Letters to Penthouse XXXXV

by Penthouse International

  Usually by nine o’clock I am dressed and waiting for Todd’s knock on the door. One recent Monday, my boyfriend and I were running late, so I hadn’t had time to change out of my negligee by the time Todd arrived. I let him in, apologizing for not being dressed properly, and said that I hoped he wasn’t embarrassed to see me wearing my tiny baby-doll. I could tell from the lustful look in his eyes, however, that he didn’t mind at all. I don’t know why, but at that moment I blurted out that my boyfriend always fucks me before he leaves for work in the morning and leaves my pussy oozing come. I told him I usually take a shower before his arrival, but I hadn’t yet had the chance.

  I started to leave the room, but impulsively I turned back toward him. I suggested that maybe his first chore of the morning should be to clean out my pussy with his tongue. I grabbed him by his choker, led him to an armchair, pushed him down to his knees, and sat myself in front of him. I draped my legs over the arms of the chair and told him to get going. He immediately slurped up the come that had dribbled down my thigh and then got to work cleaning my pussy.

  Todd’s tongue was a gift. My boyfriend would never go down on me after sex, but my little maid ate my creamy pussy without hesitation. Whenever he stopped to take a breath, I nudged his head back down and told him I would tell him when I was satisfied. He continued lapping at my cunt for more than forty-five minutes, which made me wetter and wetter. After I had multiple orgasms and was sated, I pushed him away and told him to prepare my breakfast while I showered and dressed.

  Cleaning my pussy has become Todd’s first chore of the morning. Within seconds of his arrival, he heads straight for the chair and kneels before it, waiting for me to sit down. On one of those occasions just last week, I looked at him with a smirk on my face and told him I had a surprise. That morning my boyfriend had loaded up my ass with come, so I knelt on the chair and presented my dripping hole to Todd. I enjoyed having his tongue licking me back there, and I rubbed my clit until I came while his tongue probed my backdoor. Having Todd clean my ass made him truly submissive to me. I adore him, and he will always be my special maid.

  —Ms. Isabella K., Trenton, New Jersey

  She Turns a Vanilla Guy into a Dedicated Spankophile

  Some men seem like they are born spankers. They probably spank every girl they sleep with, and even consider it a requirement for sex. Unfortunately for me—a dedicated spankee—I rarely seem to meet guys like that. So I’ve developed a system for goading my vanilla boyfriends into becoming ass-smacking dominants who love to “punish” my bottom. It’s a tricky process because, ultimately, I don’t want to be the one in charge; I want them to come up with scenes and ways to spank me all on their own.

  Fortunately, I have a great ass, if I do say so myself. What I usually do is wear ultrashort skirts that simply draw the male eye toward my bottom, so it’s impossible to ignore. That’s how I reel the boys in. I met my latest boyfriend, Rob, while roller-skating near the beach. He kept checking me out, and finally I stopped and said hi. “Nice outfit,” he said, admiring my tiny skirt.

  “I like to wear as little as possible.” I told him.

  “I can see that.” He then asked if he could buy me a soda, and we each got giant cups of Coke and walked and talked. When I was ready to skate home, he asked if he could drive me there.

  When we got in his car, we immediately began making out. His hands went to my ass and started squeezing my butt cheeks. But just as I was angling for him to swat me on my bottom, he moved upward to feast on my nipples. My nipples are very sensitive, so I didn’t mind, but I was itching for a spanking.

  “I’ve been such a bad girl today,” I said. “I told my boss I was sick, so I could go out and play at the beach.”

  “Mmm-hmm,” he said, continuing to suck my nubs.

  “I really deserve to be punished for that,” I continued, pushing the conversation in the kinky direction I wanted it to go.

  Then I pulled away from him and basically climbed into his lap to spread myself out across the length of the bench seat. My skirt was so short that it inevitably rose up, revealing my bottom, visible save for the spot covered by my tiny G-string. I was very wet, and more than ready to be spanked.

  “Are you trying to tell me something, Clarissa?” he asked as he started massaging my butt cheeks. I could tell he was getting closer to that glorious point where a man starts to imagine himself raising his hand and striking my ass. I felt the vibe in the crowded car change as his breathing became heavier.

