Before I start delving into this story I would like to first warn you that this is why I made my rule about discussing sex. Just to recap, I stated that I would only discuss sex if it was absolutely crucial to the story.
Without beating round the bush, sex is absolutely crucial to this tale.
If you don’t want to read it then I recommend closing this page now before you go on further. I have argued with myself over this story because I feared it would be crude but it’s one of my funnier stories so I couldn’t leave it out!
Besides, I promised I would be honest throughout so here goes….
I had actually met Jack* way back in 2009 on a night out with the girls but I never really spoke to him again and nothing happened but in 2015 when I bumped into him we said hello and did the small talk catch up. Jack was extremely handsome and confident just as I remembered.
I was still feeling a little gutted about how Jamie (my previous post) had left things with me so I wasn’t exactly looking to rush into anything, but when Jack asked me if I fancied going for a drink sometime, I decided why the hell not? A good looking, confident and funny guy had asked me out so I was not saying no to this.
Besides, it was a nice confident boost and made me feel good about myself.
My first date with Jack landed on the same day as one of the England World Cup Rugby games which we both wanted to watch so luckily we planned our date at a bar where the game would be shown. I walked in and instantly felt butterflies because I think I’d forgotten just how hot Jack is!
The place was rammed so at the bar we ended up standing close (the butterflies loved that) and ordered drinks. Throughout the night we laughed, a lot, talked about our jobs, family and of course watched the game at the same time. He even made comments about how awesome it was I was so into Rugby; RESULT! I’m scoring points with this one so I know it’s going well.
Once the game finished we moved on to another pub and sat and talked for hours! Jack had the same sense of humour as me and made me laugh until my stomach hurt. As it got to 1am we realised it was probably time to head home and say our goodbyes…. Now stop what you’re thinking right now! We did not have sex on our first date. We didn’t even kiss thank you.
Me and Jack continued chatting and organised a second and third date.
Our second date went pretty much how the first one went and the third date is where things got interesting. On our third date, Jack asked me out for cocktails and then dinner. I met him in a bar and we had some cocktails alongside more laughing. Yes, ok so we laughed a lot. After cocktails we went across the road for dinner. One thing you should know about tonight is that I had got the train in so I could have a few drinks. The last train home is just after midnight. One thing you should know about me is that I don’t drink wine! Wine gets me drunk too quickly and I don’t even really like the taste. While ordering dinner I settled to drink a coke and some water to keep sober after our cocktails.
Jack had a different idea because while I nipped off to the loo, he ordered a bottle of wine to the table for us. Oh bollocks! I couldn’t tell him I hated drinking wine so I sat and drank two glasses of wine with dinner – No no no!
By the time the bill came I was tipsy and trying my best to act as sober as possible. Jack had other ideas and suggested going somewhere else for another drink. I enjoyed his company so much I didn’t want the night to end yet so I agreed and we got another drink. That’s it now, I’ve mixed my rum based cocktails with two glasses of wine and now a southern comfort.
I’m feeling drunk and oh my god what time is it?? I’ve missed the last train home!
A taxi home will cost me £60 which is my only option now. Jack has to get a taxi home too and he does live on the way so maybe we could share a taxi and split the costs. Ok this sounds plausible. On the walk down to the taxi rank it suddenly dawns on me that Jack hasn’t tried to kiss me once and this is the end of our third date! Well then I’ll have to take that bull by the proverbial horns and take the lead.
As we walk over a little bridge with the lights around us I take his hand and pull him towards me and we kiss. The sound of the river beneath our feet; the fairy lights hung in the willow tree behind us and the quiet air of us being alone standing on that stone bridge. I know, how ridiculously romantic and perfectly set for our first kiss.
My dutch courage had timed that perfectly!
Anyway, we’ve kissed now and so we get in a taxi and give the driver the address for our first stop; Jack’s house. We kiss again in the taxi and as we pull up to Jack’s house, I find myself thinking screw it so I get out with him and thank the taxi driver (after we paid him of course). I am 24 years old and single and I’ve always lived my life being boring and having a guard up so why the hell not! I like this guy and he seems to like me so I’m going to live a little.
