LETTERS TO
PENTHOUSE
XXXX
Extreme Sex
Beyond Triple X
THE EDITORS OF
PENTHOUSE MAGAZINE
NEW YORK BOSTON
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Table of Contents
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IT JUST GOT HOTTER
Life—and lust!—begins at 40. LETTERS TO PENTHOUSE® XXXX, that is. Now discover how fans of the world’s unchallenged #1 forum for all things sexual are still finding new ways of pushing the erotic envelope. Celebrate this quadruple-X event with virgin swingers and moaning masqueraders, amorous office mates and gyrating gym rats, oral addicts and backdoor lovers, strip poker players and one shockingly grown-up babysitter. You, too, can share in their pleasure.
Having just completed this latest installment of the Letters to Penthouse series, I am in awe. This is the 40th title in this compendium of erotic writing! For years our loyal readers have indulged us by providing the most provocative form of entertainment available—stories of their naughtiest sexual experiences! We think it’s obvious that you have enjoyed them—as the number of volumes indicates—and it’s our wish that you continue to enjoy them for many years to come. Just thinking about doing a silver anniversary stirs the mind, curious about just what you’ll come up with in the following years.
In this compilation of debaucherous tales, we have pulled out all the stops and made it hot and heavy, just for you. There are titillating tales of Clusterfucks and Swinging, Domination and Discipline, and Different Strokes. Prepare to be whisked away by the tawdry tales of first-time fucking, as well as backdoor banging fun. Push the envelope and let your imagination run wild and your fantasies explode! Thrill to the stories of the uninhibited and unleashed. It’s all about the joys of sex in whatever situation you may find yourself.
If this is your first venture into this genre, let us welcome you to the blissfully wondrous world of our readers’ lustful encounters of the sinful kind. If you’ve read any of our other titles, then you know you’re in for a satisfying read.
Kathy Cavanaugh
Senior Managing Editor
He Worked His Way Through College, and Through His Boss’s Wife
I am a 19-year-old male working my way through college. When I was home last summer, Hal, an electrician who was the stepfather of an old friend of mine, asked me if I wanted to work with him during the summer to make a little extra cash. I said sure, but I had no idea what I was in for.
What I hadn’t realized was that Hal’s wife, May, was also working with him. Now this was a woman who I had fantasized about many times when I was younger. When I came over to hang out with her son, she would often be out on the deck tanning in the sun. She was about 40 years old that summer, but if I didn’t know that I would have guessed that she was in her late 20s. She stood about five feet six and had sandy blond hair and a great, toned body, which she kept in shape by working with her husband. She also had intense blue eyes and an enchanting smile. In a word, she was beautiful.
I would come to the job site each day, and would be tantalized by her all day long. She didn’t do it intentionally, but she did it just the same. She usually wore denim shorts (did I mention that she had great legs?) and a tank top. We would work all day long in the hot sun, pulling heavy wire and working up a good sweat. She looked so sexy, all glistening and drenched with perspiration. By the time I got home I would hardly be able to contain myself. I would beat off while thinking of her sucking my cock, or of ramming her doggie-style. Working with her every day was driving me completely crazy with desire.
At one point work started to get slow, and Hal put me to work in his office, cleaning and organizing it. There was less work for May as well, and as the shop was located right next to their house, I would once again be tantalized by his wife while she sunbathed.
One day I was working in the shop while Hal was out at a building site. May had been tanning on the deck as usual, but around noon she came over to ask me if I wanted some lunch. At the time I was trying to move a heavy box, and she offered to give me a hand with it. As we were moving it she knocked over a box of bolts, and in all the confusion one of her large, luscious breasts fell out of her bikini.
My eyes nearly popped out of my head, but May just kind of chuckled and quickly put her boob back in, saying, “Oops!” She bent down and started picking up the bolts, and as she straightened up she saw the obvious tent in my pants. She looked at me with a little smile and said, “Did you like what you saw?” All I could do was nod stupidly.
“Would you like to see more?” May asked.
