stop. Her hands slid up my shirt and found my tits. She squeezed them firmly and then pushed them together. "I'm going to abuse the shit out of you," she whispered in my ear. "You're going to let my daughter and her boyfriend do whatever they want to you." I reached within myself and found the courage to ask something I'd been wondering for a long time: "Why?" It was a legitimate question. My step-mother and I had been carrying on an affair for months. She always initiated our fuck sessions and made sure I left feeling totally humiliated. But none of my questions mattered to Ann. She slapped me across the face when I asked. "I feel like it, and I can," she said. "Anymore questions?" I shook my head, thinking there was only one conclusion: my step-mother was an insane nymphomaniac. Ann turned her head and yelled, "Holly, bring James in here!" My step-sister, Holly, was five years older than me and almost as hot as her mom. She usually looked flat-chested but not when she stepped into my bedroom with James. She wore a white corset that pushed up her tits, making them seem twice their actual size. She had on fishnet stockings and sheer panties that showed off her muff. Holly didn't wax it. She had a big poof of hair -- retro style. I loved it. James was with her, carrying a brown shopping bag. I'd never met him. He looked clean enough and reminded me of Brad Pitt. "Give him the bag," Ann said. I peeked inside. There were heaps of satin and lace. A shot of perfume hit me in the nose. "You know the drill, bitch," Ann said. "Get dressed." James plunked down on my bed with Ann and Holly settling in on either side of him. All smiling, they watched me pull a bra out of the bag. I wasn't used to having an audience while I dressed up. "Are you going to stay there?" I asked. Ann smiled devilishly. "How else can we mock you?" Holly and James giggled. "Go on, faggot," Holly said. "Get dressed." "Yeah, you fuckin' weirdo," James said. He leaned over and licked Holly's ear. She moaned. Ann reached over and rubbed James' cock over his jeans. "We're all waiting," Ann said. I stripped naked and dumped the bag's contents onto my chair. Dressing in front of an audience felt awkward. I'd cross-dressed before. But I always dressed and then presented myself when I finished. Thankfully, I immediately saw that dressing up wasn't going to be as difficult as usual. No tricky clasps this time. I slid on a pair of sparkling, sliver bell-bottoms that squeezed my booty like shrink wrap. The matching top was a chest curtain that covered my tits and belly but little else. The only thing holding it on was a thin strap around the neck and one around the back. A pair of silver, six-inch heels finished off the outfit. Everything slipped on with no problem. I didn't have to mess with as much as a zipper. I struck a pose with one hand on my hip and a loose wrist hanging in the air. "Tah-dah!" I said. "What do ya think?" James lunged at me. Ann grabbed him by the waist and pulled him back on the bed. "Not yet, baby," Ann said. "You'll get your chance." Ann didn't have to tell me I still had work to do. I went for the make up bag. Slut-red lipstick. Heavy black eyeliner and mascara. It all went on thick, followed by gray eye shadow. I sprayed myself with perfume and put on auburn, pageboy wig. Now, I looked and smelled like a real whore. Ann positioned herself behind James, sitting with her legs spread out on either side of him. She slipped her hands up his shirt and licked his earlobe. James tried to lunge at me again. Ann pulled him back. "Not yet," she said. "Holly, why don't you show your brother how a real woman operates?" Holly arched an eyebrow. "Gladly," she said. Holly walked over to me with the sexiest switch I've ever seen. Our eyes locked together. She came within a half inch of my face. Her breath smelled like cinnamon. Without asking permission, Holly pinched my nipples and rolled them in her fingers. "You fuckin' whore weirdo," she said. As my knees weakened, Holly pushed me back into my chair. She went to the computer and clicked a few times. One of the cum-shot videos popped onto the screen: a blonde who looked vaguely like Ann took shots in the face as a techno soundtrack played in the background. Ann was sucking James' neck while he rubbed the bulge in his jeans. Holly paced like a lion in a cage across from the antelope exhibit. "You piece of shit," she said. "You fucking like porn? Hm? You like cum shot videos?" I didn't know what to say. I froze. Holly wound up and slapped