Diary of a Human Dilator

I’ve been thinking; as much as a large majority of my posts focus around swirly and often disjointed story lines about boys, I’ve never given you the boy’s perspective. And now I’m in the privileged position to be occasionally sleeping with a semi-literate human dilator who knows about the blog, is a regular reader and has a recurring role; it would be a shame not to abuse this as much as I abuse him right?

……………….

Let’s start with the truth shall we?  Sleeping with A didn’t exactly happen how/why I first imagined it would.

From Day 1 of Sixth Form I had a burning desire for A; I found her incredibly sexy. I wouldn’t have said, “yeah, she’s beautiful/gorgeous/pretty”, I would’ve said “she’s really hot, and I really want to fuck her.” I don’t know what it was that made me want her, I don’t know what it is that makes me want her again and again. I think it may have been the persona; the impression I get from her. She knows she’s hot and she knows other people think she’s hot, to be fair to her she plays on this very well. The thing I notice most is The Strut. I’m convinced she’s taught herself this special walk; perfected it through years of practice. No, that’s just me being sad, but in all seriousness: IT IS SEXY.

As I was saying, I had this longing for her, in a completely sexual way. When we first properly met I had a girlfriend, and A was getting close to Mark. Me and A picked the same option for Thursday mornings at the start of year 13; and I suppose this is where it all started. I had my complaints about my girlfriend and A had hers about Mark. There was a spark there, definitely. I think it was just that we’re very similar but in weird ways. So yeah, we got closer and closer until one Wednesday evening I get a text saying something along the lines of:

 “I’ve been thinking a lot about this, and I’ve decided I’m going to tell you something about me tomorrow morning that not many people know.” I panicked. A quickly confirmed it wasn’t cancer which put my mind at rest for a while; then I started to wonder, “what the fuck is it then?”

Thursday morning came and she told me all about V and this blog I’m now starring in, which I read in an awkward silence as A tried to look busy. I finished reading it and wanted to give her a hug- the stubborn bitch was having none of it- made me feel a right tit.

Fast forward a few months, Sophie (my ex) and I are over, and the whole Mark thing got seriously screwed up (as I’m sure you have read!). At this point sleeping with her wasn’t the first thing that popped in to my head; but as the weeks went on, A had no one to piss about with and I guess I was just there! There was a mutual attraction, and we’d got together a few times on drunken nights out. Then it became a little more serious. I made it clear to A I was willing to be a human dilator, partly because I genuinely wanted to help a mate, and partly because that burning desire I mentioned earlier was still there.

I don’t know why, but she took a while to accept my proposal. She did accept it in the end, and after that the night of her shindig approached quickly. I remember texting A a few days before, asking the crucial question: “shall I bring any, err...? x” When she replied with a yes, I started to believe I was actually going to have sex with A! This was very good news.

There were already a lot of people there when I arrived at A’s house and I have to say I was pretty content with whom I was (potentially) sleeping with that night... She looked hot, I’m telling you. In fact, it can’t have taken us much longer than an hour to sneak off somewhere for the first time. It was all very well planned; even though we were metres away we would be texting each other, looking for the next opportunity for excitement. And if we weren’t texting there would be discreet passing comments, “upstairs in two...” No reply would be needed. 

From arriving and playing a bit of poker to getting the last text of the night from A saying “I’m going to bed...” it’s all rather a blur. I remember having a drunken sing-along session with a few people; I remember playing pool a few times; and I remember going to vacant rooms with A for a few snogs. But honestly, that’s all I can clearly remember.

Back to that text. I won’t lie to you; I didn’t need to be hinted at twice. Within a couple of minutes of reading that text I had said “I’m off to bed, night” to the others and gone up the stairs towards A’s room. I bet I did one of them walks where you want to sprint but you can’t, so just end up looking stupid. It didn’t matter, no one saw.

I got to the end of the landing and knocked on the door, confirming my identity. A let me in and shut the door firmly behind me. Before either of us could speak a word we were at it again- her back to the wall this time. Hands searching all over each other’s bodies, it wasn’t long ‘till my t-shirt was off. Our lips still locked, I spun A round so her back was to the bed. I slowly started to take steps forward, urging A to edge back closer to the bed. Now, I don’t remember feeling that drunk, but I can’t have been in total control because I didn’t judge how far away the bed was, and we ending up tumbling onto it and laughing quietly. This also didn’t matter, we were enjoying ourselves.

We proceeded to get into bed, most of our clothes already littering A’s bedroom floor. I was having a lot of fun, it seemed like A was too. I’m pretty sure I made all of the ‘first moves’ up until the actual sex part- that I was unsure about, I left it for A to decide as and when we did that.

After a lengthy, but very enjoyable ‘warm up’, she eventually said it. She was ready. I was definitely ready, but slightly scared too. My biggest fear was causing any terrible pain, I really, really didn’t want to do that, because if I did it would turn me off hugely, let alone A. Despite saying “sorry, is it hurting?” a few times, I really enjoyed it- it wasn’t at all what I expected, but I’m guessing A just has a pretty high pain threshold. So, even when she let me know she’d had enough, I was pretty satisfied. Mentally anyway. Weirdly, it didn’t bother me that I didn’t ‘finish’, as such.

Perhaps the most surprising, and pleasing thing came after the sex. I was shocked. I expected a sort of “wham, bam, thank you mam” scenario from A, but I got the opposite. We spoke for a while, and then she rolled over, picked up my arm and put it round her body. This satisfied me the most; as despite the pseudonym A has assigned to me and my role in this blog, I love to be cuddled up to. What a soppy git I am.

Cas