Letters to Penthouse XXXXV

by Penthouse International

  “At twenty, we’ll be done,” I told him, and I made the last eight count. He took them like a man, impressing me with his stamina. When I was done, I let him sit down, knowing that would reawaken the sensation of his spanking. His hard dick popped up, as if begging. “Now, you’ve shown a very good ability to take instruction, and I will be preparing tasks for our twice-a-week sessions. As we progress with our play, you will be allowed to seek release. Until I give you the okay, however, you are not to orgasm in my home. Do you understand?”

  Josh nodded, then got dressed and left. I received a thank-you email later that night, and I immediately began plotting our next wicked session.

  —Ms. Natasha V., Via Email

  Window Display Inspires Vacationing Couple to Try a Little S&M of Their Own

  I had never really thought about doing anything kinky until my husband, Nate, and I were on vacation in New York City. Well, maybe once or twice I’d had dreams about being sexually “tormented” and then woken up wet and horny, but it was never anything I’d discussed with Nate.

  While on our trip, we happened to walk by an upscale lingerie/sex toy store. Their provocative window display caught my eye—and Nate’s. Two female mannequins were wearing exquisite lingerie, and one was blindfolded, while the other held a crystal-studded riding crop. In the background, there were all kinds of kinky accessories. The display was hot, yet tasteful, and I couldn’t stop staring at the scene… and imagining myself in such a scenario.

  One look at Nate let me know that he was intrigued, too. At that point, I didn’t know whether I was more interested in being a domme or a sub, in holding the crop or yielding to it, but I did know that my panties were suddenly very, very wet. It wasn’t that we didn’t have stores like that at home, but we’re so busy with our jobs, we’d never bothered to stop in any of them. Nate paused and wrapped his arm around me to pull me back against him. “Let’s look in here,” he said, gesturing toward the erotic display.

  Obviously he didn’t have to work hard to convince me, and, holding hands, we entered the store. I was pleasantly surprised that it wasn’t tawdry in the least. In fact, it was as elegant and intriguing as the window had suggested it might be, and my eyes jumped from one corner of the store to another. I looked at Nate, and he seemed as excited as I was by all of the naughty possibilities.

  The store’s saleswomen were friendly, and a bit flirtatious, but they didn’t pressure us to buy or try anything. They simply showed us the offerings, and we took it from there. I could feel the sensual tension sparking between Nate and me, something I’d been hoping would happen on our trip, but it was spiked with something new: the desire for kink.

  When Nate grabbed my wrists and tugged them behind my back, then momentarily secured them with a set of padded handcuffs, my nipples tingled, and I realized I wanted to rush back to our hotel to finish what we’d started. The staff looked on in an amused way as if they’d seen that sort of behavior a million times. We took our time perusing their offerings, finally settling on an expensive whip—though Nate also tested out a pink paddle on my skirt-covered bottom—and a blindfold that said, “Treat me like the whore that I am.” I trembled at the thought of having Nate place it over my eyes, immersing me in darkness and putting me in my place.

  We walked back to our hotel, giddy with anticipation. We kept stopping to make out on the street, and at one point Nate lightly smacked my ass, something he’d never do at home, and I knew that our sex life was about to change permanently. When we got inside our room, instead of him sitting down and taking off his shoes, he started kissing me. Well, more like attacking me with his tongue; Nate pressed me against the wall and made me breathless with both his kisses and his roaming hands.

  “You bring out the beast in me, Mel,” he said, as I mock-struggled to escape his grasp. I didn’t want to get away in the least, but writhing in his arms turned me on. My pussy was dripping wet by this point, and while I wanted to continue our kinky play, I was also desperate to be fucked. Nate knew it, too, because he brought his hand between my legs and pressed against the wet fabric he found there.

