Letters to Penthouse XXXX

by Penthouse International

  When the fucking began the guys decided to have their own contest to see which of them could last the longest inside me. The rule was that each man had to last two minutes before giving way to the next man in line, who would then take his two minutes, and so on, all of them taking as many turns as they could before coming, until only one guy was left.

  All too soon I learned just how experienced these guys were at this game. Each of them fucked me slowly and steadily for his allotted time. With all of them being so laid-back and easygoing, it was hard for me to achieve the orgasms I desired. It soon turned into a fucking marathon, as the men paced themselves, each trying to outlast the others. On and on it went, while all of them took a first turn, then a second, then a third. Finally one of the men climaxed, and then another, and then quickly the third man. Then it was down to a two-man fuck-off, winner take all.

  The man who had originally approached me won the prize at last, as I lay there exhausted. My cunt was saturated with sperm, my thighs were covered with slick and slippery come. When I stood up all their come oozed down onto my legs. I walked bowlegged into a shower, where I let the hot water soothe and refresh my body and mind.

  The men were in the bedroom waiting for me when I came out. These guys may have been middle-aged, but they seemed to be tireless. More money was offered, and when I was asked to get on the bed on my hands and knees, I did so. I figured they were going to take me doggie-style, but then I became aware that the man behind me was lubing up his cock, and before I knew it he had taken hold of my hips and was probing with it at my virgin ass.

  I bit the pillow and clutched at the bedspread as he slid himself slowly into my rear passage. It felt strange at first, but gradually I was filled with a new kind of erotic sensation, which brought cries of passion from my mouth as he took me, slowly at first, then harder and faster, until we both yelled loudly as his throbbing prick filled my ass with hot come.

  I had achieved a really intense, mind-blowing orgasm, and was on an adrenaline-fueled sexual high. I looked around to see the other four guys all sporting lust-driven hard-ons, which thrilled me to the core. Without any preliminaries, I was gang-fucked again, but this time they didn’t bother to hold back. It was hard and wild, and I came again and again. They all came at me at once, and in the end I was penetrated in my cunt and my ass, with a third cock in my mouth and another in each of my hands.

  At last we all fell into an exhausted sleep. I woke up the next morning to find myself between two of the men on the king-size bed. I was feeling very well fucked and a little mischievous, not to mention rich. I got up on my knees and proceeded to awaken one of the sleeping men with a blowjob. The other one woke up as I was doing it. He got behind me and took me doggie-style. I managed to gulp down the first guy’s sperm before I came.

  I went out to the living room of the suite and saw two more guys sleeping on the twin sofas. I knelt on the floor and gave one of them a blowjob, too. When he came in my mouth I didn’t swallow it right away; I opened my mouth and showed him his sperm puddled on my tongue. Then I tilted my head back and swallowed it all down, letting him see my throat moving as I did so. “Yum yum,” I said, and he laughed and kissed me.

  The guy on the other couch now got up and bent me over the coffee table. He put a lot of spit on his dick and slowly stuck it up my ass. I began to moan right away, and I climaxed three times before he shot inside me.

  The fifth man was in the shower, so I went in and joined him. He took me standing up, against the wall, with my legs wrapped around him and the hot water pouring down on us. I came again, and then I went to my knees and cleaned him off with my mouth.

  The men ordered breakfast from room service. I stayed naked as I joined them at the table out on the balcony. There was an envelope on my plate, with a fat wad of bills inside it. I smiled at them. “Thanks,” I said. “Maybe after breakfast I can do something to earn this.” And everybody laughed.

  I thought back on those early adventures as I left my old dorm room after fucking all those college boys. It was exciting to be back on campus again, reliving the old days and finding new young people to swing with. And I still had two weeks to go! I would certainly have a lot to tell my husband about when I got home.

  —R.C., Tulsa, Oklahoma

  How to Get a Little Head in Business Without Really Fucking

  While at a newsstand the other day, I flipped through a copy of Penthouse Letters. I was pleasantly surprised to find a “Domination and Discipline” section, and I bought a copy of the magazine right away. My recent experience at work fits right in.