me across the cheek. It stung like hell. "That's it!" Ann said. "Hit 'em again." Holly backhanded my other cheek. Now both sides of my face stung. "Get up and show me how you dance," she said. With the porno soundtrack setting the beat, I stood up and undulated my body like a stripper. James was damn-near salivating. I grabbed him by the knees and spread open his legs. I dropped my ass onto the stiff bulge in his pants and dry humped him. His hands ran up my back, then down to my waistline. He started to peel off my pants but then suddenly stopped. "Uh-uh," Ann said. "Just like the strip club: look but don't touch." She'd grabbed his hands and held them at his sides. I turned around and fell to my knees. I put my lips on James' bulge and blew. My hot breath enveloped his cock, as his eyes rolled back into his head. Ann was rolling his nipples between her fingers. We brought him near climax together. Ann sucked his earlobe, while I rubbed the crown of my head against his cock. James wriggle with ecstasy. Ann kept his arms pinned. I heard her breath into his ear. "Wanna see this bitch violated?" she asked. "Yeah," James breathed back. Ann smiled. "Holly," she said. "Get the dildo." I knew what was coming, so I backed off of James and got on all fours on the floor. Holly pulled my pants down to my knees. I heard her switch on the vibrator. "Mmmmm," I said. "I can't wait to get plowed up the ass." I licked my lips while look James dead in the eyes. They burned with lust. Ann was whispering something I couldn't hear in his ear. He liked whatever she said. His cock flinched beneath his jeans. Holly spread open my ass cheeks and dropped a dollop of lube onto my corn hole. The cool gel gave me goose bumps. But it was nothing compared to what came next. Holly shoved the rounded head of the fuck stick into my hole. She didn't go all the way. Just enough to get my attention. I yelped. Holly started pumping my ass slowly and gently, delving deeper into my fuck box on each down stroke. My body radiated with pleasure. The dildo went in cool and slow and came out fast and hot. Ann rubbed her pussy. She seductively licked her lips. She'd forgotten all about James and could barely contain herself. I suddenly realized she wasn't looking at me. Ann was focused like a laser beam on her daughter. "C'mere slut," Ann said. Holly jammed about three-quarters of the toy up my ass. She rushed to the bed and flopped down on her back. She peeled down the corset's bra cups, leaving her perky tits exposed. Ann pushed aside James. He stood and stumbled a few steps, while Ann tossed her bikini top across the room. Ann and Holly sucked each other's nips in a 69-position. Ann took the top, letting her tit drop into her daughter's mouth. James watched in disbelief for about three seconds. Then he lunged at me. This time, Ann wasn't there to stop him. He went right for the vibrator humming in my ass. James took over pumping duties -- and showed no mercy. He went hard and fast from the start. It was an angry fuck, like he wanted to hurt and humiliate me. "You little fuckin' slut," he said through gritted teeth. Nothing could've felt better. James took me to a higher plane of ecstasy each time he plunged the vibrator into me. Pre-cum dripped out of my cock, and I hadn't even touched it. Ann and Holly moved on to licking each other's pussies. Holly writhed. Ann moaned. James yanked the vibrator out of my ass and pulled down his pants. He forced his meat inside of me and pumped hard. His balls slapped off my ass. His thrusts came in rapid succession. He grunted every time. I moaned and asked for more. James must've had at least nine inches. I've been fucked before but never so deeply. His thrusts touched parts of me I didn't know existed. I had to fight to hold in my cum. James fucked for a long time. I squeezed my eyes shut about halfway through. When I opened them, Ann had Holly in the doggy-style position with her ass cheeks spread out. Ann's tongue probed her daughter's butt hole. When James couldn't hold it anymore, he pulled out of my ass and flipped me on my back. He kneeled next to me and unleashed a torrent of jizz onto my face. I opened my mouth. Salty cum landed on my tongue and slid down my throat. Ann and Holly broke apart and came to me. Holly lapped the cum off the left side of my face. Ann did the same on the right. After my face was clean, it seemed we were done. Ann, Holly and James flopped onto the bed in post-coitus ecstasy. They giggled. Sitting on the floor, I didn't