Letters to Penthouse XXXXV Read online

  My face felt warm. He was inspecting me with the intensity with which I inspect the work by my team. Usually, I am on the other side of this sort of interaction. I think this is why I get so turned on being Aaron’s submissive. It is such a different sensation for me.

  Breakfast forgotten, Aaron pulled me onto the bed with him so I was on his lap, face-to-face. He stroked my breasts and then bent to suck my nipples. I could feel how wet I was getting. Aaron felt it, too, since I had no panties on and was straddling his body. I was definitely creating a damp spot on the crotch of his navy pajama bottoms.

  “What made you dress like this?” he whispered to me as he started to play with my clit.

  “I saw the apron in a catalog,” I told him, “and I couldn’t resist.”

  “And the shoes?”

  I couldn’t explain the shoes. They’d called out to me. I could never wear shoes like that to work. I’d had to buy them for home.

  “I want to fuck you from behind,” Aaron said, “so I can play with the ties on your apron.”

  Quickly, I climbed into position on the bed. Aaron stripped and got behind me. At first, he gripped my hips and slid his cock between my pussy lips, not entering me, simply getting the head and the shaft nice and wet. While he fucked my split, he played with the ties on the apron, exactly as he’d described. He arranged the strings to fall between the cheeks of my ass. That tickled, and I jumped, but Aaron kept up what he was doing. Then he parted my ass cheeks and let the apron strings dangle right against my exposed hole. I began to tremble. I love when Aaron plays with my asshole. The extra stimulation always makes me come so much harder.

  When I began mewling, desperate for some type of satisfaction, Aaron thrust his cock into my pussy, one hard, fast stroke, and then sealed his body to mine. My cunt muscles started to squeeze his dick helplessly. I wanted more. I wanted him to start pounding into me. Aaron would not.

  Now he lifted the strings and just danced the tips over my asshole. I could feel my backdoor clenching and unclenching, as if winking at him. I was helpless. I think Aaron liked the way my pussy was tightening on his rod as well, because he continued to tease and torment me, not fucking me, simply playing with me.

  The outfit seemed to really bring out a new side of Aaron.

  “You like that,” he said, stating the obvious. I wanted to say, “Yes, but I need more. I need you to fuck me.” Yet I knew that if I tried to rush Aaron, he’d slow down further. He doesn’t give me what I want when I ask. He always makes me wait.

  “Why do you like having your asshole played with?”

  I was glad he was fucking me from behind so he could not see my face. Talking like this is always embarrassing for me. “It just feels naughty,” I said, hoping that was enough of a confession for him.

  “It is naughty,” Aaron agreed, and he gently parted the cheeks of my ass, spreading me open. Things were going differently than I had expected. My dreams of simply being fucked in the apron were taking a turn toward anal. Aaron traced his thumb over my asshole, and then asked, “Where’s the lube?”

  I pointed to the bedside table. He reached over me to pull out the drawer and grab the bottle. Quickly, he lubed up my backdoor, taking extra time to slip his pointer finger inside me and give me a little fucking with the tip. I groaned and pressed my face into the mattress, really raising my hips up for him. Aaron now started to thrust his cock in and out of my pussy. But I knew he wasn’t doing that to get me off. He was lubing up his cock with my copious juices.

  Surprising me, Aaron pulled out and flipped me over. I was on my back, looking up at him, malleable as he hoisted my legs over his shoulders and parted my ass cheeks once more. We’d never had anal sex in this position before. I was flushed with heat, lust, and shame as he speared me with the head of his cock, grinding his way into my well-lubed asshole.

  “Your shoes are so sexy,” Aaron said, moving my legs so he could admire my heels while he fucked me. “And that little apron. I want you to wear this outfit all weekend. Just the apron, heels, and nothing else.”

  He was rocking in and out of me now, fucking my ass as hard and fast as he does my cunt. But he took pity on me and let one hand slip down to my clit, which he pinched and teased in rhythm to his thrusts. I realized I was holding my breath. I’d inhale, and then forget to exhale for several seconds. That gave way to a new breathing rhythm: panting. The pleasure was building—the sensation of having my ass filled and my clit stroked taking me higher and higher.

