Letters to Penthouse XXXXV

by Penthouse International

  “Yes, ma’am. Please cane me,” he said. Normally that wasn’t something I’d do on a first date, but Matt was so eager, I couldn’t resist his cute, perfect butt. I rapped the toy against his ass, relishing its sound as it landed. Then I did it again, each blow forming a thin red line on his buttocks. I kept going, striping his skin until he was trembling in my lap. I gave one final, extra-hard blow, then pushed the toys aside to alternately pinch, fondle, and gently stroke his bottom. When he sat up, his dick was impossibly hard.

  “Thank you, ma’am,” he said.

  “You’re very welcome. You may go now, and when you get home, I want you to masturbate and think about being tied up while I flog you. Then email me and tell me what that will feel like. If I like what I read, I’ll invite you back.” I sent him off with his raging hard-on in his pants while I diddled myself to a satisfying climax. I have no doubt that Matt will be back, and next time I plan to make him write to Penthouse Variations and detail every last moment of our session.

  —Ms. Suzanne M., Boston, Massachusetts

  Butch Domme and Her Girlfriend Are Tickled Pink

  Alice is my girlfriend—and my submissive. She thinks she has me wrapped around her sexy little finger, just because I’ve been known to melt when she sits in my lap and wriggles against me. I consider myself butch, even though there have been times I’ve let a woman top me. I do sometimes wear lipstick and have a great set of tits, but my preferred clothing is a leather jacket, a white T-shirt, faded jeans, and mean-looking black boots. Alice complements me by wearing sundresses, or tight miniskirts and tops, and bright-red lipstick that looks phenomenal with her shiny black hair and pale skin. She’s a knockout—and she’s as perverted as I am.

  We’re a great pair, and I often find myself thinking about her throughout the day, imagining the look on her face right before she comes, seeing her begging me to shove one more finger inside her or to spank her a little bit harder. She sometimes dresses up in Donna Reed–like homemaker dresses, and that’s when she wants me to play my roughest with her.

  Recently, I decided to buy her a present, though it was really a present for me, because I love nothing more than watching her squirm. This time, though, the present didn’t look sadistic or scary. In fact, it looked girlie and sweet and innocent, like her. It was a pink feather tickler I’d purchased from our local sex toy store. Sure, they’d had monstrously large dildos, nipple clamps, gags, collars, and other crazy devices, but the seeming innocence of this toy appealed to me. I also got some pink bondage tape and some furry pink handcuffs, because even though she likes to wear black, Alice also has a soft spot for girlie colors—and I like teasing her so much that one present didn’t seem like enough.

  I stuffed the toys in my backpack and texted her before I hopped on my motorcycle, telling her to be naked when I arrived. Since she loves adventure and surprises, not to mention nudity, I knew she’d be excited. She’s usually wandering around our house in only a bra and panties, anyway. She’s even answered the door dressed like that, to the amused—and aroused—reaction of pizza deliverymen, the mailman, and once even our landlord.

  My clit swelled with excitement and my nipples hardened as I thought about her pretty blonde hair and sensuous pink lips. When I turned my key in the lock, I felt her trying to open the door from the other side. I liked that she was as eager for me as I was for her. Both of us were ready to let everything else go while we indulged our carnal desires. When I got inside our place, I saw that Alice was, indeed, naked. The sight of her puckered nipples, sleek pussy, and pretty pink lips nearly made me swoon. I greeted her with an aggressive kiss, our tongues wrestling desperately, as if we’d been apart for weeks.

  “What’d you bring me?” she asked, an expectant look on her face.

  “What makes you so sure I have something for you?” I asked.

  “I can just tell.”

  “I think you need to sit down and wait for me—and not be such a smartass. Maybe your present is the chance to suck my cock, you horny girl.”

  That day, like most, I was packing a strap-on, because Alice gets giddy at the sight of a dick hanging from between my legs. Even though her eyes revealed her excitement, she obediently sat down to wait for me—but her patience didn’t last long.

