Letters to Penthouse XXXII Read online

  Mistress Jessica stopped, leaving my backside feeling like it was on fire, the waves of accumulated heat adding to my arousal. “Turn around, slave, and show your obedience to your mistress,” she said. I did, looking up at a naked Mistress Donna. “You shall begin by kissing her feet and work your way up her body,” she said, forcibly grabbing me by the hair and shoving my head down to Mistress’s beautifully pedicured toenails. I was so grateful to have some flesh-on-flesh contact with my beloved Mistress Donna that I devoured her tiny toes, shoving my tongue in the crevices, then taking each one individually into my mouth. I kissed the top of her foot and polished each heel and sole with my tongue, which she mashed down against my mouth.

  Then Mistress Jessica grabbed me again, directing me to glide my tongue up Mistress Donna’s long, smooth legs until I reached her beautiful pussy. There, I once again feasted, and I didn’t need an ounce of instruction from anyone in how to please her. My cock was going crazy but I tried to ignore it, content in the knowledge that this time, I was doing what I was put on this earth to do—give pleasure to the woman who controls, cares for, and possesses me. My tongue knew exactly what to do as it slid into her wet tunnel, arching upward, then swirling around to stroke her special spots, before easing back to focus on her clit. Soon she was moaning and her juices rained down on me. I buried my face in her cunt to catch all of her nectar. I stayed there until her shivers subsided, and I’d swallowed a good amount of her sweet cream.

  “Very good, my slave,” she said, patting me on my head. “Now get back in your cage while I say goodbye to Mistress Jessica, and maybe tomorrow I’ll let you relieve yourself.” I’m happy to say that after a night spent with one serious case of blue balls, Mistress Donna let me fuck her into oblivion the next morning, and any problems of the sort that got me in trouble have been swiftly eradicated. However, that doesn’t mean I don’t mess up on purpose once in a while, because with my mistress, the punishment is often quite rewarding in and of itself.

  —Mr. Jerry K., Providence, Rhode Island

  What This Sub Wants in His Next Domme

  I’m a forty-three-year-old, healthy, successful businessman, and I’ve yet to find the right domme to give me what I crave. I’ve come close a few times, but my past lovers never quite hit the mark, so to speak. They’d be interested for a few weeks, then revert back to wanting me to make all the plans, take charge in the bedroom, and generally have the upper hand. They couldn’t understand why I got off when they topped me.

  So I’ve spent the last few years mapping out exactly what I need in a mistress, so that when I meet her, I’ll know she’s the one. Here’s what I imagine our life will be like, especially when I’ve misbehaved. She writes out a list of rules for me at the start of our relationship. I’m to follow them to a tee, and if I don’t, I will be punished. She has various forms of discipline, but the one she likes best is to make me strip naked in front of her, then put on a pair of tight panties. They are not hers, but my own—a special pair she got for me that traps my cock tightly. However, I’m so turned on that my dick swells inside the panties, making my bulge visible.

  While I have the panties on, she makes me get down on my knees in front of her. I don’t need much prodding because I love servicing her, but rather than having me lick her pussy, she teaches me the art of cocksucking. She makes me watch video after video where girls take guys’ huge dicks down their throats. “Do you see that girl right there?” she asks, pointing to the one who is swallowing the largest dick. “That’s gonna be you—but it’s my dick you’re gonna be deep-throating.”

  I groan upon hearing her words because sucking a cock, whether another guy’s or a woman’s pseudodick, has always been something that’s made me hard. I’ve never had the courage to tell anyone, even my mistresses, because I thought it might be pushing the envelope. But with my dream domme, it’s not only permissible, but a plus for me to want to learn to give the perfect blowjob. Watching so many women get their mouths stuffed full of cock has me so hard I’m aching, but my mistress doesn’t let me touch myself.

