Straight guy tries anal play for the first time, makes hilarious rookie mistake

Man tried anal play for the first time (it didn't go well) | Photo: Wikimedia

A straight guy has tried anal play for the first time, but in doing so made a rookie mistake.

Reddit user Boraicholol, who we’ll Steve, takes medication for ADD/ADHD.

He also occasionally is prescribed Viagra for antidepressants. As a part of that, he often finds himself in what he calls a ‘neverending fap mania’.

What happened when a straight guy tried anal play for the first time

Writing on the Today I Fucked Up subreddit, he said he had taken his daily pill early on in the day.

He said: ‘In any situation where you’re on stimulants, porn always finds it’s way into your dopamine filled mind. I grab my lube, my towel, and put some porn on. After 45 minutes of furiously pounding my meat like Michael J Fox on meth, I decided to experiment. This is the moment where I fucked up.

‘I had always heard that the prostate was the males G-spot. I decided to put this to the test. My girlfriend never liked cockrings so I had one left, I lubed up my ass and stuck it in there.

‘I had a hold of the rubber part that is intended for your cock, and the actual cock ring was in my ass vibrating. What followed was an amazing orgasm and release from my elongated self love.

‘At this point the post-cum shame kicks in. Looking down at myself, cum on my stomach, lube everywhere, and a vibrating cock ring in my ass. Needless to say there was great shame felt, and I wanted to put this behind me as quickly as possible.

‘I grabbed the towel beside me to clean up, the hand that grabbed the towel was the hand holding the rubber part of the cockring. Upon realizing my mistake, my asshole clinched in panic and my cockring decided to take a tour to my colon.’

‘What followed was utter panic’ 

Rule one with anal play: always use a flared end.

Steve continued: ‘What followed was utter panic. This thing was still vibrating and I couldn’t find it.

‘I went to my bathroom and decided to get serious. I sat on my toilet and lubed up my asshole and I stuck one finger up me bum and could just feel the rubber part, this continued for 30 minutes until I finally hooked my finger around it.

‘The hard part was dragging it out. Nails do not feel good when they are clawing the inside of your ass.

‘After another 5 minutes of this, I almost get it out but my finger slips and it goes right back up there.

‘Cue 30 minutes later I’m back to almost getting it out. Finally, I just decide to pull it out and deal with the damages left to my ass later. I got it out along with plenty of shit on my finger to go with it.

‘The rest of the night was spent in the shower sitting down and contemplating my life.’

Lessons learned

You may have some questions. For example, why not try and force it out?

Steve said he is susceptible to hemorrhoids and would prefer to avoid them.

Why not wait?

‘Didn’t feel like waiting for the daily log,’ he said.

‘Despite the damage to my ass I’m glad I got it out, the vibrating was driving me crazy. Imagine just trying to sleep and feeling a constant bzzzz in your asshole.’

But will he tell anyone, like his girlfriend?

He said: ‘This will go with me to the grave.’

See also

Study reveals different masturbation habits of gay and straight people

Meet the gay men who think not masturbating gives them superpowers

A lot more straight men are using dildos to masturbate than you might think