Here’s an attention-grabbing headline from the UK Sun: “I had a gay holiday fling with Taliban terrorist—then I tried to leave country & machine guns were pointed at my head.” The New York Post had a slightly different take: “I took a vacation with the Taliban—and fell in love with a terrorist as we watched ‘Gossip Girl.’”
But the subject of these articles, 30-year-old Brit Toyosi Osideinde, is not some reckless thrillseeker. And though the tone of the coverage of his adventures is a little overblown—he did not actually fall “in love” with the Afghani lover who he believed to be with the Taliban—they do capture some of the wild adventures Osideinde has had.
Osideinde was born in Nigeria but grew up in the U.K. and had never left the country prior to 2015. Though he studied psychology, he became a financial advisor and worked as one in Milan, Italy, for seven years. During that time, his travel adventures took him to more conventional travel destinations like Lake Como and Vienna. In 2022, he had a revelation: the world was an amazing place and he wanted to see as much of it as possible without exception—and he had earned enough money to do so. If he was told that a place was unsafe for a visitor—especially a Black gay man with a penchant for fashion and flamboyance—he was all the more curious about it.
“I’ve been told all my life that when you’re gay, you can’t go to this place. They don’t like the gays, they don’t like the Blacks,” says Osideinde in an interview from Latvia, where he was staying for three weeks. “I want to go there and see with my own two eyes because I keep hearing all these rumours. I wanted to go and be hated and see that, ‘Okay, they do actually hate the gays.’ But I’ve never had issues in any country I’ve been to, not even Saudi Arabia, not even when I’m wearing my little gay shorts. I just want to just keep proving people wrong—that your sexuality or who you sleep with restricts you from going to certain parts of the world.”
Among the 70 countries he’s visited so far are: Ukraine, which is currently at war fighting off a Russian invasion; Afghanistan, where Taliban rule has come down hard on women and minorities with strict morality laws, and where kidnapping, terrorism and general lawlessness are common; Saudi Arabia, which has the death penalty for homosexuality; and Oman, Iraq and Pakistan, where homosexuality is illegal. “A lot of the countries I’ve been to, it’s illegal to be gay, to have gay sex. But when you do it in private, they don’t care. When I go on the apps in Oman, there are so many people there. Nobody cares.”
“My motivations are different for every country. For Ukraine, it was to see Ukraine despite the war, to see people there living real lives. It was a 24-hour bus journey from Latvia, so I was just like, ‘Do you know what? I’m probably not going to be here again so let’s do it.’ With the Middle East, I love the food, I love the culture, I love the people. The men are hot. For Belarus, I love anything about Soviet Union history and communism.”
In places like Afghanistan, Oman, Pakistan, Saudi Arabia and Belarus, Osideinde is frequently the only foreigner around, which he thinks works to his advantage. “I attract a lot of attention because unfortunately, Black people don’t really travel to these places. White people don’t either, of course.” He often uses a local guide and takes great care to be respectful of each country’s culture and religion when he’s out in public.
Pink Ticket Travel asked Osideinde about the highlights and lowlights of his extreme travels and about the ethics of what he does.
You made U.K. tabloid headlines with an interview where you talked about hooking up with a Taliban security guard at your hotel who had a machine gun, and how you watched Gossip Girl together. How exactly did that unfold?
I had no intention of hooking up in Afghanistan. But in that part of the world, they’re all a bit gay. Even at checkpoints, they’re flirting with me. It happens all the time. This guy. I was like, “You’re hot. Fine.” But he kept knocking at the door of my hotel room to check on me. It was my first night in Kabul and he was checking on me every five minutes. “Do you need wifi?” “Your food has arrived.” “Do you need water?” “Do you need this or that?” Finally, he came into my room and I was like, “Fine, show me your penis. You clearly want to.” He did and I was like, “Okay, let’s just do stuff.” And we just kept on doing stuff.
So we’ve kept in touch. We don’t speak the same language. And I’m not going back to Afghanistan again anytime soon, so there’s really no need to keep in touch.
How did you know he’s with the Taliban? You can’t really know for sure, I guess.
Everybody’s with the Taliban there. They all have their pretty machine guns that they take with them everywhere they go. I didn’t touch his gun, obviously, because I don’t believe in guns.
I guess part of the reason you wouldn’t go back to Afghanistan is because you had such a hard time leaving.
The scariest moment was when I crossed the border from Afghanistan back to Pakistan. I underestimated how intense it would be. People don’t do that. Foreigners don’t do that. They saw me as a terrorist straight away because why else would I be in Afghanistan. They assigned me a full bodyguard of four military men with heavy guns who had to follow me to every single place I went to. I couldn’t leave. I couldn’t just go down the street for pomegranate juice. They were following me everywhere I went. After I crossed the border, I had to sign loads of things and go to different places. There were police officers or army personnel driving me around, vehicles in front of me as well, with their sirens on, clearing the road. I felt very important, but kind of scared. They were just so mean and rude, and they literally had machine guns in my face every two seconds. I was in the middle of one of the most dangerous borders in the world, thinking, “I’m going to be stuck here forever.”
Do you have ethical qualms about visiting these places? You could set off an international political incident or, I don’t know, get kidnapped, and then the U.K. would have to dedicate resources to rescuing you.
No. Okay. Afghanistan has no consulate, no embassy. If you die in Afghanistan, that’s the end of the story. If you get kidnapped [travelling as I did], that’s your fault. I do my research. I watch a lot of YouTube videos. I speak to people who have been there before. I get a tour guide who has been used by someone else, and I check the reviews. You just have to be very smart. I’m a very smart person.
What’s been the hardest place to get laid?
I don’t think there’s a country where it’s hard. The gays, we’re all over the world. We’re everywhere, and men just love sex. Maybe Saudi. In Saudi, I went out in the evening and I was walking around a square. It’s a very vibrant place. I met someone again because I’m Black. I can’t remember if he came up to me or I came up to him. We just started talking and we exchanged numbers and I was like, “Do you want to come back to my hotel?” He came back to my hotel.
How about, say, Belarus?
That was just Grindr. The guy I met there actually threw up on my dick. Which is weird. People in Belarus had their faces on their profiles, so I knew it wasn’t going to be a big deal.
And Ukraine?
Ukraine is so horny. And when I say horny, I mean horny. I had maybe 70 or 80 messages in the first hour. Again, Black privilege. When you’re Black, and they’re not used to seeing people like you in the culture, they’re just obsessed. I had a lot of sex.
What was the most surprising moment?
I went to Oman in 2023. I’d crossed the border from the United Arab Emirates. This guy was talking to me on Grindr. At that point, I was restricting myself to foreigners, other tourists. But this local was just desperate to meet me. I was like, “Fine, come to my hotel.” He came in the full dishdasha, the full white long robe. I was like, “This is an absolute trap. He’s trying to kill me.” I just waited. I didn’t get naked. I was going to wait for him to make the first move. Then he just pulled up the robe and his dick was out. I was like, “Fine.”
Have you ever been robbed or physically harmed?
No, no.
Would you recommend any other LGBTQ+ people follow in your footsteps, or do you think this is just for people who are extremely adventurous, like yourself? If so, what advice would you give them?
You need to respect that you’re leaving your culture and stepping into someone else’s. You need to follow the rules. You can’t go around kissing in public and doing whatever. In private, it’s different.
Where are you off to next?
Georgia. Then I’m planning to move to South Korea in June to teach English, that’s my next career path. And obviously while I’m there, I’ll be doing North Korea.
This interview has been edited for length and clarity.
