Letters To Penthouse XXVII

The First Time Is the Hottest


By Penthouse International

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What could be hotter than a wild encounter between two erotically adventurous people? A wild hot encounter with “three or more” erotically adventurous people. These letters from “Penthouse” magazine detail how everyday couples and singles add to their sexual pleasure. Original.



Erotica from Penthouse

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Erotica from Penthouse III

Letters to Penthouse I

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Letters to Penthouse XXI

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Penthouse Uncensored I

Penthouse Uncensored II

Penthouse Uncensored III

Penthouse Uncensored IV

Penthouse Uncensored V

Penthouse Uncensored VI

Penthouse Variations

26 Nights: A Sexual Adventure

Penthouse: Naughty by Nature

Penthouse: Between the Sheets

Penthouse Erotic Video Guide

Penthouse Unleashed: Sex Tips


My European-born wife loves the television series Sex and the City, which is a big surprise to me, since she never uses vulgarities of any kind. As a former teacher, Katarina claims it's a waste of good language and time.

To me it's a girl show—produced by, dressed by, aimed at, and loved by girls. Talented? Gifted? Sure, to the max, but not for most guys. Except for last week's show, titled "Mister Pussy." I was into my standard girl-show escape routine, typing on the computer that we have rather foolishly right smack in the center of our family room. The episode title immediately caught my attention. I had all I could do to keep from yelling out, "Plagiarists! Mister Pussy is my title!" Maybe that's what caused me to pay attention to the blatantly sexual dialogue. In any case, I was impressed and even educated by the episode.

I always knew my Katarina was unusual in her distaste for being eaten. This episode validated my instincts. She went along with it during our courtship, I imagine because she knew how much I crave oral sex as my basic foreplay. The show had Katarina and me in stitches. This obsessive cunt-lapper would turn every casual conversation around to oral sex during anything he thought of as a date. At the table he would eat a peach or pear by splitting it and then licking and sucking, devouring the contents with noisy pleasure. Later he would bed the girl and just eat her. Not fuck her or, for that matter, even kiss her above the waist.

Because he specialized in eating pussy, Samantha, the character played by Kim Cattrall, tagged him Mister Pussy, and it stuck. "Oh," Samantha said. "You don't marry a guy like Mister Pussy. You just savor his talents."

My Katarina thought the tears rolling down my cheeks were from hysterical laughter alone. They were not. My memory bank jammed recalling two, no three relationships I had endured—yes, endured—eons ago, when I was single.

In my old neighborhood in New York, it was well-known that Jewish girls love to be eaten. Okay, okay, write me hate mail, toss eggs at me, and call me bad names! But I have never met a Jewish woman who did not want to be devoured. One and all, they adored my lips, tongue, and Italian nose piercing their labia during sex play.

The word spread around the neighborhood. It was even rumored that the local synagogue was abuzz about the gentile boy who was the reigning monarch of muff-diving. And friends, I loved it! When the guy who had introduced me into his crowd told me about the title I had acquired, he seemed embarrassed for me.

"Stan," I said, "I am proud to be of service to your beautiful ladies."

One warm Saturday night in July, Stan and I double-dated at a rock concert. He took Ellen, and I took her best friend Joy. Both were very attractive, but Ellen was stacked with a set of double-D hooters that turned heads. Joy? Glorified nipples and a padded bra.

Stan had known both girls since they were kids. Sex seemed at all times fair game for conversation, and it was clear that Joy had told Ellen each lick of our dates. After the concert, back in Joy's finished basement, we were all making out like crazy on a long sofa, and I kept hearing the girls speaking softly between kisses, announcing to each other blow-by-blow, like at a billiards match.

"He's squeezing my left titty," Joy would whisper to Ellen, whose face was close enough for Joy to kiss as they spoke. Then Ellen would say with more than a little theatrics, "He's got two fingers up my cunt!" I was shocked by the language, but fascinated by the excitement dirty talk seemed to give them.

Almost like twin brothers thinking alike, Stan and I began to cross-touch the girls as they continued their love talk to each other. It was a jolt to hear Ellen tell Joy that I was tweaking her clitty.

