Boys behind the boobs: we spoke to the freshers who won the Jailbreak challenge

They really milked it


Meet Simon and Jack, the freshers who took on the Jailbreak challenge last weekend.

Dressed as giant boobs for the journey, they were the winning team racking up an impressive 1681 miles to Istanbul. To top it off, they even made it back in time for their 10am exam.

We spoke to the boys behind the boobs:

What gave you the idea for the costume?

We had to come up with a team name in the jailbreak meeting, and I suggested that we should be called “a pair of tits”. The organisers then talked about wearing costumes for fundraising and I half jokingly said “oh do you wanna dress up as a pair of tits?” and Jack was like “yeah, why not?”

How long did it take to make?

It took seven hours each to paper mâché two giant beach balls, then three hours each to paint them and cut the holes. Including the time for shopping and the work put in by our various helpers it must have been at least 30. Shout-out to our friend Alyssa. It was bloody hard work!

How did people react to the costume?

We cut a hole out the middle of the nipple, and that was our means to collect money. When people asked how to give us the money, we’d say “Oh just stick it in the nipple” and they’d laugh and reach deeper in pocket. People loved the fun of it!

One of our best stock lines was “we see you looking at our tits”, and I think the highlight was the girl who kissed me and gave me a fiver at the same time.

However it wasn’t all good. We got punched, rugby tackled, someone threw a beer at Jack and Simon nearly got taken out by a shard of glass.

There were also a lot people that thought it would be funny to hit the boobs and lick our tits. All for a good cause though.

Most dangerous moment?

It felt a bit ropey walking down the curry mile. It was the first time we’d shown the world our pair of tits, and we did get a bit of abuse from cars and some strange looks from more traditional families.

What was your weirdest experience?

When we were fundraising, and this girl suddenly piped up saying: “I’ll get my tits out if it can make you some money. I’ll get them out for a tenner.” And we were just like “Are you going to give the money to us, or do we give it to you?” Next thing we know her boyfriend runs out in his boxers, we had no idea what was going on. We didn’t really think it was painting the best image for breast cancer… so we legged it.

What was the first thing you did in Istanbul?

We were in Istanbul for 22 hours, and when we arrived it was freezing. Jack only had a shirt and shorts – he’s hard as nails!

We were looking very lost, and this guy clearly realised we were white, so he turns around and asks whether we’d heard Syrian music before. He was very friendly, and turns out he’d escaped Syria two weeks before and his whole family was still there. He and his three friends showed us around.

It was also Election Day when we went, and we were told to be careful because things might kick off… fortunately nothing did.


Did you meet anyone interesting along the way?

We met a Turkish guy from Istanbul and he let us sleep on hid sofa for the night, he was the strangest guy we’d ever met. He was so philosophical and he genuinely believed in a proper communist state.

We just wanted to have a bit of fun and celebrate. And he just talked about globalisation and the breakdown of local culture and whatnot. At this point we had been up for 30 hours in a row, and he kept us up until three. His eyes were mysteriously red… I guess it was nice to see that kind of perspective though.

Best part of the trip?

We went for this delicious mixed grill, which was genuinely one of the best meals I’ve had this year. It’s your generic kind of kebab food you’d get at like three am in the middle of Manchester, but it was just better quality, better flavour. Manchester’s not quite as good though. We won when we ate that kebab.

We also went down to the riverside that night and we hopped on this ferry for 80p – very cheap. You could see the whole skyline of Istanbul and its just incredible, really beautiful.

Any close calls?

We’d booked a cheap return-flight ticket, but we got to the airport about five minutes before the plane boarded and had to get in an hour-long queue.

We had a lucky escape and jumped to the front of the queue only to find that our flight was delayed anyway.

How much money did you raise?

We have raised £604.28 for charity so far and £511.00 for the traveling.

We wouldn’t have made half of the money without the costumes – not even close.


Do you have any tips for those wanting to try it next year?

Flights are the fastest way, make sure you have fun and remember leaving straight away is not the best way to do it – we were the last to leave! People were in Portugal before we left the students union.

Would you do it again?

In a heartbeat!

Any final words?

Thanks to everyone who donated to Breast Cancer Care UK and to everyone that helped us get to Istanbul. Also a special thanks to the kind people who helped us sculpt our Tits.
If you didn’t get a chance to donate, Simon and Jack are still raising money for Breast Cancer here.