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10 Greatest Penthouse Letter Subjects Of All Time

By David Grant
Published Aug 22, 2015

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Penthouse Letters have covered a range of topics over the years. Here are the greatest submissions ever sent to the popular adult magazine.
"I never thought this would happen to me...", a line that is now classic thanks to Penthouse Letters, a section reserved in the popular adult magazine for stories. For many years these stories have been a staple of Penthouse, this is a list of the most popular scenarios readers have enjoyed.
Growing up in the eighties there were three magazines teenage boys wanted: Playboy, Penthouse and Hustler. Despite the name, Penthouse was always more Hustler versus Playboy. One area it differentiated from the others was through running section known as Penthouse forum where they printed sexy letters sent in by readers. These stories are and have always been accompanied with colorful photos of hardcore adult situations. The stories are supposedly real, but definitely embellished and in many cases, probably flat-out fiction. Regardless of true or false, these stories are fantasies for the reader.
Honorable mention goes to “Jailhouse Stories”. That’s right, this subject, a mainstay didn’t even make the list! Jailhouse sex stories go one of several directions; it could be a gay sex, guard sex, or even better, escape sex. In case you haven’t figured it out, the one common component to all of these stories is sex.
This list has everything ranging from chance encounters to multiple partners to painful situations. Grab your favorite beverage and for Christ’s sake, pull up your pants, man! This is a list of the greatest Penthouse letter subjects of all time.
“I never thought I would be into pain, but now whenever I smell leather I think of him.”
These stories typically fall into one of two scenarios; first one is that someone gets an appointment as a gift or suggestion. I guess this is the gift for the girl or guy who doesn’t do spa days. Anyway, the person is usually shy and conservative until they feel the leather hit their bottom. The second scenario is the “dating a dominatrix” situation. Many guys fantasize about, but are probably too scared to put themselves in this situation. According to the letters, those who dare are rewarded for their sense of adventure.
“I never thought it would happen to me, but seeing my High School sweetheart after 20 years…”
The old friend tale is often a coincidental encounter followed by “coffee” and then a Fatal Attraction type romp nearby. The good story tellers have a back story of how this boy (starting quarterback in high school) would never talk to her, but now she has finally had him and it was spectacular. At some point the tale may even turn vengeful (again, Fatal Attraction ) where the girl rights her wrongful past, leaving him naked and tied to a bedpost while she calls his wife (who just happened to be the head cheerleader in high school). Yeah, revenge stories are always the best.
“I’ve never been with another woman so you can understand my surprise when she took my hand and placed it…”
One of the more popular topics is lesbians, specifically first-time lesbians. The storyline is often that the girl is very shy and surprised by how fast she is turned on by her friend. Keep in mind this isn’t two men, these are women; the climate is sensual until of course she gets really turned on with a combination of candles, touching and margaritas. I don’t know what the Penthouse Letter phrase is, but I know in movies it’s known as the money shot!
“I never thought I would write a letter to Penthouse, but then again, I was never that into bikers until recently when…”
I don’t know why (maybe it’s the sex on motorcycle fantasy), but people love biker stories. Too many drinks in a bar that is only lit by a neon Pabst sign is often the initial setting. Usually the letter is submitted by a naïve valley girl or uptight east coast girl who tells the tale of night of sweaty Harley guy sex. “It was as if I was with a bear!” These forum letters were very popular in the late seventies, so much hair back then…
“I’ve always wondered about my neighbor Rick until the day…”
The settings are limitless, but the plot is often the same. These letters could go the direction of “dress up” or something more aggressive such as a rape fantasy; however, it’s usually something more basic. It sure seems like a lot of people really lust for their neighbor who just happens to stop over looking for sugar, cigarettes or really anything but sex. A girl is watching her shirtless neighbor mow the lawn and minutes later he’s on her deck enjoying a glass of lemonade. Minutes later all clothes are off and it’s kinky time. These fantasies never happen, I mean, who makes lemonade anymore?
