The Feminine Psychology of Sissies

The Psychology of the Feminine Element in the Homosexuality of Sissies

Author's note: This essay is merely a personal observation, questioning and exploration of the Feminine Element in the Homosexuality of Sissies. While I very much enjoy writing pornographic stories using these themes, this is not intended as an erotic piece though there may be passages I relay that are highly sexual based on personal experiences. Pertinent 'hard' footnoted sources will be available upon request, with quotes and observations from outside sources. This is not necessarily a scientific paper, nor is intended to be, akin to the Kinsey Report or studies by Ray Blanchard. It is by no means complete on the subject and certain aspects may have been overlooked. The basis for this article is my own intimate experience and observations on the subject matter while hopefully being objective and professional, yet whimsical and fun.

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In this jumbled world of gender and sexuality there are many elements that blur the lines of crossdressers - men who love being feminine in dress and mannerisms, if you may, if only in the privacy of the "closet". This closet may be a place where only they go or they may bring in lovers to this mostly private world. The spectrum is wide from men who simply like to masturbate in a pair of panties (can't blame them, feels kinda good) to crossdressers who dabble in it when wife is away (if wifey only knew!) to people with gender dysphoria or people who are transgender (truly the world is a more wonderful and accepting place today, thankfully), to 'shemales', fembois and 'ladyboys' quite well represented from around the globe (booking a trip to Brazil or Thailand?) to drag queens who are nearly mainstream (thank you RuPaul, et al.).

For the purposes of this article, I will deal with another type of gender bending sexuality found somewhere in the spectrum of cross dressing, the "sissy" community. I will refer to "sissies" as men who cross-dress and seek homosexual activities with other men. No offense is intended to males who cross-dress and do not seek homosexual liaisons, or to those transitioning or otherwise gender reflective. Sissy is a pejorative term, especially in the U.S., for an effeminate boy or man, with connotations of being homosexual or cowardly. The use of the word "sissy" here is not used in the typical deriding manner towards men who embrace femininity in dressing and actions. Many crossdressers with homosexual inclinations do embrace the label of "sissy" to identify with how they feel and how they act. In fact, self-identifying as a "sissy" it even gives them a sense of belonging in this sexual subset.

"The term sissy has historically been used among school children as a "relentlessly negative" insult implying immaturity and gender or sexual deviance. It has been identified as "sexist" in guidance issued to schools in the United Kingdom and described as "just as unacceptable as racist and homophobic language." The terms gender creative, pink boy, and tomgirl have been suggested as polite alternatives. (Oh really?) The Japanese word bishōnen is also a polite term for a man or boy with gentle or feminine attributes." (Pink boy has a certain authentic ring to it!)

"The word sissy in its original meaning of "sister" entered American English around 1840-1850 and acquired its pejorative meaning around 1885-1890; the verb sissify appeared in 1900-1905. In comparison, the word tomboy is approximately three centuries older, dating to 1545-55."

"By the 1930s, "there was no more damning insult than to be called a sissy" and the word was widely used by American football coaches and sports writers to disparage rival teams and encourage ferocious player behavior. The use of the word sissy was "ubiquitous" among delinquent American youth of the 1930s; the term was used to provoke boys to join gangs, demean boys who violated group norms, force compliance with the mandates of masculinity, and justify violence (including sexual violence) against younger and weaker children. Good students were taunted as sissies and clothing styles associated with higher social classes were demeaned as sissified. Among members of a Detroit youth gang in 1938-39, sissy was "the ultimate slur" used to tease and taunt other boys, as a rationalization for violence against rivals, and as an excuse for not observing the dictums of middle-class decorum and morality."

"By the late 1980s, some men began to reclaim the term sissy for themselves. The spelling variation cissy was used in British English, at least prior to the mid 1970s." (external quote)

A 'stroll' through the steamier side of the XXX blog servers, you will find quite a variety of these sissy types, with many thousands of men who partake in crossdressing and often have sex with other men. While some crossdressers claim to be 100% straight and insist it is not a sexual activity; that it is not sexual is something up for debate. While some of these crossdressing men do not intend to have sex with other men and don't identify as "sissies", give them a nod to their principles and restraint and accept their word on this (just don't let wifey find out, and if she does know, accepts and maybe even participates with them in this, more power to both of them).

