I Lost My Top Virginity to a Hot, Muscular, Alcoholic, Well-Endowed Whore

I was so fucking clueless. I had never fucked a guy. Oh, I had fooled around a lot, mind you. One by one, I had kissed about 20 cute boys, I had jacked off with about half of them, and I had even sucked and had been serviced by a couple of them, but now I wanted to fuck guys, guys, lots of guys. I was no longer scared. I resolved to get laid no matter what. This would be my Great Leap Forward, or better yet, my Great Fuck Forward.

I went to my favorite gay beach bar, and there he was: the man I wanted to put my penis in. He was average height, with an angelic face and big muscles. I couldn't keep my eyes off those pecs, those biceps, that butt. He was beautiful. He was at the counter ordering a beer.

My mouth went dry. I was afraid, but I told myself, "Go for it!" I walked up, said hello, and asked how he was doing. He face lit up. He said he was fine. His name was Roberto, and the conversation flowed from there. I couldn't believe my luck. We must have talked for a couple of hours. He also put away a good many beers --much more than me.

I looked at my watch and told myself, "You better make a move, big guy." I held his hand and caressed his arm. He smiled and asked, "So, are we going to fuck?"

"If we want," I answered. Roberto and I talked some more. Then, he took me to his hotel room. It had a big beachfront patio. The view of the night ocean was breathtaking. There I was, with a hot guy in a high-rise room in the sky.

We sat down on the bed and started French kissing and touching each other. We got so horny, that we stood up and undressed. His pecs were big and gorgeous. He had obviously trimmed down his body hair, but it had grown out a little, and that was hot. Then, Roberto took off his pants, and out popped his dick.

"Damn!" I reacted. "You're huge!"

"Thanks, man," he said.

 

We jumped on the bed naked and went right to it. We kissed, sucked nips, and serviced dicks. We especially enjoyed running our lips up and down the undersides of each other's shafts. Roberto told me to suck his balls, but I said I was afraid. (I hadn't gotten into teabagging yet.)

We made out some more. Then in the heat of it all, he said, "I want to fuck you, I want to fuck you, I want to fuck you." Clueless me! I hadn't taken the initiative. What was I waiting for?

"You're not fucking me with that big thing!" I answered. He laughed. I got on top of him and told myself, "It's now or never." I slipped on a condom, slapped on some lube, and started caressing his ass with my dickhead. At first, Roberto was apprehensive, but I kept gently rubbing my dick on his starfish, and he started to relax. My hot boy looked into my eyes and began to breathe slowly and deeply. Without words, he wanted me to enter him.

I pushed my dick in a little, but withdrew, because I was about to cum. I was so inexperienced! I tried again, but had to withdraw. I was too close to the Point of No Return. Ironically, Roberto enjoyed me tapping at his back door. He began to say, "Oh...oh...oh..." over and over. I slowly got control of myself and pushed my dick a little in and a little out, a little in and a little out, back and forth, back and forth, and slowly, slowly, I finally got my dick inside my beautiful muscular stud without blowing my load.

Another irony: My inexperience had inadvertently taught me how to slowly and softly enter a guy. A triple irony: I had started to learn how to separate dry orgasms from ejaculation. What first time luck!

 

I began to fuck Roberto. I couldn't believe it. I was actually fucking a guy for the first time --and not just any guy: a hot, beautiful muscle boy with a big dick. Roberto looked at me with the greatest expression of pleasure. It felt fantastic! I was fucking a Greek god. Why did I wait so long? It was as if I was fucking darkness.

 

Oh God, this is too much. I'm losing control. I came inside of Roberto after only a minute. (I was still green on the dry orgasm vs. splooge thing.)

My boy was enjoying being top-flipped, but after cumming, in my inexperience, I got up and slipped my dick out of him, instead of enjoying some post-cum fucking. He looked down, saw my unsheathed dick, and asked, "Where's the condom?"

I noticed it was gone and said, "I don't know. Is it inside you?" He got up and laughed. "Probably," he said. He pulled the condom out of his ass and dropped it in the trash.

