Letters to Penthouse XXXXV

by Penthouse International

  When I agreed to bring Jesse along on a double date with my friend Linda and her boyfriend, Rick, I knew my fiancé would flip. According to him, Linda is the most annoying person on the planet, and Rick isn’t much better. He knew she and I were close, and he tolerated her and Rick when he had to, but he’d long ago made it clear that double dates were off limits. Making plans for the four of us to get dinner together was going way beyond what Jesse would find acceptable, and I knew when he found out I’d be punished—and I couldn’t wait!

  I told Jesse about the double date only a few hours before we were supposed to meet Linda and Rick, and he flipped, as predicted. He stormed around the house getting ready for our date, and when we got in the car, he gave me an earful. There was “How dare you!” and “You’re going to pay for this!” and, my favorite, “You’re getting a spanking when we get home!”

  Jesse wasn’t really as mad as he seemed to be; he was just using his annoyance as an excuse. I like when he’s aggressive and dominates me, and one of our favorite ways to get into the game is for me to “misbehave.” I do something I know he won’t be thrilled about, and then he takes control and “punishes” me for it. It’s our favorite way to get in the mood, and I knew that when we got home, I was in for a fantastic spanking.

  All through dinner with my friends, Jesse hinted at what would happen later that evening, and by the time we left the restaurant, my panties were soaking wet. I tried not to appear too eager, but I knew my fiancé could tell how anxious I was to get in the bedroom and over his knee.

  As soon as we got into the house, Jesse and I rushed to the bedroom and assumed our roles as dom and sub, respectively. Jesse took charge immediately, ordering me to undress down to my panties. I did a sexy striptease for him, shimmying out of my jeans and blouse, and then waited for his next command. He was still fully clothed, but I could already see the bulge in his jeans. I knew it was going to be a good night.

  Jesse sat on the edge of the bed and called me over to him. He had me lie across his lap, still in my underwear, and he rubbed my ass through my silky boyshorts. His touch was soft and gentle, but I knew it wouldn’t stay that way, and I couldn’t wait for the spanking to begin.

  He teased me for another minute, making me wriggle in his lap as I anxiously awaited the first smack. When it finally came, I moaned in delight. His hand slapped my ass through my panties, the silk barely dulling the impact, and it felt incredible. Even the sound, the muffled thud, was arousing. The second blow landed a few seconds later, his hand making contact in the exact same spot and increasing the pleasure I was feeling 100 percent.

  More smacks started to land in quick succession, and each one made me gasp and moan as shock waves of ecstasy shot through me. And when Jesse finally pulled my panties out of the way, the feelings only grew more intense.

  Jesse continued to scold me as I lay across his thighs, his erection growing and pressing against my stomach. It was clear that I wasn’t the only one getting turned on by his dominant behavior. Each time his hand hit my ass, his stiff cock throbbed against me, and my juices were soon dripping onto his pants as heat pooled in my center.

  His smacks got harder, and my butt jiggled each time his hand connected with my bottom. The more forceful the spanking, the better it felt, and he was giving me the most pleasurable punishment I could have imagined. When he started delivering the slaps with more frequency, I moaned loudly, my sounds of excitement nearly drowning out Jesse’s comments about what a bad girl I’d been.

  He continued to pick up the pace until he was rhythmically slapping my ass, and then he suddenly stopped. My butt was hot and tingling, but I still wanted more.

  Jesse apparently wanted more, too, but not more spanking. He told me to get up, and when I did, my panties fell to the floor. I stepped out of them and let Jesse push me to the bed. As soon as I was sprawled across the mattress, Jesse started ripping off his clothes, and in less than a minute he was climbing on the bed with me. His hard cock bobbed in front of him as he moved toward me. I saw a drop of precome glistening from the tip, and I couldn’t wait to feel his dick slide into me.

  He kissed me hard as he crawled over me, and I thought he was going to thrust into me and start fucking me right away. Instead, he rolled onto his back, taking me with him, and I landed on top of him. We quickly repositioned ourselves, and then Jesse guided me down onto his stiff cock.

