Letters to Penthouse V

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ISBN: 978-0-446-50627-4

First eBook Edition: August 1995

OTHER BOOKS IN THE SERIES:

Erotica from Penthouse

More Erotica from Penthouse

Erotica from Penthouse III

Letters to Penthouse I

Letters to Penthouse II

Letters to Penthouse III

Letters to Penthouse IV

Letters to Penthouse V

Letters to Penthouse VI

Letters to Penthouse VII

Letters to Penthouse VIII

Letters to Penthouse IX

Letters to Penthouse X

Letters to Penthouse XI

Letters to Penthouse XII

Letters to Penthouse XIII

Letters to Penthouse XIV

Letters to Penthouse XV

Letters to Penthouse XVI

Letters to Penthouse XVII

Letters to Penthouse XVIII

Letters to Penthouse XIX

Letters to Penthouse XX

Letters to Penthouse XXI

Letters to Penthouse XXII

Letters to Penthouse XXIII

Letters to Penthouse XXIV

Letters to Penthouse XXV

Letters to Penthouse XXVI

Letters to Penthouse XXVII

Letters to Penthouse XXVIII

Letters to Penthouse XXIX

Penthouse Uncensored I

Penthouse Uncensored II

Penthouse Uncensored III

Penthouse Uncensored IV

Penthouse Uncensored V

Penthouse Variations

26 Nights: A Sexual Adventure

Penthouse: Naughty by Nature

Penthouse: Between the Sheets

Penthouse Erotic Video Guide

Domination & Discipline

WHEN THE "BABY" MISBEHAVES, THE SITTER MUST PUNISH HIM

Reading your magazine has prompted me to write about something that happened to me when I was eighteen. My parents worked, so we had a female college student living with us. In exchange for a place to stay, Amanda did housework and "babysat" me. Amanda was a pretty girl with large breasts.

During my summer vacation, I started hiding in the closet of her bedroom while she was in the shower. When Amanda would come out, I'd watch her get dressed.

One day I must have made some noise, because she caught me in the closet with my dick in my hand. Was she mad! She threatened to tell my parents when they got home, and I was so scared and embarrassed, I started begging her not to tell.

After she cooled off a little, Amanda got me to agree that I deserved to be punished, and said that we could work something out.

Amanda ordered me to get undressed and lie across her knees so she could give me a spanking. She spanked my ass until it was red and sore, then laughed at me because my dick was rock-hard. That was just the beginning.

Amanda proceeded to make me her "little slave boy." I had to put on her silky panties and do all the housework. To make sure I didn't tell my parents, she took pictures of me wearing her panties and pushing the vacuum. She swore she'd give copies of the pictures to all my friends if I spoke a word to anybody. Later that day she made me eat her pussy and lick her asshole. She also spanked me again, and this time I came in her panties, so she made me eat my own come.

The rest of the summer, while my friends were partying at the beach, I spent most of my time serving my mistress. On Saturday nights, when my parents went out to dinner, Amanda made me model her lingerie for her friends. By the end of the evening, I would have eaten the girls out, been spanked at least once, and led to the bedroom, where the girls would tie me up and take turns sticking dildos up my rear end.

When Amanda finally graduated from college, she fucked me once, burned the pictures and said it had been fun. I haven't seen her since, but I actually miss being her slave. I've dated a lot of women since then, but have never been in a relationship that was as satisfying. I will continue to look for the right woman to be my next mistress.—K.D., Portland, Maine

A GIRLFRIEND ENSURES THAT THE PUNISHMENT FITS THE CRIME

After reading about guys who were forced by their wives or girlfriends to suck cock, I thought I would relate an experience I had a few years ago.

I was dating a girl named Dana who was absolutely beautiful. She was thirty-two years old, five feet nine inches tall and one hundred twenty-five pounds with thick, flowing brown hair, sparkling blue eyes, a perfect smile and a body that would make a centerfold jealous. She was a definite head-turner, and she knew it. We had been dating for about a year when I made the mistake of having a fling with a sexy girl I had met at work. Dana found out and called me at home to tell me that I had humiliated her by sleeping with this girl and that she didn't want to see me any more. I told her I was sorry and begged her to give me a second chance. She said that she would think it over, and told me to come to her house the next evening at seven o'clock for her answer.

I knocked on her door at seven o'clock on the dot. When Dana let me in, I saw that her friend Charles was visiting. Charles is very openly gay.

