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I Lost My Virginity to a Straight Boy
There’s a way to burst through the shame gay men are made to feel about homosexuality.
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I was 19 when I first had full-on sex with another man. I was at college, living in dorms, and the experience—aside from the usual horrifying awkwardness and somewhat spontaneity of the occasion—was completely and utterly unremarkable aside from one thing: the guy I slept with identified as straight.
The whole thing went down near the end of my freshman year at a party, at which people from the whole dorm floor were drunk and celebrating, carelessly streaming in and out of each other’s rooms, following the various different pop songs until one room took their fancy. I can remember, although I'd had some drinks, sitting alone in my friend’s room on a single bed, the mattress overly springy and with a coarse plastic coating, attempting to stream a song over our dorm’s spotty Internet connection.
It was late (or early, depending on your outlook on the world) when I was joined by the boy who was living in the room next to mine, way back on the other side of the building. He was clearly intoxicated, but it was a party after all and who was I, quite drunk myself, to judge. The minutiae of exactly how things developed from us being together in that room to us having slightly unsuccessful sex in a bathroom in a different corridor have since escaped me. All I know is that one moment we were talking and the next minute, well... we weren’t. I didn’t tell him that I’d never had sex with someone before; instead, saturated with vodka and inflated by nerves, I was swept up in the motions.
Before that night, I had hardly been a nun. When I was a teenager, I was precocious and restless. As the only out young gay kid at my school, I took the advancement of my sexual experiences into my own hands and I did what we all do: I bought a fake ID and hit the gay clubs. Out on the scene I had thrilling and, now looking back, precarious hook ups with guys, going far but never all the way. I know now as LGBTQ people we can define exactly what constitutes sex for ourselves, but when you’re young and your only sex education comes in the shape of illegally downloaded Sean Cody videos, penetration seems like the end all be all.
Still, as I grew into my late-teens, venues started to crack down harder on underage drinking, and it soon became increasingly difficult to go and hook up with guys much older than myself. I felt, in my increasingly anxious and deflated state, that I was being left behind. My first year at college, apart from being grueling mentally, was hardly a sexual smorgasbord of one-night-stands and hook-ups. Instead, I reverted to my teenage years, pining after straight boys who I knew I had no chance in hell with... until that night.
I’d love to say that I felt empowered by fucking my first guy, but the whole experience left a lot to be desired. While I knew it wouldn’t be like a gay college erotica I’d read on Nifty.org (gay canon, really), I rather naively wasn’t expecting the fall out. The boy told his then-girlfriend (who I knew about), saying I had come on to him but that nothing had really happened. Although one thing I can vividly remember was that it was quite literally the other way around, the visceral shock of being somewhat shoved back in the closet and denied the celebratory expungement of my virginity was palpable.
For the next year, we’d hook-up on and off, usually at 3 a.m. after we’d been out partying. We’d meet surreptitiously in dark and make out in the cold British weather on a park bench before venturing back to his place to have sex. And while at the beginning I felt like I had the upper hand in the situation—I was the one who was out and comfortable in my sexuality, right?—after each time we met became more secretive and more dirty, I began to feel secretive, dirty, and most of all shameful . I’m not sure whether I really fell for the guy or not, but I do know that at the end of it he was just using me to get off.
I never learned whether the boy I lost my virginity to was struggling with his sexuality. I think, when I look back now and occasionally find myself tumbling through his Facebook page, that he wasn’t. I believe it was just sex, or at least that’s what I have tell myself now to avoid slipping into a memory induced k-hole. I realize I fell into that old gay adage of placing my feelings on a person who, for whatever reason, was never going to invest them back in me. Worst of all, though, the shame attached to the memories of those first times marred how I would approach sex for years.
It was listening to Years & Years’ new song “Sanctify,” and seeing the band’s out gay singer Olly Alexander talk about how the song was inspired his sexual trysts with straight men, that I realized that these feelings are way more common than people let on. Sure, I know all about gay guys having sex with straight guys, but it felt reassuring to see him describe the “saint and sinner role” he embodied during those experiences, and to hear the uncertainty and melancholy weaved into the song.
More than anything though, was the repeated lyrical mantra of “I won’t be ashamed.” Because as queer people, we’re buried in lifetime’s worth of shame so vivid and searing that oftentimes it’s crippling. Bursting through that shame is our badge of honor, our beautifully united experience. And maybe, like the song says, that does sanctify our sex lives and makes us just a little bit holy.
