My First Time

I was a bit of a late starter when it came to sex. Both of my (younger) brothers had lost their virginity before I lost mine. A memory that I am less than proud of was having my brothers (loudly) discussing my “Richard Branson Airlines” status whilst sitting down to dinner during a wedding we were invited to.

My first time came around with a lovely woman that I met and dated for a while. It was early winter and I had driven through a cold night with plenty of fog to visit her for the evening. I remember the winding country roads. I particularly remember the two deer that jumped out into the middle of the road and stopped. They watched me come to a screaming halt within spitting distance of them before nodding as if to say “Hm. Interesting.” before bounding back off into the night.

The decision for me to stay overnight at her place was a joint one. We were both looking forward to spending the night together. We had kissed. We had played silly games together. We shared a common interest in books and we were both studying for our degrees.

The evening went well. We had enjoyed each other’s company and were looking forward to sharing a bed. There was the usual nervousness about sorting ourselves out in the bathroom before we both snuggled down under a blanket on a bed that was far too small for two people.

“And then disaster struck. It was clear that we both had no idea of what we were doing”

Then disaster struck. It was clear that we both had no idea what we were doing. Oh sure. We had both had Sex Education at school and understood that “Part P” needed to be fitted with a condom and then slid into “Slot V”. Oh my God, what a mess!

“It is funny to think about it now, but at the time it was sooo embarrasing.”

I don’t think that I had ever opened a condom packet before. It was surprisingly more difficult than I expected. Concentrating on putting the condom on, meant that I was no longer thinking about my girl and sex. Which in turn led to me losing my erection. It is funny to think about it now, but at the time it was sooo embarrassing.

Having finally succeeded at task “fit condom”, we attempted to move on to task fit Penis into Vagina. As you can imagine, my woman was not sexually stimulated by the struggle to open the condom packet and was quite dry.

Attempting to stuff my wrapped penis into her dry vagina was quite painful for her and we were not able to have sex that night at all

In short, my first sexual experience was a disaster. Where was the Hollywood experience with soft music, heavy breathing, and sweaty bodies having a good time, that we were both looking for?

Luckily for me, the woman that I was with was truly amazing. The most important thing for her was that we try again another time.

Coming up in Sex 101

…I’ll pass on some tips about how to make sure that your first experience is better than mine – even if you are both virgins.

Stay safe, have fun