The Etiquette of Casual Sex

The Etiquette of Casual Sex

Since the 1960s, with its Sexual Revolution, sex outside the context of marriage is no longer considered “wrong.” But even with casual, non-committal sex, there is comportment. There are Do’s, and there are Don’ts. And, for the most part, the do’s and don’ts are all aimed at promoting and maintaining human dignity, no matter how brief, impersonal, or fleeting the sexual encounter. A gentleman’s aim should be to make every sexual experience physically, mentally, emotionally, and socially uplifting for himself and his partner. As such, comportment is required before, during, and after sex.

Pre-Sex Etiquette

Is it impolite to ask for sex on the first date?

There was a time—until the middle of the 1960s—when intimate kissing on the first date was considered “inappropriate,” and only persons of “relaxed morals” would engage in such behavior. Actual, full-blown sex on the first date was tantamount to prostitution—but without monetary compensation. Today, sex is oftentimes the reason for the date or the litmus test for whether there will be subsequent dates. Therefore, given present-day attitudes towards sex, it is “acceptable” for a 21st -century gentleman to request sex on the first date. But it is still to be expected that the request will be politely denied. And what is of paramount importance is that the party making the request understand that “No” means “No!” and that any subsequent request or “motion for reconsideration” is regarded as most inappropriate and grounds for immediate termination of the date.

What is the best way to politely broach the subject of hygiene during casual sex?

One of the most troublesome issues with casual sex is hygiene. Because of the spontaneous, unplanned, impersonal circumstances typically associated with casual sex, the parties involved rarely have time for pre-sex hygiene, and rarely do they share consistent standards for hygiene. How, then, is the issue best raised?

It is often said that “cleanliness is next to godliness.” But cleanliness is also next to sexiness—(unless otherwise specified and agreed!) And notwithstanding Napoleon’s supposed notorious admonition to Empress Josephine, “Don’t wash, I am coming home!” (After all, they were a married couple and were therefore privy to, and presumably tolerant or accepting of, each other’s most intimate preferences and penchants), the anecdotal evidence seems to suggest that people generally prefer clean sex over raunchy, smelly, filthy sex—especially when when it comes to casual sex with people who are little more than strangers.

But if there is one sure way to insult a person to his very core, it is to call to his attention his lack of proper hygiene. Even a big, strong man can become emotionally disarmed if informed disapprovingly of his underarm odor.

One of the most tactful ways to ensure pre-sex hygiene is to incorporate it into foreplay, paying special attention to body parts that will figure significantly during the sex act. A gentleman can invite his lover to a joint bath or shower as part of foreplay. And while enjoying the joint bath or shower, special attention could be devoted to special body parts that are likely to figure significantly in the subsequent sex-act: A gentleman with a fetish for feet, for example, may want to offer his lover a pedicure; a fan of fellatio, a connoisseur of cunnilingus, or an advocate for anilingus, may wish to assist in administering penile pampering or a douche or an enema. The oftentimes-neglected navel, poetically referred to as “the body’s little cup,” (provided that it is an “iny,” not an “outy”!) should be gently cleaned with an alcohol-moistened cotton ball or ear swab in the event a gentleman invites his sex partner to a drink of his “liquid pearls.” Sloughing creams, perfumed oils, and moisturizers can all be incorporated into cleansing and massage rituals aimed at discretely addressing matters pertaining to hygiene. Besides—especially for gentlemen fond of frequent casual sex—cleanliness erases traces of prior sexual encounters: No lady needs to discover another lady’s lipstick on her lover’s “dipstick”; and no lover needs to smell lingering nuances of Elizabeth Taylor’s White Diamonds on a lover’s family jewels. Kissing should be preceded by proper oral hygiene. Therefore, a gentleman should always have extra supplies of individually wrapped, soft-bristled toothbrushes and other oral hygiene products to offer to his sex partners. (See chapter, “Hygiene.” See also chapter “Your Place or Mine?”). Fresh, easy-to-eat fruits with high concentrations of Vitamins C and D should also be readily available to ensure sweet-smelling breath and a sweet-tasting mouth throughout the sexual encounter.

Who is responsible for furnishing the sex-related supplies?