  I am a divorced, thirty-five-year-old male who works in a large office complex. An executive secretary was recently transferred in from another large city. Suzanne is in her late forties and divorced. Her five-nine frame, long brown hair, and large 38D breasts immediately caught my eye.

  Although I do not work in her department, I found myself making repeated excuses just to talk to her. Her response was always cool and aloof. Finally I got the nerve to ask her to lunch. She declined and told me directly that she was not interested. I guess I was not surprised. All the men in the office had been drooling over her since she arrived, and besides, I had never had any luck with older women.

  Four months later I left the office at about seven. In the parking garage, I found Suzanne at her car, which would not start. I offered her a ride home, and she reluctantly and coolly accepted. I tried to make small talk on the way, but she just glared at me as if I was a child.

  When we reached her condo, I asked if I could come up for a drink. This really upset her. She turned to face me and in no uncertain terms stated that men do not ask for such a privilege, they only receive permission. Suzanne went on to say that I should quit pestering her. She only enjoyed men who would go out of their way to please her, and she said I just didn’t look like the type.

  I had always been dumbstruck by her beauty, but now I found myself turned on by her commanding tone. I said that I would go out of my way to please her, to which she just laughed. “Ring my apartment bell tomorrow night at eight, not one minute earlier or later.” With this she left the car.

  I sat in disbelief. I did not know what was going on, but I did know that my dick was rock-hard.

  The next day at work she ignored me. I found myself at her apartment slightly early. I stared at my watch and, exactly at eight, rang the buzzer. “Come up, Don,” the disembodied voice intoned.

  When she opened the door, I stood gawking at her. She was wearing a skintight dark blue dress, blue hose, and high heels. “Come in,” she said.

  I sat on the sofa and she sat in an armchair facing me. “Don,” she said, “I am a very fussy person and I hope that you have not wasted my time tonight. We must understand each other. I never raise my voice or become upset, but when I ask something of you, I expect an immediate response. Of course, you said that you would go out of your way to please me. Is this true, Don?”

  “Yes,” I answered, and then she cut me off.

  “If you need to talk, I will let you know. The bar is in the corner; I’ll have a bourbon over ice.” I walked over to the bar, mixing us both a drink. When I returned, she took her drink and asked, “Who offered you a drink?” I was fumbling for words when she instructed me to pour the extra drink down the sink, which I dutifully did.

  “Come here, Don.” I walked over to the armchair and looked at her. I felt like a child who had just been scolded. “Don, do you still want to please me?”

  “Yes,” I said. She looked me right in the eye and said, “Kneel.” Drunk with her beauty, I knelt at her feet. Slowly she crossed her legs and instructed me to remove her extended shoe. “Do not lay it down, Don. Stand it up properly.” For the next hour or so, I massaged her feet under her careful direction. Finally she rose from the chair. “If you choose to continue, I will see you next Tuesday at eight,” and with that she left the room. There I was, kneeling at her chair, mystified. I did not understand, but my cock was rock-hard. I stood a
nd left.

  The next week at work, she acted as if I did not exist. Still, I could not wait for Tuesday night. At the appointed time, I rang the buzzer. “Come up, Don.”

  This time she wore a very low-cut dress. Also, she wore no hose, but her tanned legs looked outstanding. When I stood in the doorway awestruck, she stated that if I found the dress too distracting, I could leave. I dumbly shook my head. “Have a seat on the sofa, Don.” Again, she sat across from me.

  “Don, if I ask you to do something for me, will you do it?”

  “Yes,” I said.

  “Well, if you will do what I say, does that mean you are obedient to me?”

  “I don’t know,” I responded. “I never thought about it.”

  “Yes or no, Don?” she snapped.

  I lowered my head slightly and murmured, “Yes.”

  “Well then, say it. Say that you will be obedient to me.” I heard myself saying, “I will be obedient to you.”

  “Very good, Don.” She smiled. “Bring me a drink.”

  When I returned she instructed me to go to the bathroom and come back naked. I hesitated momentarily and she said that if I did not do as she said, I could leave immediately. Soon, I stood in front of her naked. “Kneel, and hurry about it,” she commanded.