  Aaron said, “I am going to fuck the daylights out of you this weekend. After this, we’re going to shower off, and then I’m going to 69 with you. And then I’m going to fuck you out on the deck. By Monday, you’re going to be lost in a haze of lust.”

  I already was. I came as Aaron bucked hard and filled my ass with his load. And then I waited while he gently slid out of me, removed my shoes, and let me undo the apron. We went to the bathroom together to take a shower, and the whole time I thought of Aaron’s promises. I had tried to surprise him, but he’d turned the tables on me. Like any good dom will do.

  —Ms. Abby M., Portsmouth, Virginia

  Disastrous Dinner Party Leads to Punishment for a Clumsy Slave

  My girlfriends and I take turns hosting monthly dinner parties, and last month it was my turn. Our dinners are pretty standard affairs except for one thing: We’re all dominatrices. That means that in addition to the six of us, there are also six submissives present for every dinner. They’re always put to work, serving and cleaning up and refilling drinks, and they’re always on their best behavior. If they’re not, they know that they’ll be in trouble with not only their own mistress, but the hostess as well.

  Robert, my sub, has never gotten in trouble at another domme’s party. He knows that any mistake he makes will reflect poorly on me, so he’s always extra cautious when we’re out in public. The punishment he would receive if he ever embarrassed me in front of anyone, especially other dommes, would be severe. But when I had the ladies over for dinner the other night, Robert was less than the perfect servant.

  It started while we were setting up and preparing dinner. I was in the kitchen, checking on the roast, when I heard something break in the dining room. Robert slunk back in to tell me about it a moment later, apologizing profusely for breaking one of my wineglasses. I explained that he’d be punished for it after the party, but if he were on his best behavior for the rest of the night, I would take that into consideration.

  Ten minutes later, as I was in the bedroom putting the finishing touches on my outfit before my guests arrived, I heard a crash in the kitchen. When I got out there to see what was wrong, I saw a pot lying in the middle of the floor, all the vegetables scattered and mashed around it. Half my dinner was gone, and my guests were scheduled to arrive any minute. Robert was in hot water, and he knew it. He was crouched on the floor, cleaning up the mess, with his head bowed. If I had had time, I would have punished him then, but as I was reading him the riot act, the doorbell rang. While Robert stayed in the kitchen to finish cleaning, I went to get the door.

  Things went well once the guests arrived, and there were no other incidents as we dined and chatted. The night was slowly coming to a close, with the women heading home with their subs, until there were only two of us left—four if you count Robert, and Lana’s slave, Steven. And that’s when it happened. Robert was clearing the coffee cups and dessert plates when he bumped into Steve, who was picking up his mistress’s purse so they could leave. The tray Robert was holding went flying, causing coffee to spill on the living-room carpet and a piece of cake to land next to my girlfriend, missing her lap by a hair.

  Everything stopped at once. Mistress Lana straightened her skirt, stood, and led Steven from the room after saying a brusque good-night. Then it was just Robert and me.

  “How could you?” I barked. “You’ve been nothing but trouble all day. What do you have to say for yourself?”

  “I’m sorry, Mistress,” Robert said from the floor,
where he was trying to clean up the latest mess.

  I told him to finish tidying the living room and then meet me in the bedroom for his punishment. I was mad, but I also knew that Robert hadn’t meant to do any harm. I actually wondered if he’d made a fool of himself on purpose to get me to punish him. It had been a while since our last session. While I waited for him, I started getting out all my implements, from crops and floggers to whips, paddles, and cuffs. Robert was about to get the most intense punishment of his life.

  As soon as Robert entered the room, I had him strip out of the butler’s outfit I’d made him wear for the evening and had him lean against the wall with his arms and legs spread. I picked up my favorite flogger and walked behind him, then swung. The tails landed on his ass with a thud, and even though this was supposed to be punishment, I heard Robert moan with pleasure.