Jack opens the door and we walk inside. Right, last chance to switch off and stop reading because this is it! Jack turns around to me and he pulls me closer to kiss me deeply and passionately. His hands are finding their way into my hair and I’m thinking “wow. This is going to be amazing”. Jack picks me up (with ease I might add so I must not need the gym that much) and sits me on the edge of the kitchen table. Clothes are being pulled over heads and I’m still thinking this will be incredible!
We rush upstairs in our underwear and into his room.
What happens now is not at all the fun, living life, incredible night I was expecting.
Without going into too much detail, most of you will understand the importance of foreplay. I don’t want to sound crude but you don’t drive a car with no oil in it. When you’re cooking you prepare your ingredients. Preparation is key otherwise it will just be an extremely uncomfortable experience for everyone involved; especially a girl!
Before I can even think about foreplay, Jack has removed my knickers and he’s gone in for the kill. He’s plunged right in without any warning whatsoever.
Holy crap this is uncomfortable and slightly painful.
How he can’t see the discomfort all over my face I don’t know because I am not hiding it well. Anyway, moving on. Once it was all over for him we turned and went to sleep. My Mum picked me up the next day and I explained the whole ordeal to her.
Jack and I continued chatting because he was clearly none the wiser of his mistake. I, however, spent the next few days dealing with what felt like friction burn!
Four of my closest girl friends found the whole thing hilarious and even coined the nickname Dry Boy for Jack. After a few days I decided I had to tell him how uncomfortable I was feeling now because I was filled with anxiety of ever having sex with him again. I sent him a text message saying that “maybe next time we could engage in a little more foreplay? I’ve been feeling a little sore since our antics”.
That message could be the end.
He might be so embarrassed that he never talks to me again. He replied laughing and saying it was the best message he’d ever received. Thank god his sense of humour is as good as I thought. He promised that next time would be better. All it took was a message being honest. Our fourth date was organised and Jack planned on cooking me dinner.
The fourth date came around and Jack cooked me a delicious dinner at his house. There was no embarrassment and neither of us mentioned my message (phew).
Then, it happened.
We went upstairs and I have no idea what he was doing but Jack tried some kind of foreplay. His action was very quick and could only be compared to tapping a teaspoon on a hard boiled egg to break the shell.
Before I knew it, I was experiencing de ja vu from our last night together.
This was it. If I stayed with Jack, I was destined to experience nights like this every time. Jack was amazing. He was incredibly good looking, funny, confident and we had a great time together but what do I do? The next day I left after breakfast and, again, he was none the wiser. I sat with friends and asked them for advice about what I should do. I didn’t want to end things but I didn’t want to hurt his feelings.
We just weren’t sexually compatible.
I felt so disheartened but didn’t want to give up so I carried on as if nothing had happened. I continued chatting with Jack and decided that at some point before our next date, I would have to be honest and talk to him about it. We just liked different things and maybe I was different to girls he’d been with previously in that I needed more attention in that area before the main event.
I never got a chance to talk to him or see him again because Jack ended things with me.
One Monday morning he sent me a message explaining that he was moving jobs and moving house so he just didn’t have time to date anyone. Well I appreciated his honesty (or what I thought was honesty). Maybe he could sense that we just didn’t fit sexually. Maybe my message had hurt his pride and he couldn’t deal with it.
Who knows but he definitely wasn’t honest with me.
Less than a week after ending it with me my friend messaged me with a picture of him on a date, in the same restaurant as her, at the table right next to her!!
She took the photo subtly but it was definitely him. I was updated throughout the night and apparently the girl he was with spent most of the night looking in the mirror at herself; charming. Later that night I heard news from my inside spy that he had taken his date to the pub…. THAT I WORK IN!
He knows I work there because he used to come in and see me while I was working including Valentine’s Day! Luckily I wasn’t working that night but he didn’t know that. For all he knew I was working a shift and would potentially even serve them at the bar so he could rub it in my face that actually he’d lied to me and just didn’t have the balls to be honest (I see a theme running through most of my blog posts now – the men I choose lie). Another of my secret spies passed on that Jack’s date was such a delight that she repeatedly stood outside the front of the pub and stuck her fingers down her throat to make herself sick (charming).
What was he thinking taking someone on a date to the pub he knows I work in, after telling me he doesn’t have time to date? What happened to just being honest?
So that’s Jack.
To anyone who was offended by my post, I would apologise but I gave you plenty of warning about the sex bit. You have only yourself to blame for letting your curiosity get the better of you.
Leave a Reply