Letters to Penthouse XXXXIX

by Penthouse International, Nikki J, Samantha St. Charles, Lorenzo De Leon

Genres: Women's Fiction; Romance Anthologies & Collections

Synopsis

In this edition of Letters to Penthouse, men and women confess every exquisite detail of their torrid affairs, sensual adventures, and wild one-night stands. No adventure is too daring-no kink too dirty. Married couples, perfect strangers, frisky friends, and randy roommates mix and match their desires-and share every sizzling detail of their erotic exploits.

Release date: May 27, 2014

Publisher: Grand Central Publishing

Print pages: 368

Sample

Matt and I went to our friends’ last house party with only one objective in mind: to swap partners with Elaine and Ralph. The two of them are in an open relationship, and Matt and I swing, so we knew it was possible. We’d wanted to swap with them for months, but we’d never really had the chance. Their party seemed like the perfect opportunity.

We had a good time drinking and talking with everyone, and the rowdy game of charades that broke out was surprisingly entertaining, too, but we couldn’t wait for things to wind down. As people started to leave, Matt and I made a point of offering to stay behind to help clean. It would get us alone with our hosts and open the door for some sexy swapping.

After the last guest left, Matt and Elaine started picking up the discarded cans and cups while Ralph and I rinsed out beer bottles and washed dishes. I started flirting with Ralph as soon as we were alone in the kitchen, touching his arm and bumping into him whenever I tried to move around the room. He flirted right back, copping a feel whenever he could and saying everything in a suggestive manner. Even “You wash, I’ll dry” managed to sound dirty when Ralph said it.

We were in the middle of washing the dishes when Ralph accidentally splashed some water on me. It soaked through my thin white T-shirt in no time, and I playfully fought with him, assuming he’d done it on purpose. In the middle of our struggle, Ralph grabbed my head in his hands and pulled me in for a hot kiss. I dropped the sponge I was holding, and the empty tumbler, and kissed him back, forgetting all about the dishes I’d volunteered to wash.

As we kissed, my wet hands traveled under his tight T-shirt, while he worked his fingers into the loose waist of my shorts. We touched each other everywhere we could reach, and when we ran out of readily available flesh, we started pulling off each other’s clothes.

As we stripped, shirts flew one way and shorts the other, but it wasn’t until we were down to our underwear that we realized we didn’t want to get it on in the messy kitchen. Ralph grabbed my hand then and pulled me into the living room, but he stopped almost as soon as he walked through the doorway. On the futon across the room were Matt and Elaine, already midfuck. It looked like our partners had gotten a head start!

Ralph and I stared at them for a minute, then he dragged me into the room and headed for the couch. He sat down across the room from the other couple, pulled me into his lap, and resumed kissing and fondling me.

Ralph made a move to unclasp my bra, and as soon as it was off, he leaned in and started sucking my tits. He laved my nipples with his tongue, then traced circles around each areola. He was driving me crazy with his attention to my tits, and I started moaning quietly, my noises blending with the moans and groans coming from across the room. He kept at my nipples for a while, but eventually I pushed him away and moved in to take a turn sucking his nipples instead. He seemed to like it, and I felt his cock twitch against me through our underwear as I nipped and sucked on the tiny buds.

The nipple play lasted for maybe five minutes before we finally stood up from the couch and pulled off our underwear. As I stepped out of my panties, I glanced over at the futon and saw Elaine on top of my boyfriend, riding him in the reverse cowgirl position. They were maybe ten feet away from us, so close that I could almost reach out and touch them, and watching them going at it was really getting my juices flowing.

Once Ralph had his underwear off, too, he pulled me back on the couch, this time pushing me onto my back and then joining me. He put one knee on the couch and left his other foot on the floor, then pulled me into his lap, angling my hips upward a bit. As he slid his cock into me, the position seemed to make him go deeper than his seven-inch cock should have allowed, and he filled me nicely.

He had me moaning from the first thrust, and I only got louder as he picked up his pace. As he continued fucking me, he used one hand to hold me in place while he moved his other hand to my pussy and started to rub my clit. While he was focused on me, I turned my head to look at my boyfriend again. Elaine had turned around by then and Matt was sucking her tits while they fucked, or at least he was trying to. He seemed to be having a hard time reaching her tits with her still riding him.

Watching the other two humping each other was arousing, and the more I watched them, the harder I tried to meet Ralph stroke for stroke.