Dana called me into her bedroom and told me that she would give me one more chance, but that I would have to be punished. She said that since I'd humiliated her, she was going to humiliate me. If I wanted to get back together with her, I would have to have sex with Charles while she watched. I just stood there in disbelief. Dana said she would give me until the count of ten to make up my mind.

When she got to ten, I still hadn't said a word, so she grabbed me by the arm and told me to leave. I pleaded with her, but she held firm. She then informed me that she was going to call one of her friends from work, go over to his house and fuck his brains out. She knew that would get to me, so I agreed to her terms. She said that because I'd hesitated, I would have to ask her permission to have sex with Charles. She ordered me to get on my knees and beg to suck his cock. Dana told me that she was going to teach me a lesson I'd never forget. She wanted to watch Charles fuck me up the ass, and wanted to watch me kiss, lick and suck his cock.

I was led back into the living room, where Dana ordered me to do a striptease. Once naked I was told to dance around the room and pose for them. Dana then put lipstick, makeup, a wig, a garter belt and stockings on me. Then I was instructed to undress Charles. He had blond hair and a muscular build. But as good-looking as he was, I was not at all interested in having sex with him.

Once Charles was nude, Dana ordered me to kiss and lick every inch of his body, starting with his toes. I was told to save his cock for last. When I got up to his chin, Dana made me French-kiss him. Charles put his hand behind my head and shoved his tongue down my throat. Dana told me to kiss and lick his cock. While I did it, Dana taunted me, and really making the most out of the situation. Then she told me to beg Charles for permission to suck his cock. I paused for a few seconds, and Dana yelled, "Do it!"

I dropped to my knees and said, "Please, sir. May I please suck your cock? Please? I beg of you, sir, please let me suck your big cock."

Dana really got off on this, and made me plead for about ten minutes. Then she said, "Okay, you can suck it, but first I want to watch him fuck you in the ass."

They bent me over a chair, and Charles stuck his cock up my rear and pounded away. Dana asked me how it felt to be fucked up the ass. "You like it, don't you?" she yelled.

"Yes, ma'am, I like being fucked in the ass."

Dana told Charles not to come, because she wanted him to come in my mouth so she could watch me swallow it. Charles pulled his cock out of my ass. After running to the bathroom to wash it off, he came back and shoved it in my mouth. Dana told me to suck it until he came. She was incredibly aroused, and really turned up the verbal humiliation. She said, "Suck that cock!"

I stopped sucking his cock momentarily. Dana was quick to slap my cock and start yelling at me again. "Put that cock back in your mouth and start sucking it. Suck it until he shoots his load in your mouth. You better swallow it all."

I felt Charles's cock start to throb. Dana saw the scared look on my face and put her hand behind my head, ordering me to swallow every drop. Charles exploded in my mouth, and I tried to back away, but Dana kept me in place.

Before the evening was over, Dana forced me to masturbate for them. I had never masturbated in front of anyone before, and it only added to my embarrassment. She had me ejaculate on Charles's cock, then lick it all off. While I was licking my own come, Charles got hard again. Dana smiled and said, "Suck him off. I don't think you've had enough come tonight."

I sucked Charles's cock until he shot his load into my mouth.

Dana informed me that if I ever pissed her off again, I would receive the same kind of punishment. I dated her for two years after that incident, and the punishment was repeated at least two dozen times during that period. I was so infatuated with her, I couldn't stand the thought of her leaving me.—J.M., Indianapolis, Indiana

SHE PROMISED TO HONOR AND OBEY—IT'S NOT NICE TO BREAK PROMISES

I am a twenty-six-year-old man who has been married for over three years. When I was in college and masturbated frequently, I had elaborate fantasies about complete domination over women.

Before getting married, sex between my wife Gina and me was frequent and passionate, but stayed pretty much on the normal side. Occasionally we experimented with ice cubes or whipped cream, but these episodes were far too infrequent for me.

Things continued this way until about a year and a half ago, when we hit a dry slump. To pick things back up, I suggested that we talk dirty to each other in bed. Gina took to this better than I'd expected, and soon we were talking trash to each other during every sex session we had. This excited me very much, and perked our sex life back up. It also seemed to make Gina more uninhibited and experimental. We even ordered a sex toy through a catalog! Then, about six months ago, it happened!

We were getting ready to fuck and leafing through Penthouse Letters to get ideas for something different to do, when we read a letter about a woman tied spread-eagle to a bed. "It's a shame we don't have any rope. We could try that," Gina said.

It surprised me to hear her say that. "Would you really want to do that?" I asked.

She just shrugged and said, "Sure."

