Letters to Penthouse XXXII Read online

  “Then you should have gone at lunchtime! Or last week. Great job. Well, I’m not eating this crap,” she said, opening the box and perusing its offerings. She took one chocolate and held it up to my lips. I dutifully opened wide, and she pushed it in. I chewed it, feeling its gooey cherry center exploding in my mouth, though it tasted bitter, not sweet. Then she upended the box and dumped all the chocolates on the floor. “That’s what I think of your ‘gift,’” she said. “Clean up that mess, put these flowers in a vase, and then get yourself downstairs,” she said harshly.

  I cringed at her tone but was thrilled by her words—the basement was where our home dungeon was. She stalked out of the room, and I hurriedly gathered the remaining candy, throwing it into the trash, then put the flowers in water. By the time I made it downstairs, my cock was hard with anticipation. When I saw her holding a red suede flogger, I knew I was in for a thorough punishment—one that I craved 100 percent. She lightly whacked the toy against her palm. “You’re overdressed—strip!” she ordered, and I did, presenting my naked body for her inspection.

  I heard a jangling sound and realized she was planning to rig me up by my wrists and ankles, securing me in place so I couldn’t move. I shuddered, my breathing altered by the excitement of being at her mercy. My cock stood up proudly as I stepped into place, raising my arms so she could secure them with the cuffs. She then did the same to my ankles. “That’s better. Now you’re ready to give me a little Valentine’s Day gift— your body,” she said approvingly, squeezing my ass as if testing melons at the supermarket.

  “Are you ready to offer up a proper gift to me?” she asked, as she delivered a stern smack on my ass.

  “Yes, Mistress,” I said, exulting in the warmth her slap had delivered.

  “Good,” she said, and then picked up the flogger. I heard it whizzing through the air right before I felt it land on my ass, the combined force of the soft strands creating a sting upon my flesh. She gave me a good whacking on the behind before moving down to an even more sensitive area—the backs of my legs. My upper thighs hummed as she whipped me there. Each time the flogger connected with my skin, my cock twitched. I had the choice of shutting my eyes, staring straight ahead at the wall, or looking down at my cock. I chose the latter, watching its firmness bob without being able to touch or stroke it.

  Then she moved her target up to my back. “I should be sitting in my favorite chair eating Godiva while you massage my feet,” she said as she swung the flogger. “But no, you had to go and ruin Valentine’s Day for me,” my mistress chastised me as she struck my strong shoulders, making my bonds rattle as my body shook. The combined effect of the flogger hitting my upper back and her words made my cock twitch with excitement. The heavy thudding of the flogger resounded in my ears and the arousing sensation of its impact swept through my body.

  My back was warm, but I knew it could take even more than my ass. “Are you sorry yet?” she asked, which was her way of finding out if I wanted to continue.

  “I couldn’t help it!” I whined, knowing this would cause her to strike me harder. She did, unleashing her annoyance directly onto my backside, then she switched locations. The flogger seamlessly stroked one shoulder and then the next, while she twirled it expertly. From experience, I knew she was wielding the whip in figure eights. I’d seen her practice these motions and knew it was a sight to behold. I was grateful for my bonds, as they let me absorb her blows without causing her to miss her target.

  “Count to fourteen,” she ordered, another reference to my failure to meet the holiday’s standards. She flogged each ass cheek fourteen times, while I said each number, followed by, “Thank you, Mistress.” She dropped the flogger by my feet when she was done and pressed her body up against mine. Her fingers wrapped around my cock and I moaned.

  “What do you have to say for yourself, slave?” she asked.

  “I’m sorry, Dorothea. I should have known better and been more prepared. You deserve better, especially on Valentine’s Day. I’ll do anything to make it up to you,” I said in apology.

  “Indeed you will,” she said, taking her hand off my cock in order to release me. “Now lie down on the floor!” Her voice retained its edge, even though we were about to fuck. We have a standing joke about which positions we like—I love being on top, and so does she. Most of the time, however, we do it her way, and if I’m being punished, I’m always on the bottom. But on my birthday and special occasions, she’ll let me climb on top of her and slam my cock inside her. Since she outweighs me by thirty pounds, when she’s above me she can push my hips down and keep me in place—not that I really mind, because it turns me on to please her.