Then, he asked me to get another condom, put it on my index and middle fingers, lube it up, and finger his ass. I obliged, and he enjoyed the ass play. After a little while, he spewed all over his large pecs and washboard abs and enjoyed orgasmic contractions that lasted half a minute. (Cumming while on your back is more intense and long-lasting.)

It was the most beautiful thing I had ever seen: a well-built studly guy enjoying himself. I threw away the second condom, collapsed onto Roberto, and felt his warm cum on my chest and abs. I had done it! I was a real man now! I wish I hadn't waited so long. We rested together like that for a little while and kissed a few times.

 

 

I invited him to the shower, but Roberto's drunk ass declined. He just used his shirt to wipe off the cum and jumped back in bed, which I thought was disgusting. I showered alone unfortunately and joined him back in bed.

Roberto went right to sleep, but I had trouble. I was too keyed up. I had lost my virginity in the most awkward and beautiful way possible. Finally, I dozed off. We woke up at the crack of dawn. Roberto reached over and started pulling on my dick to make me hard. I asked him if he had another condom, and he said no. Naive me! I had brought only two. What a barebacker he was! A gay man without condoms in the room --or so he said.

To be safe, I decided to do a mutual jack-off. I got on top of him, put my hard cock next to his, and humped away until we blew our loads. We showered together after this time. Roberto said he had to visit his parents. So, we made a date for that night, and I walked home. I felt so different. I had taken the plunge. I was a man with one lay under his belt.

That night, Roberto and I walked on the beach and sat on a low-curving palm tree. He told me how he was going to donate sperm to a lesbian couple to father a child. He was already interviewing prospects. What a beautiful idea!  I had never thought about such a thing: to be a gay guy --and a father! I was in awe of the possibility. We made out for a little while. Then, we drove to the nightclub. To my dismay, Roberto got drunk again, saw another guy he was attracted to, and French kissed him in the middle of the dancefloor.

I was crushed. My Roberto was a slut and a lush. I knew he was a tourist. I knew it would have to end, but not this way, not this soon, not this disco. Roberto began inviting guys left and right to his hotel room. Another tourist named Humberto introduced himself to me and told me I was cute. Out of revenge, I danced with my new boy and kissed him some. It looked hot, but it was nothing serious.

 

Roberto hardly noticed. He was too busy drinking and lining up group sex dates. My drunk-out-of-his-mind, first lover followed me out of the club. He wanted me to come to his room again, but I told him no thanks. I wasn't an orgy kind of guy. He offered to at least drive me home. I allowed him that, which I shouldn't have done. He was wasted, but there was no accident.

 

Roberto was good-looking. He had nice, big muscles. He was also a stupid alcoholic whore. I never saw him again. I was sad and glad at the same time, but I got over it. Two weeks later, I was making out with another guy. I dated another, then another, then another. I quickly learned how to be multiorgasmic: I was controlling my dry and real orgasms in no time. I even lost my bottom virginity, but that's another story.

At any rate, I've come a long way since Roberto. In fact, I've become a much better man than he ever was. I'm bulked up from the gym. Periodization is a great thing. I'm good in bed. I enjoy watching my partner enjoy himself. I'm romantic. I've had long-term boyfriends. I'm casual. I can do short term, too. Whatever you want. I'm a great guy. Want to go out?

Photo credits:

Sex pictures 1, 3, 6, 7 -- Yuri & Peter from Sean Cody:

     (Yuri is topping);

Solo pictures 2, 4, 11 -- Jeremy from Sean Cody; 

Loud trade picture 5 -- Kurt & Trey from Sean Cody:

     (Kurt is topping);

Shower picture 8 -- Hawaii: Isaac & Jake from Sean Cody:

     (Isaac is on the right);

White sheet picture 9 -- Gay Amsterdam from bestgaycities.com; 

Nightclub picture 10 -- Unknown origin.

I've Got One Thing to Say: Fly That Fucking Flag!