  “Yes, I am. I’m a bad girl who needs to be spanked. I deserve whatever punishment you want to give me,” I said, wiggling a little to emphasize my point. I bit my lip in anticipation as I awaited his next move.

  “You certainly do have a beautiful ass. But I’ve never spanked a girl before,” he said, his voice trembling with nerves, but I could tell he was also intrigued.

  “You can do it,” I said. “Just hit the middle part of my ass. You can do it as hard as you want. And if it helps, getting spanked makes me totally horny. All I want to do after I get spanked is suck cock and get fucked hard.”

  Well, that was all the encouragement Rob needed. He brought his hand down on my right cheek with a stinging slap. “Yeah,” I whispered as he did it again.

  “That’s pretty,” he said, and I turned and looked as best I could. Already, my normally pale cheeks were pink. “Put your head back down,” he growled, quickly catching on that I love to be ordered around. I’m not just a spankophile; I’m also a dedicated submissive, so letting a man control and “punish” me is the key to my sexual happiness.

  Then Rob started to experiment. He shifted angles and cupped his hand in different ways to vary the sensations he was delivering. Instead of waiting a few seconds between smacks, he went full force, whap-whap-whapping the same spot over and over again. The pleasurable pain was compounded as he swatted me repeatedly.

  “You like that, don’t you, Clarissa? I can smell how turned on you’re getting,” he said as he kept reddening my bottom. For someone who was new to spanking, Rob was a fast learner.

  I was getting so hot; I needed to be fucked immediately, but I knew that after giving him the power to spank me, I couldn’t stop him and demand his cock. He teased me by rubbing my wet pussy, but only pushing his fingers slightly inside me. “You’re nice and tight,” he said. “I bet my cock will feel good stretching you out.”

  I moaned, unable to properly speak. I was aware, though, that we were still in his car. Yes, we were on a desolate street, but even I wouldn’t be so bold as to fuck someone where we could possibly get arrested. “How badly do you want it?” he asked as he kept spanking me. I knew “it” was his cock, and I responded right away.

  “I’ll do anything to get it. I need you to fuck me as hard as you’re spanking me,” I said, and then cried out as he delivered his hardest smack yet.

  Rob pulled me up so I was straddling his hips, then kissed me hard. “You are a bad girl. I’ve never done anything like this before and look how hard you’ve made me,” he said, pushing me back far enough so he could show me his dick. I went back to my seat, my ass throbbing, as he drove me to his place.

  There, he took out a sturdy leather belt and whipped my bottom with it. My butt was on fire, but in a good way. Each stroke was powerful and deliberate, and I started to wonder if Rob was as innocent about S&M as he had initially seemed. Then he made me kiss the belt before bending me over his bed. “I’m sure you give great blowjobs, Clarissa, but I need to fuck you.” He plunged inside me, his dick as strong and powerful as the slaps he’d delivered earlier.

  I came in under two minutes, and he made sure to punctuate my orgasmic exclamations with even more smacks. Then he gave me what I’d wanted before—his cock in my mouth. I sucked Rob to orgasm, with him thrusting his dick between my lips. I was on my knees, my sore bottom resting against my feet, as his come shot down my throat. I swallowed every drop, and then he drew me a bath. That was the start of a beautiful, kinky relationship th
at has grown as we’ve found new ways to enhance our spanking fun.

  —Ms. Clarissa K., Venice Beach, California

  Her Forgetfulness Is Cause for a Corrective Whipping

  I’m not a forgetful person when I’m on the job; I can’t afford to be, since I run a high-end shop that caters to wealthy clients. It wouldn’t be long before I’d be out of business if I mixed up orders or sent the wrong items. But while work’s been fine, I’ve been letting things slip in my personal life. My first guess as to why that was the case was that I’m so preoccupied with the details of my job that minor chores, like picking up the dry cleaning, didn’t seem as important to me. But I eventually realized that my “accidental” actions might be connected to my subliminal hunger for kink. After I thought about it, I decided that my screwups must’ve come about because of my subconscious desire to be punished.

  My husband and I try to divvy up household duties as best we can, and I know Wes’s job as a lawyer keeps him busy, too, so he relies on me to do my share. He’d been patient with my recent spate of forgetfulness, but I could tell that I was pushing my luck.

