Letters to Penthouse XXXXIV

Exposed: Unexpected Horny Hookups


By Penthouse International

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The naughtiest hookups, the dirtiest deeds, and the most sinful tell-alls… Letters to Penthouse XXXXIV celebrates hot and steamy sexual encounters that are a notch above triple X. Readers will savor this collection of letters, all handpicked by the Editors of Penthouse.


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Welcome to the stockrooms and bedrooms, garages and galleries, beaches and barrooms of Penthouse readers. Meet the nurses and neighbors, strippers and strangers, mechanics and movie stars who never hesitate to open the door when erotic opportunity comes knocking. They know the hottest hookups require no appointment. And what you don't see coming will get you going… all night long.



Is there anything hotter than a surprise fling? There's something terrific about an unexpected, pulse-pounding romp that sends you into an orgasmic tailspin. You go to work or head to your appointment with no thoughts of your dirty desires crossing your mind. But then…

You hadn't planned on fucking your doctor, but the opportunity presented itself, so you took it! A near miss on the interstate leads to a different kind of front-end collision. A warm summer's day finds you in the checkout line buying some beer when suddenly you see your old college crush. One thing leads to another and the next thing you know, you're facedown in your sheets with his hard, throbbing meat stick probing your tingling cunt. And why shouldn't your husband fuck your BFF if her partner is lacking in the good-lovin' department? Sure you merely planned to meet for dinner, but the only logical dessert is you, your husband, and your BFF slapping your sweaty bodies together.

All of these lascivious lays started out innocently enough. No planning, no force needed, just a few twists of fate to turn all the best laid plans on their heads. Enter an erotic world where there are no holds (or holes) barred. A world where no matter if you're young or old, a wealthy businessman or a weary driver, you can easily become the pursuer—or the prey. Unexpected encounters are the most intense sexual hookups. You never know what will happen.

Read on,

Kathy Cavanaugh

Senior Managing Editor

Penthouse Letters

Prison Pleasures

I thought I was going to lose my mind. I'd just been talking to my girlfriend—I was allowed one phone call a week—and she'd told me that she had found someone else. She'd explained that waiting for me to get out of prison was just too much for her, and she wanted to break up.

I went back to my cell—it was an open-cell floor—and thought about how Aretha and I used to fuck. Aretha was short and black, with a huge firm ass that any man would love to stick his jimmy into. I'm about six feet, brown, with shoulder-length dreadlocks. As I sat on my bunk the guard shift changed. The evening shift was over and the graveyard shift was coming on.

I felt pretty shitty over losing my girlfriend of five years, and I suddenly felt the urge to fuck somebody. The officer now coming onto my floor was a hot little blonde-haired babe with what looked to be a great set of tits. She couldn't have been more than five feet one. She walked past my cell as she started on her initial rounds, and I saw she was beautiful. She seemed very friendly; she was smiling as she walked past my cubicle. I casually turned sideways, hoping she would notice my hard-on, but if she did she gave no sign.

I knew I had to do something to get her attention. I didn't know what would happen, but I figured the worst they could do was take me to the hole. I waited until about three-thirty in the morning, when the blonde made her rounds again, and everyone was sleeping except me. As she passed my cell my jimmy was peeking out of the hole of my boxers, and it was rock-hard.

I had a towel over my head so she would think I was sleeping, but by peeking out I could see her expression. As she approached my cell she looked in, opened her mouth in a gasp, and then laughed. Then she tapped on the bars. I pretended to wake up. All she did was point at my thing with her stick, which made it even harder. I rubbed it for a second, then put it back in my boxers, and she walked away.

I waited till she got back to her post, and then I slipped out of my cell and made my way over there. I had come this far, I couldn't turn back now. As I approached her post, I told her, "Officer, I can't sleep."

She tried to look tough, the way they all do. "What do you want me to do about it?" she demanded.

It was now or never. "Well, I could think of a few things," I said. "I mean, everybody is asleep, so we could…"

She just looked at me. She could have radioed for backup and they would have beat me up and put me in the hole right then and there. But instead she just sat there.

"Can I use your bathroom?" I asked her, even though the prisoners' bathroom was right next to hers and wide open. When she said yes, I knew I had it made.

Inside the bathroom I stood there with the light off for about five minutes. Finally she tapped lightly on the door and asked if I was all right. "Come inside, officer," I said.

She came in, and I was standing there stroking my cock. She looked very nervous, but she didn't move. I grabbed her hand gently and put it on my rod. She wrapped her fingers around it and said, "I could lose my job." I shushed her by kissing her wildly on the mouth.

