First Time For Everything: Screwing My Gay Best Friend

Posted by: Anonymous Filed in: sex
11:00AM, Tuesday October 20th 2009

Comments (32)

First Time For Everything: Sex With My Gay Best Friend

“I’ve never even kissed a woman,” Adam said. One of my best friends on the planet, Adam was unequivocally gay—the kind of caricature personality who lisped, wore pink, plucked his eyebrows, flicked his wrists, and decorated his apartment in rainbows. He was my first call when a guy I was dating was being a jerk, the one who was always up for an impromptu shopping mission or who’d dance with me until the wee hours of the night at an ‘80s club. Technically, he was everything I’d want in a boyfriend: smart, funny, kind and gorgeous—too gorgeous to be straight, as the saying goes. But since he was gay, I barely noticed.

But as he said those words, our faces were inches apart and we were locked in that trance-like pull of an inevitable kiss. We were at a party, dancing to New Order. And soon our lips locked and we were full-on making out. As I felt his hands squeeze my butt, I backed up and stared at him. “You’re an amazing kisser,” he said, with a wink.

Next thing I knew, we were back at my place.

We laughed as our shirts came off and he fumbled with my bra like a 15-year-old boy. “Sorry,” he said, as I demonstrated how to unhook it and flung it across the room. He stared at my breasts, and not with the normal “Oooh boobies!” expression guys get—this was pure wonder, with an underbelly of fear. He seemed to be thinking, “What the eff do I do with these things?” Luckily, he figured it out.

Soon, I was unzipping his pants and going down on him. He returned the favor. “I’ve never seen one this close up,” he said, as my legs wrapped around his back.

“Just pretend like you’re kissing it,” I told him.

Soon, he was reaching for a condom and we were having sex. And it was good. Really good. Afterward, I laid my head on his shoulder, he wrapped his arms around me, and we fell asleep. In the morning, when I woke up, he was nowhere to be found—he’d snuck out in the middle of the night. And I was completely mortified. Had I really gotten so drunk that I’d just screwed my gay best friend? I’d accidentally slept with friends before, and knew that it generally lead to nothing but awkwardness. And that was without the whole issue of sexual orientation hanging over our heads.

A few nights later, as I walked to a friend’s birthday party where I knew Adam would be, I felt intense trepidation. It had been 72 hours, and we hadn’t so much as exchanged an email acknowledging what had happened. As I walked into the bar and saw the group, Adam waved. I greeted the birthday girl and headed straight to him. He gave me a big hug and everything seemed totally ... normal. We sat next to each other downing gin and tonics, gabbing as normal, and I felt a huge sense of relief that our friendship wasn’t permanently damaged. As the night wound down, and I said my goodbyes to the group, Adam grabbed his jacket. “I’ll walk you home,” he said.

Is he going to say anything?, I thought, far too anxious to bring up the obvious myself. The answer was no. But when we arrived at my door, he kissed me again and we were right back upstairs, doing it on the couch.

Over the next few months, Adam became my regular booty call. If we were out together, when the urge kicked in, we’d quietly leave and head to my apartment. Other nights, one of us would call around midnight. He could walk to my place in less then 10 minutes.

For me, this was fun and games, a way to have great sex with someone I loved but without the complications of an actual relationship. And I will be the first to admit it, it was the ultimate ego boost. This is a guy who wasn’t sexually attracted to women, and yet he was very attracted to me. I was so freaking hot that I turned a gay man straight! And I loved being the only woman he’d ever boned. It was a specialness that’s hard to find with someone in your late 20s, when most of the firsts are long since gone.

But for Adam, this affair wasn’t so benign. It took a few months for the meaning of it to sink in for him—he was enjoying a sexual relationship with a woman and wasn’t the Kinsey 6 he’d always assumed himself to be. In a way, sleeping with me shook his entire identity. He’d soldiered through harassment from jocks and rednecks over his sexuality in the Southern town where he grew up. He’d come out to his Baptist parents and spent years repairing his relationship with them. He’d assumed he’d done all of these things because being gay was the crux of who he was. Now he wasn’t 100 percent sure. Yes, he was primarily attracted to men. But now women were on the menu, too. Soon, he hatched a theory that maybe he and his female roommate of many years (a lesbian, naturally) were meant to get married and have children, as if I were some gateway drug to women. A few weeks later, he told me he couldn’t see me anymore. I completely understood.