  I lay down, shaking with excitement at finally coming close to my beloved’s pussy. She roughly got on top of me and sank down onto me, holding the base of my cock and moving around, as if I were nothing more than a sex toy to her. I know I’m more than that, but we both like it when she occasionally acts like I’m not. No matter what, fucking her feels amazing and knowing that she was getting off because of my cock provoked me, too. “Don’t come until I do!” she barked, her eyes shut as she focused intently on her own pleasure. I didn’t say a word. I simply lay back and enjoyed the feel of her pussy clutching my dick tightly, until I heard her breath start to come in fast little pants. Her cunt got tighter and tighter, until I felt a rush of wetness surround me. “Okay,” she said quietly, and I bucked up into her. It only took a few humps before I was shooting my hot come deep into her hole. We shared a look of passion as we recovered.

  Then she immediately snapped back into her dominant role. “I expect you to make this up to me tomorrow,” she said before rising and heading to take a bath—alone.

  The next night I went all out, getting an extremely expensive package of truffles, mints, solid chocolate, and assorted treats. I even got her some chocolate-covered strawberries—nothing is too good for my wife. I presented the package to her and she regally accepted it, opening the boxes and savoring a piece from each. I looked on with my mouth watering. I was hungry for chocolate—and her. But instead of sharing her bounty, she closed the boxes and locked them in her desk drawer. “Next year, if you get me my gift on time, I’ll share them with you,” she said. Dorothea did, however, let me taste her sweet pussy, and I consider that more than a fair trade-off. I’m lucky to have such a demanding wife, and I will do everything I can to serve her faithfully in the future.

  —Mr. Floyd S., Washington, D.C.

  Chills and Thrills for a Cranky Gal on a Sweltering Indian Summer Night

  Summer wouldn’t seem to leave this year. Now, don’t get me wrong, I enjoy sunshine as much as the next girl, but after a sweltering July and equally brutal August, I was ready to move to the Antarctic. And then, just when I thought the haven of a crisp autumn was approaching, Indian summer swooped into town.

  My boyfriend, Will, came over to visit one sticky night last month and was greeted by more of my complaints. I was in a really bitchy mood since I came home and discovered that my air conditioner had stopped working. He sat at the kitchen table, observing my plight and my ranting that someone was going to die if the radio station played “Summer in the City” one more time. Wordlessly, he stripped off his T-shirt. He leaned back in the chair, his skin glowing in the moist heat. As my grumbling escalated, he tried to appear concerned but couldn’t help laughing at me. This got me incensed.

  “I’m suffering and all you can do is laugh,” I said, exasperated. “You think this is funny.”

  Will looked me straight in the eye and said, “I think that you need to cool down.” He jumped out of his chair and in one smooth motion threw me over his shoulder. I kicked and pounded on his sweat-slicked back, demanding that he let me go. Once I realized that he was heading for the bedroom, my struggle became more playful. Will dumped me on the bed and climbed atop me, straddling my hips.

  “What are you doing?” I asked, giggling.

  “You’ll see soon enough,” he said with a smile. Will s
tretched to reach the corner of the bed. His chest was inches from my face. I sat up and flicked my tongue across a tiny nipple. I turned my head to see what he was reaching for and saw him grabbing the belt from my bathrobe, which was hanging on the headboard. Will grabbed both my hands and pulled them over my head. I felt the cool metal of the headboard on the insides of my wrists, as he brought them through the bars and snugly tied the terrycloth belt around them.

  “Don’t go anywhere,” he warned. “I’ll be right back.” Will climbed off the bed and left the room. I heard some noises coming from the kitchen but had no idea what he might be up to. The anticipation of what was to come, and the new thrill of being bound and helpless, had my heart racing. I fidgeted in my bonds, tapping my fingernails against the headboard. Will returned a few minutes later and placed a metal bowl on the night table.

  Keeping his eyes locked on mine, Will slowly undid his button fly and dropped his jeans to the floor. My eyes immediately focused on his cock, which was beginning to swell. I squeezed my legs together nervously. “So whaddaya got for me?” I asked in a whisper.