She kissed me back, and I was surprised by her passion. When we broke the kiss, she said, "Hurry up, before someone comes!" I couldn't believe my good luck. I dropped my sweatpants and shorts down around my ankles and helped her with her belt. As her pants fell down I told her to lean over the sink, which she did. For a minute I just stood there looking at her sweet, firm ass as it stuck out toward me

Getting behind her, I immediately sank my stick right down to the hilt. She moaned. I started to work back and forth, moving harder with each thrust. She was moaning, "Faster, come on, faster!" I started to pound her, her ass smacking against my thighs. It had been so long since I'd fucked that I knew it wouldn't last long. I stuck my hands under her light blue shirt and felt those beautiful tits as I banged her. She reached under with one hand and put it over mine. I thrust harder now, tweaking her nipples. She turned her head back and began kissing me.

She moaned out that she wanted us to come together, and that was all I could handle. I blew my load right up inside her, and she came, too. I wanted to stay there and hold her tits, but she broke away from me. She took a wad of tissue and wiped the come that was dripping down her leg, then pulled all her gear back on. I pulled my sweats back up, and she kissed me and told me to go to bed. I asked her when she would be working this floor again, and she told me, "I'll wake you up when I do!"

Then, with a quick squeeze of my cock, she went back to her post. I went back to my cell, thinking that prison wasn't so bad after all.

—Name and address withheld     

Oh, Doctor!

When my husband was promoted this spring, we moved to a small town in Virginia. After having spent most of our lives in the big city, we were glad for the opportunity to live in a small community, where we would have the chance to meet and know our neighbors.

Shortly after moving in I developed a slight but nagging illness. I decided to visit a doctor, and since I didn't really know anyone yet who I could ask for a recommendation, I looked in the phone book and made an appointment at a nearby clinic. Since I was a new patient, the receptionist had me fill out all the forms and insurance papers. After finishing those I only had to wait a few minutes until a nurse called my name and led me back to an examination room.

While she took my vitals, I briefly described how I felt and why I was there. When she finished she told me that since I was a new patient the doctor would want to give me a complete physical exam. She handed me a gown and told me to undress.

I was a little nervous as I waited; this was the first time in years that I had been examined by anyone other than our family doctor. Within minutes there was a knock on the door, and in walked the nurse and the doctor. I guessed his age to be about the same as mine, and with his warm smile and southern tan, he could almost have been described as a hunk.

Normally I'm very nervous about examinations, but because of the doctor's easy manner and smile, I soon found myself completely at ease. Even with the sheet lowered as he examined my breasts, or pulled back as I lay at the end of the table while he performed the pelvic exam, I was relaxed. And more surprisingly, by the time he was done and said I could get dressed, I was almost disappointed.

Unable to find anything wrong, he wanted to schedule additional tests at the hospital the following week. In addition to the normal blood work, he also scheduled me for a barium enema and X-rays.

Before leaving, I stopped at the reception desk to pay for the visit. As the receptionist looked at my check, she saw my address and remarked that my husband and I must be neighbors of the doctor, who lived on the same street. I was taken aback. I knew that in a small town everyone knew each other, but this was more than I expected. When I got home I checked the doctor's home address. The receptionist had been right; he lived just across the street.

When John, my husband, got home that night I told him about my exam and the tests that were scheduled. He was glad I had found a doctor that I liked. However, when I told him where he lived, his reaction was different.

At first he didn't want me to go back. "No neighbor of mine is going to examine my wife," he said. "Find another doctor." But the more we talked about it, the more I realized how much I liked that doctor. I finally told him that I didn't want to change, and by the end of the week he reluctantly agreed.

The morning of the tests, John was more nervous than I was. Knowing that our neighbor, even if he was a doctor, was going to do these tests on me put him totally on edge.

When I arrived at the hospital, both the nurse and the doctor were already there. He explained the procedure to me. I would be given three preliminary enemas to cleanse my system before being given the barium enema and the X-rays. After he left the room, the nurse handed me a small sheet, telling me to undress and lie facedown on the table.

The sheet was only large enough to cover my front, leaving my entire backside bare. I felt more naked than ever as I waited. They both returned a few minutes later, and the nurse prepped me as the doctor readied the equipment. Both ends of the table were lowered, until my bottom was higher than my head and feet. After spreading my legs and telling me to relax and be calm, the nurse began to insert a thermometer into my rectum. I felt both apprehensive and embarrassed; I'd never had an enema before.