  I took my time putting my things away, washing my hands, and getting a snack in the kitchen—basically I ignored her. Even though I was as horny as she had to be and eager to show her the toys, this little bit of role-playing enforced my dominance over her. Finally, I was ready, but when I walked into the living room, I didn’t find my sexy girlfriend sitting quietly in place. I found Alice sprawled across the couch, lying on her stomach. Her face was buried in the couch cushions, and she was energetically humping her fingers.

  “What are you doing?” I snarled.

  “Um, nothing?” she asked, sitting up and looking at me with the guiltiest expression on her face.

  I walked over to her and grabbed her hand. It was drenched with her honey. “Nothing? Then why are your fingers wet? You know, I bought some things for you just for fun, but now I have a real reason to punish you!” I scolded playfully.

  Alice mock-cowered before me, even though I knew she’d probably been diddling herself on purpose in hopes that I’d catch her. I told her to kneel on the cushions, facing the back of the couch, and to put her arms behind her back. When she did, I fished the handcuffs out of my bag and fastened them around her wrists. I picked up the tickler, and she squirmed as I ran it along the crack of her ass and over her bound wrists. She tried to kick out at me but lost her balance. I turned her around and leaned down to suck on one nipple. She let out a rip-roaring shout.

  “Shhh,” I said, as I played with the pretty pink tickler, making it dance across her breasts and then under her neck. Alice alternated between giggling and trembling with arousal. But when her laughter turned into loud moans, I pulled out the bondage tape.

  “Since you can’t keep quiet, I’m going to have to force you to behave,” I said. She knew I was serious, and she pressed her lips flat so I could place the tape over them. Though I love her squeals of delight when I’m fucking her, there’s something about seeing Alice gagged—whether it’s with a ball gag or a pair of panties or bondage tape—that gets to me.

  I continued tickling her, placing her on her back on the couch and then letting the feathers caress the soles of her feet, her inner thighs, and her pussy. Her sex was glistening with dew, and I was hungry to taste her, but I waited, teasing her until she was moaning loudly against the tape and thrashing all around. I played with her nipples a little, liking that she was so immobilized. Then I sat her up and got on my knees to eat her out. I’m not really a mean top; I love to give her pleasure, but like it best when it’s done my way. I thrust my hand down my pants and stroked my pussy as I ate her cunt.

  Feeling her respond to me while she was bound was exciting for both of us. I shoved my tongue deep inside her while using the tickler to stroke any bit of exposed flesh I could reach. Her orgasm hit her hard, and her pussy gushed as she moaned against the tape, which I then tore off because I wanted her to suck the extra-large dick I had stuffed in my pants.

  “You’re beautiful,” I told her, as I ran my finger over her lips. “Do you want to keep wearing the cuffs while you suck my cock, or should I remove them and free your hands?”

  Alice opted for staying bound, just as I’d expected, because that’s the kind of kinky girl she is. We switched places, so that I was sitting on the couch with my pants off, while she knelt before me and worshiped my dildo. As her head bobbed up and down on my cock, the base of it pressed against my sex, making me ache. Alice is the perfect cocksucker, alternating between slow and fast mouth actions. When her lips moved down to swallow my dick whole, I almost forgot that the faux cock wasn’t really a part of my body—that’s how good she is!

  Soon I was trembling with a climax of my own, one brought on by all the sexy friction and her lusty groans. I stood and pulled off th
e strap-on, and then Alice gently lapped at my sex until I grabbed her for a kiss. When I finally released her, she grinned at me and then picked up the tickler.

  “I wonder what you’d do if I used this on you!” And because I was in such a relaxed mood, I let her tickle me a little, until we collapsed in an aroused heap and finger-fucked each other to another round of orgasms.

  I can’t get enough of Alice, or our toy collection, and fortunately, neither can she!