I felt dizzy. I just stood there, wide-eyed, and nodded again. Then I started babbling, blurting out to her about how I had fantasized about her many times, and how I would masturbate while thinking of her. She smiled and took a couple of steps toward me, never taking her eyes from mine.
“Really?” she said then. “Were your fantasies kind of like this?” Then she reached out, gently grabbed me by the back of the neck, and pulled me closer, placing my hand on her breast and kissing me like I had never been kissed before. Our tongues slithered over and around each other, reaching and sliding. I pushed her top aside and felt her hard nipple in my hand, while my other hand reached around and squeezed her beautiful ass. She tore off my shirt and ran her hands all over my chest and arms.
“Mmm, you have such a hard young body!” she said in a low voice. Then she leaned forward and started licking and kissing my nipples. She moved down over my stomach, stopping to stick her tongue in my belly button. Then she knelt on the floor and undid my pants. There was a stepladder behind me, and I sat down on it as she pulled my boots and socks off, then slid down my pants and boxers.
My cock was purple and throbbing now. May grabbed it firmly at the base, and a drop of precome fell onto her cheek. She looked up at me and licked the end of my dick. Then she took the head in her mouth and swirled her tongue around it. She licked the shaft from base to tip. Then she slowly slid all eight inches of it into her throat and turned her head from side to side. It felt so good, I thought I might pass out. She then proceeded to slide her lips up and down my whole length, all the while fondling my balls.
I reached out to run my hand through her hair. May put one of her fingers in her now dripping pussy, then pulled it out and slowly slid it into my asshole. I was a little startled at first, but I couldn’t believe how good it felt. She slid her finger in all the way, wiggled it a bit, and then began to move it in and out in rhythm with her bobbing head.
Faster and faster that head moved, until she was practically pounding her face into my lap. I couldn’t hold back anymore, and she pulled her finger out of my ass as I erupted deep in her throat. I spasmed so hard my cock popped out of her mouth and shot two globs of hot come onto her face before she could get it back. She kept sucking until I stopped twitching and started to go soft. Then she wiped my come off her face and licked it from her hand, all the time humming with approval.
My head was still swimming as May took me by the hand and pulled me, weak-legged, into her house and up to her bedroom. There she removed her bathing suit and lay down on the bed, pulling me with her. We kissed again passionately, and then I moved down to her tits and then to her belly. I licked her inner thighs and moved up to her smoothly shaven pussy. I licked her cunt lips and then slid my tongue between them as far as it could go. Then I moved up to her clit, and she squirmed as I twirled my tongue around it. “Eat me, please!” she yelled, grabbing my head and pulling it into her juicy pussy.
That was it. I lashed savagely at her with my tongue as she ground my face in harder. I rubbed her clit with my thumb, stuck my middle finger in her
ass and pounded away. May came and came hard, bucking against my face. Her hot juices gushed out of her and streamed down my chin, dripping onto the sheets. Once she stopped orgasming she rolled over onto her hands and knees, her ass sticking up at me. “Fuck me!” she cried out. “Fuck me deep and hard!”
I took my cock in my hand and slid it over her crotch, from her belly to the top of her ass crack and then back down. I did this about three times, until she gasped out, “Oh, God, please put that hard cock inside me!” I brought my dick to her entrance then, and slowly slid it into that luscious pussy, inch by inch. May quivered with each inch. I proceeded to fuck her slow and deep, until she moaned, “Oh, just fuck me!” With that I grabbed her hips and increased my speed until I was pounding her as hard as I could. She was moaning loudly now, and this got me going even more. I turned her onto one hip so I could see her face and watch her tits bouncing as I pounded her. She came violently again, her juices gushing around my cock. But I wasn’t done.
“Oh, Christ, you’re still hard!” May panted when she finished spasming. “Oh, baby, fuck me in the ass with that big dick!” So I pulled out and slowly slid my cock into her tight, beautiful ass. As I began to fuck her that way, she reached over to her bedside table, grabbed a vibrator, and slid it into her cunt. I could feel the vibrations through the thin wall separating her ass and pussy. I pounded her harder and harder until we both exploded, and I shot a load of come deep inside her tight ass.