  Will didn’t answer as he straddled me once more. With my legs pinned underneath him, I couldn’t escape. “I said you needed to cool down,” he reasoned as he reached into the bowl and held up a dripping ice cube. With the other hand, he pushed my T-shirt over my breasts and pushed down the cups of my bra so my flesh spilled over the lace. A hiss slipped through my teeth as Will traced the ice around one of my pink nipples. I tried to squirm but his weight kept me in place. Whenever the cube made contact with my flesh, my hips bucked from the icy thrill. My nipple quickly became numb. Drops of water dripped down my breast and tickled my armpit. He moved to my left breast. Soon both nipples were tight and as firm as pencil erasers.

  Will took his time circling my left nipple with the ice. When he finally sucked it between his lips, I gasped at the burning sensation of fire and ice. His hot mouth soon revived it from its desensitized state. Coaxing my nipple back to life, he moved from simple licks to harsh bites. His sharp nips made me yelp with the sweet agony. After his temperature treatment, my nipples seemed extra-sensitive.

  Will climbed off me. He grabbed the waistband of my bicycle shorts and pulled them over my hips. He brought the bowl to the bed and placed it next to me. I heard the floating cubes clink against the metal. Will dipped his hand into the bowl and scooped up another piece of ice. “Open your legs, sweetheart,” he whispered. I bent my knees and slowly spread my legs for him.

  His eyes were locked on my pussy. A thread of wetness was already seeping out of me and trailing down the cleft between my ass cheeks. I held my breath as I waited for his touch. Will circled my clitoris with the ice. My hips jumped and I yanked at my bonds when it made contact. “Don’t move,” he commanded quietly. I struggled to obey him.

  Cries of rapture escaped my lips as this precious torment continued. Will was rubbing the ice directly on my clitoris and I moaned. He kept this up for a few more moments, until he was satisfied with my reactions. He then moved downward, rubbing the ice along my pussy lips. He nudged them open with a finger. “Ahh, Will, no,” I whispered, as I felt the ice cube slip inside me. He didn’t listen to my pleas, because he knew that my gentle protests were part of the game.

  The chill of the ice was radiating in my womb. Will leaned down and sucked the icy nub of my clitoris between his lips. He rolled his tongue around it, warming it with his mouth. My hands clasped the bar that I was tethered to. The melting ice and my love juice soaked the mattress. Each lap at my sex increased my arousal and added to the wet spot underneath me. His panting breaths fanning my cunt proved that he was just as turned on as I was.

  He looked up at me and growled, “God, I want to fuck you.”

  “I won’t stop you,” I joked breathlessly. Will climbed on top of me, sighing as he slipped his cock into the cool depths of my cunt. For a moment, he just lay there, savoring the feel of my chilled pussy. Then he began fucking me slowly, picking up speed until he was pounding into me. It may have been the combination of Will’s wintry touch and my being his bound captive, or that Will is the greatest fuck I’ve ever had, because with little effort, his talented cock soon brought me to a screaming orgasm. Before I could catch my breath, he jammed his cock inside me, filling me with his creamy come.

  I never did get the air conditioner fixed, but that’s okay. Will came up with more than enough ideas to help me keep my cool. I can’t wait to see what he does this winter to keep me warm!

  —Ms. Madeline D., Arlington, Virginia

  When He Misbehaves, His Punishment Comes From Two Harsh Mistresses

  Mistress Donna had been dissatisfied with my performance as her slave/husband. She kept hinting that I hadn’t been living up to my end of our agreement. I wasn’t giving her enough sex and was generally failing in my duties. Since I live to please her, I wanted to do anything I could to make it up to her.

  As it turned out, my “punishment” wasn’t exactly a huge hardship for me. “It seems you can’t manage to follow simple orders, my slave,” she said, staring down at me as I knelt before her, “so I’ve called in some reinforcements. My friend, who you’ll address as Mistress Jessica, is going to help me discipline you. Now go upstairs and get into your cage,” she concluded, sweeping by me.

  I scurried upstairs and got into the cage she’d bought especially for me—it’s extra large, and I can move around, but when I’m inside it, I’m not to make a sound and she can do with me as she wishes, which I find incredibly exciting. I was extremely curious about my new mistress, but kept quiet as I tried to be obedient in my cage. Finally, the moment of truth arrived. Mistress Donna came in and let me out, fastening my “Slave Jerry” collar around my neck and attaching a metal chain that she used to lead me down the stairs.