see what was so funny. My balls ached. I needed some relief. An insane anger welled up inside me. I looked at my step mother. She had a spot of James' cum on her chin. I lunged at her, pinning her to the bed. I forced open her legs and shoved my cock inside her, while Holly and James watched in astonishment. Ann wriggled, making a feeble effort to resist. But she quickly acquiesced. All it took was three pumps for me to shoot my jizz into her pussy. As I shot, I looked into her eyes and yelled, "Fuckin' whore!" Revenge was mine. I'd taken so much humiliation from her and her fuck buddies. This time, it was her turn. After I dismounted, Ann spit in my face. She pinned me on my back and leapt onto me. Her knees landed by my ears. Her glistening pussy hovered over my nose. "Eat your own cum out of my pussy!" she yelled. I had no choice. Not that I wanted one. Her hot, wet pussy looked appetizing. I stuck my tongue up inside her. She smelled musty and tasted salty. Her juices and mine mingled inside her cunt. It was tough to tell which was mine and which was hers. I just sucked up anything that oozed out. After a few minutes of moaning, Ann pulled away and laid on top of me. Our eyes locked together like laser beams inches apart. I thought for a second she was going to hurt me. Instead, she laid a long, passionate French kiss on me. I lost myself in her mouth. And then, finally, it was over. Ann looked at me for a second like she was going to tell me she loved me. "Fuckin' whore," she said. Holly and James giggled. Ann had humiliated me again. It seemed there was no way for me to win. Ann could use my own perversions against me -- and she knew it. They all gathered their clothes and left my bedroom without saying a word. None was needed. We all understood that we'd be doing it all again soon. Stepmom's Sex Shocker Ch. 06 My step-mother, Ann, jolted me out of my dreams by slapping me across the face. "Rise 'n' shine, bitch," she said. "I need some entertainment." My eyes strained against the sunlight streamining into my bedroom window. Ann stood next to my bed with her hands on her hips. She wore a purple, push-up bra and a matching thong. Her ample bush pushed against the sheer fabric. She dropped a tangle of lace and silk on my chest. "Put it on," she said. I picked up one of the lacy garments by my fingertips. It was a bra identical to the one Ann was wearing. The panties on my chest were also the same. I was still in a dreamy haze "You want me to wear this?" I asked. Ann's answer couldn't have been clearer. She wound up and back-handed me across the face like a pimp. Without a word, I sat up and threw back the covers. I slipped off my boxers and put on the thong. As the string slid up my backside, my balls and cock settled neatly into the triangle up front. I hooked the bra behind my back and then slid my arms through the straps. The cups held my tits like a pair of hands. Ann frowned and shook her head. "You dirty, little whore," she said. Ann kneeled on the bed next to me. She pinched my nipples and leaned in close. Her breath smelled like mint. "You're mine, faggot," she said, while rolling my nipples between her fingers. Her deep, brown eyes swallowed me whole. Her cruel gaze made me yearn for her abuse. "I want you to go into the bathroom," she said. "Put on your dress, shave and do your make-up. Everything you need will be in there." Ann followed me down the hall and into the bathroom. I found a black cocktail dress hanging on the door. She watched me pull it over my head. The fabric squeezed me in all the right places from my thighs to my shoulders. After I shaved, Ann watched me lay on the make-up extra thick. Black eyeliner. Mascara. Red lipstick. I looked and felt like a whore. "Not bad," she said. "For a faggot bitch." Ann opened a closet and pulled out a pair of black high heels. My feet slipped comfortably into them. Ann slid on a pair of her own heels and grabbed me by the hand. She led me down the stairs to the foyer where she opened another closet. Ann put on an overcoat that covered everything above her knees. She reached up to a shelf and pulled out a red duffle bag. She handed it to me. "A t-shirt and jeans are inside," Ann said. "You can put them on when we're done." I quietly wondered, "Done with what?" But Ann didn't explain further. She grabbed me by the hand and led me to the Mercedes parked in the garage. Ann opened the passenger door for me. I looked at her. "Get in," she said. "I'm going out in public like this?" I asked. Ann