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There are things in this world that you can never understand until you’ve had a penis inside of your anus. Lucky for us gay/bi men, there are quite a number of us who know exactly how that feels. Here are 15 things only bottoms understand. (And if you wanna know the struggle tops go through, head over here. )
Let’s start with the best part of anal play: prostate stimulation . The attempt to describe the sensation is utterly useless. The feeling is truly ineffable. It’s heavenly. Euphoric. Unlike any other bodily sensation we’ve ever experienced. Thank the gods for gently tucking that almond-size gland 3 inches inside of our behinds.
Bottoms are a dime a dozen. It seems like every gay guy out there is a bottom, and when you think you’ve met someone who’s definitely a top…nope. He too is a bottom. Just a very masculine bottom.
It’s quite the feeling, being unable to walk straight after being pounded. Your gait is off as you awkwardly limp more to one side.
Not all of us do it, but the ones who do know exactly what I’m talking about. It’s an interesting experience, to say the least.
YASSSS. When the man you love finishes inside you, there is nothing better in this world.
We each have our own method that we swear by: the soapy finger, a douche, Imodium, etc. But no matter how we clean, it’s always a process. And if you’re like me, 25 minutes after you clean, you always have to poop, and it’s a pain in the freakin’ ass. (Not the good kind.)
It’s such a quick transition, the pain to pleasure switch. Where it goes from you being too tight and it hurting, to you being just right and his penis feeling amazing.
It feels amazing when he finishes while he’s inside you, but it’s also incredible when you finish while he’s inside you. Your ejacuations feel stronger and more intense when you finish with someone inside of you.
Yeah, not something that tops really have to worry about. Bottoms, on the other hand, we get them quite often. Here are some tips to help you get rid of those pesky anal fissures if you’re having trouble.
Even after you clean extensively, you know that having a guy poke around down there might stir things up. And if we get too into our heads, we can’t enjoy the sex because we’re too concerned about our own cleanliness.
Your date suggests an Indian restaurant that he claims you will love. NOPE. Definitely not doing that. Thai? Absolutely not. Tops don’t have to worry about what they’re having for dinner on a date. Bottoms on the other hand? Yes, we need to plan accordingly.
The struggle is real. I’m of the belief that you can skip leg day if you really worked your glutes and quads during sex.
I know, I know. It’s not the end of the world. You can also have him go a second time, but sometimes, when you really want to get pounded for awhile and he orgasms very quickly, it can be a bit of a downer.
A switch goes off in your mind, and you turn from an unassuming, suit-wearing businessman, to a sexy AF pornstar. You start riding him like the beast you are.
All of those post-coital hormones flowing in your brain ( i.e. dopamine and oxytocin ). All of the hormones that make you feel SO. DAMN. GOOD.
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The best gay sex positions: How do gay men have sex?
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As anyone who’s ever had gay sex, thought about gay sex or watched gay sex will know there are endless combinations possible gay sex positions. But where to start? What feels best? How do you gay men have sex?
This guide to the four most accessible – and we reckon most pleasurable – gay sex positions will help get you started.
Before we get stuck into how to stick it in, we’d always condone safer sex and recommend you read our guide to PrEP , and always use condoms when having sex.
What works for you and your partner/s will depend on your shape and size. And for once, we’re not talking about cocks.
If you’re a tall man and the guy you’re having sex with is much shorter, you’ll be able to fuck in positions that a pair of beefy fellas wouldn’t find comfortable.
At the end of the day it’s all about angles, different levels of flexibility and being able to hold or change positions.
Most of these gay sex positions are anal sex positions, but there are some non-penetrative sexual positions at the end too.
If you’re after more anal sex reading, here’s another general guide on how to have anal sex that covers douching, communication, lube and some other stuff.
We’re going to look at gay sex positions from the point of view of a top and a bottom.
If you’re versatile (and we encourage you all to be), lucky you, you can do both. In some gay sex positions the top leads the action, and in some the bottom takes the lead.
So pay attention or you might miss your turn.
Interested in finding out why some guys are top and some are bottom? Here’s a scientific study from 2017 that talks about it .