  I delivered a dozen lashes with the flogger, each one stronger than the last, and each time the leather made contact with his ass, Robert would arch his back and moan softly. I know how much he enjoys his punishments, and even though they’re meant to teach him a lesson, I get as turned on as he does when I flog him. The more I struck his ass, the more aroused I became, and by the time I’d reached lash number twelve, my panties were soaked.

  As much as I wanted to get myself off, I knew I had to continue the punishment so he would know how upset I was, and I replaced the flogger with one of my crops. I hit him more swiftly with the crop, landing dozens of strokes in a few moments. I struck him over and over, hitting his ass and thighs until his skin started to flush pink and I saw his dick standing ramrod straight. He was practically ready to explode, and I knew if I continued he might actually come without me laying a hand on his cock.

  I moved Robert to the bed and fastened a belt around his waist, one that had two cuffs attached to it. I cuffed his wrists to his sides and pushed him down so he was lying on the bed. Then I hiked up my skirt, slid my panties off, and climbed onto the bed, settling over Robert’s face.

  “You were a bad boy,” I told him, “but I’m willing to let you make it up to me. You will eat my pussy until I come, and if I think you’ve done it good enough, you may be rewarded.”

  “Yes, Mistress,” Robert mumbled from between my thighs. And then he started to lick.

  In addition to being a well-behaved submissive—most of the time—Robert is also an excellent pussy-eater, and he has never failed to bring me to climax with his tongue. I was still irritated by his clumsiness, but as soon as I felt his tongue brush against my pussy, I started to melt. He licked up and down my slit for a moment before moving to my clit. He circled the hard little bud several times, then flicked it with the tip of his tongue. It felt incredible, and I knew I’d be rewarding him at the end of the night no matter what.

  Robert continued to lick my pussy, thrusting his tongue between my lips, until I forgot all about his earlier errors and could think only of getting off. I started to ride his tongue, and within a couple of minutes, I was coming. It was the fastest he’d ever made me climax, and I knew that the anger I’d felt when he’d stumbled in front of Mistress Lana had helped fuel my orgasm. It was an intense feeling, and it took several long minutes for me come back down to earth. When I did, I climbed off Robert’s face, pulled down my skirt, and looked at my dutiful submissive. His face was covered with my juice, and his dick was really hard.

  I reached down to Robert’s dick and gripped it tight in my fist. “You were a bad boy today,” I said, repeating my earlier comment, “but you did a very good job of pleasing your mistress tonight, too. For that, I’m going to reward you.”

  Robert smiled. “Yes, Mistress.”

  “Don’t come until I tell you to,” I reminded him. He nodded.

  I started to jerk his cock. His hips arched up to thrust into my palm as I stroked him, and I knew he would climax even faster than I had. I reminded him again not to come until I’d given him permission, and then I continued to pump his cock. As soon as I saw a drop of precome ooze out of the tip, I knew he was ready, and I jerked him off a little more forcefully. It took only six or seven strokes, and then I felt his dick start throbbing in my hand. He was going to come. I watched him for a moment as he tried to control his climax and wait for my go-ahead, and I savored the power I had over him. Then I told him he could come, and as he started to spurt, I removed my hand, getting out of the way of his shooting semen.

  When he was done and had calmed down, I freed his hands and allowed him to clean himself up before sending him back to the kitchen to finish the party cleanup. He’d pleased me sexually, but that didn’t mean his work was done.

  Our next dinner party is tomorrow night, and Robert is coming with me to Mistress Lana’s. I have a feeling he’s going to be extremely well-behaved this time, but if he’s not, I have the perfect whip picked out for his punishment…

  —Ms. Joanna E., Tampa, Florida

  Spanking Is Her Biggest Passion, and She Owes It All to Her Master

  I didn’t get my first erotic spanking until I turned thirty, but let me tell you, I’ve spent the past four years making up for lost time. I guess none of my previous boyfriends had been as adventurous as my now-husband, Maurice. We met at a rodeo, and he joked about roping me in. I went home with him that night, and he did wrap his leather belt around me, tugging me into his arms.