hit me with another pimp-style backhand. "Yes," she said. "Any other questions?" I got in the Mercedes without another word. We drove in silence for about 45 minutes to a Holiday Inn about three towns over. Ann parked in front and turned off the car. "Follow me," she said. We went into the front lobby. Carrying the duffle bag, I made my walk as feminine as possible, but I knew I wasn't passable as a woman. I could feel strangers' mocking eyes on me. I tried to ignore them. A group of men in business suits sitting in a lounge area chuckled as I passed. "Hey, baby," one of them said. The rest howled with laughter. I followed Ann to an open elevator door. She hit the button for 12, the top floor. When the doors shut, we were alone. Ann slid behind me and grabbed my tits. She pulled me in to her body. Her tits pressed against my back, as her minty breath caressed my neck. "You like being humiliated, don't you, bitch?" she whispered. Ann pinched my nipples and started rolling them between her thumbs and forefingers. "Yes," I said breathlessly. When the elevator stopped at the fourth floor, the door opened with a ding. A guy in a golf shirt stepped inside and hit 12. Ann refused to let go of my tits. The guy tried to pretend to not notice, even though my cock was pitching a tent with my dress. "I'm gonna fuck the shit out of you," Ann whispered in my ear. I'm not sure if the guy heard, but he looked up. When the elevator opened, the guy scurried out and down the hall to the right. Ann released my tits, grabbed my hand and led me to the left. At room 1217, she drew a card out of her purse and inserted it into the electronic lock. The room was a suite with a king-size bed and a view of the suburbs. It was all traffic-clogged roads, strip malls and office buildings for as far as the eye could see. We were in the tallest building for miles, so we had total privacy, even with the curtains open. Ann didn't waste any time. As soon as the door shut, she said, "Hands up!" I dropped the bag on the floor and raised my hands. Ann pulled the dress over my head. Then she yanked my panties to my ankles. I stepped out of them. "Get on the bed now," she said. "Doggy-style." I obeyed, while Ann shrugged off her coat and then dug through the duffle bag. Her hand emerged with a chrome dildo and a tube of lube. She kneeled on the bed behind me. "Spread your ass cheeks," she said. I did as I was told. Ann put a dollop of lube on her index finger and then touched it to my asshole. Goosebumps formed on my arms. She massaged the entryway for a minute and then slowly pushed her finger inside me. My butthole loosened up. I was ready for anything. Ann pulled out her finger. I braced for the dildo, clenching the bedspread and squeezing shut my eyes. I took a deep breath and held it. And then... Nothing. Releasing my breath, I began to turn my head to see what was the matter. That's when she hit me. Ann pumped the plastic cock inside of me. "Uh!" I said. Ann pulled the dildo about halfway back. "I love abusing you," she said. My spine tingled. "Do you like being abused?" Ann asked. I grunted. Ann pushed the dildo forward. I arched my back. "Answer me, bitch!" she yelled. "Yes, mommy!" I screeched. "Abuse me some more! I'm your little cunt!" Ann slammed the dildo all the way up my ass. It felt as if she'd pushed a button deep inside me for the first time. I felt humiliation, pleasure and pain all at once. My cock swelled. Ann slowly pulled back until the dildo was a half cunt hair from leaving my ass entirely. Breathing heavily, she paused. I knew something violent was coming. My fingers balled into tense fists. And then... Nothing. Ann just sat there with the tip of the dildo barely inside my bunghole. I relaxed my hands. It seemed that Ann had decided to show mercy. I started to turn my head to look back at her. "Thank you, mommy, for sparing my ass--," I started to say. Ann hit me again, her toy prick blasting inside of me like a nuclear bomb. "Whore!" she yelled. My body shuddered. Ann withdrew slowly. She paused and pounded me again. "Cunt!" And again. "Twat!" And again. "I fucking hate you!" Ann yanked the dildo out of my ass. With astounding strength, she grabbed me by the hips and rolled me onto my back. The bed shook. I thought the head board was going to fall off. I looked up at Ann. Her brow was furrowed. She drew back her arm and smacked me across the cheek. "You are a piece of shit," she said. My cock was ready to explode. Ann dropped down and took my entire schlong into her