I watched as the doctor assembled the equipment. I noticed a large hose-like device, and surprisingly, the thought of that thing being inserted into my ass excited me. The nurse removed the thermometer, and even knowing what was next, I wasn't prepared for the sensation I felt. While the nurse parted my cheeks the doctor slipped a well-greased, gloved finger into my waiting anus and proceeded to lubricate it thoroughly until I began to quiver from the sensation. The nurse continued to spread my cheeks as the doctor withdrew his finger and then slowly inserted several inches of hose into my anus.

Once he was satisfied that the hose was in far enough, a warm solution was allowed to flow into me, filling my rectum. A clamp was then fitted onto the hose, and the table was returned to its level position. After helping me off the table, the nurse walked me to the bathroom while I clutched the sheet around me, the hose dangling between my legs. As I straddled the toilet, she reached between my legs and gently pulled out the hose. As I expelled the liquid I fell onto the seat, feeling almost as if I had just experienced an orgasm.

Returning to the table, I was no longer embarrassed. In fact, the thought of having the procedure repeated heightened my feeling of excitement. Taking my place on the table again, I willingly spread my legs, secretly looking forward to the hose and the warm solution again filling my rectum.

I made it to the bathroom by myself this time, and as I expelled the liquid I again found myself trembling from the sensation. Unable to control the feeling, I felt the sheet slip from my fingers and fall to the floor. As I got ready to leave the bathroom. I stared at the sheet on the floor. I was so hot now, I didn't care who saw me; in fact, I wanted them to see me. Besides, I rationalized to myself, between my exam last week and the tests today, there wasn't anything left of me that the doctor hadn't seen or touched. Leaving the sheet where it was, I returned to the room totally naked. If either the doctor or the nurse was surprised, they didn't show it, nor did they say anything.

Returning to the room after the third and final cleansing, I was surprised to see that another man had joined us. He was a lab technician, there to assist with the X-rays. Still on a sexual high, even with this stranger in the room I made no effort to cover myself. I could tell he was more than surprised by my nakedness, and as he set up his equipment his eyes never left me.

Once more I assumed my position on the table. The nurse again parted my cheeks and the doctor inserted the hose. As the solution flowed into me I could feel my stomach expand, trying to accommodate the volume of it. This time, after clamping the hose and leveling the table, the doctor asked me to roll over and scoot to the end of the table.

With both the doctor and the technician watching, the nurse positioned the stirrups and placed my feet in them. With my legs up and open and the hose extending from my rectum, I lay naked in front of them. I remained that way for about twenty minutes, unable to move until the X-rays were taken and reviewed.

That night, as I told John about my day, I could see that he was turned on as much as I was. "Secretly," he confided, "I was turned on all day, knowing what you were going through, knowing that another man—our neighbor—was seeing you naked."

My illness turned out to be a minor one, easily treated with antibiotics. Since then we see our neighbor often. In fact he and John are good friends, often golfing together. And guess who continues to be my doctor?

—M.J., Bluefield, Virginia    

Fire Down Below

It was about seven o'clock on a Wednesday morning when I was awakened by a knock on my door. I sleepily got out of bed, and as I went to the door, trying to pull my robe around me, the knocking became more frantic. Wondering what the hell was going on, I opened the door, still tying the belt of my robe. Standing there before me was the most handsome man I have ever seen, dressed in a fireman's uniform. I suddenly snapped awake.

"Is there a problem?" I asked.

The man told me there had been a small fire in the apartment next to mine, and he needed to make sure everything was okay on my side. I invited him in and led him into my bedroom, which shared a wall with the apartment next door. As I did so I was suddenly very aware that I had nothing on under my thin robe, and that he was probably getting quite a show.

In the bedroom he inspected the walls, and as I watched him I felt myself getting very turned on by this strange man, who I was sure had checked out the shape of my ass through my robe. When he asked if he could move a dresser over to check the wall behind it, I got up and went to help him. As I leaned over, my robe fell open, giving him a full view of my breasts. I stood up quickly and pulled the robe around me. I thought I saw him blush just slightly, but there was also a small smile on his lips. He told me that everything looked fine—and then added hastily that he was talking about the wall.

As we walked back through the apartment I thanked him for checking on me, and he said it was his pleasure, adding that he was sorry he woke me, but now I could go back to bed. "No," I said, "I'm just going to fix some coffee and breakfast."

"That sounds nice," he said.

I looked at him for a minute. I couldn't believe what I was about to say, but I said it. "What time do you get off?"

I saw his eyebrows rise. "I'll be back at nine," he replied. "If that's an invitation." I told him it most definitely was.

As the door closed behind him I took a deep breath, then ran inside to shower. I was incredibly turned on. I reached down to feel my pussy, and it was wet. I played with myself a little under the warm water, but not too much. I didn't want to waste it.