  “You want my cock, don’t you?” he asked. “Or do you need to be punished?” He continued to toy with me, this time slipping his fingers into my panties. But when I didn’t answer him, his fingers got a little rougher. He pinched my clit hard, and I yelped. It hurt a little, but it also made me gasp with delight. Then he ripped my panties right off me! Clearly, we didn’t need our new toys for him to take control of me. “I’m in charge tonight, Mel. You’re going to do what I say and then maybe, if you do a good job, I’ll give you my dick. And maybe I won’t.”

  I loved him more in that moment than I ever had. I was so thrilled he wanted to go on this sexual adventure with me. Then I quickly got back into submissive mode, already taking to the changed dynamic between us. Nate ordered me to shut my eyes, and then he slipped the blindfold over them. “That’s because you’re a whore. My little whore.” The words were so dirty and sweet at the same time that they made me shiver with delight. “Say it, Melissa. Tell me you’re my whore.”

  “I’m your whore, Nate,” I said, amazed at how such simple words and actions had electrified us. Nate bent me over the bed, and then hiked up my skirt. I was already bare on the bottom because he’d ripped off my panties. He moved away, and I focused on what I was hearing, since I could no longer see. I felt both exposed and dirty.

  A second later the whip whizzed through the air and snapped against my flesh. It wasn’t a serious lash—that came next—but it still signaled that we were no longer playing around. “Are you ready for more?” Nate asked.

  “Yes, sir,” I said, and then he tapped my right butt cheek with the end of the whip. I moaned, even though I barely felt the whip. I moaned because I wanted more, because he seemed to be teasing me. The next lash was slightly harder, and I thrust my bottom higher into the air, inviting the next strike. My breathing shifted from my mouth to my nose, deep breaths in and out as I focused entirely on the sensations and emotions that I was feeling. Then the whip started striking me in earnest. Nate used the toy the way the sexy saleslady at the shop had shown us (we’d each gotten to hold it and practice on a faux butt they had in the store).

  But this wasn’t practice. This was real—and intense, and the heat from the lash suffused my skin. Yes, it hurt, but that paled in comparison to the way it made my pussy ache with pleasure. Nate intuitively knew where to strike me, how to ease up, then hit harder. When he put down the whip, I sighed in disappointment. That was only momentary, though, because he then joined me on the bed and administered a hand-spanking. “You’re a very naughty girl, aren’t you?” he asked softly. I knew that seeing my butt blush and watching me willingly and eagerly submit had turned him on.

  “Yes, I am. I’ll do anything you want me to,” I told him. Well, what he wanted was for me to suck his cock, which I’d been craving for hours. It was a huge tease; I’d start to deep-throat him, and then he’d pull me off and spank me hard. It was so sexy, and we each fed off the other’s desire. After I’d gotten spanked, I was so turned on that I’d swallow him whole in one motion, my arousal increasing my hunger for his dick.

  When he was on the verge of coming, though, he stopped and told me to bend over the bed again. He spread my legs wide and then did something unexpected, though I should have anticipated it—he spanked my pussy! It felt so good I whimpered, and soon I was crying out as his hand alternated between my ass and my cunt, offering smack after glorious smack.

  Then it was time for his dick, and he plunged into me without any preamble. One moment I was simply an open, waiting pussy, the next I was being filled with a dick that felt even bigger than usual. Maybe he was just that turned on, or I was; I’m not sure, but each movement sent pleasure racing through my body. I was wild, making so much noise that he grabbed me by the hair and said, “Shut up. I’ll tell you when you can make noise.” It was so sexy that I had to bite my lip to keep from moaning. Usually Nate likes
me to be loud, but I guess he just wanted to assert his dominance, which was fine by me.

  I quieted down and then the only noise was from our bodies meeting: my pussy’s squishy-sounding wetness as he took what he wanted from me, punctuated by the occasional smack against my ass. He kept fucking me for what felt like a long time, before unleashing his load onto my back, then ordering me to make myself come while he watched.

  Nate’s final act of dominance over me that night was to order room service for us and make me answer the door while wearing only my skimpy nightie. I blushed as I gave the surprised-looking bellhop a tip. That was only the start of our dirty adventures, which have continued at home with our new toys. Now we’re looking to find play parties where we can share our kinky fun with others!