  I knelt and my cock started to stiffen. She smiled and looked very pleased. I removed her shoe and carefully stood it upright. As I massaged her feet, she asked, “Would you like to see me naked, Don?”

  “Oh, yes,” I replied eagerly.

  She laughed and said, “That is something that you must earn. Kiss my feet.” In no time, I was licking and kissing every inch of her feet. This seemed to excite her immensely. I did not think that I could get any hotter at this point. Finally she instructed me to replace her heels and to move slightly away from her, still on my knees.

  “Don, do you remember what you said earlier?”

  “Yes, Suzanne, I do.”

  “Very well. Masturbate for me.” When I hesitated, she spoke in a very commanding voice. “When I speak to you, you do as you are told immediately. Let’s go, pump that cock and fill your hand with come.”

  I began to beat off furiously. I wanted so badly to please her. My humiliation, combined with her beauty, really sent me soaring, and I soon came in my hand. “Very good, Don. Very good indeed. Now crawl toward me.” I moved closer to the armchair. She instructed me to show her my come-filled hand. I obeyed, seeking her approval. “Well, Don, you will have to learn to come more. There is hardly anything there for you to eat!”

  With that she stood. “We have had our fun, Don. If you choose, I will see you next week at eight. However, do not show up if you are not prepared to obey. You must demonstrate total obedience to me. If you are not willing to do exactly what I say, when I say it, I have no interest in you. Do you understand?”

  “Yes,” I said immediately.

  “Also, from now on you are not to have any sex unless I allow it. Not even with your hand!” She laughed and walked into the other room, closing the door behind her.

  There I knelt, my hand filled with come. I cleaned up and left. I could not sleep that night, I felt so humiliated. My cock was made rock-hard with just the thought of the night’s exploits.

  She ignored me all week, but all I could do was think about her. I was constantly hard, but for some reason I did not want to have any sex without her. I was totally captivated with her. Would I go back? What did she mean about eating my come?

  When I rang the buzzer at eight, I knew what the answer would be. “Come up, Don.”

  She was wearing a red halter, a short, skintight skirt, red hose, and high heels. The view of her tits nearly made me pass out.

  We began our ritual, sitting across from each other. “Don, is there something you want to tell me?” I knew the answer by the look on her face.

  “Yes, Suzanne. I want to be obedient to you.”

  “Very good, Don, you are learning well. However, from now on you will address me as Miss Suzanne.”

  “Yes, Miss Suzanne,” I said.

  “Very good, Don. I’ll have my drink now. Return naked with it.” When I walked back into the room naked, carrying her drink, she smiled and ordered me to kneel.

  As I massaged her feet, she asked, “Did you come this week, Don?”

  “No,” I said.

  “Very good. Would you like to come tonight?”

  “Oh, yes, Miss Suzanne.” She just laughed.

  When I finished her massage, she instructed me to put her heels back on her feet and to sit back on the floor, away from the armchair. She stood and spun around. “Do you like my body, Don?”

  “Oh, yes, Miss Suzanne.” She looked hot and my cock was on fire. She asked me if I would like to hold her breasts. “Oh, yes, Miss Suzanne,” I literally yelled back.

  “You’ll have to work for it,” was all she said.

  She walked toward me. “Kiss my foot, Don.” I bowed and kissed her shoe. “Lick it clean,” she said, and I did as instructed. “You lick very well, Don. Would you like to lick my ass?”

  “Oh, yes!” I wanted to do anything I could to touch her.

  “Well, Don, I’ll trade you. I’ll let you lick my ass if you eat your come for me. Are you interested?” I hesitated. “You will eat your come or leave immediately. Now what will it be?”

  “I’ll stay,” I responded.

  “Good boy.” She smiled. She seemed very excited. She loosened her skirt and it fell to the floor. Standing before me, garters, hose, heels and halter, her pussy stared me right in the face.