mouth. Her head bobbed three times. I couldn't hold on. Our eyes met as I shot my load. I'd never cum so hard in my life. I must've sprayed a gallon of goo. Ann took every drop and held it in her mouth. After sucking the last drop from my pecker, Ann pulled herself up until her face was even with mine. Her deep, brown eyes blazed with hatred. Like a dam ready to burst, her sealed lips held back my jizz. I knew what was coming. "Do it," I whispered. Ann drew a deep breath through her nose. As her chest rose, I opened my mouth and closed my eyes. The dam burst. Cum splattered all over my face. I felt it running down my cheeks and trickling down my neck. Some of the salty mess landed on my tongue. I closed my mouth and swallowed. The jizz effortlessly slid down my throat. When I opened my eyes, Ann's face was still there, glaring at me. She rubbed the goo into my face and then made me lick the palm of her hand. "You fucking disgust me," she said. I felt humiliated-- and loved it. I didn't want it to end. Ann wasn't about to let it. She went to the phone on the nightstand and picked up the receiver. She dialed a few numbers, paused and then said, "Yeah, we're ready. Send the first one in." The knock at the door came almost instantly. "I hope you're ready for some punishment because you're about to get it," Ann said. "There are five perverts next door. Each one gave me $500. Know what that buys them?" I shook my head. "Ten minutes with you," Ann said. "Anything they want." She opened the door. A dark-haired beefcake of a man stepped inside. His biceps strained the sleeves of his black T-shirt. The lump in his jeans extended most of the way down his thigh. He looked at my face and nodded. "Mmmm," he said. "I like it." Ann went to the overnight bag on the desk and pulled out a video camera. She flipped open the side viewer. "And don't forget," she said, "with your purchase today, I'll send you a souvenir video for free." Beefcake smirked. "Cute," he said. The guy grimaced at me. He looked like a lion three hours before feeding time. And I was his prey. I shuddered. "On your knees, bitch," Beefcake said. I slid off the bed, took two sexy steps and dropped to my knees in front of him. Beefcake unzipped his jeans and hunched over to push them to his ankles. He wasn't wearing underwear. His cock almost smacked my chin when he stood up. As a former football player, I've been in a lot of locker rooms. But I've never seen a thick-a-saurus quite like this. The guy had at least nine inches. I wrapped my lips around the head and slowly slid my head down the shaft. I made it about a third of the way down before my mouth was full. I pulled back and inhaled deeply through my nose, preparing for another dip. "Don't tease me, cunt!" Beefcake yelled. He grabbed the sides of my head and thrust his whole salami into my mouth. I gagged. But the guy showed no mercy. He pulled back and rammed me again. "Take it, bitch," he said. I loosened my throat and decided to let him do whatever he wanted. I had no choice anyway. The guy relentlessly and repeatedly forced his cock into my mouth. I made sure to keep my teeth out of the way. Every time he thrust himself forward, my nose dipped into his curly, black pubic hairs. He smelled like Polo cologne. Beefcake didn't last long. After about 30 strokes, he pulled out of my mouth and aimed his prick at my face. I threw back my head and opened my mouth. The guy either had terrific aim or was incredibly lucky. Almost every drop splattered across my tongue. When he finished, I sealed my lips and swallowed. The guy pulled up his pants, pivoted and walked out of the room, slamming the door behind him. Beefcake didn't even say thanks or good-bye. "Another satisfied customer," Ann said. The phone on the desk rang. Ann picked it up. "Hello," she said. After a pause, Ann nodded and said, "OK, consider it done." She hung up. "The next guy doesn't even want to see your face," Ann said. "He wants you on the bed with your asscheeks spread." I climbed onto the bed and got in the doggy-style position. Burying my head in a pillow, I used both hands to spread open my buttcheeks. Ann got the tube of lube and put a dab on her index finger. She worked the lube around the entry to my bunghole. Three hard knocks at the door shook the room, as she put the cap back on the tube. Ann rushed to answer. I heard the door swing open and bang against the wall. Short, quick footsteps came toward me. The door closed. I heard a swift swishing as the client's pants fell to