  —Ms. Melissa H., Houston, Texas

  Inventive Domme Decks the Halls—and Her Submissive Husband

  Before this past Christmas season, I could never get my husband to help me decorate the tree. As with the cooking, cleaning, and other household chores, Dean wouldn’t lift a finger. This year, though, I got an idea while shopping for decorations. Instead of using tinsel garland solely to decorate the tree, maybe I could use it in a way that would get my husband’s attention and help me express my unhappiness with his attitude. In other words, I could use the shiny garland to bind him tight and teach him a lesson.

  I bought more tinsel than I needed, but I kept my plan a secret. Unsurprisingly, when the designated day and time to trim the tree arrived, Dean was nowhere to be found—not in the living room, not in the garage, nowhere. I called his cell and got directed to voicemail. I was getting genuinely annoyed, so I texted him: GET. HOME. NOW.

  Half an hour later, he sheepishly walked in. “Sorry, baby,” he said.

  “You will be sorry by the time I’m done with you!”

  I saw a flicker of nervousness and excitement wash over Dean’s face, and it only served to turn me on and stoke my desire to dominate him.

  I’d laid out the packages of silver, red, and green tinsel as my husband watched. “What’s all this?” Dean asked, observing my abundance of garland.

  “You’ll find out soon enough. Now get over here,” I commanded, picking up a Christmas necktie that he’d gotten last year from a neighbor. He looked at me curiously before obeying my command, quickly catching on when I wrapped the hideous necktie around his eyes as an impromptu blindfold; at least it was good for something. As I secured the tie, I realized that this was my true Christmas present: the chance to have my way with my recalcitrant husband.

  Once the tie was firmly in place, I said, “Now put your hands behind your back.” The stern tone of my voice dared him to protest. However, he didn’t and simply obeyed me. I picked up a length of the silver tinsel and tied his wrists together, completing it by fastening it with a bow. The kinky yet festive sight made me feel better, as did the way his mouth looked as it formed an “O” as his expression mirrored his disbelief.

  Having him blindfolded and helpless made my pussy ache. The sight of him was so arousing that I was tempted to fuck him right away, but I knew that wasn’t the way to instill discipline. So while he stood there meekly, I took off my clothes, narrating the action as I removed each article of clothing, wanting to be sure he knew what he was missing. I let my hip brush against his fingers, but when he tried to grab me, I pulled back and denied him. I laughed out loud when Dean almost fell as he tried to reach for me.

  “I think you need to sit down,” I said, leading him to the couch. Once he was seated, I bound his ankles. “Hmm… what’s missing? Oh yeah, you can still talk.” I looked around and then grabbed my red panties and shoved them in his mouth before making a tinselgarland collar. With that bit of green metallic fluff wrapped around his neck, he was perfectly suited to be my pervy little helper.

  “Now stay right there,” I said. “I’m going to work on the tree.” With that, I put on some carols and went about decorating, humming along and occasionally sneaking peeks at my bound husband. A few times, I heard him trying to speak, but he couldn’t. All that came out through my panties were muffled noises, and the sound turned me on.

  Finally, I was done with my decorating, and I removed his blindfold, so he could see my handiwork—and my nude figure. Somehow, he seemed more interested in me than the tree, but I wanted to hear him praise my skills, so I plucked the panty gag from between his lips.

  “Tell me how nice the tree looks—no thanks to you.”

  “It’s gorgeous—and so are you, Kelly.”

  “Thank you,” I replied. “Now, how are you going to get back in my good graces?”

  “However you like,” he wisely replied.

  “Very good. I’m going to keep you tied up, but I’m going to take out your cock and ride it until I’m satisfied. You are not to come. If you do, you’ll be in big trouble. Is that understood?”