It has been said through studies that perhaps 90% of crossdressers identify as heterosexuals, though the percentage of men who do cross-dress is mostly unknown as it is a mostly private and hidden activity. If 1 to 5% of the male population has engaged in crossdressing and then only 10% of that 1 to 5% engaged in homosexual activity then the percentage of "sissies" would be relatively quite small. Personally I believe crossdressing is all about sex and that these sexual impulses are but a facet of the biology of the male sex drive.

In our 'civilized' society, sex is guided by certain societal boundaries such as marriage, consent, protection of children and the handicapped, dating and relationship rituals. For the male of the species, the sex drive is paramount; truly it is a powerful 'life force' that drives sexual desire from adolescence to old age. This sex drive/life force is in many ways no different that the spawning of the salmon, the beasts in the forests to living things great and small from a tiny microbe to the flowers, grasses and trees and all organic living matter. In our more open and hopefully less repressive world heterosexual relationships still occupy the lion's share of sexual interaction. Homosexual and bisexual lifestyles have reached a stage of acceptance in less repressive countries and more open societies.

Getting back to the male sex drive, as the true life force of the male of the species it is the most powerful driving force in every male, straight or homosexual or any shade of sexuality in between. In human mating rituals it is played upon and used to their advantage by females, though after marriage it is often corralled, controlled and held in check. Biologically speaking the need for males to ejaculate daily and many times during the week is a phenomenon known to males but often ignored by females, hoping the issue would "just go away", much like the over eager puppy that just won't leave you alone. Homosexual couples often have an understanding that gay sex is a focal point of their relationship and undertake quite a number more sexual connections during an average week than do corresponding heterosexual couples.

The psychology of a "Sissy" is rooted in adoration of females and of the lovely trappings of femininity and the many feminine accouterments. Perhaps it is a deviation of the stereotype of the "flaming homosexual", those males who unashamedly make a show of their feminine gayness - looking part male, part female with androgynous clothing, but with perhaps lipstick, eyeshadow, mascara, painted nails, yet with an appearance that you knew they were male but their feminine elements left you knowing there was no doubt they were homosexual.

With a sissy the ideal would be to be completely feminine in dress and appearance, so much so that they could pass as women for the most part, only being discovered as a male when disrobed by another person. A six foot two one hundred seventy-five pound forty-nine year old man might have a difficult time being truly passable 'en femme' but for that person the sensation of looking, acting and being feminine is a thrill beyond belief.

This is a private, hidden crossing of the line, in your day to day life with wife, work and family there is no outward inkling that you have a secret self. No one would venture to guess that in secret you dress as a woman and seek sexual encounters with other males....you hope. This is a self that adores the precious time when able to transform from your public persona into a desirable feminine creature. For many of us there is no urgent desire to come "out" and let the world know of our femininity and homosexual desires.

Crossdressing is not gender dysphoria or transgender transsexualism though crossdressing can be manifest in the latter two. Speaking for myself I do not feel like a woman trapped in a man's body. I know I'm a man and there are many things I do well as a man and enjoy doing well as a man. My sexual journey has evolved and I may have always been a closet homosexual even with 2 marriages and numerous wonderful sexy girlfriends.

So digging deeper, what are the elements, the 'triggers' that lead outwardly appearing 'heterosexual' men to have feminine desires leading to crossdressing and possibly homosexual encounters while dressed? What are the life experiences or upbringing that lead to this type of closet sexuality? In the gay community many gay males are turned on by the masculinity of other males; 'sissies' worship both the femininity and beauty of women and the 'alpha' masculinity of men.

