James and all his penises

Recently, I met up with my friend, Ruth, for the first time in ages.

Ruth is a legend – a bit unreliable but infinitely supportive and compassionate, and hilarious. We met when I was her supervisor, several years ago. 

Recently, she said “being friends with you is like the bit in the Wizard of Oz, where it suddenly goes into colour.”

I’m not sure what it means but I love it.

Ruth is the one who often mixes up words or names, sometimes hilariously.

One time we were talking about my ex and his family. I was about to say “and of course, his Dad is a vicar.” But at the same time, she said “oh yeah, his Dad’s a Pope, isn’t he?”

She struggled to remember ‘Whippersnapper’, and would say “what’s happening with the Whistle-blower?”

In fact, this time, she said “have you heard any more from the Whistle-snapper?”

This time, I was telling her all about the saga with James – the guy I was friends with in 2011, when he was my friend’s neighbour. 

We were kind of friends who slept together for a while, before he got a girlfriend and I moved away. 

Over the last 5 years, every so often, he gets back in touch and says things he definitely shouldn’t, when he has a girlfriend.

Usually, I’ve assertively shunned his advances, but this time, I haven’t. 

Over the last month or two, we’ve been in touch a lot, and had full-on text sex, complete with naked photos, 3 times.

I feel terrible, as he has a girlfriend, even though it’s on very shaky ground.

It seems like they are only living together because they have a tiny boy.

Last time I wrote about him, I knew I needed to wrap things up, as this has ‘bad idea’ written all over it. Even if we aren’t having sex in person, it would be very easy for me, James, his girlfriend and his one-year-old son to get really hurt.

A week after that, we were texting each other. I was quite bored on a Sunday afternoon, and I texted him saying that.

Usually, I avoid texting him first, because I don’t want him to get a text when he’s with his girlfriend, and arouse suspicion. However, he always seemed to be on his own on Sundays.

I said I was bored. He replied saying he was in a pub but would text me later, and sent me selfie of him and his son in the pub.

On Sundays, he often seemed to go for walks in the country with his little boy on his back, so at first I assumed he was alone with his son, maybe after a walk.

But then I thought maybe he was with his girlfriend too.

Shit, maybe it’s not as over between them as it seems.

He never did text me back later, and then I didn’t hear from him all week. 

I felt OK about not hearing from him and realised it needed to end anyway. Maybe he and his girlfriend had rekindled their love over a Sunday roast.

A week later, on a Saturday night, he texted me saying he was livid!

We had a bit more of a general chat, that evening, as he seemed too drunk for serious chat.

He even accidentally called me on Whatsapp, much to my delight, as I’m always doing this.


The next day, we chatted all evening, about cooking for ages, then about the flat I was trying to buy. 

Then, the conversation moved on from properties with gardens, to al fresco sex, to him suggesting text sex.

I said “can I ask what your exact situation is, relationship-wise?”

Then I added “sorry – horrible timing if you’d just got your cock out!”

He was evasive – told me what I already knew about them sleeping in separate rooms but “trying to do the best they can for the boy.”


I wasn’t quite done. I was still trying to get to the bottom of what happens with his phone – whether she reads his messages or would ask who it was when I text. I still don’t feel clear on this.


After a while, I asked if he had anything he wanted to ask me. I was half-joking, and just expected him to say “can we have text sex now please?”

But he didn’t.


I was really surprised he felt like that. And touched.

When I first broke up with Balthazar, I had nowhere to live and was staying with a different friend every night. I often stayed with James and he was as good as some of my lifelong friends, even though we’d only known each other a few months.

Obviously, he had an ulterior motive, especially as it was during one of those sleepovers that I first found myself naked in his bed, but still.

When Balthazar died, I learnt not to take anything for granted from people, in terms of support – people are funny about death. Most people I’m close to were wonderful, and basically kept me alive, but some people I’m close to didn’t know what to do. 

People are terrified of saying the wrong thing after a death, but now I know you can’t really say anything to make it better and you can’t say much to make it worse, but just saying anything and keeping talking is what helps.

Some people I barely knew were surprisingly amazing, others weren’t. I had no opinion about James’s reaction to Balthazar’s death. We’d already been drifting apart.