That night while we fucked, I imagined that Gina was tied down, and I came like never before. Afterward, when we were getting dressed, I told her that most of my fantasies concerned bondage, domination and discipline. I thought that comment would be soon forgotten. Boy, was I wrong!

The next night while lying in bed, Gina told me that it had always been her fantasy to be completely under my control. I couldn't believe my ears! "I'll do anything," she said. "I'm your little girl."

My heart was pounding rapidly, and I didn't know what to do at first. Finally I stood up, walked over to the wall and leaned against it. "Come here," I said.

Gina came over and stood in front of me, waiting for my next command. "Get on your knees and rub my cock all over your face," I ordered. Gina has an adorable face, and watching her rub my cock all over it was driving me wild. She was panting like a slut in heat. I could tell she was really enjoying it. I then told her to begin sucking my cock. When I had her pick up the pace, I told her that right before I came, I was going to pull out of her mouth and come all over her face. "Would you like me to do that?" I asked. She nodded. I told her to beg for it, "Oh please, Daddy. Let me suck you until you squirt your come all over me. I'll be a good girl, I promise!" she whimpered. After I came, she looked up at me and smiled, my come dripping all over her.

After wiping her off, I instructed her to lie on the bed and not to move, make a sound or come while I played with her. I spent about twenty minutes playing with and sucking her tits and cunt until she could take no more and began moaning and squirming around on the bed. I told her what a bad girl she had been. "And what happens to bad girls?" I asked her.

"They get punished," she replied.

"Well, then get up on all fours," I ordered.

I then got my belt and began spanking her ass. I started off lightly because I didn't want to hurt her, but when I saw she didn't mind, I began spanking her in earnest.

After tiring of this, I stopped. I told her she was a good girl for taking her punishment, and now it was time for her reward. I plunged my tongue into her delicious pussy. She was so wet and hot, I had her coming in no time. After she came I decided it was time to explore some more new ground. I had fantasized before about eating her sweet ass, but was afraid she would think it was weird. Now I didn't care, because I knew I was in control. I started tonguing her butt. "Do you like this?" I asked her.

"Do you?" was her reply.

When I told her I did, she said, "Then so do I. I want whatever you want. I'm here to be your plaything." I was in heaven!

I decided that I wanted to have my ass eaten. I got up on all fours and commanded her to lick my asshole. There's nothing like having a woman's tongue up your ass! Unfortunately, I couldn't enjoy it for too long, because I was ready to fuck.

Gina got on all fours, and I plunged my cock in to the hilt and fucked her harder than I'd ever fucked her before. While we fucked she yelled, "Oh yes, Daddy! Beat your little girl! Make it hurt, I love it!" Needless to say, this sexual encounter was a huge success!

Since that night I've ordered bondage equipment through the mail. I have tied Gina up and treated her like a slave countless times. Once I left her tied to the bed with a dildo in her cunt and a vibrator up her ass while I went downstairs, smoked a cigarette and watched television for twenty minutes. The whole time she was sobbing for me to come upstairs and eat her pussy.

Sometimes we have "normal" sex, but even then we both know who's in charge, and if she gets out of line, I'll remind her.—Name and address withheld

HE STARTED THE DAY A SIMPLE MAN—NOW HE'S A FANCY NANCY

I'm writing to tell you about my transformation from a simple man to a submissive slave. It all started when I fantasized about what it would be like to dress as a woman. I had never worn women's clothing before, but I really wanted to try it, so one day I worked up the nerve to go into a lingerie store.

As I entered the store, I was really nervous. I made sure no one was there except me and the saleslady. She walked up to me and asked if I needed any help. Her name was Annabel. She was unbelievably beautiful and dressed very sexily. I couldn't take my eyes off her. She was tall and slim with long blonde hair and blue eyes. I blushed furiously.

Annabel smiled and said, "Can I help you pick something out for your wife or your girlfriend?"

I said, "No, thanks. I'll just look around." I had no idea what I was looking for, and my hands were sweating from nervousness.

After about ten minutes, Annabel came over to me. I was looking through the panties and bras, trying to figure out what size would fit me. Annabel asked, "What size do you need?"

I said, "I don't know."

She asked, "How big is she?"

I gulped and said, "About my size."

At that point I thought I would die of embarrassment. Annabel just smiled, looked right at me and said, "Are these for you? Tell me the truth, because I can help you find the right size."

I looked into her eyes and said yes. Annabel said, "This is your first time, isn't it?" Again I said yes. Annabel just took my hand and said, "You've come to the right place. We're both going to have fun with this."