It is said that “a soldier never goes into battle without his helmet,” and that “a plumber never shows up for work without his toolbox.” But the general rule is that the host should provide all the necessary supplies—from clean sheets and towels to hygiene products to condoms and lubricants to clean-up supplies. The safety rule, however, is that when it comes to matters of health and well-being, each adult is ultimately responsible for ensuring his/her health and well-being. Whenever body fluids are being exchanged, appropriate caution must be exercised. And sex, because of the inherent intimacy associated therewith, is an ideal environment for the transfer of of germs, viruses, and diseases. Therefore, in order to minimize the transmission of sexually transmittable diseases and the incidence of unwanted pregnancy, special attention must be paid to the quality and efficacy of condoms. The effectiveness of condoms stored in gentlemen’s wallets and kept beyond their expiration dates can be compromised. Properly fitting condoms of a gentleman’s preferred brand may be ceremoniously purchased in the company of his lover as a part of foreplay. [A person too embarrassed to purchase or to be in the presence of a person purchasing condoms is too immature for sex]. When condoms and other safety supplies are not available, sexual intercourse should be postponed. There are countless ways to engage in safer intimacy without engaging in unsafe sexual intercourse.

Should sexual parameters be established before sex?

Answer: “no and yes.” The general, “sexy” answer is a resounding “No!” Sex tends to be better done rather than said. Establishing—contract-like—what is “permissible” and what is “off-limits” is likely to take the “y” out of “sexy,” leaving only boring “sex” and putting a pall-like damper upon the spontaneous, delightfully surprising, act-and-respond nature of sex. That said, when the proverbial red flag goes aflutter, a gentleman may (and should) state certain boundaries so as to avoid any mid-way misunderstandings. Walking into a bedroom equipped with whips and chains and slings and handcuffs would be sufficient grounds for a man who objects to SMBD to unequivocally state his objections and request consensus on more conventional methods of copulation. And, of course, drugs or any substance that is likely to compromise informed judgment should be avoided before and during sex. In essence, a gentleman need not verbalize his parameters beforehand to his sexual partner, but he should certainly establish parameters in his own mind so that, in the heat of sex, when his “other head” is doing most of the “thinking,” personal boundaries have are already clearly established and can be more easily delineated, especially in the dark….

Should a person disclose health or physical conditions and bodily functions that may adversely impact his/her sex partner’s health and/or enjoyment of sex?

Any condition that is likely to jeopardize health or the enjoyment of sex should be disclosed beforehand. A lady on her menstrual cycle, for example, should notify her sex partner. And, of course, persons suffering from any health condition that could impede the enjoyment of sex or compromise a sex partner’s health should fully disclose in advance so that the sex partner may make an informed decision as to whether to engage the sexual encounter. Transparency and “the naked truth” are critical components of sex-etiquette.

Is it okay to “lie” to a casual-sex partner?

As the age-old adage goes, “If you can’t say something positive, say nothing at all.” The fact is that most people, even the so-called “beautiful people,” feel some insecurities about their bodies, and those insecurities must generally be laid bare during sex.

The general rule is that a gentleman should be very generous with his compliments to his casual-sex lover. After all, what would be the point of “brutal honesty” ? A lover is generally incapable of “correcting” his physical flaws during the casual-sex meeting, so why raise or confirm the issue? Just as a gentleman would compliment the cook of a modest meal or thank the bearer of a duplicitous gift, a casual-sex lover equipped what the legendary actor David Niven may have euphemistically referred to as “short comings” should be made to feel as “big” as possible, even if at the expense of exaggeration. The fact is that people—especially casual lovers whom one may never see again in life—feel better when being positively complimented than when being told cold, hard truths. Sex should be an uplifting, confidence-building experience. Telling a modestly endowed lover who invites comment about his/her inadequacies, “I am sure it will get the job done,” or “Well, at least you will never need bra implants” is more likely to produce an infinitely more positive sexual experience than “Yes, I prefer nine inches—minimum!” or “You sure are no Dolly Parton….” “I had no idea you were this sexy when we were at the bar” is likely to do more for boosting the confidence of a lover than any alcoholic beverage or energy drink.

Lovers should be generously complimented before, during, and after casual sex. After all, there is an element to casual sex that is part-acting, part-fantasy, and a willing suspense of unflattering reality is generally most appreciated—with little or no collateral adverse side-effects.

What is the correct way to depart the love-bed before sunrise the following morning?

Whenever a gentleman must leave the sex-bed before normal waking hours of the following morning, he must notify his lover prior to entering the bed. And whenever it is agreed that a gentleman will leave the sex-bed whilst his lover is likely to be asleep, the gentleman must arrive at the encounter prepared with a pre-purchased, pre-wrapped present and accompanying handwritten note to leave on “his side of the bed” so that when his lover awakens to be greeted by the gentleman’s absence, he is properly represented by his forethought.

During-Sex Etiquette

What is the best way to politely refuse certain sex-acts?