When I was done I collapsed next to her and we spooned, with my softening cock still inside her. I fondled her tits and kissed her until she said we’d better get up before her husband got home. Before I left she told me this had been great, but that it had to be a onetime thing, and wouldn’t happen again. And it didn’t. But even though I am still a young man, I can’t help wondering if I will ever have anybody that good again. I can only hope so.
—Name and address withheld
They Couldn’t Afford the Car, but His Sexy Wife Made a Deal
Four months ago my wife, Helen, had her 37th birthday, and for some reason she started to get a little nervous about entering middle age. She stepped up her visits to the gym, started watching her diet more closely, and changed her hairstyle.
Helen is something of a classic Midwestern girl next door. She’s five feet five, weighs 125 pounds, and is in very good condition, with a nice tan. She has delicious 36C breasts, a 25-inch waist, and a perfect pear-shaped ass.
For a while now Helen and I have been thinking about getting a convertible sports car. A couple of weeks ago we stopped in at a few dealers and looked at some used vehicles of the type we wanted. There was one particular red car that my wife was quite fond of, but the price was about three or four thousand dollars over the limit we had set. On the way home, I mentioned to Helen that the way the salesman had been looking at her, she might be able to talk him down in price quite a bit. Helen admitted she had noticed his interest, and acknowledged he had seemed kind of cute, but said she thought he was just anxious to sell a car. But she seemed flattered that the salesman, who I figured was about 10 years younger than she was, had paid so much attention to her, and I began teasing her about how she could seduce this young guy so we could get the car she liked for the price we wanted to pay. Helen took it as a joke.
The following day I suggested to Helen that we should go and test-drive that convertible. I told her to wear a short skirt and sexy top, just in case I needed help in negotiating, and somewhat to my surprise, she did so. Sure enough, the same salesman was there, and eager to wait on us. We found out that his name was Ray, and that he was 28 and single, and was selling cars while he finished his MBA.
I then suggested that Helen take the car out for a test-drive with Ray. Ray seemed to enjoy watching her climb into the driver’s seat, showing a lot of leg as she adjusted the seat and found the pedals. Ray pointed out all the features, and they were off.
About 15 minutes later they returned. Helen was very excited about the car, and Ray was amping up the sales pressure, well aware that we were interested. We spent the next half hour in his office, going over the details of a possible purchase, but as closing time neared we were still two grand apart. Ray seemed heartsick that we weren’t willing to cave in on the price. As we walked toward our car I turned to Ray and told him I was hoping he could think of some way to make this deal work, adding that Helen would do just about anything to get that car.
On the way home Helen asked me what I had meant by that comment, and I repeated my thought about how maybe a nice little romp in the sack would persuade Ray to come down on the price, adding that it would also fulfill my long-term fantasy of watching my wife get fucked by another guy. Helen again treated this as a preposterous suggestion. A few minutes later she reached over and grabbed my crotch, teasing me about having a hard-on from thinking about her getting screwed. I told her that she looked a little flushed herself; her nipples were rock-hard, and I would have bet that her panties were damp as well. Helen said nothing to this, and I ended our conversation by noting that it would be a good experience for her to get fucked by another man at this point in her life.
A few days later Ray called to ask if we’d had any further thoughts about raising our offer. I said not really, but suggested that perhaps he could come over for a drink that Friday night to continue the negotiations. Ray said that sounded like a good idea, and we agreed that he would come over around nine o’clock, after work.
That night I mentioned to Helen that Ray would be coming by the house on Friday. “Just in case you’re in the mood to seduce him,” I told her. She didn’t bother to reply.
The next day I went shopping for Helen. I purchased a pink satin and lace bustier, matching pink satin thong panties, pink stockings, a pink silk blouse, and a short pink skirt, and that night I gave it all to Helen. She thought the outfit was very nice and sexy, but was not sure just where she might wear it. I, of course, suggested that it might be a good outfit to wear when Ray came by on Friday evening.