Then she said, "If you listen to me and do what I say, you're going to look great. Now go to the dressing room, and I will bring you a few things to try on."

I went to the dressing room without saying a word. I couldn't believe I was in a ladies' dressing room, ready to try on lingerie with a beautiful saleslady just outside the curtain. I was afraid someone might come in, but she said, "Don't worry, it's almost closing time."

She handed me a pair of sexy black lace panties and a matching bra. I put them on—they fit perfectly. Annabel said, "Let me see," and opened the curtain.

I felt a bit humiliated, yet excited at the same time. Annabel giggled, "Don't you look sexy. Let me see what else I can find for you." When she walked away, I left the curtain open.

She came back holding a pair of lacy black nylons and a matching garter belt. Then she went to the storage room and returned carrying a blond wig. She smiled and said, "Try this on."

The hair came down to my shoulders, long and silky. I told her I felt like a complete woman. Annabel said, "I think I will rename you Nancy. Step out here, Nancy, and let me get a good look at you."

I stood in front of her, waiting for her approval. She could tell how excited I was by the size of the bulge in my panties. "By the looks of things, you're having as much fun as I am. There are a few things missing, but unfortunately, I don't have them here, I will have to go next door to the dress shop."

With that she walked out the door. A few minutes later, she returned with a bulging shopping bag. She pulled out a sexy red minidress, matching pumps and a black belt.

I put the garments on right there in front of her. I felt so at ease with her by that point. She said, "Now sit down and let me apply your makeup."

First she applied foundation, then blush, eye shadow and bright-red lipstick. When she was through, she said, "Now look in the mirror and see what a pretty young thing you have become." I felt so feminine.

Just then two ladies entered the store. I didn't know what to do. Annabel said, "Don't worry, they're friends of mine," before calling them over. I was so nervous, not knowing what they would think when they got closer. Annabel introduced them as Tatiana and Babette. Babette smiled and said, "And who is she?" To my utter dismay, Annabel told them the entire situation. Tatiana and Babette seemed to take it in stride, but I decided it was time to leave.

When I went back to the dressing room, I found that my clothes were gone. I looked over at the ladies. Annabel said, "If you are going to leave without my permission, then you will have to leave as Nancy."

I walked over to Annabel and asked permission to leave. She said, "You must learn to listen to me. Now, as your first punishment, I want you to take off your dress and show Tatiana and Babette what you are wearing underneath."

As I slowly took off my dress, I became excited and had no way to hide it. Annabel said, "Put your hands on your hips and turn around so we can see all of you. Do it now." In a loud voice, Tatiana said, "Look how sexy she is in her garter belt and nylons."

Babette said, "Annabel, I think she should be punished for getting so excited in her panties. Just look at that bulge!" Tatiana agreed.

Becoming more nervous, I said that I couldn't help it if my cock was hard. Annabel said, "What was that I heard you say? From now on that is your pussy. Have you got that? Now I want you to ask Babette if you can pull your panties down and rub your pussy."

I couldn't believe what I was doing, but I looked at Babette and did as I was told. She smiled and said, "Yes, but only pull them down to just above your knees. Do it slowly."

Annabel pulled a camera out of her bag and said, "Here, Tatiana. As Nancy rubs her pussy for us, take some pictures."

I slowly pulled my black lace panties down and my hard cock—I mean pussy—popped out. I started rubbing it slowly. I was so excited, I knew it wouldn't be long before I came. Soon huge globs of spunk were landing on the floor. The girls laughed the whole time. Annabel said, "Now didn't that feel good? I think you need to thank Babette for letting you come."

Still holding my pussy in my hand, I thanked Babette for letting me masturbate. She smiled and said, "Annabel, I think you've won this one over."

Annabel then stroked my cheek and said, "There are going to be some rules. Do you want to be my live-in maid? Answer yes or no."

I said, "Yes."

Holding up my "man" clothes for me to see, she said, "Take one last look, because you won't be needing these any more." With that she threw them in the garbage.

Annabel continued, "From now on you will wear what I tell you to wear, except when you go to work, but you must wear pretty lingerie under your work clothes." Babette and Tatiana watched me intently to see if I would agree to Annabel's terms.

I said, "Yes. I will do as you say."

"Good!" she exclaimed happily. "Now go put your dress back on and fix your lipstick. We need to buy you more clothes and makeup of your own."

Babette added, "And she will also need a razor to shave all her body hair."