the floor. The headboard banged against the wall as the guy pounced on the bed. An iron grip fell upon my hips. He pumped himself inside me all at nice. I never saw his meat rod, but it had to be at least as long as Ann's dildo. The guy fucked like he was mad at something. He took long, punishing strokes. Each one was harder than the last. The best part was that he never made a sound. Not a single grunt or moan. It was like getting fucked by a serial killer. Some people might find that creepy. Not me. My prick felt like bursting. But I held back. I knew the guy was about to cum when I felt him shake. He pulled out and blasted a load on my back. It was a big one. The jizz ran down my spine and dripped down my buttcheeks. There was a silent pause. Then the guy snapped his fingers twice. "Oh," Ann said. "You want me to clean him up? OK." Ann dragged her tongue across the small of my back, smacking her lips dramatically as she lapped up the guy's jizz. She worked her way to my ass crack. Ann didn't shy away from it. To the contrary. Her licking intensified as she buried her face into my upper crack and then made her way down. Pausing at my bunghole, Ann spread open my cheeks with her fingertips and dug her tongue inside me. My cock felt like bursting again. But she pulled out before I came. "Time's up," she said to the customer. I heard him pull up his pants and walk to the door. When it shut, I flipped over on my back. Ann looked at my boner and shook her head with a smile peeking out the corner of her mouth. "Fuckin' weirdo bitch," she said under her breath. The phone on the desk rang. Ann picked it up. She nodded a couple times and said, "Yeah. It's your money. You can do whatever you want." Ann hung up and went to the door. "Get ready," she said. "Because here comes the grand finale." Ann didn't even wait for the knock. When she swung open the door, three guys stepped in. They lined up along the edge of the bed. A guy in a Brooks Brothers suit glared at me. A blonde surfer dude smiled eagerly. A dark-haired Latino in tight jeans licked his lips. Ann aimed the video camera at them. "Go to it, boys," she said. "The clock is running." No one needed to be told twice. The three of them had a coordinated attack that they'd clearly planned before coming in the room. They flung clothes into the corner and leapt on the bed. Brooks Brothers hoisted my legs above his shoulders and pressed his cock into my asshole. I grunted involuntarily as his meat filled my pipe. The Latin guy kneeled next to my head to my left. Surfer boy did the same to my right. They pointed their cocks at my face and started stroking themselves. Brooks Brothers was working hard. He furrowed his brow as he plowed my ass. A trickle of sweat dripped down his temple. It was my first time taking cock in the missionary position. I liked it. I knew my legs would be sore the next day, but the guy's dick was hitting a special place inside me. A cum volcano bubbled inside me. There must've been one inside the Latin guy, too. He came first, erupting on my face in powerful spurts. The sight of cum dripping down my face triggered a chain reaction. The surfer guy popped next, adding to the mess on my face. As I licked the salty jizz off my lips, Brooks Brothers pulled out and dropped his load on my stomach. Cum dripped down my cheeks and pooled in my bellybutton. Brooks Brothers fell back on the bed. "Fuck," he said breathlessly. Ann handed the camera to him and flopped onto her back next to me with her legs open. "Fuck me," she said. Brooks Brothers aimed the camera at me as I rolled onto my stepmother. She guided my prick into her hot, wet pussy and squeezed my titties as I began slowly pumping her. Cum dripped off of my face and splattered onto her cheeks and nose. Ann opened her mouth to catch the drops on her tongue. I lowered my head to give her a long, slow kiss. As soon as our tongues met, I shot my gook. Her pussy accepted it like a hungry mouth. Time no longer had any meaning. Our tongues wrestled, as cum flowed out of me. After I squeezed the last drop out of my prick, Ann pushed me off of her. She sat up and pointed at the three clients. "You three got the bonus plan," she said. "But time's up." They put on their clothes and scampered out of the room. When the door closed, Ann went into the bathroom to clean up. I did the same when she finished. I threw my bra in the garbage and put on my t-shirt and jeans. "Let's go," Ann said. We drove all the way home without saying a word to each other.