Ralph kept increasing the pace as he fucked me, and soon he was banging me hard, his balls slapping against my ass as he pumped into me. His finger was moving faster on my clit, and my climax built as we fucked. I felt my body tingling with pleasure, and then it seemed as if waves of excitement were washing over me. Ralph had made me come faster than anyone had in a while, but he didn’t stop fucking me yet. He didn’t even slow down.

He pounded away at me, bringing me to a second, equally explosive climax before he finally came himself, and he pulled out in time to shoot his load across my stomach. I love watching my partners come, and I loved that Ralph knew to do it without being told when and where. It’s so much hotter when the guy doesn’t have to ask.

After he came, he moved to sit on the couch, and I collapsed on my back before turning to see what the other two were doing. I’d been so caught up in my own pleasure that I hadn’t been paying attention to them, and I saw that they’d finished by then, too, and were already curled up on the futon, half asleep.

Ralph and I rested for a few minutes, catching our breath, then took a shower together—and fucked one more time—before getting back to work cleaning up the house. By the time we’d finished, Matt and Elaine were awake. My boyfriend and I left then, but as soon as we got home, we celebrated our successful swap with a wild fuck before crawling into bed for some much-needed sleep.

—Ms. Rebecca R., Longview, Texas    

My wife, Sophia, is a total clotheshorse. I don’t mind, because she has a beautiful body. I’m happy to support her shopping habit if it means I get to see her in sexy outfits. Whether she’s donning see-through lingerie, tight short-shorts, miniskirts, or tops that accentuate her large breasts, I’m a fan.

Recently, however, one of her shopping adventures led us to explore something new: cross-dressing. Sophia was sitting in front of her computer while wearing a matching pink and white bra-and-panty set as she shopped for new lingerie. She was so excited about a new nightie she was about to order that she called me over to look at it. It was a sexy little number in leopard-print, with lace along the edges.

“Can you picture me in this?” she asked dreamily. I sure could, and my cock instantly hardened at the image my mind conjured.

I whispered in her ear, telling her exactly what I’d do to her while she was wearing it. My dirty words were followed up with kisses along her neck as I caressed her breasts and teased her nipples into taut peaks. In hindsight, I can tell that my little distraction is what caused her to order the wrong size. It was an error that we didn’t discover until two days later when her package arrived. There was my sweet Sophia, ripping open the envelope, eager to see her new nightie. Imagine her surprise when she realized she’d received an extra-large, rather than a small.

My wife was only mildly disappointed. Exchanging it would be easy enough, she explained to me as she held the garment against her body and looked in the mirror. She scrunched her brow as she assessed the nightie, as if confirming that it was indeed too large for her. Then her facial expression changed, and I could tell that she’d gotten a wicked idea.

“Come here for a sec, honey,” she said in a singsong way that let me know my hunch was correct. “Obviously this is too big for me but… I think it would fit you.”

I stared at her, a little stunned. Me? Try on a women’s nightie? She held it up to me, raising herself up on her toes to reach my shoulders. I’m six feet tall—nearly a foot taller than her.

“I think you’d look good in it,” she purred.

As much as her suggestion surprised me, I also realized that my cock was rapidly hardening—and it stiffened even more when I snatched the silky garment from her hand.

Sophia nodded at me encouragingly, and I headed into the bathroom. I quickly stripped and slipped the silky nightie over my head. Sophia was right; it did fit me. Well, it might’ve fit better if my hard cock weren’t tenting the front of it, but that couldn’t be helped. The sensual fabric caressed my skin, feeling so different from the cottons and polyesters that I was used to wearing. I liked the way my nipples showed through the lace cups, and I admired myself in the mirror for a few minutes before returning to Sophia, wondering what her reaction would be.

She eyed me up and down, and I felt myself blushing. It was clear that she was ogling me the way guys check out girls… and I liked it!

Sophia walked toward me, and her smile was that of a pure sex kitten. She placed her hand on my chest, her fingertips toying with the lace trim. “Hey, hot stuff,” she said in a deep, sensual voice.

“Hey,” I responded, not able to say or think too much. My achingly hard cock was a distraction, one that only grew as she slid her hand down my body to caress my erection through the silky material. Her handjobs are always wonderful, but this time was different. The way my body was responding to these new sensations and the gleam in her eyes told me that this wasn’t the last time I would be dressing in clothes meant for a woman.

Feeling the soft fabric caressing my shaft brought me to the edge of climax, and when she got on her knees, dipped her head beneath my nightie, and started sucking my dick, I was a goner. I came in giant spurts of hot cream, rubbing the fabric against my chest as Sophia gobbled up my load.

I loved the feeling of that negligee so much that Sophia ordered me some panties that were made of a similar fabric in a rainbow of sensual colors.