  —Ms. Liz F., Via Email

  When the Ladies Come to Visit, She Hires a New “Maid” to Serve Their Every Whim

  When Steve and I married, I did not realize he was a football addict. That meant he and his buddies watched football in our media room every day possible. There were college games on Saturday, and pro games on Sunday and Monday. Not only did I feel like a football widow, but I was also being run ragged as their hostess. I found myself buying goodies and drinks for the game days, making sandwiches and dips, and serving snacks all the time. It was annoying, not only because it filled up my free time, but also because it interfered with my preparations for my weekly book club.

  The book club I belong to meets at our home. Since we have a spacious house, I had volunteered to host. That turned out to be a mistake. It was a chore preparing and serving snacks and refreshments for ten to sixteen women every week. Yes, the women chipped in to help with the cost, but I was the one constantly running to and from the kitchen. Realizing I was frazzled between his football gatherings and the book club meetings, Steve offered to reciprocate by serving my guests so I could enjoy time with my friends. I did not hesitate to accept his generous offer.

  For the first few weeks, everything went great. I was relaxed, and Steve was very helpful. The problem was the women. Some of them said that Steve’s presence put a damper on the conversation, especially when they were discussing the sexual prowess—or lack thereof—of their husbands and boyfriends, many of whom were friends with Steve. I explained that Steve was reciprocating for me being the hostess for his football buddies, but it didn’t matter to them. Finally, the girls decided to contribute ten dollars each so I could hire a maid, and they could freely gossip. The offer was appreciated, but it defeated the purpose of Steve pitching in.

  Steve and I discussed the issue, and I told him I did not want to let him off the hook so easily. He shrugged his shoulders, and I looked at the pile of money sitting on the kitchen counter. Suddenly, I had a great idea. Steve is not very tall, only about five-foot-six. He is slender and has gentle facial features, including extremely fine facial hair. I smiled and suggested that I could dress him up as a woman and he could serve my guests in drag. Steve laughed like crazy. He said there was nothing I could do to make him doll up as a woman. I told him maybe there was something I could offer him in return.

  This is the second marriage for both of us. Steve is thirty-five and I am forty. My first husband liked oral sex, but he had the nasty habit of forcing my mouth completely over his cock. He would hold the back of my head while he dumped his load down my throat. Because of his behavior, I swore that my next lover or husband would never get a blowjob from me. For five years I stuck to my guns and denied Steve, even though I knew he’d never treat me like my ex did. I coyly suggested that if Steve permitted me to dress him as a woman, I would give him a blowjob and swallow his load. I told him to think about the offer. I motioned to the pile of money. It was more than enough to buy him a nice outfit—nothing cheap like a French maid’s outfit, but a tasteful ensemble. Three days later, Steve agreed to try it once. If the girls discovered him, it would have been at least a good joke.

  That evening Steve and I went to the mall to get his clothes. I decided on a knee-length black skirt and a long-sleeved white blouse. In the lingerie department, I selected a lacy white bra in size 38A, white nylon panties, a white garter belt, and a lacy white slip. I couldn’t decide if Steve would look better in black or nude stockings, so I bought a pair of each. In the shoe department, I selected a pair of black pumps with modest heels. I didn’t want him tripping and falling all over the place. Lastly, we went to a wig shop. There I chose a long black curly wig that would come down past his shoulders. We passed by the makeup counters; because Steve and I have similar coloring, I’d have everything I needed at home to transform him into my perfect housemaid.

  Over the weekend, I had Steve walk around the house in his high heels in a feminine manner. I also instructed him in proper female decorum. I had him practice bending at the knees rather than bending over at the waist to pick up something. If he had to sit, I had him cross his legs in a modest fashion. And of course, I had Steve practice serving drinks and refreshments.

  On the fateful day, I had Steve shave his face, legs, and the backs of his hands and fingers. I filed his nails and painted them a vivid red, which would match his lip gloss. Fully made up and adorned with his black wig, Steve looked feminine and very sexy; my pussy was getting moist from the sight of him. My husband was silent as I helped him put on the bra and then hooked him in. I rolled the nude stockings up his legs and attached them to his garter belt, slid the white nylon panties over his sexy ass, and dropped the white slip over his slender frame. Next I had Steve don the white sheer blouse, which buttoned in the back. I loved the look of the straps from the bra and slip showing through the sheer fabric of his blouse, especially the lace of the slip. He stepped into the black skirt, which also buttoned in the back. Finally, I tied a white apron around his waist. Steve looked ravishing. He decided to call his femme persona “Alana.”