There he/she was: RuPaul in a sequined Confederate battle flag dress, playing the role of Miss Rachel Tensions in the 1995 movie To Wong Foo, Thanks for Everything! Julie Newmar. This was the shocking image to end all controversy. This was gay, drag, black, and Neo-Confederate --all at the same time. What could uptight, puritanical civil rights leaders say?

Here he/she was: A black man playing a woman in a sparkling Southern nationalist outfit. This was the minor role that roared. This was power, irony, comedy, and independence. What could deferent white liberals say?

What could anyone say? It's amazing. RuPaul is still a phenomenon that dares not speak its name. It's 2010, for God's sake! Many blacks still can't own up to the down low --and that flag! That flag! RuPaul completely disarms the white supremacists, when he/she wears it from time to time. The racists are speechless. The politically correct pussies are dumbfounded. He/she is not afraid.

There he was: A black model sporting --gasp!-- a Confederate battle flag shirt --but wait! The flag's colors are different. It's red, black, and green: the African nationalist colors first suggested by Marcus Garvey (1887-1940). (Africa sometimes favors the red, gold, and green of Ethiopia, but we won't belabor the point.)

Get this: Garvey, like Abraham Lincoln before him, wanted to send American blacks "back" to Africa. He didn't get very far with that idea, but he was the father of Pan-Africanism. The red, black, and green are his most visible legacy.

There it was: the shirt's unlucky number 13, or was it? The flag has 13 stars, which stand for the number of Confederate states. Weren't there only 11? Yes, but Missouri and Kentucky sent delegations to the Confederate Congress. So, they counted. Don't you just fucking love American history?

Who made this shirt? NuSouth Apparel of Charleston, South Carolina did. Owners Sherman Evans and Ángel Quintero sold clothes bearing the refashioned symbol. They came up with the idea in the early 90s, while promoting the rap band Da Phlayva. Evans and Quintero later opened NuSouth in 1997. The Confederate battle flag in Pan-African colors was an attempt at racial unity.

People had lots to say about this one. It made quite a splash in the press. Some liked it, others hated it, but everyone agreed that it was an original idea. Unfortunately, NuSouth is no more. It closed in 2004, according to the South Carolina Secretary of State's Office.

There they are: Two black men sporting Confederate battle flags! Are you fucking kidding me? This image is an Internet favorite, but not everyone knows the story behind it.

Anthony Hervey (left) and his brother Harry are protesting the 2000 closure of the Eight Flags Display on US 90 by Harrison County, Mississippi. The County closed the beachfront monument after receiving protests about the Confederate battle flag, which symbolized one of eight historical governments that ruled the area.

Anthony Hervey claims that he's a descendant of a Black Confederate. What the hell? Who was a Black Confederate? A slave who worked for Confederate troops? A slave who defended his master's family and property? A free black who fought for the South? While historians debate the definitions and numbers of official and unofficial black fighters of the Confederacy, today's black Neo-Confederates take up the flag against racial polarization, political correctness, and anti-Southern historical interpretation.

What do all these guys have in common? They're strong. They're courageous. They take the flag and make it their own. They refuse to be drama queens about history. They refuse to give ammunition to the enemy. They've taken away the only weapon white supremacists have.

Perhaps the funniest take on this nuclear bomb of reverse psychology is Blind Supremacy from Chappelle's Show (Season 1 / 2003). Comedian Dave Chappelle plays Clayton Bigsby, a blind white supremacist who's unaware that he's black. The two-part sketch takes the form of a fake documentary by Frontline, the PBS documentary series.

Chappelle's Show
Frontline - Clayton Bigsby
http://www.comedycentral.com/
Buy Chappelle's Show DVDs Black Comedy True Hollywood Story

Chappelle's Show
Frontline - Clayton Bigsby, Pt 2
http://www.comedycentral.com/
Buy Chappelle's Show DVDs Black Comedy True Hollywood Story

The Confederate battle flag only makes a cameo in Part 2 of this hilarious skit, but the greater point is that Chappelle turns racism on its head. All the insults lose their power, when blacks take ownership of them. It's like black rappers saying nigger a gillion times.