What is the root of this desire for emulation and adoration of female beauty, the desire to possess femininity, the desire to be a feminine sex object to a male? Granted, there are younger males with feminine features and homosexual tendencies who can easily transform themselves into feminine creatures that you could barely discern they were genetic males. There are crossdressers that only profess to have sex with other crossdressers, that since their lover also is "female", that this is not gay sex (really? come on, aren't two sissies having sex with each other twice as gay?) claiming that they are "trans-lesbians", not homosexual males (in feminine attire). The "sissy" culture is one of men dressing sluttishly and proud of their submissive feminine role and love of cock. On porn blogs, there are page after page displaying 'man' after 'man' dressed 'en femme', some classy and refined perhaps reminding you of a proper 'society' middle aged woman, others in flimsy lingerie, erections waving proudly.

"Cross-dressing can be traced back to the Greek, Norse and Hindu societies, yet there is no agreement as to the reason that some men have a need to cross-dress, and others would not even consider it. Cross-dressing has been around for centuries yet has largely been done in the secrecy of one's home rather than in public." ((external quote)) Depending on the source, studies have shown that anywhere from 10% to as many as 90% of men have cross-dressed in their lives. "Femminielli or femmenielli (singular femminiello, cf. Standard Italian femmina, "a female", -ello, masculine diminutive suffix) is a term used to refer to a population of homosexual males with markedly feminine gender expression in traditional Neapolitan culture. It may be hard to define this term within modern Western notions of "gay men" versus "trans women" since both these categories overlap to a degree in the case of femminielli ((external quote))."

"But in truth, cross-dressing is grounded in a highly logical and universal desire: the wish to be, for a time, the gender one admires, is excited by -- and perhaps loves. Dressing like a woman is merely a dramatic, yet essentially reasonable, way of getting closer to the experiences of the sex one is profoundly curious about -- and yet has been (somewhat arbitrarily) barred from. We know cross-dressing well enough in other areas of life and then think nothing of it. Women can look elegant and stylish in jeans and a blazer, even cowboy boots. A five-year-old boy living in a suburb of Copenhagen who develops an interest in the lifestyle and attitudes of the cow herders of the Arizona plains would be heartily encouraged to dress up in a hat, jeans and waistcoat and aim his pistol at an imaginary Indian chief -- so as to assuage his desire to get a little closer to the subject of his fascination."

"We should accept that the adult crossdresser is no different. He too wants to inhabit the experiences of a group of people he is keen on. He seeks to know what it would be like to cross his legs in a tight cocktail dress, to walk across a marble floor in a pair of heels, to feel a grey cotton bra strap encasing his back, to put a little silver bracelet around his wrist, to feel the breeze on his bare waxed arms and to stroke his smooth long legs in the bath. He might extend to imagining what it would be like to kiss a man as a woman, to feel bristles that are normally his on lips as soft as those of the lovers he has known. Admiring himself in the mirror in a pair of black tights, the cross-dresser samples the intense, fascinating satisfaction of being simultaneously himself and the object of his desire." ((external quote))

The two paragraphs above may hold a key to those who cross-dress and engage in homosexual behavior. An overweight middle aged man in full feminine attire would unlikely be able to ever encounter a situation (even not dressed as a female) to have sex with a nubile young woman on display in the many countless images available on the internet (or prior to the online world, one of the lovelies portrayed in Playboy or other similar magazines). The aforementioned male certainly would find it easy, however, to experience the sensations in attire and actions of a female engaging in sexual activities with another man. A sissy knows the titillating sensation of being in a sexy, silky dress or lingerie, high heels and lovely lipstick and be desired by and having sex with a man. These are sensations that at one point in his life he felt as a heterosexual man towards a woman dressed in attire that he now wears. What is the flashpoint, the magic potion, the elixir that will completely reverse roles in this equation?

On what leads a man to become and embrace "sissydom" is a complex question, perhaps too broad for this essay. In the adoration of females and femininity is there a "desire to be desired" from unrequited intentions with the opposite sex or lack of acknowledgement sexually and emotionally by a current partner? Another line of thought is that straight males are naturally so very interested in and excited by females. Thus, straight males are infatuated with things that are feminine, so it is an instinctive curiosity is to explore what it's like. (...yeah, right. How many "straight" males dress in drag to suck cock?) But what about those who cross the line from simply donning a skirt, a bra, a pair of panties to see what it feels like, to those who don a skirt, a bra, a pair of panties to see what it feels having sex with a man?