  Alana performed her duties flawlessly. She served drinks, snacks, tea, and coffee without drawing any undue attention. Of course, Alana was able to hear some rather risqué conversations, especially about some of her buddies, but she didn’t say a word. At the end of the evening, some of the women told me the conversation had flowed better without Steve around. I was thrilled. We had pulled it off! When the girls left, there was another pile of ten-dollar bills on the table. The girls expected Alana to be back the following week to serve us.

  Alana came over to me with a knowing grin. It was time for me to keep my end of the bargain. I stepped behind Alana, unbuttoned and removed her skirt, and told her to hold up her slip. I knelt before Alana and released her cock from her white panties, and she was suddenly my husband again—although clad in sexy lingerie. As I sucked on his seven-inch cock, I looked up at Steve with wanton eyes. I caressed his balls and took his cock down to the hilt, enjoying every minute of it. When he began to erupt, I took him down deep and consumed his entire load. I never had experienced such a tremendous amount of come from any man. After licking his dick clean, I stood up, glanced at the pile of tens, and asked if Alana was available for next week. Steve assured me she was, telling me that dressing as a woman was a small price to pay for such an expert blowjob.

  We took the money and went to buy Alana another outfit. The charade continued week after week. Alana presented herself in black skirts that went from knee-length to floor-length to mini. We bought black dresses and black jumpers, as well as more frilly white blouses. As Alana became more accustomed to high heels, their height increased up to five inches.

  It has been more than a year, and the girls are none the wiser, and Steve gets a blowjob every week. We did take it further than I thought Steve would be willing to go, but he seems to really enjoy dressing up as a woman. It turns him on, and not just because he knows he’ll be rewarded with oral sex. Once or twice a month, I doll Alana up and we go out to dinner and a movie or a play.

  In the evening, I love to dress Alana up in a nightgown and have “lesbian” sex with her. Sometimes after we have sex and my pussy is full of come, I’ll have Alana lick me clean. However, I only give Steve blowjobs after book-club meetings. Our sex life has never been better!

  —Ms. Larissa I., Portland, Oregon

  An Officer and Her Gentleman Switch Roles When She Needs a Proper Punishment

  My husband and I are both involved in law enforcement. I’m
a detective on the local police force, and he’s an attorney. A lot of people think that makes me the more powerful partner in our relationship, since my job is more rough-and-tumble, but that’s not how it works at all. At work, I may be a dominant woman with a harsh attitude, but at home, it’s Richard who’s the dominant one—at least in the bedroom.

  When it comes to sex play, we prefer a dominant/submissive relationship. After a long day at work, I like having someone I love and trust take control of me, and I know Richard enjoys it, too.

  When I got home from work last Friday, Richard was waiting for me at the door, a pair of handcuffs dangling from one hand. As soon as I saw the cuffs, I knew I was in trouble—and I was thrilled!

  “You’re late again,” he told me. “And you didn’t call. You know what that means.” It meant I was about to be punished, and that seemed like the perfect end to a long Friday.

  As soon as the door was closed, he ordered me to strip, and I shed my clothes slowly, doing the most seductive striptease I could manage, considering my excitement. He watched, amused by my attempts to arouse him, but I could tell that he was turned on, too.

  When I was naked, Richard handcuffed my wrists behind my back and guided me into our bedroom. He helped me kneel on the floor, then moved around in front of me. While I was naked, my husband was still fully dressed, but as soon as I was on my knees, he pulled off his belt and unzipped his fly. His cock was already hard, and when he pulled his pants open, it immediately sprang out. It was right in front of my face, and the tip bobbed only centimeters from my lips. I wanted to suck it into my mouth, but I knew I couldn’t do anything until Richard told me to.