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10 Greatest Penthouse Letter Subjects Of All Time

Over the years, Penthouse Letters have addressed a variety of subjects. Here are the best contributions ever made to the well-known adult magazine. Thanks to Penthouse Letters, a section set aside in the well-known adult magazine for stories, the phrase “I never thought this would happen to me…” has become a cliché. This is a collection of the most well-liked situations readers have found entertaining during the many years these stories have been a mainstay of Penthouse.

Playboy, Penthouse, and Hustler were the three publications that teen guys desired when they were growing up in the 1980s. Penthouse was never more Hustler than Playboy, despite its moniker. One feature that set it apart from the competition was the Penthouse Forum, where readers could submit sexual letters to be published. These tales have always been accompanied by vivid images of extreme adult scenarios. The stories are purportedly true, yet they are undoubtedly inflated and, in many instances, almost certainly fiction. These tales are fantasies for the reader, whether they are true or false.

“Jailhouse Stories” deserves special note. Yes, this topic, a mainstay, didn’t even appear on the list! Jailhouse sex tales can take a number of different turns; they could involve gay liaisons, guard liaisons, or—even better—escape liaisons. If you haven’t guessed it, sex is the one element that all of these tales have in common.

Everything from random encounters to several partners to distressing circumstances are included on this list. Pull up your pants, for Christ’s sake, and grab your prefered beverage. Here is a ranking of the top Penthouse letter subjects ever.


10 Greatest Penthouse Letter Subjects Of All TimeEvery time I smell leather now, I think of him, which is something I never thought I would be into.

One of two scenarios often applies to these tales: the first is the situation in which someone receives an appointment as a gift or recommendation. This is, I suppose, the gift for the woman or man who avoids spa days. Anyway, until the leather touches their bottom, the person is typically reserved and shy. The “dating a dominatrix” circumstance is the second scenario. Although many guys fantasise about it, they are undoubtedly too afraid to act on their fantasies. The texts claim that individuals who are brave are rewarded for their spirit of adventure.

Old Friend

10 Greatest Penthouse Letter Subjects Of All Time“Seeing my high school sweetheart after 20 years was something I never thought would happen to me,”

The story of the old acquaintance involves a chance meeting, “coffee,” and then a neighbouring frolic a la Fatal Attraction. The best storytellers have a backstory about how this boy (her high school’s starting quarterback) would never speak to her, but that she finally got him and it was amazing. It’s possible that the story will eventually take a vindictive turn (again, think of Fatal Attraction) in which the girl makes up for her wrongdoings by leaving the man bound to a bedpost while she calls his wife, who just so happened to be the head cheerleader in high school. Yes, stories of retribution are the finest.


10 Greatest Penthouse Letter Subjects Of All TimeYou can appreciate my surprise when she took my hand and placed it — I’ve never been with another lady.

Lesbians, especially first-time lesbians, are among the more well-liked subjects. A common plot point is that the girl is quite bashful and is shocked by how quickly her friend turns her on. Remember that these are women, not two males, and that the atmosphere is sensual up until the point where candles, caressing, and margaritas combine to really turn her on. I’m not sure what the Penthouse Letter term means, but I do know that it’s called the money shot in movies.


10 Greatest Penthouse Letter Subjects Of All Time

I never imagined that I would write a letter to Penthouse, but then again, until recently, I never really got into bikers.

I have no idea why, but maybe it’s because people enjoy fantasising about having sex while riding a motorcycle. The original setting is frequently having too many drinks in a tavern that is only lit by a neon Pabst sign. Typically, a gullible east coast female or naive valley girl who had sex with a sweaty Harley guy submits the letter. I felt like I was with a bear, she said. There was a lot of hair back then, and these forum letters were highly popular.


10 Greatest Penthouse Letter Subjects Of All Time

“Until the day, I often wondered what my neighbour Rick was doing.

There are countless places, but the storyline is frequently the same. These messages might be about “dressing up” or something more violent, like a rape fantasy, but usually they are about something simpler. There certainly seems to be a lot of lust for neighbours who just so happen to stop by searching for candy, smokes, or practically anything other than sex. A girl is watching her neighbour, who is shirtless, mow the yard; moments later, he is on her porch sipping lemonade. After a short while, everything is undone and it’s kinky time. These fantasies never come true—I mean, who still makes lemonade?


10 Greatest Penthouse Letter Subjects Of All TimeI’ve always been a quiet, shy girl, so you can imagine my surprise when…

The celebrity isn’t named for a variety of reasons, although there are generally hints. For illustration’s sake, let’s use the made-up phrase, “I don’t want to say who it was, but he was well travelled and had No Reservations!” Penthouse letters discussing celebrity meetings frequently take place at hotels, which makes sense but also appeals to a larger audience. What if his guards discover us? Is he wedded? What if we’re spotted by a tabloid news service? The celebrity sex encounter becomes more and more exciting as the danger increases.

Police Officer

10 Greatest Penthouse Letter Subjects Of All Time

“I often fantasise about having sex with men in uniform, but I never thought this would actually happen to me.”

A girl’s position of power might turn on her, especially if there are additional perks, it should be noted. A good letter will depict a stressed-out woman rushing home after a challenging day at work only to be stopped by a hot cop. The girl pulls up her skirt, leaving the ticket and the worry behind as the two end up in the backseat, forgetting about everything wrong with the world and simply enjoying the moment—which is a very naughty moment.

Pool Guy

10 Greatest Penthouse Letter Subjects Of All Time

“Honestly, I was just working on my tan when he walked over and introduced himself.”

This is one of the more cliche situations, but it does occur, at least in the realm of Penthouse letters. The pool boy is ripped, tan, and frequently wet. He has excellent massage abilities and strong hands for applying sunscreen (or sun tan lotion before the 1990s). The pool house, movable beach chairs, or merely the pool are all available for use once you’re “ready” for some playtime. This letter can also be addressed to the milkman, cable guy, or mailman. Do you recall the days when milk was delivered? Milk guy sex back then had to have been incredible!

The Mom

10 Greatest Penthouse Letter Subjects Of All TimeAlthough I had always thought her mother was gorgeous, it wasn’t until her breast touched mine.

The ideal candidates for this specific tale are teenage boys, who often go one of two paths. The first is the trio of mothers and daughters, or just the mother (far more risky). All it takes is a simple compliment or a breast brush. Hell, it might only require a gentle touch on the kneecap. Keep in mind that since these are young males, every time a breast is touched, sex occurs. A excellent back story that makes the passion seem more genuine is a bonus for “tutoring” or mentor/protégé relationships.


10 Greatest Penthouse Letter Subjects Of All TimeI never imagined I’d be in a trio, but one summer night, my girlfriend invited her neighbour over.

The traditional trio A couple and an acquaintance (another girl; keep in mind that this is Penthouse) are brought together by a Penthouse letter. Alcohol frequently speeds up the process, and before you know it, what was once a pretty tight game of twister under the covers has become even closer. It develops into a story of discovery and joy, fulfilling many people’s dreams and fantasies. There is only one restriction: refrain from discussing the fallout. There isn’t enough alcohol in the world in real life to keep those partnerships together!