I decided to try the same game. I urged Joy, "Let me taste Ellen?" A few hushed moments passed while she thought it over. Then she just nodded. Ellen was surprised but pleased when Stan moved aside. She lifted her short mini, exposing her panty-clad cunt and ass. I asked Joy to remove her soul mate's panties. Ellen's moans told the story as my mouth met her pungent pussy lips. Meanwhile Stan was caressing Joy's thighs. Then he buried his face in his old high school prom date's bush.

That night our Jewish princesses came about four times, but none from fucking. Yes, Mister Pussy was in his groove!

—R.W., Princeton, New Jersey  


I have to say, on behalf of the American male population, that we love dicksuckers. The ability to suck a fat dick is the quality that's most important in a woman. Let me tell you my latest tale.

I'm a paralegal. Recently I noticed that a lady who came into our office for legal advice had big red succulent lips, the kind that can suck the "lolli" right off a lollipop. She eventually confided in me about the problems she was having with her husband that made her want a divorce. My boss was out that day, so I gave her my card and said to call anytime she needed someone to talk to.

She called me the next evening from a local motel, after an argument with her husband. I got to the motel as quickly as I could, and found her watching a porno flick where a lot of dicksucking was going on. I had a hard time staying cool. I could just imagine her big red lips sliding up and down my big black meat. I tried to console her, but she hushed me and told me to sit down. She moved between my legs, unzipped my pants, pulled out my dick, and sucked me into a coma. I mean, she slid up and down, swirled her tongue, and cupped my balls all at the same time. She was a dicksucking delight. She slid up and down until I was ready to shoot my load.

She noticed this and stopped her sucking on a dime. She had been drinking beforehand, and now reached for her drink, grabbed my dick, and directed it into the drink, where I shot my load. She removed my dick from the glass and cleaned it off with her lips, then drank the drink. She called this a "come island iced tea." I thanked her and left.

A day or two later I received a phone call at work and was asked to go back to the same motel room at seven that evening. She would be waiting for me.

I made it there by quarter to seven. To my surprise, she had two girlfriends with her. I wondered if I could handle this! I got naked, and she pulled out my dick and went right to work. One of the girlfriends licked my balls, the other one sat on my face. I lapped up her wet pussy while the two other women gave me the blowjob of my life. After I shot my load, the second dicksucker managed to wake mine up with her repertory. Between the dual dickjob and the juicy pussy I was munching, I was in convulsions. At this point I had an out-of-body experience, seeing trees and waterfalls and butterflies. I looked down at myself and saw myself getting this great treatment. I jacked off and came on the flowers.

All of a sudden I was back in the room. It was time to fuck. I laid the three women down side by side and moved back and forth among them, giving fifty or so pumps before switching. This went on for about half a million strokes, until I brought each of them to climax. Then the fun began. The four of us got in the shower and started all over!

The best kind of woman is a dicksucking one.

—H.W., Cleveland, Ohio  


I'm a happily married twenty-six-year-old woman with an affinity for sucking cock. With my petite figure, red hair, green eyes, and ability to take it all the way to the back of my throat, few men would decline an opportunity to have me give them blowjobs.

A few months ago I was introduced to the attorney of a friend of mine. I knew right away that I was in trouble. Even though I knew it was wrong at the time, I just couldn't help myself around this guy, and it was pretty clear to both of us that the sexual attraction was mutual. He's very good-looking—tall, with broad shoulders, gorgeous brown eyes, and a tight ass. It began with some suggestive talk, and I knew that it wouldn't end until I had his cock in my mouth.

The reality turned out to be way better than I had even dared to imagine. I love to take him in my mouth, using the tip of my tongue to lick up and down his long, thick cock. As I lick, I begin to close my mouth and, using the entire length of my tongue, I draw him to the back of my throat and continue sucking and sucking as I look up into his big brown eyes. His cock throbs as it glides in and out of my throat, and my pussy becomes increasingly wet. Often when I feel him pulse and shoot his hot, sweet come down my throat, it's enough to make me come!

For the past four months we've enjoyed these stolen moments as often as we can. Recently, he brought up the idea of anal sex and described his fantasy to me. I had never done anything like it, yet surprisingly became aroused at the idea. One Friday, with both of us fully clothed, he came up behind me and began grinding his cock against my ass while whispering in my ear how good it would be to fuck my ass. I was so wet that I thought I might come when he moved one hand around the front and up between my legs to rub my clit. With the other hand he played with my boobs and squeezed my nipples.

