Letters to Penthouse V Read online

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  Copyright © 1995 by Penthouse International, Limited

  All rights reserved. Except as permitted under the U.S. Copyright Act of 1976, no part of this publication may be reproduced, distributed, or transmitted in any form or by any means, or stored in a database or retrieval system, without the prior written permission of the publisher.

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  Cover design by Don Puckey

  Warner Books

  Hachette Book Group

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  New York, NY 10017

  Visit our Web site at www.HachetteBookGroup.com

  ISBN: 978-0-446-50627-4

  First eBook Edition: August 1995

  Contents

  Introduction

  Domination & Discipline

  Three-For-All

  Head & Tail

  Pursuit & Capture

  Different Strokes

  Someone’s Watching

  Crowd Scenes

  Serendipity

  Girls & Girls/Boys & Boys

  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

  The great thing about sex is that there are so many ways to enjoy it, so many twists and turns on the road to orgasm. Many of our readers travel the reliable, tried-and-true highway on their journey to the ultimate pleasure. More daring folks delight in discovering the more challenging but perhaps even more satisfying routes to their final carnal destination. This collection of letters includes everything from the traditional to the outrageous. There’s something for everyone. So fasten your seat belt and get ready for a ride you’re not likely to forget.

  John Borrelli

  Senior Editor

  Penthouse Special Publications

  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 h
er 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.”