A man and woman are lying on a bed, covered by a sheet, with their bare feet poking out from underneath the sheets.
Sexual Health
November 10, 2023
5 Mins

First Time Sex (From A Man's Perspective): Staycation Gone Wrong!

Having sex for the first time can be exciting, awkward and or even lackluster. Some guys might find their first times to be nerve-wracking experiences due to societal pressure to perform in bed. John* tells us of his disastrous first-time encounter with his long-term girlfriend, Alice*, during their anniversary staycation and why things happened the way they did. *Names were changed to protect their identities

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The Staycation Build-Up

A hotel room with a queen-sized bed with a view of the surrounding high-rise buildings.

I was 23 and in my first year at university. I had been together with my first girlfriend ever Alice* for the longest time, ever since we were in junior college. It was nearing our 4th anniversary when Alice brought up the idea of us having sex together. It would be her first time, and mine too. 

While there were some heated moments between us before, mostly heavy petting when our parents were away, this was the real thing! I remember already feeling a little nervous and anxious when I said yes (very enthusiastically, I might add). 

But it was finally happening! 

I wanted to make our first time as special as possible, so I splurged on a weekend staycation for our anniversary. This way, we could have privacy and wouldn't be interrupted by nosy family members. 

A couple (man and woman) sitting intimately next to each other as they drink wine and whiskey.

We had a great day at the beach and even went to a steakhouse for a romantic candlelit dinner. Alice was wearing a low-cut red dress which showed off her ahem assets that I couldn't stop looking at. As the dinner went on, I found myself thinking about what was going to happen later.

Don't get me wrong; I couldn't wait to get back to our hotel room! But in the week leading up to our anniversary, all I could think about was what it would be like, and whether I would be good at it. I had looked up some tutorials, watched plenty of dirty videos, trimmed down there and picked up some stuff from the drugstore (while avoiding eye contact with the cashier), yet I didn't feel ready at all. 

I had decided to order a beer to go with my steak, hoping it would take the edge off so I could relax and fully enjoy the lovely evening with my girlfriend. 

The dessert had come and gone, and the bill was paid for. Finally, it was time. 

The (Anti) Climax: Couldn't Get It In The First Time

A banana placed downwards at the crotch of a pair of jeans.

Alice was definitely eager, and we even started making out in the lift on our way back to the room. Things were getting heated, and clothes started coming off. 

The room was dark when I grabbed the box of condoms I had bought. My hands were shaking from the nerves and the adrenaline, that I nearly dropped the first condom as I was ripping the packet open. I was semi-hard at that point, and I struggled to put on the first condom with the lube making it more fiddly to handle. I gave up on the first condom after a few more tries and threw it away before opening up a second one. I ended up putting the second condom inside out and had to toss that one away too. 

By the time I got to the third condom, I was starting to lose my erection, which made it even harder to put on. After the fourth condom failed, I was fully soft.

Alice caught on to how upset and frustrated I was and she tried her best to make light of the very awkward situation. She reassured me that we could try another time and appreciated how much effort I had put into making this anniversary special for us. 

We spent the rest of the evening cuddling, and eventually, Alice fell asleep. 

However, I felt terrible and couldn't sleep the entire night. 

It was my first time ever and I couldn't even get the condom on. 

Sexual Performance Anxiety Or Something Else?

A man covering his face while he sits on a leather couch in a dark room.

Nothing else happened during the staycation and we both went home. 

Even though Alice told me it was okay, I felt incredibly humiliated and my confidence took such a big hit. I felt guilty that I wasn't able to give my girlfriend the pleasure and intimacy she deserved. I felt

Why wasn't I able to get it up? 

Was I not in the mood and didn't find my girlfriend sexually attractive? Was my penis broken? Would I never be able to get it hard enough to put on a condom? 

All these questions raced through my mind in the days after and affected my sleep at night. 

So What Happened That Night? 

Eventually I decided to look it up on the internet so I could figure out what went wrong and why it happened. 

My research turned up that what I experienced wasn't an isolated incident and that many men faced it too.  Because of my inexperience and nervousness about having sex for the first time, together with the bad choice to have a beer at dinner, it was highly likely that I had experienced erectile dysfunction that night. 

Erectile dysfunction (ED) is a sexual condition that affects your ability to get or maintain an erection long enough for sex. While I vaguely knew about ED beforehand, I always thought it was an issue that older men faced. Guess it doesn't discriminate against age. 

ED can be caused by psychological factors like stress, performance anxiety and depression. That's 2 out of 3 ticked off for why my night ended up the way it did. Booze can also cause ED and funnily enough it's called Whiskey Dick! It's true, look it up! 

ED can be a sign of bigger health issues like cardiovascular disease, high blood pressure and diabetes. So if any of you guys also faced what I did, go speak to your doctor and get yourself checked out.

A banana with condom fitted on it.

After wasting practically half a box of condoms that night, I also decided to learn how to actually put it on. So I practiced on bananas, on myself, and practically anything dick-shaped. Practice does make perfect, and I got used to how finicky the condom was and how to put it on correctly the first time round. 

Pro tip: Maybe have the lights on when you put the condom on your first try. 

It Isn't Like The (Dirty) Movies 

Another realization I had after this experience was that not everything was like the movies. More specifically the dirty movies. You know the ones. 

I was expecting to be able to get hard and go hard from the get-go. The scene I had wanted to replicate after seeing it in porn was that I could be jackhammering all night long and my girlfriend would let out some string of moans and maybe even screams. 

Obviously that wasn't what happened. 

This unrealistic expectation probably added to my stress and performance anxiety, making it harder for me to get hard. 

A Happy Ending 

A couple (man and woman) wearing watches, holding hands together.

Alice and I eventually found another opportunity to try again, this time on a trip to Japan. 

We took it a lot slower this time, spending a lot more time for foreplay. I managed to get hard and had no issues putting on the condom. 

I wish I could say it was amazing and exactly how I thought it would go the second time round. But it was still a little awkward. That said, it was definitely a big improvement from the first time and we got to experience being intimate with each other on a whole new level. 

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Erectile Dysfunction
Better Sex
Erectile Dysfunction
Speak to a doctor for prescribed treatments to improve bedroom performance
Written by our Editorial Team
Last updated