"Yes," Annabel said. "I expect your legs, underarms, chest and genitals to be smooth. You got that?"

I moved in with Annabel that very night. One day she told me that she had told her boss, Vince, about me. He wanted to meet me, so I had to come to the store and hang around all day. Annabel even made me assist some of the customers. I looked pretty good, but I think some of them could tell I was really a man.

Near the end of the day, Tatiana and Babette came in to see if Vince had arrived.

Just then he walked in. He was big and well-built with dark hair. Annabel locked the doors and brought Vince over to me. He said, "I hear you suck a mean dildo." I was so nervous, I couldn't respond.

Annabel turned to me and said, "Nancy, the girls and I set this up for you. Now do as you're told. Kneel in front of Vince and ask permission to undo his pants and suck his cock."

I assumed the position, knowing there was no going back. Vince gave me a big smile and said, "Get to it, Nancy." Babette squealed and said, "I've got to get this on videotape."

I pulled Vince's pants down to his ankles. After I removed his underwear, his big cock nearly hit me in the nose. As I was about to suck my first cock, Babette yelled, "Hold it! Annabel, make Nancy fix her lipstick"

Annabel handed me a tube of bright red lipstick. I applied it slowly as Babette got it all on film. By that time pre-come was dripping from Vince's cock. Annabel said, "Go ahead, take it in your mouth."

And that's just what I did. I couldn't believe how natural it felt. Before long I had so much of his cock in my mouth that my nose was nestled against his balls. Vince grabbed my hair and said he was ready to come. Annabel said, "Nancy, I want you to swallow it all."

Just then Vince started shooting his load down my throat. I swallowed as much as I could, but some dripped out the corners of my mouth. After Vince left, Annabel said, "Girls, I think Nancy is one of us now. And even if she doesn't think so, we have the tape to prove it."—N.E., Roanoke, Virginia

BORED WITH MARRIAGE, A HORNY LADY BECOMES A NASTY MISTRESS

I'm a thirty-year-old, married female. I am considered very attractive, with long red hair, a cute little ass and firm breasts. My husband works all day, then spends the evening getting drunk in some bar. He is usually so drunk by the time he gets home, I haven't set eyes on his cock in over two years.

Because I am a very horny woman, I fell in the habit of fingering myself several times a day. Recently, however, I've found a new way to satisfy myself, and my new lovers are more than eager to satisfy my lust for sex.

I got into domination about six months ago after I started reading your magazine. Now I am treated like a queen by my sex slaves. I've known Ned and his foxy wife Erica for many years. I've always wanted to fuck both of them, so I put a plan into action.

Erica is a hairdresser with short blonde hair, tits nearly as big as mine and a knockout body. I called her at her salon, told her I needed a haircut and asked if she would stop by my house on her way home. She said she'd be by around six o'clock that evening. My next task was to get Ned to come over to my house before six. That was no problem. I called him up and asked him to help me move some furniture. He arrived at my house at four in the afternoon. I was wearing a pair of tight shorts and a skimpy tank top. Ned gave my body a good once-over as I led him down to the rec room in the basement. "What do you need moved?" he asked.

"Me," I replied, removing my top, freeing my juicy tits and grabbing his crotch.

Ned said, "I'd like to, but I don't screw around on Erica."

I pushed him onto the bed and tied his hands to the posts with the ropes I had placed there for this occasion. Then I pulled down his jeans and ripped off his shorts, exposing his tasty dick. All the while Ned was begging me to let him go. "Not until I fuck your brains out," I said before ravaging his cock with my mouth. It didn't take long to bring his cock to attention.

I took off my shorts and lowered my aching pussy onto his cock. As I fucked him I told him that his sweet wife was coming by shortly, and that soon she would also be my prisoner. Soon Ned shot his load deep into my pussy. "I wonder what your beloved Erica will say when she finds your come inside me," I teased.

"Please don't say anything," Ned asked. I just laughed. Then I took one of my dildos, greased it up and stuck it deep inside Ned's tight ass. "That better be there when I get back," I warned, "or your wife will get a good whipping."

I took a bandanna and gagged his mouth with it. "See you soon, big boy," I said as I headed upstairs. I put on a robe, hid a pair of handcuffs under a sofa cushion and waited for Erica. She showed up shortly after six.

Her skilled hands and fingers gave my scalp a good massage as she washed and conditioned my hair. When she admired my beautiful red hair, I said, "It's all natural. Here, see for yourself." With that I opened my robe and let her gaze at my flaming-red pussy. "Very nice," Erica cooed.