In the end, sleeping together did kill our friendship. I went from seeing Adam many times a week to seeing him just a few times a year. Even now, years later—when he’s fully back to his full gay, glorious self—there still feels like there’s an awkwardness between us. A gigantic elephant in the room that neither of us is willing to talk about. Sometimes around him, I feel like a dirty secret—I know he’s never told anyone about our time together, even people who’ve known us both for a decade. He’s brushed our relationship off as a temporary moment of confusion, something to be forgotten.

Let’s just say that next time I feel like making out with a gay friend, I’ll go home and take a cold shower instead.

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Tags: sex advice, first time for everything, gay men

Comments (32)

comments

Kiki T
wrote on October 20 2009 @ 10:09 am: [report]

OMG, that sucks. I made out with my gay friend when i was a teenager for fun. we were smoking clove cigarettes and my lips were all sweeet and I was saying i wanted to make out with someone…we were in a car with two other friends and my friend offered to kiss me, my gay friend…I laughed, but then we decided to do it for fun with my two friends in the front seat looking on and making comments, like “omg they are really going at it,” but it was more like a science experiment than a passionate kiss in any way…i had hardly kissed too many guys at that point, so it was like practice and well for him, it was just confirmation that it was not his thing…but that is my story and we are still friends to this day.

amandabear
wrote on October 20 2009 @ 10:19 am: [report]

Yikes. I made out with my gay bff once. It was so incredibly awkward afterward, and neither of us mentioned it again. Luckily it didn’t damage the friendship, though.

hlnbabe
wrote on October 20 2009 @ 10:31 am: [report]

there’s always a curious attraction between all close friends, of either sex or orientation.

lea322
wrote on October 20 2009 @ 10:45 am: [report]

In my opinion, this story highlights why a person’s sexuality should NOT be the “crux” of who they are. Being generous, being loving, being compassionate…those are traits that should be the very center of a person, not who they happen to be attracted to.

SouthOC
wrote on October 20 2009 @ 10:59 am: [report]

I don’t believe that players can change teams, so getting involved with someone who “plays for the other team” seems too risky to me.

My brother in-law is gay, and as a result I have become friends with a lot of gay men. We aren’t just acquaintances, but actually caring friends.

They know I’m 100% straight, and respect me for it. They are who they are, and I respect them for it.

Most of them have tried “breeder sex” and express that they came away feeling really weird and compromised by the experience.

My 2 cents…

MissChaotic
wrote on October 20 2009 @ 11:16 am: [report]

I feel like there are no true orientations. If you find someone who is your soulmate, whether they are male or female, they are your soulmate. After all, we as females can be straight and still have “girl crushes” on other females and prefer to be with men, and I’m sure the same goes for men, yet they’re just not as open about it.

I say do you and whatever floats your boat.

NomChompsky
wrote on October 20 2009 @ 11:17 am: [report]

I’m not sure why this is supposed to be an interesting story. I screw my gay best friend all the time and nobody ever wants to hear about it.

tabby
wrote on October 20 2009 @ 11:30 am: [report]

I used to have sex with my gay best friend too. It was really hot and great, but luckily for both of us he moved out of state to go to grad school and I got into a committed relationship. Now we can hang out when he comes to town and not have to worry about it being weird. But if he hadn’t have moved… Well, then our story likely would have also ended poorly.

Queen Frostine
wrote on October 20 2009 @ 12:08 pm: [report]

I had a summer fling with a bi guy until we parted for college. He had been with one girl and one guy and was in an experiment phase. I don’t think he ever really settled on being one way or the other. I think he just fell in love with people instead of gender.

sunrise
wrote on October 20 2009 @ 03:15 pm: [report]

wow, i’m really glad this isn’t totally unheard of… i had a shortlived affair with a gay friend of mine once. he told me that i was the only woman he’d ever been sexually attracted to, and asked if we could make out… we wound up sleeping together, and it was hot, but it was weird because he wasn’t used to female anatomy. things ended kind of weirdly and we dont really talk anymore, but it was a really interesting experience.