“I’ve always been a shy girl who kept to herself, so you can imagine my shock when…”
For many reasons the celebrity is not named, but there’s usually clues. For example (not actual) “I don’t want to say who it was, but he was well traveled and had No Reservation s!” Penthouse letters dealing with celebrity encounters are often in a hotel which make sense, but also lends itself to a much broader audience. What if his security catches us? Is he married? What if a tabloid news service sees us? Each layer of danger adds more and more excitement to the celebrity sex encounter.
“I often fantasize about having sex with men in uniform, but I never thought this would happen to me.”
There is something to be said about the position of power and how this can turn on a girl, especially if there are added benefits. A good letter will paint the picture of a stressed woman speeding home after a rough day of work only to get pulled over by a buff cop. The girl hikes up her skirt and not only is the ticket an afterthought, but so is the stress as the two end up in the backseat forgetting about all the bad things and living in the moment, a very naughty moment it is.
“Honestly I was just working on my tan when he walked over and introduced himself.”
One of the more cliché predicaments, but this happens, at least in the world of Penthouse letters it happens. The pool boy is tan, ripped and often wet. He has strong hands for applying sunscreen (or sun tan lotion prior to nineties) and impeccable massage skills. Once “ready” there are a lot of options for play time that include the pool house, adjustable beach chairs or simply, the pool. Other variations of this letter include the cable guy, mail man or milk man. Remember when people had milk delivered? I bet milk man sex was amazing back then!
“I had always found her mom attractive, but it wasn’t until her breast brushed up against me…”
Teenage boys work best for this particular yarn and usually go one of two directions. First is the mom and daughter threesome or just mom (much more dangerous). An innocent compliment or brush of a breast is all it takes. Hell, an innocent brush of a knee cap may be all it takes. Remember, these are young boys; the brush of a breast equals sex 100 percent of the time! Bonus for “tutoring” or mentor/protégée relationships, builds a good back story that makes the passion more real.
“I never thought I would be involved in a threesome, but one summer night my girlfriend brought over her neighbor…”
The classic threesome Penthouse letter puts a couple and an acquaintance (another girl – remember, this is Penthouse) together. The alcohol usually moves things along and before you know it a very close game of twister has turned into an even closer game of twister under the sheets. It turns into a tale of exploration and ecstasy, the dream and fantasy of many. There is only one rule: Do not talk about the aftermath. In real life there isn’t enough alcohol in the world to save those relationships!
David S. Grant is the author of several books including "Blood: The New Red." He writes about pop culture and humor, he is also a degenerate gambler (which he also writes about). You can reach David on Twitter @david_s_grant and his website www.pulpscribbler.com. David lives and works in New York City.

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Enthralled: Paranormal Diversions by Melissa Marr and Kelley Armstrong
WILD, WANTON WOMAN SHARES HER SEXPERTISE WITH OUR READERS
I am a thirty-nine-year-old woman who wants to share the details of my fucking, sucking and exhibitionism with my fellow Penthouse Letters readers. I live with a man who shares my philosophy on sex and love. Not only do we agree on everything, but he actively promotes situations that allow me to fulfill all of my sexual desires.
It is very difficult for me to describe the pure animal pleasure I get when I am with my lover and have the opportunity to fuck other men and women. I love the sex and the physical release, but I also get off on having my man watch me perform. I love feeling a good, hard cock fucking me while I flirt with my lover or hold his hand. Reaching orgasm is normally a very special moment for me, and being able to share this moment with my lover makes me so hot that I would gladly do it every night.
I have participated in almost every sexual situation that I can think of. Although I enjoy them all, my favorite is when a man or a woman spends the night with us in bed. If we're with a man, of course I sleep between him and my lover and just revel in the glory of being the center of attention. If it is a woman who's spending the night, I put her in the middle and, after my guy fucks her, I eat that come-filled pussy with such relish that most of the women ask me if I'm a lesbian.