  Instead, when I’ve taken in about as much on-screen fellatio as my brain can handle, she reappears wearing nothing except a gigantic black dick strapped around her hips. As turned on as I am, for a moment I hesitate. I want to suck it, but will I be able to? I decide that I’m up for the challenge, especially since if I want to stay in this relationship, I’ll have to at least give it a try. I know that if it really is too much for me to handle, my mistress will ease up, but I want to take the whole thing for her. She keeps the porn playing, but mutes the TV. “I want to be able to hear your moans as you swallow this big cock—I got the largest one they had, just for you!” she exclaims. She looks so happy as she lowers herself down onto the couch and gets comfortable.

  As I kneel before her on the carpet, my hard cock presses against my stomach within the confines of the panties. I lean forward, open my mouth, and take my first taste of dick. Even though hers is made of silicone, it’s warm and I could swear it tastes like her. Maybe that’s because I’m so near her precious pussy. Guided by her fingertips nudging the back of my neck, I find a way to open up and take the entire monster cock down my throat. It feels good and triggers something in my body that makes my dick even harder. I worry that I might come in the panties, which is against the rules, but I don’t care as I slide back up, letting the smooth head deliver unfamiliar sensations to my mouth.

  She clearly likes the way I suck her cock because she keeps moaning and thrusting up into me. “You look so pretty in those panties, almost like a girl, except you have that big hard-on. Maybe I’ll have to teach you how to hide it better in the future,” she says, making said erection jerk wildly in my panties. I ignore it though, focusing on the cock in my mouth as if it were alive, liking how it gets easier to slide up and down the wetter the toy gets. I put my whole body into my efforts, wanting to please her—and not just because that’s part of my job requirements.

  She instills in me a desire to be my best self, to be her ultimate servant, but also to be the best person I can be. Even while I’m down on my knees sucking her cock, I feel more proud of myself than ever and know that positive energy will transfer to the rest of my life. When my colleagues tell me I look great, like I’ve lost weight, I smile a secret smile and laugh it off, knowing that my inner glow has come from my new role and my success as her slave.

  Whereas I had initially thought the cock was too big, by the time she’s come from the base of her dick rubbing against her clit, I’m already longing for a bigger one, one that will truly challenge my hungry mouth. I don’t dare express this to her, lest she take it as criticism. I will wait for her to decide if and when I should advance in the rungs of service.

  My perfect mistress will also give me household chores and watch over me to make sure I’m doing them right, and correct me when I’d do wrong. She will make me go outside to rake the yard, wearing nothing but a tight, red thong—one that leaves nothing to the imagination. She will inspect every inch of her property and haul me over by the scruff of my neck to point out my errors. She won’t care that others can see into our yard and may wonder about the nature of our relationship, because she’s so secure in the dance that the two of us do—mistress and slave, domme and sub.

  In return, I will get hard at the mere thought of her stern gaze, her commanding bark, or the click of her sharp, spiked heels on the floor. She will hover over me in my dreams, and my heartbeat will quicken when I think she has spied me doing something naughty—even if I’ve done nothing wrong. I will always strive to improve, for her sake and my own, and it will make both of us happy. Our house will always be spotless because she will demand that I get down on my hands and knees with a scrub brush—or even a toothbrush—in order to make every surface absolutely spotless.

  Her dominion over my life will not be contained to just the bedroom or our household. She will call to check up on me at work, offering little suggestions about what I should eat for lunch or
what kind of shoes I should purchase. I know that when I please her by performing these tasks, she will sometimes take my cock and slam it inside her slick, perfect pussy. However, she will save fucking for special occasions to make me truly appreciate her cunt, even though it’s practically all I think about, night and day. She will often climb on top of me when she’s awoken, demanding that I start the morning with my tongue inside her hole.

  “You’re such a good little pussy licker and look so cute in your panties. I should really let all the wives of your coworkers know what they’re missing out on,” she’ll say.