NomChompsky
wrote on October 20 2009 @ 03:30 pm: [report]

@ Bethlyn

Chumpsky, eh? Is that a dig?

Kate134
wrote on October 20 2009 @ 04:23 pm: [report]

Lol I’m a switch hitter but Dan Savage says it the best:
“Gay people can have heterosexual sex, of course, and most gay people have straight sex before coming out. (Gay guys have straight sex in high school like straight guys have gay sex in prison: under duress.) But the relevant question, DREW, isn’t “How gay is this ass-fing experiment?” but “What’s going through my mind during this ass-fing experiment?”

When I f-ed girls, I secretly wished/ pretended they were boys. So worry about what’s going on in your head, DREW, and not what’s going on in your ass.”

Oreo
wrote on October 20 2009 @ 05:20 pm: [report]

Wow. Powerful story.

My own theory is that sex (as a physical action) is a fun and satisfying experience regardless of the form it takes from a purely physical perspective. The difference is the mental and social perspectives that come along for the ride.

I am an absolutely 100% straight male (granted, a male with a strongly defined feminine side, but not bi or TG). That being said, I’m sure that, from a physical perspective, sex with a man would be a physically satisfying experience. It’s an experience that I choose not to explore because of my attraction to women and my lack of attraction to men, but I’m not naive enough to believe that a sex act with a man would be without its own physical pleasures.

The X factor in this situation is the emotional attachment between the two of you. Regardless of the form or strength of the feelings, the two of you loved each other. When an opportunity arose to physically express that love, the both of you enjoyed the experience. However, when the mental and social aftertaste took effect in your friend’s mind, he made the decision that it could not continue, as it had called into question everything he knew about himself (just as I’m sure a straight person faces this struggle the first time they have a homosexual sex encounter).

I’d like to say that the awkwardness between the two of you can be worked out and you could remain close friends, but that would probably take a lot of communication and understanding for both parties. At very least, he was able to explore this aspect of himself in a way that was completely safe with someone who truly cares about him and who is not using the experience to hurt him (begging him to turn straight, outing him as being possibly straight to his social network, you get the idea).

I’m sorry that the two of you are not as close of friends as you once were. That is a regrettable outcome, but the sexual relationship isn’t something I would regret. Life is a journey, and though it may not seem like it, this experience was likely more mutually beneficial than harmful. If you feel comfortable enough to get together with him over coffee and put a proper closure to the issue, I don’t think a friendship reconnection would be impossible based on what you have said. Granted, I’m making a lot of assumptions, but that’s my impression. Thank you for sharing your story.

coljack
wrote on October 20 2009 @ 06:04 pm: [report]

Am I the only one who’s wondering whether the guy wasn’t actually a straight genius? Or whether the column is actually Anonymous’s fantasy? The sex part has a weird Penthouse Forum kind of tone to it, and while I can believe a truly gay guy could have eyes-closed vaginal sex, I have a really hard time buying the idea of a gay guy going down on a woman.

_jsw_
wrote on October 20 2009 @ 06:53 pm: [report]

@coljack: I dunno if the story’s accurate, but I do know that I’m going to introduce myself to all new women as gay. This seems like an excellent way to get to them.

Except, well, damn it, I’ll have to make sure they never look at this site.

JazzHale
wrote on October 20 2009 @ 11:41 pm: [report]

Woah! This hit home for me, that’s why I just had to join Frisky! lol I was so in love with my bff that was gay, and I finally told him. But I never knew he was gay, bc he dated girls! Long story short, I’m glad he turned me down. smh I actually was mad he kissed other girls and not me! Not anymore after this story.

canadiancutie
wrote on October 21 2009 @ 12:08 am: [report]

I’M SUPPOSED TO BE IN BED RIGHT NOW. But this is just so juicy… I just had to read it.

hey_tsu
wrote on October 21 2009 @ 01:50 am: [report]

My gay guy friends talk about having made out with girls before and yada yada. It really intrigues me, although I could never imagine having sex with one of them. They’re like a second set of girlfriends haha!