  The situation came to a head the other day when I forgot to book our vacation cruise in time to take advantage of a special discount. Despite having a reminder pop up on my phone and another land in my inbox, the day went by without me booking the trip. I kept meaning to do it, but more important stuff kept coming up. Later that night, when Wes asked me if I’d taken care of the arrangements, the look on my face told him everything.

  On the outside, Wes and I don’t look like kinky people—but we are. I love getting spanked and serving my husband, and he loves being the boss, telling me what to do, and most of all, taking me over his knee. For us, it’s not only incredibly hot, but a way to destress and let off steam. Our workday cares fade into the background as his hand or his belt connects with my ass. I can’t explain why, but I find our scenes to be a dirty form of relaxation and recreation, and while it’s not a necessity, a bit of role-playing or an element of “punishment” adds to the occasion for me.

  We’d both been so busy lately that it had been weeks since we’d enjoyed a kinky scene. I guess I’d been itching to be punished, so without realizing it, I created an opportunity for myself. I knew how important this trip was to Wes and how much he wanted to save the extra cash. Not booking this trip was the perfect way to push his buttons.

  In response to his annoyance and disbelief, I said, “I’m sorry. There’s no excuse for what I did. I was very bad.” My words, along with my subdued tone, let him know that I was entering submissive mode. Seeing my downcast eyes and hearing my voice was like flicking a switch for him. He fell into character right away.

  “You’re right—you’ve been very bad, Trudy. A grown woman like yourself needs to be held accountable. You’ve been irresponsible and deserve to be punished.” I nodded. “I want you to call tomorrow and make the arrangements for our cruise, so I’m going to help you remember to do it. Get undressed and bend over the bed. I’m going to give you twenty with my belt. After each lash, I want you to say, ‘I won’t forget the reservations.’ You’re going to be reminded every time you sit tomorrow.”

  I stripped as ordered, but before he began to whip me, he made me kiss the tip of his belt. That act always makes my pussy drip with wetness—the smell of the leather, the acknowledgment that it will soon slice through the air and strike my bare ass. Wes likes the sound the belt makes, and he cracked it the air before hitting my right ass cheek. I muffled my groan as I remembered his instructions. “I won’t forget the reservations,” I said as quickly as I could. No sooner were the words out of my mouth than the next lash landed upon my left ass cheek, and I repeated the words again.

  I focused on breathing deeply, because even though I enjoy being punished—by his hand, belt, or any other implement—it does hurt, and breathing helps me process the sensations. Even though the belt’s impact was harsh, my cunt responded to each lash, growing wetter with every stroke. We settled into a steady rhythm, but the second Wes felt I was comfortable, he struck the tops of my thighs, making me squeal. He knows I’m extra-sensitive there. It’s a fine line to walk, but he does it expertly, bringing me just the right amount of pleasure/pain. “Very good, Trudy,” he said after lash number eight, running his fingers along my hot skin and tracing the marks he was leaving on my flesh. I didn’t have to see them to know they were there.

  Then it was time for my final twelve lashes, and he made them count. At one point I clenched my butt cheeks tightly, steeling myself for the blow. “Come on now, Trudy, you know I’m not going to hit you if you do that.” That was his ingenious way of getting me to relax; I wanted the spanking more than I didn’t want it. I always do. So I took another deep breath and prepared myself for the pleasure as well as the pain. When it came, it was intense, but wonderful, too, and my pussy was getting slicker and slicker. When the final blow landed, the warmth from my ass had extended throughout my lower half, making me tingle all over.

  “My bad, bad girl,” he sighed, and then leaned down to kiss each ass cheek.

  Wes got on the bed and unzipped his jeans to free his cock, before motioning me to climb aboard. I sat down on his erection, my dripping pussy enveloping him in one smooth motion. He grabbed my sore ass and gripped it extra-hard as he controlled the movement of my cunt up and down his shaft. “Your pussy is making my cock shiny with your juices,” he said. “Now touch yourself, Trudy, touch that sweet clit for me.”

