Recently, I was discussing with a friend of mine about our first time having sex.  Many of us, even though we are gay, had our first time with a woman.  I will admit it, I am not a gold star gay, I have had sex with women.  I thought it was the path I was supposed to go.  I fantasized about men, but I never thought it was possible to actually let it go any further than fantasy.  I am very thankful that I realized that I was wrong about this. This is the conversation we had about our first time:

ME:  The first two times I had sex with women sort of defined my ideas of sex. The first time was a lot of fun, far too brief, and with a condom.  The second time (and there is a lot of emotional baggage attached to this time), it was without a condom, and it just felt nasty to me.  I like the feel of lube, especially silicone-based lube because it does mirror that silky feel, but it was just something about the vaginal juices that just grossed me out.  I’ve tried to go down on women, but the greasy feeling of pubic hair/vaginal region just really turned me off.  I’ve never understood it.  That second time, no matter how hard I tried, I was never able to have an orgasm.  The ickiness of the feel, and the fact that she was very loose and wet, just didn’t allow me to reach orgasm, and we went at it for a while.  Is it just me, or do other guys get turned off by this?  I assume a lot of gay guys do, but I really would like a different perspective on this.  I have had sex with women since those initial two times, but I guess all women have unique vaginas like men and the uniqueness of our penises. 

HIM:  I was drunk as a skunk my first time fucking and eating a pussy and couldn’t even find the hole [fucking wise] – was aiming for the right area but couldn’t plant my dick in it.  It wasn’t a good experience for either.  I felt [right after] a complete failure, in the “male” dept.  She had to lead my dick to her hole.  I wasn’t all  that hard to begin with.  The whole affair was, in my mind’s eye, a complete failure.   Needless to say, we never continued dating.

ME:  I totally understand the trying to find the hole part on the first time you fucked a girl.  I am right there with you.  It is very difficult the first time.  I wonder if all guys have that problem.  It’s very embarrassing, but oh well, you eventually get over it.  When I was older and had sex with a woman again, it wasn’t so difficult.  Just glad that I wasn’t the only one who had that happen their first time.

HIM:  I am convinced that every guy the first time he has sex will fumble in some way.  I don’t care how macho he considers himself.  I’d never seen a pussy before and I sure wasn’t acquainted with the pussy anatomy – I just thought it was a hole of some kind.  And for me the first time was in the dark.  It’s not like I could look for it or anything.  Hell, I didn’t know what to be aiming for in the first place.  If it’s your first time – you just don’t know.  But after a couple of times you learn how to geolocate one with just using your dick.  The pussy hair doesn’t help.  It hides everything.  That’s why I so love having sex, exclusively, with another guy.  I’m 100% familiar with the equipment, I know what it does, and I know how it works and what works it 

The first time I had sex with a guy, I had not problem finding the equipment.  The first time I fucked a guy, my dick slid into his ass as naturally as it could be.  There was no fumbling, there was just perfect harmony.  This may be because I had had sex with several women before this, but I do think that we are more familiar with a man’s body.

So my questions are these:  Was your first time with a man or woman?  Was that first time awkward?  Was it easier when you compared your first time with a man or with a woman?  Why?  I would love to know your answers guys. I am curious to know if it is universal that the first time is always awkward or if some of us are just born with the ability to be a great lover.

Raised during the Harlem Renaissance, James Baldwin established his reputation with his first novel, Go Tell It On The Mountain  in 1953, an autobiographical tale of growing up in Harlem. He became one of the leading African-American authors of his generation, known for novels and essays that tackled black-white and hetero-homosexual relationships. He was particularly a noted essayist during the Civil Rights movement of the 1960s. Baldwin turned to writing after being encouraged by Richard Wright, and, like Wright, left the U.S. after World War II and moved to France. His novels, including Giovanni’s Room (1956), Another Country (1962) and Just Above My Head (1979), all deal with the struggle for individuality against intolerance. He also wrote several plays, including Blues For Mister Charlie (1964), and Evidence of Things Not Seen (1986), a book about racially-motivated child murders in Atlanta.

A groundbreaking novel for its exploration of homosexuality, James Baldwin’s Giovanni’s Room (1956) holds a unique place in the American and African American literary traditions. Baldwin published it against the advice of Alfred Knopf, who published his acclaimed debut novel, Go Tell It on the Mountain (1953); editors warned Baldwin that he would jeopardize his potential as a ““Negro”” author by writing a book about white male sexual and cultural identity. However, the determined Baldwin found a British publisher, Mark Joseph, and Dial Press eventually published Giovanni’s Room in America.

The first-person narrative centers around David, a white American attempting to “find himself” in France. The novel opens in the present with David recalling his internecine upbringing and an adolescent homosexual encounter. In Paris awaiting the return of his girlfriend and possible fiancée, Hella, David engages in a torrid affair with Giovanni, an Italian bartender. Giovanni loves him unashamedly, and they live together for two months; however, David transforms Giovanni’s room into a symbol of their “dirty” relationship. Upon Hella’s return from Spain, David abruptly leaves the destitute Giovanni, who has been fired by bar owner Guillaume, a “disgusting old fairy.” David’s desertion psychologically destroys Giovanni, who enters a sexually and economically predatory gay underworld. Giovanni eventually murders Guillaume, who reneges on a promise to rehire him in exchange for sex; he is later caught and sentenced to death.

Meanwhile, David, despondent over his mistreatment of Giovanni and the truth about his homosexuality, attempts to rejuvenate himself via marriage. But upon discovering him and a sailor in a gay bar, Hella vows to return to America, wishing “I’d never left it.” The novel’s closing tableau replicates its opening: David ponders Giovanni’s impending execution and his complicity in his erstwhile lover’s demise.

Giovanni’s Room fuses the personal, the actual, and the fictional: Baldwin exorcises demons surrounding his own sexual identity while simultaneously capturing the subterranean milieu he encountered in Paris during the late 1940s and early 1950s; he bases the murder plot on an actual crime involving the killing of an older man who purportedly propositioned a younger one; and he weaves a Jamesian tale of expatriate Americans fleeing their “complex fate” in search of their “true” selves. The novel received favorable reviews, many critics applauding Baldwin’s restrained yet powerful handling of a “controversial” subject. Ultimately, the book is more than a study of sexual identity, as Baldwin himself posited: “It is not so much about homosexuality, it is what happens if you are so afraid that you finally cannot love anybody.” Giovanni’s Room maintains a seminal place in American, African American, and gay and lesbian literary studies.

Giovanni’s Room was the first gay novel I ever read.  I found it utterly fascinating and it began my life long pursuit and love of gay novels. It is not a happy novel, but it is well worth reading.  Baldwin became and inspiration to me.  Recently while listening to NPR, Morning Edition did a story about a a new collection of his works edited by Randall Kenan called The Cross of Redemption.  Here is an excerpt from the transcripts of this story:

The writer James Baldwin once made a scathing comment about his fellow Americans: “It is astonishing that in a country so devoted to the individual, so many people should be afraid to speak.”

As an openly gay, African-American writer living through the battle for civil rights, Baldwin had reason to be afraid — and yet, he wasn’t. A television interviewer once asked Baldwin to describe the challenges he faced starting his career as “a black, impoverished homosexual,” to which Baldwin laughed and replied: “I thought I’d hit the jackpot.”

I wish that all of the GLBT population in the world could feel each day like they’d “hit the jackpot.”