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Top 10 Greatest Penthouse Letter Subjects Of All Time

Top 10 Greatest Penthouse Letter Subjects Of All Time

“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.


10. Dominatrix

penthouse letter

“I never thought I would be into pain, but now whenever I smell leather I think of him.”

Whenever we hear “sex education,” most people imagine a high school health class teacher outlining the basics: monthly periods, the human development cycle, birth control, and maybe an uncomfortable informational film. However, the topics in these classes barely skim the surface of the depth and breadth of our human sexuality.

For each individual, sexuality is a process of self-discovery, and it can be one of the most invigorating journeys of your life.Did you know that both male and female genitals come from the same embryonic tissue and are identical in the first stage of fetal development? During the whole first stage, the sex of the fetus remains undetermined. After the first stage, the addition of a Y chromosome produces testosterone, which leads to the external and internal sexual differentiation of a male, or an additional X chromosome will prompt production of estrogen, leading to a female.


9. Old Friend

penthouse letter

“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.


8. Lesbian

penthouse letter

“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!


7. Bikers

penthouse letter

“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…


6. Fantasy

penthouse letter

“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?

5. Celebrity

penthouse letter

“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 Reservations!” 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.


4. Police Officer

penthouse letter

“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.


3. Pool Guy

penthouse letter

“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!


2. The Mom

penthouse letter

“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 relationships, builds a good back story that makes the passion more real.


1. Threesome

penthouse letter

“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!

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