  “Yes, ma’am,” he said. I fished his cock out of his pants, pleased when I felt how hard it was. I unfastened his pants all the way and had him rise off the cushions for a moment so I could tug his slacks and underwear down to his bound ankles. Once he was as naked as I needed him to be, I straddled him and slowly descended to envelop his erection in my throbbing cunt. The carols had ended, so I hummed to myself as I enjoyed my festive little sex toy.

  “At least your cock does what I want,” I said, sighing as his erection filled me completely. He just moaned in response, keeping his eyes locked on my bouncing breasts as I rode him energetically. “If you’d been here to help when I needed you, I’d allow you to come inside me right now. But you didn’t, so you can’t.” I continued taunting him through my first, second, and then final orgasm. Then I jumped off him, leaving his shiny dick waving in the air. His disappointment was palpable.

  Sated and happy, I untied Dean and pointed to the packages of red tinsel. “Trim the tree with that—in an attractive way—and maybe I’ll let you come.”

  Let me tell you, after I took my bath, I came down to see not only the tree beautifully trimmed but my man in the kitchen making dinner. I was so pleased that I fucked him and let him shoot inside my pussy. He was so thankful, he nearly wept with gratitude.

  Dean may be a bit absentminded at times, but he knows how to make it up to me, and that’s a lesson I don’t mind if he has to relearn every year.

  —Ms. Kelly R., Cherry Hill, New Jersey

  Businesswoman Pimps Her Favorite New “Girl” to Her Exclusive Clientele

  I’m a successful businesswoman in the “hospitality” industry. I have numerous clients who have extraordinary tastes, so my stable of women is varied and substantial. I have the perfect date for everyone. However, the most difficult sexual preference to line up is a young, innocent cross-dresser. I have a number of important men who desire a fresh-faced burgeoning transvestite. When I am able to cultivate TVs who match my clients’ preferences, they’re usually only suitable candidates for several years, while they still have the fresh-faced beauty that my customers desire. The hardest part of the process is finding an appropriate candidate and grooming him to be the most beautiful woman he can be. I currently employ Daniel, a vivacious young man who goes by the name Danielle when he is dressed in his feminine finery. Daniel is in very good shape and works in a profession that gives him enough free time to be in my employ.

  I met Daniel two years ago in a nightclub, a few days before Halloween. I always scope out parties with costume contests, because there are always several cross-dressers in the crowd. The trick is to find one who’s unattached, and who has the kind of sleek, feminine body type my clients crave. When I found Daniel, he was alone by the bar and was an ideal candidate for my needs. He seemed content to be out en femme, and he didn’t seem like he was posturing to impress women.

  From a short distance, I admired Daniel from head to toe. I caught his eye, and he smiled at me. I asked him whether he was a guy or a girl. He blushed and admitted to being a male. Daniel was very passable, but he lacked the refinement and carriage of a
biological woman. I admired his outfit and his perfectly applied makeup. His walk wasn’t bad, but his hips and ass didn’t have that special feminine sway when he moved. I could tell that he needed some additional training.

  I complimented Daniel on his choice of attire. He was wearing a black sheath dress that fell to midthigh, stylish three-inch black heels, and black stockings. He also wore a nicely styled blonde wig, which was clearly synthetic. And although his nails were manicured, he’d neglected to shave his fingers and the backs of his hands. He clearly needed the firm, guiding hand of a dominant woman.

  I struck up a conversation with him and eventually invited him to sit with me. I bought him several drinks and asked him to dance. As we swayed to the music, I whispered in his ear that I thought he looked sexy and moved my hand to his crotch, cupping his hard-on through the delicate fabric of his dress. I told him that I had to check for myself that he was really a guy because he looked so womanly. I fed his ego, and he eagerly ate up my compliments. After several hours of flirtation, I invited him back to my place. As I drove him home, my hand kept wandering into his lap to tease his swollen cock. He might have looked like a lady, but he felt like a completely aroused man.

  Once inside my place, I poured us some wine and asked him to show off his entire outfit to me. He started to sway in a sexy manner and raised the hem of his dress to reveal his slinky black slip and then his high-cut panties. Daniel had very good taste in lingerie.