ChocoBoo
wrote on October 21 2009 @ 02:46 am: [report]

Weird/sad/hot story. @coljack: Maybe this guy was a straight genius! The sweet “I’m your,gay, confused, best friend. Kiss me and help me make my mind up!” plot would have definitely worked on me

SamL
wrote on October 21 2009 @ 02:48 am: [report]

I guess it would depend on which gay friend…. I don’t think I could go for the really fem ones; my head would keep asking; “Why are you not having sex with a woman?” And I might have a similar problem with the really butch gay friends as well….. Mind thinking; “Why are you not in bed with a straight man?”

Still, never say never!

Sam xxx

Secret Story Time
wrote on October 21 2009 @ 10:21 am: [report]

That is a surprising story, but I think most women wonder what it would be like to do it with a gay man. All women wonder about men and their love of anal sex, as many women are in fear of this type of lovemaking.

bogart4017
wrote on October 21 2009 @ 12:55 pm: [report]

You had to be able to predict the ending of this story. I’ve seen it 100 times. Its like theres this built-in something in women who want to sleep with gay men and men who swear one night with them will turn a gay woman straight. Two responsibilities i don’t ever want. “Straightening out” a gay woman and (2)deflowering a virgin.

EarthGoddess
wrote on October 21 2009 @ 01:25 pm: [report]

I used to mess around with my gay bff in college all the time ... we were inseparable and it was always so hot with him .. glad I’m not alone!

DFTCTB's
wrote on October 21 2009 @ 08:27 pm: [report]

Siigh…I wish I could have boned my gay ex bff. Whenever we made out he just got this “holding down the chunks” look on his face.

Loves2Spooge
wrote on October 22 2009 @ 11:46 am: [report]

Does this actually happen?

Cray-zay

majicksand
wrote on October 24 2009 @ 01:43 pm: [report]

One of my gay friends actually did marry a lesbian. They both wanted children, so they got married and had two. They both knowingly continued to date their preferred gender discreetly throughout the marriage. At some point one or the other of them wanted to carry an extra-marital relationship to the next level, so they amicably divorced. They are still friends and share joint custody of their children.

KatieKozAreI
wrote on October 27 2009 @ 12:42 pm: [report]

my best friend is gay. he is one of the most amazing guys ever. i’m just so glad we have a brother or sister kind of relationship. i don’t have to worry about losing him over that stuff.

purplerose
wrote on November 3 2009 @ 03:00 pm: [report]

Well this just tells the story of my life! My bestfriend is gay and for the past year now we have been sleeping together randomly. In the beginning it was constant! and honestly it was usually him who started it! We are still bestfriends though! We have been friends for nearly 9 years now and that will never ever change! We don’t really do it much anymore.. but the odd time we will. We both agree that its #&@$% up and doesnt make sense because he is 100% gay, but oh well. We both agree that sex is sex, it’s better to be having sex with each other then whoring ourselves out. But I knowww I will never ever lose him! We love each other way too much.

Dutch Guy
wrote on November 22 2009 @ 04:17 pm: [report]

Some of the best sex of my life was with a gal I met online who had only lesbian lovers until she was 25. The first guy she had was a 17 yr old co-worker she had gotten close to and they lost their “opposite sex” virginity together. I met her more than 15 years after that with her sexuality having evolved into being bisexual. She was as skilled and enthusiastic as anyone I’ve ever made love to and has me wondering about sexual variability.

annie07
wrote on December 5 2009 @ 06:47 pm: [report]

Wow. This is essentially the story of the past year of my life. My gay friend kissed me about a year ago, told me that he’s liked me for a year but that we shouldn’t let this go any further… now a year later, we’re having sex and I don’t know where he stands on this weird situation. Problem is, I’ve liked him too. To me, it’s not just sex, but I don’t know if it’s fair to even want anything more… At least I know I’m not alone I guess.

_bigred_
wrote on January 22 2010 @ 01:38 am: [report]

This makes me really sad, that his curiosity for you and your willingness, ultimately ruined yall’s friendship. It seemed like you two really loved each other too, maybe not like a straight guy would love you, but still, really sad.