Many of the “green lights,” “red lights,” an “proceed-with-caution amber lights” of sex are turned on and off via the lingua franca of sex: body language. Rarely are words used or required. And verbosity and sex are known to make for estranged bedfellows. A request for anilingus that is responded to with a gentle kiss on the cheek—of the buttocks but no more—sends a clear message of “Thanks, but no thanks.” Likewise, a slight movement of the head—away—when the tip of a tongue is inserted into the ear is heard loud and clear without the utterance of a word.

Are there any taboos left in 21st -century casual sex?

Many sex-acts that were considered aberrant, lewd, or, at best, taboo, in the 1950s are today considered conventional to the point of “compulsory.” Times have changed, and so have gentlemen….

Anal Sex, Anilingus, and Cunnilingus

With the increasing legalization of same-sex marriage in much of the Western World since the dawn of the 21st century, anal sex and cunnilingus have left the realm of the “forbidden” and have taken up prominent residence in the “mainstream”; and those sex-acts are experiencing widespread “cross-over” appeal. It is no longer, for example, considered “improper” for a gentleman to request anal sex with his partner—male or female.

Anal Sex

Because of the nature of anal sex (and other sex-acts involving the stimulation of the anus), an enema should be administered as instructed by the manufacturer and/or by one’s physician prior to engaging in the act—unless otherwise mutually agreed upon.

Condoms should always be used when engaging in anal sex with casual-sex partners; and proper lubrication should be used in order to ensure comfort and minimize the risk of damage to the extremely delicate anal and rectal tissues. The penetrator should pay special attention to the requests, responses (spoken and unspoken), and comfort of the person being penetrated—not only in the initial stages of the act, but also throughout its duration.


Because of the nature of anilingus, an enema should be administered (as instructed by the manufacturer and/or by one’s physician) prior to the act—unless otherwise mutually agreed upon. In anilingus, the tongue is used to stroke, and thereby stimulate, the anus and, to the extent possible, the rectum. Connoisseurs of anilingus caution against the use of the mouth to “suck-pull” the anus since such stimulation may result in the development of hemorrhoids. It is advised and considered in good taste for a lover, after administering anilingus, to take temporary leave of the love-bed in order to refresh his/her mouth. (After all, there are likely to be many other uses for that same mouth thereafter….)


Cunnilingus should be preceded by a feminine douche, administered as directed by the manufacturer and/or one’s physician—unless otherwise mutually agreed upon. Sex-etiquette allows for the lady receiving the cunnilingus to direct the servicing partner verbally and non-verbally so that she may best derive pleasure. At the end of the day, no man intimately understands female genitalia like a woman, and she should therefore be deferred to in matters pertaining thereto. Unlike in anilingus, it is considered in poor taste for a gentleman, after administering cunnilingus, to take leave of the love-bed in order to refresh his mouth.


As a courtesy to the fellator, a gentleman should wash his genitals prior to receiving fellatio—unless otherwise mutually agreed upon. Sex-etiquette allows for the man receiving fellatio to direct the servicing partner verbally and non-verbally so as to best derive pleasure. Because of the prevalence of masturbation within the male gender, men are exceedingly familiar with their genitals and where and how they respond to erotic stimulus. (It is said that the average man would be able to detect even an eyelash in the mouth of the fellator during fellatio). Unlike in anilingus, it is considered in poor taste for a gentleman, after administering fellatio, to take leave of the love-bed in order to refresh his mouth.

For many men, fellatio is at once the most intimate and intimidating androcentric sex-act as it exposes the recipient’s vulnerability, oftentimes rendering him scared stiff (in more ways than one!) for fear of decapitation or other irreparable harm to his prized penis.

Os impurum; Irrumatio

Os impurum, the act of oral sex where a man forces his penis into the mouth of another person (usually a man), and irrumatio (also known as “interfemoral sex”), the act of thrusting one’s penis between breasts, upper thighs, feet, etc., for the purpose of imparting and deriving sexual pleasure, have extended beyond the confines of sex clubs and fetish parties and have made their way into mainstream bedrooms. When introducing such practices to his partners, a gentleman should assume the role of instructor, guiding his pupils patiently and gently through the techniques associated with those practices.

Sex Toys

Every boy knows that toys can make for good fun. And sex toys are no exception. Sex toys are no longer taboo; today they are routinely introduced into foreplay and during sex to enhance those experiences.

Sex toys must be thoroughly cleaned and disinfected immediately before use and prior to being stored away after use. The type of toy dictates the most appropriate cleaning method to be employed: anti-bacterial soap and hot water; diluted chlorine bleach; and/or isopropyl/ethyl alcohol. As a courtesy to one’s sex partner, sex toys should be cleaned in his/her presence (After all, there is no telling where a particular sex toy has been played with in the past!)