It is incredibly intoxicating dressing as a woman. Anyone who has dabbled with cross dressing knows. The lure. The sensitivity. The excitement. The indulgence. The hidden self. The secret pleasures. The taboo, forbidden endeavor. The fantasy. The release. For most of us, more than likely it started with a pair of panties. Wife's. Sister's. Some other family member or some other feminine undergarment. The wondrous colors. The feminine embellishments of tiny bows, tiny flowers, lace trim. The forbidden sensation of the soft sensuous material on the male genitalia. Exciting stimulation beyond belief. Then a bra or a camisole. Stockings. If it fits, then a dress, if not you buy one for yourself. You buy yourself sexy, slutty clothing your wife would never wear but you find exhilarating.....and the makeup. Lipstick. Eye shadow. Mascara. Rouge. Nail polish if you are brave & have time.

Amateurish at first you find out how to make yourself prettier, just like girls do. It's a secret indulgent world you hope no one finds out about.....unless you have bisexual tendencies...then.... how can a male being dressed and femme not feel some sort of gayness even if he is dressed in female clothing in the company of his wife or girlfriend? Two crossdressers together almost always would lead to mutual masturbation at the least: kissing and fellatio much more certainly.

Being dressed 'en femme' stir very strong homosexual longings for me. The femininity I felt in homosexual encounters predated the internet by many years. It was just something I felt when hooking up with a guy; being in panties and lingerie just felt right, felt wonderful and natural. That was who I was sexually with men, the feminine one. I can't quite put my finger on it why I have always felt so incredibly feminine in my homosexuality. Women have a beauty that is so stimulating in their bodies and with makeup and feminine clothing it is mysterious and intoxicating.

I love the female form; beautiful faces and flowing hair, the lovely breasts, svelte stomachs, hottie asses and long lovely legs - add in the myriad of amazing undergarments to fashionable clothing accenting their beauty it just adds to the fire that burns in a crossdresser's psyche. Years ago I went to a gay bar when my first wife was out of town and wore panties underneath. Between marriages I had quite a few homosexual encounters; for some of them I wore panties or stockings and corsets. During other homosexual encounters, even wearing no lingerie, I always just felt so sensuously feminine.

I hooked up once in the 1990's with a T-girl for pay; she put me in stockings and a long wig and led me in front of a mirror - she was a bit chubby and not all that cute but my long legs and skinny frame it was scintillating seeing myself so femme with an equally femme person. I would hook up with guys late at night and wear stockings, panties and a merry widow under my male clothes, it just felt so natural being femme for a guy. While living with a straight roommate, he had upstairs apartment and mine was downstairs I snuck a guy in my room in the early evening and we started kissing. Just then my girlfriend called (a hottie blond) and I was on the phone with her 20 minutes while the guy waited for me. Then we got naked and made love - it was fantastic kissing him and playing with his cock. I then sucked him off tasting every drop then we kissed and nuzzled for the longest time till he got hard again then he fucked me - all while my straight roommate was upstairs.

There was one encounter just before marrying my 2nd wife she was out of town and I brought over a young guy and we dressed in wifey's lingerie and sucked each other off. Now in my 2nd marriage I have always masturbated in her panties (that I have bought her many dozens of). I had dabbled in crossdressing but nothing too involved. I have always had a 'secret self'; a closet homosexual who from time to time loved the thrill of a clandestine encounter. I brought a guy over when wife was visiting folks and I dressed up in stockings, garter belt panties and satin baby doll, he loved it and so did I, I just loved sucking his cock probably taking him by surprise with my hungry open mouth gay kiss as we played in bed....another guy who I brought over, we got naked and sucked on each other, then I excused myself and came back in panties and a camisole. My impromptu addition of lingerie thrilled us both.

Somehow (no not somehow, it was a porn blog) I gravitated towards a sissy mindset doing things I had never done before like shaving my legs and underarms. Where before my crossdressing was very awkward and amateurish it developed some finesse to where I looked pretty hot in a sexy dress; I finally got some high heels and that did it - WOW! how can a crossdresser not be enamored wearing sexy high heels?