I think it was at this point that Helen realized how serious I was about having her attempt to seduce Ray. She looked at me for a long time and then asked if I was sure I could handle seeing her with another man. How would I react if she really enjoyed it? I told her I hoped she would, but that I knew we loved each other and didn’t think anything could change that. Without another word, Helen picked up the outfit and went into the bedroom to try it on.
When she came out I couldn’t get over how stunning she looked. The hem of her skirt was a few inches below the top of her gartered stockings, and when she sat down it was quite easy to get a teasing glimpse of her stocking tops. The fit was perfect. Helen admitted that the outfit made her feel elegant, sexy, and a little naughty. I told her that she looked tempting as hell, and that if she wasn’t interested in getting something going with Ray, she probably shouldn’t wear that outfit on Friday night.
All day Friday I kept wondering how Helen would react when Ray showed up, and whether anything would happen. My plan was to have Ray join us on our covered patio, adjacent to our pool and hot tub. The weather was beautiful, warm but not too hot. The patio refrigerator was stocked with drinks and snacks, and as the time approached I put some CDs on the stereo. At a few minutes before nine Helen emerged from our bedroom, again wearing the pink outfit, to which she had added a pair of sexy strap sandals. I handed her a strong margarita and told her how gorgeous she looked, adding that it looked like she was planning to seduce Ray after all. Helen just smiled and said she would take things one step at a time.
At 9:15 the doorbell rang. Helen and I both went to answer it, and as I opened it we were startled to find that Ray was not alone. He quickly introduced us to Matt, the manager of the dealership where he worked. Matt’s first words were, “You’re right, Ray, she is beautiful.”
Helen was a little flustered. She was self-conscious about her outfit, and I sensed that she was even a little disappointed, as it appeared that our plans for the evening were dashed. Ray qui
ckly explained that he was not authorized to negotiate a lower price on the car, so he’d brought Matt along, in case we were still interested.
Matt looked to be about 45 years old, in very good shape, well groomed and with the communication skills and demeanor of a successful businessman. He was polite and gracious, as was Ray. I invited both men out to the patio for a beer. Helen had another margarita, and we chatted for the next half hour or so. Both men obviously enjoyed Helen’s company, watching her every move as well as they could without seeming rude. We all got along well and enjoyed the appetizers, booze, and music, but when we got around to talking about the car, neither side seemed ready to budge.
At one point I mentioned to Matt and Ray that Helen enjoyed dancing, and suggested that they might like to dance with her. Ray went first, asking her if she’d care to join him for a slow dance. Helen gave me a funny look, but accepted the invitation.
Ray held her closely but politely as they danced on the patio. I danced with her next, gently placing my hands on her ass as we moved to the music. Helen whispered in my ear, with mock disappointment, that it was too bad Matt had crashed the party and spoiled my plan. I whispered back to her that Matt’s presence didn’t really spoil anything; it just made things more interesting. Helen picked up my meaning immediately. “Are you serious?” she whispered. “Oh, my God, you are!”
“Look,” I told her. “Twenty years from now, when you look back, I’ll bet you’ll wish you’d given it a try.”
The song ended then, and I headed off to fix another drink. As another song started, Helen turned to Matt and said, “It’s your turn.”
Helen danced with Matt a little more closely than she had with Ray, and his hands wandered a little lower, almost resting on her bottom. Ray was next to dance with her, and now he appeared to realize that we were interested in more than negotiating car prices. One of his hands boldly explored Helen’s ass as she nuzzled her head in his neck. The mood was becoming electric. Before the song was over Ray had both hands on her ass and was slowly hiking up her skirt, in plain view of both Matt and me. I felt my cock getting stiff as her stocking tops and garter straps were revealed. Then her ass cheeks came into view, the garter straps and thong panties emphasizing her beautiful curves.
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