  That night he made me fondle his cock through his pants, the hardness making me long to have it inside me. I moaned, giving myself away. “How badly do you want me to fuck you, Jeanette?” he asked.

  “Very badly,” I said truthfully.

  “Badly enough to take a spanking before you get my dick?” he asked.

  “Yes, anything,” I replied, even though I didn’t know whether I would enjoy being spanked. There was something about the way he said it, though, that made me think I might like it. I trusted him not to cross the line and do something that I wouldn’t find a turn-on.

  To his credit, Maurice paced himself—and me. He spread me across his lap while I was wearing nothing but a thong. Every time he spanked me, even the light slaps he used during the warm-up, made my underwear nestle deeper into the crack of my ass. “How does that feel, Jeanette?” he asked.

  “Good,” I managed to say, even though the word was an understatement. I felt exposed and aroused all at once. It was unlike anything I’d ever experienced. The exhibitionist in me liked being on display. Even though the only person I was exhibiting my ass to was Maurice, the concept was still unusual in my naïve erotic experience.

  And the sweet sting of his hand as it connected with my ass! I treasured the way his hand struck my cheek, completely covering it and making me feel so small. I’d always thought my butt was too flat, but Maurice showed me how sexy it could be. When he dipped his fingers under my thong and stroked my pussy, I knew I’d found my passion. I wanted to be spanked all the time!

  “Harder,” I begged him when he resumed giving me light taps.

  “Ask nicely, my pet,” he instructed. “And call me Master.”

  “Please, Master, I’d like some harder swats. As hard as you want.” I had said the word “Master” because he requested it, but as soon as it left my lips, I knew that using it was for me as well. I was surrendering far more than my ass to him, and as he gave me those harder smacks I craved, I knew I would marry him if he asked. It wasn’t only the special sensation he was delivering, the way each smack let me feel his cock hardening beneath me and the way it made my pussy wet. It was that he had known what I needed even before I did.

  That first spanking lasted more than an hour. I didn’t have any marks on me when he was done, to my disappointment, because he kept switching between hard and soft swats to keep me on edge. He told me later that I had to earn the right have stripes across my bottom.

  These days, we like to go to our local BDSM group and show off our spanking skills. I beam with pride when Maurice praises my ass, especially when he shows it off to other people. We don’t play with others, but I’ve been
a spanking demo bottom on occasion, and Maurice allows audience members to hand him items to spank me with.

  Last night, I was blindfolded, so I had no idea what I was going to get hit with next. I think the first item used was a wooden paddle. Maurice warmed me up lightly with his hand, making me tremble. My hands were planted on the floor as my long, blonde hair tumbled down. “See how quickly her skin turns red? That’s one of the things I love about her ass,” he told the assembled crowd.

  He asked them how many times he should spank me with the paddle. Someone called out “a hundred times,” but he settled on twenty. I had to count out each one, adding, “Thank you, Master!” after every swat. Even though I get off on calling him by his honorific, and do consider myself to be under his control when it comes to sex, I still blushed as I counted aloud. He didn’t steadily increase the force he used, but instead gave me twenty very hard smacks. Then he soothed me by rubbing his hand against my overheated skin.

  “I think she deserves more than that, don’t you?” he asked the crowd. I turned my face toward the audience. I was sure if I could open my eyes, I’d see men there with erections straining their pants. Sometimes I fantasize about what it would be like to play with other people, but if that’s going to happen, it will be Maurice’s decision. Instead, to get through the next particularly challenging set of punishment, I pictured myself with a stranger’s cock in my mouth.

  I could tell right away that Maurice was whipping me with a small flogger. At first, it felt pleasant, just a light thudding against my buttocks. Then he really threw his weight into it, and I squirmed, making him hold me tighter with his free hand. How well I behave during a spanking usually determines what kind of fucking we’ll do later. If I was very good, he’d screw me doggie-style, my favorite. If I moved around too much, I’d have to suck his cock, and maybe he’d finger-fuck me later (but since I love giving blowjobs, this isn’t really such a bad scenario). If I really wail and make noise, which can feel good to me sometimes, I know that my ass is going to take a pounding.