I was all dressed and had started the coffee when I heard his knock on the door. My nipples were suddenly hard. I called out for him to come in, telling him I was in the kitchen. When he walked into the room I had to catch my breath. He looked so yummy in his black T-shirt and jeans that I wanted to drop to my knees right there on the kitchen floor and suck his cock.

My hand was shaking as I handed him a cup of coffee. I felt his eyes follow me as I moved across the room to the toaster. "Lost the robe, huh?" he said. I laughed nervously and said I was sorry about that morning, and he said there was nothing to be sorry for; he'd enjoyed it. I felt awkward as I put some bread in the toaster, talking about anything I could think of, just to keep myself from begging him to fuck me.

I was so distracted that the bread started burning, and when I tried to pop it out the toaster got stuck. For a minute I didn't know what to do, and then I felt him behind me, his hand reaching around me as he calmly pulled the plug. I turned to him, laughing and saying, "Boy, am I glad you were here!"

"Me, too," he said, and then he took hold of the back of my head and kissed me hard on the mouth. When he stopped I was panting. "By the way," he said, "my name is Tony."

"Jill," I said weakly, and with that I felt his hands start to roam all over my body. As they slid across my ass he told me he wanted to see what had looked so good to him earlier on. Then he unbuttoned my jean shorts and slid them down over my hips, kissing my stomach as he stood back up. I felt his hands on my ass again, his finger sliding under my thong and into my crotch, and I thought I was going to come right there.

But the next thing I knew his hands had moved to my breasts. "I saw these before," he murmured. "But now I want to feel them and suck on your nipples." He pulled my tank top over my head and lowered his mouth to my breasts, his warm tongue on one nipple and his fingers playing with the other. My hand was on the back of his head, pulling him closer. With my other hand I tugged at the back of his shirt, and he straightened to allow me to pull it off over his head.

Looking into his eyes now, I brought my hands to his jeans, telling him that I had wanted to do this from the time he walked through my door. I unbuttoned the jeans and tugged them down, and his hard cock popped out. In a second I was down on my knees. Taking him in my hands, I ran my tongue up the shaft, and he let out a soft moan as I sucked the head into my mouth. I felt his hands in my hair, gently guiding me as I took him all the way into my throat. I cupped his balls in my hand and heard him groan. His hips began to move slowly, and I rejoiced in the feeling of him fucking my mouth.

When I felt his balls start to tighten I pulled away and stood up. My panties were soaking wet. I started to take them off, but he stopped me. Picking me up in his strong arms, he placed me on the kitchen table and told me to lie back. My pussy was in his face as he sat down in a chair. I could feel his breath through my panties. I grabbed the edges of the table and let out a long, slow moan, lifting my hips as he kissed my pussy. Only then did he pull my panties off. A second later his mouth was on me again, and I felt his tongue licking upward to my clit. I shuddered as he sucked it into his mouth. Then he put two fingers into my pussy and started finger-fucking me. It was too much. I grabbed his head and screamed his name as I went into the most earth-shattering orgasm I'd had in years, my hips bucking with wave after wave of pleasure.

When I felt his hands pulling at me I slid off the table and onto his lap, straddling him. I locked my hands behind his head as he lifted me onto his cock, and we started to move together. I leaned in to kiss his neck. Oh God, it felt so good that I never wanted it to stop. But I obeyed eagerly when he told me to get up and lean over the table.

I felt him pressing against me from behind and I squirmed against him, begging him to fuck me. He rubbed his cock up and down my smooth wetness, then slowly slid it in, his hands on my hips pulling me closer. When I thought it couldn't possibly get any better, I felt his moistened finger pressing at my asshole. I came again immediately, the table shaking beneath my body.

Tony growled in my ear that he wanted to come in my ass. As he pushed his cock slowly into my rear end, another orgasm took me over, and I could hardly catch my breath. After only a few strokes I felt his hot come spurting into me, and I loved hearing his loud cry of pleasure.

When he slid out of me I turned to face him, our bodies pressed together as I told him how incredible he was. Later, as I watched him get dressed, I couldn't stop myself from asking if I would see him again. Tony smiled at me and said that this fire was so hot that it would take him many visits to put it out.

—J.M., Miami, Florida    

While Hubby Sleeps

Last week my wife, Grace, and I went out for a meal with an old friend of Grace's named Rachel, and her husband, Roger. Grace and Rachel hadn't seen each other for ages, so they had lots to talk about. We had never met Roger before, and he turned out to be a real jerk. He was something of an egotistical snob, and after a while I couldn't even stand to talk to him.