  I looked where he was looking—at his cock sliding in and out of me—and stroked my clit. It wasn’t long before the overwhelming sensation of my orgasm washed over me, and I trembled as I came, my cunt tightening around his shaft. He tapped my ass lightly, and I tumbled forward, hugging and kissing him as he rammed his dick upward and came with a loud groan. I felt the hot splash of his cream inside me and smiled as I buried my face in his neck.

  “You look so beautiful,” he said as he pulled me off him and turned me over onto my side so he could admire my ass. For the first time in weeks, I felt completely satisfied.

  When he went to take a shower, I picked up the phone and called the travel agency. It was a few hours past the official cutoff for the discount, but I was hoping maybe they’d cut me a break. As it turned out, they had a cancellation and were more than willing to book us on the exact cruise we’d wanted—at the lower price. I was thrilled. Not only had we gotten the deal, I’d received a sexy punishment as a bonus!

  I told Wes the happy news when he emerged from the bathroom, wearing just a towel. “That’s wonderful, Trudy. I hope you don’t think that your spanking was in vain, though.”

  “Not at all. In fact, I might need another one tomorrow. I’ll have to see what I can do to warrant it.”

  He grinned at me, then dropped the towel and slid into bed, his cock once again hard and ready.

  —Ms. Trudy L., Baltimore, Maryland

  She Discovers Her Inner Domme and Makes All His Dreams Come True

  When Chris told me he wanted to hire a dominatrix, I wasn’t really surprised. He’d always seemed to like domineering women, and more than a few times when we were dating he’d playfully asked me to spank him because he’d “been a bad boy.” It wasn’t until we broke up that he started discussing his desire to be controlled, though.

  I told him I’d help him find a domme, and we created online personal ads on a bunch of fetish websites. I even accompanied him to a few fetish parties when the ads didn’t yield a suitable domme for him. No matter what we did, though, he couldn’t seem to find anyone who was offering the kind of domination he sought. I was starting to think we’d never find the perfect mistress for Chris—and that’s when he propositioned me.

  “Do you think you could do it?” he asked me one day at lunch. We’d been discussing what he should do next to try to find a dominatrix he could work with when, out of nowhere, he asked me to take on the role of his fantasy mistress.

  The idea was intriguing, to say the least, but I
wasn’t sure I could play the part very well. Besides that, Chris was my ex, and I didn’t know whether we should be getting involved in any kind of sex play. I didn’t want to say no right off the bat, though, so I told him I’d think about it and let him know in a few days.

  All weekend, all I did was think about Chris’s proposition. The idea of dominating him aroused me, and after all the work we’d done to try to find a woman to top him, I thought I had a good idea of what he wanted. I’d been spanked by partners a few times, and had met a dominatrix who’d shown me a few tricks at one of the parties Chris and I had gone to, so I felt like I knew enough for us to try it out. And, to be honest, I was still incredibly attracted to him, so the thought of ending up in bed with him again was pretty appealing. When we met for lunch the following Monday, I told him I would do it.

  That Saturday, Chris came over to my apartment. I met him at the door wearing a leather corset he’d bought me when we were dating, a pair of leather pants, and sky-high heels. I had a riding crop in my hand—it seemed like the perfect accessory—and I slapped it against my leather-clad leg, doing my best to look fierce.

  Chris bowed his head when he saw me and mumbled, “Good evening, Mistress,” before stepping into my apartment. I led him to the living room and had him get on his knees. I told him he’d been bad and that I thought he needed to be punished.

  “Do you agree, slave?” I asked, my voice loud and harsh.

  “Yes, ma’am,” he said, his head still bowed as he knelt on the floor in front of me.

  I swatted his ass gently with the crop, his pants softening the already-light impact, and he moaned quietly. I didn’t think he felt much from the light taps, but simply having me play the role of his dominatrix seemed to make him hot.

  I flicked my wrist harder, making the crop hit him with more force, and listened as he moaned a little louder. I continued this for a few minutes before having him stand up and walk over to the couch. I had him lean over the back of the sofa, and then I started smacking his ass with my bare hand. He still had his pants on, but I was able to hit him harder than I had with the crop, and he seemed to enjoy it. He started wiggling his ass at me, and his moans stretched out long and low.