Jack Smith|13.12.2013|Feature Real stories Someone Like Me
As first times go I was pretty lucky.

If you’ve seen My Sex Life and Everyone Else’s you’ll know I’ve never had sex with a woman. Nor do I think I ever will. You see, I’ve always been the biggest fan of d**k. Ever since I laid eyes on one in my brother’s hardcore porn mag at the tender age of 11, I couldn’t stop fantasising about getting my hands around one of those mesmerising appendages.

You can imagine then, after my first oral sexual experience and literally fist pumping the air in front of the bathroom mirror post-blow, when it came to full, penetrative anal sex with another dude, while there were things I was certainly unsure of, it would be a lie to say I wasn’t excited.

My first time with another man was a few days after my 16th birthday. He was older; a customer of the restaurant I was working at, and he had this great big smile he would fix on me every time I looked over. I wasn’t out of the closet to my parents then, but my colleagues knew, so when his party all got up to leave I summoned the courage and asked him if he enjoyed his meal.

The next thing you know we’re exchanging numbers, arranging to meet the following evening and voila: I’m on my back, naked in his bed, he’s lifting my legs onto his shoulders and while smearing lubricant onto the condom he’s just put on, he asks me if I’m “ready”.

All the fun and excitement suddenly disappeared and all that ran through my head was: A) how much is this going to hurt? And B) I pray to God I don’t literally s**t myself. Luckily, I think he saw the panic in my eyes because he assured me he would “go slow”.

There’s no denying it wasn’t painful (I think, aptly, the exact words I used were “f**k me that hurts”), but after a while the burning stopped and it felt good. I guess the fact that a hot, naked man was on top wasn’t so shabby either. After a while it started to hurt again so we stopped. The next morning we did it again.

As first times go I was pretty lucky. I’m still grateful for the understanding and compassion the man who I shared my first time with showed to me, because apart from making my experience more comfortable, it taught me to treat other guys that way.

Jack is one of the stars of our documentary My Sex Life & Everyone Else’s, which featured on MTV UK. Watch it here.

Follow Jack @jackarthursmith.

What do you think about Jack’s first time?