  She’d never follow through with that sexy threat, but she taunts me with the idea of sharing my secrets with the world. She’ll snap her fingers, and I’ll instantly harden. She’ll trail one long fingernail down my arm when we are in the car and laugh when she sees my erection sprout up. Best of all, I’ll know that she loves me for my truly slavish devotion and wants what’s best for me—to be under her control, utterly and completely. She is worth waiting for, and if any women who fit this bill are reading this, I would love to hear from you. Until then, I’ll be waiting and dreaming about my perfect mistress.

  —Mr. Dennis K., Little Rock, Arkansas

  Girl Has Beginner’s Luck at Intro-to-Kink Class and Gets a Very Hot Lesson

  Last week, my best friend, Jane, convinced me to go with her to an introduction to S&M class. It’s something that she’s wanted to try for a long time, and she wanted some company. It didn’t sound like my cup of tea, but I’m willing to try anything once. When we got there, we found twenty people seated in a circle. Contrary to my expectations, the students looked pretty normal, not dressed in the leather and chains I was expecting.

  The instructor, Carl, was a nice guy who patiently explained some of the basic activities of S&M, how to do them safely, and why some people got off on doing them. I could feel Jane practically bouncing up and down in her seat with excitement, while I took it all in, finding myself becoming more and more intrigued. When Carl was done talking and answering questions, he had us all move around the room to different stations where we could experience a number of kinky activities, from bondage to hot wax to spanking. I turned to Jane, and she looked back at me with a huge smile on her face before scampering off to get spanked. I wandered over to the bondage station and watched a girl get strung up to a cross, her arms above her head and her legs spread, each limb shackled to the wood. My nipples hardened as I watched her pretend to struggle, trying in vain to escape her bonds. It was her boyfriend who was leading the demo, and they’d clearly done this many times before. When he tugged her hair, then whispered something in her ear while sliding his hand between her legs and rubbing her pussy, she blushed.

  I was amazed not only at the variety of offerings, but by my own reaction. I’d gone to the class on a lark, not really expecting to learn much or be too engaged, but all of a sudden, I wanted to try everything! Watching the woman struggle helplessly—clearly enjoying herself and getting off on being bound—unleashed something inside me. And I knew the man I wanted to do the job! I’d noticed a young, muscular guy sitting in the back checking me out. He was holding a small paddle in his hand that he kept tapping against his palm while gazing around the room, as if searching for the perfect victim. “Me, me, me!” I wanted to cry, but instead, I gradually sidled over to him as we watched the same bondage demonstration.

  After a simmering minute of intense stares, he stuck out his hand and said, “I’m Rob. I’m known around here as the resident top. You look like you’re pretty new to the scene, so if you have any questions, just ask.” On the surface, his words were innocent, but his voice conveyed his very kinky interest. His eyes roamed all along my body while his fingers slid up and down the small leather paddle, and I was smitten once again.

  “Actually, Rob, this is my first time here, and I’m very curious to try out everything. Would you be interested in showing me the ropes, so to speak?” As I said it, I stepped closer and placed my hand over his, easing the paddle behind me so it rubbed against my ass.

  “Gladly,” he said, locking both my wrists in his hand and escorting me over to a corner. I gave Jane a thumbs-up sign, stripped out of all of my clothes but my underwear, and settled myself against the wall. “First, I like to start with a warm-up,” Rob said, and he began to knead my back and my ass, squeezing deeply with his big, strong hands. Once my body felt like it had melted into the wall, he spanked me with his hand. It didn’t at all hurt like I thought it would; I felt a sharp sting the moment his bare hand connected with my skin, but that was immediately followed by a fabulous warmth that radiated throughout my lower half and ignited delicious feelings inside my body.

  His hand was firm yet somehow soft, and he rapidly built up his tempo, explaining what he was doing every step of the way. “Now your ass is getting a little redder, and I’m building up your tolerance so you’ll be able to enjoy the paddle even more. Some implements deliver a deeper impact, more of a thud, while my hand and this little leather slapper provide more of a sting.” His breathing was also getting increasingly heavy as he exerted more and more effort. He moved from side to side so his hand struck me evenly. I felt myself getting wet and started to worry that even with my panties on, my pussy juice was going to leak down my leg.