  The vision greeting me at the foot of the stairs made me catch my breath. Now, Mistress Donna is beautiful: tall, brunette, perfectly curvy and pretty. But Mistress Jessica was at least a decade younger, perkier and more petite, with bright red hair, a pierced nose, and a beautiful tattoo of a mermaid running down her left thigh. She wore tall black heels and a black teddy with garters and black stockings. She lit a cigarette and Mistress Donna instructed me to hold out my hands to catch the ashes. I cupped my palms, peering up into the sparkling green eyes of this second woman who would be dominating me. She took a long puff, then blew out the smoke in a haughty gesture. Years of practice have gotten me so accustomed to this behavior that I didn’t even flinch. She blew a few more puffs in my direction, then grabbed me by the ear, tugging me upward. With her in her heels, we were about the same height, but I felt tiny and submissive next to her inherent superiority.

  Jessica dug her fingers into the space between my neck and the collar, keeping them resting there as I swallowed heavily. “Slave, I understand you’ve been very bad. Well, I’m going to make sure that you learn a lesson that you won’t soon forget!” I was already quivering at the tone of her voice, anticipating her sensual dominance of me. “Do you understand me?” she shouted loudly, right in my face. “Yes, Mistress,” I replied quietly, bowing my head.

  “You’ve been taking your mistress for granted and it’s high time you be punished for your neglect,” she said, grabbing my leash as she propelled me forward. I had to hurry to follow her, but watching her firm, sexy ass and flaming hair got my cock hard. I’d be lucky if these two would even let me masturbate at the end of our scene after being such a bad boy.

  Mistress Donna was right behind me, and she’d somehow picked up her riding crop, slapping my ass with it as we made our way upstairs. When we got to the dungeon room, they sat me down on a padded leather seat and used a variety of ropes to tie me to the chair, making sure I couldn’t escape—not that I wanted to. Then they teased me by rubbing each of their bodies against me. I was still dressed, and my cock was pressing urgently against my zipper, my arousal almost painful in its intensity.

  The sight of these two gorgeous women intent on teachin
g me a lesson made me want to promise to do anything if they’d only let me come. Mistress Jessica leaned down and pinched my nipple, then turned her head so she could suck on Mistress Donna’s. My open legs gave them access to my cock, but they chose to ignore it. I heard my mistress moan and longed for a taste of any part of her, but she moved away when I grunted. “A slave is not entitled to sex with his mistress, he must earn it,” said Mistress Jessica as she sat down on the bed, facing me, and beckoned Mistress Donna to join her.

  They made me watch, unable to move, as they devoured each other, hands tangling in each other’s hair, mouths sucking on each other’s breasts, as they battled for supremacy. Finally, Mistress Donna gave in and let Mistress Jessica pin her to the bed, giving me a perfect view of my mistress as I’d never seen her before—her body bucking under her friend’s practiced fingers. One hand held her wrists down and the other parted her pussy lips and made her jerk and gasp. I was amazed—and as horny as all get-out. As Mistress Jessica probed my mistress’s cunt until she cried out in pleasure, my hard dick struggled to get free. When Mistress Donna had caught her breath, she looked over at me with a smile. “See how easy it is to give your mistress a good fucking when she needs it?”

  I moaned, overwhelmed with the need to touch or be touched by at least one of them. Fortunately, they took pity on me and untied me, but my exciting ordeal wasn’t over yet. When my hand discreetly moved to stroke my cock through my pants, Mistress Jessica slapped it away. “You haven’t earned the right to touch your cock just yet,” she said. “Go face the wall and place your hands above your head.”

  I’d gotten used to Mistress Jessica’s voice ordering me around. It felt even more special to have two mistresses commanding me rather than just one. Mistress Donna warmed me up with several smacks to my ass, her breathing becoming heavy and more erratic as she hit me, then Mistress Jessica moved in. She ordered Mistress Donna to undo my pants and lift up my shirt. With my pants and boxers down at my ankles, she flogged me, letting the suede strips of her whip bite into my skin, striping my shoulder blades, then my ass, then the backs of my thighs. I maintained my position as best I could, my naked cock pressed against the wall. The beating felt so good I thought I might come without even touching my penis directly, which had never happened before, but if I did, I knew there would be a price to pay.