  It felt good to have him inside me, and I was so excited that as soon as his dick filled me, I started to ride him. As I slid up and down his shaft, Jesse started to spank me again, one hand smacking my ass while his other held my hip and guided me. My butt tingled as I rode him, my cheeks alternately slapping his thighs and being slapped by his palm. It was an arousing combination of sensations, and my pussy started to spasm and clench around his dick as my climax approached.

  When I felt Jesse’s cock start to throb inside me, I knew he was getting close, too. He started to spank me a little harder—as hard as he could in our current position—and it urged me on, making me move faster and bringing me even closer to my own orgasm. It only took another minute of fucking and spanking to get us off, with Jesse digging his fingers into my ass as he filled my pussy. My juices flowed freely over his shaft a moment later as I climaxed. It felt incredible.

  When Jesse and I went to bed that night, I was already thinking about what I could do to earn my next punishment. I remembered Linda mentioning she and Rick were going to rent a house on the shore for a week the following month, and I made a mental note to call her and see if she would mind if Jesse and I tagged along for a few days at the beach. I knew that would infuriate him—and I couldn’t wait to feel the spanking that would inspire him to give me!

  —Ms. Katherine H., Mobile, Alabama

  Former Submissive Brings Out Her Domme Side with the Help of Some New Playthings

  When I saw the padded cuffs at the sex-toy store, I knew that’s what I’d buy with the gift certificate I’d won in a raffle. I have a few vibrators, and even a butt plug, and while I’d been tied up with scarves and other household items that were pressed into kinky service, I’d never owned a pair of proper cuffs.

  I took my time examining the options and testing out different cuffs on my wrist, though you can’t truly tell what being bound by a lover will be like until it happens. My boyfriend, Charles, is fabulous, and surely would’ve come with me to the store if I’d asked, but I wanted to surprise him; we’d both been busy lately and our sex life had been full of quickies. Hot quickies, mind you, where we both came, but I wanted us to have a sexual experience we could savor.

  In my fantasies, Charles tied me up and took his time doing things to me—wicked things that made me moan and gasp and shudder. I wasn’t sure what all of them were, but I couldn’t wait to find out.

  Unable to choose, I decided to ask for some advice. I told the clerk, whose name was Luke, that I wanted bonds that were sturdy. At first I was nervous telling a complete stranger about my sex plans, but he set me at ease. He was efficient and businesslike, but also friendly. I’d been testing the cuffs on just one arm, but I wasn’t satisfied—then he asked if he could help me with anything. “Could you cuff my wrists behind my back?” I asked, holding up a pair of padded black and purple leather cuffs. I mean, surely he’d done it before, but asking that favor made me blush.

  Luke was kind and said he’d be happy to do that for me. I placed my hands behind my back, and he strapped on the cuffs. I yanked at my bonds, and right away I realized that I couldn’t escape—and that made my pussy drip!

  “You like it, don’t you?” he asked, snapping me out of my reverie.

  “Yes,” I said. “I can’t escape, but that’s really sexy.”

  “Well, they look fabulous,” he said, leading me backward toward a full-length mirror where I could gaze over my shoulder and ogle my bound wrists. He was right, and I had a feeling Charles would appreciate the sight.

  Luke uncuffed me, and I kept looking around, figuring that since
I was in the store already, I should see what else I could get to add to my fun. “What about this?” Luke suggested, running a pink feather tickler along my neck. I giggled. “Just imagine this against your armpits with your arms bound above your head. You’d have to beg for mercy.” His tone wasn’t flirtatious, although the words had a definite effect on me.

  “Okay,” I said, dropping the tickler into my basket. Next I picked up a package of rope and looked at it skeptically. I didn’t think rope would be comfortable, but Luke showed me that it wasn’t plain old rope. It was specially made bondage rope, which felt soft against my skin. “Okay, I’ll take that, too.” Then I spied a pink blindfold and thought, Why not? I also selected some black tape before finally leaving the store, my wallet lighter but my entire body pulsing with desire.