That put me over the edge. I began an incredible orgasm that soaked my pants almost all the way through. Afterward, I said I couldn't wait for him to slip his cock in my pussy and my ass, as he said he loved to do.

That evening, after I did the usual family things, I fixed myself a bubble bath, complete with candles. I meant to practice for his cock. I sat on the edge of the tub playing with my boobs, then licked my nipples as I thought about his hard cock fucking my ass. I came in minutes. Then I lowered myself in the water and lay back, spreading my legs so I felt the hot water rushing over my clit and in the opening of my pussy. I imagined his voice whispering in my ear and almost felt his warm breath against my neck. I resumed licking and sucking my nipples while moving my right hand down to rub my clit.

It didn't take long before I was coming again. With my right hand on my clit and the middle finger of my left hand sliding in and out of my pussy, I fantasized that he was watching me with his beautiful brown eyes, his smiling face approving of my every move and moan. I slid my finger in my pussy as far as it would go and massaged my G-spot while slipping my ring finger in my ass. I lay there completely filled, fucking myself harder and harder until I eventually came again. If fucking my ass by myself produced orgasms like this, I knew I needed his hard cock inside me soon.

The following week I whispered a few details of my adventures in his ear. I knew things would eventually get hot when I saw the look on his face and his hard cock bulging through his slacks. He said his only regret was not having been there to watch me get myself off. At that moment I wanted nothing more than to suck on his cock. He stood and moved to close the door to the conference room where we were talking. As he stood behind my chair he started playing with my tits, squeezing them the way he does so well. He said to take off my pants and panties. Fearing that if someone walked in the front office I'd need them nearby, I only slipped them down to my knees, then bent over on the chair in front of me.

At his suggestion, I rubbed my clit and slipped a finger in myself. He unzipped his slacks and held his hard-on to my face, urging, "Suck me." I did, using my left hand to guide him in and out of my mouth. I kept fingering my pussy. It was so exciting to feel him swell to an even more impressive size.

Then he stopped me from sucking him. He slipped a finger in me to feel how wet I was, then asked, "Would you like me fuck you now?"

I eagerly answered yes.

He left the room just long enough for me to slip my pants and panties all the way off and to prolong the thrill of anticipation. When he returned, he turned me around and bent me over the conference table. Again he said to rub my clit, and I did. Knowing I would soon have him in my pussy, plowing me to orgasm, gave me such a rush that the moment he entered me, I came all over his cock. He made me even hotter by sliding his finger in and out of my ass. His relentless fucking, combined with his finger work in my ass and my handiwork on my clit, finally brought me to another orgasm.

When I calmed down, he patted my ass and said, "Now what I want you to do is suck my cock until I shoot."

He sat on a chair, and I knelt on the floor between his outstretched legs. With his hand he gently guided my face to his hard-on. Wanting to give him the pleasure he had just given me, I put my open mouth around him and licked slowly until I felt his cock reach the back of my throat. I wrapped my lips and tongue around him tightly and sucked away. Pulling myself halfway up his cock, I slid a hand around it and stroked with both hand and mouth. Feeling his cock pulse in my mouth, I tightened my grip and sucked harder, until he blew.

We never did get around to him fucking my ass. But you can bet I'll write and tell fellow readers all about it as soon as we do.

—J.E., St. Petersburg, Florida  


You've probably heard the joke: What does every man want for his fortieth birthday? Two twenty-year-olds. It was certainly true of me. As I approached forty, whenever I saw a beautiful young woman, I fantasized about sex with her. About a week before my birthday, I had to go out of town on business. My wife decided to hire a stripper to come to my hotel room and put on a show, thinking this would embarrass the hell out of me and get me over my obsession.

It didn't quite work out that way!

The stripper, Annie, was a beautiful Asian girl with dark hair down to her ass. She was about five feet five, with great tits. She said she was twenty-two, but she looked much younger. She came to my room posing as a maid, asking if she could turn down my bed. She walked over and pulled the covers down, then sat on the edge of the bed and without taking her eyes off me undid her blouse, one button at a time, until her breasts were exposed. I just stood there and stared, with my heart nearly stopped.