When my panties arrived, Sophia told me she was going to select which ones I should wear first. They weren’t just different colors, but different styles, too—French-cut briefs, lacy bikinis, and even a hot-pink thong! I didn’t think the latter would work well on me, but I was game. Besides, the idea of wearing panties my wife had selected for me added a layer of hotness to the whole endeavor. “Let’s try these,” she said, holding up a pair of purple lace bikinis.

“Okay,” I said eagerly, then took my clothes off right there and stepped into the delicate panties. I slid them up my legs and adjusted my stiff cock, aware that my erection was threatening to crest above the waistband. The panties couldn’t really accommodate my hefty package, but I think that only made it a more sexy sight. The panties fit snugly, and I enjoyed the tight fit as much as I enjoyed the texture of the lace hugging my cock and balls.

I looked at Sophia and saw that she’d dipped her hand into her own panties. “You look so hot, baby.” She stepped closer and stroked my balls through the fabric with her free hand. “I want you to fuck me while you’re wearing those,” she said as she peeled down the waistband just enough for my cock to poke out.

“I’ll fuck you however you want me to,” I told her, and then she led me into the bedroom, got naked, and ordered me on top of her. With her hands fondling my lace-covered butt cheeks, she guided my dick into her pussy. Knowing she was excited, plus the feeling of the panties against my skin, made me even more aroused. I plunged into her cunt, feeling her fingers clutching and releasing my ass as I thrust in and out of her.

“I’m not gonna last long, baby,” I warned her. I shut my eyes as I focused on her hot, tight pussy surrounding my pistoning cock, her hands gripping my bottom, and the silky panties bunched against my balls. Soon I was coming, pumping my seed into Sophia.

“Yeah, I want it,” she said, “all of it.” I gave her as much as I had in me, then I stayed nestled inside her as I kissed her. When I finally pulled out and took off the panties, they had some of Sophia’s juices on them, as well as my come.

“I think the thong should be next, and that you should wear it tonight—when we go out to dinner,” she proclaimed.

As I thought about the top of the pink thong peeking out over my jeans, I got turned on. I put on the thong and discovered that the way it ran along the crack of my ass—something I’d heard Sophia complain about when she wore this style—actually felt good. It was stimulating in a different but just as arousing way.

“We need to get you more thongs,” she said matter-of-factly as she groped my behind. “That makes your ass look amazing.”

The two of us went out to dinner, and knowing that I was wearing panties the whole time turned both of us on. When we got home, we fucked like crazy.

Having me wear lingerie has definitely added some extra spice to our lovemaking. Who knows what Sophia will have me wear next?

—Mr. Dave S., Minneapolis, Minnesota    

 

While many of my friends went on fun vacations during winter break, I had to forgo that luxury. I needed to get a job in order to sustain myself through my last semester of college. I was having a tough time finding a position and was starting to despair when I spotted a flyer at the supermarket. A woman in the neighborhood was looking for a guy to do lawn work and some home repairs. I thought I was qualified, since I had experience doing various odd jobs, like house-painting and carpentry, so I decided to go for it.

I called the number on the flyer and made an appointment to meet the lady of the house that afternoon, promptly showing up at the appointed hour. The woman who answered the door was really pretty, with her brown hair swept back and a hint of wine-colored gloss coating her lips. She was older than me, so I assumed she was married. “It’s nice to meet you, Mrs.…” I said, fishing for her last name as I shook her hand.

“Call me Kate—and there is no mister,” she immediately replied, looking me up and down. It seemed like she was sizing me up for something other than what the flyer had advertised. I’ll admit that even though I was feeling a little uncertain, my cock twitched in my jeans. She might have been older—but she was hot.

After that brief pause, Kate asked me about my experience and nodded approvingly. She then led me through her home, pointing out areas of disrepair. Her place was huge, the biggest house I’d ever been in, and though it was in pretty good shape, she showed me which rooms she wanted repainted and noted a few things that needed to be replaced or repaired, like broken doorknobs and cracked floor tiles.

We chatted for about an hour, though it was less like a formal interview and more like a casual conversation. Kate was at least fifteen years older than me, and I was impressed by her poise and natural beauty. She told me that she’d been married but had been divorced for two years. As she spoke, she pulled a clip out of her hair and shook out her tresses, making her look even more beautiful and carefree. I was incredibly attracted to her. Up until that point, I’d only had sex with one girl. It had been okay, but the experience wasn’t earth-shattering. I couldn’t keep myself from wondering what sex with Kate would be like. Her self-assured nature and years of experience were like an aphrodisiac to me.