We've heard all the reasons against the flag: It's racist. It's a Klan symbol. It symbolizes slavery. It's a redneck banner. It represents segregation. The South lost; get over it.

Can a flag be racist? Well, if it can be, then the American flag is the most racist flag of all! The Stars and Stripes flew over the Northern abandonment of Reconstruction, which set back civil rights a hundred years. Count them: one hundred fucking long years! A century of Jim Crow! It also flew over the genocide of Native Americans. It was even the flag of Japanese American internment. We could go on and on. Its sins are many.

For the record, I'm a goddamn, card-carrying member of the NAACP. Look and learn. I have fought against de facto segregation. I have produced fair media depictions of different races and ethnicities. My human rights credentials are in order.

I believe that minorities --be they gays, women, blacks, or Martians-- should always fight from a position of strength. We should take up the flag, reinvent it, make it our own, and rally everyone around it. We should recognize positive uses of the flag: We use it to stage battle reinactments. We use it to honor the Confederate dead. We use it to teach students about the Civil War. We use it to round out RuPaul's wardrobe.

Speaking of which, what does RuPaul have to do with masculine gay guys? Nothing --and everything! We may not ask him/her out on a date. We have hard-ons for butch and athletic guys, but we do admire his/her courage, we certainly enjoy his/her comedy, and we appreciate his/her honest ambiguity about gender: hence, his/her use of he/she, his/her, and him/her.

Back to the flag, we should defang racist abuses of the rebel symbol:

Hey cracker, put down that flag! Robert E. Lee looked down on white trash like you.

Go on! Get out of here, you goddamn rednecks! How dare you desecrate the flag of Southern honor?

Hey, hey KKK! How many relatives did you fuck today?

Yo' mama is a nigger-lover.

Forget Oprah and her sniveling, crybaby drama over the mere sight of the flag, the mere mention of slavery, the mere suggestion of segregation. Suppression of history is a pathetic tool of the weak. Black history is a courageous, glorious, riveting rag-to-riches story. African Americans literally built American civilization with their own hands. We do them honor by bravely using the flag to disarm our enemies. No Fear should be our motto, just like the clothing company that bears the name: http://www.nofear.com/.

I proudly wear my http://www.flagclothes.com/ Confederate (battle flag) polo shirt, and sometimes people say I look like a Neo-Nazi skinhead. I show them my NAACP membership card. I tell them I'm honoring my two Confederate soldier ancestors. I say, "You judged a book by its cover. Isn't that what racism is all about?" Talk about having a conversation about race.

For something different, there's always http://www.dixieoutfitters.com/. Their clothes range from the overt to under-the-radar symbolism designed to subvert school bans on Neo-Confederate imagery. There are countless other stores that sell the South in all its glory.


The campaign to bury the flag and forget American history is a complete failure. It divides people. It makes for silly political melodrama. It trivializes the civil rights movement. It makes liberals look like a bunch of weak, cowardly, namby-pamby whiners.

It's time for a new approach. It's time to stare at the flag. It's time to imagine new positive uses for it.
What about the gay rebel flag? Well, that's a step in the right direction. If it becomes popular, it could be the biggest reinterpretation since NuSouth's African nationalist version. Why, it could even be the quinessential Southern symbol of the fucking Twenty-First Century!


We can all have fun with this. We can reshape the future with this. We can bring constituencies together with this. The opinion, "The flag belongs in a museum," is such a goddamn cop-out. In politics, that's called sitting in two seats with one butt. It never ceases to amaze me how many politically correct wankers there still are in the Age of the Internet. The Confederate battle flag no more "belongs in a museum" than the First Amendment does.

Civil rights leaders, deferent white liberals, and the politically correct speech police treat minorities like children. We don't need to be "protected" from racist speech. We don't need to be "rescued" from homophobia. We can fight this battle ourselves, and we have just the flag to do it. The thing we feared most will be our salvation.

(John McDermott contributed the information about NuSouth's closing. He is the business editor of The Post and Courier in Charleston, South Carolina.)