  When I arrived home, I was bursting with excitement. The whole time I’d been shopping, I’d imagined Charles using all these new playthings on me—placing the tape over my nipples, cuffing my wrists behind my back, wrapping purple rope around my ankles. What I hadn’t counted on was that Charles was curious about being bound, too. I didn’t know the idea of being my captive would make his dick rock hard! I found that out as soon as I told him about my shopping adventure, and he started wrapping one of the cuffs around his wrist. The sight really turned me on.

  “I guess you’re going first,” I said, taking out the tickler and brushing it teasingly against his cheek. “Why don’t you strip for me?”

  He smiled and started to pull his clothes off his body as fast as he could, but I stopped him. “No, not like that. Like a stripper. Slowly. I’m not in a hurry—are you?”

  “No,” he said, but I could tell that wasn’t true. Part of him was extremely eager for me to work my magic on him and didn’t want to wait. However, as Charles began to slowly undo each button of his corduroys, I found that I was the one getting impatient. Finally, he was down to his briefs, which I told him to keep on.

  At his frown, I added, “Don’t worry, you’ll get to take them off—if I give you permission.” Then I did to Charles what Luke had done to me: secured his hands behind his back. “I think you need to be blindfolded,” I added. He groaned, and I noticed his cock twitch in his briefs. I settled the pink blindfold over his eyes and then I surveyed him, wondering what I should try next. I traced the feather tickler along his neck and over each nipple, then over his flat stomach, before putting it down. Knowing he couldn’t see me, I silently removed my top and bra, and then played with my nipples, tugging and twisting them until they were as hard as I could get them.

  “Guess what I’m doing?” Charles moaned in response. “Guess!” I shouted, wishing I had a whip. It was amazing how easily I could slide into this stern persona—and like it!

  “Touching your pussy?” he asked.

  “Wrong!” I said, coming closer and tweaking his nipples. “I think for that you are going to get some tape over your mouth.” I didn’t ask him what he thought; I just started to peel off some of the black tape. He trembled before me, but as I stepped closer, Charles shut his mouth so I could place the tape over his lips.

  Then I pressed my chest against his, making sure he could feel how hard my nipples were. “I was touching my nipples, pinching them. I’d let you do it, but your hands are otherwise engaged.” I laughed, but stopped when I looked at his cock, which was making a wet spot on his underwear.

  “In fact, I’m doing it now,” I said truthfully as I returned to massaging my nipples, only this time I also sank to the floor and ran my tongue along the outline of his cock. I was suddenly eager to touch it, pulling the waistband down and letting his erection pop up in front of me. Kneeling before him, I took his cock in my mouth. I liked that he couldn’t do anything but stand there. No, it wasn’t “torture,” but it was different from our usual blowjobs, where he talked dirty to me and told me how naughty I was for loving to suck cock. This time I was in charge, and I savored every minute. I spent plenty of time fondling his balls, and when I deep-throated him, instead of staying down there, I did it for just a second or two, before pulling back. Usually I let him come in my mouth, but this time I wanted to fuck him.

  “I’m going to release your arms so I can reposition you, but I’m going to keep the blindfold and tape on, and then I’m going to fuck you. You’re going to wait to come until I do. Do you understand?” He nodded his head.

  I unfastened the cuffs and led him over to the bed. He settled onto his back and dutifully raised his arms so I could reattach the cuffs, weaving their chain through the headboard’s slats. I straddled his hips, sinking my wet cunt onto his shaft. This felt new and exciting, because he couldn’t see or talk to me. I took the opportunity to call him my slut and “a pretty little thing in your pink blindfold.” His cock responded mightily, so I kept going, rocking back and forth energetically. When I was about to come, I leaned forward and impulsively ripped the black tape off his lips simply so I could kiss him.

  For a moment, I wished I had his hands on my hips or grabbing my ass. Then I forgot about that as I rode him to climax. I realized I could’ve teased him by getting up and leaving him with a hard dick, but I’m not that sadistic. I kept riding him, knowing it was only a matter of time before he gave me his come. When I tweaked his nipples, that’s what pushed him over the edge. He filled me with his cream as he moaned with delight.

  I slid off Charles and removed the blindfold first, then the cuffs. “Wow,” he said.

  “I know.” I grinned. “That was intense. I wasn’t planning on topping you.”

  “I’m glad you did—that was hot.”

  That trip to the toy store really opened up a new world to us, one in which my boyfriend is my submissive lover—and we couldn’t be happier.

  —Ms. Lila R., Alameda, California

  She’ll Keep Her Neighbor’s Sissy Secret—for a Price

  While my boyfriend commutes to work every day, I toil at home. I run my own business from my home office, which is on the second floor of our rented house. My office window happens to overlook our neighbor’s patio. I usually hear nothing from next door during the day. However, several weeks ago I heard the clicking of high heels on the concrete driveway. My first thought was that my neighbor, Todd, had a female friend over at his house, and being a little nosy, I thought I’d take a peek.

  I went over to the window and looked outside. I saw a cute blonde dressed in an adorable French maid outfit. I was careful to keep my presence a secret because I didn’t want to interrupt the romantic play that I figured Todd and this woman were having. But then something happened that threw me for a loop: The woman’s cell phone rang, but when she answered the call, I heard Todd’s voice! My God, I thought, Todd is a cross-dresser!

  I stood by the window, listening and watching, and I finally went downstairs and opened the sliding door, which led out to the backyard. I quietly kicked off my shoes and snuck closer to the fence. I peered through, and, yep, there was Todd in full makeup, a blonde wig, and that sweet French maid uniform. I climbed up onto a lounge chair near the fence, looked over, and startled the hell out of him. He realized right away that I’d discovered his secret, so he didn’t run. He knew it was too late for that. He stuttered and stammered, telling me that he liked to dress up while he cleaned his house, adding that he thought I’d gone for the day because he saw my car pull out of the driveway that morning. What he didn’t realize is that my boyfriend’s car was in the shop, so he’d borrowed mine.

  Todd stood there staring at me, his beautiful face blushing. I took it upon myself to make the next move, and came around the fence to pay him a more personal visit. Once I was there, I made him strut around the yard. Those four-inch heels made a sexy click-clacking sound, and when he twirled, his white petticoats flared out. I loved the way he looked. To be honest, it kind of turned me on.

  Todd looked worried and begged me not to tell a soul. With a twinkle in my eye, I told him I wouldn’t—but that it would cost him.

  Since Todd worked the twi
light shift, from four o’clock to midnight, I knew he had the daytime free. I suggested that he could be my maid, because I hated keeping house while trying to operate my business. That suggestion must have hit a submissive nerve in him because he jumped at the chance. I took him by the hand and pulled him over to my house. I instructed him to get busy washing the dishes. Since it was Friday, I told him I would make up a list of his weekly chores, and that on Monday I expected my maid to appear promptly at nine in the morning.

  On Monday morning, Todd was on my doorstep in his freshly laundered and ironed French maid uniform, including stiff, white petticoats and a white lace cap perched atop his blonde wig. I showed Todd his work schedule. Every morning, he was to wash the dishes from the night before, wash the breakfast dishes, prepare my lunch, and clean up afterward. On Monday, he had to change the linens on the bed. Tuesday he had to do the laundry and ironing, as well as vacuum. Wednesday and Thursday were for odd jobs, like dusting and cleaning out the refrigerator. Each afternoon before my boyfriend came home, Todd had to water the plants in the garden. If there were no other chores to do, I’d put him to work performing secretarial duties in my office.

  I soon found that with Todd’s help, I was able to generate more revenue. I decided to reward Todd with gifts of new dresses—smart-looking professional outfits that added to the atmosphere of a real office. After doing his housework in the morning, Todd would change from his uniform into his business clothes and become my pretty secretary. He looked beautiful in a dress, hosiery, and heels. We started taking breaks away from the house, having lunch at local restaurants and shopping together at the mall. Todd and I became close friends.