As she continued her tour, I tried to pretend I was paying attention to what she was saying, but mostly I was checking out Kate’s ass and daydreaming. She was wearing jeans, which I hadn’t expected because her house was so lavish, but the denim hugged her ass perfectly. Although her figure was trim, she still had a lush bottom. My mind was instantly flooded with images of me kneeling behind her, tonguing her curvy behind, which made my cock stiffen immediately. I had to get my hard-on under control or I might get fired before I even started!

I took a few deep breaths and managed to quell my arousal somewhat, thinking of anything but what she’d look like naked. Kate asked me when I could start, and I told her immediately. She was pleased, telling me I was hired and asking me to join her for lunch. I gladly did, and realized that I enjoyed talking to her as much as I enjoyed looking at her.

I started the very next day, and I quickly found that her list of daily tasks was not enough to fill an entire eight-hour workday. To pass the time, I started to explore her home, spending much of my free time in her library. Though one day I passed by her bedroom and the door was ajar. Kate was out getting a massage, and I knew she’d be gone for at least two hours. Unable to resist, I opened the door and wandered inside. Just standing in her bedroom made me horny, and I wondered when Kate had last had sex.

As I stood daydreaming near her bed, Kate’s housekeeper walked by and clucked her tongue. “You shouldn’t be in there. I’m going to tell Kate you were in her room,” Pamela said.

“I’m sorry,” I said, flustered at being caught where I shouldn’t be. “It won’t happen again.”

Pamela shook her head and walked off. I scurried out of the room, embarrassed and nervous about what my boss’s reaction would be.

When Kate returned, I steeled myself for the inevitable firing—except that’s not what happened. Kate called me into her office and told me to shut the door. “Pamela told me she saw you in my room today.” I started to open my mouth, not to deny the charge, but to apologize. However, my sexy boss cut me off by raising her hand. She leaned forward and said in a low but urgent voice, “I want you to tell me what you were doing in my room without my permission.”

“I wanted to see what it looked like. I was curious about you—” Kate cut me off again with a gesture. I was sure I was blushing.

“Your behavior is inexcusable. While I’m not going to fire you—I will have to punish you.”

My cock was rock-hard in one second flat. The stern look in her eyes told me she meant business, and I can’t lie: I was totally turned on. Kate stood up and walked toward me, stopping right in front of me. I was trembling, overwhelmed with relief that I wasn’t getting fired, but nervous and aroused over what her punishment might entail.

“I have a feeling that you want to be punished. Most bad boys do.” She smiled at me, not wickedly, but almost sweetly. “Now, before we begin, I want you to tell me what you were thinking about while you were standing in my room.”

“I was thinking about what you might look like when you’re in bed. Whether you sleep naked or wear lingerie.” I looked at her, and she was staring intently at me, so I added, “And whether you use a vibrator or your fingers to get yourself off.”

“My, my, you’ve been doing a lot of thinking about me,” she said. “Did your cock get hard from thinking about those things?”

“Y-yes, it did,” I answered.

“Well, then, we’re going to go into my bedroom right now, so you can show me how hard you get.”

Kate marched me into her room, and on the way, we passed Pamela, who’d ratted me out. I wondered if she’d ever been subjected to one of Kate’s punishments. Nobody said a word, but I felt Pamela’s eyes on me as we passed. Kate led me into her bedroom and shut the door, making a show of turning the lock.

“Take off your pants and stroke yourself. Show me what you’ve got,” she said, without missing a beat.

I lowered my pants and took my dick in hand, looking at her for approval before I started stroking it. Normally I go very quickly, but I sensed that Kate would appreciate a slower show. It was very different from jerking off at home alone because I was all too aware that she was staring at me.

I lazily stroked my meat while Kate silently circled me, eventually stopping a few steps behind me. My hand stilled, and Kate slapped my ass—hard. “I didn’t tell you to stop,” she hissed in my ear.

“I-I’m sorry, Kate,” I said, resuming my stroking as she started spanking me. She was stronger than I gave her credit for, her delicate hand packing quite a punch. I gritted my teeth, trying not to come as she spanked my bare ass again and again. I was soon gasping and groaning, knowing that my inevitable release was fast approaching. My ass was burning, and my cock was ready to explode.

“I want you to come now—but don’t you dare dirty my carpet.” Struggling to obey her and desperate for release, I cupped my free hand under my dick, jerking myself erratically while Kate spanked me harder and faster. I moaned and came in my palm, shuddering as I climaxed and her hand stilled.