By the time we finished the meal Grace, Rachel, and I were getting on famously, but Roger was sulking and ignoring us all, and to make things worse, he'd gotten completely shit-faced on wine. We got a cab back to our place, and I had to help Rachel put Roger to bed in the spare room. As soon as his head touched the pillow he was out like a light.

The girls and I went and sat in the front room, and before long we were all talking about Roger and putting him down. Rachel started going on about what a shitty lover he was, and how he never made her come. Then, completely out of the blue, Grace suggested that I fuck her. Rachel and I looked each other, and then Rachel said, "Yeah, good idea."

My heart was thumping like mad as she got up and walked over to me. She sat on my lap, stroking my cock through my jeans as we started kissing. Grace stood up and stripped off her clothes, then came over and undressed Rachel, while we continued to kiss. Rachel undid my trousers and started to play with my hard-on, and Grace knelt on the floor to lick Rachel's pussy. I couldn't believe this was happening, but I wasn't going to look a gift horse in the mouth. Rachel slid to the floor and began licking up and down my dick, then took it into her mouth. When Grace joined her I thought I was in heaven. Two beautiful women sucking me off—and I wasn't even dreaming!

As Rachel sucked my cock, Grace stroked it with her hand, and as I looked down at them I felt my spunk rising. Grace realized I was about to come and pulled my cock out of Rachel's mouth, continuing to stroke it until I spurted all over Rachel's face.

Grace licked the last dribbles of come off my dick, then pushed Rachel onto her back, licking my spunk off her face before kissing her passionately. Rachel responded by slipping a hand down between Grace's legs and stroking her cunt, and then she slipped a finger into Grace's pussy hole and she went wild. Rachel turned around so that the two girls were in 69 position, and they began to lick each other out. They started off gently, but within a couple of minutes they had their tongues buried deep in each other's cunts and were writhing around all over the place.

Of course as I watched this it didn't take long for my dick to get hard again, and I knelt behind Grace and slid my cock up her cunt while Rachel licked it. Grace's twat was soaking and my cock slipped in and out of it really easily, causing her juices to dribble out of her hole and run down into Rachel's mouth. I was playing with both girls' tits as I fucked my wife, and then Grace started coming as Rachel licked her clit, and I pumped my cock into her in time with her spasms.

When Grace recovered she said she wanted to see me fuck Rachel, so I pulled my cock out of Grace and climbed on top of her friend. She guided me in and I rode her sweet body for all I was worth, feeling her tight pussy clinging to my boner with every thrust. Rachel climaxed twice, and when Grace started to suck her pert little tits she came again. I fucked her long and hard, and finally emptied my balls into her clinging pussy, kissing her deeply as I came.

Once we'd got our breath back we went upstairs to clean ourselves up, and ended up doing it all again, this time in the bathroom.

We finally slipped into bed around five in the morning. Rachel and Roger left the next day, but Rachel promised to visit my wife again as soon as possible—without Roger. We're both looking forward to that.

—B.H., Milwaukee, Wisconsin    

Fixing Her Furnace

I have been happily married for eighteen years. My husband and I have enjoyed a good sex life for most of that time, but in recent years, much to my frustration, his job has taken him away from home for extended periods of time.

This winter was unusually cold and snowy, and in late December our furnace quit working. I called a friend who works with an oil company for help, and she immediately sent out two servicemen, who arrived within an hour. I let them in and we went straight to our furnace room. The taller one introduced himself as Hal, and his friend as Matt. The two of them went immediately to work and had the furnace up and running within five minutes.

I had been waiting in the rec room, just off the furnace room, and when Hal told me they were done, I said I couldn't believe they had been so fast. Hal moved toward me, placed his hand on my hip and asked if there was anything else he could help me with. My heart was suddenly pounding hard, and I knew I was damp between the legs. I meant to say no thanks, but I found myself threading a finger through his belt loop. Hal grinned, then pulled me closer and kissed me. I moaned and kissed him back. Then he asked again if there wasn't something he could do for me. It had been over three weeks since my husband had left, and I guess I just needed it bad. This time my answer was, "Well, maybe there are one or two things…"

He quickly pulled my sweatshirt over my head and told me to take his dick out. My hands shook as I worked his zipper while he massaged my nipples. I finally freed his dick and started to stroke it, quickly bringing it to full erection. He popped his top button and slid his jeans over his hard butt, then sat back on our couch and told me to suck his dick. I was breathing hard now, and I automatically went to my knees, slipped his cock between my lips, and started sucking. It was the first time since before my marriage that another man's cock had been inside me.


On Sale
Aug 28, 2012
Page Count
304 pages

Penthouse International

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