This week, The Undateable Gay goes to prison... Not as an inmate, but to run a social event for gay and bi prisoners.

This week, The Undateable Gay goes to prison… Not as an inmate, but to run a social event for gay and bi prisoners.

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When I was first invited to visit a male prison and do an interactive social group with the LGBT community inside, I sh*t myself and nearly didn’t commit to the project.

What the fuck was I going to talk about? Yes, I grew up on quite a rough council estate where crime was high but luckily I’d avoided prison, unlike many of the boys I grew up with.

The closest I’d ever been on the wrong side of the law was the time I got thrown into the police cells at Brighton nick for being drunk and disorderly. But that’s a story for another day.

As I pulled up at the prison, it was very daunting. There was this massive building in front of my eyes, surrounded by barbed wire. It was lucky I’d taken a couple of Imodium that morning, let me tell you.

I was given a tour when I first arrived and it’s very surprising how much it actually looked like the Bad Girls set. I was scared of bumping into any real-life prisoners. I wasn’t sure what the rough, macho, non-gay ones would make of this mincing homo.

As 2 pm came closer, it was time for me to be escorted to the chapel to begin my LGBT group with the gay prisoners. Yes, it was being held in the chapel. The irony wasn’t lost on me.

As I was being taken into the chapel, an officer stopped me at the main doors and asked for my name. I obligingly gave it and she announced I wasn’t on the list so I couldn’t gain entry.

Looking very confused, another officer came to my rescue.

“He’s not a prisoner. He’s the guest speaker!”

Realising her mistake, she let me through but I couldn’t help blurting out, “Do I look like a prisoner?”

I sat down in the chapel after I’d organised the chairs into a circle, a la Alcoholics Anonymous style. My only other option was a straight line and that was far too formal for my liking.

Sweaty palms and heart palpitations, I saw the big hand heading towards the 2. I didn’t know what to expect. I’d been told I had a man who murdered his husband and an arsonist, among others.

As they entered, my butterflies escaped through the bars. The husband killer came in and shook my hand, whilst hugging me and kissing me on the cheek. The rest made similar entrances and greetings and automatically put me at ease.

I’d been far too focused on the fact that I was in a prison and forgotten that in reality, I was just talking to fellow human beings who also happen to be gay. And just so happen to have made mistakes.

Each person had their own individuality and within seconds, I’d forgotten I was even inside a prison. We talked, we laughed and we discussed sex. A LOT.

After an hour, a prison buffet was bought into the room for us. It looked bloody delicious. Even though I must confess I was a little wary of eating it after being told it had been prepared by the prisoners in the prison kitchen.

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One of the gay prisoners, Mike, who I took quite a shine to (and he to me), assured me that as long as I wasn’t a paedophile, the food was quite safe to eat. I told him I was guilty of many things, but that wasn’t one of them.

Whilst shoving a prison-issued cheese roll into my gob, a big Zimbabwean prisoner came and grabbed me by the arm,

“You look so good! My cell number is 427 if you want to come back later!”

I nearly choked on my cheese roll and managed to choke out the words,

“I think you’d split me in two!” which was met with roars of laughter from the whole group. His tight grey jogging bottoms left little to the imagination and it was clear to see he was MORE than well endowed.

They talked about their lives and it left me feeling rather humbled. Yes, I got bullied at school for being gay but on the whole, I’ve been widely accepted by my family and friends. But some of these men have been abandoned by their families for being homosexual. One of the men was even imprisoned in Russia for attending a gay pride event. It certainly opened my eyes.

I think it was refreshing for them to be a part of this social group and be able to freely express themselves and their sexuality without any fear.

Before I was leaving, the prisoners were begging me to go back. They loved our afternoon and it went on much longer than I expected.

After three hours, the officers were having to chuck me out because we had gone on for far too long and I was putting out the schedules. But it was honestly one of the best experiences of my life. Much better than any money I’ve ever raised for charity. Actually doing a random act, something worthwhile on the front line, from one gay boy to my fellow LGBT community.

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My final words were from Mike.

“I get out in seven weeks. How can I contact you?”

I quite fancied him. He was just my type so it would have been rude to discriminate against him just because he’s in prison. So I made sure to tell him how to contact me.

About the author: Mark Woollard

Mark David Woollard graduated from Brunel University, West London in 2009 with a Bachelor of Arts degree in Creative Writing and Journalism. Since then, he has written for many publications as a freelance writer. He has been ‘The Undateable Gay’ for The Gay UK magazine since 2015 where he documents his unsuccessful dating life. He wrote an opinion column for the national Student Times, discussing LGBT issues.

He also writes educational pieces for ‘Massage World’ magazine, giving advice to Reflexologists about treating certain ailments. He authored a novella in 2013 entitled ‘The Fun and Frolics of FIFI a L’Orange’, the crazy adventures of a drag queen.

And is currently working on a series of LGBT books for children and a collection of flash fiction.

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