“Now clean yourself up, and draw me a bath,” Kate ordered, as I stood there with my face no doubt as red as my ass. I immediately scurried off to do her bidding.

When I emerged from the bathroom to tell her that her bath was ready, she looked as beautiful and demanding as ever, clad in a silky robe and high-heeled slippers.

“I hope you’ve learned that I have very high expectations for my employees, Eric. Tomorrow, I expect a handwritten note of apology from you.” She squeezed my chin as she stared into my eyes. “And remember—I’ll be watching you.”

From that day forward, I strove to please Kate, but her punishments were often so exciting that I wasn’t always on my best behavior. She didn’t hesitate to take me over her knee at a moment’s notice.

Once all of the home repairs were complete, Kate started to have me serve her in the bedroom, drawing her nightly bath and eating her to climax before she’d retire for the evening with me curled up at the foot of her bed.

My winter break is soon drawing to a close, but I’m hoping that Kate will still need me. I am happy to be her servant in the bedroom and out.

—Mr. Eric L., Gainesville, Florida    

 

Toni and I are always eager to see our friends Raymond and Maria, a couple from out of town who we met through a hobby club. Nothing sexual had ever happened between us, but I’d always been aroused by Maria’s fabulous body, and I knew that my wife thought Raymond was attractive, too.

The four of us meet often during the year, and when I recently suggested they spend the weekend at our place, they readily accepted my invitation. Though racy thoughts did run through my mind, I didn’t believe anything would happen other than me being able to see Maria in a bathing suit; I was hoping for a very small bikini.

They arrived on Friday, a little before sunset, and Maria didn’t disappoint. She showed up in short-shorts and a T-shirt with nothing underneath it. Her nipples jutted out through the thin material, and it took all I had not to stare. I fixed us all margaritas, which they took to their room while they changed into their swimwear.

Again, I was not disappointed. Maria came out in the sort of bikini I’d hoped for. In fact, it was even tinier than I’d imagined, and her smallish breasts swelled up over the tiny top. Toni also had on a two-piece, but it was a little more modest. I wondered if seeing Maria wearing that small outfit would inspire Toni to retrieve the special bikini I bought her for our anniversary—a skimpy two-piece she only wears when we’re alone in the pool.

I kept the margaritas flowing while we sat in the shallow end of the pool and talked. I knew our guests could relax. Our yard has a high privacy fence with bushes to keep us hidden from prying eyes; in fact, Toni and I often fuck outdoors.

I tried not to stare at Maria’s titties, but it was difficult. My amused wife caught me ogling our guest more than once, and Raymond didn’t seem to mind my roving eye, either. In fact, he began relating some stories about their nude escapades, which involved frolicking in hot tubs.

“Don’t let us stop you,” I said, already imagining Maria naked.

“Maybe after another margarita,” Ray shot back.

I got out of the pool and raced to the refrigerator for the pitcher. I was getting a hard-on thinking about us getting nude with Raymond and Maria, so I hurried back to the pool to pour our guests more drinks.

Maria was giggling, and I figured she was aware of the predicament in my pants. There wasn’t much I could do to hide my impressive erection in my swim trunks. By now, Toni was definitely tipsy. Occasionally, she bumped her titties into Raymond, which didn’t go unnoticed by Maria and me. My shy wife was sexually flirting with another guy, and I was enjoying the show.

“Oh, the heck with it,” I heard Maria say as she took off her top. I sucked in my breath. Her breasts were one of the prettiest pairs I’d ever seen. I know I’m in the minority when I say I prefer smaller tits, but Maria’s were superb, with small areolas and short protruding nipples.

Raymond was next to drop his suit, and I was right behind him. Then Maria took off her bottoms, but it was hard to see anything through the water. We all looked at Toni to see if she would join in. I was so proud of my wife as she flung her top all the way to the patio. Her bottoms didn’t quite make it out of the pool, landing in the deep blue water.

Now that we were nude, we continued to talk. Actually, nothing more happened, other than me drinking in the sight of Maria’s titties and Raymond taking notice of Toni’s. Finally, our friends said they were tired and wanted to turn in a bit early. Maria said she hoped we didn’t mind. Of course, we didn’t. Toni and I were as ready to fuck as I’m sure they were. We were anxious to get some privacy to sate our lust.

We all slept past midmorning. I brought some pastries and coffee out to the patio, where Maria was sitting in her T-shirt without a bra again. She was always nice to look at, but those titties made the sight even nicer.

Just past noon, I volunteered to go pick up some pizza. We have this really great place not too far away, but they don’t take phone orders and there is usually a line. Maria volunteered to . . .