My exhibitionism is geared toward attracting attention to myself when we're out in public. My lover and I always go out of our way to come up with different methods of showing me off. It's really a very exciting game!
Naturally, I usually wear short skirts, and I love it when people check out my long legs. I also enjoy going braless, and always walk in such a way that ensures my tits bounce as much as possible. When we're drinking in a bar, I'll use the men's room rather than the ladies' room. You should see the looks on some men's faces when I walk in! At home, when I'm expecting company, I've been known to answer the door wearing only my bra and panties. I love to see how a married man reacts in front of his wife!
Even though I have many tricks, my absolute favorite exhibi-tionistic game is to flash my hot pussy in public. For example, when we go out drinking, I always sit on a bar stool rather than in a booth so that I can expose my pussy. My skirts, which are short to begin with, usually ride up a little above mid-thigh when I sit. I make sure it rides up high enough on my legs so that anyone sitting near me has a direct view of my panties or my naked cunt. My lover and I have this game down to a science. We are most amused when guys come over to talk to me and are unable to take their eyes away from my crotch. More than once I've reached orgasm like this, and let me tell you, it's a trip to be sitting on a bar stool while a guy stares at your crotch and you know that you're about to come. Occasionally, when I do wear panties, I've been known to pull off my panties and toss them to the guy who was staring at my pussy. As I leave, I smile and say, “Thanks for watching. Keep the panties as my present to you.” That always leaves them slack-jawed.
I'm sure I could go on and on about my sexual antics, but writing this letter has made me so horny that I just have to fuck my man. I'm so glad that my lover and I are totally in tune when it comes to sex!— T.V., San Diego, California
EXHIBITIONISTIC BACKYARD BALLERS DISCOVER SPLENDOR IN THE GRASS
My lover Toni and I decided to watch an X-rated movie one night recently. We sat close beside each other on the sofa and soon were getting hot as we kissed passionately and watched the writhing bodies.
When I noticed Toni's hard nipples standing up under her shirt, I couldn't resist gently tweaking them. In response, she slid her hand across my thigh and massaged the growing bulge in my jeans. It wasn't long before she had slid off the sofa and onto the floor in front of me. With a deft motion she unzipped my pants and freed my cock, which was aching for relief by this time. She slowly ran her tongue up and down the shaft before sucking the tip into her mouth. I was transfixed by the sight of her full, red lips wrapped around my cock, making it rock hard.
Once she had me good and wet, Toni stroked me with her hand and fondled my balls until a drop of clear, sticky pre-come oozed from the tip. Toni licked it up and told me she loved the taste.
I asked her to turn the TV off so we could concentrate on our own pleasure. Toni switched it off and stripped off her jeans and panties, exposing her partially shaved mound. Then she climbed back onto the sofa and straddled me. She slowly lowered her hot, wet pussy down onto my cock. We both watched as her beautiful pussy engulfed every inch of my cock. I groaned with pleasure as she slid all the way down to my balls. Toni began riding my cock while I kneaded her large breasts. The feeling was incredible.
I suddenly got the urge to make love to Toni while standing up, so I reached under her legs and grabbed hold of her ass-cheeks. At first she was surprised as I stood up, holding her in my arms, and began pumping into her, because we had never fucked in this position, before. But always quick to adapt to any situation, she merely held on to my shoulders and wrapped her legs around my waist as she bounced up and down on my cock. Toni got very excited and, after a few minutes, asked me to fuck her from behind, which is probably our favorite position.
We went into the dining room and Toni leaned over the table. She reached back to spread her pussy lips wide open while I rubbed the head of my cock along her slit. The pink folds glistened with her sweet juices. Holding her by the hips, I slowly drove the full length of my cock deep into her. She moaned with pleasure, and so did I. I started to fuck her faster, and she responded with cries of “Fuck me harder!” Toni came two times in quick succession, and I was getting close to orgasm myself.
I asked her if she would suck my cock some m
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