  When he began using the paddle, I felt the difference immediately. It was firmer and made my ass sting more, but it also made my pussy twitch. I started fantasizing about Rob’s cock, wondering how big it was and how it would feel inside me. Carl had explained that some people simply like to be spanked, and some like to combine spanking and sex; I could tell from my throbbing cunt that I definitely fell into the latter group. I must have let out a little moan, because Rob leaned down and said to me, “You’re a natural at this, Selma. We’re going to have to make a private play date so I can go even further with you.”

  I trembled at his words, and even though we couldn’t have sex right then, I was getting completely turned on. I’d forgotten about Jane and everyone else in the room and was focused solely on what Rob was doing to me. After a few more firm smacks, he stopped, rubbing my sore ass to soothe the sting. “Now I’m going to tie you up and have some fun,” he said, his voice taking on a serious tone. He rustled through his large black bag before pulling out a coil of white rope. Another tremor passed through my body; I’d never been tied up before, but all of a sudden I remembered once fantasizing about being bound and helpless while a hot stranger had his way with me. Rob said it was okay to get totally naked, and I was so turned on that I did so immediately. Rob placed the rope between my legs, tugging upward as he tied intricate knots all around my body. He looped the rope around my breasts and tied it behind me, so my tits jutted out. Then he laid out a yoga mat and had me lie on top of it, before he brought out a candle.

  “I’m going to light this and drip the wax onto your body. It’s made especially for this purpose and smells like vanilla. Just wait, you’ll love it.” I was a little nervous, but the moment the first drop landed on my skin, I was in heaven. It was hot, but cooled off almost right away, clinging to my skin. The scent wafted through the air while Rob moved all around me, creating a pretty pattern on my skin. I looked up and saw that a crowd had formed around us, eager to see what was happening. Somehow, I’d become the class’s main attraction! He used the same slow build-up process he’d used to spank me, and I found that I reveled in not being able to escape. He’d placed my hands above my head and tied my wrists together, and the more I squirmed, the wetter I got. I watched as the wax fell from a few inches above me and splattered onto my skin. I grew to anticipate and even crave the sensation as the wax landed on my tender flesh.

  When Rob moved lower, hovering right over my shaved pussy, I almost asked him to stop, but decided instead to see how this latest sensation would feel. To my delight, the wax felt hot but arousing—the blood rushing to my pussy lips made me long to fuck Rob all night. He continued trailing up and down each leg until the candle was almost us
ed up and my body was covered in wax. He poured some onto my stomach, then rubbed it in. By then, his every touch was sending me closer to my orgasm. I knew we couldn’t start fucking in the middle of the room, but when he put down the candle, loosened the rope to give him access to my cunt, then brushed his fingers through my wetness, I moaned. With a few thrusts of his fat fingers inside my dripping-wet cunt, I was coming. My body curled into a ball as my pussy gripped his fingers urgently while I climaxed. I smiled when the room exploded in applause as he pulled his fingers out and sucked on them. He offered me his fingers to taste, which I gratefully did, dreaming of sucking his cock in the same way. My whole body tingled with arousal from what we’d just enjoyed together.

  “Wow, you’re quite the teacher,” I said to Rob, slipping him my phone number. “I definitely want to take you up on that private play date, sooner rather than later,” I told him, giving him a deep, sensual kiss.

  —Ms. Selma D., San Francisco, California

  A Personals Ad Leads Him to the Ideal Mistress

  Recently, I was totally bored and began reading my local paper from cover to cover. I soon found myself at the back, looking over the classified ads. My eyes were skimming the personals when I found one woman’s ad that caused me to pause and my cock to stir in my pants. It read: