Letters to Penthouse XXXII

by Penthouse International

  But the next morning, as we emerged from our blissful postsex sleep, I said to her, “I have an idea that I think could be a lot of fun for both of us. I want you to tie me up and tickle me, and you have one hour to make me laugh. If you succeed, then we have sex however and wherever you want—if you don’t, then I get to pick. Just the idea of not being able to move while you tease and tickle me has made me so hard,” I said, putting her hand on my cock so she could feel how stony my cock had become.

  “Okay, I’ll do it,” she said, her eyes twinkling. “But only if my friend, Helen, can join us. She’ll be there for backup, which is perfect because she loves tickling almost as much as I do.” Who was I to say no to another hot girl joining my fantasy? We scheduled our little tickle challenge for the next night, and from that moment on, it was all I could think about.

  Finally, the moment of truth arrived. At Beth’s request, my attire consisted solely of silk boxers. I was absolutely confident and figured that even on the off chance that I lost, I was still in for a sexy night. Beth had gone all out, procuring a special chair that would enable her to tie me firmly to it. First, she secured my arms to the chair, making sure they were extended upward so she had room to reach my armpits. I knew what was in store for me, and was slightly apprehensive about the tickling to come, but I was even more aroused at the pleasures that awaited me. Then she took a feather duster and trailed it along my skin, making sure to poke the ticklish toy under my arms while I bit my lip so as not to take any chances. Then the duster trailed lower, down over my nipples, which had hardened into little pebbles, and along the thin fabric of my boxers. When the warm-up was over, Beth peeled off my boxers, then cuffed my ankles to the chair legs. The sensation of not being able to move made my cock all the harder. I tested my bonds but happily found that I couldn’t escape, though that didn’t prevent me from wiggling, reveling in my bondage.

  Helen looked at the clock, then gave Beth the okay to start. Now, with a serious, determined look on her face, Beth began by lightly massaging me from head to toe. I wasn’t writhing too much, but when she began blowing warm air against my most ticklish spots, like along the side of my neck and under my arms, I started to squirm. Her fingernails trailed along my skin, searching for weak spots. She kept looking from her hands to my face, checking my expression to see if she could sense where she should pounce. If I twitched even a little, she giggled, as if hoping her laugh would be contagious. She pinched my cheeks and tweaked my nose, hoping for a sudden fit of laughs, but I held my own. My cock, though, was as hard as a rock, standing upright as Beth tried every trick she could think of to get me to crack up.

  I held out fairly well through the first half hour as Beth began repeating “kitchy-kitchy-koo” as she used a combination of her fingers, breasts, and the duster to get me to laugh. Helen joined her side, too, taunting me by saying, “Well, I guess he’s just not that ticklish.” Little did I know that they were about to gang up on my biggest weakness—my foot fetish!

  Helen walked toward me, the timer in her hand and a stern look on her face. “Let’s get serious,” she said, before running her fingers from my inner thigh, right near my cock, all the way down my legs. I twitched and squirmed as if trying to escape, even though the tickling was making me more and more aroused.

  Then, in a way that seemed choreographed, they each pulled up a chair on either side of me. Crossing their legs, the women slowly dangled their high-heeled pumps by their toes, right in front of me. I felt my face turn bright red with embarrassment; there was no way I was going to be able to resist their gorgeous feet lined up so temptingly before my eyes!

  I stared at the images of the soles of their shoes, and behind that, their delicately arched feet. They smiled as my cock began to twitch and bulge, and there was nothing I could do to relieve my arousal. “What do we have here?” Beth asked as she fondled my cock. Then Helen made a stealth attack, raising her foot to rub it under my armpit, while also giving me a view of her thong straining against her pussy lips. I was so caught up in Beth’s stroking of my cock and the beautiful image in front of me that I let a little giggle escape my lips, hoping they wouldn’t notice, but that was quite a futile wish.

  “Did you hear something, Beth?” Helen asked, revving up her actions, her hands roaming under my neck and her fingertips teasing my armpit at once. Beth immediately stopped stroking my cock, leaving it bobbing in my lap.

  “I think that was a laugh. And after only thirty minutes. That’s all you could hold out, Chuckie?” she asked, her mouth curving into a smile. Then both women began to fiendishly tickle me, one at my feet, one at my ribs and underarms. I was so weak from the foot tease, I was completely lost and my laughter echoed loudly through the room as they proceeded to tease my whole body, every touch of theirs setting off a new round of giggles until I was guffawing hysterically. I could hardly stop, though I was hoping that soon they’d pause in their tickle torture to pay some attention to my cock.

  But those gals had something else in mind. Beth took a deep breath, trying to stave off her own laughter, then pulled away and sat back in the chair. “Helen, come over here for a minute, I need your help with something,” she said, her voice trailing off breathlessly, and when Helen looked up, Beth was naked in her seat, her legs spread as her fingers stroked her pussy lips. Helen’s eyes went wide, and she immediately stopped tickling me and crawled straight on over to her friend’s delicious offering, our tickle game forgotten as she dived between Beth’s legs to lap at her cunt. The lusty sounds of her oral attentions made me moan, and I writhed against my bonds, to no avail. This was a new level of temptation, and I thought I might come without anyone touching me at all. I watched Beth’s eyes shut and her hands clamp down on Helen’s head as she ground her pussy against her friend’s mouth until she came.

  You might think that after all that waiting, strung up in my chair, they would have untied me, but they weren’t done having fun with me yet. They did, however, finally take note of my cock, and Beth rewarded me with a smile. “Well, Chuck, you failed to live up to your promised goal, but you’ve been a very good boy otherwise, so I think you deserve a blowjob. But there’s a catch—I’m going to suck your cock while Helen continues to tickle you.” I opened my mouth, not sure what I would say or if I should pretend to protest. But the minute her sweet lips parted and took my cockhead between them, I knew that I’d be more than happy to “suffer” any amount of tickling for this exquisite sensation. I laughed and moaned as Helen used her nails and fingertips to get at my most sensitive spots, scooting around Beth, who had swallowed my entire cock between her gleaming wet lips. Both women were doing such an excellent job at their respective tasks, I felt like I’d died and gone to some special kind of kinky heaven.

  As Beth began to speed up, sensing that I was about to come, Helen put an end to her tickling and instead offered me a nipple to suck on. I flicked her nub, watching as she slipped a hand between her legs to play with her pussy, and my mouth got more animated as Beth kept up the pressure until I simply had to come. “Yes, I’m coming!” I screamed as I pumped a load of hot come into Beth’s mouth. I could feel her swallow once, then again, making sure she got every last drop, while Helen also sighed with pleasure as she reached her climax.

  When the girls finally unleashed me, we were all grinning. “Well, you two proved to have better tactics, but I think I still came out a winner. But the most important thing is that we all came!” They laughed with me, and I pulled Beth close for a kiss. When I’d pegged Beth as the type who’d be up for anything, I hadn’t really been expecting things between us to get quite so wild, but with Beth, you never know what’s in store. I can’t wait to see what our sexual future holds.

  —Mr. Chuck H., Portland, Oregon

  Spanking Machine Gives Single Guy What His Ass Truly Needs

  When I was twenty-five, I discovered the one thing that turns me on the most: getting spanked. As a successful football player in college and then a budding investment banker, i
t had never occurred to me that instead of being the one in charge in the bedroom, I could bend over and receive the most glorious sensations from a dominant woman. When one particularly feisty girlfriend, Carla, encouraged me to see what being smacked on the ass felt like, I discovered a whole new world of pleasure. I still sometimes jerk off thinking about the way she hit me, her palm landing in the perfect spot and sending shivers of excitement rippling through my body. She was into it, too, and not only knew where to strike for maximum impact, but told me what a greedy boy I was for wanting to be spanked so hard.

  But ever since Carla and I split up, I’ve never been able to duplicate that same spanking magic with another woman. Some have made halfhearted attempts, but I knew they weren’t really into it, which made it harder to lose myself in the moment. Plus, my job had gotten busier, meaning heavier travel and less time to meet women. So when I was browsing online and saw a Web site advertising a spanking machine, I knew I had to have it. My job is such that I have more money than time, so instead of wasting my rare free evenings searching for the perfect domme to spank me into submission, I would buy a machine to do it for me! It cost many hundreds of dollars, but I could well afford it, and I knew it would be worth every penny for the chance to get spanked heartily whenever I desired.

  When the large box arrived on my doorstep, I felt my face turn red as I signed for it. Lugging it into the house, I could already feel my cock responding to the impending promise of as much ass-smacking as I could take. I opened the box and immediately set up my new “workout” machine in my gym—this would be one exercise I’d never complain about! The instructions were simple, and I soon had the machine assembled. It featured a large paddle that I could activate to automatically keep on spanking. I undressed in a flash, momentarily stroking my hard cock before climbing aboard.

  I turned the toy to its lowest setting at first, finding that even those simple smacks made me whimper out loud. It had been so long since I’d gotten properly spanked that everything felt good. The paddle was stiff and strong, delivering powerful smacks. I wiggled around, positioning my ass so the wood hit me flat across both cheeks. Knowing that it could go on as long as I desired made me even more relaxed—I didn’t have to worry about anyone’s arm getting tired. Instead, I indulged in the sheer hedonism of hearing the loud slaps and feeling them reverberate throughout my body.

  I reached beneath myself to hold my cock, letting the spanking machine do its work. Then I decided to crank it up, having gotten used to the intensity of the smacks it was delivering. I rested my head against the leather bench, inhaling the pungent scent of the upholstery as the whacks came harder and more frequently. My butt was getting pleasantly warm, and with each round of blows, my ass acclimated to the sweet pain of the paddle. I began talking out loud to the imaginary mistress overseeing my necessary punishment.

  “Yes, I’ve been a bad boy. I deserve everything you’re doling out. Please, don’t stop. I haven’t learned my lesson yet,” I babbled as I submitted to the machine’s thwacks. I was stroking my cock, clutching my hardness in my fist as my ass turned pink. I wanted to wait a while before climaxing, so I turned the machine off and went to admire my behind in the mirror. The machine is truly a miraculous invention—there’d be no way I could ever properly spank myself, and it did a better job than any person ever could. I suddenly realized why women love their vibrators as much as they say.

  My buttocks were warm to the touch, and my normally white skin was streaked with shades of pink. When I squeezed my ass cheeks, I gasped at the pleasurable feeling that coursed through me. Clearly, it was time for more spanking. I climbed back on top of the machine, settling in for an even more intense session. This time around, I cranked it up to maximum capacity. I was immediately struck with unrelenting blows from the paddle. It showed no mercy, but gave me exactly what I wanted—to be spanked long and hard. I’m tough, and once I’ve been warmed up, my ass can take a lot, so letting the mechanical paddle wallop my hungry buttocks again and again was like a dream come true, harking back to those heady, halcyon days under Carla’s powerful hand.

  With my ass raised in the air and my cock throbbing, I felt totally submissive and surrendered to the machine. I looked behind me, almost expecting to find Carla standing over me to make sure I took my punishment. Each whack stung, but was followed by those ripples of pleasure that are unlike any other erotic sensation, including sliding my cock into a woman’s tight, wet pussy. Getting spanked gives me something no other activity can, and it doesn’t matter who’s doing it—a woman or a machine. I let the paddle strike both my ass cheeks at once, my cock responding to each blow. The more I took of the paddle’s vigorous hits, the closer I got to my orgasm.

  I shut my eyes and, with my hand jerking my dick, I reveled in the machine’s blows, enjoying them after such a long hiatus from my favorite activity. In fact, the more I got spanked, the better it felt, with the wood landing in the same spot over and over again. The machine was bringing me to incredible heights of uncontrollable arousal.

  “Yes, make my ass red!” I cried out to the air, wishing that I had an audience to see the paddle slapping against my ass. Instead, I had the sound of each whack ringing in my ears and the excitement of feeling my butt literally taking a beating. I shifted once again so the paddle landed on my upper thighs. I braced one hand on the bench—holding tightly—and used the other to frantically stroke my desperate dick.

  I knew the machine was configured so that someone could be strapped down to it, and I could see why—as much as I enjoyed the blows, my natural instinct was to squirm around when the feeling became intense. Instead, I told myself to count to ten, and that I’d have to come within that time frame or else the machine would be turned off. I squeezed my fist tighter around my length, while the machine kept right on spanking me.

  I met my self-imposed deadline with two seconds to spare, spurting a load of hot white come all over the seat. Fortunately, the manufacturers must have assumed people would be prone to ejaculating on their furniture. When I turned the machine off and got up, I found it easy to clean. I left my new toy set up in the middle of the gym and headed out to take a shower, before sinking back against my cool sheets, which were the perfect balm to quickly soothe my tender butt cheeks.

  I hope that someday I’ll find a woman whom I can share the excitement of spanking with; maybe we could even take turns submitting to the machine’s strokes. For now, though, I’m more than content to indulge in my love of spanking all by myself, with a little help from my mechanical friend.

  —Mr. (name and address withheld)

  My Husband Gets What He Deserves When I Cotop Him With My Hot Friend

  I’d always shared many secrets about my sex life with my best friend, Nicole. There was nothing that my husband, Mark, and I did together that she wasn’t privy to, as is the way of many best friends. But my wicked little Nicole has an even dirtier mind than I do, and as I told her about our erotic adventures, little did I know she was cooking up some scenarios of her own. Although she knew all about our sex play, she and I had never crossed the line and played together—until recently.

  When I said to her, “I’m in the mood for something different lately, something wild,” I was hardly anticipating her reply.

  She looked at me, then tilted her head back and seemed to mull over my question before turning back to me with a cunning smile on her face. “Let’s go up to my cabin next weekend and take Mark with us. We can top him together,” she said, her eyes lighting up at the kinky prospect. When she saw the look of shock on my face, she was quick to reassure me. “Don’t worry, Laura. I don’t have designs on your man. I’ll watch for the most part and be there to guide you. I think it’d be a hoot to see him doing our bidding. Don’t you?”

  As she talked about it, I was envisioning Mark wearing only a skimpy pair of tight briefs as he knelt before both of us. Even before I spoke, I felt a stirring in my pussy that let me know this was something I needed to try. We weren’t tot
al newcomers to kinky play, but she sounded like she was going to up the ante in our BDSM stakes. “Okay,” I said. “Let’s go for it.” I had a feeling Mark would be more than amenable, especially since Nicole was involved. Sure enough, when I told him, he got a huge hard-on and told me he’d be happy to serve us both. While he’d never formally said as much, I’d always suspected he’d had a little crush on her.

  In fact, he loved the idea so much that he had already moved from our casual, everyday mode of interaction to his fully submissive posture. Kneeling adoringly at my feet, he said, “It will be my honor to serve my mistress in any way she desires.”

  I knew it would be both an honor and a pleasure, but I didn’t say anything else to him. Instead, I let him lick my aroused pussy to show how delighted he was with this new state of affairs.

  Ever since I first brought up the weekend trip, he’d been asking me what was going to take place. I finally had to tell him that the more he talked, the more I was going to ignore him, but the truth was, I didn’t really know what Nicole had in mind for us, and part of my growing excitement was coming from the idea of following her lead.

  I called her before the trip to see what I might need to bring. “Just relax, Laura. I’ve got it all under control. You know how to handle him. Make sure you dress sexy and I’ll take care of the rest,” she promised, and something about the tone of her voice let me know she wanted to take care of me, too.

  For the ride up, I wore my shortest skirt along with a sheer red blouse, no bra, and killer high heels. After all, I wasn’t going to be the one driving! One of the perks of having a submissive partner is that I get to delegate certain duties, like driving. He gathered our luggage and loaded it into the car while I sat in my seat, admiring my shoes. Then he drove off, stopping every time I told him I needed to get something to drink or a snack. He would immediately pull over, get it for me, then quickly return to the car.