I Had a Gay Holiday Fling with a Taliban Terrorist - Nigerian-British Tourist Toyosi Osideinde

Toyosi Osideinde with Taliban members in Afghanistan (no pictures in this story show Toyosi's lover)

Toyosi Osideinde, a 30-year-old financial adviser from Bath, Somerset, has shared harrowing and deeply personal experiences from a recent six-day trip to Afghanistan, a country under strict Taliban control since the withdrawal of U.S. forces in 2022. Known for his love of extreme travel, Toyosi has visited 69 countries, including Syria, Iraq, and Belarus. However, he described his Afghanistan journey as the most dangerous and intense yet.

Toyosi entered Afghanistan via Pakistan, flying into Islamabad and traveling overland to Peshawar before crossing the volatile border into Taliban territory. Despite global travel advisories against visiting Afghanistan, he proceeded, seeking what he called the ultimate thrill.

The financial adviser likes to visit dangerous countries

Upon arrival, he was interrogated by armed Taliban members, an experience he described as terrifying. “I had machine guns pointed at my head and was interrogated 24/7,” he recalled. He said travelers are scrutinized when exiting the country, often flagged and treated with suspicion.

While traveling through Kabul, Nangarhar, and Bamyan, Toyosi reported being constantly monitored by Taliban operatives. He noted the total lack of embassy support, unlike in other high-risk regions he had visited, saying, “If something happens to me, I am on my own.”

Toyosi said he was treated like a celebrity in Afghanistan

Despite the oppressive environment, Toyosi experienced a surprising level of attention from locals, likening the experience to celebrity status. He described people following him for hours, seeking photos, and being approached for YouTube videos. In public spaces like banks and markets, he was often treated with deference and allowed to skip lines.

One of the most unexpected parts of his journey was a romantic fling with a Taliban member who worked as a security guard in his Kabul hotel. The two spent evenings watching Gossip Girl, eating takeaway, and forming a temporary but passionate connection, despite language barriers and Afghanistan’s brutal stance on homosexuality. “He would love showing me his guns,” Toyosi said. “We didn’t talk much because he didn’t speak English and I didn’t speak Farsi.”

Toyosi spent six days in Afghanistan in November

Homosexuality is strictly prohibited and punishable by death under Taliban rule, adding significant risk to the encounter. Toyosi, who typically uses Grindr to meet men while abroad, said he avoided the app entirely in Afghanistan and Saudi Arabia for safety reasons.

While Toyosi’s stay included some moments of personal connection and cultural insight—such as seeing women working in banks and shopping without face coverings—he acknowledged the deep repression still prevalent under the Taliban regime, especially toward women and the LGBTQ+ community.

Toyosi outside the Blue Mosque in Kabul

His return to Pakistan was fraught with tension. Toyosi reported being closely followed by four armed officers for two days, unable to move freely even for simple errands. “There were so many points during the trip where I was like: This is it — you made your bed, this was stupid and now it's time to die.”

Despite the dangers, Toyosi continues his pursuit of high-risk travel. He plans to take a 26-hour bus from Latvia to Ukraine, amid the ongoing war with Russia, and will soon relocate to Georgia. Funding his travels through a flexible remote job as a self-employed financial adviser based in Italy, he said he works in the mornings before exploring in the afternoons. “I wear a suit top and shorts during meetings,” he joked.

Toyosi’s story is a stark reminder of the extreme risks associated with travel to conflict zones, particularly under authoritarian regimes where personal freedoms are heavily restricted.