  “Don, your cock is dripping. You know what to do, don’t you?” With my finger I rubbed the come off the head of my cock. Without thinking, I placed the finger in my mouth. “Very good, Don. You are going to make a fine little whore. Now come here and lick my ass. Touch me only with your tongue.” She leaned over the armchair and I raced on my knees to her. I began kissing and licking her ass. “Come on, Don, you know what I want. Show me the whore that you are. Fuck my asshole with your tongue,” she commanded. I tongued her wildly. She began to rub her pussy and soon exploded into orgasm. I licked her pliant asshole until she instructed me to stop.

  She dropped down onto the chair. “Not bad,” she said with a grin on her face. “We’ll have to teach you how to worship asshole. Now, Don, I’m going to hold out my hand and count to ten. When I reach ten, you will fill my hand with your come. If you fail me, you will leave for good.” She held out her hand and I pumped wildly. I didn’t want to leave. On ten, I filled her hand. I had never come more in my life.

  “Beg for it,” she demanded as she held her hand up.

  “Please, Miss Suzanne, let me eat my come for you. Let me show you the whore that I am.”

  “Eat slowly, Don,” and she held her hand to my lips. Slowly, I licked her hand clean.

  “Good little whore. I will see you next week,” she said.

  These events happened over a year ago, and to this day, every Tuesday night, I do whatever it takes to please Miss Suzanne. We have never actually had intercourse in the conventional sense. The closest we have come is when she straps on a dildo to fuck me. According to Suzanne, good little whores constantly need a good fucking. I agree. I beg for it. Also, I have yet to hold Miss Suzanne’s naked breasts, but I’ll let you know when I do.

  —D.B., Chicago, Illinois

  Ever Play Lucky Seven? Like Strip Poker, Only Different

  My beautiful wife, Rhoda, and I had nearly come to the end of a weeklong vacation at a gorgeous resort on the California coast. For our final night we decided to go to one of the sports bars nearby, watch a ballgame and have a few drinks.

  I’m proud to say that my wife is a very attractive woman, with a body that always gets a lot of looks. Although we are in our 40s, she can still pass for someone in her late 20s, and the clothes she wears contribute to her youthful looks. On that night she looked great as always as we walked the block to the sports bar. She wore tight blue shorts that showed
off her perfect legs, and a nice tight halter top, revealing just the right amount of cleavage.

  At the bar we sat in a booth and had a few drinks. Everything was fine until a storm caused the game we were watching to go into a rain delay. It showed no sign of ending, and we were thinking about returning to the hotel, when one of us spotted the dart board on one wall, and we decided to play a few games.

  We had played for about 20 minutes when we saw that two young guys were waiting to play also. So we finished up our game and were about to go back to our booth, when one of them asked if we would like to play teams, us against them. We said why not, and as we played we found out that their names were Kirk and Ed, that they were both going to medical school, and that they were in the area on a weekend break from their studies. Both of the guys were good-looking and seemed to be pretty fit. Kirk was about five feet ten and was the more talkative of the two, while Ed was about six feet four, very reserved and quiet.

  Rhoda was a pretty good darts player, and she was making the rest of us look silly. We played for about 30 minutes, with Rhoda and me winning every game. Kirk then suggested that the loser of the next game should buy a round of drinks. We agreed, and once again, because of Rhoda, we won easily. Kirk and Ed ordered the drinks, and then suggested we raise the stakes and make a little cash wager on the next game.

  I was about to say no when Rhoda asked, “How much?” The guys had a brief consultation, and then Kirk suggested $200. I immediately told him that was too much for us, but again Rhoda interrupted. I didn’t know if it was the booze or the two good-looking college boys or what, but she seemed anxious to accept the bet. I told her I didn’t even have that much cash on me, to which she replied, “So what? We’re going to win anyway.”

  At that point Kirk said that they would raise the bet to $500. I laughed and told him that if I didn’t have $200 on me, I certainly didn’t have $500. Kirk said that was no problem; they would adjust the stakes. If we won they would pay us the $500, and if they won, Rhoda and I would go to their hotel room and play another game called “Lucky Seven.” Rhoda said yes before I could even ask them what the hell Lucky Seven was. Kirk said they would explain it to us later, and we began to play again.