Raunchy Talk

There was a time when very little was said during sex. But since the 1970s, with the proliferation of pornographic films in which something or anything—even if nonsensical—had to be said in order to compensate for the lack of well-written scripts and talented dramatic acting, raunchy talk has become part and parcel to casual sex. Today, the general rule is: Unless objected to, raunchy talk may be used to punctuate casual sex. Within the context of role-playing in the fantasy-like act of casual sex, name-calling, profanity, etc., are all fair game. And, of course, even within the parameters of “raunchy,” a gentleman would avoid using language that is likely to offend.

Requests To Swallow Semen

The drinking of semen—even one’s own, and even more so another’s—is considered one of the most intimate acts of sex, second only to the ultimate result of sex, the birth of a child. The drinking of another’s semen is the equivalent of becoming one with another’s soul, his core, his inner being. But the enjoyment of the flavor of semen, it is said, is an acquired taste: The bodily fluid is said to typically possess a bitter, slightly salty flavor. (Beer, other alcoholic beverages, red meats, asparagus, and cigarette smoke are just a few of the items that are said to intensify the natural bitterness of semen). But according to connoisseurs, semen’s flavor may be sweetened to a fruit nectar-like flavor if the donor consumes copious amounts of fresh pineapple in the days immediately preceding the discharge. So it might behoove a gentleman who is fond of offering his “man-milk” for cocktail sips to stock up on fresh pineapples. After all, sweet generally trumps bitter in matters sensual.

But whether bitter or sweet or bitter-sweet, no gentleman should demand that his semen be consumed: Only mothers have the right to demand that their children drink milk! A gentleman may, however, politely request that his semen be drunk, or he may inquire as to his partner’s interest in the consumption of semen, graciously accepting any decline of the offer as definitive. If, however, a gentleman’s request is accepted, the gentleman should acknowledge the act as a priceless gift—from the beneficiary to the donor—conducting himself accordingly.

Is there a Cardinal Rule of Casual Sex?

In all matters pertaining to sex, the cardinal rule applies: Do unto others as you would have them do unto you. As such, except for acts anatomically exclusive to the different sexes or particular to the different-sex roles, a gentleman should request nothing of a sex partner that the gentleman would not reciprocate. He, for example, should not request fellatio but then refuse cunnilingus; or a gentleman should not ask for anilingus then refuse the courtesy in return. Likewise, for a man to request fellatio or that his semen be drunk then refuse to thereafter kiss that same mouth that pleased him or honored him, would be in exceedingly poor taste.

Post-Sex Etiquette

What should a gentleman do after orgasm?

Post-sex etiquette is at least as important as pre-sex and during-sex etiquette, for it leaves a lasting impression and provides some indication as to the nature of the lovers. No gentleman would leave the love-bed immediately after orgasm; several minutes should be spent together in affectionate embrace. Thereafter, he should request permission to take temporary leave of the bed so that he can make preparations to further pamper his sex partner. A gentleman should treat his sex partner—female or male—like royalty. Sex is one of humanity’s most profound expressions, and it should be engaged in with ceremony, respect, and dignity. Each time a man engages in sex, his aim should be to make the experience the best and most beautiful sex—ever.

Who is responsible for cleaning up after sex?

Sex can be “messy,” and it is a gentleman’s duty to refresh his lover and the love-bed. Fresh towels should be used to cover any “wet spots” on the bed; and a gentleman should return to the bed with a large bowl of fragrant, warm water (Fresh lime or lemon “wagon wheels” floating atop the water is a good choice) and clean face towels to be used to clean up then refresh his lover’s body then his own before he rejoins his lover in the bed for additional affectionate embracing and conversation. After sufficient time has elapsed, the gentleman should invite his lover to join him for a bath or shower.

When should a sex partner depart after casual sex?

Whether a lover will spend the night or depart after casual sex should be established and communicated before sex. (See “Pre-Sex Etiquette” above). When a lover must depart before morning, a gentleman should accompany his lover as far as discretion permits—whether to the door; to the curb to hail a taxi; to the lover’s private vehicle; or to the train or subway station, for example. When a lover will spend the night, all courtesies that should be extended to house guests should be extended to the overnight lover. (See chapter, “Your Place or Mine?”).

Should a casual-sex partner be called the following day?

Calling a lover the following morning is compulsory—unless the lover spent the night! And unless discretion dictates otherwise, a handwritten thank-you letter should be mailed the following day. Emails, text messages, etc., are acceptable—if supplemented with a handwritten message. Also, a lover should always be presented with a memento (small but meaningful) of the love-making.

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