She stood up and slid her blouse off her shoulders, letting it hit the floor. She then came to me and started to unbutton my shirt. She took it off, then reached down to rub my crotch. I had no idea what was going on, but I was hard as a rock! This young thing, looking good enough to eat, sat on the bed and undid my zipper, then my belt, and pushed my pants down. With her hands on my ass, she pulled me to her and kissed the head of my dick. Then she took it in her mouth, an inch at a time, seeming to know exactly what I wanted—her mouth was so warm, so soft. My dick isn't small, but she took the entire thing in. She'd pull me completely out of her mouth, then slide me back down her throat. Just watching her was enough to make me want to come. Every time she took my cock down her throat, I thought I would explode. Soon I knew I couldn't last much longer. I placed my hands on her bobbing head and buried my cock in her, obviously about to come. She held me there as I started to spurt. It was an incredible sensation, as if she didn't even have to make an effort to swallow. My come just slid down her throat.

When I finished coming, she started sucking again, to be sure she got every drop out of me. She must have spent at least ten more minutes at it. Finally she pulled my dick out of her mouth and kissed the head. Then she put on her blouse and walked to the door. I followed her, in shock, not knowing what to say or do. As she said good-bye, she kissed me on the lips and said she was a birthday gift from my wife. Then she left.

When I got home, my wife asked if my gift had gotten me over my obsession with younger women. Of course, I lied.

—J.N., Kansas City, Missouri  


Recently I have been trying to get my wife to share some of her sexual fantasies with me. As I'm sure most women are, she was reluctant to do so. We've been married for eleven years now, and our sex life has become a little routine. One night—one when I'd been able to get her to orgasm—I asked again.

"Oh, all right," she said finally. "I'll tell you, but you have to tell me yours too."

Believe it or not, I hadn't even thought of telling her my fantasies! But I said, "Sure," willing to say just about anything to get her to share with me.

"I've always heard that guys are obsessed with watching two girls together. Well, I've always been captivated by the idea of watching two guys taking care of each other." As she said this she kind of blushed but also had a devilish look, as if she were trying to read my reaction. "I don't know," she went on, "but the thought of watching one guy fucking another guy's mouth—you know, doing to him what most guys always seem to dream about doing to nearly any girl—that really turns me on."

My fantasy also involved oral sex, but with me on the receiving end. She found it a little boring and very predictable, as I am always trying to convince her to suck me off more often.

Over the next few days, I couldn't get her fantasy out of my head. In fact, I was becoming a little obsessed with the thought of what it would be like to get face-fucked by another guy. I decided that I would explore my feelings and see where they took me. I went to an adult bookstore a couple of towns away. I walked around, getting acclimated to the place and also, more importantly, checking to make sure there was no one there who might know me.

I went in one of the booths and chose a video involving guys with guys. I must have been in there about a half hour, and I have to admit that I was getting a little turned on by the action onscreen. One guy was on his knees while another held his head and briskly fucked his face. Just then I heard a knocking. I assumed it was the booth door, as I had been in there a while. I looked through the spy hole. There was no one there. There was another knock, and I realized it was coming from the booth next door. I looked in that direction and saw something I had missed when I came in, a small door about crotch-high.

Knowing what was waiting for me, I decided, Why not see what develops? In the back of my mind, I figured I might just get a blowjob out of this. I bent over and opened the door, and was greeted by a hard cock. I backed away but couldn't take my eyes off it. Without thinking, I reached out and grabbed it. It started to move like it had a mind of its own. Its owner was fucking my hand.

After a minute or so, feeling the friction build up, I knew from experience that a little lubrication was needed to make the experience more pleasurable. I drooled onto my palm and then resumed helping this guy out.

As I sat there, mesmerized by the fact that I had a guy's dick in my hand sawing back and forth, I froze. I noticed that he had a black tattoo on his groin, which I recognized. It belonged to a guy who went to the same gym as I did—in my own town. I was now in danger of being discovered, and was about to back away, but just then the package in my hands began to grow just a little more. Then I watched as it began to pulse out a strong load of come.

I sat back in the booth trying to figure out what to do. Then I heard movement next door, and looked down as another cock, this one bigger than the first, appeared. I got up to leave, then realized that the guy I had just given a handjob was probably right outside the door! Meanwhile the big cock poking through the wall was waving at me in invitation. A thousand thoughts ran through my head. I decided that since I couldn't leave, I might as well make the best of it. I again reached out and grabbed the cock being offered.