I told him that I did feel aggrieved with Tim, but not him, and reminded him of times he was a good friend.

The next day was a Monday. He texted me something about fingering me, while I was away in a meeting and my phone was face up on my desk, in full view of my colleague, and the message flashed up on the screen. I don’t know if she saw.

I met up with Ruth that night and told her all about it.

She asked what he looked like and I tried to find a photo he’d sent me of his face.

It was funny – he sent me a lot of photos him and his son, or just his son on his own. 

He also sent me a lot of photos of his penis.

When my phone said “James has sent you an image”, I never knew if it was going to be of his kid or his cock.

Ruth asked why I thought he did this.

I said “well, I think with his little boy, he’s just really proud of him, and wants to show him off.”

Then I laughed and added “and with his penis, I think he’s just really proud of it, and wants to show it off.”

James is really handsome. I found the photo I’d been looking for and showed Ruth.

“Oh he’s really hot. You said definitely have sex with him. And then tell me everything.”

“Shit, sorry, all the thumbnails from our other photos are showing up along the bottom!”

“Oh yes! You’ve got lovely breasts.” Ruth said.

By the time she gave me my phone back, she was nearly as well-acquainted with James’s penis as I am.

When we said goodbye, she said “tell me what happens with James and all his penises!”

She meant “James and all his penis photos” but it made me laugh – like he was a monster from a sexual Greek myth.

Since then, it’s changed. One minute I was thinking where the hell is this going to go next?! 

But now it’s pretty much over.

First, the next time we had text sex, I didn’t like the way he was hectoring me for not sending my breasts quickly enough.

3 minutes had gone by, and I appreciate that might be a long time in wank-erection-hours, but I think, really, if a lady is sending you a photo of her breasts, you should pipe down and be grateful.

Every time, I get really stressed out. For one thing, I’ve never sent my actual breasts to anyone else, and I’m not 100% comfortable with it, ethically, especially because of his situation.

Secondly, I’m not sure how comfortable I am from a body confidence point of view. I swear my breasts are a completely different size every day, and I’m always worried they’ve shrunk since last time.

Thirdly, my breasts always have this annoying halo of horrible black hairs around the nipple (I really think we women should break the silence on this, as at least one of my female friends has confirmed she gets this too).

So, as soon as it’s photography time, I’m hastily grabbing the tweezers after spotting a few rogue ones. Half the time, they’re ingrown hairs instead of standard ones, so plucking them involves picking and squeezing and sometimes blood and pus. Which I don’t want in the photo.

So the last thing I need when contending with all this stressful and frenetic nonsense is someone hurrying me.

So that happened, and I was nonplussed, but the rest of the text sex went very well.

The last time we spoke was a few weeks ago.

He texted me saying “tell me how you are” and we had a nice chat. It seemed like he was really interested in how I am.

We were talking about our lives a bit, then he said he was “in bed. Hard as usual.”

Now I’m reading this back, it doesn’t seem that bad, but at the time it made me feel the opposite of turned on.

If anything, we should’ve been in the text-sex equivalent of the honeymoon period. 

But this felt like the equivalent of that feeling when you’ve been in a relationship for years, and you’re just trying to enjoy your book in bed, but an erection is unceremoniously being pressed against you under the duvet.

17 thoughts on “James and all his penises

  1. You’re right about that… it’s starting to feel a little too comfortable already. It’s shocking considering you were never really dating! Haha

    Ruth sounds like a blast… and so do you! I love that she described you as the color part in The Wizard of Oz.

    Liked by 2 people

  2. I wonder if there is name for the place where the excitement vanishes, and the analysis starts? When things are not quite real, they call it “uncanny valley” – there should be an equivalent.

    Liked by 1 person

  3. Love this post on so many levels. Firstly, text-sex what is that? In the rest of the world we call it sexting 😉 Secondly, I have absolutely no hairs around my nipples and even before my breast reduction I didn’t! Thirdly, he sounds like a desperate and demanding twat. Sorry to be blunt, but cheating on the mother of his child and not even having the guts to do it in person? I am just so over these guys who want a wank partner, where it’s all about their gratification 😦

    Like

  4. Pingback: Interview with Dater Analysis – Unleashing the Cougar!

  5. Pingback: Whatever happened to… | Dater Analysis

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s