This gay sex position may sound boring, but it’s not, we promise. It’s one of the easiest positions for a top, and not especially difficult for a bottom.
During gay sex, if you’re engaging in foreplay and sucking his cock while he’s laying down, keep licking, kissing and sucking as you move your mouth down towards his balls.
Then go further, toward his perineum (the bit between his balls and his ass) and then his butthole.
Bottom: if you’re enjoying this, give him a few moans and wriggle your asshole a bit closer to where his tongue is.
If he’s keen, keep eating his ass. Open his ass cheeks and get in there deep with your tongue. If you can, and body shapes and sizes depend on this, lift his ass up a bit.
A pillow under the bottom’s butt can help to raise his asshole up for easier access and comfort for both parties.
Start rubbing your cock against his hole. Spit on your cock. Use lube, and condoms if you’re going ahead with penetrative sex.
The gay missionary position is good for maintaining eye contact and clear communication during anal sex.
You can penetrate your partner slowly and carefully, keeping an eye on the target. You can build up a momentum that you’re both comfortable with. And it’s easy to get back in if you slip out, because you can see everything clearly.
Once you’re both comfortable, try holding his legs back if you’re Top. Or putting them over your shoulders if you want to get really deep.
Bottom: you could also hold your legs back yourself, behind the knees or by your feet if you’re flexible enough!
If you’re new to getting f**ked, or nervous about taking a big dick, this gay sex position could be good for you, because as a bottom, you’ll have the control.
It’s a good one for gaining confidence when it comes to taking cock – if it starts to hurt, you can slow down, and lower yourself onto him at your own pace.
You need a certain amount of athleticism to be able to ride your man. You want to be going up and down, and slightly back and forth, at the same time. A bit like riding a horse.
If you’re bigger built than your top, or if you’re a bigger guy in general this one can be tricky as gravity is against you. Be careful not to crush the chap under you or he’ll be at risk of losing his erection.
If you’re both standing up – and you may well be if you’re f**king in a sauna, sex club, dance floor, kitchen, etc, bending over for a top, or bending someone over, can be a winner.
Whether this is comfortable or not for the bottom will depend on, you guessed it – angles.
Men’s rectums are all different, so your height difference, cock shape and size, and the angle that you’re f**king him in, will all play a part in how successful (pleasurable) this gem of a position will be.
Top: start slow and give him time to get comfortable.
Bottom: telling him you’re going to back onto his cock and thus leading the action / setting the pace can help.
Adjust your stance by sticking your ass up and out more, until you find the most comfortable position.
Tops: this is a good one if you and your partner like to f**k hard. Hold onto his waist and draw your whole body into him. Or hold onto his shoulders with him bent right over backwards if he enjoys a more upwards thrust.
This one is trickier than it looks because you’ll need to position your ass in a way that makes it easy for your top to penetrate you.
It’s either going to work or it’s not. If you’re top, get behind your man, who should be in front of you on all fours. If your cock lines up nicely with his asshole, you’re winning.
If the angles require some gymnastics or penetration at an awkward angle, it could be painful for you both. Give it a go by all means, but it’s probably worth trying something else.
Bottoms: also note, your knees can get sore, and you can’t see your partner’s face clearly, so it’s harder to see if you’re both enjoying it.
One of the best, and not just because you can carry on watching Netflix. Bottoms – lay on your side with your ass turned out. It might help to open your ass cheeks up so your top can find your sweet spot.
Top: once you’re in, carefully lay down next to your partner and put your arms around him.
This can be a really intimate position, as you can hold him tight, kissing his neck and face. There’s also the potential to pump away pretty hard. It’s all in the hips!
Of course there are a tonne more complicated positions like the greasy vine sparkler and the unicorn (or something), but do the four we’ve covered well and you’ll be cuming back to them again and again.
Gay men don’t have to have anal sex.
Try the best oral sex position for you and your partner… the 69.
Getting into a good 69 position can be tricky, and there are different ways to do it.
If you’re a similar height, lay side by side, ‘top to tail,’ so your faces are in each other’s crotch. Different heights? The taller guy can curve into a V shape so that your bits are in the right places.
If you’re a bit more athletic, another way to do this involves your partner laying down, face up. Get into a push-up style position, with your mouths and cocks lined up. In this position you can f**k his mouth from above.
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