As I started to pull on it, the guy decided that he wanted more, or at least that's what I figured as he withdrew it for a second or two, then pushed it back at me. When I grabbed it again, he pulled back, then after a second or two pushed it back again. I got the message. I was torn about what to do. Then I remembered that I didn't want to leave the booth, and convinced myself that I would do this just once and no one would ever know.

I got down on my knees and leaned over and got my face close to it. There was a slight muskiness that both turned me on and made me a little queasy. I gave it a few licks. It tasted better than I expected, but it wasn't candy! After slathering over it for a minute or so, my mouth opened of its own accord, and I put my lips around the head.

I moved forward slowly to take a little of it in my mouth. I was surprised at the texture, fleshy but extremely hard. The guy was trying to push more of it in my mouth, but I had the ability to control how much I took. It comforted me to realize that I did have control over this event, and I began to take more and more of it, until the head bumped up against the back of my throat. I had around three-quarters of the guy's shaft stuck in my face now, and I was starting to get excited.

I have no idea how long I bobbed back and forth on this thing, but suddenly it pulsed strongly. It felt like my mouth was being filled with a garden hose. I backed off in surprise, but as the taste registered on my tongue, I realized that I wanted more. I quickly fit the cockhead back in my mouth and started to swallow as fast as I could. After what felt like five minutes, it started to go soft, and I fought to hold on to it longer. But the guy pulled back, and the head escaped my grip with a slurpy pop.

I sat back and reveled in this incredible feeling, and then I caught sight of more movement in the other booth. I panicked when I saw a fleshy black rod coming toward me. This thing must have been ten inches long, and immensely thick. I had no idea how or if I would be able to get any part of it in my mouth. I reached over and started to stroke it softly. Then the temptation got the better of me, and I had to taste it. I leaned down and started to lick it, then opened as wide as I could and tried to take it in. The owner backed off a little, but I kept my lips fastened to it like glue. Then, without warning, he rammed it as far in my mouth as he could.

I backed off only a little, and ended up with about six inches buried in my face. I grabbed it at the base and bobbed back and forth, taking as much as I could each time. When I felt it bump against the back of my mouth, I paused, took a breath, and pushed down as far as I could, forcing the thing into my throat. I repeated this a few times, and before long I removed my hand and found my forehead bouncing against the wall. I had done it! I had taken this entire monster down my throat.

I was so thrilled that I didn't realize at first when the giant cock began to pump a load of come straight down my gullet. I never hesitated this time. I simply swallowed as fast as I could. I had become a come-loving cocksucker, and suddenly I couldn't get enough!

This monster was replaced with another, and then another, until I lost track of how many cocks I had sucked or how many loads I had swallowed. My neck was getting sore from bobbing back and forth, so I just put my mouth up against the hole and let the guys just fuck my face at their will. To catch my breath I jerked a couple off, but I made sure my mouth was there to swallow every load that was pumped my way.

Throughout this whole scene I kept thinking I had to get out of there. But the image of that first guy, and the fact that he would recognize me, kept me rooted in place. The entire store paraded into the next booth, and I'm pretty sure some of the guys came back for seconds.

The image of me on my knees getting face-fucked and what my wife would think flashed through my mind over and over. My feelings were spinning around and around—between asking myself if I might be gay to wishing I wasn't there to being incredibly turned on by the pleasure I was able to give these horny guys. The anonymity of having a wall between me and them also gave me a false sense of security.

Eventually, after a big dick finished erupting in my mouth, there were no more there to take its place. I had sucked off all comers. I closed the glory-hole door, wiped off my face, looked out the spy hole and, seeing no one there, decided it was safe to exit. The only person still in the store was the guy behind the counter.

"Hey, that was pretty special," he said to me as I emerged. "I don't think I've ever seen a line of satisfied guys like that one. Just about everyone got right back in line when you finished them off. A couple of guys even called their buddies. We haven't been this busy since that married lady with the spider tattoo pulled a train through the same hole. Up until now she held the record for taking on the most guys, but you put her to shame. There's only one problem, though. I couldn't leave the counter, so I missed out on all the fun. Any chance of me getting a turn?"

I just looked at the guy and turned to the door. I said, "Maybe next time," as I walked out of the store. It wasn't till I got to my car that something suddenly hit me. My wife has a spider tattoo.

R.B., Manchester, New Hampshire  


On Sale
Dec 1, 2006
Page Count
320 pages

Penthouse International

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